Lady Jane is copyrighted (c) 2000 by RJMcD.
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LADY JANE               by RJMcD                      © 2000

 

John felt a sudden sense of loneliness after seeing his sister and boyfriend off to a vacation in the Swiss Alps. As the airplane climbed into the sky he turned from the observation window and wondered what he would do with himself for the three months of summer vacation. His parents were away at their Canadian lodge, a trip they took every year. This year he didn't feel like going with them. That was something he had done as a child, and he wasn't a child anymore. But not going may have been a mistake. He had absolutely nothing to do for the next three months, and going to the lodge, even though it was with his parents, might have been better than sitting around watching television.

He thought about his sister Debbie, and Debbie's boyfriend Sean, and how they were going to enjoy Europe all summer. He obviously couldn't tag along. There was no other option really but to stay home by himself.

John had broken up with his long legged girlfriend Heather at the end of the school year, and now he thought briefly about calling her. But the breakup had been especially bitter. Not at first, though he had ended up saying a lot of hurtful things in the heat of the moment that he later regretted.

The truth of the matter was that he had no longer found Heather either arousing or very interesting. She had looked on his lack of interest as a personal rejection and lit into him, defensive all the way. He had tried to be nice, saying the standard things like they had just grown apart, but she wasn't having any of that. Weren't there a dozen other guys who wanted her? Of course, but... Wasn't she pretty, she demanded. Sure, he told her, but... Wasn't she good in bed, she hollered. Yes, but... What was he, some kind of fag? That's when John lost it and started slamming her back with cruel things he now wished he had never said. She retorted with things just as cruel, even threatening to get her jock brother to beat him up. It got so bad that she had slapped him, and for John that was it. He walked out as fast as he could, his anger so high that he was afraid he was going to hit her back.

So calling Heather was obviously out. Even if she had calmed down in the last two weeks it was doubtful she'd talk to him. He wasn't even sure he was that lonely yet. Heck, he'd only been by himself for a few hours! There must be other ways to occupy the time.

John wasn't interested in doing anything much outdoors. Having been born with a small frame that didn't fit with the rough sports like soccer and football, and being too short for basketball, he had been left to play tennis, golf and a few other sports, none of which had enough appeal to get him seriously involved. He did a little running but not enough to even call it a hobby. He had been on the school track team one year, but the demanding hours of practice went beyond the small amount of joy he took from being on the team and he hadn't signed up the following year.

He drove back to his family’s suburban home. With no clear idea about how to spend his time he ended up turning on the television just to provide some noise and company, and puttered around until bedtime.

The next day John got up early, skipped breakfast, and wandered around the house. Again he turned the television on for company but paid it little attention.

The following day was pretty much the same, the monotony broken only by a trip to the mall and a short run in the afternoon. He rented two movies and watched them both that evening. Wonderful, he thought, I've got the entire house to myself all summer and I can do anything I want, whenever I want, and I sit around twenty-four hours a day and do nothing.

On the fourth day he went exploring. His sister Debbie was three years older than he was and he decided to explore her room, something he would not normally have done. He found her diary in a drawer, but it was locked and he placed it back in the drawer. There were no love letters or anything interesting in the papers in her desk and he was about to leave when he decided to open the closet.

Why would any girl have so many shoes, he wondered, looking at the floor of the closet, which was covered with everything from sandals and sneakers to boots and even two pair of high heels. He remembered seeing Debbie in the various pairs of boots during the winter but in the high heels only when their cousin got married and she participated in the ceremony. She wore one of the three pair of sandals a lot during the summer, but there were a couple dozen pairs of shoes and sneakers he didn't recall ever seeing her wear. Then again, it wasn't something a brother would notice.

On the top shelf there were at least two dozen shoeboxes and John opened a few out of curiosity. Another pair of heels, this time really fancy with clear bottoms and black straps, more boots, and many more casual shoes.

The shoes were kind of interesting, especially the high heels because they were so strictly feminine. The casual shoes could almost be worn by either sex. Maybe they would still look like girls shoes, but with the high heel shoes there would be absolutely no doubt. That, he figured, is why he looked at them a little longer and why he noticed that they were probably close to the right size for him. Wouldn't it be funny to try them on, he thought. No way. He put the heels back in the box and placed the box in the proper place. No sense letting Debbie know he'd gone through her things while she was away.

His sister had a lot of casual clothes, including jeans and blouses, and not too much in the way of dress up clothes. There were a couple nice dresses and silky blouses and mini skirts, the kind of thing you wear on a dinner date or to a nice party. John took the hangers out and held them up, again thinking how the casual stuff could almost be worn by either a guy or a girl, but not the dressy stuff. As a joke he held a couple dresses up to himself and stood in front of the full-length mirror on the closet door, just to see how they'd look. His own jeans extending out the bottom made the dress look wrong, and for a second he considered taking the jeans off and holding the dress up again. But that was too far out.

It was in the fanciest dress, the one Debbie had worn to the wedding, that he found the key. At first he hadn't even seen the pocket. It was no bigger than a folded dollar bill and the opening was in the folds of the dress. But when he straightened the front of the dress against himself he felt the hardness of the key through the fabric.

It was a small key attached to a red ribbon, the same kind of red ribbon that was sticking out of the bottom of Debbie's locked diary, to be used as a book marker.

He didn't want to mess up the bed so he sat in the hard desk chair and took the diary out of the drawer. The key fit perfectly.

It was a one year diary which immediately made him wonder if there were other years hidden somewhere. If this one was interesting enough he decided he would look for others. Besides, this started with January 1 so there were only five months filled out. Not much.

The first entry was on January 2nd and it said that the writer had never kept a diary before but thought it might be fun and was glad that her aunt had given it to her for Christmas. That answered one of John's questions. This was the only diary around.

The first few weeks of entries were pretty boring. Debbie had used the first initial of everyone's name and he found a few references to himself, but nothing revealing. Then in early February Debbie had met Sean. She seemed crazy about him from the first, and had immediately developed a stereotypical girlish crush. Quickly though, the relationship seemed to get more and more serious, and by the end of the month she was writing that she had gone to bed with him. That made John sit up. He couldn't imagine his sister having sex with anyone.

The writing in March became more detailed and hotter as Debbie gained confidence in writing, and confidence that the diary was locked and private. She described the first time she gave Sean head and how he taught her the techniques he liked. She described the different positions they used when having sex and which felt the best. In fact, as the weekends piled up the book turned hotter and hotter and John found himself getting an erection as he read.

He snapped the book shut and let out a breath. This is none of my business, he thought. He felt guilty and weird about getting an erection. He sure had no sexual interest in his sister and it was just the actions she described that had given him the erection. It was as if it was some other girl. But it wasn't some other girl, it was Debbie, so he locked the diary and put the key back in the dress. He shouldn't even have been in her room in the first place.

By the time he had returned to the front room, turned on the TV, gone to the 'fridge to get a Coke, and seated himself on the couch, half his erection was gone and he was able to put his mind on other things.

 

 

Part Two

 

My first Saturday and I've got nothing planned for tonight, John thought. This is not turning into a great summer.

He was checking the newspaper to see if anything was happening in town when the doorbell rang. When he opened the door he was startled and alarmed to see it was Heather and Bill, her jock brother.

"Can we come in for a second, John?" she asked sweetly.

Stunned, he didn't answer and the big guy pushed by him with a, "Thanks", followed by Heather.

John automatically closed the door and turned to face them.

"What...uh...How..."

"Speechless, huh?" Heather asked, rhetorically. "I guess you didn't expect to see me again, did you?"

"No, I...Well it's good to see you," John said, as his mind raced, trying to figure out if he was in a dangerous situation, or if she just wanted to talk and brought her big brother along to make sure he'd listen.

"Yeah, I'll bet," she said. She turned to her brother. "Go ahead," she said.

Her brother sighed. He hesitated for a minute, looked at her, seemed to decide something, and said, "You know, having a kid sister isn't all that great."

"Just go ahead," she said firmly. "You promised."

"Right, right," he said. He turned to John and held out his hand as if to shake. John, still confused by what was happening, held out his hand. Bill grabbed it, jerked John forward, and landed a solid punch to his gut. John doubled over and on the way was met with Bill's knee, catching him square in the chest. That straightened him up and he felt a hard fist land in the dead center of his chest. It knocked what little wind that remained right out of him and caused terrible pain. He was totally defenseless at that point and Bill began punching him at random, keeping almost all the blows away from his face where the marks would have shown.

When John went down, Bill moved around his writhing body, kicking him over and over again. The last shot was right between the legs and a painful jolt of electricity seemed to fly through John's body just before he passed out.

When he awoke every muscle in his body screamed at him with pain. The most irritating thing was that someone was tapping him on the face and telling him to wake up. He opened his eyes and saw it was Heather, and almost at the same time he realized he was sitting on the couch, that he was bare-chested and that his wrists were tied behind his back.

"What the h..." he started but before he could finish the question his ex-girlfriend slapped him so hard across the mouth that he fell over on the couch, his head spinning.

"Let's get this done," he heard her say through a fog.

"Heather..." Bill started.

"You promised!" she said.

There was a slight pause during which John started to regain his senses, only to be roughly grabbed by the shoulders and pulled forward. Unable to catch himself because of his tied wrists, his knees hit the floor with a bang. Bill held him in place until he got his balance.

"Open your mouth," the jock said.

John turned his head and was met with a shock. He had been stripped to the waist, but Bill had stripped in the opposite way. He was naked from the waist down. With one hand the boy was pulling John's head toward his naked member.

"No...no..." John mumbled.

Bill held him in place and delivered a sharp blow to John's neck. John instinctively screamed and pulled back, but the grip on his head was too strong and he stayed in place.

"This is what you get for raping my sister," Bill said.

"Raping?....I never..."

Another blow cut him off.

"We figured you'd lie, you bastard," Bill said. "Now open your mouth."

"Nooooo," John moaned.

"Make him," Heather said urgently.

"Just wait a minute," Bill said. "Shit, I wish you had some other ideas on getting back at him."

"You promised," she said in a demanding tone.

"Right," Bill said. "Shit."

He pulled John's face back in line with his limp member and said, "There's no getting out of this, John. Heather's going to get her picture or, well, what we decided is if you refused I'd beat you up some more, and if you still refuse we'd cut off your pecker and nuts. So you got no choice. I don't care for this any more than you do, believe me, but after what you did to my sister I figure I've got to defend her and go along with whatever it is she wants, to even the score and make her feel decent again. I told her I'd go along with whatever she wanted, and go as far as necessary."

Picture? John still wasn't thinking clearly and the last part of what Bill said hadn't sunk in yet, but somewhere in the first part there had been something about Heather getting a picture. He turned his head slightly before Bill's powerful grip stopped him, then tried to focus out of the corner of his eye. There was Heather with a camera in her hands!

Bill jerked his face back forward. "You don't have any choices so open your mouth and let's get this damn thing over with," he said.

The last part of Bill's speech was now sinking in. They were going to cut off his private parts if he didn't do what they said. There was also something about being beaten up more. He didn't think he could stand that. They had him. He was in pain, weak, confused and defenseless. He opened his mouth.

Bill lifted his limp organ and placed it between John's lips.

"Geez," he said. "Shoot your damn picture, Heather."

"Close his lips," she said.

Bill looked down. "You heard what she said. Let's get this over with."

John numbly did as he was told.

They heard a click.

"Did the flash go off?" Heather asked.

"No the flash didn't go off!" Bill said. "C'mon, will ya!"

Heather fiddled with the camera controls and tried again. This time the flash went off. Bill immediately withdrew.

"I'm glad that's over," he said.

"Wait, wait, wait," Heather said excitedly. "Look, you're starting to get stiff."

"I am not!" her brother said. He looked down and saw he was lying. Not by much, but he was lying.

"Make him suck it!" she said.

"Damn it, Heather, I will not. You got a picture. That's enough," Bill said.

"Bill, pleeeeze. After he forced me to do that to him, I want to make sure I have a really good picture. We've come this far," she pleaded. "Just a second more."

"I'm not that way," Bill said. "You know that!"

"I knoooow," Heather pleaded. "You're not even in the picture. But make him pay for what he did. I want to see him punished good. It's the only way it will make things right. It's the only way I can go on with my life, Bill. You're supposed to protect me. You didn't protect me when he raped me and made me do that with my mouth. Make it right for me, Bill. Please, please, please."

"It won't work anyway," Bill said.

"Try! Pretend it's Susie. Close your eyes," Heather begged. "You're not even in the picture, anyway. Please help me, Bill."

Her pleadings were so persuasive that even John might have been convinced had he not known that it was all a lie from the very beginning. For Heather it was just a matter of getting back at him for dumping her and saying some cruel things to her when she attacked him. He opened his mouth and tried to tell Bill that, but all that came out was a groan and a mutter.

"Heather, damn it..." Bill started. "Alright, alright, but don't you ever tell a damn soul about this as long as you live!"

"I won't, I promise,' she said with obvious delight.

John, who was still trying to form a protest, felt the almost limp organ slide between his lips. He tried to pull away but Bill's strong grip on the back of his head prevented it.

"Make him suck it," Heather directed.

"You heard her," Bill said. "And I'm not any more crazy about this any than you are, but if it makes things right for what you did, then that's the way it is."

John remained still.

"He's not doing it," Heather complained.

"I know it!" Bill said. He looked down at his dick. "I can't say I feel right about you seeing my dick," he told his sister.

John remained still. He had the urge to swallow but didn't. He wanted to breath through his mouth, but was both afraid to open wide enough and afraid the movement would excite the organ.

"Look, man," Bill said. "She's already got the first picture. This one won't matter any more or any less. But if you don't do what my sister wants, you're going to get your pecker cut off. So you better start suc....well, you know….doing what she wants."

It was true. The first picture would wreck him so what difference did it really make? John didn't like the idea of sucking on the thing in his mouth, but how much worse was that really?

"He's doing it," Heather said.

"Don't you think I know that?" her brother said. "Enough for you?"

"It's growing," she said.

Bill didn't say anything at first, then muttered, "I'm imagining it's Susie."

Heather watched her ex-boyfriend hesitantly suck on her brother's sex organ, and she saw the organ grow.

"I want to get two or three good ones," she said, moving a little closer.

"Heather!" Bill protested.

"Just two or three," she said and snapped off a shot. The flash worked fine.

John had no idea what he was doing. His brain was still in a semi-stupor. Too much craziness had happened too fast, along with too much pain. The only clue he had about what he was doing was his memory of one girl who had done it to him. Even then his movements were hesitant and reluctant and clumsy. But no matter how little he did, however, it seemed to be having a huge effect as the dick in his mouth, which quickly stiffened to its maximum size. He felt as if he couldn't breath, and as if his lips were stretched wide.

The flash went off again. Suddenly the pole was pulled from his mouth.

"Bill!" Heather protested.

"You said a couple pictures," her brother said, reaching for his shorts. "You got your damn pictures!"

"I want to see you come in his mouth," she said.

"No fucking way!" Bill said. "I don't care if you're satisfied or not, this is as far as it goes." He pulled on his shorts and reached for his jeans.

Heather was about to continue her protests but saw that her brother had had enough. It had taken her more than a week of crying, lying and manipulating to get him to finally agree to her plan, and she had to admit that she would have been happy with just the first picture. Now she had two more, both with her bastard ex-boyfriend's mouth wrapped around a fully stiff dick. Secretly she counted herself lucky.

Bill, now fully dressed, told the still kneeling John, "You can work those wrists loose in a little while. Anybody finds out about this and those pictures get mailed all over town, with a nice set of 8 x 10s to your parents. Understand?"

When John didn't answer Bill slapped him on the head. "Understand?"

John nodded.

Bill headed for the door and Heather went up to John. "You don't break up with me," she whispered. "I break up with you."

She followed her brother out the door.

It took John nearly half an hour to work free of the cords around his wrists. The first thing he did was brush his teeth and gargle twice. That was followed by a long, hot shower. Even though it was the afternoon he went immediately to bed. Too sore and too drained to think about what had just happened to him, he fell instantly asleep and didn't wake for fifteen hours.

 

 

 

Part Three

 

He was stiff and sore for the better part of the following week. He rarely left the house and spent some time thinking about what had happened to him. Heather was a bitch, of course, and he should have seen that all along. That she would go as far as she went was a complete surprise, however. He half expected to hear from her about the photos, but the phone didn't ring.

By Friday he was feeling pretty good. Bill had been careful, almost professional, in hitting him in such a way that it didn't leave any marks. He went for a long drive, just to have something to do, and stopped by a park downtown to walk out a few kinks.

Friday night he was back to his normal six hours of sleep and Saturday he woke up with no soreness at all. In the morning he went back to his sister's bedroom and read more of her diary. As soon as he started getting another erection he put it away, feeling strange about getting excited over descriptions of his sister having sex. He was drawn to her closet again, and this time he stripped to his underwear and put on one her fancy dresses. It wouldn't zip up the back and when he looked in the mirror he saw his hairy legs and male face. It looked stupid and he felt stupid, and he immediately took off the dress and hung it back up. He read a few more pages of the diary, but when he found himself aroused again while reading her description of swallowing come for the first time he quickly slapped it shut and put it in the drawer.

He watched an early tennis match on television, then changed into a bathing suit and went out and washed and waxed his car. The sky changed from cloudy to sunny and he worked up a sweat, so when he finished he showered and changed into fresh clothing. At 3:00 the phone rang.

"Hello."

There was silence at the other end, followed by a click.

Wrong numbers were just the worst. They bugged him, and he thought of something to say if the phone rang again. It didn't. He went back to the television and found a pre-game program for a college football game. Thirty minutes later the doorbell rang.

He couldn't have been more surprised when he opened the door and saw Heather.

"Hi, asshole," she said and brushed past him into the house.

He turned and watched her make herself at home on the couch. She put a brown envelope was on the coffee table and said, "Close the door, asshole."

John closed the door and said, "What do you want?"

"Come over here," she said.

He stood still.

"Come over here," she said sternly.

Not wanting to start trouble, he walked over to the couch, feeling very much like a school boy standing in front of the principal's desk.

"Surprised to see me?" she asked with a slight smile.

"Yes."

"I've got something to show you," she said. She glanced at her watch, then picked up the brown envelope. She opened the clasp and looked inside. Carefully, she slid an 8 x 10 color photograph from the envelope and handed it to him.

John looked at the picture and his knees went weak and his hand shook. It was a picture of Bill and himself. It only showed Bill from the waist down and John from the waist up, so they both appeared completely naked. Bill's face was not in the picture, of course. But his limp dick was, and it was in John's mouth.

"Thought you'd like it," Heather said. "Imagine how all your friends and neighbors and family and classmates would like it."

Terrified, John said, "You wouldn't."

"I might," Heather said. "I've got more, and the negatives to make as many as I want." She reached in the envelope and took out a second photograph. "But I think this one would cause more of a stir, don't you?"

She held out the second picture and John reached blindly for it. His head was spinning and his whole body trembled. The picture was similar to the first, but this time the camera had moved closer and the cock in John's mouth was stiff. You couldn't tell from his expression that he was doing this against his will, and there were no marks visible on his face or body. For all anyone would know it was completely voluntary.

He dropped the photos, unable to hold them in his trembling hands.

"But this is really the best," Heather said, ignoring the dropped pictures. She handed him the third photo.

This was taken at an even closer distance and the cock was now clearly fully hard and halfway in John's mouth.

"Oh no," he moaned.

"Oh yes, asshole," Heather said, her voice hardening. "Don't you ever think you can drop me and get away with it. I remember every single thing you said to me that day, and I swore I'd figure out a way to make you pay for it. Well I did, and you will."

"Y-Y-your not going to show these to anyone..." he began to plead.

"That's up to you," she said. She picked the pictures off the table and picked the others from the floor, sliding all of them back into the envelope.

"What do you want?"

"Ah, that's the question isn't it?" she said. "What I want is to humiliate you and teach you a lesson. But the real question is What will you do to stop those pictures from being sent all over town? Which they will be if anything happens to me, by the way, so forget that. So the question is, What will you do to get the pictures and the negatives back?"

"Anything," John said immediately.

"Anything? That's a lot," Heather said. "Think about that before you promise it."

John thought. "I won't kill anybody or anything like that," he said.

"Duh," Heather said. "Of course not. Let's put it this way. I want you to be my slave, and I intend to humiliate and degrade you. I'm really going to make you pay. Not in public. We'll do it right here. But you'll have to do things that you'll hate doing, that's the whole point. The more disgusting things I can think of the better, and I have a wicked imagination. And you'll have to obey me totally no matter how much you hate what I tell you to do."

John didn't say anything. He was still shaking from the shock.

"That," she said, "or I get the printing presses going."

"Here in the house?" he asked to confirm what she said. "Not in public? There's no sense..."

"Here in the house," she said. "Behind closed doors."

"No more pictures," he said.

"I don't need any more, do I?" she said with a wicked grin.

"No more pictures," he said again.

"No more pictures," she agreed. "And when I'm done with you, you can have all the pictures and negatives. But remember, to get them back you'll have to be so humiliated you'll never be able to look me in the eye again. You'll remember this, and fear me the rest of your life."

John looked at her. Despite her cuteness, despite her frequently charming personality, he realized he had somehow flipped a switch in her, and that he would be in for a very rough time. She was making it plain that she wasn't going to go easy on him.

"When does this start?" he asked.

"As soon as we agree," she said, "although agree isn't exactly the right word. See, I planned to do this even before I convinced my brother that you had raped me and forced me to have oral sex with you. And I did it in such a way that it would be impossible for you to refuse. You don't have any choice but to do as I say, and you know it. So agree isn't the right word. Understand might be better. It starts as soon as you understand that you have no choice."

John was getting his trembling under control, but the fear inside him was turning into a sense of total and utter defeat. Just as his knees had turned to rubber when he saw the first picture, his will was doing the same. How could this insanity have happened? Why had he been so thoughtlessly cruel when they argued about splitting up? How had he not recognized that Heather had such a nasty streak? How had things gotten so far so fast?

But it was all true. He had no choice. For all practical purposes Heather owned him.

"So, if you understand that you will be my total and complete slave for the next two weeks we can get started," she said.

"Two weeks!" he blurted.

"That's what I demand," she said. "Of course I won't be over here every night...or maybe I will. I don't think so, but it doesn't matter because whatever I decide is what will happen. For two weeks you will forget your mind even exists. It will be my mind controlling your body and brain. You will do every disgusting and humiliating thing I want you do for the next two weeks, and then you'll get your pictures and negatives and no one else will ever see them. Two weeks, and things will be set right in our relationship to each other." She paused and looked directly into his eyes. "Do you understand?"

He didn't want to answer, didn't want to face the inevitable.

"Do you understand?" she said firmly.

John nodded.

"Never nod to me," she said. "When I ask you something you answer out loud, understand?"

"Yes," he said.

"Yes to which question, asshole?"

"Yes to both," he said.

She stared at him for a moment more then seemed to relax. "Good. There's a large brown suitcase in the trunk of my case. Here are the keys. Bring it in."

John took the keys from her hand and turned toward the door.

"Stop!"

He froze, then turned back to her.

"You will always show deference to me," Heather said. "When I gave you the keys you should have said thank you."

"Thank you," John said.

"Come to think of it, you should call me Ma'am," she said. "No. Mistress. You will call me Mistress from now on. Understand, slave boy?"

After just the slightest hesitation John said, "Yes Mistress". Though he had given in to Heather's blackmail, it had been on a rational, mental level. With those two simple words he fully accepted the situation on an emotional level as well.

"Now hurry up with the suitcase."

"Yes Mistress."

Saying that the second time was easier. The first time, and the reason for the hesitation, was that by using the phrase he was acknowledging to her that he was totally beaten. It also seemed unnatural to be so subservient to a girl that was not only a year younger than he was, but five inches shorter as well. But he'd done it, and he would continue to do it because he had no other choice.

The suitcase wasn't especially heavy though it was obviously nearly full. He brought it into the front room and put it down next to the coffee table.

"Unzip your fly," Heather said.

"What?"

"NEVER question me!" she shouted at him. "NEVER hesitate when I tell you to do something! You will obey me immediately or you'll be very, very sorry. Is that clear?"

"I'm sorry," he said quickly. "I was just surp..."

"I don't want any excuses," she said, still angry. "And you forgot to call me Mistress! Do you want me to take the negatives and have a hundred prints made of each?"

"No! No, Mistress. I'm sorry. Please forgive me. I was surprised, Mistress. Please don't. I'll be okay. I'm really sorry, Mistress," he blurted.

"It will not happen again," she said.

He stared at her for a moment, then seemed to regain control of himself.

"I told you to unzip your fly," she said.

"Yes Mistress," he said and unzipped his fly.

"Take it out," she said.

He did.

"Now play with it," she said.

He realized she was establishing their positions right from the start, but had absolutely no way to resist her. Even when he tried to think of their relationship before the breakup, and how she had been eager to please him during their months of dating, it all seemed a blur.

"Not getting anywhere are we?" she said mockingly.

"No Mistress," he said as he flipped his limp member around.

"Come here."

He walked over to her. Still seated on the couch, she reached out and grabbed his organ, rubbing here thumb over the head and gently stroking the shaft. It immediately came to life, stiffening under her manipulations.

"That's better," she said. "Okay, clear everything off the coffee table."

John did as he was told, his stiff cock still protruding from his open fly.

"Now take off all your clothes," she commanded.

John followed her instructions. By this time he had lost some of his stiffness.

"Stand at the end of the coffee table," she said.

"Yes Mistress."

"Good. Now masturbate for me. I want to watch you jerk yourself off."

John began stroking his shaft and thought about what he was in for. Masturbating in front of a girl because she owned you was humiliating enough, but it was frightening to think this was the first thing he was having her do. It could only get worse.

He got a good grip on his hard shaft and pumped his fist up and down. She was going to get what she wanted, no doubt about that. He could feel the excitement building. His climax was coming closer and closer. Did she want him to just shoot off like this? It would go all over the coffee table for sure.

"Pump it faster," Heather said.

"Yes Mistress."

John did as he was told, increasing the tempo of his strokes and feeling the pressure build in his balls.

"Faster!" she ordered.

"Yes Mistress."

He pumped faster and faster.

"Tell me just before you shoot your stuff," she said.

"Yes Mistress. I'm close."

He stroked his rod with just the right pressure and speed, rubbing the head with his thumb as often as possible.

"Now, Mistress," he groaned.

"You have my permission to come," she said.

John exploded, the white cum flying out of his cock and landing in a wide pattern all over the dark coffee table. He continued to pump and a second and third load jumped into the air. He felt exhilaration, relief and humiliation all at the same time. This girl that he used to date had made him get naked and jerk off in front of her while she remained fully clothed and in command. It was one of the strangest experiences of his life, but judging by the force of his explosion and the amount of thick liquid on the shiny surface of the coffee table it was one that was sexually stimulating.

Heather laughed. "You can clean that up later," she said. "Take my suitcase to your bedroom."

"Yes Mistress."

She stood up, making sure to get in the lead while he got the suitcase, and they walked to his room.

 

 

 

Part Four

 

John guessed that Heather was planning to spend the weekend, judging by the amount of clothing in the big suitcase. She had him take out three satchels, two small and one large but very light, and follow her to the master bathroom. She waved at the small chair in front of the mirror and told him to sit.

"Turn this way," she said.

She felt his smooth face and at first he thought she was going to lean forward and kiss him, but she pulled away.

As she opened the two smaller satchels and starting taking out the various bottles she said, "In thinking about how to get back at you I considered a lot of different things I could have made you do, as my slave. They were all pretty cool, but they didn't hang together, if you know what I mean. Then I got this great idea. What would be more humiliating for a guy than to have to dress up like a girl and act like a girl for two weeks? Once I got that idea all the rest of it fell into place."

She began applying a flesh-toned liquid to his face.

John was trying to understand what you was saying. Dress up like a girl? Act like a girl? Sure, that was no picnic, but didn't guys sometimes do that for those parody plays at different universities. That was funny. Of course, if she meant he had to stay dressed as a girl for two whole weeks it wouldn't be so funny, and that's probably what she meant. Still, he would be in the house and no one would see him. Kinky. Uncomfortable. Awkward. And yes, humiliating, but hardly the end of the world.

The make-up was going a little far, but he could live with that, too. He'd just sit there and take it until she felt satisfied; then it'd be all over.

She really seemed to be taking her time, using all kinds of different products. There were creams that went all over his face, three or four different things around his eyes, more cream on his cheeks, brushes all over the place, and finally lipstick. It all felt funny. He caught a quick glimpse of himself out of the corner of his eye when she had him turn his head, but it was too quick to see anything. She was going full out, that's for sure. She worked on him for an hour or more, pausing to give him a critical examination four or five times, and then adding or subtracting something here and there.

"Not bad," she said when she was done.

John started to turn toward the mirror.

"Look at me!"

His head whipped back.

"Do not do anything without permission," she said. "Do you understand that? I don't want to have to tell you again."

"Yes Mistress."

"Now go fill the tub halfway up with warm water, not hot," she said.

"Yes Mistress."

He did as he was told and got into the tub as instructed. Following the girl's directions he sat there, lathering his body from the neck down, then rinsing off.

"Here," she said, handing him a can of shaving cream. "Let the water out of the tub and put this everywhere you have hair, from the neck down."

"Yes Mistress."

She had him shave every part of his body that he could reach, and she shaved the rest for him.

He rinsed off and toweled dry.

"Now we're getting somewhere," she said with a smile. "Come with me."

He followed her out of the room, stealing a glance in the big mirror and being shocked by what he saw. She had done a magical job with the make-up, making him look almost totally like a girl. His smooth body added a lot to the effect and his lack of pubic hair made him look younger. Of course the short hair on his head and the male equipment in the middle of his body immediately revealed who he really was.

If Heather was out to humiliate him by making him look like a girl she was having an effect. It wasn't so much the make-up, or even the shaving, as it was the fact that she was doing to him whatever she wanted to do and he was obeying. That, in fact, was almost all of it. The girl thing was really kind of fun in an odd way. He felt less stressed rather than more stressed which surprised him. He had never realized it before but being manly was apparently stressful in some way. Naked, shaved, and in full make-up he felt very self-conscious, but also a little relaxed, as if he had a second face to hide behind and secretly look out at the world. Following orders wasn't actually all that bad, either. At least not yet. But who knew what little Heather had in store for him?

In his bedroom she had him sit on the bed. She opened the large satchel and took out a blond wig and some bobby pins.

"I think I'd like to see you as a blonde bimbo," she said as she centered the wig on his head. She brushed any stray hairs under the wig and used the bobby pins to hold it in place.

Standing back she looked at him, then smiled.

"Amazing," she said, and checked her watch. "Good."

For the next couple minutes John watched her unpack selected items from the suitcase.

"I'll have you put everything away later," she said. "Do you know what size shoes you wear?"

"Size 8 Mistress."

"Umm. Well, we'll see." She tossed him a flat package. "Open that. I'll show you how to put them on."

John looked at the package and discovered it contained a pair of black stockings. Things were beginning to get out of hand.

During the next thirty minutes Heather presented John with black satin thong panties, a stuffed black lace bra, a black silk blouse and black mini skirt. The shoes were less of a problem than she thought they might be. The fact that the black high heels were simply a platform with straps that wrapped around the feet and ankles, made them adjustable to slightly different size feet.

Heather helped John stand up. He was shaky standing on his toes, and the heels seemed to wobble on their own, as if they were protesting the presence of his male feet.

"Stand still," Heather commanded.

"Yes Mistress."

He finally managed to bring his shaky ankles under control, though he was afraid that if he moved he would end up on the floor.

Heather looked him up and down. "Not bad, not bad," she mused. "In fact, very damn good. With your slim frame and those cheekbones you had all the natural makings of a good-looking girl. And those legs are fabulous! Half the girls in the world would kill to look that sexy in a mini skirt. You are one pretty thing, let me tell you that."

"Thank you Mistress," John said, though considering the compliment it wasn't easy to say.

"We have to do something about your name," Heather said. "We can't keep calling you John can we, dear? How 'bout.....Jo? No, too much like a guy's name, and you're not a guy any more, are you?"

He hesitated, unsure for a second what to say, then answered, "No Mistress."

"Right. You're a girl from this moment on and you're going to get to know how a girl feels," Heather said. "Let's see..... JoAnna? No. I don't like it. Of course we don't have to stick to J names... How 'bout Jane? Jane. Yeah, I like that. Cute, all girl, short. Jane. It fits. From now on that's your name. Do you like your new name, Jane?"

"Yes Mistress."

"Oh, and when you talk, try to do it in a sexy whisper, but loud enough so I can hear you. I don't want to have to be bothered by a man's voice coming out of a woman's body. Think you can do that?

"Yes Mistress."

"Mmmmm. Well, not too bad, I guess. Just don't do any more talking than is absolutely necessary."

"Yes Mistress."

"That was a little better," Heather said. "Damn, you really are pretty as hell. I've amazed myself. We could probably go to the mall right now and I'm not sure anybody would notice, as long as you kept your mouth shut. Except for walking in heels. We've got to do something about that."

She checked her watch again. "We'll spend a few minutes on that. This is very basic but I want you to pay very close attention. When a girl has a dress or skirt on – and that's all you're going to be wearing for the next two weeks – she always keeps her legs together when she's sitting down. And when she sits down or stands up, she keeps her legs together. That means from the ankles to the...well, all the way up. If you can't get the angle to get up, then scoot toward the edge of the seat with your shoes against the bottom of the chair and twist your knees to one side. Sometimes you have to put your hands on your knees for pressure to help you get up. When you sit down you cross your legs one over the other, not an ankle on a knee like a guy. Do you understand?

"Yes, Mistress."

"You're a girl now," Heather said, "and you have to do everything right, or I'm going to be very pissed. You do not want me pissed at you, do you Jane?"

"No, Mistress."

"Not unless you want it to be photo day for everybody you know – and lots of people you don't know."

John shuddered.

For the next forty-five minutes she had John practice moving while wearing high heels. First one foot forward, shift weight, back, then to the sides, then backward, then two tiny steps forward, and on and on until he thought his calves were going to explode.

"Let's try a walk," Heather said, leading him out of the bedroom, down the hall and into the front room. He was far behind her because of the tiny steps he had to take to retain his balance. Even then, he had to catch the wall two or three times to keep from falling over.

"Walk to the couch and sit down," Heather said.

John did, remembering to keep his legs together as he sat, and crossing them at the knees once he was settled.

"You're a natural girl," Heather said. "That explains why my charms didn't keep working on you. It will never excuse the things you said to me, but I'm evening that score in the next two weeks. Okay, now stand up, and remember to keep your legs together."

As John went through the practice he couldn't help thinking about the dig that Heather had thrown him. A natural girl? No doubt she said that just to humiliate him a little more, and justify her own failure in being able to keep him attracted. Still, he had seen himself in the mirror, and if he didn't know he was seeing himself there's no doubt he would have found the image reflected back at him to be both beautiful and very sexy. Almost any girl's appearance was helped by high heels, black stockings and a mini skirt, but the girl in the reflection appeared to have the natural figure that made the attire spectacular.

Heather was right about the make-up, too. He didn't know anything about cheekbones and all the stuff she had talked about, but he had to admit that the girl in the reflection was hot. He would have made a pass at her in any club and anywhere else. It was hard to remember that she was he. But then of course Heather – Mistress Heather that is – wanted him to be a girl for two weeks, and it was in his own best interest to try to think and behave that way, just as thoroughly as he could. The clothes helped a lot. The silky panties and the thong riding between his cheeks sure gave his smooth skin a feminine feel. Shaving his body had a big effect, not only in his appearance but in the way he felt. Then there was the wig and make-up. The blonde wig was a full, wavy thing and, although it felt a little bit artificial, there were plenty of girls who wore wigs and must have felt the same way. All in all he had to admit that looking and feeling like a girl, especially a slim, hot, good-looking girl, wasn't the worst feeling in the world. If Heather knew his real reaction and was out to humiliate him by creating this transformation she would be disappointed. This was going to be two weeks of fun play acting that he would never have had the balls to try without being forced to do it.

He was still practicing his sitting and standing when the doorbell rang. A panic came over his face and he looked to Heather. She smiled and checked her watch. "Sit down," she told him.

"But..."

"I said, sit down," she repeated firmly.

He sat down, remembering to keep his legs together in the process, and crossing them when he was seated.

Heather started for the door.

"Wait!" he blurted.

She whipped around and said, "That's it! You're history!"

"NO!" he said, real panic in his voice. "Please, Mistress! I'm sorry! Please don't! Mistress! You're my Mistress and I'm your slave and I'm sorry. Pleeeeze forgive me! It was a surprise. I panicked! Please forgive me! Please! I will never, never, question anything you say ever again! I swear!"

Heather looked at him and the doorbell rang again.

"I own you for the next two weeks," she said. "You don't seem to understand that. If I can't get back at you this way, then the only thing I can do is send everyone copies of these photographs."

"I know, Mistress, I know. I understand. It was panic. Surprise! I'm sorry. It will never happen again. For the next two weeks I will never let surprise get the best of me like that. You own me. I understand that. I have no choice. I understand that. You're the boss. More. It was a stupid thing for me to do. I'm a dummy. An asshole. Please forgive me. Give me another chance, Mistress. Please......please."

Heather stared at him. The doorbell rang a third time but she didn't appear to hear it. She had a lot of humiliation in store for him, just as much humiliation as he had given her for breaking up with her and saying those horrible things to her. He deserved everything he was going to get. Spreading the pictures around would finish him, but it wasn't direct and personal like the plans she had for him for the next two weeks. And he'd tell everyone how the pictures got taken, and some people would believe him. That would piss off her brother, and cause problems for her, too. And mailing the pictures would be like getting back at him in a remote way. She wanted it personal, direct and in his face.

"Last time," she warned. "I'm going to pass this because this is new to you, and I know you would honestly rather spend the next two weeks taking my humiliation than have me mail these pictures. So I don't think you were disobeying me, and I think you did panic. But it can't happen again. Surprise or no surprise, you've got to be a good little girl and take whatever shit I dish out to you. I'm going to enjoy watching you crawl and that's the only reason I'm going to give you another chance. But let me make one thing perfectly clear. If it happens again no amount of begging will change my mind. You will be history."

She stared at him until he said, "Yes Mistress."

"I should have you answer the door, you prick" she said. And with that she went to the door and peeped through the circular lens. Finding that it was who she expected, she opened the door and stepped aside.

The guy who walked in was of medium height and build, and seemed to know Heather, for he kissed her briefly on the lips before turning into the room and discovering John/Jane.

"Whoa, what's this?" he said.

Heather smiled and took him by the arm. As they stepped toward the couch she said, "This is the girl I was telling you about this afternoon. Her name is Jane."

"Hello, Jane," he said with a smile.

Before John could answer Heather cut in. "Jane doesn't talk much," she said. "Jane, this is Bobby. Bobby and I have known each other for a couple months but just started dating last week. We've been out twice so far, and I felt I could confide in him. I told him you were a very special girl, and suggested he come over and meet you tonight."

John was flustered, unable to say anything, and not sure what was going on but suspecting this was going to be a far different evening than he had anticipated. Practicing walking and sitting were no longer in the cards.

"Outside of telling Bobby you were a special girl and that you were under my control, I didn't really say much more. I thought I'd wait until I saw how you turned out and how Bobby reacted to you. I'm pleased with both." She turned to the guy, "Why don't we sit down?"

She steered Bobby to the center of the couch and took a seat at the other end.

"Bobby's a pretty fast mover," Heather said. "On our first date he got me to go to bed with him. Not that there's anything serious between us. We just seemed to have a couple things in common, and hit it off real good. We think we'll be more friends than lovers."

"Right," Bobby said. "Not that I'm not going to take your beautiful body to bed from time to time..."

"MMMmmmm," she said with a smile.

"But," he continued, "we figure we're going to be more like friends who fuck."

"Exactly," Heather said. "And friends who share."

Bobby turned and smiled at Jane. "If Heather hadn't told me I would have never guessed," he said.

"Would you like to see the proof?" Heather suggested.

Bobby hesitated. "No thanks. I believe you. Right now let's keep the illusion, if you know what I mean." He slowly looked Jane up and down, from the crown of her blonde hair to the tips of her black strap on high heels. "Amazing," he said, almost to himself. He turned back to Heather. "I really can't believe it. I mean I can, I don't doubt you, but...." He laughed. "What can I say?"

"Well, since you know we're friends and I invited you over here tonight and that I won't be jealous, why don't you kiss the new girl...." She leaned around Bobby and looked directly into Jane's eyes, "....and I'm sure she'll kiss you back. Let me know just how good a kisser she is. As I told you, she's completely under my control and I'm instructing her now to do whatever you want."

Bobby raised his eyebrows at hearing this and turned back to Jane, who looked shyly downward. He and Heather hadn't discussed anything about the evening in advance, so the suggestion was a surprise to him. And contrary to what Heather had said, his real motive for making a play for the long-legged blonde was because Heather had something he badly wanted. He wasn't thrilled with either her propensity to put down people, or her very modest intelligence. The body was very fine, however, and the sex had been a bonus. He had guided their relationship as quickly as possible into "friends who fuck", but he knew as soon as he got what he was after she would be out of his life. Until then, he needed to humor her and keep her happy.

For Jane, the idea of kissing a guy was somehow more frightening than what she had had to do with Bill. That had been mechanical, motionless and passive, for the most part, Kissing, on the other hand, was intimate and personal and active. She didn't know if she could do it, and at the same time knew she had to. Heather was leaving her no choice and she even wanted a report on how good a kisser she was. No matter how weird it was, she was being forced to perform as good as she possibly could.

Bobby put his arm around her shoulders and smiled at her. She gave him a weak smile back. "This is a new one for me," he said, again mainly to himself, "but you are a beauty."

With that he leaned forward and kissed Jane.

Backing away wasn't an option and Jane sat motionless at first. Having a guy kiss her was very strange, though if she put her mind to it it wasn't really all that different from being kissed by a girl. Heather wanted a report on her cooperation so she better try and do what she could to respond. She moved her head and lips.

When Bobby slipped his tongue into her mouth she froze. His soft wet tongue explored the insides of her mouth, finding her own tongue. She wiggled hers a little and his tongue responded. The tongues caressed each other inside her mouth, then his withdrew slightly and he kissed her open mouthed. She knew it was time to slide her tongue into his mouth and she steeled herself for it. When she did extend her tongue, sliding between his lips, he moaned slightly. This is what Heather wanted, no doubt. Jane increased her efforts and soon the couple was indulged in a wet, hot make-out session. Bobby's strong hands gripped her shoulders and waist and pulled her to him, while their tongues played with each other.

When Bobby broke the kiss Jane was surprised to find herself breathing heavily, and more surprised to find she had the beginnings of an erection.

"Well?" Heather asked.

"She kisses good," Bobby said with a smile. "She gives good tongue."

"Well it's about time to find out if she gives good head, too," Heather said.

Jane wasn't as shocked as she could have been. Ever since Bobby walked in the front door she had a suspicion that she would be made to perform like a real girl. The thought had gradually settled in her brain, giving her a little time to get used to it without actually facing it straight on. Still, it would take all the will power she had to actually do something so foreign.

"I want to see her undressed first," Bobby said, "if that's okay with you."

"She'll take off her skirt and blouse but she leaves the rest on," Heather said.

"Keep the illusion going," Bobby said, again sounding like he was talking to himself more than Heather.

"Jane, stand up and take off your skirt and blouse," Heather said.

Jane moved awkwardly to her feet, remembering to keep her legs together. Once she was standing she took a moment to gain her balance in the high heels. The silky blouse unbuttoned down the front and it was only her trembling fingers that made it take so long to get undone. The silky material slid down her smooth arms and she tossed the garment on a chair. The mini skirt unzipped down the side and she suddenly realized that when she took that off her semi-erection would show through the front of the black satin french cut thong. Unfortunately, like so much of her life at the moment, there wasn't any other option. She had to do what she was told.

Jane unzipped the mini skirt, held it a moment, then let it drop to the floor. Quickly she turned around and sat down on the couch. If either Heather or Bobby saw the bulge in her panties neither one said anything.

Now wearing nothing but a black bra, black satin panties cut so high on the sides that they covered almost nothing, stockings and high heels Jane was as self-conscious as she'd ever been in her life.

"Very pretty," Bobby said admiringly. "Very, very pretty, and very sexy, too. Hell, you are one hot young thing let me tell you." He turned his head the other way, "Heather, you sure know how to pick 'em."

Heather liked the compliments on Jane's girlishness because she knew how embarrassing that was to John, but she was less sure about Bobby getting hot over Jane. The object was to humiliate Jane, not make her feel good, so Heather determined to keep a close eye on her slave, to see whether the compliments were making her feel good or bad. In the meantime she supposed that it would help Bobby get aroused, something she had had her doubts about when she first told him about her Jane. But then that was before he saw what a pretty girl John was. She slid her hand over Bobby's lap and could feel the beginnings of his erection. Well, making him physically able to participate in John's humiliation didn't look it was going to be any problem at all.

"Ohhhhh, Heather, you want some of that?" Bobby asked as he felt the girl's hand on his crotch.

"I want the new girl to satisfy you first," Heather said. "Why don't you stand up and I'll have Jane undress you. She's never taken a guy's pants off before, and of course never touched a guy's cock."

"Sounds like a plan to me," Bobby said. He stood up, directly facing the couch, so he was turned toward neither Heather on one side or Jane on the other.

"Undress him, Jane," Heather ordered.

"Yes, Mistress."

Jane reached up with both hands and undid Bobby's belt buckle. The button at the top was next, and then she pulled down his zipper. With little effort she wiggled his pants down his hips to the floor, and he stepped out of them. He lifted one foot and Jane removed his shoe and sock, doing the same with the other foot. She put a pretty manicured hand on each side of his briefs and pulled them all the way down to the floor.

Jane had been going on automatic to that point. She was used to taking off a man's pants, shoes, socks and shorts – just not the same items on another man. The automatic part ended at this point, as she looked straight ahead and found her vision filled with naked hips, a hairy set of men's balls, and a cock that was half-way on its path to a full erection.

Jane subconsciously compared the organ to her own and decided that Bobby had her beat by an inch. But it wasn't size that occupied her at the moment. It was what she had to do next.

"Take it in your hand and stroke it," Heather commanded.

Jane was actually glad to hear the instructions. She would much rather move by command than to act in what would appear to be a voluntary way. If Heather hadn't said anything but "Start, Jane" or something like that, then each action have been her decision. That would have been far worse than to simply do what she was told.

She wrapped her soft fingers around the organ and it immediately jerked to life, hardening slightly. It felt really weird to have a cock in her hand. Her hand even looked strange. The red nail polish and ring that Heather had supplied somehow made her fingers look longer, softer and smoother. It had to be an illusion and maybe it was just the nail polish that triggered the idea that her hand was a lady's hand and therefore should appear soft and smooth. Whatever the reason it sure was effective.

She started to slowly stroke the cock as Heather had told her to do. The meat grew just as slowly, gradually getting firmer and firmer until it was rock solid. She gave it a quick stroke and Bobby moaned.

"Use your other hand to play with his balls," Heather said.

Jane moved her other hand and gentled cupped Bobby's balls in her fingers. They bounced as she stroked his cock and she was careful not to squeeze the hairy sack. For a second the thought that she was actually caressing a man's balls, and pumping his stiff cock, passed through her head. Somehow, probably because she was obediently following orders, the whole thing seemed unreal to her. The hands she saw were gentle and graceful and didn't look like the hands she was familiar with.

No doubt it was real to Bobby. His cock was stretched to the max and became as hard as could be. He was watching Jane play with him and occasionally throwing his head back, moaning quietly. Few girls in his experience had ever fondled his cock and balls as skillfully as this hot blonde.

"I don't want you going off in the air," Heather told him. "I think it's about time our new girl got her oral cherry popped by finding out what its like to have a man's hard cock in her mouth. Jane, I want you to suck his cock. And suck it good, with lots of passion. Let him know that you're just wild about sucking on his stiff pole. I want to see one very hot, very enthusiastic blowjob. I want to see you swallow it all, lick it while you suck it, and really put your heart into it. Drive him up a wall with your eagerness to please him. Make him come big and hard, and when he does I want you to just keep sucking his stick and swallowing his come until you've totally drained his balls dry. Now go ahead."

Jane thought she was going to die. That was just the kind of command she hoped she would never hear Heather issue. She was hoping for slow, step-by-step instructions. Do this, now do this, now do that, now the other way. She could have withstood that and told herself she was just doing what she was told at every step. But now her Mistress had issued her a broad but very specific command, and the order insisted that she be a very active participant in the act. Every movement, from beginning to end, would be her decision, at her initiative, and it all had to be "enthusiastic" and "from the heart", to use Heather's words.

As much as she understood what was at stake she wasn't sure she could do this. Bobby seemed like a nice guy, but he was still a guy, and the idea of putting his cock in her mouth was alien enough. To be commanded to be enthusiastic and passionate about it required all the will power in the world, plus a good measure of forgetfulness. She would have to forget she was a guy, and that all this was Heather's way of humiliating her. She would think of herself as a girl. That might help, if she could bring off such a far out bit of mental juggling. But even with that she was overwhelmed by Heather's command to show Bobby she was "wild about sucking on his hot pole."

If that wasn't enough to put her head into a spin, the final command was the most humiliating of all. Jane was supposed to let Bobby shoot his come into her mouth and swallow all of it. That was the most astounding thing she'd ever been told to do in her entire life. Let a man have his orgasm inside her mouth! How could she do that? Her mouth was so personal and private, and now she was supposed to not only let a stiff cock enter there, but when that cock got super aroused and reached a sexual climax she was supposed to let it ejaculate onto her tongue, against the insides of her cheeks, on the roof of her mouth, and then let the warm sperm trickle down her throat. And do it "enthusiastically"! The wildness of the thought left her dazed.

Heather insisted the blowjob be good, be more than good, but she had no idea in this world how to do that. She had zero experience, had never even thought about the idea, and now it was demanded of her that she be both enthusiastic and skillful. She knew better than to disappoint Heather, but she wasn't sure exactly how to go about pleasing her. The only thing she could hope for was that maybe Bobby would let her know what to do. Not that she could envision herself doing it right, or fooling him into believing that she was enjoying what she was doing and eager to please him. Then again Bobby probably didn't care if she was sucking him with honest enthusiasm, or faked and forced enthusiasm. No doubt the only thing that concerned him was whether or not it felt good.

"No more stalling, Jane," Heather said. "Do it."

Jane scooted forward to the edge of the couch. Her hands and his organ were now within inches of her face and she let out a sigh, surprised that she'd been tensely holding her breath. She closed her eyes for a moment to gather her will power.

"Wet your lips, baby," Bobby said.

She slid her tongue out and did as she was told. It delayed the inevitable for a moment. She tried to think of something else to stall with but quickly realize that stalling too much would probably displease Heather. Trying not to think of what she was actually doing, she lowered Bobby's firm cock to a horizontal position and moved forward slightly. Her soft, red lips touched the tip of his cock and she pushed herself to begin. Her lips parted, sliding around the rounded wedge formed by the head of the cock. She stopped before the head was inside. The reality of what she was doing suddenly hit her and she couldn't go on, but she couldn't withdraw either so she just stopped.

In a moment she got control of herself. She also got over some of her fears. This, she thought, is humiliating but not as bad as I thought it would be. After all, it's only a part of the human body. I have to do this, and I can do this.

She leaned forward slowly, and her lips slipped off the widest part of the cock head and wrapped around the shaft. Bobby's erection felt larger than it looked.

"I don't want to feel your teeth," Bobby said, "just your lips and tongue."

She gave a brief nod to acknowledge the directions and was surprised to hear him moan. She had just learned something.

Jane took another inch of cock into her mouth and paused again. Her breath, out of a combination of fear of the unknown and nervousness, was coming in harder and harder pants. With the organ in her mouth she was forced to breath through her nose and her nostrils flared in and out as her heartbeat increased.

She moved forward again and now had half the organ inside her mouth. It felt so much thicker than it looked that it amazed her. And warmer. She didn't recall it feeling so warm in her hand.

Heather had said to lick it when it was in her mouth, so she lifted her wet tongue and slid it across the underside of Bobby's erection. That made him moan again. She tried to slide her tongue up the sides of his cock with the goal of licking it all over but only got partway up. It didn't seem to matter to him because it was clear he was enjoying everything she was doing.

After a minute she stopped licking him and moved back, letting the cock slowly slip free. She was out of breath and had to get her breathing under control. There was a slight urge to gag but nothing severe, and it disappeared as soon as the organ was out of her mouth.

Well, she thought, it could be worse. In fact, it's not really all that bad. Not, she realized, exactly passionate but Bobby seemed to like it. Still, Bobby wasn't the one she had to please, Heather was. Or rather she had to please both of them.

She wet her lips again, kissed the tip of the cock, and slid her lips over the head and down the shaft. She knew that a blowjob was an in and out sort of thing and she began doing that. Her red lips formed a tight circle as they slid from the tip to half way down the pole and back again. After a minute of this action she was actually getting used to having the aroused cock in her mouth.

Without knowing why, other than that she had to add something interesting to the blowjob, she turned her head to the side and let the head of Bobby's cock slide along the inside of her cheek as she continued with the in and out sucking. After half a dozen strokes she turned and let the head slide along the inside of her other cheek.

She returned to the direct in and out, holding on to the base of his erection with a circle of her thumb and first finger. His balls bounced against the palm of her hand. It was obvious that he was trying to stand still and let her provide all the motion and all the stimulation, but it was equally obvious that at times she was getting to him so intensely that he couldn't help but react with very short thrusts of his hips.

She was still breathing strongly through her nose and needed to break away and get some air. Her panting was now caused less by fear and nervousness, and more by what could only be described as enthusiasm. She wasn't excited, but she was starting to suck with some of the eagerness that Heather wanted. The better she performed the sooner it would be over, and that was the explanation she gave herself for her seemingly enthusiastic behavior. Deep inside was the small seed of a thought that she was actually beginning to enjoy herself a little. Exactly why she wasn't sure. The truth was that she was beginning to think of herself more and more as a girl who was pleasing a man. In her clearest moments she knew that wasn't true, but she also knew that the fantasy was coming closer and closer to becoming a reality.

She let Bobby's cock slip from her lips again and took in a deep breath. Now what? She couldn't just sit there on the edge of the couch and make the two of them wait until she started breathing normally. To keep him aroused, and to keep Heather happy, she wet her tongue and began licking the organ. At first she twirled her tongue around the head of the cock, tracing the curves, leaving it shiny and wet, then she pushed the pole against his belly and began long, slow licks from the base of the cock all the way to the head. As with almost everything else she'd done it caused a positive reaction in the guy standing in front of her and she again heard him moan. She smiled slightly, a little amused at how her actions brought such a powerful reaction.

By then her breathing was perfectly normal, even though she felt a little positive tension. She hesitated to call it excitement but reluctantly admitted to herself that that's probably what is was. She didn't want to think about it, and in fact had no time to think about it. She had to increase the pleasure Bobby was feeling if she wanted to pull this off successfully.

Jane wet her lips and slipped the throbbing cock back into her mouth. She forced herself to let it go deeper than it had before, and fully three quarters of the stiff member was in her mouth before she had to stop. She sucked him without moving in and out, creating suction then letting it go, over and over. From time to time she whipped the cock with her warm tongue. Then she suddenly changed to a medium rapid in and out movement, running her soft red lips up and down the length of the cock. Bobby's hips started to tremble and he started moaning again.

She was pleased with her success. From starting out thinking the whole thing was insanely impossible, she had brought herself to the point where she felt almost as if she was in control. If he got too aroused she could back off, and that would make him back off. If her mouth started going wild on his dick he instantly reacted with shudders and moans. She began to enjoy playing him, running him up and down the sexual tension ladder.

After a few minutes of truly enthusiastic sucking she knew she had to come up with some other variation. She didn't have a clue as to what that could be until she realized his balls were still bouncing again the palm of her hand. Should she stop and lick his balls? Could she bring herself to tongue the hairy sack? The thought wasn't appealing and she didn't know for sure if Bobby would like it. Well, that wasn't exactly true, either. She knew he would. It was just an excuse because she didn't want to do it. Sucking on his cock was turning out not to be such a hard thing after all. She had even surprised herself by enjoying parts of it, especially the reactions she got from her every new move. Truthfully, the whole thing wasn't bad. Being dressed up and made up as a pretty girl was sort of like playing a role in a movie, and she was beginning to pride herself on how well she was doing. At least judging by the cock in her mouth. It was swelling to the bursting point and was harder than she ever imagined it would get. It kept getting hotter, too, and Bobby's hips were now twitching almost constantly.

She slid her left hand up his naked thigh and touched his balls.

"Oh, baby," he moaned.

His reaction delighted her and she began lightly caressing his balls as she sucked on his pole.

"Baby! Oh damn!" he groaned.

Suddenly it hit her that she was driving him toward his climax. Everything she had done was getting him more and more aroused, and she could feel how tightly wound up he was. She had avoided thinking about what it was all leading up to but now it stared her boldly in the face. He was going to come soon. If she continued sucking, and caressing his cock with her tongue, if she kept fondling his balls, he was going to reach a point where nothing could hold him back. She had let herself get lost in the fun of role playing, of being a pretty girl getting her boyfriend all excited, and forgotten the reality of where it all would lead.

Jane slowed her in and out sucking and let her tongue settle to the bottom on her mouth. Her fingers stopped moving on his balls.

"Don't stop!" Heather yelped. "Get him off, damn it!"

Jane felt a rush of anxiety. Her stockinged legs pressed tightly together as a way to channel some of the tension from her head. This is it, she thought. I made him this excited so what did I expect?

She resumed sucking, and started moving her tongue over the straining cock. Realizing that she was still in control in some way she dove into finishing what she'd started. Her slim fingers began to again fondle his balls. She drove her lips farther down the shaft, rapidly bouncing her head up and down and keeping her lips firmly circling the cock.

"Yeah!" Bobby shouted. "Oh, yeah! Yes, yes yes!"

His hips jerked and twitched. Jane passionately sucked, excited by all the pleasure she was creating. She was causing it all. Bobby was going out of his mind, and all because she was exciting him with her mouth. She bounced faster and faster, always keeping the expanding cock in a tight grip with her lips and trying to move her tongue against the throbbing organ.

"YES!" Bobby yelped.

The first jet of come was released just as she had most of the cock in her mouth, and it hit the back of her mouth with a force that shocked her. She opened her mouth but instinctively knew that she had to continue and immediately wrapped her lips around him again. The come had pooled in the back of her mouth and she was trying not to swallow it when the second spurt erupted. The cock jumped in her mouth and she felt the warm come hit her tongue and slide to the back of her mouth. That was too much to contain and she opened her throat and swallowed the liquid.

Bobby's hips were now jerking uncontrollably. He pumped forward and shot off again. His cock had been aimed a little sideways and the jet hit the inside of Jane's cheek. She backed off until only the head of Bobby's cock was in her mouth and managed to swallow quickly. She had no idea how much more man juice he was going to deliver but she knew she better keep going if she was going to please him completely.

She continued to suck and was rewarded with a small shot of sperm. By now her neck was sore with the effort, and she felt it safe to slow her movements a little. Bobby's cock still jumped whenever she touched it with her tongue but his body movements were beginning to settle down. The cock in her mouth twitched and she tasted a final couple drops of the pearly white liquid. She swallowed, and then washed the remaining honey off his cock.

Gradually the organ began to shrink, and Jane was surprised to find that she was reluctant to leave it. After all the excitement, all the passion, and all the tension it was difficult to believe it was over. Bobby had obviously been more than satisfied. The big question was whether or not Heather was pleased.

When the organ had shrunk to its unaroused state she let it slip from her lips.

Bobby reached down and lifted her chin. She looked at him and turned a scarlet red with embarrassment. He knew everything about her. He obviously knew of Heather's control, though he just as obviously didn't know what that was all about. He also knew what was in Jane's panties. And he saw how she had turned from reluctant and fearful to enthusiastic. He had watched her blow him and even swallow his come. She tried to turn away in shame but his strong hand held her in place. He bent down close to her and said, "That was fantastic." He kissed her lightly on the lips. She was too stunned and confused to respond, but when he kissed her a second time, sliding his tongue into her mouth, she opened her lips and slid her own tongue forward.

Bobby stood up. "Fantastic, doll," he said. He turned to Heather. "In fact, after I rest up a little I think I could go for round two."

"Not a chance," Heather said. "Pull your pants up, you're going home. My new slave has got a lot of learning to do. I want to make her into a complete girl and that means teaching her how to walk properly in heels and a whole bunch of other stuff. I'll see you tomorrow. You can take me to lunch."

That obviously didn't please Bobby but he didn't argue. Heather apparently wore the pants in their relationship, at lest to some extent. Jane wondered if there was something going on there that she didn't know about. Bobby wasn't being bossed around like she was and it was apparent he didn't want to piss Heather off. Then again, Jane thought, why should he when Heather could provide him with a treat like Jane. She blushed again at the thought of how she'd been made to perform with a stranger.

Bobby dressed slowly but once he was ready he didn't linger. He asked Heather where she wanted to go for lunch, and Heather said she'd call him and let him know. Then Bobby kissed her, turned and winked at Jane and was out the door.

"Well," Heather said, "you're quite the little slut, aren't you?" She waited for a reply.

"Yes Mistress," Jane said.

Heather smiled. "I thought he was going to shake right out of his skin, especially there at the end when he was coming in your mouth." She again paused for a reply.

"Yes Mistress."

"I never let boys come in my mouth," Heather said. "It's so degrading. But you seemed really eager to taste his stuff. You were going at it there at the end like you could have swallowed a gallon of that goo."

The pause told Jane that she was being commanded to respond and she did. "Yes Mistress."

"If I let boys come in my mouth like that I'd feel I'd gone as low as I could go," Heather said, trying to drive home the humiliation. "And to swallow that slime? No way! If a boy came in my mouth I'd spit it in his face, and he could finish off in the air for all I cared. It's so cheap and slutty. But you...I never saw anyone suck on a cock so enthusiastically. You weren't faking it, either. I could tell. You really, really loved it. I think you're just a natural born slut." She turned away without waiting for a reply. "Come with me," she said.

Jane got up from the couch, remembering to keep her stockings legs together as she did, and unsteadily followed Heather to the other side of the room.

"You've got a long way to go before I'm going to be happy with you," Heather said. "I have to admit that you pass the appearance test a lot better than I ever imagined, but appearance is only a small part of what I want to accomplish. I want you transformed totally into a girl before I'm through with you, and that means being able to walk normally in heels. Of course that's just the beginning. I'm going to teach you how to give me a pedicure, and apply make-up, and a whole bunch of other stuff. But you look like an asshole trying to walk in heels so we'll start with that. Go back to the couch and get your skirt and blouse and put them on – and you better not fall."

Jane was still coming down from the confusion of her encounter with Bobby. Some of the things Heather had said to her were obviously just meant to make her feel bad, part of her getting back for the cruel things that had been said when they broke up. But there were other things that had sliced right through her because there was a substantial element of truth in them. She had lost it. At moments when she was servicing Bobby she had forgotten that she was being forced to do it and had actually gotten involved in pleasuring him, in turning him on. At times she had felt proud of the effect her actions were having, and considering that it was her first time giving oral sex, and considering what she had in her panties, she was stunned to remember that after she'd resigned herself to the task and gotten over her fears and reluctance, that she had enjoyed giving the guy pleasure. It was especially unnerving to think of the cock exploding in her mouth. Though it was true that Heather had unbelievable power over her, she was now sure that if she had gagged and spit out the white liquid that even Heather would have cut her some slack. But she hadn't gagged and she hadn't spit and she hadn't really disliked it. It was strange and new, but it was a reward of sorts and the most positive sign possible that she had been successful in arousing the organ to the highest point possible.

All of which was totally confusing and disorienting. Heather had watched her every move and had zeroed in on the truth in order to humiliate her with it. It was working. She knew she shouldn't have reacted like she did, but she also knew she wasn't sure exactly how she felt about that. Heather wasn't going to give her time to think about it, either, so there was no immediate possibility of resolving that confusion and those doubts. Heather was going to keep pushing, and Jane had no choice but to go along with it. She headed toward her blouse and mini skirt on the couch, trying to keep her ankles stiff by taking small, mincing steps.

 

 

 

Part Five

 

Jane awoke when the alarm went off at noon. Heather had kept her practicing her walk for hours, and then decided to teach her make-up, followed by another session of walking in high heels. Then she had Jane unpack the rest of the suitcase, hang up appropriate items, and put the rest away in drawers. After that Heather had her sit and stand, sit and stand, until she thought her legs would give out from under her. Heather even gave her instructions in how to stand so her legs and body would look their best. The lessons went on until well after midnight.

Sometime during the early part of the evening Heather stopped calling Jane "asshole" and started calling her "slut". She also never missed an opportunity to make her do something extremely female, such as taking a whiz by hiking up her skirt, lowering her panties, and sitting on the seat. But all in all it was more physically exhausting than humiliating. Not that Heather didn't get her digs in any time she could. It was just that her emphasis seemed to be more on forcing Jane into feminization than anything else. For a guy, that was supposed to be the worst thing possible, but Jane discovered that she didn't feel very bad about it. Some of the things were surprisingly interesting, and walking in heels she took as a challenge.

As she rolled out of bed she realized she still wore the pink nighty that Heather had made her don before she left. Her Mistress had instructed her that she should continue with the female charade twenty four hours a day, whether Heather was there or not, and the lace nighty was part of that.

So were the pink high-heeled slippers, with the ruffles at the toe. Jane considered pushing them aside but thought better of it. Suppose Heather popped in unexpectedly. She had demanded a key and Jane had given her one, so it was likely she would try to surprise her. Better to wear them than be caught in another room, without time to run and get them, if Heather showed up. She slipped them on and stood up.

The pain shot through her calves and into her knees and she fell back on the bed. The hours of walking on her toes last night were showing up. She swung her legs onto the bed, leaving the high-heeled slippers on the floor, and began massaging her silken calves. She watched herself, seeing her slim fingers with the red nail polish rubbing the smooth, hairless skin of her legs. How girlish looking, she thought, reacting neither positively or negatively to the thought.

She did the stretching exercises Heather had told her to do and followed that with a hot shower. By then her legs were feeling much better and she was able to wear the pink high-heeled slippers without any trouble.

After breakfast, if that's what a 1 o'clock p.m. meal can be called, she stretched some more and then went into the main bathroom. There, she found all of the bottles and jars Heather had used on her the night before, and later had taught her how to use. She busied herself with her make-up.

When Heather unlocked the door and walked in a few hours later Jane had just stood up and was starting to again practice walking in high heels.

"Good girl," Heather said when she saw what Jane was doing. "Come with me." With no more greeting than that, Heather turned and headed down the hall.

In the main bathroom Heather touched up some of Jane's make-up. Except for the odd cutting comment about Jane's ineptitude in applying certain parts of the make-up she worked in silence, and Jane knew better than to speak without being spoken to. She wondered what was in store for her on this, the second day of her two-week sentence. And that's what it was, a sentence. She had been sentenced to two weeks as a slave. Two weeks acting the role of a girl and doing everything Heather commanded. She was sure Heather would keep her playing the girl role for all that time. She had been as much as told that and she'd resigned herself to the fact. There was no escaping this sentence.

Last night she had been so exhausted that she'd fallen asleep as soon as her head hit the pillow. But this morning she had had time to think. The previous night began to look like a strange, remote dream to her. When she thought about her actions she almost believed she had been drugged or something. It was complicated and confusing. In the light of morning she couldn't understand her behavior and almost convinced itself that the events with Heather's friend Bobby hadn't happened. Or at least hadn't happened the way they had happened. Or that they had happened the way she knew they had happened, but it was only because he had temporarily lost his mind. How could he have behaved so completely like a girl? It didn't make any sense. How could she have been forced to perform oral sex on a guy? That was amazing. How could she have liked it? That was the most confusing part of all. She hadn't liked it, not at first. She hadn't liked getting dressed in the sexy stockings and all the rest, though he did remember that it at one time seemed kind of fun. She hadn't liked having to wear make-up and a wig. It did complete the look and the role she was playing, and he remembered seeing herself in the mirror and thinking that that was one hot babe reflected back at him. It was all so confusing. He got mixed up trying to understand her feelings, not even sure if he was thinking like John or Jane. Too weird.

Heather finished touching up Jane's make-up and said, "Come on. And don't forget to call me Mistress. I want you to do that all the time for two weeks."

"Yes Mistress," Jane said.

Heather led her to the bedroom and instructed her to take out certain items of clothing. "This is what I want you to wear today," she said.

It wasn't very different from what she had been forced to wear the day before. Heather made her stand naked and put on a thin red lace garter belt, cinching it tight around her waist. The next item, not surprisingly, was a new pair of red stockings. That was followed by another pair of satin thong panties, also in red, which she slipped on over the garter belt, and a matching stuffed lace bra. Except for the color it was almost an identical match to what she'd worn the day before.

"Red undies are a good color for a slut," Heather said.

Instead of a mini skirt and blouse, however, Heather wanted the slight variation of a long silky black dress. Only when Jane had slipped it on did she realize that the dress had a long slit up one leg that came all the way up to the belt at her waist. Standing still the slit was unnoticeable but when she made the slightest movement it parted and revealed most of her leg. How much was revealed was determined by how she moved, and at one point, when she stepped aside to let Heather pass, she exposed the entire length of her stocking and some bare flesh above it.

The high heels Heather had picked out were black strap-ons and when Jane stood up after putting them on, she saw that the silky dress covered her ankles, leaving only the front of her feet and the shoes exposed. The thought passed through Jane's mind that it was a pretty dressy outfit for 5:00 o'clock in the afternoon. Then again, if the idea was to feminize him – and that was Heather's idea of punishment – it was far more effective than any casual clothes could ever have been.

Heather opened the closet door, revealing the full-length mirror on the back. "Stand over here and look at yourself," she said.

"Yes Mistress." Jane walked to the spot Heather had indicated, careful not to wobble on the high heels.

The elegant girl that looked back at him was truly a sight to behold. She was beautiful, slim, curvy, and gave off a sexual glow. Her face was pretty, her hair fixed more stylishly than yesterday, and the soft fabric of her dress clung to her body. Even her smooth, hairless arms and slender hands projected a femininity that was inviting.

Since the alarm had gone off that morning Jane had been mixed up, trying to deal with the events of the night before and her troubling actions and reactions. Nothing seemed to fall logically in place no matter how hard she thought about it. Yet somehow since Heather had arrived, and she had been preoccupied with being fixed up and fixing herself up, the confusion had settled into a remote part of her brain. She still knew her real name, but at the same time found herself settling almost completely into the role that Heather had commanded that she play. The look in the mirror finished the job. It was a girl that looked back at her, and a beautiful girl at that. She wasn't divorced from reality, it was just that reality didn't seem to fit in the picture. She hadn't flipped out. She knew what she had between her legs and knew what was going on. But at the same time she discovered that she was stepping into the Heather-created role more willingly than she had yesterday. It was no longer a new and strange role for one thing. She knew the part. And now that she could walk gracefully in high heels, stand and sit like a girl did, and move around without fear of falling on her face, it was easier to feel comfortable in stockings, a bra and all the rest. Even the wig didn't seem as heavy or awkward as it had yesterday.

"Don't fall in love with yourself, slut," Heather said, breaking Jane's concentration on the lovely girl in the mirror.

"Yes Mistress. I mean no Mistress," Jane stammered.

Heather was about to say something else when the doorbell rang.

Jane froze. She had figured that she hadn't seen the last of Bobby, not with the fun he'd had at her expense last night, but she had expected that Heather would invite him over during the coming weekend, not the very next day after their first embarrassing encounter. It was plain that Heather was going to give him a very bad time for much of the two weeks that she owned him. It looked like Bobby would be visiting them frequently during that time and that his humiliation would come often. That frightened her. One experience had been difficult enough to deal with. Three or four times in two weeks would have an accumulated effect that he wasn't sure she could handle. If once had mixed her up so badly that she didn't know whether to think of herself as "he" or "she", what would happen if it was repeated three or four times in the remaining thirteen days?

But it didn't have to be Bobby at the door. It could be a salesman or somebody looking for directions. It could be anybody. If they saw her, and weren't expecting John to be home, she knew she could pass as a girl. From what she'd seen in the mirror she wouldn't have any problems there. That is, as long as it was a stranger. Even if she passed in front of a neighbor or someone she knew slightly how would Heather explain her? How fast could she get rid of them?

She nervously obeyed Heather's instructions and followed her to the door, standing to the side as Heather looked through the small round peep lens.

Heather came away from the peep and smiled harshly at Jane. Then she opened the door.

Jane quickly stepped behind the door but wasn't at all surprised to see Bobby step inside. What did surprise and scare her was that he was followed by another guy.

Bobby kissed Heather and said hello, then turned to Jane and held out his arms. "No kiss for me?" he asked with a grin.

Highly aware that the other guy was intently staring at her she nervously leaned toward Bobby and kissed him on the lips.

Bobby turned to his buddy and asked, "Didn't I tell you?"

The second guy, who was the same height as Bobby but a few pounds lighter, continued to stare at Jane. She self-consciously drew into herself, glancing at Heather for some kind of direction. Heather ignored her.

Bobby's friend was now staring so piercingly that he squinted.

"Well?" Bobby said.

The guy straightened up. "Bullshit," he said.

Bobby and Heather both laughed.

"Nope," Heather said, "no bullshit. You'll find out. Kevin, meet my slut Jane."

Kevin held out his hand and Jane placed hers daintily in his grasp. Kevin held it longer than normal but finally released it. "Bullshit," he said again, and again Heather and Bobby laughed.

"Alright, everybody to the couch," Heather said, taking the commanding role right away.

Jane was very nervous, and hesitantly brought up the rear as the foursome went to the couch. When Heather and Bobby took one end, and Kevin found himself in the middle of the couch, she had no choice but to sit next to him. She crossed her legs and the slit in the dress slid open, revealing her entire leg and a bit of flesh above her stockings.

"Whew!" Kevin said, glancing at the beautiful curves she exposed.

"Kevin is a friend of Bobby's," Heather explained, "a trusted friend. I decided we'd have a double date today. and we told Kevin about you at lunch. He has some serious reservations but I said once he got a look at you they would all disappear." She turned to the new guy. "Well Kevin, have they?"

"You're conning me," Kevin said. "No way. I don't get the joke but what you said about...her...can't be true."

"Don't you trust me?" Heather asked.

"Truthfully? No." Kevin said.

"Okay, then why don't you satisfy yourself?"

Kevin didn't say anything. He turned and looked at Jane again, squinting his eyes as if he was trying to see through her.

"I don't understand the joke," he said finally. "I'll find out eventually if what you said was true, but I don't think it is. I can't believe that."

"See for yourself," Heather said.

Kevin hesitated before reaching out and placing a hand on Jane's beautiful thigh. She could feel the nervousness in his fingers and wondered if he could feel the nervousness she was experiencing in her entire body. A strange guy that she'd just met moments ago was putting a hand on her stockinged leg, and one glance at Heather told her she wasn't going to do anything about it.

Kevin's hand moved slightly over the silk covered flesh.

"Spread your legs, slut," Heather said.

Jane took a breath and did what she was told. The slit in the gown revealed her entire leg and part of her hip now, but covered the most important area.

Kevin slipped his hand under the dress and felt bare thigh above the stocking tops. He turned around to look at Bobby and Heather, and both of them were grinning at him. He turned to look at Jane but her expression was frozen. She knew the look was the result of fear at what might happen, but he took it to be challenging and slid his hand further under her dress. His fingers stopped at the edge of the satin panties, but finding them seemed to give him the courage to go on and his hand went down and covered her crotch. The bulge in the panties was immediately obvious, but Kevin moved his fingers around longer than necessary before withdrawing his hand.

"Un-fucking-believable," he finally said.

He looked at Jane, who was now flushed, and shook his head. Turning to the others on the couch he said, "You weren't kidding. I never would have believed it but she's a he."

"Think of her as a she," Bobby said. "A beautiful girl, that's all."

"I'm not sure I can," Kevin said.

"Yes, you can," Heather said with a tone that said it was settled. "Last night my slut gave Bobby one hell of a blowjob..."

"Absolutely," Bobby chimed in.

Heather gave him the evil eye, not liking to be interrupted. He seemed to settle back into the couch.

"As I was saying," Heather said, "last night she blew Bobby for my entertainment, but tonight I want him. That's why I asked him if he had any friends he could trust, and why he invited you to lunch with us."

"You're not going to have a problem with this, are you buddy?" Bobby asked, seeing that his friend was staying quiet.

Kevin took a long time before answering. "I'm not sure. I guess if she did you... I don't know. This is pretty weird. She's beautiful all right.. I call her she?"

Bobby laughed, "Sure."

"Okay, she's beautiful, like I said. But I'm not sure anything will happen, if you know what I mean," Kevin said.

"To be honest, I wasn't either," Bobby said. "Heather said wait until I see her. and I did. That did it for me. Plus, she gives really great head."

Jane, whose blushing had subsided, now lit up again, her face red enough to match her bra and panties. How could he say she gave great head? That was horrible! She didn't. She didn't even know what she was doing. Heather made her do those things. And she was offended by the two guys sitting there discussing her oral skills, as if she wasn't even there! Besides she had no oral skills. This whole thing was completely new to her, and she had just done what she had to do.

"I could try it," Kevin said, and the other three all realized at the same time that his protests were suddenly less than sincere.

Bobby and Heather both relaxed, as if the convincing was all over. Kevin, they were sure, just wanted to protest a little so they didn't get "the wrong idea" about him.

"Sure, try it," Bobby said, not even making the effort to pretend to have to make Kevin change his mind.

"You ought to see her naked," Heather said, knowing that the guy needed some more face saving gestures.

"No way!" Kevin said quickly, and Heather realized she'd said the wrong thing.

"Not naked," she corrected. "Just in her panties, bra and stockings, like she was for Bobby."

"That's the way she was for you, buddy?" Kevin asked.

"Yep."

Kevin pretended to think about it for a minute. "I guess if she leaves her bra and panties on... I don't want to see anything."

"You won't see anything but a very pretty girl on her knees, sucking you off," Heather said. "Agreed?"

"Well, I'll give it a try," Kevin said.

"Good!" Heather said, clapping her hands together. She turned to Bobby and wrapped her arms around him. "Tonight you're mine." Bobby worked his arms around her and they began making out.

Kevin just sat there watching them out of the corner of his eye. Jane didn't know what to do. There was no secret now as to what Heather expected of her, and Kevin was a nice looking guy. The only thing she had against him was his hypocrisy, and really that wasn't so objectionable. He probably honestly was at least a little hesitant, and he hadn't pushed his protests to an irritating level. It was just kind of an ego, guy thing. Then again, maybe he really didn't find her attractive. No, not considering the way he had acted earlier, and the compliments he paid her appearance. Maybe it was the confusion. It was a new situation for him, just as it was almost new to Jane.

She waited, but he still didn't move. Maybe she should make the first move. Heather would we mad if things didn't get rolling and she sure didn't want that. Not knowing what else to do she put a hand on his shoulder. He jumped so violently that Bobby and Heather broke off kissing. Jane noticed that Heather already had Bobby's shirt undone and her blouse was off.

"What are you waiting for, an invitation?" Bobby asked his friend.

Kevin shook his head and turned around to face Jane. Bobby and Heather went back at it.

Kevin put his arm around Jane and pulled her to him. Their lips met, but instead of the wet, open mouthed kiss she expect he remained still and cold. They broke, and he pulled her back, kissing her again. It was an improvement but he still held back. While they kissed Jane slipped her hand up his thigh and found his crotch. She felt him stiffen slightly, and she massaged the bump between his legs until it began to increase in size. That seemed to improve his attitude, because he now pressed his lips against hers and slid his tongue into her mouth. She continued to massage his crotch while they made out. Once his hand started up her side toward her bra, stopped, and retreated.

Jane broke away from him and whispered, "Wait." She stood up and unzipped her dress. If Heather wanted her to be the entertainment, she would have to get the show going on her own. It was clear that Kevin was still unsure of the situation and having trouble getting over the hump. She let the silky gown fall to her feet.

Kevin's reaction was all she could have wanted. His eyes opened wide, and he smiled as he looked her up and down. Her long legs were the center of his attention and the red stockings, garter belt, high heels and satin thong panties held his eyes. He reached out but his hand stopped inches from her thigh. He looked up at her.

She smiled and nodded and felt his firm hand begin caressing her legs. He put a little pressure on her hip and she turned obediently. He used both hands to feel the firm balls of her bottom, her naked hips, and the back of her legs.

Jane turned back to him and held out her hands. He held them and stood next to her. This time when they kissed it was with feeling. Kevin pulled her tightly against him and ran his hands over her naked skin. His tongue darted around her in mouth and played with hers when she entered his mouth.

"Much better!" Heather called out to them.

The standing couple stopped kissing and turned to see a naked Heather leaning over an equally naked Bobby, her head bouncing up and down in his lap. The sight of the other couple seemed to push Kevin over the edge, and he rapidly stripped out of his clothes. When he pushed down his shorts Jane saw that his cock was standing stiffly to attention. It was obvious, no matter how he tried to hide it or how little he would admit it to himself, that he found her extremely sexy and arousing.

Jane slipped to her knees in front of him and captured his bobbing penis between her wet lips. He was a little smaller than Bobby's but not by much. More in circumference than length. Her lips tightly gripped the rod, and slid three-quarters of the way down it. She was amazed at herself for being so bold. She hadn't even waited for Heather to command she perform oral sex on Kevin, though of course it was plain what was expected of her.

With the cock still in her mouth she rocked her tongue back and forth along the underside, pleased when she felt him shudder. She continued using her tongue to turn him on, turning her head sideways so she could get her tongue to lick the top of the organ. It seemed to swell in her mouth. And this was the guy who wasn't sure anything would happen! If she was learning anything, it was that a hot wet, warm mouth would produce a very sure result.

"See, I told you she was a slut," Heather said. "I want a full report from you when she's done. I've told her to be eager and passionate. You'll report to me after she's blown you. And don't worry about coming. She loves getting guys to go off in her mouth, and she swallows every drop. If she doesn't, she'll have to answer to...AHHHH!"

As aroused as Kevin was, even he turned to see what had happened. Bobby was kneeling in front of the couch, his stiff tool embedded in Heather's hot pussy. Her beautiful body was twisting and turning as Bobby put it to her, her breasts bouncing with the rhythm of his thrusts. Heather noticed the motion of the other couple and caught Jane watching them fuck. "None of this for you, slut, even if you could," Heather said. "My plans call for you to give Bobby's friend the blowjob of his life, and that's all."

Jane was more than relieved. She obviously knew that she couldn't satisfy Kevin the same way Heather was pleasing Bobby, but she also knew there was another way, though the thought had never entered her mind until Heather's statement. That would be way, way too much. She was surprised to discover that she wasn't very upset about having to perform a second blowjob, but the thought of having sex the other way was too scary to even think about. She needed to focus on what was in front of her, especially since she was finding it wasn't all that unpleasant. When Kevin turned back to her, she eagerly drew his cock back into her mouth and resumed sucking and licking.

Kevin was also considering what Heather had said. As the beautiful slim blonde that knelt before him eagerly sucked his hard-on he couldn't help but think about Heather saying that the girl was going to let him shoot off in her mouth, and then swallow his come. He'd had two girlfriends who had given him blowjobs, but neither one had allowed him to go off in their mouths. One tried once but said she didn't like it. The other never would try. Now this hot looking chick – and that's how he thought of Jane – was going to not only let him do it, but she was going to swallow his come. The thought made him more excited than he'd ever been in his life.

Jane felt Kevin shake, and she lowered his hands from his hips to his knees to steady him. Still sucking on his stiff cock, she gripped his knees with all her strength.

"Wait a second," Kevin said.

She backed off the cock and looked up at him. He smiled and sat down on the couch, his legs spread. "Okay, go ahead," he said.

Instead of taking the pole back into her mouth Jane grabbed the head and held it against his body. She began licking the cock, left to right, top to bottom, up one side and down the other. Every variation seemed to turn him on more than the last.

"Lick my balls, baby," he moaned.

That was something she hadn't wanted to hear. She looked at the hairy sack and wondered how to get out of the request. Unfortunately Heather seemed to be paying as much attention to her as she was to the guy who had his dick in her pussy, and she called over, "Do it, slut."

Now she had no choice. She probably would have done it anyway, knowing that Heather had told Kevin he would have to report on Jane's attitude and ability later. But even the possibility of distracting Kevin with some other thrill was lost to her now.

Jane bent lower, as Kevin spread his legs wide to give her easy access. Her tongue tentatively pressed against his balls. No response from the guy. She tried again, dragging her wet tongue across one ball and to the other.

"Mmmmmmmm."

She tried again, thinking that this was something she hadn't had to do with Bobby, and something she hoped she would never have to do again. She wet her lips and pressed her mouth against Kevin's balls. Her tongue slid around the sack, bringing more quiet moans from above. After three or four more swipes she didn't mind the act any longer. Anything, it seemed, turned out to be at least okay, and sometimes downright enjoyable, after she got over the fear of the unknown.

She continued licking his balls, finding out what moves and what pressure seemed to get him the most aroused. She delighted in each discovery, and was delighted again as her actions brought more and more intense reactions.

"Come up here and finish," Kevin finally said.

Jane took his pulsating cock into her mouth and started sucking him with long, slow, wet movements.

This was it, she realized. The fun of sucking, the thrill of feeling a hot, hard cock in her mouth and knowing it was that way because she made it that way, would all come to an end when this virtual stranger reached his climax. And he would have that climax in her mouth. Her memories of Bobby's orgasm were vague and mixed up. She was sure she couldn't have liked letting him shoot off in her mouth, but on the other hand she sometimes thought that she had enjoyed it. Enjoyed it? A guy coming in her mouth? No way. She was troubled by the fact that she didn't remember it more clearly.

Kevin's cock twitched and for a second she thought he was going to go off right away, but it was only a single twitch and she kept sucking. Long, deep, slow movements of her mouth seemed to get the most reaction from him, and she repeatedly slid her soft lips down the length of his dick. At one point she realized that she was actually getting the whole thing in her mouth, the head bumping against her throat. Her natural gag reflex kicked in the first few times the head of his cock touched her throat, but she exercised some will power and made the reflex disappear. She was astounded that she could do that, and kept pushing her lips down to his pubic hair and getting the entire cock into her mouth. Of course the head of his cock blocked off her air every time it pushed into the opening of her throat, but she quickly learned how to time the deep sucking with her breathing. Kevin seemed to love that more than anything she'd done. He came unglued the first time she sucked the entire length of his cock into her mouth and he stayed unglued as long as she kept doing it.

She vaguely heard passionate yelps and exclamations off to the side and knew it was Heather and Bobby reaching their orgasms. But the other couple meant nothing to her at the moment. Her entire focus was on the throbbing cock in her mouth and she was alert to each bit of swelling and twitching. Kevin started moving his hips around, never thrusting forward to drive his cock into her mouth but instead grinding in a small side-to-side motion.

Jane guessed that he had to be close to coming. The idea didn't displease her at all. Getting him to come was the goal of all she'd been doing. Now she thought she remembered that she had enjoyed Bobby's orgasm for the same reason. It was the ultimate proof that she was successful. By making him come she had shown that she was sexy, and that she knew how to please her man. Making Kevin come would show the same thing. She redoubled her efforts.

Kevin wasn't loud during sex but he kept up an almost continuous moaning, and Jane could tell by the change in tone and time between moans just how far along she had brought him. She remembered Bobby telling her to fondle his balls toward the end of his blowjob and she now did the same for Kevin. It was just what he needed. His hips lifted off the couch, burying his entire cock in Jane's mouth, and the pole pumped out a giant shot of thick, white come. Jane swallowed frantically, trying to run her mouth up and down his cock at the same time. At that point she felt she was in complete control, milking the staff with her lips and taking a second large spurt of Kevin's come.

Kevin collapsed on the couch and she followed him down, unwilling to let the twitching cock out of her mouth. She squeezed the organ with her lips, starting at the base and pulling all the way to the head and was rewarded with a final bit of liquid. She continued a gentle sucking but could draw nothing else.

"My slut comes through again," Heather said. "And Kevin, you said nothing would happen..."

Kevin was too drained and exhausted to even try to reply. He lifted his head a little and looked down at the pretty blonde girl. His now shriveling cock was still in her mouth and though it was difficult to tell for sure it looked like she had a smile on her face.

Bobby got up off his knees, his equally limp dick slipping out of Heather's soaking pussy. It was plain that he, too, was exhausted. Heather, still full of energy, swung her legs around and reached for her panties.

"Wait a minute, Heather," Bobby said. "As soon as us guys rest up a little, you're only going to have to take those off again."

"Not hardly," Heather said. "The party's over. Jane has a lot more training to go through. You and Kevin get dressed and hit the road."

"Wham, bam and thank you Sir?"

"You got it," Heather said.

"I don't think so," Bobby said.

"I SAY so," Heather said firmly. "And you know you'll do what I tell you to do, or you'll be jerking off in your bathroom every night. And I'll pull the plug on the deal we've got, and you'll never what my grandfather left me."

Bobby frowned but started getting dressed.

"And you," Heather said, turning to Kevin. "I told you I wanted a report on Jane's blowjob. Well, report."

Kevin let out a breath and gathered enough strength to get to a sitting position. When he did so he pulled his dick out of Jane's mouth and it flopped against the couch.

"The best I've ever had," he said simply.

"That can't be saying much," Heather said.

"Hey, you didn't have to say that," Kevin said, obviously hurt. "I've had my share and...she..." he stumbled on the word "...Jane here, gives great head."

"I saw you when you shot off. She must have swallowed your stuff," Heather said.

"Like it was ice cream," he said. "Two big shots. I think I came more than I ever did in my life. She really worked me up, and she gulped it down as quick as can be."

Heather seemed to dislike the compliments Kevin was paying to Jane's abilities, but be pleased that the girl had followed her orders so thoroughly. "Okay," she said. "You can go now. Hurry up and get dressed and get out of here."

Jane, still on her knees in front of the couch, had equally mixed feelings about what Kevin had said. She was hurt by the way they talked about her as if she had no feelings at all, but she was also proud that Kevin was obviously wildly happy with the way she had performed.

She was less divided about the subject they were actually talking about. A guy had had his orgasm in her mouth again. A different guy from the one yesterday, and equally a stranger. She had let him...no, made him...shoot off his come while his hard cock was in her mouth. As she remembered the same thing with Bobby, she wasn't at all sure whether she had liked it or disliked it. That part of her memory was still confused. But there was no doubt she had been thrilled the second time. When she felt Kevin explode she distinctly recalled a wave of pleasure sweeping over her body. He may have been a reluctant participant at first, but she had won him over, and given him what he told Heather was the best blowjob he'd ever had. The proof was in the coming. The two giant spurts of liquid couldn't be disguised as anything other than a massive release of very intense sexual pleasure. He had started out feeling negative about her, but she had made him enjoy her more than he had enjoyed anyone else. There was definitely a strong sense of victory and success in having him reach his climax in her sucking mouth.

The guys both dressed quickly and Heather pushed them out the door. Bobby tried to make a date with her for lunch the next day but she put him off. When she'd closed the door behind them she turned to Jane and said, "Time to clean up."

Jane started to get up off her knees but Heather stopped her with a command to stay where she was. The long legged brunette walked over to the couch and sat in front of Jane exactly where Kevin had been sitting.

"Time for you to clean me up," Heather said. "Bobby shot a load of come in my pussy, and I'm all sticky down there. I want a little lesbian action from my slut. Lick me clean."

The gender twists befuddled Jane for a moment. What made her dive into the wet and shiny slit in front of her, was her now automatic response to any command from Heather. She simply obeyed. Besides, she was getting a bonus. Heather said that her pussy was full of Bobby's come and she thought Bobby was a really nice guy.

 

 

 

Part Six

 

The third day of her two-week sentence started late again. Heather had kept her up until well past midnight, forcing her to walk, sit, bend and stand in an increasingly feminine style. She even made her slow dance all by herself, wearing high heels, though Jane wasn't able to pull that off without repeatedly tripping. There was another make-up lesson, and some instructions on styling the wig. At one point Heather made her hold a couple dozen shirts and blouses up to her chest, one at a time, to see what color complimented her complexion. She made Jane try on casual clothing like jeans, toreador pants and girls' slacks. After the fourth pair she said, "No pants for you. Your legs are just too good to cover up. I'm going to make you wear mini skirts and dresses only."

Jane simply did whatever Heather told her to do. At times she felt like a mannequin, at other times she felt as if they were just two girlfriends sharing make-up secrets, and at still other times she felt like a slave who was being ordered around.

Heather, for her part, had started out being bossy, and each day seemed to take her ownership of Jane more and more for granted, sure that Jane would