by Gingerfred Man
Chapter One – Big Changes
Mom and I have only had each other since Dad ran away with a pizza-delivery girl three years ago and we did just fine, thank you. Mom had been smart enough to siphon off cash from their joint accounts when Dad started ordering pizzas seven days a week, so money was not a problem. She had always been a stay-at-home Mom, which we both liked very much.
That was why I couldn't understand why she wanted to make all those big changes.
She didn't need to go back to work. She said she needed it for her "sanity" and "to feel fulfilled." Wasn't it fulfilling enough just to take care of me?
Then she laid the really big one on me. I was going to a babysitter every day after school! Me! Fourteen years old and never been babysat!
My protests were loud, frequent and intense. But Mom was adamant.
"You'll love going to Mrs. Evans' home every day, Charlie," she said. "I've checked things out there very carefully and her babysitting 'methods' will be very agreeable to you. Anyway, there are other boys you know there, so it'll be fun for you."
It was true that Mrs. Evans babysat David, Mark and Paul too. I knew those guys since kindergarten, but it was demeaning to be babysat at our age. We were in high school for goodness sakes. When I spoke to the three boys about it, they were very enthusiastic about me joining them and said I would be very happy at the Evans' home.
I didn't care what they said. It was humiliating.
Why couldn't things just stay the way they were?
Chapter Two – Welcome to the Sitter
I was miserable that Monday morning when Mom dolled up for her first day on the job. I had to admit that she looked very good. But I was mad at her for the situation she had put me in.
I pulled a face in a last attempt to change her mind, or at least to make Mom feel really bad about her decision. It was in vain.
"Remember, Charlie," Mom said as she put in her gold-hoop earring. "The bus driver knows to drop you at the Evans' and the other boys will be getting off there too. You get the A-3 bus, not the A-7 and no funny business or I'll warm your bottom, drag you over there and have Mrs. Evans spank your bare-bottom too."
Whoa! Mom's darkside. I didn't see that very often. It was time to toe the line.
That day after school, I got on the stinking A-3 bus and sat with David, Mark and Paul. They were good guys, but not my bunch. And kind of wimpy for my taste.
Sighing, I got off the bus with the three lads when we reached the Evans' street and walked with them to meet my fate.
How bad could it be?
Mrs. Evans opened the door to greet us. She was an attractive, 40-something woman, who, Mom said, loved children, but had none of her own.
She smelled very nice when she kissed me in welcome and I guess I was surprised that she had a nice dress, stockings and heels on in the afternoon in her own home. Mom dressed like that all the time, but so few women seemed to any more.
David, Mark and Paul made a big fuss over Mrs. Evans. Each gave her a big hug and kiss that told me they really enjoyed their afternoons at her home.
The nice lady took us to her kitchen to give us milk and cookies, then she released the other boys. "Go get changed into your play clothes, boys," she said. "I'll explain some of the house rules to Charlie."
Play clothes? Did they keep them there? I didn't have any. Mom didn't say anything about that. Already, I was feeling out of step. The boys giggled a little when Mrs. Evans said "play clothes." They even gave me funny looks. When they saw my lack of comprehension, they giggled even more.
Mrs. Evans took me into the family room, [she called it the "playroom"], sat me on a couch and sat across from me on a chair. We spent a pleasant 20 minutes or so discussing mostly me and I didn't hear anything about "house rules."
Then I did. "Charlie," she said. "I love children and have been in childcare for many years. It's taught me a few lessons. The biggest one, I guess, is that boys your age are very hard to manage. You're wild and unruly. Like little beasts. At first, I tried to control boys with bare-bottom spankings and lots of corner time, then naked spankings, but nothing worked. So I discovered a solution that was right for everyone and made everyone deliriously happy. I made unruly boys into sweet, little angels."
I didn't like the sound of that one little bit. What kind of awfulness could she do that was more of a deterrent to bad behavior than a naked spanking?
In a moment, I had my answer.
"You can come in now, angels," Mrs. Evans said.
I looked toward the door and saw my immediate future. And it scared me half to death.
Three lovely, feminine, teenage masterpieces entered the room on their very high heels, their beautiful frocks showing off their femininity to full advantage. Pretty, swaying bottoms topped killer legs swathed in silky stockings. Their hair, though short and boyish, was styled and beribboned. Their faces were cosmetic masterpieces.
My first reaction was as a hetero guy. I got a thick, throbbing erection. My second reaction was as a condemned prisoner. My erection dissipated. Beads of fearful sweat covered my brow.
The three lovely babes were David, Mark and Paul. And I was able to add two and two very quickly about what was next for me.
Chapter Three – The Newest Angel
What kind of pit had I fallen into? Did Mrs. Evans actually expect me to…….
David, Mark and Paul looked me over as if they had never seen me before. "He's a pretty one, Mrs. Evans," Mark said with a girlish squeal.
Was this the boy I sat next to on the bus half an hour ago? And had known all my life? He looked like a pretty girl and acted like a little faggot.
Paul and David were no better. I couldn't stop looking at their legs under their short skirts. And their heels were so high that their pretty bottoms were sticking out. And wiggling. Oh no. My erection was back. How humiliating.
Mrs. Evans said to the three girlish boys, "Charlie has real potential. Would you little sissies like to help me show him how pretty he can be?"
They all nodded enthusiastically. "Can we 'relax' him first, Mrs. Evans?" Paul asked.
"Of course, Honey," she said. "Charlie, would you remove your trousers, please?"
Raw fear gripped my throat. I wouldn't. I couldn't. "No!!!!" I screamed.
Mrs. Evans' facial expression turned very dark. I learned quickly that it was a rare expression, and one to be avoided at all costs. "You don't disobey me or Mr. Evans, Charlie. That's the path to anarchy. You just used up your one freebie. Every act of disobedience after this will be punished. Trousers off. Now."
I was young and stupid. Again I screamed "NO!"
Mrs. Evans was a lot quicker than I thought.
She grabbed me and had my trousers down and off me in seconds. She was very strong and those three little sissy faggots, David, Mark and Paul watched Mrs. Evans wrath with horror. They didn't move a manicured finger to help me. And they didn't leave the room either as Mrs. Evans held me firmly in one arm and grabbed a straight-back chair with the other. She placed the chair in the center of the room, turned the back to me and the seat away. Then she ordered me to drape myself over the back of the chair, with my hands on the seat. My bottom was bare and exposed and that woman could see it all. She could probably see my balls too. Oh, it was horrible.
And then it got a lot worse. "Stand on your toes, Charlie," she said, "and hold your bottom up for the smacks I'm going to give it. Mark, David, and Paul will watch your well-deserved humiliation after your open defiance."
I wondered if an apology was in order.
That appeared to no longer be an option.
I got up on my toes and presented myself for my first spanking since I was nine. It was excruciatingly embarrassing, especially, surprisingly, the "on-your-toes" part.
Then it got painful.
Mrs. Evans could swing a hairbrush. She smacked my right cheek with strength and enthusiasm, as if she were exorcising the demons that boys carry around with them.
I yelled. And got off my toes.
Mrs. Evans said, "Back on your toes, Charlie, or I'll add to your dozen."
Eleven more? Ouch.
Reluctantly, I got back on my toes and somehow lived through eleven more smacks. Luckily, she didn't hit my dangling balls, which was the only fact of all that mess that pleased me in the least.
Well, something must have pleased me, though, because I had the biggest erection of my young life. Which made everything all the more humiliating. As did the half-giggling stares of the three sissy-ass senoritas.
I began to sob softly, then a bit more loudly as I reached for my pants to cover my shame. But my pants were gone and my shame stood tall, red and throbbing. My bottom was red and throbbing too.
I bowed my head as Mrs. Evans led me to the corner.
"You just stand there and no touching that sassy bottom of yours, young man," Mrs. Evans said. "And no touching your stiff 'little gentleman' either. Soon enough, you'll see the soft pleasures of obeying me."
Fat chance, I sniffled to myself in the corner. When Mom hears about how I was treated, she'll come back with a big stick and teach Mrs. Evans a lesson.
I was imagining multiple misfortunes for Mrs. Evans, many maiming and/or fatal, as I stood on one leg and then the other as my bottom blazed. It hurt! I had been warned not to take my eyes off the corner and I certainly didn't want another "warm-up." So I obeyed.
And listened to some very strange goings-on behind me.
My three "friends" showed me no sympathy, engaged as they were in what I deduced was a daily ritual of faggotry.
"Oh, Paulie, it's so hot and hard," Mark's voice said. Clearly he wasn't talking about an algebra problem we were assigned that day for homework.
"I know, Markie," the disgusting-little-sissy-faggot Paul said. "It gets like that whenever I think of your red lips caressing it."
I wasn't sure what David was doing until he said, "Go ahead and get on your knees and suck it, Mark. I'll just skin my little peeny and watch. Then I'll do you, you little fox."
I was sickened, but my little guy wouldn't go down. Even worse, I was afraid it would….. Oh, please no, I thought. I couldn't cum. Not in front of these faggots. They would think….. Oh, please, no.
I couldn't see, but I was pretty sure that those slurping sounds I heard were made by Mark's mouth on Paul's cock. And those little, excited squeals were Paul's reaction to having his cock sucked by another boy. Another boy dressed in stockings and heels and garter belt and panties.
It was evil. I hated it. Mom would know everything! All the kids at school would know and I would put a stop to it. Right after I stopped cumming six globs of my thickest cream into Mrs. Evans' corner.
I couldn't help it, OK? The way Paul was squealing and saying in the girliest voice, "Oh, Markie. Your tongue is heavenly. Keep doing that. Ohhhhhh! Markie, darling! I'm cumming! I love you, Markie. Swallow it all! Ahhhhhhhhhhh!
It all just hit a button in me I didn't know I had. That was why I creamed so hard. I was so ashamed, especially since I knew my indiscretion would be discovered. You can't hide a pint of cum.
I prayed that they would stop, but apparently, they were enjoying themselves. I heard Mark and Paul kissing and swapping tongues, promising each other "undying, sissy love," whatever that was.
Boys in frillies kissing. Glossed lips against glossed lips. Tongues dueling tongues. New, harder erections. I was picturing it all. And so was my cock, which was once more in a very painful state.
"OK, lovergirls. Don't hog each other," David said. "I get a turn, don't I?
Mark and Paul must have broken it off. Only Paul had cum (and me, unfortunately) so the two horniest started slurping and kissing as I heard Paul clump to the other side of the room in his high heels.
What a predicament. If I could only hold out for another hour or so, then spill the beans to Mom, this nightmare would end. Then I could tell an analyst about it when I was 40, and he could tell me why, despite my disgust, it all made me erect and produced a cum blizzard.
I heard Mrs. Evans re-enter the room and I tensed up. I didn't want my bottom to blaze anew, so I stood silent, facing the wall.
"Hello, Darlings! Having a good time? David, I think you should suck Mark's popsy now or he'll be ill from seminal back-up. Good boy. On your knees. Now lick his nice helmet. Mmmmm. He likes that. Put your tongue in his peehole, Darling. Slowly, Darlings. There's no rush in peeny sucking. You know Mark likes that. Look, he's shuddering with pleasure. You're doing a wonderful job. Now don't neglect his pretty bag. Look how his little peanuts hang, ready for your kisses and licks. Very nice. I think he's going to give you a sweet creamy reward. Put the whole popsy in your mouth, David, and catch it all. Good boy. Oh, Mark, I love the way you squeal during pleasure.'
Unnhhhhh. I was a hairbreadth away from cumming again myself. Was I crazy? Was I gay?
Then Mrs. Evans turned her attention to me.
I didn't like that.
"My goodness, Charlie. You've made a cummy mess in my corner."
The three little creampuffs giggled loud and long at that observation, then resumed their sodomy.
I trembled with fear. Was that a hairbrush offense?
"I'm glad you enjoyed the company of my little angels, even though you couldn't see them. They're a horny little bunch. I think it's time you came out of the corner."
Even that scared me. She would see my erection. And I would be prey to that band of ….whatever they were. But I complied.
When I turned around, everyone ooohed and aaahed. I have a very nice-sized cock for a boy my age and it was frighteningly erect.
"That's a very pretty cock you have there, young man," Mrs. Evans said. "Are you going to be a good boy and let me take care of you now?"
I didn't have a lot of options so I said yes. At least until Mom picked me up in less than an hour.
"Good," she said, and smiled sweetly. "What I wanted to do, before you defied me by not removing your trousers, was to give you your first panties. But I see that's not possible at the moment."
Whew! I was very relieved. I didn't want panties!
But she continued. "Your pricklet is too stiff. It'll need to be properly drained before we can put this lovely, sheer pair of pink dazzlers on you."
What did that mean????
"Paul, I don't think you've had your RDA of protein today and poor Charlie is in such a terrible state. Can you help him?"
"Yes, ma'am," the asskissing little robot said. Oh, man, was I going to enjoy watching the boys in school kick those faggots' asses when I narced on them.
What was he going to do to me?
Mrs. Evans put a lacy, thick, pink pillow at my feet and Paul put his stockinged knees squarely on it. Then he kissed my cock!
Right on the head!
And it leaked very badly. I felt stirrings of an impending spermstorm in my gut as I considered my options. Run, without pants, from the room and out the door. Refuse and take another spanking. Submit to this faggotish assault.
The third option seemed to promise the least pain, so I stood there and tried not to shame myself by cumming. But then a second pink pillow went down behind me. And Mark was on his knees. Parting my bottom cheeks. And kissing the hole even I didn't touch very often.
My eyes watered from mental humiliation and physical ecstasy. I closed the lids, then felt David's soft, warm, glossed lips covering my own. It wasn't fair. I shouldn't have enjoyed any of it. But it was I who stuck my tongue into David's wet mouth. It was I who moaned with suffocating pleasure as I tensed my anus on Mark's tongue and pumped a huge load of hot goo into Paul's slurping mouth.
It was fabulous!!!!
But, of course, I would never do it again.
I was breathing very heavily and still whimpering softly when my balls stopped their pumping and began to ache.
David had stopped kissing me and Mrs. Evans, Mark and Paul were standing, facing me.
"Did you like that?" Mark asked.
I hated to admit it, but Mark was the cutest of the three. His hair was kind of sandy blond and he had the prettiest eyes. Those lashes were to die for.
What was I thinking?
Rather than answer Mark's question, I made a face, looked down and said nothing.
"It's OK, Honey," David said. "We've all been there. There were older boys here when we started. Lots of them. And it took some getting used to."
David was kind of cute too. He looked great in that pink top and those black stockings really showed off his legs beautifully.
Paul added, "It's lots of fun here. And there's more to do than just what we did today. We play games and we take field trips. And sometimes, Mr. Evans gets home from work early and that's extra-special fun!"
Did he mean? Ickkkkk!!!!
Still, I don't think that if I woke up with Paul, dressed as he was, next to me in bed, I would kick him out. His lips were big and red and puffy. And his bottom was plump and inviting.
I shook my head hard to clear it of all the gunk of the last few hours. Then I realized that I had yet another erection.
"You still can't get those panties on with that big boy, Charlie," David said. Without asking permission, he dropped to his knees and expertly, lovingly polished my knob. Just to be sure I would enjoy it, Mark licked two fingers and inserted them into my bottom. Ohhhhhhh. That was more intense than the cocksucking. I would have protested, but those beautiful, red lips of Paul covered my mouth.
It was too much for me. I wasn't responsible for the awful, gay, cummy, kissy way I responded. Yes I was eager and even <blush> reached into Paul's panties and stroked his cock as he kissed me. But I was overmatched. So was Paul. As it turned out, I'm an excellent kisser, and the masturbatory motions I had taught myself seemed to work very well on Paul.
The feel of Paul's hot cum on my fingers, his moans as he came, his tongue in my mouth, Mark's talented fingers rubbing my innermost parts, and David's tongue swirling around my cockhead, took me to the highest mountain in paradise. I cried out as I released my boy's cream into David's loving mouth.
In between orgasmic spurts, the shame hit me. When the orgasm stopped, only the shame remained.
But all three of them were kissing me as Mrs. Evans looked on with approval. Like I had joined their faggot club or something. Which I hadn't. And wouldn't. Ever.
But I let Mrs. Evans slide a pair of panties that must have weighed half an ounce up my boyish legs. When she tucked my drooping cock and sore balls into them, she seemed to linger a little with the cock-touching. Since she was an actual female, I allowed myself to enjoy it.
Not that she would be removed from my list of those who must suffer my vengeance.
Those darned panties felt awfully good on my young package, though. Cool and silky.
At a signal, the boys left to get back into their male clothes as Mrs. Evans handed me the trousers I came in with.
I put them on as she lectured me. "You boys all start out as you did today, Charlie. Frankly, I would have rejected you if you hadn't. I don't want THOSE kinds of boys. My boys LEARN to enjoy sissy pleasures and are better people for it. Happier people."
Hah! I thought. Maybe those pouffies, but not me. I'm calling the FBI and the CIA as soon as I get home and breaking this party up.
Mrs. Evans rose from her chair and retrieved a package. "Here are a week's worth of panties, Charlie. I want you to wear them all the time now. There's a nice selection there. You can hand wash them if you wish. There are also two pretty nighties that I want you to sleep in from now on. Your mother will probably get you more."
Panties!?!? Nighties!?!? Not when my Mom hears of this.
The three sissies came back to the so-called "playroom." They were dressed as normal boys, with all make-up removed. I knew they were wearing panties and, for some reason, that was stirring my poor, over-exerted cock.
It was time to leave. I ran out, quivering with relief when I saw my Mom's SUV and her sweet, greeting wave. Safe at last, I thought.
Chapter Four – Not so fast
I tumbled into Mom's car and slammed the door firmly shut. Sanctuary!! I peeked out the window at Mark, Paul and David being loaded into their Mom's SUVs. Why didn't their moms put a stop to that sodomy pit. Were babysitters that scarce? Did the moms even know? Well, mine was about to find out.
"How was your afternoon. Sweetheart?" Mom asked as she kissed me.
Mom pulled away as I hooked up my seat belt. I began to cry.
Mom asked, "What happened? Are you all right?"
I savored the moment. Then I spilled the beans. "It was horrible, Mom! Mrs. Evans dressed the boys like girls. And she wanted me to dress like that. But I resisted and she spanked me. And the boys did 'things' with each other. Queer things!"
That should do it, I thought.
"You resisted? Whatever for? I hope Mrs. Evans didn't hurt you badly, but you shouldn't have defied your babysitter."
I just looked at Mom. And reevaluated the situation. And asked, "You knew what goes on there, Mom, and you sent me anyway?"
Mom smiled prettily. "Of course I knew, Honey. What kind of mother would put you into a situation I hadn't checked out?"
My jaw hung slackly. I was doomed.
Mom explained, "I'm a single parent with a boy. The responsible thing to do is to take some of the rough edges off you, sweetheart. Mark, Paul and David's mothers say their boys are sweet and loving now. And they love their time as girls. Most of the time that they're home, they dress en femme."
"Sweetie," Mom said, "I did spend three minutes on my cell phone with Mrs. Evans a few moments ago and she told me that there were certain aspects of the afternoon that you seemed to….enjoy."
Mom knew my shame. The one person whose opinion really matters to me got a report that I'm a simpering little faggot who cums in boys' mouths and kisses and wanks boys to orgasm. It wasn't my fault! It was the situation. My cock betrayed me!
Mom, my only ally had just sold me to the enemy.
We pulled into our driveway.
We said nothing to each other until, after I set the table, she placed a microwave, mystery-meat dinner in front of me. Showing maturity I didn't know I had, I asked Mom, "How was your first day at work?" Life isn't all about me. I knew that even at 14.
Mom hugged me when I said that and her eyes were misty. She nattered on about her new job for 10 minutes or so.
Then she turned back to my problems. "Do you have panties on now, Charlie?"
I turned crimson, and nodded.
Mom pressed. "How do they feel?"
"Mommmmm!!!!" I said.
She asked the same question.
"OK, I guess," I said.
Mom seemed pleased with that answer. "Did Mrs. Evans give you the nighties I bought for you?"
The conspiracy deepened! "Yes, Mom."
"Why don't you do your homework, then get into one of them and come sit and watch TV with me?"
Things just kept getting worse. But I agreed.
I finished my homework at about nine. It shouldn't have taken that long, but I was thinking about what had happened to me and what was about to happen. Modeling a girl's nightie for my Mom. Facing that sissy situation the next day.
I washed my face and hands and went winkie. I stripped naked, including the removal of my pink ball caressers. Then I looked at the two nighties. They were both babydolls and very short. One was pink with white, ruffled trim. The other was baby blue with little pink rosettes.
What a choice!
Blue seemed marginally more masculine, so I slipped it on. Oh. It felt delightful. Soft and cool and caressing. And my stiff condition was back.
The nightie was so short! If I stretched at all, my balls were dangling below the hem. I looked in my full-length mirror at a very strange sight – a boy in a very girlish nightie. The nightie made me look almost….pretty. With a little blush and lipstick…some attention to the eyes.
What was I saying?
My immediate problem was that the garment was displaying my goodies, so, reluctantly, I looked among the panties that Mrs. Evans had given me and found a white pair. I put them on. Better. I brushed my boyish hair, flouncing it up just a little.
I didn't wear my boys' slippers, choosing the barefoot option.
I was cute, in spite of myself.
Then I went downstairs to display the temporarily-amended-under-protest me to Mom.
I didn't expect to see Mom in a pretty nightie as well, but she was. And she looked great.
She also looked happy to see that I had done as she asked.
Mom's smile was broad and warm. "You're so cute, Charlie," Mom squealed happily. "Turn around. I want to see everything."
I did as Mom asked.
I was blushing a little as I spun around, but it was all new to me. Guys don't know how to be pretty. We don't know what being pretty means – what power it has. Girls grow up with pretty and learn how to handle it. I was having difficulty being pretty in front of my Mom, for goodness sakes.
It wasn't bad being pretty. For my Mom, at least.
"You're adorable!" Mom said, and I felt a good-sized slab of my masculinity fall off.
No problem, I thought. Lots more masculinity where that came from.
Mom said, "Come closer, Honey."
It was OK, because I knew Mom would never try any funny business with me.
But I was a little worried when she pulled my panties up and over my omnipresent erection, and down my legs. "Step out of those panties, Charlie. No one wears panties to bed."
They don't? Oh.
I had a problem. My wispy, teeny nightie barely covered my package. And my package was most unruly. I didn't want Mom….I mean….you know what I mean.
Mom understood. "Don't be afraid, Sweetheart. I'm not going to do anything naughty. I just want us to sit next to each other on the couch, cuddle, and watch a little TV. Then we need to go to bed – our own beds – and get some rest.
That sounded OK. Good in fact.
I sat next to Mom and cuddled next to her. We had always been close, but even more so since Dad found the girl with extra toppings and ran off.
Mom smelled so nice. And she was so pretty and feminine. And she had her arm around me. Just her arm.
Oh, please no. My little poppet was throbbing again and had escaped its silky confinement. I tried to hide it, but Mom just said, "It's OK, Charlie. I know it's just a build-up of all your girlish excitement. Sweet boys like you get overheated when they participate in femininity.
"That's a very nice 'little man' you have there. Pretty big for your age. And red, swollen and throbbing. I haven't seen it in a few years. It's a good thing your father passed on something good to you."
Too much information! But Mom was mostly right about all of that.
An old Cheers rerun was on, but all I could think of was the crazy, excited state I had been in since arriving at the Evans' a few hours earlier. Did femininity excite me? Apparently so.
I tried to watch Sam and Diane trade quips, but all I could think of was a prayer: Please don't let me cum in front of my Mom.
Then I thought of Mark, Paul and David and how pretty they were. And how they had sucked my cock and done other incredible things. I smelled Mom's perfume. Felt her body heat. Felt my nightie against my sensitive skin. Thought of that tongue in my bottom and kissing those pretty boys. I gasped.
Mom produced a couple of Kleenex from the folds of her nightie and held them over my exposed tinkler. Expertly, Mom caught my sissyish goo as I helplessly spurted glob after sticky glob.
Mom was incredible. She wiped my drooping private parts clean, kissed me on the forehead and said, "Why don't you go to bed, now, Sweetie?"
"Yes, Mom," I said, and gave her a big hug.
My Mom is the best.
Chapter Five -- Lessons
I went to bed that night in a mixed state – embarrassed, dreadful, exhausted, dehydrated, yet still rather randy.
Mom insisted that I wear that emasculating nightie to bed. I protested, but not so vehemently that she would change her mind and let me take it off. Being honest, it excited me.
Despite yet another erection, the first unmilked one of that day, I fell asleep. Being very tired, I slept soundly, without dreams, until seized by a very vivid one early the next morning: I was in the nightie I went to bed in, wearing very high, stiletto heels like Mark, Paul and David. I was walking through the halls at school, carrying my books and wiggling my almost-exposed bottom. Classes were changing and the halls were jammed with kids. No one was paying attention to me until suddenly, one mean boy pointed at me and yelled, "Hey, look at the faggot!" It was as if everyone realized I was there at once. They all stopped walking, looked at me and began to laugh. I tried to run, but I was surrounded. I tried to pull the hem of my nightie down to cover my growing erection, but my cock was out of control. It kept growing and my balls were aching and everyone was mocking me and then I began to spurt my cum like a firehose. It was so powerful in the dream that it knocked me to my knees.
Then I woke up.
The room was full of daylight. My eyes were moist with tears. The lower part of my nightie was drenched with the biggest load of cum I had ever produced.
From that dream. What was happening to me?
It was a huge relief for me to be wearing my boy clothes for school, although Mom insisted that I wear the panties (wispy yellow things that would assault my privates with girlish teasing all that day). I was also apprehensive about my after-school activities, though I had resolved never to get a spanking again.
I saw Mark, David and Paul at various times during the day and they all acted the same way to me that they always had. A small, very small, part of me wished that one of them would drag me into a boys' room stall, pull my panties down and suck the cum out of my sore balls. A very, very small part of me.
When we got off the A-3 bus and entered Mrs. Evans' home, my strange new world was again at hand.
That time, like the other "sat" sissyboys, I kissed Mrs. Evans and greeted her warmly.
She was sweet and pleasant as she had always been, except for that time she had activated my posterior.
"Charlie," she said, "My sweet sissy boys and I are going to show you how to dress and act like a sweet, pretty girl. I guarantee you'll love it. And we'll know you love it because we'll see your erections and your titanic, repeated ejaculations of your sissy cream. You can't hide it and you can't say it didn't happen. Boys, take Charlie to the shower, clean him up and shave his legs."
If I were to get a spanking for defiance, that would have been the moment. What was going to happen to me?
"With pleasure," spokesman David said for the three little perverts. "Come with us, Missy," he said.
Oh, gloom. Oh, doom. Oh, big erection on the verge of a monster cum.
We went to a big bedroom, apparently the one where the boy-to-sissy conversions occurred each day. The sissy trio stripped naked and instructed me to do the same. As Mrs. Evans predicted, my excitement was obvious, despite myself. Oh, my.
Mark took my hand and kissed me. Then he rubbed his naked body against me, rubbing cock-to-cock David and Paul were in a similar clinch. Without girlish clothes, it all seemed so gay. So I closed my eyes and pretended that I was the boy and Mark was the girl. Mark was a great kisser and his fingers rubbing my tender anus as his cock rubbed mine did me in. I was whimpering and shooting gooey blasts against Mark's flat stomach. Then he squealed, like a little sissy faggot, and began to pump his hot juice all over me.
It was heavenly. Not that I would have admitted that at the time. Even under oath.
My best friend, Mr. Shame, returned, and I broke off from Mark's naked embrace just as I heard Paul and David kissing and cumming all over each other a few feet away.
Mrs. Evans had a really big shower. With four water nozzles and lots of room to move around. I stayed in my corner, thank you, and turned my back on all the faggotry going on around me. I didn't want Mr. Shame all over me again.
When we were cleaned up, we left the shower and dried off. Again, I kept my distance from the "freehanded" sissies over there. But then it was time to follow Mrs. Evans' instructions. Still-naked Mark lathered up my right leg and began to shave it.
Mark took his time. When he had relieved my first leg of its hirsuteness, he washed the remaining soap off, then rubbed lotion luxuriously from my inner thighs to my little toes.
Guess what? I got a stiffie.
Just when I was panting with need, Mark stood up, turned around, wiggled his tight bottom at me and left to get dressed. A lingerie-clad Paul replaced him and gave my left leg equally arousing attention. When he rubbed lotion between my toes I was a feather-touch away from a big, cummy mess.
It was David, asking me to stand up and grab my ankles.
"I'm not taking a sissy's cock in my bottom. Spank me if you must, but……"
David chuckled. "Relax. I'm going to shave your bottom. We all do it. It's very nice."
I bent over. And had my bottomcheeks lathered. And the soft, inner folds of my buttocks. Then David shaved me there, copping more-than-what-one-would-consider-a-fair-number of feels. When he shaved all around my wrinkled rosebud, then rubbed lotion everywhere, that was all for me. I began to whimper and gasp. Then I let my second big load of the afternoon breathe free.
Maybe that would calm me down, I thought.
I was wrong. The boys, who by now were all fully dressed and made up (spectacularly, I must admit) took me over to a chair by the window and sat me down. They showed me how to roll my stockings into a doughnut, then slowly, sensuously ease each one up my smooth, silky legs.
How do women get dressed without cumming all over themselves every time? The answer is that they don't usually get dressed like women.
I was all hard and sore again, just from the stockings. The garter belt I put on next sort of made things more critical for me. That snapping on of those hooky things had me in a dither and then I did a dumb thing. I slipped on a pair of three-inch stiletto sandals, stood (with some difficulty) on them, and tottered over to a full-length mirror.
Oh! Red alert. I looked so girlie. I felt so girlie. Even without make-up. I was panting as I looked at myself. I was turned on by myself.
The boys knew what I was going through. Paul got up and stood behind me. He reached around my right hip and began to skin my doodle up and down, as he said, "You're very pretty, Charlie. You have beautiful legs. Do those stockings feel good on you?"
I whimpered affirmatively, nodding my head.
It was more and more difficult to stand in those heels. My head was reeling. Where was that Mr. Shame guy when I needed him?
My peehole was pointed at the mirror and I could see it drooling sticky ooze. The tiny peelips were opening and closing. My legs felt incredible. My cock felt even better. My balls clutched and my eyes locked onto my peelips in the mirror. They parted and spewed out one….two……three….four sticky globs of sperm. Ohhhhhhh.
We cleaned up, then I heard a commotion outside. The three sissies were peeking out the window. "What is it?" I asked.
David said, "The football team walks by here every day before and after practice. The field is three blocks from the locker room, so they walk. I guess you didn't hear them yesterday. We watch every day. Some of those boys are so HUNKY!"
Oh, no, I thought. They were attracted to boys! Icckkkk! I would never.
Mark had his skirt up and panties down. He was stroking his penis head and groaning, "Billy Brockman….mmmmmmmm."
It keeps getting worse, I thought. Paul helped his sissy friend by getting on his knees and sucking his cock very sweetly.
After their inevitable, cummy conclusion, I sat for my first make-up lesson.
Wow. Those guys sure knew how to enhance their beauty with cosmetics. And they were very good teachers. When they had finished with me, I had the basics down and their cocks up.
"You're the prettiest of us all, Charlie," Mark said, as Paul and David nodded agreement.
The mirror told me they were right. Now what? I wondered.
Chapter Six – Fun and games
Over the next few days, I really tried to stay away from the worst of the stuff the three experienced sissies seemed to take as second nature. Even though my needs had become such that I think I would have imploded if I hadn't dallied a little with the three pretty boys. I let them suck my cock, but I wouldn't suck theirs. I did kiss them and stroke them to big cums – I'm only human – but I didn't put my fingers in the pansies' rosy buttholess. I had standards, even though I was stiff as a parking fine in New York every time they fingered my pootie.
I was a bit surprised that no one pushed a stiff cock into a companion's pretty bottom. I was afraid to ask about it though, lest someone suggest that it be done to me.
The sissies played all these stupid games that I, of course, was above. They would play "Who's harder?" a game where, say David would judge whether Mark or Paul's stiffie was harder. It would always degenerate into the game's winner, loser and judge all losing their stiffies and a large portion of their bodily fluids.
Then they would have contests about who could cum first, or most, or farthest.
Every day they would run to the windows as the football team went to practice and returned. The sight of all those masculine boys seemed to whip up those three little pansies. They would groan and make all sorts of lewd observations and speculations. Then they would suck, lick and wank each other into a messy state.
That was beneath me. I had no interest in boys or men. At that time, of course, I was mostly interested in my beautiful self.
At Mrs. Evans' and at my home, where I began to dress en femme in the evenings, I would spend a great deal of time admiring something I had never had before – beauty. It wasn't the kind of beauty I would have wanted, I guessed. It was feminine beauty. But, hey! It was beauty.
I worked on my make-up technique and got very good at it. The effects were dazzling. I would actually choke up when I saw my made-up face in the mirror. My hair was short, but it didn't detract from my lovely, though false, femininity.
Mom seemed to really enjoy my "activities." She and I spent hours talking about hair and clothes and, get this, "feelings."
I enjoyed it all very much. Even as I worried constantly about where it was all going.
On Tuesday of my second week, Mrs. Evans asked me to do something that I was sure meant the end of my life.
"Charlie," she said, "I'm all out of milk and eggs and I need them to make my husband's dinner. Could you run down to the corner store for me?"
Normally, this would not have been a problem. At that moment, however, I was wearing a pink blouse, 13-inch, black miniskirt, black stockings and four-inch-stiletto pumps.
I asked two stupid questions: "Can I change into my boy things first?" Answer: "No, I need them now, Charlie." <Perspiring, shaking with fear> "Could one of the other boys do it?" Answer: "Yes they could, but I asked you, Charlie."
I would have to go into the world like this. Alone.
"You'd better hurry, Charlie," Mrs. Evans said. "The football players will be back in 45 minutes."
Omigosh!!! That would be horrible, I thought. I took ten dollars from Mrs. Evans and the directions to the corner grocery (two blocks east, one block north). I looked at the other three, all of whom seemed to be enjoying my discomfort tremendously. Was it some sort of initiation? Probably.
I took a deep breath and stepped out of the front door. No one was on the street. But they would be, so I'd better move. I wouldn't want to wiggle past 50 horny football players.
Got my bearings and walked east. No picnic in those big heels. My bottom was sticking out and wiggling and there was no one there to see. Thank goodness, right?
One block away, a 30-something man stepped out of his house and walked halfway down his driveway. His eyes were locked on me and he had a very dumb expression on his face. It was as if he were dazzled or something. Can you imagine? Me, dazzling a man?
I shouldn't have thought about that. My cock stirred and I did not want a tented mini telling everyone what I was packing in my panties. Still, it was very exciting to think that a stranger thought I was beautiful.
Red alert! A block away from the store, as I turned left, I saw two teenage boys in a car slowing down to get a look at me. They were driving in my direction, at the speed that I was wiggling, and one of them even called out, "Hey Baby! What's your name?"
Hadn't those bad boys any manners? Had they never seen a pretty girl in stockings, short, tight skirt and big heels before? Not that I was a girl. But I guess I looked like one. Maybe they hadn't seen anyone dressed femmy in a while, so I forgave them. But I didn't favor them with a glance.
I did smile a little to myself as I stepped into the grocery store. It was a small, Mom and Pop place and only Pop was there.
Pop was acting as if it were his lucky day. "May I help you, Miss?"
They all think I'm a girl, I thought. Oh no, my stiffie was sort of returning.
I spoke, "Yes, sir. I need a dozen eggs, a quart of milk and a can of tomato soup [a late add-on to the list]."
"I'll get the milk and eggs if you'll just get the soup on that bottom shelf."
Well, he was very nice. I gave him a 500-watt smile, which almost knocked him over. Then I turned, saw the soup, and bent over to grab it. The wrong way. Bending at the waist. Showing my panties, stocking tops, garter straps and white thighs to the nice man. I realized my error when I heard a soft groan. Oh, dear, I thought, as I straightened up. How humiliating.
When I turned around, the man was turning away to get the milk and eggs. I was red as a beet and he was trembling as he bagged the groceries and I paid him. He walked me to the door, opened it for me, touched my arm and said, "Come back any time, Miss."
He was so sweet and it was all my fault, so I gave him a 1,000-watt smile. He closed and locked the door behind me and put the "Closed" sign up. I wonder what he wanted to do after I left.
Those bad boys in the car were gone when I left the store, darn it. And I didn't see any other males until I passed the house with the man I had seen before in the driveway. He had the hood of his car up and was pretending to fix something, but what I think he was doing was looking at my pretty legs and bottom. I was carrying my bag in front of me to hide what had become a full stiffie, and I gave my audience an extra little wiggle as I went by.
All in all, the trip was kind of fun.
When I got inside Mrs. Evans' house, they all looked at me expectantly. All I did was drop my panties and lift my skirts for some relief. I got plenty.
By Friday of my second week at Mrs. Evans, I was walking easily in the biggest heels and looking good enough for "Sissy Beat" magazine, the teen sissy magazine whose naughty issues were all over the Evans' house.
Those three pouffers were always talking about some article or other they read in that dumb magazine. I looked at it now and then, but it was always stuff about hair, make-up and sex with boys. The letters were strange, like the one that got a Dr. Laura-attitude-type answer when someone asked, "Dear Sissy Beat: I'm a 16-year-old sissy in Memphis. My boyfriend wants to go all the way, but I'm scared. What should I do?" Sissy Beat's response: "Are you sure you're a sissy? Did some girl write this letter? Of course you should go all the way. You should suck your boyfriend's cock during the first hour of any date, no later than that or he'll think he's with a girl. And you should always, always take your boyfriend's cock into your tight little pussy whenever and however he wants it – on the first date, second date, between dates, while he's brushing his teeth or eating his Cheerios. Lots of times on every date. You're a sissy! Be proud."
And another letter that drew a more thoughtful response, "Dear Sissy Beat: I'm an 18-year-old sissy in Peoria. When I suck cock, I always wonder whether I should take my boyfriend's cum into my mouth and swallow it or let him splatter my face with it. What's your advice?" Sissy Beat's response: "Good question and one that has troubled sissykind for centuries. There's something tremendously emasculating, intimate and submissive about sucking down all of a man's cum without spilling a drop while on one's knees in one's frilliest lingerie. It's also wonderful to have a sissy's warm, moist mouth on a cockhead until the last tingly spasm of orgasm has subsided. Still, the degradation and humiliation a man imposes on his submissive sissy as he spurts his seed all over her pretty face, marking his sissy as his own little cumslut, is an experience every man and sissy thoroughly enjoy as well. Our recommendation, mix it up. Since, during a night with your man you should be blowing him at least twice (in addition to four other cums in your open, willing bottom), let him experience some of each. Keep the mystery in your relationship. But most importantly, do what makes your man (if he's good to you) happy."
I also really liked the letter that said, "Dear Sissy Beat: My boyfriend is a real jerk. He calls me nasty names like 'faggot' and 'bitch' and never even kisses my clitty. He never says he loves me and acts like I'm his whore or something. What should I do?" Sissy Beat's response: "Get out the dump truck and drive it over him when he's asleep. Sissies are only submissive to men who adore them and worship their femininity. There are THOUSANDS of nice guys out there praying for the opportunity to have a relationship with someone like you. Don't stay with a loser."
See. There was a whole world out there that I never saw until I got to Mrs. Evans' house.
That day, the others said they wanted to spend the afternoon playing at being lingerie models and wanted to know if I would participate. Since I knew I was the fairest of them all, I was eager to show my form.
We got transformed quickly then went to the playroom to dress in a variety of lingerie, sissying back and forth along our makeshift "runway" in our four-inch stilettos, blowing kisses at the "audience."
It was good, clean, sissy fun until we took our break to watch the boys walking to football practice.
Usually we watched from the upstairs window, but that day, we were on the ground floor, so we peeked from behind the drapes in the sliding, glass door.
Then something bad happened. For me. And later for Mark, David and Paul.
The little creampuffs had a mean-spirited plan and they moved very quickly to implement it. In a flash, Mark slid the door open, as Paul and David pushed me out, closed the door, locked it, and pulled the curtains shut.
I was left standing outside, wearing a black, lacy bra; wispy, sheer panties that barely concealed my stiff willie; sheer, silky, seamed, black stockings; and black, four-inch-stiletto-mule sandals. Across the street, 20 feet away, were 50 young men in complete football regalia. And they were all looking at me.
Those sissy bastards! I would kill them. Right after I stopped crying from fear and shame.
The football players stopped and stared at me. I stood frozen for a second. Then a boy laughed. Then a second boy. All of them. My worst nightmare.
I covered my privates with my hands. [Had they seen my boyish "package" through those thin panties? The shame if they did!!!!] I ran, in a panicked state, wiggling my bottom as the huge heels forced me to do. The football players hooted in derision as I ran completely around the house to the front door. I pounded on it, ringing the bell and begging Mrs. Evans to let me in. She opened the door almost instantly, pulled me in, closed the door and hugged me through my racking sobs.
When she had me calmed down, she sat me down and called for my three tormentors. They were peeking at me and giggling.
Mrs. Evans was not amused.
"I'm calling my husband. He'll deal with you very bad boys."
That seemed to chill the three nancyboys. For the first time since I had known them, Mark, David and Paul looked worried. I had never met Mr. Evans, though they had.
I was ruined. How could ever go to school on Monday? Someone must have recognized me. It would be all over school that I was a card-carrying queer, who dressed in skimpy lingerie and was erect because of it. It wasn't true! The queer part, I mean. I was a victim of two strange women (Mom and Mrs. Evans) and three actual pussyboys.
I kept crying as Mrs. Evans called her husband. I sneaked looks at David, Paul and Mark, who had obviously thought they would have been in for, at most, six on each bottomcheek from Mrs. Evans' hairbrush. This was clearly going to be much more severe and they seemed frightened.
Well good, I thought. Served them right for robbing me of what was left of my masculinity.
Only ten minutes later, the front door opened and Mr. Evans stormed in. He spotted me as I saw him. He was a VERY handsome man. Tall, rugged, mid-40s. Broad shoulders, narrow waist, 6-2, 220 pounds of manly muscle.
I'm ashamed to say that I got a big stiffie looking at him. I didn't know why. But it my panties were filled with my own cock as I looked at a truly beautiful man.
What was I thinking?
Anyway, he was sweet and nice to me too, hugging me and apologizing for the rude treatment I had received in his home from three little creampuffs who were about to pay for their sins.
He hugged me so closely that I think he felt my stiff cock against his leg. I know I felt his. It was iron-hard and apparently enormous.
"Excuse me, Dear," Mr. Evans said. "I have to punish some offenders."
Thank goodness I wasn't being punished by that beautiful man, I thought. I'd probably cum often and humiliate myself thoroughly.
The sniveling condemned were in the "playroom". I heard Mr. Evans call out, "Paul. You're first."
Paul moaned. It's good to get it over with, but the punisher still has all his strength when you're the first victim.
Paul deserved it. They all did. I reminded myself of that, though I did feel just a twinge of sorrow for him.
Mark was facing one corner of the "playroom," David in another. I sat, uncomfortably, in the middle. The boys' panties were down and around their knees. They both had half-erections and were whimpering with fear.
Mrs. Evans sat next to me. "Are you all right, Charlie?" she asked.
"I'm worried that I was recognized and the kids will humiliate me in school.'
She gave me a knowing look. "Oh, I think it's much more complicated than that," she said.
From upstairs, I heard some hard whacks falling on plump, pink, naked flesh, followed by the pitiful screams of the punished.
I was very uncomfortable. "Is it bare bottom?" I asked Mrs. Evans.
She chuckled. "It's bare everything, Charlie. Mr. Evans is buck naked and so, except for his stockings and heels, is Paul."
"Why is Mr. Evans naked, Mrs. Evans?"
Before she could respond, I heard my answer. The screams had stopped and squeals, gasps and pants had started. The sounds a girl makes when she's being well and thoroughly fucked.
"Sweetheart," Mrs. Evans said. "You can't spank a sissy at Paul's stage of development without fucking him after. He would implode. And so would Mark and David."
Omigosh. That man, that beautiful man, was dominating Paul, disciplining him. Marking him with his hot seed. Fucking the blazing-red, sore, pretty bottom that he just disciplined. Naked. Rampant.
Mrs. Evans recognized my predicament. She freed my cock from my panties, gave me three or four delicious strokes, then produced several Kleenex just in time to catch my sticky splashes. It was gut-wrenching to imagine what was going on upstairs.
I thought my orgasm would never end. The thought of being spanked hard, then fucked by a beautiful, naked man was very disturbing to me. And horribly arousing.
Things got worse when Paul entered the playroom.
Paul's appearance told the story. He was wearing only black stockings and his fuck-me pumps. His cock was completely limp, but drooling the goo of what appeared to be multiple cums. His stomach was drenched with cum. His eye make-up was smeared with his tears.
The real show, though, was when Paul turned and stood, facing his corner. His bottomhole was gaping open, at least an inch-and-a-half in diameter, and cum was drooling out freely. His poor bottom was fiery red. I felt bad for him, happy for him and, startlingly, envious.
I stared at Paul's gaping bottomhole until "Smack!" followed by "No, please, I'll be good!" from upstairs told me that Mark was getting his punishment. From that naked hunk. Followed by a sound fucking. I had never fucked or been fucked. It sounded very intense. That was good, right?
I began to wonder if Mr. Evans would have the stamina to spank and fuck all three of them. Oh, my. My poor stiffie was threatening to poke a second bellybutton in me.
Mrs. Evans was always there to help.
"Paul," she said to the whipped and fucked sissy. "Have you apologized to Charlie for your mean, humiliating prank?"
"<Sniffle> No, Mrs. Evans"
"Well, I think that he would forgive you if you helped him a little. Charlie's condition appears to be quite serious."
Paul got the hint. He left his corner and got on his knees in front of me. Mrs. Evans left us alone.
Paul took my cock into his pretty mouth. I had to say, "Paul, I didn't want you guys punished like that. Honest."
Paul stopped sucking for a second, looked up at me and smiled. "I know," he said. "We were all hoping we'd get Mr. Evans' punishment. It's fantastic! Sorry we embarrassed you, but you needed some loosening up."
Then he resumed his skilled cocklicking and ballsucking.
Those little scamps, I thought, as that wonderful feeling overtook me and I gave him a luscious, creamy meal.
Mark rejoined us 20 minutes later. His bottom was gaping, drenched and drooling thick, manly goo. And, despite an even redder bottom that Paul's, he seemed very pleased.
David went off to meet his fate as Mark "apologized" to me by licking my bottomhole until I blew a big load all over my stomach. David's pleas for "harder fucking" excited me tremendously.
When David returned, I looked at the clock. Mr. Evans had spanked and fucked three sissies in 82 minutes. Que hombre!!!!
David's apology involved kissing me as he massaged my prostate with three fingers until I came so hard I almost passed out.
The afternoon started off badly for me, but it certainly improved.
David was back in his corner and I was lying on my back on the playroom couch, when Mrs. Evans returned. She sat next to me and said, "My husband wanted to know if some loving attention from him, minus the spanking of course, would make you feel better?"
Omigosh!!!! I couldn't. I wouldn't. Could I? Doesn't that man ever get tired of sissy pussy? Omigosh!!!!!"
I considered it. Seriously. But then I said, "Thank you, Mrs. Evans and please thank Mr. Evans, but I couldn't."
She smiled. "Of course you could, Sweetie. Look how stiff the idea has made you….even after all those cums of yours."
It was true. I was hard as advanced nanoscience. But that was my body. My mind said no and that was final.
Mrs. Evans was very understanding. She took my red, sore popsy in her soft, ladylike hand, manipulated it very nicely and said, "I know you won't do it today, Charlie, but I have to tell you that a man, my man, on top of you is the treat of a lifetime. He's fucked me thousands of times and each time it's better. He'll dominate you and make you his helpless little girl. He'll penetrate you with something you thought could never get inside you. Once it's in, you'll never want it to leave. It will rub against your prostate as his rough, manly lips kiss you and his tongue explores your mouth. Oh, Sweetie, I think you like that idea. Ohhh. That was a big spurt! And so was that one. Where's it all coming from? Another. Lots of hot, sticky sperm from your pretty balls. You're becoming a sissy all right. Isn't it wonderful?"
Chapter Seven – The Other Side of Things
I was exhausted, confused and in dread of Monday at school when Mom picked me up at the Evans' home that Friday afternoon.
In keeping with our new openness with each other, I actually told Mom every detail of what had happened to me that afternoon, especially my fear of what would happen to me at school if any football players had recognized me.
"Oh, Sweetie," Mom said. "It's much more complicated than that."
That was almost exactly what Mrs. Evans had said. I began to ask Mom what she meant by that when she dropped a big bomb on me.
"I'm going to need you to help me out with something, Charlie," Mom said.
That was odd. Mom was usually fiercely self-sufficient.
She continued. "I have a date tomorrow night, Sweetie, with a very nice man I met at work."
I was very happy for her. It had been a long time for Mom without a man. "That's wonderful, Mom," I said. I gave her a big hug.
"Thank you, Sweetheart. I need you to go along with me on something. The man, his name is Colin, and I were chatting and I sort of told him you were a girl."
I was supposed to pretend that I was a girl when I met Mom's new boyfriend? I could never pull that off. What if they hit it off? What if they got married? I'd have to be a pretend-girl for life.
I started to tell her all that when she said, "There's more."
"Colin was so excited. He has a daughter your age. He wants the two of you to keep each other company while he and I are on our date. He also sort of suggested that you stay with Grace, his daughter, all night – a sleepover. Can you do that? For me?"
I wanted to say, "Mom, that's insane. How long do you think I'll be able to conceal my true gender from a man and his daughter? This sounds like the plot for a lesser Shakespeare comedy."
Instead, since Mom apparently needed this date and this guy very much, I said, "I'll try Mom."
Mom hugged me gratefully.
My only hope was that Grace was a real bowser and I wouldn't get a telltale stiffie all night.
No such luck. When Mom and I showed up at her friend Colin's very nice house, I was scared out of my wits. Humiliation was the least of my problems. I was only hoping Colin wasn't an NRA member who believed in direct action against young men who pose as girls in order to sleep with his very fine daughter.
And I mean VERY fine.
Grace was about an inch taller than my five-foot eight. With her three-inch stilettos and my four-inchers, we were equal at six feet. Mom advised me against wearing such high heels, but I knew I would have never been convincing as a girl without the confidence that skyscraper, stick-out-your-butt-and-tone-your-legs heels gave me.
Grace's face was Miss-Teen-America-finalist pretty. Long, honey-blonde hair with cascades of golden ringlets. Bright, sky-blue eyes. Full, red lips. The prettiest little nose. And her body was the kind you see in your wet dreams. Thin waist, wide hips, C-cup gazongas, and stocking-caressed legs to die for.
I didn't look bad myself. If Grace was a 10, I had primped myself into a 9.7 for that evening.
I hoped I wasn't drooling, but I must say that it appeared to me that Grace was every bit interested in my beauty as I was in hers.
Mom and Colin kissed hello. Oh, my. From that kiss, I was pretty sure that Mom would be sleeping in Colin's bed that night. That was why they arranged for me to sleep over with Grace.
Mom deserved a good tumble and I was happy for her. But there was still that little matter of me spending time at close quarters with someone who thought I was a girl. And the gloom of an impending Monday when I would be facing a high school full of kids who may already have heard that I was a panty-wearing faggot.
I decided that one humiliating predicament at a time was all I could handle. So I concentrated on Grace. Goodness, she was beautiful. She gave me a sweet kiss on my powdered cheek and insisted on carrying my bag to her room. We said goodbye to her dad and my mom, who were going to dinner, then walked up the stairs hand-in-hand.
She had a nice, soft, warm hand. Hand-holding was the first time I had ever gotten that far with a girl. A real one, I mean. Not the ersatz version in Mark, Paul and David. Although I wasn't putting them down. They were girlier than 95% of the girls in the world.
But not girlier than Grace. Grace squealed with happiness as she showed me around her room and the upstairs. "You can use these towels," she said, "And this hair dryer, if you didn't bring your own."
Never having been to a girl's sleepover before, I was, as Mom suggested, following Grace's lead.
When we got back to Grace's room, she sat on the bed as I unpacked my things. Mom had suggested that I make a big deal out of unpacking and packing, as girls do. I didn't have much stuff with me, but a girl needs her cosmetics and her frillies.
"What would you like to do, Charlie?" Grace said. "Is that short for Charlene?"
Mom had prepared me for both questions. "Whatever you want to do, Grace. And yes, it's Charlene."
Grace smiled. A dazzler. "Let's heat up some pizza, then fix each other's hair and paint each other's nails."
There was still enough boy in me that watching a Stallone car chase would have been more fun, but I kind of wanted to see what my toesies would look like painted.
Grace was a lot of fun. And she made great pizza. I had to remember to eat in small bites, but I enjoyed it a lot. She told me all about her family, but she didn't have many friends, since she and her dad had only been in town three months.
"I'm your friend now, Grace," I said.
Grace hugged me. She smelled great! And those big titties against my flat chest made Mr. Willie commit his first sin of stiffness of the evening.
"Charlie," Grace said, "I haven't seen you around school."
"Uh, yeah," I said. "We must have different classes."
Oh, man. What would I do when she wanted to meet me at school on Monday? Monday was shaping up as a VERY bad day.
We cleaned up the dinner things and went back upstairs.
"Let's get into our nighties before we do the nails, OK, Charlie?"
"Sure, Grace," I agreed. Thank goodness Mom had allowed me to bring a nightie that hung to my knees and wasn't one of those see-through things.
Grace began to get undressed. Right there. In front of me. She pulled her pretty dress over her head and there she was. In her bra, slip, panties, and stay-up stockings. Oh, please no, not a stiffie…..Oh. There it was. Rats.
How could I ever avoid discovery?
Omigosh!!!! Grace had her bra off and the two prettiest puppies in the world (and their wet noses) were breathing free air.
Grace seemed to be completely unaware that I was gazing upon her naked, delicious body as she chattered away about this and that. Oh, my!
Realizing that I needed to start undressing soon or Grace would think I was a teen lesbian hot for her body, I took off my dress and laid it on the bed. I turned the side of me with the stiff cock trying to escape from the over-challenged panties away from Grace and tried to keep up my end of the conversation.
My heart skipped when I heard Grace squeal, "Ohhhh!"
Was I busted?
"You wear a garter belt! That's awesome! Oh, I love girlie stuff like that! Almost no one wants to be girlie anymore."
I wanted to turn around and hug her, but "Mr. Johnson" would have ruined what was becoming a very nice party.
"Thanks, Grace," I said. "I'm sorry I'm so modest."
That was quick thinking, eh?
"You're so cute, Charlie. And very girlie. You're legs are so beautiful in those stockings. I'm very envious."
What a situation. I'm the girl of my dreams' dream girl.
Grace kept getting undressed until she was naked; then she slipped on a pink nightie that barely covered her moist, hairy, beautiful pussy. I sneaked little peeks over my shoulder at her as I took off my stockings and panties and put on my pretty nightie. Thank goodness it was loose and gave me some protection from detection. I slid my feet into the puffy little four-inch mules Mom had bought me that morning.
"Come sit on the bed, Charlie," Grace said. "Let me do your toenails first."
I sat on the bed and was very happy that I had let Mark give me a pedicure two days earlier. He never got around to painting the nails, since he was more interested in sucking my cock, but the nails looked pretty good.
I pointed the toes of my right foot for Grace. "You have very nice nails, Charlie. Is dark red polish OK?"
Another chip off the old masculinity. "Yes, thanks, Grace."
Grace put the cottonballs between my toes and chatted happily with me about all kinds of things as she put two beautiful coats of polish on me. My toes looked incredible! I wiggled them happily. Thank goodness I was careful not to expose my boyish package to Grace as she handled my little toesies. The intimacy of the act had me in an agitated state.
When it was my turn to do Grace's toes, it was gratifying to me that she seemed to enjoy it very much. She shuddered with pleasure as I lovingly attended to her precious little footsies. I wanted to bring them to my mouth and kiss them, but that would have been very dangerous.
Unlike me, Grace showed no modesty. She held her feet and legs in ways that lifted her nightie and exposed the lips of her moist, hairy, exquisite pussy to me. It was so wet that I could smell it over the acridness of the polish. Grace was turned on.
When I finished painting and was done admiring the perfection of Grace's pretty toes (and pussy), I got up to put the equipment away. Then I turned around and saw Grace on her back on her bed, propped up by her pillows. Her nightie was held up by her left hand and she was fingering what appeared to be a stiff, slick, half-inch-tall, tiny cock at the top of her vagina.
"Oh, Charlie," she said through a sexual haze. "What you must think of me. We've just met and I'm acting crazy. I've never done this before, EVER, in front of anyone. It's just that I saw you naked and you're so pretty and sweet and innocent and …..I like boys, Charlie, but I like girls too. And for some reason, I'm more attracted to you than I ever was to anyone in my life. Don't hate me, Charlie, but I have to cum soon or I'll just die."
She liked boys and girls. She was hot for me, I guessed, because I was both. Sometimes lemons definitely become lemonade. I did what any gentleman pretending to be a lady would do. I lay next to her, kissed her tonguily and fingered her clitoris.
She liked it a like, if one can interpret spasms, and screams as being appreciative.
Then I did what I never did to the three sissyboys. I had her sit on the side of her bed as I went to my knees and licked and slurped and sucked all her private parts until she came so many times that she pleaded with me to stop. When I did stop, she screamed out, "Why'd you stop?" I chuckled and resumed my pussy adoration.
Finally, after a good hour of a very fine meal that gave me a very wet face, my new friend pulled me to her side on the bed and kissed me into a semi-coma. Then she said, "My turn!"
I knew that this was the moment. Would she scream for the police? Would she run downstairs to retrieve a large Ginzu knife?
I lay on my back and spread my legs. Grace knelt between my legs and eased up my nightie, very slowly. She was enjoying herself a lot.
When she revealed my dangling nut bag, I saw puzzlement on Grace's beautiful face. When she quickly lifted the hem to reveal my stiff, red, throbbing, large weapon, her face went neutral. Moment of truth. Drum roll.
Then Grace smiled broadly.
"So that's why I wanted you so badly. You're the best of everything. I love cock, but boys can be so crude and rough. I love pretty girls, but they can be so nasty. You're perfect."
Indeed I was. Perfectly enraptured when I felt the first female lips around my cock, then squealed girlishly as she attacked my libido with all her weapons. She seemed to enjoy tormenting me. Each time I was about to cum from her sucking my balls, for example , she would withdraw and let me cool off. After 25 INTENSE minutes of that, my eventual cum almost blew a hole in Grace's throat.
That was amazing!
It got better.
She sucked me to another firm stand, then got onto her back and spread her legs. "I'm soaked, you're stiff. Whaddaya say, sailor?"
And to think. I was worried that it would be a difficult evening.
Chapter Eight – Monday, Monday
Grace and I had an incredible night, and so did Mom and Colin.
I had empty balls and a big crush on a girl who was crazy about my girlishness when Mom and I returned home at noon on Sunday.
My confusion was immense. And Monday loomed.
"Mom," I said, "My life is so complicated right now that I can't think straight."
"That's true, Sweetie," Mom said. "But are you having fun? Do you like being girlie? Dressing in stockings and heels? Being a sex toy for a pretty girl and three pretty sissies?"
I thought for a second or two more. "I love it, Mom. I've never enjoyed anything half as much. And you know what, Mom? I'm good at it. I'm beautiful. And I love being beautiful. Grace would have looked at me as she would an insect if she knew me as a boy."
Mom hugged me. "You're right about everything, Charlie. But I know there are still unexplored issues for you."
I tensed up. What did Mom know?
She continued. "I spoke to Mrs. Evans about Friday and your….'reactions' to your playmates' encounters with Mr. Evans."
<Gulp> Mrs. Evans had a big mouth. "That's the part that has me confused, Mom. Some of me doesn't want to do 'things' with boys and men, but some of me is excited by it."
Then I made the big leap. "Mom," I said. "The really strange thing about my night with Grace was that, while I loved it and all, I was, I don't know….envious of Grace. You know what I mean?"
Mom nodded. "Tell me more," she said.
What a jerk I was. I had just dined at an all-you-can-eat pussy buffet and I was complaining. But I knew what else I wanted, so I said it. "I wanted to be Grace more than I wanted to be me. I wanted to be the one with the boobs, on the bottom, being the girl to the man, who's in charge of me. Does that make sense, Mom?"
Mom's eyes filled with tears as she hugged me. "How could anyone so young have so much good sense?" she said. "Submission to a good, adoring man is the greatest of feminine pleasures, Sweetie. You recognize that inherently, while most women never figure that out. I love you, so much, Charlie!"
Mom and I shared something that moment as girls that I could never have experienced as her son. It was great.
I hoped Mom would visit me a lot in the hospital when I was in traction from the beatings I was sure I would get on Monday at school.
My Sunday night was filled with dreams. Mr. Evans and I were in bed. He was saying, "I'm going to fuck you now, Charlie. You know you want it. And you're going to get it. So get on your back and spread your legs."
Dream me was sweating and whimpering, "Oh, please, Mr. Evans, I'm not sure! I'm not ready! I don't……"
"You want to say, 'I don't want to,' Charlie, but you can't. Because you know you do. You want to kiss me and suck my cock. You want to feel a man's admiration and his lust. You want to drive him wild with your sexiness and beauty, then have him mount you and fuck you until you cum and scream and cum again. So get on your back. Charlie, skin those panties down, and open your legs for me. That's a good sissy. Sweetie. Very good. You're very beautiful there too, Charlie. Lovely pink parts. We're going to have a wonderful fuck, you and me."
I was in a panic as Dream Mr. Evans slipped pillows under my hips to get a better angle. And then he was on top of me. Ohhhhhh noooooo. He was too big, too strong. I couldn't get away. And he was….kissing me. That was very nice. Very nice. He was gentle and loving. A great kisser. And he was rubbing something huge against my bottomhole. He had greased his cock down with something but it was still going to hurt, I knew it would. Then he was kissing me and pushing his big thing into me.
Aaaaaaaahhhhhhh. The real me was awake and cumming like a new oil well. Spurts like Old Faithful and splashes everywhere. I was breathing very heavily.
When I calmed down, I realized. Dream Mr. Evans was right. I was ready to try it with men and boys.
It was the men and boys who scared me when I went off to school that Monday. Even though I had been wearing panties every day for two weeks, Mom asked if I would rather wear boxers that day. I said, "Panties are who I am now, Mom. That's what I'll wear."
I had more guts than brains.
No one assaulted me on the bus. So far so good. There was no group of designated stoners by a quarry to put me to death the biblical way. Another point for me.
When I got in school, nothing had changed. Huh? I guessed I looked so different as a girl in Panty Boy's Secret lingerie, no one had recognized me.
Almost no one.
By lunchtime, I figured I was home free and I began wondering how I could get in the sack with Mr. Evans without getting welts of my bottom first.
I was interrupted by a tap on the shoulder. It was Jason Roberts, a guy who was 16 and two years ahead of me. I had known on and off since kindergarten. We had been in grade school band together and some youth teams, even though he was bigger and stronger and but now he was…..omigosh!!!! A football player.
I was terrified. Did it show? What was he going to do?
He spoke, "Hi, Charlie. How are you?"
"OK, Jason," I said through my fear. "I haven't seen you for a while."
Jason looked at me and smiled. "I saw you, Charlie. Friday afternoon on the way to the football field."
My eyes widened with fear. I was about to cry when he said, "Don't worry. No one else recognized you. They all wondered who it was, but no one knew, except me. And I'll never tell."
Ohhh. What a friend! I wanted to hug him. Instead I said, "Thank you so much, Jason. You saved my life. It's not what you think. It's a long story."
Jason smiled and touched my arm the way a boy touches a girl's arm. "I'd love to hear it. Can I take you out to dinner and a movie on Friday?"
My chin hit my chest. Did he say what I thought he had?
I asked, "When you say, 'out,' do you mean……"
"On a date," Jason said. "A boy, that's me. A girl, that's you. I think you're the prettiest girl I've ever seen."
Oh my. And I had been dreading THIS?
"Well sure," I said, "Yeah, OK. I'd like that a lot. OK."
"Wonderful," he said. And then he kissed me on the cheek. Holy cow!!!! Had anyone seen? No. My cheek was burning. Ohhh. Friday. I couldn't wait.
Chapter Nine – Joining the Club at last.
I think it was that Monday afternoon when David, Mark and Paul first noticed my change in attitude.
I had decided, quite logically, that if I were to be dating boys, I had better start learning how to suck cock. I mean, it livens up any date, doesn't it?
We had gotten into our playclothes and were still in the upstairs bedroom when I sort of stood in front of Paul, pulled his panties down and began to stroke his cock.
I had always thought he was the prettiest of the three and I loved those full, red, glossed lips of his. They felt very nice against my wet, lipsticked mouth as I kissed and stroked him until he was panting and gasping.
He was getting very close to his first creamy emission of the day (always the thickest), when I stopped wanking and kissing him. He was very disappointed until I hit my knees and held his cock at the base.
He looked at me with wide eyes. Mark and David, who had been engaged in their own forms of debauchery, stopped to watch us with great interest.
Paul said, "Are you going to…..?"
My answer was to kiss his cockhead, swirling my tongue and plowing through the gooey coating his prior excitement had produced.
It was very tasty. And I loved the groan the little nancyboy gave when I tongued his peehole. Not wanting him to cum too soon, I removed my lips from his red throbber and began to lick his smooth, hairless balls. Paul gave a little sissy squeal at that and I could hear Mark and David cheering me on as I sucked first one, then the other little Paulie walnut. They were considering the possibilities of having me as a full-fledged member of their sissy squad.
Then I got extra bad. I licked two fingers of my right hand, then eased them into Paul's tight, hot hole as I capped his cock with my warm mouth.
That did it for Miss Paul.
He was crying for his mama as he shot jet after spunky jet into my mouth. I had never tasted cum before and the aroma and texture were all surprises. Nice surprises that I swallowed greedily. But not completely. Paul's ejaculation was so big that some spilled out of the sides if my mouth, coating my cheeks with sissy cream.
I was such a little cum slut. And that part of my life had just begun.
We never made it down to the playroom that day. The four of us got onto the room's double bed and we engaged in every sodomistic combination (except anal intercourse) we could dream up. I sucked each pantyboy's cock and swallowed his cum. They all sucked me to a creamy blaster and I ate each of there bottomholes until they were sobbing as they came.
When we were exhausted, we talked.
"OK," David said. "I'll be the nosy one. What happened to you?"
I reached over to stroke David's drooping cock as Mark stroked mine and Paul kissed me.
I broke the kiss and said, "I had a change of heart. And I have a date."
They all whooped at that. "You little tramp," Mark said. Who's the unlucky guy?"
More whooping! "He's a stud muffin! Way to go," Paul said.
"No wonder you wanted to start sucking cock," David said. "You'll want to suck his five minutes after you're in his car. He's hot."
I was suddenly jealous. "Have any of you ever been with Jason?"
They giggled. "Don't worry, Honey. He's all yours. We each have plenty of boyfriends."
They had boyfriends? Stupid me. I never thought about that.
I asked for details and got them. Lots of them. Those three had been around with about 25 guys at school. And some of Mrs. Evans' previous "clients" had been with many more.
Apparently, it was no big deal at our school to date a sissy. In fact, guys were sort of looked up to if they did. Everyone knew that a sissy was sweet and feminine, never had a period, and had a raging sex drive. So what was not to like? Mark, Paul and David dated the guys pretty openly, mostly on weekends.
So maybe I wouldn't be exposed someday and burned at a stake.
Needless to say, I enjoyed my afternoons at Mrs. Evans' a lot more after that.
Chapter Ten – Jason's lucky night (and mine)
I didn't go to Mrs. Evans' that Friday, which meant a) I had plenty of time to primp and bathe and shave and curl and all that for my date with Jason and b) my ball bag was full of cum and I was horny as a dilemma.
Mom had bought me a beautiful LBD (little black dress) and after two-and-a-half hours of intensive feminizing, I slipped it over my head. I strode to the full-length mirror in my five-inch-stiletto, come-fuck-me pumps and admired myself. Mom had also bought me a long, blonde fall, since my hair was still months away from bring long enough to really style. I looked good as a blonde and I loved the way my "hair" moved.
I was wearing several maxipads over my cock to ensure that I didn't stain my dress with a cum of anticipation or self-adoration. Those are easy cums to have, but not very satisfying.
Mom arrived at six and praised and fussed over me until Jason arrived half an hour later.
Jason's eyes nearly left their sockets when he saw me and I'm not sure, but I think he needed a maxi-pad when he checked out my legs and bottom.
Mom embarrassed me a little with her fawning over me. Then she redeemed herself by saying to us, "Now remember, kids, no sex in a car or dark alley. Come back here and go to Charlie's room. I'll just turn my hearing aid off and go to bed."
Why aren't more mothers as understanding as my Mom?
Jason didn't hide me. He took me around and introduced me to lots of people. Then he took me to a really nice restaurant with cloth napkins and everything. He held the door and held my chair. I really felt like a lady. A special lady at that.
After dinner he helped me into the car, then got into the driver's seat and said, "Would you like to go to a movie or should I …uh…take you home?"
"Take me home, please, Jason," I said. "I can't wait for you any longer."
It was true. My ballbag was in the red zone.
It moved into crimson when he kissed me.
The sweet boy was an outstanding kisser. It was so different from kissing a girl or a sissy. I had never felt as girlish as I did at that moment. Then things got even better.
Jason's naughty hand pulled my skirts up and he reached into my panties for my girlish clitty.
He broke off the kiss and said, "I was worried about you and your cum level, Sweetheart. You could get cum poisoning. Hold your skirts up and I promise it won't go on your pretty dress. Jason aimed my cocklet straight ahead as he kissed me deeply. He handled me so deliciously. I was so randy. His warm hand felt so good. He was so manly. Ohhhh. I felt a wall collapse inside me and I began to shoot cum straight at his dashboard. I felt so happy that I gave the girliest little squeal as much of my remaining, troublesome masculinity left me.
True to Jason's word, not one squirmy little sperm landed on my pretty dress. I thought he would use a Kleenex or something to clean me off, but instead, he leaned over and licked my cockhead back to mint condition.
I like that boy.
I offered to help him visit heaven, but he said he could wait until he was naked with me in bed.
That image made me rockhard again.
We arrived home and, true to her promise, Mom was invisible. I led my man to my room and then kissed him like I meant it. In my big heels, we were the same height, which makes kissing very comfortable.
I turned around and asked Jason to unzip me. He did so, giving my bottom as nice feelup in the process.
I shucked my dress off over my head, then hung it in my closet. When I came back, Jason was completely nude and all his clothes were on the floor. Another basic difference between the genders.
I liked what I saw. He was a beautiful specimen. And his cock belonged in an art gallery.
I was in my bra, slip, stockings, garter belt, panties and heels, exactly as he had seen me when my sissy "sisters" had played their mean trick on me a week earlier. But this time there was no fear and no humiliation.
I removed my slip and stood before Jason. He took me to my bed and laid me down.
Jason's first interest was in my bra. Maybe it was silly to wear a bra with no titties, but it made me feel more feminine. And I loved the feel of it against my nipples. Jason lifted the bra and kissed my right nipple. I arched my back, squealed and came hard, drenching my panties.
That surprised us both. Apparently, I loved having my nipples sucked. And they were very sensitive and connected on a direct line to my genitalia.
Jason exploited this new knowledge without mercy.
First, he pulled down my cummy panties, exposing my wet, limp pricklet to the elements.
Then he put some of my expended cum on two fingers and transferred it all to my tiny bottomhole. He rubbed my own goo around my anus, then inserted one, then two fingers in me.
By that time, I was shuddering with pleasure and anticipation and my cock was half-stiff yet again.
Sadly for me, he removed his fingers from my bottom, but then, oh joy, he scooped up more spurties and used his fingers to rub it around the insides of my anal canal.
I was ¾ hard again as he ran his fingers in and out of my "pussy." I gasped each time he went in.
Then Jason got serious. He fingerfucked me mercilessly as he began to kiss, lick and suck both virginal nipples. Oh, Mama. The sensations. I was panting and mewing as he kept it up and kept it up. Then I surrendered to him completely as I felt six frantic globs of cum evacuate my girlish body.
It had been a really good date so far and I was pretty sure even better things would happen.
I was right.
"Can I suck you now, Jason," I asked through an orgasmic fog.
"No, Sweetheart," he said. "I'm saving this erection for your pussy."
My moment had arrived.
Total emasculation. I was going to allow, no, beg a man to do something no real male would allow. I was going to be a man's fuck toy. His little girl. His possession.
Lead me to it.
I lifted my legs and spread them, just as in my naughty, Mr. Evans dream.
Jason mounted me, then kissed me. Mmmmm. I wiggled my bottom in invitation.
Jason was very aroused. He placed his wet tip on my cum-slicked anus and wedged the head partway in. I gasped and whimpered for more.
I got more. He pushed and the whole, thick mushroom was in.
I think I gurgled or something. It hurt just a teensy, then it was pure pleasure. I reached around him to grab his butt, then pulled him to me. The whole thick, red thing popped in. (I know that wasn't a submissive move, but I was still learning.)
That time I did scream. A happy scream. Didn't want Mom calling 911. And the last itty bit of my masculinity checked out and got a cab to the airport.
My man was in me. Fucking me. Loving me. Mastering me as he does everything he can to please me. I was climbing steps of ecstasy, each steeper, but more intense than the last. When I did cum, it was unlike any cum I had ever had. It seemed to come from within me. It took a long time to build, and a long time to subside. It was a girlish cum. My first. And I wanted more. Lots more.
I had four more that night as Jason had three. His curfew was 1 a.m. or we would still be "doing it," that's how great it was.
I never even sucked his cock that night, but on our next date, the following Friday, I led off with a four-star blowjob for my man. Get the first one in your belly, girls. It's the creamiest and most delicious.
My life is awfully good right now. I have my sissy sisters during the week, Jason on Fridays, Grace on Saturdays and I rest up on Sundays. And then there's the whole idea of Mr. Evans. Maybe I should do something really naughty and get "disciplined."
And to think, I didn't want to be sissysat.
Comments? Ideas for future stories? Just let me know at firstname.lastname@example.org
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