Crystal's StorySite


Forced to Dress Up

by Kim Babe


Here is the ultimate story about forced dressing. It's a true story about what happened to me in the mid 70's. Because I didn't have access to any girl's clothes at home, I started sneaking (breaking) into my neighbor's homes and trying on their stuff. I know it's wrong now, but back then I…well, we all have regrets I suppose.

Getting back to my story, I would enter the house when the family was gone and have a grand time fulfilling my fantasies. It was exciting not knowing what delightful, feminine things I would find next. Once I found a 'adult' baby dress with accessories that Sarah (the one in this story) had worn to a Halloween party. I spent the day in a playpen wearing diapers, sucking on pacifiers and bottles, playing with dolls, and pretending I was a 1-year old little girl. Yes, it was wrong but like I said, I didn't think about that until the day I got caught. Here is the story of that day and what came from it. Maybe some of you can relate to what happened to me.


It had been a week of bliss. I had spent the last seven days indulging and trying on every dress, skirt, and nightgown that my friend's mother and sister own. It had been simple enough to achieve. I had unlocked a window before they left on vacation and crawl through it. Once inside I was like a kid at the carnival. The clothes; all those wonderful, feminine clothes, from the work outfits to the silky prom dresses loaded with lace and ruffles, were just begging to be worn. I even found a French Maids outfit Mrs. Jennings had hidden away for those sex games with her husband. Unfortunately, I didn't discover the real prize until the last day. There, hidden in a corner on the top shelve, was a box wrapped in brown paper and tied with white string. Inside was the silkiest, prettiest, most feminine wedding dress I had ever seen. It was covered with lace and beads, and tiny white bows around the hem and neckline.

Carelessly I lifted the dress from the box and removed the crumple paper inside the sleeves. With shaking hands I put the dress on, along with the sheer wedding veil. Standing in front of the mirror wearing the wedding gown and blonde wig Mrs. Jennings owned, I imagined myself walking down the isle and being seen by hundreds of people. The excitement of the moment was too much, and I slipped out of the dress and into a long, silky nightie lavished generously with lace to relieve myself. Afterwards I went to put the dress away and discovered a huge problem. The dress had been professionally packed, and no matter how hard I tried I couldn't get it back into the box the way it had been.

"Mrs. Jennings won't notice," I concluded as I put the box back on the high shelve where I had found it. I did a last check to make sure everything else was in place and slipped out of the house.


Three weeks later I approached the Jennings home with some apprehension. Mrs. Jennings had called me the night before and asked if I could come over and help Dave move some stuff. What made me suspicious was that my friend was supposed to have gone fishing with his father that weekend. Had he gotten in trouble at the last minute and been grounded. I nervously rang the doorbell and waited for Dave's sister, Sarah, to answer.

"Hi Jim," she smiled in a way that made me uneasy. I could almost sense I was in trouble. If she hadn't grabbed my arm and pulled me inside, I may have turned and left. "Mom, Jim's here," she called out.

"Oh good," her mother called from her bedroom in a normal voice. But when Mrs. Jennings came down the steps she was wearing an ugly frown. It was more than just a frown; it was a look of pure anger. Then I noticed Sarah didn't look too please either.

"Where's David?" I asked, feeling very uncomfortable about the way they were acting toward me.

"With his father," Mrs. Jennings answered curtly. Her pretty face with its short, blonde hair and attractive body suddenly seemed hard and stern. "In here, young man. We need to talk!"

Now I knew I was in trouble, but there was no way to leave with Sarah blocking the door. Mrs. Jennings grabbed my hand and with great force pulled me into the living room and sat me in a chair. She stared at me with angry, merciless eyes, and I knew I was in big, big trouble. She pointed her finger at me in an accusing manner and stated, "You were wearing my things, weren't you!"

"What? No…of course not," I stammered.

"DON'T LIE TO ME!" she yelled. "I have a witness who saw you going into my house. I could have you ARRESTED you little PERVERT…and I WILL unless you tell me the truth! Now, you were wearing my things and I want to know why!"

I swallowed hard and tried to think up a good lie. "I wasn't wearing your clothes; I was…only looking at them."

"Looking at them?" she answered somewhat surprise. "Why?"

"Well I…. I don't really know why, Mrs. Jennings, ma'am. You always look so pretty in your clothes. I guess I just wanted to get a closer look at them."

"I see, and that goes for Sarah's clothes as well?"

I snuck a peek at Sarah who stood close by with a silent, stern expression on her face. Did they know? I had been careful – damn careful about putting their stuff away. How could they really know what I had done? They had to be guessing.

"I…I just looked at your dresses, that's all. I didn't go through your underwear if that's what you mean."

"LIAR!" Mrs. Jennings snarled as she picked up the phone. "I'm calling the police. Perhaps they, and YOUR MOTHER, can get the truth out of you."

"NO!" I shouted in panic. "Please, not them."

"Tell me the TRUTH right now or I WILL call them," she threatened while holding the phone in her hand.

I hung my head in embarrassment. My ears and cheeks burned as I muttered out the next words. "Okay, I guess I did try on a few things. I'm…I'm sorry.

"So you were WEARING my clothes," Mrs. Jennings roared. "For what PURPOSE?"

"I don't…I don't know," I responded with frighten tears. Even my mother, who seemed to lose her temper with me on a daily basis, had never been this angry toward me. For a moment I thought Mrs. Jennings might slap me if I gave her the wrong answer.

"Yes you do, and I want to KNOW WHY!" she demanded angrily. "I want to know why you took out my wedding dress and wore it. And if you give me a 'I don't know answer' again I swear I'm calling the police."

I had run out of lies, or maybe I was too afraid to try. I sniffed and whispered, "I guess…I guess I just wanted to know what it felt like to wear it."

"Really," she mocked while hanging up the phone. "Well why didn't you say so? That's the first thing you've said so far that makes sense."

"It…it does?" I looked at her in surprise.

"Of course," she replied in a mellow, but still anger tone. "You were curious and wanted to find out. Sarah used to do the same thing until I taught her a lesson."

"Well, I've certainly learned my lesson, Mrs. Jennings. I'm sorry… so very sorry for what I did. I'll go now." I tried to get up but she pushed me back into the chair again.

"Where do you think you're going?" she hissed. "You wanted to be me…and now you're going to get your chance!"

"I…I don't understand," I stuttered nervously

Sarah giggled, and her mother got a wicked grin on her lips. "Follow me and you will. Oh, a word of warning young man. If you disobey me once or try to leave without permission I'm calling the police. Is that clear?"

"Yeee…eeees…sss." I answered.

Mrs. Jennings grabbed my hand and forced me up the steps to her bedroom. On entering the bedroom I noticed a sheet was lying on the bed covering up something. Mrs. Jennings went to her closet and pulled out her wedding dress. Immediately my legs turned to rubber as she carried it in my direction and hung the dress on the back of the door. Sarah noticed my reaction and grinned. "Look mom. He's so excited that he's about to faint."

"That's common among brides who are about to get ready for their 'big' day," she smirked.

"Big…day. Look, Mrs. Jennings. I'm really, really…really sorry about what I did and all…."

"Good," she interrupted abruptly. "But being caught won't stop you from doing this to me again, so I'm going to indulged you in your fantasy. You wanted to know how it felt to wear my wedding dress and be a bride young man, and now you're going to get your chance…in SPADES!"

She yanked the sheet off the bed, uncovering all kinds of feminine objects meant to go with the dress. Panties, stockings, and a stiff lacy petticoat were among the items she had laid out for me.

"Strip," she ordered then added, "And make sure you turn around so we don't have to see your thing."


"One more 'but' and I call the police," she threatened. "Now take your clothes off!"

I did as she ordered, knowing if I disobeyed her command she would follow through with her threats. As I removed my underwear Sarah giggled.

"Cute butt," she observed and then noticed something else. "Look how smooth his legs are, mom. Looks like Jimmy-girl shaved his legs."

"So it seems," Mrs. Jennings agreed. She reached down and tossed me a pair of panties off the bed. "Here, put these on so my daughter doesn't have to keep viewing your behind." I held the panties in my hands. They were white, soft, and felt cold. Running down both sides were lace roses embroidered into the silk material.

"Stop fondling 'your' panties and put them on," Mrs. Jennings ordered.

With my back to them, I stepped into the panties and slowly pulled them to my waist. The panties were made of a different material than what I had wore before, and they clung to my dick like a magnet to metal.

"Don't you DARE play with yourself in front of us," Mrs. Jennings warned me. "If your hand even moves in that direction you'll be sorry. Now, put this on."

She tossed me a panty girdle with snaps on the legs. I slid it on and felt it crush the silky panties against my penis. The action caused me to shiver in sexual delight.

"Good, now turn around," Mrs. Jennings ordered like a drill sergeant. I did as I was told, and Sarah approached with a huge smile. In her hands she was holding open a white lacy bra.

"Hands out," she instructed crisply. I did as she said. I didn't dare disobey either of them now. Sarah pushed one loop of the bra over my left hand and did the same with the right. Then she stood behind me and pulled the bra tightly around my chest and fastened it. The bra was too small and dug hard into his skin. "You'll get use to the discomfort," she giggled while snapping the back of my bra with a grin. Mrs. Jennings approached and stuck some fake breasts into the bra cups, making them firm and round.

"There," Mrs. Jennings half-grinned. "You're starting to shape up."

"Looks like he has something on his chest that he wants to get off," Sarah added. Both women laughed as I blushed in embarrassment.

"Awww, our little princess is embarrassed by our comments," Mrs. Jennings observed humorously. Then just as quickly her smile faded and she became angry again. "Perhaps you'll think twice about going through my things again. Now sit on the bed."

I did as she commanded, and Mrs. Jennings handed me a pair of silk stockings to wear. I rolled one pair up and stuck my foot in. Slowly and carefully I worked the stocking over my knee and up my leg. When I was done, Sarah knelt and snapped the stockings to the girdle. Then I did the same with the other pair and the process was repeated.

Mrs. Jennings picked up the puffy, white petticoat and snapped it in the air a few times. It seemed to swell even more, and she held it in front of my face to see. It was white as snow, with multiple rows of thick flower lace that was strung around the outside. The bellowed effect of the petticoat was due to no less than five tiers of crisp nylon tulle chiffon with a comfortable satin inner layer.

The petticoat was placed on the floor, and I was told to step into it. Fearing what she might do if I disobey her, I did as I was told. Sarah lifted the ruffled fluff up my body and snapped the waistband around my waist when it was in place. Mrs. Jennings re-appeared holding a full, lacy white slip. I remember the slip well; because it was the prettiest slip I had ever seen. It had a flower lace design that started at the bodice and went down the hem. Around the chest and hem was a feminine, flower lace. It was absolutely gorgeous, and a crime to cover up.

"Hands up," she instructed. Mrs. Jennings positioned the silky slip over my arms and head, and with quick tugged slide it over my body. The slip ended up covering almost the entire petticoat.

My brain was on sexual overload and I found myself getting very hard. How I wish I could reach down and relieve myself. My reaction to the slip didn't go unnoticed by Mrs. Jennings. In a cold and hard voice she lashed, "So, you think this is fun, do you? That this is some kind of game for your sexual amusement." Then in a more sinister tone she whispered, "Well princess, the fun hasn't even started yet."

I swallowed hard at her threat as she turned to where the wedding gown was hanging. Mrs. Jennings carefully unzipped the dress and took it off the hanger. Then she held the wedding gown against me, and this seemed to cause her anger to grow.

"It looks like the dress will fit…but then you already know that, don't you," she spoke harshly. "My wedding dress…MY WEDDING DRESS! If you want to wear it so badly then you're going to do this right. How does your transformation feel so far princess?"

"I'm…I'm ready to stop," I stuttered.

"Stop?" she questioned in mocked seriousness. "Prevent you from living out your perverted fantasy? Oh no, we're not stopping now. I have big plans for you! Big plans my dear."

"What are they?" I whimpered.

A cruel smile appeared on her face. "Look at him, Sarah. He's crying, just like a bride on her wedding day. Why he's…she's becoming emotional." Then Mrs. Jennings voice became harsh again. "If you think crying is going to get you out of this you're wrong young lady. This is your fantasy, and I'm going to complete it for you. Now keep your hands up."

Mrs. Jennings motioned her daughter to follow her lead, and together they lifted the dress over my head. Slowly it was lowered over me, and I could feel the silky material brushing against my face. My hands and arms were worked into the lace sleeves, and collar was brought over my shoulders. Both ladies labored to get the dress position properly; twisting the hem and straightening the bodice so it was in place. Then Mrs. Jennings stepped behind me and placed one hand on the zipper.

"Take a deep breath and hold," she commanded. Slowly I felt the zipper being worked past my waist, up my back, and finally ending between my shoulders. As she zipped the dress I felt it grow tighter as it slowly sealed me in. The dress pushed firmly against the petticoat, which was fighting to maintain its bell shape appearance. Mrs. Jennings tugged at the zipper a few times and hooked the top together. Then she stepped in front of me and nodded with silent approval.

"Not bad, but we still have a ways to go princess. It's time for the next phase of your fantasy.

Mrs. Jennings walked to her vanity table and motioned me to join her. Although the table wasn't very far away, I had a heck of a time getting to it. The dress was heavy and constricting, and the petticoat rustled loudly with every step I took.

"I guess we don't have to worry about you running away," Mrs. Jennings stated calmly. She placed the chair against the back of the dress and said, "Okay, sit down now."

The dress was so thick that I couldn't even feel the chair as I sat. All I could feel was the mounds of silk and lace caressing my smooth, silk-encased legs. Mrs. Jennings draped a sheet over me. "I'm not taking any chances getting makeup on this dress, although I'm going to have it dry cleaned after this and you're going to pay for it young lady," she insisted.

While Mrs. Jennings was busy with the sheet, Sarah had grabbed her mother's wig off its stand. She shook it violently for a few seconds, and then used a stiff brush to fluff it out. Once Dave's sister was satisfied, she stood behind me and pushed the wig firmly onto my head. I watched myself in the mirror change from being a boy in a dress to a young woman with long, blonde hair. Sarah took the brush again and stroked the wig to get it just right. Mrs. Jennings left and returned with a large, black box. She set it on the makeup table and took out a pair of tweezers.

"Your eyebrows are a mess," she announced. "I'm going to thin them out a little…and don't you start carrying on about the pain or I'll make them look so feminine you'll have to wear a dress for a month just to look right." She grabbed an eyebrow and yanked. I winced in pain but never said a word.

"It hurts to be pretty," she commented in a stern tone while pulling out some more hairs. Then she took her scissors and thinned my eyebrows even more. "Much better. Now for your makeup."

Sarah and Mrs. Jennings approached like mad scientists, holding brushes and powders in their hands. They attacked my face with vigor, using the magic of their makeup skills to bring out my most feminine features. The rouge was applied carefully and evenly, after the foundation had been added. The eye shadow and mascara was brushed on to highlight my eyelashes and blue eyes. Sarah did my fingernails, filing them to a soft point and painting on some red nail polish, while Mrs. Jennings added the finishing touches to my face and hair. From her black box Mrs. Jennings pulled out a bottle of perfume, and generously sprayed it to different parts of my body. It smelled super sweet and feminine.

As the time past I got hot sitting there in the dress. All that silk and nylon I was wearing trapped my body heat, making me feel like I was roasting in an oven. I could feel beads of sweat forming over parts of my body. Mrs. Jennings noticed my discomfort and, perhaps in an act of mercy, turned on a fan and pointed it at me.

"We should've put baby powder on her first," Sarah pointed out.

"I thought about that, but I wasn't about to have either one of us touch his body," Mrs. Jennings commented while fluffing out the wig a little. "She'll just have to accept that this is part of the price for being beautiful, isn't that right princess?"

"You know mom, we really need to think up a name for her."

"Yes, I suppose you're right. What do you think dear, Darlene? Pat?"

"How about Kimberly, or Kim for short," Sarah suggested with a small grin.

"Kimberly, what a lovely, 'feminine' name," Mrs. Jennings smiled evilly. "Do you like that name, princess?"

I lowered my eyes and blushed, causing Mrs. Jennings to laugh. "Aww…look honey. Our princess likes her new name but is too embarrassed to say so." Mrs. Jennings finished with the wig and turned back to her black box. From it she pulled out a tube of red lipstick and opened it. "Pucker up, Kimberly."

She moved closer, and I felt the cool taste of lipstick being applied to my lips. Sarah stood next to her and smiled, obviously enjoying the predicament I was in. When Mrs. Jennings was done she stepped back and admired her work. "Now it's time for the crowning glory," she said.

From the box Mrs. Jennings carefully lifted her wedding veil and fluffed it out using her hands. Then she approached and in the mirror I saw her place it gently on my head. She fussed with the veil to get it the way she wanted, then stepped sideways to see how it looked.
"Perfect…everything is perfect," Mrs. Jennings said. Then she grasped her hands against her chest and giggled, "Oh, you look lovely, Kimberly. You look like you were born to wear that dress." Sarah joined on the teasing.

"You're so right, mom. Imagine if we had dressed him in one of your frilly negligees."

Mrs. Jennings clapped her hands and laugh. "We still can, dear. You would like that, wouldn't you, Kimberly?"

I blushed in embarrassment and shook his head in shame. "Please," I begged. "I've learned my lesson. I swear I'll never do this again. You had your fun, please…let me go."

Mrs. Jennings angrily grabbed my chin and forced me to look at her. "Fun? You think we're doing this for 'our' fun? This is your fantasy young lady, not ours. It was you who wanted to wear my wedding dress; we had nothing to do with your decision. My daughter and I are only trying to make your dream come true. If you don't like the way it's turning out, don't blame us for that."

"You don't have to be so mean about it," I sniffed.

"Mean," Mrs. Jennings lectured bitterly. "Should I be 'happy' that some stranger was going through my underwear and trying them on? Do you think I should be more understanding of your needs because you're only 15? What about my rights and my needs? The only reason why you're sorry is because you got caught. If I had my way I would've turned you over to the police, and let them and your parents handle this, but my daughter convinced me not. Mean? Turning you in would be 'mean'. Not only would you have to face your parents, but you would have a record for the rest of your life. How does time in a juvenile detention center sound, mister? How does all your classmates knowing about your little secret grab you? You haven't seen me be mean yet, young lady!"

I started to sob, knowing she was right. Sarah handed me a handkerchief while her mother looked on with almost no compassion. Dave's sister patted me on the back and in a comforting tone said, "It's okay, Kimberly. Just do as we say and everything will turn out all right for you. Don't cry, sweetie."

"I'm glad we used the water-proof mascara, " Mrs. Jennings exclaimed, a little disgusted at my crying. "Take care of her while I get the camera."

"You committed the worse sin," Sarah explained softly after her mother left the room. "My mother can't stand it when anyone uses her things without her permission. She gets mad at me if I borrow something of hers without asking. Then again, I was a little peeved when I discovered you had been through my things."

"I'm…I'm sorry," I sobbed. "I didn't think about your feelings at the time. Can't you stop this somehow?"

Sarah shook her head. "No, I can't. My mother won't stop until she sees this thing through. She's super pissed and wants to punish you. It took my best effort to convince her not to turn you over to the police and expose your um…hobby."

"Why did you do that after what I did to you?" I sniffed, feeling even guiltier now for what I had done.

"I don't know, I kind of like you. I'm not in love with you or anything, but I always thought you were a nice, sensitive guy. Now I understand why." She paused for a moment. "Despite what my mom might be feeling, I've found dressing you up kind of fun. Maybe next time I'll dress you as my little sister."

"Next…next time. You mean, it won't end here?"

"Well, as long as my mother isn't around it doesn't have to," she winked. "I'll think about it. Now, if I were you I would do everything my mother tells you to do to the letter. Once she calms down then she'll let you go. She's been waiting for this moment for weeks."

Mrs. Jennings entered the bedroom with a camera in her hands. She pointed at the shoes on the bed. "Sarah dear, please help Kimberly with her shoes so I can take some pictures. Oh, and don't forget her garter."

Sarah smiled and lifted the skirt and thick petticoat off one of my legs. As she slid the blue ruffled garter on, Mrs. Jennings took some pictures. Then Sarah took a pair of white, two inches heels and placed them on my feet. After she was done, Sarah lowered the dress and petticoat and brushed it out.

"I brought those shoes just for you, so you could wear them with this dress," Mrs. Jennings commented. "Your feet were much too big for our shoes. Now, time to stand up princess and begin phase three of my operation."

"What's…what's phase three?"

An evil smile crossed Mrs. Jennings lips. "You'll find out soon enough my dear. Take our hands." Sarah stood on one side and Mrs. Jennings on the other. Together they held my hands and on the count of three lifted me out of the chair. It was my first pair of high heels, and I found myself wobbling as I stood.

"Follow me, Kimberly," Mrs. Jennings ordered. "Sarah, grab her train."

Slowly I walked toward the steps, being unable to do otherwise. The dress and thick petticoat prevented me from moving very faster, and my first time in heels made walking a real effort. Sarah followed behind me, holding on to my train and giggling at my efforts.

"You need to sway more," Mrs. Jennings commented. "You don't walk like a mature woman yet. Wiggle your hips."

Going down the steps was an even slowly process than walking. Mrs. Jennings stood in front so I wouldn't fall while Sarah help me hold on to a large portion of the dress. The petticoat rustled as my legs brushed against it with every step I took. By now my body was wet with perspiration and I felt like I was swimming in the dress. I had to brush the hair out of my eyes several times as I took each step carefully. When we got to the bottom Mrs. Jennings led me to the living room.

"What….what now?" I asked nervously.

"The best part," Mrs. Jennings exclaimed. She walked over to the bay windows and removed the curtains. Their home faced a busy street, and windows actually hung a little over the sidewalk. "Come here, Kimberly."

"No," I shook my head fearfully and back up into Sarah. She grabbed hold of my arms and held me in place.

"I said come here," Mrs. Jennings demanded in a hard tone. "Your public awaits you."

"Please Mrs. Jennings, please," I begged. "I'm sorry for what I did. Please don't make me do what I think you want me to do."

"Look at him cry, Sarah," Mrs. Jennings commented harshly. "We should've dressed him like a little girl and let him play with your dolls. Now, COME HERE YOUNG LADY."

"Pleeeeease," I begged, now scared to death. What if someone came by and recognized me? Mrs. Jennings walked over and frowned.

"I'm sure you think I'm a mean old BITCH, don't you. Well I'm not. I'm giving you exactly what you wanted. A chance to wear my wedding gown and be admired in it...and you're going to do it too or I'll call your mother and the cops. Be thankful Sarah and I did our best to make you look like a 'real' girl. If you're worried someone is going to know it's you in that getup, then your fears are groundless. Wait, let me show you."

Mrs. Jennings left the room and returned a minute later with a full-length mirror in her hands. She placed it in front of me and grinned at my reaction. I couldn't believe the change. I didn't look like a boy anymore; I looked like a young woman. I was beautiful.

"See, I told you your fears were groundless. Now, step in front of the windows. Oh, and hold on to these." She thrust a large bouquet of flowers into my hand.

"But…but what am I suppose to do?" I asked as Mrs. Jennings dragged me to the window.

"Stand there and be admired, young lady. And don't forget to smile." Mrs. Jennings positioned me in bay window area, and I looked out at the busy street. Several women walked by and smiled at me. A couple of women waiting at the traffic light noticed me as well. The passenger nudged the driver, and both took a good, long look at me.

"Now," Mrs. Jennings said calmly as she got down on her knees and fussed with the dress. You can either stand there and pretend to be a mannequin or, you can smile and wave at the people going by. This is your fantasy young lady, so you'll decide what to do. You may be able to fool the people in the cars, but those who walk by are going to notice you're a real person."

"I…I want to change now," I pleaded. The thought that someone may discover who I was horrified me.

"Change, but we just got started," she taunted. "Oh no, you're not going to change yet. You wanted to be me, and now you're getting your chance. You'll stand there for a good long time and be admired, just as you wanted to be. Look, here comes someone now. Smile pretty, dear."

There were three teenage girls about my age coming down the street, their ponytails swinging as they walked. One of them spotted me standing there and nudged the other two. They stopped outside the window and gawked in admiration. Then one girl said something to the others and they giggled before leaving. I found myself fidgeting like a cat on a hot, tin roof.

"See," Mrs. Jennings explained as she fluffed the skirt out a little more. "They think you look pretty. All you have to do is stand there and let people admire you."

More cars stopped at the traffic light, and the people inside the cars looked in my direction. I felt my cheeks burn when four ladies in a small van gave me their full attention. As an added bonus, Mrs. Jennings made me turn around so they could see the back of the dress, with it's huge, satin bow. The ladies smiled with appreciation at my efforts.

This went on for hours. I stood in front of the windows as hundreds of people drove and walked by. A couple of ladies stood there for so long that Mrs. Jennings invited them inside for a closer look. I sashayed nervously around the room so they could observe the flow of the dress. The ladies kept saying how pretty I looked, and then Mrs. Jennings told them that the bride to be was really her nephew who was being punished for going through her things. The ladies laughed with evil delight, and chastise me for being such a 'naughty girl'. Mrs. Jennings smiled and told them she didn't think there would be any more problems from me after this. Each of them posed with me for a picture, and rubbed their hands up and down my silky dress laughing and commenting about how 'pretty' and 'feminine' I looked. I felt total humiliated.

After what seemed like an eternity Mrs. Jennings finally let me go back upstairs to change back into my own clothes. They help me out of the dress and petticoat, then removed the makeup. Mrs. Jennings still seemed upset, but not like she had been when this all started. After I was dressed in my old clothes she presented me with a slip of paper.

"What's this?" I asked.

"This is your bill," she replied. "Open it up." I did and my eyes almost bugged out. The charges were over $300.

"I don't understand."

"It's all right there," she explained. "Dry cleaning and re-packaging my wedding dress; $90. Makeup and supplies; $23. New shoes, $25. There's more; underwear, pictures, Sarah and my charges for helping you get ready. It's all on that list. I expect payment in 30 days."

"But I don't have that kind of money," I protested

"Sure you do," she insisted. "I heard you talking to my son last week about the money you had saved up for a car. What was that amount? About $800 I believe?" I gulped and nodded.

She smiled coldly. "Then I'll expect your payment in 30 days. Only then will you get the stuff I purchased for your perverted fantasy, and the pictures too. If you don't pay me, I'm sure your mother will be very interested in those pictures. Any questions?"

"Um, no," I replied a little rejected. What could he say?

"Good," Mrs. Jennings smiled. Then she grabbed my chin and in a firmer tone said, "I hope you've learned your lesson, Jim. If I catch you wearing my stuff again I'll try more extreme measures. Now go home and don't let me catch you doing this again."

Mrs. Jennings shooed me outside and closed the door. Two weeks later I paid her for that day, and nothing else was said until…

It seems Sarah had her own fantasies about boys in dresses, and came to me with an offer I couldn't refuse. When Mrs. Jennings discovered what was going on she really hit the roof, but that's another story to be told.

The end




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