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Room 209 First Sex as a Crossdresser

crossdresser – trans – interracial – lgbt – first time – virgin – black cock – crossdressing – natural tits – braI've been crossdressing for much of my life, as far back as I can remember. I would even go to sleep as a k** and pray that I would wake up in a girl's body. In the last few years, now that I live by myself, I spent about $1,000 on a whole wardrobe of women's clothes for myself - bras, thongs, dresses, tops, stockings, lingerie, make-up, perfume, etc... I have also been overweight...

My Date with a Crossdresser

A couple of months ago, I was contacted by a crossdresser here at Xhamster. She has asked me not to reveal her identity.We arranged to meet one night at a motel near the Pittsburgh International Airport. I arrived at the agreed time, but when I knocked on her door she told me she wasn't ready yet and asked me to wait half an hour. I agreed.Half an hour later, I returned to her room, but she still wasn't ready. She was apologetic, and asked me if I would rather come back in another half hour, or...

Crossdresser Turns Gay To Seduce His Tailor

Hi all! I am a family man with a loving wife, but she doesn’t know about my crossdressing. It just so happened that she had gone to her mother’s place during her pregnancy, and I got ample time for my crossdressing. I did all of my shopping on Myntra and bought myself some nice soft satin sarees, dresses, gowns, tops, high-heel shoes, a makeup kit, perfumes, and loads of bras. I was waiting for the delivery like a curious kid waits for their birthday gifts. Finally, the day arrived and the...

Gay Male

olderman and mature crossdresser part 1

It was just a normal friday day so I went to the store to buy some food for the week.I wore a jean mini skirt and pink t-shirt and tan pantyhose with my 3"heels and make up and all. As I made my way down thru the ailse I notice a older tall gray haired slim man following me.Well I gave him a couple bending over shots and eye contact.I made my way to the check out an seen him in other line.I finshed checking out when I got outside to load my bags in my car he was parked next to me.He spoke to me...

My first time with another crossdresser

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my brother and sister. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer...

Crossdresser wanting some dick on the road

I`ve been crossdressing since I was 20 years old.One of my favorite things to do is get all dressed up in womens clothes and drive around on the open road.Several years ago I was mad at my ex wife for doing some stupid shit with our checking account and we were split up for some well needed cooling off time.The more I got to thinking about her stupidity the more I got to smoking some pot and drinking a few mixed drinks to get the crap off my mind.I got pretty stoned and decided to get dolled...

My first Crossdresser Part One

When she walked in to the restaurant I knew I was in trouble. It was the end of three long days at the convention and I was tired. I had come down to the NASCAR Cafe for a sandwich, mainly because it was the only bar in the Sahara that didn't have video poker...I lose a lot of money playing video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's strutting toward a table.Convincing she was not, a crossdresser without question. But pretty, really...

A Crossdresser 8217 s Life

Hi! This is my first story on ISS so don’t be harsh on me. This isn’t a real story, but a fantasy which i am going to share with you,though the characters are real. I am a boy(21)(crossdresser) doing my engineering in Bangalore in a reputed college. I stay at one of my fathers friends house, his name is Rajesh. His first wife died due to cancer so he married again. His new wifes name is Rajni. Rajni, in her 30s, is a damn hot woman with a plus size figure. Now lets move on to story… Initially i...

Gay Male

Telling Mom I m A Crossdresser Part 2 The Adult Store

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived. It was just past 9am when I heard a fumbling at the door, my mother had walked in with her heels in her hands and her clothes hanging loose...

Crossdressing

Danni The Crossdresser First Time Sissy

by - sissy debbie This is a true story about what happened to me after graduating high school and how I became a sissy for woman who was nearly twice as old as me. --------------------- The summer after my senior year of high school a neighbor asked me to look after her house and her cat for a week while she took a trip with some friends. Her name was Heidi and she was an attractive woman about 38 years old. She just wanted me to stop in and check on everything a few times. I...

Nenu Crossdresser Nunchi Gay

Hi, na peru ajay. nenu tenth class ki vachinappatiki naku crossdressing alavatu ayyindi. enduko emo telidu, kani adavalla laga chira, jackettu vesukovatam istham. mukhamga Bra and Panty. ma inti venaka oka portion lo vunde oka ammayyi thana battalu vutiki bayata aresedi. ala aresina vatilo thana Bra lu kuda vundevi. mamuluga avi sayantram avi tisesedi. kani oko sari marichipoyo emo battalu tisedi kadu. ala tiyanappudo leka oko sari Valla bathroom lone vadilesina battallono (valla bathroom...

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when she stood up. A box fell from her hands and onto the floor. Being the nice guy that I am, I picked it up...

Crossdressing

Crossdresser ke saath maza

Hello frnds.How is everybody.I recently got another hot encounter in July 2008.It happend at my sis home.Both my sis and her husband work for an MNC.They had recently employed a new maid.They were supposed to go to Pune for some seminar from their company.Since this new maid is new in town and has nowhere to go so my sis said me to stay at her at home so that maid will not face any difficulty.i said ok.I understood the problem and said ok for the proposal.So i reached her home on the day on the...

Incest

CL Memories 1 Crossdresser True Story

I used to get a lot of fun out of CL. I'll post some short stories about some of my experiences there. I sure do miss it. This happened about 10 years ago. I was divorced and living alone, and playing whenever I got the hots and had a good opportunity.I checked CL one weekend night to see if there was any fun to be had, and found a post from a crossdresser visiting a nearby city and looking for company. She (I'll use that pronoun here) had a room in a local motel for the night. I responded to...

Auto Ride Made Me A Crossdresser Whore 8211 Part 5

Except for some dirty and humiliating ones, most of Raghav’s dialogue will be in English in this part about the crossdresser whore. I thought that it is easier for me than translating each of the dialogues. The ride home was uneventful. I just sat dumbfounded in the back seat while Ragahv just fled the auto fast. In a short time, we reached my place. I picked my bags and climbed the stairs. Raghav followed me, carrying another small bag. Where did he get it from? I am sure he was spotting a...

Gay Male

The Pink Dress

The Pink Dress All Michael wanted to do was to wear the prettiest dress he ever saw; he knew he'd look so lovely, but he faced challenges from strange places By Katherine Day (Copyright 2007) During the Depression of the 1930s, even a 10-cent child's haircut was a luxury that Michael's parents could hardly afford, and Michael's light brown hair was long, giving him an a most girlish appearance. Even as a little boy, he...

Next Time I ll Wear the Dress

Next Time I'll Wear the Dress I was shoving paper around on my desk keeping half an eye on the clock waiting for lunch to come around. I had a date that I was really looking forward to. Doris and I had been friends a long time ago but hadn't been in touch for a while. We ran into each other over the weekend and decided it was time to meet up for some long lost conversation. Beep! Beep! Beep! The phone on my desk alerted me to an incoming call. I snatched the receiver from the...

Tight Dresses

Reddit Tight Dresses, aka r/TightDresses! I love to see sexy girls dressed up and ready for action, and seeing them in a tight little dress, just gives my dick life. Lucky for all of the perverts online, /r/tightdresses/ is a subreddit filled with pictures of horny girls who are wearing their sexiest dress. Of course, all the dresses are tight and showing off their curves quite nicely.Lots of images of amateurs and known models.The whole point of this subreddit is to focus on the babes who love...

Reddit NSFW List

The Day I Left My Wedding Dress On A Train

The Day I Left My Wedding Dress On A Train ANNE-MARIE: "I'd had my wedding day all planned out ever since I was a little girl, I'd been obsessed by weddings ever since my Auntie chose me to be a flower girl at hers. I knew the type of venue I wanted, the flowers, the colours my bridesmaids would wear, the music I'd dance to, I had a good idea about the kind of man I wanted to marry too. And of course I had my dream wedding dress. I would be a fairy tale princess for the day, gloriously...

My First Dress

My First Dress by Sissy Susie It all started the day mum had to take my sister Sandra to London for the day. My sister's school orchestra were playing in the regional finals of a competition. As there would be a lot of waiting around mum had decided that I would spend the day with my aunt Caroline and my twin cousins Becky and Kirsty. I did not mind because although the twins were fourteen, two years older than me, they enjoyed things like football and we even played it together,...

Sister s Party Dress

SISTER'S PARTY DRESS By Beth Ann My name is Andy; this is the story of how I got caught wearing my little sister's dress and the circumstances that followed. I have embellished the story, but the basic events actually occurred. School came to an end; it had been the first year of school for my little sister Jenny. Kindergarten was good for Jenny, she made many new friends and was well liked by everybody. Jenny was a particularly cute and bouncy little girl who loved to wear the...

WWAC The Un pleated Non dress

WWAC: The Un-pleated Non-dress by Ashley B. D. Zacharias?I hereby call this meeting of the Wicked Women’s Adventure Club to order.? Lydia looked at the four women sitting around the table and nodded. ?I would like to take this opportunity to introduce our newest member, Miss Amelia Cox.? The four other members nodded at the young woman with the short blond hair and muttered soft words of welcome. She nodded back, nervously. The introduction was needlessly formal because she had met three of...

Dress Code

Dress Code by Brian [email protected] I wrote this back in 1999. Be kind. If you review history, you'd be surprised to see how often a small event can have the most monumental results. If the driver of Archduke Ferdinand hadn't taken a wrong turn in 1914 he wouldn't have been assassinated and the world wouldn't have been plunged into The Great War. If Lincoln hadn't gone to the theater that night, he never would have been shot. If Hitler had been a really good artist, then he...

The Periwinkle Blue Dress

The Periwinkle Blue Dress A man buys a dress for himself ... and then pays for it. That was the set-up from my first story, "The Green Dress." This is an alternate version of that story, with the same initial premise and same characters from my "The Dress" series. But people and events are different, leading to a different place. I hope you like the alternative. The Purchase "Can I help you find anything?" the salesgirl said. It was just after opening, and I was...

The Dress Shop Part Two

CHAPTER FIVE TRAINING WEEKEND We started Saturday with another failed attempt at love making. Within about 30 seconds of Beth playing with my penis, I gave in and orgasmed. I wasn't even erect, but just the sight of my beautiful, stunning girlfriend playing with me was enough to tip me over the edge. Once again, like last night, there was no evident frustration from Beth. Only embarrassment from me. "Awwww. Such a pretty penis!", Beth remarked, grinning and playing with it in...

SRU The Prom Dress

I rarely do stories in which the narration is in the first- person view, but for some stories it's appropriate. For some it's not. And I thought this story would seem better with first-person narration so I did it. It has more vulgarity than my stories would usually have, but the main character (who narrates it) is a male jerk, and that's how people like him talk, so I did it to make it seem more real. I decided to do this story, because my other stories were talking a bit too...

The Son Dress Part One

Frank's eyes fluttered open and he was dimly aware of the soft morning light edging around his bedroom draperies. But he was keenly aware of his hard and throbbing cock. The dream he had on waking swam hazily into his mind's eye and he saw the soft hem of the dress float across the slick fabric of a nylon stocking covered thigh. His finger traced along that smooth thigh to the tab of a garter and easily followed that one suspender to a perfectly taunt and silky pair of panties. ...

The Gold Dress

It was the summer I was 17, and I had just finished school. Both my parents were at work, and both my younger brothers still had school. But since my exams were finished, I was on holidays. During the day I was free to hang around the house alone, and do what I wanted. We were quite a happy family. I felt like we were always blessed with good health, and reasonable wealth. My parents both had good jobs and were able to afford a big house. In fact, back then, my parents were the only...

My Sister s Wedding Dress

My Sister's Wedding Dress A lot of people have asked me why I do what I do. To be honest I can't really explain it. It has just always been a part of me. While I can't explain why, I can only tell my story. This is my true confession and it is nice to be able to say what cannot be spoken. I have to admit I have had this fantasy & deep desire to be a bride since I was little. I'm dying to tell my story! Confession helps bear the secret. Growing up, secretly I loved seeing...

Ethan s Prom Dress

Ethan, like a lot of teenagers was subconscious about his body, although he did have more reasons than most boys as he suffered from a form of gynecomastia, a condition that gave him perfectly formed, feminine breasts. He also secretly wishes to wear skirts and dresses, which would be a perfect combination if he wasn't too embarrassed by both his body and his desire to follow through with this idea. So instead he bandages his chest flat each morning and desperately tries to hide all of...

The Dress Punishment

The Dress Punishment Katie Leone Being in the principal's office is never a good place to be, especially after you get caught doing something wrong. It makes you feel kind of nervous when you're sitting there waiting for the man in charge to come back in when you know he's getting all the dirt on you that he could. All I can do is sit here and look at the wood panel walls and watch the second hand of the clock move slowly. "Tick, tick, tick," the...

Just Normal Wearing A Dress

Just Normal to Wear a Dress I woke up in some hospital. I could not remember how I got there, but the nurses were telling me I am ok, I survived my auto accident and I will recover just fine, as they kept smiling. I felt fine, was ready to go home but they wouldn't let me. One nurse after another came in asking questions to test my memory. The head nurse told me I had to stay one more night so they could watch me. A younger nurse came in to help me with my shower. She came right...

Edie Adventures in Panties and Dresses

"Edie:" Adventures in Panties and Dresses (1-5/5) by Princess Pervette When I was eleven, I was the toughest kid in the neighborhood. The one who came home with black eyes (but who gave more black eyes than he got), the one who was always ready for a fight, a real scrapper. What nobody knew was that this young neighborhood tough liked to wear girls' panties. It had started one afternoon when my sister asked me to get a handkerchief out of her dresser, and while I was looking for...

To Dress with Spirit

TO DRESS WITH SPIRIT "You know the locals say it's haunted," said my quirky friend Elena as we turned into the long carriage drive which led to the country house hotel in which I'd gained an internship. Her eyes were laughing as she said this, and I pinched her arm jokingly. "Pull the other one." We were both too worldly and rational to believe in ghosts. I'd heard the rumours about the hotel when I talked to people about the internship opportunity, and of course I'd dismissed...

The Wedding Dress

The Wedding Dress by Sheila Anne Morgan I have always been slightly overweight, but now I seemed to have put on an additional ten pounds I couldn't seem to lose, as much as I tried. My wife of five years, Maureen, said, "You know what, Randy, you just need the proper incentive to lose that extra weight." "Maureen, I've tried everything, I just...

Baby Chloe in his Satin Baby Dress Bag

Baby Chloe in his Satin Baby Dress Bag "Hello, Sheila. Come in. Do you want some help with your stuff? Oh my, there's such a lot of it." "Yes, Andrea. Help me wheel everything inside the door and we can leave it in the hall for the time being. Until we've got him ready..." The two women shared a giggle across one of the trolleys. "Is he under sedation?" asked the doctor, pulling the first one inside the door for Andrea to take it from her and park it along her hallway near the...

Forced To Dress Up

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...

Damn Dress Code

Damn Dress Code By Margaret Jeanette Hannah Muggins was getting dressed. She put on her blue pants suit and she could hear her husband, Ray, on the computer in the next room. He was playing games from the sound effects she heard. She wished he didn't spend some much time playing games on the computer. Hannah was very successful. She owned six stores in town and a family restaurant. She employed good managers in every one of them. Right now she was negotiating to buy a liquor store....

Punishment Dress

In the span of history, until relatively recently, a beating was given across the bare flesh, and dress had a significance limited to the procedures and drama of its removal. Before the great change, the chances were that a victim would be crudely stripped and flogged without more ado, but, if dress played any part at all, it was as an agent of humiliation rather than as a layer of protection: a soldier was the more shamed by being stripped of his full-dress uniform, and, by the same token,...

The Dress Shop

The Dress Shop By Margaret Jeanette Sarah Watson was having a great day. She was selling like a house afire. Every customer left with something to spruce up their wardrobe. She was on a roll. It made her feel superb and vibrant. That night at supper she told Tom, her husband, about how her day went. She was so enthused that Tom caught it and it made him happy to see his wife so animated. He had been skeptical when she wanted to buy into a partnership with Marjorie Lane to buy...

Her Sexy Dress

HER SEXY DRESS by Throne "Dear," Marla said patiently, "are you almost done on the computer? We were going to go out and find me a dress for your company party. It wouldn't look good for the owner of Mindswap to show up with his spouse in what she wore to the previous party." "I know," Rich Roman said, not looking away from the computer screen. "I just need to okay these letters Jamison wants to send out." "Really? Do you have to approve EVERY note your vice-president writes? ...

Forced to Dress II

This is a sequel to my first story, "Forced to Dress up!" For a couple of months I had been meeting Nancy at her house to dress when everyone else was gone. On this particular day my best friend, David, was away for weekend with his father and Mrs. Jennings wasn't going to be back home until late that evening. That meant an entire day to lounge around in women's clothes and act girlish. Why Nancy let me dress in her clothes I don't really know. She had her reason and I didn't ask for...

The Red Dress part 1

The Red Dress - Part 1 Final installment in the adventures of a husband who buys himself a dress. Husband comes out for a charity event, wearing a red dress of course. A few months ago, my wife caught me after I secretly purchased a dress for myself. Since that fateful day, I've steadily slipped deeper and deeper into feminimity, all at the hands of my wife, Ann, and her wickedly inventive best friend, Susie. Since our casino adventure, the three of us spent more time...

All Curled up in a Yellow Dress

All Curled up in a Yellow Dress By Sissie Maid Cuckold A few days had gone by since Jane had enjoyed time with her handsome Black lover Ken and she noticed that Susie was getting a little defiant. Jane called Susie to her and when Susie arrived she gave a half hearted curtsey that deeply angered Jane. Instead of lashing out at him immediately and putting the pansy husband in his place she decided to play a little game with him and see what was going on. "Susan, you don't seem to be...

The Green Dress

The Green Dress By Margaret Jeanette Jessie Taylor sat at the kitchen table with her math book open in front of her. Her neighbor, a boy named Jeff Filz, sat next to her. He said, "Algebra isn't hard if you take it one step at a time. Now, look at this problem. It's simple if you look at the parts." He went on to explain how to dissect the problem. She suddenly understood what he was showing her. He was a math whiz. She continued on and did the next four problems without...

The Green Dress

The Green Dress A man buys a dress for himself ... and then pays for it. Note: the first half of this story is true. The second half I alternately wish and dread will come true. Part 1 "Can I help you find anything?" the salesgirl said. I was standing at a sale rack in a women's wear store. The salesgirl was a young girl in her late teens or early twenties. She's pretty cute, I thought reflexively. For a moment, I froze. Was I really going to go through with...

The Dress Shop Part Three

CHAPTER SEVEN THE FIRST DAY After overhearing the conversation yesterday, I was more nervous than ever. Since the conversation, Beth hadn't even eluded to it. That morning, however, Beth seemed worried too. It was clear she knew that the placement at Amy's dress shop could lead to some big freelancing contracts down the line with her magazine. And a permanent job for me. I also think she thought her reputation was on the line. Beth was sitting on the sofa, fiddling with the hem of...

Daddy With a Blue Dress

Daddy With a Blue Dress By Cassandra Morgan Sometimes, things go bump in the night. There are noises. A floor creaks. Voices carry. The cat knocks over a lamp. The wind blows the shade. And kids hear. Billy Adams was only six, but he knew about odd noises. He used to believe he had a monster in his closet, and it was thing that made those noises in the night. But it wasn't true. Nothing lived under the bed, or in the bathroom, or down the hall. Billy was old enough to...

A Pink and White Dress

A Pink and White Dress Janet L. Stickney [email protected] If you were to say that I was scared, you would be right. I stood there completely dressed as girl! And I mean complete, from the skin out, including panties, white pantyhose, a bra stuffed with socks, and a party style dress that did nothing but scream femininity. Pink, with white lace trim, short enough to reveal my knees, pushed out by the three petticoats enough to make it sway with every step I took. My hair,...

Pink and White Dress

A Pink and White Dress Janet L. Stickney [email protected] If you were to say that I was scared, you would be right. I stood there completely dressed as girl, complete from the skin out, including panties, white pantyhose, a bra stuffed with socks, and a party style dress that did nothing but scream femininity. Pink, with white lace trim, short enough to reveal my knees, pushed out by the three petticoats enough to make it sway with every step I took. My hair, once...

The Little Black Dress of Joy

The Little Black Dress of Joy. By Tanya H. ONE. I first saw That Dress in the window of a charity shop in the high street of the town where I once lived. An ordinary Saturday, just after midday, I had just finished work, an undemanding morning clinic, and had a middling, pleasant walk separating me from my house and a shower. I was 26, single, dark haired, apparently easy on the eyes and working as a staff nurse in a small, private, outpatients unit on the edge of town. They called...

Another My First Dress Story

ANOTHER "MY FIRST DRESS" STORY BY JANICE I was about ten years old when I wore my first dress. My sister, Alice, who is one year older than me, was away at Girl Scout camp, it was raining and I was bored. My mother was in the basement doing laundry. I went into my sister's room to see if she had something to play with, maybe I could find a coloring book or something. I could not find anything and as I turned to...

The Dress Code

Mike wheeled the car into the parking space outside the dirty, non-descript building that was his place of employment. Without thinking he slid into a too small parking space, the only kind that were available in the too small lot, and slid the lever into park. Mike had seen it all before, after 40 plus years in the business he was used to the up and down cycles. This one had all the earmarks of the company going under: gradual loss of customers as technology changed and the...

Office Dress Up

Office Dress up [email protected] "Hi Honey, what have you been up to all day?" I was laying on the sofa reading a magazine. The rain had been misting through the morning and Lucy was unbundling herself in the foyer. Her sandy blond hair damped down just enough so that it twirled when she unwound the scarf from around her neck. "Just went down to salon and got my legs waxed." "Ouch did it hurt?" "No, it only hurts the first couple times. Maybe...

The Blue Dress

THE BLUE DRESS BY JANICE My sister, Gwen, had had a birthday last month. Our grandmother gave her a beautiful blue dress. Gwen said that it made her look too young, she was 12 years old and not a little girl anymore; I am eleven and my name is Norman. I thought her dress was beautiful and was dying to wear it, but, being a boy, that was out of the question; or was it? I know that boys do not wear dresses, so when...

The Lady s House Part 1 of 3 Three Dresses for Charlie

The Lady's House Part 1 of 3: Three Dresses for Charlie By Gail Blue The tires made a dull thunk-thunk noise as they ran across the cobble stone street. The bus looked out of place next to 1800s style shops and houses. Just a few blocks away, the town was more modern, though still well- mannered and quaint. But in the town center, there were no cars, and no modern electronics were visible from the street. Charles got off the bus behind a load of Japanese tourists. He tried...

The Dress Redux

It was Monday at lunchtime and one of the first warm days of the spring and the sun felt amazing on my naked body as I lounged on the patio for some much-needed sun. It felt so good to feel the sun again on my body as I took some time for myself during a work break.But my reveling was soon interrupted by my phone chirping a notification of a text message; ‘Hey, do you have time for a chat? Want to ask you something.’ It was a message from my ex-boyfriend Chris. We had a long-term and intense...

Wife Lovers

The Unlucky Winner Or Fruitcake and the Dresses of Doom

The Unlucky Winner -Or Fruitcake and the Dresses of Doom ? by: Emma Smith Being the third adventure of the mildly loveable (so he says), but entirely mad (so we say), scientist Otto Von Fruitcake. Authors Note: When we left our friend at the end of the previous story his cunning but silly plan had totally failed. So there's no change there then. His assistant is soon to be married to a rich and hunky playboy. This is thanks to the now broken sex-changing Flip Gun. You'll notice...

Moms Dress

Moms dress Janet L Stickney [email protected] My mom likes to look at those web sites have a lot of pictures on them, and once in a while they show a girl wearing her moms prom dress or wedding gown or some other very nice dress. Sometimes she sees a womanless pageant or contest and she almost always points out the very best looking boys to me, and some of those boys dressed as girls looked better than their mom! I never gave it any thought, although I do however, like to dress...

The Perfect Dress

I sat by the living room door, eagerly awaiting with nervous anticipation. The seconds felt like hours as the hands on the clock on the wall slowly swept by each tick mark. Every few minutes I'd peek out between the blinds, hoping to catch a glimpse of the package that I knew would change my life. I'd saved up for months just to be able to order this, forgoing lunch every day at school and doing odd jobs around the neighborhood to supplement what meager income I made from working as a...

Tricked into wearing a dress pt1

As a student at college I wanted a bicycle for Christmas. I hadn't past my driving test and even if I had, I couldn't afford to run one with my Saturday job wages. My parents didn't have much money so I didn't ask for an expensive model by name, anything would do. I didn't think they could go far wrong or could they?They did attempt to wrap it with some festive paper and ribbon. Unfortunately nothing could hide its bright bubble-gum pink, wicker shopping basket or step-through frame. I cringed...

The Little Black Dress of Joy Part 4

The Little Black Dress of Joy. Part 4. By Tanya H. Even though I'd fallen happily in love with a soldier, my relationship with the British Army was, I thought, nicely at arm's length. Nina told me stories of the people she worked with, she shyly told me some more about life on tour, but knowing her regimental mates knew my history grew into a wall I couldn't climb over, meaning I hadn't actually met any of them. Nina may have been disappointed in that, after all they were her other...

The Boy Who Would Be Prom Queen Chapter 16 Prom Dress Shopping

"So, what's wrong, Zoey?" Tyler asked. "You spent all of your money giving her a makeover and overnight popularity and you're just going to throw it away? When she's so cute and sexy." "No, it's not like that," she responded. "I actually like her." Olivia laughed and turned to Deanna. "See, I told you she was a lesbian." "You were right about everything," Dee cackled. "Including her falling in love." "Pay up, Dee." Dee handed over a wad of cash to Olivia. "It was so sweet,"...

A Young Hitchhiker In A Blue Satin Dress

“Fuck you, Robbie!” Anna screamed as she stormed off. She and her boyfriend Robbie, along with her friend Carrie, had been drinking a bottle of vodka stolen from her dad’s liquor cabinet. They sat in the cool, dry grass on the edge of the school football field, Robbie in between the two girls, and as the moon rose they began to get drunk for the first time. They were each twelve years old. Across the field, beyond the bleachers, music emanated from the gym where the junior high dance...

Party Dress

Rebecca didn't want to go to the office party. Being only one of a few women in her company she had little in common with her colleagues and she could count on one hand those she'd want to see after working hours. She already knew who would get drunk and who would argue too loudly. There would be bad chicken and a deejay playing music that she didn't like. Yet, here she was, in a hotel room, putting on a party dress.Rebecca's husband Ben loved these events. He liked the food, the liquor, and...

The Irresistible Dress

I entered the store as soon as it opened. I knew entering this early helped to ensure I would be the only customer so I could try on the boot cut jeans I wanted to buy. I said hello to the saleswoman and quickly wandered over to the jeans section but as I did I noticed a rack of new dresses. The one that stopped me dead in my tracks was a simple sleeveless sheath, but I loved the simple color pattern and I could tell the shape of the dress would hug my body. The saleswoman approached me before...

Crossdressing

My girlfriend caught me wearing a dress

My name is Billy, and I'm twenty-six. I have black hair, and brown eyes. I have a girlfriend that I've been seeing for a few years now. I should mention, that I occasionally like to dress up. I'm not talking wearing a tux, I'm talking about wearing a dress. That's right, I'm a cross dresser. Very few people know about it, and my girlfriend, Phebe, wasn't one of them. My mom knew, and a couple friends knew, but that was it. My friends knew, because they also had this weird fetish. We would get...

Crossdressing

My Little Black Dress

My Little Black Dress Janet L. Stickney [email protected] I had gone out to pick up a few items I needed, like pantyhose and new eye shadow, just another fear filled adventure into the outer world. I always felt edgy buying those things that guys didn't usually buy, so I had gotten dressed and bravely went out once again to buy the few things I needed, before I scurried home. I had yet to have anyone figure out that I wasn't a girl, or, at the very least, if they did, they...

The Dress

Mondays are always rough at work and this one was a particularly difficult one making me stay at the office until well past six in the evening. All I could think about on the drive home was a nice glass of wine with Jean and thankfully, when I arrived, I found a note on the kitchen island and an empty wine glass. ‘I am out on the patio. Come have some wine when you get home,’ it read.I took off my tie and made my way outside, wine glass in hand. It was a warm and breezy late spring evening...

Wife Lovers

His First Time In A Dress

The next morning, Andrew woke up to find a text from Emily on his phone.“Come over at 11,” it read. “Gr8 idea 4 2nite.”That sounded intriguing, he thought. He showered, made himself some breakfast, then ambled over to Cavendish Hall. When he got to Emily’s room, Calum was already there, sitting with his feet on the table and nursing a cup of coffee.“Hey, Andy,” he said with a wave. “Last night, eh? Wow. My arse is still sore from the banging you gave it.”“That’s cool,” said Andrew, trying to...

Crossdressing

Latex Dress

Latex Dress When my sexy sixteen-year-old daughter said that she needed a special dress to wear up on stage for her solo during the school musical I thought to myself, “Why not.” Then I was sorry. When I took Valerie to the mall to shop I had no idea that they even sold dresses like that. She picked out a bright red skin-tight latex dress. If I could have seen the slit in her pussy I would have sworn that it was painted on. It fit her like a second skin. I had no idea that my...

And Dresses for All

And Dresses for All... By Rosie "This one's from your mother-in-law," my mom says, handing me a neatly wrapped parcel. I kneel down to the Christmas tree and start unwrapping. Clothes, I think, as I feel the soft contents. Suddenly, I spot a flash of purple-toned floral print satin underneath the wrapped paper. As if struck by lightning, I stop. Panicking, I look at my wife. "You told her?" I whisper to her. Janice shrugs dismissingly, as if she had done nothing at all, but...

Deja Vu AscendancyChapter 65 The Best Dress I Have Ever Seen in My Life

Saturday, April 16, 2005 (Continued) We saw Cindy's car arrive as close to 7pm as made no difference, making me suspect that Julia had been specific in her instructions. Cindy walked up the path carrying something fairly large and reflective, although I couldn't see much of it. I opened the door as she neared it, and she walked right in. The mystery of the object was quickly solved. It was my HUGE first place trophy. The damned thing was big enough to mount in the front yard with a...

The Irresistible Dress

The Irresistible Dress I just wanted some new jeans but I couldn't resist the dress. I entered the store as soon as it opened. In fact I had been waiting in the parking lot and watching for the woman to unlock the door and open the store. I knew entering this early helped to ensure I would be the only customer so I could try on the boot cut jeans I wanted to buy. I said hello to the saleswoman and quickly wandered over to the jeans section but as I did I noticed a rack of new...

My Little Black Dress

My Little Black Dress ethan susan Janet L. Stickney [email protected] I had gone out to pick up a few items I needed, like pantyhose and new eye shadow, just another fear filled adventure into the outer world. I always felt edgy buying those things that guys didn't usually buy, so I had gotten dressed and bravely went out once again to buy the few things I needed, before I scurried home. I had yet to have anyone figure out that I wasn't a girl, or, at the very least, if they...

The Yellow Dress

The Yellow Dress by Pamela [email protected] After my mom and dad divorced, a couple of years later my mom married a pretty nice guy named Phil who has a son, Ted, and a daughter, Kate, from his previous marriage. Phil has custody of his kids only during the summer so as soon as school let out in early June, Ted and Kate flew to our town and moved into our house. I had only met Ted and Kate once before which was six months earlier at my mom's wedding and I thought they...

The Son Dress Part Two

Lisa pulled up to the stoplight and glanced over at her stepson plucking at the hem of his dress. The red sun dress with the white polka-dots had ridden up when he sat down in the car, and exposed his nylon covered knees and the bright red net crinoline beneath the skirt. "Don't fidget so, Frankie," Lisa cautioned. "You can smooth out your dress when we get to the mall and you get out of the car. The crinoline rides up when you sit down. Actually, it's very cute like that...

Tricked into wearing a dress pt2

'She's fantastic,' Tina smiled enthusiastically, 'devastatingly attractive.''Maybe but doesn't he look a complete sissy?' adds Julia.'Precisely and I do believe,' Mary says triumphantly, 'our new girl enjoys being a sissy.'The girls all nod and the room is filled with dramatic oohs and arhs as they point out favourite bits to each other. Tina loved my hair, Julia my legs, Jill my tits and Mary my dress. Me I loved everything. Even my old bubble-gum pink bike, my initial source of ridicule had...

Max the dress and me

Max, the dress and me Janet L. Stickney [email protected] As the wind toyed with the hem of my dress I stood there basking in the glory with the mere fact that I had done it. I had actually gotten dressed, left the house, and walked to the lake. I stood there a moment longer, then walked down the beach to the boat ramp, turned around and walked back home. I was so excited when I was back home that I could barely stand it, and once again coated my lips with the red lipstick. The...

Max the Dress and Me

Max, the dress and me Janet L. Stickney [email protected] As the wind toyed with the hem of my dress I stood there basking in the glory with the mere fact that I had done it. I had actually gotten dressed, left the house, and walked to the lake. I stood there a moment longer, then walked down the beach to the boat ramp, turned around and walked back home. I was so excited when I was back home that I could barely stand it, and once again coated my lips with the red lipstick. The...

Dress for success

I lost my job and couldn't find another straight away. We realised that we couldn't keep up the mortgage payments and had to put the house up for sale. Fortunately, it sold quickly and we moved into my mother-in- law's house. Did I say FORTUNATELY? I don't think my wife's mother ever really approved of me and was never slow to criticise. However she had a large enough house and had never remarried after my father-in-law died. My wife Helen got a part-time secretarial post, so at least...

The Perfect Dress

She walked past the shop again, the one she often browsed the vintage clothes through the window of but never went in because it never seemed open and had never displayed its hours. She stopped again. That dress. It was perfect. If only she could try it on but looking at the door...she almost gasped. The sign turned to open. At long last.She pushed the door open to the jangle of bells above her head and stepped timidly inside letting the door go and jumping as it closed more heavily than she...

Lesbian

Samantha s Dress FittingChapter 1

I was trying to save money, so I didn't have cable. However there was a basketball game on that I wanted to watch and my friends James and Mandy did have cable. I had gone to high school with James, and he had married a woman with a daughter a few years ago. I stopped by often, so I went over to their house to watch the game there. Midway through the first half, Mandy came downstairs holding a dress. "Samantha! Come try this dress on. I'm going to be out of town on a business trip right...

A Frilly White Dress for John

The Adventures of Joanna and John ? by: Joanna Maguire. This is a true story first starting when I was about 8 years old I can remember most of the incident clearly. Years later when my mother passed on, amongst her things was a black and white photograph of myself in a white frilly dress with the girl called Ann who was dressed similarly, both of us holding dolls in a garden setting. I do not remember the photograph being taken. But my father was always taking pictures with his...

The Yellow Dress

The Yellow Dress More crossdressing adventures at the hands of Ann and her girlfriend, Susie. Jennifer wears a new yellow dress to a casino. Will luck be a lady tonight? By now, you've probably heard of my situation. My name is Jennifer -- at least, that's my name when I'm crossdressed. After my wife found a dress I secretly had purchased for myself, she put me on a course of crossdressing at her beck and call and, most embarrassingly, at the whim of her girlfriend and my...

The Dress Code Sassy Secretary Gets Hers

My name is Vanessa Tan and I work as a secretary for an engineering company that employs about five hundred or so personnel. Specifically I work as the departmental secretary for Sales Support where I make travel arrangements, organise meetings and contractual conferences for about thirty senior engineers, managers and a director. We are the face of the company, and as such, there is a dress code we must adhere to. Last Week - The New Dress Code Office personnel are required to dress formally...

The Silver Dress

There was no way I could afford anything at the store, not even for Lisa. Money was tight, and our planned night at the club was our first treat in a long time, so splurging even more was a bad idea. Still, I'd just received a raise at work, and I wanted to celebrate with something a little extra. A sexy outfit would make her feel great and give me something fun to look at. Pity everything was so expensive. How could so little fabric cost so much? I'd was about ready to give up and try...

Damsel In Dis Dress

Damsel In Dis-Dress I was finally packed and ready to head home. I finished my last exam a few days ago so my summer was starting now. My name is Sam and I am a 19 year old college student. I just finished my second year at college. I was heading home, it was about a five hour drive, but luckily my friend Kimberly was coming with me. She lived a few hours away from me, but I was going to drive her to my place where she would stay for a few days then her parents would pick her up...

Little Black Dress Part 1

There might have been a more delicious way to wake up, but to that Aaron Debeney had yet to be introduced. The sucking started in his dreams, slow, wet and rhythmic. Gradually his mind unwrapped itself from swathes of sleep. Fully conscious he found himself bone-hard and the sensation ongoing. Apparently the weekend had arrived.Peering under the duvet he saw a familiar platinum-blonde head bobbing industriously. He could not help but admire the architecture of his own manhood, as those pink...

Reluctance

The Wedding Dress Club

The Wedding Dress Club When I met Sean, I was convinced I'd found the perfect man. And as he recited his vows to me on our wedding day, I felt like the luckiest girl in the world. I was marrying a man who was promising to care for me and love me unconditionally for the rest of our lives. He told me he adored more than any other woman in the whole world. Things were great for the first few years, I loved being married and we had a lot of fun together. Our friends would comment on how...

The Punishment Dress

Claire was walking home from school feeling sad. She used to enjoy school but had been struggling since her mum died 3 months ago. Her school grades had become worse and she was glad that it was now a week's holiday so that she could spend time with her father.But her father was making other plans. He watched his beautiful 16 year old daughter as she walked through the front gate. He had plans for this beautiful brunette who was was a bit of a brat. Of course she was grieving for her mother but...

4th Dimension Men in Dresses

4th Dimension: Men In Dresses By Busko John is a bodybuilder. All that is male in society is common to him. John is more Rambo than Sylvester Stalone will ever be. Heavily built by his 5 days a week at the gym he is a hunk to all the girls. They all want to date him. John however is very shy, everybody thinks. John has a secret. He loves to wear female underwear. He would even wear dresses if he could, but western society 'prohibits' men to dress the way they want. Women can...

The Dress

The Dress It was shortly after the 38th birthday of Kevin Gordon that the clouds of depression came rolling in. He was a funk. There was no other way to describe it. He took to lying in bed on weekday mornings instead of playing tennis. He stayed home at night rather than go to the movies. He didn't joke much, didn't talk much. Except for his wife, Tina, he was a hermit, keeping the outside world at an arm's distance. Tina worried. She asked him what was wrong a dozen times a day....

The Cabin Scenario 1 the Nightdress

It’s late when we arrive and pitch dark, deep in the forest. We round a bend of the dirt track and the headlights give you your first view of my cabin. Except, when I look round, you’re asleep. ‘Julie, ‘ I whisper in your ear. ‘We’re here.’ You open your drowsy eyes and smile. ‘Mmm, I like it Grandad. Can I explore?’ ‘Sure, honey. Here’s the key. You go ahead while I get the bags out of the boot.’ By the time I enter, you’ve found the bed. ‘This your bed, Grandad?’ You bounce on it. ‘I love...

First Swing Party in a Prom Dress

Cindy and Dennis stand outside the large mansion that has a swinger's party tonight. Dennis had called yesterday and got an enthusiastic invitation. Cindy was a cute blonde 18 year old recent high school grad. She is wearing her beautiful pink prom gown that barely holds in her full breasts and shows off her slim figure and firm small ass. Dennis told her to dress very nicely and Cindy had learned the hard way not to say no to Dennis. He had spanked her sweet ass until it was beet red when she...

Dress like your daughter day

Dress like your daughter day: It started when my oldest daughter, Claire, was sent home from school. It turned out that despite the fact that I had told both my daughters what I expected of them which was that they dress modestly when they went to school and that they not wear the kind of make-up that Claire had started to wear or that they not wear miniskirts to school, Claire had started to do just that. Furthermore I didn't know about this because they either left for...

Dress Rehearsal

Dress Rehearsal By Sue-Lyn Burton Copyright 2000 For six weeks now Jack had been working for the local theatre company, rewiring the building. He did it as a favour to his neighbour, Jenny, who flashed her pretty blue eyes and Jack agreed to give his labour free of charge to get the building safe enough to meet the local fire codes. Over the weeks Jack worked for a local builder during the day and in the evening he went to the theatre and worked till about 11.30pm. He was...

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