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Cocktail Party at Bill Michelles

Introduction: Encounter With Wifes Boss and His Wife I had known about Sues office escapades for several months now and still kept it a secret. I had seen Bill and Michelle several times and no one acted strange in any way, although I secretly had a massive desire to have sex with Michelle. We were invited to a cocktail party at Bill and Michelles house, with some of their friends and neighbors. Sue was the only person from the office invited and the party was a semi-formal get together that...

Cocktail Party Groping

Bree is invited to a cocktail party by some friends of friends of mine. The party is at the Dallas Country Club. There were between forty and fifty guests, which barely made a dent in all the space they had available in the ball room. She is wearing a mid-length fairly low cut black cocktail dress. As usual, that is all she is wearing. The dress had darts in the front so there is some support for her breasts. It is obvious to everybody that she wasn't wearing a bra. On a few occasions she...

Cocktail Party

consutant in Washington D.C.. I was attending the cocktail party along with other political people and business executives. Karen put on her skin color thigh highs and garter belt. She had always preferred them over regular panty hose so that She wouldn't have to worry about tugging on them late into the evening. She threw over a sheer pink blouse that moved with her body and pulled up a gray pencil skirt that hugged her hips. And nice black heels to top it off. I put on my gray slacks...

Cocktail Party Wife

John's friend Jane Doe and her husband Jack Doe decided that they fancied having a cocktail party where they and all their friends could get dressed up to celebrate and have a proper party before everyone started getting pregnant or moving from their hometown. There was a few married couples there and my Ex-Girlfriend Jessica and a few other stragglers. Everyone knew everyone else as we'd all been either friends for years or had been at school with each other. Jane was a hottie who I had wanted...

Cocktails with Katy

We had been living in our new house for over a year and had gotten to know our various neighbours pretty well. It was a new development on the outskirts of our city so we had all moved into our houses at roughly the same time, giving us all something in common when initially engaging in small talk. We lived at the end of a small row backing on to the embankment separating the houses from the motorway. Our rear gardens were all separated by fences which were six-feet high at the house end,...

Cocktail Anyone

It was a business trip and tonight was your typical cocktail dinner reception, people floating around pretending to network with people that they know they will never contact or speak to again in order to be cordial. It was during that “networking”, we met. At the time I thought nothing of us meeting and chatting. I didn’t even have one lustful thought or any inkling of an idea that this six foot tall, dark haired hunk was going to be more than a cordial hello, not until the evening ended that...

Cocktail Pool Orgy

On Saturday morning, Janet announced that she’d invited her sister, Rosemary, and Rosemary’s boyfriend over for an alfresco lunch. We went to the market in the morning and bought fresh bread, cheese and cold meats, as well as a plentiful supply of local wine; very cheap and very good, as I’d already discovered. The local beer was mostly gassy and expensive, but the wine was better even than the varieties I’d drunk in the UK. Like the Australians, the South Africans had clearly learnt the trick...

Cocktail Pool Orgy

On Saturday morning, Janet announced that she’d invited her sister, Rosemary, and Rosemary’s boyfriend over for an alfresco lunch. We went to the market in the morning and bought fresh bread, cheese and cold meats, as well as a plentiful supply of local wine; very cheap and very good, as I’d already discovered. The local beer was mostly gassy and expensive, but the wine was better even than the varieties I’d drunk in the UK. Like the Australians, the South Africans had clearly learnt the trick...

Cocktail Anyone

It was a business trip and tonight was your typical cocktail dinner reception, people floating around pretending to network with people that they know they will never contact or speak to again in order to be cordial. It was during that “networking”, we met. At the time I thought nothing of us meeting and chatting. I didn’t even have one lustful thought or any inkling of an idea that this six foot tall, dark haired hunk was going to be more than a cordial hello, not until the evening ended that...

The Dressmaker

THE DRESSMAKER By Lisa Lovelace I had utterly the most horrid crisis in my boudoir on Wednesday morning. Phineas and I had responded s'il vous pla?t to a Thursday night soiree at the Gardners' on Chestnut Street, on the coveted south slope of Beacon Hill. It was the grandest house to which we had yet been invited - and the gorgeous new gown that I planned to wear lay in ruins. It was two-layered floor-length tulle over light gold taffeta, embroidered with purple and plum flowers. The ...

Cocktails

At the age of twenty-five, I had firmly committed myself to a solitary existence. I felt that I really didn’t need the encumbrance of a partner who would complicate my life in any way of form. To me, visiting my local bar for sexual gratification was completely satisfactory, and the glory hole section, in particular, totally took care of my carnal needs.If I may explain: Sucking anonymous dick and swallowing spunk was all I needed in life and any further impediments, left me stone-cold. Okay,...

Cocktails at Candy Pass

Jane Anderson put the teapot on the stove. “What you need is a proper drink!” she said out loud. In her living room; a few feet away, sat her sister-in-law, Sybil; upset because she’d discovered her husband Jake was cheating on her! Jake sure was a handsome hunk, given half a chance Jane mused... Jane went over to the cabinet and took out a bottle of brandy. She supposed she ought to be a little more sympathetic, because her own husband Eddy was Sybil’s brother! Jane was tall and buxom, her...

The Scarlet Witch Versus The Hairdresser

Chapter 1. Recap and Introduction In her first encounter with the infamous follicle felon, the Hairdresser, the mutant heroine known as the Scarlet Witch, and commonly simply referred to as Scarlet though Wanda was her Christian name, had been lured into his diabolical styling salon under the premise of a beauty make over and hair coiffure. However, instead of a relaxing hair appointment to enhance her already natural beauty and provide a boost to her self-esteem, the Scarlet Witch had only...

Cocktail Party Surprise

I stand by the door. Hesitant, she walks in. Heather walks through the room as I remain watching. Her arms crossed, her hand covering her mouth as I smile and watch. As she slowly walks along the room, I watch the red dress she is wearing swish across her ass as she walks, I can't help it. Heather walks behind the couch and runs her hand gently across the pillows, her fingers caressing the fringe as she goes. I want those fingers running down my arms, over my chest, through my hair. I offer to...

Cocktail Waitress Wanted

The place was essentially a rip-off of Hooters. The waitresses wore short shorts or mini skirts and tank tops tied in a knot around their midriff. We classified the waitresses as models and paid them more than standard waitresses to enable us to select only attractive girls and not worry about a lawsuit from some fat ass with a bad attitude. The first interviews were pretty much what you might expect, girls in their early 20’s that were looking to make a few more dollars than working...

Cocktail the first sip

Lisa tossed and turned one last time and then she gave up the idea of going back to sleep. She ran her fingers through her hair, thinking about whether to hit the shower or make some coffee first. She finally made a high bun and sat up on the bed to head to the kitchen, and that’s when she saw Bob sitting on the couch and staring with a piercing gaze set onto her face. She sauntered slowly to him, picked him up in her lap and caresses the furry arched back to hear a reassuring purr and a mew....

Cocktail

Late into the summer evening the steel bands were still in full song. You could hear them even above the hubble-bubble of Frank's patrons. Anyway, the doors and windows were open. It was steaming, man.Our eyes met across the tables. Guys came to Frank's Bar to find other guys and hopefully get laid. He was a lager drinker, a good sign. I was on iced cider, the latest craze. He was coloured, probably Caribbean. This part of London had its share, especially on carnival day.When he went to get a...

Cocktail Table

A few weeks ago, I received an Email from a young man who was a graduate student at a University in a city a few hours from where I live. He said that he is an avid fan of my stories that are posted in alt.sex.stories. He and his girlfriend read them all. In fact, they have been sharing them with a group of friends at the University. This isn't just any group of friends-they are a sort of club that engages in mate-swapping and group sex. There are twelve of them all together, all couples. So...

Chapter 5 Playing with a New Friend While Dresse

While my friend Jim was pretty much my best buddy, I never tried to involve him in my panty play. I didn’t believe he would go for it, and I was afraid to suggest it to him for fear I would lose his friendship and become the object of his ridicule.I did meet another boy my age, and I discovered he shared my passion for nylon. His name was Dale. He also had a mature woman fan the flames of his passion. It was his mother, but, as he told me, she merely facilitated his enjoyment of her...

First Time With Crossdressers

For once, I actually decided to look at some of the other categories on the streaming sites I'd visit. So many things came up under fetish. Some of it I don't get but to each their own. A BBW was mixed in with the fetish and as I had expected before hand, it wasn't my cup of tea. Several videos had girls dominating guys in leather or latex outfits. I liked how tight they were, showing off every curve of their body, leaving little to the imagination. Upon thought, I had never been...

Chronicles With Sexy Crossdressers

My email id is Do not forget to let me know how this sex story was. Who knows, we might get even lucky if everything goes well ;) Clean shaved men inside female clothes (or people who are known by the name crossdressers) are my new found favorites. Believe me, I always make it a point to taste every bit of them with passion and fire. My hands and tongue never leave an inch of their body. Hairless, like women and the ‘EXTRA’ jackpot called ‘COCK’, is simply divine. This is a story of how a...

Playing Dressup

My parents have a library. I was a very lucky girl growing up, not because of the collection of classics that they had in leather bound editions, or even the enormous number of new books that they seemed to add constantly from visits to the book store or from various book clubs that they belonged to. I liked a lot of those, but my favorite books in their collection weren’t actually on the shelves in the spare room that we used as a library, they were in dusty boxes stacked in the garage and...

In her Dressingroom

With a make-up wipe I took the orange glaze, the white glitter and the sweat of my face. It was always such a satisfying moment. After the show was done, my muscles sore, I would take off the sweaty costume of the Sugarplum fairy, but before I jumped into the shower of my private dressing room I first took the make-up off my face. Seeing the Sugarplum fairy disappear and my own face reappear. A moment of self care. A moment off calm, no sounds, no music, just the soft rumbling of the...

Cuckoldress

The Jamaican culture is rife with cuckold stories, white women bored with their husbands taking advantage of numerous available lovers to satisfy their needs. I went to school with the product of many such unions. Later as I matured sexually, I listened as the old bulls told of interesting liaisons, with the tourist women, who frequented our idyllic island looking for the same. So it was one night a bunch of us young ‘Turks’ were hanging out scoping the women hoping to get lucky before the...

Babs dresss

My father used to look after and maintain the garden of a local business man who had a large mansion, and at times I would go with him to cut some flowers for the lady of the house to decorate the lounge and other rooms . She would show me how to do flower arranging using the flowers and ferns, she was always very nice and pleasant with me because they had no c***dren of their own, and would at times she would ask me to tea after school. I always agreed because my parents were always arguing,...

Filipa becomes a cuckoldress

Filipa had been annoyed by her boyfriend Mark for sometime now about getting into cuckolding . She had resisted the idea of dating and sleeping with other men because of her religious upbringing but recently she had become more comfortable with the idea.She had been chatting with several guys online and was starting to feel a connection with one in particular "Derek" .He had been trying to persuade her to meet him for a drink. he was tall 6,2 to be exact with a muscular ripped body and a great...

Black BBW Cuckoldress

I meant Janine on live links. Actually I was drunk when I called the line. Just hoping to talk a woman while I jacked my little pink dicklet. In my introduction I mentioned that I was into cuckolding, and SPH, and that I had preference for BBW's. This was in the Detroit area so most of the ladies on the line were African-American. Her ad stated that she liked to have her asshole licked, and was looking for a long term relationship where she could really control the person she was with. At the...

The Irish Cuckoldress

"I finally got a date with her!", I shout loudly as I walk home. Of course the people around me have no idea who or what I am talking about, nor do they care. Her name is Claire and is an absolute Goddess. https://es.xhamster.com/photos/gallery/4582166/104421822She is 6 feet tall, blonde, big titts, long legs, and a body that a porn star only has. She is beyond beautiful and pretty. I have tried for months to get a date with this amazing wonder like woman but have always been rejected due to...

Marrying a cuckodress

So it's my wedding day, i look at my future husband as i walk down the aisle and see his smile, then i look at his best man and wonder if i'm rally doing the right thing getting married. It wasn't that Alex wasn't a nice guy, he totally was and he was the sweetest guy i'd ever met, but i was just used to being with dickheads, a lot of dickheads , and didn't know if someone like Alex could handle a woman like me. I knew he was very inexperienced, although we hadn't actually done anything much...

cuckoldress

Today my very lucky & equally pathetic cuck bitch hand delivered me a £500.00 cash tribute along with a bottle of champagne, some vodka, flowers & cocktail shaker..he thought he was just dropping them off & meeting my bf in preparation for our big joint session in a couple of weeks..nothing could of prepared slut for what I had in store for him....Here in his words is part one..After a near sleepless night thinking about the day to come it was with eagerness and trepidation I set...

Black Cuckoldress

I met Shanice at work three years ago. We worked for a manufacturing company, I worked in the plant and she worked in the lab. It was at the company Christmas party that we really had a chance to talk. I had such a great time with her at the party that I decided to ask her out. Things progressed from there and soon we were dating on a regular basis. I can still remember the first time we had sex. Shanice is a beautiful, athletic black woman. I had never seen a naked black woman up close before...

Babs dresss

My father used to look after and maintain the garden of a local business man who had a large mansion, and at times I would go with him to cut some flowers for the lady of the house to decorate the lounge and other rooms . She would show me how to do flower arranging using the flowers and ferns, she was always very nice and pleasant with me because they had no c***dren of their own, and would at times she would ask me to tea after school. I always agreed because my parents were always arguing,...

Military School Crosdresser

MILITARY SCHOOL CROSSDRESSER By Kresha Matay PART 1 Tim was a sensitive young boy, bright and intelligent, but lacking many of the physical characteristics of Joe, his father. The father had wanted a son who was interested in sports, hunting and fishing just like himself. Unfortunately, through no fault of his own, young Tim couldn't measure up to the desired image. Joe had expected his son to grow up to "be a chip off the old block" and when he didn't, his father felt...

Mommy s Darling 2 Playing Dressup

Mommy's Darling 2: Playing Dress Up - By Billie Lovelace At twelve, I was deeply conflicted. On the one hand, I was a normal boy. At school I liked sports, roughhousing, and teasing girls. On the other hand, mother hated masculine aggressiveness. So at home I was more girlish. I played the piano, did housework, and spent hours with mother -- brushing her hair, polishing her nails, and helping her in and out of her high heels. It was so confusing. I wanted to be like other boys....

1 900 DRESSUP

1-900-DRESSUP By Ricky I'm sure that you have seen an ad or two (or twenty) for one of those 900 phone services. They usually have neat names like 1-900-HOT-HOTT, which is a real number that a teenage neighbor called twice on my garage phone before I caught him. If I ever could understand why someone would pay $25 for the first four minutes of talk when for a smaller monetary investment you could go to a bar somewhere and buy some floozy a few drinks and get the talk live, or...

Sidedressing

Sidedressing By Tyrone Slothrop Older sisters can be a boy's good friend and most effective torturer. Bernadette, charged with watching her little brother, was getting bored and decided to see how far she could manipulate him. Nothing nasty just keeping her hand in. Practice makes perfect. "Ralphie, come here, I want to try a new game." Ralph heard his sister and put down his videogame. He wandered into her room. At thirteen he was fairly average in height, about five feet...

Babs dresss

My father used to look after and maintain the garden of a local business man who had a large mansion, and at times I would go with him to cut some flowers for the lady of the house to decorate the lounge and other rooms . She would show me how to do flower arranging using the flowers and ferns, she was always very nice and pleasant with me because they had no c***dren of their own, and would at times she would ask me to tea after school. I always agreed because my parents were always arguing,...

Playing Dressup

My parents have a library. I was a very lucky girl growing up, not because of the collection of classics that they had in leather bound editions, or even the enormous number of new books that they seemed to add constantly from visits to the book store or from various book clubs that they belonged to. I liked a lot of those, but my favorite books in their collection weren't actually on the shelves in the spare room that we used as a library, they were in dusty boxes stacked in the garage and...

Confessions of a Cuckoldress

Confessions of a CuckoldressHi! I’m Melissa. I’m just a regular gal that has a very active sex drive. I found a great solution to the age old problem white women have had since the beginning of time and this is my story about how I found this solution.We white gals love our white boys. They are great for cuddling, doing housework, showering us with affection and of course worshipping us. The problem with white boys is their little dicks! What is a girl to do when she is in love with a white boy...

Cuckoldress

The Jamaican culture is rife with cuckold stories; white women bored with their husbands taking advantage of numerous available lovers to satisfy their needs. I went to school with the product of many such unions.Later as I matured sexually, I listened as the old bulls told of interesting liaisons, with the tourist women, who frequented our idyllic island looking for the same.So it was one night a bunch of us young "Turks" were hanging out scoping the women hoping to get lucky before the night...

Custom Cuckoldress

Tonight's the night. My boyfriend has been insistent that I try to fuck another man. I've been hesitant because it seems so bizarre, but, ultimately if we do it safely, I guess once can't hurt, right? We've had a few group dates with an African American man named Markus, and decided he'll be the one. I'm fairly anxious, I've never been with anyone other than my boyfriend. I've been trying to keep my head on my shoulders. We arrive to the hotel. Underneath my clothes I'm wearing some dangerous...

Confession and testament of a crossdresser

Italy, september 2011. Sorry for bad english, I try to write correctly but don't know if I did. From tonight, I was a crossdresser. I'm been crossdresser from 12 to one day before my 27th birthday. Irony. I begin to have an answer to the question: "What feel girl?" Yes, a simple question. What feel girl when wear panty, tights, dress, skirt? What feel a woman in heels, purse, with her hair falling down the shoulder? What feel a teenage when begin to make up herself? When wear lipstick,...

My Qualifications to Write About Crossdressing

My Qualifications to Write About Crossdressing By Ricky How ironic! While looking for something in my files the other day I found I have been writing about crossdressing more than 10 years now. The problem is, I now realize I am completely unqualified to be a crossdresser, let alone a writer on the subject. Think about it, just what are the qualifications for a crossdresser? Surely you've read a multitude of "true life stories" in the crossdressing magazines. Perhaps if we...

outside the hairdressers

My wife had gone to the hairdressers, I was sat round the corner in the car waiting for her, it was opposite the employment office, where all the screbs go to get money off the state, it was a run down area but I never felt unsafe, as I was sat there I reached for a cigarette, as I opened the packet a girl was next to the car, she said "Do you have a spare cigaretts", I said "Maybe".She was around 20, long brown hair, slightly chubby, wearing a trakkie bottom and a white top. She said "I really...

Fantasy I have with my hairdresser

My name is Gary and I’m married and I’ve had this thing about a hair dresser I use to visit. Her name is Deena and she’s twenty years younger than me. I haven’t had Deena cut my hair in a couple of years and missed her. So I called her for an appointment as I was thinking about her recently. “Hi Gary, it’s been a while,” she said answering the call. “I know. I’ve been extremely busy with work.” “What can I do for you?” All...

The hairdresser

The place I used to work at last yr had a hairdresser that came in on a regular basis to do the older ladies hair , I noticed her from the word go as she was such a sexy little thing, about 5” 1 and blonde with a sweet little figure and a lovely set off boobs, a little older than I was but at the time I didn’t know by how much, over a few weeks and a little small talk I asked her if she would like to have dinner, and with a little persuasion from a colleague she agreed, I made dinner and we had...

Lockdown Hairdresser

Like most self-employed people Becky was struggling as a hairdresser during lockdown. No clients meant no money, but the bills didn’t seem to stop. She’d already resorted to cancelling every subscription she had and had even sold her TV on eBay. But she was still short of cash. At twenty-six years old and living the single life she had no one to help with the bills.Out of desperation she’d texted one of her clients to see if he needed a haircut and didn’t mind breaking the lockdown rules to...

Milwaukee Cuckold rsquo s Wife and the Crossdresser

Judy used several sites over the years to find her friends with benefits. She never tells me until afterwards what she has done. It’s rare she tells me anything in advance. One day she advised me the k**s were at my parents and she was entertaining that night and I would have to stay in the family room. My curiosity was getting the better of me.She went and took a shower and asked me to come in and shave her pussy. She had me paint her fingernails and toenails. Once she was ready she put on her...

Teenage crossdresser

Here are the usual disclaimers this story is for adults only if you are viewing this andare not 18 years of age or older please close this page immediatly.There is no cross dressing in the story but this is how I began my transformation fromregular boy into cock suckking teenage crossdresser.We were having a really hot heat wave. i meat with my older brother (wear red shorts, and a black T-shirt) wanted me to get out of the house and off the computer so she suggested a movie. I felt wierd going...

Amazing Night With A Sexy Crossdresser

Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one. I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and...

An Introduction to Crossdressing

Up until this point in time my crossdressing has consisted of wearing stockings or pantyhose and enjoying some anal penetration with one of my toys. I have recently had strong desires to move further but really didn’t know anyone that could help me. I was chatting recently with one of my friends on Lush about our mutual desires and needs. I had said that I really would like to do the whole deal at least one time to see if I’m really as into it as I thought I was. I also mentioned that it wasn’t...

Hypnotized Into Wearing Dresses

"Hypnotized Into Wearing Dresses" By Alana Gloria knocked on the door of the dressing room, and Dr. Specks invited her in. He sat at his dressing table getting ready for his stage show. "Can I help you?" he asked. "I'm Gloria Stoner. I understand you were once able to hypnotize a man into wearing dresses. You got him so he experienced severe stomach cramps if he didn't dress like a woman. Is that correct?" Dr. Specks motioned Gloria into a chair, and said, "That was...

Wet Dreams to Crossdressing

Confessions of a Crossdresser I am a crossdresser. It is an addiction. I’ve tried, but I really can’t stop myself: fantasies, endless looking at pornography, shopping, dressing, masturbation, and inevitably, seeking men to please. I started out as a young teen as a panty fantasizer and have progressed to where I am today. I think that I am pretty “normal”: dating girls, and now a responsible man, married with a f****y. But, I have evolved to a cock sucking crossdresser. I’m writing to try to...

An Introduction To My Crossdressing

Many of the crossdressing life stories I've read on Lush have similar beginnings. The early adolescence, the mother's or sister's clothes, the masturbation! It's fifty years since my first urge to dress in feminine garments, and ever since then, it has been an integral part of my colourful life.I remember the day fairly vividly. I was settling down in our bathroom, to do what EVERY adolescent does at that age. Wank! My inspiration back in those days were my mum's pals, her sister, and a couple...

The Hairdresser

He walked into the New Horizons Hair Salon. It was a unisex salon but the majority of the clientele were female, mostly middle aged and upper class. He had stumbled upon this place when in desperate need of a haircut some two years ago. He was to be the best man at a wedding at the time and thought he ought to make more of an effort with his grooming.He had been shown to a seat by Paula, a tall brunette. She was late twenties and very attractive. Long hair held back in a ponytail, beautiful...

The hairdresser

This happened in 2010Donna used the same hairdresser for over ten years. She was an Indian girl, really pretty and only recently married. She's called Gina, 30 years old, 5'5", thin with dark hair and extremely pretty. As Donna wanted her hair doing for a party we were going to Gina offered to open her shop late so she could have her hair done the same evening.Friday came round quickly, as I dropped Donna off at 6pm, the town was quiet and there was no-one in the salon, I told her I'd be back...

Girlfriend s Hairdresser

“Look, honey,” proclaimed Kamron as he held a mirror in front of his client.“I like it,” she declared with a smile. “How much,” she asked.“Fifty-five,” the five-foot-nine-inch big booty effeminate hairdresser replied.“Alright,” she said digging through her purse. “Oh damn. I left my billfold in my other purse. Do you mind if I get Tavares to drop it off when he gets off work,” she inquired referring to her live-in boyfriend that worked at the auto parts factory in town.“Yeah, chile. That’s...

Night Trawling The Crossdresser

The streets of Pomona live two lives. Like maternal twins, they coexist in parallel, appearing as virtually identical to those merely passing through its old and storied neighborhoods. During the day, with the sun high overhead, myriads of people — whether they’re commuters traveling like drones or soccer moms distracted by their busy lives — they choke the streets in a constant pulse of life. Each person is absorbed by their own petty concerns, each oblivious to what is happening on the...

my life as a sissy crossdresser

it should be noted that i did not ask for this disposition to crossdress, rather it was presented to me quite by accident. circa 1958...grade school PTA fashion show. PTA fathers were asked to put on a fashion show dressed as their better halves. my dad was right in the mix. I remember he wore some mid calf, grey business suit w/jacket, tan stockings and black heels. i remember this because he practiced dressing days before the show. he wore some makeup and a wig. not very passable, but not...

Hitchhiking teen crossdresser

It was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter, I had my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to...

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...

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...

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...

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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...

Wedding Dresses

My name is Jason. I am 24 years old and work as an apprentice with a pretty good photographer called William. As well as his normal weddings and portraits, William does photo shoots for clothing and product brochures, and other similar projects. William charges a lot of money for the brochure shoots but offers the guarantee that if his work is not to the customers liking he will retake the pictures for free. I have worked with William for nearly 3 years and so far he has never had an...

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...

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 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...

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...

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...

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,...

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? ...

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...

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 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...

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...

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...

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...

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...

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...

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...

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