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Crossdresser s Surprise

A Crossdresser' s Surprise - by: by Deborah Pinto I guess I should have seen it coming. My wife, Virginia, and I were drifting apart sexually, and I should have suspected that she was having an affair. Afterall, we had not made love in over a year except for one night she had come home a little drunk from her office Christmas party and had virtually raped me in the middle of the night. I remember her laughing and saying, "Tim, what's wrong with you tonight? You feel so tiny inside...

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...

Crossdresser s Placement Agency

I know it's a little dated, but read it anyway. Crossdresser's Placement Agency By Ricky With apologies to those of you who weren't around to listen to radio in the sixties, I'll start this with a famous quote. In the immortal words of the Chicken Man: "They're everywhere, they're everywhere." Crossdressers, that is. In the last week everywhere I look I see a crossdresser, right out there in public. First there was the color coordinated Dennis Rodman with green hair and...

The Crossdresser s Quiz

The Crossdresser's Quiz By Ricky I have recently been educated. After all these years of simply wearing frilly clothes and thinking them feminine I have finally found out the secret of how to be a real woman. And all because my car is a clunker that just passed 100,000 miles... It happened this way. As soon as the odometer turned over, every time I got in the car something else major broke down. Within 3 weeks I replaced the rear main seal, the fuel injectors, water pump,...

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...

A Crossdresser s Night in the Park

A Crossdresser's Night in the Park cd, bdsm, con, mm, anal, oral, toy Last night I was on line in a crossdresser chat room where I was talking with Master Brian about me being a pain loving, submissive, bisexual crossdresser who was looking a master to use and abuse me. As we talked Master Brian asked me if I was dressed as a woman while I was on line with him. I told him that I was and then he asked me what I was wearing. I told him that I was all dressed up wearing a black silk...

Crossdresser s Paradise

Crossdresser's Paradise By RogerGirl Charles had just returned from his summer trip with Stan and Desiree. It was a rare time of year since both his parents were home at their main mansion. Charles was feeling nervous, but felt he had to finally tell his parents about Charlene, his feminine side, and that he was bisexual. He walked into the kitchen where his parents were eating lunch. His father, Simon, came from a long line of wealthy businessmen and had expanded his family's...

The Halloween Crosdressing Mistake

The Halloween Crossdressing Mistake My wife Stacy and I were standing in a room with about 30 other people. The room, was one of those fancy ballrooms that you only find in old universities, or houses that were owned by people with entirely too much money. I mean really, who has the extra money just lying around to build a ballroom!? You can use these things what, four times a year if you are lucky? Well, I digress. So we are standing there in this ballroom, at what is...

A Cross Dresser s Revenge

CROSS DRESSERS REVENGE BY JANICE I was fifteen years old when I was beaten up and raped by three big adults. I was on my way home from Martial Arts school when it happened. I was pretty good, tops in my class, but that was little help to a teen age boy against three big drunks, aside from being beat up, I was also sexually assaulted. The three of them were arrested a few days later but not for what they did to me,...

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...

Dressmaker s Dummy

I was happy now that Kasia and I had moved in together. Not only did it mean that we no longer had to take turns going to each other’s place, but it also meant that I had closer access to a supply of her soiled panties. Kasia was a cute Polish girl, 23 years old, with deep blue eyes, shoulder-length hair trimmed in a cute bob, and a body to die for. We had decided trying to live together to see how we would manage as a couple, with the intent of marrying the following year if all went well. So...

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...

Crossdresser s Spanking Scene

My roommate and I were both bi and part-time cross-dressers. We were also familiar with consensual B & D and had already worked out several code words, then went a step further and wrote scenes for each other, so that when we're in the mood, we could call up the scene rather than try to explain it or coach someone through it. Sometimes we did a scene to please each other sometimes we asked for a scene because we were in a specific mood. So it was that I got an e-mail at work, which...

Grausame Gedanken zur Dressur sch ner fetter Frauen

Betrachtungen ?ber die Dressur sch?ner DamenDiese Fortsetzngs-Geschichte ist ?brigens den Autoren "darkreal" gewidmet, deren sch?ne Geschichte ("Der Million?rsclub") hoffentlich bald eine angemessene Fortsetzng bekommt. Ich bin schon sehr gespannt?Und nun zu den Betrachtungen: Ich wohnte vor einiger Zeit in einer Ein-Raumwohnung im 6. Stock eines gro?en Mietshauses in der kleinen Stadt H. In die gro?e Wohnung direkt nebenan ist vor 2 Wochen eine Frau mir ihrer Tochter eingezogen. Wir Hausbewohner ...

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...

Lisa Lee Xdressing Adventures

I have been crossdressing since I was about 14 and by the time I was 18 or so I was meeting with guys I met online for sex and I loved it! I got married to a hot and sexy lady when I was 23 and I thought that might take care of my tranny urges but in reality it only made it worse. I now have to go long periods between playing dress up and it’s often all I can think of so when I do have the opportunity I tend to get pretty wild, like I did a few weeks ago…. My wife went...

Alice s Very Naughty Adventures Chapter XXII The Dressmaker s Shop

“I hope you enjoyed your nap, Alice.”Alice opened her eyes slowly, yawning as the owl-faced seamstress helped her to sit up.“I had such a strange dream, Mitzy,” she murmured, stretching her arms up above her head before settling her hands upon her lap with a soft sigh. “There was a very rude centaur. And I met a lion and unicorn and I inspired them to go on an adventure. Oh, I do hope it’s a grand one. And then I attended a lavish party at a palace and I was wooed by a handsome Sargeant-Major...

Becoming Xdresser Samantha

My first true experience as Samantha.At the time I was living and working overseas. To the outside world I was just your normal 21 year old really skinny guy living and working and enjoying life on the islands. Of course I had my little secret which I kept hidden from my colleagues and friends. Although I wore panties a lot of the time, I did not own much else as far female attire for fear of being discovered.It happened one evening while I was working in a restaurant doing a photo program for...

A Xdresser with a new Master

Being a cross dresser and serving a Master can sometimes be very rewarding and humiliating at the same time.This is one of those occasions. I had recently met a new Master and was learning the ropes on how to serve and please. I received a message from my Master informing me that he was coming to town and that I was to meet him for breakfast in the restaurant at his hotel at 8am. I was instructed that I was to arrive wearing the black corset with black fishnet stockings and black satin and lace...

Dirty cuckoldress Jayde

When I first arrived abroad and started living with Mandy, my aunt, a few years back, Mandy had a carer coming in the daytime, to help with various things, as my aunt is elderly and disabled. Her carer, Jayde, was GORGEOUS…the best looking woman I personally think is possible;a jaunty little rock chick with long, luxurious hair, and eyes like dark pools, and the prettiest, most atrractive face and figure you could ever find. A few tattoos finished off her exotic little hippy-chick appearance. I...

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...

As a virgin cross dressor wife

Hi. to all. I'm Prabha. I'm a regular visitor of this site. I always think of sharing my experience with all u? And finally thought of writing this.. it is my own experience . On one holiday in September 2008, I am alone in my flat. I am having a feminine body and also a crossdressser. As I am free and no one could contact me for that day, my mind directed to wear ladies garments as per my wish as no one can tease me for wearing cross dress. For me, sari is the most sexiest dress of all, and so...

Jaq Invites Crossdresser Over

Anyone who follows our adventures will know what type of lifestyle we lead.A short while ago Jaq got chatting to a crossdresser online. It turned out that he only lived a short drive from where we live. Kieran was twenty-two, his pictures looked amazing. Jaq asked me if she could invite Kieran to visit, an offer that I could not refuse.All was set for the Friday evening. To say we were excited would be an understatement. Jaq and I showered and dressed. Jaq looked amazing as always in a very...

A Crossdresser Gets Caught

Johnny was gentle and had slightly feminine mannerisms for a guy. He had had quite a few escapades with women, a couple of failed marriages and a dozen or so relationships but all had fizzled out. He had never thought about the fact that maybe he was gay or bisexual and although he was not homophobic he thought the idea was not for him. He found women attractive and loved them wearing sexy lingerie and became almost obsessed with lingerie and all its variations, sometimes even more than the...

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...

Crossdresser for mature couple

I am a bi crossdresser....love some pussy or cock. I registered on an fabswingers looking for a meeting with similar people.I was actively looking for an older couple to have some fun with. To cut a long story short, I finally got talking to a guy called Bill. He and his wife could entertain a gurl like me for a fun filled evening, if I was game. We both had a list of dos and donts for the night and we went over a few ground rules etc.I was to be their maid and waitress for the evening. They...

A Crossdresser s Night in the Park

Last night I was on line in a crossdresser chat room where I was talking with Master Brian about me being a pain loving, submissive, bisexual crossdresser who was looking a master to use and abuse me. As we talked Master Brian asked me if I was dressed as a woman while I was on line with him. I told him that I was and then he asked me what I was wearing. I told him that I was all dressed up wearing a black silk mini skirtwith a black stretchy lace blouse. Master Brian then asked me what I had...

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...

crossdresser s 1st time

hi, im new to this. this happened about 3 years ago now.I had started off the night being at my ex gfs house looking at her sexy underwear thinking how it would feel etc. so, having just started a new job I felt it was time to relax a little while she was out working (from 10pm til 6am). from this simple thought I became massively aroused and started trying on her underwear, make up, and even a wig that was in the apartment. soon enough, I was looking like a slutty crossdresser.I thought enough...

mature crossdresser 18 year old PART 1

Myself being a fulltime crossdresser and wear mini skirt and dresses all the time an high heels. A few weeks ago some new people move in across the street from me to be extact it was a woman and her 18 yr son.I talked to her few times and she was very nice and in our talks asked her if it bother her that i was a cd/tv she said nope. Well after couple weeks we became good friends and found out her son was shy and kind of a nerd. One day she came over to me and was little upset over something she...

Portrait of a Crossdresser as a Young Man

Portrait of a crossdresser as a young man By Sara Keltaine I didn't write this for others but instead as an outlet to release the demons that have haunted me since I was a child. Some might think this story funny, others might think it sad, and the people that think they know me the best would be shocked. I'm writing under a pseudonym that has become my alter ego but I will get into why's of that later. I've been told I was a happy infant and my memories of that time...

The Crossdresser Body Swap Part 1

The Crossdresser Body Swap Chapter 1 Ashleigh finished polishing her toenails with a final dab of red nail paint. She rolled onto her belly whilst letting her feet dangle off the bed to dry. She noticed the time on her phone and let out a sigh of annoyance, her neighbours would be coming around for another dinner night soon. Ashleigh always thought they were a weird bunch, always practicing meditation in their garden, plus their house was littered with all this voodoo and spiritual...

Crossdresser Got Caught By The Neighbor

Hello readers, my name is Rajesh, a 24-year-old guy who likes to dress like a girl. I am in Australia now. This story will tell you how a crossdresser got caught by a neighbor and had to do whatever the neighbor ordered. His name is Roy (name changed), he is 6’1 height with a well-built body, and he is in his late 50’s. I recently had to move to another unit as my old unit’s lease got finished. On a Friday morning, I was leaving for my office. I saw an old man (who lives in the next door unit)...

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...

First time crossdressing with another CD

This is part one of a story, from a former user. I’d like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great. First Time Crossdressing with a mate part 1 This is a work of fiction, though someday I hope to make it a reality. —– It was the height of summer, and my girlfriend was out of town for 2 weeks. I’d had a handful of experiences with guys before, but ever since I...

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...

First time crossdressing with another CD

This is part one of a story, from a former user. I'd like to read the continuation, or anything else written by them. I enjoy the stories as much as the pics and videos, they all get to the right part of me. Any help would be great.First Time Crossdressing with a mate part 1 This is a work of fiction, though someday I hope to make it a reality. ----- It was the height of summer, and my girlfriend was out of town for 2 weeks. I'd had a handful of experiences with guys before, but ever since I...

Friday night crossdressing fun part two

Friday night crossdressing. Doing a favor for a gay neighbor gets me more exposure when a friend finds out I like crossdressing. Continued… Gail walks up to Candice, leans over and they start making out. Before I knew it everyone had a partner and they were all making out except Mark and I. As I said before, Mark and I have known eachother since grade four. I heard he made a pass to another guy once but I thought it was just a rumor. I've always liked crossdressing but didn't consider...

Wedding Anniversary

Introduction: A gangbang, sex sex and more sex Standing in front of the little shop, I take another look at the address. A shiver runs down my back when I look at the note in my hand, and see that this is definitely the right address. I pull my shoulders back, and straighten my back, well, if this is the place Shaun wants me to go, I will go in. The tattoo parlor is not a place I would normally visit, especially on my own. It looks more like something out of the Rocky Horror Picture Show than...

Wedding Tease

Ben had something different on his mind – Jess. He loved seeing her get all dressed up, wearing heels that made her legs look long and shapely, a dress hanging delicately off her shoulders and fluttering around her thighs. She was wearing bright red lipstick outlining the curves of her lips, and eyeshadow that made her eyes look an even deeper brown than normal. He couldn’t get his thoughts off of her. Sitting next to her at this table wasn’t helping things, her leg occasionally brushing...

Wedding Night 0

She stood over me, while stroking my hair, and started to work herself out of her tank top. She kissed me on the cheek, I turned kissing her on the lips. Deborah's hands glided over my back and I held her stroking her hair. She shivered when I ran my hands down her back, and experimentally, I let my fingers run lower and lower over her tight ass. I whispered in her ear, asking if she was alright, and she responded by removing her shirt revealing medium firm pert breasts with protruding...

wedding Anniversary 0

It was 10 years later, we were celebrating our anniversary. We had been out for a meal and had had sex twice that night (I said we had sex, not made love), he was a good husband but all we ever did was have sex, a quick missionary position shag, then he would roll over and go to sleep. In our first few years together it was twice every night, but then we fell into the “married routine”, some weeks, I was lucky if we had sex at all.……. Chapter 1 …….So, the morning after the night...

Wedding Night 1

I put on my white dress sandals and I went down stairs to the party we dance, ate and talked it was a wonderful time when Kevin asked me to dance and as we where dancing he whispered in my ear I cant wait for tonight I have been waiting for this night for 1 year and after he said that I agreed with him even though I was truly scared not of Kevin but it was going to be my first time being with a man sexually not to mention I have never even seen a man naked so yes I had a scary night coming to...

wedding Anniversary 1

The tattoo parlor is not a place I would normally visit, especially on my own. It looks more like something out of the Rocky Horror Picture Show than a place my husband would visit. Pictures of men and women in different poses, showing off their tattoos, and pierced body parts fill every inch of the walls. A picture of a woman with various studs in her pussy draws my attention, and I can’t help but stare at it. “You must be Sue, my name is Arthur. Won’t you take a seat, and I’ll be right...

Wedding Day

Grace gives herself a quick once over in the mirror, her hair and make up are flawless, her tiara is positioned perfectly, and she looks every inch the blushing bride. The photographer is setting up his tripod and flash on the other side of the room, and while he’s occupied, Grace takes the opportunity to watch him. He seems to be in decent shape so she assumes he looks after himself. His movements are quick and purposeful, definitely a professional. She smiles as she thinks of him...

Wedding Night Cuckold

This is a story about Samantha, a young white woman in her late 20’s, and her fiancé Eric. Samantha has jet black hair that goes roughly half way down her back, blazing green eyes, and a very petite figure (think 32-22-32). Eric is a white man also in his late 20’s and has light brown hair and blue eyes, and is pretty athletic. Samantha also has a twin, Annabella, who looks just like her except Annabella’s eyes are blue. This is their sixth story. Other stories featuring them include...

Wedding Nerves

Katy Harrison was 23 years old and about to get married. Her husband to be, Tony, was the only man she had ever loved and she couldn't be more happier. She had met Tony when she was only 18 and he was the only man she had ever slept with, indeed the only man she had ever done anything of a sexual nature with. It didn't bother Katy though, Tony was kind and a gentle, caring lover. Katy felt fulfilled and excited about her big day. Katy's best friend was Leanne, it was strange that they were best...

Wedding

With friends like these who need enemies. When one of your friends decides to do something a little different and stabs you in the back. Everything in my relationship was wonderful, my wife and I were getting married for the love we had. It was the first time that we were to be together, before that we hardly touched each other but she insisted that we had to get to marriage. My friends decide to make me a bachelor party. As every man I finally decided to make the most of my latest adventure,...

Wedding day whore part 4

Apologies for the delay in the latest adventure of our whore Lisa. I hope it doesn't disappoint. Please let me know your thoughts good or bad.Lisa was fast asleep, she was having a dream about being groped by 1 of the hotel staff. He was black and a total stranger to her, yet she was allowing him to put his hands all over her body. As the stranger moved his hands over her body he softly played with her tits, stroked and caressed her body. Lisas breathing was increasing, her body thrusting...

Wedding Cake Island Part 2

We both climbed off Spike to let him up and Rupali and I undressed. “Okay, foreplay dummy, on the bench.” Ruplai lay on the yellow board, legs out straight and a big cheesy grin on her face. I climbed around the other side of the board and motioned Spike in so that we knelt either side of her pussy. Spike looked pretty focussed, so I snapped my fingers in front of his face. “This is for your benefit, you know,” I scolded. “You want her to come, don’t you?” “I made her come before,” he said...

Wedding Anniversary Passion part 3

We must have fallen asleep and when I woke, Marina was still nestled spooned naked beside me. I slipped out of the bed, covering her gently will the bedsheet and went to shower. When I returned to the bedroom, Marina was just beginning to stir. She opened her eyes and smiled, “You should have woken me – that shower’s big enough for both of us!” “You needed the rest for tonight” I replied, “and we need to get to get ready for dinner, but after that…”.If you’ve ever been to Kilronan Castle,...

Wedding Anniversary Passion Part 2

After a quick clean up, we grabbed our sports bags and headed down to the spa. We’d never been to a spa before, so were unsure what to expect so we each brought a towel, not that I expected to need it given the prices, and I had brought my usual loose swimming shorts and Marina her black one-piece swimsuit.The girl on the spa reception was very nice and explained that there’d been a slight mistake in our booking and that they couldn’t accommodate our treatment for a further 90 minutes, but we...

Wedding day whore part 3

Please read parts 1 and 2 first for this story to make sense. Feel free to leave me comments and suggestions on what should happen next.As soon as the pictures had sent to mark, lisa stood up and went to the bathroom to get herself cleaned up. As she stood at the sink looking in the mirror at the naked woman in front of her with cum dripping down her face and clinging to her eye lids she started to cry, how had she let it go this far? why did she ever fuck those strippers? how could her friends...

Wedding gift

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Wedding Night With My Son

After being alone for 12 years since my ex-husband left me with our son, I was getting no sex. By the time my son Rocky was “old enough”, I had noticed how much of a young man he was turning into. The fire in my pussy built with each passing day. Things changed when Rocky turned 19. I began to tease him. He looked so sexy, tall and muscular. I was in lust with my own son and my day came when his girlfriend dumped him. That night I he came home drunk and I comforted him. He put his arms round...

Wedding night 2

I moved near her and placed my hands over her neck. I slowly traced it down and rested it on top of her left mound. She moaned and pressed her hands over mine tightly. I felt and massaged her soft breasts softly. She uttered slight gasps as I lowered my lips to kiss her again. This time I took her lower lip into my teeth and nibbled at it. Meanwhile my hands were busy unhooking her blouse. I was struggling with the last hook with which she helped free it off her body. I stripped her blouse off...

wedding day whore 3

Please read parts 1 and 2 first for this story to make sense. Feel free to leave me comments and suggestions on what should happen next. As soon as the pictures had sent to mark, lisa stood up and went to the bathroom to get herself cleaned up. As she stood at the sink looking in the mirror at the naked woman in front of her with cum dripping down her face and clinging to her eye lids she started to cry, how had she let it go this far? why did she ever fuck those strippers? how could her...

Wedding Gift

Lisette and Samantha were not only neighbors, growing up together in the same housing development but they were also best friends. They shared everything with each other, from elementary school through high school, closer than sisters with bonds unbreakable. The two girls grew up with memories of laughter and tears, excitement of new lovers and provided a shoulder to cry on through heartbreaks. Lisette was the more outgoing of the two. She learnt early on, being the only child, how to...

WeddingChapter 6

“Where’s your keys, George?” asked Frank conversationally. The last guests had just left, and it was just the four of them still at the country club. “In my pocket,” replied the father of the groom, confused by the question. “You sure? Let me see them.” George shrugged and reached into his pocket, pulling them out and jingling them in Dave’s face. “You’re right,” remarked Frank, reaching out and snagging them. He thrust them into his pocket. “You won’t be needing them tonight.” “What?”...

Wedding PresentChapter 2

A COMPANY PICNIC When Taylor and I returned from our honeymoon, we were invited to a company picnic the following weekend for the senior staff. Dave pointed out that I would be the only manager level person at the event and it would be a great opportunity to position myself for further advancement. He went to great lengths to explain to me that the business world wasn’t like the church and that Taylor should dress in a cheery little sundress, like you find at the mall. Taylor was delighted...

Wedding BetChapter 2 First Date and Consummation

Mindy sat in the car in shock looking at the ring. She’d look at me and then at the ring. Her incredulity showed. She said, “You don’t even know me.” I laughed, “And vice versa, but we are engaged.” I popped open the glove compartment opposite her and pulled a folded page out and gave it to her. “Read this. We’ll get your lawyer to go over it, too. It’s my proposal for a prenuptial agreement – just notes at this stage. See if there’s anything you don’t like.” Mindy silently read the...

Wedding BetChapter 5 How to Watch a Hockey Game

Blake and I had been known to trade several thousand dollars back and forth as we bet on various NHL hockey games. The Stanley Cup was up for grabs and the whole season had gotten more exciting. Thursday night I invited Blake over to watch the Bruins-Blues game with me. As requested he arrived about seven o’clock with a huge pepperoni pizza and a dozen beers. We got the beers on ice and quickly set up in my media room. Mindy swung through the condo on the way home from work and said hello....

Wedding BetChapter 6 Couple Seduction

Kyle and Jess connected with us Friday right after work at my condo. We took my big luxury car to drive to Paicines. The traffic wasn’t that bad for some reason, so the trip took ninety minutes. The drive turned out to be a nice time where we got to know each other. Each of us took turns talking about our background and jobs. I talked about the real estate market, Kyle described what he did regarding investments and trust management, Mindy described her small chain of boutiques for western...

Wedding BetChapter 7 Dinner Party Extraordinaire

Mindy and I planned a small dinner party at my condo. Mindy was intent on completing the sexual rounds with my friends and she wanted me to complete doing her friends. Moreover, she wanted to also fuck Wade, Tina’s fiancé, again. Thus, I invited Blake, Doug, Kyle, Kent, and Wade to our potluck dinner. Mindy invited Tina (Wade’s fiancée), Beth, Heather, Dana, and Jessica (Kyle’s fiancé). As Mindy put it, we had gender balance, so no one needed to sit on the sidelines once the fucking...

Wedding BetChapter 14 Marriage Bait

“My butt still hurts” The group of us sitting in the ranch’s living room laughed. Taylor instructed, “All things in moderation, my dear.” Kat was standing and rubbing her glutes with both hands and obviously flexing her Kegel muscles, “But you were doing it.” “I was, but not as energetically as you were, plus I’ve had anal sex many times before. That was your first time. You needed to be a little kinder to yourself, plus Mitch isn’t the smallest man alive. He did try to take his time with...

Wedding BetChapter 15 Naughty Wife

I had a closing on some land in South San Jose, but the lawyer’s office was in San Francisco and the meeting started at four-thirty. I’d taken Margo with me since she’d set up part of the financing with Bank of San Francisco. I also knew we were doomed on the trip back to Menlo Park to sit for an extra hour in traffic on every major artery heading south out of the city. I’d already texted Mindy about our likely tardiness. Margo and I stopped at a fast-food place and got what passed for...

Wedding BetChapter 16 Retribution

The chimes went off in the ranch’s foyer. Whenever somebody had driven more than a hundred feet inside the main gate they went off. The nice thing about that is that it gave those at the house about a five-minute warning before someone would come through the front door from the nicely bricked turnaround in front of the house. There were no cars showing that night; I’d put my large Mercedes in the garage when I arrived in mid-afternoon with Blake, Kim, and Connie. Mindy surreptitiously sent...

Wedding BetChapter 17 Dominoes

My business week was filled with a lot of time out of the office. I’d gotten approval from two different planning boards to re-plat two different large parcels of land I’d bought at basically fire sales. One was on the north end of Marin County north of San Francisco over the Golden Gate Bridge, and the other in the middle of Santa Clara County on the way towards the ranch in Paicines. Given traffic it was taking two hours or more to drive between the two of them. I met with two general...

Wedding BetChapter 18 The Last Holdout

We’d managed to capture four adjacent tables in Coyotes, the bar and lounge where I’d been the subject of a bet that resulted in me proposing to Mindy and subsequently marrying her about nine months earlier. Each table was small, enough to hold a few beers and one or two plates of bar food. The Friday night band seemed loud, as usual, and conversation was limited to between numbers, band breaks, or during the quieter slow dances. The ‘women folk’ were gathered around two of the tables: Mindy...

Wedding day whore 4

Please let me know your thoughts good or bad. Lisa was fast asleep, she was having a dream about being groped by 1 of the hotel staff. He was black and a total stranger to her, yet she was allowing him to put his hands all over her body. As the stranger moved his hands over her body he softly played with her tits, stroked and caressed her body. Lisas breathing was increasing, her body thrusting towards the dark hands that moved over her body. Lisa didnt want his hands anywhere but on her...

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"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...

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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...

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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...

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I have been a crossdressing Mistress for several years now. I have a petite body and always looked good in a dress. I take on many slaves but my favorites are other men who look great in dress. This is a story about my favorite slave I have ever trained.I had been anticipating the arrival of my new toy all week, and he was moments away. My new slave, eager to be trained under my heels. The first time I saw him I had brief fantasies of my hands and mouth exploring every inch of his petite and...

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I went through a period in the '80s and '90s when I was very much into crossdressing and being a bottom. I didn't write these events down at the time, but I wish I had. As the events come to memory, I'll write and post them. Here's one such story:In the '90s, I was married, and my wife didn't (as far as I knew, anyway) know about my bi or crossdressing interests. I loved her very much, but I had these other desires I never shared with her. I kept a small bag of lingerie, condoms, and lube...

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Dresses Aren't Bad By Margaret Jeanette Samantha Monroe sat in her office waiting for Leland Keyes to come by. He was president of the leading bank in town and she handled his investments. He wanted to diversify more. She was all prepared for him. She ran the major investment firm in town and ruled it with an iron fist. She took no guff from anyone. She was all business. She had finished today's Wall Street Journal and was up on just about every investment opportunity. ...

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Births Deaths and Marriages A Short Story By Maryanne Peters Allan Bingley was not the sort of man who you might think of as a criminal. He has a small open and honest looking face on a small non-descript body, slightly flabby. He had very little hair on his head. Alopecia rather than pattern baldness, had robbed him of his hair when he was not yet thirty. His mother assured him that it would grow back. It never did. And now she was dead. He did not need money so much that...

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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...

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It had been 6 months since I received my last haircut. The top was still thin but my sides were getting to be bushy and the length on the back was long and it was just starting to cover my eyes. I had moved about 5 months ago and decide to go and check around town for a new place that was not a barber shop or a over priced hair salon. I stopped in a Vietnamese restaurant in a strip mall about 15 minutes from my house and sat down for lunch when I saw a small building in the back of the...

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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...

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“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...

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After a short summer vacation with too much to do, I thought I'd get my hair done before the school doors open for the year. One thing, one project, one crisis lead to another and I just couldn't get to my usual hair stylist in time. I called three days before school started and she was booked solid, right through the following week. So out of desperation, and with my eyes closed tight, I prayed that things would work out as I, with great hesitation, opened the heavy metal door of this new...

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One of my girlfriends after my divorce was a hairdresser, very useful in more than one way ! Been going out for a couple months , fucked a few times, all going well when I asked her if she cut cut my hair , “no probs hun” was her reply . So next evening after work I had been invited over for tea and to stay , all or offspring were staying at with partners so a free night . On arrival at hers , the house smelt lovely of a full roast dinner , her kitchen table laid with cutlery and her barbers...

Private Vasilisa Lisa Teen Hairdresser Addicted To Anal

Today on www.private.com, we introduce you to Vasilisa Lisa, a sexy teen hairdresser with a beautiful tattooed body who has come to Private Specials, Anal Chicks ready to go the extra mile to satisfy her customers. Getting the Vasilisa treatment today is the lucky Andrew Fire, and he soon finds out that this sexy new girl is just as skilled with her tongue as she is with scissors. Then enjoy this young debutant’s incredible figure in action as she goes on to take a hard and deep anal pounding...

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Young Cross Dressers Secrets *Sandy was busting at the seams to tell someone some very exciting secrets she was keeping. She couldnt tell anyone she knows. She decided to tell them here. __After reading My Bra and Panties are Missing, my own real story kept nagging at me to be told, but I wasnt sure how. I decided to change all the names and write a story all about this secret world I stumbled into. I started getting very horny just thinking about all that had happened&hellip,. __My story...

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I was in my mid 40's and divorced and living a great life. I ran my own successful from home and lived in a large house in it's own grounds at least 5 miles from my nearest neighbour.Whilst I was single I had an active sex life having been lucky enough to know 3 ladies who were unattached and had no need for a long term relationships but were happy to meet up for sex or go away for a break all no strings attached. They all knew of each other and I was aware they saw other men or ladies if they...

crossdresser violation

My house is a small two-bedroom cottage with a study, lounge and combined kitchen-dining room. My bedroom has an ensuite. It is located in a quiet cul-de-sac in a quiet neighbourhood where everyone keeps to themselves. It is perfect for me. Perfect because I am single (due to a messy divorce where she got everything except the debts), perfect because I work odd hours, and prefect because I like my privacy; oh, and also perfect because I am a closet transvestite. Like most...

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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...

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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...

CD crossdresser daughter rsquo s bitch

Note : This story is completely fictional!How did I end up like this? On my hands and knees dressed in just sexy stockings and suspenders and a lacy corset, my face in slutty make up, my lips wrapped around my daughter's boyfriend's cock while my daughter herself rammed an eight inch strapon up my arse. The worst of it was, humiliated though I felt, this was really turning me on. This is the story of how I became my daughter's bitch and how I came to love it.I suppose I shouldn't have let...

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This is a continuation of my Crossdresser to Trans Escort series.After my first fuck for money with the restaurant owner, things escalated. I arrived at work the next morning wearing a pair of black trousers, black blouse and flat ballet shoes. The owner called me into the back office before we opened up for the customers. He was sitting behind his desk wearing a tight black t-shirt which showed off his tanned skin and bulging muscles. 'I really enjoyed our transaction last night' he grinned,...

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I woke up with my hands bound, my mouth gagged, and my ass plugged. The bed I was on was comfortable enough. This was just a reminder that these parts of my body were no longer mine to do with as I pleased. For tonight would be my wedding night. For months we had planned things out. Picking out a dress, a place for the ceremony, all the things that brides do with their future husbands. But for me, it also included a regimen of hormones to complete my becoming as feminine as can be for my man. I...

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Backstory - I just turned 19, in college and still live in my hometown with my parents. I've been crossdressing on and off for the last probably 10-12 years. Till I was about 15 it was just whatever my sister or mom had that I could get my hands on while they were gone. Then when I was 15, I would order some online, or sneak out and go to a store right before they'd close. I've only told two girls, one who didn't believe me and the other who was supportive but didn't really care. For the last...

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...

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