Dressing Up indian porn

Caught in Wife s Nylons

I love the feel of the stockings on my legs. The elegant theatre of rolling the nylon and placing over my toes and then slowly stretching and smoothing them up my legs. The detail of clipping over the suspenders and then slipping my feet into the high heels. I like to stand in front of the long mirror and let my eyes slowly rise from the black patent heels over the slight wrinkle of nylon on my instep, up my legs to the band of the stocking tops. And then my cock slowly dripping pre-cum,...

Crossdressing

Becky was born

Hello everybody, my name is Becky, this is the story of how I was born.I was 16 when I first started cross-dressing back in the seventies. I had been accosted by a man and masturbated him in the men’s washroom in the park. I still remember what he said about me. He said I looked so much like a girl even though I was a boy. After that happened, that statement stuck in my head. A little time after that, with that statement still floating around up in my head, I decided I would dress as a girl and...

Crossdressing

Seduction of Piper

I want to thank Farmgal who's sexiness inspired this erotic and steamy tale. Thank you Farmgal, I enjoyed writing my sexy fantasy of seducing you.Stephanie was attending the check out register at Victoria’s Secrete when an extremely sexy woman strolled into the store. Stephanie’s heart beat faster and her eyes locked on this sexy woman as she sauntered towards the display of the new line of sexy panties and bras. The woman’s eyes locked with Stephanie’s for more than a few seconds. Stephanie’s...

Crossdressing

Getting More Than I Went For

Recently I have started looking online for woman’s clothes that I could wear incognito. I am on the larger size so I was searching plus size stores when I found something on one of the websites. It was a black lace bandeau which seems to be a bra-like garment that you can wear without straps. It seemed very sexy and I thought, perfect, no straps and it should be tight enough that no one would notice.I couldn’t order and have it shipped to the house for fear of getting caught by my family. Then...

Crossdressing

Crossdressing for sex

The act of crossdressing for sex is incredibly arousing. It gets me in the mood for the debauchery to come and allows me to come Brooke the cock loving whore. Even having been dressing for over twenty years, I still look forward to it. Adding to the experience I like to dress while my lover waits in another room. I want them to sit there thinking about what I am doing, what I’m putting on, what I will look like when I enter the room. I want their imagination to flow, and I want their cock...

my first cross dressing play time

i sucked my first cock the other day. i posted a ad on craigs saying i like to cross dress and would like to find somebody to dress up with and take turns being sluts to each other and then i posted a few pics of me from my xhamster profile and actually got alot of replies. it took a few weeks but i finaly found somebody that like to dress up and he came over during the day and we started watching porn and i pulled out all my slut clothes and we picked out things that we wanted the other person...

Cindy s makeover

I would like to share my latest cross-dressing experience. Like many cross-dressers, I dress up part-time. I am married and my wife does not know of my fetish of warning woman clothing. My dressing need stems from my enjoyment to the attention I received from admires. I am new at this cross-dressing having only started dressing five years ago. Many cross-dressers started their fetish when they were young, preteen or in their teens. As a cross-dresser, I now pay more attention to woman's...

Crossdressing

Cum Dress for Me

Cum and Dress for Me…Part 1By: ManndeeI saw the advert in my local paper - it just jumped out at me! Then I was surfing the internet, usual stuff, looking for something to get horny over… WHAM!!! The same advert appeared within three days of seeing the advert in the paper. I'm not into that hocus pocus stuff, but it seemed weird that within three days I had seen the same advert. I felt compelled to do something about it. I tried to reason with myself about it. In the end it was like a message,...

Dawn Visits Kansas Chapters One Six

Prologue:In an earlier story, Dan Becomes Dawn, Dan had stopped in Denver, coming out as Dawn, a crossdresser, to former neighbors. At a swinging party the next night, Dawn had met, and connected with, Patti. She accompanied Dawn to Steamboat Springs on a business trip for two nights. Dawn worked three more days, then returned to the former neighbors’ home for a second weekend before returning to Florida. Meanwhile, Patti visited her daughter in Aspen, then returned to her parents’ farm in...

Crossdressing

Kaitlyn

(Saturday, Dec. 14, 2013)Mitch was expecting someone. He paced his living room floor nervously, anticipating the person’s arrival. As he took another step, he wobbled and nearly turned an ankle. “Stupid heels,” he muttered. He was still getting used to walking in high heels. He’d just put them on about fifteen minutes ago. He glanced down at the high heeled sandals, his exposed feet and his red, painted toenails. Is this for real? He asked himself. He heard the sound of a car door slam. His...

Crossdressing

My Neighbor s Wife Pt 2

Suddenly, I was awake. Or was I just dreaming? It was hard to tell. Then I tried to move but couldn't. I could feel that what I was wearing when I last conscious, had been removed. I was naked, except... The last thing I remember was being face down and Carol on top of me steadily fucking my ass, somewhere in all that pleasure and pain, I must have either past out or have withdrawn inward. But now. What was going on? I began to realize Carol had found the bottom drawer of the dresser. The...

Crossdressing

JOANNE SLAM A LIFETIME OF CROSSDRESSING hellip Almost

JOANNE SLAM - A LIFETIME OF CROSSDRESSING…..Almost!!!I have been doing this for a long time, cross dressing and my wanton ways with my transvestite fetish, my feelings of bi-sexuality and the thoughts of being “The Nasty Looking Slut” when I would look at porn magazines. This was in the late 60s and early 70’s mind you so I was seeing very cool, I thought anyway, looking back now it was that vintage lingerie and under-garments style and as a teenager it was most likely finding these kinds of...

576 Shadow Oak Drive Part 2

As Molly drove down the highway, I sat in the passenger seat. Although I had always had a feminine side, I was experiencing all kinds of new emotions and feelings that I hadn't felt before when dressed. I don't know exactly what brought it out. Maybe it was the love and support of Molly. Maybe it was seeing myself truly dolled-up for the first time, seeing my own cleavage, having my manhood taped and pushed back. Whatever it was, for the first time in my life I felt more girl than man. Molly...

Crossdressing

My New Life As A TGurl Slut Introduction

I love cock. I've always lusted after cock and the older I got the more I wanted it. I've slept with getting on for a hundred girls and done things most men can only dream about, like lesbian thresomes with a girlfriend and one of her friends or some other babe.But secretly I craved big hard cock to suck and fuck. I've always wanted to please hunky, horny men and be their slut....but up until a couple of months ago I'd never been with another man or tgirl.OMG how my life has changed and I want...

Crossdressing

My New Life As A TGurl Slut Introduction

I love cock. I've always lusted after cock and the older I got the more I wanted it. I've slept with getting on for a hundred girls and done things most men can only dream about, like lesbian thresomes with a girlfriend and one of her friends or some other babe.But secretly I craved big hard cock to suck and fuck. I've always wanted to please hunky, horny men and be their slut....but up until a couple of months ago I'd never been with another man or tgirl.OMG how my life has changed and I want...

Crossdressing

Wedding Night Part One

As a tranny callboy/escort, I was always fulfilling the fantasies of lots of gay and bisexual men. But there was a fantasy of my own I had had for awhile that I wanted to fulfill with a handsome bisexual escort myself. I wanted to hire a handsome stud escort to pretend he was my hubby and have honeymoon sex with me like I was a bride on her wedding night.Every single girl fantasizes about having a big handsome man to please every night, to sleep with her and spoon together after sex, feeling...

Crossdressing

Crossdressing Charlie Episode 2 High Waisted Skirt

CROSSDRESSING CHARLIE Episode 2 HIGH WAISTED SKIRT "Oh Charlie, you're burning up!" said Mom. She took her hand off of his forehead and read the thermometer. She then left the room to get some medicine. Charlie took the thermometer out of his mouth, held it up against the lamp on the bedside locker, grabbed his hot water bottle and placed it on his face. He left it there for a few seconds before he heard approaching footsteps echoing from the hallway. He slipped the hot water...

Being Joann

I sat in front of my computer and started surfing transgendered sites when I came across an article on psychiatrists specializing in cross-dressers, transvestites, and transsexuals. Some of their treatments included a psychological evaluation, hormone therapy, group sessions, and preoperative assistance. The mail order hormones I was taking were having some positive effects, but I read there were better and safer hormone medicines available by prescription. also really wanted to get some breast...

Crossdressing

OMG Last Night

I suppose I'd better start at the beginning. Well, my femme name is Carly Hughes.I'm a 47-year-old male who has probably been cross-dressing since he was seven. I started dressing in my mum's and sister's clothes. I've built up stashes of clothes many times and binned them through guilt. I've probably wasted so much cash it's unbelievable.Anyway, I've done all the manly things in my life like football, being a jack the lad, getting married, becoming a dad, etc. Through all the years my...

Crossdressing

Damsel In Dis Dress

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

My Crossed Life Chapter 6 Valleys Peaks The Professor

The sexual high of Halloween weekend came crashing down three weeks later when Missy stopped by my house unexpectedly. She was in tears. I assumed the worst, thinking something had happened at school. It was far worse. Missy’s brother and I had grown apart. I was a jock by day, diva by night kind of guy. He was kind of a stoner who had abandoned our friend group. So while it wasn’t surprising he wasn’t the one delivering the news, having a tearful Missy show up at my front door was.“My family...

Crossdressing

A Trip to the Mall

I love sex and I've never been in a committed relationship. Slut is a label I wear with pride and I have the credentials to back it up. But that day I just felt a little extra wild.As bold as I can be, I've never just approached a stranger for sex. I usually meet people in gay bars or on dating apps. Some just approach me. I felt like I needed to put some bait on the hook to make it known I might be open for business. I looked at the clothing I had hanging in the closet. Most of my...

Crossdressing

Jessie s Fantasy Chapter 5 Afterthoughts

After Tracy mouthed, “I love you” to me, I knew right then and there that Tracy not only loved me as a male but also me as Jessie. I could feel my cheeks get warm and flushed from her comment and my thoughts. This was turning out to be the best day of my life. My thoughts were interrupted when Mark’s cock softened to the point that he slid out of my backside. Now my thoughts were replaced by something totally different.It was the thought of sudden emptiness. Something that truly belonged, but...

Crossdressing

Confessions of a Sex Crazy Cross Dresser Part 4

Hi Everyone, I hope you like these chapters, please let me know if you want the next two. Chapter 7: Triangle of Fun I slept great that night with a full stomach of drink, food and Peter’s cum. I woke up on Friday and thought this is going to be a hell of a weekend. I played around with my cameras and had finally figured out how to use the self timer on the 35mm and how to use all the options on my movie camera. They were both relatively new as I bought them in Phoenix, just before moving back...

Crossdressing

Becoming Sarah

I was driving home from a work trip. That is how it started. There was roughly 85 miles to home. I had been driving for about an hour when my mind began wandering the way it always does when I'm not preoccupied. It always goes to the same place. For the better part of five years, I have been cross-dressing in secret whenever I have the house to myself. Sometimes I do it because it excites me sexually, and sometimes I do it just because it feels right. The way silky panties slide around on...

Crossdressing

Jamie s Gradual Grooming Part 3a

I gradually woke up from a deep and warm sleep. My slow awakening became very sudden as I came to two realisations. One, I was wearing underwear from the night before and two, they were wet! I quickly pulled the duvet up and over my head, as if lots of people were watching. I slowly put my hands into my panties and felt a warm liquid all over them, I'd had a wet dream. Straight away I tried to think about what I had dreamt, but I couldn't recall. I wondered what Mike would say and what he would...

Crossdressing

Another Road Trip Story

With trembling fingers, he began to pack his large suitcase. First, he started with some of the silkiest and sexiest lingerie in his extensive collection. At least a half dozen silk and lace bikini panties along with tiny silky thongs were placed inside first along with their matching bras.Garter belts made of satin and silk came next. A half a dozen pairs of black nylons that were either seamed or patterned shared a spot along with crotchless pantyhose. Four long silky full slips each boasting...

Crossdressing

Ultimate fetish dressing

0. She was sitting on the edge of her bathtub completely naked looking out into her bedroom with a kind of thill of anticipation. She had had a full bath and had just finished shaving her body except for her beautiful dark hair. She also had been given several huge cleansing enemas, until what she expelled was as clear as water. She wasn't a perfect girl, she new, slightly smaller than usual with her 163 cm, and she wasn't as thin as some of her friends, but she had full breasts and an inviting...

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...

Max the dress and me

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

Max the Dress and Me

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

Looking for Tess Dressed just So

Looking for Tess, Dressed just So by MadQuill Please remember this is a copyrighted work and all legal disclaimers apply. This story is a subtly revised version of the story "Dressed So". The intent is a response to a comment from a reader. She suggested that the story "belongs in the Lesbian category. I arrived here from a 'stories like this reference'. I found myself captivated by your series that was romantic, with character development, and quite different; re: lesbian and...

Remembering that first time dressed

HI! I have been crossdressing since I was about 7-years-Old. Just the other day a lady friend of mine, (who knows I'm a crossdresser), anyway, she asked me how I first started dressing. She also wanted to know what made me put on a dress in the first place? It's funny, I haven't told that many people how I started out. I would just say that I was hooked with this great feeling I had as soon as I put the dress on. I was hooked so bad that I would steal and hide one of my sister's party...

Crossdressing with my Girlfriend and Boyfriend Part 2

Cross-dressing Days with my Girlfriend and Boyfriend By Cindybelle PART 2 The next morning when I got up, very late, the first things I noticed were the clothes I'd worn last night scattered on the floor, Aubrey's white party dress and her shoes, and the tights and panties that Cathy had provided. Looking further I noticed someone, probably mom or Cathy, had also returned the orange satin pants and top from yesterday plus...

Towards an Advanced Degree Part One

At age eighteen I had finally made it into one of the best universities in the country, yet my true life lessons and deepest learning would ironically take place for me during the weekends. I’ve had the complicated urge to dress up as a girl since my early teens. Eventually I consciously chose to act on my need to do so. Though I live a mostly normal existence and also do enjoy my male side, I was driven to find out more about the feminine side of my persona. A year ago at age seventeen my...

Crossdressing

A Maid Story

It had been a long day and Paul was tired. After a week of traveling and a full day of meetings, Paul was ready to unwind with his wife, Marie. They were what many people might describe as soul-mates. They were best friends who shared their deepest, darkest secrets with one another and who regularly consulted with one another on a wide variety of topics. Their love life had suffered lately and had grown somewhat predictable but that didn’t bother Paul too much. There was so much...

Crossdressing

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...

Crossdressing

My Sexual Odyssey Part 2 Becoming a Slut

After having had a few experiences, I became slightly more comfortable with my sexuality. I decided to branch out a bit, and see what life had to offer. I wondered whether there were any bars or clubs that I could go to to meet people who were looking for someone like me, so I went online and discovered, that yes, there were quite a few such places. It is so wonderful having the internet at times like these; I have no idea how I would have learned about these things without being able to go...

Crossdressing

Dan a k a Becca

Dan had been fascinated with women’s panties since he had found a pair belonging to his sister accidentally mixed in with his clothing. He had rubbed them against his face feeling the silky smoothness. He kept them for a few days until he heard his sister asking about them, then made a pretense of finding them stuck in between the washer and dryer. After that, whenever he had the chance, he would try to sneak in a few strokes against his cheek with a pair of her panties. When his sister threw...

Crossdressing

Born To Be A Babe Part Two

After discovering that I enjoyed wearing sexy little panties, tasting cum and having a big vibrator in my ass, I began to have these auto-erotic sessions, every day.While wearing panties and playing with my ass with a dildo, I would lay in my bed and fantasize about all the big cocks I wanted to satisfy for men. While I was only 16 years-old, I had decided I was a girl and I wanted to wear sexy lingerie and be with men. The only place I had ever had men come on to me was walking down the street...

Crossdressing

An Unforgettable Halloween

This past Halloween I took advantage of a chance to attend a charity Halloween ball. I had to travel for business to a city in upstate New York for a few days, and my first day there I saw an advertisement for an annual Halloween costume ball taking place in the mansion of local philanthropist. The annual party raises a significant amount of money for a designated charitable foundation. This year all proceeds were designated to go to Hospice. The cause itself was good enough reason for me to...

Crossdressing

The Red Dress part 1

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

Sissy Blane s Liquid Assets

I became familiar with the Plumrose Dossier one cool February morning when it was read to me in the private rooms of Madame H at the Clinic.***I'd arrived that morning for my weekly 'therapy' and had only enough time to hang up my outer clothes in the Sissies' cloakroom and don my Eva Gabor wig before a facilitator poked her head in and told me I was wanted in Madame H’s office immediately. Even at that point I knew this couldn't be good so I shrugged into a nylon dressing gown and followed her...

Crossdressing

Chasing Skirts

When I entered college, I was a virgin. Not to say it was particularly unusual; I was a quiet, nerdy kid. I wasn’t ugly by any stretch of the imagination, but a little short, not very masculine, a little self-conscious and not hugely used to interacting with girls.I was eager to change this fact, but I felt like something of a romantic; I didn’t want a random hook-up, and besides, I wasn’t sure I had the confidence or know how to make anything happen that way.What I was sure of, was that there...

Crossdressing

Neighbor fun

It was a typical Friday night. I would hurry home from work to complete my ritual. Take all of the necessary steps for a lot of anal sex, shave all over and transition from a male to a female. I put on a typical “uniform” for the trip to his house. A lacy black top with a lacy black bra under (looked more like a teddy than a top), a short pleated black skirt, black stocking, garter, and fuck me shoes. I wore his favorite wig, long straight blond hair and just enough makeup to be subtle. I was...

Crossdressing

Attractive To A Fault

Events in our lives can often change us in ways we never expect. In my case I certainly felt different as a young boy. I possessed very real, mysterious, unexplainable, emotions that I can describe only as feminine needs, in spite of being athletic and quite normal in appearance. These internal feline longings and desires were intense and drew me to all kinds of feminine things.I knew that I loved to feel like and even look like a girl. In my youth I would secretly dress up like one though my...

Crossdressing

The Sexy Girl Next Door Part One

As a sweet sixteen-year-old boy, I started my life of having transvestite proclivities. Being sexy for men and making their cocks hard for me became my favorite thing to do for pleasure. I already had a boyfriend, the blonde college boy lifeguard at my community swimming pool. He had seen me wearing some sexy little hot pants and come on to me, one day. The fact that he was handsome and all the girls wanted his cock made me proud to be the girl who was getting to suck him, daily. Every day, I...

Crossdressing

A Trip To Joann s

It had been three months since my wife went away for four days giving me the opportunity to be a free woman. I was missing that wonderful weekend of unbridled sex and cross-dressing. There were no more opportunities on the horizon leaving me quite hopeless. In my despair, I surfed the internet for porn and cross-dressing sites when I came across a site called “Joann’s Shop”. It had the greatest selection of clothing, wigs, undergarments, and breast forms I had ever seen before. They also had...

Crossdressing

Karen Goes Out

I was so nervous I was almost sick. For years I'd dreamed of going to a bar that catered to the LGBT community but I'd always come up with an excuse not to, no matter how flimsy it might be. Yes, I'd gone out in public several times, shopping mainly, but also banking, getting gas, and even meeting with other girls like myself. So far, the only sex I'd indulged in while dressed had been primarily with my hand or a dildo and not with any other human being. To make matters worse, I'd only been...

Crossdressing

Crossdressing Charlie Episode 12 Seventeen

CROSSDRESSING CHARLIE Episode 12 SEVENTEEN It is the 12th June, ten days after the shopping/cinema date and Charlie has not heard from Dave. He sits in the back garden on his deck chair, staring out into the dusk sky as the sun slowly sank down behind the distant housing estate. It is a warm mid-Junes evening and the sky is painted with pinks, reds and oranges across the dark blue canvas. Even the stars were beginning to protrude through the blackest parts of the sky. It is truly...

Dan Becomes Dawn Chapters Seven Eleven

Chapter Seven: After The Party"That was an interesting evening. What did you think when Jean took me away?""We have known Harry and Jean for quite a while and have swapped with them and Clint and Debbie a few times. We knew what was happening and were not concerned," answered Marie."I guess you and Patti have hooked up. Is she going to Steamboat Springs with you?" Asked Andrew."Yes, I am going to meet her at Harry and Jean's at one o'clock tomorrow. She will follow me to Steamboat, but will...

Crossdressing

Dressed Just So

Dressed Just So by MadQuill As evening approached I entered my dressing room and set the glass of Chardonnay on the bureau. I had planned to wear a simple black dress but decided a white V-neck with a fitted waist and open back would look best. Due to a hectic work schedule I'd lost nearly two kilos over the past two weeks and decided to enjoy the slimness. This mild winter allowed some freedom from the boots and long sleeves and a sheer nude pair of hose would suffice. I selected...

The very first time with lots more to come

I guess we all remember our “first time”, and in my case the first time I was with a man while dressed was a awesome experience that I still remember vividly, and it happened by accident. I started crossdressing when I was about 14 due to my fascination with sexy women. The first time I slipped into a bra and panties and put on mascara and lipstick I knew I was hooked. I felt all tingly and excited like never before and after that I dressed up as often as I could. My single mom...

Crossdressing

A Close Encounter Part 1

A few weeks ago my wife remarked on how "the gals" hadn't had a night out in months and suggested that we should perhaps go out later that evening."What! Yeah, sure! What's brought that on?" It wasn't like Judy hadn't been around, on the contrary, she'd been around twice last week.I'm one of those cross-dressers whose wife gladly shares her wardrobe. And Samantha's the kind of wife that guys with my quirky habit can only dream of. We've been out together as a couple of girls on countless...

Crossdressing

Lisa s Lessons

I used to spend a lot of time away from home for my job. It had its downsides, but it gave me a chance to do my favourite thing: show off. My toolbox had a locked compartment containing a small selection of cam-suitable wardrobe items: a single camisole, a few panties, and two pairs of nylons - one thigh-high and the other to the waist.I travelled a mostly predictable route, so I was a regular at several hotels around the region. Along with racking up enough points to take my wife on a nice...

Crossdressing

Dawn Visits Kansas Chapters Twelve Eighteen

Chapter Twelve: MondayPart 1: Morning – County Clerk’s OfficeI woke at sunrise, eased out of bed, trying to not disturb Patti, gathered clothing, and went into the bathroom. Showered and shaved, I put on panties and bra, did my makeup, put on my wig and stud earrings. I slipped on my navy floral V-neck dress and tip-toed out of the bedroom, closing the door before slipping on my black open-toe two-inch heels.I went into the kitchen and started a pot of coffee, then to the office and powered up...

Crossdressing

Dan Becomes Dawn Chapters Three Six

Chapter Three: Coming Out! I felt much more confident, to the point of euphoria, as I drove to meet Andrew and Marie. Just having the seat belt bisect my bosom was a thrill.I found the correct address, parked in the driveway, took a deep breath, retrieved my purse and the bottle of vodka, went up the steps to the front door.Seconds after I rang the doorbell, Andrew answered. "Good evening, Dawn. You look fantastic. Please come in.""Thank you, Andrew. I am just a little nervous." I handed him...

Crossdressing

A Night to Remember or to Forget

As a petite, pretty, and now fairly confident young transvestite, I feel fortunate to have discovered so many things about myself. I am proud to have a slim, smooth and well-exercised shape. I have longish streaked blonde hair and my goal is to always develop and improve my feminine elegance.My friends tell me I possess a very strong believability in my appearance as a young woman. I think it is due to the constant experimentation and hours of practice that I joyfully spend in front of my...

Crossdressing

I did not know I had a disorder

I did not know I had a disorder CindyUSA I am not sure if I should be embarrassed, ashamed, depressed about my condition. I do not look unwell; does it show? I look normal to my wife, family and co-workers. I wonder if they know about my disorder. If they had, why did they not tell me? Like most illness, they start slow and build up and suddenly, bang; right between the eyes it hits you. Maybe for years I suspected, but not wanting to admit that to me. I did not think my condition was...

Crossdressing

First Night Nerves

My name is Timothy. I live in a large city in the English Midlands with my girlfriend Debbie. We are both 22 years old and have lived very happily together for over three years. We both work in a call centre for a large financial organisation. I am not tall – 5' 4" on a good day – and have always been very slim. I am blonde with blue eyes and very fair skin. Debbie is two inches shorter than me, with long brown hair and a lovely rounded figure, not in any way fat. We both enjoy fitness,...

Crossdressing

Not just another day dressing up as Gemma

Not just another day dressing up as Gemma Marks and Spencer is a wonderful shop. Their gorgeous lingerie is worn by so many women. They sell some wonderful dresses, skirts and blouses too. I often wear their women's clothes and derive a huge amount of pleasure from doing so. That paragraph could have been written by thousands of women living in the UK, however I'm not a woman. My name is Gemma and I'm a Transvestite or if you like, A Crossdresser. I'd even own up to being something...

The Change Up

Finally a break comes my way. The children are off to college, the wife has to go out of the country for two months on business. I can’t remember the last time we had sex. She used to dress in all types of lingerie for me. It helped me suppress some of my crossdressing desires. That stopped and my crossdressing started to grow again. What an opportunity for me, I can change up and dress the entire time except for when I have to go to the office. Lucky me, most times I work from home. Sunday, my...

Crossdressing

Freedom What The Hell Do I Do With It

Freedom? What to do with a large lottery win. So, I returned to the world of being a single man. A liberation of sorts, a return to uncertainty at a certain age. It is a scary place to be, ejected from the family home and to set up again. Sure I have the comforts. Sure, I have all my books, the CD’s, plenty of DVDs. Ok, the furniture in the new place isn’t that good yet and I could do with a new mattress, but hey, a few weeks and that will be put right. I can get on and decorate the new...

Crossdressing

Two Cowboys and One Dancehall Girl Part One

I live in a town where the national rodeo cowboys come to town every year. And each time they come the testosterone level in town goes up, immensely. All of the big handsome, strong men in spurs and chaps and jeans and western-cut shirts and cowboy boots and cowboy hats get my clitty dick stirring down in my little panties when I see them around town in their pickup trucks or sitting tall in the saddle on horseback. They look rough and rugged and ready. And I'd be lying if I didn't tell you...

Crossdressing

The Early Steps of an Odd Couple

Louisa and I were of the same age, lived with our mothers only a few streets from each other, and attended the same Secondary school. Yet, we had never met. In the 1950s, the belief that boys and girls should be kept apart and raised separately still held sway and was strictly enforced. Incredible as it may seem today, a boy or girl observed so much as talking to each other would certainly be punished for wanton behaviour. Believe me, there were plenty of busybodies and miseries around only too...

Crossdressing

A Satin Dream Comes True

I’d explored my fantasies with a transsexual escort several times and after my last encounter, which was the basic girlfriend experience, though she did wear a corset and stockings with satin panties as I asked. She was very open to fantasy play I have long had a scene I’d wanted to play out and she seemed to be the perfect gentle dominant.Now my thing is dress up. My iconic Mistress isn’t the hard core type. She’s actually quite playful and gentle but she is definitely in charge. My vision is...

Crossdressing

The Panty Princess

Jane and I had only been living together for three weeks when I was caught red-handed. I was mortified when I saw her in the mirror, standing behind me with her mouth wide open. She had managed to come through the front door, up the stairs and into the bedroom without making any noise. I tried to explain that it was the first time I’d ever done such a thing, but she was having none of it. For the next hour we sat on the edge of the bed while she bombarded me with questions about my sexuality,...

Crossdressing

Happy to be Used Pt 6

Sir now knew I was his slut and would question nothing he told me to do. Though I presume this excited him, there is no way it excited him as much as it excited me.I was distracted every waking minute thinking about past experiences and future erotic scenes to come. I spent hours day dreaming and was masturbating at least four times a day. Every time I masturbated I shoved something up my ass.I worked endlessly on improving my feminine image. I spent all my time in feminine clothing at home...

Crossdressing

Getting Caught By A Friend and First Blow Job

After my first time dressing in my sisters clothes and imagining being with a man, I dressed every chance I got when my family wasn’t home. It had been four years since I started and now when I dressed it always included fantasy about being with a man and masturbation. I had grown up into a proper slut that craved cock and needed to be deflowered of her virginity. Only anal I ever had was a small brush handle up my ass, but I wanted so bad for a real cock. I have experienced all my sisters...

Crossdressing

Colour By Design

I wouldn’t say I had a fetish.Isn’t wanting to look fabulous perfectly normal? I hate to say, but when you are the wrong side of middle age you readily grab any potential advantage with both hands. Particularly when you were born a male and your feminine side finally, finally, wins the identity battle.And that’s despite the cruelty of the rolling years removing the last illusions of youthly glow. I never used to believe the cliché that ‘youth is wasted on the young’. In my humble opinion, it's...

Crossdressing

My Secret Revealed

My life was pretty good. I had an excellent job that paid well and afforded a nice mobile home. I played baseball on the company team and had a bevy of office hotties show up to the games to cheer me on, I even dated a few of them briefly. It was the nights that I really looked forward to.Once the day was done and I was safely behind the drawn drapes and locked doors of my trailer that I indulged myself in my new habit. Fresh from a shower I dug out the erotic lingerie that he had...

Crossdressing

Caught

I see all these girls with the first time or the first time they got caught dressing and it turns me on looking back and thinking of mine. Well I was young when I started getting into my moms and soon to be step sister’s clothes. My mother divorced my father when I was young but never really knew my dad do to the fact that he was always in the military and my mother was tired of moving place to place. She started dating a man, Rick, which had a daughter, Melissa that was several years older....

Crossdressing

Stefanie s Crossdressing Memoirs Vol 6

I've decided to switch the category for these over from blog post to sex story, as at this point in my adventures as a gay crossdresser, I had pretty much hit my stride dressing up and finding men and other crossdressers online to have sex with. So I guess you could say my posts moving forward will be a little more "action" oriented. Plus at this point it is hard to remember all of my experiences chronologically, and for the most part that's really kind of irrelevant. If any of you are...

A Paper to The Society of Crossdressing Hardware Engineers

SOME NOTES ON THE DESIGN OF CROSSDRESSING HARDWARE There are several difficulties to be overcome in the design of self-crossdressing hardware. This paper will enumerate them and offer suggestions to remediate the problems. 1) Determining the sex of the hardware. Actually, determining the sex of the hardware is not a formidable task. The primary problem occurs because design engineers have no discernible knowledge of sex. After all, anyone who spends their day in front of a...

Humor

A Fantasy

I have been dressing in women’sclothes since I was little. My grandmother used to dress me up in her old dresses and pretend I was her granddaughter. As I grew older it started becoming more of a sexual fascination and turn on for me. I have been more a closet cross dresser getting clothes here and there and then dressing up and having incredible masturbation sessions looking at tranny porn. Only in the recent couple of years I have discovered about sissy maids and bondage and bdsm and how it...

Crossdressing

A new friend

As I had a nice, big empty house I did what any good 17 year old would do. That first weekend I had a massive house party! I took a night off from dressing up and invited everyone I knew and when it came to the big night there were plenty of people, including a few I didn't know. I chatted to people and made new friends, sharing drinks and having fun. There was one girl there in particular who caught my eye. She was quite petite but curvy, long blonde hair and beautiful blue eyes and her name...

Crossdressing

48 Hours Chapter 1

Chapter 1: Sexual EqualityIt was Saturday morning, they were both lying in bed awake and the tension was almost suffocating. At last, Chris had the courage to speak."Look, I'm sorry, but I just can't switch on like a computer at least not right now, I need something to get me going. I do love you, but all this stress with my job just makes it really hard for me.""Or not hard!" came the barbed reply from Lynn."Well, that's helpful... It is pretty frustrating for me, you know! All I'm saying is I...

Crossdressing

Always Up for a Party

I got home late. What a night! I had gone to the video booth at the bookstore horny as hell but in my wildest dreams I could not have imagined the outcome. Oh sure, I expected sex. I had yet to leave those dark little booths without a mouthful of cum, an ass full of cum or having my balls sucked dry but tonight … tonight! Not only had my ass been filled in the booth but at Trevor’s party I had been fucked like a cum slut, no doubt earning me a reputation as well as a nice little bonus. I smiled...

Crossdressing

Extended Vacation

Hi Everyone...this is the first chapter of my second book. I will publish more chapters if you like this one. Extended Vacation Chapter 1 Hello my name is Cassandra. You can call me Cassie (or Sandy, but recently, I like Cassie). I have been cross dressing for many years. However, the last year, since I turned 40, I have been dressing more than I ever have in my entire life. I made a very smart decision two years ago in regards to my cross dressing. I spent almost a year preparing to be...

Crossdressing

From dream to reality

My name is William. I am the eldest of a family of four kids, two boys and two girls. At the time I was seventeen. We lived in a small town, and my parents were well respected. I did well at school, played and succeeded in sports. I was and still am living an intense inner life fantasising on my sporting exploits and sensual encounters. In those days, it was just as normal for teenage boys as well as girls to be baby-sitting at their parent’s friends and neighbours to make a few bucks. For...

Crossdressing

Dressing room

It was a month after my first sexual encounter with Manisha – a lot has happened. We had the kingdom to ourselves cause we shared a dorm room, she was my roommate, my lover, my sex toy, my everything at that moment. We had sex almost every day, and today was not going to be any different. I don’t know why, but that day I was extremely horny. The kind of horniness I was experiencing was the kind you don’t experience often in your life. It’s the kind you just need to satisfy as soon as possible,...

Lesbian

Dressing Room

It was a month after my first sexual encounter with Sarah - a lot has happened. We had the kingdom to ourselves cause we shared a dorm room, she was my roommate, my lover, my sex toy, my everything at that moment. We had sex almost every day, and today was not going to be any different. I don't know why, but that day I was extremely horny. The kind of horniness I was experiencing was the kind you don't experience often in your life. It's the kind you just need to satisfy as soon as possible,...

Meeting Clair

I was on my way home from the Minneapolis metro area. I was going right past the outlet mall and need to pick up some pantyhose to replenish my supply. I wear pantyhose everyday since I had my varicose vein surgery. The doctor suggested that I wear support hose to keep the problem from coming back. The nurse at the vascular surgeons office suggested that I wear Hanes Alive pantyhose as they were the right compression and that they would stay up better than thigh highs. She knows I work...

Crossdressing

Simran A crossdresser part 2

Well after my little adventure in the bathroom with my mom's panties, I went out for a couple of drinks with my friends. But, in spite of having company, the only thing that kept playing in my mind was the feel of those satin panties and how horny I had felt in them. All I could imagine was getting back to the house as soon as possible, before my parents returned, and having one more go at it. I returned around seven in the evening. Since my parents had a convenience store, I knew they wouldn't...

Crossdressing

Being Sissy To My Brother In Law

Jenny knows I love to wear her sexy undies and lingerie but obviously apart from her it was a secret kept from everyone else. One day while jenny was out, I was feeling particularly randy so went to our bedroom & rummaged through her panty drawers. My hand felt the smooth shiny material of a pair of red satin tanga panties and I immediately got a twitch in my flaccid cock. Satin are my favourite. I thought maybe a pair of stockings would be good too. These were in the wardrobe drawer and on...

Crossdressing

48 Hours Chapter 4

Chapter 4: An Interesting TailChris stirred, and momentarily wondered why he felt so nice, quickly realising that Lynn was at work on his cock again. He closed his eyes and enjoyed the feeling as he grew in her mouth, the subtle vibration of her moans causing him to twitch and shiver.He looked down, and she looked up, running her tongue from his balls to his glans and then, not stopping, over his chest, kissing gently as she progressed until finally placing her moist warm lips on his."Hello...

Crossdressing

A Sweet College Girl In Love

I went to college in a beach town in California where all of the girls wore their little thong bikinis to the beach and showed off their asses for boys with very friendly results. I noticed that when the girls were bending over while playing volleyball in their little thong bikinis, the boys all looked at them with hungry eyes that I liked a man to have for me. The sweet little college girls would have their asses tan, even in winter. The hot girls in school all went to tanning salons and got...

Crossdressing

July 4th Celebration

On July first I returned home from our health club. Ann was packing my suitcase for a mini vacation at a bayside resort. My suitcase was filled with all my girlie things: lubes, vibes, wrist and ankle restraints and the paddle she used on me when I was bad. She also said Ben, his brother Josh, and two others were joining us. Before continuing, I should mention how I became the man I am and how Ann took charge of me. My wife Ann and I met in college and had been married for twenty-five happy...

Crossdressing

Dressing room encounter

‘Babe, can you come here and help me with this?’ I walk back into the dressing room as your open the door. I’m greeted by your long bare legs as my eyes begin to travel up your body. As you giggle you say, ‘here sweetie…my eyes are here.’ My eyes finally meet yours and you can’t help but notice that wickedness that you’ve seen before. After a brief moment, you lightly grasp my cock through my shorts and give it a quick squeeze. ‘Behave,’ you lightly whisper so the other customers don’t hear...

Dressing room encounter

"Babe, can you come here and help me with this?" I walk back into the dressing room as your open the door. I'm greeted by your long bare legs as my eyes begin to travel up your body. As you giggle you say, "here sweetie...my eyes are here." My eyes finally meet yours and you can't help but notice that wickedness that you've seen before. After a brief moment, you lightly grasp my cock through my shorts and give it a quick squeeze. "Behave," you lightly whisper so the other customers don't hear...

Love Stories

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...

Big Green

Loosely based on true events and it is my first story so please be easy. Being a Marine for most meant traveling, working out and above all alpha males only. For me all of this was of interest but I didn't work out and I was definitely not an "Alpha Male". Slim in stature I stood all of five foot, six inches weighing in at a whopping 145 pounds. I wasn't much to look at in a uniform but out of one was another story, I could dress with the best and I looked good doing it, that was the best part....

Crossdressing

Prom Night

When I was in high school, I was seventeen-years-old and dating an older man. He was forty-years-old and very handsome. He had taken me out to dinner and for ice cream and for walks on the beach. We had held hands and kissed but had never gone any further, but I knew he wanted to go further by the way he looked at me when we were riding in his car. I would see him looking down at my sexy, smooth tan legs and I would know, instinctively, he wanted what I had between them. Darryl had already been...

Crossdressing

Jenny Mike Fantasy Sunday

MICHELLE’S POV The alarm was buzzing, and I couldn’t understand why. We never set it to go off on Sundays. I tried to open my eyes as best as I could. It was only 9 a.m.! I reached over and tried to shut the darn thing off. After a couple of failed attempts, I finally found my target. The awful noise stopped. I turned around realized that James was no longer in the bed with me. “James?” No answer. I got out of bed and headed for the bathroom, certain he’d be in the shower. I was surprised to...

Crossdressing

A surprise helping hand

When I initially started to cross dress I would borrow things from those around me. At first it was my sister, then when I visited my father I would wear my step mother's things and eventually my girlfriend's. Mostly without their knowledge, of course. I was always as careful as I could possibly be, replacing things just as they had been left and making sure I had plenty of time when I indulged my habit. When we first moved to my home town when I was very small there was a family next door who...

Crossdressing

Crossdressing gangbang

This is not my story. But loved it so much that I was not able to stop myself from sharing with you all.. please do give your response to As I waved goodbye to my wife as she pulled out of our driveway for a weekend business trip a smile began to grow on my face. Anticipating another entire weekend all alone, and thinking of my plans to indulge my deepest fantasies, caused goose bumps to run up and down my arms. Heading back into the house I grabbed a cool glass of water to quench my thirst...

Lesbian

Sharon Goes The Distance

When I woke up Saturday morning, I knew it would be a very eventful day. My wife, Donna, had been making plans for quite some time, which included me dressing up as Sharon, my female alter ego. Three years ago, I had confessed to Donna my desire to wear feminine attire from time to time and she had embraced it more than I could ever imagine. In fact, she took pictures of me all dressed up or even while she fucked me with her large strap on dildo. We posted these photos on a free, picture...

Crossdressing

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