Crossdressers indian porn

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

Rite Of Passage John Or Jennifer

John turned eighteen that day. His father was at work. His mother and sister Lisa were spending the day shopping, saying they wouldn't get back until very late in the afternoon. He decided he wanted to pamper himself, celebrating in the best way possible. That way was by dressing up as a female. John had been a crossdresser since he was sixteen. He believed he had managed to keep that part of himself hidden from the rest of the family.After taking a luxurious bubble bath, he carefully made up...

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

The Brother Bride

My twin sister Julie and I had always been close. Growing up, we shared each other’s deepest secrets. I had always told her I would do anything for her.Julie was a girly-girl, and loved being female. She had said she would be happy if she could wear dresses and heels all the time. Her wardrobe reflected that. She had also known about my urge to wear female clothes since we were young, and being my dear sister, never told anyone else. She told me she could never mock me or embarrass me in front...

Crossdressing

Sex with a crossdressing in a public toilet

Friday came and I'd bought a new outfit just for the occasion. I slipped into my low rise boy shorts (black with white spots and white lacing), tucking my penis in where it wouldn't get in the way of course. I put on my matching bra, filling it with my C cup breast forms and then put on my black stockings with pink ribbon at the top, pulling them all the way up my thighs. I put on my very short black skirt next, sliding it up so far as to just barely cover my rear end. Fortunately, I'd...

Practice Pays Off

It was a beautiful Saturday late afternoon. I was done with all the things I had to do around the house. My wife was gone for the weekend and I was feeling a bit bored. I thought I would take a shower, shave and pull out the makeup and see if I could do myself any justice in looking passable. Many attempts before had failed, but I was getting a little better each time.I got out of the shower and was nice and clean, smooth from head to toe and went to the bedroom and pulled on a pair of my...

Crossdressing

Turning into a Middle Age Slut Part 1

I have had the crossdressing bug for many years and have collected some items to fully dress with, such as a wig, makeup, fake boobs and all that makes me look as fem looking as possible. Being in my mid fifties however, there was really no way that I was going to be truly passable or that hot, so I thought Over the years, I collected my lingerie, heels, wigs and experimented with makeup. I mostly took it with me on travel to experiment with in the hotel rooms. I bought most of the stuff off...

Crossdressing

Shall I Tell You About My Wife

Time has been exceptionally kind to my wife Samantha. As a sixth form teenager, her stunning looks, along with her 36 DD's, attracted the attention of the male students and some teachers at her school. Her chestnut brown hair flowed down to her waist, and her face wouldn't have looked out of place in any beauty pageant. It was no wonder that she had an everlasting stream of suitors clamouring for her attention.She lost her virginity at seventeen, after several attempts, to James the school...

Crossdressing

A Close Encounter Part 3

Homeward Bound "Well, how was it for you?" My question was directed at my wife's reflection in the rearview mirror. She looked quite fresh considering that she'd just been fucked. "Yeh, it was good! Pass me a tissue, babe." Sam stretched an arm between the front seats. "It was certainly different!" Paul's assessment of the last hour's shenanigans raised a chortle. "Not 'aff!" I concurred in a deep baritone totally alien to my look. While Samantha wiped some of Ross's cum from her...

Crossdressing

Crossdresser and I at Costco

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

Crossdresser Stories 8211 Assfucking in panties

I have been ‘mildly’ crossdressing for over a year now. I say ‘mildly’ because I am not into full feminization, I just love the feel and look of lace panties when they are hugging a good looking cock, not to mention the taboo. I have taken to wearing stockings too which feel amazing, it’s like having your whole lower half caressed persistently. I have thought of wearing a bra but, although I can almost imagine how amazing it would feel, I don’t think men look...

Telling Mom Im A Crossdresser

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5’10’ in height. She is also a fairly busty woman with a 30DD chest with about 35′ hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first few times she had a surprised look on her face and left. However, after a few times she seemed not to care...

Wonderful crossdressing shopping experience

Following is a true account of my recent experience of shopping for clothes (crossdresser, no sex). I just wanted to share a couple of very pleasant experiences I had shopping at the Natick Mall near Boston. It was the first time ever that I managed to shop with confidence and without any stress. I really want to give compliments to lovely women who made this possible (in case any one of you ever went to shop there, tell them about this story). The first experience I had was at a small...

Crossdressing Domina gets a new slave

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...

Crossdressing Fun From A Womans Point of View

I have enjoyed reading the stories written by men to get a better understanding of what it is like to crossdress. As a woman, I find that I really enjoy and am very aroused with a feminized man. I guess I have always been a bit of a tomboy and enjoy doing athletic things, so being with a man that is the opposite seems natural to me. I used to play gender swap cross dress role play with my ex boyfriend. It started one afternoon when he came back from playing basketball. I had just finished...

Happy to be Used Pt 9

The next day I woke up very early. I would have expected to sleep in since I got home after 2:00 a.m. but the clock said 6:00 a.m. when I opened my eyes. I lay in bed reliving the events and my performance from the previous night. The sex was amazing. The double penetration was mind blowing. But what really kept me smiling was my convincing female performance.No one suggested I was a guy all night. No one hinted at knowing my secret. I lived an entire night as a woman and was treated like...

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

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

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

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

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

Caught and punished by my manager part 1

My job as a sales rep meant I had to work away a lot, traveling around the country to various events and conferences. It suited my lifestyle as it meant I was able to indulge in my secret obsession of crossdressing. Every week I'd pack my suitcase with a new outfit of sexy lingerie, heels, wigs, makeup, a vibrating cock; all the things I’d need to satisfy my sexual urges each night when I’d finished work. The hotels were great as the rooms always had a shower, a large bed and lots of mirrors to...

Crossdressing

A Condition of Endearment

I am a young, petite, passable and enthusiastic transvestite. I’ve been crossdressing and working on improving my look and appearance ever since I was a sixteen year old boy. Now after two years of weekends dressed in public as Cari, I had developed quite an attractive look and appearance. It often seemed at times, that many a man would come my way.Because of my exotic and sexy appearance, things could get interesting at times. When you are dressed as an alluring, sensual woman in high heels,...

Crossdressing

From Sam to Sarah A genre bending story of sexual and personal discovery Chapter 2

The anticipation was eating me alive. My girlfriend, Aubrey, a strikingly sexy, gorgeous, blonde, polyamorous, bombshell grad-student and I had been living together for about three months. She had taken my virginity and was the dominant one in the relationship. She had been fucking another guy, Scott, every other weekend for about two months, and I had finally asked if I could be there in the room next time he fucked her.She sat there, pensively deliberating. Her adorable eyebrows were...

Crossdressing

Sex With Wife Who Doesn t Know

A little about myself. I have been married for 40 years. I work in a professional career and I secretly like to cross dress. My wife does not know, or, I suspect she might, but prefers to not acknowledge it.I started dressing about twenty years ago when our two daughters were off to college and we were empty nesters. Out of curiosity I tried my wife’s panties on one day while she was gone. It really felt good – different. I was not sure this was right and afraid of getting caught so I did not...

Crossdressing

How to Treat a Lady

Being a pretty, petite, believably passable crossdresser makes me a very happy person. I have been dressing up as a sexy girl while daring to go out in public for the past two years since I was sixteen. I have had this urge and desire to dress as a female for as long as I can remember so I have gradually come to accept that I have a feminine side that needs to be nurtured and encouraged.I have managed to accrue several wigs, dozens of dresses, many pairs of high heels and enough makeup to last...

Crossdressing

Forced Crossdressing Stories

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't your thing but you have ideas, send me a message. I'd love to hear of anything you come up with.

Transsexual

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

My first time in a bar

For a while now I had been chatting with a sweet guy named Allen, who was bisexual and was eager to meet a crossdresser. He was very muscular and handsome, a hard body but with friendly eyes. He seemed to really like my pictures and said he had cum, stroking himself, while looking at them several times, and was eager to meet me in person. He wanted to meet in a bar which is something I had never done before. I have had sex outdoors before but in a secluded spot, I had only toyed with the idea...

Crossdressing

My 2 AM Phone Call Part Five

Bondage means different things to different people. To some, it just means being tied up, but I always felt that true bondage means a lot more. It can mean total surrender to the situation I find myself in and total embracing of the situation, knowing I can't do anything about it.When I looked more carefully at the machine that was in front of me, I realized that this was to be a special challenge. It was pretty clear I was going to be positioned on the machine in such a way that I could not...

Crossdressing

Being Christy Part 3

My experiences with Jenny and James had been amazing, but summer drew to an end and it was time for me to take up my place at university. I didn’t need much and only took a couple of bags with me, but the move did mean saying goodbye to my sister’s wardrobe. My parents gave me a lift to my student digs and after some typically over the top parental farewells, I was left alone three hundred miles from home.Settling in to student life was simple. There was an immediate social network in my fellow...

Crossdressing

She Made My Dream Cum True

I had been seeing Ellie for a few months before I told her about my little secret. We enjoyed straight sex, but something was always missing for me. After I told her about Vanessa, and my desires to dress up and be treated like a woman, I was really scared she was going to cut and run, but she actually was interested in knowing more. I confessed some of my innermost desires to her. I told her about how I loved being with her, but that I really wanted to know what it was like to be with a...

Crossdressing

My best friends dick

I was a closet crossdresser with a crush on my best friend and finally, after we had both graduated I worked up the courage to show him how I felt. I invited him only and met him at the door dressed in my sexiest/sluttiest outfit. I fell to know knees and gave him his first bj. It was also the first j I had ever given. It was wonderful for the both of us. It was something I had wanted to do for a long time and he had no idea that I was into cross dressing or wanting to be with a guy. After...

Crossdressing

crossdresser confession part 1

I really loved my wife; she was the most beautiful creature I have ever known. Tall, brunette and the longest legs you have ever seen. Myrtle's beautiful face is framed by her gorgeous brown hair. She was about 5'8" and had a great ass. Her curves were soft and very feminine, not a big chest but nice and perky tits I loved to play with.She would drive me crazy when she donned a pair of pantyhose and heels with a short skirt. She didn't know it, but she would not have been able to keep my hands...

Crossdressing

The Best of Both Worlds 2

"Oh, God, Daniel!" Arya cried out in ecstasy, as her body came to orgasm. Sitting on top of Daniel, she let her body bounce on him, as he shot a load of cum into her with every upward thrust. She screamed excitedly with each push that Daniel gave until he was finally finished, and Arya rolled off and lay beside him.The sex had been both exhilarating and disappointing. As always, it physically felt incredible, as Daniel certainly knew what he was doing in bed. The problem that brought the...

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...

It Wasn t Love But It Sure Felt Good

Al called me first thing Saturday morning to express how much he enjoyed our time together last night. He also asked if we could do it again soon. I told him that we could this coming Friday if he was available. I could show him some of my other outfits and the pictures that he took of me as well. He gleefully responded that it was a date.As the week progressed ever so slowly, we spoke at least twice a day and were both looking forward to Friday night. I spent my free time trying to decide on...

Crossdressing

First Time For Everything

I have been crossdressing since my mid-teens, from sneaking a pair of my sister's knickers to sneaking into the gardens of my parents' neighbors and pinching underwear from washing lines. In my late teens, when I found girls and sex, I purged any clothing that I had and managed to put the ’urge’ behind me. I settled down and got married.Unfortunately for me (or not?), my wife liked to wear very sexy underwear, stockings, and very revealing outfits. This meant there were a lot of these ‘things’...

Crossdressing

Jenny and Mike Date Night

It’s Friday night, but for me and my wife it’s Date Night. Most couples have date nights on Saturday, but we have it on Friday nights to get an early start on the weekends. Michelle and I have been married for a little over two years now and we live a very happy life. I was not always so happy because I am a crossdresser and have been dressing up ever since I was 16. I met Michelle when we were in college in 2005. She was studying law, while I was in the IT field. We met at a college party and...

Crossdressing

The Compromise Part 1

My wife, Ally, and I have been married for eight years. What once could be considered a torrid love affair had subsequently lost its sexual passion. We don’t have any children, both being career focused, but our sex life had become quite stagnant from the steady grind of life and over-familiarity we had with one another’s sexual tastes. That is, until one crazy night changed everything. About one year ago, we were fighting constantly. We didn’t know why, but we were both at our wits end with...

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 Irresistible Dress

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

Crossdressing

Crossdressing With Walt pt2

Walt and I headed out to the living room and as i sat down, Walt went into the kitchen and came back with two beers. As he sat down next to me he handed me a beer and for the next several minutes we sat there quietly drinking our beers. Walt finished his first and after he put his empty can aside he looked over at me. "You were fuckin' great" he said as he moved his hand over and laid it on my crotch. We were both still had on our outfits and as he now started to caress my crotch, I looked at...

Made Maryanne Part 2

When I woke up the following morning, I immediately became aware of the situation. It was difficult not to notice the pretty white cotton and lace nor the fact that I was wearing it. I quickly recalled the events of the previous night, feeling ashamed at having been caught masturbating. I knew that Beatrice somehow wanted to make a point by telling me to wear her nightdress, but I had no clue why. I rolled over to see her watching me. She was wide awake, looking as beautiful as ever with her...

Crossdressing

Crossdress Rendevous

I had to be out of town for a few of days for a demonstration an I knew there was a alternate lifestyle club located there and so I decided to take along with me a white silk dress, bra and panties and white hose and a pair of white stiletto heels. I didn't tell Carmen that I was hoping to connect with another man for sex, me dressed as a crossdresser in my outfit. I had finished early with the demonstration and went back to my motel and quietly changed into my white outfit. I left the motel...

Office Caught 2

I couldn't focus, my head was racing with all kind of thoughts. I had no idea what this would result in. My manager and teammate noticed something was wrong. I just told them I was coming down with something and felt ill. As there was only about an hour before closing time, my boss told be to finish early and get myself home, dosed up and to recuperate over the weekend. I didn't need to be told twice, this meant I could escape before bumping into Helen and being confronted about wearing...

Crossdressing

Office Caught

My name is Peter. I'm twenty three and I'm a member of the small internal IT team at a large corporation. It's a typical office setup and our small team of three were kept busy with the day to day tasks; failures, PCs and printers and general support. I'm generally pretty quiet and unassuming and, whilst polite and good at small talk, I'm pretty shy, so just keep my head down and do my job. I joined as a junior aged twenty one straight from University. The office was full of people of all ages...

Crossdressing

Erica Meets Sarah Part 1

I woke up alone on Saturday morning in my nylon blue g-string and nothing more. I wanted to feel it the instant I woke up, my sexually charged femininity, I wanted to feel it all day. Today I'm not a man, today I'm the girl every man wants. Today I'm a slut, your slut. I showered and shaved myself smooth. Ridding myself of body hair was always the first step. Nothing could make me feel more feminine than smooth skin from head to toe. I plucked my eyebrows and moisturized. I moisturized...

Crossdressing

Park n Play

Being the social butterfly that I can be at times, I was checking a website that listed my area to see of there were any 'cruising' areas I could check out in hopes to share my fetish for crossdressing and pleasure. There were several areas, too many to choose from, so I opted for a forested state park. Since much of the funding for the parks in Ohio have been suspended or cut, the chances of being targeted by a park ranger or law enforcement for public indecency can be pretty low. I've heard...

Crossdressing

She Made Me Do It

Something inside me just grabbed hold of my male shackles and snapped them in two; discarding them into the depths of depravity. I had been writing stories about crossdressing and transsexuals all week. I had been looking at girly pictures, not the feminine girl ones, the ones that had dicks. Some of them were absolutely gorgeous, far better looking than some women and I wanted to be one of them. I really did. I particularly loved the ones with the pink underwear and black bows. I have a few of...

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

The Wedding Proposal chapter I

I slowly let the sheer, white stockings slide up along my closely shaven legs. They were smooth as silk, and no hint of coarseness caught the fabric as I stepped into them. The broad bands of elaborate lace hugged my thighs and made me feel great. Four straps, each decorated with a small silk ribbon, held the stockings attached to the garter belt I wore around my waist. The coarse lace felt tight around my body, but I loved the feeling of the feminine garment. It filled me with joy and arousal....

Crossdressing

Jaime s Way part 2

I awoke to feel the dried cum on my face, ass and balls, and then remembering how I got that way made me smile. Crawling out of bed I made my way to the bathroom and took a hot shower and then easily shaved my already smooth legs. Out of the shower I brushed my hair and did what I could to make it appear more feminine. After I put on my make up I walked back to the bedroom and slipped into a pair of sheer blue panties. The cage Sherry had put on my dick prevented me from jacking off but since...

Crossdressing

I AM A Slut part 1

My roommate and I live in a nice house in a very nice neighborhood. We're roommates because of convenience and not because we're lovers. Well, not steady lovers anyway. Sandy is drop dead gorgeous and a very free spirit, meaning that when at home she is usually running around naked or nearly so. I'm a cocksucking, take it in the ass crossdresser with very little interest in women. I guess when you get down to it both Sandy and I are cum dumps. Yes, it's a strange living arrangement but we like...

Crossdressing

An Introduction To Crossdressing The Finale

Reliving our evening’s events had Jackie and Chandra pretty worked up. “You girls seem to be getting a little excited," I stated. "Are you ready for some more fun?” Simultaneously they both grunted, “Yes we are!” I leaned across the table to find them both holding the others cock and slowly working each other into a frenzy. “You should probably save some of that for back at the hotel, before you run dry,” I said. But that didn’t seem to deter their enthusiasm, until Susan walked up. “I’m done...

Crossdressing

Crossing A Different Line

In my personal journey from straight, married heterosexual to bi male, I discovered, along the way, that I was aroused by women’s lingerie. It started with trying on a pair of my wife’s nylon panties. The feel of the silky material, and the sight of how it fit, quickly brought on an erection. I used another silky pair in my hand to jack myself off, being careful not to get any cum on the panties. The orgasm was unusually powerful. In the weeks following, I pursued my new found curiosity,...

Crossdressing

The start of my life as a submissive crossdresser

I am a bisexual cross-dresser/sissy and have been enjoying my life as such for many years. It all began for me when a friend asked me to look at some of his 'girlie' magazines.We went up to his bedroom and looking through the magazine got Chris really excited and he got his cock out and started to masturbate. I couldn't take my eyes off his cock and I slowly reached out and touched it and when he removed his hand I curled my fingers around his erect shaft and began to slowly wank him.I just...

Crossdressing

Carolyn Makes Her Way Part 1

After tucking my penis and balls away, I started dressing with the basics: panties first, a sheer yellow thing, then my bra with the silicon helpers we girls so love and then a pair of black stay up stockings. Next, I stepped into a short green miniskirt which I loved primarily because of how it would reveal my bottom when I bent over and shot pool. After that came my blouse, a long sleeve silky cream colored number that I left the top two buttons open.Dressed now, I went to the vanity and...

Crossdressing

Carolyn Makes Her Way

After tucking my penis and balls away, I started dressing with the basics, panties first, a sheer yellow thing, and then my bra with the silicon helpers we girls so love, and then a pair of black stay up stockings. Next, I stepped into a short green miniskirt which I loved primarily because of house it would reveal my bottom when I bent over and shot pool. After that came my blouse, a long sleeve silky cream colored number that I left the top two buttons open. Dressed now, I went to the vanity...

Crossdressing

The Next Night Crossdresser Part 2 of 2

I woke up early from the sunlight shining through the windows. We’d forgotten to close the curtains when we collapsed into bed last night. Jenny was already awake and watching me. ‘I was just about to wake you up with a blow job,’ she smiled.‘Funny, I was thinking of doing the same to you!’ I laughed.Jenny kissed me then turned around in the bed to lay on her side so our cocks were facing each other. We both had erections already. I shuffled close and took her long cock in my mouth, closing my...

Crossdressing

Jenny Learns Her Place

His hands held my hips tightly and his very large hard cock slammed into my asshole again and again, as if he were was going to ram it all the way out my mouth. I whimpered with each long stroke while my own small dick dripped the remains of my orgasm. It was amazing that he was hard so quickly after pumping my mouth full of sweet jism, some of it even spraying onto my face. “Oh! Oh! Oh! Ooohhh fuck me good, baby,” I moaned over and over. I'd known Bobby since grade school and had even enjoyed...

Crossdressing

Simran A Crossdresser Part 3

After that rather eventful evening with Ram, I opened up to my fears and inhibitions. Now performing on cam or coming out dressed in front of an online crowd was something I could do easily. I still covered my face, since I wasn't yet ready to reveal my identity. As far as I remember, it was a couple of weeks after my interaction with Ram that I heard a commotion outside the house. I went downstairs and looked through the window, and what I saw was astonishing. People were running, screaming...

Crossdressing

First Time With A Crossdresser Part 1 of 2

I’m Scott, 36 years old and recently divorced from my wife of 12 years. It was an amicable split with no kids to complicate matters. We sold up, divided everything two ways and went on our merry way. Our sex life was good and regular but a little boring. We stuck to the same three positions – missionary, her on top and spooning. I’d give her oral but she wasn’t that keen on going down on me and her facial expression when she was blowing me put me off asking for it! I’ve never needed more than...

Crossdressing

An Introduction to Crossdressing Pt 6

After Steven leaves me at the table with Jackie and his new friend Chandra, I start to fill them in on the details. I tell them, “It’s really Jackie’s fault that I got fucked so good; since he was being so aggressive with his dance partner, I got jealous and grabbed Steven’s ass.” Then I continued with, “This led to Steven grabbing mine beneath my skirt, and then stroking my cock and balls under my panties.” Jackie interrupted with, “Forget about the dance floor, tell us what happened in the...

Crossdressing

Memoirs of a Crossdresser Chapter 1

My True Story Chapter 1: I was a kid when I first discovered women's underwear. I loved the way it made me feel. I had a friend who I'd play the normal games that kids play with, and I would always be the girl character. We were children, so nothing out of line went on, but even at a very young age, I had felt an attraction to femininity. There was something that made me feel like I should be the damsel in distress, waiting to be rescued. I remember wanting to feel girly. As I got older, my...

Crossdressing

Crossdresser to Trans Escort Part 3

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,...

Crossdresser Business Trip to South India

Sheila Boy Mon, Jun 3, 11:09 AM to meHi All.Guess you all know i am a bisexual guy and i love to crossdress whenever i get a chance and i am alone.Well as it happened I was on a work trip to chennai and bangalore some time back. It was not a planned one and my boss told me in the night that i had to go and all arrangements have been made. I reached by the afternoon flight, took a cab and checked into the hotel booked by the office. After completing all this and...

An Introduction to Crossdressing Pt 4

In Part 3, Jackie and I had our way with each other for the first time and then headed to the shower to ‘clean up’. As I was removing my feminine attributes - the wig, makeup and lingerie - it occurred to me that even without those items I still felt rather girly. Previously whenever I would change out of my lingerie back into my man clothes, my attitude would change as well. Maybe my attitude hadn’t changed this time since I had dressed all the way and given myself completely as a woman....

Crossdressing

All The Way Part 3

When I awoke it was later than usual but considering the fact that I'd been through back to back fuck marathons in as many nights, I thought it wasn't bad. Slipping out of bed I stepped into a robe and went to the potty, before looking at myself in the mirror. I was a mess so I took the time to freshen up my makeup, washing some off before putting any more back on. Satisfied with how I looked, I padded to the kitchen and started the coffee before taking out the eggs and breakfast steaks. I was...

Crossdressing

All the Way Part2

When Michael stepped inside and closed the door, he gave Kathy the same kind of kiss as his wife had. He was quite an imposing man; short cropped blonde hair, very piercing pale blue eyes, a little over six feet tall and built sturdily, weighing somewhere around two hundred pounds. My heart skipped a beat when I took in the complete picture. Now I wondered how Kathy would convince the woman to get naked while her husband was right there. Donna gave me a hug and a nice kiss and then her husband...

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

My Mother s Boyfriend My Slut

Divorce often times traumatizes the children, but in my case, it set me free from all their arguments. Dad signed the papers and walked out the door on my seventeenth birthday; it was the best present he could have ever given me. I was finally free, I could go to parties and hang with guys. Mom was the lenient one who was always gone on some major trip. I was cool with it until she brought home a boyfriend. Coming home from Europe, my mom walked through the front door, shouting, “I’m home,...

Crossdressing

Laying the Groundwork

My fiancée and I always have been a bit more adventurous than the average couple when it comes to sex. While we both enjoy the sensual feeling of pure, romantic love-making, we also tend to get a bit rough and voracious when the moment calls. In the past, we had experimented with some anal play, with me initiating most of the contact on her. Fortunately for me, her hands also had wandered a few times in the shower together. Nevertheless, this was the extent of our pushing the boundaries from...

Crossdressing

Bookstore Crossdressing

It was at an adult book store in the north part of Denver. I had just gotten a nice pair of stockings with the latex band to keep them up and I had a hot pair of heels that brought out the tramp in me. I always entered the store with the heels tucked in my jacket, so they weren’t that noticeable. Once I was inside a booth, the heels came out the clothes came off and the slut came out. The hallway was empty where the booths were so I ducked into the booth that had a video of a luscious...

Crossdressing

Married Crossdressing Fun Ch 3

“Mikki?” Caz asked. “Yeah, babe?” “I’ve been thinking...” “Always a dangerous thing,” I said, cheekily. “Yeah, whatever. Seriously, I’ve been thinking about what happens next.” “What do you mean, what happens next?” “Well, you are really beautiful but I was thinking of stepping it up a notch.” My wife Caz is the most beautiful woman I know. I love her with all my heart. She is sexually voracious. We played a little game a while ago. She saw how turned on I got when she treated me like a bitch...

Crossdressing

Married Crossdressing Fun Ch 2

Caz and I had been living in our new home for about two months. Our life was wonderful. We loved each other more deeply every day. Caz enjoyed her new job and she was really good at it. She was a beautiful, sexy woman and in the field of international finance surrounded by mainly middle-aged men, she had the advantage and wasn’t ashamed to use it to further her cause. Her company was making record profits and she had already had a pay rise. She was also in line to get a huge bonus at the end of...

Crossdressing

Married Crossdressing Fun Ch 1

I was lying on our marital bed blindfolded, with my hands cuffed to the bedhead, wearing a pair of sheer black knickers. I was waiting for my beautiful wife to come home from her date with Antwan, her big black lover. I thought back to how this all began. Caz and I met when we were both studying at the State University. I was doing an MBA having completed my degree in Business. She was finishing her degree in International Finance. She was the most beautiful woman I had seen and I thought I had...

Crossdressing

An Introduction to Crossdressing Pt 3

As I was following Jackie to the hotel I couldn’t stop looking in the rear view mirror at what was a complete transformation in my mind. I kept doing that thing where you look away and then back hoping to catch your reflection not keeping up with you because you are sure it is not you. It is probably a good thing that there were not very many cars on the road since I wasn’t paying any attention to it while I was admiring myself. I did see Jackie’s turn signal and brake lights just in time to...

Crossdressing

A Date For The Weekend Chapter 1

I've been crossdressing and living as a woman full time for years. I put a lot of time and work into transforming myself into an attractive woman that can accompany a man anywhere in public and never raise an eyebrow. I've long since moved on from having casual cheap hookups to expecting more elaborate playtimes, and generally only date men if we can plan a weekend or more together. I mean, if I spend all this time and effort I expect more payoff than ten minutes of action. I really provide a...

Crossdressing

An Introduction to Crossdressing Pt 2

So as Jacky was going through his story about how we ended up in this shop, I started to look around. I found that my initial belief that the shop was just a hair dresser was completely wrong. The shop was split in two, long ways, with the left side having about four stations for regular hair work, two stations for nails and a couple of closed rooms for massages, waxing and tanning. The right side had several racks of all sorts of women’s clothes including lingerie, dresses, shoes, wigs and...

Crossdressing

Simran A Crossdresser Part 1

Well I still remember the day back in the summer of 2010. I had just turned sixteen and was introduced to the world of cross dressing in the most fantastic way possible.I guess introductions are in order. I am Simar, an average guy from India, who goes to college, has a great family, great friends. Well something you gotta know first. My family follows sikhism so I have a beard, a mustache and body hair which I cannot remove because of religious reasons. But it is a blessing in disguise because...

Crossdressing

My birthday treat

My next door neighbour had begun helping me with my crossdressing by buying me my own clothes, and despite her initial stipulation that I continue to dress in secret, we had experienced a moment where that had all changed. Once that day had passed, Ellie and I became almost inseparable. If we weren't together, we were texting or talking on the phone. We would do everything an ordinary pair of best friends would, with the exception, of course, that Ellie would help me with my little secret....

Crossdressing

FORCED TO CROSSDRESS AND I LIKED IT PART 2

FORCED TO CROSSDRESS, AND I LIKED IT!! PART 2 I walked out of the room picking up a package that was left for me by the door and left for the bathroom to change into what was purchased for me. As soon as I entered and closed the door I rummaged through to find a pair of black lace bra, panties, garter belt and high heels which I quickly put on, eager to suck and fuck cock. As I entered my darkened room I see Xavier stretched out on my bed with his huge cock standing straight up waiting for my...

Free Clothes

I guess it is something that goes through the mind of every new or closeted crossdresser. Shopping for new clothes as a guy is awkward because it is difficult to do without making it obvious it is for you. Yeah you can go online, but it’s tough if you’re not used to the sizing and the clothes never seem to look the same as the picture. Thus, when searching for playmates on Craigslist, if you find someone purging some clothes, you have to check it out. And that’s exactly what happened. I was...

Crossdressing

Tickets please

Standing by the window, I watched as the countryside flashed by. My train had been delayed due to a dodgy signal just outside the station, but judging by the speed the driver was maintaining there shouldn't be much of a delay, thank goodness. Even though I hated my job and boss I needed the money desperately. With a sigh, I turned away from the dreary grey outside and tried to make myself comfortable on the little fold down seat. The train wasn't busy, but I needed to be on my own, at least...

Crossdressing

Crossdressed In best friends mom clothes 3

I woke up the next morning alone in bed. I didn't had a clue what time it was. But my head felt somewhat sore. I can only remember climps of what happened last night. I then realized that i was still in her lingerie, and that the door stood open to the bedroom. As i laid there, i could hear a radio going in the background. “Good Morning!. The time is now 10:30 and your listening to Radio Morning Tunes” Then Queen with bohemian rhapsody started playing. I then heard Margret started singing, and...

Crossdressing at the truck stop

Hello this is my first story I really hope you enjoy it I am a crossdressing truck driver and with my job I have a lot of time to enjoy dressing up in my truck. One night I was all dressed up in one of my sexy outfits watching some porn and thinking about trying to find a nice hard cock to suck. So I put an ad on Craigslist and got a few but none of them wanted to come to me then I got a message from a guy, he said that he was a driver and was at the truck stop. I ask him what he wanted to do...

Caught CrossDressing by Neighbour

I was enjoying a day at home doing some chores and cleaning. I couldn’t resist the urge to dress up, and was soon wearing stockings, high heels, garter belt, bra and g-string. I completed the dressing with full make up, wig and a Sexy satin French maids uniform. I put on some music, had a couple of drinks, and began to do vacuuming and the like. I was having a fun sexy time, dancing about, wearing the little maids dress. I heard my phone buzz and picked it up. There was a sms message from my...

A Crossdressing Story

***A crossdressing story***(All characters are fictitious...maybe…!)I had been dressing for a number of months when this adventure occurred. While I felt that I was learning the basics of makeup and dressing, I needed some expert advice and so I placed an AD in a local TV/TS newspaper for an understanding woman to help me with my feminine side. Little did I know what an erotic journey this would take me on! I got a number of good responses, but the best came from a woman named Debbi. Her...

Crossdresser gets more than she bargained for

My story is like many I have read on here and which I only fantasised about, till now. This story is all true, I thought about embellishing it to make it sexier but thought I’d let you know what happened just as it did. A short history of me and dressing up first.I have been crossdressing for as long as I can remember, from sneaking a pair of my sisters panties, to even sneaking into the gardens of my parents neighbours and pinching underwear from washing lines. In my late teens when I found...

Veronica fists me crossdressed Part 2

I'm sure you all know how tomorrow can turn into a year, but better late than never, right? Sorry for the delay! We didn't get to tape the finale of Veronica's session with the crossdresser with two cocks. That was a shame because it was a rare and unbelievably hot scene that will never be duplicated. But I certainly couldn't deny the woman her "pussy time" to get more tape! She was completely satisfied except for what she had planned for me. I did talk her into getting more tapes so she...

Tyrone s Crossdressing White Pussyboy

Submissive whiteboi becomes a sissy faggot pussyboy for his nigger master.It was to be a night of romance. My Nigger lover, Tyrone, gruntedas he pulled his glistening cock from my aching, cum filled asscunt. Hehad just shot a massive load of man slop into my steamy, grippingentrails. Our lovemaking had been a brutal affair, as it always is, which is just the way I like it. I am a subjugated fuck slave, nothing but a sissy faggot sperm receptacle for my dominant nigger lover.Tyrone is the envy...

Beginnings My First time as a crossdresser PT 1

( Hi I am repostng because I want to string everything together for continuity ) Everything is connected so you should start at the beginning.) (This is a true story, the conversations in it are only as accurate as my memory can supply, as this happened Thirty years ago)When I was 17 I was dating a girl from the local college. I lived in a medium sized college town in a western state and it was 1983. It was Halloween weekend and we were both drinking some wine coolers she’d bought, the drinking...

Attracting some attention

Like most people in their late teens and early twenties, I enjoyed going out to pubs and clubs. I would go out with my friends and my girlfriend, always in guy mode. I was still in the closet pretty much back then. I would dress up at home when I was alone, never venturing further than the back garden to have a sneaky cigarette in the cool evening air, but that was as far as I ever got. I would watch my girlfriend getting ready before we would go out and always feel a little touch of jealousy...

Crossdressing

Becoming John Collins Mistress Part One

Hi. My name is Chris, though some know me as Christine. I am John Collins’ mistress. We care deeply for each other. John “keeps” me. He supports me financially and in return it is my pleasure to keep his sex life exciting, as well as entertaining any of his gentleman friends who drop over. It all began innocently enough, I suppose. I had just turned eighteen and had moved out from my family’s home to be on my own. To support myself I worked as a landscaper, as well as a house painter. I was...

Crossdressing

Sexy Stewardess on a Hot Flight Part One

After arriving in Los Angeles, I became a tranny call boy to support myself. Working for an agency, I was sent to perform sex on many older rich men. Being a hot twenty year-old tranny slut with fresh meat in my panties, I instantly became one of the more popular call boys in the agency. Some men even took me out on dates for dinner then back their places or motel rooms for lots of sexy blow jobs and good fucking. I loved my work. I was especially satisfied by a handsome stud pilot who flew me...

Crossdressing

Porn Trends