Crossdressing.masturbating indian porn

A Crossdresser Gets Caught

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

Crossdressing

An Introduction To My Crossdressing

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

Crossdressing

Crossdress boy s ultimate romp

He was in his late 20s.. I'm in my late teens. the thought of meeting him really didn’t come across my mind. however I was won over by his passion and sincerity and he doesn’t even mind if I didn’t shave my legs! wow! we arranged to meet at the car park near my place, he asked me to wait for him and he'll reach in about 45mins. I went straight to my aunts drawer, looking for my favourite pieces of lingerie.. I chose to wear a black lace t-back panty... a black padded bra.. and a pair of...

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...

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

Telling Mom I m A Crossdresser Part 15 2 Kinky Girls

It had been a week since Mom and I spent the 4 days at the spa and hung out with my old babysitter Laci and for a while it was back into our old routine of working and coming home. Day after day I kept thinking about how her warm wet pussy felt wrapped around my cock while the feel of a sexy thong rubbed against my asshole.I came home one day to find my mom was packing a bag. I asked her what she was doing and she told me that she was going out for the weekend to visit an old friend from high...

Crossdressing

Telling Mom I m A Crossdresser Part 7 The Spa

I could barely sit for days after Mistress Keri thoroughly tanned my hide and I had to take almost a week off so that I could heal. My mom knew this to and said we should go on a “girls” weekend to a spa for cross dressers and women, she also said that since it was for others like me then I could spend the entire trip as Missy.I loved that idea and hurried upstairs to pack Missy’s bag. I packed the essentials including a mini dress, a few different pairs of bras and panties, a very sexy and...

Crossdressing

masturbating for a woman on a video site while crossdresing

After years of crossdressing I joined a site that lets me show off a little. I started by reading the stories and then filled out a profile. I added pictures and found it quite satisfying getting comments and friend requests from others.As time went by I found myself enjoying chatting with others on the site and doing some role playing. The chatting was hot and I really liked sending pictures of myself to those who seemed to like how I looked. I guess this is really where the story begins.One...

Masturbation

Ashley s Crossdressing Adventures

It's Sunday and Mommy wants to hear what sissy things I have been up to, and don't leave anything out Sissy Ash, Don't be shy, out with it sissy, I already know you love being a complete sissy!Did you buy anything sissy? Yes Mommy, I did, I want to hear, everything you bought you little sissy, let mommy remove your bra, to access your sissy nipples,Mommy I bought 4 pairs of sheer nylon panties to add to my collection, pink, blue, white and yellow.What else sissy? I ordered 3 packages of...

Crossdressing

First time crossdressing with a friend

My lovely new Malaysian friend emerged from the bathroom, moving shyly in the low light. He was wearing thigh-high stockings, cute little panties and a matching top that was tied at the front.My heart leaped at this gorgeous sight. He had advertised that he wanted to hook up with someone who appreciated fembois, and I was very eager to indulge his fantasies and mine!We had agreed that we were going to enjoy a girl's night together, and so he started playing some lesbian porn on his computer....

Crossdressing

Night Trawling The Crossdresser

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

Crossdressing

Telling Mom I m A Crossdresser part 13 Missy s Turn

Sorry not much sex in this one but its a lead up to 13.5 and I hope you enjoy both of them. Once mom and I had gotten our car back, we took it out for a spin and I have to say it worked and looked like new. It had everything from a new paint job to new parts in the engine. Now in all honesty, I did have to go back a few times and give Ray a few blowjobs to help pay for them but it was definitely worth it and I didn’t mind sucking his huge cock anyway. Mom helped as well by going over to “visit”...

Crossdressing

Telling Mom I m A Crossdresser Part 11 Girl time

Part 11It had been a while since my last time as Missy. I had been doing some jobs for people, nothing special mostly working on decks and mowing lawns for neighbors to not only keep up appearances so as to not give to much suspicion of where my money was coming from. This continued for what seemed like 2 weeks before and started to wonder if my fun as Missy had ended.I walked in the door to find mom on the phone. I decided to go to get a drink before I got in the shower to cool off so I got...

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

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

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

Telling Mom I m A Crossdresser Part 7 5 Amateur Pole Dancers

After our time at the spa, I spent a lot of time in my room trying out all the new sex toys we got from Richard and Monica. They were all exciting in their own ways and I came so much with each one. Some vibrated, some went deep and some felt good stretching my ass wide. The feeling of all the sensations I could get from my new plastic and electric friends were amazing and found myself spending long hours with them. Once I was finished, I had to stop to rest as they had left me completely...

Crossdressing

Wet Dreams to Crossdressing

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

Jaime s Way Part 1

I'd only been married a very short time when my wife came home and caught me masturbating while wearing a pair of panties and a bra. This in itself was bad enough but then she caught me again, and then again. The first time she caught me she was shocked and appalled but the twentieth time or so that she found me wearing panties and bra and with a dildo in my ass she really lowered the boom on me. “Are you a fucking fagot? Is that why you wear women's undies while you jack off? Do you try and...

Crossdressing

Teenage CD Awakening Part II

I had crossed the Rubicon. I had tried on my sister's panties for the first time. Now I felt guilty. Incredibly guilty, and dirty. I went to school as normal the next day, but despite the guilt I couldn't get the amazing thrill of trying on that little pair of blue and white striped cotton panties out of my head. As 3.30pm and with it the school bell neared, the overwhelming urge to do it again overcame my guilt. I was ready and willing to try on my sister's panties once more, as soon as...

Crossdressing

Room 209 First Sex as a Crossdresser

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

Ladies Night at the Leather Bar Part 1

Chloe McGill never led me astray. I was a fulltime, tax paying citizen of Astrayville long before I met her - I just wasn't that good at it. Then Chloe came along, and that girl has ended up getting me into some of the most outrageous adventures. I adore her. It must be made clear how much more she is than just a cohort in gangbangs and sexual trysts of all sorts and sizes. She is the most influential person in my life after my parents. She found me as an insecure fledgling bisexual...

Crossdressing

Jessi s coming out party

Hi everyone. My name is Jessi, I'm 23 and I have been a crossdresser for over three years. Recently I decided to go full time and was going to met up with some friends to come out to them. I arranged to go hang out with them at my friend Derek's house, them thinking I was still coming as my old self. My roommate, who started my path into crossdressing (that's a whole other story), told me if I was going to come out to friends that I should do it in style. She lent me her cream colored dress...

Crossdressing

Caught Crossdressing by Aunt Sharon

Caught Crossdressing by Aunt Sharon Story by Kresha Matay "I wonder where Brad is? He knows you're coming, you'd think he'd stick around. Oh, I hope he'll turn up soon, otherwise you'll have to drive back in the dark." "Rita, don't worry about the boy so much. Brad is like every other sixteen year old boy. He's probably driving around with his friends looking for girls and forgot I was coming!" "Well, aah, I don't think so!" His mother stumbled to say. "That's something you and I...

A Night of Firsts

I have been crossdressing in private since I was young. Now in my late forties and after three failed marriages, I had decided to step outside as Jessica.So after a lot of planning over several months, the day had finally come.I stepped in the bath as JD and shaved any hairs on my body that should not be there. It did not take long as I had been preparing my body for weeks to be smooth. I stepped out of the bath as Jessica and dried myself off. I wrapped the towel around myself just like any...

Crossdressing

Teenage CD Awakening Part I

As a child I lived in a town in the North of England. It was a fairly conservative place, where boys were expected to grow up to be men, and girls to become women. Despite this my mother was a fairly liberal person, and by the time I’d reached the age of 17 the topic of sex had already been raised in our house. Sex between men and women of course, with the aim or perhaps the danger of making babies! This was in 1979. Although my skinny body was still hairless my interest in sex and my desire to...

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

Terry Gets It In The End

The converted attic was my room and it gave me loads of privacy. So as I grew up I could wear the clothes I liked, as long as I stayed in my room. By the time I was a senior in high school, I kept my toe nails painted all the time and I wore panties every day. At night I wore frilly little night gowns and more likely than not I would masturbate, always fantasizing that I was the girl and some faceless guy was fucking the shit out of me. I learned to dance and I loved the way my skirt flew up...

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

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

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

Mom made me a Fluffer

For most of my life I never knew exactly what my mom had done for work, neither did I know who my dad was. As such I just continued with life and thought to myself that I would find out what she did in time.My curiosity first peaked when I was 16, I was looking for my moms purse so I could exchange some of the money I got mowing lawns for people around my neighborhood for different bills. My search eventually leads to her underwear drawer where I do find her stash of extra money so I can change...

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

CD caught masturbating

CD caught masturbating.My name is James, I am 44yrs old, I have enjoyed dressing up in womens clothing since I was a teen. I was raised in a home with just my mom and older sister. Whenever I was alone I would sneak into my mothers bedroom, pick out a sexy outfit and transform into Jaime, my female persona. I was now 18yrs old.One early Saturday my mother and sister headed out shopping, as soon as I heard the car leave, I locked the front door and I headed to mothers room to dress up like a...

First time crossdressing with another CD

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

First time crossdressing with another CD

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

When Girls Are Away Boys Do Play

The boys were left home alone after their respective girlfriends had gone off on a hen weekend together. They soon started enjoying themselves, getting high and playing video games. After a few more beers, the talk turned to sex. They were both pretty fit and got a lot of it so there were plenty of stories to tell. As they became increasingly confessional, they both became more horny.Kris couldn’t resist showing Marcel a video of his girlfriend Tina sucking him off, spunk dripping down her...

Crossdressing

Uncle Joe

I had just returned from a long solitary afternoon walk in the forest. The house looked really pretty in the snow, with its fairy lights adorning the rafters and windows. In fact, it was quite picture perfect, so I stopped to take a photo. I framed the house against the white valley in the background, making sure that I included the lush green fir tree to the right of the house and avoided the somewhat tacky lighted plastic reindeer in the middle of the garden. The sun was low in wintery...

Crossdressing

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

My Road to Cross dressing part 2

I had dressed up since I was a teenager but it was only occasionally. Usually, it was just lingerie and it was always for me and just for masturbation. It was about ten years ago that I decided I wanted to go further and start using makeup and breast forms and wigs etcetera.Quite by chance one day, I rang an old friend just for a chat. I found out that he had rented his house out while he was travelling. The person on the other end of the line was a woman, or so I thought. We got talking and I...

Crossdressing

The Transformation of Ms K Part 1

By day, I'm an average Korean guy, a bit on the fat side, my whole life I haven't been very attractive to women. I'm very timid and shy as a boy, very much a beta. I never even had sex until after college and my dating life has always been pathetic. I've always had a bit of a tight rubber and latex fetish. As I became older, I began buying some pieces of latex and dressing like a submissive rubber boy, tight leggings and tops and rubber hoods. Movie villains dressed in tight leather outfits...

Crossdressing

Crossdresser porn story 1

Ray Hirsch sat at a desk filling out form after form. It was amazing, the information that an employer required before you could start working at a new job: health insurance forms, Social Security, etc., and etc. He was now filling out a questionnaire on his background which would be used to conduct a security investigation, since his work might involve working on classified government projects. He stopped for a minute at the question: List any aliases you have used. “I wonder if I should...

Punished

I glanced around the second hand clothing shop to make sure that no one had seen me pick out the pink, pleated netball skirt from the rack. I hid it beneath a pair of long pants in my hand. I felt my heart start to beat furiously as I stood next to the change room and caught the attention of the shop assistant by waving the pair of pants I was carrying, and the hidden netball skirt in front of me. He nodded and with a smile on his face motioned me to enter the change room. I entered, and...

Crossdressing

Bisexual Crossdresser Fucked By Drunken Roommate

Hello, people. I am Sahil. I am currently living in Mumbai in a shared apartment with my roommate Raj. We both doing our engineering from different colleges in Mumbai. This story is based on my and my roommate’s real life experience. Which is how I am engaged in a sexual relationship with Raj. Let us start with the introduction. Introduction: Sahil The author of the story. I am 24 years old. Since I was at 14 I have a very strange fantasy of Crossdressing as a beautiful girl. Whenever I was...

Getting A Grip On The Situation Part 3

Ken was sent home in plenty of time so Vanessa could become Van again. Van thought about the morning events as he stepped in the shower to remove his makeup and continued thinking when he returned to his room and carefully hid Vanessa's clothing and makeup. This long and laborious process was necessary as discovery by his parents would be disastrous for him.Still wrapped in a towel he then collected all of Vanessa's semen-stained lingerie and hid them in the basement, he would wash them when...

Crossdressing

Where Did My Damn Key Go Part 3

Four days; I've dealt with four grueling days of not being able to touch myself. Jesus, how can anyone even do this without even going insane?!Ever since I crossed paths with that dominating bimbo, my entire routine had changed. And to be honest, I was surprised at how much sex was in my life. From the moment I woke up to the second I crashed and fell asleep, my mind was very frequently in the gutter, wondering when I was going to get some ass or where can I go to beat one off real quick....

Crossdressing

CD caught masturbating

My name is James, I am 44yrs old, I have enjoyed dressing up in womens clothing since I was a teen. I was raised in a home with just my mom and older sister. Whenever I was alone I would sneak into my mothers bedroom, pick out a sexy outfit and transform into Jaime, my female persona. I was now 18yrs old.One early Saturday my mother and sister headed out shopping, as soon as I heard the car leave, I locked the front door and I headed to mothers room to dress up like a little slut and...

Tennis

Sandra and I had been going out together for about six months. She was the perfect looking girl for me, with her beautiful freckled face, slim turned-up nose, pouty red lips, light green eyes, long blonde hair that she usually kept in a ponytail or braids, a great body topped with perky B-cup tits, and a cute firm ass that just screamed to be pumped. She was only 23, but Sandra already knew what she wanted out of life, and wasn’t afraid to go for it. She had met her latest acquaintance at the...

Crossdressing

Crossdressed in public

hi ppl i m rohit….i m 16 yrs old and i live in delhi…i love to crossdress when i m all alone. i hv been doing this sicne i was 13 yrs old.i used to wear my mom’s clothes n gaze myself at mirror. though i was not a gay but i wanted to try gay sex once by turning to a women. it was in d month of june when my parents had to go to noida for some work and i was left all alone at home for a week. one evening i thought i should try crossdressing and go out to enjoy in public n tease some ppl.i...

Gay Male

A Crossdresser 8217 s Life

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

Gay Male

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

My First Time Out On The Town All Dolled Up

It was Christmas time but still warm in Los Angeles. I was living in West LA and heard about a club called Club Sex Addict in the valley, a haven for crossdressers. I had a fairly extensive warddrobe that I bought in a Culver City lingerie shop. I just bit the bullet and went there and told the girl who worked there that I was a CD and she would help my pick out sexy slutty stuff to wear.I'm middle aged but have been dressing up in secret for years, but I really had the urge to get out in...

Crossdressing

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...

Mike s new girlfriend

It started as a typical Monday really; I waved my wife off to work and then went upstairs for a long bubble bath and shave, as I stood drying myself and rubbing baby lotion into my body my cock started to grow as I got excited about the morning ahead. I quickly put on sweat pants and then raced to the outbuilding at the back of the garden to fulfil my cross-dressing desires. I opened the door to the outbuilding and pulled down the dressing up trunk from the roof rafters, my heart was beating...

Crossdressing

A Crossdresser rsquo s Life

Initially i use to wear my sisters dresses or my mothers bra,panties,saree,blouse,petticoat and see myself in a mirror and admire myself. Though i wasnt so good at makeup, i used to apply lipstick and put some jewellery items. It couldnt make me look like a girl but the feel of women’s clothes turned me on. And then i used to masturbate after my every crossdressing session, thinking about being fucked by a guy. But then as i grew up chances of being alone became less and i had to kill my desire...

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 Neighbour s Knickers Part 1

It was a sultry summer night but it wasn’t the muggy air that was making me hot. It was my clothes. I’d felt the urge to dress up in a very sexy outfit. My preparations had started much earlier in the day, and they had been thorough: my whole body was clean and smooth, shaved so that there was not the slightest hint of hair anywhere other than on my head. My heart thumped wildly as I made my selection: a schoolgirl gym skirt and top, with bra, blue panties and stiletto heels. I felt sexier...

Crossdressing

Across The Street Part 3

Mike was leaning back in his desk chair enjoying the after-effects of his orgasm. He leaned forward and looked into his telescope to check on Leann. He saw that she was still in her chair with her eyes closed and her legs spread, floating down from her orgasmic high.As he flopped back in his chair, he still couldn't believe it. The girl he had been spying and masturbating to her dancing image was actually a male dressed as a female. What surprised Mike the most, was the fact that he was not...

Crossdressing

Across The Street Part 3

Mike was leaning back in his desk chair enjoying the after-effects of his orgasm. He leaned forward and looked into his telescope to check on Leann. He saw that she was still in her chair with her eyes closed and her legs spread, floating down from her orgasmic high.As he flopped back in his chair, he still couldn't believe it. The girl he had been spying and masturbating to her dancing image was actually a male dressed as a female. What surprised Mike the most, was the fact that he was not...

Crossdressing

Erica Loves It Part 1

For my entire life, I've always thought it was so unfair that girls gotto wear all the really cool clothes. They were softer material, better color choices, and looked so much better. In fact, when I was very young I wore dresses whenever I got to play with the girl next door, but that was always for the tea parties and such we liked to have. But by the time I discovered sex and masturbation I really did want to wear a dress and not just for a tea party. When I was sixteen, I began wearing...

Crossdressing

Bookstore Bunny Gang Bang

Dressing as a sexy girl is my favorite way to meet men and have fun. There are so many different sexy outfits a girl can wear to attract men and turn them on, they ensure it never gets boring for a man. Every girl wants to be her sexiest when wearing lingerie and I am no different. Recently, I was on a business trip which included spending the night in a motel located across the street from an adult bookstore. Immediately upon checking into the motel, I got the urge to dress up in sexy...

Crossdressing

Unexpected Turn of Events

I sat in my favourite bar sipping at my glass of Chardonnay; I had been coming to ‘The R Lounge’ for a couple of years. I watched the guy talking to his friends across the room. They were all dressed with a bit if style but he had caught my attention. He was wearing trousers with a casual blue and black stripped shirt. He was probably five feet nine inches tall. He had an average build; not to slim but trim enough to know that he tried to stay fit. I guessed he was around forty years old. But...

Crossdressing

The Adventures of Patty

“You're wearing my things again!” Brenda screamed when she came home early from community college and found me prancing around the house in one of her short skirts. “Take them off, you little pervert!” It wouldn't be nearly as bad if I were her little sister and trying on her clothes but I was her brother. But it wasn't as bad as it could be. I mean, if she knew what Tommy and I had been doing just two short hours ago, she'd really be pissed. Truthfully, Tommy and I had never really done...

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...

Summer dressing

It was the mid 1980s, I was 20 years old and it was the summer holidays. For the long break from college I'd managed to find a vacation job in Kent in the south of England. It wasn't brilliant but I was going to get some experience of working with computers, and earn a bit of money to keep me going during term time. The company was based in a small town where I had found a room in a house with a fairly old-fashioned landlady. The freedom of being fairly anonymous in this new job and town was...

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

Mother and Crossdressing Son Fantasy

Mother and Crossdressing Son FantasyThe story is about how my passion for wearing women's lingerie helped me to establish a more intimate relationship with my mother.I'm a 42-year-old man and I still live at home with my mother. My Father passed away 20 years ago. We live in a suburban bungalow and I have a nice little apartment in the basement. It's not as private as I would like. That's important because four years ago after discovering a number of chat sites where men present themselves in...

Getting A Grip On The Situation

As our story opens we find sixteen-year-old Ken almost naked and laying at Vanessa's side enjoying the slow descent from his orgasmic high. The wonderful feeling is made even better by the fact that Vanessa's body is pressed against him and one of her satiny smooth legs is on top of his leg.He smiles to himself as he glances over at her and recalls her asking him not to tell anyone. It was a request that was not really necessary. Being jacked off by your buddy that was dressed and made up as...

Crossdressing

The Motel And Black Lingerie

I had been on the road most of the day, having travelled almost six hundred kilometers in an effort to visit some of my most important clients. So, it was a relief when I arrived at the motel and was able to check in and get into my room.After checking my e-mails, I decided to head to the bar for a relaxing drink before contemplating what to choose from the restaurant menu.The bar was nearly empty, with only the barmaid and one other guest in attendance. This was good – I really felt that I...

Crossdressing

Finding Tammy

John knocked on the door to his friend’s house and it swung gently open. The latest chart music boomed from inside. He called out, “Hi its John?”No answer; so he went further in the house the music was coming from upstairs so John went to investigate. He needed to find someone so he could pick up the money. The music was louder upstairs and though he called out again no one answered.Then he saw his friend’s thirty year old son Tim. He was dancing around in a red lace thong to the music. Tim saw...

Crossdressing

Taking That First Step

Lance was seated on a bench on the tree-lined sidewalk waiting for the store to open. Despite the warm morning air he began to sweat and his heart pounded in his chest, this was a bold step for him. Now, this particular store was located in an older but still very popular outdoor shopping center despite the malls springing up everywhere. It was commonly referred to as a specialty shop, their specialty was women's lingerie.Before he knew it he saw the attractive saleslady approach the door and...

Crossdressing

All the Way Part 1

I'd only been married a little over a year when my wife came home early and found me jacking off using a pair of her panties and to be sure, this wasn't the first time. There I was lying in bed with her wispy little nylon panties wrapped around my dick and cumming like nobody's business. I was so wrapped up in my own pleasure that I hadn't even noticed her standing in the doorway watching me. “Are you having fun?” Her voice scared the shit out of me and my erection faded much faster than...

Crossdressing

A Terrific Threesome Part One

When my girlfriend and I moved into our new apartment, the tall handsome maintenance man came by to put a hand-held spray-jet nozzle on our shower for us. I was home alone and dressed in a sexy little pair of Sherry's panties when he arrived and I put on her little short black silk robe to answer the door. When I opened the door, the maintenance man's eyes went directly down to my soft, smooth-shaved legs down below Sherry's little black silk robe. The man standing before me was so tall and had...

Crossdressing

The Man In The Window II

Nick and Di were the last two diners in Luigi's trattoria, though the patron seemed unconcerned about them remaining so late. He wandered across to their corner table, placed two small glasses in front of them and poured a colourless liquid into each."Compliments of the house signora e signore!""You always know it's going-home time when Luigi offers you a free Grappa," Di said with a chuckle.Nick nodded his thanks and took some coins from his pocket to leave as a tip in the saucer with the...

Crossdressing

Six Months

After all those years of longing to be free, stuck in relationships with women that frowned upon my cross dressing, I was still very much relishing my freedom. I was dressing every moment I could, the minute I got home from work every single day; a mini dress, heels and stockings were what I craved so desperately. I had been living alone now for a couple of years and would have thought he urge would have sated by now but I still hungered to be feminine at every moment. I am five foot six, small...

Crossdressing

Wearing Her Panties

Let me just start out by saying this, I’m a straight guy. I love women. I love everything about them from their gorgeous breasts and pussies to their shapely legs and asses. I’ve never been attracted to men. Never. I have no problem with guys that like other guys. That guy is just not me.But I love wearing women’s underclothes. They are so much softer than men’s clothing. The lacy panties and smooth silky chemises feel amazing on my body and really turn me on.I’m not a real big guy, I’m about...

Crossdressing

How My Crossdressing Began

Let me find where to start. That may sound like a simple parameter but for a few reasons, it's less clear. I recall as a c***d being magnetized to the colour sales junk mail delivered to the house weekly. Pictures of women in underwear fascinated me and I even collected a few of my favorite cut outs. I even recall making a paper bra to try on. That didn't go too well I don't think. My next step was peeking at my mums underwear drawers for things that looked like the ones in the pamphlets....

The Making of Kairi Fox Part 2

For the next few days, it was safe to say my anxiety was through the roof. Every notification, email and slight noise from my laptop sent me into a frenzy of confusion and a little bit of horniness. Someone had been recording my dress-up sessions through my webcam. I had taped over it now and made sure that nothing could be seen. Everything I did online was careful, and I began using a VPN just for extra security. Sarina. Mistress, apparently. She already knew, though. Fuck.My days were wrought...

Crossdressing

The Slut Within

I was 22 years old at the time, and I had been crossdressing for a few years. For some reason I could never control my desire to put on women's clothes and prance around my apartment looking all sexy and slutty. Normally I can never decide what specifically to wear as I like to change it up all the time, from wearing latex lingerie to sexy roleplay outfits and beyond. I am 5'9 with a slim build, shaved body and long brown hair and eyes, with a 5 inch clitty cock. I had never had sex with a man...

Crossdressing

Webmeets Diary Ch 01

Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible.I was nineteen when I found the site. Like most male nineteen year olds, in fact like most males past the start of puberty, I had sex on the brain a lot,...

Crossdressing

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

Becoming Jessica

April 1987It had become a bit of a Saturday ritual. I’d cycle over to Matthew’s house mid-morning, and we’d spend the day doing boy stuff together. We were both into sport and keeping fit, so we’d maybe go for a three-mile run, do some fitness training in the garden, then watch TV or goof around in his room in the afternoon.Matthew’s mum and dad were very pretty laid back. They usually went shopping after lunch, and Louise, Matthew’s hot younger sister, was mostly out with her latest boyfriend,...

Crossdressing

My Own Story

I have been into pantyhose for as long as I remember. I am not sure why I love them so much, but I can't seem to get enough, especially how beautiful women's legs look when they are wearing them.When I was sixteen I remember playing around my mothers nylon covered legs when she came home from work. She would always wear very sheer hose and had wonderful legs.During the summers when she and my father would be working I would try on her knee highs and would love the way they felt and looked. As...

Crossdressing

For Mistress Sarafina Part One

Alice was clad in a tight pair of black lace silken panties that felt so smooth upon her caged genitals. This pair of panties, more so than any other pair Alice owned sent aroused shivers up and down her whole body whenever she was made to wear them by her Mistress. Mistress Sarafina had left Alice a detailed text message earlier in the day explaining what Mistress Sarafina expected from Alice when Mistress Sarafina returned home later in the day at 4pm. It was now 3:55pm and Alice was making...

Crossdressing

When Danny Met Judy

When Paul and Sue announced they were taking a holiday in the new year, I was as eager as they were for that week to come. We had a reciprocal arrangement, whereby the couple that remained at home would periodically look into the other's house, to water plants, remove the build-up of mail behind the front door and just generally check for anything untoward. I'd just dropped them off at the airport when on my journey home I received a text from Sue. "I think I might have left my hair...

Crossdressing

Bobbie Is In Denial

I woke up the next morning naked with Amy spooning me. She was fully clothed, even had her high heels still on. My mouth was dry and my ass was sore. I felt like a rag that had been rung out. What happened?Then I remembered kneeling in front of Joe, my ass hanging out like a juicy ham, practically panting and drooling over his thinly clothed cock. My sore little cocklet, which for some reason was tucked between my curled up legs, was already hard and leaking precum. Sometimes I push my cock...

Crossdressing

How It Started

At twenty five and being a blonde haired blue eyed light skinned guy, I had little hair except on my head. So, it didn't take long to achieve the smooth feminine look that I wanted. Of course, I left some "down below" because I looked young and if I shaved it all off I feared looking underage. My blonde hair was long, during the week I wore it in a guy style. On the weekends it was different, it was curly and girly.So, I was preparing for my weekly encounter. I had my hair looking pretty and my...

Crossdressing

Exploration Discovery II

After my neighbor, Jack, caught me dressed and made me his girl, my mind was awash with conflicting thoughts and emotions. I had been dressing as an added thrill to masturbating for years, and had fantasized about being with a man, but always considered it just fantasy. I never thought of actually doing it, but now, it had gone from fantasy to reality in just a few hours.Not only had I actually sucked a man’s dick, and let him fuck me, but I had loved every minute of it and couldn’t get the...

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

Being Christy Part 1

The summer before I went to university was hot. Really hot. It barely rained for weeks and when it did, it came down in torrential downpours. The air would get heavy during the course of the hot humid mornings and by lunchtime the clouds would darken and you could feel that it was going to be getting very wet, very soon. The day I first met Jenny and James I’d been into town in the morning, had a look in the record shops (this was when you’d still find the big chains on the high street, along...

Crossdressing

My date with Ben part 3

I was invited to Ben’s house for dinner Saturday evening and spent the day getting ready. His wife Susie was looking forward to meeting me again and getting to know me better. I was unsure how the evening was going to go, but I decided that I was going to try and enjoy it as much as possible. I spent the afternoon getting ready, and shaved smooth all over, hoping that Ben and I would get to be together again. I moisturized after my shower, and enjoyed the smooth feeling of my body. I had...

Crossdressing

My oddesy 2 Liam

It had been a few weeks since Glen's puzzling rejection and I was in a slump. I hated my body more than I had in years. Not even sneaking into my sister's old room and playing dress-up could cheer me. And my best friend noticed. Liam was in most of my classes at school and we knew each other since third grade. He had olive skin and a solid German build. Noticing my gloomy disposition he decided to do something about it. My phone buzzes on a slow Friday afternoon. "Hey, man. I know you're...

Crossdressing

Ever tried dogging

Nick steered his sleek silver turbo-charged coupe across the deserted Cambridgeshire by-roads towards Ely. The town was justly known as 'the ship of the Fens', as the tower of its majestic 16th century cathedral was like a navigational lode star. Ely's train station was only a few hundred yards from the cathedral and Cathy stood waiting in the shade of the station building's canopy. She wore the shortest of floral print dresses, with pink fishnet stockings and open-toed high heels, revealing...

Crossdressing

even more crossdressing fantasy

frannie again and i am still lusting with wishful fantasy - i love dressing but i really crave sucking cock while wearing my womens clothing - mmmm mmmm - munching on masculine meat is a treat i always think about when i am heeled in my wig so when i heard from my reluctant friend from up north, i got real excited thinking about going down on his meaty manhood in pantyhose - third time a charm maybe ? his previous two visits were on a friday but this time he suggested a monday - ahh the window...

A Picnic in the Park

It was a beautiful spring day, the kind of day a girl starts to think about wearing her new bikini to show off her hot body for lots of men. I was feeling frisky and thought meeting some new men would be fun. There was a county park near my town where lots of men go to meet up for some good blowjobs and hot encounters. I planned to go there today.My new bikini still had the tags on it and was smelling fresh and new when I pulled it out of the drawer. It was a sexy little silver bikini with a...

Crossdressing

Vanessa Spends a Night Semi alone

One night I was laying around bored, so I decided to get all sexied up for no one but me. I got out one of my favorite outfits, which you can see in my picture. I was so excited as I undressed, and laid everything out that I was about to slip on.First I put on my sexy Victoria's Secret thong. It was white with black lace, and it felt so hot as it slid on. Then, I put on the matching bra. It had a lot of padding, so even though I have a little bit of a chest, it really helped to give me that...

Crossdressing

Belle brings back a girl

Lucy was lazing around in the living room when she heard Belle drunkenly try to scrape the key in the front door's lock. She heard giggling - a second voice. A woman's. Lucy put her tattered copy of Asimov's Second Foundation down on the coffee table and owled the door with interest, her nylon legs sprawled across the arm of the sofa. Lucy and Belle were both avid readers. Between them they made their way through perhaps 8 to 12 books a month. More, when they had no university deadlines or...

Crossdressing

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