Dress Up indian porn

Two Girls Are Better Than One

My girlfriend, Sherry, had nice, big C-cup titties and a face like a young Marilyn Monroe. Needless to say, she got hit on by lots of men wherever she went. She was also a nyphomaniac who liked to be fucked ten times a day, so we had a great sex life. She found out I enjoyed wearing lingerie, so, as part of our sex play, she would dress me up in her panties and bras and stockings and put lipstick and makeup and eye shadow on me. This kept me hard for her for hours and she really enjoyed all the...

From dream to reality

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

The Beauty And The King I

Carol King was the lesbian who used to pass as a man. Big Bro procured call girls for her every week. One night, however, he demanded a raise in his commission for obtaining the call girls as her sexual partners. Carol reluctantly made the deal with him before taking Dee as her girlfriend for 72. The prolonged GFE session turned out to be a momentous opportunity for both the girls to accept each other as life partners. Cast of Characters:Title Characters:Carol Maxine King AKA Carlos Maxwell...

Discovery Part 2

It had been an amazing year for Kyle. At eighteen he attended his first get together for those that cross dressed and their supporters. It the first time since the urge to dress up came upon him he finally felt safe and accepted.Over the following months, he perfected his skills at makeup along with dressing, walking and talking like a female. Soon he was one hundred percent passable in any light and he couldn't have been happier. It happened one afternoon that Kyle's secret had been discovered...

Guys Don t Wear Dresses

Guys don't wear dresses Janet L. Stickney [email protected] I knew that I wasn't going to do it. After all, guys don't wear dresses, at least not any guys I know anyway! But she stood there looking at me with a very determined look on her face, one I was very familiar with. As I looked at the clothes I swallowed hard, wondering if it was true. That I would look sensational as a girl that is. Mom thought so, and made it clear that she wanted me to at least try it. There was going...

Stefanie s Crossdressing Memoirs Vol 6

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

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...

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...

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...

Damn Dress Code

Damn Dress Code By Margaret Jeanette Hannah Muggins was getting dressed. She put on her blue pants suit and she could hear her husband, Ray, on the computer in the next room. He was playing games from the sound effects she heard. She wished he didn't spend some much time playing games on the computer. Hannah was very successful. She owned six stores in town and a family restaurant. She employed good managers in every one of them. Right now she was negotiating to buy a liquor store....

The Early Steps of an Odd Couple

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

Crossdressing Charlie Episode 12 Seventeen

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

Dressing Up For The First Time Part 2

Dressing in my sisters clothes became a regular thing after about 2 months of doing it, I would use her vibrator on my ass at least once a week. My family was gone more often so it gave me plenty of time to prefect doing my make up, hair and shaving my legs. One night when my family WAS home i was looking for a pen to write a card. I went to my parents room to look for one and on my step mom's dresser was a small blue key, i had no clue what it would go to and for some reason it seemed...

Noodles Part 2

Mark and I were still smiling and reveling from our exciting private dance with Amber, as he pointed the car towards my neighborhood. Ever since Mark mentioned that Sunday nights are Ladies Night, I wanted to know more. I prodded him, "What's so crazy about it?""OK," Mark began. "For starters, 'ladies' don't pay cover. They get free champagne for the first hour. And their private shows are half-price. So when I say it's 'crazy', dude, it's packed. Mostly T-girls and crossdressers. They...

My Crossed Life Chapter 6 Valleys Peaks The Professor

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

My hottie night with two crossdressers

When I was 27 years old and single, I really liked going to shows at night, to nightclubs, especially when it came to beautiful women. One day I went to a transvestite show and was fascinated.These men dressed as women groomed themselves more than any of the women he knew; her wardrobe, her makeup, even her movements, were more feminine than any woman's.I started visiting an exclusive nightclub, where every night there were transvestite performances imitating well-known artists and singers.I...

I did not know I had a disorder

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

Dogging Cross Dressing and Porno

This new friendship proved to be fun and fulfilling, the girlfriend and the wife quickly became best buddies and the location of our nights together changed to her house. If we had nothing organised and they were free we spend Fridays or Saturday evenings in each other company. Usually just talking and drinking but more often than not some form of sexual encounter. Even vanilla fucking was done in each other company and the girls enjoyed playing with each other exploring the lesbian side of...

Prom Night

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

A Weekend Getaway To Crossdress In Public ndash Part 1

Hi All, I am 32 years old married guy without any c***dren living in California. I believe I have had the bisexual urges since my early c***dhood. But I somehow developed a new fantasy to cross-dress in last couple of years. Since then I have been thinking about it pretty much all the time and been trying to explore it. Couple months ago my wife went out with her friends for lunch on a Saturday afternoon. I figured it would be a great time to try some of my wife’s clothes. I immediately went to...

And It Begins

There seems to be a common belief, if you want to call it that, that there are basically three “levels” of Crossdressers or Crossdressing. The first of these is what is referred to as fetish dressing. These people have no intention of doing anything other than wearing items of feminine attire. They have no desire to even attempt to emulate the female persona. This is purely a very temporary thing for little more than the thrill of it. The next group that they describe are interested in...

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...

Put it on

I was living and working in London, my first job after college. No chance of having a place of my own with these crazy house prices and this being my first job at the age of 23, so I rented a room from a guy older than me, in his mid-30s. His name was Steve and he was a masculine type, split up from his wife but seeing a feisty Spanish woman called Manuela. There were big arguments now and again but at least the sex sounded good, if the rather loud sighs, moans, groans and shrieking I could...

Jacqueline s interview

Jacqueline's interview by mya fantasy story description in this story a 21 year old proud and confident crossdresser named jacqueline agrees to be part of a research study being carried out by a psychology professor named chris. This is a complete transcript of the interview consisting of over 30 questions. Note: the interview questions are in upper case text and were written by a human (me) using the pen name mya fantasy. The answers are those provided by chatgpt without any...

Crossroads Ch 02

The second chapter in this crazy little tale. I really loved my little adventure out as a woman. I liked the power I had over men. I was seriously thinking that I would like to live as a woman full time. That would be quite a commitment and one that would change my life forever. As I said before I worked for a really liberal company and one day I got up some courage and went to my boss. I explained to her my desire to live in public as a woman. She smiled and was very understanding and said...

still more crossdressing fantasy

hey again - franny the tranny here looking to share more wanton acts of pantyhose lust with my new foundling - a fetish friend who fufilled my oral desire with gobs of cum all over my face - he had really touched my slut side as i savored his sperm but this satsifaction was short lived as i craved morei am such a pantyhose whore constantly dressing and reaching out to other pantyhose preverts on line - i enjoy making crossdress / encasement vids for posting - a regular addict to exploring my...

Stranger Fuck

I noticed the time strike 10pm on my watch as I got out of the cab outside the Red Circle. Hopefully tonight I was going to get lucky. After paying the cabbie and stepping out of the cab, I fixed my tight pink and black striped dress as I stood outside the club. The Red Circle was the most notorious Sex Clubs in the city where couples and singles went to hook up. Tonight was their Gender Bender Fetish night, which is why I had got dressed up tonight.I have been crossdressing since I was quite...

Magic Dress 2

Magic Dress 2 David Peterson and Katherine Davies were in their fifties. They were not married, but some years ago they had met at a party. They had many common interests, and they seemed to click. After a year she had asked him if he wanted to move into her apartment. "Oh?" "Do you have any complaints?" "Well, no." "Then what's the problem? You are renting your small apartment. I own this one, and it has plenty of room for two." He had looked at her for close to a...

A Weekend Getaway To Crossdress In Public 8211 Part 1

Hello All, I am 32 years old married guy without any children living in California and a fan of Indian sex stories. I believe I have had the bisexual urgent since my early childhood. But I somehow developed a new fantasy to cross-dress somehow in last couple of years. Couple months ago my wife went out with her friends for lunch on a Saturday afternoon. I figured it would be a great time to try some of my wife’s clothes. I immediately went to our bedroom and searched for her clothes in her...

A Cross Dresser s tale

You may think of me as Fiona, and I am a cross-dresser.A story by Erica inspired me to pen my saga of cross-dressing. I am also a recovering alcoholic, with a few days over 19 years without a drink as I write this, and I suppose the two tales are intertwined to some extent. Not that I am a saint by any means, a lot of people with a lot less time have a better sobriety than I. But I learned that alcohol is a poison to me, so I avoid it. I just do irrational things when I add alcohol to my...

Lil red dress

After a big night out I was finally on my bus home walking up to back seat I saw a girl passed out in tiny red dress sitting beside her my first thought was if I could fuck her on back seat without her waking up so I slid my hand in her top and pinched her nipple she didn’t even stir so I lifted her dress her panties looked damp pulling them to 1 side her pussy was flooded with cum it was obvious she’d been fucked by quite a few pulling my hard cock out I pumped into her sloppy sleeping...

Tight Dresses

Reddit Tight Dresses, aka r/TightDresses! I love to see sexy girls dressed up and ready for action, and seeing them in a tight little dress, just gives my dick life. Lucky for all of the perverts online, /r/tightdresses/ is a subreddit filled with pictures of horny girls who are wearing their sexiest dress. Of course, all the dresses are tight and showing off their curves quite nicely.Lots of images of amateurs and known models.The whole point of this subreddit is to focus on the babes who love...

Reddit NSFW List

576 Shadow Oak Drive Part 1

I met Molly on a seemingly random day. How could I ever have known she would change me forever? It was late April and I was working behind the cash register of a local department store. I was eighteen, just out of high school, and didn't have any sort of plan for my future. I figured that I would take a least a year off before applying to any universities. I liked working at the department store not only because of the discounts, but because I had figured out a way to sneak some of the clothes,...

My first halloween dressed

My First Halloween (Dressed) By tied2ava I had been invited to a Halloween costume party by a former co worker and had accepted even though my wife had refused to go saying her usual costume parties are stupid and a waste of time! After deciding to go I thought about what kind of costume I could wear? I thought of all the usual costumes vampire, bum, army solder, batman and so forth then came upon the idea of dressing up (I have been a deep closet cross dresser for years) I figure...

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,...

A boy s femininity awakened Part one

In the North East of Scotland, large families were the norm even up into the 1950s. So, when I attended the local Primary School, there were scores of children of my age there, all shapes, sizes, and temperaments. This meld of kids meant that I didn’t stand out from the crowd despite being a softy. My time at Primary School was therefore quite comfortable and peaceful, but this situation changed when I moved up to the Senior Secondary School. The overriding ethos of the school was that boys...

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...

Caught cross dressed part 1

My name is Philip. I am married to a beautiful woman called Helen, and a few days ago... I did something very stupid! My wife, her mother, her beautician, my P.A. from work, and any of their friends, (in fact, anyone that they choose,) are now completely in control of my life. They are my Mistresses, and I am fully subservient to their every desire. In fact, I am now nothing more than their sex-slave!Recently, whilst I thought that my wife was visiting her mother, and would not be back all...

How to please your girlfriend

(Some of this story may be slightly fabricated, but don't worry about what is and what isn't, just enjoy the story.)It was back in February when me and my girlfriend plus a few friends decided to go to a con. We hung out together and thought it would be fun. A friend bought my ticket and the closer it got to the con, the more we were excited. Not only did we get more excited, the closer we got, the more my girlfriend begged me to cross dress."Pleasepleasepleasepleaseplease!!!""No. N-O. That's...

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....

A Tale Of Crossdresser

Hey, this is my first story that I am writing but not definite new to the glorious crossdressing field, Kindly forgive me if there are any mistakes, suggestions are welcomed people who are moving to Bangalore or in Bangalore if they want to my friends or a hook up we a cross dresser can contact me at m First, I don’t have a perfect girl figure but I wanted to be dressed as a girl, do a girl activity from a long time but it didn’t come true. I always used to wear my mom’s clothes like bra &...

My Neighbor s Wife

Carol, my neighbor's wife, had been suspecting for some time it seems, and when her husband had to go away for several days she took it upon herself to confirm her suspicions. That was the beginning. It was early morning when there was a knock at the door. I thought 'What the fuck? No one comes to my door!'I was surprised to find Carol at the door. Although Carol was smokin' hot. She had long wavy blond hair, ample breasts, a nice ass, and long slender legs. I think it is mutual when I say we...

My First Dress

My First Dress by Sissy Susie It all started the day mum had to take my sister Sandra to London for the day. My sister's school orchestra were playing in the regional finals of a competition. As there would be a lot of waiting around mum had decided that I would spend the day with my aunt Caroline and my twin cousins Becky and Kirsty. I did not mind because although the twins were fourteen, two years older than me, they enjoyed things like football and we even played it together,...

Hedonistic Crossdressing Part 3

The best way to describe Vince, probaly is that he was a socially functioning pervert. I had no idea just how varied, and intense, his sense of erotica was, but I was going to find out as time went on. Perhaps the worst thing is (or best perhaps, depending on your point of view), is that I became quite the little "apprentice", you might say. I'd been his "guest" for only a few hours, and I'd experienced more than I'd ever dreamed. I've dressed, I've sucked my first ever cock, been fucked...

Dress like your daughter day

Dress like your daughter day: It started when my oldest daughter, Claire, was sent home from school. It turned out that despite the fact that I had told both my daughters what I expected of them which was that they dress modestly when they went to school and that they not wear the kind of make-up that Claire had started to wear or that they not wear miniskirts to school, Claire had started to do just that. Furthermore I didn't know about this because they either left for...

Dressed for Disaster The Sequel

FORWARD: This is the final episode of the Dressed for Disaster trilogy, by the author of The Jessica Project, a gender-bending thriller now available on-line from all major booksellers. DRESSED FOR DISASTER - THE SEQUEL (c) 2002 by Nom de Plume Patrick Summers wandered the streets of lower Manhattan in an aimless fog, the chaos surrounding him a lurid backdrop for the turmoil between his ears. He had just suffered two tremendous shocks: his narrow escape from the collapse of...

A Trip To Joann s

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

We All Have Our Stories

I want to present a few short vignettes concerning crossdressing. A most interesting and individual form of sexual gratification and fulfillment. The first story concerns a strong man, happily married and happy with the sex he is getting from his wife, but something seems missing in his life. He often walks the streets and window shops, but seems to be drawn to the windows displaying ladies' wear, from dresses, to frilly underwear, to stylish shoes. He is drawn to it all. And he forms the...

How I became Jayne The Crossdresser

It started in 1976,around August,I had just met John a guy my around my age,who lived alone near me. He wasn't shy to admit he was gay,and I was curious,and I told him one Friday after we got back from the pub about my interest. Before I knew it John & I had undressed & I had Johns cock in my mouth,sucking him off,& he soon quaked into an orgasm,cumming in my mouth so fast I gagged slightly before I managed to swallow most of it.John was keen to make it a pleasure for me &...

Blueberry Fields Forever

I have been cross-dressing in secret since I was in my late teens. Over the years, I have accumulated quite a wardrobe and whenever I get a chance I like to get dressed. When there is little time, I just throw on a sexy bra, panties, and genderless outer clothes like a sweat suit and sneak off to the local adult bookstore in a totally non-passable condition. There I can usually find some dick to suck or someone to fuck my ass. Sometimes when the family is away, I get fully dressed in clearly...

Mistress Hannah s Pathetic Husband Part 5

I was making progress as a slave but unkown to me, one of my stories helped Mistress Hannah see an opportunity for a particularly fun afternoon and a chance to help an old friend through a rough spot in her marriage. Several months of aerobic classes and feminization had increased my stamina and made me more comfortable when we spent our Sunday evenings out for dinner and as member/patrons at the theater club where I had been displayed on my coming-out evening. The pumping of my boobs and cock...

Becoming a Sissy

For the longest time I can remember loving the look of pantyhose on a woman. It made their legs look so sexy and especially when they wore heels. I would always jack off while looking at pictures of women in pantyhose in magazines. So one day after turning sixteen I got the nerve to try on a pair of my aunt's hose. OMG they felt amazing and the way they made my legs look so smooth and sexy was a huge turn on. So mush that I had to lay there and masturbate. They also made me feel feminine. I'd...

Lewd Tales 8211 Part 10 Dressing Up Mom

Thank you all for showing great support. It’s been a while since I wrote. Got held up with work and other stuff. You guys have shown so much patience. But, no more waiting. Here’s the next part! Narrated by David. I got back home by around the afternoon. I went in, but there was no one to be found. Everyone must be in their rooms. I, too, was tired and went inside my room to freshen up. While I was washing my face, someone opened my door. Mom: At last, you came. Me: It’s not...

My Neighbor s Wife Pt 2

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

The Cross Dresser and The Big Fat Fuck

As soon as the door closed to her place Debbie started squeezing me tight. Before I knew it I was the one with my dress around my ankles. Soon I was being pulled down the hall to Debbie’s bedroom. While I sat on her bed, Debbie went in her bathroom to freshen up. When she came out she was wearing a sexy red night gown. If it weren’t for the fact it was a size 6X you might have thought Debbie bought the thing at Victoria’s Secret. ...

The Cross Dresser and The Big Fat Fuck

As soon as the door closed to her place Debbie started squeezing me tight. Before I knew it I was the one with my dress around my ankles. Soon I was being pulled down the hall to Debbie's bedroom. While I sat on her bed, Debbie went in her bathroom to freshen up. When she came out she was wearing a sexy red night gown. If it weren't for the fact it was a size 6X you might have thought Debbie bought the thing at Victoria's Secret. ...

Surprise at Girls Night Out

Surprise on Girls Night Out in New Jersey I explained in an earlier story that my life took a strange turn when I turned forty. I had not been cross dressing for many years, but I had the urge again to bring out my alter ego and the urge was stronger than ever. I really prepared for Cassie, short for Cassandra (I also go by Sandy) by taking a year to buy all the things I needed and get into great shape so I could wear sexier outfits. Sorry to all of you faithful readers that know all about...

Working It

I’ve needed some repairs and painting done in a bedroom for a long time and decided to get some estimates. I had a water leak in the ceiling, and there was a hole there since it was fixed a month ago. Several professional painters came in and they all wanted $700 or more to do the job. I decided to ask my friends if they knew someone who might do it for less. One of my friends told me about Jim, a young guy going to college, who also has a painting business on the side. She told me that he...

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...

Caught Used and Loving It

I knew I had time now; my wife had gone out with her friendsand wouldn’t be back until 10pm at the earliest. As it was only 6:30, I knew I could spend time getting ready before playing around on the computer and enjoying a nice relaxing but exciting orgasm. My cock was more than ready as I hadn’t had sex for over a week and no chance to masturbate either due to either the kids being around or my wife not being in the mood. So as soon as she was out the door, I looked out of the window to watch...

How Hockey predisposed me to be a Cross Dresser

I had a thought the other day, my hockey equipment has a number of striking similarities to lingerie!To set the stage, I am a cross dresser. Like most of us, I love everything about ladies undergarments. I like seeing lingerie in stores, on models, on women, on men and of course on me! I love the feel when I am dressed up. I love the taboo of wearing them. I love the thrill of being "underdressed", that is wearing lots of lingerie under your manly clothes, when I go to work. I especially...

Jenny Mike A Day out

I woke up in the morning with Michelle’s arm around me. We were spooning. She was the big spoon. I held on-to her arm stroking it gently as I recalled how ‘Mike’ and I had gotten it on in the living room the previous night. ‘Mike’ had fucked me on numerous occasions in the past, but my ass was still sore after what we had gotten up-to last night! God it was so hot! I turned my head to look at the clock on the night-stand and saw that it was 9:30 a.m. I slowly lifted Michelle’s arm from around...

Friday night crossdressing

Silky long sleeved blouse and skirt? A dress? Or just lounge around in my lingerie. Parking my truck my anticipation only grew to full out excitement, a huge smile was plastered on my scruffy face. I was almost skipping up the sidewalk. I'm sure some of my nosy neighbors saw me but I didn't care. It was a long week to hide Lisa within me. Once inside my apartment, I quickly got undressed from my work clothes and stood in front of the floor length mirror to admire my lingerie I always...

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...

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...

CAUGHT WEARING MY UNDIES

CAUGHT WEARING MY UNDIES. Having recently been left quite a large sum of money by my late aunt in her will, I decided to buy my own house, and start my own business as a handyman. Because I was bored with my present location in the north of England, I moved down to the midlands and bought a very nice isolated cottage about 20 miles south of Birmingham on the outskirts of a small town, and after a few weeks of settling into my new home, I put adverts in several of the more rural papers, in...

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It was his own fault. He had spent far too long admiring himself in the mirror and revelling at the sight of the erotic garments he had donned and time had slipped away from him. Just the feeling of these silky garments against his skin made him hard as they always did and a masturbation session would soon follow.The mirror on one side of his sliding closet doors reflected the image of a tall and tanned young man with long dark hair and slightly feminine features. If he had been born a girl,...

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...

How Andrew became Andrea The Conclusion

It was easily one of the best summers of his teenage years. Now along with being allowed to indulge himself in his secret desire, he had sex with the stunning Lacy on a regular basis. She had become a friend, lover, employer and tutor. When school resumed in the fall he was forced to limit his visits as there was homework and studies that needed his attention. However when his parents went on weekend trips he spent the entire time at Lacy's dressed in the lingerie she provided. Halloween was...

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...

Anonymous Encounter

Well it was a boring day. It was fairly hot outside,somewhere around 93 degrees. The sun was shining, there were very few puffy clouds in the sky, and I was home alone. As usually happens when I am bored and home alone, I was horny as hell. I wanted to jerk myself off, but I wanted to do it to something different than the normal porn that I usually watch. I figured since no one would be back at the house until tomorrow, I would take the time and dress up and do my makeup and hair and really go...

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I hadn’t noticed the time, and I’d missed the last train home. The student party was fun, but I was in a bit of a panic not knowing what to do. People were leaving, and the crowd was thinning out. If it had gone on for several more hours, I would have stayed there and taken the first train in the morning, but that didn’t look likely. The hostess was already clearing up. I figured she’d be dropping hints at the last remaining people to go home soon. “What’s up?” said Zak, looking at me with...

Crossdresser Turns Gay To Seduce His Tailor

Hi all! I am a family man with a loving wife, but she doesn’t know about my crossdressing. It just so happened that she had gone to her mother’s place during her pregnancy, and I got ample time for my crossdressing. I did all of my shopping on Myntra and bought myself some nice soft satin sarees, dresses, gowns, tops, high-heel shoes, a makeup kit, perfumes, and loads of bras. I was waiting for the delivery like a curious kid waits for their birthday gifts. Finally, the day arrived and the...

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...

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

Happily Ever After Finally a Princess at Disney World Part 1

This is a follow up to Finally a Princess which had six parts. You do not have to read that to follow this. I incorporated the back story into part one of this series. If you really want to get to know these characters though you would probably want to start, there. This story is either Pre-COVID at Disney or in a world where COVID never existed. Happily Ever After- Finally a Princess at Disney World Part 1 I was in the kitchen when Sarah got home from the grocery store. ...

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I met Robyn in one of the chat rooms on Lush Stories. She too was a cross-dresser, but far more committed to it than myself. She was a full-time dresser on hormones and is probably considered a T-girl. It was a strange relationship. We were both gurls constantly looking for cock, yet, at the same time, teasing each other like two lesbians. With so much role-playing and cybersex amongst the multitude of participants in the chat rooms, it is difficult to separate reality and fantasy. I...

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I woke up the next morning with Lisa sucking on my little clitty, making it hard. I pulled her panties to the side and began to kiss her beautiful pussy and suck and lick on her clit. I began to plunge my tongue as deep as I could into her hot wet honey hole. Lisa was about to make me cum, then she stopped. She knew just where my breaking point was. She turned around and sat down on my hard clitty and buried it in her sweet pussy. She began to ride me faster and faster, until I exploded inside...

Becky s Video

I suppose I was the one that first mentioned porn to Nikki. We'd been chatting on a girls' night out and laughed abut how I'd never found any porn in the house. She giggled and said I was bound to find some sooner or later – all men had some, somewhere. A few days later, I'd completely forgotten our drunken conversation and so when Nikki showed up at mine after you'd gone out with your friends, I was surprised when she mentioned it. We'd both had a few glasses of wine at that point and when...

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

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A seductive CD fulfills some of my secret fantasies. And I bring him pleasure into the bargain.Jeez, you bust your ass all year to be among the top sales people so you can get invited to the annual conference. Supposed to be in Hawaii or Vegas or somewhere exciting. And what happens? The company needs to save some money and holds it in the city where it's based. Cincinnati. For fuck's sake. I nearly didn't bother but there'd been some lay-offs already this year, so I decided I should go. You...

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This is a work of Fantasy. I hope you enjoy.Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly she was jealous of my legs. She was a petite sexy woman and we were almost the same size but I still had my own stuff that I’d secretly obtained from eBay and op shops.I didn’t consider myself bisexual,...

Crossdressed And Became A Complete Girl

Hello everyone..I’m harsh aka ayesha..I’m a regular reader of Indian sex stories and always search for stories of gay crossdressers.Before starting my first real life gay experience let me introduce myself..I’m a 24-year-old boy who wants to be treated like a teenage girl..Wants to be pampered.Wanna be treated as a wife for my man at home.His girlfriend when we are outside and as his slut when we are in bed.. I come from ranchi..I am slim, fair and height 5’8″..I m very curious about sex.I...

Spying on my sissy slut husband

Part oneI am married to a very sweet guy. We are both twenty-two years old and have been married for two years. Our sex life is great; he is very horny and affectionate. I never have to ask for sex as he is always willing and able.He is a Social worker and I am a nurse. We met while he was in the hospital where I work. He was working on a child abuse case. He isn’t a hunk by any means, in fact, quite the opposite; he is very feminine. Maybe him being this way attracted me to him as I had...

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Im not an author in any way but I would like to tell you about my latest crossdressing adventures. I have been crossdressing for many years but maybe only twice in a year when the mood took my fancy and only ever indoors, the feel off nylon on my legs would get me very aroused and looking at my self in the mirror wearing high heels and a very short skirt had my cock pumping and I always had an intense orgasm, but over the last few years it has became more frequent and not confined to indoors...

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

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...

amatuer crossdressing prostitute

So it started out by just a regular day. Work was really becoming a drag, and it was only 11:00 am, and my mind started wandering about what I was going to do when work was over for the day. I stopped at the mall on my lunch break and when I was done at the food court I decided to stroll through Dillard’s on the way back to the parking lot. I couldn’t help but pass through their lingerie section and noticed the cutest little bra and panty set. It was kind of a purplish flower ensemble that I...

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The Impossible Dress By Emma Smith Wednesday It's been playing on my mind again lately. It always happens at this time of year. It's wedding season again and some more of my friends are getting married. There's nothing wrong with that; I like them both and I wish them all the best. It's just that my chances of ever getting married seem to be zero. I've always wondered what I'd look like if I did marry but I've never known how to make it happen. I confess I did nearly get to be...

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The Feminization of Michael. Chapter 1 How I had found myself in this predicament Ill never fully understand. Ok I guess it was my own fault but why I didn’t kick against it when I could Ill never know. I had been involved in a sordid night of drink drugs and sex with a young transsexual hooker! Including her/him putting a bra and panties on me! I didn’t know any of this until my wife, Sue, confronted me with the brown envelope with pictures and a blackmail note. I had been caught before...

Surrendering In To Temptation Part 2

Later that day, as Grant was chilling in his room recalling the events of the morning, his sister Jessica knocked on his open door and then poked her head inside."Thanks for bringing up my laundry," she said with a smile."Not a biggie," was his response.Carrying his sister's basket to her room wasn't done out of guilt as he had performed this task before, it was done to give him a few more minutes of caressing her silky panties between his sensitive fingers. As he stood inside his sister's...

Desperate Enough to Cross Dress

A couple of months ago I was on a business trip to a major city. I was looking forward to visiting the city and the opportunities that it should offer to have some extramarital fun, as I like to have some man-to-man action on my business trips. To my disappointment, the meeting was held at an office in a remote industrial park far from the city, where there was one lone hotel and nothing else but empty office buildings after-hours. I had to endure a business dinner at the hotel dining room and...

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...

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All Dressed Up but Nowhere to Go By Jena Corso Edited By Angela Meyers Out of the bad sometimes we find some good!!! In fact during these horific times we must find some good! So if you are cross dressing and wrestling with so much? Dress and enjoy staying dressed! Embrace your female side and live in "her" shoes as long as you can and use this time to find out about if this is what you want or who you should be! Stay Safe and I have loved hearing from so many during this...

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 Charlie Episode 3 Relinquishment

CROSSDRESSING CHARLIE Episode 3 RELINQUISHMENT Charlie stared at the door as if it were a wave of fire rapidly heading toward him. His eyes watered and his hands trembled with shock. His could hear his mother's heels clicking against the shiny wooden floor getting louder and louder as she approached her bedroom door. Then, something electric shocked Charlie's brain which broke him free from his frozen state as adrenaline pumped through his body. He jumped to his feet and turned for...

A Night of Firsts pt 1

'Oh my God, this was the night,' I thought to myself. 'I'm finally going to go out dressed.'I work for a small company and get to travel a bit, but I've really only dressed in hotels when I could drive as flying with all my things makes me really nervous. The idea of me and a travel bag being examined and having a stranger discover my femme things just didn't do it for me.However, this time was different. As I only was going three hours away and staying in a larger city, I had access to a...

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