Crossdresser 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...

An Introduction to Crossdressing

Up until this point in time my crossdressing has consisted of wearing stockings or pantyhose and enjoying some anal penetration with one of my toys. I have recently had strong desires to move further but really didn’t know anyone that could help me. I was chatting recently with one of my friends on Lush about our mutual desires and needs. I had said that I really would like to do the whole deal at least one time to see if I’m really as into it as I thought I was. I also mentioned that it wasn’t...

Jaq Invites Crossdresser Over

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

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...

Crossdresser in Love

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

Telling Mom I m A Crossdresser Part 2 The Adult Store

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived. It was just past 9am when I heard a fumbling at the door, my mother had walked in with her heels in her hands and her clothes hanging loose...

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...

Telling Mom I m A Crossdresser

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

An Introduction to Crossdressing Pt 5

As Jackie and I pulled up to the club my mind was racing. My main concern is whether we look passable, and that if we don’t, that we might be laughed at and teased. As I expressed my concerns to Jackie, he said, "Remember that we are at a place for people like us who are a little different." As his statement sinks into my thick skull, all my anxiety starts to slip away. For the first time in a long time, I start to feel fearless. Being fearless is one thing, but making sure we look hot is...

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 Domina gets a new slave

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

Crossdressing Fun From A Woman s Point of View

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

Caught by the Neighbor Crossdressing While Home Al

Do you know a crossdresser who got caught in the act?This is a real life story of a crossdresser caught in the act!This happened around when I was 15 yrs. old.As my sisters were off at college and it was just my mom and I at our apt. I was home from school as we didn’t have any school that day. But my mom was still at work. So I got myself all dressed up looking pretty. As I thought I will make it a girl’s day in. I decided to wear a pair of my mom’s dark navy pantyhose with one of my...

Crossdresser s Placement Agency

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

Carolyn Makes Her Way part 3

Once I dragged my tenderized ass out of bed, tender because Mike had used a cane on me last night, I dressed in pantyhose, a navy blue, loose skirt, a cream colored satin blouse, black pumps with four inch heels, and a bra. After applying my makeup I took a look at myself in the mirror, making sure I looked good enough to conduct an interview at the leather goods store we were opening in just a few days. I decided I looked business like enough. My first order of business today was a stop at the...

First Time With Crossdressers

For once, I actually decided to look at some of the other categories on the streaming sites I'd visit. So many things came up under fetish. Some of it I don't get but to each their own. A BBW was mixed in with the fetish and as I had expected before hand, it wasn't my cup of tea. Several videos had girls dominating guys in leather or latex outfits. I liked how tight they were, showing off every curve of their body, leaving little to the imagination. Upon thought, I had never been...

Chronicles With Sexy Crossdressers

My email id is Do not forget to let me know how this sex story was. Who knows, we might get even lucky if everything goes well ;) Clean shaved men inside female clothes (or people who are known by the name crossdressers) are my new found favorites. Believe me, I always make it a point to taste every bit of them with passion and fire. My hands and tongue never leave an inch of their body. Hairless, like women and the ‘EXTRA’ jackpot called ‘COCK’, is simply divine. This is a story of how a...

The Crossdresser s Club

The Crossdresser's Club By Tammy Richards CHAPTER 1: THE DISCOVERY It was the Saturday before Christmas. Natalie was in the attic looking for boxes to wrap the last few presents, while John was running last-minute errands. As she dug through a pile of boxes in the corner, she happened to open a large box that had been pushed behind the rest. Imagine her surprise when she discovered that the box was full of women's clothes. There were dresses, lingerie, high heels, even a...

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...

My first halloween night as a teen CD

This is halloween!! A day that everyone goes out and dresses up in costumes and other things, and go to parties and drink and show off their wild side until the wee hours of the next day. And I thought to myself, since everyone goes out and wears costumes, why not dress up myself into something wild and willy?? Or in fact, why not dress up in a manner of expressing who I am and what I feel inside?? That gave me a great idea. While I am still 16 and seeing many older men getting off on younger...

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...

Dawn Visits Kansas Chapters Seven Eleven

Chapter Seven: WednesdayPart 1: Morning - Business UpdateI woke at sunrise, but Patti was still sound asleep, so I snuck out of bed, gathered lingerie, clothing, shoes, wig, and purse going into the bath to shower and shave. My dress for the day was a very simple, short-sleeve tie-waist shirtdress in tartan. After getting dressed and applying my makeup, I tiptoed out of the bedroom, closing the door behind me. Then I put on my two-inch black open-toe heels and went into the kitchen to make...

Sissy Blane in the Hart of the Valley

When I got home from the Hollywood Hills I barely had the strength to remove my makeup. I was so exhausted I just wanted to flop on the bed and pass out, but I persevered and undressed properly, removed all makeup and even put my wig back on its wig head.But when I was finally between the covers my brain refused to cooperate, rethinking the night's events, imagining how they may have looked to an observer, or to Harold Plumrose himself. I saw my lap as he must have seen it as he hovered...

Dawn And Patti Move To Denver Part Three

Part Three: A New HomeAt one-thirty, we left for the title company offices. First American Title Company was located less than two miles from the hotel, and the same distance from our new home. Teresa met us in the lobby.“Thank you for inviting Laura and me to the inaugural party tomorrow. I understand Andrew and Marie, as well as Harry and Jean, will also be there. We look forward to the evening. It should be a fun time. Let us get you the keys to your new home!”Teresa led us into the title...

A Crossdresser s Night in the Park

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

The Crossdresser Body Swap Part 1

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

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...

My Foggy Late Night Story

It was a cold, wet December night. Here I was in my room, feeling exhausted, and laying on my bed doing the whole Netflix and chill thing. I had just pulled a long afternoon and evening event with my college study group. We spent the day as total masochists painfully cramming whatever we could into our tired brains for our finals. It had worn me out so much that I didn’t want to do anything, including exercising, which was another problem I had to deal with since I hadn't exercised in nearly a...

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...

Crossdresser s Paradise

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

My Qualifications to Write About Crossdressing

My Qualifications to Write About Crossdressing By Ricky How ironic! While looking for something in my files the other day I found I have been writing about crossdressing more than 10 years now. The problem is, I now realize I am completely unqualified to be a crossdresser, let alone a writer on the subject. Think about it, just what are the qualifications for a crossdresser? Surely you've read a multitude of "true life stories" in the crossdressing magazines. Perhaps if we...

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...

Spying On My Sissy Slut Husband Part Two

After my last story of how my husband and I became lesbian lovers with him dressed as a female, both of us thought a lot about what was next for us. I did tell him that I wanted to see him with a man. Then that got me to thinking about a bisexual couple to play with. A bi woman for me and a bi guy willing to fuck a crossdresser. That would be perfect but so hard to find.My husband and I set a date for our attempt to find him a one-night stand playmate to fuck him. The rules were set. We...

Vicky s First Time

I was very open about crossdressing when I met my wife when we were in our 20s. She has been very supportive and helpful. She helps me with my hair, makeup, and picking outfits. We started having sex with me dressed up as Vicky. This soon escalated to her taking me with a strap on. I loved the times she would fuck my ass with her cock. I had never considered myself gay or bisexual but the feeling of her cock inside me opened up the possibility for more.One Thursday she told me that we were...

What Happened After Police Arrest

Hi.I am now a mature gay crossdresser.A bit of history of my life as a crossdresser.I have been gay for as long as I can remember. I have always lusted after men. As with most crossdressers, I have tried to be (normal) but have always returned.I even got married and still am officially. Very rarely did I get hard for sex and was often punished for my failure, ordered to lick her out. I only enjoyed the punishment and luckily, she found sex elsewhere.Many encounters leading to my first anal and...

Jaime s Way part 3

As Jeff closed the door he grabbed me by the hand and spun me around, pulling my nude body close to his, breathing in my perfume before locking his lips over mine. My fingers found the button on his jeans and opened them with urgency, more than a little pleased when his huge cock sprung out. “Damn, I want you so badly, Jaime,” Jeff moaned when he broke the kiss. “I'm yours to do with as you please,” I answered and wondered where that cheesy line had come from. Pulling his jeans and shorts down,...

Jaime s Way Part 3

As Jeff closed the door he grabbed me by the hand and spun me around, pulling my nude body close to his, breathing in my perfume before locking his lips over mine. My fingers found the button on his jeans and opened them with urgency, more than a little pleased when his huge cock sprung out. “Damn, I want you so badly, Jaime,” Jeff moaned when he broke the kiss. “I'm yours to do with as you please,” I answered and wondered where THAT cheesy line had had come from. Pulling his jeans and shorts...

My Crossdressing Teen Neighbor

There is a duplex across the street, the kind with an ill arranged addition that sprouts out of the top and basically looks like shit. It's a slum lord house, geared toward your average broke ass people. You'd think I was complaining, but I am actually quite glad such a place is right in plain view. There is a young couple that lives there, hipster punk types. The dude is nice enough but a little awkward, but the blonde chick is a little flat chested blonde hottie with piercings and pastel...

My first Crossdresser Part One

When she walked in to the restaurant I knew I was in trouble. It was the end of three long days at the convention and I was tired. I had come down to the NASCAR Cafe for a sandwich, mainly because it was the only bar in the Sahara that didn't have video poker...I lose a lot of money playing video poker. Well there I am with my beer and sandwich, and I glance toward the entrance just as she's strutting toward a table.Convincing she was not, a crossdresser without question. But pretty, really...

The Late Crossdressing Husband

THE LATE CROSSDRESSING HUSBAND by enduringshades Edith and I had known each other since we were teenagers. We went shopping together and often met for lunch or coffee. Friday night used to be our Girls Night Out when we dressed to the nines and headed for our favourite bar. Then we got married (not to each other!) and stopped going out together. Edith was still a party girl, but I stayed at home with my wife, Betty. I never told Betty that I was a crossdresser. I missed being...

First Time With A Hot Crossdresser

My email id is Please contact me for any queries, doubts or proposals. I usually work late nights, and leave home by 1 am. I take a rickshaw for home, which happens to cross this one spot where post-midnight you usually find young crossdressers here on business at the side of the road. They are dressed mostly in skimpy western outfits, some of them are really attractive. That’s saying a lot coming from me, for a 26-year-old straight guy. I’ve never been bi-curious either. It’s been months I’ve...

crossdresser violation

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

crossdressers first time with a guy

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

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...

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...

Confession and testament of a crossdresser

Italy, september 2011. Sorry for bad english, I try to write correctly but don't know if I did. From tonight, I was a crossdresser. I'm been crossdresser from 12 to one day before my 27th birthday. Irony. I begin to have an answer to the question: "What feel girl?" Yes, a simple question. What feel girl when wear panty, tights, dress, skirt? What feel a woman in heels, purse, with her hair falling down the shoulder? What feel a teenage when begin to make up herself? When wear lipstick,...

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...

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...

The Crossdresser s Quiz

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

Picking up a Crossdresser in a Bar

This happened about 20 years ago. The basic events are completely true, but in those days I drank a lot, so I don't remember many of the details. For the purposes of a good story, I made up a few things to fill in the blanks in my memory.It was a weekend, and my wife had taken the k**s to visit her father 400 miles away. I was alone at the house, and I knew an opportunity when I saw it. At the time we lived in a small city, and there was a gay bar in town that advertised a weekly drag show on...

Alexia s Tale Chapter 2 Online Exploration

Looks like it's never gonna stop," Alexia muttered, the warm vapor from the cocoa rising past her face like a discounted sauna. Her voice pitched higher, much to her liking, she continued, "twenty-four years old, with a job as a writer. Yet I'm bored."The maroon cardigan wrapped her exposed shoulders, but did little to envelop her breasts upon which she rested her hands that held the cocoa. Her legs, warmed by the stockings, lay crossed to one side, elegantly covering what the skirt wouldn't....

Nice surprise for the delivery man

I'm a crossdresser in my early 20's and still live at home unfortunately. The day started as it usually does when I'm home alone, dressing up. On this day I had gone for a pink G-string with a matching bra, my breast forms, and some tight leggings which showed off my pert bum very nicely. A black lace top and of course my light brown shoulder-length wig and my make-up. I was in a bit of a horny mood so I went for the red lipstick and lip gloss to give them a sparkle, red nail varnish with...

Dawn Visits Kansas Chapters Twelve Eighteen

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

Portrait of a Crossdresser as a Young Man

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

A Night to Remember or to Forget

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

Kaitlyn

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

Made my hubby crossdress and get fucked by bbc

Finally convinced me husband to stop watching me take big cocks and to put on a pair of heels and to get fucked while its my turn to watch him!ive always loved being a cuckold wife, meeting new people, having fun wherever it happens to be at, it really improved our marriage, finally i took it to the next step.i spend alot of time at nights checking out mostly pics on xhamster and few videos. ive always been turned on by crossdressers, cumshots, and a few others fetishes im into. this time i...

Crossdress Sex 8211 Mami Fucks Using Strapon

Hi my name is Sunil(although I call myself Sunita). I 29 and I am a beautiful crossdresser with very nice body. I own three beauty parlor in Delhi, and I am always dressed as a girl. I go out wearing woman clothing and no one can say that I am a boy. Now coming to the story, it happened 10 years ago. I was 19 then. I was bottom crossdresser then also and had sex with many top guys until then. I was fair and my body was very girly. I had a round bubbly ass although my boobs weren’t developed...

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...

A crossdressers first time fantasy

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...

Crossdressed In Best Friend rsquo s Mom rsquo s Clothes 8

I arrived at my step dad's place and paid the cab driver, plus tips. My body was shaking with nervousness and found myself in doubt if I should do this. I got in the elevator and pressed ‘4’. I held my bottle of ‘Pink’ firmly in my hands and the elevator stopped and opened.I walked down the hallway to Steve's front door. Breathe in and breathe out. I rang the doorbell and I was just gonna tell him that ‘It is me, Brian’. But then, the thought of me sucking his cock and everything that happened...

My First Time with a cross dresser

Growing up, like many children I went through phases. I would climb trees and play football, then as I reached my mid-teens I continued these phases but also became a lot more sexually aware, thanks to the porn magazines and porn films usually belonging to my mates dads or older brothers.Now I am in my late teens and at college.One day my Dad made a pot of tea and breakfast.“Did you sleep well, son?” he asked as I entered the kitchen.“Not bad thanks, Dad, how about you?” I replied.“Pretty good...

Dressing up

This is a series of stories rather than one story. It talks of my experiences as a crossdresser. My first experience as a crossdresser came as a teenager when I tried out some of the clothes belonging to a woman who was staying at our home. She was a gorgeous French woman with very pretty clothes and I did enjoy trying them on, but primarily as it got me closer to this woman who was way out of my league. When away from home the first time I bought a few clothes through a mail order catalogue -...

First time going out for a while

I haven't been dressing much lately. I haven't been doing anything fun really. I've had a lot going on, and just haven't had the time. Friday night when I got home from work, I just plopped down on my couch as usual. I don't know what made me horny, I hadn't been out in weeks, hadn't fucked in months, hell I hadn't even jacked off for a week, but for whatever reason I was rock hard and couldn't think about anything other than getting off. If that’s going to happen, I am going to have...

Discovery

How did I end up in this position? This was the thought running through my head as I lay face down across the bed. My mind flashed back to the moment it all began. It was a beautiful Sunday morning with a cool springtime breeze blowing through the open window. I was cleaning the house. I hated cleaning, mostly because it is never fully done. No matter how much cleaning you do, there will always be more. I'd have much rather been out enjoying the nice spring day, but it had to be done. Then it...

My New Boyfriend

I recently moved to a new town and joined a gym. It's not one of those fancy gyms with weight machines, a latte bar, and women in spandex running around trying to be noticed by men. It's a sweaty men's gym with barbells and dumbbells that require men to double up and spot for each other. The first day I was there, Jack "Kell" Kellson, a solid built six-foot-three-inch muscle boy my age, came over and spotted for me, right away. Since he seemed to like spotting for me, we developed a friendship....

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...

Roomate

RoommateIt had been a hell of a year with a divorce, a new job that had me traveling more and having to move into shared housing because my ex was sucking my bank account dry. Carl, my roommate, was a decent enough guy. I found the room on dougslist.org and we seemed to be compatible. He was neat without being compulsive about it, was a working student and was not inclined to throw wild parties. I had not been dating thanks to the bad break up, but in the two months I had been living there I...

Milwaukee Cuckold rsquo s Wife and the Crossdresser

Judy used several sites over the years to find her friends with benefits. She never tells me until afterwards what she has done. It’s rare she tells me anything in advance. One day she advised me the k**s were at my parents and she was entertaining that night and I would have to stay in the family room. My curiosity was getting the better of me.She went and took a shower and asked me to come in and shave her pussy. She had me paint her fingernails and toenails. Once she was ready she put on her...

Crossdresser for mature couple

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

A Crossdresser s Night in the Park

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

Teenage crossdresser

Here are the usual disclaimers this story is for adults only if you are viewing this andare not 18 years of age or older please close this page immediatly.There is no cross dressing in the story but this is how I began my transformation fromregular boy into cock suckking teenage crossdresser.We were having a really hot heat wave. i meat with my older brother (wear red shorts, and a black T-shirt) wanted me to get out of the house and off the computer so she suggested a movie. I felt wierd going...

crossdresser s 1st time

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

mature crossdresser 18 year old PART 1

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

Crossdresser Got Caught By The Neighbor

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

Amazing Night With A Sexy Crossdresser

Any ways, it had been awhile, and I wasn’t in any sort of relationship at the time, and the thought of being with a tranny again had started to be on my mind. Luckily, this was before Craigslist dropped its casual encounters section, so it was relatively easy to look for hook ups, and being there was a TS/Crossdresser section, I could easily contact one. I remember looking through postings, hoping to find one that was attractive enough, because as I’m sure you know, many cross dressers and...

my life as a sissy crossdresser

it should be noted that i did not ask for this disposition to crossdress, rather it was presented to me quite by accident. circa 1958...grade school PTA fashion show. PTA fathers were asked to put on a fashion show dressed as their better halves. my dad was right in the mix. I remember he wore some mid calf, grey business suit w/jacket, tan stockings and black heels. i remember this because he practiced dressing days before the show. he wore some makeup and a wig. not very passable, but not...

Craigslist crossdresser

It finally happened. I got a response! I’d been corresponding with him on Craigslist, but then suddenly Craigslist personals were banned. I tried to reply to the Craigslist generated email that I thought was his, but I’d deleted all of his email’s in a moment of weakness. Now I had no way to get in touch with him. He’d posted about hosting crossdressers and providing a safe, relaxed place for us to fulfill our fantasies. He said he would be gentle. I’d told him who I was, that I liked to wear...

Crossdressers first gay encounters

I had met Steve thru a gay dating site, we exchanged messages over a few weeks and then finally agreed to meet. I was very nervous on the way over to Steve's for two reasons. One was it was going to be my first gay encounter. The Second reason, and one i had only agreed to after Steve's insistence, was that i was going completely cross-dressed. I'd gotten dressed at home as Steve wanted. Putting on a satin and lace garter belt which i attached to lace top suspender stockings, then a lace bra...

crossdressers first blowjob

had been a private cd for years and along with that secret I always wanted to give head .. but always to nervous . I used to be a long distance hgv driver and park up at night it what I call , naughty laybys . we all know the sort . did see quite a few things going on in them . especially single men turning up with hard cocks wanting some fun . most nights I would get dressed up and climb out and walk up and down and seeing if anyone saw me , then quickly run back to the lorry and hide . it was...

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...

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...

Cd crossdresser sissy caught by mom and dad

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

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...

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...

Frank

Frank didn’t vocalize his orgasms. So I never knew he’d cum until he stopped his motion and pulled out of me. Then I’d look over my shoulder with a smile and ask, “Did you cum?”And Frank, already backing off the bed, his big cock curving downward now, would reply, “Yeah.”Although normally quite chatty, in the immediate aftermath of sex Frank turned into a man of few words, a regular Clint Eastwood (though not nearly as tall or handsome). Without having to be asked I would back off the bed as...

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...

Danni The Crossdresser First Time Sissy

by - sissy debbie This is a true story about what happened to me after graduating high school and how I became a sissy for woman who was nearly twice as old as me. --------------------- The summer after my senior year of high school a neighbor asked me to look after her house and her cat for a week while she took a trip with some friends. Her name was Heidi and she was an attractive woman about 38 years old. She just wanted me to stop in and check on everything a few times. I...

Nenu Crossdresser Nunchi Gay

Hi, na peru ajay. nenu tenth class ki vachinappatiki naku crossdressing alavatu ayyindi. enduko emo telidu, kani adavalla laga chira, jackettu vesukovatam istham. mukhamga Bra and Panty. ma inti venaka oka portion lo vunde oka ammayyi thana battalu vutiki bayata aresedi. ala aresina vatilo thana Bra lu kuda vundevi. mamuluga avi sayantram avi tisesedi. kani oko sari marichipoyo emo battalu tisedi kadu. ala tiyanappudo leka oko sari Valla bathroom lone vadilesina battallono (valla bathroom...

Losing my virginity

I'm a 21 year old attractive crossdresser from Mumbai, India. I am sharing a true story of how my roommate turned into a permanent fuck buddy!I've been crossdressing for 10 yrs now and have my own collection of all kinds of stuff you can think of. I moved into the city 2 years back and rented an apartment with a guy called Vishal who I didn't know at the time. The first few days went in unpacking and setting up my room and trying to build a decent rapport with Vishal, have some drinks once a...

Ladies Night at the Leather Bar Part 2

Now that you've met Chloe in Part One:Today I want to remind myself of how much I owe her for luring me into the circumstances wherein I met a beautiful man, a man who would change not only my life, but my basic conception of myself. I found him in the most unexpected of places. A place where Chloe brought me.SUMMER 2011. THE SAN FERNANDO VALLEY.I had just gotten home from work, put on my makeup and changed into some old, torn black fishnets and garter belt, but I couldn't decide on a top. I...

Pam s First Time

Just a few days of spring break left and I was planning on making the most of it. Well, the most for me anyway. I'm a crossdresser and I have been for a long time. All through high school I'd secretly dressed, slowly building a wardrobe of pretty panties, a few skirts and blouses, bras, my silicon boobies, and most importantly, my shoes. The most important thing I had going for me, at least from my point of view, was my stature, which was slight, no, it was petite. I have one year of college...

CD crossdresser daughter rsquo s bitch

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

Hitchhiking teen crossdresser

It was a 200 mile journey from the city to the outskirts of a small town by the countryside where I live, I have hitchhiked this road many a time but this day proves to be an exhilarating adventure into my first cross-dressing sexual encounter, I had my large backpack I carried with me with my belongings including in secret my lingerie, heels makeup etc. about 60 or so miles out a 4 wheel drive hauling a horse trailer pulled up alongside me, rolled down the passenger window a man who seemed to...

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...

My first time with another crossdresser

In this story, I'll go in depth on how I became the "girl" that i am today. It all started when i was about 5 years old. I obviously wasnt sexualy active way back then, but thats the age i remember i fell in love with pantyhose. One night after my parents came back from a wedding, i was home with my brother and sister. They came home, changed and what not and went to bed. well my mother who changed in the bathroom left everything that she wore in there. i happened to pick up her pair of sheer...

Porn Trends