Crossdressers indian porn

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...

Crossdressing

A Crossdresser Gets Caught

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

Crossdressing

An Introduction to 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...

Crossdressing

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...

Crossdressing

Night Trawling The Crossdresser

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

Crossdressing

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

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...

Crossdressing

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

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...

Crossdressing

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...

Crossdressing

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...

Crossdressing

Crossdresser and I at Costco

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

Crossdressing

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...

Gay Male

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...

Crossdressing

Uncle Joe

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

Crossdressing

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...

Gay Male

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...

Crossdressing

Crossdresser porn story 1

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

My Road to Cross dressing part 2

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

Crossdressing

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...

Crossdressing

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...

Crossdressing

A Night of Firsts

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

Crossdressing

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...

Realized Fantasies Chapter 1 Exposure

Steve wasn’t sure, but he thought he heard the bathroom door close. He was in the shower and the bathroom fan was running, so he stopped for a moment to listen. Maybe one of the guys came in to use the toilet, he wondered.“Hello?” he said aloud.No reply. It was probably just one of the other guys getting something they’d left in the bathroom, he thought. Steve was one of the last to shower, and the other guys had left a variety of toiletry items at the sink. So he went on showering but hurried...

Crossdressing

Missy Returns

It had been a long time from the seven days I spent with my studs, but sadly I went off to school and Missy had to go on an extended vacation. However, school did not work out as planned and I found myself in a new city and my own apartment with a small job. I had to help pay the bills. For a while I lived with a roommate who was a little homophobic and despised the ideas of trannies. He never found out that I was Missy but had come across the site once and never recognized me. Eventually, he...

Crossdressing

b Incidents in a Crossdressers Life Part 5 b

Incidents in a Crossdressers Life: Part 5After our last escapade, Sarah (a boy who grew up as a girl) went home and left her soiled Smurf printed panties behind and I snatched them up before I headed home. Buddy smiled as I sniffed the crotch. She demanded I lick the crust. I was being too playful so she walked up and forced them into my mouth. I guess I was not done for the night no matter how exhausted and cumless I felt. The panties in my mouth instantly got my eraser nipples hard and up...

Truck Stop Tranny Sluts

My girlfriend and lover Candi and I were driving back to her place for some steamy tranny sex after a night of partying at a tranny/gay bar in town when we passed a truck stop on the highway. Buzzed and horny as we were, we laughed about stopping in the lot and doing so hookin’ as a means to get us some trucker cock. After a minute or two of silence, Candi said lets do it and before I could answer she was turning back for the truck stop! Candi and I are both bisexual crossdressers and we pass...

Crossdressing

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...

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...

Crossdressing

Crossdressers Rush

If you have a fixed aversion to cross-dressing sissies, you may wish to go elsewhere. However, my story isn’t about that, although it provides the protagonist vehicle. It’s about control… self-control, losing control, being controlled and everything out of control. I hope you enjoy my style ….. p.s. If my humble contribution offends or annoys any readers, I sincerely apologize. My intent was merely to provide a brief moment of stimulating entertainment. Comment and ask for the saga...

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...

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...

Crossdressing

The Transformation of Ms K Part 1

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

Crossdressing

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...

Crossdressing

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...

Crossdressing

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...

Crossdressing

Kaitlyn

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

Crossdressing

Terry Gets It In The End

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

Crossdressing

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...

The Change Up

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

Crossdressing

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...

Crossdressing

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...

Crossdressing

Ladies Night at the Leather Bar Part 1

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

Crossdressing

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,...

Crossdressing

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...

Crossdressing

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 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 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...

Crossdressing

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...

Caught in My Girlfriend s Panties

Bella was wearing a black and white checkered wrap dress. The deep-v neckline teased her ample cleavage. Without seeing it, I knew she was also wearing a half-slip and lingerie chosen to please me. I pinned her to the foyer wall as soon as we entered her house. We kissed. I grabbed her soft ass.She had a midwestern look with fair skin, dirty blond hair, and blue eyes. She was fit, but not slender, with a big sexy ass, smooth thighs, and nice bell-shaped tits. I took her hand and led her to...

Crossdressing

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...

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...

Crossdressing

Taking That First Step A New Chapter Begins

The Summer was drawing to a close, and Lance would soon return to school for his senior year. As excited as he was about his final year, he was saddened that meant no more early morning rendezvous with the stunning Cassandra.It had been a great Summer. Thanks to her assistance Lance had taken his desire to crossdress to a whole new level and he became Lana. In order to complete his stunning transformation he spent many hours in his room at night working on his skill at makeup. Over...

Crossdressing

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...

Crossdressing

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...

Crossdressing

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....

Crossdressing

Crossdress swaps clothes and gets assfucked in pub

A few years ago I was on a weekend trip to Brussels and Amsterdam with some friends, and found out a girl I knew from Ukraine was now living in Lille, not so far away, so I decided to make a quick trip to see her the evening before we were due to fly home. I caught the train from Brussels to Lille and she and her boyfriend picked me up at the station. She was a short, curvy blonde, with equally large breasts and ass. She loved wearing sexy outfits which showed them off. This evening she was...

Girlfriend Catches Me Crossdressing

At this point I have been crossdressing for many years. I started out with my mother’s panties and bras. I would wait till she had gone to work and then go to her room and pick out one of my favorite matching bra and panties. I would lay on her bed and stroke my cock though the soft silky material, dreaming of her walking in and catching me and telling me what a little faggot I am. It never took me long to cum. This fantasy never came to be, but wanting to get caught stayed with me.A few years...

JOANNE SLAM A LIFETIME OF CROSSDRESSING hellip Almost

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

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...

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...

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...

Crossdressing

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...

Dan Becomes Dawn

Chapter One: The InvitationI work from home and am able to dress enfemme most days.Today I am wearing a pink flower-pattern, button front blouse, knee-length white a-line skirt, a pair of white walking sandals with a wavy, medium brown wig and clip-on earrings. Under that I am wearing a corset to flatten my gut, matching white lace panties and underwire 40-D bra to support adhesive-attached breast forms, which give me a comfortable bosom.I had just received a call from an investment group...

Crossdressing

One On The Way

Ryan arrived home from work earlier than normal thanks to lighter than normal rush hour traffic and he was quite happy. This would give him plenty of time to get ready and ensure that his mobile home was clean enough to receive visitors. Once satisfied on the condition of his place, he stripped off his work clothes and headed to the shower.He spent an extra amount of time allowing the warm soapy water to clean every inch of his body. Still dripping with warm water, he reached out of the shower...

Crossdressing

A Night to Herself in London

DISCLAIMER: This is a fantasy story depicting sexual acts involving adults. The story is intended for adult readers only.-----------------------------She'd been working hard in the lead up to this night for months. It takes alot of planning and discipline to look and feel as good as she did as she began to prepare.The day had been spent exercising, fasting and hydrating. As she stepped into the shower after finally finishing cleaning herself out, she sighed deeply since now the fun could...

Crossdressing

Being Joann

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

Crossdressing

My First Time Out On The Town All Dolled Up

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

Crossdressing

Crossdressing Friends

I forgot about my dvd and took the picture. It was inspiration for several orgasms. A long black haired wig hung down to his shoulders and a black leather corset was squeezing his body tightly. I only wished that the picture went down further so I could see his cock. Part of me wanted to tell him that I knew. At least then, we would both have someone to share this interest with. I figured I’d talk to him about sexual interests and fetishes, see where it led. “So…Joe. What kind...

Another Road Trip Story

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

Crossdressing

Being a Bride

The alarm went off and I turned over in bed, I could not believe the day had finally come. I slipped out of bed and adjusted my satin night dress, fixed one of the spaghetti straps on my shoulder and covered one of my breasts that was exposed.In the kitchen I got myself a juice and croissant and sat at the table.My thoughts went back several months to my first meeting with Steve, I had signed up to a website that helped crossdressers like me hook up with men who wanted to be with people like...

Crossdressing

Further Exploration

After Jerry kissed me goodnight and returned to his own room, I had time to reflect. Sex with him was so different than it had been with Jack. Jack took his time, slowly and steadily pumping his hard shaft in my man-pussy and making me feel like his special girl. Jerry was passionate and urgent, riding me hard and making me feel special in a whole different, slutty, way. I was Jerry’s special little slut, and I loved every second of being pummeled by his big thick cock. There was no doubt that...

Crossdressing

Sissy Blane and the Hydraulic Inevitable

The story so far: debt-ridden Sissy Blane's first obligatory date with Mr. Plumrose is about to take place. '...there's nothing good or bad, but thinking makes it so.' The truth of the old saying occurred to me as I awoke on the fateful Friday and was surprised to discover that I was looking forward to the events of the coming evening.Arising from my bed feeling energized I bounced downstairs to make a breakfast of oatmeal and raisins and some french-press coffee. I decided that would be it,...

Crossdressing

A Young Crossdressers Beginnings

( . Y . )I just found out my Mom told a whole group of parents about an incident when she caught me in her cloths. Specifically, she caught me in her bra, panties, panty hose, and makeup. I am approaching thirty-five years old now and the individual that told me must have heard it from his mother, who was one of the other parents. We used to go camping every year and one night when the k**s were playing or sleeping the parents were talking. She let it slip that she caught me in her room with...

Night at the Video Store part 3

There I was a sissy bimbo dressed like a slut in a short black micro mini skirt, spike heels, lots of junk jewelry, huge platinum blonde wig, shoulder strap white fur purse and, of course, perfect make up.I had never been to this video theatre before and was nervous at first, but I waited for my eyes to adjust to the darkness and then moved into the theatre area. Screen five was recommended to me by the door girl, who I knew from other theatres. She knew I was a cross dresser and a bimbo slut...

Crossdressing

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...

My first crossdressed cocksucking true story

It happend few years ago. My ex gave me a "hall pass" to explore my sexuality although she didn't like me dolled up and looking like a cheap slut.I was chatting for some time with this man on the IRC. He liked crossdressers, boys on the way to become fem sluts. He was mature, around 50. And he was also travelling through Europe.One day, he caught me online and told me that he will be passing my town and stopping by in the hotel. I was supposed to meet him on friday night at the hotel. He gave...

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...

crossdressers first time

i first started to wear tights when i was 18,i was shocked when i first realised i loved tight panties and sheer tights. i was staying with my friends mother who was 65 at the time,she wore the sexiest lingerie i had ever seen,especially on a woman that age,but i felt drawn to the sheer stockings. the next day i was taking a bath when i noticed them on the wash basket,i had an urge to wear them,i was very shocked by this desire but had to!i slipped them on taking care not to rip them,they were...

Toni Encounters Greg

Anthony Lorimer was aged in his early thirties. Over the last year or so, he had progressed from occasionally putting on his now estranged wife's underwear when she was not at home, to the stage that he was now at of going out fully dressed and made up as a woman. When dressed Anthony became Toni and, in part due to his build and bone structure, he became a very attractive female.In the early days, he would wank whilst wearing his wife's knickers but now he had become so adept at becoming 'she'...

Crossdressing

Second Encounter Ch 4

I awaken at the first rays of light streaming through the curtains. I slip out of bed, freshen up in the bathroom, and make my way to the kitchen. I start the coffee pot, and soon the rich aroma fills the cottage. I hear you in the bathroom, and soon you make an entrance into the kitchen. "Good morning, Sunshine," I quip, " How did you sleep?""Solid as a rock," you say as you rub your eyes."Coffee?" I ask."Absolutely!" you say with gusto."What would you like in it?" I ask."Cream, and lots of...

Crossdressing

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...

Crossdressing

Second Encounter conclusion

We grab a blanket and step out into the cool evening. The ocean breeze feels great and the sky is beginning to lighten in the east. We walk naked down the beach, delighting in each other's company. We chat like schoolgirls, and I am overcome with a feeling of happiness and joy. We soon reach the secluded cove we had visited the night before. As we approach it, we hear the unmistakable sound of sexual ecstasy. We top the dune and behold Jill and Jasmine locked in a passionate sixty-nine...

Crossdressing

Noodles Part 7

Lori is coming back home tonight, I had to remind myself. Mark and I slept together last night, then I had to tell him goodbye this morning. That was a bittersweet ending to an amazing weekend. I washed all the laundry and sheets, putting everything back the way it was before my wife went out of town. I hadn't heard anything from Mark since he left this morning. That's probably for the best anyway, I reasoned. I need to get my head right and remember my masculine identity. Lori will be...

Crossdressing

Crossdressing Porn Story 2

Jack let himself in the front door. It had been a long day at the store. He’d noticed Ray’s Porsche in the garage. “Honey, I’m home.” From the kitchen came a sweet “Hi Janice how was your day.” “Pretty rough.” “Well just sit down on the couch and relax. I’ll have dinner ready in jiff.” They had divided up the house chores and Jack was glad that Ray had taken over the cooking. The meals were always delicious. Ray walked in...

Jaime s Way Part 1

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

Crossdressing

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...

My first Forced Femme Crossdressing experience wit

Forced Femme CrossdressingForced Femme Crossdressing had never crossed my mind. Certainly not that day. I had been lounging in my PJs one evening early last December. My fiancé Melissa was working 2nd shift rotation. When her best friend Dawn showed up at our front door. She invited herself in when I opened it. When Dawn and I are alone, she always teases me about my bisexual tendencies. It was my own fault for letting them slip one night when I had way too much to drink. Which Melissa had...

Caught Crossdressing by Aunt Sharon

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

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...

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...

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...

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...

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