Crossdressing.masturbating indian porn

My first time with a man

I had been into dressing in kinky little latex skirts and dresses for years. I loved the way they felt against my skin. Playing on my own had been enough until now, I had toys and vidoes to amuse me but the thrill of being fondled and fucked by a real guy was now too much to resist. I decided to try the online sex sites to find someone and find someone I did. He had looked at the pictures I had placed on the site and was bursting to get his hands on me, a thought that made me tingle with...

Crossdressing

A Hotel With Candy

I got out of bed and looked at my sexy green camisole with bright pink fishnets, bra and panties that I liked to sleep in after I had just spent the night masturbating with my favorite dildo. I looked back at my nightstand to find it was still beside my pillow where I had left it the previous night and stilled wrapped in a condom all sticky with my favorite lube, strawberry flavored.I finally had gotten sick of fake cocks and wanted to try a real one. I went on to my favorite CD website and...

Crossdressing

Smooth Sensation

God I was glad to be home, a two-hour train nightmare. Every stop from Liverpool Street London on the 6pm slow train to the dreary little Essex village that was the only place I could afford to rent a studio flat. My only consolation was the bag of goodies I brought in my lunchtime and the anticipation that tomorrow was Friday and my big night in with my mysterious blind date. I had been living in my little studio flat for about a year and I have to admit, after a string of disastrous...

Crossdressing

Maid to be Submissive Part One

As I stared up at the ceiling, contemplating my own existence, I couldn't help but retrace the last few weeks in my mind. My girlfriend had just broken up with me, apparently, she had met someone else and had been cheating on me for months.The same week, I found out that my company was laying people off and I was about to lose my job too. This is how I ended up at age twenty-five, living with my mom again.It wasn't all bad, I thought, trying to convince myself. My mom owned a long-stay motel,...

Crossdressing

Maid to be Submissive part 1

As I stared up at the ceiling, contemplating my own existence, I couldn't help but retrace the last few weeks in my mind. My girlfriend had just broken up with me, apparently, she had met someone else and had been cheating on me for months.The same week, I found out that my company was laying people off and I was about to lose my job too. This is how I ended up at age twenty-five, living with my mom again.It wasn't all bad, I thought, trying to convince myself. My mom owned a long-stay motel,...

Crossdressing

The Path to Satin Liv and James Meet Again

LivI walk down the hallway, spotting you at the party. I haven't seen you in so long. I swing my long hair over my shoulder, sliding up behind you as my hand slips across your ass. I pretend to act innocent while reaching for a cup of punch. Leaning in to whisper, I say, "It's been so long. I took a walk down memory lane and missed so much." My hand trails up your back then away as a guest walks by. I lean in again. "Meet me upstairs. I have a surprise in my purse." I set the punch down,...

Crossdressing

My First Sissygasm

This is a true story about the first time I felt the sensation of cumming like a girl. I don’t mean a prostate orgasm, where you ejaculate through anal penetration, but my first time feeling what I can only describe as a full body sissygasm. It was another night alone, dressing up in my apartment. I was feeling really girly and really horny. I took my time getting myself dressed up. After a nice long shower, I shaved my legs and any other annoying body hair. I got out, dried myself off,...

Crossdressing

A First Time For Everything

Matt looked exceptionally young for his age and blessed with a complexion that meant he wasn’t all that troubled by facial hair. Spots were non-existent, always had been, even in his teens. Yet at twenty-eight years old you could never classify him as normal. His slim body, born out of long legs and a standard-sized upper torso fulfilled all his needs. He couldn’t be described as ripped at all. In fact, with the right hair, makeup and clothes he would pass as a woman.It wasn’t that he hadn’t...

Crossdressing

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

Jaime s Way part 2

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

Crossdressing

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...

Crossdressing

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...

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...

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

All The Way Part 3

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

Crossdressing

First Time In 19 years

I met my wife in 1989 and we were married 2 years later. Since the day I met her,I gave up my sexual encounters with men and focused on her. We have a great relationship and a beautiful daughter who is on her way to college. Two weeks ago my wife went away on a business trip to San Diego and my daughter went to Arizona to spend time with the grandparents before she left for school. I never gave up my passion for lingerie and kept most of my things from early on and still bought new ones to...

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...

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

Jenny Learns Her Place

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

Crossdressing

crossdresser ashley this my story

hi my name is ashley,I'm 48,and have been crossdrssing since I was 14.its about the time I discover masturbation.when ever I would take a bath or a shower I would take out of the hamper my sister panties and bra sit the and stroke my cock thru the material.often I'd find a pair of pantyhose,and would slip them on.felt so hot wearing them,I even wore them to school.lot times if no one was home I would sneek down to our shop that we had out back where you could not see it.inside I would strech...

Confessions of a Sex Crazy Cross Dresser

The Confessions of a Sex-Crazy Cross Dresser Book I: The incredible first few weeksChapter 1: Panties Thief and the Late Night Swim My name is Sandy. My name is Tony. I know it sounds confusing, but when you are a cross dresser life is always confusing. Just the terminology alone to describe you…crossdresser or cross dresser? Transvestite, tranny, she-male and many other names used to describe people like me can make you confused. I prefer to be called a cross dresser and yes you can call me...

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

Mia s Story

Before I start, a little about myself: I am Korean but born in the U.S. in Jonesboro, Georgia. Jonesboro is about twenty miles south of Atlanta. I am a third-generation Korean American so no I don't speak Korean and the only accent I have is a southern accent, not a Korean one. I was born a male and two months premature. While I was not born with any birth defects, as I got older, I never fully developed as other boys my age did. At the age of sixteen, I was much shorter, thinner, and had a...

Crossdressing

Getting A Grip On The Situation The Conclusion

"You OK, son?" Dad asked Van as he saw him shift constantly in his kitchen chair."Yeah, Pops, I'm fine, just a little sore. Went to the BMX park and for a couple of hours and then a group of us raced through the woods," Van responded."You need to slow down. That's too much abuse on your body for one day, " his parent responded knowingly.'If you only knew,' Van said to himself before he excuses himself from the kitchen table.Once safely in his room, he removed the small butt plug he...

Crossdressing

Dana Finds A Lover

I've been dressing since I was ten, always being careful to never be seen by anyone. The whole time I grew up I'd never had any girlie clothes of my own but I'd always worn my sister's things, even used her makeup. I always made certain that she never ran out of makeup too quickly. When I knew I had the house to myself, I would dress up and pretend I was a girl. These sessions ended in a great masturbation with something usually deep in my tight little asshole, or boy pussy or ass pussy, as...

Crossdressing

Surrendering to Temptation 3

Grant returned to his room on rubbery legs due to his recent masturbation session. Clad in his sister's nightie, panties, and pantyhose while he masturbated gave him the most intense orgasm that he had ever experienced up to that time. He thought about the nightgown that he had worn, washed, and hidden in the basement and decided not to return it to his sister's room.Since his sister admitted that she no longer wore them, he was sure that it wouldn't be missed. He would recover it and hide it...

Crossdressing

Hidden in Plain Sight

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

Crossdressing

Evening In The Office

The normal workday had finished and I gladly filed away the tedious paperwork that I had been toiling with over the past few hours. Knowing that I wasn’t going to depart for a number of hours, I went to the common tea room and made myself a cup of coffee.Back in my office, I sat back, sipped my coffee and contemplated my plan for the next hour and a half before the evening students started to arrive. By now, the building had emptied of the usual complement of tutors and students, and so I knew...

Crossdressing

Across The Street The Conclusion

Mike left his telescope at the window even though it wasn't used any longer; his laptop was the new tool of choice. Every night around midnight he would receive a chat request and a second later Leann's beautiful face would fill his screen. There was the usual small talk about their day as Mike stared at her pretty face.They didn't have to talk about sex. Between her looks, dress and voice Mike always got hard. Leann seemed to be able to sense when he was ready and would start her music and...

Crossdressing

Across The Street The Conclusion

Mike left his telescope at the window even though it wasn't used any longer; his laptop was the new tool of choice. Every night around midnight he would receive a chat request and a second later Leann's beautiful face would fill his screen. There was the usual small talk about their day as Mike stared at her pretty face.They didn't have to talk about sex. Between her looks, dress and voice Mike always got hard. Leann seemed to be able to sense when he was ready and would start her music and...

Crossdressing

Now Or Never

He was nervous as he drove to the mall. He had to remind himself that nobody knew what was really going on, and that men purchased lingerie all the time for the wives and girlfriends. Except his purchases wouldn’t be for his wife, who had unceremoniously left him two years earlier with little explanation. He had revealed a few of his fetishes and kinks to her, which she had given off the impression that she was okay with at the time, but that had all been a façade. Apparently she wasn’t as okay...

Crossdressing

Dan a k a Becca

Dan had been fascinated with women’s panties since he had found a pair belonging to his sister accidentally mixed in with his clothing. He had rubbed them against his face feeling the silky smoothness. He kept them for a few days until he heard his sister asking about them, then made a pretense of finding them stuck in between the washer and dryer. After that, whenever he had the chance, he would try to sneak in a few strokes against his cheek with a pair of her panties. When his sister threw...

Crossdressing

A Lifelong Love Of Lingerie

At the time I was sixteen, my mother was divorced and living with me, and she still worked and was gone until late in the afternoon on some days, so I would have the house to myself. I did not have access to porn until later, but there was Cosmopolitan magazine and other magazines which had the sorts of ads and stories that intrigued me, underwear ads, tampon ads - they all did the trick. I am still very turned on by the picture from the little pamphlet that came inside a box of tampons showing...

Crossdressing

No Strings Attached Penitence Chapter 19

My fingertips graze against the silken, soft fabric, then travel under, greeting taut, warm, muscular skin. Low, gentle moans hang heavy with lust; sexual heat rising as my nipples are pinched, grow erect and brush against the satiny material. My tongue trails over my bottom lip as my need elevates and I reach down, finally, and touch smooth, unyielding steel whilst my mind becomes flooded with indecency."Mmm, Ashleigh... Ahh, fuck!"The flash of pain from my sensitive flesh, being crushed...

Crossdressing

A CROSSDRESSING APPRENTICESHIP

I went to a boarding school . Contrary to public perception it was not a hotbed of buggery . Actually the only instance of it I knew of was hearing a slightly distressed call from another boy ( we slept in dormitories with eight beds ) when another more physically mature boy had climbed into his bed . I was falling asleep as this happened and did not track the outcome . Of course as we progressed through puberty sex - masturbation - was common ; pretty much daily ,and joyful accusations - 'you...

Gay

Getting Caught By A Friend and First Blow Job

After my first time dressing in my sisters clothes and imagining being with a man, I dressed every chance I got when my family wasn’t home. It had been four years since I started and now when I dressed it always included fantasy about being with a man and masturbation. I had grown up into a proper slut that craved cock and needed to be deflowered of her virginity. Only anal I ever had was a small brush handle up my ass, but I wanted so bad for a real cock. I have experienced all my sisters...

Crossdressing

The lady in 237 Conclusion

As his orgasm ebbed Nick pushed himself off the wall and headed to the bathroom to clean off. Once complete he wrapped a large bath towel around himself instead of finding the clothes he arrived in and returned to the bar where he found Candice waiting for him. He took a seat on the stool next to her and she slid a fresh drink toward him and they once again clinked glasses.As he watched her drink he still could not see any trace of a male in the female next to him. As they drank in silence Nick...

Crossdressing

Getting A Grip On The Situation Part 2

Ken felt himself being shaken and heard a voice urging him to wake up. When he opened his eyes he didn't know where he was for a second until he turned his head and saw Vanessa next to him."Hey babe, you've got to get up and moving. It's getting late and my parents will be home," she said softly.Ken was out of bed like a shot and quickly redressed. He must have been so deeply asleep that he was unaware of Vanessa leaving the bed. She was now dressed in a short terrycloth robe and he still...

Crossdressing

The Shopping Spree

After a morning of shopping, I went for a hamburger. As I sat there with my bag of goodies by my side, a man in his early thirties sat down at the table next to me. He beamed a smile at me and said hello. It was unusual for people in the city to be friendly to strangers, but then again, he didn’t look like a man from the city. He must have been in his mid-thirties. His face was rugged, and his hair was unkempt. His clothing was clean, but it looked worn. I guess he must have been a manual...

Crossdressing

Daddy not Dad

I discovered my bisexual inclinations fairly early in life, so by the time I was nineteen, I had done nearly everything you could do with any combination of genders and numbers. I'm a regular guy on the outside, but in private I am comfortable in both the masculine and the ultra-feminine role. I could pass on the street as a hot, high-heeled slut, blowing straight guys in their cars, or go butch, lowering my jeans to fuck a truck driver in the ass behind a truck stop. I loved it all.I also...

Crossdressing

Initiating Stephanie

* Discovery *The first time I set eyes on her, she was wearing the sluttiest underwear one can imagine. Totally oblivious to my presence, she was admiring her scantily clad body in the full-length mirror on the wall. The lingerie was black, my favourite colour, sheer in texture and cut to a design that left little to the imagination. Black leather, ankle boots adorned her feet and complimented the black hold ups she was wearing. She was admiring herself in a full-length mirror and hadn't seen...

Crossdressing

Michelle Gives It Up

When my best friend, Jimmy, left my house late that afternoon he was a very well satisfied guy, sexually. For the two years prior we'd had quite a few mutual masturbation sessions. This had progressed from jacking off while talking about various girls we knew in school to jacking off each other. Of course, at that time neither of us had actually done anything with a girl, but that never slowed us down - quite the opposite. One day he convinced me to wear some of his sister's clothes, namely a...

Crossdressing

A Little Naughty Fun When My Wife Is Away

When I was in high school, I always loved to dress in women’s clothes. The problem is I'm a guy. Whenever my mother was out, I'd always go into her room and try on her intimate apparel. I just loved how it felt on my skin. I'd especially liked how her bras and panties felt. I loved to get dressed in her dresses and even apply make-up. I really never told anybody about this. The lacier the better. I especially liked satin panties. They always felt real nice pressed against my cock. Fast...

Crossdressing

The Secretary Part 1

A lot of my stories are based upon the more formative years of my sexuality. Things are much less complicated these days. There's less sneaking around as I am not quite so in the closet any more, as well as the fact I live alone in my own apartment. I divide my time quite evenly between my identities although work is somewhere I still don't bring my cross dressing. Sometimes I feel like a super hero, by day I'm a mild mannered office man but away from the work I am "Super Jess"- spreading joy...

Crossdressing

While the Cats are Away

Thursday night, mom is going to visit relatives out of town; dad is away on a business trip and not supposed to be back until Saturday. It took a lot of convincing that being sixteen is old enough to be able to stay home by myself and not have to go with mom to visit relatives. Dad was going to be home in two days and I would be going with him to the family ranch. Finally my mom relented and made me promise to be careful and stay out of trouble.After waiting for an extremely long fifteen...

Crossdressing

From dream to reality

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

Crossdressing

Compulsive masturbators

Anonymous asked: can any man be turned into a sissy, even if at the start he really doesnt want itI don’t know. I suppose it all depends on their mental fortitude. But I imagine after prolonged forced chastity, the male mind will grow weak to influence and suggestion if it means the reward of sexual release. If the influence and suggestion at the time is that of feminization and bi/homosexuality, combined to exposure of related erotic images, video, and art, I’d assume that even the strongest...

Mariah My Wank Mistress

We first made contact about three years ago, on one of those dirty dating sites. I was showing my tranny profile, Velvet, at the time, and was being hit on by a bunch of dirty old men, when this "Mariah" person said, "Hi." I was in a pretty sarcastic mood at the time, and was slightly peed off, as the guys I had been chatting to were only interested in one thing, getting their rocks-off. Anyway, Mariah said she liked what she saw, just loved sexy trannies, enjoyed reading my profile, and...

Crossdressing

Pumped While Wearing His Pumps

What a place to be stuck! Under a sign that says Coors Road and practically dying of thirst. I was now two-thirds of the way across the United States but perhaps the most difficult portion of my cross-country hitchhiking adventure lay ahead. It is all deserts from there on the outskirts of Albuquerque to the Pacific coast, my ultimate destination. I had left from Maine four days earlier and was starting to tire of the road. My most recent ride had been with a guy who picked me up in Denver. A...

Crossdressing

The Panty Princess

Jane and I had only been living together for three weeks when I was caught red-handed. I was mortified when I saw her in the mirror, standing behind me with her mouth wide open. She had managed to come through the front door, up the stairs and into the bedroom without making any noise. I tried to explain that it was the first time I’d ever done such a thing, but she was having none of it. For the next hour we sat on the edge of the bed while she bombarded me with questions about my sexuality,...

Crossdressing

Dressmaker s Dummy

I was happy now that Kasia and I had moved in together. Not only did it mean that we no longer had to take turns going to each other’s place, but it also meant that I had closer access to a supply of her soiled panties. Kasia was a cute Polish girl, 23 years old, with deep blue eyes, shoulder-length hair trimmed in a cute bob, and a body to die for. We had decided trying to live together to see how we would manage as a couple, with the intent of marrying the following year if all went well. So...

Crossdressing

Our Sissy Slave

Let me remind you how you came to be in this situation before you refuse. I've been bi-sexual since I was old enough to have noticed how horny women made me. From the moment I noticed, I was unstoppable. My dominant personality seemed to bring me more girlfriends than I could really use. But I always thought the only thing better than a submissive girl is a submissive boy. And what really turns me the fuck on is to take something precious and submissive and to transform it into my own little...

Crossdressing

Caught by Uncle in Aunts things

When I was a young boy, I started to find a fascination with feminine things. Not sure how it started, but one day I found myself trying on some of my Moms things and enjoyed the feeling. The issue I found early was that my Mom was very vanilla in her things, so I started to explore with an Aunts things, one I spent a lot of time with, as her son and I were very close. She had very sexy panties, bras, slips and pantyhose, so I would sneak them into the bathroom at her house, put them on and...

Crossdressing

Crossdressing gangbang

This is not my story. But loved it so much that I was not able to stop myself from sharing with you all.. please do give your response to As I waved goodbye to my wife as she pulled out of our driveway for a weekend business trip a smile began to grow on my face. Anticipating another entire weekend all alone, and thinking of my plans to indulge my deepest fantasies, caused goose bumps to run up and down my arms. Heading back into the house I grabbed a cool glass of water to quench my thirst...

Lesbian

Surviving The Covid 19 Lockdown

Tristan or Tris as he preferred to be addressed had everything he needed to survive the mandatory lockdown. His larder was so well stocked that it would be about six months before he would need to worry. He was ahead on his bills and mortgage payments and he had money in the bank so that was not a worry.He had purchased one of the top-of-the-line gyms on the market today not too long ago cause he found one at a decent price. Now he could continue with his fitness regime without interruption of...

Crossdressing

No Strings Attached The Reunion Chapter 25

It's the first Friday in October, and I sit in front of my dressing table, with my hair in rollers, rechecking my phone for the umpteenth time today before tossing it away in annoyance. My calls and texts haven't been returned by Justin in several months. Still, I'd hoped that today would be different with it being my birthday. Selena is also ignoring my attempts to apologise and my offering of the hand of friendship. I knew at some point that she would grow to dislike me, so I should have...

Crossdressing

Noodles Part 3

The morning greeted me with a gentle ray of light escaping from the corner of the blinds on my bedroom window. As the fog between sleep and awake began to dissipate, I remembered why I was waking up wearing a dress. I went to bed as a girl last night. And I had decided that I wanted to wake up as one in the morning. I pulled the covers off of me and smiled at the sight of my beautiful shape. I hadn't even removed my heels. As the rest of my senses caught up to my eyes, I suddenly remembered...

Crossdressing

Caught in Wife s Nylons

I love the feel of the stockings on my legs. The elegant theatre of rolling the nylon and placing over my toes and then slowly stretching and smoothing them up my legs. The detail of clipping over the suspenders and then slipping my feet into the high heels. I like to stand in front of the long mirror and let my eyes slowly rise from the black patent heels over the slight wrinkle of nylon on my instep, up my legs to the band of the stocking tops. And then my cock slowly dripping pre-cum,...

Crossdressing

Edging With A Friend

Been spending a lot of time recently with a new friend. We've been getting together over a little wine, some soft lights, oil, towels, and watching each other indulge in no-holds-barred self-love - which includes anything we are into, like mirrors, oil, vibrators, nipple clamps (that's all me!).My new friend is a half-Chinese university student in his mid-twenties who I met online. We nervously hooked up a few months ago, fumbled around with each other, decided that we really felt comfortable...

Masturbation

Becky was born

Hello everybody, my name is Becky, this is the story of how I was born.I was 16 when I first started cross-dressing back in the seventies. I had been accosted by a man and masturbated him in the men’s washroom in the park. I still remember what he said about me. He said I looked so much like a girl even though I was a boy. After that happened, that statement stuck in my head. A little time after that, with that statement still floating around up in my head, I decided I would dress as a girl and...

Crossdressing

Office sissy 4

It was the third day at the office, in my new role as the office sissy, and with the new rules, which allowed anyone there to play with me. I was in my office as usual, but I had brought more clothes in. So this time I was in a bikini, meaning a thong bottom and a bikini top holding my flat titties. Both were in matching light pink, which always seemed the right color for me these days, and the thong was barely enough in front to cover my usually at least semi-hard 'clitty'. I had thin pink...

Crossdressing

The End In

The following afternoon, I can’t concentrate on the class I’m supposed to be giving. Jordan sits in the middle row. The lecture still interests him, but his eyes lose focus every once in a while as he switches positions. He’s being a good girl.One of the other students asks whether the air-conditioning is ever going to be repaired. I can only offer her a shrug and a commiserative smile. The superintendent has promised to take care of it but has idled by the overgrown orchard all day. Perhaps,...

Crossdressing

The Subjugation

The hellish temperatures prevail as the term kicks off. No one can concentrate on the classes, mainly because of Jordan. His presence offends the prude girls, and the slutty ones can’t take their eyes off him. The only other teacher – who lives in the village – is perplexed, but I’ve asked her to be tolerant. Apparently, the boy hasn’t revealed his treatment to her nor anyone else. That’s an auspicious sign.My last year’s pets have grown. One of them is acting as if nothing had happened between...

Crossdressing

Milked On The Train

I was still a virgin, at my advanced age (17), but aroused a lot, loved reading sex scenes in books, imagining it, touching myself. I traveled every day on a crowded train, on the way to my classes. One day I was standing, as usual, holding on to the pole while the train rocked and slowly made its way.An older man, maybe forties, was holding on to the pole across from me. He was taller, holding on lower on the pole, and as the train rocked at one point my groin hit the back of his hand. I...

Crossdressing

Neighbor Camilla

This is a work of fiction, if you do not like it move to another post.Chapter 1:I sit looking out my window thinking about my life and the past couple of years, living in the city in this nice apartment with wonderful neighbors and now friends. I first moved in and the older man that lives next door, Alex, offered to help. I was glad for the help, and as the day went found myself more and more attracted to him. I knew he was attracted to me, the number of time I caught him looking at me and my...

Crossdressing

My First Time In Public I The Slutty Girl

This is my confession number one.When it happened, I was much younger – probably twenty-three years old. I always considered myself an outsider, social gatherings make me feel uneasy. I still remember my first crush in middle school. I couldn’t express any feelings or emotions to that girl in my class, the one I felt for.I knew I had no chance; she was the outgoing “slutty” teenager that dressed more provocatively than the other and me the shy chubby nobody that no one would notice. Well, I was...

Crossdressing

The Making Of Tara

I grew up in a small town where nothing really happened. It was a nice upbringing far away from the inner cities and their problems. My school was safe and since I was very young, I would walk to school by myself. My parents seldom locked the doors and on the weekends there were neighbourhood BBQ’s. My friends and I would play street hockey outside our houses or football in a nearby park.As far as girls went there were a few but since it was such a small town everyone was concerned about their...

Crossdressing

Beginnings at the Adult Book Store

There are two types of cross-dressers. The first are those who dress all the time. They are usually quite passable since they spend a great deal of time and effort. The second are wannabe women who live in a world where there are circumstances that prevent them from being full-time out of the closet cross-dressers. They are usually not passable since they cannot shave their entire bodies, grow and style their hair, purchase and maintain a female wardrobe, and/or learn and understand make-up. I...

Crossdressing

Bobbie Breaks

Our routine continued for the rest of the time Amy was away on business. I would ask for money, and Joe would usually unbuckle his pants without a word. I’d give him a blowjob, and he’d give me some cash. I enjoyed it because it was the only time I was allowed to take my bra off.I channeled my frustration at having my girls locked away into being the biggest thot I could. He didn’t want to see my free swinging titties? Fine. He was gonna see every other inch of my body at every opportunity. And...

Crossdressing

Under His Thumb

I was sitting at my desk in a t-shirt and running shorts when my roommate Dave came in. He saw the towel I’d dropped on the floor, and immediately his nostrils flared.“How many times have I told you to hang up your towel?” he said as he bent over to pick it up. He hung it on a hook on my closet door. I looked back at him and rolled my eyes.“You’re so anal,” I said, turning back to my computer screen.Just then, I felt his strong hand grab my skinny biceps and yank me out of my chair.“Unnh!!” I...

Crossdressing

Femme Boy Gets Cock Drunk

I’m not a very masculine guy. In fact, I’m downright girly. I blame my body. I’m 5’3” and weigh 110lbs, but the first thing people notice is my fat ass. It’s fat, tight, and juicy. It’s the kind of ass that women these days pay a queen’s ransom for. It flares out with my wide hips from a narrow waist and flat stomach and is complemented by proportionally thick thighs. My calves are well-defined, my ankles thin and delicate, as is my upper body. Other than my ass and thighs, the only fat on me...

Crossdressing

The Cardboard Fort

I discovered at a young age that I had a desire to wear female clothing, but not just any clothing, it had to be silk and or satin. I thought maybe it was a phase I was going through. I figured if I ignored these desires they would pass. Ignoring them didn't work and they became more intense. I often found myself sitting and staring at the lingerie section of the large Sears catalogue with the same intensity as I once perused the toy section. The images on the slick pages of full and half...

Crossdressing

My Road to Cross dressing Part 3

From the first time I dressed, there was always a sexual element. I used to find the time to wear something feminine and wank myself. It went hand in hand, so to speak. One of the things I loved doing was getting dressed up and laying on my bed with my legs over my head and wanking.When it was time, I would cum in my own mouth. I did it so many times but it was always uncomfortable, but I used to cum anyway. I didn’t swallow but spat it out, every time. I also used to kneel in front of the...

Crossdressing

Andrew Andrea

My mum and I lived on the outskirts of a small Scottish village. John and his mother Beth were our neighbors, and he and I were best friends from an early age, sharing everything as we grew up. At Primary School and then Senior Secondary School, we were an inseparable pair, supporting each other through the good and bad times. This idyll came to an end when we had just turned sixteen. He and his mom moved away from the area to go look after a sick relative.The house was quickly re-occupied and...

Crossdressing

Part 1 Abandoned Parking Lot

It begins...Well, I found out that Anne fucked that professor again. She came to my dorm, drunk at 3 am, fighting with me, calling me a little bitch and pussy, and she began slapping my face. I won’t even get started on what she was on about.I tried calming her down, but whenever I said anything she just slapped me, or if I tried to stop her from drinking more from her loaded thermos, she pushed me.She said, “I’m going to F*** that professor again. By the way, his cock, is like, way bigger than...

Crossdressing

Caught

It seemed to Ken that time had slowed down to a snails pace as he watched the events unfold before him. The door to his sister's bedroom seemed to take forever to open and for Connie to step inside. Connie's head was down as she placed something in her purse before it rose up. That act also seemed to take forever as did her eyes growing wide as she took in the scene in front of her.Ken could blame no one but himself as had been pushing his luck as of late, but never imagined that he would...

Crossdressing

My Secret Revealed

My life was pretty good. I had an excellent job that paid well and afforded a nice mobile home. I played baseball on the company team and had a bevy of office hotties show up to the games to cheer me on, I even dated a few of them briefly. It was the nights that I really looked forward to.Once the day was done and I was safely behind the drawn drapes and locked doors of my trailer that I indulged myself in my new habit. Fresh from a shower I dug out the erotic lingerie that he had...

Crossdressing

slut on the town

I got put in a full nelson the other night by a naked black guy. It happened in a video preview booth at Corey's Adult Video store in Oakland. I had been hanging out in the arcade, wearing just a black two-piece string bikini, and a pair of fire engine red high heels.I had been there for about a half hour, but I hadn't seen anyone. But it was early, only 3.30 p.m. Then I heard the buzzer go off and I knew someone had entered the arcade. I stood near a corner, waiting. It was pretty dark in the...

Crossdressing

Sissy Blane s Liquid Assets

I became familiar with the Plumrose Dossier one cool February morning when it was read to me in the private rooms of Madame H at the Clinic.***I'd arrived that morning for my weekly 'therapy' and had only enough time to hang up my outer clothes in the Sissies' cloakroom and don my Eva Gabor wig before a facilitator poked her head in and told me I was wanted in Madame H’s office immediately. Even at that point I knew this couldn't be good so I shrugged into a nylon dressing gown and followed her...

Crossdressing

My Mother s Boyfriend My Slut part 2

The day had been wonderful, seeing my slut skewered on my strap on. His nipples peeking through his netted shirt as he begged to come with me buried deep inside of him. After he came all over his chest and face, I had exited the room, needing my own release. I headed for the shower, happy to leave him to clean up his mess. With the taste of him still on my lips, I turned on the water. Feeling the splash along my sensitive skin, I rubbed my thighs together as my hands began working my tender...

Crossdressing

Deann Finds Out

Jimmy sat up in bed and felt the dry cum on his belly from last night's masturbation. A quick look at the clock told him his parent's had already left for work and their weekend trip so he knew he had nothing to worry about. The plans he had for the day could begin right now. Stepping out of bed, he padded to the bathroom and began the process. A long shower began the day. He made sure his shapely legs were shaved silky smooth before moving to his underarms and then to his pubic area. He liked...

Crossdressing

Jenny Learns Her Place Part 2

“Thank you, Master,” I said as I slowly brought myself to my feet, tears of pain rolling down my cheeks. I couldn't see my ass but it was probably purple with bruising and I was happy with that. Bobby would now know that I could withstand a hard spanking with the paddle without falling back on the safe word. “And for good measure,” Bobby said and put the clips back on my nipples. Wincing with the incredible pain, I managed to stand straight. The nipple clips hurt much more this time than the...

Crossdressing

Nights in pink satin

It finally had happened. Paul couldn't resist the urge anymore. The urge to wear women's clothing. The urge to be degraded and humiliated. The first thing he had done was to have a shower and remove all his body hair. Gazing at his naked self in the mirror, he was pleased with the results. Forcing down a shudder of anticipation and excitement, he reached for the first garment. The feel of the silvery satin panties held in his hands was electric. Unable to help himself, his penis swelled and...

Crossdressing

My Crossdressing Story

My Cross-dressing StoryAll 100% true.I was about 13 when I was home alone during the day, I went into my (older) sister’s bedroom and saw her school dress on the floor. For some reason, I thought I would try it on, so I undressed, put it on, and paraded in front of the mirror (no underwear). My immature little penis got stiff, but I had yet to discover the delights of ejaculation.I walked around upstairs for about 30 minutes, then took it off and put my boy clothes back on.The next year we...

The Sexy Girl Next Door Part One

As a sweet sixteen-year-old boy, I started my life of having transvestite proclivities. Being sexy for men and making their cocks hard for me became my favorite thing to do for pleasure. I already had a boyfriend, the blonde college boy lifeguard at my community swimming pool. He had seen me wearing some sexy little hot pants and come on to me, one day. The fact that he was handsome and all the girls wanted his cock made me proud to be the girl who was getting to suck him, daily. Every day, I...

Crossdressing

My Sexual Odyssey Part 1 How I Got Started

I was always extremely sensuous, expressed in the love of the feel of satin and silk, as well as the feel of going barefoot, which was nearly impossible in the city, even indoors, not part of the culture. Where I live now it is, and so I go not only barefoot but also nude when at home. I don’t know if this is significant or not. However, the first time I noticed anything unusual was probably when I saw a film on TV in which a boy masqueraded as a girl for some reason or other. I recall how...

Crossdressing

How my Best friend gave me what I always wanted

The day started from me being all alone in the house for a full day. My parents and sister were out and wouldn't be home until the next day. I decided that I would give my best friend a call and get her to come over to see me, we hadn't seen each other in quite some time. She was just as eager to see me as I was her and we were both very excited as we really enjoy each other's company.Now my best friend and I had a very normal friendship. Although I'd always had fantasies about her as she was...

Crossdressing

My First Time Final Chapter

The Friday that Lydia told me about had finally arrived and she would be bringing some of her friends over for drinks after work, and I was to serve them as Melissa. Lydia had also advised me that unlike the dominatrix persona I used during my first outing on Halloween, Melissa the maid, was totally subservient. That morning after my usual visit to the gym I cleaned the house and set up the bar. I had become a combination of nervous, excited, and scared while preforming these tasks as the hours...

Crossdressing

Anonymous Encounter

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

Crossdressing

A Great Date

I was so excited to sign online and see a message from my sexy college boy. We hadn't spoken in a while and I guessed that we would never get the chance to finally meet. Many a night had I masturbated thinking about his lovely cock, though I had only pictures to please me. It turned out that he had been thinking about me too. "I can't get you out of my mind," he said. "I need to meet you. Let's go on a date sometime." He knew that I wanted so badly to have a sweet man take me out on a real...

Crossdressing

Not What You Think I Am

Marriage can be a lonely place, two folks living together and yet being so far apart. It never used to be like that but I guess it comes with the ageing process; a mid-life crisis. To overcome our frustrations, my wife decided we would spend more time together away from our comfortable home, so one weekend every month we hire a log cabin at a campsite that sits between the forest and the lake. It might have been better to spend weekends apart and, realistically, that is exactly what we do!...

Crossdressing

Caught Used and Loving It

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

Crossdressing

Sissy at the Bookstore

I had gone to adult bookstores for many years and had done it in drag many times but never dressed as a sissy and never during the day. On this day I was so involved in humiliating myself that I decided that I need to take that extra step and I did.I had checked into an adult motel the night before and booked for two days so I had a lot of time on my hands. The night before I had pranced around in front of other guests, both men and women, dressed in sexy women's clothing and had a wonderful...

Crossdressing

Always Up for a Party

I got home late. What a night! I had gone to the video booth at the bookstore horny as hell but in my wildest dreams I could not have imagined the outcome. Oh sure, I expected sex. I had yet to leave those dark little booths without a mouthful of cum, an ass full of cum or having my balls sucked dry but tonight … tonight! Not only had my ass been filled in the booth but at Trevor’s party I had been fucked like a cum slut, no doubt earning me a reputation as well as a nice little bonus. I smiled...

Crossdressing

Mistress Lucy takes control

Belle had finished disrobing and stood in her bra and thong, both pink, following Lucy's command. The latter stood in front of her girlfriend and, with a light touch of the shoulder, pushed Belle down on to the bed. Belle looked up at Lucy expectantly, eyes wide. Neither girl wore any makeup; they'd been awake for a couple of hours and, having spent the morning in the kitchen loafing around in their pajamas, drinking endless amounts of white tea from their cafetiere, both girls were just about...

Crossdressing

Halloween Trick or Treat Surprise

Chapter 1 –Susan Charity Event To my surprise Susie my wife of 15 years comes home from one of her many business trips. She is all excited about a Halloween costume party fund raiser, for non profit that supports women studies. The invitation states, the best couple for this evening will receive a free weekend in Bermuda. She wants’ us to go as couple switching genders. Let me explain, when we got married years ago, she was an extremely sexy size 12, 5’ 5” with fantastic curves, huge D cups...

Crossdressing

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