Crossdresser indian porn

Tied and Taken

I had always had fun and gotten excitement from crossdressing and bondage play. After my first encounter with Chris, I was forced to accept the fact that I had desires and needs that I had suppressed for years. After having been tied up and mouth fucked by Chris, I realized that I didn't just like dressing up like a girl. I just didn't get a kick out of being tied up. I wanted to be a "damsel in distress" at the mercy of a man, to be helpless before him, to be used as a woman as he saw fit. My...

Crossdressing

Crossdressing Charlie Episode 11 Under His Thumb

CROSSDRESSING CHARLIE Episode 11 UNDER HIS THUMB Prue watched him get into the car from the top of the steps. Dave, who was still standing outside of his car, stared at Prue maliciously. She returned the gesture, glaring intently with apprehension before watching him swing into the car. Dave was quieter than usual as he settled himself at the wheel. He looked unnerved, doubtful, and even a little irritated. He turned the key in the ignition and the engine revved up like a vicious...

Teenage CD Awakening Part II

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

Crossdressing

Webmeets Diary Ch 04

Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible.As I neared the end of my university course I had less and less time for playing around on adult personals sites, and spent most of my free time planning my...

Crossdressing

Been A Long Time

Once I got married I pretty much gave up my crossdressing lifestyle to lead a more "normal" life.You know,settle down,have a couple of kids. I was a happily married man with two kids,what could be missing? Well one day while at work,I was on the internet and stumbled onto a crossdressing website,and all kinds of memories came rushing back to me. The feeling of sexy panties,bras and hose.The feel of a hard cock pushing it's way past my lips and down my throat.The taste of a hot load of cum. As...

Crossdressing

First time with a man

I have been crossdressing since the age of 11 years old. I never really considered myself anything other than straight. Up until I turned 19. I often fantasized about other guys when I was dressed but that's as far as I took it. The year was 1984 and one day I decided to stay home from work to play. I get dressed up in a pair of purple satin string bikini panties,matching bra,black thigh highs and garter and a short silk spaghetti strap nightie,that barely covered my ass. After playing around...

Crossdressing

Crossdressing Vignettes True Story

I went through a period in the '80s and '90s when I was very much into crossdressing and being a bottom. I didn't write these events down at the time, but I wish I had. As the events come to memory, I'll write and post them. Here's one such story:In the '90s, I was married, and my wife didn't (as far as I knew, anyway) know about my bi or crossdressing interests. I loved her very much, but I had these other desires I never shared with her. I kept a small bag of lingerie, condoms, and lube...

Brittany s Adventures Part 1

You can say everything started at a young age when I started having this new but strange desire to look through my sister's clothes and underwear drawer. A little while after when everyone was out of the house and I made sure nobody was coming back I tried them on. It was at sixteen when I put on my first pair of panties and it changed my world forever. I still remember that magical feeling when the skirt fit me just right and curved my body into this beautiful feminine form.As a growing...

Crossdressing

My Crossed Life Chapter 5 A Very Happy Halloween

The days couldn’t go by fast enough as I patiently waited for the last weekend of October. While crossdressing on Halloween seemed all too cliché, Missy and I had collaborated on quite an outfit that undoubtedly would be my most outlandish and revealing look yet. Missy and her friend Laura had decided that a trio of slutty pirates would be the perfect opportunity for Jenni to make her college campus debut. Missy said she was up for the challenge to make me undeniably passable as long as I was...

Crossdressing

My First Walk On The Wild Side

It wasn't until I was in my mid-twenties that I plucked up the courage to leave the house dressed as a young woman. Initially, it was short walks to the end of our street (a relatively quiet suburban road in a relatively quiet town). My hair was fairly long in those days, with blonde streaks through a feather-cut. I'd comb down a fringe to my brows to give me a more feminine look. Over the years, I had tinkered with make-up, and by the time I was ready for a "Walks On The Wild Side", I was...

Crossdressing

Ashley s Crossdressing Adventures

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

Crossdressing

The Train Comes Off The Tracks Chapter 2

I arrived home after a crazy night at work. To recap; my supervisor found me wearing women’s underwear, made me eat her out, then fucked me with her nightstick. Now I am basically her bitch. What is my next step? She said I should be better prepared. How the heck could you be prepared for what happened last night? Never in a million years would I have guessed my supervisor would be pegging me with a nightstick. I had to decide how far I was willing to go with this, and figure out what I needed...

Crossdressing

First time crossdressing with a friend

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

Crossdressing

The Making of Kairi Fox Part 2

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

Crossdressing

A Trip to the Mall

I love sex and I've never been in a committed relationship. Slut is a label I wear with pride and I have the credentials to back it up. But that day I just felt a little extra wild.As bold as I can be, I've never just approached a stranger for sex. I usually meet people in gay bars or on dating apps. Some just approach me. I felt like I needed to put some bait on the hook to make it known I might be open for business. I looked at the clothing I had hanging in the closet. Most of my...

Crossdressing

Freedom What The Hell Do I Do With It

Freedom? What to do with a large lottery win. So, I returned to the world of being a single man. A liberation of sorts, a return to uncertainty at a certain age. It is a scary place to be, ejected from the family home and to set up again. Sure I have the comforts. Sure, I have all my books, the CD’s, plenty of DVDs. Ok, the furniture in the new place isn’t that good yet and I could do with a new mattress, but hey, a few weeks and that will be put right. I can get on and decorate the new...

Crossdressing

Sex with a crossdressing in a public toilet

Friday came and I'd bought a new outfit just for the occasion. I slipped into my low rise boy shorts (black with white spots and white lacing), tucking my penis in where it wouldn't get in the way of course. I put on my matching bra, filling it with my C cup breast forms and then put on my black stockings with pink ribbon at the top, pulling them all the way up my thighs. I put on my very short black skirt next, sliding it up so far as to just barely cover my rear end. Fortunately, I'd...

Turning into a Middle Age Slut Part 1

I have had the crossdressing bug for many years and have collected some items to fully dress with, such as a wig, makeup, fake boobs and all that makes me look as fem looking as possible. Being in my mid fifties however, there was really no way that I was going to be truly passable or that hot, so I thought Over the years, I collected my lingerie, heels, wigs and experimented with makeup. I mostly took it with me on travel to experiment with in the hotel rooms. I bought most of the stuff off...

Crossdressing

Shall I Tell You About My Wife

Time has been exceptionally kind to my wife Samantha. As a sixth form teenager, her stunning looks, along with her 36 DD's, attracted the attention of the male students and some teachers at her school. Her chestnut brown hair flowed down to her waist, and her face wouldn't have looked out of place in any beauty pageant. It was no wonder that she had an everlasting stream of suitors clamouring for her attention.She lost her virginity at seventeen, after several attempts, to James the school...

Crossdressing

A Close Encounter Part 3

Homeward Bound "Well, how was it for you?" My question was directed at my wife's reflection in the rearview mirror. She looked quite fresh considering that she'd just been fucked. "Yeh, it was good! Pass me a tissue, babe." Sam stretched an arm between the front seats. "It was certainly different!" Paul's assessment of the last hour's shenanigans raised a chortle. "Not 'aff!" I concurred in a deep baritone totally alien to my look. While Samantha wiped some of Ross's cum from her...

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 Fun From A Womans 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...

Happy to be Used Pt 9

The next day I woke up very early. I would have expected to sleep in since I got home after 2:00 a.m. but the clock said 6:00 a.m. when I opened my eyes. I lay in bed reliving the events and my performance from the previous night. The sex was amazing. The double penetration was mind blowing. But what really kept me smiling was my convincing female performance.No one suggested I was a guy all night. No one hinted at knowing my secret. I lived an entire night as a woman and was treated like...

Crossdressing

A Close Encounter Part 1

A few weeks ago my wife remarked on how "the gals" hadn't had a night out in months and suggested that we should perhaps go out later that evening."What! Yeah, sure! What's brought that on?" It wasn't like Judy hadn't been around, on the contrary, she'd been around twice last week.I'm one of those cross-dressers whose wife gladly shares her wardrobe. And Samantha's the kind of wife that guys with my quirky habit can only dream of. We've been out together as a couple of girls on countless...

Crossdressing

My New Life As A TGurl Slut Introduction

I love cock. I've always lusted after cock and the older I got the more I wanted it. I've slept with getting on for a hundred girls and done things most men can only dream about, like lesbian thresomes with a girlfriend and one of her friends or some other babe.But secretly I craved big hard cock to suck and fuck. I've always wanted to please hunky, horny men and be their slut....but up until a couple of months ago I'd never been with another man or tgirl.OMG how my life has changed and I want...

Crossdressing

My New Life As A TGurl Slut Introduction

I love cock. I've always lusted after cock and the older I got the more I wanted it. I've slept with getting on for a hundred girls and done things most men can only dream about, like lesbian thresomes with a girlfriend and one of her friends or some other babe.But secretly I craved big hard cock to suck and fuck. I've always wanted to please hunky, horny men and be their slut....but up until a couple of months ago I'd never been with another man or tgirl.OMG how my life has changed and I want...

Crossdressing

Lisa s Lessons

I used to spend a lot of time away from home for my job. It had its downsides, but it gave me a chance to do my favourite thing: show off. My toolbox had a locked compartment containing a small selection of cam-suitable wardrobe items: a single camisole, a few panties, and two pairs of nylons - one thigh-high and the other to the waist.I travelled a mostly predictable route, so I was a regular at several hotels around the region. Along with racking up enough points to take my wife on a nice...

Crossdressing

Caught and punished by my manager part 1

My job as a sales rep meant I had to work away a lot, traveling around the country to various events and conferences. It suited my lifestyle as it meant I was able to indulge in my secret obsession of crossdressing. Every week I'd pack my suitcase with a new outfit of sexy lingerie, heels, wigs, makeup, a vibrating cock; all the things I’d need to satisfy my sexual urges each night when I’d finished work. The hotels were great as the rooms always had a shower, a large bed and lots of mirrors to...

Crossdressing

A Condition of Endearment

I am a young, petite, passable and enthusiastic transvestite. I’ve been crossdressing and working on improving my look and appearance ever since I was a sixteen year old boy. Now after two years of weekends dressed in public as Cari, I had developed quite an attractive look and appearance. It often seemed at times, that many a man would come my way.Because of my exotic and sexy appearance, things could get interesting at times. When you are dressed as an alluring, sensual woman in high heels,...

Crossdressing

From Sam to Sarah A genre bending story of sexual and personal discovery Chapter 2

The anticipation was eating me alive. My girlfriend, Aubrey, a strikingly sexy, gorgeous, blonde, polyamorous, bombshell grad-student and I had been living together for about three months. She had taken my virginity and was the dominant one in the relationship. She had been fucking another guy, Scott, every other weekend for about two months, and I had finally asked if I could be there in the room next time he fucked her.She sat there, pensively deliberating. Her adorable eyebrows were...

Crossdressing

Sex With Wife Who Doesn t Know

A little about myself. I have been married for 40 years. I work in a professional career and I secretly like to cross dress. My wife does not know, or, I suspect she might, but prefers to not acknowledge it.I started dressing about twenty years ago when our two daughters were off to college and we were empty nesters. Out of curiosity I tried my wife’s panties on one day while she was gone. It really felt good – different. I was not sure this was right and afraid of getting caught so I did not...

Crossdressing

Forced Crossdressing Stories

All of these stories share a central theme of Crossdressing. Rather than add yet another story for one of my ideas, new ones will now go here. I'm making the call, out loud, for additional authors to add their own threads and work with me. I would love anyone interested in any of these stories or my previous ones to add their own threads. If writing isn't your thing but you have ideas, send me a message. I'd love to hear of anything you come up with.

Transsexual

My 2 AM Phone Call Part Five

Bondage means different things to different people. To some, it just means being tied up, but I always felt that true bondage means a lot more. It can mean total surrender to the situation I find myself in and total embracing of the situation, knowing I can't do anything about it.When I looked more carefully at the machine that was in front of me, I realized that this was to be a special challenge. It was pretty clear I was going to be positioned on the machine in such a way that I could not...

Crossdressing

Crossdressing for sex

The act of crossdressing for sex is incredibly arousing. It gets me in the mood for the debauchery to come and allows me to come Brooke the cock loving whore. Even having been dressing for over twenty years, I still look forward to it. Adding to the experience I like to dress while my lover waits in another room. I want them to sit there thinking about what I am doing, what I’m putting on, what I will look like when I enter the room. I want their imagination to flow, and I want their cock...

First Time For Everything

I have been crossdressing since my mid-teens, from sneaking a pair of my sister's knickers to sneaking into the gardens of my parents' neighbors and pinching underwear from washing lines. In my late teens, when I found girls and sex, I purged any clothing that I had and managed to put the ’urge’ behind me. I settled down and got married.Unfortunately for me (or not?), my wife liked to wear very sexy underwear, stockings, and very revealing outfits. This meant there were a lot of these ‘things’...

Crossdressing

The Compromise Part 1

My wife, Ally, and I have been married for eight years. What once could be considered a torrid love affair had subsequently lost its sexual passion. We don’t have any children, both being career focused, but our sex life had become quite stagnant from the steady grind of life and over-familiarity we had with one another’s sexual tastes. That is, until one crazy night changed everything. About one year ago, we were fighting constantly. We didn’t know why, but we were both at our wits end with...

Crossdressing

An Unforgettable Halloween

This past Halloween I took advantage of a chance to attend a charity Halloween ball. I had to travel for business to a city in upstate New York for a few days, and my first day there I saw an advertisement for an annual Halloween costume ball taking place in the mansion of local philanthropist. The annual party raises a significant amount of money for a designated charitable foundation. This year all proceeds were designated to go to Hospice. The cause itself was good enough reason for me to...

Crossdressing

The Irresistible Dress

I entered the store as soon as it opened. I knew entering this early helped to ensure I would be the only customer so I could try on the boot cut jeans I wanted to buy. I said hello to the saleswoman and quickly wandered over to the jeans section but as I did I noticed a rack of new dresses. The one that stopped me dead in my tracks was a simple sleeveless sheath, but I loved the simple color pattern and I could tell the shape of the dress would hug my body. The saleswoman approached me before...

Crossdressing

Made Maryanne Part 2

When I woke up the following morning, I immediately became aware of the situation. It was difficult not to notice the pretty white cotton and lace nor the fact that I was wearing it. I quickly recalled the events of the previous night, feeling ashamed at having been caught masturbating. I knew that Beatrice somehow wanted to make a point by telling me to wear her nightdress, but I had no clue why. I rolled over to see her watching me. She was wide awake, looking as beautiful as ever with her...

Crossdressing

Office Caught 2

I couldn't focus, my head was racing with all kind of thoughts. I had no idea what this would result in. My manager and teammate noticed something was wrong. I just told them I was coming down with something and felt ill. As there was only about an hour before closing time, my boss told be to finish early and get myself home, dosed up and to recuperate over the weekend. I didn't need to be told twice, this meant I could escape before bumping into Helen and being confronted about wearing...

Crossdressing

Erica Meets Sarah Part 1

I woke up alone on Saturday morning in my nylon blue g-string and nothing more. I wanted to feel it the instant I woke up, my sexually charged femininity, I wanted to feel it all day. Today I'm not a man, today I'm the girl every man wants. Today I'm a slut, your slut. I showered and shaved myself smooth. Ridding myself of body hair was always the first step. Nothing could make me feel more feminine than smooth skin from head to toe. I plucked my eyebrows and moisturized. I moisturized...

Crossdressing

Park n Play

Being the social butterfly that I can be at times, I was checking a website that listed my area to see of there were any 'cruising' areas I could check out in hopes to share my fetish for crossdressing and pleasure. There were several areas, too many to choose from, so I opted for a forested state park. Since much of the funding for the parks in Ohio have been suspended or cut, the chances of being targeted by a park ranger or law enforcement for public indecency can be pretty low. I've heard...

Crossdressing

She Made Me Do It

Something inside me just grabbed hold of my male shackles and snapped them in two; discarding them into the depths of depravity. I had been writing stories about crossdressing and transsexuals all week. I had been looking at girly pictures, not the feminine girl ones, the ones that had dicks. Some of them were absolutely gorgeous, far better looking than some women and I wanted to be one of them. I really did. I particularly loved the ones with the pink underwear and black bows. I have a few of...

Crossdressing

Karen Goes Out

I was so nervous I was almost sick. For years I'd dreamed of going to a bar that catered to the LGBT community but I'd always come up with an excuse not to, no matter how flimsy it might be. Yes, I'd gone out in public several times, shopping mainly, but also banking, getting gas, and even meeting with other girls like myself. So far, the only sex I'd indulged in while dressed had been primarily with my hand or a dildo and not with any other human being. To make matters worse, I'd only been...

Crossdressing

The Wedding Proposal chapter I

I slowly let the sheer, white stockings slide up along my closely shaven legs. They were smooth as silk, and no hint of coarseness caught the fabric as I stepped into them. The broad bands of elaborate lace hugged my thighs and made me feel great. Four straps, each decorated with a small silk ribbon, held the stockings attached to the garter belt I wore around my waist. The coarse lace felt tight around my body, but I loved the feeling of the feminine garment. It filled me with joy and arousal....

Crossdressing

An Introduction To Crossdressing The Finale

Reliving our evening’s events had Jackie and Chandra pretty worked up. “You girls seem to be getting a little excited," I stated. "Are you ready for some more fun?” Simultaneously they both grunted, “Yes we are!” I leaned across the table to find them both holding the others cock and slowly working each other into a frenzy. “You should probably save some of that for back at the hotel, before you run dry,” I said. But that didn’t seem to deter their enthusiasm, until Susan walked up. “I’m done...

Crossdressing

Crossing A Different Line

In my personal journey from straight, married heterosexual to bi male, I discovered, along the way, that I was aroused by women’s lingerie. It started with trying on a pair of my wife’s nylon panties. The feel of the silky material, and the sight of how it fit, quickly brought on an erection. I used another silky pair in my hand to jack myself off, being careful not to get any cum on the panties. The orgasm was unusually powerful. In the weeks following, I pursued my new found curiosity,...

Crossdressing

An Introduction to Crossdressing Pt 6

After Steven leaves me at the table with Jackie and his new friend Chandra, I start to fill them in on the details. I tell them, “It’s really Jackie’s fault that I got fucked so good; since he was being so aggressive with his dance partner, I got jealous and grabbed Steven’s ass.” Then I continued with, “This led to Steven grabbing mine beneath my skirt, and then stroking my cock and balls under my panties.” Jackie interrupted with, “Forget about the dance floor, tell us what happened in the...

Crossdressing

An Introduction to Crossdressing Pt 4

In Part 3, Jackie and I had our way with each other for the first time and then headed to the shower to ‘clean up’. As I was removing my feminine attributes - the wig, makeup and lingerie - it occurred to me that even without those items I still felt rather girly. Previously whenever I would change out of my lingerie back into my man clothes, my attitude would change as well. Maybe my attitude hadn’t changed this time since I had dressed all the way and given myself completely as a woman....

Crossdressing

My Mother s Boyfriend My Slut

Divorce often times traumatizes the children, but in my case, it set me free from all their arguments. Dad signed the papers and walked out the door on my seventeenth birthday; it was the best present he could have ever given me. I was finally free, I could go to parties and hang with guys. Mom was the lenient one who was always gone on some major trip. I was cool with it until she brought home a boyfriend. Coming home from Europe, my mom walked through the front door, shouting, “I’m home,...

Crossdressing

Laying the Groundwork

My fiancée and I always have been a bit more adventurous than the average couple when it comes to sex. While we both enjoy the sensual feeling of pure, romantic love-making, we also tend to get a bit rough and voracious when the moment calls. In the past, we had experimented with some anal play, with me initiating most of the contact on her. Fortunately for me, her hands also had wandered a few times in the shower together. Nevertheless, this was the extent of our pushing the boundaries from...

Crossdressing

Bookstore Crossdressing

It was at an adult book store in the north part of Denver. I had just gotten a nice pair of stockings with the latex band to keep them up and I had a hot pair of heels that brought out the tramp in me. I always entered the store with the heels tucked in my jacket, so they weren’t that noticeable. Once I was inside a booth, the heels came out the clothes came off and the slut came out. The hallway was empty where the booths were so I ducked into the booth that had a video of a luscious...

Crossdressing

Married Crossdressing Fun Ch 3

“Mikki?” Caz asked. “Yeah, babe?” “I’ve been thinking...” “Always a dangerous thing,” I said, cheekily. “Yeah, whatever. Seriously, I’ve been thinking about what happens next.” “What do you mean, what happens next?” “Well, you are really beautiful but I was thinking of stepping it up a notch.” My wife Caz is the most beautiful woman I know. I love her with all my heart. She is sexually voracious. We played a little game a while ago. She saw how turned on I got when she treated me like a bitch...

Crossdressing

Married Crossdressing Fun Ch 2

Caz and I had been living in our new home for about two months. Our life was wonderful. We loved each other more deeply every day. Caz enjoyed her new job and she was really good at it. She was a beautiful, sexy woman and in the field of international finance surrounded by mainly middle-aged men, she had the advantage and wasn’t ashamed to use it to further her cause. Her company was making record profits and she had already had a pay rise. She was also in line to get a huge bonus at the end of...

Crossdressing

Married Crossdressing Fun Ch 1

I was lying on our marital bed blindfolded, with my hands cuffed to the bedhead, wearing a pair of sheer black knickers. I was waiting for my beautiful wife to come home from her date with Antwan, her big black lover. I thought back to how this all began. Caz and I met when we were both studying at the State University. I was doing an MBA having completed my degree in Business. She was finishing her degree in International Finance. She was the most beautiful woman I had seen and I thought I had...

Crossdressing

An Introduction to Crossdressing Pt 3

As I was following Jackie to the hotel I couldn’t stop looking in the rear view mirror at what was a complete transformation in my mind. I kept doing that thing where you look away and then back hoping to catch your reflection not keeping up with you because you are sure it is not you. It is probably a good thing that there were not very many cars on the road since I wasn’t paying any attention to it while I was admiring myself. I did see Jackie’s turn signal and brake lights just in time to...

Crossdressing

A Date For The Weekend Chapter 1

I've been crossdressing and living as a woman full time for years. I put a lot of time and work into transforming myself into an attractive woman that can accompany a man anywhere in public and never raise an eyebrow. I've long since moved on from having casual cheap hookups to expecting more elaborate playtimes, and generally only date men if we can plan a weekend or more together. I mean, if I spend all this time and effort I expect more payoff than ten minutes of action. I really provide a...

Crossdressing

An Introduction to Crossdressing Pt 2

So as Jacky was going through his story about how we ended up in this shop, I started to look around. I found that my initial belief that the shop was just a hair dresser was completely wrong. The shop was split in two, long ways, with the left side having about four stations for regular hair work, two stations for nails and a couple of closed rooms for massages, waxing and tanning. The right side had several racks of all sorts of women’s clothes including lingerie, dresses, shoes, wigs and...

Crossdressing

My birthday treat

My next door neighbour had begun helping me with my crossdressing by buying me my own clothes, and despite her initial stipulation that I continue to dress in secret, we had experienced a moment where that had all changed. Once that day had passed, Ellie and I became almost inseparable. If we weren't together, we were texting or talking on the phone. We would do everything an ordinary pair of best friends would, with the exception, of course, that Ellie would help me with my little secret....

Crossdressing

FORCED TO CROSSDRESS AND I LIKED IT PART 2

FORCED TO CROSSDRESS, AND I LIKED IT!! PART 2 I walked out of the room picking up a package that was left for me by the door and left for the bathroom to change into what was purchased for me. As soon as I entered and closed the door I rummaged through to find a pair of black lace bra, panties, garter belt and high heels which I quickly put on, eager to suck and fuck cock. As I entered my darkened room I see Xavier stretched out on my bed with his huge cock standing straight up waiting for my...

Tickets please

Standing by the window, I watched as the countryside flashed by. My train had been delayed due to a dodgy signal just outside the station, but judging by the speed the driver was maintaining there shouldn't be much of a delay, thank goodness. Even though I hated my job and boss I needed the money desperately. With a sigh, I turned away from the dreary grey outside and tried to make myself comfortable on the little fold down seat. The train wasn't busy, but I needed to be on my own, at least...

Crossdressing

Crossdressing at the truck stop

Hello this is my first story I really hope you enjoy it I am a crossdressing truck driver and with my job I have a lot of time to enjoy dressing up in my truck. One night I was all dressed up in one of my sexy outfits watching some porn and thinking about trying to find a nice hard cock to suck. So I put an ad on Craigslist and got a few but none of them wanted to come to me then I got a message from a guy, he said that he was a driver and was at the truck stop. I ask him what he wanted to do...

Caught CrossDressing by Neighbour

I was enjoying a day at home doing some chores and cleaning. I couldn’t resist the urge to dress up, and was soon wearing stockings, high heels, garter belt, bra and g-string. I completed the dressing with full make up, wig and a Sexy satin French maids uniform. I put on some music, had a couple of drinks, and began to do vacuuming and the like. I was having a fun sexy time, dancing about, wearing the little maids dress. I heard my phone buzz and picked it up. There was a sms message from my...

A Crossdressing Story

***A crossdressing story***(All characters are fictitious...maybe…!)I had been dressing for a number of months when this adventure occurred. While I felt that I was learning the basics of makeup and dressing, I needed some expert advice and so I placed an AD in a local TV/TS newspaper for an understanding woman to help me with my feminine side. Little did I know what an erotic journey this would take me on! I got a number of good responses, but the best came from a woman named Debbi. Her...

Attracting some attention

Like most people in their late teens and early twenties, I enjoyed going out to pubs and clubs. I would go out with my friends and my girlfriend, always in guy mode. I was still in the closet pretty much back then. I would dress up at home when I was alone, never venturing further than the back garden to have a sneaky cigarette in the cool evening air, but that was as far as I ever got. I would watch my girlfriend getting ready before we would go out and always feel a little touch of jealousy...

Crossdressing

Becoming John Collins Mistress Part One

Hi. My name is Chris, though some know me as Christine. I am John Collins’ mistress. We care deeply for each other. John “keeps” me. He supports me financially and in return it is my pleasure to keep his sex life exciting, as well as entertaining any of his gentleman friends who drop over. It all began innocently enough, I suppose. I had just turned eighteen and had moved out from my family’s home to be on my own. To support myself I worked as a landscaper, as well as a house painter. I was...

Crossdressing

Meeting One of the Neighbors

Tom was almost seventy. We lived on adjacent streets and his property backed on mine. I had moved in only a couple of weeks earlier. I was renting the place. I was so excited to be on my own at last, especially because I loved to crossdress. My new freedom was exhilarating. One day I’d been in my back yard in the late evening, dressed in a cute white bikini. I was lying face down on a lounger, my bikini briefs down low enough to free my cock and ass. There had been a full moon that evening...

Crossdressing

Steve the Crossdressing Cat Lover

My boyfriend, Steve, has a lot of cats. I can't tell you exactly how many because the little critters come and go out the pet door and scatter as their furry little paws please.Steve lives on a farm. Well, it's kind of a farm. I mean, he has a lot of land, but he doesn't exactly grow anything on it except cats from what I've seen. And he has a barn, too. You'd think with all that land Steve has that he'd keep a couple of horses to ride but no. The barn is filled with cats that curl up and sleep...

Crossdressing

Mother and Crossdressing Son Fantasy

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

A surprise ass fucking in panties

A very curious thing happened to me the other day and I feel I need to share it with you... I have been 'mildly’ crossdressing for over a year now. I say 'mildly' because I am not into full feminization, I just love the feel and look of lace panties when they are hugging a good looking cock, not to mention the taboo. I have taken to wearing stockings too which feel amazing, it's like having your whole lower half caressed persistently. I have thought of wearing a bra but, although I can almost...

Crossdressing

Caught By My Girlfriend

Hitting puberty late in high school had its disadvantages. A slender, almost feminine body and a small dick was not something a lot of women tended to go for, however, I was lucky enough to find Adrian. We hit it off right away, shared many things in common and we couldn’t get enough of each other. She was gorgeous, standing at six feet, she was just as tall as me. Her beautiful crystal blue eyes made me weak at the knees. Things were going great, I would arrange various "date nights" for us...

Crossdressing

still more crossdressing fantasy

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

Crossdressing at the cinema

I placed an advert on Craigslist as I fancied something new. I'd been crossdressing for a while and had met a few people for fun but wanted to try something a bit more exciting. My advert was looking for someone to meet in public for sex with me dressed in lingerie. A few replies came but the one that caught my eye wanted to meet in an adult cinema in London near city road. I heard of this place and fancied trying it out. We agreed to meet at 11am in a coffee shop nearby and go to the cinema...

The Sexy Secretary Gives at the Office

Working as a tranny escort is my favorite way to earn money and get lots of cock, at the same time. I love to put on sexy panties and show off my body to men, so it is a job I enjoy doing the most. The fact that lots of men really like me and call me back again and again makes me feel wonderful, as well.I have long hair that makes me look like a woman from behind and my breasts are big for a man's and they get played with and sucked on like a woman's. In fact, most of my clients tell me I'm...

Crossdressing

Vanessa s First Date

This is a memoir of my first time meeting a man. I'd been crossdressing for many years. I had many fun nights dressing up and playing with my toys but I wanted something more. I liked to get on the phone with guys and play around. I had my favorite toys to use, especially my eight inch dildo and my butt plug. I really got into my phone sessions, but I felt like I wanted to go further. There was a nice guy who I had been talking to for a while, and I got to know a little better than the average...

Crossdressing

Wife s crossdressing fantasy Part 3

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. My Wife's Cross dressing Fantasy 3 Then my wife looked at me and said “Happy anniversary darling.” How did she know the effect this experience would have on me. I was changed forever. It was such a wonderful experience. She deserved that I come up with something just as exciting for her, but what? I thought and thought, but I couldn't think of anything to equal what she did for me on our anniversary....

Crossdressing

My Night at the XXX Video Theatre Part One

It was almost 2 AM when I pulled into the Big Town XXX video theatre in the southeast part of where I live. It was a Saturday and the parking lot was full. I had never been to this particular theatre but it was in the adult theatre chain that I had been visiting for the past two years. Each theatre is different depending usually on the part of town where it is located. Southest part of my city is rough. It is predominately African American. This theatre is in a small run-down strip shopping...

Crossdressing

Wife s Crossdressing Fantasy Part 2

This is a work of fiction. Any resemblance to any person, or incident is strictly coincidental. Since my wife shared her fantasy with me and made me her bitch, our love life has changed. Now I always have something cute and satiny on, whether it is panties under my boy's clothes, or a silk nighty at night in bed. I love being my wife's bitch and I can never go back to who I was before. When our anniversary came around, a month or so after my initiation to dressing up, my wife announced to me...

Crossdressing

Wife s Crossdressing Fantasy

This is a work of fiction. Any resemblance to persons or incidents is coincidental. My adventure began while I was a senior in high school. My mother took me to the dentist. It was late afternoon and shortly after I was called into the examination room the receptionist and assistant went home. The dentist then closed the door of the room we were in. He walked over to me and started making small talk... I guess to make me feel at ease. We talked about many things. He told me I was cute and that...

Crossdressing

crossdress in tight flared jeans went out in publi

well i have always crossdress and dressed up in my house but that recently has turned boring. i figure do something more thrilling and excited. i desided to put my tight junior size 9 flared jeans and go in public. I know that if someone saw me i probably ganna get laught at. so i started practicing by wearing the jeans and going outside my house like in the back when it was night. it really felt so good. the tightness on my hips and ass and seeing the sexy flare of the jeans made me feel so...

Crossdressing internet ad part 1

I have been crossdressing for several years mostly at home going to the theaters some and to local bars. I was on my way to the Theater one night and stop at a service station and was being hit on by a couple different guys. I flirted back a little then one guy came up to me at the gas pump and said I would love to eat that pussy. I smiled and said maybe next time. When I got home it got me thinking that maybe I should go on a CD date. I looked on a couple dating and personal sites and one...

Kissing Crossdressing Cousins

For as long as I can remember, I have always been drawn to wearing women's clothing. When I was 4 years old, my mother would take me shopping and I would throw tantrums if my she didn't take me to look at the girls clothes too. I would try on pants but only on one condition: I got to look at the dresses when we were done!When I was 5 years old, I wanted to be Princess Leia for Halloween. My mother thought it was adorable and was more than happy to buy me the costume. The following year, I...

Mom made me a Fluffer

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

Crossdressing

Seduction of Piper

I want to thank Farmgal who's sexiness inspired this erotic and steamy tale. Thank you Farmgal, I enjoyed writing my sexy fantasy of seducing you.Stephanie was attending the check out register at Victoria’s Secrete when an extremely sexy woman strolled into the store. Stephanie’s heart beat faster and her eyes locked on this sexy woman as she sauntered towards the display of the new line of sexy panties and bras. The woman’s eyes locked with Stephanie’s for more than a few seconds. Stephanie’s...

Crossdressing

Making Scents of Crossdressing

Making Scents of Crossdressing By Ricky I am a hi-tech person. I work and play with some of the latest computers and electronic equipment, have stereo speakers in every room of the house, and can bore you for hours with torrents of jargon on just about any subject you care to name. When I don my feminine attire I have a fondness for synthetics, those modern wonders of the laboratories of some multinational chemical giant. Who else but those hi-tech wizards could turn a barrel...

Humor

Crossdressing with my Girlfriend and Boyfriend Part 3

Crossdressing with my Girlfriend and Boyfriend By Cindybelle Part 3 At the rehearsal on Friday night Mrs Cartwright asked me how my mother was getting on with the dresses for the show. "She has just about finished two dresses for me, including the wedding dress," I said. "I'm sure they will be very pretty, she did so well with your costume for Dorothy last time I can't wait to see them," replied Mrs Cartwright. I...

Crossdressing with my Girlfriend and Boyfriend Part 4

Crossdressing with my Girlfriend and Boyfriend By Cindybelle Part 4 Oh no, I thought, I sensed that dizzy feeling coming over me again, there was so much going on in my life I didn't understand, with my mom, with Jason and with Aubrey as well and now Janette was going to tell me about mom and dad and being brave. I sat with my own thoughts for a while and then I noticed we were not driving home. "Where are we...

Crossdressing Charlie Episode 2 High Waisted Skirt

CROSSDRESSING CHARLIE Episode 2 HIGH WAISTED SKIRT "Oh Charlie, you're burning up!" said Mom. She took her hand off of his forehead and read the thermometer. She then left the room to get some medicine. Charlie took the thermometer out of his mouth, held it up against the lamp on the bedside locker, grabbed his hot water bottle and placed it on his face. He left it there for a few seconds before he heard approaching footsteps echoing from the hallway. He slipped the hot water...

Crossdressing Charlie Episode 3 Relinquishment

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

Crossdressing Charlie Episode 4 Lust

CROSSDRESSING CHARLIE Episode 4 Lust The sky was blue. Yes, just blue, not a cloud to be seen. Every so often a light sliver jet could be seen, trailing white smoke behind it. The sun hung over the city like a warm light bulb, belting its warm rays unto the necks of people within the hustle and bustle of the packed streets. People wore shorts, t-shirts, sunglasses and sun cream, making the most of the rarely seen good weather. The sounds of construction workers banging and drilling...

Crossdressing Charlie Episode 5 Rachel s Date

CROSSDRESSING CHARLIE Episode 5 RACHEL'S DATE Rachel sat in front of her makeup station brushing her hair whilst humming a soft happy tune. She had just dried her hair after getting out of the shower. She was dressed only her in bathrobe as she wasn't in the least bit cold because outside the sun was splitting the rocks and melting the tar on the roads. As soon as she was done brushing her hair into a silky shiny doo she walked over to her chest of drawers and began to put on her...

Crossdressing Charlie Episode 6 The Tennis Uniform

CROSSDRESSING CHARLIE Episode 6 THE TENNIS UNIFORM Since Charlie and Rachel's day of sorrow three weeks ago, much has been altered in their lives. For a brief time they became closer than ever as they shared their feelings with each other. Emotions of pain, jealousy, hurt; anger and betrayal were common occurrences of feeling in their deep immersive conversations. Despite the fact that their mother felt alienated and that she was alone in the universe she still felt a glimmer...

Crossdressing Charlie Episode 8 Family and Nightmares

CROSSDRESSING CHARLIE Episode 8 FAMILY AND NIGHTMARES His eyes opened quickly. The first thing that came into view was his bedroom door. His heart slowed down as he exhaled into his pillow. It was just a dream. He thought. Well of course it was! His eye's swirled about in their sockets like a startled animals as he rolled over onto his back and licked the inside of his mouth. That usual morning taste was in his mouth and he couldn't wait to get his hands on his toothbrush. He...

Crossdressing Charlie Episode 9 Everybody s Crazy

CROSSDRESSING CHARLIE Episode 9 EVERYBODY'S CRAZY "What are we going to do now?" Charlie yelled over the loud rush of passing cars. "I don't know!" cried Rachel, tears streaming down her face. "Well we can't just hang around the streets all night!" shouted Charlie. Rachel didn't say anything back. She continued to walk briskly ahead of Charlie as if she knew where she was going. Dusk was rapidly descending into night and the skyline of the distant city buildings was...

Crossdressing Charlie Episode 10 Prudence Svahnstrom

CROSSDRESSING CHARLIE Episode 10 PRUDENCE SVAHNSTROM The moment that Charlie was told that he would be moving out of his current home he could not help but feel a little sad at first. However, the more he thought about the prospect the more it made him feel hopeful for a brighter future. For so long he had been stuck in a never-ending chasm of darkness and now there was a light at the end of the tunnel. It was something to look forward to, something to root for and above all else a...

Crossdressing Charlie Episode 12 Seventeen

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

Crossdressing Charlie Episode 13 Hide and Seek

CROSSDRESSING CHARLIE Episode 13 HIDE AND SEEK TWO YEARS AGO... Dave watched the raindrops roll down the windowpane and morph into one another before they dripped away. Outside, it was pelting down so hard that it looked like the rain was coming up from beneath. He watched people scurry down the street with umbrellas, newspapers, and briefcases over their heads to protect their precious haircuts. It was dreadful weather. However, he was safely inside a nice warm caf? with a cup of t...

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