Dressing Up indian porn

My Little Black Dress

My Little Black Dress Janet L. Stickney [email protected] I had gone out to pick up a few items I needed, like pantyhose and new eye shadow, just another fear filled adventure into the outer world. I always felt edgy buying those things that guys didn't usually buy, so I had gotten dressed and bravely went out once again to buy the few things I needed, before I scurried home. I had yet to have anyone figure out that I wasn't a girl, or, at the very least, if they did, they...

My Little Black Dress

My Little Black Dress ethan susan Janet L. Stickney [email protected] I had gone out to pick up a few items I needed, like pantyhose and new eye shadow, just another fear filled adventure into the outer world. I always felt edgy buying those things that guys didn't usually buy, so I had gotten dressed and bravely went out once again to buy the few things I needed, before I scurried home. I had yet to have anyone figure out that I wasn't a girl, or, at the very least, if they...

Jack s Little Bitch

Steph had been gone for about one week out of her two week visit to her Mom. She'd asked me to pick up the mail and water the plants while she was away, because her boyfriend, Jack, was also going to be away for the month on a business trip abroad. “Jack wouldn’t remember to water the plants even if he was there,” said Steph, laughing. “At least I can trust you.” Steph was right inasmuch as I could be trusted to look after the place whilst both she and Jack were away, but sadly I couldn’t...

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

Making friends with my housemates

People always react in different ways when they find out about my cross dressing. Girls are usually more accepting than guys but everyone is different. I was twenty-two when I went to university and decided I would be completely open about it with everyone I met there. I found that most people were pretty cool with it, although some took some time to get used to it. I spent the first year living in halls with three girls and two boys, and thanks to the first night together where we all had a...

Crossdressing

My New Life As A T Gurl Slut Pt 3 Nine Cocks in 48 Hours

I was going to be the gurls' slutty French maid for the night and couldn't wait to get to Karen's so the fun could start with four hot t-gurls and four hot cocks for my mouth and ass. Lucy picked me up, and as soon as I got in her 4x4, I slipped out of my jeans to reveal my knee-length black boots, black lace top hold ups, black suspenders, and wet look black micro mini skirt. I unzipped my jacket to show off my sexy black bra around my C cup tits that were firmly attached making me feel sooo...

Crossdressing

My New Life As A T Gurl Slut Pt 3 Nine Cocks in 48 Hours

I was going to be the gurls' slutty French maid for the night and couldn't wait to get to Karen's so the fun could start with four hot t-gurls and four hot cocks for my mouth and ass. Lucy picked me up, and as soon as I got in her 4x4, I slipped out of my jeans to reveal my knee-length black boots, black lace top hold ups, black suspenders, and wet look black micro mini skirt. I unzipped my jacket to show off my sexy black bra around my C cup tits that were firmly attached making me feel sooo...

Crossdressing

crossdresser confession part 1

I really loved my wife; she was the most beautiful creature I have ever known. Tall, brunette and the longest legs you have ever seen. Myrtle's beautiful face is framed by her gorgeous brown hair. She was about 5'8" and had a great ass. Her curves were soft and very feminine, not a big chest but nice and perky tits I loved to play with.She would drive me crazy when she donned a pair of pantyhose and heels with a short skirt. She didn't know it, but she would not have been able to keep my hands...

Crossdressing

A Nanny Femtastic Chapter 1

A NANNY FEMTASTIC! Chapter 1 My story starts during a very bleak time in my life where I was unable to find continuous work of any meaningful type. I had, I suppose, looking back now, rather stupidly pursued Child and Nursery Care as a further education route. Much to my parents consternation! Yes I was the only guy in the college but I thought I would soon move into management positions and my career path would take off! It was actually cool to have so many women around me, and I did have...

Crossdressing

Auntie s Panties

I was supposed to be home alone that day.At least that was the plan.It was the break between college semesters and I was staying near the beach with my uncle and his girlfriend, Pam. The plan had originally been to come down with a pal and spend the week blowing off steam before classes started back. A supervised vacation in the eyes of my parents --one where I couldn't get into too much trouble since there was adult supervision.But, at the last minute, my friend had to back out. I could have...

Crossdressing

How I got started dressing my true story

As far back as I can rememeber I have always gravitated towards fem things. As a young boy I played with whatever girls clothes I could get my hands on. Which wasn't much. At 12 y/o I had a few pairs a panties and bras stolen from my cousins. One thanksgiving after dinner the girls changed and one of them left behind a black knee length dress and white pantyhose in the guest bedroom. I was so excited when I found them...needless to say she never saw that dress again. With the bra and panties I...

Six Months

After all those years of longing to be free, stuck in relationships with women that frowned upon my cross dressing, I was still very much relishing my freedom. I was dressing every moment I could, the minute I got home from work every single day; a mini dress, heels and stockings were what I craved so desperately. I had been living alone now for a couple of years and would have thought he urge would have sated by now but I still hungered to be feminine at every moment. I am five foot six, small...

Crossdressing

Caught in My Girlfriend s Panties

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

Crossdressing

A Crossdresser Gets Caught

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

Crossdressing

Weekend Discovery 2

Simone's eyes grew wide when she realized that the stunning blond she was sitting next to was, in reality, her boss and the object of her most intimate desires. Now she had seen transvestites and drag queens before, but none of them looked this good. She was sitting just mere inches away from his face and still couldn't see any trace of Andrew Lippincott. Without warning Andrea leaned forward and gently placed her lips on Simone .When their lips touched a bolt of pure desire shot through...

Crossdressing

Can t I Have Them Both

Waking up to the sound of my alarm blaring, I roll over and slam on it. Of course it doesn't go off, just crashes to the floor. I know I shouldn't have stayed up so late last night playing video games, but what can I say? Too late now, I suppose. I reach down to pick up the clock, seeing the time blinking at me. Getting out of bed, I grab the shower before anyone else can. I know what it’s like in this household in the mornings. My two sisters will fight like crazy for the bathroom. I get why,...

Crossdressing

Felix becomes Felicity Chaopter 3

FELIX becomes FELICITY Chapter 3 ..He bent forward and thrust his large hands up my skirt on my thighs with his thumbs resting on the root of my penis, and put his face close to mine, “You had better be a good girl for everyone’s sakes sweetness. I know you love your Mum and Sister!” He slowly moved his hands up to my breasts and squeezed them hard looking into my eyes. I was speechless. “Yes I have a soft spot for sexy little girls like you.” With that he pulled away and walked into the...

Crossdressing

Night Out Ch 5 Shopping Spree

June's heart was racing; he visibly shook. Sweaty palms, nervous demeanor, he may as well be a dealer based on his level of suspicion–he'd just be noted as a bad one.The bag he carried felt heavy despite not holding anything of significant weight. Its contents may as well equate to a full ton due to the knowledge of what was inside.It was crazy to think a few moments ago this very man was imagining bending Evy over the next sturdy object he could see. Their games of teasing each other after...

Crossdressing

Becoming C Her

I remember when I first felt it - silk. It was the most luxurious fabric my hands had ever touched. My fingers handled it with care in the department store. I was a teenager shopping when I noticed the silk nightgowns donned by the mannequins, draped so elegantly over their bodies. My body responded immediately and I had to buy some. That day, I bought a long nightgown and three pairs of panties - my first purchases in ladies' apparel.In the privacy of my bedroom, I slipped the panties on and...

Crossdressing

Second Place Winner

I’ve been dressing up as a girl in dresses and going out in public for the past two years since entering college. My goal has always been to be as pretty and as believably female as possible, when I choose to dress up as a female. I am blessed with being short and slim with facial features that can make me very realistic in make-up. Blonde hair extensions, false eyelashes, and glue on nails complete a look that can be credibly convincing according to friends!I have always tried to work my...

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

Friend Becomes My First Part 1

This is a true story of my first time having sex dressed a girlIt finally happened, and it was a dream come true. I started dressing as a girl when I was 17. For me, it started with a thong I stole from my mom's drawer which eventually went on to lingerie, to normal clothes, and all the way to dressing fully. Im now 24, and all I wanted to do was to show myself to a man and be the little slut I know I can be. I tried online a few times but being in the closet and meeting randomly made me really...

Crossdressing

An Unforgetable Experience

I will never forget the day Carrie enter my secret world. It was the summer I was 17, I had been dressing my sisters clothes since I was about 8yo. In more recent years I had started buying a few of my own clothes and lingerie nylons and make-up. It was a Saturday and I was home alone and decided it would be a good day to dress and be girlie, excited about my day I waxed my legs and bikini line painted my nails a soft pink and took a relaxing bath with lavender bath beads, feeling very sexy I...

Crossdressing

Uncharted Territory

Of all the activities that Cal Markus imagined he'd be doing on his summer vacation, this was not one of them. Here he was in his longtime friend John's attic wearing an almost sheer pair of black silk panties over a pair of black crotchless pantyhose and seated in front of a large lit makeup table as his friend was busily bustling around the room depositing items of makeup on the table.The sensation of the silky panties against his skin was unbelievable as was the sight of his cock pushing...

Crossdressing

Sissy Blane and the Hydraulic Inevitable

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

Crossdressing

Memoirs of a Crossdresser Chapter 1

My True Story Chapter 1: I was a kid when I first discovered women's underwear. I loved the way it made me feel. I had a friend who I'd play the normal games that kids play with, and I would always be the girl character. We were children, so nothing out of line went on, but even at a very young age, I had felt an attraction to femininity. There was something that made me feel like I should be the damsel in distress, waiting to be rescued. I remember wanting to feel girly. As I got older, my...

Crossdressing

A New Friend at the Adult Toy Store

I decided to go to my favorite Adult Toy Store. Now, this is not one of those dark, dingy places that make you feel uncomfortable. It is well lit and attractive. The people who work there are very nice, polite, helpful and make you feel right at home. So I can go and feel at ease while I browse. This store carries lingerie, clothing for clubs or stripping, stripper shoes, toys, and videos. Because I was driving straight to this store and then home again I decided to be a little more daring...

Crossdressing

Discovery

Discovery, one of the greatest fears he has. All others take a backseat to his fear of being discovered indulging in his passion. You see Kyle is a cross dresser.Like so may others he doesn't know where this desire to dress up came from, but soon it was too strong to ignore. He started out with pilfering a few items from his sister's room and wearing them behind closed doors when the house was empty. But it wasn't enough.To his delight he discovered that there were literally hundreds of sites...

Crossdressing

My First Encounter

I had been cross dressing for years but only in private. I had also had a thing for bondage for a long time. A couple of years ago, I met two other cross dressers who were into bondage. We had been getting together every couple of months and playing bondage games with each other. We would take turns tying each other up and taking photos and videos. But, it was always clear that the other two were completely straight and nothing sexual would be involved. I was fine with that as I thought that I...

Crossdressing

A weekend with Nancy part 2

Nancy informed Alice that she would be using the bedroom to dress me, and that she should pick out an outfit consisting of no fewer than seven articles, gather her make-up and whatever else she required and then use another room to get dressed. Furthermore, Nancy informed Alice if she didn't like what she was wearing when she returned that she would be punished, and to not waste any time dressing as she would require her help in transforming me. I had the feeling that no matter what she came...

Crossdressing

The Feminisation of Michael Chapter 6

The Feminisation of Michael. Chapter 6 The taxi dropped me off at a top hotel in London. I checked in as Miss Michaela Wilson. My new name! I had credit cards and bank account details sorted out when I was in hospital so had a purse full of plastic! A bit like I now had a bra full as well! After the porter had left me alone in my suite of rooms I just collapsed onto my bed. What an amazing few months I thought. This is now the start of a new life as a totally new person, in every way! ...

Crossdressing

Working It

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

Crossdressing

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

Uncle Joe

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

Crossdressing

Triplet X Love Times 2 Book 1 The Honeymoon WeekChapter 7 Salad Undressing

It had taken the girls very little time to go to the mall and return with their purchases. Hannah's most difficult problem was figuring out how to add a new camera to the existing wireless surveillance system, yet keep it invisible from other users of the network, that is, from the boys. It didn't take her long to figure it out though, and in no time the 'F10' key of their computer was controlling a private, password protected, camera that, after testing, they then sneaked into the boys'...

Special Soiree

“Amanda” was fully dressed when “she” opened the door. She almost shyly greeted her close friend “Suzette.” “Hi Suzette. It’s been a while,” Amanda said.Suzette had an unhappy expression on her face. “I know, too long.” Then she looked around clearly nervous.Amanda knew that sensation, and opened the door wider. “Please, come in.”“Thank you, Amanda,” Suzette said her confidence returning immediately. She strolled past Amanda into an apartment she had visited a few times in the past. Amanda...

Crossdressing

My New BFF Part Two

It was midnight by the time I got home from Tiffany's. I took off my shirt and pants and put on the silk nightie she gave me over the bra and panties I wore home. The feeling was exquisite. It felt so comfortable when I got in bed that I fell asleep within minutes.When I woke up the next morning, I reluctantly took my lingerie off so I could take my morning shower before starting my workday. I work at home on my computer taking and entering sales orders and customer assistance for an office...

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

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

Where Did My Damn Key Go Part 3

Four days; I've dealt with four grueling days of not being able to touch myself. Jesus, how can anyone even do this without even going insane?!Ever since I crossed paths with that dominating bimbo, my entire routine had changed. And to be honest, I was surprised at how much sex was in my life. From the moment I woke up to the second I crashed and fell asleep, my mind was very frequently in the gutter, wondering when I was going to get some ass or where can I go to beat one off real quick....

Crossdressing

One On The Way Part 2

On Saturday morning, Ryan was alone sitting at his kitchen table enjoying his morning coffee and cigarette. Normally, Belinda was with him but she got a call from her job offering her some overtime and she bolted. As he smoked, he thought about Belinda's newest request. It seems that dressing in lingerie wasn't enough for her, she wanted to see him in a wig and makeup.While dressing in lingerie was definitely out of his comfort zone, this newest suggestion went way beyond what he was prepared...

Crossdressing

My First Time Part 3

As Lydia had promised, on the first day of her vacation I got my first lessons in high heels. It took most of the day before I was able to walk across the room and not fall on my face, and these were only a moderate heel. I took her to dinner to celebrate and, at her request, I wore the satin thong under my jeans.Lydia could not resist reaching out and squeezing the bulge in my jeans, and her knowing that my cock was encased in satin thong made her hotter that normal. I even unzipped at her...

Crossdressing

Dressing Room Creampie

While no one was looking, she grabbed my hand and pulled me into the dressing room with her. We were at one of the more upscale clothing stores at the mall, where the dressing rooms are down a little hallway and have full-length doors. We weren't exactly isolated, but no one could see us, and if we were quiet, probably no one would bother us. I had been following her around the mall all morning and getting pretty bored. But as she pushed me against the wall and kissed me, I realized that she...

Exhibitionism

Provocative Dress

Disclaimer: This is a story. Fiction. It is not real. It should not be real. If you believe this sort of stuff should actually be perpetrated upon non-consenting beings you are a danger to society and should be treated accordingly.Provocative DressShe was a virgin when they married. So was he, she said. I knew that already. She'd blogged about it in her blog. She blogged about all sorts of things: her kids, the weather, their little homestead with it's chickens and goats, but the parts I loved...

Just Normal Wearing A Dress

Just Normal to Wear a Dress I woke up in some hospital. I could not remember how I got there, but the nurses were telling me I am ok, I survived my auto accident and I will recover just fine, as they kept smiling. I felt fine, was ready to go home but they wouldn't let me. One nurse after another came in asking questions to test my memory. The head nurse told me I had to stay one more night so they could watch me. A younger nurse came in to help me with my shower. She came right...

My First Time Dressed as a Girl PT 2 Aftermath

My First Time Dressed as a Girl,(PT 2) Aftermath Hi Reposting an account of how I got started XXXdressing so that the first month is properly documented because it was what set my behavior for the next three decades).(The events of this story are true and reflect what happened thirty years ago the first time I went all out and dressed as a female. The conversations in it may not be completely accurate, as this was a long time ago, but are as accurate as my memory of these past events can...

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

intro to the world of cross dressing 1

My family was middle class mutt of a family. My mom brought two daughters and one son, Tammy, Lilly, and Teddy, or “Tee” as we call him, into the marriage; she had with my dad, and they had two, my brother and me. My full brother’s name is Ken, and I’m Sam. My dad was an accountant and a part-time college professor at the local community college, and my mom stayed at home as a housewife. We were all dragged to church every Sunday and when we became of age we were allowed to choose whether or...

Sexual awaking 2 The cross dressing Journey

Cont. from Sexual AwakeningsAnd then, there were my sister’s clothes. I’d always had an attraction for female clothes. Even as a boy I loved looking at the women’s and girls’ section in my mother’s catalogues. I mostly looked at the underwear. It was exciting to see girls and women in bras and knickers. I loved slips too. They looked so smooth and silky. Strangely, at that time, I had a fascination for directoire knickers and can remember dreaming about wearing them. I also enjoyed looking at...

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...

A Night of Firsts pt 2

I opened the door to the club and walked inside. From the outside, the older brick building looked sort of run down, but once inside I found myself in a club with large bar on one side, polished brass railings, mirrors, subdued lighting, tasteful seats at the bar, hardwood floors, tables, a few booths further away and at the very end of the club a large stage with karaoke being sung. This was no seedy dive bar, thank goodness.The lights, the music (karaoke music is always so loud as if...

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

Spying On My Sissy Slut Husband Part Two

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

Crossdressing

Being Suggestive

As a young college student my life and my dedication to the joys of being a transvestite had become conflicting. I had to put my college classes first, but living off campus made my female life so much more workable on weekends. I now looked at my sexy mini-skirted flirty self in a very different way now that I had discovered that attracting men had a quite enjoyable side. I realized that there were at least some men in the world that I could trust, and I finally felt so free to be the feminine...

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

48 Hours Chapter 2

Chapter 2: Let's Make UpLynn walked into the bedroom and threw the bags down on the bed, a white lacy suspender belt falling out from one of them."Wow," smiled Chris, "you weren't kidding about the weekend.""I certainly wasn't. Now lose the dressing gown and turn around. Shut your eyes too, keep them shut until I say otherwise, and remember, no more questions."Chris did as he was told. He really wished he could watch her undress and put on that new lingerie.He heard her pull off her dress and...

Crossdressing

The Beauty And The King I

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

Crossdressing

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

Three nights in London night 3 Irene rocks

I woke up looking into the smiling face of a pretty redhead. Sunlight was streaming through the curtains of her bedroom. "Good morning, Irene," she said, and she kissed me on my nose. I smiled back and slowly remembered my adventures of yesterday. When I moved my legs it dawned on me that I was still fully dressed. I even had my high heeled boots on. My skimpy black dress was pulled up and revealed the tops of nude holdup stockings. The front zipper of Gabrielle's leather dress was open and...

Crossdressing

All the Way Part 1

I'd only been married a little over a year when my wife came home early and found me jacking off using a pair of her panties and to be sure, this wasn't the first time. There I was lying in bed with her wispy little nylon panties wrapped around my dick and cumming like nobody's business. I was so wrapped up in my own pleasure that I hadn't even noticed her standing in the doorway watching me. “Are you having fun?” Her voice scared the shit out of me and my erection faded much faster than...

Crossdressing

Derek and Amy Derek s Turn

As I walked into the hotel room hours in advance, my cock was rock hard with anticipation. The last time me, my lover Amy, and her husband Matt were all together, it was my dear love Amy's turn to be in charge. Amy had Matt and I dress like two Fifties sluts. The kind of girls uptight parents used to believe would cause the downfall of society. It was both Matt and I's first times with other males though not my first time dressed up. He is still fairly new to this as his wife just discovered...

Crossdressing

Shopping with the Boss s Daughter

I came home from work after a successful morning meeting where we finalized a big project. I decided to celebrate by going out to buy a new dress. I changed out of my business suit and grabbed a quick shower to shave smooth. I put on my make-up, choosing to go with a conservative look for the day with a pink lipstick. I got dressed with black panties and bra, and pulled on the silky nylons and attached them to my black lacy garter belt. I then slipped into a long navy skirt with matching blazer...

Crossdressing

Brent Lets Brenda Go Out And Play

BrendaBrenda walked into the bar area of the restaurant. As she strolled through, several of the guys at the bar just stared. She looked ravishing in a black cocktail dress, her three-inch heels, and long flowing red hair. She headed directly towards a table where another man and woman sat sipping drinks.As she approached, the man stood up and gave her a hug and kiss that would’ve started a small fire in the forest. Then before sitting down, she leaned over and gave the woman a kiss that...

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

Dan Becomes Dawn

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

Crossdressing

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

Becoming Anthea

My name is Anthony and I am twenty-two years old. I have extra-long dark hair and darker eyes. I tie my hair into a ponytail and have a close trimmed beard. I look handsome and enjoy keeping myself in shape. I am a lucky guy as I have a very sexy girlfriend who is two years older than me. Zoe and I met at a mutual friend’s party and hit it off right away. She has short blonde hair and blue eyes. Her small beautiful mouth sits beneath a cute button nose. All in all, Zoe is a goddess and I love...

Crossdressing

Glimpses of Consequences

GLIMPSES OF CONSEQUENCESBy DrBill"HOWA we going to start?" The ritual joke having been followed by the ritual groans, the Housewives of Worthington Acres came to order. The group had evolved from informal visits for coffee and complaining to a neighborhood organization of sorts. While the meetings still tended to be primarily boast and bitch sessions, they also traded useful information and occasionally took on neighborhood improvement projects and the like. But they did not try to pretend that...

Crossdressing

Surprise at Girls Night Out

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

Crossdressing

And It Begins

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

Crossdressing

Chris s First Oral Experience

My name is Christopher, I’m twenty-eight years old, and have my own apartment. I work for a company which furnishes custom programs for businesses. We build the programs in our office, then some of us have to go to the customer to implement it, train their employees, then monitor it for a few weeks to assure it operates properly.While we’re at the customers, we look for improvements that can be made so we can expand the program, increasing our charges to them. This starts a cycle of going back...

Crossdressing

My Early Story

From my earliest memory, I liked trying on girls' things. My mom’s slips, sister’s panties, even my aunt’s nightie, (that is another story). I even went as far as dressing up completely when I was home alone. Mostly I wore my sister’s things. I loved her short shorts and halter tops. We were about the same size even though I was a year older. I didn't necessarily want to be a girl, just dress up and pretend. I loved to feel like a sexy, pretty girl. But, of course I always hid it from...

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

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...

Punished

I glanced around the second hand clothing shop to make sure that no one had seen me pick out the pink, pleated netball skirt from the rack. I hid it beneath a pair of long pants in my hand. I felt my heart start to beat furiously as I stood next to the change room and caught the attention of the shop assistant by waving the pair of pants I was carrying, and the hidden netball skirt in front of me. He nodded and with a smile on his face motioned me to enter the change room. I entered, and...

Crossdressing

Two girlfriends stay in for the night

The other day I came home from work and was looking forward to spending the evening with my wife. We had the next day off, and it was going to be great to just get some time with her. After I was home and settled my wife Dawn came and found me and told me she wanted to spend the evening with a girlfriend and have some fun. I was a little disappointed, but a few seconds later, she told me that she had some plans for her and her girlfriend Ashlynn, which is the other name I go by, and suddenly I...

Crossdressing

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

Dressed to Thrill Part 1

Introduction: a secret desire Dressed To Thrill Part 1 It was only a matter of time before my wife discovered what I am, and I discovered her need to dominate and control me. We worked different hours and I was often in the house alone which only encouraged my kinky tendencies. When she was away or had meetings she would get up and go to work early and I would stay home until it was time to go out later. It began innocently enough I suppose with looking at things on the internet and whilst my...

Dressed Up For The Special One

This is on ISS and I love the response I get it to post submitting the story. I have seen dressing up since so many years, I also wished God granted me a wish to a girl by myself. But I know that won’t be possible. It was a while since I dressed up since I last visited Goa in February. But I was badly waiting for a few chances to meet someone but failed to meet. A guy named ‘P’ wrote to me on my email, saying that he liked my story. We were chatting a lot of times. He was replying very very...

Gay Male

Confessions of a Sex Crazy Cross Dresser Part 2

Chapter 3: New York with Linda I didn’t really get a lot of time to think about what I had just done with Carlos. I fell asleep shortly after he left due to all the drinks I put away during the night. I actually fell asleep on my couch, still full dressed except for my jacket and shoes. When I woke up, I had a headache and was starving; I never even had a piece of the pizza Carlos brought. It was 2:00 in the morning and I was scared to look in the mirror.I took a shower to clean off the make up...

Crossdressing

The Girl Within Me

After the evacuation of the Vietnam war, my grandparents arrived in America as refugees. Several years later, my mother was born and grew up in the states. She received a good education and would become a successful architect. My mother then met a white American boy, my dad, and got happily married.Sadly, I remember little of my father, who tragically died in a motor vehicle accident when I was seven-years-old. Although she infrequently dated after, that she never remarried.Given my mother’s...

Crossdressing

Crossdressing with my Girlfriend

My girlfriend and I had been dating for several years and our sex life had basically become non-existent. It had been at least a year since we last had sex, and probably another six months before that. The problem was, as much as I loved her, I had developed a different kind of attraction.For some deep-rooted reason, I had grown a craving for ladies' clothing. Lingerie, stockings, high heels; all drove me crazy with lust. Eventually, this led to me dressing and wearing slutty outfits, gaining a...

Love Stories

My Transition Chapter 4 Crossdressing I

I was a straight-acting 24-year old slim and fit man, once upon a time. Then Sally got inside my head and now, I crave cock. I have evolved from being a school-jock and a dick to being fucked by an older man, then on the weekends by a DJ. I had my ass broken in by a big black guy when the club I frequent was closed. Only for a motorbike gang to dress me as a girl and fuck me silly. At work, I dared not test the waters and dress like a woman but at night I evolved into a full-on...

Dressed to Thrill Part 1

It was only a matter of time before my wife discovered what I am, and I discovered her need to dominate and control me. We worked different hours and I was often in the house alone which only encouraged my kinky tendencies. When she was away or had meetings she would get up and go to work early and I would stay home until it was time to go out later. It began innocently enough I suppose with looking at things on the internet and whilst my wife is an incredibly sexy and curvaceous woman...

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

The Wedding Present

Chardonnay had been Phil’s live in sissy lover and constant companion for just coming up to two years. She wanted to do something very special for him and had saved enough money at last. She phoned an exclusive hotel, giving great detail into what she required. She made a few more calls that afternoon while Phil was working. As she finished the last call, she gave a huge grin to herself in the hallway mirror.Phil had given her an engagement ring the previous year, which she found such a delight...

Crossdressing

my discovery

Here are some stories about my sex life and exploration of who I am.Before I started cross-dressing, I fell in love with high heels, mainly cumming in high heels. When I was younger, my parents used to have a large walk-in wardrobe and when they would go out at night I'd search for my dads porno mags. One night when I was reading some mags and my parents were out, I got a bit too excited and realized I had to cum. I looked around every for a place to blow my load without leaving any evidence...

Crossdressing

48 Hours Chapter 3

Chris spent a couple of hours mowing the lawn, cleaning the car, and all the other normal weekend jobs that need getting out of the way, the only difference from normal being that he was still wearing the panties and camisole under his jeans and tee-shirt. From time to time he practiced speaking in his feminine voice, working on making it more consistent.Lynn had gone out again, and when she returned, she asked Chris if he had anything in mind for the evening, but he said he was easy."In that...

Crossdressing

Caught Crossdressing by my wife

Caught cross-dressing by my wifeI have always been a cross dresser and enjoyed it. When I got married I put all my special clothes in the basement and lived a normal life. One day I was home from a trip early and found my wife was doing the laundry. There on the top of the pile were her pink knickers. I remembered I loved the feel of silk on my body. She left the room and I picked them up and I was running my hand across them and soon I was feeling and rubbing my cock which quickly became...

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

crossdressing with my moms friend

Mom opened my bedroom door. she stood there in the doorway and stared at me obviously repulsed. after 10 or so seconds she closed the door and walked away.i was mortified. i was kneeling on my bed, with her clothing catalogue open at the lingerie section laying on the bed before me, hard cock in hand. But most embarrasing.....i was wearing my mom's black bra, suspender belt and black stockings....her black panties were thrown onto the bedroom floor, cast aside when the urge to cum had become...

With the wifes help

Last night I finally lived a long time dream of mine. My wife Melody of three years came home from work around 7pm and told me to follow her upstairs. Once we arrived in the bedroom, she laid back on the bed and spread her legs wide for me. She was dressed in a long white light cotton dress with a floral print and a belt cinched at the waist. The dress fell long enough to conceal most of her knee high black shiny leather boots. As I looked down at her beautiful shaven pussy, I saw first that...

Crossdressing

How I Turned My Man Into A Whore

I always felt that to live my sexuality fully, I needed more than the traditional. The usual sex, after a while, bored me and I needed to change and look for something else, whether it was another man or another experience, but without ever being able to feel satisfied. After many adventures that momentarily satiated my need for pleasure, my body felt painfully unsatisfied. There had to be more, much more! But in that search, I could not find "my two", my pair, someone who resonated with me to...

Crossdressing

Carla Meets Mister Theobald

Karl Baxter was an unmarried man aged forty who spent a lot of his time as attractive thirty-something Carla Baker. Throughout his twenties and early thirties, Karl had had sexual liaisons with both females and males but if he were to express a preference at that time it would have been for cock rather than cunt. At about the age of thirty-five, Karl had started to dress, from time to time, as a female although in the early weeks and months of doing it he never ventured outside. As confidence...

Crossdressing

Caught by the Neighbor Crossdressing While Home Al

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

Wife Gets Even Chapter 2

Amy said, “So I think you are going to need to take next week off from work. I guess you could go to work with your new look if you want to but I am doubting you will want to subject yourself to the ridicule and questions about your look. You should get some sleep so you are ready to go in the morning. Have coffee made by seven and make sure you shave your face and body again.”I simply nodded my head in agreement and said, “Okay.”I was up at sunrise and made sure I brought coffee to Amy by...

Crossdressing

Jessie Caught in the Act

Sue and I were starting to catch our breath from our office session when suddenly someone started knocking on the door. “Jesse! You’re late to your meeting with me! What in the hell was all of that noise coming from your office? I sounded like someone was having sex in there!” Now I knew I was going to get it. That was my manager Steve. Steve burst through the door and his mouth immediately dropped. After what seemed like eternity, he shouted out, “What the hell is going on? Two of my employees...

Crossdressing

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