Crossdressing

HollyInPantyhose

Adventures in a Woman’s Body – Chapter 5: Secretarial Duties

Serving some very important people as the secretary

John waited for me to finish eating my cum burger, and then he told me to get up because we were leaving. I stood back up onto my six inch stilettos and walked with his arm around me, which firmly grabbed my ass. We exited the food court and made our way to his office building. The mall had a vast underground network so we were able to walk to his workplace without going outdoors. Along the...Read On

Added: 02 Jul 2014 | Category: Crossdressing | Avg Score: 4.88 | Words: 1,919 | Tags: crossdress  pantyhose  vibrator  high heels  slut  cum  humiliation   | 3 Comments

shootersr9

Jason and Kym ~ Part Two

A story about self-discovery, now turns into a rollercoaster ride!

 Later that same night, I strolled down to my favorite watering hole to tip a few strong drinks in the hopes of either clearing my head or dulling the noises within. After flirting over those drinks with a short blonde haired gal named Kym, we stepped out onto the dance floor to press our bodies against one another to an old Jonny Cash tune. She’d been waiting for some guy to meet her for...Read On

Added: 28 Jun 2014 | Category: Crossdressing | Avg Score: 4.67 | Words: 6,995 | Tags: bisexual  kissing  oral  cock  anal  pussy  tits   | 4 Comments

mtnbiker1

A Lifelong Love Of Lingerie

An introduction to a lifelong love affair with women's clothes

At the time I was sixteen, my mother was divorced and living with me, and she still worked and was gone until late in the afternoon on some days, so I would have the house to myself. I did not have access to porn until later, but there was Cosmopolitan magazine and other magazines which had the sorts of ads and stories that intrigued me, underwear ads, tampon ads - they all did the trick. I...Read On

Added: 27 Jun 2014 | Category: Crossdressing | Avg Score: 3.89 | Words: 1,478 | Tags: lingerie  masturbation  sex toys  pantyhose  girdles  bras  foundation garments   | 3 Comments

Jess_cd

Learning To Be Submissive - Part 2

My second meeting with Jack

I arrived slightly earlier than I was meant to. After our first meeting I had been given specific instructions. Jack had allowed me to shower and change back into my normal clothes. Once I had returned to the kitchen, I found a note with a key. "Today you excelled yourself, but you have more to learn. Next week on Monday you are to come directly here after you finish for the day. I will...Read On

Added: 20 Jun 2014 | Category: Crossdressing | Avg Score: 4.8 | Words: 1,956 | Tags: maid  lingerie  submission  oral  anal  cum   | 8 Comments

SxyJackyLeggs

What I Do When I'm Alone

The fun I have when I am alone.

With the wife off to work today, I decide to indulge in my fetish. I wait a little bit till I know she is at work and it's upstairs I go. I take my computer with me to chat with friends and others I happen to meet in chat rooms. I lie down on my bed and start chatting with people and seeing which friends are on. It takes about an hour before I finally find someone to chat with. What follows...Read On

Added: 19 Jun 2014 | Category: Crossdressing | Avg Score: 4.63 | Words: 1,066 | Tags: crossdressing  toys  masturbation   | 16 Comments

jerrixdresser

Night at the Video Store, part 3

bimbo crossdresser cruises video store in Black part of town

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

Added: 14 Jun 2014 | Category: Crossdressing | Avg Score: 4 | Words: 936 | Tags: crossdressing  anal  black     | 3 Comments

marietv

I am Sissy

a fantasy of a taken slave by a pirate captain

The year was 1888. My name was Sebastian but I was now called Sissy since I was taken a slave. My father’s merchant ship was captured and sunk by the pirate crew of the Black Bess. I alone was saved for Captain Booth's pleasure. He was an escaped convict from the prison island of Australia. He was a huge beast of a black man, dark ebony skin stretched tight over enormous muscles that...Read On

Added: 07 Jun 2014 | Category: Crossdressing | Avg Score: 5 | Words: 1,902 | Tags: creampied  transvestite  big cock  master/slave   | 13 Comments

Jess_cd

Learning to be submissive - part 1

A gift comes at a cost

Before the days of internet chat rooms and social media I was very lonely as a young cross dresser. I can't speak for everyone of course but I would use telephone messaging services to talk to like minded people. I had received my first mobile phone for a recent birthday and I would often call up to chat to people. Sometimes things would turn into phone sex and on the rare occasion I would...Read On

Added: 02 Jun 2014 | Category: Crossdressing | Avg Score: 4.84 | Words: 2,200 | Tags: lingerie  oral  anal  cross dressing  stockings  submission   | 15 Comments

vanessagrrl

Memories

Reminiscing about time spent before dating

Just for fun, I though it might be nice to share some of the experiences I went through on my way to becoming the sexy slut I am. Before I had the confidence to fully dress and go out, and to go on the few dates I've been on, I was completely closeted. The only way I could express my girly side was through playing on the phone and all alone. I loved dressing up a few times a week. I...Read On

Added: 30 May 2014 | Category: Crossdressing | Avg Score: 4.78 | Words: 619 | Tags: crossdressing  toys  phone sex  ass play   | 6 Comments

Jess_cd

The Secretary - Part 1

I receive an interesting job offer

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...Read On

Added: 24 May 2014 | Category: Crossdressing | Avg Score: 4.92 | Words: 2,045 | Tags: lingerie  masturbation  domination   | 13 Comments

Jess_cd

Returning To Old Habits

After an extended break, I return to an old hobby.

Like many cross dressers, I found my habit has a certain ebb and flow. I would bury myself into my kinky hobby for several weeks, only to hide everything away again. I used to have purges too from time to time, where I'd convince myself it was wrong and throw my clothes away, swearing I'd never do it again. The last time I purged was in my mid twenties. I'd been with my then girlfriend for...Read On

Added: 22 May 2014 | Category: Crossdressing | Avg Score: 4.93 | Words: 1,399 | Tags: solo  cross dressing  lingerie  toys  masturbation   | 12 Comments

CallmeJulie

Call Me Julie part 5

Julie is not the only one with a secret.

Kelly is kissing me passionately, and I am kissing her back. Her hands are all over me as she feels me up. My tucked package is straining against the material of my panties as she grabs and gropes at my feminine attired body. Her hand snakes its way under my dress and into my panties, which she pulls down enough to release my cock, and tugs on it vigorously. She breaks the kiss and snakes down...Read On

Added: 19 May 2014 | Category: Crossdressing | Avg Score: 5 | Words: 646 | Tags: bi  oral  anal  dp   | 3 Comments

Jess_cd

My birthday treat

After months of helping me dress, my neighbour plans a special night.

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...Read On

Added: 18 May 2014 | Category: Crossdressing | Avg Score: 4.89 | Words: 1,822 | Tags: crossdressing  helping  oral  lingerie  strap on   | 15 Comments

Jess_cd

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...Read On

Added: 14 May 2014 | Category: Crossdressing | Avg Score: 4.8 | Words: 2,157 | Tags: lingerie  straight sex  oral  toys  dressing   | 5 Comments

SkittleMonster

Jack's Dirty Secret

Jack walked into his bedroom, seeing his wife laying on the bed with a dildo in hand.

Jack and Mary had been married for ten years or so. Mary never thought that Jack would keep such a large secret from her. She sat at the house all day and did laundry, Jack's and hers. She never usually did his since he's picky, but she was bored and it needed to be done. As she was putting away some of Jack's clothing in his dresser, she saw something. It was a shiny pair of silk gray...Read On

Added: 08 May 2014 | Category: Crossdressing | Avg Score: 4.78 | Words: 1,355 | Tags: wife  husband  anal  vaginal  sex  love  marriage   | 7 Comments

Jess_cd

One of my first times

My first time with a guy

They say you never forget your first time. For me that's kind of true but in my attempts to seduce over the years I've claimed to have so many first times and I definitely don't remember all of them. Being bisexual and, of course, with my dual gender identities I have probably had more first times than most though. I was still cross-dressing in secret in my late teens and I'd never had...Read On

Added: 04 May 2014 | Category: Crossdressing | Avg Score: 4.76 | Words: 1,146 | Tags: cross dressing  gay  anal   | 12 Comments

transgurl

My Oddesy 1 - Glen (here and gone)

A (mostly) true story of my first time dressing for another

"But mum. I'm too sick to go to school." I give my best fake cough. It was late senior year and I had been busting my balls for months. I just want a day at home alone. She finally replies after a minute of withering glares. "Fine. I'll call the school. But you're seeing a doctor Monday if this persists. I'll be back around five." "Sure. Whatever." I lay perfectly still until the sound of...Read On

Added: 01 May 2014 | Category: Crossdressing | Avg Score: 4.7 | Words: 1,412 | Tags: first time  oral  lingerie  crossdressing   | 15 Comments

Jess_cd

A surprise helping hand

Getting caught paid off, in more ways than one

When I initially started to cross dress I would borrow things from those around me. At first it was my sister, then when I visited my father I would wear my step mother's things and eventually my girlfriend's. Mostly without their knowledge, of course. I was always as careful as I could possibly be, replacing things just as they had been left and making sure I had plenty of time when I...Read On

Added: 25 Apr 2014 | Category: Crossdressing | Avg Score: 4.92 | Words: 3,185 | Tags: crossdressing  lingerie  full sex  neighbour   | 12 Comments

CallmeJulie

While the Cats are Away

Kelly's best friend catches him dressed up

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

Added: 21 Apr 2014 | Category: Crossdressing | Avg Score: 4.88 | Words: 1,850 | Tags: crossdressing  threesome   | 12 Comments

SxyJackyLeggs

My wife finally indulges in my fantasy

This story is a work of fiction I wrote for my wife.

I come home from work to find you dressed in your sexy jeans, a tighttee shirt, and a pair of heels. I can tell you are horny by the way you tell me to get into the shower and that my clothes are laid out for me after I finish cleaning up. My cock throbs as I shower and lather my body up with some scented soap. I know you want me squeaky clean so I insert a soapy finger into my ass,...Read On

Added: 19 Apr 2014 | Category: Crossdressing | Avg Score: 4.89 | Words: 1,188 | Tags: crossdressing  sub   | 9 Comments

CallmeJulie

Call Me Julie Part 4

Julie is not the only one in for a surprise.

Scott coaxed me out of the car and we walked the ten feet to the front door, he was practically dragging me while reassuring me that everything would be alright. "Kelly is expecting us, don't you worry about a thing." "She is expecting me? Dressed up like this? Somehow I don't think you are telling me everything Scott, if this ends badly I will be kicking your sweet ass," I told him. ...Read On

Added: 09 Apr 2014 | Category: Crossdressing | Avg Score: 5 | Words: 779 | Tags: crossdressing  threesome   | 5 Comments

CallmeJulie

Call Me Julie part 3

The night gets more interesting

I stretched and reached out like a cat waking from a nap. Scott was resting on his side with his elbow down and his head resting on his hand looking down at me. "Enjoy your nap?" he asked as he stroked my shoulder. "How long was I out, how long have you been watching me?" I replied. "Not too long on either of your questions," he replied. I glanced at the clock and it read 8:00,...Read On

Added: 04 Apr 2014 | Category: Crossdressing | Avg Score: 5 | Words: 1,102 | Tags: military  crossdressing   | 7 Comments

allfours

Carl, Carla and Hannah - Epilogue

The conclusion.

It's now been nearly a year since Hannah and I got married, and my goodness, what a year it's been! As soon as we reached the Bahamas on our honeymoon, Hannah and I (as Carla, naturally) had an absolute wonderful time. The days were full of warm sunshine, and the nights were full of... well, I think you can guess! When we got back, my plan to live full-time as Carla started well. After a...Read On

Added: 21 Mar 2014 | Category: Crossdressing | Avg Score: 5 | Words: 2,500 | Tags: transformation  transgender  oral  anal   | 12 Comments

jerrixdresser

Night at the Video Store, Part 2

a sissy, very blonde, bimbo slut goes to a video store in a rough, black part of a big city.....

There were some strong, black street toughs in the SUV, but they got quiet when they saw me step off the curb into the parking lot. My nipples began to get hard under my little black micro mini dress and I could tell they were looking at them. I must admit, my platinum blonde wig, a huge Vegas style wig that went down my back to my butt, swung right and left as I moved my head back and...Read On

Added: 15 Mar 2014 | Category: Crossdressing | Avg Score: 3 | Words: 722 | Tags: crossdressing  sissy bimbo  sissy slut  video store  black guys   | 3 Comments

allfours

Carl, Carla and Hannah - Part 25

The Honeymoon Party - the final chapter.

A knock at the door broke our reverie. Hannah turned to me quite pointedly and said that I should answer it. I looked at her questioningly, but she just gave me her mischievious grin. "Call it my wedding present to you, Carla," she said, enigmatically. "Now, go see who's there." Bewildered, I walked to the door of the suite, loving the sound of my wedding train rustling behind me. As far as...Read On

Added: 15 Mar 2014 | Category: Crossdressing | Avg Score: 5 | Words: 2,826 | Tags: crossdressing  oral  anal  transformation  bisexual  group   | 3 Comments