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Crossdressing

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18

Wedding Night: Part One

My fantasy night of being a married girl in bed with her hubby comes true.

As a tranny callboy/escort, I was always fulfilling the fantasies of lots of gay and bisexual men. But there was a fantasy of my own I had had for awhile that I wanted to fulfill with a handsome bisexual escort myself. I wanted to hire a handsome stud escort to pretend he was my hubby and have honeymoon sex with me like I was a bride on her wedding night. Every single girl fantasizes...Read On

16

Bookstore Bunny Gang Bang

Dressing as a Playboy bunny at the bookstore lands Courtney four big cocks.

Dressing as a sexy girl is my favorite way to meet men and have fun. There are so many different sexy outfits a girl can wear to attract men and turn them on, they ensure it never gets boring for a man. Every girl wants to be her sexiest when wearing lingerie and I am no different. Recently, I was on a business trip which included spending the night in a motel located across the street from...Read On

34

Carl, Carla and Hannah - Part 1

Carl gets pegged by his girlfriend

It's funny the places life leads you to. Sometimes you think you know where you want to go, be who you want to be, and then from nowhere something or someone comes along and knocks you way off course. For example, if you'd have told me a year ago that on my wedding night I'd be on my knees being spit-roasted by two guys while dressed in my wife's wedding dress, I'd have said you were crazy....Read On

20

Roomate

An introduction to a new side of my roomate

Roommate It had been a hell of a year with a divorce, a new job that had me traveling more and having to move into shared housing because my ex was sucking my bank account dry. Carl, my roommate, was a decent enough guy. I found the room on dougslist.org and we seemed to be compatible. He was neat without being compulsive about it, was a working student and was not inclined to throw...Read On

19

My New Neighbor

Slender cross dresser can't resist well-hung guys.

I'm a slender, thirty-two year old, bi white male. I've been cross dressing since my teens and love the look and feel of wearing women's clothes. I'm not into all the heavy stuff like wigs, breast forms, padding etc. I mostly wear lace panties, bras, lingerie, garter belts, sheer nylons and heels. I was blessed with long legs, a slim waist, nice round hips and a very shapely little ass. As...Read On

7

A Fantasy Come True

My wife and I went on a four day vacation to Charleston to enjoy the sights and especially to enjoy the nights. Our first night there I was no sure how it would go. I was wandering if my wife could really get in the role of being a Dominatrix. Would she really enjoy having DD as her Slave? Could my wife become the Dominatrix that I want and need? All my questions were answered that night. ...Read On

22

Nice surprise for the delivery man

Me and the delivery man get cosy

I'm a crossdresser in my early 20's and still live at home unfortunately. The day started as it usually does when I'm home alone, dressing up. On this day I had gone for a pink G-string with a matching bra, my breast forms, and some tight leggings which showed off my pert bum very nicely. A black lace top and of course my light brown shoulder-length wig and my make-up. I was in a bit of...Read On

36

Becoming Chloe

Caught in my wife's lingerie...

It was a mistake. I realise that now. I just don't know what came over me. One minute I was tidying the bedroom and the next minute I'm lying on the bed in my wife's basque and stockings, and using her panties to have the most fantastic wank I've ever had. I realise now that it probably wasn't a good idea to go through her underwear drawer while she was at her Mother's, but the lure of...Read On

49

Picked up in the Toilets

How an encounter in a public toilet turns into a lot more.

Here I was just turned 16, I liked to dress in girl's clothes and was very curious about cock, no about sex. Oh, god yes! My hormones were driving me mad with the desire to not only dress up whenever I could but also to have sex. Anything I saw in newspapers or magazines about women, girls or with sexual meaning had my mind just a blur of indecent thoughts. This particular day I had...Read On

19

A weekend with Nancy part 3

Get used to it, you're going to be my bitch alot from now on.

Upon arriving back at the car Nancy said that we had to hurry to our next destination because it would be closing soon and then she instructed me to drive while Alice and herself got in the backseat. "Honey, do you know that porn shop up the road a couple of miles?" said Nancy. I nodded that yes I did and I was instructed to drive there quickly. At the porn shop, Nancy suggested that I...Read On

12

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

59

The Change Up

Sexy outfit gets Deedra some lucky action

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

17

Working It

I get my house painted for panties!

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...Read On

19

Bo Peep and the neighbor

crossdresser role play

It had been a hot summer and I had no luck finding a job. My parents did not seem to understand that there just weren't that many companies hiring that year due to the economy so they had really been pressuring me to find a job. They all wanted someone with experience but having just graduated high school I had none. I was nearly at my wits end so when I was asked to house sit for my uncle...Read On

25

Becoming Mary - Part I

A girl discovers her dominance while a guy discovers his submissiveness

Lucy and I had been living together for a couple of months when it all started. She was in her early twenties, and I was a couple of years younger. Up until I moved in with her, I’d lived my parents. My stay-at-home mother had taken care of all the household chores while my father went out to work. It was the typical old-fashioned family structure. From day one, living with Lucy was proving...Read On

26

Vicky's Education

Vicky is taken to a gloryhole to enhance her oral skills.

My wife was very pleased with how I had performed as Vicky. My cross-dressing had progressed from a sexual role play with my wife to her setting me up for my first sexual experience with a man. At the same time, she had picked up her own guy and had taken him back to our bedroom. She cuckolded me and had me clean up her pussy after I got home.  From that time on, the only time I was not...Read On

19

Pam's First Time

Jerry is a friend from way back and meets Pam while looking for his friend, Kevin

Just a few days of spring break left and I was planning on making the most of it. Well, the most for me anyway. I'm a crossdresser and I have been for a long time. All through high school I'd secretly dressed, slowly building a wardrobe of pretty panties, a few skirts and blouses, bras, my silicon boobies, and most importantly, my shoes. The most important thing I had going for me, at...Read On

9

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

13

Andrew to Andrea - Chapter 2

Andrea's first small steps.

In all honesty, I should have been mortified by the events of the past few minutes, but I wasn’t…I was excited. I walked into our bathroom and set up the steamiest shower that I thought my skin could handle. I grabbed for my body wash, but realized the scent might be too masculine, so I set it back and grabbed my wife’s. It had a slight scent of vanilla and had a couple of butters and oils...Read On

36

Cindytranee meets the maintenance crew

Cindytranee gets caught crossdressing and gets fucked by three men

This is a true story that happened a few years ago when Iwas living in an apartment complex while looking for a house. I had taken a small one bedroom on the 2 nd floor. It was very nice and private and I really enjoyed being there. This was the first time in years that I had lived alone and I loved it. It gave me the freedom to enjoy my favorite thing, cross dressing and having sex with as...Read On

12

serving my master part 1

I'm a submissive panty wearing sissy

    My name is Chris I may have a penis but deep down I was born a girl. I have long red hair baby blue eyes a soft shapely hairless body and an overpowering obsession for wearing frilly lingerie. My obsession started at a young age I found a pair of my sisters panties in the bathroom and took them back to my room. I stripped off my clothes and rubbed the dirty panties over my...Read On

4

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

14

First Time In 19 years

I met my wife in 1989 and we were married 2 years later. Since the day I met her,I gave up my sexual encounters with men and focused on her. We have a great relationship and a beautiful daughter who is on her way to college. Two weeks ago my wife went away on a business trip to San Diego and my daughter went to Arizona to spend time with the grandparents before she left for school. I...Read On

11

Luck ran out

Everybody runs out of luck!! There i was again wearing my G/F's bridesmaid dress with the 4 inch wedges, bra, thongs and stockings this time. While wearing this wonderful outfit i yet again decided to tie myself up while everyone was out of the house. but this time i put myself into a tight hogtie using cable ties, with a realise mechanism of sizzors. So there i was enjoying the feel...Read On

12

The Ultimate Fantasy

Paul enjoys his ultimate fantasy - an evening dressed as a bride

Paul couldn’t walk fast enough. His heart was pounding and he kept checking the time on his iPhone every couple of minutes. It was only a ten minute walk to the hotel but it seemed to Paul that he would never get there. He knew that Marie has something very special planned for him and he couldn’t wait to find out! The day started normally enough. Paul was up before anyone else in the house...Read On

8

Crossdresser in Love

A closeted crossdresser finds love with man

I woke up with my hands bound, my mouth gagged, and my ass plugged. The bed I was on was comfortable enough. This was just a reminder that these parts of my body were no longer mine to do with as I pleased. For tonight would be my wedding night. For months we had planned things out. Picking out a dress, a place for the ceremony, all the things that brides do with their future husbands. But...Read On

47

The Neighbour's Knickers - Part 1

A man who just can't resist the opportunity to get into his neighbour's knickers

It was a sultry summer night but it wasn’t the muggy air that was making me hot. It was my clothes. I’d felt the urge to dress up in a very sexy outfit. My preparations had started much earlier in the day, and they had been thorough: my whole body was clean and smooth, shaved so that there was not the slightest hint of hair anywhere other than on my head. My heart thumped wildly as I...Read On

30

Telling Mom I’m A Crossdresser Part 5: Movie Night and Gangbangs

5th installment of Missy, Plz rate and comment. :)

I had decided to take a few days off from being Missy after Stan and Roger had left and my mom and I were finished with our little girl time. I spent the next few days just continuing with life as normal except for the throbbing pain in my asshole and my cock from the 3 days of constant sex. I couldn’t stop thinking about all the things I had done as Missy and all the kinky fetishes I...Read On

11

The perfect day...

A t-girl's experience of getting dressed for ACTION!

The perfect day… The time was drawing near. He would have the house to himself! The realisation of a whole 4-month's planning would now come to fruition. It had been a while since he had gone out all dolled up, and now was a fresh opportunity to see his progress as a woman. He had been busy – his make-up collection had swelled considerably, and the addition of several choice pieces...Read On

17

In Wonderland, Pt. 2

To recap, our protagonist didn't want to dress up for a halloween party, so his girlfriends decided it was time he joined in the fun. They styled his hair, did his makeup and put him into an 'Alice' dress. However, the disguise worked a little too well, as Chris Smith has taken 'Tilly' back to his house after a passionate kiss on the street corner... Chris put his key in the door...Read On