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Crossdressing

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9

Sharon Goes The Distance

David becomes Sharon at his wife's request

When I woke up Saturday morning, I knew it would be a very eventful day. My wife, Donna, had been making plans for quite some time, which included me dressing up as Sharon, my female alter ego. Three years ago, I had confessed to Donna my desire to wear feminine attire from time to time and she had embraced it more than I could ever imagine. In fact, she took pictures of me all dressed up or...Read On

31

Always Up for a Party

Trevor's idea of a party, with me as entertainment

I got home late. What a night! I had gone to the video booth at the bookstore horny as hell but in my wildest dreams I could not have imagined the outcome. Oh sure, I expected sex. I had yet to leave those dark little booths without a mouthful of cum, an ass full of cum or having my balls sucked dry but tonight … tonight! Not only had my ass been filled in the booth but at Trevor’s party...Read On

26

High Fashion Queen

A transformation changes the lives of two college friends.

I felt like such a loser. It was Friday night and instead of going out and hitting the clubs to dance, drink, and have fun, I was in my dorm room with my best friend. We had known each other since the 6th grade and today was his birthday. No one should be left alone on their birthday right? To be honest, I didn’t really feel like going out anyway. My boyfriend, who I had been seeing for...Read On

17

Wife Gets Even - Chapter 1

A husband takes advantage of his wife over a bet but the wife gets a chance to turn the tables.

My wife and I get together with our neighbors to play cards to play cards about once a month. We generally have a good time but there are no stakes involved. For a poker player like me who is accustomed to gambling for large amounts of money playing just for fun is a little, well… boring. One night about a month ago, I tried to make the game a little interesting by including some drinking....Read On

28

Keeping A Secret

The drive home from the Cities was always long. After work I had stopped at Kim’s to change and emerged as Samantha. I drove to the meeting and then went out for a drink (or maybe two) with some of the other ‘girls’. By the time I was half way home my eyes just wouldn't stay open any longer. I decided to pull over in a secluded wayside rest area. If I could just catch a little catnap I knew...Read On

13

A Night at the Ambassador

An early evening of debauchery earns kudos for a crossdresser.

While on business in Colorado Springs, I had the opportunity to visit one of the adult theaters that I had visited previously. Although the booth area was in full swing, the booths had no doors and there was no privacy what so ever. One could still have a good time if they were so inclined. The attendants were cool and they did not mind the actions of others as long as there were...Read On

20

Being Christy - Part 2

Caught by the neighbour!

To be honest, I was panicking. From the outside I looked like an average teenager. Skinny black jeans. Indie band tee, maybe a size too small on my Bowie-thin frame. Cherry red Converse high tops. Straight dark hair cut into a fashionable (if you were an NME reading indie-kid) boy bob. But underneath I was sporting skimpy black panties and stockings and suspenders, all ‘borrowed’ from...Read On

16

Wedding Night For Ken And Barbie: Part One

Catching the garter at my cousin's wedding gets me a honeymoon fuck like the bride.

When I went to my cousin's wedding in Monterey, California stag, at the reception dinner she had me seated next to the only other male stag invitee, the photographer. He was my age and tall and we hit it off, immediately. Ken was a sports car enthusiast and he told me about the thrilling rides he took along the Pacific Coast Highway. He talked about the beautiful views at scenic lookout...Read On

Wifey's Panties

What a hottie little sissy bitch I have become.

Our phone sex is always so hot; you egg me on in so many ways. My wife has no idea how much I wear her panties not to mention her lingerie, stockings and dresses. We talk about what I'd wear when we get together as I suck your cock. You always have me send you pictures of me dressed in panties, stockings and high heels, telling me how perfectly stunning my penis looks in silky panties and...Read On

26

Changing Room

I had finally worked up the courage to explain to my wife that I liked to wear panties. I dressed off and on in her clothes for years, and she didn't suspect a thing. Before that, when I was single, I had taken to snatching the odd pair of panties out of the dryer in whatever apartment building I was living at the time. When I was a little boy I had always wanted to be pretty like a girl,...Read On

23

Two Girls Are Better Than One

My girlfriend sets me up with other men we share.

My girlfriend, Sherry, had nice, big C-cup titties and a face like a young Marilyn Monroe. Needless to say, she got hit on by lots of men wherever she went. She was also a nyphomaniac who liked to be fucked ten times a day, so we had a great sex life. She found out I enjoyed wearing lingerie, so, as part of our sex play, she would dress me up in her panties and bras and stockings and...Read On

19

Meeting One of the Neighbors

I meet one of my neighbors and he invites me over for drinks.

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...Read On

17

The Irresistible Dress

I just wanted some new jeans but I couldn’t resist the 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...Read On

11

An Afternoon with Suzie C*cksucker

A Mistress directs a scene with two sissies

One of the strangest relationships I've had over the years was with awoman named Laura. She saw my profile on Yahoo and dropped me a note. It was like manna from heaven. She was very into the idea of fucking a man in the ass with a strap-on dildo. She'd not done it before but had fantasized about it for years. Would I be willing to help? You bet! We chatted for a long time before we...Read On

14

Call me Julie

Never assume you have complete privacy.

Coming back to garrison, after a yearlong deployment, is one of the best things ever. Imagine having to go a year without having your favorite lingerie to change into, and not being able to shave and pamper your body as you would like. As it so happens, we just got back the day before yesterday, and after all the clean-up and inspections, we are being given a four day weekend. My...Read On

14

From Anton to Antonia

Anton discovers a feminine side to his sexuality

The first sex I had with a couple was my boss and some woman we just met in a hotel bar. I liked it, so the boss told me to put out an ad. An advert in Craigslist for my area was all it took. Posted in the casual section under M4WM and a photo of me from the shoulder down, I had a flood of answers. I chose Julian and Rosemary, they were mid- thirties, still twice my age and arranged to...Read On

15

A Sweet College Girl In Love

As a sweet college girly boy, I dated a real big hunk with a ten inch cock.

I went to college in a beach town in California where all of the girls wore their little thong bikinis to the beach and showed off their asses for boys with very friendly results. I noticed that when the girls were bending over while playing volleyball in their little thong bikinis, the boys all looked at them with hungry eyes that I liked a man to have for me.  The sweet little college...Read On

8

Telling Mom I'm A Crossdresser Part 15: 2 Kinky Girls.

Part 15 is finally here :) plz enjoy as Missy enjoys a night with Laci alone!!

It had been a week since Mom and I spent the 4 days at the spa and hung out with my old babysitter Laci and for a while it was back into our old routine of working and coming home. Day after day I kept thinking about how her warm wet pussy felt wrapped around my cock while the feel of a sexy thong rubbed against my asshole. I came home one day to find my mom was packing a bag. I asked her...Read On

17

A Terrific Threesome: Part One

Wearing my girlfriend's panties leads to a big cock for both of us. .

When my girlfriend and I moved into our new apartment, the tall handsome maintenance man came by to put a hand-held spray-jet nozzle on our shower for us. I was home alone and dressed in a sexy little pair of Sherry's panties when he arrived and I put on her little short black silk robe to answer the door. When I opened the door, the maintenance man's eyes went directly down to my...Read On

15

My First Time - Part 2, or The Beginning

Once was not enough

It was about two weeks after Halloween that the dreams began. I began to dream about being transformed again. I was able to recall the feel of the silky garment against my skin, the sensation of the nylons brushing against each other as I walked. I recalled all the women at the party who danced with me and rubbed my silk covered ass. "You feel like a real girl," more than one said, and I...Read On

11

How to please your girlfriend

When she gives me the puppy dog eyes, I can't resist....

(Some of this story may be slightly fabricated, but don't worry about what is and what isn't, just enjoy the story.) It was back in February when me and my girlfriend plus a few friends decided to go to a con. We hung out together and thought it would be fun. A friend bought my ticket and the closer it got to the con, the more we were excited. Not only did we get more excited, the closer...Read On

7

Missy Returns

It had been a long time from the seven days I spent with my studs, but sadly I went off to school and Missy had to go on an extended vacation. However, school did not work out as planned and I found myself in a new city and my own apartment with a small job. I had to help pay the bills. For a while I lived with a roommate who was a little homophobic and despised the ideas of trannies. He...Read On

7

The Afterparty Part 2

As Summer lay in a pool of sperm soaken sheets, she dazed in and out from the hangover and the multiple orgasms she just had. She dazed in and out, coming into consciousness as she heard voices of two men down the hall. Neither one was the voice of Pete. The door was still open and the voices got closer. It took a lot of her strength just to try and pry her legs close as much as possible...Read On

31

Jessi's coming out party

Jessi comes out to several friends and has an interesting night.

Hi everyone. My name is Jessi, I'm 23 and I have been a crossdresser for over three years. Recently I decided to go full time and was going to met up with some friends to come out to them. I arranged to go hang out with them at my friend Derek's house, them thinking I was still coming as my old self. My roommate, who started my path into crossdressing (that's a whole other story), told me if...Read On

10

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

22

Initiating Stephanie

Stephanie's secret is discovered and exploited

** Discovery ** The first time I set eyes on her, she was wearing the sluttiest underwear one can imagine. Totally oblivious to my presence, she was admiring her scantily clad body in the full-length mirror on the wall. The lingerie was black, my favourite colour , sheer in texture and cut to a design that left little to the imagination. Black leather, ankle boots adorned her feet...Read On

5

Warehouse slut

There I sat at my computer, ready for another morning of chatting with my new online lover, much like all other mornings for the last two weeks.  It had become quite routine for us to chat for about an hour in the mornings, then off to our lives.  I was, quite honestly, starting to lose interest, figuring he was just another of the "Internet fakes".  We have all run into them, the guys who...Read On

18

A Great Date

A first date that I hoped might lead to a first steady boyfriend

I was so excited to sign online and see a message from my sexy college boy. We hadn't spoken in a while and I guessed that we would never get the chance to finally meet. Many a night had I masturbated thinking about his lovely cock, though I had only pictures to please me. It turned out that he had been thinking about me too. "I can't get you out of my mind," he said. "I need to meet you....Read On

24

The Compromise: Part 1

A suggestion from a counselor sets in motion a fantasy compromise that changes my life forever.

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. ...Read On

18

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...Read On