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Crossdressing

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26

The Feminisation of Michael. - Chapter 7

The Feminisation of Michael. Chapter 7 I settled in at Stanmore House quickly and Sam helped a lot and we would spend most days together with her showing me around the estate. I soon persuaded Sam to wear prettier things and we were often seen., me blonde, her brunette, rushing around giggling in little floral dresses. Alternatively we would ride the beautiful horses in...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

15

Explorations beyond my expectations

My introduction to pegging, cross dressing and so much more

I was nineteen at the time and Lili was my first college girlfriend. She was a virgin when we met. I had only had one intimate girlfriend before her. We loved to explore together and every weekend her roommate would leave town on Friday night and wouldn't return until Sunday evening, giving us plenty of time to explore and play. She knew I liked ass play from conversations about things...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

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

Mistress Hannah's Pathetic Husband Part 4

Mistress takes the humiliation to a new level

The third and final day of my transformative weekend started poorly. I had aches and pains all over. My neck and back and thigh muscles were sore. I had a little irritation from body hair that was growing back. And of course, my asshole felt all stretched out and very tender. I wondered if it would ever feel tight again. I also wondered what the evening would hold. I couldn't imagine that...Read On

14

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

8

My wife takes what she needs and wants

Normally conservative wife suddenly decides what she is going to take what she needs

I'm a very lucky husband. I have an extremely sexy wife, who is open minded, and loves to please. If she has any faults, it's that she doesn't realize how sexy she is. At 37, she has extremely long red hair (which she jokingly calls stripper hair, but it's actually the truth because it's so sexy how long it is and how it falls against her backside), really fantastic legs, nice curves, lots...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

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

11

The Feminisation of Michael. - Chapter 5

The Feminisation of Michael. Chapter 5 I found out later that I had been in a coma for two months.  I was unrecognisable and unconscious but still just alive. I remember waking up and being totally lost and I didn’t feel like me. Sue was there when I woke and the memory of her face returned as did the events of the run up to that fateful night. When I first woke, I couldn’t...Read On

26

A Whole New Me - Part 2

Lisa finds out what I've been up to

I had just finished cleaning up in the bathroom. A spontaneous encounter with my best friend whilst wearing my girlfriend’s thong had left me a bit of a mess and as for the thong... well I guess I’d need to find something new. Fully cleaned up, I ran naked into our bedroom and started looking through Lisa’s drawers for a new pair of panties. I wasn’t sure how I’d explain my change to her...Read On

19

The start of my life as a submissive crossdresser

First forays into crossdressing and giving handjobs

I am a bisexual cross-dresser/sissy and have been enjoying my life as such for many years. It all began for me when a friend asked me to look at some of his 'girlie' magazines. We went up to his bedroom and looking through the magazine got Chris really excited and he got his cock out and started to masturbate. I couldn't take my eyes off his cock and I slowly reached out and touched it and...Read On

36

Motel Fun for College Crossdresser

A young college student enjoys a girly getaway at a nearby motel.

Before I start the story I want to describe the setting so you get a better idea: it's a highway side motel, very rundown and not very cleanly, not a dump either but not the best place to have a family sleep that's for sure. The layout of the motel is a rectangle. The rooms surround the rectangle's perimeter, in the center there is a pool, a park area, and a parking lot. There is a...Read On

8

Glimpses of Consequences

Davey's mother tries to teach him a lesson.

GLIMPSES OF CONSEQUENCES By 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...Read On

19

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

17

The Worm Turns Part 2: The Routine

After establishing a routine, a surprise visit by a man took my tranformation to a new level.

Before I even realized it, we had fallen into a pattern of visits to the sisters’ salon. On a weekly basis, I was having my hair set, my nails done, and my make-up applied expertly by some combination of Kim and/or Kristie. Often one would do the work while the other recorded the proceedings on video or with a digital still camera. Several of the photos made their way onto the mirrors of...Read On

43

Gang banged at a private club

This is what happened when a friend took me to a private members only gay, bi, and transgender party

After yet another hot weekend at my friend Heberto’s house, I was packing up and getting ready to go home when he told me he had something “special" in mind for us next weekend. I begged him to tell me what he had in mind but he refused. So I left. My curiosity was peaked. The week dragged on thinking about all of the possibilities. The anticipation was killing me. Finally Friday...Read On

18

First Time, First Fuck, New Porn Star

A story I wrote while on a short break from my Missy series. Don't worry, I just need inspiration.

I am just a normal guy however I have what some would call an abnormal fetish. I am a 23 year old guy and I like to wear and dress up as womanly as possible. I am 5’9, a little chubby but can still pass as a woman, with brown hair, brown eyes and a 5 inch cock. One night I had gone out with one of my friends and had gone drinking to a few bars. As we went from place to place we started...Read On

39

Curious No More

I used to call myself bi-curious, but now I know!

I began dressing in my sister's clothes. I would get so hard and excited when I felt the soft panties against my cock and the bra wrapped tightly around me. But my dress up time was always short. Now that I live on my own I have my own femme wardrobe and plenty of time to dress and perfect my makeup and appearance. The more I dressed and the longer I stayed dressed, the more I wondered what...Read On

13

Dressmaker's Dummy

Girls always knows best

I was happy now that Kasia and I had moved in together. Not only did it mean that we no longer had to take turns going to each other’s place, but it also meant that I had closer access to a supply of her soiled panties. Kasia was a cute Polish girl, 23 years old, with deep blue eyes, shoulder-length hair trimmed in a cute bob, and a body to die for. We had decided trying to live together to...Read On

13

Confessions of a Sex Crazy Cross Dresser Part 2

Chapters 3 and 4

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....Read On

13

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

37

Carlos and The Garter Belt

Carlos finally takes the plunge

Carlos sat in the car for a moment looking up at the sign of the sex shop. He had been in the shop on more than one occasion. A lubricant here and a toy there, to spice up the bedroom with the wife. This trip was not for that purpose. Every time he was in the shop, he was drawn to the lingerie section. In the past, when the sales girl would approach, he would say he was just looking...Read On

30

Telling Mom I’m A Crossdresser Part 4: Repeat Business and Roleplays

4th installment of Missy :) please rate and comment :)

When my mom and I had gotten home, I immediately ran into the house to take a shower and change as quick as I could. I re-shaved my entire body and removed my makeup so that I could start from scratch and apply it again. Once I was finished with my makeup, I see a new outfit laid out on my bed. This was a cute nurse outfit with a short tight skirt that barely covered my ass. It was also...Read On

11

Capri

My first driving lesson

Friend of the family -Bi Curious story This is my very first story, I hope you enjoy reading it and I hope it inspires you to contribute My name is Jools I grew up in the west country from the late 60’s until the present day My tale based on a true story happen in 1970. At the time I would be at the tender age of 16. When your young the time can't pass...Read On

10

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

4

Crossdresser's Spanking Scene

The CD to CD variation of an erotic 'spanking leads to sex' scene, already posted.

My roommate and I were both bi and part-time cross-dressers. We were also familiar with consensual B & D and had already worked out several code words, then went a step further and wrote scenes for each other, so that when we're in the mood, we could call up the scene rather than try to explain it or coach someone through it.   Sometimes we did a scene to please each other sometimes we...Read On

21

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

17

I am Suzie

This is my fantasy.

The coach was lubing up his cock. It actually was getting bigger. The veins along the shaft were thick and gorged. I could not take my eyes off it. Then he started humping the crack of my ass. I knew he was letting me feel how huge he was against my ass. I was so turned on that I started to wiggle my ass and grind his cock. He enjoyed that so much, he stopped humping me and let me do all...Read On