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Crossdressing

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12

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

8

An Unforgettable Halloween

Tessa gets tricked at a Halloween ball but it turns out to be an unforgettable treat.

This past Halloween I took advantage of a chance to attend a charity Halloween ball. I had to travel for business to a city in upstate New York for a few days, and my first day there I saw an advertisement for an annual Halloween costume ball taking place in the mansion of local philanthropist. The annual party raises a significant amount of money for a designated charitable foundation. This...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

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

33

Sucking My Best Friend's Cock

He never expected that I was sissy and never dreamed he would be one of my lovers

This happened when I was beginning to dress up as Mel frequently.  Saturdays were the best days for me, except that my friend Pete would always stop by in the middle of the afternoon, so I always needed to be changed back into my boy clothes before he showed up.  One Saturday morning I decided that it was time for Pete to meet Mel. I took a warm bath, removed my unwanted hair and applied...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

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

9

Ready & Waiting (In my wife's lingerie)

My wife has me dress up in her lingerie while she goes off to get a massage.

“Billy, can I see you in the bedroom?” I walked down the hall and into the bedroom, surprised to see lingerie laid out on the bed. I asked, “What’s this?” “We’re going to play a little game today. I need to de-stress, and you’re going to help me.” “Help you how?” “Take off your clothes and go shower.” After my shower, I returned to the bedroom completely naked. And erect. I kissed Betty....Read On

22

Adventures in a Woman’s Body – Chapter 3: Used by Strangers

I become their powerless cumslut

I put his softening cock back into his pants as he parked the car. He got out and I crawled up after him. Having been on my knees for so long, my knees were aching and my legs were sore, but at least my feet got a rest from walking in my seven inch black stilettos. “What’s your name, by the way?” I asked him, since I don’t know what to call him by. “Just call me your Daddy, sugarslut.”...Read On

7

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

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

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

25

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

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

6

Leslie becomes the man of the house and I his princess

I learn to love being a girl

Now every night I'm being fucked by Leslie, and everyday I'm the woman of the house. Leslie starts by tutoring me in speech and wiggling. I'm dressing 24/7. Leslie even schedules me for electrolysis, my face first then the rest of my body, including a permanent Brazil cut. I find myself forgetting that I ever was ever a guy. After having my hair cut and nails done at a real salon, Leslie...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

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

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

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

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

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

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

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

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

11

Wet crossdressing fiesta M/M

Hot male on male cross-dressing action

Heading back through Texas I stopped off at the same porno shop in San Antonio, only this time I made sure to get myself a hotel room, because I already knew at that time I was going to get a man that night. I was in the mind set to please. Rubbing my cock all the way there until I got to the hotel room having it set up for wet sex. This time as well I remembered to shave my legs, dick...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

29

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

16

Busted by a bud

Caught on home turf.

It's a hot summer day in 1994. Nowhere is a small, fairly poor, rural Illinois town; the kind of town where nobody locks their doors. Summer seems to be an average 19 year old. He goes to a small community college and works on the weekend's. He's kind of quiet and doesn't like to be around his parents. Both parents have jobs where they have to work the night shift. Summer's mom works for...Read On

10

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