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Crossdressing

20

A New Level

Things escalate for Vanessa and her man

Greg and I had been seeing each other for a little while at this point, and things were going great. We had gone on a few dates and I loved how he always treated me like a lady. He made me feel so sweet, sexy, and vulnerable. Tonight was four months since our first night together and I wanted to surprise him with something a little special. I bought a long coat, and I thought it would be fun...Read On

42

Caught, Used and Loving it Part 2

My descent continues

It had been two weeks since I had been caught and used by the mystery woman and her boyfriend. They had left as quietly as they came, and I was left kneeling on the floor dressed in all my best female clothing, cum dripping off my face, and my own cock dribbling cum on the floor. Since then, I had had only two emails. One was sent immediately after they had left and contained ten pictures...Read On

16

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

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

22

My First Time

A true Halloween cross-dressing story

I met Lydia while living in Florida. I had recently won a law suit and didn’t need to find employment for a while, so I spent the first three months partying. A good friend had sponsored my membership at a well known and popular yacht club. They had a public side and a members-only side; the members-only side had better bands and more folks. If you parked your yacht and paid the docking...Read On

18

Hitch-hiking Baby Doll: Part Two

Being a sexy girlyboy for a trucker stud leads to lots of sexy pleasures.

I woke my trucker stud up in the middle of the night by sucking on his cock and making it hard for him. When I had him good and hard, I climbed back up between his legs and let him put it in me again. His cock was nice and big and my ass was good and tight. It felt good to feel like a girl receiving anal from her big Daddy. While we lay on our sides in his bunk and fucked, my trucker...Read On

19

Hitch-hiking Baby Doll: Part One

Hitching a ride with a trucker leads to loads of fun for this sexy little tranny boy.

I hadn't been in his cab for more than a half hour when the driver who picked me up, brought up the subject of sex to me. "Last week, I had a guy and girl riding with me and they both liked giving me blow jobs. And, you know, if I closed my eyes, I couldn't tell the difference of which one was sucking me off. They were both excellent at sucking cock." "That sounds like you had a fun ride,"...Read On

21

A Picnic in the Park

Wearing my sexy thong bikini to the park leads to hot action with a big stud.

It was a beautiful spring day, the kind of day a girl starts to think about wearing her new bikini to show off her hot body for lots of men. I was feeling frisky and thought meeting some new men would be fun. There was a county park near my town where lots of men go to meet up for some good blowjobs and hot encounters. I planned to go there today. My new bikini still had the tags on it and...Read On

10

In Her Shoes Part 3

This is the final part so please read both other parts to this story to understand it fully.

I guided Peter into the main shopping mall in town leading him straight into a shoe shop. The girl in the shop fetched a few pairs for me to try on and I relished asking Peters opinion. He tried not to look too obvious that he was hooked on my shoes and feet. I 'hummed' and 'ahmmed' a short while, telling the girl I was undecided and may well be back later. Grabbing his arm once more we...Read On

33

Seducing Uncle Frank

A tale of a Crossdresser seducing his attractive Uncle.

This is a story that happened some time ago, when I seduced my Uncle Frank. Uncle Frank Uncle Frank was married to my mum's sister. He was about 10 years older than Aunt May, and it was both their second marriages. Uncle Frank had an Italian father, French mother, three older sisters, loads of nephews and nieces, and had property in Kensington, the Algarve, and Telluride. You could say he...Read On

25

Mariah... My Wank Mistress

How I met Mariah, a crossdresser's dream...

We first made contact about three years ago, on one of those dirty dating sites. I was showing my tranny profile, Velvet, at the time, and was being hit on by a bunch of dirty old men, when this "Mariah" person said, "Hi." I was in a pretty sarcastic mood at the time, and was slightly peed off, as the guys I had been chatting to were only interested in one thing, getting their rocks-off. ...Read On

6

The Night Of A Thousand Dreams

I hope you enjoy

There was a few odd looking drugs laying on the side from a party. Being bored I decided to see what they were all about, I had dabbled before but had no idea what they all were. I had seen someone use a bottle with an inhaler on it, one good slug later I felt good. I looked through my wardrobe and decided that all guys seem to go for the more cute look in a girl. As I was feeling daring...Read On

21

Not What You Think I Am

Excited by the young looking woman who is such a surprise.

Marriage can be a lonely place, two folks living together and yet being so far apart. It never used to be like that but I guess it comes with the ageing process; a mid-life crisis. To overcome our frustrations, my wife decided we would spend more time together away from our comfortable home, so one weekend every month we hire a log cabin at a campsite that sits between the forest and the lake....Read On

80

Caught, Used and Loving It!

I was caught dressing up as female and used like a toy

I knew I had time now; my wife had gone out with her friendsand wouldn’t be back until 10pm at the earliest. As it was only 6:30, I knew I could spend time getting ready before playing around on the computer and enjoying a nice relaxing but exciting orgasm. My cock was more than ready as I hadn’t had sex for over a week and no chance to masturbate either due to either the kids being around or...Read On

19

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

15

Tammy, Lisa, and Karen part 3

Please read: Tammy, Lisa, and Karen part 1 and 2 first

I woke up the next morning with Lisa sucking on my little clitty, making it hard. I pulled her panties to the side and began to kiss her beautiful pussy and suck and lick on her clit. I began to plunge my tongue as deep as I could into her hot wet honey hole. Lisa was about to make me cum, then she stopped. She knew just where my breaking point was. She turned around and sat down on my...Read On

16

Club Night

Wearing my sexy minidress out to the club, I give the boys lots of thrills.

I hadn't been at the club very long when he came over to me: a very handsome man, tall with dark hair and blue eyes. "You have a perfect ass," he said. I was wearing a sexy, little minidress which barely covered my ass and I knew it would turn men on, but I didn't know it was going to happen this quickly. I smiled up at the tall stranger. "I'm flattered," I said. "I'd like to pull up...Read On

9

In Her Shoes Part 2

This is the second part of In Her Shoes so to fully understand what’s gone on

please read the first part. After a short time of resting my feet on Peter’s bum I now slipped my foot back rubbing the sandal against his balls and cock. His knees started to widen slightly as I teased I could see his balls quickly rise up and tighten as they had before. His cock was now straight along my foot and his body was rocking back and forth in time with my foot. I could feel...Read On

15

From One To Another-Part 2

two sides of a chair

I rushed into my new consignment shop job, the one that Allison had help me get. The shop was actually a duplex. One part Mary's home, the other her shop. I was a few minutes late and apologized to Mary Elle the owner. Telling her that my Biology teacher was on my case about missing assignments and had kept me after school.  Mary Elle looked at me and suggested a nice warm shower to help...Read On

8

Porn Star Babe: Part Two

Time to get the lttle sluts on the set for some hot tranny action.

Being a sexy girly boy about to make her debut as a porn actress with two handsome, well-hung studs was so exciting to me. And having my friend, Chrissie Licks, along to show me how it is done was especially re-assuring. Chrissie and I were naked and about to get into our sexy lingerie for the shoot when Summer Cox, another hot tranny porn star, came to help us with our hair and make-up....Read On

32

Sissy at the Bookstore

Or how I humiliated myself in drag

I had gone to adult bookstores for many years and had done it in drag many times but never dressed as a sissy and never during the day. On this day I was so involved in humiliating myself that I decided that I need to take that extra step and I did. I had checked into an adult motel the night before and booked for two days so I had a lot of time on my hands. The night before I had pranced...Read On

17

Porn Star Babe: Part One

Making her first porno movie, Courtney discovers all the pleasures of being a porn star.

As a hot, 20 year-old girly boy, I was invited by another girly boy to star in a porn movie with her. It sounded fun and I was adventurous sexually, anyway. So, becoming an actress getting lots of big loads of cum from her handsome co-stars was very exciting to me. The movie was shot in a private house where I drove to with my girlfriend, Chrissie Licks, a pretty, 21 year-old, aspiring...Read On

21

From One To Another

a woman is born

I was raised by my aunt due to unknown circumstances in my life. Although she was puritanical and strict I loved her. She had some rules for me. For example, I needed to say Grace before every meal and go to church every Sunday. I needed to read the scriptures on a daily basis and she monitored the TV shows I watched. I was not allowed to listen to modern music or read magazines. This...Read On

29

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

3

A Panty Boy in Paradise: Part One

Being an escort for men leads to new sexual adventures for Courtney.

I wasn't sure how it was going to go. My new client hadn't given me any specifics. But I was excited about the glamour of being on a yacht with a rich older man and his young crew. We would be sailing for the weekend to the Bahamas and I would have my own cabin to sleep in and take naps during the day. All expenses, including the lingerie and bikini bathing suits I would wear, were paid for....Read On

19

In Her Shoes

I opened my online mail box as usual, looking down the list in case any new spam was in amongst the thirty-seven mails I had received. As I scrolled down the page I noticed a new mail from one of the sites I used to find new partners for sex. I clicked it open straight away not wanting to waste any time, hoping that this mail for once was from someone more sane and rational than the usual,...Read On

13

Vanessa Spends a Night Semi-alone

One night I was laying around bored, so I decided to get all sexied up for no one but me. I got out one of my favorite outfits, which you can see in my picture. I was so excited as I undressed, and laid everything out that I was about to slip on. First I put on my sexy Victoria's Secret thong. It was white with black lace, and it felt so hot as it slid on. Then, I put on the matching bra. It...Read On

45

Born To Be A Babe: Part Two

Wearing a sexy pair of hot pants, I go looking for men at the adult bookstore.

After discovering that I enjoyed wearing sexy little panties, tasting cum and having a big vibrator in my ass, I began to have these auto-erotic sessions, every day.While wearing panties and playing with my ass with a dildo, I would lay in my bed and fantasize about all the big cocks I wanted to satisfy for men. While I was only 16 years-old, I had decided I was a girl and I wanted to wear...Read On

14

The Sexy Secretary Gives at the Office

Working as a tranny escort, I get dressed up as a sexy secretary.

Working as a tranny escort is my favorite way to earn money and get lots of cock, at the same time. I love to put on sexy panties and show off my body to men, so it is a job I enjoy doing the most. The fact that lots of men really like me and call me back again and again makes me feel wonderful, as well. I have long hair that makes me look like a woman from behind and my breasts are big for...Read On

45

My First Time with a cross dresser

Introduction to crossdressers

Growing up, like many children I went through phases. I would climb trees and play football, then as I reached my mid-teens I continued these phases but also became a lot more sexually aware, thanks to the porn magazines and porn films usually belonging to my mates dads or older brothers. Now I am in my late teens and at college. One day my Dad made a pot of tea and breakfast.“Did you...Read On