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Crossdressing

21

July 4th Celebration

My wife Ann sets up a mini vacation over the 4th of July.

On July first I returned home from our health club. Ann was packing my suitcase for a mini vacation at a bayside resort. My suitcase was filled with all my girlie things: lubes, vibes, wrist and ankle restraints and the paddle she used on me when I was bad. She also said Ben, his brother Josh, and two others were joining us. Before continuing, I should mention how I became the man I am...Read On

27

The Wrong Twin, Part Two

Enter Francesca

As Willy led me by the hand up the stairs, I couldn’t help but look at the smoothly shaven legs and the short plaid skirt that were clearly being presented for my viewing pleasure. Sheer white socks with fold-down frills at the top accented her open-toed black high heeled shoes. There was a nice casual sway to the hips as she negotiated the stairs. I got a glimpse of pink panties underneath...Read On

6

The Business Trip - Part 1

A man has a wild experience on an unexpected business trip.

I work for a small web design company in northern Connecticut. We acquired a rather large account with a lawn care company in Virginia, and my boss asked me to go with him to present the design we had created, since I was the only other male at the company. My boss told me he didn’t want any of the women to think he was hitting on them. Never having been asked to go on a business trip for...Read On

8

Just the Two of Us, or Four

Vanessa and Greg fail at trying to spend a night alone

As time went on, the line was beginning to blur between me being Greg's girlfriend and Amber's pet. Greg decided that we needed a night alone. That didn't work out exactly as planned. He booked us into a lovely, fancy hotel in the heart of the city. Next up was going to be a nice dinner at a gourmet restaurant, and then we'd see where the night went from there. I wanted to impress, so I took...Read On

27

The Wrong Twin

Willy was my first....

The Halls moved into my neighborhood when I was entering my senior year in high school. Typical Midwestern town, typlcal high school, and I had the typical Catholic upbringing, which meant I was still a frustrated virgin. I had spent most of my upbringing helping out with chores on the family farm, and was therefore outdoors a lot; the result was I was tanned, blondish brown hair that I wore...Read On

20

Caught!

Crossdresser is caught by his flatmate and fuckec

I stood in front of my full length mirror wearing my new black heels. Not just the heels of course! I had a sexy, short black dress to go with them. Underneath, I had some incredible purple and black underwear; all silk and lace. I twisted on my heels and pulled my dress up a little, wiggling my thong covered ass at the mirror pretending somebody could see... ...And that’s when he knocked!...Read On

22

Caught By My Girlfriend

Hitting puberty late in high school had its disadvantages. A slender, almost feminine body and a small dick was not something a lot of women tended to go for, however, I was lucky enough to find Adrian. We hit it off right away, shared many things in common and we couldn’t get enough of each other. She was gorgeous, standing at six feet, she was just as tall as me. Her beautiful crystal blue...Read On

20

An Uneven Romance - Part Two

He's taken further into her strange, kinky world

“Hey, Sam.” I jumped and spun around, startled. One of my housemates, Mark, had walked into the kitchen where I was preparing breakfast for Sarah, the incredible girl I’d brought home the night before. Sarah was a pretty special girl; after a night spent with my head between her legs she had eventually let me cum this morning. She’d somehow coaxed me into wearing her wet panties from...Read On

36

An Uneven Romance

He picks up the girl of his dreams only to find himself being used

I couldn’t believe I’d gotten her home with me. We’d met in a bar when I was drinking with my friends, I spotted her early in the night but didn’t have the courage to talk to her. She looked perfect. She was slim, with long red hair that came down to a tight, round ass. When she turned around, I saw she had a truly beautiful face but there was a sexy, dangerous look in her eyes that scared...Read On

24

Anonymous Encounter

An Anonymous Encounter of a Crossdresser with someone from Adult Friend Finder!

Well it was a boring day. It was fairly hot outside,somewhere around 93 degrees. The sun was shining, there were very few puffy clouds in the sky, and I was home alone. As usually happens when I am bored and home alone, I was horny as hell. I wanted to jerk myself off, but I wanted to do it to something different than the normal porn that I usually watch. I figured since no one would be back...Read On

9

film fun

I get fucked while her husband films it

I met Lucy on the net, she was a married BBW with massive breasts (46g) and ass to match and loved to dress how I like my ladies to. That means mini skirt, high heels, stockings and suspenders and a low cut top.  We had met a couple of times before I got to meet her husband Ray.  Lucy and Ray had arranged to come to my house one Saturday night for some food , drink and fun, but I had no...Read On

43

From Shock to Awe...some

The day my sex life was unexpectedly changed forever by a loving wife

To this day, I don't know what caused my wife to come home early from work that morning, and although at the time I was sick to my stomach with dread and fear when she walked in on me, I'm now glad that it happened. For the first time in over ten years of marriage, we can now finally talk about what sexual desires we have. But I'm getting ahead of myself. Let me back up a bit. I met my...Read On

11

First Night Nerves - Part 2

Tina agrees to meet Barry without 'the girls'

I sat by myself on the bus, my briefcase on my knees, counting the stops and wishing it would go faster. Since Barry’s text message last night and his surreptitious call to my mobile that morning, I had been so excited, planning what I would wear to please him most. Debbie hadn’t heard the beep on my phone so didn’t know that I would be meeting him without her that afternoon. So far I had...Read On

7

Starting to Have Fun as a Slave Girl

Vanessa is won at an auction to do one man's bidding for the night

Greg and I had resumed our relationship as normal after my experience at Mistress Amber's. I was enjoying being his girlfriend. He treated me so nicely, and we enjoyed our time together. It was the most intense sex life I had ever had with anyone. For the most part he enjoyed being the dominant one, and he was happy to make me his little fucktoy after a nice night out. But it was that line...Read On

28

My New Sissy Life

A sissy lives out her ultimate dream.

I was so stunned I was unable to speak. I only thought things like this existed in my fantasies and could never actually exist in the real world. It had been three weeks since I found an ad posted online seeking two submissive males for "training." I read the description which said, "Attention sissy boys! Have you ever wished that you were a trained sissy slut? Of course we both know the...Read On

32

First Night Nerves

Nervous Tim becomes Tina and loses her virginity

My name is Timothy. I live in a large city in the English Midlands with my girlfriend Debbie. We are both 22 years old and have lived very happily together for over three years. We both work in a call centre for a large financial organisation. I am not tall – 5' 4" on a good day – and have always been very slim. I am blonde with blue eyes and very fair skin. Debbie is two inches shorter than...Read On

13

Transitioning and Bound

Vanessa and her man find a mutual pleasure - her with other men

It had been a while since I started the hormones, and I couldn't have been happier. I was looking and feeling more womanly than I ever thought possible. It brought me a new confidence when I was in public, and made me feel so much sexier, and girly when I was in the bedroom. My breasts weren't that big, but they were growing over time. I had a nice handful, and Greg said he loved to suck on...Read On

16

First Meeting with a CD

A cross dresser experiences his dreams with a man

It was strange, he contacted me first and his profile stated he was looking for a domme or trans to submit to. I guess the hidden desire to please a man won out. We communicated through mail and messenger for months. We even met for coffee and some groping, where I tested his desire for nipple play, some severe pinching and even squeezed his sac to express the control I wanted and what he...Read On

37

Dirty Little Me

Caught, with panties on and my pants down...

Rushing around all day, it seemed like this was starting become a ritual for my Fridays but this particular Friday I would never forget!  Waking up late as usual I flew out the the door as fast as I could, not giving any thought to what I had done the night before. As usual my boss wasn't too pleased but I never really minded his attitude because everything he lacked in personality he made...Read On

19

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

32

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

20

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

9

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

36

My First Time With A Hot Sensual Lady - With A Lovely Cock

A shy bi guy has his first amazing encounter with a beautiful lady who also has a beautiful cock

Although I'd never been with a man before, my online chats and contacts usually ended up being with men - they seemed to be so much more horny and available than women. Either I was doing something wrong or women weren't into online sex all that much! Anyway, for years it's always been a hobby, an indulgence if you like, never turning into real contact, just a fantasy that I look forward...Read On

32

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