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Crossdressing

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11

Weekend Discovery 3

Simone was left alone in a room that held the most extensive collection of lingerie that she had ever seen outside of a retail store. She was amazed that she was as turned on as she was and not shocked at the current events. She had gone to her boss's house to confess just how much she wanted him and to see if the feeling was mutual. She was momentarily heartbroken when a stunning...Read On

11

Becoming Chloe - Part 24

Chloe loses her virginity...

We sat sipping our wine, our feet rubbing each other. I felt contented and just a little woozy from the alcohol as I cuddled up to my man. We sat like this for a while, content in each other's company, like countless other couples up and down the country on a Saturday night. Occasionally Colin would kiss me, and sometimes I would steal a kiss from him. Slowly we moved so that Colin was laying...Read On

11

The Joy Of Becoming A Girl Without Kknowing It

Can it be that i have an effect on ... it

Thankfully a decent spring day arrived. With its coming brought out my need to be dressed, become and behave girlie and fem. I studied the weather patterns and made my plans to dress En-Femme with it. So that day finally was here. A joyfulness overcame me as I looked out my bedroom window and saw the sun glowing brightly. The sounds of chirping, singing birds was loud, crisp and happy. The...Read On

11

Weekend Discovery 2

Simone's eyes grew wide when she realized that the stunning blond she was sitting next to was, in reality, her boss and the object of her most intimate desires. Now she had seen transvestites and drag queens before, but none of them looked this good. She was sitting just mere inches away from his face and still couldn't see any trace of Andrew Lippincott. Without warning Andrea leaned...Read On

11

Trio

A secret assignation in a country hotel turns into an unusual menage a trois

Dusk. As he turned off the highway into the country park hotel, Nick was relieved to note that its car park was barely a quarter full. Pulling his overnight bag from the back seat, he headed for the brightly-lit reception lobby. A giggly gang of women were disembarking from a mini-coach. Most were clearly very drunk. In the hotel's spacious lobby he quickly spotted Mark,...Read On

87

Vicky's First Time

My first time having sex as Vicky

I was very open about crossdressing when I met my wife when we were in our 20s. She has been very supportive and helpful. She helps me with my hair, makeup, and picking outfits. We started having sex with me dressed up as Vicky. This soon escalated to her taking me with a strap on. I loved the times she would fuck my ass with her cock. I had never considered myself gay or bisexual but the...Read On

66
Audio version available

In My Panties!!!

Sarah discovers Larry's secret.

Larry and Sarah were your typical yuppie couple working two professional careers. Larry a techno wiz was the research and development department head at a local manufacturer while Sarah was the office manager at a local Saturn car dealership. Their weekends off work were filled with their hobbies of camping and outdoor fun. Both loved nature and enjoyed their time together on beaches and in...Read On

54

Little Black Dress

The events were all the result of a lost bet.

I pulled in the driveway, and saw that my wife was already home. My thought was that she’s home early. I unlocked the door and went in. A few feet inside the door was my work stool with a box on it with a note taped to the top. I opened it and started to read. Hun, I’ve decided that tonight is the night I want to collect on our bet. You are to follow...Read On

45

Summer dressing

Long hot summer for crossdressing student doing vacation job

It was the mid 1980s, I was 20 years old and it was the summer holidays. For the long break from college I'd managed to find a vacation job in Kent in the south of England. It wasn't brilliant but I was going to get some experience of working with computers, and earn a bit of money to keep me going during term time. The company was based in a small town where I had found a room in a house with...Read On

33

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

31

Tammy, Lisa, and Karen part 2

Man discovers his fantasy with more than one woman.

Please read "Tammy, Lisa, and Karen Part 1" first. I walked out the store looking at the bag of lingerie in my hand and my cock was so hard, I could barely walk. Lisa wanted me to be pretty for our date. I only had some lipstick and eye shadow at home; I needed to figure out how I was going to make myself pretty for her. That's when I walked past the the answer, but could I really do it? ...Read On

31

Confessions of a Ladyboy - Part 1

He helps me resolve my boy/girl confused sexuality dilemma

I was eighteen and new in the boy's hostel. No one had wanted me at home. I had never known my father. I saw my mother go out with a different man almost every night ever since I was old enough to remember such things. She taught me some valuable lessons - how to be attractive, how to carry myself, how to be seductive, how to do my makeup. She always said, "You are such a cute boy, you...Read On

23

Terry Gets It In The End

Terry's girlfriend finds him in panties and leads him down the path.

The converted attic was my room and it gave me loads of privacy. So as I grew up I could wear the clothes I liked, as long as I stayed in my room. By the time I was a senior in high school, I kept my toe nails painted all the time and I wore panties every day. At night I wore frilly little night gowns and more likely than not I would masturbate, always fantasizing that I was the girl and...Read On

10

A weekend with Nancy: part 2

Nancy, that was the best blow job I ever had, she's awesome, Dan replied.

 Nancy informed Alice that she would be using the bedroom to dress me, and that she should pick out an outfit consisting of no fewer than seven articles, gather her make-up and whatever else she required and then use another room to get dressed. Furthermore, Nancy informed Alice if she didn't like what she was wearing when she returned that she would be punished, and to not waste any...Read On

10

Suzie and Cindy are taken to their first gay club

this is my fantasy life

As Cindy walked into the room with the outfit I picked for her, she had a distinct glow of a satisfied girl. Harry and Jack added pink nail polish, matching garter belt, thigh high fishnet stockings, jewelry, high heels and they cut bangs into her hair. She really was pretty. The three of them stood there while I was still riding Joe's cock, he was in no hurry. I must be becoming a good...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

Mistress Hannah's Pathetic Husband Part 5

I serve lunch to sorority sisters

I was making progress as a slave but unkown to me, one of my stories helped Mistress Hannah see an opportunity for a particularly fun afternoon and a chance to help an old friend through a rough spot in her marriage. Several months of aerobic classes and feminization had increased my stamina and made me more comfortable when we spent our Sunday evenings out for dinner and as member/patrons at...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

10

Fantasy Meets Reality at the Peep Show

A crossdresser's fantasy comes true

I pushed my way through the purple curtain to the cashier’s booth. He looked up from his newspaper and asked me how many tokens I wanted. I figured a stack of twenty would be enough to complete my mission. I’d been there several times before but this would be my first time taking things further. My heart was beating fast as I scooped up the tokens and made my way to the viewing room. As...Read On

10

How Andrew became Andrea Part 3

Andrew leaned back on the couch feeling the warm cum had just let loose in his panties beginning to cool and a stain become visible on his slip. "Looks like you will have to clean up and change," Lacy said with a smile. "Looks like," Andy responded. "Shall I pick out something or would you like to?" "I would like you to." Andy headed to the bathroom where he removed his cum...Read On

51

The Panty Princess

Dominant girlfriend discovers her love for submissive boyfriend

Jane and I had only been living together for three weeks when I was caught red-handed. I was mortified when I saw her in the mirror, standing behind me with her mouth wide open. She had managed to come through the front door, up the stairs and into the bedroom without making any noise. I tried to explain that it was the first time I’d ever done such a thing, but she was having none of it. ...Read On

40
Audio version available

My first time

First time with a CD. First gay experience.

My first story. And it is the true story of my first encounter with a CD. With a click of the mouse, I had committed… I was going to meet a cross dresser just a few miles from home. Could I go through with it? Is it really what I wanted? Who was I kidding? Of course I wanted it. Now it was time to just suck it up, princess. I took a quick shower and the dressed in my tiniest,...Read On

37

Debbie's Place

A crossdresser gets more than he bargained for

My girlfriend, Linda, was kicking me out of the apartment for the night because her sister, Sandra, was coming to stay. Linda didn’t want her parents to know that she and I were living in sin together. I found it all a bit far-fetched that a girl of 23 years old either couldn’t or wouldn’t tell her parents where to stick their beliefs. But, I knew well enough not to argue with Linda over...Read On

29

Meeting Carla

A friend introduces me to Carla

I hadn’t seen Mark for almost a year. His father had found a new job and subsequently his family had moved to another state. I’d known Mark since the beginning of high-school and I was really looking forward to seeing him again. We’d become friends since day one and it had come as quite a shock when he told me he was leaving. Not only had we seen each other in school each day, but we’d hung...Read On

29

The Change Up - Part 4 - Tower Chair

Deedra shows how big a slut she is and becomes a member of Elsie’s VIP club!

Looking through the sheer curtains of the cabana, I see about a dozen people looking at both of us. Some I just met tonight and others that I don't recognize. Then Emily says to me, "Since you been a naughty cum slut again, I will have you service some of the VIP members tonight! Remember don't talk to anyone and only whisper into my ear." Cuddling next to Emily, I think back to the...Read On

21

Telling Mom I'm A Crossdresser Part 7: The Spa

Missy and his mom go to a spa and meet some new friends.

I could barely sit for days after Mistress Keri thoroughly tanned my hide and I had to take almost a week off so that I could heal. My mom knew this to and said we should go on a “girls” weekend to a spa for cross dressers and women, she also said that since it was for others like me then I could spend the entire trip as Missy. I loved that idea and hurried upstairs to pack Missy’s bag....Read On

21

Punished

A crossdresser finds himself punished.

I glanced around the second hand clothing shop to make sure that no one had seen me pick out the pink, pleated netball skirt from the rack. I hid it beneath a pair of long pants in my hand. I felt my heart start to beat furiously as I stood next to the change room and caught the attention of the shop assistant by waving the pair of pants I was carrying, and the hidden netball skirt in...Read On

21

Crossing A Different Line

A married family man's growing interst in female lingerie leads to his being taken as a woman.

In my personal journey from straight, married heterosexual to bi male, I discovered, along the way, that I was aroused by women’s lingerie. It started with trying on a pair of my wife’s nylon panties. The feel of the silky material, and the sight of how it fit, quickly brought on an erection. I used another silky pair in my hand to jack myself off, being careful not to get any cum on the...Read On

21

First Time With A Crossdresser: Part 1 of 2

Scott looks for something different after his divorce and finds Jenny

I’m Scott, 36 years old and recently divorced from my wife of 12 years. It was an amicable split with no kids to complicate matters. We sold up, divided everything two ways and went on our merry way. Our sex life was good and regular but a little boring. We stuck to the same three positions – missionary, her on top and spooning. I’d give her oral but she wasn’t that keen on going down on...Read On

21

becoming a cock worshipper

I first realized I was bi the summer after high school. Up until then I had only been really interested in girls. Like any high school guy I watched a lot of porn and soon realized that I really liked really nasty deep throat blow job scenes.  I especially enjoyed watching a girl choke and gag and cover a hard cock in her spit. I also realized that my favorite scenes always involved a...Read On