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11

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

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

56

Becoming Ginna

First time sucking cock, first time fucked, first time girl !

We were just over 16 years old when I and my childhood best friend Tim, discovered masturbation. And once we did, we couldn't have enough of it. More often than not we would be at secluded places jerking off over porn magazines. From then onwards I realised I was getting more excited watching Tim masturbating rather than the porn, and soon I started wondering rather intensively how would his...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

44

The Party

It happened one halloween

I am a closet cd. It was Halloween. My wife called from work and said she wanted to go to a party at a friends house. It was a costume party. She said she had a costume and I was to wear one as well. What, I don’t have one. Yes you do, your going as a girl. But I’ve never done this. Well you’re going to tonight. No one will care because it’s a costume party so get dressed...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

32

Family Friend Outing

A family friend fucks me after outing myself to him

A few years ago I went back home to Greece for Easter to see my folks and enjoy a bit of the sun. My folks live in a small town where it’s impossible to get any cock if you are not out. As any typical small town where everyone knows everyone, coming out to a few people becomes coming out to the entire town after a few days. So naturally I spent most of my time gagging for cock in silence. ...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

22

How Andrew became Andrea Part 2

"Did you cum?" Lacy asked. "Yeah," he answered trying not to look at her. "No need to feel embarrassed. Its all right." "I think I better go," he said and stood to leave. "Can you come over tomorrow?" "Yes, if you want me to." "Yes, I want you to. I will have a proposition for you," she said as she escorted him to the door. "A proposition? What kind?" "Tomorrow," she said...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

Crossroads

A young man explores his feminine side.

A crazy little story where a young man finds out if his hidden desires are what he really wants. This all started with my desire to see what it felt like to have big breasts. That's a little odd for a guy. I was a normal heterosexual guy who dated some in high school and now that I was in my mid 20's I found myself at a crossroad. A couple of years ago I had decided to...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

The Next Night - Crossdresser: Part 2 of 2

The next night and a second session with Jenny.

I woke up early from the sunlight shining through the windows. We’d forgotten to close the curtains when we collapsed into bed last night. Jenny was already awake and watching me.  ‘I was just about to wake you up with a blow job,’ she smiled. ‘Funny, I was thinking of doing the same to you!’ I laughed. Jenny kissed me then turned around in the bed to lay on her side so our cocks were...Read On

10

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

10

Toby's Story

Now this doesn't happen every day!

  I had been admiring myself in the full length mirror for the umpteenth time in the last hour, as girls like us do, when I heard a vehicle draw into the driveway. Under normal circumstances, this would not be cause for concern. But circumstances were far from normal. I was miles from my home, in my friend Annabelle's house, and fully dressed in her clothes, and caked in her cosmetics! ...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

50

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

39

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

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

20

Caribean Vacation part 2

Lost luggage leads to wearing girlfriend's panties as a swim suit and more

We strolled down the hall to the elevator. I did not notice what floor we went to, as I was so pre-occupied examining my sexy self in the reflective surface of the elevator. We got off the elevator and walked down the hall to a door marked 469. “This isn’t the dining room,” I objected. “No, this isn’t,” she replied as she knocked on the door. “Who’s room is this.” I asked. Before...Read On

20

My wife finally indulges in my fantasy

This story is a work of fiction I wrote for my wife.

I come home from work to find you dressed in your sexy jeans, a tighttee shirt, and a pair of heels. I can tell you are horny by the way you tell me to get into the shower and that my clothes are laid out for me after I finish cleaning up. My cock throbs as I shower and lather my body up with some scented soap. I know you want me squeaky clean so I insert a soapy finger into my ass,...Read On

The Day My Secret Was Discovered

My wife surprises me.

My wife and I have been happily married for four years. She is the dominant one in this marriage. Just recently I have discovered how much I enjoy wearing women's clothes. I love how the panties feel between my ass cheeks. The silkiness of the nylons on my legs as I slide them causes an erection every time.  My wife had no idea until one day when I had Friday off from work. As soon as she...Read On