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24

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

15

A Sweet College Girl In Love

As a sweet college girly boy, I dated a real big hunk with a ten inch cock.

I went to college in a beach town in California where all of the girls wore their little thong bikinis to the beach and showed off their asses for boys with very friendly results. I noticed that when the girls were bending over while playing volleyball in their little thong bikinis, the boys all looked at them with hungry eyes that I liked a man to have for me.  The sweet little college...Read On

13

A Night at the Ambassador

An early evening of debauchery earns kudos for a crossdresser.

While on business in Colorado Springs, I had the opportunity to visit one of the adult theaters that I had visited previously. Although the booth area was in full swing, the booths had no doors and there was no privacy what so ever. One could still have a good time if they were so inclined. The attendants were cool and they did not mind the actions of others as long as there were...Read On

4

Family Support

from the title u may think more than what it actually is i only have one family person who knows my cousin who is a lesbian she phones me up anytime she is alone for me to come and dress in her things.  Any way to my story my cousin had phoned me up one day and told me to come over it was only a five minute walk and i was so excited.  when  i arrived she told me to go up to her room and once...Read On

11

How to please your girlfriend

When she gives me the puppy dog eyes, I can't resist....

(Some of this story may be slightly fabricated, but don't worry about what is and what isn't, just enjoy the story.) It was back in February when me and my girlfriend plus a few friends decided to go to a con. We hung out together and thought it would be fun. A friend bought my ticket and the closer it got to the con, the more we were excited. Not only did we get more excited, the closer...Read On

18

A Terrific Threesome: Part One

Wearing my girlfriend's panties leads to a big cock for both of us. .

When my girlfriend and I moved into our new apartment, the tall handsome maintenance man came by to put a hand-held spray-jet nozzle on our shower for us. I was home alone and dressed in a sexy little pair of Sherry's panties when he arrived and I put on her little short black silk robe to answer the door. When I opened the door, the maintenance man's eyes went directly down to my...Read On

11

Peer Pressure, Both Ways...

Girlfriend's boyfriend cums to the rescue!

"Fucking pervert, fucking pouffe, tosser, sissy...." Lenny had become accustomed to these names over the years, as he went about minding his own business, but the lads from out of town were relentless, as they began pushing and shoving Lenny. He tried to walk away, but they roughed him up a bit, before laughing hysterically and then shooting off. Lenny wasn't physically hurt, just a...Read On

13

From Anton to Antonia

Anton discovers a feminine side to his sexuality

The first sex I had with a couple was my boss and some woman we just met in a hotel bar. I liked it, so the boss told me to put out an ad. An advert in Craigslist for my area was all it took. Posted in the casual section under M4WM and a photo of me from the shoulder down, I had a flood of answers. I chose Julian and Rosemary, they were mid- thirties, still twice my age and arranged to...Read On

13

An Old Friend

Found out by a friend - hope the length is not a turn off...

   Jerri is a close friend whom I have known for a long time. I was on an interview board for her when she joined the volunteer fire department. I was a little skeptical about her joining, especially since her husband seemed to be rather indifferent about it, but was overridden by the rest of the board. As time went on, she proved herself to be one of the top responders and an...Read On

10

Learning To Be Submissive - Part 2

My second meeting with Jack

I arrived slightly earlier than I was meant to. After our first meeting I had been given specific instructions. Jack had allowed me to shower and change back into my normal clothes. Once I had returned to the kitchen, I found a note with a key. "Today you excelled yourself, but you have more to learn. Next week on Monday you are to come directly here after you finish for the day. I will...Read On

3

Satin2

As Cloe and I walked into the lingerie department her eyes lit up, hey what do you think to that? In the corner was a stunning silk dress all in black with a sexy halter neck and a large slit up one side. Imagine that dress with stockings and suspenders 4” heel and you wearing it she said. Our basket was already full of sexy items; Cloe pulled the dress form the rail and asked me to...Read On

23

Christmas At The Salon

Fun for everyone at Susans beauty school...

Back in October I introduced my friend Susan to boys that wanted to be girls for her beauty school.They would come in for help with their hair and makeup and her students could practice on them.Everyone had a ball and it worked out very well. Soon the girls realized that this was a dream come true for the boys and became more demanding of them.Keeping the place clean was just one of their...Read On

18

My First Boyfriend Part Four

I suck off a bunch of guys at a party and take two home to have a foursome

The drive home from the party was quiet because I had sucked off ten guys at the party and my mouth was sore and we were pretty drunk too. Two of his friends were following us home I assumed to have sex and party. I lay on the seat with my head in Steve's lap and rested while we listened to the radio. I asked Steve how were going to keep those two from finding out I wasn’t a real girl and...Read On

7

Missy Returns

It had been a long time from the seven days I spent with my studs, but sadly I went off to school and Missy had to go on an extended vacation. However, school did not work out as planned and I found myself in a new city and my own apartment with a small job. I had to help pay the bills. For a while I lived with a roommate who was a little homophobic and despised the ideas of trannies. He...Read On

8

Telling Mom I'm A Crossdresser Part 15: 2 Kinky Girls.

Part 15 is finally here :) plz enjoy as Missy enjoys a night with Laci alone!!

It had been a week since Mom and I spent the 4 days at the spa and hung out with my old babysitter Laci and for a while it was back into our old routine of working and coming home. Day after day I kept thinking about how her warm wet pussy felt wrapped around my cock while the feel of a sexy thong rubbed against my asshole. I came home one day to find my mom was packing a bag. I asked her...Read On

14

I was a wartime TV for the US Army

Reform school teenager is offered a unique chance to serve the troops during WWII

  'I was a Wartime Transvestite for Uncle Sam!               TJ Ryder                                            Chapter 1           Reform School Romance!     I couldn't believe that all I got from my uncle Bill when he died after all he said to me about my being his favorite grand nephew was an old diary from World War II.    I mean I thought we got along pretty darn good, and its not...Read On

25

High Fashion Queen

A transformation changes the lives of two college friends.

I felt like such a loser. It was Friday night and instead of going out and hitting the clubs to dance, drink, and have fun, I was in my dorm room with my best friend. We had known each other since the 6th grade and today was his birthday. No one should be left alone on their birthday right? To be honest, I didn’t really feel like going out anyway. My boyfriend, who I had been seeing for...Read On

29

Jessi's coming out party

Jessi comes out to several friends and has an interesting night.

Hi everyone. My name is Jessi, I'm 23 and I have been a crossdresser for over three years. Recently I decided to go full time and was going to met up with some friends to come out to them. I arranged to go hang out with them at my friend Derek's house, them thinking I was still coming as my old self. My roommate, who started my path into crossdressing (that's a whole other story), told me if...Read On

19

Jessie's Time for Payback

After Jessie's Reward, it is time for payback!

After Dan left me with his cum dripping out of my ass, I kept replaying his words before he left. “Jessie, you were amazing! I can’t wait to tell all the guys at work about this!” It was Friday night. Dan was the first one to make me feel like a woman, but now I had another dilemma. How am I going to face him and all of my co-workers if he indeed tells everyone about me? I woke up...Read On

8

This one is for Tracy

Submission of a crossdresser to his boyfriend's girlfriend.

This story requires a short preamble. I had e-mailed erotic stories and fantasies back and forth with my friend Paul for several months. He liked to be a dominant, so one day I asked him to send me exacting instructions on how he would like me to masturbate, which I would have to do and then describe back to him. He sent the instructions, which involved me getting fully cross-dressed...Read On

27

The Pool Man

Sunbathing near the swimming pool, I turn on the handsome new pool man.

It was June and time for sunbathing by the pool in my backyard. To my pleasant surprise, I saw that the pool man the company sent this year was young and handsome with a muscular body and porn star mustache. I was instantly attracted to him the first time he came and we hit it off quickly. I was wearing a pair of cut-off shorts with a sexy black thong panty underneath. And I felt very sexy...Read On

8

Adventures of Kristof and Marci - Part 1

After a long internet relationship, Kristof and Marci finally get together to explore their fetishes

ADVENTURES OF KRISTOF AND MARCI PART I The Meeting I sat on the chair in front of the computer, wearing a tiny black swing skirt, black nylons and red high heels.   Beneath the skirt I wore a little pale pink lycra thong and I was naked from the waist up, save for the chain that hung at my chest, the ends connected to each nipple by a little clip.   ‘I really need to pee’...Read On

26

Just Needed A Drink

I didn't know what kind of bar it was.

My travel plans had been totally messed up. Weather was to blame. A huge pattern of thunderstorms sweeping up the East Coast had screwed up more than a hundred flights, including mine. As a consequence I got into Boston about five hours later than I'd planned on. I was tired, irritable and, well, generally quite unhappy about life. The cab ride to my downtown hotel was uneventful but the...Read On

30

Vanessa Goes All the Way

A few months after having my first date, I was feeling kind of anxious about not really allowing myself to go further. I had plenty of guys interested, but I wasn't really ready to make that move. I had been talking to this sexy college boy for a few weeks, but we couldn't set up anything solid. We finally nailed down a date, but he had some last minute issue come up, and had to cancel. I...Read On

6

GAG-A-RIFIC BARRY

Brittany and Jenna take revenge on Barry.

When I first met Barry, I immediately noticed that his smile was gorgeous.   The second thing I noticed about him was how great his ass looked in tight jeans.   He was flirtatious and playful.   Barry and I had been dating just a month when we made a bet on a basketball game.   I won the bet and jokingly said that I wanted Barry to wear a pair of my panties.   Barry blushed but...Read On

20

My First Date

I had met Pete over an on-line dating site, and we had chatted for several weeks and developed a rapport when we decided to have our first real date. We agreed to meet at a local shopping mall parking lot and would do some shopping together. I spent the morning shaving my body smooth and getting ready. I went with a natural look for my make-up, and peachy pink lipstick. I slipped into a...Read On

Mistress Hannah's Pathetic Husband Part 8

A return to the body art parlor

As we tried to sleep one Friday night after Mistress Hannah had used my ass with unusual vigor, she was tossing and turning and keeping me awake. I got the impression that she was struggling with some personal demon that was becoming an urgent threat. Something had changed around the time two months earlier when I had first achieved the goal of putting my puny pud up her ass. I don't think...Read On

13

The Sexy Girl-Next-Door: Part Two

Courtney has a neighborly affair.

Once a girl gets a big hard cock in her, there is no stopping her from wanting another one in her. At least, that's how it was for me after my first fuck with my neighbor, Ben. He had just fucked me with his twelve inch cock, with a big head on it and I loved it so much I couldn't wait to do it again. Our friendship was growing like our dicks were. And I was now having an affair with my...Read On

6

An Introduction to Crossdressing Pt 2

Learning how to be a passable crossdresser

So as Jacky was going through his story about how we ended up in this shop, I started to look around. I found that my initial belief that the shop was just a hair dresser was completely wrong. The shop was split in two, long ways, with the left side having about four stations for regular hair work, two stations for nails and a couple of closed rooms for massages, waxing and tanning. 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