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Crossdressing

15

Felix becomes Felicity - Chapter 2

Life gets more girly for Felix!

FELIX  becomes FELICITY Chapter 2 My Mum and Sister went downstairs and I had a moment to myself looking in the mirror.  I didn’t recognise me in the reflection I saw a teenage girl, a very attractive teenage girl! I joined my Mum and sister downstairs. I was becoming better on the heels “Mum I have to reiterate that this all ends in 6 weeks time right?”, “Of course sweet that’s...Read On

15

felix becomes felicity

bullied into becoming a girl!

FELIX  becomes FELICITY Chapter 1 “Gynecomastia is the abnormally large development of mammary glands in males, resulting in breast enlargement……… In teenage boys this does not have to be linked to obesity……… The word Gynecomastia  derives from the Greek for woman and breast”     I logged off from my regular searches on the internet and felt sick as usual. I am 16 and a normal...Read On

14

Webmeets Diary Ch. 03

I become Sarah to meet an older couple.

Note to the reader: In this diary I will tell the true stories of my sexual encounters that have come about thanks to the internet. Some more precise details such as names and places will be left out to protect mine and others privacy, and also because they don't matter, but otherwise I will try to be as accurate and truthful as possible. I'd been using the swingers' site for more than a...Read On

40

Chrissy's First Black Cock

Chrissy gets fucked by a big black cock for the first time

  After I awoke from a deep slumber of a much needed nap, I laid there recounting memories from the night before with Todd. I got out of bed, walked to the kitchen and grabbed a soda from the fridge before sitting down on the sofa. As I sat down, a pain rippled through my ass, reminding me of the brutal fucking I had received from Todd. I sat there smoking a...Read On

10

A Gift for Daddy

A CD Sub gives her owner a new toy...

"I brought you a present, Daddy," Stephanie said, giggling, as we stood on the porch in the run-down neighborhood in the industrial part of town. The man standing inside was in the shade inside of the house and I squinted to get a look at him. "Eyes down," Stephanie hissed, elbowing me. I did as she said and smiled inwardly. She was usually very submissive and proper when we were together and...Read On

10

Crossdresser and I at Costco

I went to Costco over the weekend with my friends girlfriend. She went off shopping, and I went off to get a few things. I walked down some random isle, and saw a girl leaning down. I snuck a peek at her butt and saw a little bit of a thong showing over the top of her shorts. She was wearing a blue hoody. I looked up and saw that she had really short brown hair. I tried to see her face, when...Read On

30

Cruising The Drive In

It was a Friday night and all of my friends were at home with family. I was really bored and I asked my dad if I could take the van and go to the movies. He said it was ok and told me to be home by midnight. The van was a 1977 Chevy van, it was brown in color and had the moon windows cut into the side. It had the typical "Captain' s chairs" up front and in the back had what you'd expect from...Read On

16

Caught and the Consequences Part 4

Husband caught dressing and the wife's retribution continues

Part 4   I served dinner at 7.00pm as requested and I was made to stand by the table so that I could serve wine as their glasses were emptied and attend to them as requested. I did find the whole experience satisfying in a kind of way as I knew I was pleasing my Mistress and hopefully Sir as well, although neither of them had any conversation for me.   ...Read On

14

Group Fun

Caught outside and forced to suck.

  This is a story of what happened a long time ago. I was 20 years old. I have always been a small guy, 5-5, maybe 125lbs on a good day. All the girls called me cute and I hated it. Until I tried on my girlfriends panties. Wow, I thought how girls were so lucky to wear all this sexy stuff. Well within a year I had gathered a couple of very slutty outfits. I loved Garters and stockings,...Read On

9

Caught and the Consequences Part 3

Husband caught dressing and the wife's retribution continues

Part 3   I signed the contract and handed it back to my wife, well my Mistress now I guess.   She took it from me and said ‘Good girl’ ‘As you will have seen you are now Philippa, now go and get all your male clothes.’   ‘Can I get dressed’ I said.   She slapped me hard across the cheek. ‘When you speak it will...Read On

14

Lingerie and Domination

Lingerie Shopping and something more

I had answered an ad on telephone dating service. She described herself as a ‘bedroom dom’. I am not sure why I answered the ad and I did not really expect a reply. She phoned when I least expected. I did not think she would be interested but I had mentioned in my reply that I like to dress in lingerie — panties in particular. I met her for a drink. She was younger ( 38 ) than me and...Read On

34

Chrissy's First Bookstore Trip

Chrissy's First trip to an Adult Bookstore Arcade

After my first night dressed up like a girl in my very own clothes I started to wear panties and thigh highs under my pants when I went to class or anywhere for that matter. I couldn't get over the sexy feeling of the panties on my cock and the nylons on my legs. By now I had purchased quite a few women's clothes. I had all different colors of matching bras and thongs, I loved the way the...Read On

10

Caught and the Consequences Part 2

Crossdresser caught by wife finding our what she has in store for him

Part 2   While sitting there I went through the usual stages, despair that I had been caught, fright as to what would happen next, would she still want me as her husband or was this going to be a third divorce, and that made me feel very sad as it suddenly dawned on me how much I loved her and I quietly resolved to do anything I could to save my marriage.   ...Read On

9

Caught and the Consequences

Husband caught dressing and the wife's retribution

‘What the hell do you think you are’   I just lay there not knowing what to say and I am sure going very red under my make up.   ………..   I will go back many years and start at an earlier age.   For as long as I can remember I have cross dressed, always in private, without my partners or girlfriends knowing, totally in the closet,...Read On

26

My first halloween night as a teen CD!

My first time i dressed up like a chick and how lucky i got that whole night

This is halloween!! A day that everyone goes out and dresses up in costumes and other things, and go to parties and drink and show off their wild side until the wee hours of the next day. And I thought to myself, since everyone goes out and wears costumes, why not dress up myself into something wild and willy?? Or in fact, why not dress up in a manner of expressing who I am and what I...Read On

26

My First Real Outfit

My First Real Outfit I started completely dressing in women’s clothes shortly after high school. I didn’t really own anything of my own but I would fully dress in my mothers clothes a few times when I knew she would be gone for a few hours.. Usually it was just pantyhose, bras, and panties that I would borrow from my mom . I had experimented with it a bit when younger, stealing my...Read On

33

naughty weekend

I'm bi and it started when I was about 15, just wearing my sisters kickers and thongs. The excitement of it, the feeling of the flimsy material barely covering me.  I kept this up for 3 years until recently id been talking to a guy online who called himself seb, a guy who described himself as 'Tall, dark & handsome.'      A phrase which never really ever meant much to me, this was all up until...Read On

40

She wears the pants, over her cock

I stepped off the plane after three days travelling and was looking forward to going home after a long few weeks of travelling for work. My work regularly has me travelling and I don’t seem to get home as much as I would like anymore.   But it does make it even more enjoyable when I do get home.   Leaving the gate, I walked down the corridor, past the last security checkpoint, and toward...Read On

16

Working It

I get my house painted for panties!

I’ve needed some repairs and painting done in a bedroom for a long time and decided to get some estimates. I had a water leak in the ceiling, and there was a hole there since it was fixed a month ago. Several professional painters came in and they all wanted $700 or more to do the job. I decided to ask my friends if they knew someone who might do it for less. One of my friends told me...Read On

13

Crossroads Ch.4

Another chapter in this fantasy tale of a young man's journey into becoming who he is.

  I am on an airplane flying to Vancouver. I have an appointment with a doctor to have sexual reassignment surgery. I am so excited I can't stand it. I know this is what I want. My recent encounter with a woman convinced me. I have no doubt about it now and won't look back. We land and as we deplane I notice, as always, the admiring looks I am getting from men, including the pilots. I...Read On

11

Work Hard, Play Hard

Expect the unexpected

After a long hard day of work, everyone decided to go to the bar after work. It was a busy day and everyone was stressed out; a beer amongst friends was just what the doctor ordered. The whole gang met at a Gino's, a local bar in a small Illinois town. The bosses were buying round after round, till everyone was all nice and liquored up. There was quite the crowd; about 15 in all. Dirty...Read On

9

Crossroads Ch.3

He has to find out if this is what he wants

A tale of pure fiction and fantasy. I was actually considering going all the way. Going all the way in becoming female. I had been living as a female in all phases of my life for some time. I continued on the hormones and all my desires said I should do this. I had called the plastic surgeon who had done my breasts and explained what I wanted. She suggested going to see a doctor...Read On

15

Crossroads Ch.02

A young crossdresser take things farther.

The second chapter in this crazy little tale. I really loved my little adventure out as a woman. I liked the power I had over men. I was seriously thinking that I would like to live as a woman full time. That would be quite a commitment and one that would change my life forever. As I said before I worked for a really liberal company and one day I got up some courage and went to...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

20

What's In The Name Shazstoned

It was a Saturday night some years ago, I was home alone, it was time to dress fully for the first time. I showered and had a good shave. I started with my false eyelashes on the top and bottom of my eyes, next the foundation and powder, eye shadow, a glittery green, dark red blusher to highlight my cheeks, black eye liner and masscarra followed. I added bright red lippy, all was applied...Read On

8

Fulfilling A Girl's Male Fantasy Part 2

Jenny and her friends have a party with a surprise.

Since our first meeting had gone so well, Jennifer and I started going out together. Other than the fact that in the bedroom I was the "man" only about half the time, it was a fairly normal relationship, apart from possibly being even more open with each other about our desires. One day a couple of months after our first encounter, we were both in her room talking and listening to music. ...Read On

16

Busted by a bud

Caught on home turf.

It's a hot summer day in 1994. Nowhere is a small, fairly poor, rural Illinois town; the kind of town where nobody locks their doors. Summer seems to be an average 19 year old. He goes to a small community college and works on the weekend's. He's kind of quiet and doesn't like to be around his parents. Both parents have jobs where they have to work the night shift. Summer's mom works for...Read On

7

Serving my master part 2

This is part two of how I was transformed into a sissy maid.

  I’m a teenage white cross-dressing sissy: My master is a tall muscle bound black man. After my first encounter with him he told me to come home with him, as we walked to his car he had his hand on my ass. I felt so sexy as he fondled me. When we got into his car he grabbed me by the hair "Here’s the rule from now on I own you you’re my slave and I’m your Master, you will do everything...Read On

12

serving my master part 1

I'm a submissive panty wearing sissy

    My name is Chris I may have a penis but deep down I was born a girl. I have long red hair baby blue eyes a soft shapely hairless body and an overpowering obsession for wearing frilly lingerie. My obsession started at a young age I found a pair of my sisters panties in the bathroom and took them back to my room. I stripped off my clothes and rubbed the dirty panties over my...Read On

17

Fulfilling A Girl's Male Fantasy Part 1

Jennifer has a surprise request for Jack.

"Get undressed," the pretty brunette told me, and I obeyed. She was called Jennifer, we'd met the night before at the rock nightclub, and I'd thought that she looked gorgeous in her goth make up so she invited me back to her place. It turned out that she was eighteen and still living at home, so we locked her door and did our best to keep quiet as we fucked the night away. Now it was noon,...Read On