Crossdressing

pam1950

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

Added: 20 Nov 2009 | Category: Crossdressing | Avg Score: 4 | Tags: lingerie  domination  crossdresser   | 2 Comments

Chrissy_CD_slut

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

Added: 20 Nov 2009 | Category: Crossdressing | Avg Score: 4.56 | Tags: gay  anal  cum   | 8 Comments

philippasubmaid

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

Added: 19 Nov 2009 | Category: Crossdressing | Avg Score: 3.92 | Tags: crossdressing  dominant women  bondage  chastity   | 1 Comment

philippasubmaid

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

Added: 18 Nov 2009 | Category: Crossdressing | Avg Score: 3.43 | Tags: crossdressing  female domination  bondage   | 2 Comments

SashaCD_ThongPanties

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

Added: 13 Nov 2009 | Category: Crossdressing | Avg Score: 4.85 | Tags: thong  shower  crossdressing  anal  creampie     | 2 Comments

Chrissy_CD_slut

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

Added: 12 Nov 2009 | Category: Crossdressing | Avg Score: 4.58 | Tags: crossdressing  masturbation     | 7 Comments

LucyCoxx

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

Added: 28 Oct 2009 | Category: Crossdressing | Avg Score: 4.45 | Tags: dirty girl   | 3 Comments

ThinkKinkyThoughts

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

Added: 28 Oct 2009 | Category: Crossdressing | Avg Score: 4.81 | Tags: cross dressing  strap on   | 4 Comments

Teresab

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

Added: 26 Oct 2009 | Category: Crossdressing | Avg Score: 4.5 | Tags: crossdressing  feminization  sissy   | 7 Comments

Pudmeister

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

Added: 25 Oct 2009 | Category: Crossdressing | Avg Score: 4.38 | Tags: | 1 Comment

summer1979

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

Added: 18 Oct 2009 | Category: Crossdressing | Avg Score: 4.6 | Tags: coworker  crossdressing  drinking   | 5 Comments

Pudmeister

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

Added: 04 Oct 2009 | Category: Crossdressing | Avg Score: 4.56 | Tags: crossdressing  bisexual  

Pudmeister

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

Added: 27 Sep 2009 | Category: Crossdressing | Avg Score: 4.8 | Tags: crossdressing  big breasts  anal   | 3 Comments

Pudmeister

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

Added: 21 Sep 2009 | Category: Crossdressing | Avg Score: 4.9 | Tags: crossdressing  oral   | 5 Comments

shazstoned

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

Added: 05 Sep 2009 | Category: Crossdressing | Avg Score: 4.11 | Tags: crossdressed slut  oral  drunk.   | 10 Comments