Crossdressing

LingerieBoy

The Young Crossdresser Part 2

So after my little adventure at mom and dad's bookstore,the next couple of years were uneventful. I did have sex a couple of times with Phylis,the older lady that was part of mom and dad's swinger group. I knew that I was wanting something more,something was still missing and I kept thinking back to how the guy's cock felt as it spewed cum into my panty covered ass. Now I was 15 and...Read On

Added: 10 Jul 2008 | Category: Crossdressing | Avg Score: 4.6 | Tags:

MichelleB

My Story

 This is my story in a short form of how I became me a 22 year old black gay crossdresser. I've always had gay tendasies from as long as I can remember but at age 17 I met a guy who house I use to walk by after school and we would chat, after a while I told him about me and he said he always thought I would make a cute girl, now he was white and a bit older than me at 30.  After a couple...Read On

Added: 05 Jul 2008 | Category: Crossdressing | Avg Score: 4.73 | Tags: crossdressing   | 5 Comments

SabrinaStarr

A Visit

Husband dresses up for his wife so that they can have a little fun during the weekend

My wife knew of my enjoyment to wear women’s lingerie when we married and over the months that followed our honeymoon she had often wanted to see more of me dressed up.   I always enjoyed these times although they were not as frequent as I would have liked them to be. One Friday, after a rather long and difficult week at work, I returned home and was greeted by a tender hug and a loving...Read On

Added: 14 Jun 2008 | Category: Crossdressing | Avg Score: 4.53 | Tags: crossdressing  wife and husband  oral  strap-on     | 10 Comments

pantyslut

My Parents Friend

Get's Me Hot Every Time I think About It

The year was 1987 and I was home on leave from the military. One particular Saturday night my parents were haveing a get together with some friends so I decided to go out and try and find someone to have fun with. I couldn't decide what to wear until I just decided on what I thought would make me look sexy. I grab my things and head into the bathroom and put on my sexiest black...Read On

Added: 23 May 2008 | Category: Crossdressing | Avg Score: 4.92 | Tags: croosdressing  anal   | 4 Comments

pantyslut

First time with a man

I have been crossdressing since the age of 11 years old. I never really considered myself anything other than straight. Up until I turned 19. I often fantasized about other guys when I was dressed but that's as far as I took it. The year was 1984 and one day I decided to stay home from work to play. I get dressed up in a pair of purple satin string bikini panties,matching bra,black...Read On

Added: 29 Apr 2008 | Category: Crossdressing | Avg Score: 4.52 | Tags: man  crossdressing  anal  oral   | 19 Comments

annabell

A helping hand

Found out by a mature woman

It all started a few years ago. I was dating a girl who was bisexual. So much so that she wanted me dressed as a woman for sex. To begin with I was not sure, but eventually I came round to the idea. It was mainly just some lipstick and perfume. After a few months we split up, but I continued to dress up. One day I decided to venture out as a woman. I lay in bed thinking what I should wear....Read On

Added: 07 Apr 2008 | Category: Crossdressing | Avg Score: 4.11 | Tags: crossdressing  mature   | 8 Comments

Gina

The perfect day...

A t-girl's experience of getting dressed for ACTION!

The perfect day… The time was drawing near. He would have the house to himself! The realisation of a whole 4-month's planning would now come to fruition. It had been a while since he had gone out all dolled up, and now was a fresh opportunity to see his progress as a woman. He had been busy – his make-up collection had swelled considerably, and the addition of several choice pieces...Read On

Added: 29 Jan 2008 | Category: Crossdressing | Avg Score: 5 | Tags: | 3 Comments

SabrinaStarr

A Little Walk

A late night walk turns into a dream come true

I love autumn nights, the air is cool and the weather is still nice enough to allow for some late night strolls to the park and through near deserted streets.   Another bonus is that the nights are longer which means that I could escape the seclusion of my home earlier to enjoy the freedom of the outside while dressed as I so enjoy doing. For this particular outing I had decided to go with...Read On

Added: 18 Jan 2008 | Category: Crossdressing | Avg Score: 4.51 | Tags: high heels  oral sex   | 7 Comments

luvinia

me and my boyfriend

my day with my boyfriend

hi yesterday my boy friend came to my house when i was alone and he had brought a pair of pink salwar kameez and a red silk saree with matching lingerie. when he arrived at home i was very happy as we both were alone for whole night at my house when he came i had just come out of bathroom after having a shower when i was taking my underwear to wear he stopped me and handed the panty he...Read On

Added: 14 Jan 2008 | Category: Crossdressing | Avg Score: 3.27 | Tags: crossdressing  crossdressing sex  cd with boyfriend  

luvinia

s(he) finds her man

story when i replaced my friend at a wedding

My house was not more than 250 meters away from the bus stop where I got down; but the sudden and heavy downpour caught me totally unprepared. Being one those new housing colonies there were no houses or trees where I could take shelter. By the time I reached our new house I was drenched to my skin. My younger sister Putti who opened the door started laughing at my plight. My elder...Read On

Added: 01 Jan 2008 | Category: Crossdressing | Avg Score: 4.09 | Tags: crossdressing  crossdress     | 5 Comments

Monica111192

First Time Out

Crossdressing In Public

 This is a true story about my first time I went out dressed at a club I had been in the closet for years and up until this point only a few people had ever seen me dressed my freind Bill and some guys I went to an adult book store.  I had been dressing for Bill alot in mine and his apartment but I had this erge to go out clubbing dressed I had asked Bill several times but it seemed he...Read On

Added: 31 Dec 2007 | Category: Crossdressing | Avg Score: 4.02 | Tags: crossdressing   | 2 Comments

Monica111192

Mack and Me

Dream Of My friend and I Online

 I am a 36yr old black crossdresser who only came out the closet about four years ago going to cd bars and clubs to dance and so forth but this is about a dream I had reasonly about a guy I've been chatting with online, now we never have met yet but I do know its just a matter of time anyway here is my dream.  I was out for a night of fun in one of my regular clubs dressed for the kill in...Read On

Added: 28 Dec 2007 | Category: Crossdressing | Avg Score: 4.19 | Tags: crossdressing fantasy   | 3 Comments

jjomes

First Time Dressing

Helping a friend find his inner female

A few weeks ago my gay friend Paul phoned and asked if I would go out with him on Friday night. My husband John and I have known Paul for ages and we knew he was getting over breaking up with his long term boyfriend so I happily agreed. John stayed until Paul came round so we could all have a drink together and then he went off with a couple of his mates. After John left we had some more wine...Read On

Added: 20 Dec 2007 | Category: Crossdressing | Avg Score: 3.69 | Tags: gay  crossdressing   | 4 Comments

Kelsie

A Maid Story

Paul lives out his maid fantasy

It had been a long day and Paul was tired.   After a week of traveling and a full day of meetings, Paul was ready to unwind with his wife, Marie.   They were what many people might describe as soul-mates. They were best friends who shared their deepest, darkest secrets with one another and who regularly consulted with one another on a wide variety of topics. Their love life had...Read On

Added: 02 Nov 2007 | Category: Crossdressing | Avg Score: 4.30 | Tags: smoking  spanking  anal sex  maid   | 2 Comments

DrBill

Glimpses of Consequences

Davey's mother tries to teach him a lesson.

GLIMPSES OF CONSEQUENCES By DrBill "HOWA we going to start?" The ritual joke having been followed by the ritual groans, the Housewives of Worthington Acres came to order. The group had evolved from informal visits for coffee and complaining to a neighborhood organization of sorts. While the meetings still tended to be primarily boast and bitch sessions, they also traded useful...Read On

Added: 12 Mar 2007 | Category: Crossdressing | Avg Score: 4.57 | Tags: petticoat punishment  voyeur   | 6 Comments