Crossdressing

missunderstood98

My First Trip Out of the Closet

Crossdressing fun way over the edge

  I have wanted to write this story for many years but I hesitated to do so out of my fear of the unknown.   Since moving to Florida , I have pretty much been on my own for the first time in a long time. Let’s just say that now that I am older, I’m bolder! I no longer care who knows my sexual interests. It’s funny, because everyone I currently see understands my desires...Read On

Added: 13 Jan 2009 | Category: Crossdressing | Avg Score: 4.7 | Tags: walking on the wild side  

missunderstood98

The Rendevous

An experience on the WILD SIDE!!!

The Rendezvous   He called Saturday night just after ten. His wife was being admitted and they may induce her labor. He told me how much he missed me and how needy he was for my warm, wet mouth. I told him to be patient. His responsibility was to take good care of business. He told me that his wife was fine and that he hoped to see me on Sunday. We hung up.   I...Read On

Added: 09 Jan 2009 | Category: Crossdressing | Avg Score: 4.47 | Tags: leather and lace   | 2 Comments

PolaLeonor

Doing the landlord {Do It In Mexico (2) }

Make believe husband (cont. )

...........I got home from  my first day gone public fully dressed as a lady.         It was late in the afternoon,    I filled my bathtub with warm water ,     put in scented bathoil in it ,   laid in there for an hour and 20 min. Thinking of that day in town , when I was getting fucked by  FRANKLIN . Just thinking of that whole scenerio made me horny . I started slightly fingering my...Read On

Added: 05 Jan 2009 | Category: Crossdressing | Avg Score: 4.75 | Tags: landlord  

barryboi

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

Added: 02 Jan 2009 | Category: Crossdressing | Avg Score: 4.52 | Tags: barry  gag  cock  panty  

Teresab

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

Added: 29 Dec 2008 | Category: Crossdressing | Avg Score: 4.19 | Tags: crossdressing   | 1 Comment

larkin3445

Second Encounter

My second encounter with Chris

Second Encounter   It had been a couple of weeks since Chris and I had first met when he called me.   He had been so sweet the day we first met.   I had been very nervous when my friends had left me tied to the pillar and alone with him.   But, when he untied me, took my hand and led me to the bedroom, he had been so gentle.   He treated me so much like a woman.   I...Read On

Added: 04 Dec 2008 | Category: Crossdressing | Avg Score: 5 | Tags: bondage crossdress   | 4 Comments

PolaLeonor

Do it in Mexico

Make believe husband

I live by the border to Mexico. I am a very low key cross-dresser . I moved out of my parents house at the age of 20 . Since I was financially O.k.. , like had a great job and was very independent. I was able to buy myself everything I wanted for cross dressing. When  I turned 23 years old ,I decided that I wanted to go to Mexico and rent a house or apartment out there as a retreat or...Read On

Added: 03 Dec 2008 | Category: Crossdressing | Avg Score: 4.74 | Tags: cheating   | 3 Comments

Rachelcd

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

Added: 15 Nov 2008 | Category: Crossdressing | Avg Score: 4.5 | Tags: | 2 Comments

duke1933

Halloween

Boys will be boys

This story is not to be copied or moved to another web site Well here it is Halloween and I have an idea to dress up with my older bro and take the two younger bros out to trick or treat. When the big night came I got some of my sisters things to dress up in. I took all I needed to look just like her with the panties bra and skirt and blouse with a short jacket over it all. I must say...Read On

Added: 12 Nov 2008 | Category: Crossdressing | Avg Score: 3.89 | Tags: hot halloween for two   | 1 Comment

LingerieBoy

Been A Long Time

Once I got married I pretty much gave up my crossdressing lifestyle to lead a more "normal" life.You know,settle down,have a couple of kids. I was a happily married man with two kids,what could be missing? Well one day while at work,I was on the internet and stumbled onto a crossdressing website,and all kinds of memories came rushing back to me. The feeling of sexy panties,bras...Read On

Added: 06 Nov 2008 | Category: Crossdressing | Avg Score: 4.59 | Tags: crossdressing  glory holes  cum  swallow   | 7 Comments

simonelovesyou

Keep Silent or Be Caught

Remember be silent or be caught!! Last year my girlfriend got asked to be a bridesmaid. She of course sed yes, this ment she would have to have a bridesmaid dress. Now all cross-dresser has a dream of wearing a wedding or bridesmaids dress and i couldn't wait for her to get it and try it on. The dress was a gorgeous white satin dress from Bhs. The top was strap-less and had a...Read On

Added: 06 Nov 2008 | Category: Crossdressing | Avg Score: 3.83 | Tags: crossdressing  self bondage   | 2 Comments

larkin3445

First encounter

This is about my first sexual experience with a male while en femme.

  I had been cross dressing for years but only in private.   I had also had a thing for bondage for a long time.    A couple of years ago, I met two other cross dressers who were into bondage.   We had been getting together every couple of months and   playing bondage games with each other.   We would take turns tying each other up and taking photos and videos.   But, it was always clear...Read On

Added: 28 Oct 2008 | Category: Crossdressing | Avg Score: 4.29 | Tags: bdsm crossdressing man bondage sex   | 1 Comment

pantyboy4u2do

GurlsOut

Having been into womens clothing since an early age,as I got older I often wondered about going out dressed up and hitting a local bar as a girl. Well I finally got my chance back in 1984. I was in the Air Force stationed in North Carolina and had already made a connection with a local man down there and we had sex on a pretty regular basis. He knew of my desire and one night we decided...Read On

Added: 13 Oct 2008 | Category: Crossdressing | Avg Score: 4.34 | Tags: | 4 Comments

Chrissy_CD_slut

Dressed Up and Used

Young Crossdresser gets Fucked again

     This is a continuation of my first story "MY First Time in a Dress".  I love reading your comments, enjoy!      I avoided Dan for the next few days by playing sick.  I was not ready to go over to his house again yet.  My ass was so sore the next day I had to have some relief.  I was still having a hard time comprehending what really happened.      I finally went to his house...Read On

Added: 26 Sep 2008 | Category: Crossdressing | Avg Score: 4.77 | Tags: crossdressing  anal  reluctance   | 12 Comments

Chrissy_CD_slut

My First Time in a Dress

How I Became a Crossdresser

PART-1 When I was younger I used to go and stay at my grandmas house during the summer. It was a small country town with about 15,000 people. She lived on a quiet street and there was only a couple of other kids close to my age. I used to go and hang out with one guy, Dan who was about 3 yrs older than I and his sister, Pam who was my age. Dan and I used to go mess around everyday....Read On

Added: 05 Sep 2008 | Category: Crossdressing | Avg Score: 4.76 | Tags: crossdressing  oral  anal  creampie   | 24 Comments