Crossdressing

sarahjane

my discovery

my story of becoming a crossdresser

Here are some stories about my sex life and exploration of who I am. Before I started cross-dressing, I fell in love with high heels, mainly cumming in high heels. When I was younger, my parents used to have a large walk-in wardrobe and when they would go out at night I'd search for my dads porno mags. One night when I was reading some mags and my parents were out, I got a bit too excited...Read On

Added: 27 Jul 2010 | Category: Crossdressing | Avg Score: 4.69 | Tags: dress  heels  cum  swallow   | 4 Comments

AndicdnSC

Andrew to Andrea - Chapter 2

Andrea's first small steps.

In all honesty, I should have been mortified by the events of the past few minutes, but I wasn’t…I was excited. I walked into our bathroom and set up the steamiest shower that I thought my skin could handle. I grabbed for my body wash, but realized the scent might be too masculine, so I set it back and grabbed my wife’s. It had a slight scent of vanilla and had a couple of butters and oils...Read On

Added: 31 Jul 2011 | Category: Crossdressing | Avg Score: 4.8 | Tags: crossdressing  straight/bi  role reversal   | 6 Comments

germanwulf40

Becoming Vanessa, Part I

After catching her boyfriend cheating on her, Amelia decides to use her evidence as leverage.

It had been a long day for Amelia and her live-in boyfriend, Victor. They had just moved into a new town, and finally had all their boxes in their new house. Nothing was unpacked yet, save for their home computer, which Amelia insisted on getting hooked up straight away. "I don't see what the big rush is," said Victor, as he turned on the computer. He sat comfortably in their...Read On

Added: 26 Jun 2011 | Category: Crossdressing | Avg Score: 4.86 | Tags: crossdressing  feminization   | 5 Comments

DeedraCd

Halloween Trick or Treat Surprise

Dan and Susie go to a Halloween costume party Susie has him dress as a women and changes him forever

Chapter 1 –Susan Charity Event To my surprise Susie my wife of 15 years comes home from one of her many business trips. She is all excited about a Halloween costume party fund raiser, for non profit that supports women studies. The invitation states, the best couple for this evening will receive a free weekend in Bermuda. She wants’ us to go as couple switching genders.  Let me...Read On

Added: 24 Oct 2012 | Category: Crossdressing | Avg Score: 4.97 | Tags: first time  panties  crossdressing  t-girl  anal  transformation     | 26 Comments

Km44

Wife's Crossdressing Fantasy

My journey from boy to man to woman

This is a work of fiction. Any resemblance to persons or incidents is coincidental. My adventure began while I was a senior in high school. My mother took me to the dentist. It was late afternoon and shortly after I was called into the examination room the receptionist and assistant went home. The dentist then closed the door of the room we were in. He walked over to me and started making...Read On

Added: 29 Oct 2012 | Category: Crossdressing | Avg Score: 4.81 | Tags: crossdressing  wife   | 9 Comments

cdbottom2

Telling Mom I'm A Crossdresser Part 2: The Adult Store

Missy goes out and meets her first gloryhole. Please comment and rate all of my stories. :)

I awoke the next morning a little groggy as I slowly recalled the events that had taken place last night. I rubbed my body up and down feeling how the latex had now become a little sticky and how my ass and cock were still sore from the pounding I had taken. I read the note again left by my mother and decided to make breakfast as I was for when she arrived.   It was just past 9am when I heard...Read On

Added: 20 Feb 2012 | Category: Crossdressing | Avg Score: 4.83 | Tags: crossdressing  glory hole  anal  oral  milf  toys  masturbation   | 10 Comments

ssuzie

the summer I became Suzie

this is my fantasy

I was 18 years old and taking estrogen for about two years. As my ass and tittles started to grow my desire to dress up became all consuming. I wore sexy panties to school everyday and the excitement about getting caught, grew as well. I was very tiny for my age and picked on by the jocks at school regularly. I'm 5foot 5inches tall, with long brunette hair and blue eyes. I had no body hair and...Read On

Added: 23 Jun 2011 | Category: Crossdressing | Avg Score: 4.81 | Tags: oral  anal  crossdressing    

cdbottom2

The Slut Within part 2

part 2 of the slut within and if you like it PLZ comment :) enjoy!!!

As I continued on my knees, I felt my little thong riding up my tight little butt. My skirt got in the way of spreading my legs and my tube top and my skin was all sticky with cum. Thankfully, I wouldn’t be wearing any of this much longer. Their watching eyes so aroused my slutty nature. I took off my tube top and skirt leaving my fishnets and six inch heels. I also wore a black thong and...Read On

Added: 18 Jul 2011 | Category: Crossdressing | Avg Score: 5 | Tags: anal  exhibitionism  group sex  voyeur  bdsm  fetish  interracial   | 8 Comments

irishfella

A Valentine's day I will never forget

I awaken on a early Valentines day when I heard the sound of the the doorbell. I had to get up because I was an only child raised by my single mom who was in work. I usually sleep in some comfy panties without my mom knowing but only if she will be in work the next day. Anyway I put on some jeans and a t-shirt to open the door. When I opened the door I noticed a box on the ground which I took...Read On

Added: 16 Jul 2012 | Category: Crossdressing | Avg Score: 4.21 | Tags: incest  anal  strap on  valentines day   | 5 Comments

simonelovesyou

Luck ran out

Everybody runs out of luck!! There i was again wearing my G/F's bridesmaid dress with the 4 inch wedges, bra, thongs and stockings this time. While wearing this wonderful outfit i yet again decided to tie myself up while everyone was out of the house. but this time i put myself into a tight hogtie using cable ties, with a realise mechanism of sizzors. So there i was enjoying the feel...Read On

Added: 07 Apr 2009 | Category: Crossdressing | Avg Score: 3.65 | Tags: | 3 Comments

LisaLeeCD

Loverboy Ricky

Nasty sex with my loverboy Ricky

It’s been some time since I wrote about my crazy life as a slutty crossdresser so with some free time right now I thought I might tell you about Ricky, one of my early boyfriends when I was a teenager….   Ricky moved into our neighborhood when I was 17 and he was 18 and I had a crush on him right away. He was so damn good looking with dark brown hair, brown eyes and strong...Read On

Added: 24 Jul 2009 | Category: Crossdressing | Avg Score: 4.48 | Tags: crossdressing  anal  gay  first time   | 9 Comments

ChelseyR

In Wonderland, Pt. 2

To recap, our protagonist didn't want to dress up for a halloween party, so his girlfriends decided it was time he joined in the fun. They styled his hair, did his makeup and put him into an 'Alice' dress. However, the disguise worked a little too well, as Chris Smith has taken 'Tilly' back to his house after a passionate kiss on the street corner... Chris put his key in the door...Read On

Added: 08 Nov 2010 | Category: Crossdressing | Avg Score: 4.76 | Tags: crossdress  alice  schoolgirl  blowjob  humilation   | 7 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

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

baldie

My First Time

Fist time oral

This a fantasy of mine and my first story that I am submiting. For a long time I had thought about oral sex with another man. I was married a few times and it never really satisfied me completely, I loved sex with them but I longed for sex with a man. I had wondered what it would be like to find a man looking like a woman, I talked to female friend and she helped me to dress up like a sexy...Read On

Added: 05 Dec 2010 | Category: Crossdressing | Avg Score: 4.88 | Tags: oral  gaymale  crossdressing   | 6 Comments