Crossdressing

CindyUSA

I did not know I had a disorder

Bi man dressed for the first time to please a man

I did not know I had a disorder CindyUSA I am not sure if I should be embarrassed, ashamed, depressed about my condition. I do not look unwell; does it show? I look normal to my wife, family and co-workers. I wonder if they know about my disorder. If they had, why did they not tell me? Like most illness, they start slow and build up and suddenly, bang; right between the eyes it hits...Read On

Added: 26 Mar 2012 | Category: Crossdressing | Avg Score: 4.67 | Tags: cd  xdresser  oral  anal  bisexual   | 7 Comments

cdbottom2

Telling Mom I'm A Crossdresser Part 8: Bus Driver's and Cops

Part 8 enjoy and please comment at the bottom ;)

My mom and I spent the next few days practicing and exercising with the stripper pole until we felt confident and extremely sexy while doing it, which I have to admit did not take long. One night I came home late from my part time job I had at a local restaurant and took the bus home. I didn't have a car because I hadn’t decided on what car I wanted to get yet and what I could afford. I...Read On

Added: 20 Mar 2012 | Category: Crossdressing | Avg Score: 4.87 | Tags: crossdressing  oral sex  anal  bus driver  police officer   | 4 Comments

cdbottom2

Telling Mom I’m A Crossdresser Part 7.5: Amateur Pole Dancers

I thought I would try something a little different and involve more teasing to my story. enjoy :)

After our time at the spa, I spent a lot of time in my room trying out all the new sex toys we got from Richard and Monica. They were all exciting in their own ways and I came so much with each one. Some vibrated, some went deep and some felt good stretching my ass wide. The feeling of all the sensations I could get from my new plastic and electric friends were amazing and found myself...Read On

Added: 18 Mar 2012 | Category: Crossdressing | Avg Score: 4.64 | Tags: crossdressing  pole dancing  teasing  masturbation  toys  milf  voyeur   | 3 Comments

rushman1uk

The feeding of sissy

I hold a prominent position in a world wide business firm and make a six figure salary and had been divorced for several years. I met Wendy through a newspaper add in the singles columns, she was a knockout looking gal. We dated for some time and she moved in with me. One night when we were out having drinks she ask what my deepest secrets were. She would share hers with me in return if I...Read On

Added: 11 Mar 2012 | Category: Crossdressing | Avg Score: 3.32 | Tags: crossdressing  wife lovers   | 5 Comments

cdbottom2

Telling Mom I'm A Crossdresser Part 7: The Spa

Missy and his mom go to a spa and meet some new friends.

I could barely sit for days after Mistress Keri thoroughly tanned my hide and I had to take almost a week off so that I could heal. My mom knew this to and said we should go on a “girls” weekend to a spa for cross dressers and women, she also said that since it was for others like me then I could spend the entire trip as Missy. I loved that idea and hurried upstairs to pack Missy’s bag....Read On

Added: 05 Mar 2012 | Category: Crossdressing | Avg Score: 4.83 | Tags: crossdressing  anal  oral  exhibitionism  group sex  mature  toys   | 7 Comments

cdbottom2

Telling Mom I'm A Crossdresser Part 6: Missy and Mistress Keri

Missy has her first BDSM experience. Plz rate and comment

Up until now, I have enjoyed my time as Missy. My mom had kept me busy with clients and we pulled in a lot of extra income and I was able to experience a lot of different fantasies, However I had not had the chance to try anything involving BDSM, or not yet at least. One day I came home from mowing the lawn for an elderly woman when I walked in the door to find my mother smiling deviously at...Read On

Added: 03 Mar 2012 | Category: Crossdressing | Avg Score: 4.72 | Tags: crossdressing  anal  straight sex  bisexual  spanking  bdsm     | 5 Comments

hrny4cok

Taking Control

Wife busted me doing some of my favorite things and then took control with some role reversal

* this is a story of how my wife busted me doing some of my favorite things and then took control of the situation with some role reversal to satisfy both her and my hidden desires - enjoy! * It was one of those rare days when I was working from home and my wife had plans to be out running around with a couple of girlfriends for most of the day. Work had been dragging me down and I was...Read On

Added: 02 Mar 2012 | Category: Crossdressing | Avg Score: 4.79 | Tags: panties  stockings  strap-on  wife  femdom   | 8 Comments

cdbottom2

A Hotel With Candy

originally an audio story however became a short story. plz rate and comment.

I got out of bed and looked at my sexy green camisole with bright pink fishnets, bra and panties that I liked to sleep in after I had just spent the night masturbating with my favorite dildo. I looked back at my nightstand to find it was still beside my pillow where I had left it the previous night and stilled wrapped in a condom all sticky with my favorite lube, strawberry flavored. I...Read On

Added: 28 Feb 2012 | Category: Crossdressing | Avg Score: 4.8 | Tags: oral  anal  first time  spanking  crossdressing   | 7 Comments

cdbottom2

Telling Mom I’m A Crossdresser Part 5: Movie Night and Gangbangs

5th installment of Missy, Plz rate and comment. :)

I had decided to take a few days off from being Missy after Stan and Roger had left and my mom and I were finished with our little girl time. I spent the next few days just continuing with life as normal except for the throbbing pain in my asshole and my cock from the 3 days of constant sex. I couldn’t stop thinking about all the things I had done as Missy and all the kinky fetishes I...Read On

Added: 26 Feb 2012 | Category: Crossdressing | Avg Score: 4.91 | Tags: crossdressing  anal  oral  gangbang  milf  exhibitionism  group sex   | 3 Comments

cdbottom2

Telling Mom I’m A Crossdresser Part 4: Repeat Business and Roleplays

4th installment of Missy :) please rate and comment :)

When my mom and I had gotten home, I immediately ran into the house to take a shower and change as quick as I could. I re-shaved my entire body and removed my makeup so that I could start from scratch and apply it again. Once I was finished with my makeup, I see a new outfit laid out on my bed. This was a cute nurse outfit with a short tight skirt that barely covered my ass. It was also...Read On

Added: 25 Feb 2012 | Category: Crossdressing | Avg Score: 4.85 | Tags: crossdressing  roleplay  anal  oral  toys  group sex   | 7 Comments

cdbottom2

Telling Mom I'm A Crossdresser Part 3: Missy's Weekend

Part 3 of my Missy series :) enjoy and please rate and comment.

One day while watching T.V, my mother had come in and told me Missy’s services had been requested for the entire weekend and we needed to go shopping. I smiled as we got into the car and went to the store to buy lots more sexy clothing for me to play in. After we had bought all the clothes and makeup needed for the weekend, my mother and I went home so that she could give me the details of...Read On

Added: 22 Feb 2012 | Category: Crossdressing | Avg Score: 4.71 | Tags: anal  oral  bisexual  group sex  straight sex     | 5 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: 4.84 | Tags: crossdressing  glory hole  anal  oral  milf  toys  masturbation   | 10 Comments

cdbottom2

Telling Mom I'm A Crossdresser

A story of me being open with my mom as a crossdressing slut andher becoming my pimp. Plz comment :)

When I was younger, my dad had passed away leaving only my mom and I. She is 45 years old with long brown hair, bright green eyes and stood about 5'10" in height. She is also a fairly busty woman with a 30DD chest with about 35" hips and in pretty good shape for a woman her age. I had been crossdressing for a few years and my mother had caught me a few times wearing her clothes. The first...Read On

Added: 19 Feb 2012 | Category: Crossdressing | Avg Score: 4.83 | Tags: crossdressing  anal  oral  condom  toys  spanking  first time   | 13 Comments

Jess_cd

A new friend

As I had a nice, big empty house I did what any good 17 year old would do. That first weekend I had a massive house party! I took a night off from dressing up and invited everyone I knew and when it came to the big night there were plenty of people, including a few I didn't know. I chatted to people and made new friends, sharing drinks and having fun. There was one girl there in particular...Read On

Added: 16 Feb 2012 | Category: Crossdressing | Avg Score: 4.76 | Tags: crossdressing  straight   | 3 Comments

cindytranee

My First Boyfriend Part Five

I step out on my boyfriend and end up getting gangbanged

Things had pretty much gotten back to normal after our wildweekend a week or so before. My boyfriend Steve and I had our unofficial “honeymoon” where I had dressed in a wedding dress and we made love. I had been out dressed as a girl for the first time and had gone to a party where I sucked off a bunch of guys for money. Steve and I had taken two of those guys home with us and they all banged...Read On

Added: 08 Feb 2012 | Category: Crossdressing | Avg Score: 4.57 | Tags: oral  anal  gangbang   | 2 Comments