Crossdressing

Jess_cd

Caught by a neighbour

I've secretly been crossdressing from a young age. In my late teens, around 17, I became more adventurous. maybe because I was enjoying it more. At that age I was very slender, had long dark hair as well has having a naturally smooth and hairless body. My brother and sister were both at uni and my parents would work a lot of the time meaning I was left home alone quite a lot. I would "borrow"...Read On

Added: 07 Oct 2011 | Category: Crossdressing | Avg Score: 4.62 | Tags: dressing  neighbour   | 14 Comments

Oldphart

My day as a slut

Pleasing my Mistress

Again this is a true story from a few years ago. I had met a lady online, from a town about 40 miles away, we chatted, cammed and exchanged phone numbers. We texted and talked and eventually met, not quite in the way we wanted, but that's another story. We had met a couple of times and the opportunity arose to get her alone for a day at her house, so we planned something a bit...Read On

Added: 03 Oct 2011 | Category: Crossdressing | Avg Score: 4.53 | Tags: crossdressing  anal  spanking  oral   | 2 Comments

Oldphart

Early one morning

A surprise while walking

I work 12 hour shifts, days or nights, so I'm up at all hours. One morning, I was up at 4am to start at 6.30, so I had a quick cuppa then took the dog down to the park. It being September, it was very dark and very quiet. As I walked round the path, letting the dog do her business, I noticed a woman sitting on a bench under a street light. As I approached her, she said good morning, I...Read On

Added: 18 Sep 2011 | Category: Crossdressing | Avg Score: 4.64 | Tags: crossdressing  oral  bisexual   | 6 Comments

AshleyBarnes888

The Pageant

An unusual end-of-summer beauty pageant spices up a young man's relationship

I was happy to finally get a job, a decent job, at Sweeney, Burke, and Garcia, a law firm in Savannah, my hometown of about 25 years. The economy was still hurting and I was days away from making a decision to move to another city, so I was grateful for the opportunity that came my way to remain in my beloved city. I was hired as a temporary executive assistant for one of their...Read On

Added: 18 Sep 2011 | Category: Crossdressing | Avg Score: 4.67 | Tags: crossdressing  straight sex  anal  transformation   | 5 Comments

AshleyBarnes888

The Birth of Amber Lynn

A man plays dressup and realizes it has been the missing ingredient in his sex life

I had been dating Suzanne for about two months. She was a gorgeous woman I met while working as a computer technician at Aritech Computing. A successful sales consultant for the company, she made them a lot of money through all her sales. One look at Suzanne, and men would open their wallets to buy whatever new gadget or software she touted as being new and improved. As such, she in turn made...Read On

Added: 12 Sep 2011 | Category: Crossdressing | Avg Score: 4.92 | Tags: crossdressing  oral sex  anal sex  straight sex   | 13 Comments

AndicdnSC

Andrew to Andrea - Part 4

...the next few steps...

Chapter 4 It seemed like the time would never arrive. I watched the clock limp around the dial for the last hour between 5 and 6, but finally the time came…the time to go home. I still felt the pressure, not unpleasantly, of the plug installed by my wife yesterday, and still had the memories of the sensations that I felt each time she activated it…again, not unpleasant. Finally, I had the...Read On

Added: 08 Sep 2011 | Category: Crossdressing | Avg Score: 4.83 | Tags: crossdressing  straight/bi   | 3 Comments

AshleyBarnes888

A Night Out with Suzanne

Young man decides to support his new girlfriend's fetish and finds out a lot about who he really is

I hadn’t seen Suzanne in 15 years. She was a member at the country club where my father had worked and, despite living in separate towns, we saw each other every summer. We enjoyed each other’s company and we spent most of our days playing tennis and swimming at the pool. When I graduated from college and went into the Army, the thoughts of Suzanne were just faraway memories. Then,...Read On

Added: 07 Sep 2011 | Category: Crossdressing | Avg Score: 4.96 | Tags: crossdresssing  oral sex  straight sex  dressup  makeover   | 21 Comments

lildifferent

A Fantasy to Remember

Halloween was rapidly approaching and my girlfriend of 2 years was planning something big. She had been a stripper for 10 years and was as kinky as they come. She and I had done a lot, so only a few of her fantasies were left unfulfilled. She had already had women and men, group sex, bondage, been a submissive and a dominate. We had a no holes barred policy. I could have any hole I...Read On

Added: 20 Aug 2011 | Category: Crossdressing | Avg Score: 4.89 | Tags: crossdressing  anal  group sex  bisexual   | 5 Comments

Willingsubmissive

A Fantasy Come True

My wife and I went on a four day vacation to Charleston to enjoy the sights and especially to enjoy the nights. Our first night there I was no sure how it would go. I was wandering if my wife could really get in the role of being a Dominatrix. Would she really enjoy having DD as her Slave? Could my wife become the Dominatrix that I want and need? All my questions were answered that night. ...Read On

Added: 14 Aug 2011 | Category: Crossdressing | Avg Score: 3.83 | Tags: submissive  watersports  domination     | 4 Comments

AndicdnSC

Andrew to Andrea - Part 3

..the next step...

 BRRRRIIIIIIINNNGGGGGGGGGG!!!!!! The alarm clock that my wife and I mockingly referred to as “Baby Ben” sounded off and pulled me from what I first thought was a great dream. As my senses slowly came online, I could feel my hand laid over my naked wife’s breasts and that I wasn’t in my usual gym shorts and t-shirt. I was surrounded in silk, and it was not unpleasant, but it was a floor...Read On

Added: 04 Aug 2011 | Category: Crossdressing | Avg Score: 4.82 | Tags: crossdressing  straight/bi   | 5 Comments

Monica_2611

My First Cock

This story is my first experience with a man dressed up as Monica, my slutty alter ego. Like, most Cross Dresser’s, I started young. I grew up with plenty of women, all family members, and I remember trying on panties and strutting around at a very young age. I especially, liked wearing my Aunt’s business suits, women in business clothing has always been hot for me. However, like...Read On

Added: 01 Aug 2011 | Category: Crossdressing | Avg Score: 4.94 | Tags: crossdressing  young and older  college  blowjob   | 13 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

AndicdnSC

Andrew to Andrea (Part One)

Andrew is about to really see the other side

Hi, I'm Andrew; at least I was Andrew full time until about a month ago. I have always been fascinated by lingerie: its feel, its appearance, how it just makes a body look that much more sexy. Like most curious types I started young (at sixteen, so not all that young), swiping what I could from my sisters or cousins when I could and squirreling my prizes away until I could find time for them....Read On

Added: 29 Jul 2011 | Category: Crossdressing | Avg Score: 4.53 | Tags: crossdressing  straight/bi   | 9 Comments

robbrownn

My Day in Panties

The day I spent at work in my hot panties

I'm a 21 year old sales rep for a drinks supplier. I'm tall and skinny, and love little sexual secrets....today was just another day in this secret life. The alarm clock rang out like a drill sergeant screaming at his soldiers. 6 AM and it was already light outside. It looked like it would be yet another clear sunny hot summers day and I awoke laying naked in my bed. It appeared that my...Read On

Added: 26 Jul 2011 | Category: Crossdressing | Avg Score: 4.58 | Tags: crossdressing  masturbation   | 4 Comments

Jingle

I Still Love You Tomorrow

How could she be so forgiving? I didn't understand... Caught with the evidence of my secret on my face, my body, and in my hair, I was frozen by her stare as she stood in the bedroom doorway, eyes wide as teacups. “Oh,' she said, too shocked for anything more. I had lied to her! I wouldn't have blamed her if she had left me in that instant, but she stayed. Why? How? We sat together...Read On

Added: 22 Jul 2011 | Category: Crossdressing | Avg Score: 4.88 | Tags: toys  strapon  lesbian   | 5 Comments