Cross-Dressing

Author's Note: First story ever! Much like my unlucky protagonist, I’m a 26 year old submissive male from Brooklyn. I’ve been reading BDSM stories most of my life and finally sat down to write one, please let me know what you think! Part One: The Trap Well this certainly throws a wrench into things, Mark thought. He had just found out that his roommate was moving in with his girlfriend, leaving him all alone in a Brooklyn apartment that he could no longer afford. He had only just moved to the city two months ago, after his girlfriend of three years had left him, and he was finally starting to attract some clients as a freelance web developer. Despite being educated and working all through college, he barely had two dollars to rub together after paying for food, rent, insurance, and student loans. Everything else he wound up spending on Vanessa, who seemed to be the only person capable of bringing a smile to his face at the moment. ...

THE DOCTOR The receptionist was a tall, large breasted African-American woman with long braided hair streaked with red and gold. She looked at me like she had never seen me before although this was my third visit to Dr. Weinstein. “I have a 2 o’clock appointment,” I said. “Your name?” “Allen, Jon Allen.” She looked at the computer screen on her desk, flicked a couple of keys before saying “Oh the sissy boy, she will see you at 3.” ...

Author's Note: First time submitting a story, constructive criticism welcome. I tried to keep the paragraphs short for ease of reading as this is a bit long. There are ideas for torturing Thomas more, if people enjoy this story I will get to putting part 2 down ASAP. Also this is a work of fiction, please don’t bring the real world into with comments on the legality of what’s happening. ...

Part I I enjoy dressing as a female. I do it as much as I can. I wear nylons or tights, support panties or girdles, and bra’s regular or long line under my clothes. I have a pair of knee high boots with 4” heels that I wear when I can. I am also into bondage. Every now and then I get a chance to do both. This is the story of one of those times. I had to make a trip from Memphis to Nashville. It was to be an overnight stay. It also was going to be a daring fetish bondage trip. ...

Author's Note: This is a silly little fictional story I wrote back in 2003. Suspension of disbelief will help. Hope you enjoy it. I have been kinky for most my life, experimenting with self bondage at first, then chastity, then cross dressing in a limited fashion. It has really turned me on to be helpless, frustrated, and dressed in soft feminine clothing. There was only one thing lacking, and that was a big thing: someone else to play with. ...

Blah, blah, blah, background, get to the story, right? This is a true account of one of those rare times that things went wrong for me. I’m a planner…I plan…that’s what I do. I seek out what could go wrong before I commit to it and I nip it in the bud. This is proof, though, that when you’re helpless, anything minor, no matter how minor, can be what does you in. As far as planning goes, “good enough” is never good enough. ...

Author's Note: Just some musings from a oversexed mind Last night I finally lived a long time dream of mine. My wife Melody of three years came home from work around 7pm and told me to follow her upstairs. Once we arrived in the bedroom, she laid back on the bed and spread her legs wide for me. She was dressed in a long white light cotton dress with a floral print and a belt cinched at the waist. The dress fell long enough to conceal most of her knee high black shiny leather boots. As I looked down at her beautiful shaven pussy, I saw first that she had not worn any panties, and second that she had been fucked recently. ...

I really do not know where my love of rubber and latex started from. I recall being turned on when I found some ‘top shelf’ magazines all about rubber, Atomage being one. Previously I had been a stocking & suspender man, so I still tend to veer towards rubber stockings and nice clinging underwear rather then voluminous mack’s. Is it the smooth..(yes another magazine title from way back..), appearance of rubber? The touch of it, the encasement of one body, the aroma, or just that it’s a fetish. Well I suppose it’s all of those. ...

Debra stood helpless in the middle of the dungeon. So far the session she was involved in was rather simple and she had not quite figured out where it was going. It was rather exciting but clearly there was much more yet to come. She had arrived on time, dressed as usual. That meant cross dressed wearing normal female street appropriate attire. Of course she knew her Mistress did not like this but then that was part of the whole scene. Her Mistress had ordered her to strip down to her scanties, which she did. ...

Author's Note: This story is based on the vacation I wish I could take. Once Shelly gets home, things really change, but that’s for follow-up chapters! Chapter One It finally happened; my wife left me – on vacation – but not before she took everything I owned and put it all in storage. Well, not everything perhaps, but everything anyone would normally associate with being a man. Of course I agreed to it. I even helped pack all my male clothing and left nothing for an emergency because this was something I had wanted for a long time. ...