Crossdressers Stories

I'd met Sophia online almost a year ago, at that time I was totally unaware that she'd been enjoying some of my stories I'd posted online. She described herself as a size 14 to 16 and a widower of several years Yet again, I'd met someone older than myself, almost 15 years my senior with the same passion for 1960’s and early 70’s corsets , girdles and what I'd describe now as vintage nylon slips, the mention of other more...

So I had pulled over in to a well known services after 10pm at night, I had parked at the top lane at the top of services and really enjoyed stripping off all my male clothes and now dressing up in all sexy in stockings suspenders, French Lacy knickers, bra, blouse , skirt boots and wig plus I love doing my make up I’m sure some person spotted me in a black car, he then came and parked in my row, so in return I went and g...

After indulging my fantasies of nylons, lingerie and heels on my own for some time, I decided to be brave and see if I could be ‘used’ whilst dressed in my girly clothes. I’m not a convincing CD, so I wasn’t going to hit the streets looking for attention, so I decided to see what happened on one of my business trips, which seems to be a standard approach for discreet crossdressers. As I travel for work, I will often bring...

Part 3 After that memorable night where my friend finally dominated and sissified me, we now met on a regular basis and we're more daring with each other, well mainly him!. By now my then girlfriend had moved away to university so I had ample free time to be Christine and made the most of it dressed when at home, it felt so liberating and sensual. My friend knew this and made full use of my new sexual freedom. I got a tex...

Part 2 After that incredible night with my friend, I tried to process it all in my head. I wasn't gay? I had a girlfriend and enjoyed sex with her but also enjoyed what I did that night with my friend. For a couple of days I avoided my friend, mainly out of embarrassment but that didn't last long as he had sensed this and suggested we meet to clear the air so to speak down the local coffee shop. Invitation accepted I made...

Although this happened a long time ago I'll never forget my first experience so I'll write this as best as I can remember, I hope it invokes memories of your first experiences. This happened unexpectedly when after a night out on the town with my long time friend I crashed at his place. I'd sort of known for a while he might have gay feelings, I wasn't sure if he knew that I liked wearing women's clothes but I guess somet...