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Crossdressers Stories

crossdressers

Surprise new beginnings

Pauline finally makes a honest woman of me

It's now 18 months later and quite a lot has happened. First and more importantly my relationship with Pauline was as strong as ever, my past demons now banished thanks to Pauline's intervention. Steven and Gary had got back together and we're back on talking terms which I was genuinely happy for. My body shape had changed, that clinic offer from Pauline? My choice was obvious as I now sported a good looking 34b bust, hai...

Steven

Steven and I become lovers, however a meeting with friends was about to change all that with a surprise revelation from one of them.

The first few months after we went our separate ways was, for me, the most difficult. I'd lost my confidence, my ED raised its ugly head, then the sale of the house fell through so we were still financially connected as we rented it out with at least a steady income. Steven, however, really helped and really looked after me. Slowly my confidence returned as did my erections. He was financially well off so he lavished me w...

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...

Fantasy fulfilled

My friend arranges a threesome

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...

My friend achieves his goal

A night of discovery as my friend turns the tables on me

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 my way...

My first time

My friend takes a chance , one that'll change my life forever

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...

Crossdressing Journey - Tentative Steps

The first taste of fun, whilst wearing nylons

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...

Anonymous

First threesome

My friend introduces me to his more dominant friend

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...

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Anonymous

My continued sissyfication by my friend

My journey into being a submissive slut continues

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...

Anonymous

My first time

Unexpected evening where I accidentally inseminated my friend

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...