Party Surprise - First sex as a Crossdresser

This is a work of Fantasy. I hope you enjoy.

Stephanie and I had been married a few years and enjoyed a reasonable sex life. She knew of my dressing and although she didn’t approve she indulged me now and then and we had sex when I was dressed or with me wearing lingerie. I think secretly she was jealous of my legs. She was a petite sexy woman and we were almost the same size but I still had my own stuff that I’d secretly obtained from eBay and op shops.

I didn’t consider myself bisexual, certainly bi curious at least. I liked watching guys stroke on cam and enjoyed the odd bit of cybersex online when I she was at work. I also loved tranny porn or porn where cross dressers were involved. I loved the idea of a cock in panties.

We discussed my “desires” now and then and I did admit that maybe I’d like to feel like a woman one day. We also discussed 3somes but the idea of her having sex with someone else upset me and me having sex even with a guy was like cheating so it was a line I didn’t think I would ever cross.

But I did secretly desire sucking a cock and being anally penetrated. I used dildos and plugs and we even introduced them in the bedroom and Stephanie did enjoy fucking me with her favourite dong.

A friend of ours was having a New Year’s Eve party and as luck would have it was a costume party. I secretly wanted, well hoped, I could get all dolled up and go as a girl. We discussed what we would wear over several weeks and finally Stephanie suggested I go as a woman and she would dress in a tux and go as a man. I feigned resistance but was secretly beside myself.

Over the next few days I contemplated several outfits and with Stephanies permission I decided upon one of her favourite dresses. It was a black slinky, stretch jersey that had a cowl neck and was figure hugging. It wasn’t my favourite satin but it felt diving to wear. Teamed with seamed stay up stockings and black 6 inch heels it looked demure and sexy yet elegant. Stephanie and I went shopping for lingerie and she selected the most divine red and black satin G string panties and a red and black matching bra, together with a red satin under bust corset to improve my figure. I stopped short of trying them on in the store but god I wanted to.