[F]irst ti[M]e getting pegged

I’ve always enjoyed a bit of anal play, and had wanted to get pegged for a while. I connected with a woman online, we met for a drink and then back to my place for some excellent but fairly vanilla sex.

After that night we kept texting, and got into our fantasies. She told me she was into receiving anal and I confessed that so was I – luckily she sounded really into the idea and even owned a strap on already.

Next time we arranged to meet she asked me if she should bring anything? I responded “wine?” and then quickly added “and your strap on…?” To which she responded with a 😈.

On the night she came over to mine, we shared that bottle of wine (a nice red), chatted a little, and then found ourselves making out on the sofa.

I suggested we move it to the bedroom and she said she’d meet me there. I assumed she just wanted to use the washroom, so I thought nothing of it and went to wait.

I was sitting on the edge of the bed when she came in, wearing a lacy black bra and panties, thigh highs, and a harness containing a realistic looking dildo!

My first time with a t-girl [TM]

At the time this happened, I was a 32 year old guy. I’d just moved to a new city and didn’t really know anyone yet, so I signed up for various dating and hookup sites. I’d always been a little bit curious about the idea of meeting a t-girl, so I ticked that box while creating my profile for one site.

I exchanged messages with a few GGs, even met one of them, until one day a message from “Shari”. She was a t-girl, my age with a slim body that looked great in the outfits she was wearing in her photos. I replied right away of course!

We exchanged a few messages and pics, getting to know each other and one day she asked if I’d like to come over? She lived nearby, so I walked over stopping by the liquor store to pick up a bottle of red wine.

I arrived at her apartment and she buzzed me in. I knocked on the door and was greeted by Shari looking sexy in a short dress, fishnet stockings and sky-high heels. She greeted me with a hug and a long, deep, sensual kiss, before taking my coat and showing me where to find a corkscrew.