There’s a certain level of fun when combining some of my interests – BDSM and crossdressing, in this case. A few months ago, I got to do that when visiting a friend for a little play date. For this, Jennifer wore her slinky little red dress and black heels, and we had fun putting me in various positions on the different equipment for the camera as well as doing some light flogging and other such teasing.
Posing with a stripper pole.
Another pose with the stripper pole, squatting down, with a little upskirt look. I was not wearing my gaff underwear for this session, so this pose shows everything.
One more pose with the stripper pole.
Tied to a St. Andrew’s cross, ready for a little flogging.
Side view of me on the cross.
Sitting in a “fuck swing” that was suspended from a beam above.
Another photo of me in the “fuck swing”.
Locked in a chain cage that was attached to the ceiling.
On a spanking bench, ready to go.
On a different spanking device.
My absolute favorite time, however, was when I was simply handcuffed behind my back and forced to look at myself in the mirror. There’s something about looking at myself when I’m dressed as Jennifer that absolutely turns me on. I was feeling so many pleasurable sensations while my arms were locked behind me. It didn’t matter that I was wearing heels, either – I could have stared at myself all night.
Handcuffed to the stripper pole, staring at the mirror.
Handcuffed to the stripper pole, staring at the mirror, viewed from the other way.
You know, just standing here, handcuffed to a pole.
After a while, we changed my position just a little bit. My arms were released, and I was handcuffed again more directly, without the pole in there. Then a collar with a leash on it was placed around my neck. The other end of the leash was attached to the pole. This was slightly more comfortable, not having the pole in there and all, and it gave me a slight bit of space to move around, though I was still very much restrained.
Standing next to the pole, handcuffed, collared, and leashed.
View from behind of me handcuffed and collared.
Still thoroughly enjoying my predicament.
For some reason, when I play in drag, it intensifies everything for me. Seriously, I love it. I imagine that it’s like how, when I’m watching fetish videos online, I always imagine myself as the captive, and this helps me get into that role a little bit more when I’m actually playing. Who knows.
All in all, a fun time was had by everyone involved.