My Evolving Transition – Ch. 02 - Sex Stories

My Evolving Transition – Ch. 02

The Party:

It now had been six months since Tiffany introduced me to her strap-on. By now I had become addicted to her giving me anal sex, and my ass a real pounding and by the Christmas holidays, I had gotten so used to her fucking me with it, that I craved it.

I also started getting these migraines, so, Tiffany gave me some pills called flutamide and a box full of repeat ***********s. They did a better job of controlling my headaches than, 8 Panadols or common headache tablets could.

She was always coming up with these inventive ideas, so now I had to empty my balls into her before she would fuck me. No problem.

I would fuck her, then she fucks me.

The next hiccup in our lives was coming up.

Tiffany and her friends throw a big New Year’s Eve party at the end of the cove. She started badgering me to go with her, since Halloween. I wasn’t that big on large gatherings and, there was going to be a large turn-out, as there usually was, so she says. It was held at some old mansion, that a friend of hers owned.

So, it was the night of the party, and my heart still wasn’t into going, but she insisted. Tiffany doesn’t see her friends much and this was her chance to meet up with them again, but I’ve heard stories about these wild New Year’s and Memorial Day parties before.

Like usual I gave in to her badgering and agreed to go. Only because she bribed me by giving my ass a good pounding, before we left, with her strap-on.

Sometime after, it was dress-up ...

... time. She made me wear make-up and other crap. I wouldn’t have allowed myself to be subjected to this degradation of my character but felt a bit compliant after my pounding.

So, black eyeliner, dark purple eyeshadow, and dark blue lipstick were all I pretty much what was applied. She planned to add more but she stopped herself before going overboard. I felt like a clown, wearing all this makeup.

I was dressed like a guy with make-up.

So, we booked a taxi and drove 30 minutes to the bayside region, until we arrived at the complex’s long driveway. I was gobsmacked at the enormous layout of the estate and then the mansion house itself.

There seemed to be people mingling everywhere, inside the house, outside of it, by the pool, or by the edge of the beachhead, with clothes on, without clothes on, or somewhere in between. It seemed clothes were optional as it was on private land. I was awestruck looking around as the taxi slowed to a halt by the front doors.

Inside everyone seemed to be either chatting, flirting, or drinking, but outside they seemed to be doing whatever they wanted. We started drinking once we entered the house. The music was pounding, it was so loud that it shook the windows of the house and made my heart pace.

I didn’t feel comfortable inside but hid it from Tiffany.

Tiff found her friends and started talking to them, it was all girl talk, so I drifted away and explored the complex. Everyone was ignoring me, so I wandered around the huge ...