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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 estate.

It didn’t take long before I became bored, and I started thinking that it was a mistake coming here. It wasn’t my crowd, nor my taste in music, and not my scene full-stop. I was so bored that I started having thoughts of calling a taxi or Uber and going home.

An hour had passed and after yet another bubbly drink, I went inside the house and try to locate the restroom and take a piss.

I looked everywhere for what would resemble a toilet. I was even thinking pissing in an empty room. Someone walked near me, so I put my cock back in my pants.

Eventually, I found it. It was well hidden, no wonder I couldn’t find it. There were 5 steps downwards and towards, two doors. One door led to the garage, while the other one looked like a closet, which was the restroom, bathroom, toilets, etc.

It’s when I went to go inside, I stood there staring. It was huge, too huge for regular people. All wanted was a piss, and suddenly I thought I was at a nightclub, or a venue, or someplace big.

Why do rich people need everything so big? There were two urinals, three toilets, a shower, plus enough room to swing a cat. It was nothing like any toilet I knew of, except at school.

Once I’d finished and was washing my hands at the basin, there was a sudden noise, as the door quickly opened and slammed shut. It startled me and made me turn around in an instant.

There stood a tall dude who looked a bit intoxicated and ripped his cock out and took a pee. I couldn’t help but notice from the reflection in the mirror, that this dude was packing a big damn cock. This would have to be the first time I cock watched since Tiffany introduced me to another life.

Was it the fact I was tipsy from the wine or had my inhibitions set free, thanks to Tiffany’s bedroom games and having anal sex not that long ago?

Another dude then wandered in and spotted me looking at the big dude’s cock, thru the reflection in the mirror. I quickly finished up and was about to leave, but the new dude grabbed my arm.

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