Gary's Choice

by Major Tom

3 Jun 2020 1537 readers Score 8.8 (19 votes) PDF Mobi ePub Txt


“Hey, even though they were cheating us out of a cut of Tim’s crossdressing nightclub work I made the business decision not to tell you about it. I knew that would be too much for you. You might have gone soft and made trouble by doing something crazy by trying to take him back. Then we’d have nothing” said Robert when I called him anger.

“You’re goddam right!” I yelled. “Have you no shame?!”

“None of us has shame. We can’t afford shame, Anyway, all that’s over. Tim’s settled in that factory and it’s all’s good.”

Soon after, Robert sent me an email. “Since it’s out in the open. I took these because it was mind blowing. Mike agreed with me that the sex was never hotter than that way. We had it that way anytime we could We still do. Tim’s got some nice outfits.” Attached were several pictures of Timothy in drag. He was just as beautiful as girl as he was as a boy. I wept. Then there were videos they took. I was sickened but felt myself becoming hard. Seeing Timothy’s made up face and that wig on him as he was sucking cock was too much. His wide eyes with false eyelashes, his lined eyebrows and lips covered in red lipstick puckered around Robert’s cock was shattering. Timothy getting fucked in a dress!

I listened to another tape:

There wasn’t much acting in the videos I made. It was just sucking and fucking with black and Hispanic guys. We didn’t talk a lot, but they were friendly. I was worried about taking at the same time from two of them, but I did a little blow and it was all good.  

Gregor didn’t offer much direction. I didn’t like making them. I was afraid someone I knew would see them, but I did them anyway. One was interesting. It was a group one with four black tops, me and another bottom. I was surprised that it was Aaron. Small world, he was a guy from my town. We were both busy, and I couldn’t ask him anything., like how ended up there I never saw him again.

I stopped listening.

I had tried to block that out. It was the most horrible thing I was responsible for. It was months ago. Yuri had texted me that he had to see me. We met at his nightclub for drinks.

“Your friend’s whore son was such a great whore. Too great! Leonid, very important leader like him so much.” He showed me a video. Leonid was about 50, shaven headed and burly. His enormous angry looking cock was being sucked by Aaron. His face was made up and he was wearing a long-haired brown wig. Then it cut to Aaron in a blouse, skirt and fishnet stockings, on his back, legs spread getting fucked by Leonid who was babbling in Russian. Aaron was howling “DAH! NANA!,” Russian for “Yes! Daddy!”

“He say this whore only one who made him feel so good. Must have him all the time and want to take him back to Moscow. I could not refuse his offer. I feel bad but I had no choice.” He handed me a briefcase. “Is cash. Fair settlement based on whore’s future earnings for two years minus standard fees. Best I could do. “This for you” he handed me an envelope. “You give and explain to father…”

“What the fuck?!” yelled Jeffrey. “They sold my son?! That wasn’t part of the deal!” We were in my car outside his house. “I’m sorry. It was something none of us could have foreseen. It happened last night. He’ll be okay. His man likes him a lot and will treat him well.” What else could I say? Jeffrey took the suitcase and left. I only saw him and Susan by chance at the country club after that and we only exchanged pleasantries.

I never told him what I found out from Yuri a few months later. Leonid had been whacked by a rival and Aaron then became the other gang leader’s property. Aaron wasn’t treated like a queen anymore, he was put to work on the streets of Moscow. Doing guys in cars and alleyways. He got to wear a mink coat in winter.  

I continued listening to Timothy’s tape:

The chatting and live shows were awful. That stuff was shown all over the world. Talking dirty, begging for tips and having on sex live on camera. It’s all out there with me in it! I try not to think about that.  

Then they moved me to another apartment with Gregor. It’s really a trashy whorehouse. The other workers are cool. We’re having quick sex day and night. It’s a comedown from when Dimitri was handling me. Great hotels and a lot of interesting clients. Some were celebrities! Now, I’m giving quick blowjobs to postal workers and truckdrivers. It’s mostly getting down to business with them because we want a fast turnover. My Dad, Mike and Robert have been by a few times.

“What’s this?” said my older brother Robert when I handed him a small gift-wrapped box after he was  done fucking me. I was dressed up like a Girl Scout. “It’s a birthday present.” “Thanks!” “You can use it on your Jamaica vacation.” “Cool!” A few days later on his Instagram, I saw him wearing the light blue Speedo brief I got him. There were several pictures posted. He looked really hot in it and was having a good time with Rebecca.

Off-duty cops and firemen aren’t charged, so there’s plenty of them stopping by to get off. One young cop is real sexy and nice to me. Nick has a great body and super dick. I  look forward to him.

It was a big deal when after over a year of doing this is all sorts of ways, my Dad’s debt was repaid. There was the subtle pressure on me to keep at it. Sure, they’re all used to the money! How else, could my Dad open a new restaurant or Robert get his new place or my Mom plan my sister’s humongous wedding. Robert fills me in on all the details.

I stayed. The conditions are better, now that I’m free. Before, I was on the clock 24-hours a day with breaks. Now, I do two shifts and have eight hours to myself. My bosses are nicer to me. I even get an allowance, which my Dad set up. I go outside, run in the park and regular stuff. Hey, I’m great at what I do, and I just don’t see what else there is for me now.


by Major Tom

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