Tranny Tales Ch. 01 by erectus123,erectus123

I assumed the ex was the son of a wealthy Asian from Orange County, but I never was sure. All I knew, I had learned from Callista. The ex-boyfriend was about her age and very generous, buying her an entire wardrobe, even gifting her the dog from some expensive breeder. She told these stories of his wealth and generosity so well, but I was beginning to have my doubts that he even existed.


By the time months had passed, she had become a part of my life. Her ex had become a phantasm. She’d say he’d appeared for a few days with his extravagance and then disappear, leaving her with new clothes, perfumes, and expensive sexual devices; for example, a ‘Fuck Machine.’

Don’t know what that is? Neither did I.

This Fuck Machine was a black plywood box about one and a half feet long, a foot high, with a motorized rod that came out of the box’s side where a rubber dildo was attached. There were a variety of these dildo dicks in various sizes. When the machine was plugged in and turned on, it did the old “in and out” quite nicely. She described whipping the boyfriend with a riding crop while the machine fucked him. She wanted to do the same with me and insisted I try it.

“You’ve fucked me. Now I want to see you get fucked.”

I let her have her way, thinking maybe I’d enjoy the experience, but the dildo was too large. She screwed on a smaller cock that fit and began whipping my bare butt with the stinging riding crop. In and out of my ass, the robot ground away for about fifteen minutes. Finally, an exudate that looked like cum, but was mucus from the irritation, dripped out of me.

“Oh good, you are cuming,” she exclaimed happily. I didn’t argue with her, but I had not climaxed. That was the first and last time I had a date with the Fuck Machine and Callista as a chaperone. It wasn’t for me at all. I’m still embarrassed by my acquiescence and that she saw me like that with my naked ass up in the air being dildo raped by that damn machine.

Other than her occasional weirdo boyfriend, she catered to me sexually daily or every other day. What I specifically enjoyed was that she let me fuck her bareback. Most trannys would never have done that. Only a year or two earlier, legions were dying from HIV.

When you fuck someone regularly, you tend to be enamored or fall in love with them. At the very least, you may become very fond of them. Giving sexual pleasure is an attempt to give love. The more I fucked her, the more she sucked my cock, the more I fell in love with her, and I made the mistake of telling her so as I made love to her.

Before I knew it, I was bringing her lunch, taking her out to Philippine fast-food restaurants, giving her gifts and extra money; all seemed fine on the surface. She even decided to shave my pubic hair, saying it would make me more attractive. After that, the proverbial shit hit the fan. I wasn’t aware that she was getting high on amphetamines every afternoon, probably with my money.

On a certain Sunday, I could not reach her by phone, so suspecting the “Sim Card thing,” I stopped by early Monday morning. There I found her gay landlord Hugo. with some Mexican boy rehanging a sexual device with chains from the ceiling. Eyeing the pile of plaster on the floor, I surmised they had initially missed the ceiling studs. A section of the hall ceiling had collapsed under the weight of whoever had been hanging there. Hugo seemed quite proud of the installation, although the ceiling’s bare joists were now exposed.

Hugo stopped to introduce the young Mexican as his assistant. I didn’t know if the young man was a worker or was the one suspended in mid-air. They were still busy at work when I asked..

“Where is Callista, your tenant?” Not suspecting what had happened.

Hugo stopped rattling the chains and bent over to pick up a long screw. He responded,

“You’re her boyfriend. You should know?”

“Cut the shit, Hugo. Where is she?”

“Where is the little slut? I’ll tell you.”

My hand was tightly clenching the small Beretta pistol I always carried in my jacket pocket.

“Ok, sweetheart, it’s like this. Two days ago, the little bitch went crazy, freaked out on her drugs, and broke up the place. I had to call the police. The Judge committed her for 30 days. Maybe that will do the silly bitch some good?”

I spotted Tinkerbelle; the white poodle was still running around. She was so dirty she looked black. The dog ran to me, and I picked her up to comfort her.

I sat down in the nearest chair, holding the dog. I felt as if someone had kicked the wind out of me. I put my hand to my head and thought out loud,

“Where’d she get the drugs?”

“Oh, that black guy, the drug dealer, Slicker, you probably saw him ’round here. He’s her drug supplier, but his weed is not bad.”

Hugo looked at the young Mexican boy and mumbled something in Spanish. They both laughed.

“Can I see her?”

“Nah, they won’t let anyone but her Mom or sister visit her in the crazy house. Don’t worry, hon; she’ll be back here in thirty days. You know, sweetie, you can always swing by here if you want to get your rocks off before she shows up. Swing by here, you get it?” and

The boy must have understood that comment as he jealously tugged on Hugo’s arm. I didn’t respond,

“Thanks, Hugo. I owe you a bottle.”

“Vodka, please,” he replied, and I left.

I stopped by several times during that month to get some word from Callista, but even after a bottle of vodka, Hugo didn’t seem to know anything more. Callista hadn’t returned.

Finally, thirty days, Callista was released. She called me and once more we were together in her room. She had put on weight and was not as gaunt as before, but nothing was quite the same. The dog, now clean and white, was at her feet. I looked around and saw the birdcages were empty.

“Where are the birds?”

“Hugo snapped their necks,” she said, “The fuck said he didn’t have time to take care of them.”

That act was enough to put Hugo on my shit list for life.

“Oh yes,” Callista said, “the Fuck Machine was also missing! and a lot of other stuff.”

We had sex a few times after that. I gave her extra money, and then without warning, she disappeared from Hugo’s rented room. Her phone no longer worked.

Hugo said, “She flew the coup” and owed him rent money.

Several months later, my phone rang, Callista called me.

“Where have you been? I’ve been worried sick over you.”

“I have a new place. You said you loved me when you were fucking me. Well then, if that was true, come and see me!”

Much had changed in those months; being abandoned wasn’t pleasant, and all this drug stuff and craziness were not attractive. Also, I had found a new girlfriend who took care of me sexually. Out of some sense of obligation or guilt, I still went to see Callista.

She had rented a small basement apartment on the other side of town in a private home from a family who lived upstairs. She was giddy and had put on a lot of weight, and her tits were now huge, and so was her belly.

I hardly recognized her behavior. She had become quite dominant. She pranced around the basement in a short skirt, almost hitting her head on a low-hanging pipe. As she bent over, I could see she had no panties on.

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