Tranny Tales Ch. 01

10/23/2015 in Transgender & Crossdressers Stories

The use of the word Tranny is not intended to be disrespectful. I use it as it was used in the past as a simple description of a fem cross-dresser who, although born a male believes 'she' is really a female and responds sexually as a female. The word 'tranny,' considered politically incorrect by some, is still heard every day.

*****

This tale took place a good while ago when I was younger. Most details remain clear in my memory. Strangely, at this moment I can't remember her real name, maybe because she changed her name every month?

She was a Tranny or pre-op T-girl, if you please, about 19 years old. She complained her competitors would cancel her insertions on 'Craig's List,' and she thought changing her name in her weekly adverts would foil them.

Sometimes she was ‘Alice,’ and sometimes ‘Tigress.’ I liked the name she used when I first met her, she called herself 'Callista.' Anyone could see, even with the name changes, that the same person placed the internet advert. In her Craig' listing, she described herself, always including the phrase,

"Callista, a young ripe Filipina transsexual, seeks tender companions, open to all requests."

She used a lot of names. Who knows if the name changes had any effect on her competitors? —or was all of this a charade? When you are in the middle, you don’t always know what is really going on and what was her real name? I just don't recall.

Let me describe her; she was a young Philippine, born in the United States. I think her skin was almost white, perhaps a light creamy tan. When you buy a hot dog at night, do you really pay attention to the color of the mustard? I thought she was beautiful.

Callista had long black hair and an oval face with moderately hooded Asian eyes. Her fingers were long and graceful, and her nails long and always painted or polished in different colors. She was tall for someone of Asian descent. When I came into her room in the early mornings, I would find her in the nude, but she would roll over, silent, lower the sheet revealing her plump rear end, begging me to disrobe and mount her.

Callista had no visible hair on her body, just a few pubic wisps. Her cock and balls were so small, almost invisible, always hidden between her thighs, making her look even more feminine. I don't know how she was so well-groomed in that crazy house where she rented a room, but she was always clean, perfumed, and tasted good.

Callista loved animals. She had a little dog, a white poodle she called "Tinkerbell," and two yellow canaries, so tame they would fly around the room and land on her hand. Like most members of the third sex, she was at odds with her family, Evangelical Christians, who strongly disapproved of her lifestyle.

On more than one occasion, Callista said,
"My Dad says, 'God will punish me for what I do,' but I say God should and punish them."
Callista's family believed this young girl was the scourge of civilization and the impending biblical destruction of this world was right on her shoulders. Although they lived in Los Angeles, Callista's parents only saw her on rare occasions. Callista had left her family a few years before, forming a liaison with a wealthy Chinese student who provided the money for the dog and her possession of unusual sex toys, including an automatic "Fuck Machine." That relationship was mostly over, and now she lived in a rented room around the corner from the McDonald's in an old house populated by drug-addled degenerates.

I didn't find her from her ads on Craig's List. The first time I saw her was in the small supermarket near where I was living. As she passed me on the aisle, I immediately knew she was a T-girl. I found her attractive, and I backtracked to look at her again. To my disappointment, she had disappeared.

Several months later, on a spring afternoon, I saw her again. She wore a very short red miniskirt and a coral orange frilly blouse, walking towards the bus stop in front of the MacDonalds' wearing stylish dark sunglasses, looking like a young cute, shy Hollywood girl who had lost her way.

I certainly wasn't going to let her disappear again. I walked up to Callista, asked her name, started a conversation, I asked if she lived in my neighborhood, telling her I had seen her in the market. She seemed flattered that I remembered her,

"Oh, I used to live over there, but now I live here."

Within a few minutes, she gave me her new address and phone number.

As it happens in Los Angeles, it was a holiday weekend. The streets were empty. I called her in the morning repeatedly with no success, but I got through to her in the afternoon.

"I had to go get the phone's Sim card recharged, don't call me so much. They charge for every call even if I don't pick up."

"I'll give you money for a recharge. Can I come to see you?"

Within the hour, I was at the door of a small tumbled-down, dirty clapboard house on a side street I didn't know existed. Scraps of wood and signs of haphazard construction material littered the tiny front yard surrounded by a rusty wire chain-link fence.

Her landlord, Hugo, was the Lord of the Manor, if not the Lord of the Flies. Hugo was a tall skinny fifty-year-old long-haired gay, with a ragged beard. He always looked dirty but also dangerous. Callista's room was at the back of the house. To find Callista, I had to knock at the front door, where I was greeted by Hugo, who reminded me of Cerberus, the three-headed dog that Dante's described as the Gatekeeper to Hell. Hugo opened the creaking door, shedding old peeling lead paint, and pointed me down the hall to Callista's rented room.

Callista explained that several years ago, Hugo had inherited the broken-down house from his grandmother and was in the process of restoring it. However, even though Hugo often had a hammer in hand, progress in a significant renovation seemed very slow. The only progress appeared to be the installation of a sex swing that required round eye-hooks to be installed in the ceiling. The person standing in front of them with an erection could push the swing back and forth to facilitate anal intercourse might penetrate the person suspended with their naked ass exposed.

Hugo was always semi-nude, frequently wearing a short wife-beater armless shirt while his large genitals were in plain view. When I asked to see Callista, he seemed confused and disappointed. When I used the word 'tranny,' Hugo smiled and pointed down the hall. When my gaze fell, I could see Hugo was hung like a horse, but he was more interested in being ridden than in riding. He worked part-time in the early afternoon for a sandwich shop around the corner, doing deliveries on an old bicycle. Hugo liked to put his arm around me, squeezing my muscles, asking if I would like to come in and visit him and have a drink or smoke.

When Hugo said, "smoke," he lifted his hand to wave his fingers, indicating he had in mind "special smokes," if you know what I mean. This time period was many years before the legalization of pot. He'd pat my ass with his other hand, or he'd playfully try to grab for my cock. I did my best to avoid Hugo, who was obviously interested in more than a gay handshake. I wasn't gay, and I wasn't attracted to gay men. I narrowly confined my interest to very feminine trannies, the third sex as far as I was concerned.

I walked down the corridor strewn with plaster and knocked on Callista's door that opened into a well-organized pink room with a large bed. There was Callista, nearly nude with 'Princess,' a tiny white toy poodle on her lap. I started to play with the small dog, which broke the ice.

I looked up to see two yellow canaries in separate cages, singing happily as the afternoon sun poured through the window. For that moment, it might have been a typical household. But the heady aroma of "Chanel No. 5" filled the room, reminding me of the smell of a New York City women's canasta club card party. Callista must have splashed the perfume around the room.

Callista and I talked a while before she pulled me down on the bed with our lips locked as I relieved her of her bra and panties. The little dog jumped off the bed and scampered away, disappearing under a piece of furniture.

My head moved between her small breasts, back and forth, sucking her nipples when she grabbed me by my cock and pulled me closer to her. I was like a wrestler pinning an opponent. Her position under me gave her easy access to my cock that soon was inside her open mouth. She started to blow me rapidly, I whispered,

"I want to fuck you,"

Callista stopped sucking, rolled over belly down, and lifted to all fours, spreading her long slender legs. I fitted myself behind her doggy style. Her plump little ass was a welcome target. She handed me a dab of lube, which I'd rubbed into her anus and on my cock. I was quick to slide bareback into her tight vortex.

It was as if time had stopped. Callista moaned agreeably with each gentle thrust as I fucked her slowly. Now and then, she'd say something stupid, like

"Fuck me, Poppy,"

which was what the Latina T-girls say. But she wasn't Latina, nor was I. Finally, I could no longer contain myself. With my arms around her back, my hands squeezing each of her small pert breasts while my fingers pinched her large nipples, I came copiously, moaning and mumbling primal sounds, including,

"I love you." which really meant, "I love fucking you."

Unfortunately, I didn't speak Tagalog, or I might have said something memorable, but there was no escaping that I was well pleased. We lay coupled together like two empty trains waiting to be unloaded, undisturbed on the side tracks. I was so relaxed and sexually relieved that I fell asleep. Callista had also fallen asleep, but realizing my stupor, I awoke. As I withdrew my flaccid penis, she stirred. I took her hand in mine and whispered,

"Rest my darling, rest," hoping to make my getaway.

A few moments later, I got out of bed, put on my clothes, and left her some money on her night table. I didn't know where the bathroom was, and I didn't want to open the wrong door, so I retraced my steps to find my way out of the labyrinth. I wasn't even able to wash my dick off, so I'd just pulled on my underwear, my body smelling from perfume when she matter of factly said the oddest thing which I’ve never forgotten,

"Do you want some lotion for your cock?"

Was what I needed? Callista meant well, but it seemed a strangely personal thing to say but what could be too personal after you fucked someone in the ass? Maybe it was a good idea?
No one else had ever made such a suggestion. But as the years have passed, whenever possible, I wash my cock after sex or urination and often apply a dab of lotion, thinking of her.

That was the first time we had sex. After that day, I visited her frequently in the early mornings. The house was still, but when I arrived the door was unlocked. I'd let myself in and find my way to her room, where she was sleeping. I would crawl into bed next to her, caress her until she was amenable, and then I'd fuck her, relieving myself of every anxiety.

Afterward, I'd go for breakfast at Mac Dee's' and order the $3 breakfast with coffee, pancakes, sausage, and some yellow fluffy soggy mass that passed as scrambled eggs. If Callista was still awake, I'd invite her to accompany me. Usually, she fell back into a deep sleep after sex, at least I thought that was the reason. She’d turned sideways to shield herself from the hall light and I could see my cum leaking out of her ass and puddling onto the bed when I opened the door to leave.

It wasn't easy to remain in contact. Callista's phone was always out of service. It was some cheap burner phone sold at the 7-11 Store. Callista would forget to recharge the sim card, whatever that was, for lack of money or because of more pressing purchases.

Callista never asked for much money, compared to other T-girls I had frequented; she was a cheap lay. I say that, with respect, as she was a good lay, very satisfying, and like any good sex partner, I kept coming back for more.

With time we became friends and lovers, and without hesitation, she began to open up about her past. She talked about her ex-lover and sometimes her family. Her sister was always mad at her because the phone was out of order. I never met the sister she frequently spoke of, though not lovingly. Her father was ex-military, she rarely mentioned her Mom.

She also mentioned a black guy, 'Slicker,' who was just a friend. I had noticed him hanging around on more than one occasion.

"Boyfriend?" I said.

"No," just a friend."

I saw Slicker several times throughout my relationship with Callista, either arriving or departing, book-ending our fuck sessions. He was about my height but slighter, very dark-skinned with white sparkling teeth. He wore an oversized brown leather jacket and a blue Los Angeles Dodger baseball cap pulled down, so you never saw his eyes. Later, I found out just what the relationship was. Slicker was not her friend. He was her drug dealer.
.
She always promised me she would make other clients wear rubbers, but who really ever knows what your sex partner does when other guys are fucking her ass. You try not to think of it and. tread the path between life and death without knowing which was the high road. Such is the lure of complete sexual pleasure that can obscure the chance of contagion.

It is safe to say that the sensation of anal sex without using a condom holds no comparison to fucking while wearing a glove, albeit so much safer. I always fervently suggest using condoms until an HIV test and a monogamous relationship are established with a sex partner. If such a thing is ever possible, baring accidental condom failures, that is the safer row to hoe.

When I first met Callista, she seemed relatively passive on most topics. She was apolitical, pro-fashion, pro-sex, and she loved Filipino food. I took her frequently to a well-known Filipino restaurant. She was young, and she was fun to be with.

I liked her most the fact that she had few clients, just a wealthy boyfriend from a previous relationship, whom she had lived with for a short time and who'd shown up now and then. She said she thought she would have married him and been on easy street.

Callista said, “If he had footed the bill, I might have become a sex change and married him,”

but as I learned more about him, I wondered if he was a better candidate for the surgery than she was? In any case, same-sex marriage was not yet an option, and their romance seemed to have run its course, even with occasional fits and starts. For them, still being together seemed out of the question.

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