Tranny Tales Ch. 02

The word 'Tranny' in this story means a transsexual. Although currently not politically correct, the term is still in everyday use. This is a true story that took place in the early 1990s.

*****

I had come from a late-night business meeting on a warm June evening. The boss wanted to discuss a new supercomputer that the firm was considering acquiring. A few analysts had flown in from Germany to offer their insight.

When I left the office, it was already ten pm. I turned on the radio. Art Bell, the moderator, was talking to a nutcase who claimed that invaders from outer space had abducted him. According to the speaker, the aliens were hermaphrodites and had subjected him to unmentionable indignities of the anal variety. When Art, the interviewer, broke for news, there was an announcement,

"In moments, there will be a rare eclipse of the moon."

I pulled the car over to the side of Santa Monica Boulevard to park, opened the windows, and rolled back the moon roof. I looked up at the sky just as the moon began to be hidden by the earth's shadow. There is a rare moment during an eclipse when the sky turns dark red, and the winds gather together as if to celebrate the celestial event.

Perhaps due to the eclipse or just simple hormonal needs, I felt horny. A longhaired transsexual with a short thigh-high mini skirt and red high heels stepped out of the shadows. Her blond hair was shoulder-length, and her red blouse offered a feeble indication of female breasts, but a male voice announced,

"Hi, I'm Michael."

The voice and the attire didn't add up.

"Hi, Mike, what's up?" I answered.

"Man, this eclipse thing is cool."

"Yes, it is."

"Anyway," said Michael, I was wondering if you'd like a blowjob? I'm trying to earn a little money to visit my brother at the Army base in Oceanside."

"If a Sheriff sees you sucking my cock, Mike, both of us will be arrested."

"I don't mean here on the street. No, come back to my apartment, and we can hang out there."

He seemed like a friendly kid, probably in his early 20s with a boyish face and beautiful long hair, and he wasn't wearing a wig as most Trannies do. The West Hollywood Santa Monica Boulevard corridor was the transsexual center of this part of the world. I didn't feel any apprehension,

"Ok, Hop in."

We sat in the car on a hill on a side street and watched the eclipse for the next fifteen minutes until our necks got sore.

"Man, this is cool."

I'd tuned to some soft music from the FM channel, and Michael, without any prompting, began to tell me his life story, how he'd wound up in Los Angeles sharing a small apartment with an exceptional Tranny with whom he was in awe.

I was well aware of transsexual mentoring, where a younger ward is "adopted" and taught the ropes of being a Tranny and how to make a living through prostitution, or in polite terms, as an "escort."

"So you are headed to Oceanside? You better be careful down there with all the military."

"Oh no, it's cool. There is a Tranny bar on the outskirts of town called Bo-Bo's; it's filled with servicemen. I must have blown 12 guys in one Saturday night, and it paid for the trip."

While Michael talked on and on, I drove a distance down Santa Monica Boulevard, into Hollywood, past Cahuenga, and into a low rent district. Michael indicated we had arrived at his home base. I parked behind an old hotel building converted into small apartments. There was gravel surfacing in the parking lot. As I pulled into the lot, I could hear small stones bouncing off the tires against the car's wheel wells. An old iron staircase was attached to the back of the building and led down to the parking lot, probably once a fire escape.

Michael led the way. We climbed to the second story as the old iron steps vibrated under our feet. I realized we were entering from the rear, an old apartment house that I knew was home to a strange assortment of transsexuals, gays, and drug addicts from past intrigues. The stairway had entry into the hall on the second floor.

I followed Michael down the dark hall. He stopped in front of a door, lifted his blouse, reached into his bra, and pulled out a key. The door opened to a small room, empty except for a bed, a night table, and a flickering old black and white TV. We undressed and rested on the bed, watching an old Errol Flynn buccaneer film in Spanish.

"This is one of the few channels that work on the TV," said Mike.

I think the film was called "Captaino Blud," starring Errol Flinn. The handsome man, in his prime, was jumping from one ship deck to another, followed by many cutthroat pirates.

"Do you speak Spanish?"

"Hell no, just "taco," Michael laughed, "The damn set only picks up the high-frequency channels. Would you prefer Chinese or Korean?"

"No, this will do fine."

As we watched, Michael eased himself into position with his head on my lap with a perfunctory open mouth. With no teeth touching, he began what turned out to be an excellent blowjob. I'm never too quick getting off orally, so I let him labor on, caressing his blond hair that showed no sign of dark roots in the dim light.

Without the skirt, he was a real California boy. Michael had undressed partially; he was wearing his padded bra and panties as he continued sucking. It took a while, but he seemed enthralled, enjoying sucking my dick, and as I was a little tired of his nonstop chatter, with his mouth filled with cock, a little silence was in order, except for an occasional slurping sound. I appreciated the respite.

He coughed a few times, mumbled something about a hair in his mouth, and then the happy moment arrived. I arched my back and moaned, holding his head firmly against my cock. I came like a Sten gun set for rapid-fire. Michael quaffed the full load like a pro. I lay there for a few minutes, my heart pounding like a teenager.

The room was cool and silent except for occasional footsteps that vibrated the outside iron stairs. I whispered in Michael's ear,

"Thank you, baby."

Michael had repositioned himself, holding me in his arms; my cock was still leaking sperm against his thigh, tightly pressed against me. He seemed delighted to have me in his grasp, kissing my neck.

"I really like you," he whispered.

I liked him too. Who can turn down a cow-eyed lover with silent tears running down his cheeks? As much as I appreciated his affection, I never told him I preferred very fem trannys who seemed to be real women. Michael was far too boyish for me, and he made me feel gay, which I was willing to accept for that evening.

Such are the machinations of one who enters the twilight world seeking the "fem-fems" and not the accolades halfway there. But I was there at that moment, and when in Rome, as they say, "Roam."

I would never have said anything to hurt his feeling, so changing the subject, I asked,

"Have you lived here long?"

"No, not long, oh, oh, you have to meet my roommate, Michelle, you should meet her, a real Tranny, great breasts, big cock, you'd like her, and she is gorgeous and very cool."

I smiled and laughed. Big cocks, I was not looking for big cocks.

Mike slowly released me from his grip and sat up on the bed,

"Hey, you can take a shower if you like and hang with me as long as you want."

"Thanks, Michael."

I excused myself and used the tiny bathroom. The offer of a shower was considerate, but I just washed my cock and pubes in the sink with a small bar of soap. I carried my clothes into the bathroom, a precaution born of fear of being robbed.

I was getting ready to leave, a little tired but relaxed, and I enjoyed hanging with this young boy. As sweet as he was, he was not what I had in mind. Michael was lying on his belly in the bedroom, and I gave him a wet kiss on his plump baby ass and handed him some small bills.

He took the cash, which seemed to make him quite happy,

"You can come back, and you don't have to pay me next time," he thanked me.

"Thanks, baby,"

I kissed him on the cheek and was about to leave. Just as I opened the door, there was Michelle. She was ravishing, but Michael failed to introduce us.

I said "Hi" and "goodbye" and went out into the cool, humid evening air.

Ten days later, I started thinking about Michelle in the afternoon, and my dick got hard, so I drove over to her apartment. Most T-girls sleep during the day, and they don't get home till early morning when the Mexican laborers line up on the boulevard in the uptown direction, headed for work. At the same time, a gaggle of trannies are heading in the opposite direction, ready to sleep, their work night already completed.

I didn't know who I would find at the apartment, but I was pleased to see Michelle wearing only a tan terrycloth bathrobe when the door opened. Her large breasts were visible, pressing against the robe. She recognized me at once,

"Oh, Hi, Michael isn't here."

"I didn't come to see Michael. I came to see you."

"Oh. What do you want?"

"Well, please forgive my directness, but I really want to fuck you since you asked."

"Oh, ok, come in. You'll have to wait a few minutes."

The room smelled like candied vanilla.

"I need a few minutes to prepare myself, and if that's what you want, it's going to cost you $40."

"No problem."

She disappeared into the tiny bathroom carrying a vaginal douche with a rubber bulb attached and a plastic pitcher.

"Make yourself comfy, hon."

I took off my clothes, folded them, and set them on a spare chair. I lay down on the bed watching that same old black and white TV. This time it was a movie with a Spanish-speaking Van Johnson, a GI in Germany, on his way to a date with some Fraulein. He was driving one of those tiny Messerschmitt motorcycles with a metal body that made it look like a small car.

When the bathroom door creaked open, Michelle, wearing nothing but a pair of flip flops and a towel around her waist, came back into the room.

"Do you understand this I asked, pointing at the TV?"

"Yeah, a little," she responded.

I looked up at her, and our eyes met, and her lips barely moved into a smile. She was taller than I was, and she wasn't wearing heels, and I guessed she was in her early thirties, a few years older than I. Michele threw the towel somewhere into the corner and climbed into the bed. She was nude, and her breasts were fully curved, touching gently on her rib cage before exploding upwards. They were globes of the perfect size, and even her erect nipples pointed skywards.

Whoever the surgeon was, he was a "da Vinci," The original Leo knew what fem was; the famous artist was a Renaissance crossdresser. Art experts think he posed himself in drag in front of a mirror for a self-portrait known as the 'Mona Lisa.' In those days, most famous Florentine artists were closeted gays. Leo was run out of Florence on rumors of his taking dick in his caboose long before he invented the steam locomotive.

To return to the subject at hand, Michelle was a beauty; long brunet hair, a perfect chin, and the slender boyish hips that I preferred. The only blemish was the small remnants of childhood acne on her right cheek. It was she who smelled of exotic candied vanilla perfume, and it made me forget we were in some Hollywood dive trying to escape reality. Other than the scent, she wore no makeup except an eyeliner that set off her large dark eyes.

"I hope Michel doesn't get upset, he really liked you, but he is leaving at the end of the week anyway."

"He's a sweet kid but a little too boyish for me. You're more my style."

I kissed her hand and moved closer to kiss her lips. She turned her head away,

"Oh, it's too early for lip kissing."

I caressed her breasts and began to suck her nipples. She seemed to enjoy that. My cock was hard the instant her nipple filled my mouth. I thoroughly enjoyed sucking her tits; then, she took my hard cock in hand and leaned forward to blow me. I didn't resist. At that magic moment, the Tranny became a real woman to me, certainly sexier than most women I had experienced.

In those years, many Latin Trannies whom I had frequented disdained cock play, referring to their genitals as "that thing," inferring only a gay male would take an interest in that shameful part of their body. Penis play and being fucked by a tranny, was a gay thing. Real men frequented trannies to fuck them, not to be fucked. When a tranny was desired and penetrated anally by a straight male, it confirmed her feminine sexuality.

I didn't know how to reciprocate with my ass. I never looked at Michelle's genitals for fear it would spoil the feminine illusion, and she had the knack of tucking her cock back between her legs, so it never detracted. This scheme worked for both of us,

"Oh God, Michelle, stop blowing me. I am going to cum, and I want to fuck you."

Michelle released her lips, and my cock sprung out of her mouth like a carnival puppet. She reached for a condom on the night table, carefully rolled it onto my cock, then turned onto her belly, spreading her graceful thighs. I mounted her, still erect. Without the need for lube, I entered her slowly. She moaned and then settled down. I started to pump gently, then with more force, my belly smacking into her butt, making a slapping sound,

"Oh yes, fuck me, baby, fuck me hard, fuck me nice."

I did just that, starting slowly and then picking up pace. Unable to contain my excitement, I uttered

"Ohhhoooo."

I filled the condom full with fresh cum, as if it was a water pouch for a desert crossing. I held onto the base of the condom as I withdrew from Michelle's welcoming ass. My penis began to soften as I lay on my back for a few moments.

"Go use the bathroom if you want."

I got up from the bed, went into the small bathroom, left the door open, threw the brimming condom in the trash basket, and washed with the same small bar of hotel soap. I dried myself with a small face towel and returned to Michelle.

"I really enjoyed making love to you."

"No problem, hon, come back whenever you want."

I left her a fifty-dollar bill on the night table, put on my pants, shirt, and shoes, and made my exit. I was happy to see my car was still there, undisturbed, and off I went.

I continued to frequent Michelle for the rest of the summer. Michael disappeared, just as she said he would, and it spared me an embarrassing meeting. In fairness, I have to give credit to Michael; he sponsored Michelle as one I would like.

After our initial lovemaking, I spent a lot of time with Michelle, hoping a relationship would evolve. After our sex play, we often went out to eat. I met other trannies who lived in the hotel in the comings and goings. They assumed Michelle and I were lovers. One girl, a rather masculine big blond thinking we were a couple, invited us into her apartment to have a threesome.

"Maybe another time," I answered.

"Thanks," said Michelle, giggling, "She smells of strawberry."

We laughed about it, and we weren't looking for a threesome or a meth/crack party; we were invited to by some druggies in the hall. Drugs scared me, and I nixed that invitation.

I made love to Michelle countless times over the few months. We almost became lovers, but we remained sex partners. She was never in love with me, and there was always a missing spark in our relationship. We were friends, but she was always distant, perhaps because she was older than I was and had more experiences, including some bad ones.

She once mentioned that she almost got "married" but never finished telling me the story. Unlike Michael, she had no stories to tell or ones she wished to share. She was warm but did not say much, as if her mind was locked somewhere in another place and time.

We were friends, and we fucked; it never went beyond. I knew our relationship was based on sex and money, and I was content. She made no demands on me, I paid the price of admission, and the orgasms were fabulous. When things are good sexually, you don't do anything to change it. "If it ain't broke, don't fix," the shoe cobbler once told me.

As for the sex, we just did a lot of great fucking, as the Beetles sing, "What's wrong with that, I'd like to know." I preferred when she rolled over and offered her plumb boyish ass in a traditional variation of the missionary style, but sometimes she wanted me to lift her legs. That way, I was able to fuck her deeper. I would pump hard and reach down to grab my penis at the base and rotate it inside her to give her satisfaction.

After Michelle got used to making love with me, she would ask me if she might jerk herself off as I fucked her.

"Do you mind?"

Of course, I never minded. Usually, Michelle would pleasure herself just before I was ready to cum. I never watched. I assumed she was masturbating by the motion of her arm. Where did her cum go? I had no idea. Maybe she caught it in her hand?

We always had good fun, but she was always distant. I never knew where she came from, and I didn't ask questions. She looked like an Italian American, and her slight accent sounded like the East Coast, and I was too busy fucking her to give her an inquisition.

I was scheduled to go in for a hernia procedure and had never discussed it with her. I was fearful the surgery would end my sex life, so I called her several days after the surgery. I was still exhausted and weak; it turned out to be a serious intervention. I had put it off for a long time, and necrosis had set in. Additionally, the intradural puncture had proved ineffective anesthesia. I woke up in the middle of the surgery; and saw the professor surgeon and several young doctors assisting him. As I was feeling no pain, I said to the surgeon,

"I'm fine, continue."

" I can't operate on a moving target," replied the surgeon.

Everyone laughed, and they were forced to intubate me halfway through the operation. When the surgery was over, I vomited some corn nuts I had foolishly eaten the night before.

When I called Michelle four days later, hearing her voice was enough to give me a happy hard-on, but my voice was weak and my breathing irregular. Michelle asked,

"Are you jerking off as we talk?"

"God, no, I just had hernia surgery. Not a chance I am doing that."

I realized later that a phone call mixed with masturbation was a trick that silent callers played on Trannies. I was surprised she thought that of me, but I was in bad shape at that moment.

Once I recovered, I continued to make love to Michelle even before the stitches were removed. After proving to my satisfaction that my cock still functioned, I said to her,

"I'll see you in a few days."

"Listen, hon, I'm thinking of going up to San Francisco to see if I like it there. If I do, I'll stay there for a while."

"Ok, I'll miss you."

"Then come up to see me. Just call me on my cell."

"Ok, babe."

Knowing how difficult it would be for me to take off from work to take a trip to San Francisco, I fucked her harder than ever before and kissed her goodbye. I left her a hundred-dollar bill, and she passed out of my life but stayed in my memories forever. She walked me to the door, threw her arms around me, and as her magnificent naked breasts crushed against me, she whispered,

"If only I had met you when I was younger; you always made me feel like a real woman."

"Which you are,"

I added as she squeezed my hand. Her comment was as close to a loving moment as we were ever going to get. As we disentangled from her impromptu embrace, I glanced down for the first time. I thought,

"Oh my God, Michael was right."

Michelle had an enormous circumcised cock with a large red tip, and it was bigger than those large yellow squash that they sell in the Mexican grocery stores. Her large ball sack was stretched by two large testicles hanging low behind her cock.