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Tranny Tales Ch. 02

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The use of the word Tranny is not meant to be disrespectful; it is used as it was in the past although not politically correct at this time.


There is a rare moment during an eclipse when the sky turns dark red and winds seemingly gather together from nowhere, as if to celebrate the celestial event. I had come from a business meeting that ran late that night on a warm June evening years back. The boss wanted us to discuss a new super computer that the firm was considering acquiring. A few analysts had flown in from Germany and we were supposed to benefit from their insight and visa versa.

When I left the office, it was already about 10 pm. I flipped on the radio and there was Art Bell and some nutcase talking about invaders from outer space who had abducted him and who, according to the speaker, were some sort of hermaphrodites. These alien creatures had subjected him, as they usually do, to unmentionable indignities of the anal variety. When Art, the interviewer, broke for the news, I was surprised to hear that in moments there was going to be a rare eclipse of the moon. I pulled over to the side of the Santa Monica Boulevard, opened the windows, rolled back the moon roof and looked up at the sky just as the moon began to be hidden by the earth’s shadow.

Just at that moment, when I was feeling a little horny, a longhaired blond with a knee length skirt and red sneakers jumped out of the shadows. Her hair was shoulder length; her t-shirt offered a slight indication of breasts and a male voice announced,

“Hi, I’m Michael.”

It didn’t all add up.

“Hi Mike, what’s up?” I answered with surprise.

“Man this eclipse thing is cool.”

“Yes, it is.”

“Anyway, I was wondering if you’d like a blowjob, I’m trying to earn a little bit of money. Trying to get down to Oceanside to visit my brother at the Army base.”

“If a Sheriff sees us Mike, both of us will be arrested.”

“I don’t mean here on the street. No, come back to my apartment we can hang out there.”

He seemed like a nice kid, probably in his early 20s with a boyish face and pretty long hair rather than wearing a wig as most Trannies do. As the West Hollywood Boulevard corridor was the Tranny center in this part of the world, I didn’t feel any apprehension,

“OK. Hop in.”

We sat in the car on a high hill on a side street and watched the eclipse for the next ten or fifteen minutes.

“Man this is cool.”

I’d put some soft music on from the FM channel and Michael quickly, without any prompting began to tell me his life story and how he’d wound up in Los Angeles sharing a small apartment with an exceptional Tranny whom he was in awe of. I was well aware of the mentoring of transsexuals 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 place on the outskirts of town called Bo-Bo’s and it is filled with service men. I must have blown 12 guys in one Saturday night, paid for the trip.”

While Michael talked on and on, I drove a long way down Santa Monica Boulevard, into Hollywood, past Cahuenga into a low rent district where Michael indicated we had arrived at home base. I parked behind an old hotel building that had been converted into small apartments. There was still gravel surfacing in the parking lot and you could hear small stones bouncing off the tires against the car’s wheel wells.

From the parking lot I could see an old iron staircase attached to the back of the building, probably a fire escape afterthought. We climbed to the second story as the old iron treaded steps vibrated under our feet. It was an old apartment house that I knew from past intrigues was home to a strange assortment of transsexuals, gays and drug addicts with considerable overlap. There was a hall entry on the second floor. I followed Michael down the dark hall, he lifted up his blouse, reached into his bra and pulled out a key, opened the door to a small room, empty except for a bed, a night table, a flickering old black and white TV and little else. We undressed and rested a while on the bed watching an old Errol Flynn film in Spanish, some buccaneer film, I think it was called “Captaino Blud” where Flynn, so handsome a man in his prime, was jumping from one ship deck to another followed by a bunch of cut throat pirates.

“Do you speak Spanish?”

“”Hell no, just “taco,” he 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 kept his word and eased himself into position with his head on my lap with a perfunctory open mouth. No teeth touching, he began what turned out to be an excellent blowjob. Never too quick to getting off orally, 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. It took a while, but he seemed totally enthralled in the enjoyment of sucking my dick, and as I was a little tired of his nonstop chatter, with his mouth now filled with cock, a little silence was in order and except for an occasional slurping sound the respite was appreciated. He had undressed only partially, wearing his padded bra and panties as he continued sucking. He coughed a few times, mumbled something about his hair in his mouth and then the happy moment arrived when I arched my back and moaned, holding his head firmly against me and 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 to him, “Thank you baby.”

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

“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. But as much as I appreciated his affection, and I would have never told him so, he 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 this twilight world seeking the “fem fems” and not the “halfway there.” But I was there at that moment, and when in Rome, roam, as they say.

Of course I would never have said anything to hurt his feeling, trying to change the subject, I asked,

“Have you lived here long?”

“No, not long, oh, oh, you have to meet my room mate, Michelle, you should meet her, a real Tranny, great breasts, big cock, you’d like her, and she is really pretty and very cool.”

I smiled and laughed, big cocks, were not what I was really looking for.

He 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 my self and used the tiny bathroom. That was nice of him to offer the shower but I just washed my cock and pubes in the sink with a small bar of soap. I had carried my cloths with me, a precaution born of fear of being robbed, and was getting ready to leave. I was a little tired and relaxed and hanging with this young boy, as sweet as he was, was not what I really had in mind. I went back into the bedroom, gave Michael a kiss on his plump baby cheeks and handed him some small bills. This seemed to make him quite happy,

“You can come back and you don’t have to pay me next time,” he voiced as he thanked me.

“Thanks baby,” I kissed him again on the cheek and got up 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 evening.

Ten days later, late in the afternoon, I started thinking about Michelle and drove over to her apartment. Most T-girls sleep during the day, as they don’t get home till early morning. Then the Mexican laborers line up in the direction of uptown on the boulevard headed for work, as a gaggle of trannies are heading in the opposite direction ready to sleep. I didn’t know who I would find at the apartment, but it was my good luck that when the door finally opened it was Michelle who came to the door wearing only a tan terrycloth bathrobe. 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 since you asked, I really want to fuck you.”

“Oh, ok, come in, you’ll have to wait a few minutes. The room smelled like candied vanilla. “Oh well, 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 what looked like a plastic pitcher.

“Make your self comfy hon.”

I took off my cloths, folded them and set them on a spare chair. I lay down on the bed watching that same old black and white TV. It was a movie with a Spanish speaking Van Johnson, as a GI in Germany driving one of those tiny Messerschmitt motorcycles with a plastic body surrounding it on his way to a date with some Fraulein, when the bathroom door creaked open and 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, our eyes met. Her lips barely moved into a smile. She was tall, taller than I was, and she wasn’t wearing heels. I guessed she was in her early thirties. She threw the towel somewhere into the corner and climbed into the bed. She was nude. Her breasts were full curved, just touching gently on her rib cage before exploding upwards. They were globes of the perfect size, and even her erect nipples pointed skywards. Masterful, who ever the surgeon was, he was a “da Vinci,” The original Leo would have known what was fem, as Leonardo da Vinci was a Renaissance cross dresser that art experts think posed himself in drag in front of a mirror to painted himself as the real Mona Lisa. In those days most famous Florentine artists were closeted gays. Leo was run out of Florence on rumors of his taking it in the caboose long before he invented the steam locomotive.

But to return to the subject at hand, Michelle was a beauty; long brunet hair, a perfect chin, slender boyish hips that I preferred at that time and the only blemish was the small remnants of childhood acne on her right cheek. It was she who smelled of a candied vanilla perfume that was both exotic and flattering. It made me forget we were in some Hollywood dive trying to escape reality. Other than the scent, she wore no makeup except a little 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 its too early for lip kissing.”

I caressed her breasts and began to suck at her nipples. She seemed to enjoy that and my cock was hard the instant her nipple went into my mouth. I was thoroughly enjoying myself when she took my hard cock in hand and leaned forward to suck me. I relaxed and let her pleasure me. At that sexual moment a Tranny becomes a real woman to me, even better, certainly sexier. In those years, many of the Latin Trannies whom I had frequented distained cock play referring to their genitals as “that thing” as if to infer that only a gay male would take interest in a Tyranny’s penis. Cross fucking was a gay thing and real men frequented trannies to fuck them, not to be fucked by them. To a Tranny, being penetrated anally by a straight male was a confirmation of her feminine sexuality. I didn’t know what it was to reciprocate with my ass or even look at her genitals for fear it would spoil the illusion, and she had the knack of tucking her cock behind her so it was never a topic brought to light that detracted from her femininity. This seemed to work well for both of us,

“Oh God, stop, I going to cum, but I want to fuck you.” She released her lips and my cock sprung out of her mouth like a carnival puppet. She reached for a condom off the night table and carefully rolled it onto me, then turned over onto her belly. I mounted her, still erect, and apparently without need of lube, I entered her slowly, she moaned a bit 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, slowly and then picking up pace and unable to contain my excitement I uttered an “Ohhhoooo” and filled up that condom with cum as if it was a water pouch for the desert. I held onto the base of the condom as I withdrew my softening penis and 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 leaving the door open and threw the brimming condom in the trash basket, and with the small bar of hotel soap washed myself. I dried myself off with a small face towel and went back to Michelle.

“I really enjoyed that, making love to you.”

“No problem hon, come back when ever you want.”

I left her a fifty-dollar bill on the night table, pulled 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 I was spared an embarrassing meeting, but in all fairness, I have to give credit to Michael as he had sponsored Michelle as one I would really like.

After our initial love making, I spent a lot of time with Michelle, with the hope that a relationship would evolve. We went out to eat often after our sex play and in the cumings and goings I got to meet a few of the other trannies that lived in the small hotel. They must have 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.

We laughed about it afterwards. I wasn’t looking for a threesome.

We were also invited to a meth/crack party by some druggies in the hall, but that sacred me a little so I nixed that invitation.

I made love to Michelle countless times over the few months I knew her. We almost became lovers but more precisely I should say we were sex partners because it was obvious but she was never in love with me. Maybe because she was older or had more experiences than I did, including some bad ones. She once mentioned that she almost got “married” but never finished the story. There was always a missing spark in our relationship. We were friends but she was always a little distant, 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 somewhere in some other place and time. We were friends, we fucked, but we were not in love. It was a relationship based on sex and money and I was fully content. When things are going good sexually, you don’t do anything to change it. “If it ain’t broke, don’t fix,” as the Mexican shoe cobbler once told me. She made no demands on me, I paid the price of admission and the orgasms were fabulous.

As for the sex, it was in retrospect somewhat vanilla. 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 up her legs and fuck her as deep as possible. I would pump hard against her and reach down grabbing my penis at the base and rotate it to her satisfaction. On more than one occasion, depending on our position, after she got used to me, she would jerk her self off, saying, “Do you mind?” as I fucked her. Of course I never minded. This happened usually just before I was ready to cum, but I never watched, I just assumed that was what she was doing by the motion of her arm. Where the cum went, I had no idea, maybe she caught it in her hand?

We had good fun but she was always a little out of reach. I never even knew where she came from although from her slight accent I thought she was Italian American and had come from the East Coast. Truthfully, there never was a need to pursue conversations beyond the “uhs and ahs.”

I was scheduled to go in for a hernia operation and had never discussed it with her. Foolishly fearful that the surgery would put an end to my sex life, I called her several days afterwards. I was totally exhausted and weak, it had been a serious intervention as I had put it off for a long time, necrosis had set in and to add to the problem, the interdural puncture had proved an ineffective anesthesia. I woke up in the middle of the surgery; saw the professor surgeon and several young doctors assisting him. As I was feeling nothing I said to the surgeon,

“I’m fine, continue.”

” I can’t operate on a moving target,” replied the surgeon.

Everyone laughed and with that they intubated me halfway through the operation. When it was over I vomited some popcorn I had foolishly eaten late the night before the surgery.

As I started to say, I called Michelle up four days later and hearing her voice was enough to give me a happily vindicated hard on, but my voice was so weak and my breathing irregular so Michelle asked,

“Are you jerking off as we talk.”

“God no, I just had hernia surgery, not a chance.”

I realized that a phone call mixed with masturbation was a trick that silent callers played on Trannies back then, but I was surprised she could have thought that of me.

Once recovered, the next week I continued to make love to her even before all the stitches were removed. After proving that my cock still functioned nicely, 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 a trip to San Fran would be for me, I kissed her and fucked her harder then I ever had before, left her a hundred dollar bill and she was out of my life and into my memories forever. She walked me to the door, threw her arms around me and as her naked magnificent 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 made me feel so good. It 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 and thought, “Oh my God, Michael was right,” she had an enormous circumcised cock with a large red tip, bigger than one of those large yellow squash that they sell in the Mexican grocery stores and her ball sack was so stretched by her large testicles that it hung behind her cock and was almost of an equal length. I don’t know how, but seemingly without an order from my brain, my hand reached out and cradled her cock in my hand. It was warm and moist and swelled immediately from the slightest pressure.

“We never played with that thing did we?” I said.

Ben Esra telefonda seni bosaltmami ister misin?
Telefon Numaram: 00237 8000 92 32

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