Tranny Tales Ch. 10

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Gilda (2010) - An afternoon in heaven.
2.9k words
4.37
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10

Part 10 of the 11 part series

Updated 06/07/2023
Created 11/01/2015
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erectus123
erectus123
462 Followers

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.

TRANNY STORIES CH: 10 GILDA — 2010, AN AFTERNOON

Her name was Gilda. She wore one of those large green felt sun hats, the kind that are so large you could hide your face under it. If her face was hidden, her breasts certainly were not. They filled her shoulderless blouse like an apron full of tomatoes, big bountiful tits that cried out, "Suck me."

She was sitting in the outdoor eating section of what used to be the prime tranny restaurant in West Hollywood. If you know the place then you know they knocked it down a few years ago and now were is a big windowed Trader Joe store where we used to have the finest trannies in town spread out like flowers in a garden, all available and accessible.

The nice thing about the outdoor eating area was that you might walk right up to one of the girls sitting there with a coffee or salad or whatever, maybe she was smoking a cigarette, like Gilda was that afternoon, and you could introduce yourself. With your real name or fake name, nobody cared. As long as you didn't look like a serial murderer and had some green in your wallet, that familiar bar stool babe's "fuck off" when you made a pass at a drunken broad in a dive bar, that behavior was off the table. Instead, from the tranny girls you got a welcoming akin to the way the warm moist Chinese massage girls greet you, like a long lost relative home from the war.

Gilda spoke in a hoarse whisper, she was quite unique and I thought immediately she was patterning herself after Rita Hayworth,

"Sit down Honey," and you could taste the sweetness dripping off of the 'Honey'.

I sat right down across the table from Miss Luscious, Miss Hayworth, Miss Universe as far as I was concerned. My cock was doing handsprings in my pants. It was a hot Hollywood afternoon.

Many of the trannies you'd meet were Hispanic and you had to cobble together a bit of high school Castilian to understand them, but they still hardly understood you. If they'd speak in Spanish it was 'rapido' and you had no idea what they were saying, but it didn't matter. We all knew what we were up too. Just the same it was nice to meet up with someone who grew up in with the same cultural bedrock.

"So where are you from, and your name?" I asked.

"I'm Gilda, big boy. Are you a big boy?"

She started right away with the sexual banter.

I knew exactly which part of me she was referring to.

"Cause I'm almost a virgin"

"Almost?" I said, "I thought one was or wasn't."

She smirked, "And you, are you a virgin."

"I thought you wanted to know if I was a big boy?"

"On point, are you a big boy or rather small, a teeny weenie little man?"

I laughed,"I'm sure you could fit me into your life without too much effort."

"Oh you're shy. Ahh, let us say, are you as big as a banana?" She wasn't going to let up with the cock jokes.

"Hardly,"

"As a hot dog?" she parried.

"Yes, more like a thick sausage. Are you taking up cooking or fucking?"

That made her laugh, a deep throaty laugh, that filled the air with a puff of smoke

"What the hell are you smoking?" I'd noticed the cigarette were oval and without filters.

"Oh these are french cigarettes, Gallois, I just adore everything French."

"French fries or french kisses," I asked, reaching out to hold her other hand.

"Oh, both are good, Honey," we were back with the Honey.

"Do you have a name, Honey."

"Of course, and a birth certificate too, but you can call me Dan."

"Ok Danny, what did you have in mind?"

"Why don't we head back to a hotel or do you have an apartment?"

"I have a room Honey, we can go there, did you want to fuck me with your big cock Danny?" she squeezed my hand to accent her question.

I let that question pass, "Is it in walking distance?"

"Why, do you like hiking?"

"Well, my car is over there, the silver sports car, Miss Gilda, your chariot if you wish."

She smiled at that, "Oh I like your car."

We walked over on the cement parking lot. I opened the door. A few of her friends whistled at us.

I 'm sure they took down the car's license plate, in case I was a 'Ted Bundy.' And that was a good idea because although I wasn't looking for blood, there was a world of crazy out there. I just wanted some afternoon delight with a little traction thrown in, Some t-girls use too much lube and it is as thick and greasy as a pecan pie on a hot summer's day, and I'd been around enough to know that doesn't get me off.

As soon as I'd opened the passenger door, she was fiddling with her cigarette.

I'd rather you don't smoke in the car Gilda," she didn't look too happy.

"Well, could you put the top down, I'd prefer that."

"Sure, can do."

As I put the top down, she put the cigarettes away and started going through my cd's that were in the tray between our seats.

Now she was sweet again.

"Could we play this one?" It was a Billie Holiday reissue.

"Sure Gilda, I love your name, just push it into the slit under the radio."

She pushed the Cd into the player and the sweet melodious voice of the 1930s wound it's way out the loud speakers and into our ears.

Even though it was still daylight, the traffic on Santa Monica Boulevard was congested. I hoped no one from the office would see me. I couldn't have been more obvious with a sports car, a loud radio and a tranny hooker whose tits were just about past the point of no return.

But I assumed my luck held and we arrived at a parking lot sandwiched between some old bungalow off the main strip.

"I'm up there," she pointed.

I put up the top, locked the car and followed her up a wooden staircase to a small room on the second floor.

"Would you like a shower," she offered.

"Maybe later Gilda."

"Do you have anything to drink?"

"There's a little wine and some Mexican brandy, it's not that bad."

"Ok, I'll try that?"

"Why don't you take off your clothes Danny, I'll get it for you."

I undressed and stuck my wallet in my shoe, just a bit of safety although I felt pretty secure. I piled my folded pants, shirt and the rest over. I'd know if anyone disturbed the pile.

Gilda came out of the corner where there was a small fridge with a cold can of Coke and this half bottle of Mexican brandy. I poured myself a drink with a little brandy and offered Gilda one too but she said, " In a minute," and started to peel off her layers of clothing.

Under that big hat I wasn't sure of her age but now I could see she was probably in her mid twenties. As she unwound the green blouse her tits spilled out like dairy cream, white and fluid with substance.

"That's some pair of tits you've got."

"Yeah, I had them done in Chicago, cost me $10,000."

"Jesus."

"Yeah but they are my money makers. When the guys see these they come on like star troopers." I had to admit she was right on that.

She took off her tights and was wearing a black thong underneath.

She came closer, "Ok, I take a bit of your drink." I handed her the glass.

"Do you want me to take off the thong, or will my cock annoy you?"

"Oh that's ok, nothing about you annoys me, let it hang."

"Lots of guys when they see my cock want to suck it or have me fuck them, but that's not what a lady does."

"No? Well, whatever works for you. So you fuck the boys also?"

"If that earns the bread, of course, doesn't mean I have to enjoy it."

"So Gilda, given the choice, would you rather fuck a guy or have him blow you?" I took a sip.

"Probably I'd go with the blooey, provided he wasn't sloppy about it."

"With condom or without?"

"I have to know you a bit before I go without protection, but a condom is better, not better but safer. Nothing feels as good as raw skin."

About that time she pulled off her thong and the bulge underneath resolved into a fairly long cock, longer than mine, and that embarrassed me.

"This ok? She said, flexing her cock, it gets cramped in that tight thong."

I was seated on the bed and she approached me. She was a tall girl, taller than I had imagined, with a slender willowy figure, very feminine and now her cock, hanging like a flag at half mast was staring me right in the eye.

"You can touch it if you want?"

I reached out and unfolded it from the damp rather small balls that hung behind it.

I played with it a bit and it chubbed up.

"I like you Danny, go on, you can suck it."

I wasn't usually this interested in cock but having started on this odyssey there didn't seem to be any turning back and I was enjoying myself. As I played with her cock, her penis grew, into a long straight shaft, the diameter was like a broom handle. Without fear I opened my mouth and then she gently pushed the head right into it, like she was purposefully breaking me into something I wasn't really used to doing.

I sucked gently, the taste was fine, just a little hint of sweat or piss but nothing overwhelming. It was a hot Hollywood day after all.

As I tongued the head, she clasped my head firmly in her hands and pushed deeper into my throat at which point I gagged. I pulled back my head, her cock rested against my cheek.

"I'm sorry, I'm not really used to sucking cock."

"Oh you will be," said Gilda, "I'll teach you, you'll be an expert cock sucker Danny. You'll be my cock sucker."

I could feel my own dick flexing. This talk was turning me on more then I would have expected.

"Here, suck it some more. Try not to gage."

I didn't argue, I was better this time and when I opened my eyes I could see her smiling at me before she pulled out.

"Come into bed with me Gilda, I'd like to fuck you."

"You've finished so fast, sucking my cock?" she teased.

"I'm sorry, I really want to fuck you now. Sucking you just got me super horny, sorry."

"That's ok, just give me a few minutes to get ready."

As she walked to the bathroom, her large cock still erect and wet from my saliva, she flicked on the TV which didn't seem to work, it was fixed on a Mexican station and the video scrolled upwards so you couldn't make out what it was, although the audio was fine if you could understand it.

I got up and tried to tune in another high frequency channel but the television wasn't hooked up to an outdoor or central antenna so it was futile.

About that time Gilda returned from the bathroom, her cock had gotten smaller and she got into bed with me and her ass was cold.

"No hot water today, sorry if I freeze ya."

"No problem. So tell me where do you come from?"

"San Jose."

"Where is that?" I wasn't a native Californian.

"It's outside of San Francisco, a nice town. Cops Don't bust trannies but sometimes you have to blow them for free."

"You don't have to let them fuck you for free?"

"Nope, for fucking they pay like everyone else."

By now I was starting to like this girl. She was open and free with banter, fun to be with. No nasty side or ill temper like some t-girls I'd met who were over the hill on drugs or booze and had that bleary eyed look. She was straight forward, unashamed of who she was and what she did.

She slipped into bed alongside me and I was reaching around to hold those $10,000 tits and believe me they were as natural as any girl I ever dated.

"Do you still have sensitivity in your nipples," I asked.

"The right one is dead after the surgery, but the left on is still ok."

With that advice I started sucking on the left tit. Her nipple was small and the areola was about the size of a half dollar. As I sucked her tit she seemed to relax and started to rub by body and slowly worked her hand way down to my dick.

"Oh I can feel you are just fine, not a banana, but the perfect size as far as I'm concerned."

By now she had my dick standing upright, so she moved between my legs and started sucking my cock. Not just my cock but my balls as well, and rubbing firmly behind my balls.

"Oh that feels good, but don't make me cum yet."

She slowed down and I got up and moved behind her, she kept herself up on her arms and knees and I got into position, like two dogs in heat.

"Wait hon, take some lotion, I'm kinda tight."

"That's good, I like it tight, no bananas lately?

"You don't want to know."

"Oh I do."

"Well, later if you insist."

"It doesn't matter, all the matters is you and me."

I rubbed my cock with the clear gel.

"Do you want me to wear condom?"

"Are you clean?"

"Oh yes, I haven't fucked anyone bareback for a few years."

"Well, if that's true you can go without a glove, I trust you."

I pressed forward with my erection, but had difficulty entering her.

"She reached back taking my cock in her hand. Let me help you."

She guided me right to the spot.

"Go slowly," she said

.

God, it felt like I was like I was inside a slippery banana peel, it felt so good I wanted to cry, in fact there were tears in my eyes as I entered her slowly, working her open little by little. She certainly was tight. Her ass walls clung to my cock as if a tight fist.

"Oh this is so good, baby."

"It's good for me too, Danny boy, don't stop, keep at it"

.

With my hands holding her golden globes I took my time slowly fucking her ass with my stiff dick. Her sweet smelling hair was in my face. It wasn't a wig like most trannies, it was her real hair, blonde with bit of curl and with a heavenly odor.

Finally the moment of truth arrived and she began to contract on my cock, hard firm contractions that destroyed any possibility of continuing any longer. This was a girl who knew how to throw a pleasing fuck, a real professional fuck, the kind you will never get from a wife or girl friend.

As my cock erupted and pulse after pulse filled her firm tiny butt. Almost boyish but still padded, not boney.

"I'm cumin," I mumbled.

"Me too," she whispered and as I filled her with my cream, I reached around and grabbed her erect cock that squirted warm cum into my palm.

We lay, now collapsed, my dick in her ass, her cock in my palm.

"Rest now, enjoy the moment sweetheart. You made me very happy."

"You too, it was so good."

I thought to myself, what kind of an animal am I. This is the best thing I've ever experienced and it is all physical sensation, all cock driven, my mind wound up like some mechanical wind up toy.

Finally I slipped out, my cock now soft, her ass creaming.

"Oh my I got your hand all wet. I'm sorry," she said.

"Oh no problem, I liked it." I wondered if I should have licked it off my palm but I didn't. She put her hand over her ass so the cum wouldn't leak out and handed me a soft hand towel to dry myself.

I hung around a while, I passed on the cold water shower but promised her I'd be back. She didn't ever ask me for money, but I left a generous stipend on the bed pillow. I got dressed and

I kissed her goodbye, she was still nude and I loved the feel of her tits against my chest.

"I'll see you soon, Gilda."

"Here, take my number," she handed me a card.

It read, 'Professional Services Rendered' and in a fancy script and—'Gilda' then a phone number.

I put the card in my wallet and kissed her again, and left, walking as if there were springs under my feet, so light, all tension gone from my body and a smile I rarely wore on my face.

When I got to my car I was glad to see it was undisturbed. I got in, turned the steering wheel to get out of the lot, when my palm stuck to the leather covered wheel. It must have been some of Gilda's cum that was still on my hand, I licked a bit of it off, it tasted good, and exited the graveled decomposing cement lot.

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