Tranny Tales Ch. 06: Cumming in Sophia

Sophia of the Bourbon Wagon – a sex change?

I remember years back when coffee flavored liquor made its debut. Was it Kahlua? Maybe not. Anyway, they set up a stand inside a tent in Times Square and if you stopped and stuck your head inside, they shot an atomized spray, right through a hole in the bottom of a small paper cup; zap! –Right into your mouth. And it tasted good!

Well, the JFK Airport has improved on that skit. Last week, the King of Bourbon, a liquor company that produces several well-known brands, set up a bar and offered quarter shots of sample booze to any traveler over 18 with a few minutes to loose. A skinny black kid with reggae jerry curls was hustling up customers who were passing by. When I heard what he was selling or should I say, giving away; I climbed up the five stairs, lugging my heavy suitcase, up to the bar where a vixen that looked like Sophia Viagra was pouring shots. I asked if they had any reserve whiskey and Sophia, which strangely turned out to be her name, reached for a round bottle in the back and poured me a quarter shot, when I frowned she poured a little more in my glass, increasing it to a half shot. I drank it slowly, savoring the taste that was not really so remarkable, certainly not as remarkable as Sophia's tits and ass. I must admit when I took the hit of bourbon, and it rolled back into my throat, my eyes took in Sophia and I imagined I was drinking it out of her vagina.

"So how long have you been working here, hon?"

She opened her big eyes, her eyelashes fluttered like butterfly wings on both sides of her tiny perfect nose.

"Three months, just about, we're scheduled for six."

"Where do you call home?"

"I'm from Brazil originally." (I had figured that out from her wonderful accent that sounded like honey and raspberry syrup)

"I live in center Manhattan, they give me a hotel allowance so I'm staying with a friend, a girl friend who I used to waitress with and I'm saving a bit of money on that. Of course I help out with the rent. It is so expensive here to live in New York."

A few grammar errors aside, and that honey dripping Portuguese accent, my heart was doing flip-flops in my chest.

"How late is your gig?"

"I work till five, and then another girl, Lucie, comes in till 12pm. You would like Lucie, she is very beautiful and very sexy."

I stood there entranced. I could not take my eyes off he sparkling eyes and full glossy lips. Her breasts formed a shelf I wanted to lay my head upon.

"I'm sure Lucy is fine but I can't imagine any one more beautiful that you. How about dinner at a great steak house, the same one Broadway Joe used to own."

"Who is that?"

"Well I can see I am showing my age but Joe Namath was the most famous footballer of his day, at least here in New York where he won the second football Super Bowl way back before you, honey, were probably born."

"I think I heard of Fran. Is he the guy who just died and was married to Kathy Lee?"

"No that was Frank Gifford, his wife had his brain sent out for lunch when his cock, excuse my French, was the healthiest part of his body."

"Oh my."

"Frank, not Fran got into trouble fucking an airline stew a few years back, Kathy Lee went crazy, as if she isn't crazy enough to start with. Anyway, what do you say to a good steak dinner out tonight?"

"Could you pick me up? I hate the subways."

"Sure, no problem, just tell me where."

So Sophia wrote her number and address on little card with the "King of Bourbon" logo. I smiled, did some sort of silly bow, turned and I bounced my suitcase down the 5 stairs and rolled it out to a taxi and on to the Crisco Hotel on 5th and 48th. No, the hotel is not named after that butterball from New Jersey who thinks he can be president when he can't even keep the traffic on the Geo Washington Bridge moving.

Around 8 o'clock, I gave Sophia a call, left the Crisco and headed over to her apartment with a driver I knew. The driver drove for Uber but turned off the i-phone app when he was privately employed so he didn't have to pass a commission on to Silicon Valley. His name is Olauf, but he is not a Swede, he's a Mexican. How he got that name I'm afraid to ask.

I called Sophia up when we got there, pulled up to the curb of a nice building on 38th Street,

"I'll be right down," she answered.

I would have preferred to go upstairs but what ever worked for her was all right with me. She came out the front door wearing a large tangerine hat, dark Prada white rimed sunglasses and a low cut lace blouse. She carried a long coat in her arms knowing by nightfall it would be chilly. Instead of a dress she wore tangerine shorts and matching heels that set off her long beautiful legs. She was a knock out. Looked like a model, a Holly Golightly if I ever saw one. Tall, tight, tucked and oh my God, her breasts were just about tipping over the Magenot Line. (For those of you who are not History Buffs, the Magenot Line was a defensive wall the French built to separate Hitler's Germany from France. The Germans instead trespassed over Belgium in an end run, to conquer France in a matter of days; i.e. it's a line that hardly ever holds up.)

I jumped out of the black Mercedes to open the door; she stepped in with those 6-inch heels that made her a little taller than me, jumped in besides her and we were off.

Broadway Joe's is up on 47th and 8th. We got out at the corner and walked in a few feet because it's a one-way street like most of the odd numbered streets. Once inside Joe's, we were treated well as you might imagine and the whole restaurant turned around to check her out. I felt like a Prince escorting a Princess. The waiter lost no time in taking our order.

"Would you like some crushed garlic on the steak?"

"No, I'll pass on that as I intend to make love to this young lady for most of the night after dinner."

Everyone laughed including those dinning near and around us. I then added, "It's our honeymoon." And everyone congratulated us; Sophia just smiled as her face turned red.

The steak house dinner for two was quite good; it came with two giant baked potatoes and creamed spinach. The meat was cut very thick and burnt crisp on the outside while being red rare in the center. You can never be sure if you will get the right thick T-bone for two, but we did just fine. We'd started off with old-fashioned Martinis, a bottle of Chianti Classico, a Florentine delight that is dry with a taste of terra that becomes sweeter as you drink it with the meal. Of course we finished off the meal from the rolling desert tray with a healthy portion of chocolate dripped whipped cream filled Profiteroles (tiny cream puff balls piled high) and a small cup of double espresso.

After dinner, I phoned Olauf to meet us with his car. By now it was dark. The sky was obscured by the close-knit buildings and the chilled wind funneling up from the Hudson, a few blocks away, was cold. We got into Olauf's car as quickly as possible; he had the back seat heater running full blast.

"Have you ever been to the Sky View Motel?" I asked Sophia. "There is a view from there of Upper Manhattan that will take your breath away. Well it's just spectacular. Would you like to go?"

"Sure," my Sweet Sophia said, she was primed to trot. Olauf drove us up the curved route along the Hudson, past the Cloisters and then onto the west side highway as we made our way north, in the direction of the Tappan Zee Bridge where our Motel was located on the Westchester side. Of course I had reserved a room but they were quite empty that night. I told Olauf to get lost for a few hours and Sophia and I checked in.

When we got into the room it was cold as hell (an oxymoron) so I turned the heater up, which was one of those fancy gas units built to look like a fireplace. It ignited with a whoosh. We moved to look out the window and she could not believe her eyes. In the distance the George Washington Bridge dangled across the sky like a chain of pearls and the twinkling lights of Manhattan lay behind it. The sky was clear, the stars shone through and the half moon was bright and satisfying to look at.

"Tell me about yourself," I asked.

She seemed very relaxed leaning on her elbows in her overfilled décolleté bra

"What is there to say? I was born in a small town south of Ipanema, maybe 45 minutes away by car, here there was not the rush or violence of the big city. I grew up in a community with many Italians in our neighborhood, strange to say, but there are various neighborhood enclaves for Italians and Germans throughout costal Brazil. Even as a child I picked up enough Italian to converse. Sure, I was a promiscuous little child, sucking the butcher's dick in the back freezer while his wife stood at the counter serving the customers, but I got free meat to bring home to my Mom. I studied English in school for several years. Having summer sex with English speaking tourists helped."

"I sucked and never missed a drop of cum and offered up my ass to any one who passed and showed interest. Just one caveat, every dick had to wear a condom, and I learned most men become generous after they cum. I've seen lots of friends die, if you wonder why check and you will see they left off the condom which are free in every gay bar or club. Of course you have to avoid the drugs because then you get sloppy. I come here to the US to work a few years ago."

Out of words for the moment, we started taste testing the mini bar. She would pick a bottle. Unscrew the cap and taste it, then pass it to me, it warmed us both up. By the time we got to tasting the tenth bottle, or was it the eighth, we were not only warm but before you knew it we were sitting on the bed in our underwear. She still had her lace blouse on and a thong. Of course I left the fireplace heater on 85 degrees, which facilitated the strip down.

"I just love this tasting game; she tilted her head back and smiled."

"So Sophia, you were saying you came here to work. What work did you do?"

"I'm embarrassed to say I started as a hotel clerk but the work was so boring and my girlfriends suggested I try escorting. It paid much better and it was fun."

"Really."

"But you see I was fighting with my inner self."

"What do you mean?"

"I show you."

She stood up and dropped her thong to her ankles. Her shorts were lost some time earlier some time before. She rolled down her thong panties. "Look, you see?" revealing a nicely shaved vagina.

"I was surprised but she seemed perfectly in order."

"You look beautiful."

"No, no, no, no, you look closely you see my labia needs to be given its final touch up."

"What do you mean?"

"I mean, well, I thought you knew, I am a sex change," she pulled up her tiny thong. You didn't know?

"You mean you used to have..."

"A cock...yes, and balls but no more.

Now I am a girl."

"Oh my God, yes you are,"

I put my arms around her and embraced her.

"Yes you are my darling, yes you are."

As I released her green eyes glistened with tiny tears.

"Oh you make my eye makeup run," she said.

"I'm supposed to get the final plastic work to make my vagina perfect in a few weeks. They want you to wait a year after the surgery."

"That's great."

I kissed her on the check but she embraced me, pressing her beautiful perfect breasts into my chest.

"I feel like we are going to be friends for a very long time. I reached into my wallet and peeled of $500, this is spending money for your trip honey and I'd be happy to accompany you to the airport when you are ready to leave."

We were lost in kisses, my fingers outlining her plunging neck line. My cock was making an obvious tent pole in my shorts.

"Can we spend the night and wake up early to see the sun rise"

"Of course"

She kissed me warmly, letting her teeth nibble for the longest time on my lower lip.

Her lace blouse fell away, I took advantage of these moments to unhook her bra and when she released my lip I started to suck her nipples and when I felt she was aroused I dropped to my knees onto the floor, licking her through her thong panties until they became transparent. I started to play with her vagina but it didn't feel the same as other women.

"Here, do it like this," and in a moment she'd instructed me in how to please a sex change, rubbing a little lower to the side of the vagina where the sexual sensation was most intense"

Sensing from her breathing and how tightly she held my cock I knew we were headed down the right road, at which point she pulled her wet panties off. I worked my way back up to her breasts and when my cock was on the level of her vagina I positioned myself to enter her whispering,

"I want to fuck you."

"Oh yes, please do"

And with that I slipped my cock into paradise.

Fucking a sex change is the same as fucking any women but perhaps it is more exciting. Then there is the added bonus that she is as practiced at anal and will say as Sophia did,

"You can fuck me in the ass as well if you like"

"Who would say "No?"

After a brief period of recharge I lay my cum trail right up her butt tail, so glorious an ass that it's likes I may never fill again. This was God given perfection.

We fell asleep in each other's arms; my dick encrusted with cum residue and slept a night of utter blackness. I don't know if she left the bed to wash what must have been a liter of sperm I deposited in her sacred receptacles.

I slept for a while and awakened to some slurping noise and light pouring in from the window. When my sleep filled eyes finally opened the room was filled with light and there was a soft gurgling sound. I awoke to see Olauf, our driver had returned and was standing on her side of the bed, his fat red dick protruding from his unzipped dark trousers and nestled in Sophia's red lips. She in sucked as he came at that moment, as he grabbed her hair and forced his cock ever deeper down her throat giving her no choice but to swallow all of his seed but that little that leaked from her lips when he pulled out, still red and hard.

"Oh my God, what are you doing to her and what the fuck are you doing?

"I'm sorry Sir. She offered and I accepted."

Seeing her on her knees, her ass so near my throbbing-ly erect cock, and as I was already aroused by what I had witnessed, I didn't hesitate, I entered her ass with one full swoop, in doggy style. She maneuvered me backwards until I fell onto my back and she sat on my chest, offering Olauf a second chance which he lost no time in penetrating her vagina, stuffing his red uncut cock wider and longer than mine into her vagina and in this manner we both exercised our dominion over her, at the same time we could feel the in and out of each others cock which added a separate motion and novel feeling. We became brothers as we fucked our sweet sister through her untold orgasms. My cock stayed the course, remaining firm in Sophia's tight ass while Olauf's cock flopped out spewing his prodigious cum over my ball sack, firming up in the cool morning air as if it were Elmer's glue.

Embarrassed, Olauf took a hand towel and tried to wipe me off,

"You don't have to give me nothing for the ride sir, give it to her instead."

"Yes you've had two rides already my brother," I murmured, as I pulled my softened cock from her ass as she stood up.

"Excuse me," she said, "I have to shower."

"Wait for me," I ran after her before the bathroom door closed, "this guy's cum load is attacking my balls."

I followed her into the shower, from the bedroom I could smell smoke, Olauf was obviously smoking his after-fuck cigarette.

We washed each other in the warm shower water; I particularly scrubbed Olauf's stinging sperm off my balls.

"Did his cum burn you too?"

"Oh I'm used to that. In Brazil we call it "Queima de esperma," or "hot cum" You know in Brazil and Mexico the men eat a lot of hot peppers and it makes their sperm burn but we kind of enjoy the tingle. "

"Well I can do without it." I continued running the water on my sac until the burning diminished.

She leaned over and kissed me on my cheek, "I hope you don't mind I suck off your friend. His cock was so hard I thought it would break through his pants so I had to give him relief."

"Yes, you gave him relief twice, but that's ok, it's your right to do what ever you want to and he's a good man."

"You should let him fuck you in the ass, he has a good sized cock." she said and she smiled, winking at me.

"Thanks, but I think I can manage with fucking your ass, mine is still a virgin and it's too late for you to penetrate me."

"Oh, I could use a well lubed 12 inch giant fat dildo."

"No thank you, Olauf's cock would probably hurt less," we both laughed.

Sophia pranced nude from the shower into the bedroom, her tits jiggling as she toweled down. Nothing embarrassed her about sex or her body. She was gorgeous! She dressed quickly and we all exited.

It was early morning and there was almost no traffic in sight. Olauf stopped a few blocks from the hotel at a McDonald's drive-through where we got their abundant pancake sausage breakfast and a hot cup of Mac java. It was a Sunday morning; the highway traffic was also light. We returned to Manhattan, Olauf dropped her at her apartment, me at mine and I still gave Olauf two crisp hundreds despite his protests. So ended the sexual escapade that blows my mind even today.

(More on cumming in Sophia to come)