tagTranssexuals & CrossdressersTrini Trims the Tree

Trini Trims the Tree

byIanSaulWhitcomb©

[This story follows "Trini Plays a Trick" and "Trick or Trini," but can probably be read pretty easily on its own. I hope you enjoy it, and Merry Christmas to all!]

*

So, flying doesn't normally give me wobbly stomach. And opening up that I'm a t-girl doesn't normally make me weak in the knees. I'm even the coolest of cucumbers about what to say when my occupation comes up in conversation. ("Event coordinator" if someone's introducing me to their granny, "world's greatest escort" if it's pretty much anyone else.)

And being around rich white folks? Never a problem -- not with my client list, honey.

Which should have made the fifteen-minute flight by twin-prop, six-seater puddle-jumper from Nassau to a super-exclusive little Bahamian island for a week of Christmas-time festivities easy as easy-peasy pie with piece-of-cake chaser.

Right?

Only for some reason, I think I had crushed every bone in Wyn's hand before we even got off the runway.

"You okay?" he asked as we got airborne. His left hand covered the back of mine where I had his other one trapped in my quivering death-grip.

"Sure, yeah," I said, tossing my hair in an attempt to loosen up. It felt a little heavy and weird because I'd had it cornrowed to cut down on maintenance if we got in the water. "When do you think they're going to start the drinks service?"

He laughed. It was that warm-every-vein-and-squooshy-bit-in-your-heart laugh of his, which helped me take a deep breath and unclench some to let the circulation back in his fingers. Our hands swung easier in the aisle between our seats.

"Hopefully," he answered, "right after they send the cameraman through to get this scene on video -- you flipping out while I'm actually relaxed for a change."

"Are you?" I blinked and turned my head. Sure enough, once I got my eyes working instead of staring out the front windscreen at blue Caribbean sky, I saw he was right. "Hot damn, you are, aren't you?"

Wyn shrugged and scrunched his mouth to one side. His blue-green eyes sparkled like the tropical water along the beaches below us. "I don't know ... maybe more relieved than relaxed. We're here. It's real now. Instead of stressing and freaking, it's time to just ride it out. Whatever happens, I'm getting on a plane with you next week and flying home."

I shivered for a whole different reason and leaned across the aisle, tugging his hand to get him close enough I could put my lips on his.

Buck up, Trini, I told myself when the kiss broke and we smiled at each other and kept swinging our hands together. You're not the one who's got to introduce his transsexual hooker girlfriend to his one-percenter parents and then top it off by telling his dad he's quitting the family business. If Wyn's shaken the shaky-shakes out of his system, you got no excuse for pissing your panties.

The four-day trip from Miami had felt more like a rollercoaster than a cruise. Don't get me wrong -- we had a blast. But at least a couple times a day, at a lull in the dancing or when we finished getting a massage or decided we'd had enough of the ship's casino, I'd catch him with this look on his face and have to squeeze him close and take him for a drink or a sunset walk. Or if all else failed, get him back to the cabin and screw his brains out. That last one worked like a charm every time.

The look always came back, though. This was a high-fucking-stakes trip for Wyn. I mean, girlfriends come and girlfriends go, and even if I was a pretty big shocker of a girlfriend, a guy can get away with bringing home the wrong girl at least a time or two, even if he's from Upper East Hoity-Toityville like Wyn. But you're talking a whole other ball game with the bit about "Hey, Dad, you know that CFO thing you're lining up for me? Fuck that shit."

And as supporting and reassuring and screw-his-brains-out sexy as I stayed on the outside, every day took me up another notch on the anxiety scale as we sailed closer to this showdown.

"So why are you getting nervous all of a sudden?" Wyn asked. "That's not your normal digs."

I shrugged. But I guess it was more of an I-don't-want-to-say shrug than an I-don't-know shrug, and the look in his pretty sea-and-sunshine eyes told me he saw through it.

"Come on," he prodded, squeezing my hand when I didn't answer right away. "You're way too tough to be worried what my parents think of you. I didn't make them out to be that scary, did I?"

I shook my head, frowning.

"Then what?"

Deep breath. My dark, long-fingered hand in his. Those eyes.

I couldn't help ducking the subject in typical Trini fashion. With my best smirk sliding into place, I said, "I'm terrified if I get in a pissing match with your dad, it'll make him feel inadequate when I pull mine out and he sees it."

"Uh-huh," he said. Then he gave me a little I'm-letting-you-off-the-hook-for-now smile. "Whatever you say."

We stayed quiet a while. The plane rose, banked a couple times, then turned its nose back down. The view out the windows ... holy shit, was that ever something. I mean, I've been to the Bahamas before, on a cruise with some friends a few years earlier. The islands and the ocean and the sky are freaking amazing no matter what the angle. But from out the window of our little twin-prop plane, hanging in the middle of blue that went up forever ... just ... fucking wow. Little jewels of islets, emeralds set in gold-ring beaches floating through this crazy aquamarine that ran off to the edge of the world ... whoosh.

It couldn't help but settle down my antsy-ness.

At least until the pilot announced that we'd be circling our island and landing in a minute.

"Fuck," Wyn said, leaning across to look out my window as we made a wide turn. "Dad really out-did himself this year."

I looked too. And looked again. And looked again. "What ... wait ... did he rent a whole fucking island?"

The view out the window said that's exactly what Mister Moneybags Tate had done. We were headed for a little spear of land just big enough to have its own airstrip. A tiny cove opposite the grey line of the tarmac had two or three boats at a pier. Other than that, the greenery of the island was broken only here and there by the trappings of ultra-wealthy leisure -- a couple of villa-style houses, a crystal-blue pool, tennis courts, a tiny chapel that I guess came in handy if you wanted the place for a wedding. There weren't enough buildings to fit more than ten or fifteen guests, tops, so unless Wyn's dad had arranged to split the rental with some other group ...

"Damn, my dad likes to show off, but this is extravagant even for him. I mean, there's only five of us -- six if Liselle brings her friend Carly. I bet we're going to be outnumbered by the staff."

Welcome back, nerves. Sure wish this flight had actually had a drinks cart.

We touched down after a single circuit over the island. For the first time in my life, the plane didn't have to taxi anywhere once it landed; coming to a stop used up pretty much the whole damn landing strip, and we just turned in a circle by the maintenance building before the pilot shut down the engines with ocean to our left and a gazebo and a path leading off through the trees on our right.

"I'm guessing that's not your dad," I said, pointing to a tall black guy in a suit who stood by the end of the trail. As the props slowed, he walked across the concrete toward us showing a warmly professional smile.

Wyn laughed. "No. Probably the staff manager. The high-and-mighty Jerry Tate doesn't stand around waiting for anybody."

A few minutes later, we found ourselves headed up the steps of a ritzy beach-house, with Mr. Tompkins the staff manager preceding us to hold the door. I'd barely crossed the threshold when a crisply masculine, authoritative voice rang out from a side hall, turning my head.

"That you, Wyn?" said the voice as its owner strode into the foyer to greet us. "About time I get to meet this --"

To give him credit, he only faltered a fraction of a second when he saw me, blinking his steely grey eyes once before letting them glide onward to Wyn. The expensive, finely tailored dress-shirt he wore and the slacks and loafers that went with it said he made a habit of never meeting anyone while dressed too casually. Maybe he'd put on shorts and a polo shirt later, but not for introductions. I was glad I'd worn one of my nicer dresses.

"-- girlfriend of yours," he finished, keeping his eyebrows from tightening too much or creasing his high forehead.

"Hey, Dad," said Wyn, with a hint of oh-boy-here-it-goes in his voice. "I'd like you to meet Trini Jones. Trini, this is my father, Gerald Tate."

I held out my hand. "I can't tell you how glad I am to meet you, sir."

"Likewise, of course," he said, taking it.

No feel of nervous sweat on either of our palms ... which was good, because the second his classically sculpted face hit my retinas, I thought:

Oh, it's this Jerry.

* * *

The first thing Jerry Tate had said to me, closing his hotel room door behind us a year and a half earlier, was, "So this is a bucket-list thing, and I don't need or want any sweet-talking or play-acting. Get your clothes off and let's get to it."

Then he turned away, shucked his bathrobe, and walked to the luxury suite's bedroom without even looking back. And that was a good thing, because if he'd looked back, he might have caught me trying to keep a straight face while I undressed.

Just to be clear, I don't make a habit of looking down my nose at clients or laughing behind their backs. But there's a certain kind of guy who just has to be in control. In control of himself, in control of everybody around him, in control of every situation every day. And when that kind of guy gets an itch for my kind of scratching, he can't stand it. He's been a thousand percent sure of his sexuality his whole life -- so "sure" he usually has to demonstrate it with homophobic jokes and a string of hot-chick conquests. But for some reason, he gets this kink, and he can't stop it working at him, and working at him, and working at him. And when he finally gives in and looks me up online (this kind of guy would never ask anyone for advice on how to get his itch scratched), he always has to make excuses ("bucket list"), demonstrate his maximum alpha strut, and let me know he's absolutely, definitely, completely not going to be into it ("no sweet-talk").

I feel sorry for the poor shmucks, because I always make sure they enjoy the hell out of themselves, and they always walk away half-ashamed of how much they liked it. Okay, maybe not always. Every once in a while, I get a call-back from one of them, and he turns into a regular, and I watch him soften up over time and start turning into a real man. But I could tell Jerry wasn't going to give a call-back.

On the other hand, doing his top-dog stride into the other room, he showed me a damn fine ass -- every bit as chiseled as his jaw. Legs weren't bad either, and the play of muscle in his back and shoulders said he worked as hard to control his shape as he did controlling everything else. So I ran my tongue over my teeth and left a trail of clothes all the way to the bedroom, pretty sure I'd have a good time showing Jerry an even better time.

"Okay," I said, rubbing my hands together, my cock and tits all out and swaying as I entered the room. "So you're the boss, obviously. What do you want to do first? And is there anything I should call you?"

"Jerry," he said, eyes fixed on my crotch from his place by the bed. That hard, grey gaze narrowed and eased a few times -- maybe trying to decide what to think of the first cock besides his own that would be entering his sexual history. His broad chest expanded as he inhaled.

Since Jerry didn't seem ready to give me my marching orders, but did seem to be swelling up pretty rapidly as he stared, I untucked my handbag from my armpit, raised both arms over my head, and did a slow turn for him. Here you go, Jerr. Some sweet, firm, curvy ass for you to drool over. A nice, soft waist. Girly brown belly over lonnng, fine legs. And a big, hard, black dick to let you find out whatever it is you want to find out. What it feels like topping a t-girl? How much sexy sausage you can get down your throat?

Or how to take it, deep and fast, up your ass?

He nodded his head of fine-groomed grey hair as I finished my turn. Like a lot of my clients, he had a couple of decades on me. But he wore it better than most. "That's good. You'll definitely do. For starters, come over here and get on your knees and blow me."

I'll bet my eyes sparkled as I sashayed toward him, grinning. The jutting pole of his hard-on made it clear he didn't need any foreplay, so this was a total dominance move. I'm betting that means you want to take it in the butt, don't you, Jerry? Gotta make sure I know my place before you let me into the driver's seat, right?

Sinking to the carpet, I clicked open the handbag and fished a rubber out by touch, my eyes staying on his and my mouth just inches from the swollen, pulsing tool in front of me. With a rip of the package and then just enough suction, I held the ring of the condom flush against the ring of my lips, then leaned and sucked so that I unrolled it by going down on him.

"Damn, you're pretty good," he said when I landed my nose in the soft brown curls above his root and got the rest of his rod all the way down my throat. I could tell he meant it to sound like a throwaway compliment -- but a little hitch in his breath told me I was doing better than just "pretty good."

Let's make you feel all safe and secure in your hetero self-image, then, Jerry.

I slurped.

"Hhh-hh ..." went his breath, ragged and hot. My eyes stayed locked on his. I brought my hands up to my tits and started squeezing them, teasing them, slow and steady in time with each bob and lick I gave his sheathed-up shaft. He got his hands in my big, frizzy afro and started thrusting. "Yeahhhh."

His hips upped the pace. I rolled with it, working my neck, my lips, my tongue, my throat. Jerry had a pretty hefty cock -- long and full, plenty to gag a less-eager deep-throater than me. The feel of it sliding along my inner cheeks, my tongue, stuffing itself down my esophagus, got me horny as hell. I've always been a sucker (pun intended) for having a good prick fuck my mouth, and the way he grunted and panted as he really got pumping turned me from stiff to steel-hard.

"Uh -- uh -- uhhh... fuck ... I want to cum on those tits ..."

"Mm ... hmm," I said, in a couple of gaps where his pistoning length left my airway clear enough for me to hum the noise out.

"Fuck! Yes! Suck it -- take that cock -- all the way -- in -- nnnggg ..."

"... mm ... hmm ..."

"Ah! Ah! Ah!" I felt him starting to swell as his humping went wild. "Fuck, yeah! Get ready ..."

He had that red-faced, mouth-shaking thing going on. The bulgy neck-vein thing too.

"OAH! Guh -- huuhhh ..."

His hands left my hair. One palm pressed against my forehead and urged my face away as orgasm charged up out of his balls and along his shaft. I could hear it in his groan and feel it with my lips and tongue, and with absolutely perfect timing, I circled my hand around that ready-to-explode man-member, stripped loose the condom as my mouth pulled back, and aimed his throbbing jets right at my chest. Hot, spattering splashes of jizz blasted out across the dark flesh of my breasts.

"AH, God!" Jerry yelled, his eyes and mouth wide as he watched himself douse my rack in white, spermy seed. "Fuck!"

I thrust my boobs out as far as they'd go and milked him for every sticky streamer he had in him.

When he finished, he gave a last groan and toppled backward to the bed, arms behind him to hold him up, face turned to the ceiling. For a while, he stayed like that, frozen except for the movement of his chest and belly as he gasped.

"Jesus," he said at last, once he got enough breath back to look at me. "You've got a hell of a mouth on you."

"Thanks," I said. I kept eye contact, using one fingertip to draw slow figure-eights in the silky runnels of semen he'd shot all across my chest. Then I raised an eyebrow. "That's not all I've got on me. Any particular part you're interested in trying out next?"

His eyes dropped from my face to my splooge-smearing finger and then down to the hungry beam of my cock between my legs.

"Yeah," he said -- in charge, sure of what he wanted, and now prepared to demand it. "I've got to piss ... maybe take a dump too. Then I'm going to have you fuck me in the ass."

"Ready when you are," I replied, meeting his gaze when he brought it back to mine. I added a hungry grin, but kept the, Just like I thought! to myself.

Jerry got up and strolled to the bathroom in that virile way some guys do right after they come, like the whole world exists just to get them off and every orgasm proves it to them again. I watched the toned muscles of his ass as he went, letting myself smile and shake my head at last. I'd noticed the bare bathroom counter on the way past -- no sign of personal toiletries. And I hadn't seen luggage anywhere in the suite. All of that told me Jerry had shelled out way more to the hotel than he had any practical reason to, and since our appointment was only for two hours, every penny past a plain room and king mattress had been spent to let me know I was renting myself out to a Big Man.

I resisted the temptation to check the trash for empties and see if he'd raided the mini-bar waiting for me. You've got a job to do, Trini, babe, I told myself. Let's get ready for that instead of peeking into poor Jerry's self-confidence issues.

It didn't take much to get back in business mode. All I had to do was arrange myself on the silky-soft bed, glide a couple of fingers up and down my shaft, and think about my client's well-muscled bottom and generously sized cock.

I do like my work.

When he came out of the bathroom a few minutes later, Jerry still had his top-of-the-world poise going. I looked him up and down and licked my lips.

"You keep yourself in fine shape, Jerry," I said. He grunted as though the compliment meant nothing, but I saw a surge go through his hanging dick when I said it. "Now how do you want this well-trained piece of equipment to find its way into that shape? On the bed? The floor? Face-to-face? From behind?"

He puffed up his chest a little. "I'm going to get on my hands and knees in the middle of the bed, and you're going to give it to me so I can feel your tits on my back and watch us in the mirrors."

His head gave a toss toward the mirror-doored closet along the wall that faced the bed.

"Yes, sir," I replied, putting a slink in my voice and shifting so I could throw the bedspread back. Jerry climbed onto the sheets with me, on his knees but spine upright and shoulders squared in manly fashion. I rolled on a condom and lubed myself up as he found a spot he liked. He paid no attention to where I was -- in fact, I'd bet he deliberately positioned himself so I'd have to move around behind him, instead of him pointing his ass my way.

Sure, Jerr, I thought warmly. I'll come to you instead of you coming to me. And then I'll come in you while you're coming too.

I made sure to drop the lube bottle where it would be in arm's reach once things got going.

Running my dry hand appreciatively up his biceps and around the hard swell of his shoulder, I worked my way behind him, leaning to kiss the side of his neck and tongue the little hollow behind his ear. In my peripheral vision, the mirrors let me see an upward lurch of his cock at my attentions.

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byIanSaulWhitcomb© 18 comments/ 28745 views/ 34 favorites

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