tagTransgender & CrossdressersTrini Plays a Trick

Trini Plays a Trick


[This is my entry for the April Fool's Day Contest ... my first Literotica contest entry ever! Please vote if you like it, and thank you for reading!]

* The three of us showed up dressed to annihilate, and when the door opened and I saw the look on the guy's face, I wondered again if I was doing the right thing.

"Wyn?" I asked, giving him my patented make-them-rock-hard/put-them-at-ease smile: lips gently curving up and parted just enough to flash a hint of teeth. I was sure it was him and not one of his ass-wipe friends because no way would either of those laughing hyenas be standing there open-mouthed staring at me and Yoli and Kella with their eyes mostly on our faces. It would have been one or two up-down eye-swipes of our legs and fishnets and microskirts, then a pause on my tits, mounded up brown and ready to burst my silver top, then a big wolf-grin to let me know they were sure they'd be getting their money's worth tonight. But not this kid. His blue-green eyes spun at our outfits for a second, and then he just kept gaping from Yoli to me to Kella and back again, his whole expression painted wide by how beautiful he thought we were. It made me feel warm and happy and proud inside and then guilty at the same time. But he still hadn't answered, so I asked again, "Wyn? I'm Trini. I think you're expecting us?"

"Oh! Oh, yes," he said, and he actually held out his hand. Adorable. I laughed and shook it, and despite his shell-shock he managed just the right middle-ground of strength and gentleness to make my hand feel welcome and protected in his.

Shit, Trini. This kid does not deserve what's going to happen to him tonight.

Well, we were here. I'd just have to do my best to make things easy on the guy.

I introduced my girlfriends, seeing Wyn awestruck by Yoli's creamy Latina complexion and blood-red lips, then charmed by Kella's girl-next-door freckles and baby blues.

Then he held the door for us and said, "Come on in. This way."

When we got to the living room, it looked exactly like I expected -- giant picture-window view of downtown L.A. lit up for the night, enormous overstuffed modern leather furniture, though I was predicting a lot of black and silver and I got beige and white instead. And lounging in that puffy beige leather: the hyenas, who also looked just like I figured they would ... square jaws and clean-cut all-American faces split by toothy smiles that said they knew all-too-well how good-looking they were. A blonde and a redhead, both tall and athletic and dressed in the casually expensive clothes of young men with too much money. Well, at least I'd be parting them from some of that tonight to make up for their dickliness.

They clinked their beer bottles together and the redhead wolf-whistled as we came in the room.

Compared to his friends, Wyn didn't have a lot going for him. The guy wasn't bad-looking -- kind of ordinary, with a little rounder face and a little softer chin than the laughing jackals who'd found me on the net and secured my services. His dishwater-brown hair had that can't-quite-find-the-right-style-for-it cut, not boldly short or comfortably long, just an unremarkable in-between. Out of the three, he was the only one looking nervous -- but it was an excited nervous, almost a hopeful puppy nervous, not the kind of nerves that made me laugh inside at some clients.

"Dibs on the Hispanic chick," said the redhead. "Which one are you calling, Jack?"

The other dude chuckled. "Damn, Pete, don't you remember it's Wyn's birthday? So, Wyn. You want the black one or the brunette?"

Wyn looked from me to Kella, his mouth open hesitantly. Not like he was unsure -- I'd seen from the second he opened the door that my pushed-up cleavage and lusciously made-up face had all but a fraction of his attention. No, it was more like he was worried that picking would make him sound as tacky as his two friends. Or that it would hurt Kella's feelings to be passed over for me.

Whoa, Trini, you're going hog-wild on the assumptions there, girl. Just because he's a little meeker and nicer-looking doesn't mean he's not in the same snotty rich-kid club as his buddies.

But I couldn't help thinking Wyn was different. When Jack and Pete had described the April Fool's joke they were hiring me for, of course my first question was, "He's not going to punch my lights out when he sees, is he?" And their answer was, "Naw, Wyn couldn't hurt a fly. Mister Shy and Harmless. I'm not sure he even got himself laid in college."

The setup didn't exactly appeal to me, but I figured turning the hyenas down would only make them go find someone else, maybe someone who'd be as mean about the joke as the two of them were. And when they asked me to bring some friends, and when they agreed to the over-the-moon price I gave them, I went against my better judgment and gave in.

Now, here we all were, with poor Wyn trying to figure out how to say he'd rather fuck me than my fine freckled friend Kella.

Before he could answer Jack's question, though, the blond guy laughed again and said, "Just kidding. I'm taking the brunette."

Wyn looked relieved and took his eyes completely off Kella. It made me a smidge madder hearing how Jack and Pete treated him, especially on his birthday. But I didn't let that show in my face, because Wyn was staring into my eyes, obviously trying to figure out what to say.

"Look, honey," I said, taking his hand between both of mine and stepping closer. "I know a nervous face when I see it, but you've got nothing to worry about. Why don't we go find a little privacy where we can get you more relaxed."

He swallowed. "Uh, sure."

I glanced over at Jack, who nodded toward a hallway and said, exactly as the plan called for, "Why don't you guys take the spare room, first door on the right. Pete and I will stay here and get acquainted with these lovely ladies."

"Super," I said, with a grin and a nod to each of my friends.

Yoli immediately glided over to sit next to redheaded Pete on the couch. Kella said, "Any chance I could have something to drink?"

"Sure, babe," Jack replied. As he stood and headed for the kitchen, I led Wyn over to the hallway and down it to the first door on the right.

* * *

In the bedroom, I didn't pay much attention to the huge bed or its incredibly expensive, satiny comforter. I was looking, as subtly as I could, for the camera. Fortunately, I knew about where it would be, because Jack and Pete had been specific about positioning myself for the big reveal. They wanted to make sure the video caught both the contents of my panties and the look on Wyn's face. The mammoth dresser to one side of the room had an accessory box and a couple of picture frames on its broad top. I spotted what looked like a micro-camera peeking out between two of the photos.

With a click, I shut the door behind us. Then I tossed my purse on a corner of the mattress, turned to Wyn and pulled him close to plant my biggest, best kiss on his lips. Maybe this wasn't going to turn out the way he wanted, but I damn sure meant to give him something nice to remember for the evening.

He grunted in surprise as my tongue shot into his mouth and I got my tits pressed hard enough against his chest to make sure he really felt their curves. Then he started kissing back, his hands gliding around to my shoulders, down my spine, one to the small of my back and one to my ass. He pulled me tighter, fingers digging passionately into my butt-cheek as his tongue danced with mine just beyond his teeth. I made sure to stick my bottom as far out as I could, both to completely fill his clutching hand and to keep my crotch back from his, since I found I was already getting really hot.

After a minute or two, I pulled back.

"Let's get you lied down, sugar," I said breathily. The hunger and amazement in his eyes made me want him, made me wish I was what he wanted. He nodded, and I guided us both over to the bed, making sure that when I crawled onto him, my shoulders and hair would hide his face from the camera.

Chest-to-chest on the mattress, we kissed a little more. His hands moved along my sides, came around to feel the edges of my breasts. I couldn't believe how horny this was making me, and I had to force myself to stop and do the right thing, lifting up and away onto one elbow. He took this as an invitation to get his hand all the way onto my boob on that side, which made me gasp and made him look very happy.

"Wyn," I whispered to him as he smiled up at me. Fuck, I thought. Fuck, I should not have done this. This is going to be so awful. I went on, keeping it too low for any mike to pick up if the camera had one or if they'd planted one somewhere else in the room. "Wyn, I'm going to tell you something, and I need you to keep holding me, doing what you're doing, without saying anything."

He looked a little puzzled, but very agreeable, like he thought I meant to say something kinky. As opposed to something terrible.

"Look, honey, just ... remember, stay quiet," I whispered. Then I tried to find my courage, and went on, "Your friends are playing a joke on you."

"What?" The speed with which his expression changed told me how used to being pranked he was. I guess having an April Fools birthday did that for you. To his credit, though, he kept his voice to a whisper and kept his hands going, one on my tit and the other on my ass.

"I'm so sorry about this. Jack and Pete didn't just find any hot escort they could get hold of," I went on, quick and quiet. "They specifically wanted a T-girl."

"What?" he asked again. This time, though, he looked puzzled along with his angry simmer.

Holy shit, does he not even know what a T-girl is?

"I'm, um -- shit, I'm a she-male, Wyn. I've got a cock. I'm a chick with a dick. And there's a camera on the dresser over there to record what you look like when you see it. Jack and Pete found me on the Internet and told me how they wanted me to trick you, and had me bring along a couple of friends who aren't she-males for them. Anyway, you seem like a really nice guy, and I didn't want this to go any further and make it any worse for you than it had to be. And I don't want them to get any more satisfaction out of this than they already have, so I hope you can keep playing along, and in a minute, when I show you, you can just shrug, maybe, and say, 'Yeah, I knew those cocksuckers wouldn't do anything that nice for me.'"

Wyn kept looking up at me, his face now blank and his hands unmoving, still holding my flesh, but doing nothing with it. I felt so sad.

And then he said, "No."

"Uh ..."

"No," he repeated, as something unexpected appeared on his face -- something steely and decisive. "No, not this time. Motherfuckers. I've known those guys since middle school, but this is the last straw. I'm done. I bet they told you I'm a virgin. I keep telling them I'm not, but maybe they know it's a lie, or maybe they just can't believe I could land a girl." He was really burning now, voice low and searing like a hiss of steam off coals. His fingers clenched, digging into my ass. "I've been looking forward to this for weeks, thinking maybe they were finally going to do something actually cool for me, thinking I was finally going to get laid, and now ... just ... fuck them. I don't care what they think."

"That's good," I whispered, although I wasn't sure what he meant. "You shouldn't put up with their crap."

"No, no," he said, running the one hand up my back and kneading my breast with the other. "I'm not talking about them anymore. I'm talking about fucking someone, tonight, right now."

I blinked. "But ..."

"Listen, you're smoking hot, you've got great tits --" He squeezed the right one as if to prove his point. "-- and if there was a real chick as hot as you here right now and she said she'd let me fuck her in the ass but not the pussy, I'd be all over that. So what's the difference?"

That made me swallow, hard. My cock felt ready to burst my panties and skirt too. "Wyn, are you sure you want your first time to be --"

"I just want my first time to be done, Trini. I was ready for it to be with some slutty hooker -- I don't know why that would be any better than a hot she-male who actually wants to be nice to me."

I watched his eyes, the color of clean tropical water over coral reefs. He really meant it. And he seemed so sweet. And his hands on my body were making me killer horny.

With my heart pounding and my eyes a little teary, I smiled at him.

"Okay, then."

From beyond the door and around the corner, a shout rang out: "Yeah! Fuck, yeah, suck it, bitch!"

It sounded like Pete, which meant Yoli was working her magic. That girl has skills.

Crawling back a bit from Wyn and putting on my sexiest voice for the camera or mike, I said, "You want some of what's going on out there before we get to it, then?"

"Sure," he said, reaching for his belt buckle.

"No, sweetie, let me."

I pushed his hands aside and shifted on the bed so I was crosswise to his body, kneeling. With a patient, lingering touch, I undid his belt, undid the button of his jeans, undid his fly. His breath sped up as I tucked my fingertips beneath the waistband of his boxers, then slid my whole hand in and discovered a firm, already engorged cock waiting there. I ran my fingers down its length and then up again. Wyn bit his lip.

"Here, let's get these down," I said, tugging at his jeans. He obliged me by lifting his pelvis, and I pulled and shifted the fabric down past his hips. "Mmm, much better."

Bending down, I found the straining beam of his dick with my lips and nibbled at it through the front of his boxers, making it twitch and leap and smudging a little purple lipstick on the cloth there. Some more words of amazement rang out from the living room. I decided to try to get Wyn to come before Yoli or Kella managed the same with the other guys. He said he was a virgin, so I didn't expect that to be too difficult -- especially since Yoli and Kella are both excellent cock-teases and love to draw a blow-job out.

My fingers found the slit at the front of Wyn's boxers and snuck inside to play along his shaft, then take hold of it, then pull it out. It stood up straight and tall and beautiful the moment I got it loose -- about average in size, but one of those really gorgeous cocks, clean and straight and symmetrical and looking like Michaelangelo had sculpted it from marble. My fist went right around it and jacked once, twice, three times as I stared. Wyn moaned. I grinned at him.

Then I lowered my head and took him in.

"Oh, god, Trini," he gasped.

I kept working him with my fist, just a couple of inches of his dick inside my mouth where I could tongue all around the head and taste the pre-cum leaking from the tip. He started panting. I relaxed my grip and slid my hand down so that the thumb and forefinger encircled the root. Then I dropped my head and replaced them with my lips.

"Shit! Holy fuck! Shit!"

The beautiful rigidity of his cockflesh swelled in my mouth. Damn, I don't want to make him come that fast, I thought, freezing in place with the tip of his tool at the back of my throat. More pre-cum oozed all over the rear of my tongue. I swallowed and felt him surge again at the squeeze of my upper esophagus on his glans.

Slowly, as I waited, his cock backed away from explosion and his breathing softened, became more even. I listened for it to get mostly back to normal, hearing him murmur in between breaths and hearing my friends in the other room coax much louder sounds from their assigned partners.

Once I thought it was safe, I bobbed slowly up and down, lips and cheeks as tight and flush to his shaft as I could get them, tongue curled around to the underside of the rod, tickling, licking.

It didn't take more than a minute of this to get him right back to the edge of orgasm. Once there, I popped loose and gripped him with my hand again.

"I'm so hot to be fucked," I said, staring him in the eyes. "Do you want to fuck me?"

His voice came out rough and hungry: "Yes."

Grinning, I turned around and wiggled my ass. "It's all yours. Grab a condom and some lube out of my bag."

"Lube?" he asked, reaching for the purse as I drew my skirt slowly upward, raising the curtain on my panties and their contents. I watched his face -- Wyn wasn't much of an actor, but he made the surprise look mostly believable as his eyebrows went up along with my skirt. "Hey, is that --"

"Yeah, it's a dick. But you don't have to worry with it. You can just fuck me in the ass and pretend I'm like any other girl who likes it anal."

"Huh," he said.

"Is that okay?"

"You know what? Sure, what the hell." With a shrug, he started digging around in my purse. "Dang, there's a hell of a pile of condoms in here ..."

I blew him a kiss. "Honey, I like to be prepared for a man who can go as many rounds as I can."


And then he was popping the lid on the lube and squeezing it out all over that gorgeous cock, sheathed in my favorite thin pink latex. I shimmied my panties down just enough to reveal my asshole.

"That looks so good," I told him. "Get it in me. Fast."

He came across the bed on his knees, wide-eyed and shaking his head. "Holy shit, I can't believe I'm really going to do this."

"Believe it, baby. Do it." I put my face in the silky soft comforter and thrust my bottom up at him. Fingertips contacted my ass hesitantly, on one cheek and then the other. I could feel the sticky lube that had gotten on one hand as he slicked his rod up. Then that hand left my ass so that he could use it to guide himself, and the other hand spread flush against my butt-cheek.

The cool wet tip of his cockhead brushed my anus. I groaned.

"Oh my god, this is it ..." The anticipation in his voice made my heart flutter.

Then he pushed.

He'd managed to get the angle right, and his slow, steady pressure made everything work perfectly. I relaxed just barely enough to let him in, so that once his tip popped through, my sphincter gripped him as hard as it could and still allow penetration.

"UHH!!" I grunted, too loud to hear the start of his moan as he leaned into me, sliding and sliding and sliding until I felt his pubes in my ass-crack and his crotch flush up against my tailbone. The whimpering sound he made almost got me to come all by itself. It was one of the most glorious cock-thrusts I'd ever felt. "Wyn, Wyn, yes, babe, fill me up ..."

Panting, he bumped up against my bottom a couple of times, not actually withdrawing enough for them to be called strokes, just little millimeters of slide at full depth that made him groan and tremble. I wanted to roll my hips, snake my spine side-to-side, lunge forward and back and just fuck the hell out of the wonderful cock he had me impaled on. But I knew it would be over in seconds if I did, so I just let him go at his own speed.

"Shit," he gasped. "This is going to be really fast ..."

"That's okay, sugar. You just enjoy yourself."

"No, no, I want it to ... last ... at least a little ..."

"Well ..." I wasn't sure what to do. He was stone-still inside me, and I really wanted him to start fucking me -- really wanted to feel his fire-hose go off and dump its load inside me. But it was the guy's first time, and I also wanted it to be as special for him as it could be. "I guess just stay as still as you can, and reach around and pull my top down and manhandle my tits a little. That sound good?"

"Uhhh ... uh-huh."

He leaned forward, chest against my back, dick still speared way up inside. One hand went down to the mattress to help support his weight as he fumbled at the front of my shiny, tight top.

"Oh god," he said, "it feels so good."

"Me too, sweetie. Use both your hands. I'm pretty strong."

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