Trini Plays a Trick

My first trans story. It won't be my last. Awesome, so hot. Makes me want to do that.

I genuinely like this story . This was a breath of fresh air . I like how Wyn , and Trini clicked , but the ending , was spot on perfect . 5 stars .

Tall, African-American, relatively dark, with deep, soft, brown eyes, generous lips, and a medium/average sized nose. She has very long legs and "sexpot" cleavage. Her hair is usually a big poof of ringlet curls or natural frizz.

I don't have her do a lot of self-description, because I am not a big fan of stopping the story flow for the narrator to describe herself, and I'd rather let the reader fill in the image of their own ideal black transgender escort. Sorry if I left things too vague for your tastes, but thanks very much for asking!

I forgot if you had described her.

I think that may be the first time I've been called a master storyteller! I'm very flattered! Thank you for the high praise ... I'm glad you liked the story.

The story is fantastic! I loved that those jerks got what was due to them. You are truly a master storyteller.

Wow, what a detailed and thoughtful story structure! I think you've described the basis for a very cool story, with lots of emotional texture and personality. I would actually encourage you to write it out as a full story yourself, because you seem to have such a clear vision, and you obviously have skill at expressing yourself in writing. I find your reading of Trini more vulnerable and maybe a little younger than I was thinking ... I always think it's cool when people get something out of my writing that I wasn't expecting. I do have a couple of other Trini story ideas rattling around in my brain, though I don't know when I'll find the time to write them. Cross your fingers for me!

Thanks so much for all the imagination and time you put into your comment. I can't tell you how flattered I am that my story inspired so much creativity. Take a crack at writing it yourself, seriously! I think a lot of people would enjoy reading the results, myself included.

I'd love to see more of her. So would Wyn, I'd expect. She's his first and he's a shy boy who needs to be lured out of his shell; she's hot and he's not going to be able to forget her how much he tries.

That said, there's likely a backstory behind each of this pair. If you care to continue with this tale, here's one way I could see this going if you take the concept and (please) run with it:

Wyn's 21, reasonably intelligent, likely still in university at that age but in the final year or close to graduation. He's likely in a rather humble student apartment and carrying a fair amount of student debt by now, even though his family leads a fairly comfortable upper middle class existence. Odds are, he spent most of elementary and secondary school as the awkward kid with four eyes, zits and braces - all of which are now gone, but he did grow up being picked on and entered university more than a bit shy, missing out on all the sexual experimentation that seems to go on between students away from mum and dad for the first time to get that first taste of freedom. He feels like an underdog now, but maybe someday - once he gets himself established and builds up a bit of self-confidence - he'd be a prime catch for some gal who wouldn't have given him a second glance a decade ago. At the moment, however, he has a bigger problem - it's April and he's in the middle of the last year of final exams - some of which count for 80% of the mark for the entire course. He needs to stop worrying about Trini briefly to get his schoolwork done first and then he needs to land a good permanent job. Funny how every company wants experience but none are willing to give anyone any fresh out of a good university.

Trini's likely in her mid to late twenties and had led a somewhat more difficult life. She was never happy as a boy and always wished she had frilly dresses, pretty dolls and feminine things like her sisters. The only reason her family even tried sending her to a psychiatrist or counsellor is because they'd hoped he could "cure" her and make her live like a normal boy. Of course it doesn't work that way, at least not for someone as stubborn and determined as Trini. She waited until she was out of the house and working in a day job to begin transition, only to hit a huge obstacle: at some point after getting partway through some rather permanent physiological changes she was no longer able to continue as a male in her old job, but wasn't quite passing as a woman and had no employment references (or anything else) as a woman. She went through some harsh economic hard times, might have even landed on welfare at one point, but couldn't make ends meet - let alone afford the costs of completing her transition. As much of her family was unsupportive, she turned to a group of other transwomen as her sole allies. One of the group mentioned having spent a few years as a sex worker at some low point where there were few or no other options, but eventually left the business and was close to completing her transition. Most of the others were shocked by this revelation, but many had made their own sacrifices in different ways - one was stuck partway through transition and stuck in a public housing project on a disability pension, unable to afford SRS or other surgeries to transition, another had made some good money as a big-shot financial advisor but was biding time, waiting to sell the client list to another broker and retire early to go full-time en femme because her clients knew her as male. At least one had been on a first-name basis with the +1-800-SUICIDE operator at one particularly difficult point. With few other options, Trini did try prostitution and found that it was not an easy life - the clients seemed to treat this as some sort of freak show, but the money was good enough to get her back on her feet (or at least her knees) and pay for electrolysis, facial and voice surgery, a few key milestones which aren't SRS (sexual reassignment surgery or genital reconstructive surgery, the last and final step) but have made her pass as a beautiful woman - at least on the outside. She is making better money now and has been able to relegate the "female escort" bit to a part-time self employment (operated from a small website) and try to pick up a few college courses so that she has an exit strategy into a regular career once she either completes the transition, is no longer functional as whatever fetishised "chick with a dick shemale" her clients seem to fantasise her to be or is simply too old to be supplementing her income with sex for money. She also still hopes to reconcile with a few of her more understanding (or is that merely "least worst"?) relatives if they can be persuaded to finally accept her as a woman - but realises the sex work could be an obstacle were they to find out about it. So many plans, seemingly on hold, but there's finally this small bit of light at the end of the tunnel.

And then this bizarre call came in. It's awkward enough when someone enquires with some weird fetish like "I've always wanted a shemale dickgirl to piddle on me in the hotel bathtub" and she'd usually quote double and triple the usual prices just to try to brush them off, but this was just plain arrogant - the prospective client doesn't even want her sexually, he just wants her to put on some sort of freak show as an April 1 prank where his buddy gets to see "a surprise in her pants" and freak out as if she's some sort of mutant. Yeah, right, some surprise. More like a birth defect that she wishes at this point she never had between her legs. She's been putting on a brave face lately, but her self-esteem is quite frankly in the toilet... basically right where it's been for the last few years. Trini doesn't need this. At any price. She's hurting enough. She quotes some over-the-moon price in the hopes that they'll balk, drop the idea, maybe go play on the motorway or something. They accept. Now what? She half considers waiting until the last minute and calling back to cancel the session, but instead she discusses it with some of her friends - a few of whom have very warped minds - and a plan is born.

They show up. The three guys are there. Two of are, quite bluntly, (boy parts) and act like (boy parts). Pretty much what was expected. There's something about the third one, the birthday boy, that she just can't place. He almost seems human, nice, but at the same time awkward like a poor dear caught in the headlamps. All these days of Trini planning "I'm not going to let them hurt Trini because she's suffered enough", repeated like a stuck record a stuck record a stuck-, and now there's this other issue "I'm not going to let them hurt Wyn because he's suffered enough". Argh, where did that come from. Focus, girl, I'm a professional, right? No emotions? Oh, shit. And then, when it does hit the fan, Wyn is pretty much protectively standing between the three gurls and his two dufus "friends" for long enough for them to make their exit. Pity Trini didn't bring him with her when they made their escape. Oh well, it's over now.

Trini might have forgotten about this incident months ago, except that it made a good anecdote and her friends still get a laugh out of how this ended. Heck, she pretty much had put it out of her mind and didn't give it much thought when that e-mail showed up from "wyn@somecompany..." asking for "a date" and wondering what the price would be for one hour. She quoted the usual rate and didn't give it much of a second thought. He sent her his address and asked she wear something nice.

Um, OK, whatever. She cleans herself up, inside and out, puts on an evening gown (pretty much assuming he's just going to remove it as soon as she walks in the door anyway, but if that's what he wanted...) grabs her jacket and heads out. The address turns out to be residential, in a rather ordinary-looking apartment block. She hesitates briefly, then figures that he wouldn't have told her where he lives and where he works if he intended any real harm, then goes ahead. He answers the door. The place isn't anything to write home about, but he looks vaguely familiar from somewhere. She begins to remove her jacket and he tells her to leave her coat on. What? He doesn't want to go through with this? I suppose that figures, he does look nervous - and why is that face somehow familiar? If he does back out, will he at least reimburse the cost of the trip over here?

He grabs his coat. "We're going to dinner." He hands her an envelope full of cash and they're out the door and into a cab to the restaurant. "My treat. I owe you that much... and I miss you". Um, excuse me? I've missed something here? "I'm not April fooling. You're the only one that's actually been nice to me." And then the high-heel slipper drops. Wyn. Oh, dear. What on earth have I gotten myself into.

The restaurant looks casual enough upstairs, almost a British-style pub with the chicken wings and the fish and chips. There's a bar and a small dance floor downstairs. Wyn looks overdressed. I look overdressed. He's staring at me intently. He mentions that he chose this place because he comes here often with colleagues. The food isn't half bad, but I'm a bit curious as to why he'd pay to join me for dinner... surely there are plenty of attractive ladies who would jump at the opportunity to join him for free? Apparently he wants me. I didn't see that one coming. For crying out loud, I'm a hooker, I'm a tranny, I'm a freak and even my inferiority complex isn't as good as anyone else's. He's looking at me that way, with those puppy dog eyes, and when I begin to try to explain why this can't work he gives me this look as if I'd tried to dump him and broke his heart in a million pieces. I fall suddenly silent. If only I'd met him a decade from now, transition completed, college education completed and in some respectable job... but would he wait that long for me? Another couple walks by, seemingly absorbed in each other. Wyn looks up and there almost seems to be a glimmer of familiarity. Don't tell me, he wishes he was the other lad on a perfectly normal date with a perfectly normal woman. There's no way he could wait forever for me, is there?

He introduces me to the other lad. One of his colleagues, apparently. He asks his workmate "who's the pretty girl" and he introduces her to us as his new girlfriend. To us? I almost want to leave these two alone, but it's too late. His colleague asks about me. He wants to know how a shy boy managed to get a date with such a pretty girl. Wyn replies vaguely that "Trini is a hot babe I met at a party" and leaves it at that. Big sigh of relief. His colleague's girlfriend tells us that we make an adorable couple, then the pair wander off to grab a meal.

I ask myself, "Trini? What the heck have I gotten myself into?"

Well, no spoilers about the potential sequels, but at least one of them does involve Wyn ...

: )

Thank you for your very kind feedback!

How could this night get better? "Now that THAT'S done....Wyn, sweetheart, grab your cap and come home with me...." it would be so nice if this prank turned into love. Especially if her GIRLFRIENDS had caught video of the others to blackmail them to silence.