tagTransgender & CrossdressersTrini's Valentine Hat-Trick

Trini's Valentine Hat-Trick


[Happy Valentine's Day, everyone! Like my other contest entries, this one features transgender escort extraordinaire Trini Jones. You don't need to read the previous stories before you read this one, but there are a couple of mild spoilers for the others in it, if you're the kind who worries about spoilers. Thank you for reading, and I hope you enjoy it!]

In my line of work, February is your basic gold mine. I mean, I stay busy the other eleven months out of the year too, but February is bop-till-you-drop month, and my calendar, especially for the week of Valentine's, gets filled six or eight months ahead of time. You've got your sad-and-lonelies, your gotta-have-a-date-for-the-V-Day-partiers, and your stepping-out-of-their-usual-boundaries couples, just for starters. So for the past five Februaries, Cupid's busy season has been my busy season too, and instead of filling my head with the color pink and the calls of cooing doves, it's been bringing the color green and a nice big cha-ching! sound.

Until this year.

This year, having a high-premium paid date for the fourteenth really chapped my hide. So much so that as I knocked and then stood there on the apartment's doorstep, I kept bitching at myself for feeling less than my usual one hundred percent professionalism.

Look, Trini-beans, at least this year you have a real Valentine of your own. You're the luckiest girl in the world, right? So what if you don't get to spend the actual evening with Wyn. Get your head off him.

But Wyn was hard to get out of my head under any circumstances, and I was especially frustrated at how close we'd come to having the evening to ourselves. He'd locked down an amazing set of reservations for the twelfth, knowing that I'd been booked for V-Day since August.

And then my fourteenth had canceled.

Who cancels on me? I mean, I'm the whole package and then some. Hair, boobs, flawless chocolate skin, legs for miles and a damn fine cock. Plus, the deposit was nonrefundable! Crazy!

But I was still, like, Yay! Two Valentine's dates with Wyn!

I didn't even look at my waiting list to see if I could replace the dropout.

And then ... this email came in, from this super-sweet girl who desperately wanted to fulfill her girlfriend's fantasy three-way, and it tugged at my heartstrings until I just had to say yes. I mean, Wyn and I already had the twelfth set up, right?

So I took the appointment.

And then ... Wyn's dream job called and said they wanted him to interview on the twelfth. In Seattle. I mean, this was not just any job -- it was an executive finance position with a global charity NGO headquartered in the same town where his sister Liz lived. He'd be, like, maximizing the available funds for starving schoolkids in Africa or something.

How could I think about sad starving schoolkid faces and the chance to live near Wyn's rockin' fun sister, and say, "Nah, I think our date night is more important?"

This plus that equals no Valentine's date for Trini.


"Can you maybe just stop this, woman?" I muttered to myself. I probably didn't have more than a few seconds before the door would open and I needed my work-face on. Think about how sweet and pleading this Carol chick was making the appointment. Think about all those other Valentine's Day clients who hired you as a gift to their S.O. Some of the best, most romantic jobs you've ever had. This stuff is way less about the money than a normal night's work. And it's fucking great money on top of that.

It was a good tactic ... a couple of my favorite escort memories did float through my head. But they couldn't bump my sweetie's face out of my thoughts.

This sure would be easier if they were a hetero couple or some gay guys instead of lesbians.

(Don't get me wrong -- I love lesbians as people. I'm just not that into women, and a job always takes a little more focus on my part if no one else's penis is involved.)

It'll be fine. It'll be fine. It --

And then she opened the door, and it was fine.

"Hi," I said -- immediately, warmly, and with genuine happiness. Then I held out my hand to the adorable little creature sheltering behind her apartment door. "I'm Trini. I take it you're Carol?"

"Um ..."

Oh, Lord, could she be any cuter?

Carol Withers, it turned out, had everything I loved in a client (with the exception of a cock and personal-trainer-grade muscles).

A straight-haired brunette maybe five-two on tiptoes, she couldn't have been any less intimidating if she was made of marshmallows and cotton candy. Her eyes had a look -- a look I almost never get to see. Soft and hazel, sashaying between hesitation and excitement: full of uncertainty that wasn't timid and enthusiasm that wasn't anything to do with lust. This woman wanted something, and she wanted it really bad, and she could hardly believe she was about to get what she wanted -- and it was written all over her face that the thing she wanted, she wanted for someone else.

"Oh, Jesus, come in," she said, her eyes and the door both going wider as she stopped herself gawking. "I'm sorry, I didn't mean to just stare ..."

I laughed and moved past her into the apartment, where I found I liked Carol Withers even more. "Honey, 'Makes people stare' is the first skill on my resume."

Seriously, I don't have a resume. But if I did, that statement probably would've been true -- at least when I gussied myself up for work. I'm a good six-two in heels, usually plus another five or six inches of afro, although I'd had my hair cornrowed just before Christmas and decided I liked it that way. (Besides which, Wyn liked it that way.) My hooters will put your eye out, and my legs are even hotter than the tits. It being unseasonably warm even for L.A., I had just about all the skin showing the law allows, with a sleeveless white faux-fur vest jacket over my favorite metallic hot-pink tube-top and silver micro-skirt.

Like me, Carol's place was lots of things at once. I'm a girl, but I have some boy parts. I'm confident but sometimes I have to work at it. I'm a very genuine person who can fake almost anything. And the room I entered now had the exact same kind of this-but-thatness going on. Small (a studio apartment with one big room for both living area and bedroom) but spacious-feeling, because she didn't have much furniture and kept most of it totally spotless. Tidy but also a mess, because one corner overflowed with this chaotic jumble of art supplies hanging off the racks she used to store them. And modest but also glorious, because the paintings on and next to the easel there, and a few others on the wall, just burst with color and a whirlwind creativity completely missing from the feng shui of the rest of the room.

"Man, someone's got some art chops on them. Are you the artist, Carol, or is it your girlfriend?"

I turned back to her for some put-them-at-ease eye-contact as she shut the door, but instead of meeting my gaze, she looked past to the workspace. That Oh-shit-I'm-really-hiring-a-prostitute wildness left her eyes for a second, replaced by something I think of as sweetly brainy. It's when you see someone really smart who's in their element and comfortable with their own abilities, but not big-headed about it.

"That's me," she said. Then her eyes rolled a little on their way back to mine. "But please don't call me 'Carol.' Only my grandma does that. It's 'Carly' for anybody under eighty-nine-and-a-half."

Carly, I thought, with one of those little memory pings you don't quite process. Huh.

"Carly it is, then," I said, putting aside the more formal name from the credit card info she'd plugged into my website. "So give me the deets on our Val-Day bash here, Carly. Your email said your girlfriend's meeting us -- Elle? Does she know, or is it a surprise?"

"Oh, it's a surprise. I mean, she knows I have something planned, but she doesn't know it's this."

"And she's going to be into it, right?"

Carly nodded, her china-doll chin dipping just once. "When Elle gets a kink, it usually won't let her go until she's tried it, and she's been kinking for someone like you a lot recently."

"Cool," I said, although something uncertain still hovered behind her expression. "Sometimes surprises go great --" Like the time I met my boyfriend. "And sometimes not-so-great. I can smooth out the not-so-great in most cases, but it helps to know it might be in the cards."

"It's not." Her eyes locked on mine then, and she tried to let some tension out of her shoulders. "If I seem a little nervous, it's because ... well, it's complicated."

I smiled at her. "'Likes it complicated' is second on my resume. And I've got several tricks that work really well at getting people over their nerves. Is Elle due any second, or do we have a while for me to help you relax?"

"Um, she left her office already. If traffic's normal, she'll be here in another fifteen, twenty minutes." She walked past me to a beat-up old loveseat with a coffee table in front of it. "But you don't have to do anything for me, really. It's her I'm nervous about, not you. You want to sit down and I'll get you a glass of water or a Diet Coke?"

"Bring me whatever you're having," I said, smiling my way to the little sofa. I lounged down into one corner of it at an angle that would let my long brown legs fit between it and the coffee table. Carly walked the, like, half-a-dozen steps into her tiny kitchen and opened the fridge.

"And I do have to do something for you," I went on, "because if she's any kind of good girlfriend, she'll have a much better time if you're relaxed than if you're wound-up. And you want her to have the best time possible, right?"

She came back with a couple of soda cans, nodding. "Yeah, you're right. Of course I do. But I don't know how you can fix me being nervous. This is a really big deal for me. For us."

"How so?"

Forking over one of the drinks, she sat down in the other corner of the sofa, petite enough to fit there without coming near my stretched-out legs.

I did notice her glance at the way my silver mesh micro-skirt rode even more scandalously up my thighs because of the way I was sitting.

My client cleared her throat and made eye contact. "Well, you know what I said about Elle and kinks? She's got an appetite. I mean, I do too -- "

"I like you both already!"

Carly blushed. "The thing is, my appetite is all for her, and she's like, a sexual gourmand. We're very on-again/off-again, and that's mostly why."

"You want to be exclusive, and she wants an open relationship."

Her head shook immediately, sending waves through her silky brown hair. "No ... no, it's exactly the opposite. I'm super-monogamous, and she knows that, so when we're on-again, she won't touch anybody else. But it's not because I won't let her -- it's because she thinks it will make me unhappy. And I feel guilty about her denying herself, and then we argue about it, and before you know it, we're off-again because neither one of us wants to make the other one unhappy."

I took a sip of my soda. "Now I like you both even better. So what is it that we're doing here tonight?"

"Well ... you're going to have sex with her ..." Deep breath. "... and ... I'm going to watch, so she sees how much joy it brings me for her to get what she wants."

"Sounds straightforward enough." I sat up, brought my heels to the base of the loveseat, and leveled my big, long-lashed, brownie-brown peepers at her. "Why so twitchy about it?"

She wilted a little, and her mouth twisted. "I just -- we've been going back and forth on this for six years. And she's so ... not lonely, but she misses me. Her sex life is great -- she gets way more than her fair share -- but she's never even tried to have a love life except for me. I don't think she ever will. So I need this to work. I need us to work. And it might not. And then what will I do?"

Her hands had tangled themselves together in her lap, so I reached over and took one. "Sweetheart, just on the basis of five minutes talking to you, if it doesn't work, then you'll be loose to go find someone who's not a crazy person. Because from what I see, if it doesn't work, your girl is bazonkers."

She smiled then, though I could see that her eyes were just a touch wet. "Well, she is kind of bazonkers, but in a good way."

"Awesome." I squeezed her hand and then released it. By this point, I was feeling all gushy inside, the way those very rare best-of-the-best jobs make me feel. I really hoped this Elle chick deserved everything Carly had going on for her. "Now, how are we going to spring this on her? You're going to change clothes, I hope."

Carly blinked and looked down at her silky teal top and above-the-knee black skirt. "I like things simple, and Elle likes that I don't put on airs. This is really pretty dressy for me. What's wrong with it?"

"Nothing wrong with it at all, child -- but it's you doing you, right? Just a little spiffied up over your day-to-day."

"I guess ..." She frowned -- almost a pout. Just delicious.

"What you want to do, is look like you've got something to prove. That's your whole point tonight, right?"

"Um ... okay."

"And that get-up's something you would wear for a nice night out. Are we going out?"

Her cheeks got a bit more Valentine's Day color in them. "Well, no."

I stood up, set my soda can on the coffee table, smoothed my skirt, and held a hand out to her. "Let's go look at your closet."

Carly took my hand just long enough to get to her feet, then led me over to the bedroom side of the apartment. A door there opened to reveal a walk-in you could park your car in, assuming you're not some Hummer-driving tycoon. But big as it was, Carly seemed to use in more for storage than wardrobe.

"I'm thinking you have two options," I told her, gesturing her into the closet. "You can go cozy, show her you plan on being comfortable with this -- or you can go hot, and show her you're expecting it to fire you up."

Her nose scrunched a little. "Yeah ... I don't know if it's going to do that. I mean, I expect that seeing her happy will --"

"Carly. Honey." I put a hand on her shoulder, squeezed it, ran a finger slowly down the sleeve just short of hitting skin over her bicep. "If you have any kind of appetite, and I'm in the room doing my thing, you're either going to get fired up or I've lost my touch."

She went even redder.

"And," I said, "even if I've lost my touch, if you're dressed like it's going to fire you up, that tells her something, right?"

"Yes, but --"

I moved the finger up to her lips. "No buts. I'm looking in your eyes, Sugar. I heard it in your voice earlier. You're committed to this. You're all-in, right? But you're not letting yourself behave the way your heart feels. That's why you're nervous. Your heart's forced your brain into admitting this is what you need to do, but your brain's still not letting your heart run the show."

Those hazel eyes blinked a few times, and I took my finger away and raised an expectant eyebrow. She hiccupped and nodded.


"Great." Turning on my brightest Trini grin, I got back to the choice at hand. "So like I said, you can go cozy -- like flannel pajamas with nothing on underneath -- or you can get your sizzle going. A teddy? Lingerie? A nice satin kimono?"

Another deep breath swelled her chest up and then swooshed out. "I have a fishnet body-stocking and some black silk undies Elle gave me a long time ago. I get them out when I really want to turn her on."

"Babe, my heart's about to burst out of my chest and wrap you in a big veins-all-over-the-place hug of pride. Let's get them out and get them on you." She came back out of the closet and went to a small dresser nearby. Is that a bitsy-bit of spring in your step, Carly? While she pulled a drawer out and dug through to the back of it, I said, "And what about me? Is Elle going to want to peel me out of what I have on now, or should I do some pre-reveal peeling myself?"

Looking up from the drawer, Carly took in my pink-chrome tube-top and shimmery micro-skirt, and said, "Elle loves unwrapping presents. You should probably keep everything on."

"Can do."

A little more digging and she came up with one part of her sizzle-set, and a little more digging after that, she had the rest. The body stocking looked to-die-for, with a nice wide weave that I expected would show off her pale petite-ness perfectly.

"Sexxxy! Need any help getting things on? I always catch my toes trying to get my feet into nets like that."

"I, uh ... I can manage. Why don't you sort of stand near the closet so you can jump in if Elle gets to the door before I'm done?"


With Carly shut in the bathroom a few seconds later, I retrieved my handbag from the coffee table and stood just inside the closet door. It's going to take a smidge for her to wiggle her way into those fishnets ...

I was just too excited to hang loose on my own, waiting, so I snagged my phone and zipped off a text.

Me: Babe! Thisn's a bell-ringer! Ossum-possum-cute little chick buying me as a prezzy for her lady -- so sweet I don't even care they're girls.

Wyn texted back pretty quick ... as usual.

Him: That's great! You'll have to spill all the beans your confidentiality policy allows when you get home.

Me: It's gonna be juicy, I can tell.

Me: You going to hang with your sister tonight?

Me: She's back to Seattle tomorrow, right?

(Liz worked a couple of days a month out of their dad's company's office here in L.A.)

Him: Nah. Her friend Carly called so they're getting together.

Me: Ha! That's fu

The "nny" didn't make it out. Wyn's sister's friend Carly had been mentioned a couple times when I met the fam at Christmas. That's what pinged in my brain earlier. What if ...

Oh. Shit.

Me: Wyn what is Liz's full name?

But I didn't even need him to text back. It jumped into my brain before the next balloon could pop up.

Him: Liselle, why?





I stepped deeper into the closet and pulled the door closed after me.

Me: OMG Wyn, are Liz and Carly a thing?

Him: Not really.

Him: I mean, on-again, off-again.


Him: Mostly off.

Him: Why?

What had Carly said about Elle? She's got an appetite ... great sex life ... way more than her fair share. And wasn't that almost exactly what Liz had said at Christmas when sex came up in that giganto conversation? Trust me, I've had more than my share.

Fuck Fuck Fuck Fuck.

Me: Baby, I think this is them.

Him: Lol!

Him: Liz is going to die laughing!

Me: No, you don't get it.

Me: This is a fucking enormogasmic huge deal for this girl.

Me: OMG, please don't let it be them.

You know when your phone does that thing, where the three dots tell you your bestie is typing a text? And then it stops? And then it starts again? And then it stops again?


Three dots ...

Him: If it's them

Him: here's to you finishing the Tate family hat-trick.

(By a bizarre series of coincidences, both of Wyn's parents had engaged my services -- separately -- before I ever met him. It was a real interesting meet-the-folks Christmas.)

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