Trick or Trini

byIanSaulWhitcomb©

[Author's note: This story is a sequel to "Trini Plays a Trick," my entry in last year's April Fool's Contest. You can read it on its own, but it's probably more enjoyable if you've read the earlier story first.]

*

April to October is a pretty long time to spend working up the courage to call somebody. So even though I'd had this feeling, giving Wyn my card on his April Fool's birthday, something about the long, hot slide of summer left me convinced he'd either chickened out or lost interest.

Which meant when my phone rang two days before Halloween and the screen said "Wyndham Tate," it took me a minute.

'Wyndham.' Wyndham. Nnnn ... Wyndham? This was my personal line, and I keep a tight-ass wrap on the number, so anything short of instantaneous recognition threw me. "Who the fuck do I know named Wyn —"

Oh, shit! Really???

I jabbed the answer icon with one dark finger and put on my smoothest voice. "Wyn, sweetie! What's up?"

"Uh ... Trini?"

Goddamn, he's so fucking adorable! My heart did some jumping-jacks, and I realized how much I'd been bullshitting myself, shrugging off the fact he hadn't called all these months. "Yeah, doll. Kinda jazzed that you're ringing me on this number and not the other one. What took you so long?"

"Really?" I could hear the nerves and surprise and jolt of pleasure in the word. "Thanks, that's ... oh, sorry about not ... I've been ..."

I laughed, with my head back and everything tingling. "Ooh, I'd forgotten how cute you are when you're nervous. Keep going!"

He sort of cleared his throat, or maybe it was an attempt at a chuckle. A short pause sounded like his handsome, just-slightly-too-round face going all pink and blushy. "Man. I really hoped I'd be cooler about this."

"Honey, cool does not get me hot. You're knocking it out of the park. Please tell me you're asking me out."

Silence. Then, "Jesus, you're awesome, Trini. So, yeah ... sort of."

"Sort of? Oh, child, don't tease. Are you or aren't you?"

This one was identifiably a throat-clearing. "Yeah, definitely. You're going to think this is a wacky idea, though, and I know it's really last-minute and you're probably busy, so I have a backup if —"

"Yes."

"What?"

"Yes. I'm saying yes. What are we doing and when?"

"Haha ... great! Uh ... so, my aunt just had emergency gall-bladder surgery."

"Fuck. You are sweeping me off my goddamn feet. Is she okay?"

"Yeah, yeah, she'll be fine, she's just pissed she's not going to be able to eat spicy food any more. But the thing is, her house is like the Holy Grail for kids in her subdivision on Halloween. She's got — I mean, crazy-huge buckets of full-sized Snickers bars and Kit-Kats that she gives out every year, and since she's going to be in the hospital another couple days ..."

"Wait. Wait, our date is going to be handing out candy to neighborhood kids in the suburbs?" Without giving him a chance to answer, I went on, "I love it. But how are we supposed to get away with fucking under those conditions?"

Long pause. "Well, I wasn't assuming there would necessarily be ... fucking, you know, on the first date."

I just shivered at the words 'first date' and then gave a cackle into the phone. "Oh, there will be fucking. But I guess we can hold off until the candy runs out."

"I, uh, also figured we'd go to dinner afterwards."

"Perfect. Stuffing the kids full of Snickers, then fucking, then dinner, then more fucking."

"Christ, Trini. I think I need to hang up now and go whack off."

"Me too, baby, but when and were are we meeting up Monday night?"

"I can pick you up if you text me an address. It's in Huntington Beach, and we'll need to get there before sunset, so ..."

"Fabulous. I'm in Anaheim. You can get me around five, and if traffic's good, it'll give me time to blow you in your aunt's house before we have to set up for the trick-or-treaters."

He coughed, and for a second I wondered if I was overdoing the sex talk. Well, tough shit, Wyn. You shouldn't have made me wait six months with nothing to do but daydream about screwing your brains out.

"I'm going to assume you're at least partly joking there or else I might get a speeding ticket or crash the car in traffic on the way."

That got another laugh out of me. "Oh, honey, you just assume whatever you need to assume. I'm hanging up now so I can text you this address."

"Trini, wait —" he flashed.

"Yeah?"

"I'm just — I'm super-glad you really meant it. When you gave me your card and said I should call."

I smiled at that. "Sweetie, I give my card to just about anybody who'll take it, and I always say they should call. But I don't write this number on the back unless I mean it."

"Well ... I'm glad."

"Yeah, me too," I told him. "Monday at five, then."

"Absolutely."

* * *

So, I one-hundred percent, no exceptions, cross-my-heart-and-hope-to-die do not date customers. It's bad business and even worse as a dating strategy. But Wyn wasn't a customer — not really. True, his douchebag friends had hired me for his birthday, and true, he had fucked me that night, and true, I'd gotten paid for the evening. But the deal and the plan had been to humiliate Wyn ... make him think he was about to lose his virginity to a smoking-hot hooker, then video him at the moment he realized he'd been suckered into bed with a she-male. The two of us actually doing the deed had never been part of my negotiations with Pete and Jack.

Thankfully, we'd managed to turn the tables on his laughing-hyena pals — and even more thankfully, it involved Wyn doing a downright amazing job stuffing me full of cock. He was so sweet, and he showed so much character, and he made me feel so good, it went from being a morally queasy job to one of my best nights ever. So when it was finished, I did something I never do: I gave him my card, wrote my personal number on the back, and told him to call me "for business or pleasure" anytime he wanted — but that he had to choose one or the other and stick to it.

And he picked me.

This meek, cute, good-hearted, conventional-seeming guy had decided he'd rather date a transgender prostitute and find out who she really was than put her in his contact list as a source of reliable, mind-blowing, on-demand sex-for-hire.

It flat-out gave me goosebumps. When I got off the phone, I felt like my eyes would pop out of my head.

"Okay. I have a date. So what do I do ... what do I do ...?" First, I got my ass off the sofa. Then I tightened up the silk sash on my kimono. Then I put my hands on my hips and stared down at my purple-painted toenails. "Shit, Trini, you know how to get ready for a fucking date, don't you?"

Only I realized I didn't. Not for a date like this. Oh, I could gussy myself up and be ready to short-circuit Wyn's brain with electric sex-appeal. I could vamp. I could go get a mani-pedi tomorrow. I could pull out all the stops that needed pulling to guarantee the evening would end with me bent over something and him buried balls-deep exactly where I wanted him.

"Stop that!" I told the front of my kimono, bulging rudely out to block the view of my toes at the thought of Wyn giving it to me. The kimono didn't listen, so I looked up and started pacing, hands still dug-in at my waist.

What I didn't know how to do was get ready to spend an evening with a guy from a whole different world, sitting and chatting about things you can sit and chat about when a drivewayful of grade-school witches and ghosts and Power Rangers could show up and overhear any second. What I didn't know how to do was ...

"Oh, shit. I so have to change my costume plan!" Wyn's aunt's neighbors' kids probably would not appreciate the bikini-with-a-bulge fairy godmother outfit I'd put together for Yoli's big Halloween bash. "Oh, shit. And I've got to tell Yoli I'm ditching her shindig."

Maybe calling Yoli will switch off my panic mode. I turned back to the couch to get my phone, went to the favorites screen, scrolled a little, hit the right entry.

Ring. Ring. Tense and impatient, my toes curled in the fluffy white throw-rug in front of the sofa. Ring.

"Triniiiii!" Yoli's trademark squeal dashed away a chunk of the anxiety, just like I expected. "How's my favorite African wild-woman?"

"Hi, Yols," I said, breathing a little easier. Then I thought, Holy shit, he's got me so I can't even remember how to breathe right! "Listen, babe — there's a problem with me and your party Monday night."

"Oh no! What's the probla, chupacabra?"

"Well ... he called."

A little gasp came through the phone. "No! Yes! You see? I told you he would. Deets, deets, mi chocolate sweets!"

As I ran down the details, her oohs and ah-hah!s calmed me down even more — or maybe they didn't calm me down as much as they turned me from freaked out to all warm and giddy.

"And all this time you didn't believe me when I said not to worry!" she said once I finished.

"I know," I said. "I was just sure it was all me being silly."

Yoli laughed. "You were being silly. That's how I knew there must be something real going on. You get silly about lotsa things, Trini-bo-bini, but you don't get silly about men — especially not ones you only met once."

I couldn't help nodding, but ... "That still didn't mean he was going to call."

"Of course it did!"

Her voice sounded like she had more to add, so I waited.

"El amor," she said. "El amor es todo."

"Haha, now who's being silly?"

"Both of us! Now, what's your plan — besides breaking my heart by skipping the party?"

"I don't have a plan. Just a giant boner and a totally inappropriate costume for handing out candy in the suburbs."

Yoli laughed again. "Okay, chica. So what you do is, go take care of your boner, then drive to the costume store and see what speaks to you."

"But I don't even know what he likes. This is so crazy — I don't know a goddamn thing about him!"

"Right. And that is why you listen to your heart. Go to the store. Find something there that reminds you of you, and reminds you of him. That's all it will take, no?"

"Ohh, I hope you're right."

"I'm always right!"

I nodded slowly. "Okay, Yoli. Thanks."

She made a kissing sound and hung up, leaving the tent in the front of my kimono to remind me that at least one part of her advice needed to be followed immediately.

* * *

I smacked a suction-cup dong to my shower wall and backed into it thinking about that night. Those smart, blue-green eyes of his looking at me, seeing something he found gorgeous and amazing. Then the heat of anger and decision in them when he learned about the April Fool's trick and decided not to sit still for it. The way he took charge, said what he wanted, threw aside his virgin nerves, and slid into what should have been scary, foreign territory like he owned it.

And oh, the way he felt pushing into that territory!

The dong plugged me up nice and firm, about the right size because I'd bought it just for that reason a week or two after I met him, when the big horsey one I'd been using before didn't work right for my fantasies anymore. Folded over at the waist, with my hands on the glass enclosure in front of me, I humped that toy for all it was worth, until the lube ran down my little nut-sack and dripped off.

"Yes, Wyn ... Jesus, baby ... drive it into me ..."

I'd had to be restrained, that one time we shared together. He'd never put his dick in anyone, much less a well-skilled professional like myself, and neither of us wanted it to be over too fast. So until the very last bit, I'd kept it super-slow and gentle, stopping whenever he got too close and made his little almost-there noises, then moving again when I heard and felt him ease back from the edge of spewing. It had been some of the most beautiful sex I'd ever felt — and for sure the most beautiful I'd ever had on-the-clock. Because he appreciated it. Because he didn't just want to enjoy it, but wanted me to enjoy it.

And because, virgin or no virgin, he ended up making me enjoy it. A lot.

But I hadn't been able to do what I really wanted, which was to put my whole body into fucking the shit out of him. And the whole week afterward, I'd burned and ached for him to call and give me a chance to. And then the second week, I calmed down a little but still kept doing my best to recreate what I'd felt with him that night, with his buddies in the other room waiting for him to run out gagging in disgust and humiliation, while instead the two of us had the most fantastic time in bed and ended up embarrassing the hell out of them with a trick of our own.

And probably at least a half-dozen times a month since then, I'd done something like this: impaling myself on a slicked-up dildo, calling out his name, pretending to lead him by the penis into ever-improving heights as a lover. Slamming back against him rapid-fire, milking his delicious cock will all my considerable talents, and finding myself pole-vaulting toward orgasm quicker and more easily than I could remember doing in years.

"Oh, Wyn. Oh god, it's so good. Oh, god!"

In my head, he lowered his mouth to my earlobe and sucked it a moment as he plunged in and out of me, before whispering, Here, I'll make it feel even better.

Then I made my hand into his hand and caressed my breasts as he drove up into me — one and then the other, squeezing, kneading, tugging the nipples. At the sound of my accelerating gasps, that hand glided lower, down across my abs, along the swell and curve of my belly, until it wrapped itself around my straining, needy cock and jerked and pumped and —

"Oh, GOD, WYN!!!"

I spouted and gouted all over the floor of the shower, filled up with the glory of him and then emptied out into the oblivion of pure pleasure. Throbs of complete delight rolled through me, one after another after another, to the imagined sounds of him crying my name and coming himself.

For a bit I just hung there panting, holding myself up with my hands on my knees, the suction-cup dong still wedged deep inside me. Finally, when I had my breath back, I thanked Yoli for the good advice, slid off, and turned on the shower to wash up.

* * *

Monday afternoon, I met Wyn at the drive for my building after waiting three minutes in the lobby for him to pull up. Waiting is generally not my style, of course. I'm a lot more used to letting the guy cool his heels before I come down for a date. Only tonight, I didn't want to add even a tiny extra twinge to my suitor's nerves. I already expected him to be plenty nervous-puppy cute, and besides, there were those kids in his aunt's neighborhood who'd be let down if we were late.

And that blow-job I was drooling to give him if we got there early.

So I headed for the elevator at ten to five, realized I'd forgotten some of my accessories, went back to my apartment, grabbed them, and still arrived at eight till. It meant standing around in the lobby in my costume, but hell, it was Halloween — and it's not like I haven't been seen passing through that lobby in way more outrageous get-ups than this one. Some of my neighbors went by in biz clothes on the way in, some others in costumes of their own on the way out.

And then a brassy, sassy Tesla Model S turned in off the street, and I hurried out in my high-heeled boots to meet it.

"Oh my sweet lord," I gasped when he came around the front of the car. "What have you been up to since April?"

He laughed and looked embarrassed — two things he did equally wonderfully. "I guess I've been to the gym a couple times."

Had he ever! I just stared him up and down as he got closer. He hadn't been tubby or anything, back in April. But I'd have called him ... on the soft side. Enough of a middle that you could predict where it was headed, if its owner didn't watch the beer and ice cream over the next ten years. Well, the middle had vanished, and either he'd bulked up his shoulders or started walking with them a little squarer and more confident. Even his adorable roundish face had gone a little leaner, into out-and-out handsome territory.

"Babe, you are killing it," I told him.

"Thanks," he said, with an awkward grin and a scratch to the back of his head. "Um, I like your costume."

I struck a pose, turning sideways to him with my laser pistol out and my free hand at the waist of my red miniskirt dress. "Pshew! Pshew! I'm set on 'stun.'"

He laughed, and I tucked the plastic gun back away and practically jumped over to wrap him in a hug. It took him by surprise — he barely managed to get his hands around to my shoulders before I realized I must be overdoing it.

"Sorry," I said, letting my hold loosen and easing back to look him up and down again. "I just can't believe how glad I am to see you!"

He blinked a little, then managed to say, "Geez, it's not like I'm amazing looking the way you are."

My insides turned all chocolate-covered-caramel-on-a-hot-sidewalk gooey. I couldn't help myself; I had to lean in and kiss him, just a quick smooch on the lips, but full of a happy, shocking spark at the same time.

"Oh, yes, you are," I told him. "But we can argue about it on the way there. Take me to suburbia!"

"Yeah, sure," he said, burning bright red from the kiss. "Here, let me get this for you ..."

He side-stepped to open the door for me — more boy-scoutish than suave and gentlemanly — and I slid in, my planet-sized poofball curls brushing the inside of the roof. The car had a spotless interior, new-smelling and luxurious.

"Ready? Watch your fingers and toes," he cautioned me. I smiled up at him, and he closed the door.

Damn, he's had that hair done right since last time too, I thought as he passed in front of the hood to his side of the car. With his crisply cut new do to look at, I had a hard time remembering exactly how it had been before, but the change made the difference between stylin' brunette and ran-a-comb-through-it brown.

"So I'm disappointed you don't have a costume!" I mock-pouted as he got in and pulled his door shut.

"What?" He looked at himself, then tugged at the long sleeves of his white button-up shirt. "No, this is a costume. I just left the vest and my blaster belt in the back seat."

Glancing behind us, I saw a folded black vest and a belt and holster, with a much blockier plastic gun in it than the one that came with my red space-chick mini-dress.

"Blaster, huh? I figured you'd have the lingo down better than me. I'll stick to calling mine a laser-pistol, though. You can be all manly with your 'blaster.'"

He laughed, and the car surged forward, pushing me back in my seat without making a sound.

"Holy shit! These things are quiet!"

"Sorry — the oomph kind of sneaks up on you without the internal combustion going along with it, right?"

As he looked around us and maneuvered out into traffic, I watched him — careful, precise, nothing brazen or brash in his movements, but still not quite the same meek-postured kid I'd led into that bedroom back in April.

"Yours is a phaser, by the way," he went on. "Not as clunky or manly as 'blaster,' more elegant and civilized. Just in case you want to use the right lingo."

"I'll try to remember."

We got to a light, and he looked me over as we waited for it to turn. "So you picked that out because you figured I'd be into sci-fi?"

"No, a friend of mine said I should find something that reminded me of both of us. I kinda thought this might be your thing, and I liked the movies all right myself. I just didn't watch them like I meant to be in a trivia contest later. However ..." I nodded toward the light, which had gone green. "... a tight red skirt definitely reminded me of me."

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