Trini Trims the Tree

"Well ..." she said, flustered and taking her hand back, "I suppose, given that Wyn's brought you all this way, it really ought to be 'Merry.'"

I grinned. "Great. So ... do we want to all sit down over more drinks?"

"Oh, I really don't --" / "Yeah, I could really use a --"

Both of them stopped, mother and daughter looking at each other.

"Tell you what," Liz said, turning her gaze to me and then to Wyn. "I'm betting Dad for damn sure didn't show you guys to your bungalow, right? How about I walk you over there and give these two a chance to get in sync on their host-and-hostess mode?"

Merry just about collapsed from gratitude -- I could see it. Jerry made a casual gesture with one hand and swirled his glass of whiskey in the other, but his forehead uncrimped a bit in relief.

Beside me, Wyn scratched his head and shrugged. "Sure."

"Tompkins get your luggage already?" Liz asked, on her way to the sliding glass door that separated the great room from a wide, brick deck beyond.

"I think he said someone would deliver it for us."

As we headed outdoors, Merry called after us belatedly. "We'll see you at five for dinner, of course!"

I smiled and waved back at her. In fact, everyone smiled and waved ...

Although some of the smiles looked more comfortable than others.

* * *

"Wow," said Liz, once we'd left the patio and started our way along a path made of broad, elegant paving stones, irregular enough to look natural yet also comfortably flat and level. "Did you guys drop some kind of bombshell on Mom and Dad that I don't know about? I haven't seen them that freaked out about meeting someone since I brought home the head of the campus Young Democrats in college."

Something about her confidential but cheery tone stirred itself together with the bright Caribbean sunlight and the tang of the ocean breeze, and I felt a kink go out of my stomach muscles. Liz is all kinds of right, I decided. Wyn promised me I was going to like her, but knowing that she'd been CEO of one of their dad's companies since the age of twenty-four had left me dubious.

"I dunno," Wyn said with a dip of his brown eyebrows. "Did you really think they seemed that upset?"

Liz and I both laughed at the same moment. I looped my arm through his and squeezed him close. "Oh, honey, I'm guessing they're pretty damn tight-wound all the time, but yeah, I think I threw them for a loop."

"You don't think they, um, guessed that ... uh ..."

As he picked his way around it, his sister eyed us both. "What, that you're trans?"

I got a warm grin at that and bumped Wyn with my shoulder. "Hey, I thought you said you hadn't worked up the courage to tell her yet!"

"I didn't," he said, throwing a dash of cold water on my moment of pride in him.

"I know my way around the gender playbook," Liz told me. Our path wandered through a couple of pretty sitting areas, then around a full-size tennis court. "If you were a little shorter with a little smaller hands, I'd have been on the fence. But I pretty much knew the second I saw you, especially since Brother Bean-counter told me there might be some shoes dropping this Christmas."

"Look, Liz, I'm sorry," Wyn said. "I knew you'd be cool about it, I just --"

"Oh, shut up, you," she laughed. "If you'd told me, I'd have been dying to spring it on Dad in the middle of a board meeting just to watch him react. Trust me, I'm impressed that you're even dating a transwoman, much less that you've brought her to Christmas Week. You've really grown a pair this year -- I'm not going to bust your balls over it if wimpy old last-year Wyn nagged at you and made you too worried to tell me."

"Thanks," he said. "So, anyway, do you think they guessed too?"

Fingers in ears. La-la-la. Not hearing any of this ... fuckshit, can I tell them? 'By the way, Liz, I'm also a hooker and it might interest the both of you to know that I ...' Oh, even-bigger-fuckshit, how can I not tell Wyn?

I damn sure didn't want either of his parents to be the one to break the news to him, and who knows what they might do to keep their son from getting any deeper in with a black t-girl sex-worker?

"Ehhh," Liz said, teeter-tottering one hand. "Dad, maybe. Except I doubt his macho pride could process the fruit of his loins riding an LGBT train to Hookup Town. And Mom? No way. Would never even enter her brain."

Liz, you'd be surprised what all might enter your mom's brain ... and what she might let enter other parts of her too ... Christ, Trini, can you maybe shut this shit off?

"That's the path to mine, by the way," she said with a gesture up another paved trail. "It's called 'Stingray Place.' Just one bedroom, but goddamn, it's nice."

"We all get our own houses?" I asked. "Yikes!"

She laughed. "Did Dad already tell you the story about winning the rental in a bet?"

"Yeah," Wyn said. "I still can't figure why our folks would be acting weird, though. I mean, I did warn them ahead of time that you're black, so that's not it."

Nope. They are definitely not put off by me being black.

"Oh, just let them wig," Liz told him. "Maybe it's something else entirely. Maybe they've finally worked up the cojones to split, and seeing a happy couple makes them feel even shittier about spoiling Christmas with a divorce announcement."

"Man," he said. "That would suck."

This time, her laugh came out as a bark. "Are you kidding me? I would raise a fucking toast. I don't know why the hell they're still with each other except for the joy of stewing in their own misery. Did you know, Mom says they haven't even done it in over a year? Look, the dock and the boats are down there."

"Jesus, Liz. TMI."

"What, you don't want to know where the boats are?" She grinned and winked at me as we walked on, but I didn't manage much of a grin back.

If Wyn thinks his parents not doing it is TMI ... I am so fucked.

"Anyway, this is you guys up ahead. 'Dolphin Cay.'" In the direction she nodded, I saw a cozy, perfectly maintained tropical bungalow through some gaps in the trees. "Want me to come in, hang out, catch up on things? Or should I just let you get settled in and see you at dinner?"

Wyn looked at his watch. "I dunno. What is it, an hour till five? I guess we should get unpacked. And Trini probably wants to change for dinner."

If I hadn't known Liz worked out of the same office as Wyn once a month, I'd have insisted she come in so they could visit. Hell, it's not like I'm shy -- if she didn't mind, she could even hang out with both of us while I switched clothes. But since they'd seen each other just a couple weeks ago, and since I really needed to figure out something to say about me and Wyn's parents ... I just poked myself into smiling and said, "I am an outfit-for-every-occasion kind of girl."

"Cool." She leaned over and kissed her brother on the cheek. Then, surprisingly, she did the same thing to me. "I'm glad you're here, Trini. Wyn had it straight when he said you were a blast, I can tell. Ha! If 'straight' is the right word."

Wyn opened his mouth, but Liz stopped him with a pat on the head.

"Kidding," she said. Then she waved and turned back along the path. "See you guys in a little bit!"

'Dolphin Cay' had some fabulous billionaire beach-house architecture going on. Huge, airy, arch-topped windows. An open floor-plan that let you see straight through the house -- in our case, from the approach to the rear deck and hot tub into the kitchenette and dining area, past that into a small but stunningly furnished living space, and past that through the front window to the forward veranda and its view of the beach and sea out beyond. Over to the other side of the kitchen, a bedroom/bathroom combo that ran the full length of the house.

"Yipes," I said. "Gorgeous, but kind of exposed, don't you think?"

Wyn shrugged. "Oh, there's probably a bunch of pushbutton blinds that roll down. Or the windows self-tint with a dimmer switch."

I glanced over to see if he was joking, then realized, even if he was joking, he was probably right.

Inside, we explored the house and its minimalist elegance, then found our bags waiting in the bedroom and started unpacking.

And I tried to strategize.

So, honey ... you know how you're more or less cool with my job?

Hey, I have this pretty good idea about why your parents were acting weird.

Funny story about your mom and dad! I know you'd never guess this from looking at them, but ...

Wow. It sure is a small world sometimes.

Oh my god, Wyn, I've fucked both your parents.

"Do you think they've figured out I'm planning to quit?" he asked after a couple of minutes of silence. "I mean, what else could it be? Liz has always been able to read them better than me, so she's probably right that they haven't guessed about you."

I stopped unloading my dainties into the bureau. "Oh, sweetie, I'm sure you've got nothing to worry about."

Me, on the other hand ...

"I just don't know," he said. "It would make sense. Dad's been grooming me to be a CFO since I was twelve. He's going to blow a gasket when I tell him, and if Mom knows it's coming, she's probably squirming in terror at the prospect of a family fight with a guest there to witness."

Shit. Like he wasn't already nervous enough, and now me freaking them out is making him freak out even more than he already was.

I went over and put a hand on his shoulder, turned him and drew him to me.

"You're fine, sweetheart. I'm betting ... I mean, I'm a hundred percent sure it's me."

His chin settled over my shoulder and his arms went around me. He felt so good there, so right. How the hell was I supposed to break this to him?

"Hmmm," he sighed, with a deep breath and a loosening of the tension all through his body. "It can't be you -- you're too amazing."

Damnit, Trini! Do NOT get distracted into having sex with him!

But he had me tight against him now, and I could feel that switch clicking in the way his hands moved along my back. Not to mention what I could feel going on in his downstairs department.

He breathed into my ear.

"Think we have time to do it and get cleaned up and changed before dinner?"

Have I mentioned I have a crazy powerful sex drive? It's not normal. I mean, not normal for anybody, much less a transwoman who's been on HRT for ages. But it's part of who I am and part of why I do what I do, and for some reason Wyn knows how to fire it up more than anybody I've ever met. I think I must have been really, really, really good in a past life -- like, a saint -- and this is how karma has rewarded me.

"Ohhh," I said as he began kissing down the side of my neck, "it probably depends on how long it takes us to find the button for those blinds ..."

"Who cares," kiss (neck), "about," kiss (collarbone), "the blinds?" kiss and deep tongue-lick (cleavage), "Mom and Dad are freaking out back at the main house," zip (dress), "Liz has gone to her place," unsnap (bra), "and I'm sure the staff are paid really well to be discreet."

"Then we definitely have time," I gasped, kicking loose my sandals, shucking out of my dress, tossing away the bra. He had most of his shirt buttons undone by the time I finished undressing. "Here, let me help you get naked."

From my knees, I took care of his belt, pants button, and fly, then pulled down his slacks and undies. My favorite Freudian object stood up from its nest of curls as soon as I had it free, so I caught it with my lips and deep-throated it while I held his loafers and he stepped out of everything but his socks.

"Jesus, Trini, that's so good. Can you get on your back and I'll do the same for you?"

"Mm-hmmm," I said around a mouthful of cock. But I bobbed a couple of times before slipping off, just to hear him moan.

I'll figure out what to tell him about his parents later, I thought, popping loose and settling back to the carpet. Right now he needs me to make him feel good.

Wyn got into position on top, a thigh to either side of my face, dick and balls hanging low above my nose, filling my head with a savory masculine aroma. I licked the underside of his shaft, all the way from tip to base, then kissed and lip-nipped his swinging nut-sack. One of his hands surrounded my swollen erection, stroking gently, milking. His breath landed hot in my crotch, followed by the tip of his tongue.

With a loud, "Gluhmmm!" I swallowed him deep. My hips bucked and rocked to meet the tug of his hand as his tongue ran wet laps around the circumference of my cockroot.

"Oh, babe, yes," he whispered at the bob and twist of my head. "Uhhh, yesss ..."

I felt his lips part around the tip of my dick, sweeping down flush with the top of the fist he had gripping me. Every gland I had in the area responded with fluid enthusiasm.

"Rrrhhmmm ..."

"Uh-huh," he said, momentarily leaving my tip wet and bare. "Uh-huh!"

One of my hands had him by the tail-bone, helping me pull myself upward to engulf him. I let the other one move to the back of his head, combing the nails through his short, brown hair. He took the hint and rode his mouth all the way down on me, replacing the pumping fist with soft, damp suckling.

Even though we'd just started dating fifty-some-odd days earlier, Wyn could suck like a pro. (Which, unlike most people, I am able to say literally.) Night-by-night and week-by-week, he'd gone from talented beginner to master of fellatio. Of course, it helped that I knew what I liked and didn't shy from discussing technique (and demonstrating it). But the man had a natural talent, and the way he could flutter his inner cheeks along my rod and hit all the right spots with his tongue at the same time -- it was just magic.

And maybe the best part was how much he liked doing it.

Somehow, I could tell that the eager jab of his hips as he fucked my mouth didn't just say he enjoyed getting his dick way down my throat. Instead, I could feel and hear that he loved the way I tasted ... the way I moved and squirmed and moaned in response to his oral gymnastics.

The way -- surprisingly quickly -- he could get my hard-on to expand and tremble at the edge of orgasm.

Then the way he could dial me back, hold me where he wanted me, slowly gliding his own thing in and out of my quivering mouth.

The boy had gotten good at this, and he knew it -- and he owned it.

I came quicker than normal ... maybe I snuck up on him with a stealth squirt, or maybe he figured we should keep it short to be sure we made dinner on time. Either way, I groaned around his cock and arched my back and blew a giant squeezy-spurty load of liquid white thunderbolts. Wyn dove to the bare base of my exploding firecracker, his mouth and throat all gulping suction as I came and came and he swallowed and swallowed.

When he'd vacuumed up the last drop, I rolled him over and rotated around between his legs, keeping up my blowjob all the way. He looked really pleased with himself once he'd lifted up on his elbows to watch me work.

"I'm getting the hang of that, huh?" he asked with a grin.

"Mmm-hmmm!"

"Ooh. Wow. Mm, that's nice."

Eye-contact was my secret weapon. Different things do the trick for different guys, but with Wyn, it seemed like me staring up at him while happily hoovering his shlong turned on his motor as much as all the tonguing and slippery lips and deep-throating put together.

"Oh, God," he said. "Mmh! Mmh! Nngh ..."

"Mm-hmm."

"Yes -- ah --"

"Mm-hmmm."

"Ooh ... ooh ... eeeee ..."

"Mmmmmmmmmm --"

"FUCK!"

Jackpot. His head went back and his tool throbbed in my busy mouth and suddenly I had as much cum as I could swallow, surging out from my man's sperm-cannon and down the shooting gallery of my throat.

One bellyful of semen later, I let him slip out and crawled up along his body to kiss and hold and be happy with him.

* * *

Wyn convinced me to go casual for dinner, which started things off uncomfortably because he wore shorts and a polo shirt, I wore a skirt and halter-top, and his parents both came dressed to the nines. Mister Tate had changed into an even nicer dress shirt and slacks and added a tie. Mrs. Tate picked a regal burgundy number for her dress and had fancied up her hair and makeup as well.

Thankfully, as Wyn held my chair for me to sit down, his sister came in wearing shorts and a t-shirt, golden hair pulled back in a long ponytail.

"Oh good," she said, grinning at us. "I'm not the only fashion slacker."

Merry crimped her mouth in disapproval, but said nothing.

The early part of dinner went by smoothly, with food bought in restaurant style by a server while the cook could be heard toiling in the kitchen. We had our choice of wines; I just asked for something sweet.

Conversation over the appetizers (an oyster thing that wasn't oysters Rockefeller but looked sort of like it) stuck mostly to, "So how do you like your bungalow?" and "It's great! Very nice," kind of stuff, along with discussion of some of the island's other facilities. Pools. Hot tubs. Beachside walking path that ran most of the way around the place. Mini-marina. Jet skis. Discussing the amenities took us halfway through soup, a breezy little fish stew with hints of curry and coconut. Then Liz told an extended joke that got interrupted in the middle by delivery of our entrees, steaming filets Oscar whose smell alone just about made me drool.

Then, midway through the steaks, a pause dragged on long enough that Wyn took it for his chance.

"Yeah, um ... maybe we should just get this out of the way in case it blows up."

Everyone gave him a different sort of attention. Jerry's was the fingers-laced-together skepticism of a schoolmaster waiting to listen to a B-student's oral dissertation. Merry's held a dubious resignation, as though all too many family dinners had previously "blown up." Liz's just said, 'Ooh, I bet this is going to be good.'

"I've decided that I'm going to look for a different job next year."

Jerry delivered a withering sigh of, 'No, you only think you're going to do that.' But aloud, he just said, "Go on."

"You know those charity finance courses you said were a waste of my time? Well, they weren't just a couple of classes. I finished a whole minor in it, and --"

"Oh, God help me," his father said. "Do not tell us you're thinking of leaving a sure track for CFO to go and ride herd on compliance accounting for some bozo nonprofit."

Bristling, Wyn replied, "Yes, actually, that is what I'm --"

"I think it's great," Liz cut in. "Do you have someplace in mind?"

Before he could answer, Mister Tate said, "Great? You think it's great that he's going to throw a real career away for the sake of --"

"I'm not throwing anything away."

"-- some idiotic, bleeding-heart, probably socialist --"

All right, time to ring the bell on this one.

"Excuse me, but can I say something?" The squabble died down. For a second, I thought Wyn's dad would snap at me for interrupting, but then I saw the, 'Oh, wait, this girl has some embarrassing goods on me' lightbulb click on over his head and he composed himself.

"Look, I hate to stick my nose into the family business, but --" I gave Jerry just the tiniest tweak of my eyebrow. "I'm sure you know what it's like to want something and decide to make it happen, don't you, Mister Tate? Isn't that what entrepreneurialism is all about? You know, when you get to the bottom of it?"

I didn't even put any stress on the word 'bottom.' But the man still knew I had him by the balls when I said it.