Trini Trims the Tree

His ass clenched by a hair as I grazed one lube-slick finger up his crack. Then he relaxed, and I ran it back down with more pressure.

"Now, since this is your first time," I said, finding and caressing the tight knot of his asshole with my fingertip, "we can work our way up one finger at a time --"

Jerry shook his head and dropped forward, hands to the sheets, which took his ear at least momentarily away from my sultry breath. "I want it all at once. A hooker last year fingered me right when I was coming -- I know what a finger feels like. I want to know what it's like to be rammed."

His expression in the mirror told me not to warn him how much that might hurt, so I flared my eyes instead. "Yeah," I said, "you seem like the kind who can take it."

"That's the whole point. Let's go."

Nodding, I shifted more directly behind him and lined myself up. He didn't flinch when my tip touched down against his asshole. But he did close his eyes and set his jaw.

I raked my fingernails down his spine and pushed.

"Ngh." His muscles barely yielded at all. I kept my free hand circling on the small of his back, nails making a hint of contact that said, relax, since I knew he didn't want me to say it out loud. I pushed again. "Hnhf ..."

For my third push, I kept the pressure on, steady enough I could feel a little give. The guy's breathing sped up something fierce. Come on, Big Man, I thought, let go. Let me give you what you want.

Jerry opened his eyes and glared at me in the mirror. The voice that made it out past his clenched teeth hit somewhere between a growl and a snarl. "Do it!"

Inside, I shrugged. Outside, I gave him an of-course-sir-right-away-sir, nod, along with my well-compensated obedience.

With both hands at his waist, I jammed.

Breached him.

Rode all the way in and folded at the waist to get my nipples against his back like he'd ordered.

"AGH! SHIT!"

Jerry had some spine on him, I'll tell you. Most guys would have been all "Pull it out, pull it out!" after a second or two, but Jerr hung in like a champ even with the muscles of his asshole grabbing my root so hard the cramps must have been agony. I settled more of my weight onto that sculpted back of his, wrapped my arms around to caress his chest and knotted-six-pack abs, and put my mouth down by his ear.

"I'm going to pull out now and let you feel it a second time," I said, quietly but making sure I didn't let any hint of sympathy or mercy into my voice. "If that's okay."

He nodded, but said nothing. I could see the sweat breaking out on his pain-ridged forehead, feel the tension everywhere my body touched his body, like every muscle he had was squeezed as tight as the dick-invaded ring of his sphincter.

Peeling myself up from his back, I put my hips in retreat and felt the powerful, instinctive push of his rectal muscles all along my shaft as he expelled me. When my tip came free, I watched his butt spasm closed and waited for the twitching trembles to die down.

His panting gradually slowed, and some of the contorted lines eased in his face. "Say the word when you're ready."

"Again," he said, almost immediately, trying to show how tough he was. I couldn't tell if that was to prove something to me, or to himself.

I lined up and thrust into him again, slower this time, letting myself glide instead of ramming. His ass muscles still objected, but with less resistance than before. The stroke felt tight and sweet as heaven from my end. And the virile strength of his back made me hot to get humping. But I restrained myself, massaging his pecs and shoulders instead, nipping lightly at his earlobe as his rectum tried fiercely to drive me back out.

"Another one of those?" I whispered steamily. "Or some of this?"

My hips rolled to show him how it felt to get ass-fucked at full depth by a professional.

"Nng --" he said, somewhere between pleasure and pain. Close enough to the second, though, that I figured he'd take my offer to pull out. But even though the strain on his face said the same thing, Jerry apparently had some iron fucking will on him, because instead, he growled, "That. Fuck me."

"My pleasure," I said, grinning. Then I got things started.

Little strokes first -- out and in by just a nudge. He grimaced and grunted at each one, with his asshole still having seizures around my shaft. But with every slippery, anus-expanding thrust, I heard and felt those pain reflexes drop away, until Jerry's grunting turned the corner into the territory of damn-if-it-doesn't-feel-fucking-amazing-getting-colon-probed-by-somebody-else's-cock.

I rolled and pressed against him as I thrust, making sure he felt the pillowy flesh and brick-hard tips of my tits on his back. Sweat sprang out between us, slicking the hot plane where my belly slid along his spine. Not too far in, he started humping too.

"Uhhh ... fuck, yes," he said, his tailbone moving hungrily in response to every lunge I made. "God damn."

I wandered my right hand along his hard-working abs, past the bellybutton, to tickle at his pubic hair and then at the very erect cock I found beyond his thicket. With a grab and a firm pump, I said, "Ready for this to get some attention too?"

"Uh-huh," he said, shoving hard into my grip. "Work it."

The stiff pole of my cock against his prostate had squeezed a nice dribble of precum from his tip, and a few tight-fisted tugs brought even more swelling out. I caught a palm-full and used it to polish his knob

"Uhhh," he moaned as I treated his ass and his cockhead alike to some good, slick friction. Starting to really dig it, aren't you, Jerry? When the precum got too tacky, I reached for the bottle of lube where I'd strategically dropped it earlier and squirted myself a handful. The swipe of my fingers along his shaft, wetting him up, made him groan even more. Teasing my free hand through the hair of his chest, I rode in deep and really got to work. Like a morse code of sex, I bounced back and forth between strong, reaming cock-strokes and silky-smooth milking: uh-uh-uh/oh-oh-oh/uh-uh-uh. To top it off, I shifted and circled my upper body so that the play of my breasts along his back never let itself be forgotten. "Oh, God ..."

There we go. What's that, Jerry? Where's your can't-ever-let-it-go need for control now? Hmm. Looks like you must have dropped it somewhere.

I ran my tongue up the long muscle that bordered his throat, then sucked his earlobe between my lips. The hitch of his breath and the writhing of his torso beneath me said I had him exactly where I wanted, and when I threw a glance up at the mirrored closet doors, I found him staring at us, his mouth slack and eyes almost stunned. Wrapped around him, plunging into him, gleaming with sweat, dark against his faint country-club tan, I grinned and then blew him a reflected kiss before returning my mouth's attention to his throat and jawline and shoulder.

Three times, I got him right up to the edge. Each time, I felt the extra clench of his muscled tunnel around my shaft, or heard him give a whimper, or felt his prong turn even stiffer in my grasp. Each time, I locked my hands and hips in place and gave him a nipples-and-tits-only backrub until I heard his breathing drop a good ways back toward normal. Then I'd start again, slow, and work him steadily along the road to orgasm.

"For God's sake," he groaned on our fourth push for that summit. "Make me come this time!"

My answer was a sweet glistening swirl of my hand around his cock and a half-dozen plunging, full-depth strokes into his ass.

"AH -- AH -- FUCK!" he cried out. Then he let loose with a motherfucker of an orgasm so fierce I just had to look up into the mirror and watch it. The dick in my reflection's hand blew white streamers loose all over the sheets underneath us, throwing cum across the hotel bedding like whip-strokes. I held myself all the way inside him and kept my grip tight on his throbbing erection as he ejaculated gallon-jugs of semen everywhere. When the explosions started dying down, I gave him another cock-prod in the prostate and milked his hard-on, and he shouted and blew even more hot spunk onto the linens.

"Holy fuck," he gasped, head lowered, whole body trembling. I let go of his softening prick and put my hand down to support some of my weight, in case the quivers were him reaching the limits of his strength. "Holy fuck ..."

"So. Jerry. Do I pull out and get on my merry way, or --"

"No." The shakes left him and his head lifted, eyes sure and commanding in the mirror. "I want it all. I want to know what my ass feels like with a dick coming in it. And lift up and hammer me so I can see your knockers swinging while you do it."

"Gotcha," I said, in a tone that made it sound like I meant, Aye, aye, sir, even though I really meant, I got you good, didn't I?

I rose up from his sweat-slick back, dragging the nails of both hands along his spine as I went. Then I took hold of his waist, made eye-contact in the mirror, and drew back until only my tip remained lodged inside him.

"Hard and fast?" He nodded brusquely, so I nodded back. "Here we go, then."

I'd kept my own orgasm at a low boil through every trip pushing Jerry toward his brink. It wouldn't take much to bring me off, especially with this Big Man's domineering, masculine physique on hands and knees in front of me, waiting for me to slap it into him.

Time to find the sweet spot, Trini. Long enough he thinks he knows what a real ass-pounding feels like, not so long he gets tired of it and thinks you're overstaying your welcome. Somewhere a little short of a minute, maybe? Play it by ear.

With a quick pump of the hips, I laid into him, making sure I threw my shoulders back at the same time for maximum boob-bounce. We both grunted with the power and pleasure of that jab -- but I made sure I beat him out for loudness.

"Fuck, that's good," I said, keeping my teeth shut tight as I pulled back for another stroke. "Nnnf!"

Knit those eyebrows together, girl. Curl those lips. Show him how good it is, giving him a good buttfuck.

"Uhh! Uhh!" With every thrust, I accelerated, fingers clutching his muscled waist or digging into his ass-cheeks. "UH! Fuck, yes ..."

"Do it," Jerry commanded. "Do it!"

I put that touch of heaven into my voice as I groaned and whapped up against him. It didn't take any faking -- levering my cock into his tight hole felt fantastic. "Ooohh ... ooh ... uh --"

Faster. Faster. Face scrunched in, breath steaming through my nostrils and snarling teeth ...

"Ah ... Uh ... UH ... UHHNNG!!!"

Bingo.

The floodgates opened, and Jerry found out how a long, strong stiff one feels, blowing loose inside your ass. I threw my head and shoulders back, breasts raised high, hands clamping him to me in a vice-grip so he got the full effect of my hard on, plunged into his bowels and pumping a out fat load of semen that only the condom kept from absolutely flooding him.

"Mmmmmm," I hummed, relaxing back to vertical and opening my eyes. Moment of truth.

Jerry had what I think of as The Look.

"Was that okay?" I patted his bottom and pulled out.

"It was fine," he answered. But he didn't make eye contact.

Yep. Not going to get a call-back from Jerry. Enjoyed being a cum-bucket too much to risk a repeat.

He slid over and sat at the edge of the bed, hands on his knees. I threw a glance at the bedside clock.

"Plenty of time left on our two hours," I said. "Should we wash up and --"

"No." His back straightened. Hands moved from knees to thighs. Then he stood and turned. "I got what I needed. You can go."

"Sure," I said, scooting off the bed to fetch my handbag. I dropped the bottle of lube in it and slid a business card from the side compartment. "Here. In case you ever decide to call again."

The Look. He wanted it. Wanted to take it. Wanted me to stay so he could bend over and take it, and take it, and take it. Maybe past the two-hour mark. But he just couldn't let himself go there. Couldn't be the weak one, getting studded for someone else's pleasure. He did accept the card, though. Too much business reflex in him to flatly say no to another professional's card.

I wonder how long he's going to spend in this room, deciding whether to toss my number in the trash or put it in his pocket.

But I kept that thought to myself and headed into the suite's living area to get dressed. Jerry shut the bedroom door between us and didn't open it again.

* * *

So on the one hand, yay! I didn't have to worry about Jerry bringing up the subject of my job. I'm a fucking Einstein at reading posture, and Jerry's had gone just tense enough for me to know how scared shitless he was that his family might learn the scoop I had on him.

But on the other hand, oops, I'd fucked my boyfriend's father.

Kind of a big secret to keep from Wyn, but how in God's gonzo gonads could I possibly tell him?

"Mom not here?" Wyn asked. His voice had a hint of pins-and-needles in it, like he either wished she was there to keep his dad in line, or dreaded the possibility of having to make the same several shocking revelations more than once.

"Took the boat over to town with Liselle," Jerry said, releasing his handshake with me and switching to offer one to his son. "Shopping."

Holy shit, that's some over-the-top family PDA right there, I thought, watching Wyn and his dad shake hands.

"Come on," Jerry said, when the gratuitous show of affection wound down. "Let's ..." He tossed a glance my way. "Let's get some drinks."

We followed him through the house -- under vaulted ceilings and past ostentatious sculptures and the posh trappings of wealth. And this is just the shit that the owners decided they could spare to make their renters feel at home. Wonder what those people's house looks like.

"Nice place you found this year, Dad," said Wyn as we came into a marble-floored great room, chandeliers suspended over the furnishings. A giant but undecorated artificial Christmas tree stood in one corner with an unopened shipping crate next to it.

Mister Tate headed for a bar on the far side of the main sitting area. "Wish I could say I did it just to impress ... um, Miss Jones. But actually, I won a bet with Carlson Fenway. Loser had to put up for the winner to stay here. Twenty grand a night, five-night minimum. And I'd have been shelling out five times that on jewelry, if your mom caught me losing that kind of money. What can I get you?"

"Midori and gin," I said, not bothering to add, if they have it. Looking at the place and the size of that bar, they had it.

"Rum and coke, please," said Wyn.

Jerry mixed our drinks, and we took them over to a huge, enveloping couch and some massive armchairs. For himself, he brought a tumbler and a bottle of expensive scotch, pouring several fingers and then sitting in the chair nearest the couch where Wyn and I settled.

"Here's to a spectacular holiday visit," I said, raising my glass. The two men did likewise -- Jerry tossing back more of his drink than Wyn or I did when the toast was over. "Mm," I added after a sip. "You're a pretty good bartender, Jerry."

For half an hour or so, we nursed our drinks and made small talk ... how our flight from Nassau had been, how the cruise had been, what kind of bet Jerry had made with Carlson Fenway. (That turned out to be a game of "Fantasy Fortune 500" -- each player picked a CEO, COO, CFO, and C-all-the-other-letters-in-the-alphabet-O, then tracked the stock performance of each executive's company for the year and averaged them to find out who'd done better.) The conversation avoided any hot-button topics, and either that fact or the rum and coke settled Wyn down until he looked almost at ease in the big, overstuffed sofa.

Then a door opened somewhere, and a female voice called out, "Hello-ooo ..."

"Ah, the girls," Jerry said, standing quickly and shooting his cuffs. "We're in here, Meredith."

With a bit of echoing sandals-on-tile noise and feminine chatter, two women made their way through the house and appeared through the cove-side archway. One stood tall and ice-queen imperious, blond hair falling cleanly to her shoulders, a chic white sundress wrapping up her runway-model elegance. The other ...

Jesus fucking Christ. It was all I could do to keep from saying it out loud. You have got to be shitting me.

Merry.

* * *

The first thing Meredith Tate had said to me, once the hostess seated us at an isolated booth a year earlier, was, "So, just to be clear, I didn't actually hire you to ... you know, do what you ... well, you know."

Wife found the card, I thought. I've had this happen to me several times, surprisingly enough. Usually, the husband's "carelessness" substituted for having the balls to outright say he wanted a divorce; leaving my card where a spouse could get hold of it took some major incompetence or deliberate self-sabotage. Twice, though, it had led to some wild threesomes that hubby didn't have the guts to outright ask for.

"That's perfectly fine," I said. "The charge is the same either way, though."

Merry nodded, her prim, china-pale features struggling with propriety. She had grave hazel eyes, an unscowlable Botox forehead, and perfect deep-brown hair that probably took three professionals just to open the bottle it came out of.

"My husband ... well --"

I stopped her by moving my eyes toward the waiter who approached us over her right shoulder. We ordered our drinks, she told him that was all we'd be needing, and she gave him a hundred from her pocketbook to show she meant it.

"My husband doesn't know that I know where his secret business-card stash is. He's a very clever man, but he made the mistake of marrying a cleverer woman, and I like to keep track of what he's up to."

"So ... you set up drinks dates with all the women whose cards he brings home and hides?"

She frowned, making mid-fifties lines appear around the corners of her mouth. "No. But ... if they have websites, I do look at those. And I looked at yours."

Not approvingly, I gather.

Our cocktails came, and then the waiter beat a hasty retreat. I was a bit sorry to see him go; he had a delicious dimpled chin and an even better bottom.

"Merry," I told her, feeling uncomfortable that I had only her first name to use. Given the lady's overstarched formality, 'Mrs. So-and-so' would have rolled off my tongue more easily. "I hope you're not going to ask me for details. As I'm sure you can imagine, my line of business takes a through-the-roof amount of discretion."

Her composure gave the tiniest twitch. "I could offer much more than your fee ..."

"I wish I could take it, because I don't like to see anyone upset as a result of what I do. But I just absolutely can't. I hope you understand."

She took a deep breath and a pull on her Manhattan.

"Well then ... in general terms. Could you answer some questions about your usual clientele, without naming names?"

Oh, honey, if I don't have to name names, I'm happy to talk all night on your dime.

"Of course," I said, with a reassuring smile.

Merry nodded and thought. "First ... are most of the men who engage your services ... well, are they secretly homosexuals?"

"Almost never," I said, smile turning frank. I pointed both index fingers at the swells of my breasts. "Gay guys usually aren't into these. Or waists as curvy as mine."

"I see," she said. "That's some relief, I suppose."

Right, I thought. Cheating on you might be bad. Cheating with hookers might be worse. But cheating because he's gay? Oh dear, the embarrassment.