Business Trip

My wife always giggled when I showed her my latest assistant. I had a penchant for young, eager boys looking for the first rung of that corporate ladder. Simple eye candy to toy with my homoerotic side, and never anyone that could threaten what I had with her, and she knew it. A little fantasy. These boys would stay on for a bit, maybe initiate or engage in some casual flirting, but the job was always first: I wasn't about to jeopardize the career I made just for a physical fling with some twink in a suit (although some of them tempted me to do so). But during their tenure I'd give them guidance in the biz, make some connections for them, and then they would move on. I stayed in touch with several, and always celebrated their successes.

Of course, once the job was open I got to interview a new batch of promising business upstarts with hopeful resumes listing top-notch credentials.

"Uh-huh," my wife would say, as I conferred with her about my final few candidates. "And which is the cutest?"

Alec had come from a solid school with top marks, and in his interview was grounded, relaxed, and had that air of someone ready to learn and ready to hustle.

He came in just at the right time: quarterly reports, budgeting meetings, traveling to branches...it was all a lot to handle and Alec slipped into the overload of dates and times and emails like a champ.

I needed to take a weeklong trip out to Arizona for a set of pretentiously boring, seemingly needless meetings. On weeklong trips, I usually brought my assistant, and maybe Amy, my secretary.

As fate would have it, a snafu with booking meant we had two rooms to split between the three of us at the hotel. Alec apologized and tried to sort it out while Amy and I had martinis at the bar.

Amy, discreet and indispensable, was my age and off-limits. If anything were to happen between us, it would've happened long ago, and it didn't.

"I'm so sorry," Alec said as he came into the bar from the front desk. "I've made a big blunder. I'm so sorry."

"Oh, don't you worry about it," Amy said to the boy. "Your boss doesn't mind, do you boss?"

"Of course not, it's okay," I said, playfully. "You can bunk with Amy. She'll keep you up watching old episodes of The Golden Girls."

"Are you kidding? These trips are the few opportunities to be away from two teenagers who think they're adults and a husband who thinks he's a teenager. I'm keeping my room for myself, thank you very much."

"Would you like me to try and book you a room somewhere else?" Alec asked.

"No, we're going to have a few late nights with these meetings. Late nights will be paid for, both in hourly wages and in room service, before you even ask, Amy. I just want you to be comfortable, Alec. Okay with you?"

The young man blushed. "Sure. If it's no trouble."

Amy said, "It's no trouble."

Our first few days of marathon meetings and appointments kept us on the run. By the third day, I was ready for a break, and called for a halt. I told Alec to reschedule the anything we had after 3pm, so we could all take a breather. I sent Amy away with the company credit card to go "entertain clients," meaning she could go order for two at whatever restaurant she wanted to, plus have a spa night.

"I thought I'd hit the pool," Alec said.

"There's a pool?" I said in mock-surprise. "There's life outside this schedule?"

He laughed.

"Okay, you hit the pool and let me know what you want for dinner. Since Amy's got the card, I'll give you one of mine."

"You should hit the pool with me," he blurted out.

"I don't have a bathing suit," I said.

An hour later, I was standing in our hotel room across from Alec, holding up the "bathing suit" he had rushed out and bought for me.

"Where's the rest of it?" I asked.

"It's a Speedo." He avoided eye contact as he put tanning oil and a towel into a shoulder bag. "I've seen enough of you to know you can make it work." He caught my eye. "Uh. Sir." He then pulled out the one he bought for himself without looking at me again, and went into the bathroom. After a few minutes, he came back.

Alec was hot. Incredibly hot. Tall, skinny, toned. Hairless. An androgynous look that was tough not to drool over. And he was wearing a pair of bright yellow bikini bottoms showcasing a disproportionately large, coiled cock that proved his own bathing suit was perhaps a size too small.

He tried to act casual, finally putting a water bottle into the shoulder bag.

"You think I'll look like that?" I asked with my hand out to indicate all of him.

"Probably better," he said. His suit seemed to be getting smaller, and he blushed as he covered it with his shoulder bag and said quickly, "I'll be out at the pool, charging margaritas to the room."

I'd been keeping in shape, so I wasn't worried about stepping into this tiny outfit, and in my experience with any pool in America, you're never gonna be the worst-looking one there. I was actually delighted. I showered quickly, slipped it on, positioned my bulge, laughed. I checked in with my wife, who laughed at the pictures I sent. We had a quick conversation about Alec, and she gave assent to anything that might happen. "If he doesn't fuck you," she quipped, "I'll book a flight out there myself."

The pool area was empty, the desert beyond, except for Alec, laid out on a beach chair like a movie starlet, one leg extended, one knee drawn up, sunglasses, his giant bulge straining from his tight suit, and he was already slick with tanning oil.

"How do I look?" I asked.

He pulled his sunglasses down and looked at me.

"Good to know I can do your shopping for any occasion," he said.

I laid out. A waiter came with a pair of margaritas. And then another pair. And then some tapas. The sun baked us, and we were having a good time, mostly talking about the people we were meeting on the trip, business quickly turning to gossip, gossip quickly turning to flirting, and all the while I couldn't help but realize I was going to fuck my assistant.

Suddenly, I realized I was very drunk. And suddenly, I realized he was very drunk.

We were talking about one of the people we met here--a rather curmudgeonly-yet-fit regional manager--and Alec said, "He'd probably be a great lay."

"He wasn't," I said.

The moment hung in the air. In that pause, Alec strangely brought his towel up over his bottom half, and raised his knees in the air.

"Everything all right?" I queried, smiling. I sat up on my lounge chair and faced him.

He stammered. "Oh. I'm just...I'm just fine, thank you."

"Are you sure? What are you covering up for? I thought you were trying to get a tan.

More stammering.

"Did your bathing suit suddenly shrink?"

"Stooooop," he smiled.

"All right." I laid back down on the lounge chair.

A few more quiet moments, and I could see him sit up quickly and face me, holding his towel down over his lap.

"What was his dick like?" he

"I couldn't tell," I said. I let it hang in the air. Then I turned my head and looked into his eyes. "Mainly because I had my own cock balls-deep in his mouth in a closet off the conference room at the hotel we were at two years ago, then I bent him over and fucked him doggie-style. We were under a time crunch for a meeting, so we didn't get too far after I came down his throat."

The young man was speechless.

"How's your bathing suit?"

"You whore," Alec said.

"I'm a sucker for a good-looking twink. And he's a good-looking twink."

"Am I a good-looking twink?"

I put my hands on his knees. "Oh, yes."

Halfway inside the room and I was already on him. The sun was slanting into dusk, oranges and golds through the windows looking west. We held each other and made out, he licked my nipples and I kissed his neck and he tongued my ear and I pulled his hips to me so our suited cocks could rub one another. We were drunkenly playing at foreplay, when all I wanted to do was watch him suck my cock and see my cum all over his chest after I fucked his little boy pussy. I pulled down my suit, and he did the same and I gasped as his rod stuck out so large I wondered how I shouldn't rent another room to fit it.

We kissed in sloppy, wet, great heavings while we stroked each other.

"You're gonna suck my cock," I said, letting go of his dick and putting my hands on the side of his face while I nibbled on his lower lip.

"No I'm not," he said, and pulled back. He looked me right in the eye. "I take orders from you every day, all week." He walked into the kitchenette, and I followed his tight little ass until he hoisted himself on the counter, spread his legs, leaned back, his mast at full. "Tonight, you're going to be my bitch. Suck my dick, daddy."

I smiled, and stepped between his knees. I rubbed my hands on the inside of his thighs, and he scooted his butt towards the edge of the counter. I kissed his nipples, kissed down his torso until I came to his great post, shaved and clean. I licked his balls, then ran my tongue slowly up, up, up his massive cock, then down, then up again. I wrapped one hand around the base and still had plenty left to take into my mouth. I teased, I flicked his tip with my tongue, I gave it butterfly kissed up and down.

And then I went to work. I worked up all the spit I could while I tried to deep throat it, choking a few times and gagging for some effect as I spat and sucked, spat and sucked while keeping an airtight seal around it and used my tongue to stroke the bottom of it back and forth, back and forth, then I would come up for air and take great gulps of air while I used his spit and precum-covered dick to wipe it all over my face, dripping drool all over and making a mess while the boy watched astonished; "You like watching daddy suck your giant cock?" I asked while slathering his wetness all over my cheeks and chin, and then went back to just bobbing as fast as I could while that one hand was still wrapped around its base, squeezing. I managed to get a finger of my other hand wet and explored his asshole, with some maneuvering on his behalf since his asshole was still on the countertop, and I fingered him, blew him, made a spit-and-cum mess, and heard him breathe in huge gasps. He put his hands on my head and simply held my that way while I worked his great big dick in my mouth, seeing how far I could take him, dropping "God I love this big dick of yours" and "Your daddy's such a good little cum slut, isn't he" and "You've turned me into a cock-crazed little whore." His replies were chopped: "Shitshitshitfuckingyesyesyesyes" and "Oh daddy's such a good little cock-sucker."

He ultimately came out of his reverie and pulled my head back. "Okay okay ooooookay." He pulled my head up and kissed me, sloppy kisses filled with spit and his precum, feeling his dick against me.

"Time for daddy to get fucked," he said, and got down, leading me to the bed. He pushed me down and laid me on my back. I spread my legs, scootching my butt to the edge of the bed and pulling my knees up. "You gonna take this big cock?" he asked, while slapping his massive stick against the inside of my thighs. "You gonna watch me fuck your boy pussy with this fucking cock?"

I assented.

It hurt. (At first.)

We took it nice and slowly. He was much bigger than the dildo I let my wife peg me with, but I wasn't helpless. He got a lot of spit worked up, pushed, I took it, he'd retreat when I told him to, we breathed together, and soon enough, he was slamming into my ass while we both watched my own dick bounce from the force. He pounded and pounded and I begged him to keep fucking me. He slowed, and I could feel myself getting close to cumming as he hit my spot constantly; how could he not? He then pulled out, and ran his hands slowly up and down the inside of my thighs while he seemed to be coming down from being close himself.

"How are you liking my asshole?"

"I fucking love it, daddy. My little bottom daddy. You like taking this cock, you little slut?"

He plunged it again and grabbed onto the base of my dick like it was a handle and squeezed while started fucking me with abandon. His slender fit body glistened with sweat in the last moments of sundown, his panting rhythmic, his words increasing in dirtiness, the slap of our bodies together. His head went back, he lost himself to the sensations, and then pulled out, leaped onto the bed, straddling me as he launched his shot all over my face. It kept coming out of him, a big fat load of hot cum. "Give me your load, give me all of it, come on, yeah, fucking cum on my face Alec, do it." He then slathered it across my cheeks and chin with his cock, panting and painting with his dick as I licked it clean.

"Finish me off, finish me off," I said, "Get your Dady off while your cum drips off his face."

Alec got off the bed and pulled me up, and hurriedly got down on his knees and started sucking my cock, looking up at me and making eye contact as his cum dripped off my face. My legs were jelly from having been fucked so hard, but I stood there and let the waves of pleasure take me there, and soon enough he deep throated me as my own load got lost in his mouth. I finished and he had swallowed it all, and we both collapsed onto the bed, his cum already stiffening on my skin.

We kissed, we kissed. We fell asleep; we woke up and showered; we went to dinner.