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A New Side

A businessman discovers a new side of himself and his friend
"Ah fuck," Jerry groaned as he collapsed on to his bed.

"Quite a day, eh?" I responded.

We’d just come from a meeting that had gone badly. To say we were both in a bad mood would have been an understatement.

"That guy is a supreme piece of shit. That’s all I can say," Jerry spat out.

"Oh well, we’ve got tonight to unwind."

"Yeah, let’s hit the bar and grill across the street for some food and fuel."

Jerry got up and started to unbutton his shirt. I was already undressing to change from my business suit into something more casual for the evening. My attention kept wandering to Jerry as he stripped, lured by the sight of his slightly muscular body clad only in tight little briefs.

The bulge in the front held a particular allure for me. I’d seen my colleague naked in change rooms and showers before. Jerry was quite well endowed, especially relative to my six and a bit inches. My mind played with an erotic fantasy of running my hand over the bulge before pulling the briefs down to release his large cock. My cock stiffened a little at the thought. I pushed my fantasies aside as I always did. I had no reason to believe that Jerry, renowned for his womanizing, would have any interest in being with a man; especially a married friend and colleague.

Dressed in golf shirts and slacks, we headed down for dinner. The place was fairly quiet. We settled into a corner booth with pints of beer and steak dinners. The sound system was playing classic rock and there was a slight buzz of conversation from the few occupied tables. A hockey game was on the screens and we turned our conversation to that sport rather than dwelling on the fruitless meeting that had ruined our afternoon.

"Damn, I’m bushed," Jerry said with a yawn after dinner.

"Me, too. Between that flight and then the meeting… At least tomorrow we’re on friendly territory."

"Amen. Ralph’s a great guy."

We got up and went back to our hotel room. Jerry stripped off his golf shirt and I once again caught myself enjoying the site of his well-toned abs and chest. Then his slacks came off. The bulge in his shorts seemed bigger. Was he, perhaps, a bit erect? The thought had my cock stiffening as I undressed.

"I’m going down for a quick swim in the pool," Jerry said, walking over to pull swim trunks from his case.

Tossing them on the bed, he slipped his briefs off. His cock fell loose, dangling invitingly below neatly trimmed pubic hair and above the beautiful sack that held his balls. It wasn’t the first time I’d seen Jerry’s cock, but I hadn’t already been aroused the other times. My cock got harder and it was difficult to hide the erection as I was down to briefs myself.

"Not a bad idea. Blow off some steam before bed."


I got my swim trunks out and slipped my briefs off, feeling a bit embarrassed to be exposing my somewhat aroused penis. Jerry was occupied in pulling his trunks on but did seem to cast a glance my way. Quickly, I pulled on my swimsuit to hide it again. We put on t-shirts and slippers and headed down to the hotel’s indoor pool.

The pool area was warm, almost too warm and steamy, but that meant that the pool water was very comfortable and relaxing. We swam around in the main swimming pool for a bit, and then settled into the neighbouring whirlpool for a soak. We had the pool to ourselves and sprawled out a bit. Jerry’s leg was brushing lightly against mine. Neither of us made a move to change that.

"God, I haven’t had a good lay in weeks," Jerry groaned, lying back and closing his eyes.

"Watch out. You’ll hurt your rep," I responded with a chuckle.

"I’m sure I can trust you not to spread the word. How about you?"

I’d moaned to him about my sexless marriage before so I’m sure he already knew the answer. My wife and I had somehow managed to turn a steamy, passionate love affair into a cold, sexless marriage in under a decade. She had recently moved away to take a new position with her company and it appeared that was going to turn into a permanent separation. The only question was who would file for divorce first.

"If I had any less sex, I’d be a priest. Hell, some of them probably get laid more than I do."

Jerry chuckled and gave me a sly look.

"That why you’re so horny tonight?"

I blushed.

"What do you mean?" I asked a bit defensively.

"When we changed upstairs, you were hard. Or getting there."

"You weren’t exactly soft yourself," I shot back.

"Thought you were looking. Is that what got you hard?"

I paused, not sure what the answer should be. I went with honesty.


Jerry smiled. Under the water, his hand stroked my thigh.

"Me, too. I’ve been wondering about you for a while, now. That’s a beautiful cock you have."

His hand slid up to massage the bulge in my swim trunks. My cock hardened in response. He gently squeezed it through the thin material.

"You … you’re interested?" I stammered out.

"I’ve been with guys before. It’s fun. You?" he responded as his fingers gave my erection a light squeeze.

"It’s one of my fantasies but I’ve never done anything with a guy."

"What’s your fantasy?"

"I have these dreams about kissing a man. We’re both naked and our hands are playing with each other’s penises. Then I go down on him and suck him until he cums."

"Let’s go. I’m thinking your fantasy should come true."

The elevator ride up was torture at first. There was a young couple in the elevator with us so we didn’t dare do anything. They were pretty open, though, touching and kissing right there in front of us. After they got off, Jerry pinned me to the wall and pressed his mouth to mine. Our tongues met and slid against each other and our hands caressed each other’s bodies.

Then the door was open and we were heading to our room. The door to the room was barely closed when Jerry grabbed me and pushed me into a corner. We kissed again; a fierce, sexy kiss. Jerry rubbed the bulge in his trunks against mine, arousing both of us to full, solid erections.

"Let’s get these off," he whispered, undoing the drawstring on my trunks.

He pulled my suit down. My hard cock fell out straight. Jerry’s fingers were on it right away, slowly stroking the shaft as he kissed me again. Then I undid his trunks and slid them down. This time we rubbed our cocks against each other as we kissed. My head was reeling with a heady mix of arousal and the joy of finally enjoying a man’s body.

Pulling away from me, Jerry quickly stripped naked. I followed suit and then joined him on one of the queen-sized beds. My surprise at what was happening was fading and I started to take some control. Rolling my friend on to his back, I lay on top of him, my cock pressed alongside his between our bellies. Slowly, I rubbed against him while looking down into his eyes.

"Oh God, Alex, I am so fucking aroused," he gasped.

"Me, too," I replied, feeling my climax approaching.

I rolled off of him, not wanting to finish just yet. Laying my head on his belly, I stroked his erection with my fingers. There was a big bead of precum on the tip and I tentatively licked it off.

"How I taste, man?" he said.

"Wonderful," I answered.

I’d never given a blow job before but had received plenty. Denise had been pretty good at it in the days when we still had sex. Wrapping my lips around Jerry the way she used to do to me, I began sucking on him.

"Oh, yeah," he moaned, "Suck my cock, Alex. I love being sucked off."

His hand was on my head, stroking my hair and guiding me to take him in deeper. His size made it impossible to take him all the way in without choking on him but I tried valiantly.

"Fuck yeah," he suddenly shrieked.

His cream flooded into my mouth and I almost gagged. Somehow, I recovered and swallowed some of his load. The rest dribbled out of my mouth on to my chin and his pubic hair. Pulling my mouth off, I licked him clean. Then I moved back up to kiss him again, giving him a taste of his own semen. That led to another long bout of French kissing, tongues sliding back and forth as our naked bodies rubbed against each other.

"Your turn, amigo," Jerry finally said.

I was soon on my back. Jerry ran his tongue down my chest and belly before taking me into his mouth. With my small cock, he easily took most of it in. A finger rimmed and probed my anus as he sucked me, a sensation that was incredibly arousing and had me wondering where we might go next. Then I was seeing stars as a powerful orgasm gripped my body. Cum dribbled out of Jerry’s mouth as I flooded it with my seed.

Crawling up my body, Jerry lay down on top of me and kissed me, sliding a glob of my seed into my mouth. I wrapped my arms and legs around him and we lay together for what seemed like hours.

"How was that?" Jerry finally asked.

"Fantastic. Leaves me wanting more, though."

"Don’t worry, buddy. There’s more to come. I promise that much."

The next morning, I awoke in bed with Jerry. My cock was hard, as it often was in the morning. Memories of the night before came flooding into my mind. Instinctively, I took my cock in my hand and caressed it as I reveled in the memory of my first sexual encounter with a man.

Jerry’s eyes flickered open and he smiled at me. I reach over under the covers to find that he was also erect. His hand found my cock and we slowly stroked each other. Then Jerry moved in close, pressing his body against mine. Our erect dicks were pressed together and Jerry moved slowly against me, rubbing his cock against mine. I loved the feeling and began moving back against him, catching his rhythm so that we were moving in near-perfect synchronization.

I rolled Jerry on to his back, wanting to be on top. Moving my hips with the same rhythm we’d had together, I rubbed my cock against his. My friend and I stared into each other’s eyes. A powerful orgasm began to build inside me, growing more and more intense until I exploded, my seed pouring on to Jerry’s belly and cock. I kept moving, using the semen as lube to move faster and more smoothly against my friend’s hardness. Then he was groaning and his cum was pouring out between us to mingle with mine. I collapsed on top of him.

"Nice way to wake up, man," I whispered to Jerry before kissing his mouth.

"Amen, brother. But we do have a meeting to get to."

"I know," I answered.

We got out of bed and showered together. Then we dressed in our suits and headed to grab a bite before our meetings began.

It ended up being a long day. Even lunch was a meeting. However, it also proved to be highly productive, with a couple tentative deals underway and one that had been under negotiation finalized. It almost made up for the crap of the day before.

All through the day, my mind kept wandering back to our hotel room. I daydreamed about the feel of Jerry’s cock in my hand and in my mouth. I got hard as I recalled the orgasms of both the night and the morning; recalled being soaked in our mingled cum.

We had an hour to kill between meetings in the afternoon and Jerry slipped away. He rather mysteriously said that he had some things to pick up. By the time he returned, we were off to another meeting but in the car, he quickly flashed me a glimpse of condoms and lube in his briefcase. That got me stiff again so I distracted myself with reading over the contract we were going to discuss.

Dinner came and went. Jerry flirted as we ate in a quiet, intimate little place near the hotel. We even made out briefly in the men’s room, kissing deeply as we massaged each other’s cock through our trousers.

Back at the room, we undressed each other slowly, taking lots of time for touching and kissing. By the time we were both naked, we were also both hard. We pressed our bodies together and gently moved our cocks against one another. Our hands roamed down to massage and explore each other’s ass while we shared kiss after hot kiss.

"I want you to fuck me," Jerry said when we were both quite aroused.


"Very. I haven’t a guy up my ass in years," he answered, giving my ass a squeeze.

My fantasies about men had only touched on anal sex. It wasn’t something that I’d really thought about doing. The idea of fucking Jerry’s ass seemed very arousing in the moment, though.

Jerry got the condoms and lube out. Leading me to the bed, he lay down and spread his legs.

"Touch my asshole," he said.

I obeyed, stroking and rubbing the rim of his back passage with my finger.

"Lube your finger and put it in. See how nice and tight it is."

Squeezing some lube on to my finger, I massaged some into the opening and then eased my finger inside. It was, as he said, nice and tight. I started to imagine how wonderful it would be put my cock inside. For now, I just slowly fucked him with a finger while using my other hand to play with his cock and balls.

"Mm, yes, Alex. That is nice. Now put on a condom and lube up. I want you to fuck me. I want your cock filling my ass."

I was hard as a rock so I rolled a condom on and thoroughly coated it with the lube. Mounting my buddy, I pressed the head against his opening. Slowly, I pushed in. His tight little asshole squeezed me as I entered it, but I got in. Slowly, I began sliding in and out, fucking him with slow thrusts.

"How’s that, Alex?" Jerry said, his voice soft and a little breathless, "How’s it feel to fuck your buddy’s ass?"

"Great, man," I heard my saying, "It’s so tight. I can’t last long."

"That’s okay man, Just fuck me until you cum. Ravish my ass with that beautiful, hard cock."

I fucked him as fast and hard as the tight opening would allow. My balls slapped against his ass with each entry. Jerry was moaning and gasping. It quickly became too much.

"Oh Jesus, yes," I shouted as my orgasm hit.

It was the strongest I’d had with Jerry yet. I couldn’t stop thrusting; couldn’t stop enjoying the feel of his tight ass gripping my cock and milking my seed out. It last for several seconds, leaving me worn out and breathless.

Then I pulled out and got down between Jerry’s legs. Taking his big, stiff prick between my lips, I began sucking him, taking it in as deep as I dared. At the same time, I entered his well-lubed ass with a finger and massaged his prostate. It didn’t take much of that before he was crying out while my mouth filled with his cream. This time, I found it easier to manage and swallowed quite a bit of it.

As we showered together afterwards, I took further delight in my friend’s body. Getting my hands all soapy, I lathered him up thoroughly. Then I wrapped my fingers around his big, beautiful prick and stroked it. It began to harden again. Wrapping my arms around Jerry, I soaped myself by rubbing against his soapy body.

Soon I was getting hard again, too. Jerry turned me around and I leaned against the wall. Using the soap as lube, Jerry slid a finger inside me. It was uncomfortable at first but I quickly got used to it, especially when he began massaging my prostate. Pulling his finger out, he washed it off.

We left the tub and went back to the bedroom. I got on all fours with my thighs open. Jerry lubed his cock, and then slid a well-lubricated finger inside me. He fucked my ass with one finger, and then added a second to get me used to it. I was nervous but his careful work preparing my ass comforted and relaxed me. Still, I couldn’t help tensing a little when I felt the head of his big member start to penetrate me.

It was a bit painful, and definitely uncomfortable, at first but got better once Jerry was inside. Slowly, he fucked me while using a lubricated hand to stroke my cock underneath me. The double whammy of his hand on my cock and his cock in my ass created an amazing, intense feeling in me. I climaxed, my seed spraying out on to the bed. My ass spasmed, squeezing Jerry’s big cock as he continued to fuck me.

"Oh shit, yeah," he cried out as his cock pulsed, filling its condom with his rich, thick cream.

That was it for the night. We were both well and truly satiated. After another shared shower, we crawled into bed knowing we had to rise early for our trip home. I'd seen a new side of Jerry and, more importantly, of myself and that had me thinking rather differently about my future without Denise.
This story is protected by International Copyright Law, by the author, all rights reserved. If found posted anywhere other than with this note attached, it has been posted without my permission.

Copyright © Copyright 2018 by D. Scott Vaughan. Originally published on and may only be republished elsewhere with the author's permission and with this statement attached.

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