tagGay MaleHis Hot Gay Assistant Ch. 02

His Hot Gay Assistant Ch. 02



The project team was assembled for the Minneapolis Consulting Engagement which was to last for six months. I had contracted with four subcontractors and I would serve as the engagement manager. Of course, I would use my assistant Michelle extensively throughout the engagement to prepare progress and status reports. I arranged for two short term auto leases for the subs to use for six months. I also negotiated favorable hotel monthly rates so they didn't have to find a room each time they came to the city.

We had our kickoff meeting at the site and reviewed the goals and objectives one final time with the client. One thing I did not allow was creeping scope in an engagement. Any additional work would require a separate contract. The subs settled into the work space provided and then went about their meet and greet meetings the first day. I would be on site each Thursday for updates and client meetings.

The first week I stayed for three days and two nights. Michelle was also with me for those three days. We stayed at a different hotel than the subcontractors. For the future Thursday meetings, I would fly in Wednesday evening and I had booked my room for the length of the engagement. If I had to bring Michelle with me for any reason, he would always share the room with me. No one else had to know that.

That Monday evening, I took the subcontractors to dinner as a way of kicking off the engagement. Later Michell and I went back to our hotel room. It had been a long day and we were a bit tired but not so tired that I would pass on his hot ass that night.

We moved into the hotel room and stripped naked. We were both hard and our cocks bobbed in front of us. I got in bed and lay on my back. Michelle got in and lay beside me. He reached down and cupped my bloated balls. As he massaged my balls I felt like my entire body was on fire. His hand moved up and began to stroke me and I could feel the pre-cum he had created spread itself down my shaft. His finger grazed my dick-hole and the contact with my soft sensitive skin made me shudder. His one hand cupped my balls as his other seized my shaft and began to slide up and down stroking and squeezing it.

I felt Michelle re-position himself on my bed and then I felt his tongue begin to lap at my throbbing rod. His arms reached behind my legs and pulled me towards him while his tongue slid down to my rigid cock tasting me and sucking me. He took my balls in his mouth and pulled at them with his lips as my dick stiffened with my lustful pleasure. He sucked both balls into his mouth and his tongue danced across them in his warm cavity. I let out a low moan as his hands reached around under me to massage and squeeze my ass cheeks with his delicate hands. I felt that I could cum at any moment.

"Michelle I'm very close."

He pulled his mouth off of me and looked me in the eyes as he said, "Cliff, I want you to cum in my mouth I want to taste you first."

He then seized my dick and engulfed me in his mouth. My swollen cock collided with the roof of his mouth as he swirled his tongue around it. He sucked me hard causing me to arch my hips and then his head bobbed up and down my shaft. I felt the familiar signs of an incredible orgasm building within me. His lips were twisting around the shaft of my cock and he plunged his mouth to the base of my cock then he re-chambered and plunged again. All of a sudden, he stopped and used his tongue to stroke the underside of my cock head driving me crazy.

I was beside myself as I needed to cum. I began bucking against him in an effort to get myself off but he wouldn't move tantalizing me with his inaction. Frustrated I stopped bucking and laid there giving up on what I expected to be a great release. He had me exactly where he wanted me and then he suddenly cupped my balls as his lips surrounded my cock and he sucked me toward him. I felt the release building inside of me and I exploded into his mouth. I groaned in immense pleasure as streams of hot cum landed against the roof of his mouth and the back of his throat. I felt his throat muscles contract as he drank it down and searched for more. His mouth never left me as he continued to suck on my cock. Finally, I couldn't cum anymore and I collapsed down onto the bed as my body tingled from head to toe.

As I lay there I was lost for words as I still felt the overwhelming pleasure of more bisexual sex. I watched as Michelle lay next to me and stroked his tiny cock. I saw him stiffen and then I watched as ropes and ropes of cum shot out of his cock and covered his body from his neck to his abs. I was still rock hard and my state of desire did not escape him and he spoke to me.

"Are you ready to fuck me now. I want to feel your cock in my ass. I want you to fuck me."

"Yes, I'm ready to fuck you."

Michelle rolled over on all fours and handed me the tube of lubricant. "Take your time and prepare me for your cock and then fuck me in the ass."

I knelt behind him and I begin to caress his beautiful ass his body was delicate, hairless and flawless. Every time, I did this, I couldn't believe how much he looked like a girl from behind with his shapely curvy ass in the air and with his soft hair covering his neck and ears. I put an ample amount of lotion in my hands and rubbed it all around his rubbery ring. I inserted first one finger then two fingers in his anus preparing him for my cock.

As I sawed my fingers in and out of his anus I was getting turned on by the thought of burying my cock in his shapely ass as I had so many times. I moved closer to Michelle and lined up the head of my cock with his anal opening and began to ease it into to him. My cock head cleared his entrance and it slid right in without resistance. As always, his ass chute was warm and tight as I went deep into him. I was all the way in his ass and I started a slow fucking motion. I continued to pump his ass with deep, long, deliberate thrusts as I caressed his smooth round buttocks.

He asked me to fuck him harder and quicker. So, I picked up the pace and I started pounding his ass faster and faster. My balls started bouncing off of his balls and he was moaning with each thrust of my cock. I could feel my climax building and I knew that any moment I would shoot my seed in his ass. I tried to make it last as long as possible but to no avail, I lost it.

I fired a barrage of cum in his ass filling it to overflowing. As I continued to fuck him, my seed backed up in his rectum and began to ooze out flowing over his balls. He used his talented sphincter muscle to milk my cock and drain it of all my seed. I remained hard in his tight sheath. Michelle flattened out on the bed with me on top and my cock still in his ass. I rolled off of him and as I did my hard cock slipped from his ass. He rolled to his back and spread his legs lifting his knees to his chest.

"Fuck me again," he said urgently.

"I can't cum again right now."

"Your cock is still hard, just fuck me until I cum."

I moved between his legs much like I would with a woman and lined up my still erect cock with his anus. Michelle was also as hard as a rock and his cute little cock pointed toward his head. I pressed slightly forward and my cock moved into his hot ass. My cock went all the way in him and my balls rested on his ass.

"God, that feels so good, poke me, fuck me."

His ass was in the air and my cock was fully embedded in it. I pulled back a little and pushed forward. He groaned as I began to slowly fuck him. Each time I would start taking longer strokes. My cock head was soon at the edge of his anus before I pushed it back into him. Our fucking was making a sucking sound. Each time my balls slammed against his ass, my body and his ass made a wet slapping sound. I was so fucking hot that I crammed my cock fully into him. He held my cock and he massaged it with his sphincter. He humped up against me fucking me back as I fucked him. My bedroom smelled of sex and sweat.

"I want to cum just from you fucking me. Just keep fucking me."

I took slow long strokes in and out of his ass as Michelle pushed up into me more and more. Soon he took control and just fucked my cock. I let him fuck me with his ass. His actions began more erratic and his thrusts shorter and more powerful. He was grunting as my cock slid in and out of his hot ass. Soon my cock was barely staying in his ass. Then he slowed down and let my cock just press against his prostate. He announced that he was cumming. I watched his cum shoot between our bodies covering his chest and his abs and then oozing out around his pubes. I continued fucking him until my legs were weak. My cock slipped from his ass as I rocked back on my heels. I plopped down on the bed beside him and stared at the ceiling.

"I love getting fucked. You do like my ass."

"Yes you have a lovely ass. Let's get some sleep."


When I woke up the next morning I had a morning piss hard on. On another occasion I would have been fucking some girl senseless in the morning but not today. Not up for a workout, I passed on the fitness center. I got out of bed and walked into the bathroom. Michelle was in the bathroom standing naked at the sink and I eased by him. He purposely pushed his ass out at me and let it brush against my thigh. I smiled and grabbed his shapely buttock and then released it. I stood over the toilet and pushed down on my stiff cock to aim the urine into the bowl. It is a strange wonderful sensation when the urine runs through your stiff cock. I held my cock as it softened and I was able to pee.

"Let's go back to the bedroom," Michelle said in a raspy voice. He was clearly excited and ready to fuck again.

I walked over to Michelle as he sat on the side of the bed and pulled me in toward him. He reached up with his hands resting on my thighs he caressed my muscles causing my cock to bob about in front of him. He slid one hand across my belly wrapping his soft fingers around my shaft and pressed my cock up against my belly. Then I felt his mouth on my cock. He caressed me with his tongue, moving from deep underneath my balls to the very tip of my cock in one lingering sweep. We both moaned as his tongue swirled around my swollen cock head, his hands caressing my shaft and balls. His fingers probed between my legs.

I moved as he looked up at me, easing my legs apart as he cradled my balls in one hand, my cock in the other. His fingers reached down to rub the hard-taut skin between my balls and my ass. I moaned as I felt the hunger in his movements and I watched his tongue move across my cock. The air cooled the wet spots he left behind on my pubes. With a moan, Michelle let my cock fall away from my body so that it was swaying in front of me again. It stood straight out from my body. He glanced up at me and then back at my cock before taking me deep into his mouth.

My legs felt like jelly as I felt his hot wet mouth around my cock. He sucked me hard and drew me in deep. His tongue lashed across my cock head and I felt his teeth gently slide down my shaft. My cock jerked in his mouth as he sucked hard. My cock bulged in his mouth as I thrust forward and began to fuck his mouth. I reached for Michelle's head, feeling his silky soft hair as I plunged my cock into his mouth. His sucking matched my thrusts.

He released me and I watched as he reached for the lube. He smeared some lube over me, his hands moved across my cock and balls. He knelt on the bed on all fours and looked at me over his shoulder.

"Fuck me," he quietly requested before dropping his head down onto the bed.

I moved quickly, moving behind him, by cock bobbing and swaying in front of me. I knelt up, towering over him with my cock reaching out to him. Seconds later, my cock was buried inside him as I thrust expertly into his waiting body. I heard Michelle cry out as I drove my cock deep inside him. I could feel the heat in his ass around my cock.

"Fuck me, ugh, yeah, ugh, fuck me!"

So I did, I fucked him hard, driving into his body as deep as I could, my balls slapped against him as he reached under himself for his own cock. I fucked him long and hard and deep. His body clung to my cock and sent powerful waves of pleasure through us as we moved together. I drove into him and he pushed back to meet my thrusts. This time Michelle ejaculated and I caught a glimpse of his load landing on the bed. As he came his sphincter clenched and released around my cock. I held still in his ass until he stopped cumming. Then he rolled over, lay back on the bed and lifted his legs like a woman.

"Fuck me, fuck me like you would a woman."

I moved quickly toward him, my cock bobbing and swaying in front of me. I knelt up, towering over him with my cock reaching out to him. Seconds later, my cock was buried inside him as I thrust expertly into his waiting body. I heard him cry out as I drove my cock deep inside him. I could feel the heat in his ass around my cock. It was strange fucking him in the missionary position and I missed looking at his curvy ass.

I fucked him hard, driving into his body as deep as I could, my balls slapped against his as he reached for his own cock. I fucked him long and hard and deep. His body clung to my cock and sent powerful waves of pleasure through us as we moved together. I drove into him and he pushed back to meet my thrusts. When he came again it was like a dam bursting. His moans and groans filled the room as cum gushed onto his body. I still had not cum and I didn't think that I could in that position so I pulled out of Michelle and flipped him over on his stomach. I lifted his hips up and caressed his curvy buttocks before I slipped my cock back in his ass. Fucking him in this position was a turn on as I watched my cock slide in and out of his shapely ass. Within minutes I flooded his rectum and I felt the warmth of my seed surround my shaft.

This time when I rocked back on my heels and my cock left his ass, semen flew out of his anus. It looked like he was cumming out of his ass. The anus twitched as the syrupy liquid was forced from his rectum. I had never seen anything like it. After the first couple of spurts, my seed oozed out and trickled over his scrotum. That was enough for the morning. We cleaned up, dressed, ate a light breakfast and headed to the client site. That evening we dined alone and later returned to the hotel room. He asked me to massage his body. He took off his clothes and lay naked face down on the bed. I also took off my clothes, retrieved the hotel supplied body lotion and then straddled his body. I sat on his legs just below the buttocks and rested my soft cock in the crack of his ass.

I poured the lotion on his back and shoulders and then began to massage his pretty body. Michelle's soft skin was hairless, smooth and flawless and my hands glided over it. After several minutes of massaging the upper body I turned my attention to his ass. I massaged each of the buttocks relishing in the feel of the round firm globes. I must have massaged his gorgeous ass for at least 15 minutes. I felt my cock begin to harden again and soon I was erect. My huge hard cock was nestled in the crack of his ass and I slid my cock within the fold of the buttocks.

"You like my ass, don't you?"

"You always ask me that and you know I love your ass. I love fucking you in your perfectly shaped ass."

"Fuck me again, okay?"

I smoothed the body lotion all over my cock and then I poured some of it in the crack of his ass. I then fingered his anus making sure that it was well lubed for another round of butt fucking. Satisfied that he was sufficiently lubricated, I eased my cock into his hot ass for the third time that day. He pushed his buns up to meet my penetration and the cock slid in easily. He groaned when the thick shaft filled his anal passage again. I fucked him for what seemed to be hours before I finally came and then I collapsed on top of him. The two of us remained in the same position for several minutes before we separated. I rolled off of him and lay on my back beside the pretty young man.

"Cliff, that was so good. I love it when you fuck me and cum in my ass."

"Yes, I enjoy it too. I getting a drink from the mini bar, want one?"

"Yeah a beer would be good. What time is our flight tomorrow?"

"Not until 4:00 PM. I'll head to the office around nine and check that things are going okay and then I'll come back here and get my stuff."

We sat up in bed and enjoyed our drinks. That night I had Michelle sleep in his own bed as I wanted to sleep well and get up early. The fitness center was open 24 hours and I hoped to get a workout in the next morning. Fucking Michelle was definitely a workout but not the kind I was thinking of at the moment.

He was still asleep when I got up, put on my workout clothes and headed to the fitness center the following morning. I got in a good one-hour workout and then returned to the room. I woke Michelle up when I entered the room. He looked exhausted, I went in the bathroom to shower and shave. He was still in bed when I got dressed and I told him to stay there.

"There's really no need for you to be at the site this morning. I'll be back for lunch and then we'll leave for the airport."

I left the room putting out the Do Not Disturb sign. I checked in with the client and they were pleased so far. Then I touched base with the subcontractors and everything was fine. I went back to the hotel and by then Michelle was dressed, packed and ready to go. We checked out and stopped for lunch on the way to the airport. It had a been a successful beginning for the engagement and two days of great sex.


We were both in the office on Friday preparing reports and following up on the RFPs. I received a call from the one large firm and they had landed the one engagement for a client in Pittsburgh. They would need me for three days a week for the next six months. The Minneapolis engagement was also for six months. I needed to be in Pittsburgh on Tuesday, Wednesday and Thursday. I would be busy but the compensation was worth it.

I contacted my Minneapolis client and got permission to hold the meetings on Friday instead of Thursday. That meant I would be flying from Pittsburgh to Minneapolis on Thursday nights. Michelle would have the status reports prepare and meet me in Minneapolis on Thursday night at the hotel. We changed our hotel and flight plans to meet the new schedules.

Both engagements would wrap-up in March the following year. That meant that I would not be taking a ski vacation in Colorado this year unless I wanted to go in April. I knew that Minnesota had some decent ski areas. I could stay over some weekends and get some skiing in there. I was going to be on the road a lot and suddenly the Omni office setup seemed like overkill.

That weekend I checked with the condo real estate management company and inquired about the three-bedroom units. As it turned out, one was becoming available in a month. I put a deposit down to hold it and placed my two-bedroom unit up for sale. It was a very desirable complex and units turned over very quickly. I would run the business from the condo, setting up one of the bedrooms as an office.

For the next several weeks, work was like drinking from a firehose for Michelle and me. I moved into the three-bedroom condo and two weeks later my old unit sold. I put Michelle in charge on making the office transition and gave the Omni office my required 30-day notice. They had a waiting list so it was no big deal for me to move out. I was on the road Tuesday through Friday. On the weekends and Mondays, Michelle and I got the office set up in the condo. Michelle had purchased the office furniture and set up all our files. He was incredibly efficient.

It was mid-November before things got back to a reasonable pace. I was looking forward to Thanksgiving week as I would not have to travel and I had no plans to visit family. It would be a relaxing week. An added benefit of working from home was that office sex would now take place in the bedroom with both of us naked. Michelle had no plans for Thanksgiving so I invited him to spend to spend the day with me. I learned he was as efficient in the kitchen as he was at work.

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