tagGay MaleExecutive's Tour on the Bi Side

Executive's Tour on the Bi Side



It was 1982 and I had just been hired by a company in a Chicago suburb to manage the technology division. It was an Executive position with similar responsibility to my previous job in Ohio except that the compensation was double. My biggest disappointment with the new job was that I left my administrative assistant Susan behind at the other job. Susan was married and could not leave the state. She had not only been a good assistant but she had been the best piece of ass that I ever had. She was a great lover who liked to suck cock and take it in her marvelous ass. I was a big fan of anal sex and a day in the office didn't go by that I didn't have my cock in her mouth, pussy or ass. The office sex had been great and I would miss her dearly. I dated many women out side the office and had plenty of sex in my life but there was something very special about having sex in my office.

My name is Cliff and I am 36 years old. I stay very fit playing tennis, golf, skiing and SCUBA diving. I am 6'2" tall and 190 pounds with short brown hair and hazel eyes. In addition to my sports activities, I also work out at a fitness center whenever I can fit it into my schedule. The first three months at my new job didn't allow much time for much free time but I was able to hit the gym every morning before work. During the first three months I was also looking to hire an administrative assistant. That title had replaced the older job title of secretary in the 1980's. I was using a temporary employee who was actually an excellent employee.

I knew that it was unlikely that I would ever find someone like Susan again but I interviewed many women during that three month period in hopes that I might find someone. Most of the women were not sexually appealing and others could not meet the job requirements. The temporary employee had superior admin skills compared to the candidates and I would be better off hiring him. Yes it was a guy and I was convinced that he was gay but his work was outstanding. I finally broke down and offered Lee the job and he was thrilled to accept it.

Over the next three months Lee did an outstanding job and proved to be a very loyal employee. He proved that he could handle confidential and sensitive information. I was restructuring the division and there would be personnel changes involved. It was important that the information did not leak out before my presentation to Executive management. Lee and I worked long hours and as we did we became very close professionally. However I often caught myself looking at him in a feminine way.

Lee was about 5'6" and weighed probably no more than 150 pounds. His hair was blonde and it covered his ears and the nape of his neck. He had a slender waist and an ass that would not quit. I often thought that many a girl would kill for an ass like that. He usually wore tight fitting slacks that hugged his buttocks and showed off his curvy ass. I hadn't learned much about Lee's gay life style but I was sure that many a gay dreamed about fucking him. I had bi-sex once in my life when I was in the military stationed in Paris when I fucked this cute little French guy in his bubble butt. That was my only encounter with a guy and it seemed like I was fucking a girl in the ass. As we neared the presentation date I started to wonder what it might be like to fuck Lee in the ass and as it turned out I would learn soon enough.


The presentation was off site at a hotel. I was one item on the Friday agenda of the Executive retreat. The retreat was Thursday and Friday and we all had rooms at the hotel for Thursday night. I opted to book the hotel room for the weekend because I was in the mood for some R&R. It was a resort like setting with a golf course, swimming pool and a nice lounge. I thought that I might even get lucky and pick up some horny chick.

Lee showed up at my room early Friday morning and we put the finishing touches on the presentation. I told him to hang out in the room as I wasn't checking out and I would brief him later on how the proposal was received. I told him to order breakfast if he wanted and that I would see him after lunch. As it turned out the proposal was well received by management and I was given the green light to proceed beginning that Monday.

After lunch all the other Executives left the resort and I returned to my room and I let myself in. I didn't see Lee so I assumed that he was probably in the bathroom. I walked in and looked around and sure enough I spotted him with his back to me in the bathroom. He was completely naked and I took in his slim lines down to his perfect ass. Lee leaped in surprise and spun around when I called out his name. I stared as he turned toward me and his erect cock danced in front of him as he spun around. I was stunned and embarrassed.

"Oh my, Cliff, you scared the hell out of me," Lee gasped.

I stared at his body amazed at how much he resembled a girl when he was naked. His body was hairless and his skin flawless. From the back he looked just like a girl with a slender shapely body and a perfect bubble butt.

"I'm sorry," I apologized.

I noticed that his cock was still hard and he saw my eyes glance at it. He was certainly average in the cock department and I guessed him to be right around 6 inches with normal girth.

"Sorry about this," he said as he grabbed his erection, "I was thinking of something and I started to jerk off."

I observed Lee as he shifted his weight to one side and flipped his hand up as he replied. His body language was definitely feminine. I was surprised that his cock was still erect and I attributed that to his youthful horniness.

"Hey I just made some coffee, do you want some?"

"Sure, coffee sounds good but do me a favor and put some pants on," I replied.

Lee laughed and said, "Oh sorry about that. I went swimming and I just got back."

I still didn't know what or who he was thinking about when he was jerking off. Lee put on a snug bikini swim suit that showed off every curve of his ass. The outline of his erect cock was still visible in his swim suit. He actually looked sexier with the bikini on and I wasn't sure it was an improvement over his nakedness. I felt my cock stir as I wondered once again if he took it in the ass. Then I scolded myself for thinking about my assistant that way. I sat in a chair as Lee poured the coffee and I watched him as he served it. Lee moved like a girl and his body language clearly sent the message that he was gay. He set my coffee on the table and I watched his curvy ass as he moved over to the sofa.

Lee and I chatted while we had the coffee. He then got us refills and once again I watched his curvy body move gracefully around the room. I was sure that he was doing it on purpose. We talked about the presentation and management's approval before Lee turned the conversation toward sex.

"Cliff do you consider yourself straight or bi?" he asked.

"That's a hell of a question. Why do you ask me that?" I replied a little shocked.

"Well I know that you are straight but I also noticed the way you watch me sometimes," he answered and then asked, "Have you ever had sex with a guy before?"

"Yes but it was quite awhile ago when I was in France. I met this young French guy and he sucked my cock," I admitted.

"Did you fuck him too?" Lee pressed.

I decided to be honest, "Yes I did."

"Did you like it? Did you like fucking him?" Lee asked excitedly.

I could see his cock was still hard in his bikini when I answered him, "Actually I did Lee. He gave great head and I liked fucking him in his shapely cute ass," I replied firmly almost sounding annoyed at his persistence.

"I'm sure that you have fucked girls in the ass and have gotten blow jobs from them. Is there really any difference between a guy's mouth and a girl's mouth or a guy's asshole and a girl's asshole?" he continued.

"You know Lee based on my limited experience I would have to say no. Once you get passed the taboo that it's a guy and it is gay sex, I have to say there is no difference," I agreed.

"I hoped you would say that," he said with a smile and then asked, "Would you like to fuck me? I know that you like my ass."

In a way I wasn't surprised by the question and I thought why not. No one would know and I was horny as hell. However I decided to play it cool.

"I don't know Lee. Your offer is tempting but you are my employee," I replied.

"No one has to know and no one will know unless you tell them. We can be discreet. I have always thought that you were hot and I often thought about you fucking me. I wished your cock was sliding into my hole rather than some girl's and I would jerk off thinking about it," Lee said excitedly. "In fact that's why I was jerking off when you came in earlier."

"I have to tell you Lee before we go any further that I am not into cock," I said firmly.

"I didn't think you were and that's fine with me," he said and I noticed his voice crack this time.

From there we moved into the hotel suite bedroom and stripped naked. We were both hard and our cocks bobbed in front of us. I got in the bed and lay on my back. Lee 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.

"You have a nice cock. I was hoping that you did. It's big but not to big," he whispered as his hand ran up and down my 7+" shaft.

I felt Lee re-position himself on the 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 mouth. 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.

I whispered to him, "Lee I'm so close."

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

Lee 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 Lee 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 orgasm. Lee 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 my cum 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. I came as much as I ever had in my life even with Susan. Lee's mouth never left me as he continued to suck on my cock. Finally I couldn't cum anymore and I collapsed on 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 male sex. I watched as Lee lay next to me and stroked his cock. I saw Lee stiffen and then I watched in amazement as ropes and ropes of cum shot out of his cock and covered his body from his neck to his abs. I never knew that anyone could cum that much. I got turned on just watching Lee shoot his load and my dick was hard again. My state of desire did not escape Lee and he spoke to me.

"Cliff I would love for you to fuck me. Would you like to fuck me?" Lee said in more of a request than a question. "I want to feel your cock in my ass. I want you to fuck me," he said again.

"Yes, I want to fuck you." I admitted.

Lee rolled over on all fours and handed me a tube of lubricant. "Take your time and prepare me for your cock and then fuck me in the ass like you would fuck a girl in her ass," he said.

I knelt behind Lee and I begin to caress his beautiful ass his body was delicate, hairless and flawless. I couldn't believe how much Lee looked like a girl from behind with his shapely curvy ass in the air. I put an ample amount of lotion in my hands and rubbed it all around Lee's bung hole. Then I inserted first one finger then two fingers preparing him for my cock. Since I could not see his cock and balls, he really looked like a girl on all fours. In the early 80's it was still a time that bareback sex was common place so I didn't even think about using a condom.

I was no stranger to preparing assholes for my cock but this was the only the second time in my life that I was preparing a man's bottom. However 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. I moved closer to Lee and lined up the head of my cock with his anal opening and began to ease it into to him.

I spat on my hand and rubbed my saliva all over my cock which made it very slick when combined with the lotion. My cock head cleared his sphincter and it slid right in without resistance. His ass chute was warm and tight as I went deep into him. I was all the way in Lee's 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 ass.

Lee 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 buttocks and Lee 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 once Lee started to contract his sphincter muscle 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. Lee used his talented ass to milk my cock and drain it of all my semen. I didn't think that I would ever be soft again as I remained hard in his tight sheath. Lee's milking action weakened me and I collapsed on top of his body.

Lee flattened out on the bed with me on top and my cock still in his ass. I rolled off of him and my hard cock slipped from his ass. Lee rolled to his back and spread his legs lifting his knees to his chest.

"Fuck me again," he asked.

I moved between his legs much like I would with a girl and lined up my still erect cock with his asshole. Lee was also as hard as a rock and his beautiful young cock pointed toward his head. I pressed slightly forward and my cock moved into his hot ass. His ass actually pulled me inside and my cock went all the way in him and my balls rested on his ass.

"God, that feels so good, fuck me," Lee cried out.

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 asshole before I pushed it back into him. My 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 muscle. Lee humped up against me fucking me back as I fucked him. The room smelled of sex and sweat.

I took slow long strokes in and out of his ass as Lee 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. Lee was grunting as my cock slid in and out of his hot ass. Soon my cock was barely staying in his ass. Then Lee slowed down and let my cock just press against his prostate. He announced that he was cumming and he pulled me down to him and hugged me. I felt his cum shoot between our bodies covering our chests and our abs and then oozing out around our pubes. This set me off and I began to pound my cock in and out of his hole. I slammed my cock into his loose wet hole and I felt my balls tighten. I pressed deep into him and my seed filled his ass.

"Yes cum in my ass again. Oh I feel it I feel your hot spunk," he groaned.

I pulled, pushed and cum spurted into him making his hole wetter and warmer as my cock easily slid in and out. I continued fucking him until my legs were weak and my semen had stopped flowing. My cock slipped from his ass and Lee stroked my exhausted body. It was the first time that I had ever felt cum other than my own on my body.

"I loved fucking you. I loved your ass," I whispered.

"This is just the start of a great business relationship," Lee answered.

I checked the time and it was only 2:00 PM. It seemed as if it should be at least 5:00 PM. I offered to take Lee to lunch and he accepted. So both of us showered, dressed and went out for a late lunch. We decided to make lunch our main meal so we treated it like a dinner and had a bottle of wine with our meal. When we returned to the hotel we relaxed in front of the TV and opened another bottle of wine. We watched TV for a couple of hours before Lee took out his cock and began stroking it. It made me horny to watch him jerk off so we decided to go into the bedroom.

We were both horny but still fairly drained from the earlier activities. Lee wanted me to fuck him again and I told him that I preferred doggy style. He got on all fours on the bed and tossed me the tube of lubricant. He wiggled his curvy ass in anticipation of my fingers. I got the lube out and poured an ample amount in his asshole. I took my time fingering Lee's ass until he pleaded with me to stop teasing him and fuck him.

I knelt behind Lee and lined my cock up with his asshole and pressed forward pushing my cock head past his sphincter. Lee groaned as my large cock opened up his back door. He reached back and placed a hand on my thigh in an effort to slow the penetration. I took my time and worked my cock in slowly inch by inch until it was buried in Lee's asshole. As I fucked Lee from behind, he really looked like a girl with my cock in her ass. I could not see Lee's testicles or his cock as I fucked him as his long hair fell along side his face. He was incredibly effeminate looking.

Lee told me to fuck his ass and then he stiffened as he came and shot his wad on the bed sheet. I felt Lee's asshole contract around my cock as he shot his spunk and I picked up the pace and pounded his ass. I felt my own orgasm build up in my balls and then I felt my semen travel through my scrotum. I pressed into Lee's ass and emptied my balls deep in his rectum although there wasn't much this time. The semen oozed into Lee's rectum and gathered around my cock buried deep in his ass.

"Oh I feel it, cum in me, I feel you cumming in me!" Lee screamed and then added, "I love it cum it in me."

Lee clenched my cock with his sphincter and then released it several times as he milked every drop of cum from my cock. I stayed hard and continued to fuck Lee's ass as my semen backed out of his asshole and trickled down over his perineum.

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