Bottoming with My Mentor

This story is ALMOST entirely fictional, but maybe if I had acted upon the circumstances, it could've resulted in something like the story that I'm presenting here. Names have been changed to preserve anonymity.

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When i was in tech school back in the summer of '04, I was 28 years old and doing my clinical training at Lewis Memorial Hospital. I became very friendly with this tech there named Fred Vargas, who was much older at around 50, but took good care of himself. He was very effeminate though, but I didn't care because he was very intelligent guy and when we weren't busy with patients, we had alot of great conversations about all sorts of topics ranging from movies to music.

By mid July, people (my fellow students and the other techs) began to catch on that Fred and I spent alot of time together and teased me about the fact that he had some kind of crush on me, but I ignored that because we are adults and what does it matter what sexual orientation we are if we can have good conversations together? Anyway, right before the end of my clinical time there at the end of August, he took me aside into one of the rooms and told me that I was "like a son to him" and that he wanted to give me his number so that we could keep in touch and hang out together one day. People saw and whispered things but I didn't care and took the number, not thinking much into it.

One day late in September though, I got a call from him while I was eating lunch with a friend and watching the Jets game at a bar on the West side asking me if I wanted to meet up and hang out. I told him where I was and that we could meet up for a drink after the game. He agreed and I met him at a quiet local bar near his apartment on the Upper West Side. We had a drink and chatted for a bit until we got on the topic of music and he asked me if I wanted to come up to his place to see his collection. At that moment I began to have my suspicions about his motives but agreed anyway, and we went up to his apartment which faced other buildings uptown.

His place was spotless as I figured it would be due to his fastidious nature, and I sat on his couch while he went to get us a couple of more drinks. Then he put on some old showtunes records and showed me his impressive display of records, tapes, and CDs.

He stood close behind me while i looked, and when i bent over to read the labels on the lower shelf, i could feel the heat from his body as he stood right behind me, the crotch of his pants almost touching my ass. This made me think back to an incident when I was in a hurry and I had to get by him and I practically bumped into him. He was startled and as I passed him, he slapped my ass. At the time, I was shocked, but now I felt something different, I felt somewhat submissive to him because he was older and wiser than me, and also because he was beginning to show desire for me. We were alone and nobody had to know what happened, we were both grown men, and besides, I've always had a deep rooted desire to be dominated and even fucked in the ass like a woman. However, I had no interest in kissing or oral sex, as I felt that those acts were just too sensual. Fred was stronger than me and could take me that way, and the alcohol was loosening my mind up to the point where I was beginning to consider the possibilities here.

I began to feel a flutteriness in my stomach as I realized what could happen, and I felt my face get hot when I felt the heat of his body as he stood behind me. Then he made like he was reaching for something above my head and he pressed his crotch into my ass and I could feel his semierection rest right in between my cheeks. I reflexively stood up quickly just because the heterosexual alarms went off in my head, but then I felt him standing right behind me and he put his hands on my hips for a second before moving me over to reach at the thing again. I thought I heard him chuckle softly, but forgot about it a minute later when I saw some music that I wanted to look at more closely.

He walked by and asked me if i wanted another drink, resting his hand on my ass as he did so which made my cock throb slightly as my stomach continued fluttering. By this point I knew what was potentially coming depending upon how far I was willing to take this. I stood there terrified but also excited, staring at the music but not paying attention to it. I felt like my knees were shaking when he came back and sure enough, when he stood behind me asking what i was looking at, he wrapped his arms around my body, pressing his crotch into the seat of my pants and resting his chin on my shoulder. Then he asked me softly in my ear "well? You're here, how about we give it a try?"

At first I didn't respond, frozen with apprehension and conflicted feelings, but then I steeled myself, turned around and looked him in the eye. Then I made him swear that this was completely confidential and nobody could ever know. He rolled his eyes and nodded saying "of course, you big tough straight guys have a rep to uphold" We shook on it and he smiled and nodded his head towards the bedroom, but i nervously pointed to the bathroom first and he shrugged and went in to the bedroom to wait for me. When I got to the bathroom I stared at my reflection in the mirror and convinced myself that this was what i wanted to do, submitting to Fred and letting him penetrate me was something that would fulfill a deep dark need, but I wasn't gay. I wasn't attracted to him or any man, I just wanted to bottom with a man who was stronger and smarter than me. Then I tried to clean up as much as I could, scrubbing my asshole with soap and water as much as possible, even pushing a finger up my ass to make sure there wasnt any mess. There was nothing and my asshole felt soft and relaxed after the thorough cleansing, and I figured that would help me later on. I took the rest of my clothes off, shaking my head in disbelief that I was even going along with this, and left them in the bathroom.

Then I walked naked through the apartment to his bedroom door which was closed. I knocked and when he said "come in" I slowly opened the door and there he was, laying on his bed naked on his side smirking at me. I felt very awkward and rolled my eyes at him, but he chuckled and raised his eyebrows at me, telling me to come over to the bed. He had a small bottle of Astroglide and a condom on the night table and just knowing what he was going to do with them made my stomach churn with apprehension.

It was warm in the room though, and the shades were closed so it felt very private and that was comforting at least. He told me to sit down on the edge of the bed and patted it, and when I did, he smiled at me and told me "I've wanted this to happen for a long time because I feel a connection with you. You didn't turn your back on me or treat me differently just because of my sexual orientation...aaaannndd because you're smart and attractive.". He then chuckled and said "although, you don't have much of an ass but I won't hold that against you." Then he asked me why I had agreed to do this with him, and I just shrugged and told him that I had always been curious but until then never had the courage to act on my fantasies. I also made sure that he understood that I wasn't gay, just alittle bicurious and that this was going to be an isolated occurrence. Then I told him that I wouldn't kiss him or suck his dick or get mine sucked, I just wanted receptive anal intercourse. he rolled his eyes and shook his head but sighed and nodded in agreement.

Then he asked me if I was ready to get started so I just shrugged and said "I guess so" but I felt like I could barely talk from being so nervous. He told me to follow his directions and he would do everything he could to make it pleasurable for me. Then he sat up and reached for the lube before telling me to lay down on my stomach. I took a deep breath and began to lay prone, but not before noticing his cock for the first time; it was medium sized, maybe six inches long and the same color as his skin. It was also circumcized and protruded out from a dark nest of long pubic hair which I thought look unattractive, but I just figured that he came from an era when people didn't groom their pubes the way people did today.

Then I brought my arms above my head and rested my face away from him while I heard him crack open the Astroglide. He ran his big warm hand over my lower back and cheeks, remarking that I was kind of hairy between my balls and my asshole but they were soft hairs so it would be fine. Then I felt him grasp my asscheeks and spread them apart which made me feel so vulnerable when my asshole got it's first exposure to the air. He softly commented that I had a nice looking anus which made me blush and mutter "thanks". Then I felt him touch it with the pad of his finger. That made my asshole clench reflexively which got him chuckling softly and he told me to relax. He ran his finger down the crack of my ass which felt soft and pleasant and I felt my scrotum contract while my cock twitched underneath me.

I realized that I was breathing alittle more deeply because his touching and examining were actually turning me on, which was a little shocking because I never thought that as a straight man, that I could be aroused by another man. I guess the circumstances and the fact that it was Fred were the right combination. He seemed to notice and patted my ass saying "good..see?" I just nodded as he moved away and then came back with the Astroglide and he warned me that it was going to be cold and sure enough, I gasped softly as I felt the cool gooey lube splash against my asshole. My cheeks clenched for a second before relaxing and I felt the lube pool in the pit of my anus and run down around my balls. Then he took the pad of his finger and gently rubbed the lube up and down my asscrack and around the outside of my asshole before letting his finger rest in the sensitive pucker. His finger felt warm and soothing after the shock of the cool lube and he asked me if I was ok so far to which I nodded again. Then I felt him press his finger against my asshole and I held my breath as it slipped easily past the soft outer ring and stopped at the tighter inner one.

He told me to relax and exhale and as I did, he pushed against the inner ring until he pierced it's resistance which made me gasp and grunt from the initial burning discomfort. He quietly shushed me soothingly while pushing in firmly until I felt that he was submerged in to the palm. I was breathing deeply from the intensity and he stopped moving his hand for a minute until my body began to relax. He quietly asked me if I was ok and when I nodded, he told me that he was going to "work me open" and began turning his finger around inside me which burned the walls of my asshole and I grimaced but tried to keep quiet and still. He mentioned that he was surprised that my asshole wasn't as tight as he expected it to be, but I just shrugged and kept still. He began sawing his finger in and out which made me grunt from the friction and I could hear the wet sounds of the lube, but then he turned his palm downward and I gasped softly from the odd sensation of his finger rubbing my prostate.

It felt strange at first, but then my cock got hard underneath me because it began to feel pleasant and I couldn't help but groan softly and thrust my hips out. He chuckled softly and kept massaging my prostate and pressing against the walls of my asshole to loosen them up. My mind was reeling from a combination of the sensations and the understanding of the present situation in that I was letting Fred Vargas finger my asshole in preparation for actual intercourse. I began to unconsciously raise and lower my hips as he fingered my ass while spreading my knees apart slightly.

I had never felt so submissive before was moaning softly and breathing deeply, and sure enough, I began to feel very relaxed from the alcohol and warm privacy of the room.

He must have noticed also because he said that I was ready for the next step. He pulled his lubed finger out of my asshole with a wet slurp and it clenched reflexively for a second before relaxing again. I took the moment to reach back and touch it just to see what felt like. It was soft, sticky, and loose and i could slip my fingertip into my anal canal with hardly any resistance. He told me not to worry, that it was fine and that we were ready to go if that was ok with me. I nodded and took a deep breath before telling him to take it easy to which he responded "ok ok" before placing a cylindrical throw-pillow under my hips. This tilted them upward which also made me feel even more exposed and vulnerable because it had the added effect of making my cheeks spread apart naturally, like I was silently presenting and offering my ass to him. Then I heard him rip open the condom followed by a pause which I assumed to be the time it took for him to roll it on his cock. Finally, I heard the sound of him slathering lube all over his shaft.

Then the bed shifted as he straddled my thighs with his knees spaced far apart so that my legs were together but not touching. I felt the warmth of his inner thighs against the back of mine and my stomach churned with apprehensive anxiety. After this moment, there was no turning back; Fred was mounting me to fuck me in the ass. Sure enough, I felt his thumb pull one of my cheeks apart and then the warm blunt glans as it nestled into the pit of my asshole. It felt huge as I held my breath and stared at the bed with the sheets in my fists. I felt him increase the pressure and within seconds, felt my outer sphincter spread open around his cockhead without much difficulty. Then he leaned forward and let go of my cheek to plant that hand on the bed so he could use the leverage. The bed shifted again as he did so and in a couple of seconds, my inner sphincter dilated which made me jolt and grunt and clench my asscheeks together for a second. He muttered through clenched teeth "ok ok almost there hold on.." and his penis finally slid past the bottleneck of my asshole and up into my rectum.

I gasped and stiffened from the initial fullness inside my rectum like I had to take a huge shit, but he just kept steady and quietly said "ok it's ok, im in now". My back was straight and I gripped the sheet in my trembling fists while breathing heavily and gritting my teeth from the intense pressure in my butt. He then moved his other hand to the mattress so that he was planted above me and began to push in with his hips to sink his cock deeper into my ass. I gasped and grunted and cursed softly from the fullness and stretching, but this was it, Fred was inside me now and about to have actual anal sex with me.

He pulled his hips back slowly which burned, but then plunged back in all the way to the hilt because I felt his pubes tickle my asscheeks, and it forced my hips down into the cushion. Then he pulled back again and began fucking my ass in slow steady strokes which made me gasp and pant in time with his thrusts.

Getting fucked in the ass like this seemed very intimate and I felt very close to Fred then, like he was forever a part of me because we would always have this between us.

I heard him groan softly as he stroked in and out of my asshole, and now the friction was subsiding in favor of that pleasant rubbing against my prostate which sent fluttery waves of sensation through the inside of my body and tingles throughout my extremities. I raised my head and rested my weight on my shoulders while I kept my eyes closed to concentrate on the sensations. He breathlessly asked me if I was ok, and all I could do was nod and say "...oh yeah!..uh..uh..oh yeah!..uh.."

Up to this point, he was just raising and lowering his hips slowly to get me used to it, but then I guess he wanted more sensation so he started to increase the pace which meant that now he began bouncing off of my upturned ass, and I began to groan and gasp from the intensity. I felt his pubes brushing against my cheeks and his balls smack against the back of mine a few times, and he kept up the steady pace for a few moments which was impressive to me. because I would've been tired but i knew he was in good shape so I was in for a good hard fucking. I let my belly sag against the bed and cushion and my back arched naturally as I got pushed back and forth underneath his thrusting body, and I began to hear to moist churning sound of his cock as it plunged in and out of my asshole.

After a couple of minutes, I began to move my knees apart just to shift my position alittle, and he took the hint and sat back, pushing my knees out far apart and then placing his in between, then grabbed my hips. I felt like a woman as he began to pull me against his thrusting hips, banging against my upturned ass and fucking me deeply while I just rocked back and forth in rhythm with his thrusts and stared off into space with an unfocused gaze, letting him have his way with my ass. My asshole felt completely loose now, and he plunged in and out of it easily, grunting in his efforts, which was actually somewhat arousing due to the fact that he was enjoying taking my ass like this. For me, the submissive naughtiness and prostate stimulation were making me moan and groan like a girl, my voice jumping as he banged in and out of me. My balls dangled freely between my spread legs, and my anus was coated with the creamy mix of lube and my own rectal secretions.

The fucking he was giving me was intense, and I turned my gaze down at the bed while gasping openmouthed and gripping the comforter in my fists. He just kept his hands on my hips and pounded in and out of my ass, breathing through his nose and occasionally saying "that's it..that's it.." while all that i could utter was "fuck...shit...oh my god yeah!!..." through clenched teeth.

I felt sweat dripping onto my asscheeks from his face and heard them smacking against his groin, and my anus ached a bit from the intense fucking, but I still felt that pleasant sensation of his penis rubbing against my prostate and I concentrated on that. I arched my back as much as I could just because it felt nasty to do it, and in so doing, my gut sagged against the sheet and cushion.

Meanwhile, he kept up his pace, occasionally pulling my cheeks apart with his thumbs which I assumed was so that he could watch himself plunge in and out of my asshole. As he did this, I thought about how the women in my past must have felt as I did the same thing to them. Now I was playing the part of the woman, taking a cock up my ass and enjoying it. My head bobbed up and down slightly as he bounced me back and forth, and I tilted my head back and closed my eyes, hearing myself whimper from submissive pleasure.

He noticed and asked "so you this eh???" I nodded with my eyes closed and said "oh fuck yeah!!" between gasping pants, and he chuckled and moved his hands to my shoulders and began bucking into me hard which caused me to let out a barking grunt each time he buried himself to the hair. It was really intense and I let my head bob up and down while keeping my eyes shut tight and panting openmouthed. I surprised myself by blurting out "Oh yeah!...FUCK MY ASS, FRED!! FUCK MY ASS...FUCK IT!!" which got him breathlessly chuckling again.

The bed began to creak slightly, but otherwise the room was still warm and quiet except for the sounds of two grown men having sex with each other.

I had never felt such intense sensations all over my body from being penetrated; my limbs were tingling, my skin alternated between hot and cool and it had a light sheen of sweat, I felt the heat from his thighs on the back of my legs, his fingers firmly gripping my hips... and of course, his cock pistoning in and out of my rectum and anus.

I was glad that I gave in to temptation and surrendered to his advances, I just had to hopef that he knew how to keep a secret. At that moment though, my mind was focused entirely on the sounds and sensations of Frank fucking me in the ass.