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.
