Making Fantasy a Reality

By the time I began my second year of college, I had come to the halting realization, one both frightening and thrilling, that I had a growing sexual interest in men. It was a mystery to me how these desires had come about, as I had always been attracted only to women. Still, I could not deny that these new fantasies elicited a physical response. Often as I lay in bed after a night of socializing with roommates and friends, I imagined my bedroom door being quietly opened, one of our group slipping first into my room, then into my bed, and then into me. Lying naked in the bed, I would stroke my rigid dick and imagine how I would squirm and buck beneath the man who would eventually claim my virginity, whomever he might be.

During the fall and winter of that year, my fantasies were realized only in my imagination. I was too inhibited and inexperienced to go beyond the fantasy stage. In the spring, though, as the warm weather returned and the world began again its annual phase of renewal, a chance encounter would ultimately make real my imaginings.

One Saturday morning, I took my racket and a few cans of balls to the campus tennis courts. I went alone, intending to practice my serve and to hit balls against the practice wall. The courts were empty, save for one man, whom I judged to be in his 40's. Like me, he was serving into an empty court and then retrieving his balls and continuing. After a short time he walked over and asked if I would like to hit a few balls with him. For the next hour or so, we hit forehands and backhands over the net to each other. Although more than 20 years my senior, my new practice partner seemed especially fit. He moved about his side of the court with a smooth and powerful athleticism that seemed to come naturally to him. I was quite attracted to him, and the notion that he was a man old enough to be a father or uncle to someone my age seemed to add an element of the forbidden to my attraction.

By the time we shook hands and I left the courts that Saturday, I had learned that his name was Alan, that he was a professor of literature at the university, and that he lived near the campus. Surprisingly, in addition to these rather mundane generalities, I learned something quite specific and personal about him. As we stood sipping water during a break from the tennis, I had offhandedly asked him if he had children. He laughed and told me that he had none that he knew of - and then confided that he was gay and he didn't think it at all likely that any of the men he had fucked had become pregnant. I smiled and agreed that it was not likely. His casual reference to fucking, and in particular to fucking other men, had an immediate effect on me. I felt my heartbeat accelerate, and my face felt warmer. I don't know if he noticed, but if he did he said nothing. I felt embarrassed for having blushed like a schoolgirl, but the thought of him fucking me had suddenly leaped into my head, before I could even begin to examine the idea. He looked at me carefully for a moment, and I wondered if he suspected what I was thinking. Then the moment passed and we said our goodbyes.

Several Saturdays later, I returned to the tennis courts and was pleased to see Alan there again. This time, we exchanged telephone numbers, and over the course of a month or so we met several times for coffee and talked on the phone just to see how things were going. One day, Alan phoned and told me he hoped I would come to his house for dinner on the following Friday. I was happy to say I would love to come, but after I accepted, I was quite anxious about it. I knew that I wanted Alan to take me to bed, to be my first man. What better opportunity was there than to be alone with him at his house, after a nice dinner and some wine? And my instincts were telling me that he wanted to have me, although the signs were subtle and I was in no way experienced in reading them. I was deathly afraid of coming out and telling him my desires for him. And it is also true that, in spite of the elaborate fantasies I had conjured up about being intimate with Alan, I was afraid of the actual sexual details. I had no experience with men. I didn't know what role to play, or how to play it. What will he expect of me? In spite of my willingness to be fucked, will I be able to accommodate him when he penetrates me? Will it hurt? All these questions and more plagued me in the days leading up to that fateful Friday.

The dinner at Alan's was indeed nice, and the several glasses of wine relieved a good measure of the anxiety I felt. We sat in the living area of his house and told more of our individual histories. Then, he apologized in advance for asking such a personal question. He wanted to know if I had thought about he and I having sex. This moment was obviously a turning point. I felt my voice rising a bit as I told him that I had often fantasized about it. In a tumble of words I told him I had never been with a man before, and that the idea both turned me on and scared me. He asked me what specifically I had fantasized about, and in a nearly breathless voice I said that I had repeatedly imagined him fucking me.

And fuck me he did, multiple times throughout a long night. He took my hand and led me up the stairs. I felt flushed and a little boozy from the wine and the explicit talk of sex. When he helped me remove my clothing, my cock began to stiffen, and he sat me on the side of the bed and sucked me until I was rock hard. I lay on the bed and watched him begin to undress. When he turned toward me, fully nude, I saw a lean, smoothly muscled man. And he was definitely all man, hard pecs and arms and thighs. Alan was very well endowed. I stared at his half-hard dick, a thick long thing that swayed slowly back and forth as he walked toward me. Again, I wondered if I could accommodate him.

I held his big dick as he lay beside me. He put his tongue in my mouth and I accepted it and could not help but release a low moan. We kissed and licked and squeezed for a long time. He played with my ass and slowly began to finger-fuck me. We put ourselves in a 69 position and I sucked him while he rimmed me, moving his tongue in circles around my hole and then inserting it into me. I became conscious of a persistent sound, and realized it was me, moaning and making oohs and aahs in response to what he was doing to me.

He told me to relax and have a little more of my wine as he excused himself and left the bed. When he returned, he carried a bottle of lubricant, which he applied to my ass and then to his hard dick. He knelt between my legs, lifted them to his shoulders, and pressed the fat end of his dick against my sphincter. He was very slow and deliberate, telling me to relax in a slow, soothing voice. I felt myself being spread apart, and then he retreated slightly before pushing gently again. Then after a few moments his large glans suddenly slipped into me. I cried out involuntarily, and he stayed completely still. The pain was sharp, and it made me tense my entire body, it seemed. He grabbed by cock and squeezed hard, quietly telling me to relax. The sharp pain quickly receded, and Alan slowly worked his length into me. He lowered himself onto me and I soon was bearing his weight and accepting his long thrusts. I wrapped my legs around his waist and he fucked me for a long time, slowly at first, then with more speed, then slowly again. He held me in a tight grip and fucked me deep and hard. I sucked his tongue and put my hands in his hair.

And so throughout the remainder of the evening, and late into the night, we rutted and sucked and pinched and kissed, with Alan mounting me in various positions. Finally, I sat on him and stroked my dick until I came on his hard stomach.

In the months that followed, my confidence as a sexual partner of men improved, thanks mostly to Alan and the sexual interludes we enjoyed when we could. I met several of Alan's friends and associates, and joined Alan and one of these men in a three-way, during which both Alan and I fucked the young guy almost senseless. Alan sometimes hosted dinners at his house for a few guests, usually a partnered couple, which invariably concluded with Alan bedding one of the men while I bedded the partner in the adjoining bedroom.

Time, of course, kept passing by. All too soon I had finished college and moved on. But I still think of Alan and those days of exploration and discovery.