Tommy Boy

As a young man, I developed a strong attraction for older men. My fantasies, in the main, focused invariably on being seduced and then laid by attractive older guys. In these imaginings, I was eager to follow the lead of the experienced, and always strikingly masculine man that I conjured from thin air. Some of these fantasies were ultimately realized, and I was fortunate that each realization lived up to my imagination, and then some. The younger man being mentored, protected, and ultimately fucked by the older - professor, family friend, uncle, neighbor - was an incredibly powerful theme in my sexual imagery of those years.

As a mature man in his 50's, I have recognized that my youthful fantasies might be shared by some of the young men of today - except now, I am the experienced older man for whom these young bucks might have such fantasies. As good luck and circumstance would have it, a few years ago I found myself in just such a situation.

I have travelled constantly in the course of my work, spending months or years on different projects throughout the United States. For these assignments, I usually lease an apartment in the city where the work is conducted, and fly home once or twice each month for the weekend. I began one of these assignments, in Chicago, in the usual way: I sat across the leasing desk at an apartment complex, arranging for an apartment. The young man that sat across from me appeared to be no more than 19 or 20. He was such a beautiful boy. I expected he was quite popular with the women. As he explained the various documents and went through his normal routine of preparing the lease, I slowly began to extend my opinion of his popularity to include men. Something about him - the way he looked at me, perhaps, or the way he smiled - made me wonder if he might be playing exclusively for the boys' team. Anyway, it was a pleasant exercise to watch him and to look for subtle clues as we went through the process of signing documents and distributing keys and gate passes.

When we were finished, we stood and shook hands. I made sure to wait until he released his grip before releasing mine, and was pleased to note that he held my hand just a little bit longer than one might do on a purely casual basis. Or, perhaps this was the delusional hope of an old man for the attentions of someone 30 years his junior. I have to remind myself occasionally that the world is full of possibilities for the young and beautiful, and that the young and beautiful do not, as a rule, entertain any thoughts whatsoever of the older and less beautiful. Still, as was true for me when I was a young beauty, there are exceptions.

The young man's name was Tommy. I saw him a few days later when I found that the mailbox key I had been issued would not open my mailbox. I went into the office, held up the key, and told him it would not work for the mail, and that perhaps he had given me the key to his heart by mistake. Corny, of course. But I have always tried to cultivate a talent for being dumb in a clever way. In any case, Tommy looked at me in an appraising manner for the first time. He smiled and said no, his heart could be opened by combination, but not by key. He retrieved another key and we walked to the mailboxes together. Voila, the key worked, and I told him he was very nice. He said yes, he was nice - to nice guys. I thanked him and he walked off toward his office. I looked after him and thought, my God, what a butt on that little guy.

Some days later, as I walked across the parking area toward my car on a frosty morning, I spied Tommy looking into the engine compartment of a Toyota parked near my parking space. I walked over and we deduced that his car's battery, most likely due to the cold, was dead. I told him we might boost the engine with some cables, but he said he was running late for a class and thought he should try to find a ride instead. I was happy to oblige, and drove him to the university campus. On the way we talked about the goings-on in our lives and our backgrounds. As we rolled to a stop and he prepared to exit the car, I told him he was welcome to come by the apartment for coffee or a drink anytime he liked.

A few days later, I trudged through falling snow to retrieve my mail, and Tommy came out of the office. He pulled his coat on as he jogged over to me. He thanked me again for the ride I had given him, and for the invitation to drop by. He asked if he might come by that night, if I didn't have plans. I told him of course, I would like that. Then I teased him by suggesting that if it kept snowing at the current rate he might get snowed-in with me and have to stay overnight. Yes, corny. He laughed and told me he was sure I could find some way of entertaining him if that should happen. Then he turned and jogged back to the office.

Tommy did indeed at least pretend to be snowed-in, as he did spend the night with me. And much of it he spent with my cock in his lovely ass. He knocked on my door around 8:00 P.M., his cheeks pink from the cold wind, and with snow in his hair and on his coat. I soon warmed him up with a few glasses of merlot. We sat on the sofa and talked, not sitting especially close to each other, but not far apart, either. There seemed to be some force that slowly moved us closer, and at some point Tommy placed a leg across my thigh. I placed my hand on his leg and began stroking him from knee to hip. We sat talking in this way for some time, quite casually, I thought, given the possibilities that each of us was entertaining - that is, I assume Tommy was entertaining possibilities. I certainly was. I was thinking about how I planned to make him melt beneath me in my bed.

I told Tommy about how I had fantasized about older men when I was his age. I told him a few details of my sexual encounters with men who could have been my uncle or father. I explained that, now that I was older, I found the idea of playing the senior role for younger guys very appealing and arousing. Tommy told me he often fantasized about being with older men. He confided, haltingly and a little breathlessly, that he had always wanted his stepfather to come into his room and take him hard, but that it had only been a fantasy. Come into the bedroom and let me fuck you, I told him.

I took Tommy into the bedroom, removed his clothing, and put him on the bed. He had a beautiful body, smooth and lightly muscled. He had the most beautiful dick, a slender 5 inches with a perfectly shaped head. And his tiny bottom, with its perfectly pink bud, made me hard immediately. I climbed on the bed and lay halfway on top of him. I kissed him deeply and he responded, almost frantically. I helped him relax by holding him and whispering to him. I told him what a beauty he was, and how much I wanted him. He held my dick and squirmed beneath me. I moved down and sucked him until I sensed that he was about to unload, and then I stopped and told him I didn't want him to cum until he had first taken some of my cock. I knelt by his legs and stroked by stiff shaft, showing it to him. He said only one word: "Please."

I rolled on a condom and made myself slippery with lubricant. I could not resist licking his little hole for a moment. He had a world-class derriere, Tommy did. I lifted his legs, which he took from me and pulled toward his chest. I penetrated him slowly, and did not hurt him at all. What an unfettered joy it was to get all of me into him and start riding him. Tommy was the perfect size for me. Just right for kissing on the lips while engaging with his ass, light enough to maneuver about the bed to achieve the best leverage and angle. As I came closer to exploding in him, I leaned close to his ear and asked him if he liked his daddy's dick. This might have cued his old fantasies about his stepfather fucking him, I don't know. But in any case, he cried out - a shriek, almost - arching his back and bucking like a wild pony. He raked my back with his nails and came between us as I deposited my sperm deep inside him.

Tommy was a superb lover, eager to be fucked and a very sensual person. We became good friends while I worked in Chicago. I thoroughly enjoyed my role as someone who could be helpful to Tommy when he needed help or advice. And over time I think discovered at least part of the combination to his heart.