Where it happened: his house
Langauge: English
Sex: Male
Rating: 9
Category: Straight
Sex was nothing new to me. From the time I was 11, my best friend Sherry and I had explored and discovered all the fun things two girls could do with each other’s body. But Sherry decided on her 14th birthday that it was time we both experienced guys instead of just one another. For her first time, she decided to seduce my 17 year old brother – not that I ever thought it would take much seducing! Afterward, she told me all about it and all I could think was that it all sounded very disappointing. After she shared the details, she said something that set me thinking. She said, “Megan, I think he knew less about sex than we do!” I decided right there and then that I would find someone who did know more about it, a lot more, for my first sexual experience with a guy. I was technically still a virgin (if you don’t count Sherry’s tongue and fingers) and wanted my first time to be a really wonderful experience.
I lie in bed that night trying to think of who I knew who would have the requisite knowledge to make my first time memorable. All the guys I knew who seemed to be experienced were also self-centered slobs who didn’t interest me. But, suddenly, it hit me. What I needed was an older man, a man of the world who would know how to please, how to entice, how to fulfill. I started thinking of different men whom I knew; I even thought about Sherry’s dad but figured she would never forgive me if I did it. Finally, it hit me! A divorced man had moved into the neighborhood the year before. He had been in the army for a long time and when he retired, he bought the house up the street. He wasn’t bad looking, in pretty good shape. But that wasn’t what attracted me. Anytime I would hear him talking with my dad or mom, there was this gentleness about him that drew me. No, it wasn’t really gentleness; it was gentle strength. That’s the best I can describe it. I remember thinking once that if there was ever a crisis in the neighborhood, I hoped he would be around! That’s the kind of guy he was. I knew he was a lot older than my 14, a lot! (I later found out that Tom was actually 55. Hey, what’s 41 years when sex is involved?) But age wasn’t important to me – the fact that he seemed intelligent, experienced, strong and gentle – that’s what mattered.
The seduction was easy. I had decided to mention nothing to Sherry for fear that she would somehow screw it up. All I did, once I made up my mind, was to walk over and talk to him. First, it was just about his time in the army, all the places he had been, everything he had seen and done. I kept telling him how interesting his life had been and how boring mine was. He was open and sympathetic, agreeing that our town wasn’t exactly the liveliest place in the world.
After three or four days of general talk like that, I finally brought the subject around to boys. I asked him if I could talk to him about something that I was embarrassed to talk to my parents about. He said I could, so I told him about my friend (I wouldn’t mention Sherry’s name)and her disappointment with her first sexual experience. I told him that I knew I was ready, I was anxious to experience sex with a guy, but I didn’t want the disappointment that “my friend” found. I asked him what I should do. For the first time in all of our conversations, he hemmed and hawed and seemed unable to form a sentence. Finally, he told me that maybe I needed to find a boy who was more experienced. I told him that every guy I knew with any experience was a conceited slob and probably wouldn’t be interested in someone who looked like me. So he came to my defense and started telling me how pretty I am and how any boy would want me. And I said “Even you?” He had been shot twice while in Vietnam or somewhere, and I think I saw the same look on his face that must have been present when the bullet hit! Shock. Fear. Disbelief. They were all there. He mumbled “Do you mean do I want you?” And I answered “Yes”. He started to protest the age difference and how young I was and so on and I looked down and said “See, even you! You’re my friend and you’re not even interested!” That took him back and he seemed, for a minute, to be lost for words. Finally he asked if I really knew what I was asking for. And I knew we were at the crossroad!
How should I answer him? It tore through my mind for thirty seconds that seemed to drag on forever. And then, I knew the perfect answer. I looked at him and said “I’m asking for this!” And reached out and cupped my hand around his penis! He had obviously already made his decision because he didn’t pull back or even look shocked. He simply bent to me and kissed me, gently, insistently, lovingly.
Tom knew exactly what he was doing. Before he entered me, I had already had three orgasms. He kept asking if I was sure I didn’t need to be home at a certain time, and I kept reassuring him that we had all day. His tongue drove me insane. I thought Sherry and I had done absolutely everything two humans can do with their tongues, but Tom taught me otherwise. It was everywhere and so were his hands, his fingers. At one point, I thought I was going to pee his bed as I exploded with yet another orgasm, but he explained the g-spot to me and how it often feels like you are going to urinate when it is probed. Finally, I demanded that he just do it before the mounting excitement kill me. Although I thought I needed no lubricant, Tom insisted since it was my first time. His penis wasn’t huge, just average, maybe even a little smaller. But oh what he could do with it! He slid into me part way until we both felt that he had reached the barrier. He said, “You know, Meg, that this will hurt a little.” I assured him that I did and, with that, he withdrew the length of his penis and plunged into me. I know I cried out because it did hurt, a short, sharp pain. So he wrapped an arm beneath my head and held me to him. He whispered “I would never hurt you purposefully, but sometimes, the distance between pain and pleasure isn’t very far.” And with that, he began these slow, long strokes in and out of me, shifting position almost with each one so that each was different and unique, arousing a different spot, stirring a new sensation. Finally, I saw what looked to almost be an expression of pain on his face and he began to let the control fly away as he moved in me, faster and faster and faster. I felt it when he came – almost like a force hitting the very depths of me; but even then he didn’t stop. He kept right on moving, moving, moving until I felt yet another orgasm build within me. This one was unreal – he was holding me, kissing me, playing with my nipple, moving in and out of me and nothing could stop the wave after wave after wave of pleasure that rolled over me.
That summer, Tim ruined me for guys my age. We spent numerous days like that, playing, learning, exciting. He told me how grateful he was that I had asked him, how special it was to him that I wanted him to be my first. He continued to be my first – the first guy I ever gave head to; the first (and only guy) whom I allowed to have anal sex with me; the first guy who ever showed me just how good it can really be.
Last year, Tom passed away. They said he had a heart attack (no, I wasn’t there.) I was surprised to find that I was mentioned in his will. He left me some money and a painting he had that I loved. The will simply said “For a young girl who took the time to tell an old guy that he is special.”
There have been other guys since Tom. I’m doubt, however, there will ever be another guy like Tom.
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