I used to fantasize about an older man when I was 18. He was a family friend who was married, and I really liked his wife, but there was something about him that was so sexy. He was almost 40, but he was so confident, possessed, and whenever he was over I found myself looking at him. He would look at me as well, and we would spend long moments with our eyes locked, and we would smile at each other.
One night, he was over and our whole family was watching a video on TV. I was lying on my stomach in front of the easy chair where he was sitting. The rest of the family was on the couch, so that he and I were slightly behind them out of their view when they were looking at the TV. The lights were out, so we were only lit by the glow of the television, and about halfway through the movie he put his foot on the back of my thigh.
He was resting it there, on top of the blanket that covered me, and I immediately lost all concentration on the movie, only aware of the warm feeling of his foot on my leg. After about five minutes, what seemed like forever, he slowly moved his foot along my leg so that his toes stroked the back of my butt, and then back down my thigh all the way to the back of my knee. He moved casually, as if it were no big deal.
After a few languid strokes, he slipped his foot under the blanket, so that his foot was on my bare thigh, only his sock between his skin and mine. I was wearing shorts under the blanket, and as he kept stroking my leg with his foot, he gradually shoved my shorts upwards, so that the crotch began to tighten and pull on my lips and his toes were massaging my cheeks. Up until that moment, I had been frozen, but now I found myself relaxing and opening my legs ever so slightly. He must have noticed, because he started to stroke his toes between my inner thighs, moving a little higher each time until he was tracing a delicate line up and down my pubic region and up the crack of my ass.
I could feel how wet my panties were becoming, and my lips and clit were so swollen that it felt like I was bursting. On one of his strokes, he dug his big toe into my lips, so that they parted and the fabric of my panties and shorts rubbed my inner lips. I spasmed uncontrollably, and he dug in deeper so that his toe was rubbing against my clitoris. By now I was breathing in short, quiet panting, and my eyes were darting around the room at my mom and everybody else on the couch to see if they were noticing any of this. They seemed to be focused on the movie, which unfortunately was now almost over.
He increased the pressure of his toe on my pussy, and I began to rhythmically grind my cunt against his foot, raising my ass upwards and downwards by clenching my thighs. This had the added affect of squeezing my clit each time and I began to build towards a climax, a feeling I recognized from the same technique of squeezing my thighs that I used to masturbate sometimes when I was lying in bed. Just as I started to feel the familiar tightening that signalled the beginning of an orgasm, the movie ended and my sister turned on the light.
His foot quickly withdrew and I felt like I was left hanging. In fact, even as the lights came on, I continued to clench my thighs around where his foot had been, and the rhythmic squeezing finished off an incredibly powerful orgasm, my very first orgasm that had been caused by someone else other than myself. I guess you could say that somehow I had lost some form of my virginity to him, even though we had never actually had intercourse. But in some ways it was an even more powerful and intimate moment that night, as furtive as it was.
After the lights came one, and as I continued to lie on my stomach trembling as my orgasm subsided, it was as if the the whole thing was a figment of my imagination. He stood up and acted as if nothing had happened, and chit chatted with my mom before going to the door to go home. Usually, he would hug all of us, but this time he didn't, and even though I was watching his face intently, he only met my eyes once, giving me a quick smile before turning away.
I fantasized for years afterwards about him, usually romantic settings where he would slowly make love to me as if it were a scene in a movie. But I would almost always be masturbating at the same time in a much more violent manner, using two or three fingers to finger fuck myself in a rapid, thrusting manner that made a dirty slip slapping sound that was nothing like the slow strokes I was imagining him applying. It was only years later that I began to fantasize about him in a manner that matched the urgent thrusting of my masturbation.
I have regretted ever since that I never did anything else with him, and have always wished that he had somehow found a way to be alone with me. I would have done anything he wanted me to, would have given myself completely to him. My fantasies about him have become increasingly more explicitly about being in his control, so that I have imagined him binding me, or bending me over the back of a couch and thrusting into me from behind, holding me down on the ground as he pumps into my mouth.