Once in a while, on weekends, Frank, a friend of my dad, who operated his own limousine service, would hook me up with jobs for the day. I had gotten my driver's license a few months before, so I was able to drive his limos, and get a nice piece of change for my efforts.
One Thursday, he called me, saying that one of his drivers would not be able to work the weekend. He had a contract on Long Island for the Bachelor’s Party on Friday night, and the wedding at noon on Saturday. Since it was more than 70 miles from the city, it didn't make sense to drive all the way back at 3 or 4 am, so him, the other driver and myself would be staying in a motel and I would be paid for 2 days worth of work. Well, not only was the money great, but I had always been attracted to Frank. He was 54, short gray hair, and gold framed glasses. He was about 5'10", maybe 180 lbs, and hairy. Many times, I had fantasized about him, so the idea of maybe seeing him in his underwear while we were going to bed seemed to be the most exciting thing. We got to the motel about 3 am on Saturday morning. Jim, the third driver, who also held a regular day job, said he was going to sleep, so he took the room on the right. The door between the two rooms was open, so he went through it and said he would see us in the morning.
I showered while Frank did some paperwork. I then got in bed, though I didn't want to fall asleep, in the hope of catching Frank in his underwear when he had taken his turn in the shower. When he finally came out, he was wearing nothing but a towel. I was just frozen! The hair on his chest was still wet, I could see (or thought I saw), a tent under his towel!
Frank came toward the night table and put down his watch. I was only about two feet from what I could now definitely see was a hard on. I felt like saying something (anything), but my mouth felt dry. Frank turns toward me, puts his hand under the towel, and says, "Boy, do I need this taken care of." His hand was grabbing his now fully erect cock, less than a foot from my face.
After about two seconds of eye contact, the head of his cock was on my lips. As he shed the towel to the floor, his left hand reached for the back of my head, and started pushing me onto his dick. It seemed so huge! The rhythm was great, until he suddenly stopped. With one quick motion the sheets were torn off my body, and he was asking me to lie on my belly.
"Frank, I’ve never done this before, I’m not sure…" I hesitated.
“Relax, I’m not going to hurt you. It will hurt a bit at first, but you’ll soon get used to it, and then enjoy it." He went into his bag, and quickly produced a tube of KY, which was soon being spread to my asshole. It felt cold, but I was actually trembling with excitement!
Slowly, I could feel him entering me. I thought my ass would tear up, but he was very gentle, although I could feel more and more of him inside me. I felt like I had to go to the bathroom, but he said, "Relax, the feeling will pass. I am all in you."
After a few minutes, the feeling went from pain to great pleasure. I thought he was pulling out, but he was just starting the best part of the evening. The fucking was slow at first, but got faster and faster, until all of a sudden I heard him moaning, and I felt a hot stream fill me up inside. As he stood up, I could see that HUGE cock, still rigid. I couldn't believe I had been fucked with it!
Needless to say, I couldn't wait for our next shared room!!!
I was 19, recently out of High School. I always knew I was attracted to mature men, though I had never acted on it. There was just something very attractive about clean shaven, gray haired masculine men. Once in a while, on weekends, Frank, a friend of my dad, who operated his own limousine service, would hook me up with jobs for the day. I had gotten my driver's license a few months before,
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