I was 19 years old and in college, home on break the week after Christmas, and working in a grocery store. A former high school teacher (Tim) came into the store. He taught my favorite class and I felt I knew him pretty well. We chatted for a while about our lives then he left. The next day he called me and said he was going skiing up north and his wife was unable to make it -- and did I want to come along (he already had the condo rented, bla bla bla.)
On the way up north a car swerved around us on the highway. After they swerved in front of us, and a girl popped her head up from the lap of the driver. Tim and I laughed and started talking about sex. Had I ever had sex in a car? Gotten a blow job while driving? Etc. At a store he bought a Penthouse magazine and we read stories to each other as the other person drove.
We arrived Thursday night as it started snowing. It snowed heavily that night so the usual weekend crowd did not make it up and we had a great day Friday with new snow and no lift lines.
Friday night after we cooked and ate dinner, we were sitting around the fire and I was stretching my sore muscles in a t-shirt and gym shorts. I don't ski often and I was pretty sore. Tim put a blanket down in front of the fire and told me to lie down and he would give me a back rub. The back rub felt great, then he moved down to my legs. He went so high up my legs he gently brushed against my balls a couple of times and I was getting a hard on. Then he moved up to my butt and did a good job on my glutes and moved in to the crack of my ass with a light touch. It felt pretty damn good and my stiffy was rising.
"Turn over." Tim said.
I did, and he did not waste any time. He looked at my hard-on, giggled and said, "You seem to like this." and he gently stroked my bulge through my shorts. Then he tugged my shorts down and off. My mostly-hard dick stood up proud. Tim barely touched it as he stroked it up and down. I had never had sex with a man. I had never even thought about it, but it felt pretty damn good. As Tim gently stroked me with the lightest touch, my penis and it twitched with my heart beat and got fully erect.
Tim then took my dick between his thumb and forefinger and jerked up and down gently. I had never had such a light touch on my prick and it was amazing. Tim would stop and stroke my balls then back up to my dick -- jerk, jerk, jerk, stroke. After about ten minutes he started squeezing harder and stroking faster. I was getting pretty excited as I lay there with my eyes closed, very relaxed.