My First Guy: Cherry Busting!

This is a true story of the first time I had sex with another man. I have had sex many times since then but it stands out as one of the most erotic times I have ever had.

When I was 18 years old, I had heard a rumor that a bar on the other side of town was gay. I had always had "urges" to have sex with a man but was always scared of trying. After thinking about it for a couple days, I got brave enough to go to the bar.

It was slow for a Friday night, maybe about 7 people plus the bartender. I sat down at the bar, ordered a beer (I guess I looked old enough, I didn't get carded) and kinda watched everyone. After a while, an older guy named Gerry started chatting with me. He was about 50 ish years old 5'10 around 200lbs, with wavy salt and pepper hair and "Magnum PI" mustache. After about an hour and a half of bullshitting with him, and with the bar closing, he asked me if I wanted to go back to his house and have a beer. I said ok and followed him home. While driving, my mind was going a million miles a hour in about a million different directions. More than once, I almost turned away to drive home. But the prospect of finally seeing what it would be like to be with another guy was giving me an erection and kept my car right behind Gerry's car.

Once at Gerry's house, he turned on some music and grabbed me a beer from the fridge. He excused himself and went and let the dog out. While he was gone, I looked around the house. On his fridge was a post card showing a man's naked ass with a caption arrowed to the asses crack saying "wish you were here". This removed any doubt as to why Gerry invited me here. "That was from a good friend that just moved to Key West.", said Gerry from behind me. "Awesome place. You need to go there sometime."

We talk for awhile. He told about Key West. I told him about college. Sex came up finally and I bulshitted with him about the girls from high school. This all was over the course of 3 more beers. I had a pretty good buzz on and new I wasn't going anywhere that night. I moved a certain way and you could hear my back "creak" from across the room. I laughed and stretched out my arms and arched my back. I kinda snickered after hearing multiple "poping" sounds come from my back. At that, Gerry asked me if I wanted a back rub. "Sure" Gerry downed that last of his beer and got up and then helped me to my feet.

Staggering a little bit, he led me to his bed room and told me to stretch out on his water bed and he would be right back. Gerry turned out all his lights in the house, and when he got back to the bed room, he found me still lying on his bed, still in my close. "Silly boy. I can't rub you down with your clothing on" he said. At that he proceeded to help me get undressed while I stayed lying on the bed. As my shirt and pants came off, I felt his fingures touching my back and legs. I arched my back again as he pulled my underwear off on his own. His eyes went to my now exposed cock. I almost thought he was going to grab it but he slid off the bed and started to take off his own close. There I was, stark naked and watching him get undresses. When it came down to his taking his underwear off I saw a cock that had to be at least 8 inches and starting to get hard. He turned out the light and got back into the bed.

There he pulled out baby oil from the night stand and started to apply it to my back and shoulders. While was doing this, I felt his now rock hard cock pressing against my ass. After about 15 minutes, he started to work on my ass with the baby oil. He spent about 5 minutes on each check, and then he applies some oil on my asshole and balls. My God, I was in heaven! This man knew what he was doing. He rubbed up and down my crack pressing his fingered more and more against my asshole. He worked the tip of his index finger into my ass. At first it felt weird. Then I felt a jabbing pain. I started to move and he stopped me, telling me to relax in a very hypnotic voice. "You need this as much as I need to give it to you". His face was close to mine and he kissed my neck and worked his way up to my lips. I felt his tongue dancing in my mouth with his. I was again totally relaxed. I hadn't realized it but he had his entire index finger in my ass at that point. He added yet more oil and a he put his figure in me again.

It felt soooo goood. He started to put oil on his dick. I tried to help, but again told me to just relax. He the laid on top of my back with his hands on clamped each of my wrists, as I was spread eagle. I felt his cock getting closer to it primary target. He let go of one of my wrist long enough to for him to spread my ass cheeks apart and to guide his cock to my ass hole all the while he is kissing my lips and neck then I felt it start to enter me.

Again I started to feel to pain, but this time I just laid there. I wanted this so bad. He slowly worked it in an inch at a stroke until he was at the hilt of his cock. He Just laid there for a minute. When it seamed like I was totally relaxed again, he started to work his cock in and out of me, slow at first, but he did start to pick up speed after about 3 or 4 minutes. He kept telling me over and over how tight I was. Every once in a while he would he would stop, as to stop himself from coming to quickly. But he did start to get into a real good rhythm. I said it before, but I was really in heaven. After about 10 minutes, I felt him start to get quicker. He all of a sudden buried his cock in me and stopped. I could feel his dick throb in my ass as he started to cum. His cock started to move in and out of me again and I felt some of his warm excess cum fall onto my balls and inner leg. After a minute of him just laying on me, his cock when soft enough that it fell out of my ass. The last thing I remember was him rolling me over, and him kissing me as he played with my cock and balls, but I dozed off shortly after that.

In the morning, I woke up to him sucking on my cock. He was an expert! I exploded into his mouth after a couple minutes. We fucked and sucked for the rest of the weekend, getting dressed only once to get Chinese takeout.

We saw each other a quite a few times after that over the next couple of years, but nothing was as good as the night my ass lost its cherry!