There were 2 queen size beds in our room. Gerald pushed me back on one, then started removing my clothes. While he was working on the shoes, socks and pants/underwear, I got out of my shirt. Clothes were thrown in all directions.
We spent several minutes rolling around on the bed, making out. Gerald went down on me and true to form, I came within a minute. “Does that happen all the time, Jack?”
“Almost. It’s kind of embarrassing.”
“Don’t be embarrassed. I like the fact that you’re so turned on, that you can’t control it. And I know that it won’t take you long to get hard again.” He was gently stroking me as he was talking to me.
I sat up and brought Gerald up to give him another kiss, tasting my cum lingering on his tongue. It was time to help Gerald out. I went down on him, once again getting his cock balls deep. “Did you do that with Carl?”
I took my mouth off his cock long enough to respond. “No, but we’re working on it.” I returned to sucking on his cock.
After sucking him for a few minutes, Gerald said, “I want to fuck you, Jack. Can I do it bare?”
That stopped me. I took my mouth off of his cock and looked up at him. Before I could say anything, he said, “I’m clean. I get tested regularly and I’m on PrEP.”
I had read an article on PrEP. I knew that it was supposed to protect me from HIV, but that wasn’t the only STD out there. I really wanted to know what being fucked bare would feel like. “If you promise me that you’re clean, I’d like to try it. Do you fuck a lot of guys bare?”
“There is a group of guys at the Pit that I want to introduce you to. Most of us go bare with each other, and we all have made a promise that we won’t go bare outside of the group.” Gerald said that he would tell me more about the group, “but right now, I’d like to fuck you.”
So Gerald became my first bareback fuck. It worried me, because I didn’t expect it to feel much different, but it did, and it felt a LOT better. We started out in the missionary position. As he was entering me, he asked, “Did you send that video to your girlfriend?”
I smiled. When I sent the video, Patty had told me that she loved it. The next day, she sent me a video of her masturbating while watching the video. She said that she had cum three times the night before, imagining being in the room when it happened. I relayed this to Gerald.
“We’ll have to make a longer video for her, but right now I just want to breed this ass.” It took 20 minutes and several position changes, but Gerald did just that. At one point, I was laying on my side and Gerald was behind me. He was so much taller than me, he was able to get his lips on my nipples as he fucked me. He reached down to stroke my cock and had me cumming again shortly after. He then turned my head so that he could kiss me, and I felt him cum in my ass.
Just before he came, I felt his cock get stiffer. The helmet on his cock seemed to become more pronounced. I imagined that I could even feel the veins on the outside of his cock as it got harder. If being fucked bareback felt like this every time ….
I wondered if it would feel that much better if I were on top. I cuddled with Gerald and we talked some about PrEP and bareback sex. It had been a long day for me, and I was going to need to get up by 6. I fell asleep wondering where I was going with this. I decided that as long as it continued to be fun, I was just going to go with the flow. I knew by now that I was definitely bi-, but as much as I was enjoying the sex with guys, could I really spend my life with a guy? It was so different from what I imagined over the last few years.
*****
Rod and I teed off at 7:40, the second group in our outing. We were matched against AJ and his father, although technically, we were competing as a team with Pete and Gerald. They were in the group behind us, playing with a couple of guys that I had first met at breakfast.
Format was going to be better ball. Rod and I would each play our own ball, with the better score being recorded as our part of the team score. For example, if I had a 4 on a hole and Rod scored a 5, our team score would be 4 … if Gerald and Pete had a 4 on the same hole, our total team score would be 8. Our combined score would be added to Gerald and Pete’s combined score at the end of the round. The condo with the lowest score of the 3 would win the pot for the round. This has nothing to do with what would happen later, but for those of you who are golfers, I thought you would want to know.
Rod was playing well. We only used my score on 1 hole on the front nine, although I did manage to tie him a couple of more times. We finished the front nine at one over par, and I was feeling pretty good about our team. We had beaten AJ and Alan by 2 shots.
On the 14th hole, the horns went off warning us that there was lightning in the area. We were expected to return to the clubhouse until it was cleared. Rod was driving the cart and pulled under a cover at a rest area.
Alan said, “I think we’re supposed to return to the clubhouse.”
Rod said, “I need to take a leak. Jack and I will meet you up there.”
Alan and AJ took off. Rod said to me, “We can wait it out here. I do need to take a leak though.”
He got out of the cart and entered the restroom. After a minute, I heard him call my name. I had no idea what he might need, but I walked into the restroom. I found him with his pants down to his ankles. I had no idea he was going commando. He was stroking his cock, which was at what I assumed full mast. It was impressive to say the least. “Can you do a teammate a favor, Jack?”
He didn’t have to ask me twice. When I saw him yesterday, after he took that towel off, I wanted to get on my knees then. I took the two steps necessary and dropped to my knees. The floor was concrete, so I hoped this wasn’t going to take long.
When I put his cock in my mouth, his hand immediately went to the back of my head and he started to fuck my mouth. It didn’t take long for him to reach the back of my throat. Carl and Gerald had worked with me, getting me comfortable taking a cock into my throat. It was fairly easy with Gerald, as his cock was slender. Carl had me lay on his bed on my back to help open my throat up. This wasn’t going to be possible with Rod. He was longer and thicker than Gerald, and he was more forceful than Carl. When he pressed for entry, I did my best to relax my throat and swallow. I had to remember to breathe.
“Fuck, Jack. I would love to fuck you, but I never thought about bringing any lube with me.”
My eventual goal was to work my way up to being able to take Carl’s cock. As I swallowed his cock, I wondered what it would feel like to have this pole in my ass. Gerald was easier than Pete, because Pete’s cock was thicker than Gerald’s. I knew this wasn’t going to be as easy. When I came up for a breath, I looked up at Rod and said, “I want that, too. I’m sure that Gerald wouldn’t mind spending some time with Pete tonight.” I went back to sucking that cock.
It took about 5 minutes and Rod fed me a load of nice tasting cum. Once he was done, he had me stand up. Rod was a good 7 inches taller than me. He leaned over and kissed me, using plenty of tongue. He maneuvered me over in front of a sink. I could feel his softening cock on my back. He reached around in front of me and started taking my shorts off.