Terry's story, continued...
Over the next few weeks i thought about the thing with Jack, but didn’t want to act on it. i didn’t have the confidence to go for it and was very anxious about what the reaction would be if i did. We didn’t about it again for maybe three or four weeks.
Not much changed except for the ‘dirty talking’ during sex. There was more to our fantasies now; stuff like talking about his other friends and about me being with more than one guy at a time… things like that. Each time we had sex i became more confident. I found that i was responding to more of the things he’d say to me. Even so, sometimes i still experienced uncomfortable feelings. Being with Frank made me feel really good inside, but the basic insecurity about myself and my sexuality was still there and would creep into my head.
Like sometimes i would wonder, just a bit, in the back of my mind, whether he actually meant what he was saying to me. Is that really the way he thought of me? Was he seeing me as the ‘cum slut’ he’d call me? My thinking became more neurotic and i needed reassurance that things were still cool between us. i decided i had to talk to him about what i was feeling. i had to know.
When i brought it up to him, he said i shouldn’t think like that about it; that it was just sex talk. He said “I didn’t realize these things were bothering you. I thought it turned you on. If you want to stop, we can. Do you to stop Terry?” i immediately thought he was talking about stopping our friendship. i was startled and felt sick inside. i said “No, no, no, i didn’t mean i want us to stop being friends.” i didn’t want that at all. “Take it easy Terry. I didn’t mean stop being friends. I said we would stay friends as long as you wanted to. That’s not going to change. Okay?” That’s how screwed up my head was sometimes. “I meant do you want me to stop talking to you?” i wanted to believe him. i told myself that it made sense. i wanted to believe it was just irrational thinking on my part. i did like it very much and it did get me soo hot. i said i didn’t want him to stop.
He said “Listen, it’s totally up to you if you want to do anything with Jack or anyone else. You’re a young guy and eventually you are going have other experiences with other people. I just thought of Jack because he thinks of you as a nice guy and I know it would be a safe way for you to explore. He’s not a violent person at all, despite the way he talks sometimes, and I know he’s very tolerant. I am not trying to rush you. Take your time. Waiting until you are ready is totally cool. It’s your feelings about it that count.”
He continued talking to me and i was beginning to understand his point. He was right of course, i was young and eventually i would be with someone else. i told him how nervous i would be when that time came and he said anyone would be. i told him that i felt stupid because i didn’t know how i’d go about making it happen even if i wanted to. i said what scared me the most though was what reaction would get if i did try something. He said “I can understand how you feel. Everyone wonders that at some point. If and when it fells right, you will probably feel it and you will just have to take a chance and go for it and try not to think so much about what the reaction will be. It will either happen or it won’t.”
He said that personally he thought i could handle it but it was totally up to me and that when the time came that i wanted to explore further, he would help me with it. He said if it was to be with Jack, he could try to get to stay over some Friday night. i said i would think about it.
i was starting to lean more towards being down with it.
Thursday i told Frank that i had thought everything over and that what he had said made sense to me. i said i thought i was to go for it and since he thought i was could handle it too i would try to give it a shot that Friday. i said him i still wasn’t positive i would go through with it and he said “That’s cool Terry. It’s all about you. Tomorrow night I will try to get Jack to stay over. If he does stay and you decide not to go for it, that’s okay.”
That Friday i mostly watched videos and got zooted while the guys played cards. I was soo hot and couldn’t wait to have sex. i was totally excited by not knowing if it would be with Frank if Jack went home or with Jack if he stayed over and i went through with it.
When the game broke up, Frank talked Jack into staying. As Frank went up to his bedroom he looked at me and smiled as if to say ‘this is it if you want to go for it’ or ‘what are you going to do?’ or ‘good luck’ or whatever the next thought was that ran through my head.
Jack was a few years younger than Frank. He was 34. He was taller and very muscular. Jack and i sat in the kitchen and i watched him trying to untie his shoes. i went over and said “Let me help you with that.” “Thanks, Terry.” i got his shoes off and helped steady him up. i decided this was the time and i reached to unbutton his jeans. i love button jeans. Anyway, when he grabbed my hands i got scared but he just whispered “Not here.” i felt relieved and thought this might actually happen.
We went to his room and he removed his shirt. Mmm. What a great body he had. He said “Help me take these off” as he tried to remove his pants. i got on my knees in front of him. i pushed against his cock as i undid the buttons. He was soo hard. i slid each leg out of his pants. i unzipped mine and pushed them to the floor. This was so hot! My heart was pounding. My cock was as hard as a rock. i thought about how weird it was with Frank right upstairs. But then i thought about what he said about doing this and decided not to think about anything except doing the best i could to make Jack feel good.
i slipped off his boxers and slowly started stroking him. He was very hard. His wasn’t as long as Frank’s but was very big around. He whispered, “Go slow or it might be quick. I haven’t gotten off in a while.” i told him that was no problem. i thought i could slow things down by getting another beer and a smoking a bowl. Jack joined me. i sat on the floor between his legs with my hand rubbing his thigh as gave him a light. While we got high i would stroke him every couple of minutes. i could tell he was almost ready to cum from the start. i watched his breathing closely and when it quickened i stopped and chocked his cock off at the base to make sure he didn’t cum. i had gotten very good at keeping the excitement level high without letting things go too far. i was having a totally new experience and it was so fucking hot! i had to go easy jerking myself because i was very close to cumming as well. Jack kept smoking while i stroked his cock. i had my head on his thigh and my mouth was close to his balls. i sucked one, then the other into my mouth and gently tongued them. They popped as i pulled my mouth off them. Each time his cock would strain in my grasp and i had to stop and choke him off. i took his head in my mouth and swirled my tongue around it and started making my way down. i got to the bottom easily and he began throbbing and i stopped again. i worked his balls, and licked my way up from about an inch away from his ass (i definitely am not into kicking ass) over his balls and up to the head of his cock. He began throbbing and i stopped. i looked up and he was watching me. i started working him over as i watched him watching me. He told me i should slow down. i said that if he wanted to cum right away i could do him again if he wanted me to.
He said okay. i wrapped my hand around him. My ring finger barely touched the tip of my thumb. i used my mouth to get him wet and slid my mouth and hand up and down his cock quickly. He was getting very close and asked me if i swallowed. i said i would. i felt the first shot pass up the vein under my fingertips and i let myself cum with him. i put my hand on his stomach and just used my mouth. i felt him contract over and over. When he was done i licked the head of his cock until he gently pushed me away. He was really sensitive. He said he needed a few minutes before i started again. i went and got more beer and we took a couple of hits. i was stroking him off and on, keeping him semi-hard. He said he hadn’t had sex in over a year (hmmm… That’s why he came so much) and that it was really good and that my swallowing it turned him on a lot. i said i liked it and that i was glad he liked it. i felt the same sense of satisfaction as when i made Frank feel good. i was so fucking hot! After about 15 minutes he said he was ready for me. i wondered how much of a challenge it would be to get him off again. i had him lay on the bed and went up and knelt beside him. i was so ready. i cupped his balls in my right hand and stroked him with my left. i circled the tip of his cock with my tongue and went down deep every minute or so until i felt him cumming. My mouth was on his cock head and i tongued it as he was shooting. This time when he was done i let a little cum slide down his cock. i moved over between his legs and started cleaning him up with my tongue. i rinsed my mouth with my beer and got a hot towel from the bathroom. i put the towel around his cock and i massaged him with it until he was soft. Jack told me i was ‘fucking incredible.’ He said it been so long since I was with anybody and asked me if we i wanted do this again sometime. i said sure. i told him i should to get going and he thanked me and said he was already looking forward to the next time. i told him to sl**p well and he said he definitely would after that. i locked up on my way out…