Ok, got time for another story tonight. Will try and post another tomorrow morning before I leave out.
So the next straight boy, or shall we call this one a questioning, curious one. He was a young man who was out living here for a semester doing an internship in the area. If I remember correctly, this one we actually met on gay.com when they still had a chat room, I see they dropped that now. So anyway, we chatted away on there several times and talked about what he was doing and just doing general chat. The first couple chat sessions were not about sex, not about his interests in men, or anything like that. We spent a lot of time talking about school, college, degrees and such. The educator in me. After a while of chatting on gay.com, we talked on messenger as that was easier and he wanted to cam with me, at first it was only me on cam and only the face. There was no "dirty" stuff and we just took things slow. After a while, probably like 8 chat sessions, we got to talking about his interests and that is when I found out that he was straight but very curious about men. His interests were in older men and he made that very clear on gay.com that he only wanted to talk with older men.
He was about 22 or 23, actually I think he was a junior in college and had to go back and finish his last year after his internship. Much of our conversations to start with were about the college he was attending as that was my alma mater. So anyway, we got to chatting about his interests and he asked a lot of questions. About such things as feeling another mans cock, how does it feel to hold another cock, what does it feel like in your mouth, what does it taste like, and such. He had questions about activities that I did as a gay man and what all I have experienced. So we chatted more about that and then got into the discussion about why I was attracted to men, how I knew it, when I knew, what about a man I found attractive and such. Several conversations later we were into the discussion about anal sex. What it felt like having a cock go inside you, what it felt like to fuck a guy, why I liked fucking a guy and getting a cock inside me. So you see, we talked about a lot of stuff. We talked about meeting at various times during our conversations and he said he wanted to but only when he felt sure, safe, and that he knew me.
So we continued to chat, we eventually cammed and showed a whole lot more than just faces. He felt confident enough to show his face, and then his body, and eventually at his suggestion we jacked off. He was a tall thin guy, about 6' 1 or 2", weighed probably about 150 and rather bony. He was fairly hairless except in the right places. His ass was smooth.
So lets get to the first in person meeting as that is what you are waiting for. So we set up a date to meet and after some changes in plans T finally arrives. He enters and my first impression is that he is cute as fuck. And sorry that I didn't have pictures taken for this one and in fact this was the second straight guy I ever met up with and never thought about photographing parts for remembrances. LOL. So T comes in and we sit down and chat. We start talking about what it was that he wanted to do when he came and I look over and see that their is some action going on in the shorts he had on. I made a joke about it and he laughed and said that he was getting a rise out of things. It surprised me then and still does at how fast and how hard these straight boys can get when they are with another man and want sex.
So anyway, I suggested that maybe he do something to let that excitement get out and he stood up and dropped his shorts and boxers in one swell swoop and there he was, open to the world, shirt followed right quick, and there he stood in all of his glory with a hard cock sticking straight out. He really did have a very beautiful cock, about 7 inches in length, cut with a very nice head on it, he was pretty thick as well, and a set of tight nuts that were on the smaller side but still great. So our first meeting went with mutual oral. After he got naked I did likewise and he dropped to his knees and devoured my cock. In fact, it was like a teenage boy attacking the refrigerator after school. He slobbered all over my cock and was going to town on it. He wasn't bad but only had a one track mind on sucking. He had never been with anyone previously even a girl so he had no experience as to what to do with a cock. So we slow him down and I said here, rather that explain it to you let me show you, so he stood up and I went to work on his cock. Touching it, caressing it slowly, stroking it gently, and then my tongue on the head, the slit, sliding up and down the shaft, and then slowly taking it into my mouth and working it, making sure to tongue that head on the up stroke. There was plenty of moaning. So then after that, he wanted to go back down on me and put into practice what he learned and did a much better job. He worked and worked and it wasn't long before he had me on edge. I asked about where he wanted the cum at and he wasn't sure but after he got to sucking and when it got close, he took it right down the throat. He told me afterwards that he usually ate his own after his jack off sessions. So after I came, I went to work on his cock and he lasted about 2 minutes and shot a load in my mouth.
T came back the next week and he was ready for more. This time he wanted to be sub (he thought he was more of that anyway) and wanted to be told what to do. I told him to get undressed, not to touch his cock at all, undress me, and then to suck my cock and get it nice and hard. This meeting was supposed to be him trying anal and taking a cock. So after he got me hard and worked over we went to the bedroom and he sucked a little more and then got into the doggy position. We had talked about safe words and what it would it would mean before we ever started. So he is sitting there on all fours, ass in the air, and I ask him if he is ready to get fucked in the ass and he says yes, fuck me. Go ahead and fuck me now. So, I am all lubed up, condom on, and is ass is being fingered with lube and I just stop and put my cock up against his virgin hole and slowly started entering. Went very slow, eased it in, and when asked how he was doing he said to keep going. It wasn't long and I was all the way in and then started the slow withdrawal. Got just about out and then pushed back in slowly. By the third push in the speed started to pick up and the moaning started down below and the speed continued to increase. We had used plenty of lube so it was pretty wet. I am not sure just how long we fucked but it was probably about 5 -8 minutes and then the safe word came. So, as agreed, I stopped, and T rolled over and there on the towel was this huge load of cum, his now softening cock laying there with cum still oozing out of the head. He came while getting fucked never touching his cock. Once he came he lost his horniess and wanted to stop. He reached up, took the condom off, and stroked me off and shot my load of cum on his belly.
T came over several more visits during that semester and each time it was for anal sex. He never wanted to fuck only to get fucked. The sucking didn't last long and he wanted my cock inside him. We tried several different positions for getting fucked and each time we had the safe word. Each time while getting fucked he was hard as hell and he shot his load every time while getting fucked having never touched his cock. Each time after he came he used the safe word and we stopped and he would finish me off. I didn't have a problem with that as each fuck session lasted longer and longer each time and it was taking him longer to cum. Sadly, it wasn't long and the semester was over, his internship was done, and he had to go back to school, which is over 3 hours from where I am and it was very hard to meet up.
We have kept in touch since and we have cammed from time to time and have watched each other jack off after talking about things, usually about sex. He never went and found anyone else to have sex with and he said he didn't really want to after me until he was ready to find another person. He moved further away for his job and one time we chatted he mentioned that an older man jacked him off in a bathroom and he told me that he had purchased a
dildo to use while he jacked off. This spring I was talking with him, and he told me that he has a regular now who comes and fucks him. He still does not fuck and the sucking is only for a prelude and then he gets fucked. The guy is a married guy, older, and from what he say, is really kind of a domineering type of guy, gets jealous if he talks to others and doesn't want him to play with other guys. He doesn't suck on T and wants him to only suck him and then to get fucked. The guy insists on fucking him bare and shooting inside of him. He asked what I thought and I told him, that I thought he was being used and abused by this guy. There is one thing about being dominate and a totally different thing about being abused. I also told him that having sex bare with someone you don't intend to be with exclusive is stupid and very risky. I told him to be tested and do it regularly. So then we talked about choices and all of that and to be careful and for him to think about stuff real well. I also asked him about where he sees himself sexually and whether his curiousness has made him choose a side. He told me that when he finds a girl that he likes and wants to be with that he will stop playing with men and be exclusive with her. I asked him if he thought he could give up a cock in his ass and be happy and satisfied. He said he would. Well this activity of his regarding his curiousness and anal sex has now been going on for about 4 - 5 years so I don't know if he will be able to give up a cock in his ass.
I have a few more guys to go through and will share them yet this week with you guys.
