All This On The First Try!

I am so happy that computers ever came along. I had been married for 15 years only to discover that my wife had a man on the side, and that she was going to leave me so she could be with the other guy forever. That sure left me hanging. I was suddenly back on the dating chain after so long, and things had really changed. I went for quite a few years without dating and ended up jacking off to satisfy myself sexually. It was fine for those years, but I eventually decided doing this myself just wasn't cutting it, so I figured it was time to seek someone to take over for my hand. This is where the computer came in.
I had heard of a few websites that had some porn videos on them that were free and that actually showed full length videos. I started watching some videos and found myself deciding I couldn't wait any longer to find someone to share some sex time with because the videos just made me hornier than I already was. Some of these sites had real time video and I was at least able to experience jacking off with a woman watching me as I watched her rubbing herself off. I felt though that most of the time the women were pretty much following a script or were faking their own performance. Before very long I was getting turned off pretty quick by the fakes. I did go back every now and then to get the stimulation that came from having someone watching me, but before long that wasn't working anymore either.

I found a local hookup column on the local version of bobslist, if you know what I mean. There were a lot of women who would place an ad, but whenever I would contact them, they would want a lot more than a one-nighter or a friend with benefits hookup. I was looking for a sex buddy who I could call once in a while for some hot sex without it having to turn into a long term relationship. There aren't a lot of women out there that answer an ad for that with an older guy like me. So I tried many many ads trying to find just one halfway good looking woman who would agree to those terms and I never found her. So it was pretty much back to the video performances and jacking off, until things changed one night.

I had gone online to a new webcam site where there were about 30 chat rooms open with a different category for each room. I went through room after room looking to find a lady to share some camera time with but wasn't doing so well. Out of curiosity more than anything else I went into one room that was for Bi and Gay chat. I quickly discovered that there was one advantage to watching other guys jacking off while they were watching me jack off, and that was, you can't fake a man cumming. A guy can moan or groan all he wants to, but when you see him shoot his load you know it's for real. Suddenly I felt a little different about things. I knew these guys were genuine in their having climaxes or orgasms because I was watching them actually shoot cum. No woman could do that. She could finger herself all night if she wanted to, and I could never tell if she was enjoying it or if she was faking the whole time. With watching a guy cum, I knew it was the real deal. It made me as horny as hell and I found myself feeling that maybe a straight guy could get with another straight guy to jack off and it wouldn't be too weird. Now that bobslist thing took on a whole new light.

I went to the bobslist listings for men for men hookups and found many of them were for guys hooking up for the first time, or were straight guys looking to jack off another straight guy. I started to make some inquiries with the ads that were looking like something I'd be comfortable with. Unfortunately for me, I went months without ever finding anyone who would want to do more than trade cock pictures and what they called stats. I must have done that 10 times, but none of the guys ever got back to me after they had gotten a picture. I was about to give up on this idea too and then maybe go live in a monastery or something, because it was looking like I was never going to hook up. Then I went to visit some f****y in Wisconsin. I was there for a few days and I was getting horny, so I looked at listings for the town I was in. There was a guy looking for a first timer to get together with. I don't know if it was because I was out of town or what, but I felt a little more bold and decided to contact this guy.

I made the first contact on my laptop and said I was in town for a couple of weeks and wanted to maybe get together with him. I figured I would hear back from him the next day, so I was kind of surprised to hear back from him within 10 minutes. He said he really wanted to meet and wondered if I was familiar with a small town in Illinois, which was across the state line and about 30 miles or so from where I was. I told him I knew exactly where he was talking about and he said he was quite excited about getting together. So I grabbed my cell phone, jumped in the car, and headed toward the town he lived in. While I was driving, my phone would ring and it would be a text from him asking me some things about myself and telling me a few things about him. I mentioned I was on the road and traveling toward his town and wondered if he had a place where we could meet. He'd get back to me after a little while asking if I knew where a certain store or bar was at where we could meet before we went anywhere. Because I didn't know too much about the town I said it would have to be someplace that he could send me to so I could set my navigator right to the spot. I was growing more and more worried that this guy was maybe chickening out as I got closer and the meeting got closer to a reality. Then he would say that he wanted to try giving oral for the first time and that he really wanted to try it so he wanted to make sure I got there. He was an insurance salesman so he said he was able to change an appointment he had and that he lived right by his office so we could go to his house. I was about five miles from his house when he texted and said that if I wasn't going to try oral myself then he might not want to meet!

I had driven over 40 miles to get to this town in Illinois along the state line. I had driven here expecting to meet up with a guy who was going to swap jacking off with me. Then I thought he was going to do that and then try giving me head, because he said he had never tried oral and really wanted to try it. But now I wasn't sure anymore. His last text said if I didn't want try try giving him head too that we wouldn't be able to meet. I was ready to punk out and drive back to Wisconsin and give up on it all. Then I got another text. He had to meet a client for 45 minutes and wondered if I would mind hanging around at a diner where he could come in and meet me after his meeting. I called him instead of texting and when we talked he sounded much more willing to be flexible, but said he had done the mutual masturbation one time and got so horny that if had lube and condoms with him he would have gone for it. Him saying that made me so horny that I wanted to wait and who knows, maybe I would even be willing to try something else after jacking him off, I would just have to see. He said that was what he had meant before and that he'd see me in 45 minutes to and hour.

As I was driving up to the diner where I was going to meet the guy I saw a pharmacy, and taking the guy's lesson from his first meeting, I went in and bought a small box of condoms and a small bottle of flavored lube, picking cherry since that was the one I always tried to get my wife to try. Now I headed for the diner and began the waiting game. As each person came in I wondered if they were the guy I was going to pop my proverbial cherry with. It went right up to the full hour and I knew the guy walking in was him because he was looking at everyone in the place, waving at most, speaking to some, and then stopping when he saw me. He walked over and asked if I was Eric, and when I said I was, he said he was Don. He said he wanted to go right away so nobody got any ideas about what we were doing and that I should follow him outside to his car. He then asked me to follow him in my car and we would head to his house. Once we were there he said we could go in and get comfortable. This was finally it, and I have to say I was more nervous about this then anything else I've ever done. I am quite an adult without a doubt, but I felt like a 10 year old k** again going to stay the night at a friend's house where we would jack off and watch each other for hours. But now, I wasn't a k** anymore and wondered why it seemed so dirty now when it was all so innocent as a k**.

When we got over to Don's house, he said to come on in. I looked around as if I was going to see someone I knew checking up on me. I just couldn't shake this feeling of guilt or shame or whatever it was. Don said I should make myself at home while he went to take a shower. He asked me if I wanted to join him, but I said I would pass. "If you'd feel a bit easier about it, we could both go in the hot tub instead. " he said. That seemed comfortable enough, so I said that was a good idea. Don said, "The hot tub is in a fenced enclosure, so we don't have to worry about any prying eyes." That made me feel a lot better, and we headed for the hot tub. As we entered the fenced hot tub, Don began to undress. He said he had had a tough week and all he wanted to do now was relax. As he took off his boxers, he had a half hard cock, but mine was as hard as a rock. Just imagining what I was about to do for the first time in decades made me hornier than I had ever been. I got all of my clothes off, and it was obvious yhat Don had been waiting to see my cock. I noticed his eyes as he made a look that said he was surprised. Now I was uncomfortable again thinking I had the smallest dick he had ever seen. To my surprise though, he said my cock was pretty big, and that it looked real good. Once again I was relaxed about the whole thing.

"How do we do this?", I asked. He said to just relax and enjoy the hot tub, that everything else would happen once we went inside. He said he had a thick terry cloth bathrobe I could wear when we finished tubbing. So I laid back and let the bubbles relax me. After about 30 minutes had passed, Don got up and said he had had enough. If he stayed in any longer he would probably fall asl**p. We had made no small talk or even had any conversation for the whole 30 minutes, and now I felt like I was going to just start talking and never shut up. But Don broke the silence instead, and asked if I thought it would be best if we sat on the couch or laid on his bed. One other choice would be to lay on a blanket on the floor. I told him the floor would be good with me, and he agreed. He then said he had only been with another guy one time about two weeks earlier, and that it was the most awkward time he had ever had. I knew exactly how he felt. How do you go about doing this thing anyway? So as we both kind of laid back and then propped ourselves up on our elbows, I just went for it. His robe was open in front and I reached over and grabbed his dick with my left hand. I immediately had a real strong urge to just start sucking his dick. I think that as a man, the first thing you want someone else to do to you is to suck your cock, so I think that's where the urge came from. This being the first time I had ever touched another man's cock, and not quite being able to get past the idea of some guy cumming in my mouth, not knowing what it would feel like, or taste like, or even smell like, I couldn't make myself do it. But I will say that I was so turned on that I nearly came just at the thought of it. I knew I was going to be able to get past all of this before I left Don's house, and I was probably going to end up doing oral. I mean when you think about it, one of the strongest thioughts a guy has while he's jacking off is wishing he could suck his own dick, am I right? I look at my own dick so many times and just wish I could reach it with my mouth, so the idea of a dick in my mouth was not a strange thought to me. So I jack Don off real slow at first. I could feel him tensing up and knew he was getting ready to cum. When I felt that, I would ease back on his dick and come real close to stopping all together. He never said anything, but his face was saying, "Come on Eric! Make me cum already!" After edging him about four times I was about to make him cum, when it dawned on me that we hadn't talked about what to do when it was time to cum. Should I let him shoot straight up with it coming back down on his cock and balls? Should I let it shoot onto his belly? Or maybe I should aim it away from him and let it shoot onto the floor. Of course there was one more option, which would be me putting his cock into my mouth and letting him shoot it in my mouth. So when he tensed up and I felt him arch his back, I knew he was ready to explode. I squeezed his dick at the bottom of the shaft, and as the cum backed up into his dick, I let it go a little at a time so it would squirt much further than it might otherwise. His cum shot up about two feet straight up and came down onto his chest. I think he was really surprised though when a big blob of cum shoot up into his own face. "What in the hell was that Eric!" Don said, "I have never shot so much cum and never came so hard in my life!" Obviously, he was pleased with this technique called edging. By stopping him from cumming those four times, it backed up the cum and heightened his sexual awareness, so when he did cum, he was cumming four times at once. He had never known about the squeeze and release thing either. He said he wanted me to stay as long as it would take for me to show him how to do it himself.

Well now it was my turn. I got so turned on as I laid back that I almost came from just thinking about it. This was going to be hard for me. As strange as it may sound, I hadn't had any sex with anyone in over 25 years, and Don was going to be the first person to touch my cock in all of that time. He said to me as he began, "Remember what it is I've been wanting to try." As he said that and I knew he meant oral, I almost came again. I wasn't sure whether I should try to think of something else so I wouldn't cum too soon, or if I should just lay back and let it happen. I decided to just let it happen. Don wasn't so much jacking me off as he was squeezing my dick one finger at a time, First the little finger, then ring finger, middle, then index finger, and then start the sequence over again. I have to say that although it was a strange method, it felt great. My cock was feeling something it had never felt, and it felt good. At one point he got his mouth right down to the head of my dick and just breathed heavily on it. I felt the moisture and the heat of his breath, and just as he did this I felt one little pearl of pre-cum squeeze out of me. He was about to pull away, but it seems like just at the last moment he saw the pre-cum and he put his lips on my cock and it was almost like he kissed it from my dick. I don't think he realized how close he came to getting a face full of cum because it brought me that close to exploding. I never really thought about it before, but it must be obvious to a man when another man is about to cum. Just as I was about to tell Don I was going to cum, he took my cock in his mouth and sucked on it as I shot what felt like a gallon of cum down his throat. I didn't just cum though, I had an intense orgasm like I had never experienced before. It was an amazing feeling, and when it was done, I could hardly stand to have him touching my cock. Each little movement caused another wave of this insane orgasm, and I could barely move afterwards. I don't know if it was simply because I had been without sex for so long, or if it was because of the taboo of another man causing it was driving some deep sensual part of me. I didn't care why anyway, I just enjoyed it. It was 15 minutes before I could even move or talk to tell him what I had experienced. I think he felt like he had done it all by himself and he seemed proud of the accomplishment.

I wasn't sure what was going to happen next. I took out the cherry lube and got a big handful. I took Don's dick in my hand and very slowly rubbed the lube up and down his hard cock. He was shiverring with each stroke, like it was his first hand job, or maybe it was the anticipation that this hand job was going to end with a blow job. Whatever it was didn't matter though. I had long since lost the inhibition that made me not want to think about oral sex with another guy. I was lost in sensual bliss after having such an intense orgasm. Right now I felt like I owed it to him to return the sexual favor by taking him to the same orgasmic pleasure. I imagined each stroke of his cock as the stroke in and out of a hot wet pussy, and that started to turn me on. It didn't take long for me to switch from lubing his cock to taking his cock into my mouth. I could hardly believe I was doing this! As it turned out though, I enjoyed it as I closed my eyes and imagined I was sucking my own dick like I had dreamed of so many times while I was jacking off. I was doing to Don exactly what I would be doing to my own dick if I could reach it. Every stroke in and out was just like that stroke in and out of that wet pussy. I was hoping Don wouldn't come for a little bit, because I was actually getting off by sucking his cock. Just as I was thinking that, Don grabbed the back of my head and I could feel him tightening up, preparing to shoot into my throat, and just as I thought that, he came with a powerful blast. I didn't taste anything and I didn't smell anything besides the cherry lube as his cum went down my throat. It wasn't a bad thing at all. The problem with him finishing though was I was too horny to stop. So what now?

It was almost as if Don knew what I was thinking, and it was obvious what he was thinking. He pulled out one of the rubbers from the box, and unwrapped it. I was kind of scared thinking that he had the idea that I was hot enough to go straight from mutual masturbation, to oral, and straight into taking his cock in my ass. But them Don turned over and rolled the rubber onto my cock. I was totally freaked out, but I was so turned on that I couldn't stop what was happening. He grabbed the lube and asked me if it was supposed to go on the cock or in the ass. I didn't know and neither did he, so he got a handful and rubbed it onto my cock. He didn't just put it on me though, he stroked it on like he was slowly jacking me off. Then he took another handful and rubbed it on and in his hole. He wiped the extra onto the blanket, and then he positioned himself by laying on his back and bending his legs. I asked him if he was going to be okay, and he said he thought he would be, because he had been doing himself with a rubber cock for a while. So I did what comes naturally, and I pushed my cherry lube covered cock into Don's tight ass. It took a little pushing to get it in, and I think he was a bit uncomfortable, but I slowly began to stroke. I never thought that being so horny would lead me to doing this. I met with this guy just 1 1/2 hours ago to jack him off and to be jacked off by him, and now I had done that, sucked his dick and swallowed his cum, and now here I am fucking this guy in his ass. I hate to say so, but it felt so good. As I was stroking in and out of his ass, I took his dick in my hand and jacked him off. I thought that seemed like the right thing to do, and I think it's what I would want if I was being fucked. It turned me on too, and made this whole thing feel even better.

I found myself totally enjoying anal sex. I had anal sex many times with my wife in the past, and there was no reason to feel anything but sexual pleasure right at the moment. I was digging what I was doing, and considering he was making some satisfied groans, so was Don. So I just let myself feel nothing but the pleasure, and when I came, it was once again a huge totally satisfying orgasm. Don said he too had a similar experience and said he had never cum as hard as he did just then. We were both totally satisfied with this arrangement and had enjoyed every bit of it. By now I was exhausted and Don was too. We may have wanted to keep going all night, but we were just too physically tired to keep going. I told Don I had to get back to Wisconsin because the f****y had dinner planned for the night and since I was only in town for a few more days I had to go. I wanted to get with him one more time before I had to drive back to New Mexico, but there were too many things planned that I couldn't get away from so it just wasn't going to happen. It had been good, but it has never happened like that again. I did get with one other guy to jack off with once since then but it never went any further than that. I haven't gone from straight to gay. I don't even claim to be bi-sexual. I believe that just like we have been seeing two ladies getting together with nobody getting too upset over it, and I think it has now gotten to where two straight guys can hook up for a good time without feeling like their sexuality is threatened. I'm glad I had the chance to try it all out, and don't think I'd ever hesitate doing it again. It was good.
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Posted by jerrad
3 years ago    Views: 754
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1 year ago
awesome story, im still trying to build up the courage to meet up with a guy right in my town. ive talked to him for a while now and hes really patient..but im so nervous...plus i think about the whole "you're going to hell" thing that people throw around a lot...so that doesn't help. any help you can give me?
3 years ago
Your history drove me insane.