My first close-up with a hard cock. Some background information might help. I met Tom at a group jack that was organized on a site called the Masturbation Page Personals section. No longer active that I know of. Six of us guys got together for a jackoff session, which was a lot of fun but not really all that intimate. Although it was a major turn-on to see six hard pricks spurting their cum.
I was quite impressed with Tom's prick.
It was very thick with a really nice smooth head and he had beautiful smooth shaved balls to go with that good looking cock. So after the group jerk, I e-mailed him to see if he would like to get together for a one-on-one. We went back and forth in e-mails for a while, both saying we had hoped to do some mutual jacking at the group jackoff but I guess no one wanted to be the first to grab somebody else's cock. He was interested in a meeting with me as we both had a desire to engage in some mutual masturbation.
So after several months of stalling around, we finally got it together at a hotel. I got there first and when he showed up there was some joking around and talking. Both of us were a little hesitant but finally I broke the ice by saying let's take our clothes off. Once we were both naked on the bed, things loosened up very quickly. At first we both just jacked our own pricks and we both got hard very quickly.
After some solo stroking I asked him if he minded if I stroked his cock and he said no. I wrapped my hand around his thick prick and started pumping it and in a few minutes he was doing the same to mine. It felt really wonderful to touch another man's cock for the first time. I think it was his first time too. His thick cock looked and felt terrific in my hand. I pumped the shaft with one hand and ran the tips of my fingers from the other hand all over his smooth, shiny cockhead.
As I stroked his rigid prick, I kept looking at it and the damn thing just looked so good, I had to put my mouth on it.
So I gently placed my lips on the tip and slid them down over his smooth shiny red glans. My mouth engulfed his cockhead and I slid my lips as far down the shaft as I could. I proceeded to give him the kind of blowjob that I like to receive myself&hellip.licking up and down the shaft, swirling my tongue around the head, cuddling his smooth ballsack and even licking and sucking his nuts while jacking his throbbing stiff prick.
Shortly after I went down on him, he was sucking my cock as well and I am positive he had never done it before either.
We lay there in the 69 position sucking each other's hard pricks for quite a while. I was so into his beautiful cock that frankly what he was doing to mine was barely registering. Pretty soon we both agreed we wanted to cum but I guess neither one of us wanted the other cumming in our mouths so we finished ourselves off with our hands. I was a little sorry that I didn't at least stroke him to his orgasm but we still had two monster cums&hellip.very, very satisfying.
I would have loved to have my hands wrapped around that beautiful prick when it started squirting jism all over the place. Shortly after this I got an e-mail from Tom telling me that he and his 23 y.o. gf would like to have a threesome jack session with me. He sent me pictures of her and I couldn't believe what a little hottie she was.
Great body and one of the most beautiful pussies I have ever seen&hellip. Like every meeting with Tom, it took several weeks to put this together but finally we met for lunch at a restaurant one weekend. After a really nice lunch we got in our cars and drove to a nearby hotel where I had a room.
Once we got in the room, Tom and I both stripped down immediately but his gf, who was actually very quiet and shy, didn't want to disrobe. After much discussion she finally agreed to remove her top and bra but insisted on leaving her slacks on.
She had a very nice cute set of perfectly shaped perky tits. Not large but very, very nice. She was actually quite small. Probably weighed about 105 but nicely proportioned. Tom and I started stroking our cocks and the two of them started discussing my prick. It was a little embarrassing but having fun at the same time because they were both quite complimentary. Kind of odd to sit there with my cock on display while a man and a woman are discussing your cock almost like I was not there.
Many years ago when I was a teenager I had seen a porno flick that had two guys doing cock to cock jackoff. I thought that was really hot looking and had always wanted to try it.
So I suggested to Tom and his gf that we give it a try. Tom and I are about the same height so we stood face to face with our two erect pricks pointing straight up and pressed against one another. His gf dripped out some AstroGlide on our pricks and wrapped both hands around them and started pumping them.
Tom suggested to her that she put one of her forefingers between our dicks which turned out to be a very good idea because then as she pumped her hands up and down there was something rubbing on the sensitive underside of our cocks.
Let me tell you, the sensation of our two pricks pressed together and this beautiful young girl jacking us both off together was an incredible experience. Looking down and seeing our two dickheads pressed together with her beautiful small hands tightly gripping them was very, very hot. Unfortunately, because this was early in our session, Tom and I both wanted it to last a lot longer so we had to ask her to stop after only a few minutes or we both would have cum.
We all three lay on the bed and while I jacked my cock, Cheryl alternated sucking and stroking Tom's big prick. We played around for probably a good 30 minutes like this just keeping ourselves from cumming. I tried on several occasions to get Cheryl to take her slacks off because I really wanted to see her pussy in the flesh&hellip.so to speak…but she wouldn't do it. At one point Tom had to pee so he got up from the bed and went into the bathroom.
I continued to stroke my cock while Cheryl watched, but it was getting dry and she had the AstroGlide. I moved over closer to her to get it but she offered to put it on for me. She dripped a few drops on my prick and then started to stroke it and rub it all over my cock just as Tom came out of the bathroom. By now he had lost his hard-on but as soon as he saw what she was doing, his prick sprang to life.
Always before he had to work a little to get hard but this was instantaneous. That's when I knew that it really turned him on to see her with other guys.
I am sure he would have loved for her to blow me…or even fuck me…but it was obvious that she was really in love with the guy and I think she would have felt like she was cheating or something…even with his approval. Or maybe he was afraid she would think he didn't love her if he encouraged her to do any more than jack me off.
At that point, I lay back on the bed and she got between my legs and started giving me a really serious handjob. She had my prick drenched with lube and worked my shaft and knob with one hand while she massaged my lubed up balls with the other. It didn't take long and I was spurting out a huge load of cum all over my chest and belly&hellip.some even squirted up and hit my face.
I will give her credit…for a 23 y.o. shy girl, she sure knew how to jack a cock. Unlike many women who quit pumping the minute the cum starts to spurt, she not only kept going, she gripped my prick even tighter and pumped me harder and faster milking every last drop of semen out of my throbbing penis. After I was totally spent, she still kept milking my still turgid cock to eke out the last drops of cum.
It was one of the best handjobs I have ever had. She then moved over to Tom and between sucking his cock and pumping it&hellip.she soon had him unloading a really massive series of cumshots all over himself.
It was a really hot session even though we didn't really do anything other than handjobs&hellip.but as you all know&hellip.handjobs can be the greatest!! I did get together with them one time after that with Rhi, my Hawaiian girl friend, joining us. About the only good thing that came out of this was I did get to check out Cheryl totally naked. In fact I got some real close looks at one of the cutest pussies I have ever seen.
Also got some close up views of Tom's prick sliding in and out of her wet cunt&hellip. I had told Rhi beforehand about the time we had gotten together and Cheryl gave Tom and me the cock-to-cock jackoff.
This turned Rhi on a lot and she was anxious to try it. So the four of us hadn't been on the bed naked for more than a few minutes before I suggested to Tom that we put our cocks together so the girls could play with them.
He was more than willing so we got into position and Rhi immediately grabbed our two pricks and started jacking them. But it was very obvious that Cheryl was extremely unhappy with another woman touching Tom's cock. Tom picked up on this, as did Rhi and I, but in Tom's case his cock went limp. So from that point on Rhi and I concentrated on doing our thing while Cheryl attempted, without much success to bring Tom back to life.
She somehow managed to bring him off even though his cock never did get totally hard again. Rhi and I fucked and sucked each other while both Tom and Cheryl watched very closely and that was quite a turn-on.
Rhi finished me off with a world-class blowjob and just before I came she popped my cock out of her mouth and jacked me off all over my chest while Cheryl and Tom were on each side of us up really close taking in the action.
I noticed in particular that Cheryl seemed totally fascinated when cum started shooting out of my prick. She and I made eye contact as Rhi cleaned my cum covered prick up with her tongue. Possibly it was my imagination but I thought she gave me that look that said she wished she was the one lapping my prick with her tongue.
Shortly after this I got married (not to Rhi, but we are still good friends) and got together one more time with Tom and Cheryl for dinner so they could meet my new wife. We had some vague plans about going to a motel after dinner and doing some soft swinging but my wife decided she didn't want to do it and it was ok with me.
I have since e-mailed Tom a couple of times but with no answer. So I guess that chapter of my sex life is over. It's kind of a shame because I would really like to have the opportunity to work over Tom's big cock again. I have always felt that in our failed foursome, if I had gone down on him, I could have brought that prick to life.
Rhi knew that Tom and I had sucked each other's cocks so it wouldn't have bothered her. Tom had told Cheryl about the group jack session but she didn't know about us sucking each other pricks or our one-on-one meeting. I had asked Tom if she would have a problem if I went down on him during our foursome.
He said they had talked about it beforehand and she had said that she would get off seeing me suck his prick but he still seemed reluctant to say it was ok to do it. But to be honest, at the time we were all together, I was so into fucking and sucking Rhi while they watched, that the thought of going down on his cock and trying to get him hard never crossed my mind.
It was only after they left that I realized that I had probably missed an opportunity to get him hard. Rhi agreed that I should have given it a try…and in fact said she would have really gotten off on seeing me suck his nice thick cock. She was very disappointed that Cheryl had spoiled the whole thing. She had been looking forward to not only jacking our two cocks, but getting to suck Tom's prick and even be fucked by him.
Unfortunately, in a foursome, or any group sex deal, everyone has to be equally committed to the program and in this case one person wasn't. #####