The premise of all these stories is situations I've gotten myself into over the years that seemed to have the potential to get me laid...if I hadn't chickened out and failed to push the issue.
Next up is a running situation, oddly enough for me, one I think might actually pan out soon. But for a story's sake...here ya go!
Yet again, the backdrop to this story is this volunteer organization I belong to, and yet another guy who also belonged.
What makes Shane a little different is that he definitely played up the macho image and seemed to want everyone to see him as a stud. The reality is rather different. He wasn't all that attractive and has a sometimes irritating personality. He does however, have a rather strong reputation for somehow bedding other guys women. And even more, somehow convincing them to give him anal sex! Not exactly vanilla sex, even in the straight world!
Physically, he's about 5'8" and about 160 pounds, dirty blond hair and green eyes. Typical blond, not very hairy, and a pretty average build. Not someone who would turn heads. By the comments from some of his friends and associates from high school, I would presume that he's uncut, since one of his nicknames was "cheese dick."
I've known him since he was in high school. He's probably 10 years younger than I am. We've generally been friendly to each other, with a bit of a mutual antagonism thing happening. He was in the National Guard off and on over the years, adding to his macho self-image. He also had a tendency to want to wrestle around with me and generally be physical which isn't all that surprising actually.
Somewhere along the line, the wrestling somehow took on a sexual tone. We were pretty evenly matched, considering the size difference between us. What I didn't have in speed and moves, I could muscle my way through. And it was definitely a physical thing, with panting, grunting and lots of body contact. Often, when either of us would get the other into a vulnerable position, the other would whisper in the other's ear things like, "I should pull your pants down and fuck you right here on this table!" and "you like bending over for me, don't ya!" The odd thing was, he generally became very passive, and almost seemed to allow himself to be maneuvered into being the one bent over like that. He had to feel my bone as I would grind myself into his ass while I whispered to him.
I tend to be rather claustrophobic...grabbing me in a bear hug is likely to result in a swift swat to the crotch. He knew this, but began using it as the finale to our wrestling matches. I, of course, wouldn't intentionally injure anyone's family jewels -- generally putting your hand in a guy's crotch uninvited is enough to make them back off quickly. He started allowing himself to be wrestled into a position that if we were naked, I'd be fucking him. All the while, I'd be talking to him about fucking his ass and taking possession and doing sexual things to him. When I'd let him up, he started grabbing me in a bear hug. It earned him a swift hand in the crotch, but he basically didn't react to it. Since what I had been taught in martial arts class was don't hit, grab and hold on until your released, that's what I did. He stopped and moved a couple of steps away, but in a new twist, grabbed his crotch and announced, "you better be careful, there's more than a handful there!" Of course, my reaction was to nod with a smirk and say, "yea, right, whatever dude."
By this turn of events, I was sporting wood the rest of the day. Talk about something that was completely out of the norm, especially for someone "straight." I found out later that there were a lot of rumors at that time about my sexual orientation flying around, so he had to be aware of the fire he was playing with.
This became the routine for our wrestling sessions, but every time I grabbed his crotch, it got more and more explicit. The next time while he was telling there was more than a handful, he popped the button on his pants. Of course, I was mesmerized and couldn't look away, but still had to keep up with the smirk...basically pushing him and hoping I'd be able to see more.
One time, he came around after one of his guard weekends and bitched about how badly his back was bothering him. He complained about it for several hours actually. Finally, he asked if he could sleep on my couch. Not a completely unusual request, since I had that happen pretty regularly, although it was the first time he availed himself of it. I ended up massaging his back (through a tee-shirt and sitting on his ass) for almost an hour before I finally went to bed. Nothing else happened, but it was still a bit unusual.
The next time we wrestled, he did go a step further, unzipping and showing me the Y front of his tighty whities. He also pushed his shirt up, letting me see some of his belly. I thought I'd shit myself. The down side to this was we where in a very public area, so there wasn't any way he'd actually go through with it.
The last time this happened, we wrestled unusually hard. At one point I had him bent over a conference room table and ground myself into his ass pretty aggressively, saying to him in a rather loud and aggressive voice, " I wanna pull your pants down and slam my cock up your ass and fuck you into liking it! Wadda you think about that?" He laid there with his eyes closed until I let him up. He immediately stood up and grabbed me in a bear hug. I was already wound up from threatening to fuck him and put my hand in his crotch, but more rubbed him than grabbed anything as a threat to hurt him. He let me loose, backed away, and again told me how there was more than a handful. Same as before, I smirked and said, "yea, right, whatever!" He popped the button on his jeans again, unzipped, pulled up his shirt and grabbed his cock, which looked pretty stiff. He didn't say anything, just stood there for several seconds squeezing it. Someone entered the building just then, he quickly put everything back in order and we went on our way.
Unfortunately, he quit not long after that. This memory is pretty intense. I think about blowing him and fucking him silly. I wouldn't be adverse to letting him fuck me, as long as I got to fuck him.
Since he left, a number of events have happened. I ran into him one day at his girlfriend's house and we talked for several minutes. He was, as always, very polite and basically tried to catch up on old times. He told me that he was going back into the guard at that time. The next I knew, his unit was activated and he was sent to Iraq. I went through an area where his father worked on a regular basis, and just after he was deployed, a picture of him (the standard military one with him holding a rifle) was put on the wall with a flag. Later, we saw a picture of him in Iraq in the paper. Then his unit returned home and he was safe.
I spent a lot of time wondering how I could track him down after he returned. Those thoughts, of course, had a sexual component to them, but I also really wanted to just thank him for serving. I knew better than to call his parents, because he never really got along with them. After wondering about him for over a year, I ran into him today out of the blue. He was in his father's workplace. We chatted for about 20 minutes about old times, etc. I gave him my phone number and told him to call me, we'd do dinner somewhere.
I've been obsessed all day about the possibilities. The whole time we talked, he stood really close to me (although we couldn't have wrestled around, even if we wanted to, because of the environment), and I caught him looking at my ass and crotch several times. His bulge didn't look especially impressive, but he did rearrange himself several times.
My thoughts are to basically ask him if he remembers all those wrestling events and how he kept telling me it was more than a handful, then tell him if he had just flopped it out, I'd have sucked his cock...and see what happens!
Wish me luck!