Recently, my fantasy has been to suck a crossdresser, and I think that comes from the first of my two experiences where the guy wore panties. He just laid back on his bed and pulled his semi-hard dick out the leg of his panties and laid it back on him. I took it and began sucking. This was over 30 years ago, and being inexperienced about such things, I didn't really know how to communicate what I actually wanted that well, and so I think our desires were not that well meshed. I know he liked me sucking him, though, and not long after I started, he announced "I'm going to cum" as if he was warning me. I don't think he actually expected that I WANTED him to cum in my mouth. A few seconds later, he repeated his warning, and I continued sucking him, just giving him an "mmm" acknowledgement to let him know I heard him, and was continuing willfully. He then said, "Okay, then, I'm going to cum." and with that, he arched his back, moaned a bit, and shot it in my mouth.
His dick was pretty big, and torp**o shaped. I got what I wanted, but he didn't cum nearly as much as I had hoped. I could barely taste it. Nevertheless, when I'm honest about it, I really liked sucking him. It was disappointing afterwards, though, because he just barely sucked me a bit, then wanted me to fuck him. I didn't want that. So he finished me with a hand-job, dabbed it up with a wash-cloth, and told me I should probably go. We had to be careful since we were both military stationed overseas, and this kind of thing was not allowed at that time.
The second time was after my wife left, just a few months ago. My wife actually told me I should go find someone else sometimes, but she wasn't specific. This time, I advertised in Craig's List, and got one sane answer to the ad. This was a fellow who was married, and bi-curious, and his wife knew. We made connection, and met in a hotel room. He was a little too fascinated with the fact that "We're actually going to suck each other's cocks," and that became a bit uncomfortable as he kept going back to that point, so pretty quickly, I nudged us to move on. We got undressed, and I started sucking him first. He stopped me after a bit and started sucking me. After a bit of this, I suggested we go 69, which we did, but the way he wanted to 69 was rather uncomfortable, so after maybe just a minute, I changed it, got between his legs and started sucking him. In just about a minute, he announced, "I'm about to cum," and even before he drew another breath, he said, "I'm cumming," and started throbbing in my mouth. This fellow's dick was actually pretty small, so that was a downer, but he came much more than the first guy, and I got a much bigger taste. I swallowed it all as I did the first time.
After this, he laid me back and got between my legs and started sucking. I don't know what the deal is, but I really had trouble building to orgasm with him sucking me. Eventually, I had to use my hand to get myself to the edge. He quickly started sucking vigorously when I announced I was about to cum, and he took all of my cum in his mouth and swallowed. After swallowing, he just said, "So now we've both swallowed cum." (I didn't tell him I had swallowed cum one time before - it was so long ago that it was barely a memory anyway.) It became very awkward right after this as he seemed to suddenly become uncomfortable. He got dressed quickly, and said he'd have to evaluate the experience before deciding whether or not to meet again. He never communicated again, though.
So now, I'm separated with permission, and don't want the complication that would come with a relationship with a woman. I think an occasional meeting with a man would be less complicated. I would really like it to be a cross-dresser with a big cut dick who would pull it out the leg of his panties and let me suck him like the first experience, but this time, I would like for both people to expect the right thing. The problem is, I don't know how to meet someone like this, so I'm not sure how to even meet anybody. The fact that I sometimes want to suck dick used to bother me a lot. These days, it no longer bothers me.
- That's Juicy! 10
- Remove It! 0


