Gloving Up

The other night it was mid-evening and I needed to get up early.  I was horny as hell and didn't want to waste another night in a hotel room being celibate, so I invited over a Latino bear I'd been in contact with the other night.  He was pretty emphatic about "safe only" and wanting to know if I had condoms and lube.  So I went into it with the expectation that I'd need to wrap up.

When he arrived he was chubby and mostly smooth, but with wiry hair on his legs and ass.  He'd just gotten out of the shower, but he had a nice musky balls and ass.  His cock has an amazing foreskin (seemed like 2") but is on the small side.  Of course, like most smaller men (in my experience) he dripped a river of precum, which I love.

Hope springs eternal, however, and I employed every trick in the book to try to make him want me to slide into him unwrapped.  Actually after very very very patiently making out with him (sucking his nipples, eating his pits, and licking the inside of his ears had him reduced to jello) and after a long, relentless rim job I had him soaking and was massaging his pucker with my cock head.  If I was an asshole I'd have just slipped it in and then dealt with the reaction, but I wanted him to want it and to give me the green light to go there.  He wanted it alright, but I held back enough to make sure it was his choice.  He asked for a condom, and so I said let's keep doing everything precondom for awhile.  When I had him back on his stomach and was against his hole he grabbed the condom and I complied with his wishes.

Perhaps it was the amount of action I got early in the week with the James Taylor look alike and the Indian, perhaps it was that I failed to put lube in the condom, but rather than just being a blah, dull feeling, wearing a condom actually was abrasive.  He was loving it when I went in and I tried to build up a good feeling, but I couldn't get past a slight stinging.  I finally pulled out and asked for the two of us to stroke off.  He was close and, again like other short guys in my experience, shot a geyser of cum.  It was hot.  However, I wasn't in the mood any more and can't summon a load on demand.  I told him I was okay and invited him to clean up and leave as we both had to get up early.

I am wondering (and a tad concerned) that I might now be ruined for getting off with condoms, or even enjoying them.  For many years that was all I did, and I had no issue spewing my load into one.  Now, however, after mostly fucking bare for years it's super difficult to stay hard in one, much less to work up a load and to shoot into one.  I guess I'll have to let a load build up for several days and, when it's making my eyeballs bulge, then see whether it will spurt out inside a condom.  I actually hope I can go back there as alot of the time I'd like to make it with guys who only play safe, or I'd like to play safe until I can build up a trust relationship with the guy in encore sessions.  However, nothing beats skin to skin (pardon the pun.)