So I went with my bf and a friend (@PortaUrinal) to Jockstrap Night this past week. I think you all know which bar – I’m not going to mention the name just because DOH may not be happy with what I’m about to write… I hadn’t been to a jockstrap night before and wasn’t sure what to expect. Actually the idea of a jockstrap night didn’t really appeal to me in the past because I was self-conscious about how I would look in a jockstrap. Even this time I debated and debated and took picture after picture of myself in the mirror in a few different jockstraps I own. But to me I looked fat in all of them. Finally I settled on a black one and figured I’d wear a black t-shirt to go with it to sorta make me look a bit less fat.

I wasn’t expecting my bf to go. He likes PortaUrinal on a social basis, but gets grossed out a bit by the whole piss drinking thing. But PortaUrinal talked my bf in to going. I knew when that happened I couldn’t be quite as much of a slut as I was hoping to be, but I was hoping it would still be fun.

Then after all those photos I changed my mind on what I was going to wear at the last minute. I wanted my ass covered a little bit more than the black t-shirt was going to do, so I switched to a blue t-shirt that went a little lower and covered the top of my ass. And then I changed to a white jockstrap, since it went better with the blue t-shirt. I put on my jump boots and a pair of jeans and we were off.

I was a little worried about how I’d perform. For days prior I’d been pretty asexual – I literally felt like I had no sex drive. I mean mentally I wanted a night of being slutty, but my dick was like “eh, whatever”. So to whip it back into shape I took a Cialis that morning, and when that didn’t seem to be kicking in adequately I took part of an herbal pill. The other performance issue is that I typically don’t get hard when I drink. And we drank 3 beers at home before heading out (and then I drank 3 more pints at the bar). So things were stacked against me a bit.

We got there and it was pretty quiet. As much as I’m self conscious about my body, there were guys there who were clearly not self-conscious about their bodies. Like really big, older bears/chubs who just let it all show. Some of them are sorta cute bears, others were, um…. “not so cute”. But the bar is really accepting of whatever – it’s one of the things I really like about the bar. Not that I want to look guys I don’t find attractive, but knowing they’re accepted means I will always be accepted.

Not much was going on sexually ’cause the crowd was so sparse at first. Usually the bathrooms are where the action is on other nights, but that night the bathrooms were empty and you started seeing guys pairing up and groping/whatever over by the bar. Then after a while it progressed a bit more and the guys who were paired off were one guy backed up against another guy. Then those guys were in some awkward positions and you just know the guy in front had the other guy’s dick up his ass – and they were just standing there pretending (badly) that they weren’t actually fucking.

At one point PortaUrinal and my bf went up to the roof for a smoking break and this guy started coming onto me. Of course, with all self-doubt about my body the first thing he did was ask me to take off my t-shirt. I figured what the hell and just did it. My stocky/husky build is generally appreciated at that bar.

Then another guy came up and the one guy was playing with both of us. Dicks got massaged, and we all sorta got hardons. Mine wasn’t fully erect, but close – which is good for me given that I usually can’t get it up when I drink and I was on my 6th beer of the night. The other guy who was playing with us had an really thick dick with a mushroom head that stayed hard as a rock. I liked him a lot he struck me as really submissive. Later on I told him I liked how submissive he seemed and he said he’s actually mostly a top. Well, if he’s a top then he’s probably a really gentle top – which isn’t a bad thing…

Then a crowd developed around us, and with the crowd we got a bit more privacy so dicks were pulled out of the jockstraps and we just jacked openly. I should mention that I was wearing the big 11mm ring in my PA – which guys seemed to sorta get off on. One guy got down and started giving me a blowjob – which is never easy with a ring that big.

One of the guys around us was this twink. He’s actually a bit too old to really be a twink, but in the context of that bar he was a twink. I had commented to the thick dick guy when he first came up and was just standing near us (before the crowd formed) that I found it a bit funny how twinks these days have no qualms about showing it all, but then are pretty inhibited when they go to play. And on that note I was completely wrong for the second time that night… Guess who was the first guy who took the action from jacking and a little sucking to full on barebacking – yup – the twink.

The twink was actually a top – so going against stereoptype in yet another way. His dick was nice, but not huge. It would be a great dick for fucking someone who doesn’t usually get fucked – big enough to do the job properly but not so big that you’re going to hurt the bottom. The guy he was fucking was this older guy (50ish?) who was in great shape. He had a beautiful smooth ass.

I got pretty hard watching the twink bareback the hot daddy. I figured I’d see if I could get a turn, so in preparation I took out my PA (it would have been a complication) and in the process I dropped one of the balls. I tried to look around for it but couldn’t see it. I was thinking “shit – that was like a $75 ring – I really need to find the ball”, but I just put that thought off and concentrated on keeping my dick hard so I could fuck.

When the twink was finished the hot daddy rotated around and I took my turn.  The nice part was there were mirrors in front of me so I could watch for security behind me as I fucked (since you’re not supposed to be fucking in NYC bars). The guy’s ass felt great, but given all the performance stuff going against me I couldn’t cum. I gave him a good fuck and tried to cum, but finally felt like I was hogging his ass. My dick was softening a bit anyway, so I pulled out and this hot Latino took my place.

I looked around a bit more for the ball for my PA and couldn’t find it. So I just stayed in the area until the action died down and the crowd thinned out a bit. Eventually security did come around (after the fucking had stopped), and the guy gruffly told us to put our dicks back in our jockstraps. At that point people scattered and I was finally able to find the ball for my PA. I put my ring back in (and my shirt on) and then positioned my dick so my PA was poking out the side of my jockstrap. I liked being an exhibitionist to that extent… Think I’ll do that in the future as well…

That took a while. I was a little worried about my bf… Thought he might not like seeing me in the middle of all that, but he paired off with a hot black guy and they were having some 1-on-1 fun of their own.

Afterwards I walked around and just before we left (2:30ish) I noticed the bathroom stalls had gotten really active. You could see two sets of feet in each one. So next time I gotta remember to take my action in there to have more privacy and be able to fuck more.

So all in all a fun night. I didn’t cum, but I was happy just to be able to fuck a hot ass.