Jockstrap Night at the Eagle: Part 1

The evening begins: Six guys, five condoms, and a night that was worth losing sleep over

Jockstrap Night at the Eagle: Part 1
House Slave Fag enters Eagle bar in New York

After two months without anal sex, I finally got properly and thoroughly fucked. And I have the Eagle bar in New York to thank for it. Wednesdays are jockstrap nights and it’s the easiest opportunity for sex. The fucking area is on the side of the big room on the ground floor and it was busier than I’ve experienced there before, though it’s been a year or two since I’ve been there.

Two things made it work this time. First, they didn’t open access to the second floor, so there were more people on the ground floor than there would be otherwise. Second, security never came by to interrupt the sex, like they usually did. I never understood that in the first place. Did they need to pretend that they prohibited sexual activities because of some antiquated regulations or even current harassment from city hall? Did that stop with the current mayor or did they just stop giving a fuck? Either way, congratulations.

I got undressed as soon as I arrived, except for my chastity cage, jockstrap, black harness, and a yellow band I wore on my right arm, to signal that I could be fed piss. Though I still haven’t figured out how to appropriately ask for piss in the bathrooms downstairs. I remember some fun times in the bathrooms upstairs. And once during Folsom East I got fed piss under the bar, too.

The crowd was mixed but there were so many hot muscular guys. Honestly, I felt a little inadequate, especially as I haven’t been counting macros or working out regularly in the last few weeks of hectic travels. However, I have a feeling that the extra meat actually worked in my favor, as I looked bigger, even if I wasn’t very defined. I seemed to be quite popular and I got a lot of action. The real success was in finding guys who would agree to fuck me with a condom. I’d been worried that I was douching for nothing, but thankfully I found the right Johns and Dicks.


The first guy I played with wasn’t my usual choice, perhaps in his late 50s, but he was athletic and hung thick. I was happy to get on my knees for him and he was happy to feed me, holding my head down and drilling his thick dick into my mouth. Oh, how I love the feeling of a thick dick in my mouth and I loved how this hung daddy looked down at me with a smile and caressed my head, pushing it deeper on his cock. I felt his nipples and he moaned when I squeezed them. Or maybe it was because I took his cock all the way into my throat.

It seemed like he wasn't looking for more than oral, and when I stood up he even mentioned he was going to head somewhere, perhaps deeper into the orgy area of the bar. So I got on my knees and stole a few more moments with his thick cock down my throat before he rushed off, contented.


Next I encountered a friendly Asian guy, perhaps in his late 30s. He was defined and a little tall. I enjoyed feeling his arms. His dick was small but I was determined to please him right away. I was hungry for cock and I also appreciated that he wanted to cuddle. I was less turned on by his licking in my ear, but I didn’t stop him. I did however avoid deep kissing. I didn’t want to risk another cold or something else before my flight, but he and a couple of the other guys that night managed to steal quick kisses, but I didn’t let them get their tongues in my mouth. On the other hand, I was more than happy to kiss guys on the cheek and especially on the neck or the pecs and the biceps.

While sucking this guy's small cock, I could feel some straight hairs at the base of his cock. It wasn’t hard to reach the base, and as he moaned every time I reached it, I was happy to suck deep for him all the time. But don’t worry, his cock did grow a little bit. But just a little.

I also asked him to fuck me and he was up for using a condom. Unfortunately, he couldn’t get hard enough to fuck me. So we finally went our separate ways, though we crossed paths again a couple of times later that night. I even offered to let him try again when he seemed eager, fingering my hole and rubbing his cock against it. I was especially receptive to fingers in my hole that night. Two months without fucking will do that! But what I really wanted was more cock, and unfortunately, he still wasn’t able to get his cock into my hole, even when it was gaped open.


Finally, the third guy delivered all I needed. He was an athletic white guy in his 30s, with a little more muscle. He had a very nice body though he wasn’t especially toned. He was certainly in good shape to have a lot of stamina and fuck hard. And he had the right dick for it. So thick! I loved sucking him off. It filled my mouth and I did my best to also take it into my throat. Surprisingly, when I suggested I’d give him an XL condom, he said he didn’t need it. So modest! And here I was worried he wouldn’t want to put a condom on because it would be too tight for his thick cock.

I put lube on my hole and his cock but it hurt when he pushed in. I have a tight hole and without any foreplay, it’s not easy for me to take cock. You'd think it's the thick cocks that struggle to get in before I'm gaped, but it was the opposite that night. It was the guy with the smaller dick who couldn’t get it in. This handsome, hung, athletic guy got in right away, but it hurt. I needed to pull him out for a moment to apply more lube and he adjusted his approach too.

He showed me he wasn't just a brute. He pushed in and out with smaller thrusts, until his cock was fully inside my hole. That didn’t take long, and then he assumed a fast pace and fucked me hard, showing me real stamina. I wish he could have hugged me, but at least he put all of his athletic power into his strong deep thrusts into my hole.

I moaned loudly and that amused him — I could hear him commenting on how vocal I was. I enjoyed being subjected to this jock's locker room banter while he kept fucking me. I didn't mind making a scene and letting everyone know how hard he was fucking me. So I moaned loudly, but I didn’t stop for a moment. I let him fuck me fast and hard as much as he wanted.

I'll share about the rest of that evening in my next blog post.

Jockstrap Night at the Eagle: Part 2
The evening continues: Six guys, five condoms, and a night that was worth losing sleep over