First Time Wearing a Jockstrap

Recently I've shared a bunch of stories from my many years of off and on sexual encounters with guys, and the most fun part for me is chatting with readers. I've been having some really hot conversations with one in particular, Mark. Literally every time he messages me now, I start to get hard, like a Pavlovian response. He's handsome, intelligent, and has an amazing cock as well, and seems to know just what to say and when to say it to turn me on.

Over the years I've had a number of guys talk about me wearing a jock strap and how they'd like to fuck me in one, but I'd never done it. I'm not sure why, it was just not something I'd ever gotten around to trying. But given a rather lengthy dry spell during COVID 19 times I bought myself a big suction dildo and some black jocks. I decided in one of my chats to show both of these things off, because I thought we'd both enjoy it. What started as some normal sexy chatting turned into me sticking a 9.5" dildo to the shower wall, bending over and fucking myself with it while wearing the jock - that was a huge turn-on for me and made me think about doing that for real.

Fast forward a few weeks, and one of my longer term FWBs was back in town. Tim is 53, 6'3, a white working professional that travels a ton for work. He's also 100% top and has a narrow but crazy long dick. I'm talking its like 4" flaccid and about 8.5" hard. Just really a lot of dick, and it gets in me fairly easily because unlike a lot of really long cocks, it doesn't have a lot of girth. For a while me and Tim were getting it on 1-2x a week, but he was away in Germany for a while, and then COVID, and now traveling again, and we sort of drifted apart.

Well, after this online conversation I was really in the mood for a good fuck and I knew Tim could give it to me, so I messaged him and we made plans. I showered, cleaned myself all over (inside and out) and put on the jock, shorts, and a t-shirt and headed over. We made some chitchat - Tim is honestly a nice guy, sweet, choir boy like until some switch turns on when he gets naked and then it is all business.

Tim invited me upstairs and soon we were making out in his bedroom. He's a great kisser. I'm six feet even, so often I'm the taller one, and it is nice having to angle up and kiss; making out with Tim becomes a full body experience quickly as he puts his hands all over me, under my shirt, squeezing my chest, pinching my nipples, and then pulling my arms up and my shirt off. I had never talked with Tim about wearing a jock, but I had a feeling he would be into it. I turned around as he kissed my neck, grinding myself back into his cock, which was already growing. He put his hands back down my pants and grabbed my ass, then stopped, and pulled my shorts down.

I turned around and said, "I hope this is-" and he immediately kissed me hard, aggressively. It was incredibly hot. He pushed me toward the bed and I scooted up it as he ripped his clothes off, that long, hard cock sticking out as he climbed up the bed and then over me, pushing it in my face. I started slowly by kissing it all over, the shaft, his balls, the head, then licking it all over. Finally I opened my mouth and bounced his cock on my tongue, then started sucking him in earnest. I can't deep throat his whole dick but I can get more of it in me than others I've been with, I struggle with the really thick guys for some reason. Soon he was fucking my face a little bit more, then a little more, and soon I was gagging and drooling.

Tim pulled out and backed up, then grabbed my legs and threw them over his shoulders, almost driving me perpendicular into the bed, and then attacked my hole with his tongue. (As a side note, rimming is still a little wild to me. Physically the sensations are amazing but mentally wrapping my brain around it is hard, so I don't usually do it or let anyone do it to me. But, something about this time I felt like I didn't want to stop him.)

It didn't take long before I was moaning, and then begging - "Tim, please, I need you to fuck me. Fuck me Tim, slide that long dick all the way in me. Please, give it to me. I need to feel you in me." Finally he came up and let my body slide down, aligned his cock and slid it all the way in, with one long thrust. I gasped audibly as even though I was pretty wet, that long cock goes pretty deep and lube helps a lot. "Are you all right?"

"Yeah, I'm fine - just give me a minute," I said, getting myself back in control. It felt so different wearing something while being fucked, my cock was hard but also constrained in the jock. He slowly started moving a little as he could see I was ok, and then more and more, until he was fucking me, that dick going so deep and touching spots that made me whimper.

After some missionary, he said, "Turn over, I want to fuck you doggy in that jock. Your ass looks so fucking hot!" He stood up on the side of the bed and I repositioned myself as he lubed his cock, and then mounted me. Between the lube and already being fucked a little, this time it went in much easier and I just said, "Oh, fuck........." as he picked up the pace. He started grabbing the jock to use as leverage as he hammered my ass over and over, another new sensation that left me moaning and begging for more. I could tell he was getting close as he would edge himself, picking up the pace faster and harder before slowing down, sometimes leaving his dick in me and sometimes taking it out and adding some lube before sliding it all the way back in again.

Finally he said, "I could fuck you like this all night if you'd let me, but I need to pack for my flight tomorrow. I'm going to cum all over that hole while you're wearing that jock for me!" He fucked me hard for a few minutes, then pulled out and started jerking off. "I'm going to cum on you! Oh, fuck! Here I go!" He positioned his cock against my hole and I felt the first blast of cum shoot out, and then another. "Put it in me, please, put it in me!" I shouted as he slid it 8 inches deep in me and kept cumming. I felt him shudder again and again, breathing heavy, him leaning against me, his cock still in me. Finally he pulled out and said, "Stay right there for a second." He came back with a wipe and cleaned up my hole for me. Then we cuddled for a while, just kind of kissing and caressing. "Ok babe, I hate to do this but you need to go, I have to pack and wake up early tomorrow for my flight."

I got dressed, kissed him, and left.

I didn't go home though - I actually had to run an errand. I hadn't thought this whole thing through all that well truthfully. I stopped at the supermarket to grab a couple things I needed for dinner the next night, kind of hoping that no cum was going to leak out of me and then also that no one saw the jock I was wearing, which kept riding up a bit higher than my shorts. It was fairly late at night, so there weren't many people in there, and I didn't need a lot, but I kept imagining bending over only to have an employee see what I was wearing.

I got home without incident and changed, feeling absolutely sexually charged and horny beyond belief. I did some work, and watched some TV, and then Mark messaged me. We chatted innocently for a few before I told him I needed to tell him something, and then told him all about my night, how he'd inspired me to wear the jock and get fucked in it, and how incredible it was. Soon we were sexting and showing off for each other. Mark turns me on so much, I can't even describe it, it is almost like he says the exact perfect thing that will turn me on every single time. Often something I won't expect, but immediately love. Between that and being fucked earlier I was almost in pain from being so turned on, so I asked him if it was ok if got to cum, and he said yes. I jerked off for him and he saw me cum, and it was a lot of cum. Like, pornstar level of cum. It shot all over me, up to my neck, my chest, my stomach, everywhere. I haven't cum that much in a long time. It was almost comical how much there was. It felt amazing, it was the definition of a toe-curling orgasm. All that pent up energy from an entire day finally released.