I don't know how many times I jacked off that weekend. The memory of Jim's cock wouldn't leave my head and left my own cock in an almost constant state of arousal. The feel of his arms wrapped around me, the smell of his body, the moans he let out at the peak of sexual pleasure - all mixed together to fuel my masturbatory fantasies for days. I creamed on every inch of Jim's white compression shorts; and then again and again. Per our agreement, I would have to tell Jim what I did with his underwear but maybe I would leave out the part about fantasizing about him at the release of every load.
Monday came but I was lucky enough to be able to work from home. Things were slow at the office and I only had a couple of things that weren't due for days - which meant I had plenty of time to squeeze out another load into Jim's shorts before washing them. Of course, the best part of working from home is that you don't have to wear pants, so I was already sitting at my computer in my black low-rise briefs. Thinking about Jim and his underwear quickly got me hard and I was stuck with a bulging pouch yet again. I slid off my briefs and picked up Jim's shorts and ran the elastic waistband along the head of my cock, enjoying the textured but silky feel of the synthetic material. I wrapped a leg of the shorts around my cock and slowly began pleasuring myself until I heard my phone go off.
"Hey. You working from home today?" The text from Jim read.
"Yeah, why?" I responded.
"I'm back in town, mind if I come over? Long story. I can be there in 30min" Jim replied.
"Sure, you're welcome anytime." I texted back.
This was an unexpected but very welcome change in my day. My dick was still hard in the fabric of Jim's shorts and I realized I would have to explain just how much cum is soaked into them over the weekend - oh well. I threw my briefs back on and started to clean my place up a little bit to make is presentable. I then picked out a pair of light blue briefs to throw on after I took a shower. I was still pretty horny, but I didn't want to take the time to rub one out since Jim was only a couple minutes away. I got dressed and waited in the living room for Jim to show up.
The doorbell rang five minutes later and when I opened the door I found by buddy still decked out in his camouflage, looking pretty tired from the weekend. We greeted each other with a short hug and Jim followed me into the living room where he collapsed on the couch. He explained to me that a pipe broke in his house over the weekend and they didn't have any water. Since he was so far out in the woods, his wife couldn't get ahold of him so just turned off the water and went to her mom's house - assuming that Jim would fix it when he got home.
"Yeah, I was pretty pissed to come home to no water and a note on the table to fix the pipes. I got nothing this weekend and all I wanted to do was come home, take a shower, and chill out with a six pack. " Jim said, in an exacerbated tone.
"Damn, that sucks." I replied. "You can shower here if you want and I've got some beers in the fridge.. but don't you think 10am is a little early to start drinking." Trying to liven the mood.
"Ha, ha. Yeah, I guess you're right. However, I will take you up on the first part of that." Jim said reaching over to slap me on the back. "But first, I think we've got some business to take care of. I've got to tell you about this underwear!"
"Sure man, go for it! I've been waiting to hear what you thought." I said.
"So those green briefs... eh... they were alright, probably good for just hanging out or whatever; but the orange ones, damn, those were great for hunting. They were nice and tight and made a big difference as I was sitting and crouching in the woods. Here, let me show you!"
Jim stood up and started taking his clothes off. He stripped off a hoodie and thermal shirt to get down to a tight camouflage compression shirt. Next, he pulled off his boots and dropped his canvas pants to reveal some white thermal underwear - the bright orange briefs clearly visible underneath. Finally, the thermal pants came down to fully show Jim in all his glory - somehow, he gets hotter every time I see him.
"So like this, it used to be uncomfortable to get into this position in my boxer-briefs." Jim said as he got down on all fours. "But like these briefs hold my balls nicely and hold onto my butt so they don't bunch up like the boxers." He added while running his hand along his muscular ass and reaching to the bulging pouch holding his balls. I was getting the full show and it was hard not to reach out and take what was only a couple of feet in front of me. Jim switched to a crouching position and I could clearly see he was sporting a semi in my briefs. "And then If I'm couching there's nothing to bunch up on my legs and twist into my junk."
"Sweet man, I'm glad you liked them. I mean... you're pretty much describing why I love briefs. Why didn't you get some briefs or wear your jock to go hunting?" I said.
"You know, to be honest I never really thought about it. I would just get dressed to go hunting and threw on my boxer-briefs. I'm glad you've shown me the light, ha ha." Jim said, standing up and adjusting his slightly engorged member in my briefs. "I will definitely have to make a change for the next time. So, what about you?"
"Oh yeah, your shorts. They were nice, man. After you left on Saturday I kinda just chilled out in them most of the day. I've never tried compression shorts before, but they're pretty similar to some boxer-briefs I've got - I'll let you try a pair sometime. Ummmm... but yeah, obviously I enjoyed them so... I jacked off while wearing them on Saturday afternoon." I said with getting a smile from Jim. "So... and then I jacked off into them Saturday night, Sunday morning, a couple more times on Sunday, and then I was about to shoot another load when you texted me."
"Shit dude, you must have been horned up! I'm glad you had a good time." Jim said moving closer to me and putting his arm around me. "Those green ones you gave me were my cum rag for the weekend when I had a couple minutes away from the other guys - nice for that purpose too. There was something pretty cool about jerking into your briefs out in the woods; dunno, felt extra fun. But anyway, where are my shorts?"
I got up and walked back to my computer desk where the cum soaked shorts were still laying from my planned morning activities. I brought them back to Jim who was still beautifully standing in my living room in my tight briefs and his tight undershirt. I held up the stuff, cum-soaked garment to Jim who reached out, took it from me, and placed them onto his face for a whiff while gently rubbing his package- something I was completely not expecting.