Jim and I Pt. 02

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Friend and I experiement with underwear and each other.
4.9k words
4.77
7.1k
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Part 2 of the 8 part series

Updated 10/03/2023
Created 10/18/2022
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The next morning, I heard a loud crash coming from somewhere in my house. Hungover and groggy, I reached for my glasses and instead knocked my alarm clock off my nightstand. I finally figured out where my glasses were and went to investigate the noise. I was still just wearing my green briefs but the heat in my house prevented me from putting on anything more substantial.

I walked into the kitchen and was presented with the blue, cotton-clad ass of my friend Jim; bent over in my kitchen in nothing but his boxer-briefs. He was picking up an assortment of pots, pans, and lids off the floor and awkwardly trying to put them back in the cabinet from where they came. I stood there for awhile admiring the curve of his ass, the pronounced shape of his balls outlined by his Hanes, the hair on his legs, and the tattoo on his back. It was probably only a few seconds but it felt like and eternity to me.

"Morning bud. Nice boner." Jim said with a smile as he turned around and stood up.

"Ha, thanks... I guess. Morning wood; you know." I replied knowing full well that the six throbbing inches barely contained in my briefs was due to something far more interesting.

Jim explained that he was going to make us some pancakes for breakfast but was having some trouble finding his way around the kitchen. I showed him where everything he needed was while subtlety noticing that I wasn't the only one sporting a little wood this morning - the bulge in Jim's boxer-briefs had swollen slightly since I first came into the kitchen. I tried to take my mind off of it and started brewing a pot of coffee. While that was going, I went back to my bedroom to throw in my contacts and wash up a little bit.

When I returned to the kitchen, I found Jim throwing some finished pancakes on a plate and putting them on the table. I grabbed some for myself and sat down to join him for breakfast. I was surprised, the pancakes were really good! I complimented Jim on his as yet unknown to me cooking skills and was treated with the story of how his wife forced him to learn to cook a few things so that he wouldn't starve to death if she was away. The conversation went on from there but neither of us mentioned the activities of the night before... to the point of being obvious that we weren't going to talk about it.

"So... that movie from last night... we didn't watch all of it, did we?" Jim finally surprised me by saying after swallowing the last bite of his pancakes.

"Ummm, no; I don't think so. I think the description said like an hour and a half but we obviously didn't need that long. Why?" I said, a little nervously.

"Nice. Well, I've got some morning wood and we know you sure as hell do and I figure we might as well get our money's worth from that $4.99 rental. Want to jerk off again?"

"Sure!" I said, trying to hide my excitement. "Let's head into the living room and get it done."

I got up from the table doing nothing to hide the re-awakened boner trying to burst from my briefs. Jim got up behind me and the seven inch tent in his boxer-briefs was straining the blue fabric. I sat down on the sofa in the same position as last night and started to fight with the stupid cable box to get the movie back up and running. Instead of joining me, Jim shucked off his underwear, threw it on the recliner on the other side of the room and stood a few feet away from me slowing yanking his shaft and massaging his low-hanging, hairy balls.

"Last thing I remember is the cheerleader chick getting blasted by a couple of football guys. That had to be the end of a scene, so just go to whatever's next." Jim said while playing with himself. I obliged and skipped ahead to about halfway though the video where a new scene just started. "Yeah dude, that'll do." Jim said and took a seat on the recliner; laying back and proudly displaying his cock and balls.

The movie picked up and we both got to work on our dicks. I kept looking over to admire Jim, hoping he would do the same to me, but he was pretty focused on the movie. The scene of the study group that turned into a lesbian three-way didn't do much for me, but Jim was clearly enjoying it. His breathing was heavy, chest and brow sweaty, and he was giving long, vigorous strokes to his manhood. By the ever more audible grunting, I could tell he was close and this was putting me at the edge as well. Jim grabbed for his boxer-briefs and wrapped them tightly around his cock and continued to stroke for about ten more seconds until releasing his morning load into blue cotton. This did it for me and I picked my briefs up from next to me and shot my thick load into the pouch.

We laid there for a couple minutes recouping from our workout. As my heart rate returned to normal I heard Jim let out a groan and he stood up to stretch and looked up to watch his softening member lay atop his sweaty balls.

"Full belly and empty balls... great way to start the morning!" Jim said as he clenched his cum-soaked underwear in his right hand. He then spotted the crumpled black jockstrap he had filled with his seed the night before and picked it up off the living room floor. "Huh... all this jizz-soaked underwear might be hard to explain to the wife when she gets back and does the laundry. You mind taking care of it?"

"Sure man, no problem. It'll fit in well with the 'cumderwear' I've made this weekend" I said with a laugh. "Though I'm guessing you're out of boxers now. Do you need a pair for the rest of the day?"

"Yeah, that would be good, just give me whatever you won't miss. If you don't mind, I'll grab a shower and probably head home. I've got to take care of the dog and do a couple projects the wife gave to me to 'keep me out of trouble' during the weekend." Jim replied.

Jim headed to the guest bathroom and started up the shower - I of course admired his ass the whole time he walked down the hallway. I went to my bedroom, threw on some shorts, and opened my underwear drawer to figure out what to give Jim. I could be safe and give him a pair of plain cotton boxer-briefs I have, or maybe a little adventurous with one of my more preferred tight, synthetic boxer-briefs. Then I thought "I can give him whatever I want" and reached for something more interesting. I heard the shower turn off and a minute later Jim walked into my bedroom in just a towel waiting for what I've picked for him.

"So, I thought you'd like to try something a little different." I said as I pulled out my selection and held up a pair of grey Hanes string bikinis in front of me. "It's kinda like a jock and... I don't know... maybe you'd find it cool." I added getting more nervous about my selection.

"Right on, looks good" Jim said grabbing the garment from me. He dropped the towel and pulled on the bikinis, making sure to adjust his package to fit in the tight pouch. Jim felt the strings on his hips and slid his thumbs under them on each side. "How do I look?" He said with a smile and a snap of the elastic and turned around to walk to the bathroom to finish getting dressed. In the meantime I picked up the various articles of cum-soaked underwear from my living room and threw them in with the rest of my laundry. My fingers lingered longer on the black elastic straps of Jim's well-used jock, imagining how perfectly they framed his ass and helped to support those low hanging balls of his. I was snapped out of it my Jim coming back into my room fully dressed and ready to head out.

"Thanks again for having me over, I had a really great time. I promise I'll get your underwear back to you next week after my wife does the laundry and you can just get mine back to me whenever." Jim said.

"Absolutely. I had a great time too - you're welcome to come over whenever." I replied.

I lead Jim to the front door and gave him a pat on the back as he stepped outside. I may have let my hand linger too long feeling the musculature beneath his thin cotton t-shirt, but Jim didn't seem to mind. He turned around and gave me a hardy handshake then jumped in his pickup truck and headed home. I closed the door and immediately went back to my bedroom. I picked his jockstrap up from the laundry pile and held it in my face as I inhaled the musky smell of my friend. I ripped off my shorts and pulled the supporter up my legs and over my throbbing cock, now leaking pre-cum. I reached for my dick and gave it a couple pumps and that it was all it needed to produce my second load for the day, soaking the jock once again and mixing with Jim's own sweet juices. I laid back on my bed and drifted off to a wonderful post-orgasmic nap while still wearing the moist jockstrap.

After waking up from my short nap, I resumed my normal weekend routine. I cleaned up from breakfast, straightened up the living room, and threw Jim and I's cum-stained underwear into the wash. The rest of the weekend was pretty normal and low-key, but I just could not get the image of everything that had happened out of my head. I spent most of the time with a constant boner and relieved myself a few more times thinking about Jim and all the things that I would love to do with him. However, Sunday night came and it was time to get ready to go back to work. I packed my lunch and clothes for Monday along with Jim's now clean underwear to return to him. However, looking at the pouch of the jockstrap gave me an idea I just couldn't resist.

Monday morning I walked into the locker room around 5:50am. When I turned the corner I was greeted by a shirtless Jim who had arrived only a couple minutes before me. With his shirt over his head, he didn't see me coming, so while I passed him I reached out my hand to give him a light slap on the abs. "Good morning bud."

Jim finished pulling his polo over his head and realized what was going on. With a big smile he replied "There he is! Good morning!"

We chatted a bit and caught up with how the rest of our weekends went. Again we both expressed how much fun we had on Friday night and agreed that we would have to hang out more often. I noticed Jim was back to his normal boxer-briefs, but I didn't mind - he looks great in everything. Since I already had my workout clothes on, I just sat on the bench admiring him as we talked. However, before we headed out to the gym I stopped him.

"I've got a surprise and you've got to promise not to hate me." I said.

Jim looked up from tying his shoes and said "Ok..." in a sort of questioning tone.

"Well, I blame you for planting the seed in my head, but I had to try it." I said. I then took the waistband of my gym shorts and pulled it down a couple inches on one side to reveal the thick black waistband of Jim's college jockstrap. "I hope you don't mind, I'll give it back tomorrow. I promise." I added.

"Ha, nice. Nah I don't mind; the old guy is getting a lot of use these past couple days. Hope you like it." Jim said with a wink and a smile.

I smiled back and pulled up my shorts. Jim finished tying his shoes and we headed to the weight room. Jim and I lifted for about 45 minutes and it was just like normal - no awkwardness from the weekend or anything. I was really enjoying having Jim's jock holding my nuts and having the smooth fabric of my gym shorts rub against my exposed ass - so much so that I had to fight back growing a boner in the middle of the gym. The workout was finally over and Jim and I headed back to the locker room. I pulled off my shirt and shorts and stood around in just my buddy's now sweat soaked jock. Jim didn't mind in the least and striped naked as he put his workout clothes away and made chitchat with me. I finally removed the jock and threw it in my locker and hit the showers. I was so worked up that I debated rubbing one out in the shower, but I decided against it and just turned the water colder. I finished showering and returned to my locker to find my 6'8" god of a friend toweling himself off. We got dressed and headed back to our desks.

"So how'd you like that jock?" The instant message from Jim said about an hour or so later.

"It was good. Kinda weird not having anything cover your ass, but I got used to it after a while." I replied. "I'll probably stick to my briefs for now but thanks for letting me try it out."

"Yeah, I'm glad it's still useful after all these years." Jim sent back. After a minute or so he added "So... did you wash it before you wore it or was that in the shape I left it?"

"Yes, I definitely washed it. I like you man, but not enough to have my nuts covered in... you... LOL" I sent back, which was a lie but I didn't want Jim to think I was being weird about the situation.

"Ha ha. Cool. I'll have your stuff back for you tomorrow except for that pair you gave me Saturday morning." Jim responded. I've got to run to a meeting now but let's meet for lunch and I can tell you why I won't be able to return your stuff right away. Later!"

I closed the IM box on my computer and let my mind wonder on why there's a story on why I'm not getting my underwear back. I snapped out of it a few minutes later and resumed writing my computer code. A few hours passed and it was time for lunch. I got an IM from Jim saying to meet in the cafeteria for lunch, so I grabbed my food from the fridge and found the table where we usually sit.

"So, I hope you've got a good explanation for me." I said jokingly as I sat down across from Jim who was already assembling his sandwich.

"Well, I've got an explanation; you can be the judge if it's good or not." Jim shot back. "It's sort of a funny story so I'll get right to it." Jim added in a now more hushed tone. "After I got home on Saturday I started doing all the chores that my wife left for me. I was working up a sweat and being the only one home I just stripped down to the skivvies you gave me... by the way very comfortable for getting shit done. Anyway, when I was done I sat down on my bed and caught my reflection in the mirror and noticed... well... noticed how good I thought I looked in those briefs. So much so that I got a little excited and figured I would rub one out. Well, as it seems we both like to do, I got to the moment of truth and shot into your briefs. So... I've got a sticky pair of another guys briefs hidden in my truck because it's too awkward to explain to my wife how and why they got into our laundry."

I stared at Jim for a couple of seconds before responding "HA! That sounds like the setup to a bad gay romance novel or something. I'm guessing you're wanting me to take care of this again? That's fine, just fold them up and put them with the rest of the briefs you're retuning tomorrow; I'll do the rest. I just hope you had a good time."

"Yes, it was a good time." Jim said. "My right arm surely got a workout the past few days."

"Indeed." I replied. "So, I've got to ask... and don't take this the wrong way... but are you into underwear? I only ask cause you seem to be cool with trying different styles and you like to shoot your load into it; I like that stuff too" I added in a very hushed and nervous tone.

"Ummm... I guess I never thought about it that way, but I guess you could say that. Is that cool or weird or... gay or something?" Jim responded.

"Nah man, I think it's cool and even cooler to find someone else who thinks the same way." I replied with a re-assuring smile. "Would you... like, you know... want to like trade some pairs and stuff just to try different stuff out?"

"I feel like we've already started down that path so why not keep going." Jim said now more clearly relaxed and interested in the situation. "But how about this, we have to promise to tell each other what we thought about the pairs and what we did with them. Like I just did: the briefs were super comfortable and I filled 'em with jizz. Is that cool with you?"

"Yeah man, that sounds like a lot of fun." I said with excitement - both in my voice and in my pants. "Being completely open about it will be a lot more interesting than just 'nice boxers' or whatever. I'm 100% in."

"Great!" Jim replied. "Shit... it's almost time for some stupid HR training I need to go to. We can figure out the details of our agreement later. I'll catch up with you tomorrow in the gym, gifts in tow."

Jim headed off to his class and I cleaned up my lunch still letting what had just happened sink in. Did I really just agree to exchange underwear with a guy I have a huge crush on and agree to tell him how I jacked off in them? Awesome. The rest of the day was a blur as I threw myself into my work trying to avoid getting a boner at my desk. When I arrived home I immediately stripped off my clothes, reached into my gym bag, and filled Jim's still damp jock with another load of my cum. I threw on a pair of my favorite boxer-briefs and took the jock to the sink to wash them by hand - no reason to run a whole load of laundry. I dried and packed the jock with Jim's clean boxer-briefs into my gym bag so I could return them to him and then. The rest of the evening was like any other and I went to bed early so I would be ready to go in the gym the next morning.

Jim and I got to the locker room at the same time the next morning. He was quick to strip down to his underwear but not so quick to put his gym clothes on... almost like he was showing off for me; which I didn't mind at all. He reached into his bag a gave me the stack of clean folded briefs that he had borrowed the week before, explaining that that the one filled with his seed was wrapped in a paper towel at the center of the stack (how thoughtful). I placed the underwear in my bag and pulled out Jim's jock and boxer-briefs that I had washed for him and handed them over. I saw a quick flick of Jim's cock through his boxer-briefs as he put his hand on the material and he reached down to slowly adjust his manhood - I think he was getting excited by the underwear... nice. He thanked me and continued getting dressed and we headed out to our workout.

The rest of the day was like any other with stupid meetings and uncooperative code. I wanted to IM Jim to set up our underwear exchange, but didn't want to seem to pushy about it... maybe he had second thoughts. I hadn't heard anything from him on the subject for the rest of the week - just the normal silly internet links and general current events talk we usually have - so I figured he changed his mind... oh well. I went home Friday night after work and had a couple beers to relax for the weekend. I remembered I still had my grey string bikini's filled with Jim's cum in my laundry basked waiting to be washed, so I went back to my bedroom to fish them out. The fabric was stiff and filled with a musky mix of sweat and seamen. I held the bikinis up to my nose and inhaled the scent while I let my jeans drop to the floor; now standing in only my black low-rise briefs. My cock was instantly hard and I dropped the briefs to the floor and replaced them with the dirty string bikini. I rubbed my cock through the stiff pouch feeling the texture and imaging Jim's package contained in the thin fabric. I laid down in bed and slowly jerked my dick through the underwear until I soaked it with a new load. I pulled the bikinis off and threw them back into the laundry and fell asleep.

I was awoken shortly before 10 by the text message notification on my phone. It was strange so I groggily reached over to investigate.

"I want you to hold my nuts... in your briefs :)" The message from Jim said.

"LOL. Happy to oblige. What did you have in mind?" I replied.

"I'm going hunting this weekend and thought briefs would be cool. Can I come pick up a couple pairs tomorrow morning before I head out?" Jim texted back.

"Sure, I'm an early riser so I'll be up. I pick out some good pairs for you." I said

"Cool. I'll have something for you too, per our agreement. See you tomorrow morning around 430." Jim responded

I got out of bed and went to my underwear drawer to pick something out. I decided I would give Jim a pair of bright orange low-rise sports briefs and a dark green string bikini - I thought my color combo was clever. I then threw on a pair of boxer briefs for myself and went to the bathroom to take my contacts out before returning to bed for the rest of the night. I set my alarm for 415 in anticipation of my morning visitor.

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