Gay Erotic Stories

Jake and I have been friends/roommates for the past 3 years. We are both 21 years old and share a good deal of interests. However, Jake is a lot more athletically inclined than I am. I wear briefs almost exclusively; sometimes bikinis sometimes boxer briefs. Jake is pretty much a boxer guy but wears briefs when he is playing sports or does other activities. I had always wished I could get him into briefs full time, but I didn’t know how. Until that day…

“Alright… what is it?” I responded while looking up from the paper I was typing for school.

“Well, I’m about to go play in my IM softball game and…w ell… I need to borrow some of your underwear. I like to wear tighty-whities when I play so that everything stays in place if you know what I mean. But I didn’t get a chance to do laundry yet so I’m all out of my own. ”

“Yeah, of course you can take anything you want… as long as you can fit into it.” I said

Jake and I are pretty much the same size, though I have some pretty low-cut briefs in my collection. I got up from my chair and opened my underwear drawer for him. I looked at him and he seemed to look a bit confused and overwhelmed at the choices he had before him. I probably have about 15 or so pairs of underwear in that drawer and a few other pairs elsewhere, but I could tell that he didn’t know what to pick.

“Wow, you have a lot of underwear in here! Umm… well I don’t really know what to pick. What would you suggest?”

I looked at what I had that was clean and I gave him a pair of orange Jockey Next-to-Nothing briefs. He felt the silky material and made a strange face, but I assured him that these would keep things in place without getting in the way – all the while trying to hide the boner in my pants. He took the briefs, said thanks, and went to his room to change. A few minutes later he left for his game.

I was so turned on at that moment. Jake was wearing my briefs! I knew that I wouldn’t be able to focus on my homework until I took care of myself. I went to Jake’s room, grabbed a pair of his boxers on the top of his laundry and used them to help fuel myself to a great climax. Afterwards I went back to homework and awaited Jake’s return to see how the underwear worked out for him.

About an hour later, Jake came back into our apartment and immediately came into my room. He was smiling and I assumed that he had just won the game.

“So I guess the game went well?” I asked

“Oh yeah! We beat the crap out of them… they were awful. Although, I really think that underwear you gave me helped me out a lot. I’ve never felt so free to move while running the bases! All my… stuff was held together and it felt like I wasn’t wearing any underwear at all!” He replied.

“Ha, yeah, that’s what they’re going for with that underwear. They’re actually some of my favorites.” I said.

“I can totally see why. So… if this isn’t too weird, would it be ok if I kept the on the rest of the night? I think they would be nice to sleep in. I can wash them when I do my laundry, which will probably be tomorrow.” Jake said.

“Yeah, that’s fine. I have some other pairs like that anyway so I won’t miss them too much. And if you ever need or want to try out some of my underwear don’t be afraid to ask.” I said.

“I won’t. Let me change and we can play some Halo before we go to bed.” Jake said.

“Sure, I’ll meet you there.”

Wow. He really liked my underwear… so much he doesn’t want to take them off. Jake also seemed to be pretty open to my offer to share underwear in the future. This was getting me pretty excited, but I tried to distract myself by playing some video games.

The next morning, Jake was off to class before I woke up. This was usual and this was also the time that I ventured to his laundry basket, checked out what he wore the day before, and woke myself up with some fun ‘activities’. I walked into his room to discover the orange briefs I had let him borrow on top of his clothes pile. I picked them up, gave them a sniff, and was turned on even more. I finished up and put the briefs back on his pile so he wouldn’t think anything was going on – just like I do with all his underwear.

A few days passed and Jake finally got around to doing his laundry. He came into my room and threw the briefs at me with a big smile on his face.

“So, does this work like the library? If I return one pair do I get to check out another?” Jake asked.

“Um, sure, if you want to! Do you need my help again on picking something out?” I replied.

“No thanks, as long as you don’t mind me just going through here to find something that suits me. I can’t get over how great those briefs were, I hope you have some other good pairs in here.”

“Yeah, go ahead and take whatever you like. You could probably take a couple of pairs that look interesting, as you can see I have plenty of underwear. “

“Clearly. I think I’ll take another pair of briefs and maybe some boxer briefs.”

He looked though my underwear for about 45 seconds until he made his selections. The boxer briefs were first with a pair of black Jockey 3D-Innovations boxer briefs. Jake looked some more and pulled out a light blue pair of the Jockey Next to Nothing briefs he had tried before. With a big smile he left my room thanking me again.

This was like one of my fantasies come true! I was finally sharing my love of underwear with my roommate and friend. I’ve never shared this with anyone else, nor have I had any friends who shared an appreciation for nice undies. I’m glad I could get Jake start thinking outside of his old boxers. Trust me, he needed to update his underwear because a lot of it had holes and was just plain worn out. I know, because I’ve pretty much tired on all his boxers while he was away. But yeah, it was definitely cool.

It was the weekend and time for laundry again. Jake returned the underwear that he had borrowed with similarly good reviews of the choices that he had made.

“You know, you could buy your own underwear so that you don’t have to worry about the loaner pairs I’ve given you.”

“Yeah, but I always feel silly buying underwear. My mom usually buys it for me. And plus, I think I want to get back into briefs but I would feel so stupid buying those and having some random cashier person think about the underwear I’m buying.”

“Well, I guess I could see how you feel that way, but who cares what underwear you buy. I’ve bought some strange underwear over the years and most of the time the cashier just throws it in the back without a second thought. It’s not like they’re trying to profile your personality based on if you wear boxers or briefs or whatever.”

“Hmm, I suppose your right. Well, I do have some extra money and time. Would you mind going shopping with me? You seem to have a handle on underwear and could probably tell me what to buy and what to avoid. I want briefs I think, but nothing too gay or anything like that. What do you mean by strange underwear?”

“Well, I could probably just show you. Come on, let’s go to the store!”

We hopped in my car and first had to decide where we wanted to go to shop. There are a few different places around for underwear selection. The obvious places included Wal-Mart and Target, but there was also JC Penny, Kohls, and TJ Maxx. I helped him to understand what stores carried what type of underwear and we talked about what he wanted to buy. Finally we decided we would go to Target first since it was the closest and see how things go from there.

We walked in the door and headed to the back to the men’s department. I could tell that we both felt a little silly; two college guys buying underwear together. Luckily there wasn’t anyone back there so I knew we could have a good talk about what to buy. Jake eyed up the normal Hanes and FTL brands of briefs they had available, but thought they were too plain. He checked out some of the other Hanes lines of underwear and liked the ones with ComfortSoft or whatever. He still wasn’t sure, so I said that we could just come back if he wanted.

The next stop was Wal-Mart. Again, we went to the men’s underwear section. There were a few other people around, but not looking at underwear. We checked out the Life brand that they had there, along with the offerings from Hanes. I was also in luck because I got to show him what I meant by strange underwear. I grabbed a box of Hanes string bikinis off the rack and walked over to Jake to show him.

“Ha ha, what the hell is that?!”

“These are the strange underwear I was talking about. Don’t knock these until you try them. They were actually surprisingly comfortable. Plus, they gave a lot more freedom than regular briefs.”

“What, you actually bought and wore those? You’re pretty brave. I don’t’ think I’m quite ready for something like that. What makes them different then regular briefs?”

I showed him the picture on the box and explained how they fit on you. I was feeling brave and reached down to trace my finger along where the waistband would sit. He was a little surprised but didn’t seem to care. I didn’t want to push my luck, so I just put them back on the rack. He finally settled on a pair of the Life Sculptured Pouch briefs. I had tried these in the past. They were alright and I thought he might like them. Jake said that he wasn’t done and wanted to go to TJ Maxx.

We headed over there. Jake was interested when I told him that they usually have some more designer underwear that might have more fun styles or fabric. The men’s underwear rack seemed to be recently restocked, so there was a lot to choose from. I left him to climb through the rack himself while I looked at some other stuff. Jake finally settled on a pair of white CK hip briefs and blue 2xist sport briefs. He paid and we headed home.

“I’m pretty excited to try this new underwear on. Do you think that’s weird?” Jake asked.

“No. I always do that when I buy new underwear. Although you’ll have to show them off for me” I said jokingly.

“Alright, I guess I can do that. Hold on a minute.” Jake said.

I was pretty shocked as Jake went into this room to change underwear. We’ve changed clothes in front of each other before, but didn’t go out of the way to do it. This was really strange coming from Jake, but I didn’t argue. I guess the underwear excitement had spread to him.

Jake came out in the first pair of underwear, the CK briefs. He looked so damn hot. He’s not in the best of shape, but it works for me. His package wasn’t that big (probably as big as mine) and his but looked so nice in the tight white fabric. I instantly got a boner in my pants and tried my best to hide it, but I don’t know how well I did.

“So, what do you think? I bet I look super hot, right?” Jake said jokingly.

“Umm… wow… yeah there sexy pants! You’re putting on quite the show.” I replied trying to make it sound as lighthearted as possible while hiding my excitement for this moment I had always wanted.

Jake smiled, winked at me and went back to his room to change into the next pair. By the time he has reached the end, I could see he was definitely getting a little hard in the beautiful package I had been looking at for the past few minutes.

“Hmm, I guess this whole underwear thing has got me more excited than I thought. I think I might have to do something about this.” Jake said while grabbing his package through the 2xist briefs.

“Yeah, I know what you mean, I’ve got the same problem.” As I motioned to the excitement in my Jockeys.

“Well, you’ve seen me in my sexy undies, I think it’s only fair for me to see you” Jake winked and smiled my way.

I totally agreed and dropped my jeans to reveal the activity in my black briefs. We both stood there staring at each other gently rubbing our packages. I didn’t really know what was going on until Jake broke the silence.

“Well, let’s just get this over with. I don’t mind jacking off together if you don’t. We could both lay on my bed since its bigger than yours or the couch… if that’s not too weird.”

“No, I don’t think so. As long as keep this between us.”

“Totally”

Jake and I went into his room and I checked out his cute butt while he was converting the futon from couch to bed mode. He laid down and motioned for me to join him. We were now lying next to each other in our tight briefs massaging the now full on erections that we had. I know that I was checking him out and I was pretty sure his eyes were on me.

“Damn, I’m ready to slip out of these briefs. But to tell the truth I think I’d like to jack off into them” Jake said.

“Yeah man. I love doing that too – nice and easy to clean up. I guess we would eventually have to see each other naked sometime.” I replied

We both slowly peeled off our briefs and held them in our right hands while continuing with our actions. We were now both definitely looking at each other and gave a little giggle when we found out that we both have pretty evenly sized 6” penises. Jake closed his eyes and went off into the fantasies in his own head. I continued to take in every sight that I could. We finally both finished at the same time shooting big loads into our briefs.

“Wow, that was really fun!” Jake said.

“Ah.. yeah it was. This stays between us right?” I asked.

“Definitely. Who would I tell and why? Plus, I think that we could probably do this again sometime If you want if it doesn’t make things weird between us.”

“Sure, sounds good. I’m glad I could help you out with your whole underwear situation.”

“Yes, thanks again! I love these new briefs and I don’t think I’ll ever look back”.

We got out of the bed, gave each other one more look over, and smiled. I went to my room to throw on a pair of Jockey briefs to replace the soiled ones. Jake reached for his new Life underwear and put that on. We spent the rest of the night just hanging out in our briefs. I hope that this is not the end of our fun together.