Date: Thu, 1 Sep 2022 15:28:32 -0600 From: Oliver Day Subject: That Boy at the Pool Chapter 5 - Speedos Author's Note: This is a story about two boyfriends in high school who meet a new friend while swimming laps at the gym. As time goes on, they get to know the boy better and things progress. Looking forward to hearing what everyone thinks at oliver.day.149@gmail.com Chapter 5 - Speedos The next time we went swimming, we were all a bit less horny, so we could have a more normal conversation in the sauna. I decided to bring up the topic of Tim's swim trunks. "So Tim... you've been doing great, and I think you have a good chance of being able to make the swim team next year, but one thing still is that those trunks you wear are not going to be allowed." I said. ///"Oh... I guess you are right... So are you saying I need to start wearing a speedo like you guys?" "A speedo is one option... there is a type called jammers... they are tight like a speedo, but cover your legs too... but the important thing is just having something tight... those trunks create drag, and slow you down... so I think it's probably good for you to get used to wearing something like that... both so you are comfortable being in it in front of people, and getting used to how it feels different while swimming." ///"That makes sense... I guess I never thought about it like that... I don't really know if I mind a speedo or jammers, since legs aren't the part I'm concerned about... it's more the tightness... I'm still worried about getting... hard... in front of people..." "Well," started Sean. "I'm pretty sure both Ant and I have some older speedos that don't fit us anymore that you could have to try. I think most of them are black, which is better at hiding any potential boners, and you could get used to wearing them around us if you like... would you like us to bring them next time?" ///"You'd really do that for me?" Tim asked. You guys don't need to give me anything..." "It's not a problem Tim," I said. "We have old ones that don't fit us anymore, so they are just going to sit around or get thrown out..." ///"Well... fuck it okay... I guess I can try it next time... thanks guys..." Tim said. "No problem!" Sean and I both answered. So the next time we went swimming, Sean and I each brought a couple of our old suits to give to Tim. He tried one of them on once we got to the locker room, and seemed to enjoy how it felt. He looked really nice in it too. He had a slight boner after getting into it, so we let him hang around for a bit before we left to go swimming to let it go down a bit. I was tempted to tease him and tell him he looked sexy in the speedo, but didn't want to make his boner worse at the time, so I resisted. After only a few laps, Tim seemed to get why it was better than his old trunks. He could feel how much easier he could move through the water, and was noticeably faster at doing his laps. He continued to wear the speedos every time we would swim and seemed to get a lot more comfortable wearing such a skimpy swimsuit. He was tested a few weeks later. His mom stopped by during one of our swim sessions to see how much he had improved. Tim knew she was going to be there, and we told him he could switch back to his trunks if he wasn't comfortable being seen in the speedo by his mom, but since he knew she would need to see him wearing it once he joined the team, he decided to go for it. I could tell his mom was surprised at what he was wearing when she walked in, but she seemed fine with it. I mean, Sean and I had always been wearing one, so I guess it wasn't too surprising. His mom was so happy to see his improvement since she had seen him swim last, and gave him and us all hugs and thanked us a ton for working with him. Once we were done swimming for the night, we said goodbye to her and headed to the sauna to decompress. While we were there, Tim brought up the topic of speedos. He said that he quickly understood the practical benefit for swimming, but he also started to like how the tightness felt in general, and was sad that he had to go back to boxers after he was done swimming. "Is there a reason that you still wear boxers?" I asked Tim. ///"Well yeah... I started wearing them a few years ago when I started having to change for PE... nobody wore briefs anymore, so I switched too... and now it's all I have that fits." "Well you could switch back to briefs or something tight like boxer briefs?" Sean offered. ///"Yeah... I'd like that... but I still am trying to look str-" Tim cut himself off before he could finish the sentence, but Sean and I both caught what he almost said." "Well... if you like the tightness, why not get at least a few pairs of briefs that you can wear when you don't need to worry about changing in front of people, and you can go from there?" I suggested. "That's what I did. I never really started wearing boxers for PE, I wore briefs the whole time because I liked how they felt, I just had a few pairs of boxers to wear on top on changing days... if you want, Sean and I can go to the store with you before swimming next time and show you some that we think are the most comfortable... if you want." ///"You'd really do that with me?" he asked. "Of course," we replied. So the next time, we picked him up a little earlier than normal, so we could head to the store before it closed. Tim got a little red faced when we got to the underwear aisle, which Sean and I both understood. There were a lot of hot guys wearing very little on all the packaging. We showed Tim a few different brands and fits that we both liked, and he selected a few options. We were both surprised when all his choices were white briefs, given his fear the other day of `not looking straight," and both of us who usually wore colored briefs, but we were happy to support him in his choice. I was looking forward to seeing him wearing those tighty whities after swimming. Once he selected the ones he wanted, Sean and I grabbed them and took them to the checkout. ///"Wait, what? I was going to buy them..." he said. "I know," Sean replied. "This is our present to you for all the progress you've made in the last few months!" ///"Oh really? Well thanks... you really didn't have to do that..." he said. "We know, but we wanted to! You just better let us see you wearing them after swimming today... I bet you will look great!" I whispered. Tim blushed, but agreed. After we checked out, he pulled us each into a hug to thank us, and he gave us each a small kiss on the cheek, which we both reciprocated. We left the store and headed to the gym and did our swimming routines. After that, we sat in the sauna for a bit and then showered. As we walked back to get dressed, I looked over at Tim and was happy at how much progress he had made, not just with swimming, but just being comfortable in his body. When we started, he was skipping showers, and changing in the bathroom stalls, now he was completely naked walking from the showers back to his locker. He didn't even bother to use his towel, he was carrying it in his hand! Once we got back to the lockers, he started excitedly opening one of the packages of tighty whities that he got earlier. He put one of the pairs on and seemed super happy. We had him show them off to us and pose in a few different angles, which he was more than happy to do, and they looked very nice on him. I decided he could probably handle a bit more teasing, especially after he kind of slipped the other day and so now Sean and I were almost certain that he was gay. "Damn Tim, those look fuckin' sexy on you!" I teased. "Yeah Tim! They show off your ass and dick super well!" Sean teased, which made Tim's face go red and cock start to puff up. "Anyone who sees you in those is going to go crazy!" ///"Thanks guys... I really appreciate it," Tim said as he fell into another hug with Sean before doing the same to me. He kissed us on the cheek again, which we reciprocated again, but this time we were able to see his dick respond inside his briefs as we kissed him, and I'm sure that Tim noticed us both start to chub up inside our own briefs as we had watched him show off for us. We got dressed and drove him home. After that little show, Sean pulled off of the road after we dropped him off to have a bit of fun before he dropped me off, since neither of us could have gone to bed without cumming after seeing Tim dance around for us in his tighty whities. In the spirit of things, we didn't take our briefs off, and instead made out and rubbed our dicks together until our briefs were soiled.