All parties are 18+.
I met Kyle freshman year in a Humanities 101 class. He walked in 5 minutes late to the class and sat next to me in one of the last open seats available. It was obvious he'd taken a nap before class and overslept; he had bed head and he was in sweats and a muscle tee, obviously no underwear on underneath as I could easily make out his dick swinging back and forth before he sat down. He smiled at me, cracked some lame joke I forgot immediately, introduced himself and that was that, apparently we were friends.
After the end of that first class we exchanged cell numbers, I figured a dopey straight dude as a friend we be fun at least and he seemed the type that overflows with golden retriever energy. Over the next couple of years, Kyle and I became fast friends. He had no issue with me being openly gay, making a joke about being my wingman when I came out to him and never once changing the way he treated me.
Kyle and I would work out two to three times a week at the university gym, he'd go almost daily but my schedule was a little tighter than his so I couldn't always make it. It never failed, after we finished working out that he'd strip down in the locker room almost immediately, shamelessly strutting his stuff without a care in the world who saw. At first I'd avert my gaze, but it got to the point where curiosity won out and I looked. Kyle was hung, even soft. His uncut dick must have hung six or so inches soft and was girthy even completely limp and hung over two huge, low hanging balls.
Kyle's size became well known in the dorms within a couple of weeks, his overall lack of care about clothing carried over to trips to and from the showers and most people quickly got a full sight of his summer sausage. All of this to say once word got around, Kyle was extremely popular with the girls. The man had a constant stream of women coming to his dorm room and he always seemed to treat them well. He didn't date long with anyone, moving on quickly, but he also never strung anyone along. Kyle all in all was an upstanding dude and just about everyone liked him.
Our Junior year in college a group of eight of us decided to go on a big trip for Spring Break, settling on Cancun pretty quickly. The weeks leading up to it were filled with group planning, laying out a general budget, places to stay, traveling logistics, etc. Kyle laid claim to me as a roommate fairly early, to no one's surprise. Out of the entire group we definitely were the closest, spending most of our free time together when we weren't otherwise engaged.
The flight down was pretty nondescript, all eight of us got on the plane and mostly passed out for the ride. Once we landed we got to our hotel and setup shop, four double rooms each with a queen-sized bed.
Walking in, Kyle threw his suitcase in the corner of the room and immediately made his way to the bathroom to take a piss. "Dude I can't wait to go down to the beach and start checking out women! There's got to be so many smoking hot ladies out there just waiting to meet me!" Leaving the door open was nothing new for him, boundaries weren't much of a thing for Kyle and I was used to talking with him through various activities.
"Yeah, what you going to do with them if you do meet someone? We've got the one bed and I'm not down to join in."
"I dunno man, we'll figure it out once we get to it. I'm just horny as hell and want to see what I can pull out here. It's been a while since I last got laid." Walking out of the bathroom, Kyle started shucking his clothes, stripping naked as he walked over to his suitcase and started rooting around. "I think I'm going to go down to the pool at least and check it out, you wanna come with?"
"Yeah, let's see what we've got out there, water sounds nice." I quickly stripped as well and hunted down my swim trunks. I wasn't as ripped as Kyle was after all the work he put in at the gym but I did pretty well for myself. I was just short of a cut six pack and was damn proud of it and kept what hair that grew on my chest and junk trimmed short. While I didn't pack what Kyle had, I was doing pretty good in the dick department as well, I hung maybe three to four inches soft and got up to seven when fully hard. Hadn't had any complaints from the few guys I had hooked up with.
"Come on gay boy, let's get going!" Kyle was already out the door by the time I tied my trunks and got some flip flops and the room key. We head down to the hotel pool and were met with an expanse of mostly naked people, most around our own age and all looking for fun. The next few hours were filled with fruity drinks, stupid shenanigans and eventually a run for food at some touristy burger restaurant with the other dudes.
Around 9 that evening I was mostly drunk, tired from the travel and sun and ready to chill for the evening and pass out. Kyle had given his best to see what he could pull on the first day here and struck out, his brand of charisma not seeming to match up with any of the girls he talked with. Our group all decided to call it for the evening and headed back to our perspective rooms to chill with an agreement to meet up for breakfast the next day.
Once in the room Kyle immediately flung himself on the bed and started channel surfing. Wanting to get the chlorine off me, I ducked into the bathroom and jumped in the shower for a quick rinse down. I didn't spend long in the shower, just enough to quickly get clean and dry off. Dropping the towel to the bathroom floor, I walked out into the bedroom naked and came out to Kyle watching some cheap softcore porn with his hand down his shorts.
"Dude, what's going on?" I laughed, shocked at what I had walked into. While Kyle had always been fairly open with nudity and his body, we had never done anything remotely sexual around each other. I'd only ever seen his limp dick, never him when aroused even the few times I had tried to sneak a peak of his morning wood hadn't worked out.
"Sorry dude, I'm freaking horny as hell after all that today! It's been so long since I've got any and I've just been super keyed up." He only briefly glanced over at me when replying but never stopped what was going on under his shorts, a large bulge extending the front out obscenely.
"I thought you and Kaley were going out pretty frequently."
"I mean we were but she never wanted to do anything and then she got busy with class and that ended. Haven't had much luck after that." Finally he pulled his hand out of his trunks, still leaving a massive tent for me to see. Despite my best efforts, blood rushed to my cock and I could feel it lengthening at the sight of my friend's covered hardon.
Kyle glanced over at me again, doing a sweep of my naked self, seeming to pause on my crotch which was something I'd never observed him doing before.
"I actually wanted to ask you about something but you've gotta promise not to say anything to anyone." His tone was serious and somewhat hesitant, something I wasn't used to coming from Kyle.
"Yeah dude, what's up," I started moving over to my suitcase to grab a pair of boxers, trying to cover up my hardening dick anyway I could without drawing attention that I was getting turned on by the scene in front of me.
"Well you remember how I was seeing Erin at beginning of the semester? She was into some kinkier shit and got me to try some stuff out. And I liked it a lot but then she turned out to be a bit too out there and I ended it." Again his voice was quieter, hesitant to bring it up.
"Nothing wrong with trying out some new stuff. What kind of kinky stuff was she into?" Kyle and I rarely talked about sex stuff but it came up occasionally. Even though he was extremely gregarious, Kyle kept a lot to himself until it built up and then he'd turn to me once he needed a sounding board or someone to vent to.
"She really liked pegging and turns out I really do too. But how do you bring that up with someone without weirding them out? And since I broke it off with her it's all I can think about." He seemed distraught as he confessed, like he had tried so many things and couldn't find a solution to his problem.
"I mean if you can't find a girl that's into it, just get a dildo or something and do it to yourself. There's plenty of stuff out there, you should be able to find something that works for you." I was a bit thrown off by the topic honestly, Kyle was the last person I would think to be into ass play, while he had never shown himself to be homophobic in the least, he seemed outwardly to be more conservative in his sexual desires.
"Dude I've bought three of the damn things and it just doesn't quite work for me. I keep wanting something more and it's annoying as hell." Kyle took a deep breath, seeming to gather himself. "I've been thinking about it a lot lately and I want to try something."
"Like what dude?"
"Would you help me out?" Kyle's question was quiet and a little pleading. "It'd be a bro thing, something between us but I really want to try it and you're the only person I could trust with something like this."
"Dude, what, you're asking me to do what? Fuck you?" I was completely taken off guard by this. Kyle was straight from everything I'd experienced in the last few years and this was messing with my head. "This is the liquor talking, you're drunk."
"Nope, I didn't actually drink that much. I'm just a bit buzzed. Please dude, help me out? Jerking off isn't really doing it since I came with Erin's toy in me and now I keep thinking about the real thing being out there and it's all I can think about."
Having my best friend in front of me, obviously hard and pleading with me to fuck him was doing crazy things to my head. I would have never bet in a million years that he'd ask anything close to this of me. The more I thought about it, the hornier I got at the idea, my boxers covered cock quickly rising to attention and causing a large tent.
Looking over at my friend on the bed, I allowed myself to look at actually look at him instead of avoiding horny thoughts like I had forced myself to all this time. Kyle was maybe 5'10" with the epitome of a jock frame, with large pecs and a solid six pack that he so loved to show off at the barest excuse. He kept his chestnut brown hair long enough to occasionally pull back into a small manbun that everyone hated but he thought was sexy as hell. With his bright green eyes and killer smile, it was no wonder he was able to keep his bed occupied most nights. Now those eyes were turned on me with an almost desperate, pleading cast to them.
