This is a request from @uclafratboy and is told from his point of view.
Even as I stood at the foot of the hotel bed, listening to a complete stranger in our shower as Ty lay in the bed half dressed and feeling his freshly bred ass, I couldn’t believe everything I’d seen in the last hour.
Ty and I had been buds our whole lives. We grew up in the same neighborhood, riding bikes and terrorizing neighbors as kids and playing ball and chasing pussy as we got older. He had grown into a pretty good athlete and we’d headed to separate colleges but stayed best friends. I knew when he’d gotten his first pubes, his first pussy and his first real ass kicking. thought I knew everything about Ty. But damn was I wrong.
Our families had been vacationing together for years and the summer after freshman year was no different. We all met up at a resort in Hawaii and Ty and I had our own room. Our parents all understood what college was like and gave us freedom to drink and hang out without them. This morning they had all gone whale watching and left us with no plans beyond hanging at the resort. But that’s where the trouble started.
Ty and I had been down on the beach throwing a football and fucking around in the waves for a while when he asked me if I had noticed the “Daddy” who was watching us. I wasn’t sure what he meant, but he discretely pointed out a built, kinda hairy dude who looked to be about 40 seated nearby with his wife and kids. I started paying a bit of attention and Ty was right. He was totally watching us. He was out of earshot and we were both accusing the other of giving off such strong gay vibes that even this old straight dude noticed.
Not that there wasn’t something worth noticing. I’d been working out hard this year and was looking good and cut. But Ty was looking even better. Something about his toned muscles and soft smooth skin had him looking like a complete stud. We laughed about the “Daddy” for a while and then headed to the gym. We needed to get out of the sun and a workout seemed like a great plan.
We were in the gym for about an hour and almost wrapping up when Daddy walked in. Ty suggested we stay a bit longer to see if he’d start watching us again. I thought he was crazy, but headed to the treadmill to get in some cardio while he finished with the weights. But he didn’t seem to be in any hurry. As I ran, I watched Ty and Daddy in the mirror. Daddy was working out hard. He obviously took good care of himself and his body was incredible this close up. And he was definitely checking Ty out, but it seemed like Ty was checking him out just as hard. When Ty adjusted a clearly hard cock in his shorts while staring right at Daddy in the mirror, I chubbed up a little myself. When Daddy looked back at him in the same mirror and adjusted his growing bulge, I began to wonder how well I really knew Ty and if he knew what he was getting himself into. I decided to try to short circuit the whole thing and tried to get Ty to leave before things got out of control. But it was too late.
As I walked toward Ty, so did Daddy. He got there first and I heard him say “you better be careful staring at Men, boy. Somebody might get the wrong idea about a boy with an ass as pretty as yours.” Ty turned deeply red and I could see his cock grow even from where I was standing. He all but whispered “who said they’d have the wrong idea?” Daddy just smiled asked “have your own room or you bunking with mommy and daddy?” Ty nodded in my direction, unable to look me in the eye, and Daddy laughed again, looking me dead in the eye and saying “I’m taking this piece to your room. You’re welcome to come too, but his ass is all mine.”
I expected Ty to object at that point, explain that it was all a misunderstanding, but he just walked out. Daddy followed and so did I. It took five minutes or more to walk to our room and my mind was racing. Was Ty really going to hook up with this dude? Sure, we’d been here for a week and we were both horny as hell, but Ty was straight. But when we got in the elevator, Daddy put his big meaty hand on Ty’s ass and Ty did not move away. He moaned. Could he really be a fag?
They went in the room first and the door wasn’t even closed before Daddy was all over Ty, kissing and groping him. And Ty was moaning like a little bitch. He sounded like the fat slutty girls who are so happy to be getting play from a stud like me that they can’t stop from moaning and soaking their panties. They were completely ignoring me, so I walked past them as Ty took off his shirt and I sat down to enjoy the show. And what a fucking show.
Daddy was kissing and rubbing all over Ty, paying special attention to his ass. And Ty was loving it, feeling Daddy’s powerful chest and arms. I knew there was no going back when Daddy took Ty’s hand and put it on his growing dick. Ty moaned again and actually said “it’s so big, daddy.” The response? “If you think it feels big now, wait until it’s inside you, son.” I could not believe my ears. Was this Daddy going to fuck my best friend’s ass?
As he pushed Ty to his knees and pressed Ty’s face into his crotch, I reached full mast myself. When Daddy dropped his shorts to reveal a fat 8" uncut dick and a thick black bush, I let my own dick out of its confines and started stroking. I’d seen my roommate fuck a couple of girls this year, but I’d never seen a dude submit like this. I was rock hard and amazed at how much I was loving what I was seeing.
Ty proved to be a pretty pathetic cocksucker and Daddy got sick of hearing him gag and struggle pretty quickly. He pulled Ty up to his feet, turned him around, and pulled his shorts below his ass. He pushed Ty forward onto the bed on all fours and dove straight into his ass with his tongue. Ty’s moans were getting ridiculous and it was clear he was loving having his ass eaten like a cunt. And Daddy seemed to be loving it to. Soon he was working a finger in along with his tongue and it looked like Ty was backing his ass up trying to get Daddy’s finger deeper and deeper. That was all the hint Daddy needed as he stood up and lined his fat cock up with Ty’s hole. I could see Ty’s tight rosebud dripping with Daddys spit and his own juices as he started pushing his rod inside my best friend. In no time, Daddy was balls deep, then fucking Ty right in front of me while Ty was still wearing his damn shoes. I was as hard as I’d ever been and dripping precum all over as I stroked.
Ty was making so much noise from being fucked by this Man that Daddy pushed his face into the bed and covered his head with a pillow. But you could still hear him react to every thrust and it was soon clear from his reactions and how hard he was fucking back into Daddy’s dick that Ty was going to cum. From having a dick in his ass. And without touching his own cock. I didn’t know what to think anymore.
Daddy obviously knew these signs as well and grabbed Ty’s hips to control his bitch. Daddy held him just how he wanted and started slapping his ass furiously as he long dicked him, telling him he was about to get loaded. Even with the pillow, Ty’s moan left no doubt that he was cumming and Daddy soon followed suit with a roar. I could actually see his hairy low hanging balls contract as he unloaded inside my best friend’s spasming asshole. I shot my load so hard that it flew over my head and hit the hotel curtains. I’d never been so turned on.
Daddy pulled out and I could see the gape in Ty’s asshole, proving his ass was now a cunt to be used by Men. As Daddy headed to the shower, he looked at me and said “too bad you wasted your load. He could some practice sucking cock, but he is a natural born bottom.”
As Daddy showered and Ty lay there fingering his freshly fucked cunt, i thought about Daddy’s words. Just the thought of training my best friend to be my cocksucker had my dick chubbing up again already. This vacation just got so much better.
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