Deciding to not join the frat but still dating one of its members was the best of both worlds. I say dating because it wasn’t official. We had never been on an actual date. It was more like “friends with benefits” but I knew he wasn’t dating anyone else. He bragged about the guys checking him out and a few anonymous hookups. I had seen Ted a few times and didn’t want to stop any time soon. The difference being is that with Ted there wasn’t an emotional connection but with Brad there was a connection.
He’d send me a late night text before bed and we’d end up in these conversations. He’d send me a text in the morning just saying, thinking of you, and sometimes throughout the day he’d send me some kind of joke or invitation to meet up later. And everyone in his frat knew about me. I’d walk past all of them with a head nod or a, “what up” and they just nodded or said hi.
But that Halloween our relationship changed. It got deeper. It all started fairly innocuously a few days before the fraternity’s party while we were playing video games in the main room with one of the other members and a pledge. The pledge was in his tighty whities of course and the frat bro was chilling shirtless. I had a near constant erection in my jeans that I did my best to hide. Brad was next to me and kept teasing me and trying to distract me because I was in the lead on the racing game.
“We should play something you’re not so good at,” he said.
“I can take you on all the games,” I replied.
“Oh, that sounds like a challenge,” the frat bro said.
“Definitely a challenge,” the pledge added.
“Shut up,” the bro said with a smack to the back of the pledge’s head.
“I’d be winning if it were something I am good at. I don’t like these racing games. If it were a first person shooter I’d kick your ass.”
Normally I would have let something like this go. I would have just not said anything. Maybe he was talking out of his ass and maybe he actually could beat me, it didn’t matter, not to my ego, but there was something about sitting there with the two other guys so I decided to egg him on just a little.
“I’ll beat you on any game, any system, hell even a board game,” I said.
“There’s no way you could take me in Desert GI. I’m the best at that game. I have the top score in the frat.”
Yes, they sat around and played video games that much, usually while drinking and/or smoking weed, and I knew he had logged many hours. But so did I. Desert GI was like so many of those types of games: a map, a selection of weapons, and lots of running around trying to shoot the other person.
“Oh, I think I could take you,” I said.
“No way,” Brad said, “I’d kick your butt.”
He was in last place in the game we were playing and used his left hand to try and tickle me. At first it didn’t work but when he got under my arm pit I felt the usual tingle and started to laugh so he dropped the controller and grabbed at me with both hands. One hand under each pit he tickled until I was on my side and had fallen from first to last, laughing so hard I was nearly out of breath and seriously trying to stop myself from pissing my pants.
“Okay, I give, I give,” he forced from the my throat.
“I didn’t hear you,” he said as he kept at me.
“Please, I give,” I said.
He pulled me up into him and kissed me on the forehead. I felt his muscled arms around me and my dick was hard again making me forget for a moment about having to piss. He held me until we looked at each other and agreed that the fun was over. I looked around at the rest of the guys who didn’t seem to notice, at least not consciously, neither of them were looking at us, but the pledge in his briefs did have a slight erection. Though of course a horny eighteen year old doesn’t need much of a reason for one of those. Brad picked up his controller and started to drive again. He passed me easily and I started after him.
When we finished my dick had shriveled again and I remembered I needed to piss so I got up from the couch. I looked to Brad who had a smirk on his face from having overpowered me and tickled me until I gave up. I wanted to one up him at something, maybe even embarrass him a little.
“Okay, when I get back we play Desert GI, just the two of us,” I said, “and we see who’s the best.”
“Oh yeah?” he replied.
“That sounds like a challenge. You two should make a bet.”
“Yeah, the loser should have to spend the rest of the day in the house in his tighty whities,” the pledge said.
I could see why he would want someone else, especially Brad, to join in his embarrassment of having to walk around the frat his underwear but I shook off the idea. I wanted something else, something more. And yet as I tried to think of something I started to worry he might just beat me.
“Winner gets to pick out the loser’s Halloween costume for the party,” Brad said.
“That sounds fun,” the bro said.
I started to sweat. Was I any good? Was I better? The idea of picking out his costume brought a smirk to my face and Brad noticed. He smiled back for a moment before getting a really serious look as if he was thinking about how he’d dress me. Would it be my little swim briefs he liked so much? I could walk around in that all night, hell maybe even get some action out of it.
“Okay,” I said, “when I get back we’ll play and I’ll take your bet.”
I walked out of the room feeling the pressure of the situation and headed to the downstairs bathroom where I found a different pledge on his hands and knees in a pair of white briefs scrubbing the floor. I saw his bubble butt, his narrow waist and I got another instant erection. I love dating a frat bro, I thought, before he turned and looked up to me as if it was no big deal. I told him I needed the room and he quickly scampered out. I closed and locked it before looking at myself in the mirror.
Come Halloween night I could be walking around a party full of people in something ridiculous that Brad would pick out. It would be something humiliating I was sure, but all in good fun. I had no problem if it were something like I wore swimming or even less, I’d go nude. I wasn’t embarrassed about my body, not here, not in college. I moved to the toilet, waited until my erection softened and pissed before moving back to the sink and looking at myself in the mirror. I washed my hands, splashed cold water on my face. Brad would think up something good but I had to think up something better, I thought, and I started to think through all the costumes I had seen but nothing came to mind right away. I dried my hands, exited the bathroom and found the pledge waiting there. I saw his briefs and a thought occurred to me. Brad walking around in his tighty whities, that would be fun for me and all the pledges but I knew it wouldn’t be embarrassing for him. But the white shape, I thought of something else, a diaper and I had my idea, Brad dressed as a baby. I smiled at the pledge who went back to work in the bathroom and went back to the living room where a few other frat brothers and pledges had joined us. I spotted Kevin, briefs instead of boxers was a change for him but he was living with it, and nodded to him. He scratched at himself casually and nodded back.
“Okay, we have a little match here,” the frat bro who had been playing with us said, “Peter and Brad in a little grudge match, winner picks the loser’s Halloween costume for the party. Do either of you have any ideas?”
“I’m thinking Peter has to do full drag,” Brad said, “makeup, wig, and I get to pick out the dress. Maybe it will be a gown and maybe it will be a mini skirt, I don’t know.”
Everyone laughed a little. I smirked at Brad and tried my best to not feel intimidated. I hadn’t thought he’d make me wear a dress. I was thinking something with very little clothing, maybe no clothing, but a dress, I could pull off a dress, though a miniskirt was a little risky.
“With my thighs?” I retorted, “that might be a little embarrassing-” everyone laughed, “-but worse than that, my costume for you is dressing like a baby-” they kept laughing, “-in a diaper, and a onesie, with a pacifier-” they got louder and I could see Brad was blushing, “-and you even have to carry around a stuffed teddy bear.”
Some of the guys were laughing so hard they were bent in half. I could tell I caught the pledges imagination and they all chuckled. Brad was notorious, infamous really, for the way he treated the pledges. He especially liked to use the paddle and I had heard it was his idea for the guys to go around in their underwear, of course both had been an age old tradition everyone knew about from movies and such so maybe it was just a rumor, but I had seen him with the pledges myself and knew he had high standards, at least for them, so one night in a diaper, who wouldn’t want to see that?
“Let’s do this,” he said.
“Okay, but we don’t sit next to each other, so no cheating,” I said.
The pledge who had been playing with us changed the games and handed each of us a controller. Brad went back to the couch and I sat on a recliner nearby. He was quick to go through the menus.
“Wait, how many games?” the bro asked.
We looked around at the guys watching us then to each other.
“Best of three?” I asked.
“Best of five,” he said.
“Okay,” I said.
“Okay,” he replied.
And like that the game started. It took me some time to get used to the controller and remember all of the functions in the games. I lost the first round. But on the second I got lucky and killed him with a head shot that even I would admit wasn’t accurate as per the graphics, but hey a win is a win and he wouldn’t give that up. Round three was intense, and sweaty, like I was actually sweating, but I won. If it were best of three I would have won already but as we entered round four I was still glad we were still going because I knew I could have lost too, especially the second round so this was proving something. I looked to Brad and could tell that he was clenching his jaw. I planted a claymore mine and led him around in a circle until he got caught in the laser detector, boom he was dead and I won. I won the game and I could make him dress like a baby. He threw the controller and stormed off amongst the cheers of his frat bros and pledges who applauded my skill. I thanked them and pushed my way out of the room after him. He stomped to his room and slammed the door shut. I knocked.
“Leave me alone,” he said.
“Please, I’m sorry, we don’t have to go through with it,” I said.
The words just came out. It was my nature. I didn’t really want to humiliate him, not if he was so embarrassed. There is something fun about mischief, a prank, but if both are into it. Brad was clearly upset. I knocked again.
“Please,” he said from the other side of the door.
“It’s just me, no rubbing it in, I just want to talk,” I said.
He opened the door and let me into his room but closed it quickly and locked it. I looked up into his eyes and could tell he’d been crying, probably out of anger, I did that sometimes. He sat on his bed and I moved to his desk chair.
“We don’t have to do it,” I said.
“No, of course we have to do it. Everyone knows about it.”
“They’re not going to force you to do it,” I said. “I can talk to them.”
“No, please don’t say anything,” he said.
“Look it was my bet, I pick the costume, I could do something different,” I said.
“No, just, ugh, it’s not dressing like a baby that’s bothering me. I think I’d look good walking around in a diaper.”
“What is it then?”
“It’s the stupid game,” he said, “I mean I rarely lose and that second round there’s no way you shot me but it’s not like I would have given up the point so I can’t hold it against you. It’s just I thought I was going to win so much. I was playing so intensely and it just, just broke on me. I had this feeling about what you were doing that last round and I had seen you plant the mine but I just kept chasing you and bam I lost.”
“Oh,” I replied.
We sat there quietly looking at our feet and the floor, playing with our fingers for a long time until he finally spoke up.
“Do you want to fuck?” he asked.
“Do you mean like just, you know, jerk off and fuck around or like...”
“I want you to fuck me,” he said.
I got to my feet and pulled him up, kissed him on the lips, full and penetrative until he gave to my tongue as I pulled off his belt. I dropped it on the floor and undid his pants, pushed them down with his boxers. He grabbed at my dick through my jeans and I knew what he wanted. He wanted my dick. I pushed him away a little, pulled off his shirt. I pushed a little and he fell back onto the bed. I pulled off his shoes, his jeans, and his boxers until he was in his socks. I stood before him with a grin on my face as I stripped out of my own clothes. I got lube and condoms from his nightstand.
Buck naked I pushed his knees up as I got onto the bed. His hole right there for the taking, my dick grazed it before settling over his. I squeezed them together for a moment before putting the condom over my own. I squirted lube on my fingers, on my dick, and onto his hole. I looked down over his muscled body, his abs, his chest, his shoulders, and up into his eyes.
“I want to hear you say it.”
“Fuck me,” he replied.
I played with his hole for just a moment before sticking my dick inside of him. He had learned to relax since the first time, maybe he was using the dildo I had given him, I didn’t ask. But he gave to me and I was all the way to my balls in one thrust. I looked up to his eyes, ran my fingers up his muscled body to his neck and then to his lips that had become red and puffy. I played with his lips as I began to move slowly in his ass. I felt him relax under me and give into my dick. His own dick lay dripping against his abs. He played with it a little and the stiffer it got the tighter his hole squeezed my dick. I could feel it grab at me with his heart beat. I ran my fingers over him, over his chest. I grabbed at his pectoral muscles and twisted his nipples.
There was the sound of the creak of the bed and slapping of my balls, our breathing, sweat covered our bodies. This wasn’t a quickie. I was fucking him good and hard. I didn’t care who heard. He didn’t care. It was just us, our hot, sweaty bodies rubbing against each other, our fingers grabbed at each other. He wanted me deeper and harder, deeper and harder. I pulled out, rolled him on his side and went back at him. He grunted and grabbed a pillow, bit into it. I felt sweat run down my back, between my own cheeks, all the way to my balls. I rolled him around and we twisted the sheets with us until he was on top of me. He had the position of power but he desperately wanted only one thing from me. He rode me like I was a bull until I felt ready to burst and I rolled him down onto his chest and pushed my dick between his cheeks back into his hot, slick hole. I felt the climax. My feet curled as I lay on top of him, inside him, between his cheeks, he breathed deep. It felt like every part of me only lived in one part, my red hot dick and it was all shooting out of me. I reached down to my dick and held it as I pulled out and rolled to his side as he rolled onto his back. I hadn’t noticed but I could see his ejaculate all over his dick, in his pubic hair, and on his stomach. He must have ejaculated near the same time I did and hands free too, that was a first for me. We looked to each other and laughed, kissed, and touched at our bodies until we caught our breath.
“Are we good?” I asked.
“Better than good, and who knows it might be fun to wear a diaper,” he said.
“And maybe if you’re naughty I’ll have to give you a spanking,” I said.
“That would be fun,” he replied.
We looked up to the ceiling, felt the sweat cooling on our bodies, and were satisfied. I closed my eyes and tried to memorize that moment. Whenever someone would ask me about my happy place this would be it, well my secret happy place, the one I really think about. He reached down to my hand, his fingers interlaced with mine. Maybe we are boyfriends, I thought before falling asleep.
