Dress him like a baby for Halloween? He had made the bet and was willing to do it. He’d dress me however he’d like if he’d won. I kept thinking this over and over as I scrolled through the options online. Going to a store, there’s no way I could do that. I still sweat and my voice cracks if I have to speak while buying condoms so I decided to get everything online and with a rush delivery. And after I ordered everything I sent him a text saying what I had done. He didn’t respond right away.
[How much shit am I in?]
[A diaper can hold most of it.]
[Are we really going through with this?]
[It’s up to you. Do you still want to do it?]
[It’ll be good for a laugh.]
The thought had me smiling the rest of the day and things fell back to normal without really thinking about it. But we barely saw each other in the intervening days as we both were busy with class, homework, and our part-time jobs. When I got the notification in my mailbox that I had a package for pick-up it brought back that deviant smile and I made a special point of skipping out of the last ten minutes of work to go pick it up.
When I got back to my dorm room I wasn’t surprised to find Kevin in his boxers at his desk working on an essay. He barely acknowledged me until I dropped the box on my bed and then he looked over with a quizzical look.
“What the hell is that?” he asked.
“It’s Brad’s Halloween Party costume,” I replied.
He got up and moved to where I stood looking down at the box. I pulled the tape off, opened the top of it, and we both looked inside. He saw my vampire costume on top and shrugged his shoulders.
“So he chickened out?”
“No, that’s mine,” I answered.
I set my costume aside and we looked inside to see Brad’s costume. Kevin broke into laughter that got louder and more ridiculous as I pulled out each item.
“I can’t wait to see this,” he said.
“Me too,” I replied.
Before the party started I brought a bag full of everything I had bought for Brad to his bedroom. He let me in with a sigh and a roll of his eyes. I moved to his bed and dumped out the contents: diapers, a onesie big enough for him, a pacifier, booties, a bottle, a bib, a hat, all of the things for a costume. He chuckled nervously at it all but then he saw the extra things, baby oil and baby powder.
“What the hell is all of this?” he asked as he picked up the bottle of oil and the powder.
“It’s for your costume, so it’s authentic,” I replied.
“I don’t think we have to go this far,” he replied.
“You don’t want to get a rash,” I replied.
“I’ve either got balls of steel or I’ve got no willpower, but seeing all this stuff makes me think of how the pledges should have to dress sometime, maybe next year for Hell Week.”
“Strip down and get on the bed,” I ordered.
“Okay, let’s do this.”
He quickly did as told. He pulled off his clothes and tossed them into his hamper until he was down to his underwear. I gave him a look and he dropped those too. I had seen him naked plenty of times but it never got old. I motioned to the bed. He pushed everything aside and laid on his back.
“Are you ready?” I asked.
“I don’t think you have to do this,” he whispered.
“It’ll be more fun, for me, and maybe you, just try, besides it’ll be easier if I help.”
After applying the powder and the oil, I noticed he had an erection, a hard erection that wouldn’t go away. So I teased it until he shot all over himself, then I cleaned the mess up with a wipe and set about completing the diaper process. He laughed and blushed through the entire process, especially when I made him hold up his feet into the air so I could put the diaper under him.
When his costume was complete I pulled him to his feet and he looked into the mirror. He sighed and was about to say something but I interrupted him with a motion of my hand, then quickly picked up the pacifier and put it between his lips. He shook his head and shrugged it off so I took him by the hand and led him out of his room to the party that had already begun downstairs. We were greeted by cheers and laughter as we descended the steps.
His frat bros were merciless at first and everyone had to take a picture with him. I wanted to stop it. I wanted to run over and pull him out of it. But as it went on, as the guys seemed to notice how uncomfortable he looked they got softer with him and it became this kind of mutual joke. It also helped that some of the other guys had their own silly costumes, costumes that gave them any excuse to be half naked and show off their muscles. There were two cavemen: one in a loincloth and the other in a furry toga kind of thing. One was dressed in a singlet with no jock, just his dick there as a lump, and another was dressed as a sumo wrestler, complete with bare ass cheeks.
Nearly all of the women complimented him on his costume and by the time he made his way over to me he had filled the bottle with beer and had several shots of vodka. We moved to a corner of the room where he laughed at himself and gave me another drink. I downed it and asked him if he had any regrets.
“I did at first but it’s a costume party and everyone likes it. I’m the most popular person here,” he said.
I looked around at everyone else. I spotted Kevin across the room dressed in g-string and black bow tie with a tray of drinks. He looked glum until he saw me and pointed to Brad and gave me a thumbs up. Well, I guess everyone does something silly on Halloween, I thought. And that’s when Brad caught me off guard and pulled me into a kiss. For a moment he had the advantage until I started to kiss back. He was disarmed by my tongue as I reached around to grab his butt. Instead of the usual firm muscle I felt and heard the crinkle of the diaper and we both pulled away and laughed.
“I’m glad you’re here,” he said.
“Me too,” I replied.
Aside from our brief kiss, we danced, and we drank. And he introduced me to all of the frat brothers and the pledges. The pledges themselves got in on taking pictures with him and the more Brad drank the less he wore. Parts of his costume came off in different areas of the house, some random girl wanted to try his pacifier and we got distracted so we didn’t get that back. Someone else liked his booties and so he handed those over as well. We drank and the more he drank the more he relaxed and found himself getting comfortable until we were outside in the backyard with a few of the other guys who were pissing against the fence.
“Don’t you have to piss?” one of the guys asked.
Brad just let out a laugh and said, “too late” to which everyone including me laughed. And I looked to his face and saw the kind of relief that comes from pissing. He actually pissed in his diaper, I thought. We made our way back into the party and danced some more, danced all night until the party was ending and we headed upstairs to his room.
By the end of the night he was in just his diaper as I put one of his arms over my shoulder and helped him up the stairs to his room where we both fell into bed. I put him face down and made sure he was on the edge of the bed in case he got sick. I stripped down and got into bed behind him against the wall. I put my arm around his waist, my fingers inside the diaper and felt around to his erection. He grunted with pleasure so I kept at him, faced down he humped my hand in little motions until he ejaculated into the diaper. I pulled my hand out. We fell asleep.
In the morning I awoke to find him on his back with a smile on his face. I looked to the diaper that was swollen and thick.
“I pissed myself rather than get up. You know this is actually great for nights of heavy drinking because I didn’t have to use the bathroom.”
I shook my head as I laughed it off and moved on top of him. I looked down into his eyes. Whatever this was I didn’t want it to end and we kissed. We kissed and we fooled around a little, but when it was over and we realized we had to get out of bed he got to his feet, pulled off the diaper, and dropped it in the trash before inviting me to share the shower with him. I got out of bed and we walked through the hallway to the bathroom as if we had a mischievous secret between us.
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