Ok so I wrote a different story before another chapter here. I needed to think awhile about how I felt about this situation. Get in the mindset of me at 18 with Kenny.
So my big move ended up being rubbing my feet up and down his leg in bed. Nothing big. He seemed to enjoy it and I moved my head a little close to his, he was still smiling at me, hands at his side laughing a little from the feeling of me rubbing him with my leg. It was starting to feel like I was a machine he put a quarter in and I made him feel good and cum by his sit back and smile reaction. So I stopped everything and laid on my back and said fuck it, I'm going to bed. He was still on his side looking at me, I could tell out of the corner of my eye.
Kenny: (he leaned over and drunk whispered) We aren't going to play tonight? (He laughed a little after too)
Me: Play with me then, I'm ready....
Make him do a little work I thought. And honestly I didn't know what he meant by "play" and I was in no mood to guess after all the work I had already put into that night trying to get him to "play" with me. Lesson: A few ways to start something with another guy in your bed (if you are lucky enough for the situation), touch them and judge the reaction. I mean a guy you still aren't sure about. First Base: Shoulder, head, hands, normal areas first. Bad reaction? Write it off as a mistake, stretching etc. Second Base: Then chest (no nipples), legs, feet - less safe areas but still not too sexual. You can still write this off as a mistake, but its harder. Third Base: Then? Lower abdomen, inside thigh, face, nipples. If he isn't resisting or pushing you away by now, he is into it, but still afraid to admit it. Homerun? Dick, Ass, Balls. Thats how I learned the nature of progression with being with an amateur guy in bed. Kenny skipped to third base and started to try and rub my nipples a little bit. That got my dick hard pretty quick, and I grabbed his hand to help him rub me properly just in case he had thoughts about pulling away. I reached over and skipped to the end and rubbed his dick and balls through his boxers. I moved his hand lower to my little guy too, we would go at each other equally in this.
I wanted a blow job pretty bad, I didn't want to settle for a jerk and sleep. I was gonna see how far I could get him to go. My goal was always to fuck something (I know it sounds creepy, but in college and at 18, that was my goal) guy or girl, I didn't care. And Kenny and I had been getting along real well, and just the fact he was willing to do shit with me was enough to motivate me to try and go further. I slid down his body and started to nibble on his dick a little bit. He was the only guy I was with that still had his skin on, so I didn't really know what to expect with blowing him. He was really clean, that wasn't a problem, and when he was full mast his skin retracted completely. As I said before, he was the smallest guy I was ever with too (Not that I cared). I am not a "size queen" or any of that shit, and I think anyone who is should just fuck themselves with a baseball bat to feel better and get over it. Anyway, his dick tasted amazing (honestly, never had a dick that didn't taste amazing :) and he was loving my little lick fest going on. I wasn't full on blowing him, just testing the waters, jerking, licking his tip, inspecting his dick and balls with my eyes. I was jerking myself while I was doing this and wanted to try and see if he was willing to go just a little further. I licked my fingers and pushed his ass up, got in position and slowly fed my finger into his ass. He had no reaction at all, he was still laying down eyes closed and breathing fast. He didn't say a word...so what the hell. I pushed another finger in, real slow and started to finger fuck him while I went full speed on his dick. I stopped sucking for a minute when he started grunting and moving around, I knew he was close.
Kenny: God, keep going jesus please
Me: Ok, do you like me fingering you?
Kenny: I don't fucking care, just please keep sucking me
Me: Can we have sex? (yea I was young, and didn't know to say "can I fuck you" yet)
Kenny: Yea, sure whatever, just fucking do whatever (he was drunk of course)
So still confused, I didn't want to fuck him if he didn't want to, I don't think he understood my question. I guess you could say we were "having sex" already, I never implied fucking him in his ass. So I decided to finger him a little more and finish him with my mouth. If he wanted to fuck after or whatever I would be fine with that, and more comfortable in my head. Plus, I loved his dick and I loved tasting him; I guess at that age, and experiencing new things, I would have loved pretty much any dick. It was only another minute or so and he was trying to roll around, I held him in place and took his load in my mouth. I was still getting used to swallowing, but I made up in my head that if I blew a guy, I was going to swallow it. Plus, I didn't need to clean clothes and sheets evertime I hooked up. Decent load, nice taste obviously, I got up and kneeled over his body with my dick in his face, it was as big as it could be and leaking, waiting for something to help it release. He started to suck a little bit and went to sleep. Sucks to be me I guess. I got up and went into the bathroom and jerked off, no blue balls tonight. I know, bad ending for the night, but I'm not going to change the story from what happened to make it something that didn't happen. The good part is I sprayed the inside of the toilet stall like a fire house and was happy I had some kind of release at last, it still felt great because of what had just happened. I went back to the room and Kenny was spread eagle in the bed under my covers, I was sick of being nice and just pushed him toward the wall when I got into bed. He came back and collapsed on top of me, which felt nice actually, contact with him, his warmth and smell. I made sure to peg the door before I got in, just in case my roommate Mike got back before we got up. Pegging the door just meant you put 3 pennies in between the lock and it was impossible to open the door from the outside. I wasn't worried though, he was a late sleeper and I was an early riser. I was thinking before I finally went to sleep, Kenny sprawled over my chest, I needed more from this if it continued. I had to fuck him, and I should have that night, but my young brain and conscience got the better of me. It wouldn't the next time. I mean I wasn't going to force him into anything, but I decided to be more forceful about our fooling around sessions, be less timid.
I got up about 6am, Kenny was still sleeping on his stomach to my right. I lifted the covers off him and pulled his boxers down to get a look at his ass. It was like the rest of him, a light brown almost hairless paradise. I went a little too far and spread his ass open to look at his hole. Yep, that was something my cock needed to be inside, yep. Thats all I thought. It was amazing, little downy hair, pink around the light brown skin of the rest of his ass....I couldn't see it the night before because it was dark...but in the light, wow. I got to see the treasure I was fingering the night before, and it was getting me a little excited about the potential future. Ok thats enough, I needed to cool down a bit, so I got up and took a shower. I had to wrap my towel tight, because my dick was stretching out after my little show of hopefully what would happen. I didn't jerk off in the shower, I did what I usually did, overthought things and made dramatic plans in my head that would never work, well at least I thought they wouldn't. As a young bisexual teen in college, your mind sucks. Its always self doubt and regret. I settled on being happy with what I had with Kenny, whatever it was. At least I got a dick to suck, and occasionally I would have a mouth to put mine in, I was off the ass thing for now. I didn't want to push things in case things went bad between us. I went back to the room after the shower and Kenny was up and dressed.
Kenny: Cool night, I'll call you later if I am around.
Me: Uh, ok sounds good dude.
He left. Well I was used to this by now from him, and expected it, so it didn't really bother me anymore. And to answer all the emails "Why didn't you do this or that?" on the first night, I was 18, a kid! haha. And no, I didn't look like a kid, and I had to shave and shit, but I was still a kid mentally. I know it was different with Nick and Justin, but I was older and had more experience. Shit, I look back on my thing with Kenny and ask myself the same questions, but just having what we had was enough for me at the time. Like I said in one of my other stories, I would love to go back to 18 years old with my current brain, I would have many many more stories to tell I think haha.
Anyway, day goes on, Mike comes back, had a good night with the girl he met. Kenny called late afternoon and said his roommate left for the night and to come over and hang out. I brought some CD's with me, he didn't know if he had music to play or a computer to play music on. Mike was going to try for round 2 with this girl, and it worked out perfect. Her roommate didn't want people over, and I would be over with Kenny, so he had our room to himself. I stuffed a bottle of whiskey in my jacket for the walk to his suite. It was only upstairs, but you never know with RAs and campus police. I got to his room and he had rap going I could hear in the hall, Busta or something, really loud. I hoped he had a cassette player too, I brough some NWA my brother had gave me. I know I was only 8 or 9 when they came out with the album, but if he wanted real rap, this was it. I tried the door and it was open, so I walked in. He smiled and said hey, I pulled out the booze from my pocket and we started to drink. He had a cassette player in his sterio so I put the tape in.
Kenny: Fuck! I love NWA! Man, this is it, this is the shit!
Me: Yea I grew up with this shit man, I thought you would like it.
Kenny: Easy fuckin E mother fucker!
Easy E was in NWA, ended up dying of aids, sorry for the debbie downer shit, just trying to help out people who aren't aware of NWA. Anyway, we kept listening and drinking. I started planning in my head how the night would end. I needed to either sleep here or make it a late night because Mike wouldn't be done with his thing until late night and I didn't want to interupt him banging his new girl. I was also thinking, this would be my last attempt with Kenny if it didn't work out. I would find a chick myself and deal with all the shit that comes with girls (yes I know they suck, I'm married to one) but at least I could get my dick wet. So it was getting late and we were getting pretty shitty from drinking, Kenny had smoked a little weed, I wasn't in the mood.
Me: So, am I staying here or what, its getting late.
Kenny: (Shitfaced) Yea whatever.
He was still busy listening and focusing on the drinking, he wasn't planning the future like I was. So I decided to take the initiative and stood up next to him. He looked up at me and had his big smile going as always, never understood why he smiled all the time. Was it being nervous or just always happy, no idea to this day. He still smiles like that all the time, reminds me of things that happened :). We don't see each other that often though, but when we catch up, still had the shit eating grin and happy voice.
Me: I'm gonna stay here tonigh, I'm kinda beat so I'm gonna lay down.
Kenny: Sure, take a rest dude, I'll be in bed in a little bit.
So this was my "GRAND PLAN". Dress down to my boxers and t-shirt and lay in his bed on my back and see if he was interested in anything. Give him access to my whole body, fake sleeping, and see where things went.
Kenny: You awake Brandon?
I said nothing and didn't move. My breathing was really slow because I was relaxed and laying down for awhile.
Kenny: Brandon...hey? You with me? Shit you must be asleep already..damn.
I gave him no signs of being awake. The damn at the end helped, that meant he wanted to do something, and I would be awake quickly if he made a move. I actually had brought lube with me just in case. I had no high hopes or anything, and by "lube" I mean a plastic bad filled with vaseline....I didn't really know about anything else at that age. He got into bed and I fake stirred a little bit and woke up.
Me: Turn off the light if we are gonna sleep.
Kenny: Oh ya, sorry.
He got up and stumbled a little bit, turned the lights off and got back into bed next to me. He just layed still, not doing anything. Like I had said before, this was my last attempt at him, I mean to what I wanted from us hooking up. As much as I liked to suck dick, I didn't like having to finish myself in a bathroom stall...so that had to change. He had on boxers and I decided I was just going to do it. I reached for his waistband and pulled them down.
Me: I want to fuck you Kenny.
Kenny: Huh? Yea, whatever, I don't care....
Me: You know what that is right?
Kenny: Fuck me and get it over with.
Me: Woah, I don't want to make you do something man.
He was drunk and thought I just wanted to get him to a point to fuck him. Believe me I didn't, I was too young to know what I was doing at all, I thought he would be into it.
Kenny: I'm cool with it, just do it.
Me: Ok, thanks I guess...I don't want to hurt you or anything...
Kenny: Just fucking do it.
He rolled over on his side and I kinda felt bad about the whole thing. I grabbed the bag of vaseline I brough and lubed up my dick and his ass. I was having second thoughts, shit I was having third thoughts.
Kenny: I'm really ok with it, please lets just fuck.
Me: You don't sound like you are Kenny.
Kenny: I'm just tired I guess, go for it man, suck me after.
Ok, now I felt slightly better about what was happening. I didn't finger him at all, which was probably a mistake. I couldn't see much in the room, but I remembered what his ass looked like before. I put my engorged dickhead against his ass and pushed in. It didn't go well, he was wincing in pain, and I stopped pushing.
Kenny: It hurt, just get it over with.
I didn't know what to think, but pushed inside him again. My head popped in and I got about 3 inches in before I started humping him. I don't think he wanted or could have taken any more, but it was good enough for me. He started to actually enjoy it a little bit, and I was jerking his dick while slowly rocking in and out.
Me: Can I cum inside you?
Kenny: Yea, I don't care
So I did and it felt amazing. I jerked him off to completion, which wasn't long after I finished inside of him. First weird anal sex I ever had with another guy. My dick got hard again before falling asleep with just my mind thinking about what had happened. I was worried about the next morning and how he would take it.