Hi again. If you haven't read my first letter last week, Fooling my Roommate, you should do so now as you will be lost reading this if you don't. To sum it up last time at the end I was trying to decide how to do something that I felt would be difficult and yet exhilarating. The situation was that both my roommate and I were horny. We both were enrolled in a very strict religious college that made it impossible to take care of those needs the way you want to, we both masturbated secretly (supposedly). My roommate secretly wanted me, and even though I'm not gay, I definitely wanted to see what it would be like to masturbate together and maybe other things too. After writing that letter and reading the responses that I got back I decided that I needed to go for it all the way. The question was how.
I decided to wait till Saturday since I am off from work and wouldn't have any time constraints. I had made up my mind that I would go to bed early and be 'asleep' when Shane came home. He would then do his nightly masturbation routine, which he almost always has done for the last couple months. Then as he was 'molesting me' I would gently 'wake up' touch his arm and tell him how much I liked it and then offer to return the favor. With any luck he'd agree and we would have some badly needed fun. But what happened I never expected and I thing will be very amusing to you.
Saturday nights I always spend at the gym working out and playing basketball. So around seven I told my friends that I was tired and left to go to my dorm room. Shane usually stays out late so I was surprised that he was there watching the iron bowl. We talked for a little while and I kept trying to bring up sex but the only thing that I could get out of him was that he hated the stupid rules as much as I did. While we talked I stripped down to my jock strap and walked around a while putting the room back in order. I kept watching to see how his reaction was and I could tell he liked it. I even bent over giving him a chance to admire my ass for a couple moments while I cleaned under the bed, which he took advantage of gladly. I was just to the point where I was going ask if he needed help with the tent in his shorts when he got up and went to the fridge. I decided that I would go back to plan one, and grabbed my robe and headed for the shower.
Back from the shower I walked around getting my laundry together and taking out my contacts with my robe untied, letting it all hang out, so to speak. I could feel the sexual tension mounting and I jumped up into bed saying I would sleep good tonight. Just when I was beginning to think that my tactics hadn't worked, one of my friends, DJ, came in and wanted to talk to me. I lay there pretending to sleep as he called me and gently shook me. I heard Shane say, 'You'll never wake him up'. This made DJ shake me harder. When he did my robe slipped open and he said, 'Oh my god he's naked', to which Shane replied 'he always sleeps like that.' Dj says 'get me a marker, I have a great idea' Shane argues with him a little while worried that I'll blame him, and finally gives him a red sharpie. I thought that Dj would write some funny remark on my belly or something but instead he draws eyes and a mouth on my dick head. Pretty soon Shane comes over and they both have a blast decorating my dick and balls making it look like some kind of hairy monster. I watched the whole thing peeking under my arm.
Now there were three things that I tried to do with everything that I had in me, trying not to join in the laughter, fighting the urge to itch the tickling, and keep my dick from growing. I succeeded at all but one. You guessed it. I heard DJ say ' oh shit he's getting a hard on' This just gave them more area to decorate. They were cracking up like two little girls writing notes all over my body. Then they covered me back up and DJ left. I lay there trying to suppress my urges to itch when finally Shane went to the bathroom giving me the opportunity. And when He came back it was playtime.
Shane called my name. When I didn't respond he opened my bathrobe again and started cracking up at what they had done. By this time I had become soft but instantly as soon as he touched me I swelled up like a blowfish. (Damn I needed it sooooo bad I was going to go crazy) Pretty soon he went into his ritual of stroking me and felling my balls. It never felt better. I decided that on the count of three I'm going for it. One, Two, Three.
I slowly reached out to touch his arm as I took my arm off my eyes. I saw this horrified look on his face and then he jumped away shouting, 'Mother fuck it' at the top of voice. I tried to tell him that it was ok, but he just started throwing things at me and cussing me out. Then he grabbed his jacket and left. At first I sat there stunned and very confused. Then I thought I've got to find him.
I dressed and searched everywhere I could think of with no luck. I went back to the dorm and made a new plan to win him over. I stayed up all night tossing and turning not knowing what to expect next. Finally I fell asleep. Sunday morning I looked in the mirror at my ridiculously decorated body. It didn't seem funny any more. I faked a smile looking at it and scrubbed in the shower to get it off. After my shower I went back to the room and to my surprise Shane was there quickly throwing his stuff in a suit case. I said, 'I'm not mad Shane'. He didn't stop. 'Here I want you to read this', and I gave him a print out of my first letter. Eventually he took it and with his back to me and slowly read it. He went over and sat down on the bed. I stood there with my heart beating wildly waiting to see how his reaction would be. Then he put the letter down. After an awkward moment of silence I handed him a couple of the responses and he read them silently avoiding eye contact. As he read them I said, 'I think they're right. We should go for it.' He looked away and wiped a tear that had formed in his eye. We sat in silence for a few minutes and I realized I would have to be the one to make the next move.
I got up locked the door and sat down on his bed. He sniffed still looking down. I slid over next to him saying, 'Want to see a big hairy monster?' He smiled briefly and wiped his eyes again. Again we sat silently, then saying to myself 'oh well, here it goes' I placed my hand on his thigh. He didn't move. My body was quivering and my heart was pounding out of my ears. I let my hand slide down to his crotch. Finally he broke the silence by saying, 'That's why you walked around in your jock last night.' I whispered back, 'Yeah, I really want to do this'. Still he did not move. His crotch felt warm and moist as I started softly caressing it. I could feel his cock as it started to swell and move in his pants. 'Shane' I said, ' we both need it and we both want it, so let's just be sex buddies.' With that he gave me a big bear hug and I took the opportunity to open his pants. He lifted himself up as I pulled them down. His cock was straining at his briefs and I slowly felt the outline. Wow! I was beside myself in excitement. I pulled is briefs down and he let go of me as I slid of and knelt in front of him. I said, 'Just lay back and let me show you what I've wanted to do since the first night you touched me' He obeyed after he helped me take his pants and briefs off. I had never seen an uncircumcised cock before and played with it sliding the skin up and down the length of it. It was about the same length as mine but a little bit thinner. (I was glad about that as I knew shortly he be putting it in my ass.)
It was such a strange feeling giving pleasure to an aroused man. I played with his balls felling their weight and texture in my fingers. He quietly let me know he was enjoying it as I began to stroke it faster. I stroked him for about five minutes while feeling his balls when he took my hand and said he didn't want to cum yet. 'I really want to suck you and you can cum in my mouth', I said. With that I put his cock in my mouth. It surprised me how good it tasted, and the smell of his crotch was so overwhelming. I tried to mimic what he had done to me, moving my tongue up and down his shaft. His precum was oozing out of his cock. Soon he was grunting and his balls got tight. Load after load of warm cum filled my mouth. I milked it out with my hand as I continued to tongue his cock head. After several loads of cum it was over. I winced a little but managed to swallow the slimy mess. It was much better, then I expected.
I stood up and let my robe fall. Immediately he started laughing when he saw the remaining ink that wouldn't wash off. We laughed and laughed about the whole thing. The artwork on my body, how I had to fight from moving, the look on his face when I woke up, the look on mine when he was throwing boots and books at me. We both needed a good laugh.
Then after talking him out of withdrawing from school, we set up some ground rules for our relationship. He told me some of the story of his life; someday he wants me to post it. It is really revealing of how bigotry and negative feelings of sex can mess you up.
Then we spent the rest of the morning fooling around with each other. We both came several times. I'd never had so much pleasure in one day. And it is so much better when it's someone else doing it. Then before I went to work last night we played some more. I'm so glad I trusted my heart with this and went for it. He's really taught me a lot in the short time we've been roommates.
He'll be here again shortly, and I've decided to pretend to be asleep again. Only this time I will be on his bed. But first I'm going to try to scrub the rest of the monster off.
Ps Shane made me correct the fact that he actually is 5' 9 1/2' tall.