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Jake 'the Snake' and the Bet

Posted by: Author: Age: 19 then/Jake 18 Posted on: 1 comments
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This happened a few years ago when I was in college.


My name is Matt. I am kind of a little guy- 5'7' and skinny. I have very dark brown hair and brown eyes. I have been told I look like David Archaletta, from Idol. Personally, I don't see it but whatever! Overall, I am pretty smooth except for my pits and bush which both are really hairy. For as long as I can remember I have liked guys and always suspected I was gay, but had never been with a guy before. Then I went off to college in a small midwestern town where I met Nathan. Nathan was a junior when I was a freshman. We had a class together and were paired together for a project. One night while we were working on the project- ummm-let's just say I found out for sure that I was gay!! Nate became my first boyfriend and for almost a year we were together. Unfortunately for me, fortunate for him, he received a big scholarship to the state's university. He could not pass it up-so off he went right before the start of the fall semester. I was crushed but knew it was what was best for him. The fall semester was about to begin so I focused all my attention on the new school year as a sophomore.

I, being a second year student, was allowed to move into the dorms a day before the freshmen. I was getting settled in and, of course, was nervous about meeting my new roommate. All I knew was his name was Jake and that he was from a small farming community. Since I was from a suburb of a large town I was wondering how I would get along with a farm boy. I happened to be looking out the window when I saw a beat up old pick-up truck pull up in front of the dorm. I knew instantly it was Jake. Three guys hop out of the truck and start unloading stuff out of the truck's bed. All too soon I hear them coming down the hall. They were talking loudly about parties and pussy and how great it was going to be for Jake. The three of them came into the room carrying a beat up old duffel bag and a case of Bush Light beer. My stomach dropped-I felt as if my worst fears had just come true. Being polite and trying to manage the situation, I stuck out my hand and said 'Hi, I'm Matt.'

The cutest of the bunch, a tall well built boy with sun bleached hair and a deep dark tan, wearing only bib overalls-no shirt- exposing his slightly hairy chest-grabbed my hand 'Hi I'm Jake. Your new roommate!!'

'The snake!!' One of the other boys grunted loudly while thrusting his hips wildly.

I sat there choking down the cheap beer trying to make small talk with this motley group of hicks, patiently waiting for them to leave. After about an hour, when the beer had finally run out, they left. Seems as if they had to get back for the evening milking. Finally I was alone with my new roommate. I was actually looking forward to talking with him alone to find out if he was like his buddies or what. I could not take my eyes off this blond god as we sat across the room from one another. I figured, being the senior man in the room, that I should let him know what the deal was and lay down some ground rules.

'First off,' I started, 'I am gay. Don't worry your not my type(OK so I lied!!). But if you have a problem with that we can go to housing tomorrow and you can move.'

He smiles and says 'That's cool. I have a gay cousin and we get along just fine!'

I was greatly relieved to hear him say that. Although I was out, I didn't need him broadcasting it all over the place so I added 'Even though I am out, I would appreciate it if you would not go around telling everyone your roommate is gay.'

Still grinning, he says 'No prob dude-it's all good'.

So far so good. Things were going better than expected. I felt empowered so I continued 'Let's make a deal. I won't bring guys back to the room if you won't bring girls back to the room!'

Still grinning Jake responds 'no prob there either dude. I got my girl back home her name is Marybeth and I am gonna marry her one day!!'

We continued to talk for a while more. He seemed cool, unlike like his buddies. During the course of the next month we both settled into our routines. Jake and I got along. By no means were we best friends or anything but we got along. Interestingly enough, I never saw Jake with a girl either. Either he was being faithful to his girlfriend or he was in the closet. Jake also was not modest about walking around the room naked in front of me. Believe me I know where he got the nickname 'the snake'!!! That boy was hung!! Even limp he had to be well over five inches. He also had the sexiest thick patch of dark brown pubes I had ever seen!! I like nothing more than a guy with a great bush!! I eventually got over my shyness and would be naked in front of him as well. I am not sure, but I would almost swear that he would be eyeing me up the way I eyed him up when we were naked. Sometimes late at night I would hear him jacking off always finishing with a grunt when he came. How I longed to be the one doing that to him. Finally I got my chance!

One Saturday night neither of us had anything to do and were just hanging out in the room together. Everyone else on the floor was either out or gone for the weekend. With no one around I decided to try and make a move-but I had to be careful because I didn't want to offend him or worse!! 'So dude, how did you get the nickname 'the snake'?

'Welllllllll,' He stammers as his face turns bright red, 'I used to date this girl and she wouldn't let me fuck her because it is so big. She told some of her girlfriends and they just started calling me 'the snake'. Guess it just kinda stuck.'

'Let me get this straight,' I challenge, 'You were dating a girl and not having sex? Man, let me tell you, I would NEVER date a guy if I wasn't gettin somethin from him!!'.

Still beat red, Jake sheepishly replies, 'Well she would give me handjobs. She was really good at it too. As a matter of fact she was the best. She would make me cum every time!! Marybeth can't even do that!!'

BINGO!! My opening. 'Maybe, but there is so much more to a good handjob than just cumming! Everybody knows that if you want a great handjob you have to get one from a guy because they have the same equipment and lots of practice!!'

With a big smile and half a laugh Jake says 'You would know!!'

OK here goes. Time to make my move. 'Wanna make a bet?'


'I bet I can bring you off better than any girl could. If I do you have to be honest and tell me and then jack me off. If I don't-well then you at least get your rocks off.'

A painful moment of silence follows before Jakes says 'OK it's a bet!!'.

Jake starts to strip. First taking off this shirt, exposing his nice hairy chest. Not overly hairy like some guys but just enough to be sexy. Next he unbuttons his pants. Before he takes them off he looks at me with that sexy grin of his and inquires 'Aren't you gonna get naked too?'

That one caught me off guard a little bit. I stammer 'You'd be cool with that?'

'Fuck ya dude. I mean we've seen each other naked a lot. The only difference is our dicks are going to be hard this time!!'

With out hesitation I whip off my shirt. Then we both take off our pants. Our hard dicks are straining our tighty whities. I take my underwear off first freeing my rock hard cock. Jake goes to take his off but I stop him telling him to lie down on the bed and let me take over. Jake does as asked. I grab the lube from my drawer and walk over to his bed. The whole time he is just staring as my big hairy boner bounces as I walk to him. I sit on the bed next to him and start petting his chest hair and tickling his arm pits. Next I start caressing his hairy inner thigh. By his breathing and movements I can tell he is getting really worked up. I then trace his treasure trail down to the waisteband of his underwear. My dick is throbbing and my hands are trembling in anticipation of what lurks beneath that this cotton cloth. Unable to wait another moment, I pull down his underwear exposing the biggest, hardest, hairiest, dick I had ever seen!! It wasn't all that thick but it sure was long!! It had to be a good nine inches with another inch buried in his pubic hair!! And his big balls hung very low in his hairy sack. His man scent was intoxicating, I was in heaven and almost came right there on the spot!!

I grabbed the lube and put some on my hand. I slowly started teasing his massive head with my finger tips. He let out a little squeal of pleasure. Then I started working his shaft. First fast, then slow, then just the front, then just the back, the back, then just his ball sac, then just the head again. Sometimes I would just stop altogether and let him catch is breath. I next wrapped both hands around 'the snake' and whispered lovingly 'Fuck my hands boy fuck 'em!!!'

He starts violently thrusting his hips. I loved the sight of his big purple head popping through the top of my hands and the feel of his thick brown bush grinding into my hands. He started thrusting faster and deeper-I could see and smell his swet- I could hear his breathing change from a steady pant to moans of extasy- I could tell he was getting close. I stopped. Clearly annoyed he asks 'Why the fuck did you stop dude? I was almost finished!!'

'Ya but I'm not done with you yet boy!!' I tell him teasingly.

'Give me the lube man!'. Jake demands.

'What for?' I playfully inquire.

'You win dude. Your not even done yet and it is already the best fucking handjob I've ever had!! I want to do you while you do me so we can cum at the same time!!' Jake exclaims.

With that said, I hand him the lube and position myself so we are in a 69-his hard hairy dick in my face and mine in his. Soon I am feeling the pleasures of another boy's hand on my aching cock. He starts working me just as I am working him. We play for about another half hour before Jake begs 'Please make me cum I can't take any more!!'

We furiously start stroking each other. Again heavy pants turn to moans of pleasure. Our ball sacs pull up tight. We both start wildly fucking each other's hands. We are up tight against each other's bodies as our orgasms begin at exactly the same time. He shoots off like a rocket as do I. Cum is flying everywhere. We stroke each other through our orgasms and beyond. We continue stroking until we are completely spent and limp. We just lay there for a few minutes enjoying the feelings of pleasure still resonating through our bodies. Then we get up, grab towels, and head off to the showers to clean ourselves of all the lube and cum.

That was one hot night and I was glad I made the move. I am still not sure if Jake really had a girl back home or not. He never really talked about her and I never met her. What I am sure of is that when ever Jake was horny, which was just about every other day, he would simply ask me if I wanted to play with 'the snake'!!!!



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