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The Bet

Category: Gay Male
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I had an experience when I was nineteen and in college that I’ll never forget. My college was not a “commuter college”. Most of us lived on or near campus and there weren’t any restrictions on overnight guests so hooking up with coeds was my favorite pastime. I had more than my share of luck my first semester because word quickly got out that I sported a solid ten inches.

It’s funny how women will talk about things like that and how best friends will stab each other in the back just to get to a cock like mine.

Halfway through my freshman year, however, everything changed when I met Liz. She was thin and athletic but had tits you would normally find on much larger girls. As she wasn’t big on giving blow jobs, she never once swallowed, she more than made up for it by letting me fuck those gorgeous tits. She explained that my dick nestled in between those beauties gave her immense pleasure. She would sometimes get off when I squirted on them “just like in the movies” she used to say.

I was disappointed when she would get off that way because she was like me, a one shot wonder. Neither of us would roll over and go to sleep but we were just both too sensitive to continue. An hour later was a whole other story.

Women on campus continued to flirt and ask me if what they heard was true but I was in love with Liz and getting more than enough sex to keep me happy so I became a one woman man. Things were great until she got a grant to study abroad the second semester of our sophomore year. We lived off phone sex during the separation until we got our first phone bills. We were college students and there was no way we could afford more bills like that. We agreed to email erotic letters instead but it wasn’t the same. Luckily or not, most women had given up on me, assuming I was taken so I wasn’t faced with the temptation that I’m sure I would have given into.

The only upside was my grades were going way up and my body was getting ripped. I had nothing to do but work out and study and both my grades and body were getting A’s. I was always skinny but my 5’ 11” frame with my 32” waist finally grew shoulders and a chest. I was riding on advice from the bigger guys I met in the gym. They seemed to give me more attention than the women around campus but I never thought twice about that until one night while studying.

I was in an area known as the “vault”. It was at the bottom of the library and almost no one ever went there. There were rumors it was haunted but not really, it was just a quiet place to study. At about eleven at night I needed to stretch my legs and pee so I made my way to the vault’s restroom. For security reasons there was only a men’s room on this floor, women had to go up two flights.

While I used the urinal I was caught off guard by someone stepping up to the urinal next to me. I thought I was alone on the floor. The kid looked my age and was a bit shorter than I was and looked like I did before I started lifting weights, trim and sleek. We both did business in silence until he said, “Twenty bucks.”

“What?” I said, not understanding.

“How about a bet for twenty bucks?”

Here we go I thought. One thing I forgot to mention about my school was how expensive it is. I was a scholarship kid but many here were from very wealthy families. Twenty bucks meant a lot to me but was probably nothing to this kid. Boy I could use twenty bucks.

“What’s the bet?”

“Twenty bucks says I’m bigger than you.”

Oh this is gonna be easy I thought. Only once in gym in high school had I seen someone bigger than me. Rich boy was bluffing, which made me think it was a trick. I asked him to show the cash and he pulled out far more than a twenty. He had a huge stack of bills and I had a huge something else.

“Let’s make it forty, I said.” I had a hunch.

“Okay, I call, let me see.” He turned, with pants pulled up and I flashed. I swear he sounded just like the women who see it for the first time. I was relieved when he said I won without bothering to show me his. He extended two twenties but his hand brushed my dick on the way. I twitched. It had been a long time.

“Jesus, it’s getting bigger!” he said as I grabbed the money and went to zip up before I embarrassed myself. I couldn’t believe I was getting a hard-on in front of this guy. My dick got even harder, however, when he said, “how about double or nothing?”

I was definitely interested. I continued to zip but he grabbed my wrist to stop me. His other hand grabbed my dick. I was going to smack him but I thought of the money and, surprisingly found myself getting very stiff. It had been a long time since Liz touched me.

He bet me eighty bucks that he could get me off twice in ten minutes. I figured this was a no lose bet. I’d get a hand job, even though I’d never thought of being with a guy before and I’d get eighty bucks because there was no way he would win. One, though I was young I lasted a long time, and two, once I got off once I knew that would be it.

As soon as I agreed, Ryan, which I learned later was his name, got serious. He shoved me into a stall and forcefully ripped my pants to the ground. He only jerked me a few times before he went to his knees and took me in his mouth. I have been with many women and I never felt anything like that!

His lips were smoother than any pussy I ever had. I don’t know what he was doing but I found my legs shaking and thought I might collapse. His hand reached up and twisted one of my nipples. I enjoyed it more than I thought I would but truly I was lost in what his mouth was doing. He was further down on my cock than any woman had ever been and the softness was beyond description.

Just when I thought it couldn’t get any better I felt him slide me down his throat. I groaned as he took me all the way! He would go fast then slow and it was all I could do to hold back. I suddenly felt my orgasm rising and though time seemed to stand still I knew it was nowhere near ten minutes. He sucked even harder as I felt my dick start to throb one step away from eruption and suddenly it happened. I screamed with relief as I let go and squirted like I never had before. The wall of the stall kept me from dropping to the ground as I shot off repeatedly. Oh it felt good, and unlike Liz, he kept those wonderful lips wrapped around me the whole time.

He sucked until the last drop was gone and I started to go soft. This was my ace, as good as he was, and he was the best, I knew I couldn’t get it again within the ten minutes. He sensed this and finally let me go. I wanted to kiss him for the pleasure he gave me but I held back. He checked his watch and I was shocked to find that it had only been five minutes. Still, it would take a long time to recover from what I just went through, so another blow job wouldn’t do it in the next five minutes.

That’s why I was shocked when he dropped his pants, revealing a very impressive eight inch throbber. I thought he would conceed and just beat off but he pulled out a condom and put it on. I was shocked when he told me to bend over. I begged off saying that wasn’t the bet but he rightly reminded me the bet was he would get me off twice in ten minutes, he didn’t say how.

I was nervous but the discomfort in my dick let me know the four minutes left wouldn’t matter and the money would be mine. I did as he said and bent over. A small part of me was thrilled to be so exposed like the people I had fucked so many times. I felt a cold liquid spread around my cheeks. He had brought a lube, why should I be surprised? He was here for a reason.

I felt pain as something thick entered me. It was pain at first but the fullness of it felt surprisingly good. He moved faster and faster and my body started to warm but I knew I would win until he pulled out. I figured he had gotten off and I had won but that’s when he let me know that had been only his finger.

Still with only minutes left, the eighty bucks was surely mine, or so I thought until he pressed his dick against my ass. Immediately it felt good and as he pushed deep into me it was as if a dam burst. This was obviously not his finger but it slid in me just as easy. I felt heat and a little pain but most importantly full. I heard grunting and groaning and figured he was enjoying my virgin ass until I realized it was me making all the noise. I was shocked by what came out of my mouth. I was telling him how much I loved his thick cock deep inside me and how good he was fucking me. He asked if my ass belonged to him and I swore it did. He could do this to me anyplace, anytime. I found myself harder than I had ever been even harder than I was when he sucked me off and dick was begging for relief. I didn’t care about the bet anymore, I just knew what was happening inside me demanded I get off.

I reached for my wanting dick and knew it wouldn’t take much to explode but he grabbed my wrist and said, “You, don’t need that.” I argued and babbled that I did and who cares about the bet but he said, “trust me, you don’t need that, and you’ll enjoy what’s coming.”

I didn’t believe him and reached for my hardened dick but he grabbed both my arms which left me helpless as he fucked me with a newfound fury. He groaned about how tight I was as my own body reacted in ways I had never known. As his groans built I matched him sound for sound and my large cock stretched itself thicker than I had ever known and I suddenly breathed hard as my dick and screamed as my dick erupted without even touching it. Oh Goooood I’m cumming! I shot more than I ever thought I could and knew I lost the bet but won so much more.

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