The Serendipitous Bet

I'm a cute blonde with a baby face, athletic body, and natural D Cup breasts. Some would categorize me as the typical cheerleader girl.

I don't mind this categorization since I do enjoy being who I am. Blondes get all the fun, right?

I've always had my luck with boys, ever since I can remember myself.

Initially, I had been very embarrassed with the size of my bust, but when I noticed what impact it had on the boys I thanked god he favored me so much.

Needless to say, I learned to use this trait to my advantage.

The first real sexual intercourse I had was during my first year in college (you might think I'm kidding, but honest to god, that's the truth!). And it was more than I had bargained for.

There's a saying that "Man plans and God laughs". But this encounter opened my eyes to real hot sex and I realized how much I loved it.

----

My girlfriends (Natasha, Lauri, and Stacy) and I made it a habit to come and watch the football practices of our college team from the stadium stands. Watching these hunks running around in their tight pants caused all of us to get very wet down there.

We kept discussing the size of their dicks and had various bets on who would be lucky enough to get herself close to one of these.

I knew I had the secret weapon (well it wasn't that secret, now was it?) to make it happen.

I offered my girls a bet, that I would get at least two of these hunks to show me their members and I'd even be able to touch them. If I won, they would get a chance to view it live, but in return, they would have to share with me their most naughty secrets. If I lost, then I would have to expose myself in public (and I knew that I would not allow this to happen, so I wasn't worried). The girls agreed to play along and promised to uphold their side of the bargain if they lost.

I began planning the encounter.

I thought of the perfect discreet place, where my girls could stand watching the scene without getting caught, and I would have privacy with my two would-be subjects.

The place I chose was not far from the men's locker room. I figured it would be easy to attract my men to that location. It was a small clearing that was surrounded by a high fence. It was mostly deserted. Its entrance was not easily visible and it had a sort of a secret booth that overlooked it without being seen. I figured my girls could hide there and they would have a great view of the scene.

It was now time to plan the cover story.

The two boys I picked were Brian and Chris. They both got high marks from my girls for probably having big dicks. Of course, these were all speculations, but that's what we had to work with. ***smirk***

They were handsome, about 6'2" tall, they had athletic physiques (doh...), and they had a reputation for being honest.

I chose them since I knew they were good friends, so would probably be together anyway. They had been noticing me during their football practices and secretly watching me whenever I was around. So I assumed it would be easy to lure them.

Finally, I had to choose the timing. That was a bit tougher.

Synchronizing everyone's (my girls) schedule was not easy, being in college and all, but I decided the best time would be after practice in the afternoon when they headed home. It would be late enough so that not many people would be around.

The girls didn't have much choice if they wanted to watch me live.

Last but not least, the last piece of the puzzle, was to decide on the actual date. This was, actually relatively easy.

I decided to text Brian and tell him that I wanted to show him and Brian something and asked him to meet me in that secluded area on Tuesday at 6 p. m. (I can't remember which date it was, but it doesn't really matter, does it?)

I notified my girlfriends when this would take place and urged them to arrive at least 10 minutes earlier to get into the secret booth without getting noticed. They had to swear to me they would be quiet throughout the scene and not come out until the boys left and I remained alone. I also required them to turn off their cell phones to prevent any stupid accidents.

On Monday, the day before D-Day, I sent Brian my text message. He was intrigued and tried to inquire what was it that I wanted to share but I remained mysterious and told him to arrive on time with his body Chris. He finally agreed and said they'd be there.

During lunchtime, that day, I updated my girls, "Listen. So far everything is going as planned, Thank god!"

"You know Jesse," confessed Lauri. "Just thinking about seeing these guys' dicks already makes us wet with anticipation." And they giggled hysterically.

----

Tuesday came. I was nervous as hell throughout the day, anxiously waiting for 6 p. m.

My girls tried to cheer me up, wishing me luck ("Go break a leg".... LOL), and saying all sorts of stuff like how lucky I was bla. bla. bla.

It didn't really soothe me and for an instant, I even had misgivings on going through this ordeal. Eventually, curiosity prevailed as I was eager to see those big dicks and touch them.

At 5:45 p. m. I arrived at the scene wearing a light pink sports top, and short yoga shorts, which both left little to the imagination, and I wore my blonde hair in a ponytail. When I looked at myself in the mirror I knew no man would be able to resist my temptation.

My girls arrived just on time. I checked all their cellphones and they went up to the secret booth. I circled the place nervously back and forth, hoping nothing would go wrong.

At 6 p. m. sharp both Brian and Chris arrived.

As they were after practice, they were after a shower and smelled good. They were wearing shorts with casual sports tops. As soon as they saw me, they exchanged looks, and I could sense I'd aroused their interest as well as whatever was buried in their shorts.

"So what's going on, Jessie?" asked Brian. "What would you like to show us?"

"Well..." I began. "Actually, you see, I wanted you to show me something in exchange for what I'd show you, " I said mysteriously.

The boys exchanged looks again, however, this time realization started to sink in, Brian's eyes roamed my body while Chris poked his head around as if making sure no one was about.

"What did you have in mind?" whispered Chris.

I motioned them to come closer and gave a light squeeze to their poking members (by this time I could tell they were hard).

Brian nodded and said, "And what is it you'll be showing us in return?" I grabbed my tits and wiggled them.

Both men grinned and nodded.

Brian made another tour of the area to ensure no one was around (luckily he wasn't aware of the secret booth) before he came back.

"All's clear," he whispered.

I motioned the boys to take off their pants. They happily complied. They both wore tight boxer underwear that accentuated their big dicks.

My heart pounded in my chest as I started tracing their dicks with my fingers. I could tell they were excited as well and enjoyed the attention.

I turned to Brian and gently uncovered his dick. His was around 7.5". I've never seen a real dick that close before. It was beautiful and I couldn't take my eyes off it.

I then turned to Chris and gently uncovered his member. His dick was even bigger! I think 8" or so. Wow! I thought.

I hit the jackpot!

They stood close to me with their dicks in front of me and for a moment I just gaped at them.

Brian whispered, "Touch us."

My hands were shaking as I touched both. Both dicks were rock hard by now and they were throbbing in my palms.

At the back of my mind, I already knew I had won the bet with my fellow girls, but I was pretty sure this scene was far from over. Had I not promised the boys I would show them my tits?

Both Brian and Chris, however, had other plans. Once they had me touching their cocks, they were less interested in my tits and more in what they thought I should be doing to them.

"Kiss them," Brian ordered.

I was still holding both dicks with my hands so I dropped to my knees and moved my mouth towards Brian's dick and kissed it. As soon as I kissed it I knew I'd love dicks for the rest of my life.

I planted another kiss and another, and I heard Brian moan lightly. I decided to move to Chris. Again, marveling at his huge dick, I came closer and started kissing it as well.

This went on for a couple of minutes, and I could feel the boys' excitement grow.

My thong was already drenched and I was getting very horny.

"Lick us," Brian ordered.

While I had never intended things to go THIS far, my curiosity prevailed again. The fact that Brian took the lead in instructing me what to do made it easier for me. I made a decision that I would be a good student and try to impress my instructor. I also remembered my girls and thought what they were thinking (or doing) while watching me below.

I dropped to my knees and started licking Brian's dick. I started from his balls and moved up his shaft while I made eye contact with him. I could see his chest heaving with excitement, and that just turned me on. I then switched to Chris and did the same and got the same reaction from Chris. I switched back to Brian and circled the tip of his cock with my tongue while pressing my lips around it. I could taste his pre-cum (only later did I learn what that was.... LOL).

"God... You're good," Brian closed his eyes and moaned.

Hearing this encouragement I knew I could follow my instincts and so let them drive me in pleasing the boys.

I cupped his balls and grabbed his cock with my other hand and started going down on him.

I heard Chris say, "Yeah girl! Go for it!"

I realized my teeth could cause trouble (hey! It was my first time...) so I tried very hard to be gentle.

Up and down I went on Brian's dick and he acknowledged by pushing it deeper into my throat. Acknowledging Brian's excitement, I stopped moving and let him choose the pace. He grabbed my head with his hand and pumped my mouth.

At some point, Brian pushed his cock too deep and I gagged, causing me to drop a load of saliva on his cock.

"You're doing great," encouraged me, Brian and I resumed deep-throating him.

Meanwhile, Chris was getting impatient so he lifted my hand and directed it to his cock. I grabbed it and started stroking him.

Both boys were moaning now. And I was so turned on I wanted to finger myself, but my two hands were already occupied. What to do?

I decided to keep them excited, so I gently stood up and motioned Brian to let go of my head. They looked at me curiously as I pulled down my yoga pants and displayed my drenched thong and my round ass.

They looked at me in awe, and for a second I thought I heard a light scream coming from the direction of the secret booth. I lost a heartbeat at that moment, as it seemed the boys had also heard it.

To keep them distracted I grabbed my yoga pants and threw them at Chris's face. He turned his head back at me and motioned Brian to look at me bending over and displaying my ass to them.

Brian grabbed his cock and started jerking off while Chris approached me and motioned me to go down on him.

I kneeled over and started deep-throating his huge cock. It filled my entire mouth and the sensation was marvelous.

"Show us your tits!" ordered Brian.

I did as instructed, stood up, and took off my top. Brian and Chris gasped.

"They're HUGE!" they exclaimed as they kept jerking off while eyeballing me.

My subconscious intervened again and as if by cue I started dancing sensually in front of them.

Remember that at this point I was only wearing my thong and my tits were visible for them to enjoy. They cheered me as I moved my body and played with my tits and nipples.

Not forgetting why I initiated this dance in the first place, I decided to take control of the scene and have them work for me.

I wanted them to fuck me, but I was still a virgin and was a bit afraid of how it would feel. I decided to start with Brian as his member was smaller (yet still big, mind you).

I motioned him to lay on the ground. He removed his boxers and did as I asked while his eyes were transfixed on my tits.

I motioned to Chris to stand near Brian.

I then removed my thong and lowered myself on Brian's cock.

I heard another loud moan from the secret booth and I immediately knew what was going on there. Luckily the boys were so focused on my body they were unaware of it.

I straddled Brian.

Gently I opened my pussy lips and let Brian's dick penetrate me. I paused waiting for a sharp pain but felt nothing. I continued to lower myself until he was buried deep inside. I so was wet it just slid right in.

"Ahhhh...." I moaned. "It feels so good."

I felt Brian's dick throbbing deep inside me. I started riding him in slow motion and my tits bounced as well. Brian reached his hands and grabbed my tits.

The sensation was wonderful and I climaxed.

Chris was jerking off as he watched me ride his friend. I grabbed his cock and started sucking him.

God, I was so horny!

After I felt comfortable and realized I'd probably lost my virginity during my private masturbation sessions I concentrated on the scene.

I was fucking the boys I had been fantasizing about for months!

I knew, that by tomorrow probably the whole campus would know unless I could make the boys keep this secret between us. That was a gamble of course. If it worked out, I already had two sex partners, that would be happy to indulge me whenever I wanted. If it didn't work out, however, I didn't fret. I knew my path to conquer the entire football team was already laid down for me, and I got even more excited.

All these thoughts were running through my head as I was sucking Chris's dick.

Chris grabbed my arm and pulled me from Brian's dick. He then grabbed my ass and lifted me only to lower me down as he directed his huge cock into me.

"Ahhhh..." I gasped and he moaned loudly.

Having Brian inside me first was eventually a wise decision. My pussy lips were already parted wide and Chris's dick penetrated me relatively with ease. I felt so full and I could feel his cock in my stomach.

I held his neck with my hands as he pumped his dick into me for several good moments. He was moaning loudly and I saw Brian still on the ground watching us from below while stroking his cock feverishly.

My excitement was at its maximum and I cried out, "Fuck me! I'm cumming!!" As I reached another intense orgasm.

Then I heard Brian say, "Kneel before us. We want to cum on your tits."

Chris lowered me to the ground and they both stood before me, as I knelt before them.

They moaned loudly while their hands moved faster and faster stroking their big dicks.

I watched them masturbate in front of me as I fingered my clit to another orgasm, in anticipation for their prizes.

Their moans increased and then without warning, my face got hit by a jet of cum coming from Chris and a second later Brian's cum hit me as well on my mouth.

They moaned and kept stroking their dicks, while pointing them towards my tits and continued spraying their cum all over them.

I tasted the cum that hit me in my mouth and I loved it! I grabbed both dicks and started licking them until they fell limp. Then I grabbed a handful of the cum on my chest and swallowed it and grinned.

"Wow Jess!" panted Brian. "You were incredible!"

"Unbelievable!" Grinned Chris.

"Thanks," I said sheepishly.

They bent over me and kissed me on the cheek. I smiled broadly, knowing that I got a straight A today from my teachers!

"Can you keep this between us?" I asked hesitantly.

"You can count on us!" Brian replied and nodded seriously.

"No one will ever know," Confirmed Chris.

I smiled happily and stood up. The boys collected their clothes and dressed and I did the same.

We said our goodbyes, and I let them leave first.

When I could no longer hear them I went to the secret booth, to see what happened to my girls.

As I entered the booth I noticed that Natasha, Lauri, and Stacy were totally naked.

There was a stunned silence. They were in a state of shock at what they had just witnessed.

"Jesse!" Murmured Lauri. "You've never mentioned to us that you had this type of experience."

"Well I haven't," I replied simply.

"That didn't look like it at all, from where we stood!" cried Natasha.

"Well," and I pointed at their naked bodies "THAT, clearly didn't prevent you from enjoying yourselves, now did it?" I responded with sarcasm. "Not to say you've almost blown up the entire thing with your screams and moans!" I added angrily.

"Oh... You heard us?" Whispered Natasha.

"Yeah, I did! And so did Briand and Chris. Fortunately, I was able to distract them so that they forgot about it quickly," I relaxed and said quietly.

The girls looked at me apologetically.

"We're really sorry about that," added Stacy. "You were so hot, and these dudes had such big dicks, we couldn't help ourselves. We got so horny that... well... you saw..."

"It was the best sex scene we have ever seen," finished Lauri. "You're a natural!"

I blushed, hearing these words from my best friends. We had a group hug and they kissed me.

They quickly dressed and we left the area.

The following day we went to watch the football practice again. I wanted to see if the boys had kept their word.

Brian and Chris nodded to me and I nodded back. The other teammates gave no indication that they knew what had happened.

That is when I knew, that I had earned myself two discreet fuck buddies and I smiled a winning smile.

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The end