You Wanna Bet?

The 8th hour bell had just rung and we were all settling in to our desks when Jesse leaned over and quietly teased……
“Well Wilson……what’s the bet going to be this time?”
We were in 8th hour Geometry and Mr. Belfiori was handing back the tests that we had taken the day before. Jesse Larson and I always made “fun” bets with each other on who would get the better score on our quizzes, or tests and stuff. The bet was usually something simple like buying the other person a soda, or getting them a date with one of our friends. The odds were usually in my favor even though I was only a sophomore to Jesse being a senior. I was simply just a little bit sharper at Math than he was.
“I don’t know Jesse, what did you have in mind? Another date with Kimmie?” I teased.
Kimberly Peterson was my best friend and had been my next door neighbor since we had been in Kindergarten. She was also the only sophomore girl that had made the varsity cheerleading team and because of her over developed young body, she had become the desire of every boy in school! The last time Jesse had gotten a higher score on a Geometry test than I did, his bet winnings consisted of me convincing Kimmie to go out with him……and, it didn’t take too much convincing! Jesse was a very good looking boy with thick blond hair and bright blue eyes, and, he had the coolest car in school. Also, according to Kimmie, he was very well hung!!
And, Kimmie would know!! She had lost her virginity during the summer before our Freshman year and has been sexually active ever since. In my case……I didn’t lose my cherry until I attended an after Prom party last May, and since then I have only had a few boys that I let have their way with me! Or should I say, they let me have my way with them!!
“How about….. if I beat you today…..you meet me in front of the team locker room after school…..before the JV game…..” Jesse offered.
“Huh?”, I thought to myself. There had to be more to this than just meeting him in front of the team locker room….. And seeing as how I was on the JV cheer squad, I had to be at the JV game by 4:00. Whatever he had in mind had better not take too much time.
“OK…..I guess. And if I win, I want you to drive me to the Woodland Mall tomorrow and hang around with me while I shop for underwear!” I chuckled.
“Geez Mary……will I have to go in the stores with you?” Jesse replied, looking totally grossed out by the whole idea.
“Shhhhhh…..” I whispered as Mr. Belfiori came down our aisle, placing tests face down on desks as he walked by.
Mr. Belfiori put Jesse’s down on his desk and then put mine down on my desk as he continued to the front of the room. I immediately flipped my test over and saw a 96% marked on the top of the front sheet. ‘Not bad’ I thought as I looked the test over. A couple of dumb mistakes I had made…..probably when I had caught myself looking over and daydreaming about Jesse!!
I looked to see what Jesse had gotten on his test, and much to my surprise he had a 97% circled at the top of his test!
“One point!” I thought. “How could that happen? I had those theorems memorized!”
Oh well….
“See you after school Wilson……don’t forget……team locker room…” Jesse boasted.
What could Jesse have in mind? I hope he knew that I had to get to the JV game and couldn’t be screwing around to long after school. It was a good thing we got to wear our cheerleading uniforms to school on game days as that would be one less thing I would have to worry about.
8th hour just dragged by as we reviewed the test problems forever. Out of boredom, I even volunteered to go up to the board to work a rather long problem hoping all the boys, and probably a few of the girls too, would be checking me out in my rather short and tight cheering outfit! I loved the attention. The rest of the hour I couldn’t help but wondering what Jesse had in mind….
Finally the bell rang for the end of the hour and the end the day! The other students just flew out of Mr. Belfiori’s classroom. I headed to my locker to drop off my books and to tell one of the other JV cheerleaders that I might be a little late for the game, but that I would be there! I dropped off my stuff and headed down towards the team locker rooms. I was surprised at how quickly the school had emptied out after the final bell. It felt like I was the only person in the school. As I neared the team locker room, I saw absolutely no one in the hallways….so just where was Jesse?
“Psst…..Mary! Come in here!” I heard Jesse whisper excitedly.
I turned to see where his voice was coming from and saw that he was calling me from the small training room next to the main locker room. He had the door open just enough so I could see it was him. I walked over and he opened the door and pulled me into the tiny room. There was nothing in the trainer’s room except for a vinyl covered taping table, a bench, and an old whirlpool bath. I heard Jesse click the lock on the door as it closed quietly behind me.
“What are we doing in………” I managed to get out before Jesse covered my lips with his and began probing my mouth with his tongue. “Mmmmmppppfffff…..” was all that came out as I kissed him back the best I could. He did, after all, kind of take me by surprise!
After we finally broke our kiss, Jesse lifted me up and sat me down on the taping table so that I was barely sitting on the edge. The vinyl felt cold on my barely covered ass. Jesse gave me another wonderful tongue filled kiss as he lifted my short skirt up to my waist and hooked his fingers under the waistband of my blue, spandex cheer panties. I can’t believe I didn’t resist, but this was all happening so quickly. I didn’t have time to think about what was going on….and the heat of the moment was really turning me on! As we ended our second kiss, he pulled the spandex off my ass and down my legs to my ankles, revealing the tiny white thong I had chosen to wear this morning. I pushed my blue and white cheering shoes off and let my spandex fall to the floor. Jesse put his mouth back over mine and as we kissed I felt a tingling and dampness starting between my thighs.
Jesse gently pushed me back so that I could prop myself up on my elbows. I couldn’t take my eyes off of him as he lowered his face toward my pussy. ‘Oh my god!’ I thought….what is going on here? ‘Is he going to go down on me? Does he want me to go down on him? Oh geeez….’ I felt a wave of lust wash over my young teen body and suddenly knew what I wanted to have happen…..what I needed to have happen!!
“Mary….let me see if you are really as hairy as what I’ve heard…..” Jesse whispered as I felt my soaked thong being pulled out of my ass crack and sliding down over my thighs. Jesse pulled it over my sock covered feet and dropped it on top of my shoes. I suddenly had nothing on below the waist except for my soft, white, slouchy ankle socks that were part of my uniform.
What did he mean…. as what I’ve heard?
At the end of my Freshman year, my mother had insisted that I start taking birth control, which was a good thing considering Prom night! Anyway, after taking “the pill” for a few weeks, I experienced a few changes in my body. The first thing was that my wispy, girlish bush had suddenly decided to get very, very thick,……and the second thing, besides the fact that my boobs went from a 34B to a 34C, was that my nipples would get really, really long whenever they were excited. Now, neither of these were bad things…… my thick bush sort of hid my full pussy lips and I thought it looked pretty cool, and my nipples would get so long and sensitive that a boy could get me off by just by kissing and playing with them! BUT, nobody knew about this except for Kimmie and my ex-boyfriend, Jake. Well, there was that guy I met at the fair during the summer who stole my underwear, but he was seven years older than us and from out of town! Someone had talked….and I just couldn’t figure out why…..or who?
Jesse pushed my knees up towards me and my thighs just naturally parted for him. I felt the air hit my wet pussy.
“Holy crap Mary….your bush is incredible! I‘ve never seen a girl so hairy down there…..that is so hot….it’s beautiful!” Jesse whispered as he lowered his lips to my dripping sex.
I took that as a compliment because I was pretty sure Jesse had seen his share of girl’s pussies. And, it made me feel pretty excited to know he liked them hairy!
Jesse gently started using just the tip of his tongue to tease my clit and I could feel my button begin to swell. I was sure it was already poking out from between my hairy lips. After circling my stiff clit with his tongue for what seemed like forever, Jesse finally began sliding his tongue up and down the full length my slit, occasionally flicking it in and out of my dripping hole. I could feel that my pussy lips had fallen open and I instinctively began to slowly grind my hips against the probing of his tongue. I just couldn’t help it……god he made me horny!
“ Jesse…..that feels so good…….you know if you keep that up you are going to make me…..”
Jesse had pulled his mouth away from my pussy and leaned forward to give me a full, wet kiss on the mouth. His tongue swirled my pussy juices all around the inside of my mouth…..and I loved it! My sex tasted so good, and Jesse’s kisses were making me so hot, I knew what I had to have!!
As we kissed, Jesse pulled my tight uniform sweater up to my armpits. He slid his fingers under the bottom seam of my white sports bra and pulled it up over my tits. I let out a sigh as both of my swollen boobs fell free. Jesse broke our kiss and took a few seconds to look me over. My nipples were so hard they almost hurt! Both of them were sticking out as long as the tips of my little fingers. I let out a moan as Jesse covered the right one with his mouth and began to suck and nibble on it. He was rolling my other nipple between his thumb and finger and was pinching it quite hard.
“Oh god…….your nipples are so long……just like they said they would be…..!” Jesse whispered between kisses and bites.
“Huh? Who said?” I tried to think.
Just at that time, Jesse went back to eating my aching, hairy cunt.
“Oh Jesse…..yes…..oh yes…..don’t….stop this time!!!” I whispered heavily.
By this time, I was laying back on the taping table with my sock covered feet on Jesse’s back and my hands were holding his hands tight to my burning nipples. I was lifting my hips off the table at the same time I was trying to pull him tighter, and tighter against my pussy. I pulled my hands away from his and Jesse began to squeeze my tits a little bit harder as I felt him suck my stiff clit between his front teeth and gently bite down.
“Oh..fuck..Jesse….here I cum!!” I moaned just as my whole body shook and I felt my hot juices squirt out into Jesse’s mouth!
“Uh! Uh! Uhhhhhhh!” I groaned as the orgasm rocked through my body! “Oh my, baby!”
Jesse kept flicking his tongue over my super sensitive clit until I had cum once more and just couldn’t take it any longer. Sadly, I had to beg him to stop!
Jesse was wearing a big grin when lifted his shiny face from between my legs and stood in front of me. He started unbuckling his belt and unzipping his pants while I just stared at him in my orgasmic haze. He’s going to fuck me I thought! And, I wanted him to so badly!
Jesse succeeded in getting his jeans undone and pushed them down to his knees. I could see the bulge in his underwear and couldn’t take my eyes off it. After what seemed a lifetime, Jesse finally pushed his jockey’s down and his beautiful, hard cock sprung free. Much to my delight, Kimmie had been right…he was wonderfully hung! Oh my!
Without thinking, I reached out with my legs and began to stroke Jesse’s throbbing shaft with my sock covered feet. He moaned his approval. I don’t know what it is, but all the guys I have been with simply love the sight and feel of the soft, white, ribbed ankle socks that we wear as part of our cheer outfit. Guys like them so much that just about all the girls in school wear them on a daily basis. I am not sure why they get this sort of reaction, but I was happy about what they were doing to Jesse!!
Jesse stood in front of me and let me continue to give him a slow, deliberate, sock job. His cock was wonderful. It was the longest and thickest dick I had ever seen, but then I was still only fifteen years old and didn’t have a lot to compare it to! It had a pretty, dark pink head that was bullet shaped and looked like it would be wonderful to have in my mouth….and I sure hoped that I was going to get a chance to do that some day!!
“Do I need to wear a rub……” Jesse started.
“Oh……no!” I finished hurriedly. Little did Jesse know just how badly I wanted to feel his hot cream being pumped into me……and dripping out of me for the rest of the night! And how I wanted it, no….needed it, as soon as possible!
Letting him know how badly I wanted him to fuck me, I stopped my sock job and dug my heels behind Jesse’s hips and began to pull him towards me. Jesse reached down and guided the head of his cock so that it nestled between my slippery, swollen pussy lips. I continued to dig my heels into his ass, pulling his thick tool into my wet, tight hole. I let out a quiet grunt as Jesse’s lovely shaft slid into me with ease….the only resistance being the tightness of my youth.
“Oh Jesse….you….are….so long!” I gushed, as after a few strokes I felt the base of his prick rubbing against my sensitive clit.
“ Do me Jesse….deep…….yeah, like that!” I whispered into his ear.
I love to talk as dirty as I can to a guy whenever they are doing me. I have always had this “Little Miss Goodie Two Shoes” reputation around the school and I think guys really get turned on when they find out just how slutty I can be!
Jesse laid down on top of me and we kissed deeply as he began to slide his beautiful prick in and out of my slippery, tight cunt. Jesse moaned as I kissed and bit the side of his neck. I teased his ear with my tongue as I whispered just how good his dick felt in me. I was trying to rub the softness of my sock covered feet along his legs the best I could when I felt him begin to pick up the pace of our fucking. I was so turned on by the whole situation….having sex with my “senior crush”…….in school……in my cheerleading uniform……before a game I had to cheer at……that my pussy was simply gushing with my juices…..so much so that we were making squishy noises every time Jesse pulled out of me and then sank his tool deep inside me!
After a few minutes of heavy kissing, fucking, and moaning, Jesse pushed himself up off of me and stood between my spread legs with a sock covered ankle in each hand. I pushed myself back up onto my elbows so I could see too, and when I looked down between my legs, I could see that my swollen pussy lips were stretching out from my bush about an inch or so up Jesse’s shaft when he pulled out of me. Both Jesse’s and my pubes were soaked from all the pussy juice I was leaking! Woozy with lust from just watching, I laid back on the table and began pulling on my nipples….that sent a shock wave right down to my clit and I gasped as another orgasm swept over me.
“Oh god Jesse…..cum in me now……shoot your hot load up my pussy….” I grunted out like a whore in heat. I could feel the walls of my pussy squeezing his cock hard after my orgasm. “Do it baby…..do it!”
Jessie let go of my ankles and put his hands on my hips. I again dug my heels in his ass and pulled him hard against my cunt as he began to slam his cock in and out.
“Mary….I’m gonna cummmmmm…..uh….oh!” Jesse gushed out and I felt my insides warm up as his thick dick spurted his salty cream deep into my vagina……and again…….and again.
Jesse collapsed on top of me and I gently kissed his face. I let my legs relax and hang off the edge of the table. After only a few seconds he pushed himself back up to standing and his softening dick pulled out of me with a quiet plopping sound. I just lay on the table not quite knowing what to do. I could feel Jesse’s cum leaking out of me and I just didn’t want any of it leaking onto my skirt! I sat up on the edge of the table and pulled my sports bra back down over my swollen tits. After I had pulled my sweater back down, I hopped down onto the floor.
“Oh my god Jesse, look!” I whispered excitedly.
I stood in front of him with my legs slightly spread and holding my short cheer skirt up to my waist. A big gob of Jesse’s cum was leaking out of me and was leaving a long string of jizz from my cunt to the floor! I squeezed my pussy muscles and squirted out another big gob which splashed onto the floor…..missing my sock by about an inch! Jesse and I both started laughing as I looked for something to wipe our mess up with.
“Just leave it Mary…..it’ll be a special surprise for whatever player comes in here tonight to get taped up!” Jesse laughed.
“Yeah, sure Jesse! I am pretty sure some football player is going to get really turned on when he steps in a puddle of your cum!” I teased. “Oh god…..look at the table!”
There was pretty big puddle of our cum pooled up on the edge of the taping table. How I had managed not to slide through it when I hopped off the table was beyond me.
“We’ve got to wipe that up!” I giggled as I grabbed a towel off the edge of the whirlpool and wiped up the mix of sperm, pussy juice and curly hairs. I threw the towel into the whirlpool where there were some other towels piled up.
I picked up my little white thong and pulled it back on, adjusting it the best I could over my swollen pussy lips and sticky bush. I felt its tiny back strap pull up next to my cum covered asshole and the feeling kind of turned me on! I grabbed my spandex cheer panties and pulled them back over my thong and adjusted them so I was sure I didn’t have any stray pubes showing. I sat down on the nearby bench and put my cheer shoes back on and made sure my socks were slouched around my ankles just perfectly. I quickly rinsed my hands under the faucet next to the whirlpool tub. I looked in the mirror on the back of the door and quickly readjusted my ponytail.
“There…..I think I am already to go. Jesse……are you going to wash off at all?” I asked innocently.
Jesse took a step near me, pulled me close and gave me the sweetest kiss ever.
“I don’t think I want to wash you off of me for quite some time baby…” he answered.
My knees got weak. I know……pretty corny, but remember, I hadn’t even turned sixteen yet! I swooned!
I took a step towards the door as Jesse snapped the lock open and started to step out into the hall way when I realized just how squishy my crotch was.
“Oh-oh, Jesse…..I sure hope you don’t start leaking out of me too much while I’m cheering! What would people think?” I teased.
“Maybe they would think you should have studied harder for your Geometry test!” he laughed as he kiddingly punched me in the arm and took off down the hallway.
“One point Larson! That’s all it was….one point!” I yelled as I chased him down the hallway. But maybe……..just maybe, I wouldn’t be studying so hard for next week’s test after all !!