The High School Reunion and The Hot Cheerleader [M/F] (long)

Hey all, it’s Jonathan again. I’m here to excite you with another sumptuous story of my wonderful sexual encounters. Hold on to your junk tightly, this is a good one. (skip to ****** for the good stuff)

It all started when I attended my 10 year high school reunion. I went to a small high school in a small town, only about 100 per graduating class, so I knew most of the people in my class pretty well. Small towns are great for a couple things, you know everyone’s business and it’s boring as hell. Thus, you know who’s fucking who and that’s all you have to do. Let’s just say the small town women know how to keep you warm at night. (and some of the guys too, not my thing though)

Most of my classmates and friends had moved away to bigger cities for better jobs, but the class got along really well so the reunions were highly attended. I arrived at the 10 year reunion still single, after being divorced some years earlier. Not my ideal situation, but a bunch of my guy friends were single too so I figured we would have a good party. I had no expectations for a hookup, as the small town didn’t offer many good options that weren’t taken.

The day started off with an odd encounter, I pull into town and stop at my dad’s house to say hi. I’m not staying there, instead I am staying at my mom’s house across town, they’re divorced. As I walk into my dad’s kitchen, they are sitting around the bar having a drink and I notice one of my classmates, Anna, sitting there with my stepmother and my dad. Anna is radiant, and it causes me to just stop and stare for a moment. I finally collect myself, and tell Anna hi and let her know it’s a wonderful surprise to see her there. Really, other than a wish of mine maybe being granted by the gods, I had no idea why she would be in my dad’s house. As far as I knew, they didn’t even know each other. Turns out her family is lifelong friends with my stepmother, who I barely know, and they just ran into each other at an event so they came back to chat. Okay, so that is cool, the hottest girl of my high school class is hanging out at my dad’s house. Good start to the weekend.

Some back story on Anna and I, we were always friendly in high school but we probably only hung out a few times together. Her brother was in football with me, and she was a football cheerleader, so I knew her family from that. It was a fact that every guy in high school wanted to fuck her, she was actually voted “hottest body” in our senior yearbook. Nobody gave a fuck about PC back then. And it was true, she was so damn hot. About 5’2”, maybe 110-115 lbs, probably a size 2 but with 32D boobs, dark brown curly hair, beautifully round ass. Always smiling, always happy to see me and give me a hug. For a similar visual, [see Andie Mcdowell in this pic]( http://3.bp.blogspot.com/-0XDefyHtC-4/ThGxvI6XiLI/AAAAAAAAEo8/UsbOfKMVU4s/s1600/Andie-Macdowell-2800X2100-283.jpg) [or this pic]( http://www.gotceleb.com/wp-content/uploads/celebrities/andie-macdowell/in-tight-jeans-in-brentwood/Andie%20MacDowell%20hot%20in%20jeans-02-560×801.jpg), Anna has the same body type, hair, and great smile. Needless to say, she is exceedingly lovely and attracts a lot of attention as she likes to wear some tight clothing on a night out. And to go with the ridiculous sexy body of hers, she may be one of the nicest people I have ever met. She teaches middle school and projects a radiant beam of happiness to everyone around her.

As I make myself comfortable in a chair next to Anna, we start chatting. After a while, my dad and stepmom take off for some other engagement. I can’t really remember what Anna and I talked about, I just remember having this beautiful woman who I spent years lusting after in high school just hanging out with me. We both had long term relationships the last couple years of high school, but I don’t think I would have asked her out then. Her hotness was just too intimidating back then. However, 10 years later I have a lot more experience and confidence. And the years have clearly shown which guys turned out to be losers and which guys got their shit together. I’m the latter.

Eventually, Anna has to run to visit her parents and we say our goodbyes for the afternoon. I know I’ll see her out later as the class is getting together for some drinks. There wasn’t any overt flirting going on, and I wasn’t trying as Anna was married, or so I thought. (Small towns + married women = shotgun in your face. I know.) A few hours later, I receive a Facebook message from Anna’s best friend informing me that Anna had got divorced a year earlier. I don’t think I have ever received better news! I guess Anna didn’t want to come out and tell me that directly and I never thought to ask.

Anna’s best friend suggests the three of us go out to dinner before we meetup with the rest of the class for drinks. I am definitely down for that. We go to dinner at this nice Italian place and order a bottle of wine. After a glass of wine, Anna’s friend excuses herself and says she has to go check on her kids. Pretty sure this was all just a plan on their part so that Anna and I would have dinner to ourselves. I can’t argue, as Anna is a breath of fresh air in my dating world. We talked, flirted, and laughed for two hours before we realized we were late for the class social.

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The class reunion was as expected, we had about 2/3 of our class there. Lots of memories and fun times with good friends. Anna and I showed up together, so that got the small town talking! Then, we split up to mingle, though we would gravitate back to each other every once in a while. I started whispering short comments in her ear whenever I was near her. I started out by telling her how wonderful it was unexpectedly seeing her that day. How it was a fantastic surprise to get that message from her friend. Then, I started complimenting how she looked. She had a tight black pencil skirt on with a form fitting top. Everyone knew this was the hottest girl in the room. I whispered how hot she was. Then I started whispering about what I wanted to do to her. With each whisper, they grew increasingly sexual, and she responded delightfully with each comment I made. By the end of the night, when most people had left we were sitting on two bar stools next to each other, face to face staring in each others eyes. We couldn’t keep our hands from flirtatiously touching each other, a brush of the forearm, my hand on the small of her back, her hand on my inner knee. By then, we both knew we wanted the same thing.

But, we had a huge problem! I was staying at my mom’s house and she was staying at her parents’ house. We had nowhere to go. When the bar was closing, so this is probably about 2am, I suggested we head over to the park in town for a late night walk as neither of us wanted the night to end yet. We made our way over there and walked around the park for a bit, it was a full moon in an unlit park. She gently intertwined our hands as we walked. After a few minutes of walking to a sufficiently dark area, I mentioned how beautiful the moon looked. As she looked up at the moon, I pulled her into me and started kissing her. She reciprocated with a passion I hadn’t felt in a long time.

As we were making out, I was caressing the body of this girl I had dreamed about years earlier. I slid my hands down her back, over her ass, and then inside the back of her skirt; where I discovered she had a very tiny thong on and I had free access to caress her bare ass. I also started tracing the edges of the thong in her ass, that sent little trembles through her petite body. She was also very explorative with her hands, she slid her hand down the front of my jeans and gripped my already hard cock. Just the feeling of her hand on my cock was a sensation I will never forget, she was an expert at touching and knew how to turn me on. I whispered to her that I was going to fuck her right there in the grass. She would have let me at that point, as I had slid my other hand down the front of her skirt, past the front of her lacey thong, started rubbing her clit and then discovered her complete wetness.

But, then we had another problem, it started goddamn raining! WTF was going on! I have the chance of a lifetime to fuck the high school dream girl, albeit 10 years later and karma seems to be trying to cock block me. No idea why karma was doing that to me, I try to be a good person…

Anyway, Anna whispers in my ear that we need to get out of there and go somewhere else NOW. I have no idea where, so I tell her to hop in my rental car and we’d find a place. We drive around for 10 minutes until I find a completely dark road with no street lights on the edge of town, there are 1 or 2 houses on the street but they are a good distance away and there is no reason anyone would drive down this street. I tell her to hop in the backseat and she does in a blink of an eye, luckily the rental car is something like a Pontiac Grand Prix that has a decent size back seat. I laid her down in the backseat and started passionately kissing her. Damn, she had the most amazingly soft lips and exquisite neck of anyone. I nibbled and sucked on her neck, turning her on like crazy. She was begging me to fuck her at that point. I slipped her top off and she quickly removed her bra, exposing her beautiful mounds of joy. Her nipples were dark, perky, and sensitive. I provided ample stimulation to her beautiful breasts with my hands and tongue, not allowing a single inch of them to go unstimulated. I think she could have come just from me swirling my tongue on her nipples. But, I relented and started to kiss my way lower.

As I kissed her stomach and continued on down, she unzipped the back of her skirt, I grabbed the sides of it and, as she wiggled her hips a little to help, I slid her skirt and thong off in one swift motion. She was now completely naked in front of me. Due to the full moon, there was still plenty of light to be able to take in the astounding features of this beautiful woman laying before me. After I captured her naked image in my head, I kissed lower and followed her landing strip to her clit. Before I got the chance to dive in, she pulled me up, kissed me on the lips and told me to get naked right then. I did as instructed.

Once naked, she gave me a handjob to make sure I was hard. It wasn’t needed. She begged for me to fuck her. I pushed her legs up so that they were over my shoulders, and started teasing her pussy a little by rubbing the tip of my cock on her lips. But this is something I wanted so much, I quickly sunk my cock deep into her pussy. She let out a moan of pleasurable relief. I held there, without pumping for what seemed like a minute or two. We kissed and made out like crazy before I started thrusting.

Her pussy was so warm and wet, it was enticing me to come from the very beginning. I wanted this to last as long as I could, so I slowly pumped my hardness in and out of her. We picked up some speed as we went, she especially loved running her hands all over my chest (I am very broad shouldered with a strong upper body). Every once in a while, I would stop just to make out with her and let my edge die down. I kept this up for what seemed like an hour. (this is why you twist one out before any big dates guys.) We just kept fucking and fucking, as I shifted the positions a little, as much as we could in a backseat.

Side note – If you noticed, neither of us bothered to ask if we had a condom. Thus, I was bareback and she didn’t care. At the time, I didn’t care either. I actually remember thinking, while fucking her, that if I knocked up the hottest cheerleader from high school when we were almost 30, then I would live with it as it was worth it. I found out later she had an IUD, so she was at least being smarter than me!

At one point, I was still fucking her missionary-esque, I noticed we had shifted her legs into a weird angle in the backseat. Her right foot was touching the back passenger window, while her left foot was flat against the rear window; I guess she had not lost that flexibility from being a cheerleader. It was so hot, her tits were bouncing back and forth as I slammed into her. I almost came, but I had an amazing amount of self control that night. I abruptly stopped, she looked at me confused and I told her I never got the chance to taste that beautiful pussy of hers.

She laid her head back and gave out a loud moan as my tongue applied a long, continuous stroke of her pussy lips and clit. I then buried my head in her pussy, and licked and sucked until she squirmed so much I had to stop. At that point, she said it was my turn, she easily flipped over me and had me sit with my back against the door with one leg extended on the backseat. This gave her explicit access to my cock and balls, as she took them into her mouth and played them like a professional. And the stroking, she really knew how to slowly stroke a cock, keeping just enough pressure to be exciting but not hurting. For some reason though, maybe due to the door handle jabbing me in the back, I just was not going to come from a blowjob that night.

I had her lay back down, as there wasn’t enough headroom for me to comfortably do doggy, and I quickly guided myself back into her welcoming pussy. She hadn’t been with anyone in a while, and neither had I, so we were both letting out a lot of sexual build up. I kept fucking her for what luckily seemed like eternity since I had not come yet. She starts telling me about how she hates condoms and wouldn’t have let me use one even if I wanted to. And she begs me to blow my hot cum deep inside her.

The dirty talk really got me to the edge, so I started massaging her clit as I wanted her to have a big finish also. She loved a little circular motion with my thumb, especially when I dipped my thumb lower to coat it with her juices and brought them up to her clit. She was bucking wildly at this point and her pussy started convulsing, and I am certain the whole car was rocking, as I unloaded every drop of cum insider her beautiful quivering pussy.

After a few minutes of rest, a car drove by and scared us to get the hell out of there. We quickly dressed and I dropped her off at her parents’ house about 6am. We were both pretty worthless the next day on only 2 hours of sleep, but we were in lustful bliss. Anna came to visit me (I was living half the country away) a few months later and that is when I discovered her kinkiness, which may be the next story.

See ya next week, same fucking time, same fucking channel.

Source: reddit.com/r/gonewildstories/comments/4vn2n0/the_high_school_reunion_and_the_hot_cheerleader