The Cheerleader's Rebound [m/f] | 2016

I've read plenty of stories on this sub and I've finally decided to share a couple of my own. I've never written a story for an audience before so any feedback would be appreciated. I'm just writing these out as an excuse to work on my writing skills and share some of my favorite sexual experiences. Enjoy.

UPDATE #1: I'll just start linking all my stories together. You should find links to each story at the beginning and at the end.

I promise I won't be splitting a moment into separate parts, but every significant moment I have with a person will be separated as a different story on here. Not really sure how many of my memories I'll write in total, but I already have a couple specific experiences and people I want to write about. Hope you everyone is enjoying my memories as much as I have.

High school was an interesting time for me. I was a shy dude and mostly kept to myself. I stuck with my small group of friends, but really didn't go out very much with them outside of school. Social situations made me incredibly nervous. Despite my awkwardness, girls still found me attractive. I dated a couple girls, but none of those relationships lasted more than a few weeks. They never evolved into anything more physical because I was too nervous to make a move. All of them gave up trying, except for Amy.

I met Amy for the first time in a history class during my sophmore year. She was a cheerleader for the entirety of high school. The best way to describe her is boobs. She was a short, skinny brunette and her small frame seemed to make her tits even bigger. I went to a private Catholic school and just watching her strut into class in our school uniform made every dude's head turn.

We had assigned seating and we ended up sitting next to each other. Our history teacher was lazy and he just made us do work with our seat partners for most of the time. I ended up having to work with Amy the entire semester. We spent most of that class playing games of Pictionary and just talking. Socially, she was my complete opposite. She was very outgoing and we'd have conversations about everything. She'd occasionally vent out her problems with her boyfriend and I'd just listen. She liked that.

We were in different cliques so we didn't talk very much after that semester ended. We ended up having a math class together in our senior year. She took a seat next to me and our games of Pictionary and limitless conversations continued. She still vented to me about her boyfriend and things seemed to be escalating between them until they finally broke up early into senior year. She was pretty devastated about it.

We were encouraged to exchange numbers for the math class so that we could help each other out. After Amy's break-up, she started texting me to hang with her. Despite my nervousness, I agreed to hang out with her so she could keep her mind off of her problems. I'd pick her up and we'd go to the mall, watch movies, or just sit on the roof of my car and talk. She'd make jokes about how she knows she makes me nervous. She laughed when I revealed how my palms get sweaty whenever I talk to someone. When she made fun of my weird quirks, she never did it in a demeaning way. She actually thought it was cute. Hearing that come from her definitely gave me an ego boost.

One day, Amy texted me that she really needed help on some of our homework and she invited me to her place to so we could work together. I drove over, knocked on her door, and was immediately welcomed by Amy dressed in her cheer shorts and a tight shirt. My eyes immediately wandered up her tone legs, to her tight waist, and then to her boobs. She wasn't wearing her bra which made her nipples visible through her shirt. She just laughed and brought my mind back to reality. She knew I was checking her out.

Amy went straight to business. Math business. We actually started working on her living room couch, side-by-side. As we were working, she slowly started to scoot next to me until our thighs and shoulders were touching. The tension made my cock rock hard. I think I knew what she wanted, but I had no idea what to do. She made the decision for me.

Amy said she needed a break and got up to get some water. She came back, laid herself on the couch, and rested her feet on my thighs. She gave this devious smirk and she told me that her parents wouldn't be home for awhile. She asked me if I wanted to do anything else. I couldn't respond. She asked me if she was making me nervous. She grabbed my hands and laughed when she noticed my palms were sweaty. She then moved both my hands to her boobs. I started circling her nipples with my fingers. She moaned softly when I started doing this.

Amy asked me if I had ever done anything like this before. I answered honestly and told her it was my first time. She gave me this look of excitement and quickly straddled me. We started making out while she rubbed her ass against my dick. She took my hands and moved them to explore every inch of her body. I rubbed my hands up her smooth legs, up her flat stomach, massaged her boobs, and then finally she moved my hands to the back of her head. All these years of sexual tension were finally released. Our kisses were slow and passionate. We took the time to explore each other's mouth with our lips and tongues. Whatever she did to me, I mimicked right back.

Amy took off her shirt and laid back on the couch. We continued making out while I was on top of her. She started to guide me head down her neck with her hands. I kissed and licked my way down her neck and chest until she lead me to her boobs. I started to massage her boobs while my tongue focused on making circles around her nipples. She moaned as I did this and each moan encouraged me lick faster and suck harder.

Amy then grabbed my chin and forced me to look up at her. She asked me if I had ever been given a blow job before. She wanted to hear me say that I'd be getting my first one. She ordered me to sit up straight on the couch. Amy kneeled on the ground in front of me and lowered down my basketball shorts. She started licking up and down the length of my cock. I was in complete ecstasy.

She moaned as she took my cock in her mouth. She deep throated me and choked on my dick. I was so turned on. At first, she started bobbing her head up and down while her lips tightened around my dick. Then, I grabbed her head and started thrusting into her mouth. She just looked up at me and smiled. She took her mouth off my cock and told me to cum in her mouth. After she said that, it didn't take too long to do as she ordered. I thrusted a few more times into her warm, wet mouth and gave out a loud moan as I came. She swallowed every drop.

She immediately kissed me afterwards. It was weird since I could still taste a bit of my cum as we made out, but I thought it was still hot at the time.

We quickly got dressed because she said her parents were coming home soon. As I got ready to leave, she told me that I owed her next time.