Sexcapades of a Shy Guy – pt. 1 [MF]

Disclaimer: This story and most I intend to write involve infidelity. If that’s not your cup of tea, please move on to the next post.

So, the backstory. I have always been a shy guy. Quiet. Well-mannered. Qualities that don’t serve one too well in the dating game. But a combination of growing up in a broken home and getting access to porn at too young an age led to some sexual deviancy that would inevitably lead to some pretty entertaining stories.

This first story is how it all started.

It was my senior year of high school. My girlfriend at the time, Stephanie, and I had been dating since 7th grade. She was big into saving it for marriage. We lived in a small rural town in Ohio with pretty traditional values, so it wasn’t abnormal. And for the most part, I didn’t really have a problem with it.

Until I met Alyssa.

Alyssa was a sophomore. Alyssa was hot. Hotter than Stephanie. Alyssa was one of the only Hispanic girls in the school. She had big brown eyes, the dark hair and dark skin, as well as the curves to match. But she never left her boyfriend’s, Danny, side. Also, we’d never spoken.

She didn’t really speak to anyone, that I’d seen. So on a random Saturday night in April, when my buddy said we were going to go pick up Alyssa, I was taken way off guard.

“Alyssa who?” I said.

“Little Alyssa. The sophomore.”

“Uhh, alright then.”

We grabbed Alyssa from her house and headed to a local park, where the 3 of us chatted into the early morning hours of Sunday. My initial impression was that, not only is she hot, she’s smart. Really smart. And I was intrigued.

After I dropped my friend off, it was time to take Alyssa back to her place.

“Do you want to hang out for a bit?” She asked.

“I’m not sure Stephanie would I approve.” I joked.

“Danny probably wouldn’t either. But I won’t tell if you don’t tell. And it’s not like we’re doing anything.”

I wasn’t going to argue. We spent the next few hours on the trampoline in her backyard.

She was making it hard to not make a move. In the 5 years I’d been dating Stephanie, I had had plenty of opportunities to cheat on Stephanie. And I’d prided myself on my track record.

But something about Alyssa was different. And before I knew it, my mind was made up and I went in for a kiss.

In that moment, Pandora’s box was opened. And suddenly, Alyssa was on top of me, grinding hard against my cock.

Had she had her way, we would have fucked right there that night. But, it was too much. Before things could go further, I came hard from her grinding and all the sudden realized wtf I was doing. I gently pushed her off and told her I had to go.

Over the next few weeks, she was all I could think about. We’d pass each other in the hallways at school, still pretending to not know each other. We’d link up and make out when we could. But with her strict parents and both of us in long-term relationships, our moments were few and far between.

The best time to see each other turned out to be late night or morning before school. Both of our dad’s worked third shift, and my stepmom didn’t pay any attention. So I’d either head over to Alyssa’s late night after our dads had left or before school in the mornings.

One particular morning was different. We finally fucked. I won’t bore you with the details, because let’s be honest, who’s first experience is really THAT hot?

But after that we fucked like rabbits whenever we could. My inhibition was gone and I’d considered the internal battle with guilt about cheating a wash, so there was no more reservation.

Alyssa tried pitching to me that she was a virgin at first too. And I believed her. Initially. In retrospect, I know it was a lie. At the time, I wanted really badly to date her. Because, shit, she took my virginity. But she usually just brushed off any convo about us getting serious. I was being used. But I was using her too. So all was well.

My favorite time with Alyssa was probably when she was house sitting for her grandma. She had a friend staying with her, but we knew an opportunity when we saw it so she invited me over one night. I got there and she answered the door in just lace panties and a t-shirt. Not discreet at all, so I assumed her friend knew he deal, despite her friend knowing we were both seeing people.

It was also the first time I really got rough with her. Or any girl for that matter.

After her friend had fallen asleep, she drug me into one of the bedrooms and told me she wanted it hard.

Not really knowing what to do, I just referenced the porn I’d seen.

I grabbed Alyssa by her hair and planted her head onto the bed, so she was bent over, feet on the floor. I pulled her panties aside and started rubbing her clit, while my other hand held her head down on the bed. I remember how soaked she was.

“Hold these out of the way.” I said.

“Will you spank me?” She said.

As a shy, inexperienced dude brand new to the world of sex, the first time you hear those words it is like a paradigm shift. At least, for me it was.

But damn, did I enjoy it.

After a few firm hands to both sides of her ass, I couldn’t take it anymore. I shoved my cock in her and held her down until I pumped her full of my cum. It was the first time I’d fucked her without a condom, but I didn’t care. Neither did she.

Eventually word about Alyssa and I got out. Her and Danny broke up, and when summer came, Alyssa disappeared. She blamed me for word getting out and wanted nothing to do with me. She wouldn’t return my texts or calls. I later found out she had spent the summer with her Mon in Indiana.

Stephanie wanted to stay together and “make things work.” But I broke it off, because we both had plans to go to different colleges later that fall. I knew I had no shot at staying faithful.

Source: reddit.com/r/gonewildstories/comments/rb33wy/sexcapades_of_a_shy_guy_pt_1_mf