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Playtime with Andrew (Repost)
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Someone suggested I repost, since this doesn’t seem to have posted the first time. Enjoy!!

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Hi again! I hope you’ve all enjoyed my previous stories. This time, I thought I’d tell the story of how I met my second boyfriend, the one who really changed dating for me (though, not in a great way.) As always, names have been changed but this is all based on my real experiences.

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It all started at the beginning of my last year in college. The biggest change that year was that I’d been moved to the larger, newer dorms on campus and had a roommate again for the first time since my freshman year, so that took some getting used to.

The first week of school was mainly for freshmen to get a sense of the campus. Move-in was on a Saturday, but classes didn’t start until the following Thursday. The whole first week and a half on campus are kind of cool, with lots of events to get new students excited about the school and life in the dorms. The weekend after move-in, student staff threw a huge party at this dorm, ending with a staff talent show at the end of the night. During the events earlier in the day, I’d run into some of my friends who also lived in the dorms, and we ended up hanging out for some of the festivities. This group also included a few freshman students.

One of these freshman instantly caught my eye. His name was Andrew. He was a couple inches taller than me (which I LOVED! I’m 5’11”, and it’s rare that I find guys I like who are also taller than me). He had curly light brown hair, fair skin, and a killer smile. I quickly learned that he was gay, and my heart started fluttering. As usual, I did my best to be subtle in my flirting. At one point, our group was all in Andrew’s room and someone suggested a game of Truth or Dare. The questions and dares were somewhat mild at first, but quickly got into taboo territory. When it was Andrew’s turn, he chose Dare, and a girl dared him to put on lipstick. Everyone laughed at first, thinking he’d chicken out, but he didn’t and quickly applied the girl’s lipstick as if he’d done it all his life.

Now it was his turn to ask someone and he chose me.

“Dare,” I said, which made him grin.

“I dare you to kiss me!,” he practically shouted.

I hesitated at first, only because of the lipstick, but quickly decided to go along with it. I mean, he was cute and I was definitely attracted to him. I made my way toward him, and we locked lips, kissing for what seemed like forever but was probably only a minute or two. All around us, our friends were hollering and cheering us on.

After that, we were nearly inseparable. We quickly realized that there was a mutual attraction, and started dating and spending lots of time in each other’s dorm rooms. My roommate ended up leaving school after only a month, so I suddenly had a large room all to myself, and we spent way more time in my room than in Andrew’s.

The sex was amazing (at least I thought so at the time), and we ended up fucking like bunnies very quickly. One time, he brought over a pair of handcuffs he’d bought. The afternoon started like any other: he came over after class, and after I’d finished my homework for the day, we got into bed and started kissing. We quickly became naked, feeling each other up. After a while, he pulled away, going to his messenger bag and taking out the handcuffs he’d brought. He put the key on my desk then clamped one half on my left wrist and the other on his right. We were locked together, naked, and both of us totally turned on.

Back on the bed now, we changed positions so that I could suck his cock. It was about 6.5”, average girth, and cut, just how I liked it. I played with his balls with my free hand, while playing his nipples with the other. Soon, he wanted me to ride him. I had to get off the bed to get to my dresser for condoms, which was a bit difficult since our movement was very restricted, but we managed. I got back on the bed, rolled the condom onto his cock, and slowly lowered myself onto him.

As he slid in, I could feel myself filling up. After resting for only a moment, I started going up and down slowly, gradually increasing speed. He also started bucking his hips upward, making sure he never slipped out of me. As I rode him, Andrew started using his left hand to jack me off, so I was feeling things all over my body.

It wasn’t long before we were both getting close. I started to hear the tell-tale moans coming from his mouth, and started riding him faster and faster, willing him to cum. He started speeding up on my dick as well, and we soon came together - him inside my ass and me all over his chest.

After we’d both come down post orgasm, I slowly lifted myself off of his dick and laid next to him. We held each other for a few minutes before our chained hands got uncomfortable, and we decided to remove the handcuffs and get cleaned up. It was then that we discovered that the key was gone! He’d placed it on the corner of my desk, but I guess during our rough fucking, the bed had knocked into the desk a few times, and dropped it onto the floor. It took us about half an hour to find it, both of us freaking out about how to remove the handcuffs if we couldn’t find it. He would’ve been fine running across the dorms half naked to find a way to get them off, while I was a bit more apprehensive.

While we both were freaked out about this situation, he seemed to get a lot more angry about me not wanting to be seen even partially undressed outside my room. Unfortunately for me, I didn’t see that red flag and brushed it off after we found the key and calmed down. It was one of several, in retrospect, that I ignored, and it certainly wasn’t the last. We ended up having a very on-and-off relationship, which I finally had to end after a very ridiculous fight.

When I’d first met Andrew, I was convinced that he would change my life, and in a way he did. After all the red flags that I recognized only in looking back on our relationship, I came to realize what I wanted out of a relationship. We never spoke again after we broke up, and I held a lot of anger toward him for a few years afterward, but eventually got the closure I needed to move on.

I’m sorry this doesn’t have a happy ending, but relationships rarely do in my experience. Ah well. You live, you fuck, you learn.

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4 years ago