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Highschool is a time to explore one’s sexuality for many, and I was no exception. I had many of my “firsts” during those years: from the first times I played around with boys in the college bathrooms, to my first stable boyfriend, and even my first lesbian experience.

This time I want to tell you about the first time I had anal sex. No one you’ll see mentioned in this story was underage.

My boyfriend at the time was a boy from my college, same age as me. He was my second boyfriend. We were had fun together but I would lie if I said that we were in love. That’s why it was not heart-breaking when we broke up in June, when college was over. We used to spend our summer break in different cities, so it was no surprise for anyone that it wasn’t meant to last.

So that summer, being single and wanting to have some fun, I went out with my friends dancing at all times. After a long day at the beach getting nice and tanned, me and my besties would get together at night to do our make up and get dressed for the club.

There was this one disco where we pretty much at all times went: it was quite close to us, so easy to reach without a car, and we liked being familiar with the place. It felt like it was “our” disco!

Since we became regulars, we made friends with the guy that managed the PR and sold tickets to get in. He was quite older than us, around 30 years old. Let’s call him Brad. He was there every night, and all my friends told me that he at all times checked me out. That was true and I had already noticed that, but to be honest he checked out pretty much all the pretty girls and had sort of a reputation about hooking up with girls that danced at his club.

Anyways, me and Brad were just friendly at first, but it didn’t take long before he started flirting with me. He used to compliment how my ass looked in my tight outfits, sometimes even touch it. I went along with it, I liked the attention. Moreover, being forthcoming with him came with its perks: he started giving us discounts, free drinks, free use of the cloakroom.

One time we were on the dance floor and he was dancing with us. He got close to me and pushed against my ass under the flashing lights of the nightclub. I made myself pretty available and let him touch me as he wanted all over my body, so at one point he turned me around and kissed me in front of my friends. I liked how confident he was with his tongue, and from that night I decided that I would let him fuck me to get in for free.

We used to fuck in his SUV, in the toilets, we even fucked at his place a few times.

One night Brad invited me last minute at the club promising me some sort of VIP access to an event and a table only for us. Me and the girls already had other plans and they didn’t want to cancel, so I decided to go by myself. When I got there Brad greeted me by immediately placing his hand on my ass and welcomed me in. He basically groped me all night while dancing and he got both of us pretty drunk because all drinks were on the house. The music was great that night and the club was filled with people because a trendy DJ was being hosted.

While dancing next to our private table, he kissed me deeply and touched me under my sheath dress. He slid his fingers inside my panties and started fingering me. We were in the VIP area, but that doesn’t mean we had no people around us. The lights were low, but we were in plain sight and some of the people sitting at the nearby tables even started cheering us on. Neither of us were particularly bothered by this, but Brad took me by the hand and dragged me through the club into a private dressing room. He said that it was for staff only, so we wouldn’t be disturbed.

We got in, he locked the door behind us and he immediately pushed me on my knees. I took his cock out of his pants and gave him a very intense blowjob while looking straight at him. Then he grabbed my head and took control, going deeper and faster in my mouth, reaching my throat. He was pretty big so I couldn’t take it all, but in his last thrust, he pushed his cock as deep as it could go. I tried holding it for a few seconds but I had to push him off, leaving my mouth drooling on the floor.

He pulled me up, pulled my dress up and bent me over. I was already very wet so he got it in effortlessly and fucked me hard from behind for a few minutes. He loved being rough with me, so he grabbed my hair and pulled it back while ramming his dick inside my pussy.

When his cock slipped out because of how fast he was going, he grabbed it and tried pushing back in, but met my other hole first. He said “fuck it” and pushed. It took him a few seconds to fully get it in my ass, but thanks to how I soaked his cock with the wetness of my pussy, he managed to do that. I screamed with my eyes wide open when his entire cock was inside my ass, getting accustomed to this new sort of pleasure. He slowed down a little as we adjusted our position, and I just followed his lead. I placed my arms on a nearby table to support myself because it was so good that my knees were shaky. Brad picked up his speed again, and my brain essentially turned off. It was so fucking good, and it was getting better by the second. The small fitting room was filled with moans and screams. After roughly 3 minutes he got closer to me, resting his chest on my back, and grabbed my tits firmly. His mouth was right behind my head so I could hear him grunting and moaning clearly. Most of all, I heard his groan when he thrusted deep in my ass, squeezed my chest and came deep inside my asshole.

He just stood there for a few seconds, and only when he got it out I felt how gaped my asshole was. His cum was dripping out of my ass, but I couldn’t prevent it because my body was frozen from pleasure. Moving a single muscle would have meant completely losing control of my legs, so I just stood there with my legs wide open and my knees trembling.

When I finally got back in control of my legs, I cleaned up and got dressed.

We got out of the dressing room and Brad told me he had a few things to take care of, so he left me with some friends of his that I had already met other times. He probably put off something he had to do just to get laid, which was classic Brad. Before getting back to his tasks, he managed to let me and his friends behind the DJ booth, which was really cool.

Now, what they don’t tell you about anal sex is that you can “feel the emptiness” in your ass after it, if that makes sense. Swaying around to the music with that “empty feeling” combined with the fact that I was still leaking cum in my panties… that was just amazing.

NSFW: yes

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