Saddle Up: A Rough Recollection

My high school Italian teacher once told me that aside from graduation, the biggest moment in my life would be losing my virginity. Despite the fact that life has been fucking me over since I was born, I never expected to lose my V-card during high school. I knew that it was imminent, so in order to prepare myself, I just watched a bunch of porn each day to make sure that I would know what to do in bed. 

On a normal Tuesday summer morning, I woke up to a text from my boyfriend at the time. He asked me if I wanted to hang out. Since we were still in the first week of our honeymoon phase, I jumped at the opportunity. He gave me a half-hour to ready myself, and I bolted to the bathroom to shower. To me, cleaning myself up before seeing him was always courtesy, so I made sure to get all the grime from the previous day off me, thinking that today was going to be THE day. Being his usual self, he was outside my house 10 minutes early, and I lied to my dad and told him that I was going to practice. 

The sexual tension between us was insane on the car ride over. He took me to his mom’s house and showed me around before going up to his room. He said that he just wanted to cuddle, so I went along with it.

“Before we got this house, there was a train conductor who lived here,” he told me. “He died in my room.”

Clearly, that statement put me in the mood, and he graciously continued on, telling me that he would often wake up in the middle of the night hearing a train horn. I wasn’t horny anymore at that point. Seeing the crucifix of Jesus in his room also wasn’t helping.

He quickly pushed me down onto the bed and began kissing every inch of skin above my upper torso. As great as it felt, I never liked not being in control, so I turned the tables on him. For the next few minutes, it was a fight between us to pin each other. At one point, he even took his belt off and started whipping me. I’m not gonna lie; it really turned me on.

“Close your eyes, I got a surprise,” he told me. 

Suddenly, I felt something being wrapped around my wrist. When it clicked, I opened my eyes to find that he had handcuffed me to his bedpost. He told me that he'd picked them up as a special gift from Spencer’s, ordering me to stop struggling when I began trying to break out. Cheap handcuffs, however, were very easy to break, and I found myself pinning him down and having my way with him.

After a while, he asked the big question: “Can we have sex?” I told him my whole spiel about how I wanted to know that I would be losing my virginity to someone who loved me, and he told me he did. I figured I didn’t have anything to lose, so I gave him the OK by kissing him.

He walked over to his pencil case and pulled out a condom. Rolling it onto my penis, he told me that he didn’t have lube but to just go with it. For 20 minutes, I tried to stick it in, but it just wouldn’t budge. Each time I tried to push in, the bed kept shifting and he fell onto the floor at one point. In the end, we resorted to using spit, and eventually, it went in. 

Unlike the porn I watched, our sex was not clean or composed. I watched my pale boyfriend hit every color from pink to tomato red trying to bottom, and at one point, he slipped off the bed again. I even tried dirty talk to get us more in the mood, but I couldn’t help but start laughing hysterically when I tried. We attempted several positions until I suggested that we just blow each other to finish.

“How does it not feel to be a virgin anymore?” he giggled.

“I think the bigger question is when you’ll be able to walk straight again,” I replied as I saw him cowboy-walking out of the room.

—Amazing Al

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