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How I Narrowly Avoided My First Experience With Anal

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How I Narrowly Avoided My First Experience With Anal

About a third of the way through my college career, I had a sexual awakening of sorts. I realized the women that populated my college’s campus were open to pretty much anything I asked them to do. I consider myself a modest man. I have sex about once a month, which I feel is average, I maintain a solid B-, and I strictly adhere to a seven drink-a-night policy. It was the same with my sexual appetite; I would dip my toes into the kink but never had any desire to do anything 50 Shades-esque. So, when I ran into, let’s call her “Chelsea,” I had no idea what I had gotten myself into.

Now, I knew Chelsea for a while before we started copulating, and on the surface she seemed like a normal, albeit hot, everyday coed. When I finally managed to bring her home to my apartment after a night of drinking, I was surprised by the deviousness of her desires. She liked to bite, which at first I was into, as I had never used my teeth in sex before. She also liked to be choked, which I was not into. I was absolutely terrified I was going to end up on the evening news for manslaughter and firmly entrench myself as Big Jim’s Thursday boy in prison. Those pale in comparison to what she had in mind next.

At some point during our “love making,” she stopped me and produced a rather large silver egg looking thing from her sick bag of sexual tricks. I had no idea where it came from, what its purpose was, or what it wanted. She, while wearing the biggest shit-eating grin I had ever seen, held the silver egg thing up to my face and asked me, “Are you into penetration?” Now being a greenhorn (I was a late bloomer), I thought, “Absolutely, how else is sex done besides penetration?” So I answered with an emphatic nod. She began to maneuver herself in bed to a sitting position, cradling the silver egg thing like a precious little grenade. It was only when she whispered, “You’re going to love this” that I realized the silver egg wasn’t going in her. That sucker had my name written on it. The silver egg thing wanted me.

I pride myself on staying cool in stressful situations, and this one was no exception. I took a deep breath and screamed with everything I had, like a small child who was watching his ice cream drop off his cone, except the ice cream was my anal virginity. To my absolute horror, my shouts only made the harpy creature sitting on top of me giggle and keep moving in order to get the best shot into my anus. Realizing Chelsea had no intention of stopping despite my frantic arm waving and continuous stream of mumbled pleadings, I threw her off me and ran to the corner of the room with my hands covering my ass like a shield. I thought I was safe.

Chelsea rose from the bed like a phoenix, a demonic, deranged, brunette phoenix. Cackling like a clown (I hate clowns), she slowly made her way over to me, knowing I was cornered, and her prey had nowhere to go. Up to this point in my life, I had been in a couple fights, but never against a woman. The lesson I quickly learned was this: Women fight dirty, like Ndamukong Suh dirty. She dug her fingernails into the skin of my thighs and pushed me into the living room. I’m not a small guy, but Chels was strong. She grappled with me for close to a minute before shoving me near the couch that adorned one side of the room. What she did next was straight out of a Bruce Lee movie. She got her foot around my leg and did some sort of judo combo on my chest to push me down on the couch while using her other arm to position the silver egg insertion side up right beneath my ass.

I fell like a majestic redwood to a chainsaw, knowing that when I hit the cushion, my watertight seal was gone forever. I could only accept my fate, like the scene in Saving Private Ryan where Jackson yells at Parker to get down before the Tiger demolishes the bell tower they’re in. Nothing left to do but wait for the end. I had always thought I would lose my elasticity in some foreign country facing the choice of a long stay in the South American equivalent of Gitmo or crossing the border with a kilo in my crack. This was it — the hollowing of my soul would come at the hands of this girl.

I let out a low rumbling squeak as I hit the couch, pain exploding into my psyche. After a few moments of shock, it hit me: She missed. The silver egg thing had missed my butthole and had instead nestled itself in my taint. A wave of relief flooded over me. I had walked the razor’s edge and survived, but damn did that thing hurt. A thin smile spread across my face, a smile that Chelsea took to say that I was enjoying the experience she thought she had given me. Before I could rearrange myself to move the egg out from my sensitive and unprotected grundle, she climbed on top of me and began riding me cowgirl-style, jamming the egg further into my undercarriage. What followed was the most painful five minutes of intercourse I have ever had. Somehow the egg never tipped over under our weight and the pointy end remained firmly wedged in my fleshy fun bridge, blazing a path into my epidermis.

When we had finally finished and she stood up, I furtively snuck the egg out from underneath me and handed it back to her. “You can keep that one,” she said slyly as she got dressed and headed toward the door, blowing me a kiss as she left. As I bow-leggedly walked to the kitchen to make some post-coitus food, I made a pact with myself never to text her again, a pact I am proud to say lasted for six days — at which point I was introduced to something called a cone (I swear this girl had a rewards program at the sex toy store), but that’s a story for another time.

Image via Shutterstock

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Wooden hulled, three masted heavy frigate. Named by President George Washington.

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