I spent the summer between my 2nd and 3rd year of college suckling on the parental teat in South Florida. It was the absolute prime of my “do anything to get laid” phase. I was recently freed from a 4-year long-distance relationship that began in high school and I wanted nothing more than to have sex with as many girls as possible.
Most of the things I did that summer are not story-worthy; you can only tell the same, “I got drunk on Dom and fucked this hottie” story so many times before it gets annoying. That summer I experienced every random sex situation that a 20 year old can imagine: fucking on the beach, getting head from random girls in club bathrooms, sleeping with 3 different girls in a day, getting so drunk I passed out during sex, getting arrested for receiving fellatio in the pool at the Delano, blah, blah, blah…Jesus. What does it say about how fucked up my life is that I don’t consider these stories to be extraordinary anymore?
Anyway, while most of my stories may not be extraordinary for me, there is one very notable exception…
I was seeing one girl, “Jaime,” about twice a week. She was a fresh arrival to South Beach, having moved there 5 months ago from upstate New York as a 19 year old with a modeling contract. We met through a mutual friend who befriended her while they were shooting a TV commercial. Five weeks and lots of sex later, she thought we were dating. I knew better, but she was way too hot to bother correcting her assumption.
The ex-girlfriend of 4-years I previously spoke about was very sexually conservative. It was missionary in the dark and then straight to sleep, with maybe a blowjob on the weekends if she’d had a few glasses of wine with dinner (it was a high school relationship, I didn’t know any better). After four years of this, I was ready to experience all the things I’d missed out on (when I wasn’t cheating on her, of course).
Buttsex, known in the biz as “anal,” was one of these unknowns, and I decided that I wanted to try it. Jaime was the perfect partner: very hot and very sweet, and more importantly, very naïve and very open to suggestion.
She was reluctant at first, not understanding why we just couldn’t keep having normal sex, so I had to employ my persuasive powers:
Jaime “But…I’ve never done it.” Tucker “I’ve never done it either; it can be our thing.”
Jaime “But…I don’t know if I’ll like it.” Tucker “You won’t have to worry about getting pregnant.”
Jaime “But…I like normal sex.” Tucker “Everyone’s doing anal. It’s the new black.”
Jaime “But…I don’t know…it seems weird.” Tucker “It’s the preferred method in Europe. Especially with the runway models. Don’t you want to do runways in Europe?”
After a few weeks of this, she finally consented. Though she agreed to let me put my penis in her small hole, she extracted a promise in return:
“OK, we can try anal sex, but I want it to be special and romantic. You have to take me out to a nice place, like The Forge or Tantra, NOT one of your parent’s restaurants, and it has to be a weekend night, NOT a Monday. And you have to keep taking me out on weekends. I’m tired of being your Monday night girl.”
I made reservations for the next Friday at Tantra. Aside from being insanely expensive, Tantra is famous for having grass floors. Really; they put in new sod every week. They also advertise their food as “aphrodisiac cuisine.” Yes, at that point in my life, I thought these things worked.
Thanks to my father’s connections, I got us a corner booth in the grass room. She was quite impressed. I ordered like it was the Last Supper. No expense was spared. Two $110 bottles of merlot, veal rack, stone crabs, the Tantra Love platter–it was lavish and decadent. I was 21, stupid, and wanted to fuck Jaime in the butt; I wasn’t about to let a $400 tab get in my way.
By the time we left Tantra, this girl had doe eyes that made Bambi look like a heroin-chic CK model. She could not have been more in love with me. The entire drive back to my place she was rubbing my crotch, telling me how badly she wanted to me to fuck her, how hot I made her, etc, etc. We get back to my place and our clothes are off before we even get in the door. We collapse on the bed and start fucking. Normal vaginal sex at first, just like always.
Now, what she did not know, and what I have not told you yet, was that I had a surprise waiting for her.
[Aside: Before I tell you what the surprise was, let me make this clear: As I stand right now, 27 as of this writing, I am a bad person. At 21, I was possibly the worst person in existence. I had no regard for the feelings of others, I was narcissistic and self-absorbed to the point of psychotic delusion, and I saw other people only as a means to my happiness and not as humans worthy of respect and consideration. I have no excuse for what I did; it was wrong and I regret it. Even though I normally revel in my outlandish behavior, sometimes even I cross the line, and this is one of those situations….but of course, I’m still going to write about it.]
This was going to be my first time foraging in the ass forest, and I wanted to have a reminder of my trip, a memento I could carry with me the rest of my life…so I decided to film us.
I planned this beforehand, but I was afraid she would decline, so instead of being mature and discussing this with Jaime, I just made the executive decision to get it on camera…without telling her.
That alone is pretty bad. But instead of just setting up a hidden camera…I got my friend to hide in my closet and film it.
No really–I know that I will burn in hell. At this point, I’m just hoping that my life can serve as a warning to others.