The Day I Fisted a Transvestite

I was in New York, taking a break from Korea, and I was bored out of my mind. In Korea you can head out on a Monday afternoon, find a bar full of familiar faces, and kill boredom. Not so in New York, where everything is spaced out, cabs cost an arm and a testicle, and people don't immediately trust a stranger. All of my Yale friends were enjoying their corporate careers, not able to enjoy a few morning drinks, so I turned to the internet.
I went on Craigslist and started searching for someone who would be willing to have a few drinks. After a few drinks over the computer, I end up on the t4m section of Casual Encounters. This individual had this picture of themself in front of a mirror; blonde wig, sex worker get-up, giant sunglasses, and a massive butt-plug that somehow didn't kill their smile. I read the ad and it said that they was into "NSA sucking and swallowing, fisting, fucking, etc." I was interested in discussing why the National Security Agency sucks, and also in the etcetera. I replied to the ad, very naively, and then got a reply.
In the reply they clarified that NSA meant "no-strings attached" and then they informed me that they always wear "a red lace thong, garter belt with black fish nets, black mini skirt, and 6 inch heels," which made them taller than me. At first I just wanted to talk because I was bored, so I hop on the 4 train and head to Midtown. I was expecting to enter the sketchiest building, but it had a concierge and I got the impression that rent was $4,000 a month or more; this person had enough money to take fist all-week long, and it was apparent in the look the concierge gave me.
I take the elevator up to the apartment, and knock on the door. I hear the lock open, and then in a low-pitched, kinda-seductive voice, I hear: "come in." They was already lying on their bed, and I entered into a situation. The bed was leather, which I'm sure made for easy wiping, and there was an S&M chair to hang themself next to the bed. I say hello, my name is Joey, I'm from Washington Heights. I told them I was Puerto Rican because I didn't want to give Dominicans a bad name, and they told me that they thought Puerto Ricans were cool.
As they's lying on top of their leather bedsheets, they produce a can of Crisco all-vegetable shortening. They tell me to dip my hand into the can, and I pulled out a significant chunk. They raised their legs up in the air, and I proceeded to try and jam my fist up their very stretched anus. They screamed, "careful!" and instructed me that I had to bring my fingers together, kinda like an Italian when cursing, and that I should make the fist only once inside. After a few minutes of pushing, I found that my entire hand was inside their ass. I heard moaning, but it wasn't pain. I was then instructed to make a punching motion, and that's when things got intense. They started shaking and screaming in ecstasy, and next thing I know they ejaculate all over themself: I was hitting the prostate just right.
I felt that I had done good manual labor, and pulled out my hand. Fortunately they had flushed their innards before the fisting started, so there was no fecal matter all over the Crisco. Nonetheless, I immediately proceeded to wash my hands. Once I finished, she called me back and offered to return the favor. I figured I wasn't gonna be able to get any friction because they was so loose. Nonetheless, I slipped a rubber on and then decided to pound at that ass, missionary style. I felt like I was throwing a hot dog over a roof, so I made them cross their legs and implored to squeeze and make it tight. After a few minutes, I somehow managed to cum, took off my condom, washed my cock in the bathroom, and immediately headed back to the Bronx, no kissing, no hug goodbye, none of that gay shit.
They e-mailed me a week after that incident, and I almost hopped back on the train, but they asked that I bring them another tub of Crisco, and that I also cuddle afterwards. I didn't reply; not because I'm a cheapskate and didn't want to buy a tub, nor was it because I was outrage that they'd already run out of Crisco in merely a week, but rather because they wanted to cuddle. "Cuddle!?" I said to myself, "that's too fucking gay!"