I want a...TS prostitute

I’m a lesbian who recently ended a long-term relationship, and once the anger and sadness subsided, a tidal wave of sexual empowerment swept over me. I decided to live out my deepest, most outrageous sexual fantasy: I wanted a prostitute.

Interested specifically in a transsexual (TS) experience, I sought someone who looked as much like a woman as possible. Some male-to-female TSes have sex-reassignment surgery and some do not—I decided that the parts between the legs were negotiable so long as she was hot.

My first stop was backpage.com, a classifieds database searchable by city. As any analytical person would do, I ran through the gamut of cons in my head. I could meet up with a prostitute and be subject to a mugging, rape, murder, an STD, arrest or just a plain, old-fashioned scam. The “Brazilian beauty” listed online could turn out to be a hairy, overweight oaf with a horrendous case of gonorrhea.

I made a list of the names and numbers that piqued my curiosity, called a few and was turned down. “No mujeres,” said one. “Are you calling for your boyfriend?” asked another.

Then Tara answered the phone.

She had a thick Puerto Rican accent, with only a hint of testosterone. I told her I was nervous but ready, and she asked when I was coming over. She took my cell number and told me to meet her on a corner in Jackson Heights, Queens. After I waited for more than an hour—that traffic cop, is he looking at me?—Tara called and instructed me to meet her at her apartment, just up the block. When I reached her door, out popped a head with long, dark hair.

“Hi,” I whispered.

“Hi, come in,” she said, opening the door wide.

To my surprise, TS Tara was beautiful. Tall and shapely, with large, perky breasts trying to escape from a tiny black midriff-bearing shirt. Her face was soft and feminine—much cuter than her picture online. Her Yorkie trotted around behind a puppy gate in the kitchen, and I felt like I was visiting an old friend.

The apartment was large and bright; the scent of nectar and potpourri—plus a hint of marijuana—hung in the air. Tara ushered me into her bedroom and sat down on the edge of the bed. I told her I was nervous. She offered me a beer.

Two Coronas and a blunt later, I finally started to relax. I asked to see her naked and began pulling off my own clothes. Tara closed the curtains on her bedroom windows and pressed PLAY on her DVD player. On came a Hustler porno showing women getting fucked by black men with large penises.

I sat on the corner of the bed and watched as she undressed. She said she needed to get herself going and started to jerk off. She reached under the bed, pulled out a box of condoms and slipped one on. She then asked me to lie down and tried to penetrate me, but it felt awkward and she went soft. I wasn’t into it either: It had been ten years since I’d slept with a man.

“It’s okay,” I said. “You’re gay. I’m gay. It’s okay.” I got up to put my clothes on.

Tara wasn’t having that, though; she wanted to see it through. She called in her boyfriend, a well-built Dominican man, to help. (Apparently he’d been in the next room the whole time.) She started going down on him, which made her erect again. Figuring it might be easier for all of us if I just took it from behind (like a man, and where I didn’t have to look at their dicks), I flipped onto my stomach and let Tara penetrate me. She pumped for a bit, then traded places with her boyfriend. While he fucked me, Tara sat next to us on the bed and jerked off. Eventually, I was able to enjoy his cock pounding my G-spot.

In the end, I got what I paid for—an orgasm, plus a free oral sex show, for $150. When I left Tara’s apartment and stepped into the bright, afternoon sun, I didn’t feel dirty like I’d feared I might. It wasn’t an act conducted in the wee hours of a trashy postparty evening, or a walk of shame the morning after. I had entered on a weekday afternoon and left with the sun high in the sky.

*Writer’s name has been changed to protect them from their mother.