Freaky Behavior

Boredom and curiosity are powerful forces.

I'd been wondering what sex with a transgender woman would be like. Not enough to actually try and date one, that would require putting in more effort than I wanted. I had never actually dated a cisgender woman either. Any time I wanted to get my rocks off and didn't feel like jerking it to porn, I would just hire an escort. I had calculated that with the amount of money spent on movies and flowers and "romantic" dinners and all the other garbage that went into actually dating someone before they would let you stick your dick in their orifices, it was more cost-effective to just rent someone's charms instead. It also avoided all the complications of being in a "relationship" and having to actually care, or at least pretend to care, about someone's feelings or have to try to meet their "emotional needs".

Anyway, here I was. I called the usual number and spoke to the usual gatekeeper. He knew me pretty well by now.

"What do you want this time, Hank?"

"Something a bit different, Tom. A woman with, shall we say, a little something extra down below."

"One who's packing."

"Eeeyup."

"I have the perfect woman for you, then. Her name is Gina. Saturday at 8 pm all right?"

"Works for me."

Saturday at 7:15 pm, I did actually shower thoroughly and put on clean clothes. I'm not so much of an asshole as to not have proper hygiene when I rent the services of a woman. I even brushed my teeth right after stepping out of the shower. That probably made me more considerate than 70% of the visitors.

I arrived at 7:55, greeted Tom, paid him the usual fee (half of which would go to Gina), and was told she'd be in room 8. I proceeded that way and opened the appropriate door, entered, then closed the door behind me.

"You must be Hank. I'm Gina."

"A pleasure." I shook hands with her. She was about my height and was wearing something silky. I guessed her breasts to be C cups.

"And what can I do for you today?"

"Just a standard fucking."

"Just to clarify, you want to be the one inserting your dick into my orifice, not the other way around, correct?"

"That's correct."

"In case you were wondering, it does still work, though it's considerably smaller than it used to be, and I do prefer to receive rather than give."

"I wasn't wondering." I removed my clothes, and Gina slipped out of her silky garment. We were now both naked. Gina assisted me up onto the bed, then joined me.

"We'll need to get you ready." Gina reached down and wrapped her hand around my pole, then began stroking me to hardness.

"May I?" My eyes locked onto her chest. She nodded. I kissed through her cleavage, then began suckling her nipple.

"I know I'm supposed to be just an emotionless pro, but that actually feels nice." I switched to her other nipple, and her body actually shivered slightly. Her hand sped up its motions on my now fully hard cock.

"Mmmmmm." My reply was muffled by her nipple in my mouth. But I suckled harder and flickered my tongue a bit. She understood.

"Your cock is ready." Gina detached herself from me and reached for a condom from a stack on the table. She slipped it onto my pole. "What position would you like to fuck me in?"

"Missionary."

Gina lay on her back, dripped some lube into her butt crack, and spread her legs. I got the hint and positioned my sheathed pole at her back entrance, then worked it gently in until I was hilted.

I held my position for a second, then slid back out slightly and back in. I continued doing so until I'd established a steady rhythm. Gina squirmed and shivered beneath me, and her cock, several inches smaller than my own, got hard as I pumped in and out.

"You do like being filled." I gave Gina a smile as I continued to steadily fuck her.

"Yes."

"Go ahead and jerk that little dicklet while I fuck you, slut."

She reached a hand down and begin stroking herself as I sped up my pace a bit. Her breasts wobbled as I thrust deep inside her. I dipped my head down and suckled her nipple again for a little bit, and she quivered and moaned.

I popped my head back up and started really drilling her, thrusting in and out of her ass as fast as I could make my hips move. She instinctively sped the movement of her hand on her dick. My balls were already full and started to tighten. I figured I'd better let her know.

"I'm close to cumming." She grunted in response. I rammed my pole as deep as possible into her rear, and remained hilted as my sperm shot into the end of the condom. I waited to pull out until my rod stopped throbbing and spurting.

It wasn't until after I did so that I noticed a small amount of cum on her belly. Apparently she had made herself climax.

"Unemotional pro, huh?"

"There was a bit built up. You're the first person who has asked for me to jerk myself while being fucked in four days. And it's been a week and a half since someone asked me to fuck them and finish inside their ass."

Gina removed the condom from my pole, tied it off and tossed it into a trash can. Then she went into a small shower to rinse the sweat and cum off herself, while I got dressed. She dried off and put back on the filmy outfit she was wearing when I arrived.

"Will you be wanting my services again at some point?"

I gave her a genuine smile. "Definitely. I usually come by here about once every three weeks."

Then I stepped out of the room, closed the door behind me, gave Tom a wave as I crossed back through the reception area, and went back home. Another trip to the whorehouse finished.