I met a new Tinderoni last Week Thursday. We’ll call him Brad. He was in town for the TriBeCa Film Festival and was staying at a hotel down in the financial district. We chatted, flirted, and teased each other. He told me he was a ‘pleaser’. I was interested in finding out more.
Apparently I’m more adventurous than I gave myself credit. I guess some might say promiscuous, some might say slutty even. I say bold. I say, I know what I want, and I’m not hurting anyone by going for it. So there.
I agreed to meet him at the hotel bar for an assessment cocktail.
When I got out of the cab he was waiting out front. I was surprised that he greeted me with a full on kiss. It was pretty sexy. We got a seat at the bar. He was easy, and charming and funny. We had grapefruit margaritas that were pretty tasty. Talked movies and TV while we got buzzed and I felt like there was a good little connection there. I wasn’t about to go upstairs with him if my gut told me not to, I have pretty good intuition and while I’ll take some risks I’m not completely stupid.
The bartender asked if we wanted a second drink, we looked at each other, grinned and said no. We’re both light drinkers and that margarita had given us a pretty good little buzz. I used my usual line. “So, it’s safe to assume we aren’t mutually repulsed by each other?” That usually gets a at least a little laugh.
We headed upstairs.
The room was small, but nice, not much of a view to speak of being so far downtown. We started kissing before we got very far into the room and his hands started to roam, cupping my breasts and squeezing my ass. I slid a hand down the front of his jeans and he had a raging hard on.
We moved to the bed and started making out in earnest. I’ll give him this, he was a great kisser. Soft lips, passionate, tongue but not too much tongue. You know? Through the vent on the wall I could hear a woman softly moaning in a nearby room. It added a layer of erotica that turned me on further.
I sat up and quickly undid his belt, unzipped him and pulled his jeans off. Here’s where things started to go a bit funny.
What I had assumed was a curvature downwards because his boner was trapped in his pants continued to curve down. Even after I slid his briefs off. It wasn’t a turn off, I’m not the shallow sort. Everyone is different and we all have our quirks, lord knows I’m not a supermodel. But I was slightly concerned about the logistics. I had never seen one that curved so far south before.
I went down on him for a little bit, but he soon pulled me down and started eating me out instead. It was really hot. His good kissing really translated into good head. Before long he had me squirming and breathing hard. I grabbed a condom and slipped it over his cock. He was on his back and I straddled him, guiding that curved dick into me. It took me a few tries to get the angle right (leaning slightly back, hips tucked up) to be able to get a good rhythm going. Once I had it I started to go a bit harder, got up from my knees onto the balls of my feet for more traction and started really fucking him, but he stopped me. I think it hurt him a little bit, or he was afraid it would hurt him because of the curvature? Not sure. But I slowed down and started squeezing on my upstroke instead. Before long he was coming. We took a little break. He wanted to continue to please me. I brought along a little bullet vibe so I took it out and he made me come a second time. This time so much harder. Good I love a good vibrator. He was laying on the bed, his head on the pillows and I straddled him with my head near his feet so he had good access to me. He fingered me and rubbed my clit. I really wanted his cock back inside me, but when I asked he said he wanted to finger me. I guess he had a hang up about his cock. Too bad because beside the curve, it was a pretty nice dick.
By this time it was close to 3:30 in the morning. He offered to let me sleep over, but I didn’t really feel comfortable doing that so he gave me money for a cab ride home.
Not a bad time for a one off hotel fling.