(M)y business (t)rip surprise | 2016

This happened not long ago on a quick business trip one state over. I was developing a contract with a vendor in Woonsocket RI and instead of driving the 1.5hr trip each way two days in a row, I decided to just get a hotel room in Providence. The first day of negotiations went so well that the 2nd day was to be more or less just signing the contract. Which meant I could go out and check out a bar or two and celebrate a job well done. I took my time getting ready, had a few pregame drinks that lead me to go out with a goal: get laid. I didn't know the area at all so I just went out and walked. The first bar I came to ended up being the only one I went to. It was early still and somewhat empty. I ordered a crown royal on the rocks and just relaxed watching the TV at the bar. After a few more people showed up I started to suspect it was a gay bar and decided to straight up ask the bar tender. He confirmed but said "it's a pretty mild scene you'll be fine, sometimes straight women come here too". On my second drink a saw a gorgeous brunette come in with 3 clearly gay guys. I thought immediately that if I acted cool maybe there was a chance. She was about 5'6", 140lbs, small c-cups and sexy toned bronze legs that had fishnets and jet black 4" heels. This was accentuated by the checkered skirt and rocker tee shirt cut open at the top. She also had black thin framed glasses. It was like a punk rock librarian look. She sat at the bar alone while the guys went to the juke box, I got brave as she ordered her drink I spoke up "put that on my tab". She smiled and scooted a few seats down next to me.

"Thanks for the drink, I'm Stacey" she said

"My pleasure, I'm Paul. I am on a business trip that went better than expected so I'm glad to have someone to share a drink with" I told her.

The guys quickly found us and ribbed her "Stacey we've been here barely 10minutes and you've already found a cutie" to which she blushed and shrugged it off. The next few hours were filled with flowing drinks and HEAVY flirting. I figured I should make a move so I told her "listen I'd love to hang with you longer but if I don't head back to my hotel now I might have a hard time making it back there" she stood up and I swooped in for an incredibly sensual kiss. When the kiss broke she whispered "we can hang out longer if you take me with you..." She gave her friends the name of my hotel and we were off. The walk was a short one although I did stop and push her against a wall for a good make out on the way. When we walked into my room, we instantly went at it knowing full well where we wanted to go with this. She sat on the desk and pulled me between her legs, our tongues twirling together as we stripped each other. I pulled off her bra and sucked on her tits as she pulled out my cock and stroked it gently, still seated on the desk. She pushed me back and I stumbled on my loose pants landing right on the bed. Stacey removed my pants the rest of the way and then in one motion, cupped my balls and took my full 7.5" to the hilt. My god was she masterful in her cock sucking skills. A good 5 minutes of her throating me she stood up and I said "I want to lick you" She kind of sighed and said "well there's a slight problem with that, PLEASE don't freak out" I had no clue what she was talking about and she pulled her panties to the side, exposing a half erect perfectly trimmed cock! I literally gasped in a mixture of shock and excitement. Being with a shemale is one of my biggest fantasies, one I never imagined would come true. Seeing that I wasn't immediately turned off she took a step towards me. I looked her in the eye and opened my mouth. With one final step she rested the tip of her cock on my lip and I took it in my mouth slowly. All I can do is think about how I like to be blown and try to do the same thing. Gripping the base and stroking in circular unison to my head bobbing. Stacey takes a step back and coyly says "you said you wanted to lick me?" She then flops into the bed. I lay on top of her and passionately kiss her for a moment before sliding down between her legs, grasping them at the knee and forcing them back to expose her ass. I dove in like it was my first meal after months on a desert island. I licked deep but soft all the while stroking her cock. Not missing a beat I spun around to 69 which didn't last long because she was in heat and begged me to fuck her. I laid her back in missionary position, her legs wrapped around my waist. With a kiss I thrust into her, not stopping til I bottomed out deep inside. I would like to say I pounded her out for a good long time but that is simply not true. As I sat up and fucked her, legs now draped over my shoulders, she peaked and blew a thick load all over herself. That sight combined with all the foreplay took me over the edge and I pulled out and stood up, which Stacey matched by sitting up and opening her mouth. I shot 6 good squirts that is probably the biggest orgasm I've ever had, and she swallowed every drop! We cleaned up and she decided to stay the night, I didn't have to be at the vendors til 11am so we had part 2 in the shower in the morning. I will never forget Stacey and the wonderful surprise hidden in her panties.