Rate by The Naughty Meter
Naughty level to be set later
Categories: Anal Sex, Transvestites
Tags: trip business
Location: A hotel room
Fulfillment: I will tell you later
Nature: I will tell you later
Jade and I spent the next day working the trade show. We were on our feet all day talking to people about how our consultancy service was some how different from the others. When the crowd of people would thin out Jade would take a handful of fliers out and walk around handing them out. With her short skirt, swaying hips and low cut top she never failed to get enough attention, and contact details to fill our quota for the day. There were always some guys hitting on her but she used the flirtation to get there details to follow up on.
Towards the end of the day she came back with an invitation to a party with one of the suppliers. It would be a night of socializing, free alcohol and lots of flirting.
Jade and I went back to our rooms and agreed to meet at 7:00 to head to the party. I went into my room, changed from the official company uniform for the trade show, and into a suit for the event. I wasn’t overly happy about having to wear a suit as it meant I couldn’t relax, but this was the cost of business consultancy. At 7:00 I went to Jades room and knocked on the door. “Just a minute!” she yelled.
The door opened and my jaw dropped. Jade was in a form fitting blue dress. Very low cut with here huge breasts barely contained. “Wow…” I said.
“Easy tiger.” She giggled as we took off.
The evening was typical of a tradeshow party. There were lots of people looking to find a bit of ass. Oh and a bit of actual networking as well. The alcohol was flowing freely. Jade was quite the spectacle, actually doing the networking and building relationships, and having lots of eyes follow her every move. More than once when a guy would start getting to familiar I would walk up and make it clear that she was my date, but for most of the night I just let her do her thing.
The end of the night we headed back to our hotel. We decided to stop in at the bar for a wind down drink before heading to our rooms. The one drink turned into three, I could tell that Jade was trying to build up courage to say something. She would take a drink, take a deep breath, start to say something, then loose her nerve and say something about the weather, the sports playing on the TV or a person walking by. By the time our third drinks were done she figured it was now or never.
“I know all of this will come to an end when we get back home… “ she paused. “But…” she swallowed hard. “Come to my room and fuck me…. Please….” Her voice was pleading, but cracked as her nerve waivered.
She could see the shocked expression on my face. She went pale and turned away. It took a moment for me to regain my sences, by that time she was half way to the elevator with slumped shoulders. I had to run to catch up to her.
“Wait!” I said.
I the elevator I could see that she was crying. “I’m sorry” I said, “I just wasn’t expecting.”
“It’s ok…” she choked back tears. “I understand. It’s not like you… I mean I’m…”
“Your fine.” I said…. “Your hot…”
“I know… I’m just not your…”
I cut her off by grabbing her hand and placing it on my crotch where she could feel my growing bulge. She looked at me. I raised an eyebrow and nodded.
When the elevator door opened she rushed out pulling me behind her and moving as fast as she could. We were barely in the door when she was stripping off my clothes.
The suit jacket was on the floor, then my shirt. She stopped for a few moments to run her hands over my freshly waxed chest. Then she opened my belt and zipper, letting my pants fall to the ground. Next she got down on her knees and slipped my underpants off, coaxing my cock to life and kissing it all the way down the shaft.
Jade stood up and stepped back from me. Reaching behind her back he unzipped her dress and let it fall to the floor. She stepped back a few steps towards the bed giving me a good look at her shapely body and large breasts. She was naked now, except for her g-string. I moved forward, grabbing her by the waste and pulling her close. She closed her eyes and smiled. I started grabbing for her g-string but she stopped me with a started expression. “Wait…” she panted.
She pulled away from me and turned down the lights off. The only light was coming in from the city lights through the open window. Jade came back to the bed and stood with her back facing me. Slowly she peeled off her g-string and kicked that off.
Jade took a step back and pushed her body against mine. She felt burning hot. My cock pressed against her ass. I felt something hard.. reaching down I noticed she had a but plug inserted deep into her ass. I pulled gently at the plug. She moaned. “I was hoping all night you would say yes. I wanted to make sure I was ready for you. Ohhh….” She moaned again as I pulled the plug a bit more. “Every move tonight I could feel that inside of me, wishing it was you.”
She put a knee up on the bed and bent over, giving me full access to her ass. I pulled the plug again, this time firmer. The plug was clear; I could see her asshole expanding to let the plug free. Finally it came out. Jade moaned again.
She handed me a tube of lube. “Quickly” she begged. “I want you inside of me. I want you to fuck me. Fuck me like a woman.” She pleaded. I lubed up my rock hard cock. I was so horny, and more then a bit intoxicated, I didn’t care about anything any more but fucking. I grabbed Jade’s hips and guided my cock to the opening of her ass. The plug had worked to loosen her tight hole up enough that I could enter her ass easily. I slipped the head of my cock in and her ass quivered. A little further and her ass clenched me. I drew most of the way out and then pushed in all the way. She groaned with pleasure as I filled her ass.
Long hard thrusts in and out. I was slamming her ass and couldn’t stop. She leaned back, lifting herself up and pressing her back against me. The change of position slowed down my thrusts but didn’t stop me. “Fuck that’s good.” She moaned. “It’s been so long since I have been fucked like this.” I backed out and slammed back into her, taking her breath away.
I reached around and grabbed her tits. She moaned again as I drew out and pushed in. I reached down between her legs. She tensed up as I started playing with her cock and balls. After a moment she relaxed again realizing that I was to possessed to care. Again and again I rammed her ass home. After a few moments her cock swelled and she blew a load of cum all over the bed. Her ass clenched my thrusting cock as I continued to pound her through her orgasm.
Finally I couldn’t hold back any longer. My cock swelled to the point that Jade screamed. Over taken with lust I pushed her back down towards the bed, giving me a clear path. One last deep thrust that felt like it was going to split her in half and then release. I could feel an endless stream of cum blasting her insides.
She reached down between her legs and caressed my balls as I gently pumped the last of my cum into her ass. I pulled out of her, and she collapsed on the bed. It was a few moments before she managed to roll over onto her back. She was leaking cum from her cock, and her ass, but the satisfied smile on her face showed that she was loving every moment of it.
“Thank you” she said quietly. I smiled.