Hotel Surprise Temptation

The best visit to Chicago, my hotel bar fun, and juicy Italian Steak Sandwich.

During my last trip to Chicago, I made sure to leave time to get out, see some sights and get a local Italian Steak smothered sandwich.

The real purpose of that Chicago trip was to learn about some of our company's new software products. We spent about 8 hours each day, testing, loading and networking with other engineers from around the country. Every evening a group of 5 or 6 of us would go out for dinner and drinks. Our group consisted of 3 guys and usually 2 or 3 woman. The group ranged in age from 25 up to 45. The company always flipped the bill at our hotel so we would always end up running up the bar tab in the hotel bar. Wednesday's were Karaoke night at the hotel bar, as always, a hilarious way to get everyone loosened up. I always liked to sit back and watch everyone take their turns on stage. The women always begin with duets then eventually trying singing some slutty song where they hold the microphone like they are stroking a big thick throbbing cock.

It was Brandy's turn to sing on stage. She chose a song called, "Party like a Slut". For those not familiar, if not evident by the name, this is as provocative a song as can be played. Brandy is 5 ft 2 at best, a tight spinner body, skinny waist line with wide thick firm ass and C size breast straining against her tank top. As she mouths the song, she begins to stare right at me, pulling on the mic cord and thrusting her hips at me from across the room. Every once in a while she drug her fingers across her tight white tank top, causing her nipples to grow harder. As her song ended, she went to the table with the other woman, grabbed her purse, downed her drink and came over to sit with me.

The night was just getting interesting as Brandy slid in next to me. We decided to listen to a few of our associates attempt to sing, the whole time Brandy was staring at me with lustful eyes. After a few shots, I got up to hit the head and upon returning to the table Brandy was just standing up, slipped a napkin into my hand, kissed me on the neck and walked out. Reading the napkin I found, "give me 10 minutes, room 311." Jackpot!!

Waiting the obligatory 10 minutes I went to my room to change my shirt and hurried down the hall to Brandy's room. As I went to knock on the door, one of our other friends opened the door. With a huge grin on her face, she asked me in, handed me a drink as we walked into the mini living room. Brandy was in freshening up. Our friend, Simone, had stopped by but was waiting to see what was going on with us. Simone had known both of us for a few years. She is a tall woman, brunette hair, 45ish, big enhanced boobs and knows how to work a room. She sat across from me on the bed. I was comfortable on the couch waiting for Brandy while checking out and trying to figure out Simone. Something was definitely planned and I was ready.

After about 10 minutes of small talk with Simone, Brandy exited the powder room with a loose white tank top, sweat pants and a huge smile. As she walked right up to, straddled my lap, sat down, pulled me close and locked lips. Simone sat back on the bed, as a spectator, providing willing play by play analysis on the action. I grabbed Brandy's ass, holding her close against my growing hard cock. I could feel her to begin to grind into me. Suddenly, she stood up, spun around and sat back down, pressing her ass against my rigid cock. Brandy is now staring at Simone, like a show, as I reached under her tank top to cup her firm tits, Simone stands up and walks over to provide close attention to everything.

Simone asked if I was ready for everything. Naturally I responded with, HELL YA!. Simone guided my hands all over Brandy's body, while kissing her deeply. Brandy was riding along as if a play toy doll. Our hands begin to go lower and lower under the waist band of Brandy's sweat pants. Simone shifted from kissing Brandy to now on my lips. Her tongue darted in and out of my mouth just as we felt a rigid shaft rising from Brandy's pants. The incredible feeling of holding a silky smooth, hard lady boy tool in my hand for the first time pushed me to the brink to shooting. Never knowing that Brandy was transgender, the idea now drove me wild. Two beautiful woman playing in front of me and i get to join.

Just about then, Brandy placed her hand on top of ours, as we began to stroke her cock together. Three hands slowly slide up and down the length of her shaft, paying attention to her freshly shaven patch. Each stroke of our hands built intensity between the three of us. My free hand explored Simone's ass. As I lightly penetrated her ass hole, I heard her giggle and whisper that i can have all of that and more. I felt her push her body back against my hand, causing my fingers to go deeper into her ass. Brandy lifted up and pulled me to my feet while sliding her pants down. As I stood behind Brandy and Simone slide in behind me, our three bodies rubbing and mingling together. Brandy bent over so I could enter her man pussy. I felt Simone reach between my legs to stroke my cock, guiding it toward Brandy's tight hole simultaneously I felt her wet hot tongue lick and rim my ass. She guided my cock into Brandy's tight asshole. I reached around and stroked Brandy's beautiful curved cock. Brandy's tight hole was begging for more while Simone pushed her long pointy dripping tongue into me. Each of my thrusts began to be more deliberate, Brandy pulled away to prevent me from shooting into her. Now both Simone and Brandy pushed my face down onto the bed.

Simone crawled onto the bed to position her perfectly manicured pussy in my face. Brandy began to probe my ass with one, then two fingers. I begin to thrust forward as i feel something cool in my ass. Brandy had lubed up her fingers to loosen me up. Simone pulled my head into her snatch, diving in like a dog to water. After a minute or two i felt the pressure of something larger and more forceful than fingers in my ass. She slid her cock up, down and across my hole, ready to push in. She entered me with just the head of her glistening cock. Holding my hips, she pushed deeper and faster, thrusting until she bottomed out. As Brandy continued to mash my ass, Simone began to moan and suddenly she gushed and squirts pussy juice into my face. The sight of this triggered Brandy to pull out and and shoot her load on my ass.

At this point I was a sticky mess but both girls helped me clean up while stroking my cock. Once again fingers up my ass causing and incredible orgasm. My hips thrust uncontrollably until I came all over Brandy's beautiful face.

This night was just the first during the rest of our stay in Chicago.