I'd met Cheryl at a work function - one of those advertising awards shows where the primary purpose seems to be for as many people to get as drunk or high as they can in the shortest amount of time possible. Not that I'm being judgmental, of course. Been there, done that, got the tee- shirt. Having reached 30, I'd missed out on too many "opportunities" to continue like that because i wasnt in a fit state to take advantage. And these awards shows provided many, many of those "opportunities", trust me.
I found the dinner table that I had been allocated to and took my seat next to a lady whom I had never met before. Guessing, I would say she was somewhere between 55 and 60 so probably 25 years my senior, blonde, very well-attired in a black cocktail dress and, I couldn't help but notice, what appeared to be some very high heels. Her dress showed off her breasts with an enticing amount of cleavage.
She smiled at me, looking me directly in the eyes, as I sat down beside her. I smiled back. Throughout dinner, we chatted. A lot of the usual small talk about life, business and other pretty dull topics. However, as the evening progressed, it became clear that we were developing a connection with one another. Every now and again, she would squeeze my hand in emphasis of a point she was making. I liked that. I liked that very much. I couldn't help but look discreetly at her cleavage and tits each time she squeezed my hand. And I knew she had seen me do that more than once. That didn't stop her so she must have enjoyed the attention.
Dinner proceeded through its three courses, the obligatory after-dinner speeches and then the awards ceremony. Truly boring! It was then that she leaned in towards me, her breasts pushing against my arm, and whispered in my ear, "I'm staying in this hotel tonight. I'd be most grateful if you will escort me up to my suite. I'm feeling a little tired."
Hoping this was a euphemism for "take me up to my room and fuck me", I was more than keen to oblige. We stood up and I offered her my arm, as a gentleman would surely do, and walked through the ballroom, proud to be escorting her while navigating all the tables. We arrived, alone, at the elevator. Stepping inside, she asked me to press the button for the 29th floor. At this point, I thought she'd fall into my arms and we would embrace each other in a passionate kiss, only to be disappointed as she stepped away from me to the back of the elevator. We rode in silence until the bell chimed as we reached her floor. But, she linked arms with me again as we walked to her door.
At the door, she handed me her key card to open the door. As I opened it, she made it clear that I should follow her. On the threshold, she turned to me and reached up and kissed me. Just a gentle brush of the lips.
At that, she stepped out of her high heels. "I'm tired" she said."I'm going to find my bed." And with that, she reached behind her and unzipped her dress and let it slip to the floor. I just stood there in amazement. Within seconds she had unclipped her bra and dropped that to the floor too. She then took a couple of steps towards the bedroom and bent down at the waist and pulled down her panties. I was given an eyeful of her cute ass and shaved pussy. She looked over her shoulder, uttered "Goodnight", went into the bedroom and shut the door behind her.
