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.
I was stunned, standing there absolutely gobsmacked by what had just happened. “What do I do now?” I asked myself. “Have I just come across the biggest prick teaser ever or was that an invitation?”
I mulled this over for several minutes. On the one hand, despite her gorgeous body, she was at least 25 years older than me. But then I’ve never had an older woman… and she was definitely worth having. It was now or never or else she might be fast asleep. Driven by the erection that was announcing itself as I had been given a delightful strip tease and continued to stir in my loins, I knew the answer.
I quickly stripped all my clothes off and softly crept to her bedroom door. As quietly as I could, I opened the door. The bedroom was dark but the light from the other room cast enough of a glow to show her in bed lying on her side.
Without further hesitation, I slipped between the crisp hotel sheets as she was lying there. I couldn’t tell if she was actually asleep or not. But she didn’t stir. I spooned with her, enjoying the feel of the warmth of her body interlocked with mine.
I wrapped one arm around her and cupped one of her breasts. In response, she pushed her ass into my groin causing me to return to a semi-erect state. As we lay there, I began to lick the nape of her neck ever so softly and then gently blew on it. My hand began to pinch one of her nipples which had grown hard. She moaned softly.
Still not sure if she was awake or just reacting in her sleep, I felt her reach behind herself, grasp my stiffening cock and began to slowly stroke me to a full erection. I felt I should return the favour and, still with one hand squeezing her breasts, I slipped a finger of the other hand between her legs. She responded by lifting one leg over mine as an invitation to explore her further. I gently rubbed my fingers over her pussy to sense how wet she was and then pushed my middle finger inside her. She squeezed her pussy muscles tight around me.
She continued to stroke my cock, back and forth. It was such a lovely feeling and I was in seventh heaven.
By now, I had two fingers fucking her pussy and her cunt was dripping. With my fingers well-lubed by her pussy juice, my fingers moved to her ass. I rubbed her ass and slowly, almost imperceptibly, pushed one finger inside her. She clearly wanted me to go deeper, pushing back against my hand to force my finger further inside her ass.
“You have to fuck my cunt now while your finger is still in my ass,” she moaned. “Fuck me till you cum. I want your cum to fill me up. I want to feel your cum drip from my cunt.”
I loved to hear her talk dirty… so very dirty in the way a lady really shouldn’t but makes it seem so natural and it made me so very horny… and my erection grew even further than I could ever have imagined. Her hand guided my cock to her pussy. I was ready to thrust deep inside her but decided to tease that gorgeous cunt to heighten her arousal further. I just wanted to make her crave me even more. I stroked the head of my cock up and down her pussy lips, then pushing in ever so slightly before pulling out again. I did this four or five times before she admonished me.
“If you don’t fuck my cunt deep and hard with that cock of yours, I’ll scream,” she chided. “Now just fuck me!”
Without further hesitation, I thrust deeper and deeper inside her. With each thrust of my rigid cock, her cunt squeezed me taking me deeper. I could soon feel my cock pushing against her cervix. Her tight cunt held me.
My finger was now pushing deep into her ass. She had opened up to me as my cock and her cunt had worked together in unison as we fucked each other. With my cock in her cunt and a finger deep in her ass, we were both fast approaching orgasm. She was moaning with pleasure, constantly repeating “Oh fuck, oh fuck. Fuck me. Fuck my cunt.” almost under her breath. God, it was so sexy to hear her talk like that.
“I’m gonna cum. I’m gonna cum,” she exclaimed breathlessly. “Give it to me. Make me cum. Oh fuck, yes. Just like that. Fuck… fuck… I’m cumming. Oh… Oh… Oh. YES. FUCK. FUCK. Oooohhhh!”
Just as she reached her climax, I could feel my balls ready to empty inside her. My cock swelled inside her as I began to pump stream after stream of hot, white cum deep inside her, filling her up.
Exhausted from our sex play, we both crashed. Falling asleep with my cock still inside her and my cum beginning to slip out of her pussy was such a pleasant and calming feeling. And, when I woke up this morning, this beautiful older lady lay, still there in bed with me.