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Everything in this story is based in truth. Some creative liberties have been taken. All sexual interactions happened with consent, in safe conditions for all concerned
I’ve been blessed to be taller and stronger than most men all my life. I’m usually shy and reserved, but as I turned 30, something changed: I started getting a lot of attention from older women. Glances in the line at airport security, at hotel bars, at work (I have a pretty customer facing job) and on dating apps. The stories are usually the same: dead bedrooms, recent divorces, or stressful careers make it really hard to maintain a fulfilling relationship. The body has needs. I’m always happy to fulfil them.
I met Mariah (name changed) for the first time on a work trip. 15 or so years older than me, the very definition of a boss bitch. MBA from the Ivy League, head of Strategy at a medium sized firm who also managed to work out 2-3 times a week. I heard then (and learned later) that her husband, Corey (name changed), was equally impressive: handsome, always well dressed, a day trader that made great money betting on stocks and equities. He did especially well for himself over the pandemic.
Which is why I was caught off guard when she had me tie my belt around her neck and take pictures of her lips around my swollen cock head on her phone the second night we met at a work conference. I was happy to oblige. She took up the offer to shower in my hotel room before we started round two. When done, she stepped out in a towel as I recuperated on the couch and contemplated the rest of the evening. Her phone was in her hand and she was taking a selfie.
“Is that for me?”, I chuckled. “Honestly I prefer the in person view a lot more!”
“No, it’s for my husband. He says hi”, Mariah responded matter-of-factly. Now I was familiar to the swinger and cuckold lifestyles, having been active with partners in both situations before. But I was surprised that someone I barely knew was revealing this on the first “date”: I wasn’t even sure if this was anything more than a one night stand.
“He’s been my submissive from the moment we became exclusive. Men usually find me intimidating but he was different: he charmed me, but in the bedroom, same old shit. An exec that wants a woman to show him his place. Don’t get me wrong, I like his dick, but I like bullying him even more. We’re going through a cuckolding phase right now. You’re six inches taller than him, and your dick is thick. I sent him that picture. He almost came in his pants, the sick fuck.”
I took a few seconds to process, and didn’t say much. “What, you knew I was married. This revelation going to scare you away?”
Her eyes were smouldering. I knew that if she left my room, she would be getting dicked down by someone else within the hour. She knew what she wanted.
“No, I’m happy to participate. I have some ideas”. A smirk spread across my face as I stood up, only in my boxers. “Stay put please,” I said as a quizzical look spread across her face.
I rummaged my bag for some markers and a ruler. “Give me your phone, and bend over the table.” Silently, she walked to the hotel study-table, her face flushing pink. She slid her phone across the desk, and bent over at the hip, her ass poking through under the towel.
I started with her thighs. A sharp sting ran through her body as the ruler made impact, but she didn’t say anything. I made my way up. Inch by inch. Left then right. All the way up to her ass cheeks. When the first strike landed on her ass, she let out a yelp. As I swapped to using my palm to strike her, it changed to something resembling a growl.
“Keep your mouth shut, or I’ll have to shut it for you.”, I said in a conversational voice.
“Yes sir.” SMACK. I hit her ass with an open palm, hard. She physically shifted forward, she boobs pressing against the cool wood of the desk. She let out a yell of pain.
“What did I tell you about keeping your mouth shut?”, I said, as I smacked her again, HARD, on the other cheek. The crack echoed across the room. The silence was deafening.
“Good. I like a trainable bitch.” I spread her legs wide and put my palm amongst her folds. Warm, wet and running down her legs. She was loving this.
A few strikes followed. Palm. Ruler. Ass. Thighs. Her pale skin turned crimson. She was quiet through the whole exercise.
I took the marker and fashioned a tramp stamp on the small of her back. I captioned it “Daddy’s filthy pain slut.”
“You may speak.”, I said, as I sunk my now rock hard cock, inch by inch into her desperately needy pussy. As I buried myself balls deep in her folds and let her adjust to the new sensation she let out a groan of need and relief.
I passed her phone back to her which had been in my hand the whole time.
“Go to your recent videos and hit send. Tell Corey you’re busy and that you’ll respond to him tomorrow. He’s not allowed to touch his pathetic dick until Daddy is done filling up his pain slut.”
“Fuck meeeee…” Mariah groaned into the desk as my cock pulsed inside her. Oh I was going to… this was going to be fun.
To be continued