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Sean the Businessman
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Sean was some corporate suit-y kind of guy in his late 40s who travelled to my city once every few months for work. On our first date he’d taken me to some bougie steakhouse downtown and bought me a hundred dollar steak and top shelf whisky (which was definitely a waste, it literally just tasted like steak and whisky, but whatever). He wasn’t especially charismatic but he acted like a gentleman and made me feel like a princess so I went back to his luxury hotel room on the 45th floor and let him fuck my brains out. Afterwards I asked him how his wife was because, fucking plot twist, the out of town business guy looking for a hookup was obviously married, and he admitted it right away. I hadn’t really expected that so like an idiot I just stood there for a bit then asked how she was and he said she was good and I didn’t really know where to go from there so I angrily told him I had fun and to call me if he was ever in town again and then stormed out of the hotel room.

After my display of poise and grace I was a little surprised to get a text from him a few weeks later. And so I saw him again. Turned out he was in my city pretty often and I became his lil city hoe. I grew oddly fond of Sean over our encounters. Sometimes when I hadn’t heard from him in a while I’d catch myself wondering when he’d call next, and dare I say miss him? Ew no. Sex. That’s what I want. Not affection and connection, yuck. Gross. Orgasms. Yes. Dicks and fingers and tongues and DANGER. That’s the stuff right there. Phew, okay. Sorry. Anyway.

Sean called me his therapist, a fitting nickname, my expertise is evident in that last paragraph. He’d take me out and tell me how business is going, and I wouldn’t care at all or even know what he’s talking about but I’d smile and listen. He’d go on about quarterly profits and HR and probably less stereotypical business stuff but I literally don’t know. I just got good at knowing when to giggle or gasp based on how he said things.

But the fun part was when we’d go back to his room and he’d tell me about his personal life, mostly his wife, while we fucked. It was strangely intimate to me. I’ll curl up naked next to him on the bed and slide his cock in and out of my throat, sometimes for an hour, and he’d admire my body and the pleasure I was giving him as he relayed details of a fight he had with his wife, or how she never wants to have sex, or about great sex they had recently, or even just a fun night watching TV that reminded him why he married her. It was actually all very wholesome, in a deeply not-wholesome sort of way I suppose.

I always did all the work, unless he wanted me doggy but even then it was still a show for him. He loved long, long blowjobs, slow and sensual, and always deep in my throat. Sometimes he’d ask me to ride him or to take me from behind, but he always, always finished the same way. Me on top in reverse cowgirl bent way forward so he could see everything. He liked it nice and slow but when he got close he’d grab my ass and move me up and down himself, faster and faster. He generally stops talking about his wife at this point and starts rambling incoherently asking if I want him to put a baby in me and I would say yes please put a baby in me I would like that very much Sean. And eventually he’ll mash my ass down and hold me there as he thrusts up and I’ll feel him throbbing inside me as his legs quiver under me and I hear him make concerning gurgley mouth noise (don’t worry, he always lived). He’d hold me there well after he was done which was a little irritating because ya girl gets leg cramps but eventually he’d push me up one last time and shrinking little Sean would plop out and he’d admire the mess he made dribbling out of me for a minute or two. Or so I assume. Maybe he was sending emails idk I never looked. But then he’d let go and I’d get off and that’s it. He’d always be sure to thank me, which sounds pathetic but was low key adorable and then he’d pull the covers up over him and roll over and go to sleep without another word. I’d pick my clothes up, quietly get dressed, and leave.

I liked Sean. I never came when I fucked him, like not even close. Like not even close. But for some reason it just felt good to please him. Our sex wasn’t about me, I was just a vessel for his pleasure. And I liked it. Aside from regularly blowing loads in some girl his wife didn’t know about on the other side of the country, he seemed like a sweet loving husband and a caring father. I felt like I was doing some sort of public service by servicing him. Like he deserved a good fucking, ya know?

Anyway one time I met up with him and he informed me his wife had left him. All my attraction to him disappeared utterly and completely in that moment and so I left and blocked his number, and that was the end of that. That’s just how these things go, you know. But I will always remember him and the beautiful relationship we had.

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Posted
9 months ago