This took place a couple years ago. Let me know if you enjoy it as much as I enjoyed reliving it!
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Kate was an older woman, someone I’d met on my way out of a Q&A with a celebrity we both liked. It was a sweaty NYC summer day, that blissfully unappreciated freedom of the pre-end times, and she was behind me in line. She was nearly thirty, a former athlete and current industry professional and the face of a company with an enormous valuation, and dressed like it. Even her ‘day off’ styling was perfect, round white shades with pointed ends drawing the eye to her matching smile. When she joined the line I was leaning against the railing, dressed *fine*, but nowhere near her level. Nevertheless, she gave me a smile as she removed her shades. I smiled at Kate, but we didn’t speak. She had headphones in and I didn’t want to be a bother.
We went to our seats and, in the jumble, were seated with two people between. She asked a question, and when we all filed out I could see her dawdling at the bottom of the steps and sped up.
“You had the best question, super interesting.”
Kate smiled, “Thanks, his work is just genius, there’s so much to dissect, isn’t there?”
We walked and talked for two, three, four blocks, conversation flowing and the chemistry obvious, before we had to split, and I asked her for some way to contact her. We traded instas and she DMed me almost immediately, expressing surprise at my age.
“You’re not even twenty?! I thought you were almost my age…””haha I’ll admit, I didn’t have any intentions of spoiling that idea. Is that a problem?””What do you mean?””Does my age matter to you enough to not see me again?””Not at all.””How about next weekend then?”
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Kate found me in her lobby and we entered the elevator. I’ll admit that with the age difference of nearly a decade I was less sure of the dynamic she’d want, but the way she seemed to tilt and shrink herself, lowering her eyes, gave me the gut instinct I knew to trust. She lived high up so we had some time, so I stopped talking mid-sentence and stepped towards her, grabbing her hip in one hand and placing the other on the small of her back, pulling her towards me even as she closed her eyes and leaned towards me. The first kiss was electric, and I could feel her breathing hard against me, her breasts barely covered by her blouse rubbing against my chest. I pressed our bodies together and grabbed her ass before pushing her against the wall, Kate moaning into my mouth when her back hit the wall and her chest was squeezed between us.
Suddenly, the elevator dinged, and we broke apart. We weren’t yet at her floor, so with a smile a pregnant woman got on and pressed the floor above Kate’s. We had separated rather violently, and so the woman stood between us. Our eyes met and we smiled at one another, not a friendly or warm grin, but a feral smirk, both of us knowing what was going to happen.
The elevator halted and we quickly walked to her apartment, and I squeezed her ass and gave her earlobe a suck as she fumbled with her keys. We stumbled inside her apartment and she pulled me to her bed by the belt, sitting on it backwards as she unbuckled and pulled my pants down. Kate didn’t look at me at all, instead focusing on whipping out and immediately sucking on the tip of my cock. She closed her eyes as she tried to take more, bobbing her head as I gathered her hair in my hand. When I had her hair clenched tight, she wiggled her head as she looked up at me, her brown eyes starting to tear up as she finally took me as deep as she could, holding there until she pulled herself off, taking ragged breaths and licking the spittle that connected us.
Somehow we found ourselves naked, her perfect athlete’s body under me as I kissed my way from her lips to her lips, before nipping at her inner thigh. The cool air of her apartment made every lick shocking, so when I began sucking, licking, then releasing her clit, Kate began to gasp. I could tell she was sensitive and was determined to push her to the edge, and so continued alternating between teasing her clit and sucking each fold before finally pushing a finger inside her. She was incredibly tight, and inserting the second finger was difficult, but I loved how her back arched when I’d drag and push the pads of my long fingers until I ran out of finger to give, and how she’d groan as I removed them. Watching her react as I played with her clit and fingered her was honestly my favorite part of the night, but hearing her beg for me to just fuck her took a close second.
“Just… Get on top.” She was still shy, raised conservative, but I’ve always enjoyed hearing these shy girls push themselves.
“The way you asked me-” I sucked her clit and flicked it rapidly with my tongue inside my mouth, eliciting loud, neighbor-bothering moans from her, “-just isn’t good enough.”
“Please… Fuck me?” Kate replied hesitantly
“Again.” I said authoritatively, biting her inner thigh even harder.
She got into it now, “Please, *please* come fuck me.”
Before she finished I had already positioned my cock, and was lightly biting her nipple as I pressed myself inside her. Neither of us mentioned a condom, and she was so tight that the moment it occurred to me, the thought was banished by her explosive energy. Kate reached up and pulled me to her chest, and we kissed as I slid myself deeper, her legs trembling in the air as we moaned into each other’s mouths.
“Fuck. Your pussy- you’re so tight.”
She didn’t say anything, but as I pulled back and started to slide myself in slowly I could feel her flexing around me, and it took all my willpower not to force myself as deep as possible and cum right then. After a few more slow thrusts with our chests pressed together, I lifted myself and put her knees on either side of my head, using her as leverage to begin pounding. We’d both had a dry spell, so the normally fantastic sex was heightened by our simple desire for contact, the way her pussy gripped me begged for it to be filled, and the way my cock stretched her made her gulp and ball up the sheets in a fist, putting the other hand against the wall behind her to provide more resistance to my thrusts.
With each thrust I could feel myself getting closer, and I knew we could just go again in a couple minutes so I didn’t slow up or change positions, just dropping her legs and wrapping my right hand around her throat, my left beside her head, holding me up as I slammed her as hard and deep as I could. Suddenly her pussy tightened up around me, her hands both pressed against my chest and abdomen as if to push me away, but without any force, and her legs wrapped around me, pulling me deeper. A deep moan escaped Kate’s chest and her back arched, forcing her to stare at the wall behind her as she came. I didn’t slow up the entire time, only releasing her neck to support myself when she wrapped herself around me so I could still drive each thrust home. I watched her cum, and it was as if my orgasm was on hold until she’d finished, her incredible pussy tightening and flexing around me until she collapsed back with a huff, breathing deeply, but her legs never loosened their hold around me.
“I’m close.”
At this Kate tightened her legs around my waist, pulling me deeper and turning her head to suck on my thumb as she looked up at me with a coy smile. Again she said nothing, but I could feel how her pussy was massaging me, her control otherworldly, and after I began shooting I couldn’t help but collapse atop her, only having enough energy to make sure every drop of me reached as deep as possible.
I’ll be honest, I nearly passed the fuck out right then, but Kate started licking and nibbling on my earlobe as her pussy slowly expelled my softening cock, eventually slipping out into the cool air.
Source: reddit.com/r/gonewildstories/comments/ill2uj/seducing_an_older_woman_mf
Very fucking hot