After I got my education, career, and finances in order, I started dating. A lot. Between 2001 and 2006 I had a *lot* of sex. To this day it’s astounding because I’m a pretty gawky guy and I like to keep to myself; plus I’m bookish on top of it all.

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Kat (not her real name) and I had been out a few times. We’d been introduced by the matchmaking wife of a friend of mine, and between my aloofness and her recent divorce we were paired “just because”. I liked Kat, but what I’d known about her divorce was a lot to take in — in particular because I had never been engaged or married.

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Our first few dates were fun and enjoyable. Kat was extremely tall (6′) and as I am extremely tall she would always wear these hot high-heeled shoes that she’d been saving up for “the tall man of her dreams”. I remain delighted by a woman in heels, and she was delighted to be able to wear them with a guy that she wouldn’t tower over.

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We’d made plans to have a couple of drinks and then to grab an early dinner at this trendy place this one Sunday afternoon. I don’t know how it happened (oh, I know exactly how it happened!) but I ended up agreeing to get dressed up for this event, and Kat’s attire didn’t disappoint. The mid thigh dark dress and it’s pleasant display of cleavage. The pearl necklace. The open toed highest of heels. The pearl necklace. I wasn’t even fazed when she wore both her wedding band and engagement ring. She looked and smelled great, and when she finally gave me the address to her house that Sunday I was wondering where the day would end up. For her part of things she was also effusive in praise about the way I was dressed.

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Back then I barely drank. I would have a couple of glasses of wine, but I also ran and worked out a lot, so any amount of alcohol would absolutely crush me. After 1.5 glasses of wine at this bar I was hoping that I didn’t stagger and fall down like a giraffe. I felt like a giraffe to be sure. Then we got seated immediately (and surprisingly!) at this popular place and she immediately ordered a bottle of wine. Thankfully she drank most of it so by the time we sauntered back to her place I was mostly fine. Kat was stacked, by the way, and alcohol seemed to have very little affect on her. It’s almost like she could just drink and become even more charming, but wasn’t staggering or whatever else.

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She invited me inside, and after having unlocked the door I followed her in. After having closed the door and asking her if I should deadbolt it, I made some kind of gesture (I guess?) and next thing you know I’m pushing her against a wall and she’s practically biting my lips off. Hands roamed. Tongues tied. Lots of grunting and groaning. I’d wedged my thigh between her legs and she was dry humping it. In the meantime she was tugging at my butt cheeks and driving me into her even harder. When my hands had hiked her dress up a bit I felt bare cheeks. Commando? Thong? G-string? Oh, this was good. And then she stopped me.

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Apparently she was “already spending too much on dry cleaning” so she told me to sit on the couch while she changed. I had thought that would be the end of the night, but I was wrong. Very wrong. She emerged from her bedroom wearing her bra, sheer panties, and her sexy heels. She motioned to me and I walked towards her. She unbuttoned my dress shirt, throwing my necktie somewhere down the hall, and told me to take the shirt off. She put my shirt on with the buttons a bit crooked, and showed a lot of cleavage. We started making out again and she was first to make the next move. She undid my belt and unbuttoned my dress pants letting them slip to the floor. She pushed me towards the couch and I fell on it. Her hands snaked me out of my boxers, and then she took me in her mouth. I tried to touch and to fondle her but she slapped my hands away.

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Her mouth was hot, wet, and tight. Her lips were like pillows and the suction was fantastic. Her fingers toyed with my taint as I tried not to buck into her mouth. Some time later I told her that I was getting close, and she forced her mouth down to the hilt and I finished in her. She swallowed all of it.

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I thought we might be done, but she straddled me as I sat stupefied on her couch. That’s when I got handsy, and soon my dress shirt was discarded along with her bra and I grabbed her butt cheeks and started dry humping her against my now bare cock. It was totally obvious from her sheer panties that (a) they were of the sexist thong in the world variety and (b) that she had perfectly landscaped her area and that it was completely bare. My fingers had started to probe her warm and wet area, but she got off me and gave me the “come hither” movement with her index finger. As we stripped off our remaining clothes, and all of them were left in a trail down her hallway, we reconvened in her bedroom.

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She got on all fours and my mouth attached itself to her. Then I realized that she was completely bare and my tongue and fingers made it to her asshole. She protested at first but then sunk into what was happening and began to frig herself as I tongued her. Not too long after her body tensed up and she squirted all over me.

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I didn’t use good judgment that night and the following morning. We just never took a break, and I fucked her bareback repeatedly including cumming in her twice that night and once the following morning as I bent her over the kitchen counter. Still, those 24 hours together featured animalistic fucking like I had never experienced before. A few days later I was surprised that she didn’t want to hang out anymore. But then again she finally disclosed that she and her ex were still fucking and that maybe they’d give it another shot. Ah well.

This story was originally published here

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