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First hook-up: masturbating and more
Posted:Dec 19, 2020 8:11 pm
Last Updated:Nov 18, 2021 9:07 pm
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I shouldn't have done it.

I knew that before I started, putting an ad on Craigslist saying I was a married guy who was on the road and horny and was interested in masturbating with a woman in the room. Were there any women who would want to be a part of it? That was the gist of the ad. And it turned out that there was a woman who wanted to do that.

I was married. That's the part that doesn't work. And my wife could be a hot fuck too, when she was in the mood. She is, for instance, enormously gifted at sucking cock. She loves to do it, when she's in the mood. Gets off on the power it gives her, having a man's penis between her teeth, but doing nothing but pleasuring him, making him squirm and moan. She'd finger herself as she sucked me, opening her thighs so I could watch. But what I said about power? Sex was power to her, and she wielded it for all it was worth. Sex was on her terms, always. I could deal with that for twenty years. But then some internal tide shifted. And then I was thousands of miles from home, and horny, and wanted sex.

Her name was Elaine, and she was a lawyer. We traded emails. I got her first response when I was in the airport that morning. Juggling coffee, a bagel, and my phone as I checked my email. Just for grins I checked my secret email, the one where I tuck the hot sex pics I collect, where I get the receipts for the online sex sites I like. And there was the email, via Craigslist. That sounds really hot to me, she wrote. Coffee in one hand, bagel balanced on my thigh, phone in my hand and, suddenly, a throbbing penis. I wrote back. Cool! What else can I tell you?

We traded an email or two before my flight, then picked it up again when I got to her city. I sent her a face picture. She said I was cute. We agreed to meet in the bar at my hotel at 5 pm. I felt electrified. I had a lunch meeting that went on for hours, and when my mind wandered I'd think of her, feel a jolt of adrenaline, and anxiety, and desire. A light throb in my crotch.

I drove to the hotel and checked in. Got up to my room. Unpacked. Ninety minutes til we were supposed to meet. I answered some email, did a little more work, checked the time every three minutes. Eventually it was time. I rode the elevator up to the top floor bar, and found a place to sit. After ten minutes or so I saw her coming. Saw her see me, more like. She was cute. Dark haired. A lawyer. My age, early 40s. i got us drinks and we sat on a sofa to talk. General stuff at first, where we were from, a vague sense of what we did. You know how never really tell your casual sex partners who you are for real. We edged towards our sex lives. She was married, too. Frustrated, just like me. But she'd been venturing. She liked to fuck, and so did her husband, but she needed something more. I told her about my life, my wife, what turned me on. She asked what turned me on about masturbating in front of someone. I tried to explain it. How it was something I'd done with guys on a bunch of occasions, but since I was straight this seemed hotter. Much hotter. She was liking what I had to say, I could tell. She suggested we go to my room to talk some more.

She sat on the edge of the bed and I sat at the desk chair. You know the kind; with the wheels and black webbing, adjustable, etc. We picked up the conversation again, and she told me about an FMF she'd had with her husband and a friend. It was spontaneous; they'd jumped him while he watched tv, and soon were both kneeling in front of him, taking turns sucking his cock, handing it back and forth. Group sex is a big turn-on for me, and I started to get hard as she talked. I didn't bother to hide it. I knew why we were there, what we both wanted to do, so I reached down and rested my hand over my crotch, feeling my semi-erect penis beneath my palm. I rubbed it, and she noticed, and smiled.

This was foreign territory, but I'd had a couple of cocktails, and that sex-driven adrenaline was thick in my veins, and pulsing down to my crotch. I felt myself getting harder, and fingered it through my jeans while she watched. She was really looking at it now, so obviously the time had come for me to unzip my pants. I can't remember how long it took for all this to happen, but I unzipped, probably pulled off my jeans and left my shorts on, with my obviously erect cock inside. I reached inside to touch it, then pulled the waistband down to pull it out. She was still talking, and I was going, uh-huh, really, then what happened? and etc.. With my fully erect cock in my hand.

I kicked off my shorts and pulled my shirt off so I was naked on the chair, stroking my dick, fingering the shaft, watching her watch me and feeling extremely turned on. So was she. In one abrupt motion she pulled off her blouse, undid her bra and pulled it off. She was still watching me, but now fingering her nipples, which were already stiff. Then she kicked off her shoes and pulled her skirt off, then her panties, and she was naked on the bed, one hand on her breast the other on her clit. She opened her thighs , still watching me, her fingers slipping up and down her lips, swelling and opening, and I was pumping my penis in my fist. Is it ok if I sit on the bed, I asked. She moved over and made room for me to sit next to her.

I could smell her heat. She was still sitting up, watching me watch her watch me, and we were gasping and stroking ourselves. For how long? I don't know. She reached over and took my cock in her hand, stroking me with one hand and fingering herself with the other. Then she leaned over. "I give better mouth," she said, swooping down to take my stiff penis into her mouth. She grabbed the shaft with one hand and stroked it while she bobbed up and down, sucking me.

The guilt. It burst through me. I hadn't planned on us touching each other. I thought we'd stick with the masturbating, her watching me, maybe her joining in, but both of us in some gray area between Faithful and Adultery. Hey, if I didn't touch her it wasn't really sex, was it? Just a porn movie in 3-D. Right? Except now my cock was in her mouth, and she was good at sucking, too. I could feel the pleasure mounting. I pulled her away, got up and told her to lie down, which she did. I pushed her thighs apart and leaned down to touch her clit with the tip of my tongue. She gasped, and I started slipping my tongue up and down her slit, circling her clit and going down again, then up, then circling, then down. She was pumping her thighs in my face, and I moved one hand up, fingers extended, so when she pumped again my index finger slipped inside. It was very wet and slippery, she moaned and opened herself wider, so I slipped ithe middle finger inside her too, pumping her with them while I circled her clit with the tip of my tongue. When her pleasure seemed to be peaking I told her to take over. For some reason it felt wrong to make her come, so I let her rub her own clit while I fingered her hole, slipipng my fingers in, taking them out, sliding up an down her lips, down to her asshole, cilrcling that, then up again. She started to pant, then she started to come. It seemed like a good one.

My cock was still fully erect and dripping. I got up on my knees, moved to get on top of her and straddled her stomach. Her eyes were glued on my erection, which I took in my hand and tugged, feeling my orgasm building, and wanting to draw it out a little, to tease her, to keep it going. She watched, licking some of her juices off her fingers, performatively, I guess, and I edged closer to coming. I decided to let go, and went faster, moaning, telling her I was going to come. "Do it!" she said. And that was enough, and I started to spurt. On her neck at first, then splashing her breasts, then a jet across her face, into her hair. And there was more, another spurt across her breasts, and another, a weaker one, and I was close to finished, but i leaned forward to touch the head of my cock to her left nipple, rubbing it against her, feeling it stiffen. She took some more come on her fingers and used it to rub her other nipple. Finished, I tumbled off her and lay down crossways, not next to her. She got up on one elbow to look at me. Some come dripped down and fell across the lower breast. "That was hot," she said. I nodded. "But I think you got come in my hair...I better shower."

How did I feel? Sated. Numb. Too spaced out to feel much of anything. She showered quickly, toweled off as she came into the room, pulled on her panties and bra, then her skirt and blouse. When she was dressed she stood up to leave, and I stood too, not sure what to say or do. She took me in her arms and kissed me, gently on the lips. It was the first time we'd done that. Kissed. "That was fun," she said. "Thanks." The door opened, closed, the lock clicked, and she was gone.

I can't remember what happened that evening. Where did I eat? What did I do? Did I get turned on thinking about it later, pull up one of her pics and jack off? I don't know.

The next morning I got up early and pulled on my running clothes. The hotel was in a hilly part of town, and the neighborhood nearby was particularly steep. I set off on a little up-and-down road, then found one that went straight up. It'd hurt to take that on, so that's where I went. Sweating and gasping. Lungs on fire. My dick felt a little sore in my shorts -- I probably did jack off later that night. I felt raw. I didn't stop. My lungs burned, my thighs burned. I deserved this shit. I kept going til I got to the top. There was a vacant lot with a view of the city, and I let myself stop there, out of breath, furious, feeling just a little bit cleansed by the pain.

It wasn't the last time I'd fuck around. Just the most innocent time.
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