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Years ago, back in the days of Craigslist, and when women weren’t inundated by “HEY COME FUCK ME SIGHT UNSEEN” posts…

I wrote a simple ad. I was experimenting with a notion my newly single self had figured out; a good sweaty, sexy session was best if there was trust there. Dudes were writing advertisement asking to fuck women in the ass with no lube, degradation scenes, facials…and not realizing or caring that a woman has to trust you to want to do that with you.

So I put out an ad looking for a true FWB. Someone who I could converse with and earn that trust..and get into some hot, hot sex with. And eventually, it worked out.

She was a teacher, verbose and educated, and was curious at my use of big words and proper grammar. We talked for a while, texting back and forth, and she was so piqued at what I was offering she offered to meet me at a public place, a bar between us.

She was a true MILF in every sense of the word. Early 50s, thick in the right places. She was in a marriage of convenience, and was bored and lonely. While we talked, there was an electricity between us that she amplified by making raunchy jokes, by slyly musing as to how big my dick was, to wondering out loud if I was as good of a kisser as I looked. We went back and forth for about 20 minutes, and when a waitress came over to ask if we wanted to order anything, she looked right at me and said “no, we have an appointment” and got up to leave. I followed, obviously.

The makeout session we had in her car, whew. I get hard remembering it. Her thin lips matched my thick ones. Her hands went everywhere and got to feel for herself how big my dick was. We fogged up the windows on a cold Chicago night. Afterwards, she texted me, and I enjoyed going back and forth with her; she was literary, and made me think of old English classes and got me wondering what vocabulary she’d reach while she came…

>My students write six word memoirs
>
>I love the weight they carry
>
>Less is more; more is good
>
>Know what else is good?…Fucking.

She had a life; a husband who had a medical condition that rendered him impotent and mostly homebound. She wanted to let off steam, and I was a eager conduit. We met twice more for lengthy takeout sessions in her SUV before she could clear time to meet for our first session.

She came to my place, and we couldn’t keep our hands to ourselves, her thin lips molding into mine effortlessly. I couldn’t wait to eat her up.

She got shy about taking her bra off – “The girls aren’t what they used to be,” she demurred – but readily stepped out of her panties, slid onto my bed with her ass up in the air, and commanded “Taste me first.”

And oh, how I dug in. She tasted of earth and sweet things, and her excitement was evident. I lapped up her juices eagerly, and my enthusiasm was coached and encouraged. Breathlessly, she guided me to what made her feel good. Two fingers in, slowly working her g spot as she told me to take my time, and I obliged. Slowly, I traced her inner lips with my tongue, humming my satisfaction and ardor.

I realized some time later that I hadn’t taken off my boxers, and a gigantic spot of pre-cum had soaked through. After a while, she asked me to stop and to kiss her, and I did so. As I did, her hands found their way to the thick bulge, and she lightly caressed it. Her fingers traced the outline lightly, finally encircling it and giving it gentle squeezes.

“I see my young ward is ready for me. Whatsoever shall I do with this?” she cooed playfully.

“Prithee, take this swollen member to the hilt,” I replied gruffly, an few octave lower than my ordinary voice. Her eyebrows widened in surprise, then she smiled.

“Well then, good sir, let me have it.”

I propped a pillow under her hips – “you said you wanted it to the hilt,” I reminded her – and rubbed my dick against her clit. She giggled, and asked not to wait too long, not to be teased.

When I finally slid in, it was absolutely unreal. She gasped, eyes wide open, and emitted a low, sexy moan. I smiled, and kept going until I ran out of dick. To the hilt, as promised. I stayed still in her, not moving, feeling her contract and pulse around me. Take my time? Sure. But I don’t think you knew what you were asking for…

She began to buck her hips, and I responded by pulling all the way out. She gasped again, and looked up at me, wondering.

“You seemed to like when I first slipped in. Let me do it again.”

Her protests were cut short by me entering her again. Holding her legs open, I could feel them quiver. Her face was a picture of absolute ecstasy.

I then started to pump in and out slowly, watching my dick become wetter and wetter with her juices as she started to meet my thrusts. “Let this dick do the work,” I told her. “Let it love where it is, and how it makes you feel.”

A few more minutes in missionary, with my tongue in her mouth and my hips acting with a mind of their own – never fast, never rushing, varying the depths in which I was giving her this dick. Shallow strokes would lead to three or four deep ones, and all the while she cooed and moaned and orgasmed around me.

I finally withdrew, a long string of our combined juices still connected my dick to her receptive pussy, as she caught her breath. “Want to change positions?”

She explained that her knees weren’t very good, but I had other ideas. I flipped her onto her stomach, opened her legs just a bit, and arched down and ran my tongue from her clit up the crack of her ass. Just one long, sumptuous lick, and my tongue moving across her asshole, if only for a second, made her emit a whimper. “Oooooh, shit.”

I rated up, mounted her nice ass, and slid back into her willingness. “Close your legs a bit,” I instructed, and she did what she was told and shuddered again as I slide in her as far as I could go. “Fuck, you fill me up.”

“Wait a minute.” I slid out of her and retrieved the pillow from earlier, putting it under her hips. “Let’s try that again.”

The angle more conducive to my height, I was able to slide in to the hilt again. Her pussy became noticeably wetter, her closed legs providing a tighter fit than I had imagined. I started my thrusts again, nestling my head between her shoulder and ear, telling her how good she felt. Her responses weren’t words; just sounds signaling her willingness and pleasure.

I wasn’t gonna last long doing this. Her ass was plump enough to jiggle when I raised up and watched her asshole clench as I pumped into her.

“You’re about to make me come soon,” I informed her. “And where do sexy cougars want young paramours to do so? How dirty do you want to be? How much do you like this dick?”

Panting, she blurted out “Anywhere, baby. This pussy is yours.”

Well, no man can really withstand that, and all of my delay tactics were powerless in the face of this utterance.

I stroked a few more times, and pulled out. Still holding myself up on my forearms, in pushup position, I watched as my dick erupted on her ass and lower back. She cooed as she felt my load pool up.

I reached for a towel I had placed close by, and gingerly cleaned her up. After she caught her breath, and was satisfied that she wasn’t sticky, she flipped back onto her back and looked up at me, smiling. Her attention soon went to my dick, which was still hard.

She motioned me to come closer with her finger. “Come here.”

I leaned close; perhaps this was the snuggling period, or aftercare..?

She reached between our bodies, grabbed my still hard member, and pulled. Being guided in such a manner, I let her pull me in…right between her waiting legs. I looked up at her. “You sure?”

She responded by rubbing my dick on her clit, even slapping the head across her labia. Still slick with the mixture of our juices, she slowly began to stroke it, leaning up to put her tongue in my mouth.

She broke the kiss, and leaned back again. “Put it in, and fuck me hard.,”

I started by sliding in gingerly, going through unknown territory. My dick hadn’t stayed hard after a good nut in a very long time; I was on cloud nine, and my mind could think of nothing but sex and putting my mouth on her, putting my dick wherever she wanted me to.

She responded by putting her hand in the small of my back and drawing me in, finally locking her legs around me. My orgasm forgotten, I was hard as a rock again.

“Fuck. Me. Hard.”

“Certainly, madam.”

The next few minutes were a blur of her moaning, the squish of our skin meeting and parting, her pussy feeling incredible. I don’t remember the orgasm, but I do remember collapsing in a heap next to her, sweaty and spent and unable to talk for several minutes.

>That first push in weakens me.

During the next few weeks, she sent me various messages, answered in kind.

>I am spent. Miss your form.
>
>This brings to mind lovely images…
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>Of tongues and teeth gently pulling
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>Of hips, thighs moving as one

Moving away from six-word responses (thanks, Hemingway) we expressed a deep desire to do it all again…

>Curled up, my back to your chest, you sliding in from behind and rocking me to sleep…
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>I liked it, after I’ve been with you, to rub my pussy and smell your cock…
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>Your smells mixed with mine
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>It moves me, that cock of yours
>
>My god, I don’t know how you did what you did the last time, but it was epiphanous.

After a number of family emergencies and missed connections, she emailed me to set up a date. I emailed back, to no answer. I texted her..to no answer.

I wonder where she is now…I hope she’s okay…

NSFW: yes

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