by Joe Dreg
Current location: Illinois
Highest education received: College degree (eg., BA, BS)
Relationship status: Single
Religious affiliation: None (Atheist)
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 0
How long ago did this hookup happen? 1 Year
How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Sex with an ex
Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? About 6’1″, heavy and alluringly shapely, long black hair, almond skin, nose ring, four tattoos, pierced nipples. The most gorgeous eyes, mouth, face.
How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? Technically, it began two nights before, when after an evening of drinks and tacos, we fooled around and fucked in my art studio. Apparently, we were getting on just fine after a long time of not seeing one another/communicating. We exchanged some texts the next day suggesting that while she was in town, we should get some more alone time.
What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I picked up, let’s call her Nicole, at the nearby subway station; she had told her host she was going out to lunch with an old friend. We had a leisurely 15 minute walk back to my apartment and did some more catching up – it was clear we still had a good rapport, and we were both sort of poking fun at what we knew was the plan for the day.
Upon returning, I quickly showed her my new apartment, and when I showed her the bedroom, she wasted no time laying down on the bed, as if to say “tour’s over, come join me.”
I laid down with her and we began making out. Making out turned quickly into getting naked, and getting naked turned into her primary request for the day – sucking my cock. I laid back and Nicole hunched over me on her hands and knees, taking my entire cock into her mouth. That lasted maybe five minutes, and pretty soon I asked to kiss her pussy. She was always a little uncomfortable with cunnilingus, except when I specifically offered to kiss it. So I kissed it and sucked her clit and began fingering her. She turned over, and I started fingering her from behind, gradually increasing the number of fingers in her now seriously wet cunt.
We began fucking in a number of standard positions; missionary, legs over my shoulders on the side of the bed, piledriver-style doggy, and some face-fucking as well, all done very, very hard. It had been a while for both of us, so she began getting sore about 15 minutes in, and we took a brief cuddle break and smoked some weed.
After about 5-10 minutes of blissing out naked in a comfy bed, she asked “want to do something really filthy?” Her request was that I a) fuck her some more, b) cum in her mouth, and c) fuck her a little more while watching her swirl my cum around her her mouth before swallowing on my command. And that went just about as described. She also willfully gagged herself on my cum.
Round two began with Nicole asking for a butt plug and some lube. Totally stoned, eyes closed, she laid on her side and began gently fucking her own ass with the toy. I stood up over her and watched while she squirmed around on my bed, getting ever-deeper in her own ass. I’m sure she started talking dirty at this point, but I can’t recall any of what might have been said.
At this point I kneeled on the bed near her face and offered to let her suck my dick again, which she happily obliged, pushing the butt plug in all the while. She asked “will you slap me in the face…” which I did almost instantly, before hearing the second half of her sentence, which she finished a little flustered from the slap “….ahem, with your cock please?” She had enjoyed being slapped around in our sexcapades numerous times before, so it wasn’t SUCH a crazy presumption. Anyway, I did slap her face with my cock as requested, and smeared lots of her drool on her cheeks as well.
I asked “do you want me to start fucking your ass?” She kept her eyes closed, smiled ear to ear, and nodded her head vigorously. So she laid down the plug, and I began.
I kneeled behind her ass, as she remained reclined on her side, and started slowly entering the warm hole, slightly prickly from anus hairs. She controlled the depth and pressure and I just knealt there. When she was ready to start fucking properly, I didn’t hold back. I fucked her ass harder than I ever had before, and she laid there telling me to fuck harder. “I’m such a fucking slut,” she repeatedly moaned. I asked “What do whores do?” “They take it in the ass!” she responded.
About now, she was pleading with me to cum in her asshole, and I was fucking her pretty hard. We were both into some degree of kink, so before coming, I upped the ante. I picked up her dirty butt plug, held it near her face, and asked if she wanted it. She instantly started licking and sucking the tip, cleaning off dried lube and shit with her tongue, smiling all the way. And that was when I blew a load deep in her tight, hot, dirty ass.
Cleaning up her creampie as she tried to stand she asked “ARE WE FRIENDS NOW?”
Did you have an orgasm? Did your partner(s)? I had two, she had none, but insisted she was enjoying herself (historically, she had difficulty coming to orgasm).
What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? No precautions, but we did briefly ask one another about having been tested. We were both in the clear.
What were your REASONS for having this hookup? We were both lonely and horny and on good enough terms to have some non-committal fun.
Were alcohol or drugs involved? If so, how much? We both smoked some pot after round one, and were reasonably high for the remainder.
What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? I think we both wanted more. But geography prevented it first, and emotional distance made it final. We exchanged some dirty talk and photos over the coming months, but it was becoming pretty clear we were co-dependent, and we began, bit by bit, mutually distancing ourselves.
To whom did you talk about the hookup? How did they react? Maybe three or four close confidants. They were generally happy that I was able to have such an encounter with a minimum of emotional strife over it, but cautioned that I not read too much into the experience as a sign of true reconciliation with my ex.
Was this a consensual and/or wanted experience for you? For your partner? Yes, consensual on both sides.
Do you regret this hookup? If so, why? No regrets. It was some of the best sex I’ve ever had.
All things considered, how POSITIVE was this experience? Very positive
All things considered, how NEGATIVE was this experience? Not at all negative
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