by Charlie
Gender: Female

Age: 26
Race/ethnicity: White
Location: NYC
Highest education received: College degree (eg., BA, BS)
Occupation: Tech/Start Up
Religious affiliation: Raised atheist/non-believer
How religious are you? Not at all
How many hookup stories have you here posted before? 0

jamesspadersecretaryspanking
Spring of No Plans

How long ago did this hookup happen? 5 weeks

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, paid sex; something else.)? Old FWB revisited

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? Single partner; we had hooked up a few times previously almost 18 months ago. We met via OkCupid; I messaged him first because I was intrigued by the blatent-yet-totally-respectful way he referred to some kinks I highly suspected were mutual. If asked before this most recent hookup, I’d have had very fond memories of the sex. Eighteen months ago he had been my first hookup that was explicitly and pre-negotiated to be some D/s play. I had totally forgotten how piercing his eyes are; and misremembered his body.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? With a text message from someone I hadn’t seen/heard from in almost 18 months. Turns out he was coincidentally back in town a few weeks after my now-ex and I amicably ended things. Planning/scheduling was involved; it worked out that we both had a weekday morning free so we arranged I would go to see him.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? Oral, vaginal, and some light-to-moderate D/s play. He topped, I bottomed. No toys, but my ass and tits were bruised from the spanking and my nipples were pretty chafed. I came (multiple times, I think?); so did he (just the once).
We knew exactly what we were meeting for, and I was naked shortly after we met. He’s excellent in bed, an excellent top, and after confining safewords/hard limits (stop light/no bruises visible in work clothes), I think it went something like: spanking, me giving oral, more spanking, more me giving oral, him playing with my tits/himself before he bent me over the bed and spanked/fingered/caressed me until I was ready to beg for him to put his cock inside of me.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condoms; I also have an IUD. Testing/partners were briefly discussed afterward.

What were your REASONS for having this hookup? The timing was right; I had fond memories of our previous hook-ups and I liked the idea of my first hook-up post-breakup being with someone I knew I had chemistry & shared proclivities with.

Were alcohol or drugs involved? If so, how much? None, this was the middle-of-the-day, and we were both stone-cold-sober.

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? He hopped in the shower, we made small talk; he’s back a thousand+ miles away for work now and we both knew exactly what we were doing: a sex date, no further expectations. And I walked around glowing for a least a week.

If circumstances were different, I could definitely see myself wanting to date him; he was even more attractive than I remembered (I’m terrible at faces) and the chemistry is definitely there.

To whom did you talk about the hookup? How did they react? I like talking about sex; my ex, my best friend and my sister got more-or-less the full story. I did walk around all smirking and floating about the super-fun day-date I had; most of my circle of acquaintances don’t know I consider myself kinky so details were edited to “an old hookup was in town.”

Was this a consensual and/or wanted experience for you? For your partner? Yes, absolutely. On both counts. Post-hookup texts confirmed this.

Do you regret this hookup? If so, why? No.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? The flying/high/content feeling I walked around smirking about for days after. There’s no real “worst” but it would have been nice to play for longer.

This was my first D/s sex in a good long time; it just confirmed that I do very much like being expertly topped.

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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