by James


Gender: Male
Age: 32
Race/ethnicity: White
Current location: Boston
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Investment Banker
Relationship status: Married
Religious affiliation: Atheist
How religious are you? Not at all
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 26
How many hookup stories have you here posted before? 0

Oral With the Ex

How long ago did this hookup happen? 14 years ago

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? She was an ex-girlfriend of mine; we had sex many times while we were together but it was very vanilla.  Very little foreplay, missionary sex.  About a year after I dumped her, we ran into each other at a party.  I truly had no intention of ever speaking to her again until we bumped into each other.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? A couple of days later, she texted me and we each confessed that we were horny, and we agreed to “help each other out.”  I went over to her apartment at around 10 pm, still not knowing quite what to expect.

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 went over and after a few minutes of awkward small talk, we went to her bedroom.  We agreed there would be no kissing so as not to bring feelings back into the mix.  I pulled down her pants and went down on her until she came.  After that, she sucked my dick.  After 5 or 6 minutes, I came in her mouth and she swallowed.  I noted that she had improved in that department and she said she had given head to 6 guys in the year since we broke up and so she had some practice.  That turned me on and I asked her to blow me again, which she did, and she swallowed the load again.

Did you have an orgasm? Did your partner(s)? Yes, we both did.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None.  This was oral only, but even when we started fucking again we never used condoms even though I always came inside her, as she was always on the pill.

What were your REASONS for having this hookup? I really didn’t like her at all – hence the breakup – but was horny and wanted to get off.

Were alcohol or drugs involved? If so, how much? None.  We hooked up many times after and I sometimes was under the influence of alcohol or coke.

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 was sort of ashamed, but we kept hooking up after.  Usually she would text me and ask me to come over.  The next few times were oral only, including 69 and some ass play, and eventually we started full on fucking again, never with condoms.  She started to become emotional again and I eventually broke it off.

To whom did you talk about the hookup? How did they react? I told a few friends, who laughed it off.

Was this a consensual and/or wanted experience for you? For your partner? Yes, for both.

Do you regret this hookup? If so, why? No, but regret continuing to hook up as she became clingy and wanted a relationship, and I did not.

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 best thing, obviously, was her sucking me off and cumming in her mouth twice. Needless to say, it felt very good.  The worst was her developing feelings again.

All things considered, how POSITIVE was this experience? Fairly positive

All things considered, how NEGATIVE was this experience? A little negative

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