Oh Dorothy

by Mike

Gender: Male
Age: 39
Race/ethnicity: White
Current location: Vermont
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Chemical engineer
Relationship status: Married
Religious affiliation: None
How religious are you? Not at all
Sexual orientation: Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 19
How many hookup stories have you here posted before? None

Oh Dorothy

How long ago did this hookup happen? Approximately 10 times

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…)? Short fling

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? 5-ft 1-in Greek gal.  A little on the heavy side.  Brunette with very Big breasts.  Met her on internet.  Very pretty face.  Went out for dinner and drinks.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? On our second date we started kissing in her car and I started kissing her breasts. She invited me back to her place…

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? Once we got back to her place we drank a beer each and started kissing.  Within a few minutes I was licking her pussy and sliding my fingers in and out of her as she sat on couch.  I picked up her bottom a bit and started licking her asshole.  That was the first time I’d done that but I loved it.  I also started fingering her ass as well.  When it came time for her to return the favor she started performing oral on me while I sat on the couch.  Then, a surprise to me, she started licking my asshole after licking my balls.  That was so hot!!!  She told me she didn’t swallow but did so anyway.  We then proceeded to have vaginal sex in all different positions.  I loved the 69 and kept licking and fingering her ass.  I would pull my finger out of her anus and insert in my mouth to moisten my finger then re-insert.  I was never so turned on.  She never put her finger in my ass but rimmed my anus several times.  I wish I had called in sick to work and just had sex with her all day the next day.

Did you have an orgasm? Did your partner(s)? Yes, I had a couple.  Don’t remember if she did or not.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? Condom during vaginal sex.  No, didn’t discuss STI history.

What were your REASONS for having this hookup? I haven’t had many partners and wanted to fulfill some of my fantasies.  I had also just gotten out of a multi year relationship and was seeing who was out there.

Were alcohol or drugs involved? If so, how much? Yes, alcohol.  We were both buzzed.

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 initially felt ashamed and a little freaked out.  The sex was dirty and she was a bit heavier than I wanted in a girlfriend.  The next hookup she told me the ass play was a bit much for her.  However, she let me continue to finger and lick her asshole on previous sessions.  That’s what made it so hot…the taboo stuff I guess.  She moved from Boston back to NU but we connected a couple years later and had some good sex sessions.  Last time I saw her she blew me 2x and swallowed each time.  However, she wouldn’t let me have sex with her or lick her vagina.  That’s when I knew something had changed.  She wanted more…she is married now.

To whom did you talk about the hookup? How did they react? I never told anyone.  This occurred about 7 years ago.

Was this a consensual and/or wanted experience for you? For your partner? Yes, and I’d love to do this again!

Do you regret this hookup? If so, why? No way!!!  It was HOT!

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? I just liked the uninhibited sex.  We enjoyed all of each other and that made it so much more intense.  I felt a certain chemistry, which I don’t even feel with my own wife.  Thinking about this experience makes me wonder if I married for the right reason(s).  This was before I was married but I continue to feel that somehow I’m missing out.

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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