by SS

Gender: Male
Age: 50s
Race/ethnicity: White
Current location: USA
Highest education received: College degree (eg., BA, BS)
Occupation: Professional
Relationship status: Single
How religious are you? A little
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 20
How many hookup stories have you here posted before? 0

Registered Nurse

How long ago did this hookup happen? 6 months

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…)? FWB and more

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? I travel to Southern California quite a bit for business.  On one such trip, I went out for a late dinner at a popular, local pub with live music.  Quite by chance I sat down at the bar down next to a very cute, petite woman in her late 50’s.  Julie (who I later learned was a health care worker) was quite attractive with dark curls, mischievous blue eyes, and a great smile. Apparently she had been drinking martinis long before I arrived and was feeling no pain.

We chatted for quite a while.  During the conversation, Julie confided that she had originally arrived that evening with her boyfriend but he had left for some reason.  Several drinks later, sensing she would be receptive I told her, “I would really like to see you again.”  As she left the bar for the evening she responded, “That might be tricky”, but not before slipping me her phone number.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The next morning, I called Julie’s phone and reiterated my desire to see her.  Her job at the time was quite flexible so she agreed to drive to my hotel, pick me up, and get further acquainted over lunch.  Frankly I thought she would flake out.  But sure enough, Julie arrived at noon, and we headed out to lunch.  More fun conversation, several glasses of wine, food, then into her car for the return ride to my hotel.

As soon as we arrived in the parking lot, I asked her, “Please come inside with me”.  At first she was reluctant, but she eventually took my hand, and we headed up to my room.

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? After entering the room, I sat down on the edge of the bed facing her.  I’m quite tall so doing so put us face to face.  Despite her initial shyness, Julie slowly warmed up to me as I kissed her gently and ran my fingers through those luscious curls.  God, she smelled nice.  I lifted her hands up and she removed her blouse, then her pants.

At this point it was if I had flipped a switch, as suddenly all her inhibitions totally vanished.  Julie kneeled down, unzipped my pants, pulled out my cock, and began sucking.  Several enjoyable minutes ensued before I stopped her, removed the rest of my (and her) clothes, and joined her in bed.

Up until this point I hadn’t really appreciated what a fantastic body Julie had until her clothes were completely off.  For a petite girl (5′ 2″), she had a nice ass, and very large natural breasts (maybe 36DD), with dark nipples as large as pencil erasers.  Sticking out of her partially shaven pussy, was the largest clit I had ever experienced. (She later explained that she was on some sort of hormone therapy and that an enlarged clit was one of the side effects).  Regardless, it was gorgeous.

Parting her slit ever so gently with my hand, I immediately went down on her, and she came very quickly for me.  Again, she smelled great and tasted even better.

My turn now.  I spread her legs and slowly slipped my cock inside her.  What a feeling!  She was wet, ready, and tight.  I’m generously endowed and she eagerly took every inch of me.  Talk about a perfect fit….

I stroked her missionary for a while, then stroked her on my side while fingering that beautiful clit.  She came again.  Then some doggy, some cowgirl, then more missionary when I finished inside her.

We hugged and talked for quite a while afterwards, I walked her to her car, and then she left.

Did you have an orgasm? Did your partner(s)? Me: Yes!
Her: 3 or 4

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None.  I knew I was clean and she was in health care.

Were alcohol or drugs involved? If so, how much? I’d say that alcohol helped to remove many of our inhibitions both the night before and that day.

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? Saw her several times afterwards.  Became good friends.  Same great sex.

To whom did you talk about the hookup? How did they react? No one.

Was this a consensual and/or wanted experience for you? For your partner? Quite consensual for both of us.

Do you regret this hookup? If so, why? Not at all.

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? It was absolutely glorious sex.  In my experience the first time with a new partner is often rushed and/or awkward as it takes a while to learn preferences, etc.  Not so with Julie.  It was great from the get go.

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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