by Dan

Gender: Male
Age: 27
Race/ethnicity: White
Current location: New England
Highest education received: Some college (not currently in college)
Occupation: Media specialist
Relationship status: Single
Religious affiliation: Catholic
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 3
How many hookup stories have you here posted before? None

From Out Of The Blue

How long ago did this hookup happen? Six months 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…)? 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? “Judy” was a friend of a friend.   Someone I knew of but had no real contact with.  One day I was at my apartment when she just showed up at my door crying.  She had had a fight with her boyfriend.  By the way, the boyfriend was a co-worker of mine.  He was much bigger than me and a bit crazy.  He also owned several guns.  Anyhow, she asks if she can come in.  I say yes.  I didn’t want neighbors hearing her crying.  We get inside and she says the boyfriend and her had a terrible fight and he’d hit her a few times.  All of a sudden, she throws her arms around me and hugs me tightly.  Not wanting to be insensitive, I embrace her.  She looks up at me, tears streaming down her face…and kisses me.  I mean REALLY kisses me.  “Judy” is dark haired, shorter than me, and several years older than me.  This is making me excited.  After a l-o-n-g kiss, we break for air and she says, “Make love to me.”  OMG!  I’m in shock!  No woman has ever said that to me.  But her boyfriend will kill me if he finds out I’d slept with her.  I stammer out words to the effect that I can’t do that.  “Jim”, the boyfriend, is a co-worker and sort-of friend.  She tells me it’ll be O.K.  He doesn’t have to know.  Man, I wanted to rip her clothes off right then and there and pound her.  You won’t believe what I did next.  I told her if she still felt that way tomorrow, I’ll be right here.  Call me nuts, but I knew the boyfriend  would really do me in if I screwed her right then and there.  She calmed down and said. O.K.  She’d think it over.  She left and I wondered what I had just done.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? The next day, after she got out of work, there was a knock on my door.  There was “Judy”, not crying this time.  I let her in and closed the door.  I asked her if she had thought it over and she said yes.  We kissed and began to explore each others body.

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 undressed her except for her panties and guided her to the bed.  After removing my clothes, I gently pulled her panties off.  We were naked and embracing.  God she felt good!  We did a quick straight fuck and then did some other positions.  I enjoyed entering her from behind the most.  She had a tight little body and was easy to love.  When she sucked my dick I thought I was going to pass out.  I nearly came in her mouth but was able to save it till later.   Being an older woman, she knew what to do and when to do it.  Her tits were just the right size and had beautiful nipples.  She’d let them hang over my face so I could kiss and lick them while she sat on my cock.

Did you have an orgasm? Did your partner(s)? We both came every time we did it.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? I wore no condom.  She had her tubes tied after her daughter was born.  “Judy” encouraged me to come inside her. She had no  STD.

What were your REASONS for having this hookup? My reason for having this encounter was I was extremely horny and she had come on to me.  I took a big chance with her boyfriend finding out. Maybe that made things more exciting.  I never could figure out what attracted her to him.   He wasn’t that good looking.  He must have had a great package I guess.

Were alcohol or drugs involved? If so, how much? No drugs or alcohol were involved.  We both were quite 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? After making love for a couple of hours, I had to get ready for work.  I could have stayed in bed with this woman for several more hours it was that good.  We agreed to get together again and we did.  For her sake I’d hoped that she would tell “Jim” to take a hike but that was not to happen.  She went back to him after a while.  I told her he was going to hurt her again but she didn’t listen.  I know now we were not made for each other but we were good while it lasted.

To whom did you talk about the hookup? How did they react? I told no one.  It was too small of a town.

Was this a consensual and/or wanted experience for you? For your partner? We agreed to what we did.  As I said before, I’ve never had a woman ask me to make love to them right then and there.  I was floored and honored.

Do you regret this hookup? If so, why? I have some small regret but on the whole I’m glad it happened.  I learned a lot about life.

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 worst part was giving up this highly sexual woman who made me feel so alive and good.  After sex, we’d lay there, holding each other, kissing now and then and just staring into each others eyes.  She felt so good in my arms.

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

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

Anything else you want to add about this hookup or anything else? “Judy” was not beautiful, but she was a looker.  We enjoyed being naked with each other.  I wish we had more time explore our sexuality together.  I got the impression that she had a kinky side that she wasn’t ready to share with me yet.  She had a gentle touch when she’d caress me.  I could suck on her tits for hours.  One thing I remember I did when she came back the next day was I reached around and put my hands on her backside and said, “I love your ass!”  I was a real gentleman, eh?

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