Friend’s Best Friend

by DJ

Gender: Male
Age: 31
Race/ethnicity: White
Current location: Connecticut
Highest education received: Some college (not currently in college)
Relationship status: Married
How religious are you? Not at all
Sexual orientation: Bisexual
Any other term(s) that describe your sexual orientation/sexuality better/best? Bisexual recovering sex addict
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? Too many

Friend’s Best Friend

How long ago did this hookup happen? 2 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…)? Hookup

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? K was a girl that I had known through one of my friends. I had always been sorta flirty with her whenever we had hung out in a groups but I wasn’t terribly attracted to her. She has a nice body though, and I wouldn’t kick her out of bed by any means. She’s thin, with auburn hair and lots of freckles.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I was in between girlfriends and was dealing with some shit there. But as always, I was active on plenty of fish. I saw K had a profile on there and she decided to message me one day. She was surprised to see me on the site since it still appeared that I had a girlfriend. At least that’s how we played it on Facebook to avoid questions. I explained the situation and she we started to get flirtatious. The texts soon became sexual and we both discovered that each of us were huge sex fiends. We finally arranged to hook up one night at her place when her kids weren’t home. I showed up and we talked for a few minutes. But the fun started almost immediately.

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? She brought me into her bedroom and we started heavily making out. She was a good kisser. I grabbed her ass and groped her body all over. She took off my pants and began to suck my cock. She took it into her mouth and deep throated it better than any other woman I’d had at that point. I’d never had a girl deep throat me like that before.
I decided I wanted to return the favor so I spread her legs and unveiled her shaved, dripping wet pussy. I began to lick up and down on her lips. It was so wet, I couldn’t believe how much was dripping from her. It tasted fantastic. She came pretty quick and very hard. I wanted to continue but she told me she wanted to keep sucking my dick. So we did something I’m not usually a fan of: we 69’d.
Surprisingly, I loved it. Our bodies were the perfect size for it since I’m tall and she was very petite, she was positioned perfectly at my cock while I devoured her from below.
I rubbed her ass and ran my fingers down her spine while I licked her over and over. Her lips felt amazing on me and made it hard to focus on her pussy and throbbing clit.
I then decided I’d had enough and I flipped her off of me and slammed her down to the bed. I slid my hard cock inside her and she gasped as I entered her tight, deprived pussy. She seemed to be in ecstasy with the feeling of my meat deep inside her. I knelt down and kissed her while I slid in and out against her g spot.
I fucked her for the next hour in many different positions. We both became incredibly sweaty because it was such a lengthy session. We just really wanted to savor and enjoy each other. It felt great.
Finally, I couldn’t keep it up and I asked her if I could cum inside her. She said “please do” and proceded to beg me to fill her with my cum. I let out a loud moan and shot what felt like a giant load inside her tight, worn out pussy.

Did you have an orgasm? Did your partner(s)? Yes and yes

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? None

What were your REASONS for having this hookup? We were both very horny.

Were alcohol or drugs involved? If so, how much? None

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? Afterwards, I got cleaned up and put some clothes on. I had to leave and she was ok with it, though she wanted me to stay the night and asked if I would. I couldn’t and I left pretty quickly. She walked me out to my car and we kissed goodbye. We talked a bit more in the next few weeks but never hooked up again. I’ve only seen her once after that. It wasn’t as awkward as I expected it to be.

To whom did you talk about the hookup? How did they react? My wife now. She has met K and doesn’t understand why I wanted to fuck her because she doesn’t find her attractive. My wife also isn’t a man and doesn’t know how men think.

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

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? Best was the 69ing. Worst was that I couldn’t stay to cuddle. I actually cherish those moments.

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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