by Shaolin Monk

Gender: Male
Age: 45
Race/ethnicity: human
Location: Overseas…
Highest education received: Post-graduate degree (eg., MA, MS, PhD, JD, MD)
Occupation: Financial drivel…
Religious affiliation: Swinger
How religious are you? Not at all
Sexual orientation: Heterosexual
Any other term(s) that describe your sexual orientation/sexuality better/best: Swinger
How many hookup stories have you here posted before? 1

First nut out of the joint

How long ago did this hookup happen? Many years ago

How would you best classify this hookup: Swingers sex

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? Many years ago I went to prison as a first time non-violent drug offender but that is a whole other book. Anyway before I had to turn myself in, my friend who was a stripper took me to a swingers club in midtown Mnahattan called Checkmates. The memories of that night held me over for the entire 14 months I was locked up. When I got out they put me on home confinement and because of certain religious restrictions I was not expected to answer the phone on Friday to make sure I was confined to my home. So one night I called the stripper and asked her to please take me to the swingers club. She told me she had a boyfriend. I was like “well I just got out of prison…maybe he will be cool with you taking me just as a good Samaritan.” She told me he wouldn’t, be but suggested some online dating site. I put up a profile called “Home Confinement” with the tag line “Because I can’t come out until the end of August” and then I would spend my days at some bullshit job I had to stay out of the joint trolling profile and anytime I found one that seemed even remotely risque would write the girl telling her my deal and asking her if she ever was curious about going to a sex club and would she like to join me. Well…I must say it worked quite well shockingly and the first time was the one I remember best.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? It was a Friday night and I met some random girl for a drink after talking online. After a shot of tequila we walked over to the club, went to the lockers, disrobed and went in the back. Now keep in mind I had not had sex in over a year. And then there in the back was this smoking hot light skinned black girl totally naked except these really hot Gucci shoes on her back getting fucked by one dude while some other dude has his cock in her mouth. I was in awe. There was an older Italian gentleman on the bed with them who was probably her “benefactor”. And as I watched, wishing it was me, suddenly as if the hand of the almighty himself entered the club, the Italian guy tapped both the guys double teaming his girl on the shoulder, shooed them off, looked at her, pointed at me and uttered these unforgettable words…”Let him have some”.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? Did you have an orgasm? Did your partner(s)? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? At that point the bed cleared and I joined the girl on the bed. She sucked my dick and got it hard and than handed me a condom, rolled on her hands and knees and gave me her ass to fuck her doggie style…”One thrust”…sort of like the movie “The Deer Hunter”…I put my cock in her and bamm…I blew my load. Just like that! At that point she had no idea what happened and was reaching back trying to find my joint but I already blew my load. I started to laugh and told her and her man they were angels…that I just got out of prison on an ecstasy charge and that it had been over a year and that I would be eternally grateful. I dedicate this post to them!

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? She blew me bareback but I fucked her with a condom…

What were your REASONS for having this hookup? Well over a year without sex is a pretty good one…

Were alcohol or drugs involved? If so, how much? Not really…

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 laughed…thanked them…told them why I blew my nuts so fast and moved on! The best part of a swingers club is once you are done you don’t owe anyone anything…a pleasant smile…a thank you…and that is it. The anonymity and sheer none commitment of the act are the best parts.

To whom did you talk about the hookup? How did they react? I have told friends this story but its the first time I have written it down.

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

Do you regret this hookup? If so, why? No way

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? Well if you did not have sex for over a year what do you think?

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup or anything else: Last night I went back to the strip club from my previous story…took this stripper in the back and she rode my bare cock with her pussy (no penetration…just lubricated friction stimulation)…it was nice 🙂

What did you think about this story? Tell us in the comments!

You have a hookup story to share? Submit it here!