Random Question: Your Kinkiest Moment?

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Every so often, it occurs to me that my sex life is very "vanilla" compared to other folks out there. My idea of a "wild" time involves light spanking, wrestling and a dash of manhandling. Sure, it may leave some marks on the day after, but you can't put it in the same category as nipple clamps, restraints, etc.

Since I don't have any crazy stories to share, you're going to have to fill in the blanks for this post. What's the kinkiest thing you've ever done with a sexual partner? Tell us all the juicy details, even if you think they'll make us squirm.

– Dewitt

Photo credit: Bound Gods

To check out more kinky action, follow the JUMP:

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16 thoughts on “Random Question: Your Kinkiest Moment?

  1. Heh, my kinkiest moment was in my first year after coming out, oh so long ago. I hooked up with this hot British guy (LOVED the accent) and we went to his place. Turned out he had a partner, and both of them were into fisting. Eventually wound up fisting both of them at the same time. NOT an experience I would recommend for a young gay man still in the coming out process.

  2. ahhh the guy in the first and fifth pics is named Sal, from Rhode Island. I used to talk with him online when we were kids! I remember he took a pic of himself w/ a cucumber up his butt when he was 15/16, would definitely count as kiddie porn in hindsight lol. He used to do webcam shows all the time too. Not too surprised he does bondage porn, to be honest LOL.

  3. I was tied down to a table and got my nipples tweaked and iced until they flaked the next day. I only regret that the guy didn’t make the rope tighter.

  4. There used to be a place called “8709” in West Hollywood, California that was a “bath” house. Don’t know if it’s still there, but one night I found myself in the middle of a huge circular mattress in the middle of an arena-type room with seats all around the outer perimeter, and I was getting fucked and sucked by as many as thirty different guys for maybe an hour or more, while another thirty or forty sat around the outside watching and cheering and doing their neighbors at the same time…the good old days before AIDS. I’m lucky I’m still around to talk about it. Unbelievably good times!

  5. A friend was using my ass with some toys(Baseball bat, large dildos, orange caution cone, fisting, chrome bocce ball) while someone else was video taping it and 6 other guys were watching us and jerking off. The one thing I did that turned a guy on so much that we ended up fucking for hours after was: He put 2 chrome bocce balls in my ass, he told be to push one out and I did, he told me to push the other one out and I told him to go in and get it. He shoved his hand in my as wrapped it around the bocce ball and pulled it out. He got so turned on by that. I also have a glove with finger tip vibrators that I love to get fisted by and that is pretty kinky.

  6. Hmmmm … well some of these things might be kinky and exciting … I still rememebr the first time I was tied down to 2 full size beds with 4 corner posts … in the middle winter on a college campus … the guy took me back to school with him and when we arrived he found a belt, a robe belt, a phone cord and a piece of rope to tie me to the bed … aftering tieing me down he licked and nibbled all over my body until he got to my hot quivering member … he then proceeded to suck me and lubed up his finger and proceed to insert it up my ass … at this point I had only been fucked by him once before … so the second penetration ever was tied to beds … after getting me all worked up he starttled my head and force me to suck his dick … once I got him rock hard he pulled out lubed up and untied my legs hoisted them airborne and proceeded to probe for the hole … once finding it he slowly shoved himself into my tight ass all the way … was in there for a only a couple of seconds and proceeded to pound my tight ass for all he was worth … after he came he collapsed on my chest he pull out and cleaned up and left me tied to the bed with no covers, window open and it snowing outside.

  7. @bill — i’m actually kind of obsessed with sal from rhode island! i’ve seen his work (his studio name is CJ in kink.com) as a pain sub for men, women and transsexuals and he is extremely hot in all of them!!!

  8. I currently involved in a Master/slave relationship. I don’t think I could come up with just one kinky story to do the lifestyle justice

  9. the kinkiest i’ve had is when i was edged for hours and hours and not allowed to cum until i begged, at which point i was not allowed to cum but was edged some more. the cumshot was amazing.

  10. ohhh sooo many
    me and my x use to get really kinky, we use to play master slave alot, he would tie my wrists to my ankles, blind fold me, feed me heaps of amyl and go completely nuts…ohh how i miss it hehe
    another highlight would be being a bottom to about 10 guys at a sauna, men literally were just lined up behind me taking turns, was so hot

  11. Ive never actually done anything very kinky. i once fucked a guy in the outdoor bathroom of the SF Eagle. Guys would come in to use the urinal and catch us fucking but I didnt stop. he was a hot little Aand F model type. so as you can see,not very kinky.
    Secretly, I’ve had some rape fantasies of being forced into sex but it’s kind of weird since I’ve never taken a cock up my ass so I’ve never asked. Hit me up opn manhunt if you want to take advantage of me…please I beg you! mattressjock is my profile.

  12. I was fucking this guy over the hood of his car in the parking lot of a mostly abandoned strip mall. Then over my car, then up against one of the lamp posts, then up against the front door of the one business still operating there. After a minute of shoving his face against the glass we realized at the same moment that that business was a church. We stopped immediately… give or take ten minutes.

  13. It wasn’t so much the “act” that was kinky, but I was cruised by a hot guy in his 40’s (same age as me) out near Philly. Chatted for a while, then went back to his place. He didn’t tell me but apparently his college-age son was living with him and he was there when we arrived. Stage 1 awkward. They kissed each other on the lips passionately to say hello, before introducing me (stage 2 awkward). He then told his dad “save some for me later.” giggled, and went off to the basement. (stage 3.) I kind of wanted to run, but the guy was that fucking hot… We fucked around as planned, but afterward I had to ask the obvious questions, which he confirmed. I was part freaked out, and part turned on. The younger one is on Manhunt. lol.

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