I Need To Punish Him Until He Uses The Safe Word

eyescream

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I have always wanted to dabble in some S&M and there is no better time than now. I have been involved in a FwB relationship lately and my buddy pissed me off by telling someone something that I told him to keep a secret. His little storytelling is about to teach him a lesson. The last time I punished someone, they actually had so much fun. I want to have fun, but at his expense. I want him to feel some pain, I want him to feel the wrath of a proper punishment.

Any suggestions? Perhaps a proper spanking on his butt until it turns red, perhaps shoving something too big up his anus, perhaps tying him in a compromising position to prevent stimulation. Perhaps all of the above.

Would like to hear from straight guys. What would be extreme enough for you to go as far as uttering your safe word?
 

SamMann75

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First time my wife spanked me...i came home with my best friend, she undid my belt and pants, i thought she was being playful and joking around, then suddenly bent me over her knee and pulled down my pants and underwear to expose my cheeks and slapped soooo hard i yelped. By the time she finished i was crying and screaming stop, safe word... what do i do to stop it? She said safe word? Baby this isn't play it's punishment and spanked me 4 more times.

My friend looked shocked and uncomfortable when she finished i was too glad for it to be over and felt so bad for doing what earned me the spanking that i wasn't even embarrassed about my friend witnessing it. She calmly told me to go get changed, we were all going to another friend's bbq. I came down and my friend and wife were laughing, she lightly tapped my behind and i screamed it hurt... they both laughed.

My ass hurt all afternoon, and my wife kept sitting on my lap and occasionally she'd give a little wiggle and i had to struggle not to moan in pain as my best friend and wife giggled.
 

Bourbon34f

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I have never been into bdsm. Been an Alpha all my life... never submissive. I’m not a power trip player... and anyone who tries to control me in the bedroom will cum up disappointed.

I can see the lure of teaching him a lesson though. Breaking trust is definitely worthy of sum punishment, for sure. Tied up humiliation? Spread eagled on the bed, mebbe include others, one or two close friends to join in. Pain is fleeting, humiliation lasts a long time.

ymmv

Cheers.
 

Mike hung

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I have always wanted to dabble in some S&M and there is no better time than now. I have been involved in a FwB relationship lately and my buddy pissed me off by telling someone something that I told him to keep a secret. His little storytelling is about to teach him a lesson. The last time I punished someone, they actually had so much fun. I want to have fun, but at his expense. I want him to feel some pain, I want him to feel the wrath of a proper punishment.

Any suggestions? Perhaps a proper spanking on his butt until it turns red, perhaps shoving something too big up his anus, perhaps tying him in a compromising position to prevent stimulation. Perhaps all of the above.

Would like to hear from straight guys. What would be extreme enough for you to go as far as uttering your safe word?
Happy to help with suggestions but it'd be worth having a chat with my wife @Holly Doors ,she's the queen of bdsm
 

cofrader

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Have you tried with nothing?
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I don’t understand sm, I dont think hate as a good driver for the relationship. If I was him and read this post I will use the safe word before starting “divorce”.

Teaching him a lesson? Is he willing to learn? If he is into sm perhaps he will enjoy it and do it again for more.

I will tell you here the secret to keep secrets: