Jack off buddy wants me to fuck him

MMT22

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Not sure if I should since that is ramping it up a lot from stroking and a little sucking. I told him that full body contact, kissing and condoms are a must. He says he is exploring right now and wants to experience everything. He claims to be new to this, but he sucks dick like a pro.
 

WilliamG

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Not sure if I should since that is ramping it up a lot from stroking and a little sucking. I told him that full body contact, kissing and condoms are a must. He says he is exploring right now and wants to experience everything. He claims to be new to this, but he sucks dick like a pro.
Do you want to fuck him? That is your answer.
 

rd62624

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as WilliamG stated" Do you want to fuck him"? If you are doing to please him ; you my have regrets afterwards because you two crossed the line.
 
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1141702

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If you want to do it, do it, if not, don’t. It’s as simple as that.
 
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Lakeshore

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I had a hard time trying anal as a bottom & top with my JO & Suck buddy, took me 2+ years to even consider it. When we did it I enjoyed the sex and it made us closer as FWBs We had no problems of thinking we'd gone too far. Ultimately you'll need to weigh the pros & cons, and decide if it's something you want and if it might cause any division or negative thoughts between you two. Talk about it with your friend, it's a very intimate moment. Take your time.
 

long_uncut

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I wouldn't rush into it. I think it works best if you have a rock solid friendship first and both are sure you want to go there. Have done it and it made our friendship even stronger....but only after over a year of establishing that friendship which is still going strong after a couple of more years.
 

surfnwoody

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If you've known your buddy for a while, year or so, an your stroking an sucking now, I'd go for it. Never did anal with any of my jack off / suck buddy's, wish now that I would have. I sure love fingering an prostate play.