What is the best way to not hurt your bottom
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use lots of lube and take it slow.
also, maybe try some toys to loosen him up a bit before you get down to penetration
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yeah, totally rim him, put a lot of lube maybe with some effects (like warming gels or smth) and let him be in control. let him put it in and dictate the tempo if he's comfortable enough he will let you finish the job then.
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If the cock is very big I as a bottom prefer to start with the top on his back so that I can sit on the cock and slowly get used to the size. Then when my hole is opened, I can take it in any position and enjoy the ride.
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lube, lube, lube, and lube
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Roughing up is good some times. :cheesy2:
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My advice as a bottom would be giving a good rimjob, massage the anal area, use lub and you're all set.
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I'd be more concerned with the struggling and screaming.

Nah, kidding. Ask your bottom, of course. "Does it hurt? Lube? Slower?"
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Awwww.. I've read some replies on this post and I think that there are things I will implement the next time I'm top… still learning to be more considerate.. haha
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hurt him goddamn
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Use lubricants, foregrips, and slowly penetrate until you get relaxed
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