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Query
#1
My boyfriend and I have never tried actual penetration. He's very into having his ass touched and spanked and such. And I have rimmed him. I want to eventually get to penetration and he has expressed interest, but I'm not sure he's ready. How can I help him get ready?
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#2
I don't know... He sounds ready to me.
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#3
Hope you get what you need before someone starts lecturing "the ass is not for sex". Rolleyes

And welcome to Gayspeak.
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#4
How to have anal sex:

http://www.loveyourcondom.co.nz/great-se...-anal-sex/
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#5
It's strange. People can strip naked and get the sheets sweaty and sticky, but then when it comes time to actually TALK about it, that's when they say "I don't know - that sounds kind of weird. I'm not sure I'd be comfortable doing that." Dude, you put his tongue in his ass. You should be able to TALK about it, too. Smile So just ask. "I'd really like to try penetrating you next time we have sex. Is that something you'd be willing to try?"

Lex
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#6
Rimming.

That's all you need to know.

If that doesn't work.

Try more rimming.

Doing it a first few times you need to not worry about you getting off and make sure he does. Keep him hard, keep your hand on his weenie as much as you can. If you're limber enough you can perform oral while you penetrate him. I finish my guy that way a lot. After almost 8 years that has never become "ordinary" or routine for him. He'll lay there and go to sleep every time if I let him.

When you - two get more comfortable with it you might want to explore male multiple orgasms he can have during penetration. You can research it on line and read about here too >>> https://gayspeak.com/showthread.php?t=32...ee+orgasms once you get there, there's no turning back. hahahahahha! Anything less isn't good enough.
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