The title says it all. This weekend I'll get to pop my friends butt cherry. He's 29 and has never had a dick in his ass, although its been attempted once before(not by me.) He told me it hurt and has not tried it since. I'd love nothing more than for him to love getting fucked and want more. I'm an experienced top but taking a "rear end virginity" is special and I'd be lying if I said I wasn't nervous. Anyway, I'm looking for your magical tricks and tips or any other advice you feel like giving!
Topping a brand new bottom. Tips?
- Thread starter nookpm
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get him horned up
get him into being tied up and helpless at your mercy
take your time letting him get used to you but you stay in control going off what he says but dont be afraid to use a little bit of gentle encouragement to quickly get past the sticking points
get him into being tied up and helpless at your mercy
take your time letting him get used to you but you stay in control going off what he says but dont be afraid to use a little bit of gentle encouragement to quickly get past the sticking points
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Ready to top a 32 year old whose never had anything in his ass before. I'll let him fuck me first. Unfortunately, he's smaller than I'd prefer but I'm trying to get him in the mood. I am def planning on tying him up and some massage and spanking and some slow involvement with gradually increasing fingers > toys > me. He sounds ready for it but always is very shy and slow to respond. We've actually had an orgy with my bi roomie and her gf and the two of us but he was a bit gun shy though I did at least get to jerk him off. So small though hard, straight and beautiful cock. He has very nick balls and a washboard stomach and perfect ass so I'm really looking forward to getting things rolling. Don't want to scare him away too soon though.
hotcockalex
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curiouscam
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Getting him really turned I would say is a great start. Eating his ass out for a bit should do the trick, maybe a little finger or two while you give him head. That always gets things going. Main thing I would say is just to be patient. Being in a rush to just put it in never turns out good. Best of luck. You will have to tell us how it goes 
BigDallasDick8x6
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I'd let him sit on it. That way he controls it and will relax more. If he's afraid of your thrusts he'll just tense up and it becomes a self-fulfilling prophecy.
D_Fiona_Farvel
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The above, while he's on all fours, then, with a lubed hand, rub with a long, sweeping stroke from the shaft of his cock, over his balls and ass going up the crack. Start soft, then shorten the stroke and concentrate just from the top of his balls to about an inch after his anus and add some pressure.
Keep going until most of your (sweeping) pressure is on the hole and the pads of your fingers are brushing away from his ass and he is pushing back wanting more stimulation. Once that happens, move to circling, sweeping, and tapping the hole until it opens a bit for you (you'll see it), then move to deep, slow penetration with your fingers until he's begging for your cock.
Ime, playing with and teasing the anus first is the best way to relax it for penetration. I also like to push out while my partner sinks in and that prevents the involuntary clench that sometimes happens for unknown reasons.
take pics. :09:
illinigradman
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Having a newbie ride first is usually a good technique if he is committed to doing it. He feels like he can ease it int. Whichever way, coach him so that he takes a little and then backs off and takes a little more and backs off. It takes patience but it pays off. After full entry pull out completely and go in slow again. The second time in he will enjoy it much more.
^^^ Remember, this guys is probably used to being in control (unless he's a submissive top). So let him be in control at least until he gets into it. And don't be shy about reapplying lube.
FOREPLAY! Give him all the time he needs to relax and enjoy your fingers, tongue, and toys in his hole. Talk to him, stroke his body, kiss him -- make him feel safe and secure. If you're patient and caring, you'll almost be able to fist him, he'll be so relaxed -- and then, when you mount him, let him control the penetration. Take your time -- go slowly -- and then rest inside him while he adjusts. This first fuck is about HIM and his needs, not you and yours.
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Good luck you lucky bastard! All good advice--sounds like you go the situation under control!
Well it wasn't what I was expecting but it turned out to be a pretty amazing experience! I ate his ass for about 30 minutes. He was anxious and wanted to get it over with, I think. So I banged him with my vibrator, fingered him, then got to the fucking. I -did- ask him to ride my dick, but he preferred to be on his back...
I'll finish this up later, my break is over. Lunch is in two hours, I'll continue then.
I'll finish this up later, my break is over. Lunch is in two hours, I'll continue then.
To quickly finish this up, he took my cock for a little bit then gave up. Too bad for him I was just about to get started. Overall I enjoyed licking his ass and getting cummed on. Unfortunately for me, none of this meant anything because I am in love with another man. Regardless, thank you to everyone who posted advice in this thread! I'll be sure to pay it forward
