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Personal Advice
#3
Does he trust you explicitly?

If not, then he may be tensing up and 'scared' its going to hurt thus making things difficult.

Mind not trusting you in this matter is not always a reflection of you, other things can be under all of this causing him anxiety and inability to 'trust' fully.

One thing that may help is cuddling - spooning in the nude, you pressing up against his back, him with his back pressed up against your front. Just laying there, small talking, with your arm around him will relax him and get used to this idea of you being pressed against his back. No intent and no pressure for this to go further. Yes you may be hard and he will feel that, but your all's intent is just to lay there and be intimate.

Side to side 'spooning' position also means you will be able to control your movements a bit and go a lot slower than say doggy style or missionary style (gravity, can't trust it). So when you do get to the point where the idea of insertion seems good, you are not struggling against that terrible gravity and can actually 'poke around' a tad and rest with only a bit of dick in there....

Also try 'teasing' where you use your erect penis to massage his, um, crack.... The intent is not to press forward, but just to get him all hot and bothered with the idea that you are excited and 'knocking' on the back door. It can also be a fun way to lube up, put a bit between his butt cheeks above the anus and rub the shaft of your penis up and down the crack....

You might also want to try with him sitting down on you. This puts him in full command here and gives him the feeling of control thus he may actually relax a lot more into.

Since this is all new, its a tad scary. We all know that its going to hurt - thus we tense up a bit out of fear of the pain. Relaxing and getting use to the closeness (while fanning the flames of passion) drives that fear further down the road and makes more things possible.
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Messages In This Thread
Personal Advice - by archubbycub - 09-03-2012, 12:37 AM
Personal Advice - by ceez - 09-03-2012, 01:14 AM
Personal Advice - by Bowyn Aerrow - 09-03-2012, 01:26 AM
Personal Advice - by Blue - 09-03-2012, 02:10 AM
Personal Advice - by ChadCoxRox - 09-03-2012, 02:11 AM
Personal Advice - by archubbycub - 09-03-2012, 02:24 AM
Personal Advice - by archubbycub - 09-03-2012, 02:27 AM
Personal Advice - by Blue - 09-03-2012, 05:55 AM
Personal Advice - by dfiant - 09-03-2012, 07:49 AM
Personal Advice - by archubbycub - 09-03-2012, 11:22 AM
Personal Advice - by Maverick - 09-03-2012, 01:02 PM
Personal Advice - by bhrc - 09-03-2012, 02:56 PM
Personal Advice - by archubbycub - 09-03-2012, 04:54 PM
Personal Advice - by jamiebfd - 09-03-2012, 04:56 PM
Personal Advice - by bhrc - 09-03-2012, 05:15 PM
Personal Advice - by archubbycub - 09-03-2012, 06:07 PM
Personal Advice - by Blue - 09-03-2012, 06:17 PM
Personal Advice - by archubbycub - 09-03-2012, 07:36 PM
Personal Advice - by Blue - 09-03-2012, 11:29 PM
Personal Advice - by 57lambertr - 09-15-2012, 02:12 PM
Personal Advice - by princealbertofb - 09-15-2012, 04:01 PM
Personal Advice - by archubbycub - 09-15-2012, 04:36 PM
Personal Advice - by princealbertofb - 09-15-2012, 04:43 PM

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