So me and my friend been sucking each other off for about a year and half and I recently asked his if he wanted to do anal but he does really dose not want to do it. What should I do. I really want him to try it on me or me try it on him. Any advice can help.

Hey hon :)  Usually an aversion to anal is tied up in misinformation; that anal is painful and dirty…or makes you gay, etc.  It may be that he is okay with sucking his buddy off but getting fucked in the ass may be too much for him to handle.  Perhaps encourage him to talk to you about why he doesn’t want to give it a try.  You may want to show him the link below…everything a guy needs to know about getting fucked in the ass.  It should help to put him at ease.  Good luck!

Anal Sex Tips For Men
I really wanna try pegging. Me and my guy like anal play, I really wanna how him how amazing it is. I will and have fingered him and rimmed him but I want to be able to use more than my hand but I think he's scared. How do I reassure him? I think he'd really enjoy it. I'm all for giving him amazing orgasms, and I really wanna do it! It's hot! If he lets me use my hand/tongue, why is he scared of pegging? D;

Pegging is a super intimate and sexy experience for couples.  That’s really awesome that he lets your rim and finger him.  I think the issue some guys have is accepting something “cock shaped” in their asses and not getting hung up on what that makes them.  I would suggest buying him his own toy.  Nothing girly and nothing that resembles a cock.  Just a masculine probe…something with a bit of a curve on it to hit his sweet spot.  Something like the set below perhaps?  It can be used as a starter toy and moves up in size.  It can be used alone or in a harness.

Starter Strapon Kit

He may also associate pegging with submission and that might not sit well with him…reassure him that is not what it’s not about (unless he wants it to be).  The other thing I recommend a video that hubby and I saw before delving into pegging ourselves:

Instructional Videos

It walks a couple through cleaning, prep and pegging in a really easy going and fun way.  It’s followed up with 3 or 4 sexy pegging videos that show couples just enjoying it for pleasure.  He may be concerned with being clean enough for you and just not be comfortable expressing it.  If you can address his fears and put them to rest I bet he gives it a try ;) xoxoxo

I want my guy to enjoy anal but he's freaked out by the idea of my fingers in there.  I sometimes want to just slip my finger in unexpected but I know he'll get really mad.  Is there anyway I can help him?

I hear you darling…it sucks that somewhere along the line assplay became synonymous with being gay for guys.  Such a silly notion.  Imagine as a girl feeling like a lesbian if you dared enjoy your gspot? It’s a body part they were born with and it’s pleasurable…so why the fuck would only a select group of guys be “allowed” to play with it?  So tempting to just tie him up and have at it!  You might want to try baby steps with him.  His taint is his prostate from the outside of his body and it can be very pleasurable…slip your fingers or tongue down there and don’t go any further while you are sucking his cock.  Incorporate it into your playtime for a while and get him use to your fingers venturing down there.  Once he is comfortable and enjoying that extra sensation you can try to slide your fingertip down to his pucker and just lightly rub it.  Don’t stick around too long but tease him here and there.  It may be that his fear is associated with penetration.  Stick to the outside.  If you can get him enjoying that and maybe rimming you are doing good.  If that becomes part of your regular playtime then after a while approach him about exploring his prostate.  Educate him on how intense it can make his orgasm just to have a finger in there.  I wouldn’t recommend just surprising him with a finger in his ass one day….everyone should feel clean and prepared for assplay or they won’t enjoy themselves.  Just some thoughts…hope it helps. :) xoxoxo