Awkward boyfriend wants anal

[Justhereforthereading]

Hi guys! I would like a bit of advice on how I should go about this. My boyfriend is a bit shy and gets totally awkward when it comes to trying something new. We have been together a bit over two years now and he is so full of anxiety he has a hard time being completely comfortable with me, also I should probably mention that I am his first for everything so there were no ladies before me to have a crack at him.

Anywho onto my main point here. He's an ass man and would love to be the first guy I've had in my back door, I am totally open to this which I find funny because before him there was no way I was going to let anyone else in there. So I would love to let him have this but I need the proper stimulation as anyone does. I have ready pretty much everything in the how to category of lit on preparing yourself for anal and I have that down no problem. But I hit a snag when it comes to getting him to participate, it's been a little while now since I've started this journey. I can and have played with myself to get ready for it but I quit at one point because he was not putting any effort into it. I'm not doing this for myself so I belive that he needs to be in on the act of.

I've bought myself a butt plug since I know that he is into it and I'm even waiting on a new one with a better shape for what I need to come in the mail. I've played with my holes infront of him which I know he really enjoyed but he became all clammed up and uncomfortable when I started. It's been a minute since that has happened. As previously stated I was tired of trying when he gave nothing. Recently I had tried just telling him to play with me, which ended with me being a little frustrated and just getting onto my task of blowing him.

I have a larger problem here when it comes to getting him to do things to me. But as far as my asshole is concerned I want to know what I can do to get him comfortable with going after it no questions asked. My last attempt at it I learned that he is concerned (as I am) about getting poop on his finger because in the past after having my plug in for a minute and taking it out there is a bit there. Before this last time he was acting as if it was not a problem to him saying he knew it would get on his penis. But all of a sudden there is a change and now he is weirded out by it. Apparently keeping him from sticking his finger I'm my ass when we 69. I asked what the change was but he didn't give me much but a bit of his awkward responses.

Should I also put state that he has no problem having sex with me when I'm on my period(light flow)?
Any advice is much appreciated. I'd really love to let him have this I just don't know how when he makes it so hard. And what I mean by that is its hard to keep the mood going when things come to an awkward crashing halt
He has absolutely no confidence when it comes to this stuff so it makes it hard for him to get over that hump to give me just what I want/need from him

 

[sensualsharon]

I used to write for a sex toy website, descriptions of the products and the blog, one of the items, several actually, in the anal area were enema kits that were for use before anal. Anal enemas are also common on porn sets before shooting. So if you use that, then a good, long, soapy shower or bath, you should pretty well be free of any remnants he's worried about. If he uses a condom, no worry of said remnants on his cock, and a condom and lots of lube is always advisable for anal penetration whether cock or toys. A condom on the finger sounds a bit weird, but if you want that and he's stopped due to his fears, maybe try it? He sounds quite uptight and repressed, perhaps raised in a restrictive or religious environment. Just my thoughts though. Good luck.

 

[Learin]

There was a wonderful (and a bit funny) discussion on a similar topic not a very long time ago:

http://forum.literotica.com/showthread.php?t=1201059

Lots of great advice from lots of great people. I hope you find it useful.

 

[Justhereforthereading]

He sounds quite uptight and repressed, perhaps raised in a restrictive or religious environment. Just my thoughts though. Good luck.

Thanks for the advice I've thought of using finger condoms before (the things you find in a kitchens first aid kit) I guess the thought just left me but it has returned and I am going to give them a try. The religious part not so much but he is very much repressed due to sex being "shameful" and such. We have come quite some way on our sexual journey together so I know that him saying he just can't do something is bogus/anxiety because there is and has been room for improvement it's just a very slow journey, which I am willing to take his speed I'm just impatient so I have to remind myself to slow down.

To the other poster thank you for your reply also you helped me find my way to the blank Manual.

Thanks guys you have been very helpful, being patient with him gets to be a bit taxing at times but I do what I can to be the supportive lady he needs

 

[SquirtnBrat]

Good Luck!
I have been on a ten year journey with my awkwardly man. Time and patience and lots of communication, are your best tools.
At times I was exhausted. Ready to throw my hands up in surrender and juat walk away. But a little empathy and patience has brought us a long way. Of course I would love for him to be less "vanilla" but sometimes you have to except people for who they are.
I hope this opens up a new level of fun for you both.