Want to try anal- slightly frustrated :(

What's to understand? Not everybody likes cheeseburger.

Although I'm happy to oblige, I'm not anal crazy either.

 

Hi Rubyrain, Here It Is... you might want to print this out.

In my opinion you are jumping too far ahead.

Back up a by about a month or two. He has said he's interested, so trust that he's telling the truth about that. He just hasn't had fun with you this way before, and his mindset doesn't yet include your ass as an exciting fun place to be.

If your guy is new to playing out back, I suggest you start there. Firstly, tell him not to think about anal sex anymore for now. Remind him that you like him and have fun with him in bed (or the broom closet or where ever you two are having fun).

He needs to experience your back yard as a fun place to play and make you happy. He also needs to learn how to play back there, because to do it right is a whole different style than what you guys do with penis/vagina sex. He needs to know how to proceed and how to read you Before his penis gets involved (really).

If he is comfortable with performing orally on you, I suggest you get some coconut oil (which should be thick and creamy at room temp, but turns to oil at body temp, and also has anti-bacterial properties which is a good thing) ready so he can dip his finger tips in it. Make out with him, and tell him (calmly, and listen if he has questions) that you would like him to go down on you and while he is there to get some of the oil on his fingertip and hold it against your a**hole.

He should keep doing the oral, and just slowly wiggle his fingertip around your a**hole, and then stop and hold it against you. After a minute (or less, or more) it should slip in just a little without him pushing any harder. Tell him to just hold it there again and keep doing the oral. When you want it to go further, his hand stays still and you push your ass down onto his finger.

Once it goes in so you feel it is really slipping in (Slowly, gently) tell him to push into you. When you want it to stop going in tell him to stop and stay there. After that feels good (a few seconds or a minute) wait another, additional 20 or 30 seconds and everything should relax further for you and you'll quit holding your breath (which you probably didn't realize you were doing until now). Then tell him to push slowly into you until his hand rests against your ass.

While this is happening, be vocal about what feels good, about when he should stop or slow down. Be very clear when it feels good to you. If it makes the oral feel better (I hope so) Tell Him.

Once his finger is all the way in, and you are again feeling good and breathing ask him to wiggle his finger a little. If it feels good, Tell Him. He should be moving his finger only a little, and slowly. It's pretty delicate back there and there is plenty of time later to try more forceful action - not the first month or two!

I would think that's a great first session. Even better if you can orgasm via his tongue while his finger is inside you.

If you want to have regular sex with him after, do that.

Next session (next day, two days later? Anal doesn't have to be every time), repeat. If you want more action already, this time have him go through the whole technique the same, then slowly slide his finger out, rub lightly around your a**hole, and back in all the way and keep doing that until you orgasm from his tongue.

Next session, repeat and ask him how it feels to him. Try a teeny experiment with the finger wiggle when in and tell him more how it feels and ask him how it feels. He needs to be first comfortable with where you all are playing, and then he needs to be getting turned on because it is turning you on.

Next session, no anal play. Let him know you are enjoying him already and this is something to add, not a comment that he isn't satisfying you with regular sex. Here I mean to let him know by refusing anal play and just enjoying the sex with him. I don't suggest you use words because even to say "it's not that you're not satisfying me already...." will register in his brain that he's not satisfying you. Communicate it just by enjoying being with him and taking the pressure off of the whole anal exploration for a couple days.

Next session, have missionary sex and ask him to get the coconut oil on his finger tip and play outside, then inside your a**hole while having sex. Tell him what feels good. Hopefully you can orgasm during this so he can tell (and you can determine if) you like it.

Next session, repeat missionary sex as I described above. Tell him when he starts to touch your a**hole how exciting it is to feel him there.

Next session, tell him beforehand how you are enjoying this new stuff with him, and you want to go a little further. Have either oral sex or regular sex with one finger in your ass. Then during it tell him you want him to slowly slip in a second finger and keep it deep in there.

Repeat these sessions about 3 more times.

Now - If you are both in the mood that day/night - you are probably ready to try anal sex for the first time.

I suggest to start with missionary, and have him also work up to the two fingers in your ass during the sex - hopefully you can orgasm during this. Then tell him you're ready to try his penis in your ass. He needs to have not yet come, and he needs to be hard or this will not work.

If this doesn't quite work, I would then suggest the next time you feel ready to try anal sex, you have some penis / vagina sex, then lie on your front and he gets the oil and rubs it between your cheeks, and then slides his penis up and down between your cheeks like he's slowly screwing your ass. After a bit, push your ass back against him when he pushes. After a little bit, you take your hand and guide him against your a**hole.

OK - now when you do have anal sex, it should start just like it started with his first finger. He gets the tip in, and waits there with a gently pushing pressure, but No shoving. After a few seconds or a minute or two it should feel good to you and you should open up and he can slide slowly in. Then he should stop and wait while you catch your breath.

If it isn't going in easily, you can push out with your a**hole, as if you're pushing something else out (ya know?). That can help him slip in if he's close but not making it inside.

Always use Plenty (more) of lube (more).

Enjoy

Um. If he doesn't like performing oral on you, I don't know what to suggest. Also - mixed in between these sessions should be you performing oral on him, and some of your 'regular' sex sessions. Don't focus everything on just anal. If you do end up enjoying anal sex together, it will be better over time as you both learn what you're doing.

 

He sees bum sex as gay, and is fearful that if he gets into it it will mean he is a homer.