How do I approach this ?

[Hiplainsdrifter Senior Member Find all posts View Profile Close Hiplainsdrifter]

I've brought up the subject of anal with my fiance again recently and she said she would try it. I'm skeptical. I'd really, really like to try it. She seemed to like a finger in her ass while fucking awhile back.

I'm reluctant to push the issue, though. As many of you know, she's plain vanilla in bed.

So, I purchased a small soft dildo, maybe 3" girth (just under 1 inch diameter) and 5-6 inch length. I'd like to try it on her while fucking. I'm just not quite sure how to bring it up ?

[Hiplainsdrifter Senior Member Find all posts View Profile Close Hiplainsdrifter]

Maybe this should be moved to Woman's Perspective forum ?

[colorblind72 Senior Member Find all posts View Profile Close colorblind72]

Have an honest conversation and get a clear yes or no.
Then work on her comfort level.
If she likes a finger do a lot of finger play as part of foreplay and during sex.
Work one finger, lots of lube and then two fingers and then dick.
Go slow, lots of communication.

[dmizzle Senior Member Find all posts View Profile Close dmizzle]

My current girl laid out her hard limit was no anal. So, every now and then I would use my finger while having sex or eating pussy. She really liked it. Then one night I'm doing her from being, got my finger in her ass. She turns and asks "What are you doing." My response, "Just relax babe, I'll go nice and slow." She knew what that meant. I couldn't get in but I had lube handy. Lubed up, slid in nice and slow, after a few minutes she was taking me balls deep.

Anyway, I'm the kind of person that just lets things happen. Let the moment dictate what happens. You might want to discuss it, but don't plan it. When the time is right, make your move. If she denies you just blow it off and keep doing what you were doing. I had not had anal in forever, now my last two ladies both let me do it. And my current girl was 100% against it. But she trusts me not to hurt her and if she is uncomfortable I would stop.

Maybe start with, "Hey babe, you mentioned you might want to try anal so I picked up a little toy that might help you ease into it." If she seems interested ask if she wants to see it.

You don't want to be forceful about it, but sometimes people need a little push to try knew things, especially when it seems scary.

And to my point. My girl said she didn't particularly enjoy it. Mainly cause she was prepared, but said she is definitely down to try again. I have the Hitachi Magic Wand that I'll let her use during anal. That should do the trick.

[akaTrex Senior Member Member of the Month Jan 2016 Find all posts View Profile Close akaTrex]

You can also try a Graduated Butt Plug method. You can get them on Amazon etc.

Many women like to have traditional sex while a Butt Plug is inserted.

Helps many to work up to act of Anal.

[KMWylie Senior MemberPEGym Hero Find all posts View Profile Close KMWylie]

Two things... Communication and lubrication.

Definitely talk to her about the dildo and let her know that even if she says, "OK" now... at any point in time you will stop, she only has to say the word -- and it's totally OK if she does change her mind at any point.

[TheGreatDivider Senior Member Member of the Month Dec 2015 Find all posts View Profile Close TheGreatDivider]

She already knows you want anal, and talking about it with her when she's she's hesitant is onIy hurting your chances of trying it with her. Pressuring her is only going to make her not want to ever try having anal sex with you, so drop the issue keep doing what you've been doing. You'll get it when she's ready to try it.

My advice on first time anal is give her a few really good orgasms, through cunnilingus and sex, and gently working a finger in her ass like you have been doing. But DO NOT stick more than your head in her ass the fist time you try anal, which goes for the vibrator as well.

Let her get use to the feeling of only the head of your penis penetrating her ass without any pain or any discomfort from adjusting to the new feeling. After the first time doing this, depending on how she feels about it, you can go a little deeper but not past the second sphincter (about 2.5" past the first sphincter).

It also really helps if she's had a good day and is tipsy to slightly drunk (try tequila!). You're more likely to get to try anal on a good day, when she's feeling up for anything (seriously, tequila!), versus a bad day when she would you stay away from that area (the day after trying tequila).

[islander Senior Member Find all posts View Profile Close islander]

Op
Go real slow on this
I suggest

Start massaging her rear entrance during foreplay. Let her see how aroused she will get from that. Soaked actually completely involuntary.
Then introduce a regular vibrator to the exterior.
Then go in with a small nub
Then when behind while thrusting during regular sex massage it and even finger it. Hopefully she will orgasm from that ( intercourse while simultaneously massaging her rear entrance)
Once that happens she should be asking for it.
Just go slow cuz if she is shy and vanilla and feels pressured for this and you thrust her wrong back there ( it's a different intercourse) you are toast.

Good luck!