O.k, so here's the deal. I come from a very conservative upbringing and I teach Sunday school. I'm not exactly a pro here and I'm not exactly a prude either. I have no moral qualms with trying new positions and techniques with my husband but I just have a very hard time vocalizing what I want! I've been learning alot about anal sex and have even tried using a plug during masturbation (that he doesn't know about) and had great results. I want us to explore this together as a couple! I understand that his prostate works much like my g-spot. Sounds great, but how do I bring it up? I don't want to scare him.
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(Since I wrote this, I found out that you should try to use toys with a flared base for anal stuff, but nevertheless, this was our first (really hot!) vibrator experience together.)
My husband used to be so uptight about the anal thing-that is, when it came to him.
Well, about a month ago, I decided to show him some ways to use a vibrator on me.  When we got into bed, I played like I was a schoolteacher.  I used a matter-of-fact voice and explained everything to him while I got started and eventually vibrated my pussy to the night’s first orgasm. 
The next part really took him by surprise.  I took out another of my vibrators and put a condom on it.  I instructed him to lie on his back and hold his legs in the air.  He protested, but not as much as I thought he would!  He let me—ever-so-gently- give it to him in the ass.  The whole time I spoke to him like he was having a prostate exam or something.  I couldn’t believe how hard he got.  I finished him off with a nice blow job and the vibe whirring away in his butt.  Holy shit, he came so hard.  I don’t think I’ll be hearing any more vibrator complaints from the new recruit!
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For many men the subject of anal sex might be a little too "delicate" to even discuss. If that's the case, the introduction of your lubricated finger during oral sex might be taken better than a direct verbal invitation. Don't force things! Taking your time, gently tease the area around his perineum and see how he responds, getting closer to his anus with every stroke. Then, you might pause your oral activities and ask "Do you like this?" If his response is positive (and it may even be a moan), generously lubricate the area with your saliva or a good lubricant like Eros or Wet Platinum and insert your index finger only up to the first joint.
Continue fellating him so he can enjoy both types of stimulation simultaneously. Then, insert your finger to the next joint. If he finds this pleasurable you can slowly start to insert your finger in and out. (Make sure your fingernails are trimmed!) Try to match the tempo of your blow job with the movements of your finger until he relaxes. If he seems ready, or is moving is hips to meet your finger, you can slowly curl your finger up in the direction of his prostate.
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"Can I stick my finger up your butt" usually works for me
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Speaking as a "nice Southern lady" I understand as I come from the generation that never talked about sex or how to ask for it! Even oral sex was quite an alien concept to my group of friends. After a change of husbands in my 40's I was taught to ask for what I want and my sex life has never been better. Now I'm trying all those kinky things I never dared before (and yes, anal as well) and loving every minute! It does help to have a supportive partner.
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