I have no doubt that I am straight, but lately I've been wanting my girlfriend to put on a strap on and fuck me.

How do I ask this? My ex-girlfriend introduced me to putting her fingers inside my anus during oral sex, and ever since I have been addicted to the feeling. Should I feel ashamed when I finger my anus when going down on a girl? When my wife gives me hand jobs she sometimes puts a small vibrator in my ass. I like this it makes me get off so hard. I often wonder what it would feel like to use a larger one, but I don't know how to ask her. I don't want her to get freaked out by just coming out and asking for a bigger one.

Do you have any good ideals on how I might ask her?

Thanks for any help!

Lucky you for having met someone who introduced you to something new! You absolutely should NOT feel anything bad about what you enjoy. Many, many men enjoy the well-placed finger, whether their own or a partner's. Why not take it up a notch and position yourself in a way that lets your girlfriend have that access to you while you go down on her? Of course, doing it for yourself is just fine but feel free to clue any future partners in about what turns you on as well!

I wouldn't worry too much about freaking her out, as she's already ok with the idea of using toys on you. If you want to try something bigger, you have a few options. You could ask as she's using the small vibrator - it's quite sexy to tell someone how much you enjoy what they're doing to you, and then add, "What do you think about trying something bigger?" Or, surprise her - buy a toy you'd like to try and next time she reaches for the vibrator, have the new toy ready and ask, with a big smile, "Can we try this one?". OR - simply talk to her, talk about how much you enjoy what she does, that you're glad the two of you are comfortable enough together to explore different things, sexually. Ask if there's anything else she'd like to try which will probably lead to asking the same of you and then you can tell her. You never know - she may already be thinking the same thing!

How do I convince my wife to agree to anal sex?

My advice would be to ask her. Tell her that you think that it is really hot and you will make sure that you don’t hurt her. Make sure that she is completely relaxed. Maybe have a couple glasses of wine. If she is not relaxed it will hurt her. Make sure that you prepare her by inserting a finger or two into her anus. Use lubrication, it helps. You can use something like KY Jelly or lotion. Very slowly put your penis into your anus and tell her that if at any time she feels too uncomfortable that you will stop.

As a side note, do not pull your penis all the way out and then reinsert it fully again. This is a little painful. Good luck.

Update: From Askmen.com

Because anal sex feels good

Women love anal sex because it can feel absolutely incredible. It's different in sensation and it doesn’t feel like anything else she may have felt before -- it's deep inside, it's not her clitoris and is not in her vagina, but feels strangely like both in a sort of mixed-up combination in another part of her body. The rectum, once it’s ready, literally swallows the penis up and can’t get enough. The back passage transforms itself into a sexual playground. If the clitoris and/or vagina are stimulated while you are inside of her, it can take her to another sexual realm. Anal orgasms are possible.

I have been with my girlfriend for 6 months and we have been experimenting with anal sex. We are having trouble with her relaxing her muscles. We have used various toys and my fingers but I can not insert my penis because I'm afraid I will hurt her. Can you recommend any exercises, positions or sex toys that will help?

Patience is really the biggest thing you need to make anal sex possible. Initial penetration is always the most difficult part of anal sex -- the anus is a tight ring of flesh at the opening of the rectum designed to control the elimination of bodily waste. It is partially under voluntary control, and partially reflexive to stimulation. Your partner has to relax, and you have to go slow to coax it into opening enough to receive your penis.

Start with a well-lubricated finger or a slim (smaller than your penis) dildo. The dildo is more realistic, but your fingers can flex and feel what they're doing inside her ass. Slide one finger in slowly, letting her adjust to it. Take your finger all the way out, then push it back in again. Give her anus time to get used to this kind of activity. Then slide a second finger in. Consider how big your penis is and realize that two fingers is probably enough.

For actual intercourse, picking a position can be important. Many women want to be on top, to regulate how fast penetration occurs. Other like to lie on their stomachs, or crouch doggy-style, or to be penetrated while lying on their sides. Choose what's best before you start. As always, control yourself. Take your time and use lots of lubricant. Listen to her -- if she tells you it starts to hurt, back off.

Eventually, a time will come during your lovemaking where her anus will relax enough to allow the head of your cock to 'pop' into her. If she is completely relaxed, that pop should feel completely painless. Now just because you're inside her is no reason to start pounding away like mad. Let her body adjust. Take your time. Eventually you will both be ready for more. As a side note, a couple glasses of wine before starting may help calm her fears of pain and leave you both open to a more relaxed situation. Good luck. Be gentle.

I recently purchased some anal toys and I'm having a hard time penetrating my girlfriend. I have made sure that we use plenty of lube but she can't relax her muscles. Can you recommend any exercises or positions? I don't want to hurt her.

At first anal penetration can be a bit uncomfortable. I have always said that a few drinks beforehand never hurt. Try inserting your lubed finger first. Keep your finger inside her until you can feel her relax around it. Depending on how big your toy is, you may want to try this with two fingers. I think that ass in the air is the best position for training. As soon as you slowly take your fingers out, begin to insert the toy. Also make sure that you are keeping her stimulated by rubbing her clit. It will help her relax and keep lubricated.