Ask Peg: Strap-On Advice

Dear Peg,
I'm worried that my boyfriend might be gay. He wants me to wear a strap-on and, you know, put it in his butt. Is this normal?
Mary
Topeka, KS

Dear Mary,
I sense that you are a bit shy when it comes to discussing sex. Well, don't Worry, dear. I'm here to help. Your boyfriend is probably not gay. He is just discovering what millions of heterosexual men around the world have known for centuries. Having his prostate massaged through anal intercourse feels very good and gives him a more explosive orgasm. Just because he finds this pleasurable does not mean that he wants a man with a real penis bend him over and fuck him. After all, he’s asked you to do the honors. You must not mistake physical pleasure with sexual orientation. They are two very different things.
Peg

Dear Peg,
My husband wants to try anal sex - I mean, he wants me to use a strap-on dildo on him. We both find this fantasy exciting, but he is concerned that putting things up his ass will hurt. He says he wants to submit fully to me, but every time I get near his butt he flinches. What should I do?
Angie
Ithaca, NY

Dear Angie,
It may be that your husband likes the idea of having you fuck him, but would rather it remain an exciting fantasy. Or perhaps he is just a bit inhibited and needs a little more gentle encouragement and reassurance. The next time you make love, try massaging his butt and lower back. As you caress his buttocks and inner thighs, get closer and closer to his asshole, but don't try entering yet. Put a dollop of lube on your finger and massage it all around the outside of his pucker, till his sphincter is nice and relaxed. If you can get this far, I'd be surprised if his butt hasn't already swallowed your finger up. If not, gently push your finger in, and he should be writhing in ecstasy. Now that you've introduced him to the pleasures of anal stimulation, try getting an anal beginner's kit, which will take it up a notch. The small butt plug and small anal vibrator will whet his appetite for, ahem, larger things, like a strap-on. The Anal Eze numbing lubricant in the anal kit should make his first time smooth sailing.
Peg

Dear Peg,
My boyfriend and I love having wild strap-on sex. But sometimes the harness gets uncomfortable when we are in certain positions. Isn't there something that can give me a little more comfort? Eleanor
Flanders, WS

Dear Eleanor,
You haven't been to the toy store in a while, have you? It sounds like your harness is due for an upgrade. New harness designs are much more comfortable than they used to be. Make sure you get a model with adjustable straps and a secure waistband. SexToySex features a selection of quality harnesses, including models that feature padding to cushion your pubic bone, and a corset harness that looks hot while being functional.
Peg

Dear Peg,
I really enjoy bending my boyfriend over and giving it to him good. (He really likes it too.) But I was taught to believe that men were supposed to be the dominant sex partner. Is there something wrong with me for enjoying it so much?
Lisa,
Wilpington, CT

Dear Lisa,
For goodness sakes, woman - don't buy into oppressive sexual roles. Women have active sexual desires and feelings just as men do. There is no good reason why you shouldn't be able to indulge yours, just as there's nothing wrong with your boyfriend for wanting to explore his submissive side. You should consider yourself lucky to have a guy who is willing to let you take charge. The only reason it seems odd is because you learned certain rules about how men and women are supposed to act in bed. But wouldn't the world be a boring place if everyone blindly followed the rules? Explore your desires and have some fun. It will do you both a world of good.
Peg

Dear Peg,
My boyfriend wants to start doing some role-playing during lovemaking. He's been going crazy at the adult store buying all kinds of things including some restraints, a paddle and a strap-on that vibrates. He says he wants me to use these things on him and become a dominatrix. But I've never been the aggressor in my life. I'm scared to death that I might hurt him, especially with the dildo. What do I do?
Anna
Boise, ID

Dear Anna,
The first thing you need to do is relax. Your boyfriend would not be setting all of this up if he didn't trust you. The fact that you are worried only means that you will be extra careful when it comes to finding his limits. Choose a special safety word that he can use so that you will know when to stop what you are doing. Remember that role playing is a form of acting. Get into character and allow yourself to become the fantasy you are portraying. It is a chance to explore sides of yourself that you never knew existed before. Be brave and let the dominatrix in you come out.

If you have never used a strap-on to fuck someone before, it can be a little scary. But no more so than the first time you perform any other sex act. For a tutorial on strap-on basics, check out our guide to bending him over for the first time. Have some fun with it. You are being given the chance to be in Charge, so take advantage of it and let loose. Has he been naughty? Then give him what a bad boy deserves.
Peg