This topic was brought on by a comment I made in an earlier post called “Grilled Cheese Sandwich.” But I needed the proper motivation to write this piece. Well with the theme from “The Good, The Bad and The Ugly” playing in the background, I can man up and tackle the subject.
Men and Strap-ons
OK, what is a strap-on? It is a device where a dildo or vibrator is held in a harness that is strapped onto another person. The strap generally goes around the waist and between the legs with a holding device on the front to mount a sex toy.

Take it like a Man!
You may be thinking, “Ain’t nobody going to stuff a banana up my tailpipe!”
Fair enough.
But let’s take a closer look at why we would think think that. Lots of men would and do love engaging in anal sex with the ladies. C’mon, how many of you guys have ever watched a woman walk away and thought, even for just a second, how warm and tight that would feel? Oh yeah, pretty much all of us.
Some women have the attitude of, “If he wants me to take it back there, he can take it back there too so he knows how it feels.”
WHEW! There’s a thought. Reminds me of an old joke. Remind me to tell it to you sometime. Turns the whole world around when you think about bending over for her doesn’t it? Yet you want her to do it without a second thought, don’t you? Yeah you do.
But taking it up the ass doesn’t make her gay! Women are supposed to be all access! Since when? I don’t remember getting that email or seeing that story in the New York Times. Not even the Leisure section.
So it’s pretty much the gay thing isn’t it? I thought so. Well, like I mentioned before, don’t ever let yourself be talked into doing anything that you really, really don’t want to do. Either of you. So you may never get to enter through her backdoor. Deal with it. Nor do you have to give yours up either. But I’m going to get medical on you here.
Prostate massage. Learn it, live it, love it. Yes I know that once a year you bend over and your doctor gives you the finger. That’s different. The doc is looking for any abnormal swelling. And you know what happens when you get an enlarged prostate: constant urge to urinate, depressed libido and possibly an operation that takes away your ability for erection. Damn. Do you really want to risk that? Sure, medicine has advanced, but you might still end up needing a balloon inserted in your penis and have to pump it up like a ball before the game. Of course prostate massage is not guaranteed to eliminate risk of an enlarged prostate, but the massage is recommended by many physicians.

Learn it, love it!
If you can loosen up a little, perhaps enjoy a little rimming (God bless her!) and a finger, you could learn all about prostate massage. It can be a truly liberating experience. Incredibly intimate experience with your Lady with one hand or mouth up front and a digit or two in the back will literally blow your mind!
But your lover’s finger isn’t a rubber cock is it? Back to gay paranoia. Look, if your aren’t interested in having sex with men, a strap-on isn’t going to change your mind or character. You can be the toughest linebacker in the league and still enjoy a good ramming from your Lady. If the two of you are interested, start small. Now you understand the look on her face when you brought home that enormous dildo from the bachelor party. Consider the consequences of that sliding home inside you!
Another world turning moment, huh?
If your partner has any toys, look at them together. What scares you the least? Don’t worry. She will be attentive and she will be very concerned about your well-being. Especially if this is something she really, really wants to do. So take a shower and be sure to wash well back there.
Get comfortable and pick a position. Some men prefer doggy, so she can’t see the fear in your face the first time. Some men prefer to be on their backs so that there is instant non-verbal feedback during the playtime. Women are usually very good at picking expressions and clues that we never seem to see or even know that we are broadcasting. Some men only let their partner play with their backdoor in a BDSM setting. After all, if you are tied up you aren’t responsible for what happens to you, right? (We will explore this thought process in a different post later, after more science stuff.)
Pick a toy. Partake in some extended foreplay. See? It really is important. Use lots of lube. Let her try her finger and if that goes well, have her put in another, then a third. It will feel strange. Kind of like you want to have a bowel movement. Don’t worry, if you went earlier and washed well, nothing embarrassing should happen.
Ready? Here comes the toy. She will go slowly and treat you the way she would like to be treated. Please take note of this. You may well get your turn later in the evening. Don’t mess it up. You will feel weird. Your anus will feel stretched and will start to tingle. Some men have an orgasm right there. Some don’t. Take it like a man. You are planting the roses and doing it for her. Many of you will actually learn to enjoy it.
She will go nuts for you. You became vulnerable and opened up for her. You trusted her. You trusted her with your very manhood. And you both probably got great orgasms out of it. It could be a one time thing or could be added to your bedroom rotation. At worst, it didn’t work out and one or either of you didn’t like it. That is OK! The point is you experimented together and could be drawn closer by the experience. You understand her point of view by switching places. It’s not for everybody. If one of you likes it but the other doesn’t, well we know how to handle ourselves while staying true to a monogamous relationship don’t we?
At best, it is an incredible bonding experience. One that is fulfilling, exciting and just plain hot. There can be a lot of back and forth and marathon sex sessions are always welcome. And they start happening more and more often too!
So does taking a finger, toy or strap-on make you gay. Hell no! But it will open doors to closer intimacy and who knows what experiment is next? I wouldn’t miss it for the world.