3/11/09
Confession: I Want to Do My Boyfriend with a Strap-On

Our contributor, a woman who wishes to remain anonymous, has a confession to make.

My boyfriend’s butt is beautiful. It’s pretty. It’s plump. It fits in the palm of my hand. I can’t keep my hands off it, and simply touching it turns me on. I’ve spanked it, kissed it, rubbed it, grabbed it, bit it — and now I want to stick something in it.  A strap-on dildo to be exact. I want to bend that boy over, face down, bum up, and do him in the most dirty of ways. I want to make his prostate gland giddy with anal afternoon delight.

So last November I said to him, “I want to do you in the butt with a strap-on. I think it’s only fair.” He’s not only put his peen in my vajayjay, he’s poked me in the tush too.

“Um, no.”  He laughed nervously and changed the subject. Needless to say, this no-bullshit approach did not work.

Unwavering in my attempt to stick my strap-on dildo where the sun don’t shine, I approached him again in December with a more sensitive strategy:  “Just because I want to pack your fudge and you let me doesn’t mean you are a fudge packer, baby.”  I thought assuring him I wouldn’t think he was gay, but rather a try-anything-sexual would work for sure. Sadly, this simply wasn’t the case.

“I know,” he replied, “I just don’t want a dick in my butt.  It’s not going to feel good.”

With this important information, I devised a more detailed put-it-in-the-pooper plan.  In January, sounding oh so scientific (and as cute as can be), I spouted off some knowledge gleaned from this very site:

“The prostate gland is similar in size and shape to a walnut. It is located at the base of the bladder and surrounds the ejaculatory ducts and urethra. It is essentially the equivalent of the female G-spot, hence it’s called the P-spot.  When stimulated during anal sex, it can produce orgasms. The P-spot is your best friend and you’re ignoring him. That’s not very nice, now is it?  From what I hear he is very fun to hang out with.  Perhaps you should make a play date.”

Silence…more silence…then finally, what my pretty little ears have always wanted to hear.  “Maybe…”

After a month of many talks about how to travel the brown brick road, we agreed that purchasing a vibrating anal plug would be the best way to get things started. February arrived and with it a text message from my boyfriend that read, “I’m really excited for you to do me in the butt. Wanna buy a butt plug today?”  Hell yes I do.  Butt plug today, strap-on tomorrow!

Last week we went to Fascinations, a local sex shop, and purchased our very first 4-inch blue butt plug.  We rushed home, stripped off our clothes and jumped into bed.  He looked a bit uneasy.

“Are you sure you want to do this?” I asked him. “I only want to do this if you’re comfortable with it.”

“It’s probably going to feel like a turd,” he laughed. Not the response I was hoping for, but he bent over, face down, bum up, just as I’d imagined, and after applying a little lube I eased that blue puppy in.

I started slow and soft, in and out, in and out, then applied a bit more pressure. After a few minutes I turned on the vibrator located inside the butt plug.  It was loud.  Very loud. The longer I sat there on my knees behind him, the more I felt like I should be wearing latex gloves and a lab coat; perhaps throw in a clipboard and stethoscope as well. Probing is the word that came to mind.  It felt far too formal for my liking, and I could tell by his silence and his face in the mirror behind our bed that he was not enjoying the ride.

“Okay,” I said. “Let’s try a different approach.” We sat for a few minutes and discussed what would feel good.  We agreed that foreplay first without the butt plug was a good idea.

Some plug-free fondling led to some plug-free fellatio. And when he was good and ready, I popped the plug back in. He liked this combination of front and back attention much better, as did I. But after a while my mouth and hands needed a break, so we resumed the prostate exploration in the spooning position. I inserted the butt plug half-way in and angled it up towards his belly button to start. “That feels really good. It’s vibrating my balls.”  Then I pushed the plug all the way in and started feeling around left to right.  “That doesn’t feel so good,” he said.  So I started making soft, slow circles inside.  He liked that a lot.

After about an hour our anal endeavor was over and the search for his prostate gland was called off.  He didn’t orgasm and he was strangely quiet as we lay there. It occurred to me that maybe I was asking too much. Maybe expecting amazing orgasms from just the push of a button was unrealistic. Maybe we should have thought of the plug as a side dish rather than the main course. Maybe P-spot stimulation just doesn’t work for some guys, just like some ladies hate having their G-spot touched…

Then he turned to me, smiling, and said, “Practice makes perfect, baby. I’m ready for round two.  What about you?”

Like I said, butt plug today, strap-on tomorrow.

Interested in Your Own Butt Plug?
The Top 5 Rules of Engagement for Backdoor Toys



588 Comments

  1. Dear Madamoiselle L,

    You said you didn’t get my point. So let me please try to explain further. First, I strongly promote strap on sex and believe it should be common, and not something we do in the closet as if it is wrong. In fact, i prefer to have a woman who prefers this sex over the normal one: I prefer that she fucks me in the ass several times a weak, and that she gets the full pleasure of that and climax hard as she does me.

    With that said, I do not, however, like the woman to “use” strap on sex for something else. Most of the wives who use strap on sex are more into something else, such as him being fully feminine, cuckoldery, … This is not my opinion, as you said; rather, it is what i see from hundreds of sites and communications.

    I love the woman to think of strap on sex as a way to feel her power side in sex–that is being the penetrator–but not anything else. It’s ok if she dresses him in panties during sex, but this should not mean full feminization. Males love anal sex; they don’t need to become women to love being on the receiving side.

    I hope this site and others would greatly promote strap on sex.

    Submissively, bending over

    bim

  2. Not that I know a lot about this, in fact, I know very little, but “Bim” said quite a lot about “the type” of woman who supposedly likes this form of sex play, with a LOT of suppositions, but we were given no evidence that anything said was more than his/her opinion.

    Bim said: “Most wives who love strap on sex expect their husbands to become transgender or even transsexual.” END QUOTE You KNOW this? How? All I know is a few people who enjoy this, and NONE of the “wives” want their man to put on their panties and bra….

    I guess I don’t get Bim’s point.

  3. No matter how we try to divert the truth, the matter is: There are much more men who love strap on sex than there are women. I mean strap on sex for strap on sex, not for something else.

  4. That’s right, Mark. Very few women are really into strap on sex itself; otherwise, they would have appeared first, and then they would not link strap on sex with something else.

    Your gf might go for strap on sex for, as you said, “favor” for you, not favor for her too. So, she doesn’t like strap on sex, and because of this, she would expect you to do many submissive things for her to give you this favor. All of this is because she doesn’t love strap on sex.

    I wonder why all the sites about strap on sex when the woman herself doesn’t like it.

  5. First to Elizabeth:
    I’ve been thinking to show his article to her in an indirect way and find out what she thinks about this indirectly. Because if I do it directly, I’m sure she’s smart enough to realize I’m into it.

    Second to Bim:
    I totally agree with you and I am just like you and I hope that my lady would like the strapon sex just for the sake of it and that’s it. I don’t like her to expect me to cross dress or do it as a humiliation. I really liked you comments about this. I mean I’m exactly looking for a lady you are looking for and unfortunately they are rare. God I wish I could find a lady who just thinkin about penetrating me would make her wet. I wish there were some dating websites for this. I hope I’m wrong, but I’, quite sure my gf won’t like to be the penetrater. Maybe I could convince her to do this as a favour to me but if it’s a favour it’s not gonna satisfy me because it’s not satisfying to her.

  6. Hello all,

    I came across this site as i was searching for some forums on strap on sex. I read some of the posts and would like to share my opinion.

    First of all, I love strap on sex, or let me say I guess i love it even if i haven’t had any experience with it. In fact, i wish i could find a girlfriend or wife who prefers to be the penetrator most of the time we think of sex. I hope this becomes much more widespread.

    But the question is, how many women really love strap on sex without all the complications they gather around this lifestyle? Sorry if the word complications seems rude, but we need to deal with the problems if we want to spread out strap on sex.

    Strap on sex DOES give power to the woman and put the man in a submissive position. There is no harm in that: The woman has the right to be in a pwerful or submissive position, and so does the man.

    However, how many women love strap on sex for the power exchange they feel, rather than anything else?

    I mean, how many women love strap on sex ONLY because they love to be on the penetrator side.

    The answer is: Just a few.

    Most women who love strap on sex love it because of SOMETHING ELSE, such as cuckolding, lesbianism, sado-masochism, or humiliation (is it self-reflection). Few love it just for sexual power and satisfaction.

    Most wives who love strap on sex expect their husbands to become transgender or even transsexual. Others love strap on sex to fulfill their sadistic trends. Other love it as a humiliation, maybe because they feel so if they have free normal sexual life.

    In all these women, where is the love for strap on sex itself? Nowhere. For them, strap on sex is a medium for other lifestyles.

    In short, strap on sex is used by people from different lifestyles, such as sadomasochism and cuckolding. They are not people who love the act of penetrating itself. I hope we can differentiate between the reasons of strap on sex. For me, I love the woman who can find her power in penetrating her partner, without anything else. I mean, I love her to get wet thinking of penetrating me. I love her to “prefer” strap on sex over all other sex. It’s not just the prostate gland that makes me love strap on sex, but ALSO my submissive position bent over and penetrated.

    I hope more women “in real life” love strap on sex for itself, as the woman who posted this blog.

  7. Why don’t you just show her this article?? I mean… You probably shouldn’t show her the comment section, but read the article and ask her what she thinks. Seems like a good idea.

    Second Mark… I’m guessing you’re not the same as the first mark, but anyways- Just because it was negative for you doesn’t mean it’s negative for everyone. And it sounds like your wife had a bit of a Domme in her… Which is often really hard for women to deal with (precisely because people equate dominance with masculinity. Such BS). Sorry, but you sound rather uncaring in that situation. She wanted to fulfill a fantasy, and it’s OKAY if you didn’t enjoy it. But saying shiz like “do you realize you’re doing exactly what women have been complaining about for thousands of years”… First off – yeah, maybe she did. Maybe if more women treated guys like meat they’d stop doing the same to us. And Secondly – it’s a SEXUAL FANTASY. It’s not saying things she particularly wishes or agrees with… If she has a dominate side, she was expressing it in a way she felt comfortable doing so. AND some guys (and girls!) LIKE that kind of stuff. She should have expressed to you her entire desires there but she probably didn’t realize them. How about some understanding, instead of just judgement?

  8. I did that once with my former wife and WOW was it a negative experience. After she tried for months to get me to do it I finally did. I tried to get into it, I tried to enjoy it and when I did she did everything she possibly could to make me feel like a piece of garbage. I almost laughed. I thought “do you realize that you are now doing exactly what women have been complaining about for thousands of years”? But I didn’t say that. We are no longer together and I learned my lesson to never do that again.

    My advice to guys? Don’t ever do that ever, ever, ever unless you either think you are Gay or Bisexual and that is what she wants.

  9. Mark/Elizabeth
    I wasn’t even sure to bring up the masculine/submissive stuff ‘cept Mark mentioned how his girl was so anti gay. I don’t know what’s in her head. So you’re both right. (It isn’t either masculine feminine sub dom or any of that! I did not intend to infer that) It’s about male prostate orgasm and all the nerves in that area.

    I really wanted to point out that the way to get to that level of sex play is prostate play, other things can happen later. Took me 8 years.

    And to remind beginners to be careful about being really clean about it. (Scat is just such a turn off you probably mize well consider it your first and last time you get to do this.)

    Good luck Mark, I just can say it took time and that’s how I got there.

  10. I totally agree with you Elizabeth. I am a really masculine guy and I hate cross dressing or do anything that women like to do. But, I want to be really submissive when it comes to sex.

    But, unfortunately alot of people can’t seperate dominance/submissiveness with femininity/masculinity. All I’m afraid to bring this up with my girlfriend is the fear of this issue. Cause I’m pretty sure she’s not like you Elizabeth and she can’t differentiate between these two whole different subject.

    I am really scared stiff to bring this up with her. I love her too much and I just don’t wonna lose her for this pegging bullshit. I don’t know, but I just think in her point of view it’s too much to ask and I assume if I tell her about this, she’s gonna get mad at me. So, I’m thinking of some indirect ways to find out what she really thinks about pegging.

    Any lady here who didn’t like pegging or didn’t even know about it, but now she would give it a shot has any idea for me on how to introduce this concept to my girl?

  11. I really wish people would stop equating dominance to masculinity and submissiveness to feminity. I am (mainly) a dominant female. And in no way am I particularly masculine. Even when I’m pegging him, it’s NOT about making him FEMININE. It’s submissive. Ugh. Dominance/Submissive is not related to a particular gender!

    Oh … and NEVER EVER EVER will I be okay with scat play. Sorry, that’s unsanitary, gross and just yucky. Not every girl who’s into that kind of stuff will ever be into scat play.

  12. Mark, your question tweaked me.

    I think every guy on this list that hasn’t been pegged is thinking how the f@#k do I bring this up?

    I know, I’ve been there.

    It maybe took 8 years before we were in a sex shop and I was looking at a display and the conversation was along the lines of “whatta ya think?” “Really!!!??, I mean you want to do that???” And the amazing thing is we worked up to this point by her fisting me. (She’s got tiny hands!) My wife is not dominate enough to get off on the acting power play that pegging provides. She is GGG enough to realize there are g spots for girls and p spots for men and she loves to make me crazy. So butt play for us (and I have rarely entered hers) has been focused on prostate stimulation. (Sometime I wonder what it would be like to find a very dom woman and well, I’m married and wouldn’t stray like that. (But a guy can fantasize!) Getting pegged is very personal act and very trusting of your partner. Like she’s not going to blab about it to your friends.)

    Where do we go from there?

    Does your girl like to act masculine? The entire anti gay etc thing sounds like a bunch of “this is what I stand for, I must be … I wanted to write republican or something but don’t mean to offend… type thinking.” Perhaps she’s somewhat submissive side and perhaps equates a gay male as not masculine enough to “take her.” I don’t know, I really can’t read her mind.

    I will suggest, and this goes to all the guys wondering how the hell to get pegged, is that you some how get the knowledge in front of your significant other, that you have a prostate that is really really sensitive to stimulation. Butt plugs, and all sorts of massages can ensue.

    Here are some big words of warning. Be clean. And I’m not talking gloves or any other dental damns etc. If you think this might happen tonight, I’d personally suggest you don’t eat a damn solid piece of food all day. Soup is good for a soul. Bowel movements till you can’t do it any more. Drink your dinner is a fun way to go. You’ll be loose and ready. The result is if your first time isn’t a major “ugh, I’m not playing with your scat!” I’d bet it happens again on some kinky night. (Save the accident for some other time. It will happen.)

    And one day, you’ll be looking at the Good Vibrations website with your girl and all I’ll say is you can take a bigger one up your you know what than you think, make sure she’s happy with the harness or however its affixed, bucket of lube, seriously, and … congrats. You’re not her bitch, she’s just fucking you in a really kinky way.

  13. Wow, this was the greatest article I had ever read. But I wish I could read the same article from a man points of view who convinces his wife or girlfriend to do this with him.

    I have never tried this pegging stuff before. But I am really curious to give it a shot. I have no idea how to bring this up to my girlfriend. I totally love her and I’m scared bringing up such a fantasy to scare him off and think I am gay.

    She hates gays and crossdressers and she has told me she likes masculine men. That’s why I’m scared to ask her to peg me.

    Any idea?

  14. My man just told me that he enjoys wearing my bra; has his own silk panties, and wants me to have lesbian play with him. I use to be bisexual and this made it easier for him to admit it to me. I am going to go ahead and try it out the next time we are together. Reading these stories has me just horny as hell! I need to read a little more so I know what to do; but I am excited because it has actually been one of my fantasies for years… I had one boyfriend that explored with me when we were young; and we did just as my man now wants to. He is feminine and I am a tomboy; I guess it makes sense now that when he kisses me and makes love to me and caresses me so gently; its because it is what he wants in return. He calls himself a lesbian in a mans body; but he is very much a man. This is a great forum; I can’t wait to learn more 🙂

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