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Confession: I Want to Do My Boyfriend with a Strap-On

Wed, Mar 11, 2009

Confessions, Personal Post

Strap-on harnesses are available for sale at GoodVibrations.com

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 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.

 
 
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525 Responses to “Confession: I Want to Do My Boyfriend with a Strap-On”

  1. ehumplick Says:

    just a word for all the insecure boys that read this…think about it, every one if us has either felt the unrelenting, cold, slimy glove of doom. most of us have felt the date raped feeling of “the scope” fully inserted into our rectums, and since most doctors are boys (sorry ladies) aren’t you feeling more queer already? This is your wife, or your girlfriend, or Jenny from the block, that wants you to experience that intensity that typically only women can feel. I don’t know about any one else in the room but I can’t orgasm with out direct stimulation, if this is a way I’ll try it..hell in case it hasn’t already been said RIDE THAT PONY!

  2. Ty Says:

    That’s funny my ex-girlfriend loved my ass too and I always thought she was joking when she said she wanted to fuck me in the ass. After reading this I guess she wasn’t ha.. My response to her every time was NO FUCKING WAY.

  3. Michael Says:

    Yes, please. :)

  4. steven Says:

    I wish I could find a girl that is into this :’(

  5. Lee Says:

    Oh yes my wife and I do it a few times a month, and we love it. We use a “Feeldoe” and it is great.

  6. Rubita Says:

    I really really wanna do my bf. I have licked his butt several times and he orgasms a lot, but he doesn’t want anything inside. One night we were drunk and I brought a girl home and she put a strap-on but he didn’t want either.
    I have tried my fingers and my tongue and while I’m doing it I get so turned on.

  7. nathan Says:

    i thought my girlfriend would want to. the day i brought it up she gave me a look and smiled. as i thought she was into it, i was wrong. she was kinda grossed out. a few nights later after it slipped my mind a was awakened to cold rubber rubbing against my back… it happend and i honestly loved it. A honest uncontrolable feeling and release! all men should try it and not be ashamed.

  8. mike Says:

    i have tried this and it was great. i found someone who was willing to do it and just went for it we both loved it and she really got turned on by it.

  9. boss Says:

    can i get a hell no

  10. Natalie Says:

    My relationship is the exact opposite. He wants it but, I am kind of scared. We have been shopping for a strap on but I don’t know… It seems odd to me. Maybe I’ll like it when we do it? I just know anal hurtsssss me.

  11. Joe Says:

    I wish my wife wanted to take my ass. I am all up for chastity play, strap-on action, and “cleaning up” my mess. But she just will not have it. I am not interested in going elsewhere, I just wish my wife was willing.

  12. Kalli Says:

    I have to admit that when my “then” boyfriend approached me with the idea I freaked out internally. We never spoke of it again. One day he brought home a huge strap on and I told him that if anyone got that thing it was me. We had a really great sex life and could talk about anything. After an evening of great sex he so lovingly asked me if I would let him try it. I think I felt really strange about it for a long time, but I also was extremely aroused when I used it on him. Our relationship ended but our friendship is still going very strong. I find myself missing those days. When we catch up we always give each other a little wink. He even confided in me that there has never been anything as wonderful as our time together. I am glad I allowed myself to be open to it. Especially when I know it pleased him so.

  13. simo Says:

    i hope a girl practise with me strap-on and put her fingers in my ass but unfortunately i didn’t find who make me happy with this way

  14. lou Says:

    My ex-boyfriend loved the feeling of my tongue and fingers in his butt. I wish that my current boyfriend would let me try it with him but he thinks that it’s odd. I won’t stop trying to fulfill my fantasy so easily though.

  15. me Says:

    Im getting it next week. Cant wait

  16. Hate to admit it Says:

    I hate to admit it ! But my girlfriend playing with my ass felt amazing ! She always said she loved my ass and is always grabbing and touching it , we were drunk the other night and I was on top she kept reading further and further down my ass until there was an amazing pressure over my ass ! I couldn’t help but slide deeper inside of her moaning every time she moved her fingers ! I’ll leave it at that, but this is one thing you may think is gay but is well well worth trying out because the feeling you get is like nothing else …..

  17. feels weird admitting this Says:

    I have no attraction to anyone other than my girlfriend, female or male, but I like it when she plays with my butt. I brought the idea of a strap on up before kinda jokingly and she got weirded out. The other day I brought it up and she said it would be a good idea. So, I’m looking for a strap on now.

    We’re just human, there’s no shame in having a little fun.

  18. Just me Says:

    I might try her finger but anything else is out the picture. I saw a sit com were this old boy was tearing this girl up. Then when he finish she went in the rr & came out wearing a strap on. Rolled him over and she went to work. Boy walk funny for a week. And he kept saying “man that’s just was not right”.

  19. Mike Says:

    I wish this was my girlfriend! An ex suggested it a few years back, but I was scared at the time. Have thought about it many times since, and now I’m very interested in trying it.

  20. Emz Says:

    I had to goad my boyfriend into anal play. I begged him to let me milk him and I did. Finally, just recently, we agreed to try the pegging. Shopping for a strap-on this week. It’s awesome.

  21. jaj Says:

    i would love for a girl to understanding. giving and getting i would think would be the best

  22. Lauren Says:

    I need to find a guy that likes getting pounded. For the longest time I thought i was a lezbo for having the urge to pitch rather than catch…then i read a strap on story online and realized this is exactly what i need! its stress relieving just thinking about it.

  23. nathan Says:

    were every were most men denie it but there willing to try

  24. mattie Says:

    nathan i cant believe you posted this… it was our secret!!!!

  25. Kat Says:

    I’m glad me and my boyfriend can be open and willing to try anything. He said he loves me and would love any kind of pleasure I give him.

    I love guys with a great ass, just something I’ve been attracted to but my ex thought it was gay and I didn’t even dare go near the hole.

    It’s not gay, it’s another pleasure area and it doesn’t matter what your orientation is.

    In fact, I bet gay guys are thinking straight guys don’t know what they are missing out on haha!

    WIth the P=spot, guys can have those incredible heights that we women can.

  26. ryan Says:

    Never crossed my mind in the past. but my wife recently has found that putting her fingers inside me really turns me on during sex. this started about a month ago. well, a couple of days ago we odered a feeldoe strapless and a strapon with a harness. they should arrive within a week and we are both reall excited about our new arrival. i just hope its going to be great for both of us and stick around ( no pun intended)

  27. scott Says:

    My ex-girlfriend and I would have strap-on sex four times a year. It all started when we were going to a home show. we had sex all night in the hotel room during the night before. In the morning after our showers I was still horny. We were dressed and ready to leave for the show when I pulled up her skirt pulled down her panties, applied lots of lube. I bent her over the bed and took her ass for a good twenty minutes before I shot my load inside her back door. She complained that she had to start over and get cleaned up. I pulled up her panties and pulled down her skirt. I said no you don’t, just fix your make up, brush your hair that I was tugging on, you will be fine, the skirt will hide it.
    We got on the bus that took us to the convention center that the show was at. About an hour into the show, she leaned in real close and said to me softly.She said “My panties are soaked! In the back the lube and your cum has leaked out.Every step I make I can feel the dampness as my soaked panties, ass cheeks slide back and forth. My Skirt hides everything, but I know, You Know, and I know you know this secret.This secret of taboo sex we did, the fact of my situation as we walk around this show and no one else knows. I am ready to go back now to the hotel. I am so horny right now. The front of my panties is almost as wet as my back because I can’t stop thinking about it and what I want to do to you.” I told her we will leave in a little bit.But we came a long distance to see this show and get ideas for our new home. So I stretched it out another hour.I kept telling her we will leave in five minutes an whispered to her all the nasty things I was going to do to her when we get back o the hotel. It was pure torture to her. I could see it on her face.We ordered room service and spent the rest of the night in bed. We spent a few hours at the show the next day too.She realized That we could of left the show early the day before.
    There is a show that comes to our area four times a year.One night before that show she got horny and decided to try the new strap-on on me. She enjoyed it very much, especially because of the anticipation since we never tried it before but had bought the toy many month earlier.I came very hard that night. I caught my cum in my hand and she licked it all off and swallowed every last drop.So started the tradition of her taking my butt with her strap-on four times a year.I tell her I do this for her, that I don’t enjoy it. (But she does get a lot of cum to enjoy when she does do me.)I told her once in her ear at the show,that”I can feel her cum(lube) dripping into my panties(fruit of the looms). That got her all excited. We left then and had great sex when we got home.She bought me some sexy underwear later on, bananana hammocks, etc. One day she did me while wearing one. I came inside it. Then we went to the show. As we walked around the show she whispered “How does it feel, walking around with your cum filled underwear?” I told her I had a surprise for her. Before we left I went to the bathroom. When we got in the car I told her I bought her something at the show.I told her I will give it to her when we got home if she was a good girl. She agreed. I told her close your eyes and open your mouth. I then inserted my underwear in her mouth. I told her she had to suck on them till we get in our house then I will give her her present. We hit traffic so it took us an hour to get to our house.So when all is said and done
    switching roles, Changing asses, playing games we always use to have fun and good times.

  28. mel Says:

    My fiance and I are the kinkiest of the sorts I should say. We are a try anything once, and if we like it keep it going type of couple. I never had anal done before and when we did my gosh i fucking love it now xD. When he first told me about his darkest secret, I think he was more weirded out about it than I was. I was all for it. I love his ass. It’s so damn mmmmmmmm… I told him not to worry it does not make him queer. I tried it with my vibe and his reaction turned me on even more. So our next step is to get a strap on. I can’t wait. His fetish has turned into mine and i love it.

  29. michalis Says:

    hi to all , i always wanted it but was scared to ask , now with my soul made i can have it , and she wants do to it to me to . . . .

  30. Michael Says:

    My wife and I are just starting to discover the wonders of anal stimulation and so far it’s has been very good. I’ve been married for a long time and never even thought about this but when she started to play with my ass with her fingers I realized it felt really good. So now she’s working me with a dildo and can tell she loves doing it because she can see how much I enjoy it. Maybe a strap-on soon (I hope so).

  31. Donny Says:

    I like anal play. I do not like men. there is no attraction for men. A person who is open minded with sexual activities is not gay. FemDom is wonderful. My girlfriend loves to use toys. my ultimate fanticy is to have a 3some with 2 dominate women. i can only imagin the fun that would be.

  32. Nikki True Says:

    I love being able to do role reversal with a man I love. People tend to get very insecure about being behind a man, but thats where his g spot..or P spot as it’s called…is located. It just adds to your love making menu in my opinion.

  33. Angel Says:

    This is the yummiest stuff ever. It may take a while for your man to love it, but I can’t imagine any man turning down a good tonguing (after shower & a bit of practical preparation). Fortunately I do love anal myself after many years of not loving it at all, so he saw how intense it was for me.

  34. Angel Says:

    And plus there are so many kinky things to do to him with his legs in the air…it’s amazingly sexy.

  35. HELP!! CAN'T GET TURNED ON Says:

    Husband loves this, but I am having a rough time and it’s causing us alot of issues, How do you just get into it, it doesn’t turn me on and I’m going to check out his feeldoe and see if thisis what we need , we’ve tried a couple of times, but it is terrible for me. HOW CAN I GET USED TO THIS< PLEASE< NEED HELP FAST!!!!!!!

  36. Re: HELP!! CAN'T GET TURNED ON Says:

    Everyone is different. Do not force yourself to do something you hate unless you really want your husband to be enjoying himself. If you’re uncomfortable, don’t let anyone pressure you into doing it.

    That said, discomfort fades with familiarity. The more often you’re around it or try it, the less awkward and uncomfortable it becomes. You may come to love it, you might come to just tolerate it, but if you want to keep trying for your husband then persist. If it’s causing too much of a toll on you, desist! Keep honest in your communication with him and maybe you can work out a compromise.

  37. jim Says:

    Been doing it for years with my girlfriend. Don’t knock it until you try it.

  38. Sam Says:

    Having my girlfriend pegging myself is awesome. She asked one day if I would try it and I said yes and she has been pegging me since. It is an awesome feeling. She never fails to get me off. To anyone who hasn’t tried it I say you don’t know what you are missing.

  39. Rhonda Says:

    I have enjoyed anal sex with my boyfriend for the past couple of years. But the other day I asked him if he would let me have anal sex with him using a dildo. To my surprise he agreed and since that day he has be bending over for me when ever I want. It is a big turn on. Several times I have even pegged him to a hands free orgasm. I didn’t realize just how turned on you can get a man turned on by pegging him.

  40. Advice Says:

    A couple of months ago my boyfriend asked me to sick my finger where the sun don’t shine. i thought he liked it but aparently not :( it turns me on soooooo much but he doesn’t like it. i really wanna pound him with a strap-on………. but i can’t get him to agree to any ass play :( unless it involves mine. advice??????????

  41. Jason Says:

    Some guys are way too lucky. I’d give anything to have my cute little patootie pounded relentlessly by my gf. Sigh.

  42. Louis454 Says:

    “Peen,” “vajayjay,” “tush,” “pooper,” “fudgepacker?” Is the writer like 7 years old?

  43. jonny rocket Says:

    hmmm. i would have to think about that one.

  44. ocala john Says:

    Recently during a massage, my wife rubbed my butt with the vibrator,it felt great,without thinking,i raised to meet it the next time.soon i was on my knees and asking her to insert it. It just happened (or did it) The feeling was very intense,I did all the humping and pushing without any thoughts other than it felt great. She hasnt done it again YET, but,ive been using butt plugs to masturbate every since. im buying a strapon today.I hope she’ll use it. Ladies, if your curious, a massage with some light rubbing will tell you all you need to know.

  45. anon Says:

    As a straight male I have to say I enjoy and even have fantasies during the day about my gf putting on her strap on and doing me. Guys don’t be afraid to try it, it can feel really good. And women don’t give up asking. Keep trying and you may get your wish

  46. Mary Katherine Says:

    My current boyfriend is an ex athlete and current cyclist. He has the cutest bubble butt in his cycling shorts. I always fondle him in public when we ride together, run or at the gym just because he has the sexiest ass in compression tights. He’s a straight guy and man’s man but he likes it when I play with his ass and I think it’s hot!!

  47. yash Says:

    ahh..i am an athlete and i lov it when my girlfriend does me…i believe its only fair and sexy to explore one’s sexuality..me straight by the way..but the orgasm i get after she does me so lovingly n my voice then gets us both mad ;)

  48. hb Says:

    My wife and i have a strapon and a vibrating double dildo and we love them. We lay down facing each other, insert the double in our bums then i slip into her front and we both orgasm. all couples should try it.

  49. lady Says:

    used strapon with my BF but i didn’t like it, knowing he really likes it makes me feel bad and wondering if he is
    gay or bi


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