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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.

 
 
MORE LIKE THIS ON EMandLO.com:

 
Check out the beginner strap-on kits at GoodVibes.com

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

  1. henry Says:

    Lady, he’s not gay. He’s not bi. Don’t worry about that. It’s all about your hitting his prostate or p-spot. And maybe the role reversal.

    I wish there was a sex act for woman that guaranteed hitting the g-spot and giving them incredible orgasms, but came with a certain stigma, I’m sure most women would understand.

    Here’s a thought, does receiving oral make a woman a lesbian?

  2. Pranay Says:

    Sometimes i really wonder i am good and happy as a 21 year old virgin ! ( exclaims in horro )

  3. Gemma Says:

    I love your story, my bf and I just started this, and hopfully getting a strapon soon.

    He’s actually the one who got me into it!! plus he’s had a go with a dildo and loved it and playing with front and back at the same time he loves it. Glad we not the only ones!

    Good luck!

  4. tuffy Says:

    Wow this is such a relief my husband has been requesting this and its brought up so much confusion to me since I’ve never been exposed to the thought but reading this makes me feel awesome and ready to go!

  5. dudemon100 Says:

    i have used a dildo on myself for some time now used my ex-wife w/o her knowing, first time i had orgasm w/ it was amazing and i was hooked. I now have a g-friend that first fucked my several time w/ a dildo and we have since used a strap on she jacks my dick while fucking me and it is so hot its unbelievable. I am not gay in the least just love great sex. so open ur mind use plenty of lube and relax ur muscles and enjoy

  6. Dannie Says:

    dudemon 100: NEVER, EVER use someone else’s sex toy without their knowledge and consent, ESPECIALLY if you are using it anally. That is not only a drastic invasion of trust and privacy (and yes, there is and needs to be privacy in intimate relationships, even marriage), but cross-contamination of bacteria, fluids, etc… can lead to some TERRIBLE health repercussions. Women are advised even to have their own separate dildos for anal/vaginal use, and that’s without bringing a foreign body into it. I hope you haven’t ever used another partner’s sex toy like that again. Don’t do it. Ever.

  7. bill Says:

    I love to but fucked by a girl it feeles so good

  8. WD Says:

    I want so badly to have my wife take my ass with a strap-on. She’s great about giving me analingus and fingering . . . ooh! But no toys. I have to use them on myself when she’s not around. I’m working on her, though. Please baby, please!

    This straight man desperately wants a woman to make him her bitch.

  9. riley Says:

    Iv always wanted to do this with my husband he lets me use my finger sometimes but only because i like it haha I’m interested in using a dildo or something on him, but I’m waaay to scared to ask him, if i get rejected asking him to do something that i fantasize about …i think i would die or embarrassment! Even though he’s my husband i still have those fears or him thinking “oh shit i married a freak” he probably won’t but im still scared of the possible rejection. What are some other ways i can possibly get him into it??

  10. jwf Says:

    I always wanted my wife to try it on me but she will not even talk about it. I’ve pretty much given up on the idea but find myself fantasizing about a women with a strapon.

  11. SF Says:

    I would love for my wife to want to include anal play in our sex life, but she does not seem too interested. I am not attracted to men,but I sure like my Butt played with. And I would let her insert a strap on. but it needs to turn her on, too. We have good sex and she is ok with me masturbating, which I love, but the anal on me part would increase my pleasure levels.

  12. Billy Says:

    Hey that’s badass that so many of y’all like it, I love it up the ass
    By a woman, my girlfriend really likes it and loves to make me wear her panties and all that stuff.
    I have never been attracted to men but there is something very sexy about a woman taking you in the bedroom every now and then.
    So I love it and I think it’s cool to see so many woman into it, because when I first started liking that people I asked was like that’s gay but I didn’t care haha I’m 22 and I was 17 when I started playing with my ass but ya anyone and everyone do what you do and don’t care about what other people think

  13. Gregory Jacobson Says:

    Ive had two dreams with impailment. One where a hot chick whos one of ny friends was impailing my behind with a giant strap-on dildo. And abother where two of my buddies were getting the same from there gfs and me and mine were like huh so thats tge bew thing nowadays huh, and i once again got impailed in the bottom, and enjoyed it.

  14. james mollo Says:

    i want to try it and i am a buff sr8 guy

  15. Alicia Says:

    Ok so I *love* doing this to my boyfriend. He is so pretty and so, well, receptive, it’s just wonderful. Its a major power trip for me, especially since I use a very large dildo, I love the way I look wearing it, and I’m so much bigger than he is :P Luckily with the strap-on I use the center of the base naturally rests squarely on my clit, it really feels like a clit extension, and I usually have multiple, quality Os in a single session.

  16. Pretty and pale Says:

    Im a very open straight girl and when my bf FINALLY admitted that he liked his butt played with I jumped on it. I love to be dominant! And he just took it in stride. We got a strap on and I fucked him like crazy but before that we just would use toys and explored different things.
    My boyfriend is straight and not even bi-curious lol and what’s funnier is he is a rough and tough country boy cage fighter.
    This article makes me feel a lot better, kinda thought this was something weird that no one else really did! Glad we aren’t alone!
    I love fucking my boyfriend and he loves being fucked.
    I think it makes sex that much better when you can both trade off back and forth

  17. Hot n Ready Says:

    Riley,
    You should try writing him an erotic story about the two of you and include playing with his ass. I did this for my wife and as of now she will rub my anus during oral and intercourse. Wrote her another story and now she seems open to the idea of putting her finger in. Little steps…Until I can get her to use toys, then a strap-on, wish me luck as I wish to you!!

  18. Ivahardon Says:

    Ive been with my husband for nearly 20 years. We’ve always had a good sex life, trying new things. He’s been having anal with me for years & occasionally asked me to pop a finger in him. He recently ordered some new toys & I was shocked to see a strapless strapon amongst them!!! Well it was a massive turn on to wear it & we both had some of the best sex ever. I am looking forward to continuing our anal adventures… ;)

  19. Kirsty Says:

    Me and my partner bought a strap on last year and so far it has just stayed under the bed! Im determined to use it but hes panicking about being clean. We have an honest relationship and he can talk to me about anything but this is a real sticking point, ive tried telling him that any ‘accidents’ that do happen can be easily ignored but he still wont. We have lots of dildo’s and vibrators to use but he wont even let me use a finger :-(

    I just want to make him happy x

  20. STRAIGHT Says:

    MOST straight man are curious to try it,but its so hard for us to say(“babe suck my dick and finger my ass”).mostly coz we fear you might think we gay and how embarrassing its going to be if you say no..
    LADIES:start it easily with ass licking on blow jobs section,just make it feel natural that you not thinking its an manly but rather you enjoying it..from ass fingers to little dildos all the way to strap on we go there if we feel you dont think we not straight.

  21. Anika Says:

    After reading this article my boyfriend and I decided to try this out. So much for my British boyfriend being so “proper” lol. We found a great website http://www.sextoysforless.co.uk as we live in London now. It has a variety of strap ons and all types of lube. Now he is hooked I need to order a bigger strap on! I like the dominant feeling it gives me being in charge and watching him squirm, he he.

  22. Lolsmilyface Says:

    You are ALL WEIRD!!!!!! I love my man but would never stick anything in his ass

  23. mahmoud Says:

    woooooooooooow, i like it very much , i really want my wife do it with me, its so good sex, but i don’t know, she we understand it or not, but i really want she strap on me

  24. mahmoud Says:

    your man was very very lucky because you do it with him

  25. Lizzi Says:

    My husband has a lovely ass. When he sleeps on his stomach and just has the sheet over him I fantasize about taking the sheet off and slowly fucking him awake, which I would never do with out consent. Ive told him how much I love his ass and how much I want to lick it, finger it, and fuck it. The first time we tried we had been drinking, not a good idea. I took it too far and he didn’t want to try again. Another time, I was going down on him and massaging the patch of skin before his anus, he was really in to it and said “I know you want to do it, just go ahead”. So I lubed up and fingered his ass and he asked for more. The next night I fucked him with a dildo. He liked it for a little bit. I really want to bend the boy over and take him with a strap on until he blows. I’m so hot thinking about it and I’m hoping he opens up to it. Wish me luck.

  26. bill Says:

    my grilfriend used a strapon on me yesterday: loved it. she went slow and i climaxed with no touching at all.

  27. John Says:

    Well looking at this page all you guys and girls sound very lucky !!!
    I have been an in the closet anal fan for years since I was 17 and I am now 25 years old with a slim build and told ” im not bad looking “I have a bag that I keep in the loft with all my toys that I have collected over the years, ranging from love eggs, anal beads, vibrating butt plugs, a 7″ dildo with suction cup for riding and the big boy an 18″ double ender for when I feeling ambitious. I’m not gay just enjoy anal play.

  28. Mike Says:

    Where are all these women who want to try this on a man? Why can’t I find one? Even adds on craigslist hasn’t gotten a reply….Just an exchange of power is how I see pegging, but it seems here is the only place where women admit to such a fantasy…

  29. Dreaming Says:

    I have hint to my husband for the lay few years but he always jokes it away. While having sex I have grabbed, spanked and rubbed my finger tips over the crack of his juicey butt but have went no farther, but I could tell that it turned him on. Although he had asked me to lick his a** I have never done it. I don’t know why but I have been thinking not do this lately hoping it will lead to something more in that area.

  30. sparks Says:

    man its great you all are open about this I was sure you were out there. I moved to this town 9 years ago and the 2nd girl i was with made me. after her i was afraid i would not find another, and i sure as hell was not attracted to guys, it didnt turn me gay. much to my suprize of the next three, two were into it already and the other was not only willing but always wanted to, only was too shy to ask. any of you women out there who want to know how to work your way in. i suggest this to you: start like someone else said on him with oral that moves back and lick like you like to be licked. if you are a bit squeenish try flavored lubes. then work in a finger in like you would like it in you and just take your time and dont get carried away at first. it wont be long and he will be asking you please! my wife of the past 2 1/2 years and i make love 7 days aweek sometimes 3 or 4 times a day. she makes love to me in my butt 2 to 6 times a week. she has major orgasims almost every time she dose me. i have them too with a helping hand from her or myself! it rocks!. One other thing she uses a feeldoe and a realdoe on me. these are strapless strapons that vibrate and she weilds them like she had one all her life. took a little pratice but in a verry short time she got it butt good. and guys there is another side of this… tit for tat…. sense she gets yours.. you get hers more….. all things are legal between a couple in bond of love cuz the two = 1 its a gift from above. that is the main thing that makes us soooo different frome the beast of the field an forest.

  31. reza Says:

    i love to do this . i shy to ask my girl friend :(

  32. jan Says:

    I would like to be taken by a woman wearing a strapon. But.. Here in South Africa you do not get woman like this

  33. Shannon Says:

    Wow, I stumbled on this over night just searching random things on the Internet and I really did not know this was important in so many mens lives, was such an insight and rather sweet all of you how you all have so my courage to say so thankyou x

  34. Liza Says:

    My boyfriend jimmy loves it! At first he was shy but now he chases me around are house with the butt plug screaming ‘again again’ haha. Next stop….the strap on! :-P

  35. Lizzi Says:

    My husband and I went camping for 4 days and asked for every night! So excited he wants to get a strap on now because he wants more than my fingers. We have a dildo but I think it’s a little too big for him at the moment. I’m so glad he’s finally opened up to this. Any girls who haven’t convinced their man you should keep trying, don’t be forceful, but hint at it, use a finger to massage the area between his scrotum and anus and and maybe toy his anus some with so penetration. Good luck and I hope your patience pays off as mine did.

  36. birdie Says:

    jan – there is definately one woman in sa who wants to

  37. chaser Says:

    birdie – not easy finding a willing lady in sa… atleast no luck for sofar, lol…..

  38. daais lekker Says:

    also sa male, which my wife would consider it, made jokes about it before, but thats how far it went…

  39. Jason Says:

    So I was a straight guy until my girlfriend used a strap on!! I’m 33 now, and tried this with my girlfriend for the first time 10 years ago. I have been in about 4 serious relationships since, with several partners in between. Very very surprisingly to me…every girl that I have been with for the most part is all about doing me with a strap on!! They have all loved it, and all wanted to take it to the next level. My current girlfriend does it very frequent, at least once a week now. We use realistic dongs and tight secure harnesses. And we’re now using about 9 inches and thick dongs. For her, the bigger the better. I have to admit, it really is the greatest orgasm I have had every time she does me. I am a very masculine man in the military. I say that because this strap on play has my girlfriend taking this fetish to a crazy whole other level. She now has men come over that we meet online. She is the boss when she straps it on…and I love it. She tells me what to do with the guys (go down on them) or when to watch her with the guys. Crazy thing is, it all stems from strap on play. The thought never crossed my mind or hers before! We both love it and wouldn’t change a thing. It’s just crazy what this fetish opens up in your life. I don’t kiss other men, have sex other men, or even think they are attractive, I just simply love c*ck now. Is it just us and our chemistry? Or are other girls like this and think this type of sex is hot? Do other women want this? I just find it strange that so many women are into strap on play?? So I’m wondering if other women also would want to bring other men into the relationship?? I would love to hear some thoughts from other women. Are we just fucked up!?! Lol, or Is this common?

  40. Secret Says:

    I’ve recently started getting turned on by the idea of pegging my boyfriend. I started talking to him about it about a week ago. He said hell no. So I asked him if I could lick his ass and he said maybe. Today during 69 (with him on top) I started to lick his ass and he responded well. So I lubed a finger and started rubbing the rim. I asked him if I could put it in and he didn’t answer for quite a while. So I just did it. It immediately got me about 50x hotter. He started fingering me and sucking my clit so much harder and faster and I came. Then we had sex. Afterwords I asked him what he thought about it. He acted all shy and like he didn’t want to talk about it. When he finally did say something he said he wasn’t really that into it. I know it turned him on though. Wish me luck trying to get him to do it again.

  41. abb Says:

    Hi,all came across the site by accident and had to tell you all about my experience,ive been married for 23 years and have been a xdresser a lot longer,im a lucky having such a understanding wife who lets me indulge in my passtime with her taking part as well,now ive experimented with men b4 i married but only for sex,no kissing though,so all through out married life we have used toys on each other,and i can tell you this that we have both enjoyed far better orgasms together by doing this,she likes nothing better than putting her dick on and giving me what for,we have always used quite hard rubber strap-ons,but just recently invested in two UR3 vac-u-lock one being 6″ the other a 8″ now the feeling of these new toys are amazing yes you might say 6″ is small but by god its thick and when that is put into me, im in heaven,it hits my prostate everytime and my god,the last time i climaxed so hard was in my teens but it happens everytime she does me,so now we have the 8″ ive used it on my own but im waiting for when we do a bit of role reversal for her to hit me with it,but soon (hopefully) we are going to have a 3 some with another man (hopefully a VWE) to do us both,and i can tell you this that i am not gay,do not have any feeling towards another man,i just want to be drilled by one,and the wife wants to hear me scream like a girl lol,so to all you blokes out there,let your wife/girlfriend stick there fingers up you bum,then bring in the toys,you will love it and the orgasams well try it you will find out,and it wont mean your gay and it wont turn you gay,and to all you ladies out there go on you know you want to :)

  42. James Says:

    This is a new adventure in my relationship with my girlfriend of three years. I have always felt that I wasn’t like average guys sexually…and until 23 I had never even brought up the topic of this with a woman…but one night things just sort of progressed, and we became much closer for it. We started with fingers, and eventually I realized there was just something in me craving to be fucked by my girl. I know for some, it’s a domination thing. Not for us. I enjoy sharing roles in the relationship, and she does equally. And as a guy, it takes quite a bit of comfort with a woman to let them anywhere near that area, and vice-versa, so I think experimenting and pushing these boundaries sexually has actually benefited our relationship as a whole. I am not afraid of letting her do anything to me anymore. It builds a strong sense of trust. I wouldnt endorse anything specific, to each their own, but dont be ashamed of your own sexual desires! We all deserve to know this type of pleasure.

  43. That_chick Says:

    My bf has such a nice butt. It’s nice and round and juicy. I love grabbing a handful of it and just playing with it. Now I actually have never even thought about sticking a finger in it. I’m just very curious to know, does any “nasty stuff” come out while you’re doing it? Or any foul smell? We have never performed anything anal yet so I’m just very curious and would like to hear from some experienced people what to expect and how to do it the right way. Also for the guys that say they love it but worry that people might think they’re gay, I totally get you! U
    I am a 100% straight girl but sometimes I too fantasize about doing something sexual with a body part on the same sex as me. In no way, shape or form would I ever be emotionally attracted to a female. However, I’ve even had dreams about what it’d be like to rub genitals with a female and I have felt super embarassed about it and even like a freak b/c I’ve been curious about it. I’ve never even mentioned that to my bf for fear that he might think I’m lesbian so I totally understand what you feel. Don’t feel ashamed about it. It’s definitely normal and heck it’s your sexual life so do whatever makes you happy :)

  44. Trish Says:

    @That_chick don’t be embarrassed. I’m bisexual. I didn’t start dating women until I was in my 30′s. Sex with a woman is a beautiful and wonderful thing!! And it would probably turn your man on to hear about your fantasies. He would only be a problem for him if he felt threatened and he thought you could form an emotional bond with another woman. People are more accepting of bisexuality in women than they are of men. So I agree with you, it may be difficult for a man to ask his girlfriend for anal sex. After reading these comments I’m thinking I would like to try wearing the strap on for once and and enjoying some anal play. It sounds powerful. But I think I would have a hard time finding a man willing to try it with me.

  45. jim Says:

    I’m looking for a new girl friend who is freaky like this. S Georgia anyone :)

  46. Orin Says:

    I wish my wife would fuck me in the butt with a strap on but she is too religious!

    Reverend!

  47. Tom Borton Says:

    In reference to Trish on August 12,2012, I had it done once to me and I fully enjoyed it! As my luck would turn out, it was the last time I had it. If you would like to try it with me, I’d be more than willing!

  48. That_chick Says:

    Thanks Trish! I’m glad to know I’m not a freak for having those fantasies and maybe I will tell my bf about it. Who knows maybe he’ll even get turned on about the idea and would like to see me in action lol
    @Orin maybe you should surprise her someday with a dildo and ask if she’ll do the honor of bringing you pleasure. I know when my man asks me to do something I thought I wouldn’t like I end loving it just b/c I love hearing his light moans and knowing I’m the one that’s pleasing him.

  49. L Renee Says:

    My bf asked me to finger him and use a strap, I thought something was fqkn wrong with him, but after thinking about it and searching I stumbled upon this article and it amazes me how many men with to be taken by their gf/wife. But I seen that it’s a trust commintment that he has for me, I am so ready to make him my B****, and all the options of sex toys got my horomones flipping out ..I am going to fqk gis brains out ( Lol)

  50. jay Says:

    A couple years ago my wife wanted to do me with a strap on. I was open to the idea and while doing it for the first time I felt closer to her than any other woman I had been with in the past it was an amazingly close feeling and I am not an emotional guy but it was a very close emotional feeling. It felt so good and I regularly ask her to do me with it now. I am so glad we tried it and I love anal but only with my wife and her strap on that is. I can’t imagine sex without having my ass penetrated by her :)


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