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.
Autoandrophilia:
“Clair talked about her own sexual fantasies of sometimes wanting to play out the role of being a man in bed. She enjoyed having sex as a woman with men but also particularly enjoyed living out her sexual fantasy of being male with a penis. She particularly enjoyed the fantasy of raping someone else. This was generally… played out with female sex workers who would be accommodating and compliant with the fantasy to her satisfaction.
Clair was quite clear that although she might run these fantasies in her mind they were just sexual fantasies. She had never wanted to become a man in any way whatsoever outside of the specific living out of the sexual fantasy. She was a very feminine woman, well coiffed and manicured and very proud of her female body. Any idea of ever becoming a man in life was completely ludicrous and laughable to her and she made it quite plain that she was all woman, apart from her sexual fantasy of raping as a man.”
Someoneeeeee HELP IDK WHAT TO DO.
ANY SUGGESTIONS PLEASE LET ME KNOW.
I like my boyfriends ass sooooo much and hes not for it at all. He lets my play outside but inside he gets way to uncomfortable and just isnt for it. I like neeed to go in atleast with a finger. HELP PLZ
Had a woman do me with a strap on a few years ago and had the best orgasm of my life.
I’d love for my wife to do it, but when I ask her to do it, she replies with a “you really want me to do THAT?” and I end up feeling odd and dropping the subject.
Any ladies around Boston interested.
I’ve always had an interest in this happening to my but have never found the right woman.
hey, im a 20 year old guy and ive just started using a butt plug but have explored the area before, im trying to tempt my girlfriend into strapons etc but shes having NONE of it!!! ive explained its normal and even shown her some forums like this but all i get is “its not in my comfort zone” which is fine but if she could at least try it once!!!
OMG! I REALLY want to do my husband with a strap-on! But he has already warned me to never go near his ass! How can I convince him to at least TRY! Not saying to start off with a strap-on, but maybe a finger! When I give him head I like to lick and suck on his balls but he gets all wiggly if I get to “low”! Help, I just want to try but have no idea how!?!
I really have been wanting my girl to do this it is my ultimate fantasy, but she says she is uncorfortable with the idea i use to talk dirty to her about doin this roleplay but not so much anymore even thoughi think about it all the time wish their was a girl out there that could fullfill my fantasy heres being hopeful.
I would let my wife use a strap-on on me. She has already fingered me in the butt while we are in a 69 and I am eating her out. I really enjoy the finger and think I wouldn’t mind a strap-on at all.
wife as a joke dressed me too… OMG outta this world!! 🙂
OMGgggg im 18 and my bf is 18 and i LOVE his butt lol idk what it is but i always play with it and he lets me play because he knows i love it but he doesnt let me go in he thinks to much…what should i do!
One day I was at home and doing some things. I came up in the bed room and see a strap on in my wife night stand. I can not think about what she want me to do. She came home and I ask her about the sexy strap on. My wife say to me was one day see want me to do anal sex on me and I say to her o yes I love to do it with you and so my wife want to her bed room and put the strap on on and get sexy up for me. Then she call me to the bed room and I want in and You grils and guys can think about what we did in the bed room.
So how can I get my wife to go for it…Have tried several times to get her to perform anal intercourse…Maybe time to new playmate?
Im a teenager, and me and my boyfriend are just beginiing to experiment with anal play. it is a bit messy at times, if you finger as far as his prostate (poop on the condom) so I’d say you might want to get a douche. its a little thing that squirts water to clean the insides for cleaner play. if he has a hairy ass ( my boyfriend does)then you need to get him to wipe incase he isnt so clean there, sometimes they cant help it if there hairy. My boyfriend likes it when I ever so gently play with his bum hole when were having sex, it really gets him going when I do that. at first, just try playing with his bum through his boxers, then progress to a condom on the fingers with a little lube (or latex gloves) and play with it whilst giving him head. then when your comfortable with that try one ort two fingers and massage his prostate, the moans reeeaally turn me on and it makes me feel in control. only after your this far do I suggest you try toys and strap ons. Were not that far yet, but anal play is ALWAYS in statges and you cant rush it. good luck 😉
Hi Boston jock going to college in Boston here. I am frightened to death if i ask a girl to finger me or do me with a strapon everyone will think i am gay. Where do i find these awesome girls?
After telling my boyfriend about the idea of sticking a finger in his ass for about the first three months of us dating here and there by the fourth month i was in the kitchen and he was sitting across from me he has basketball shorts on and my feet were feeling on his dick all the way down to his ass..later that day he said that felt good and asked me to lick and finger his ass…honsestly it was a little akward when i did it but i love fingering his ass actually i was able to stick two fingers in his ass last week…..i would love to put on a strap on and just fuck him