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.
s
i’ll start off saying that i am a man, and i have had a few experiences. I’ll never forget the first time a friend of mine I slept with slipped her finger in my ass, we went from her finger to some beads to her trying to put a dildo she had but it was way to big. She then put the idea of a strap on in my head but we stopped fooling around before we could act because i found a steady girl to date. after moving in with her i found a strap on in the closet and i started thinking how great it would be if she wanted to use it on me. After a couple weeks i finally said something and she said that it was a gag gift someone got her at a party then one day she had a much smaller and curved one to hit my prostate it was only about 5 inches long and pretty thin she would fuck me so hard with that little thing but it always left me wanting more but we broke up before she wanted to get a bigger one and the one i found was way to big for me. after i broke up with her i had an older sugar moma and she would always tell me how nice my ass is and how she never liked a guys ass so much and then she asked if she bought a strap on if she could bend me over and wow i can’t even begin to explain how happy i was it had been such a long time and a couple g/f’s later since my ex used to fuck me. we went to the sex toy store and she had me pick one out i picked out the thin 7 inch one and we went home and tried it out she warmed me up with a blow job and a thin vibrator and then put it on and had me on my belly and it felt like she was really going to town on me but she said that she wasn’t going that hard or fast so i was amazed. I had to cut that off because she ended up messing with a bunch of other people and i wasn’t going to risk getting an STD. Then i meet another girl and she was really dominant and i kind of hinted things to her and one day i was on my hands and knees trying to plug something in behind the bed and she grabbed me by the hips and started “dry humping me” if you will. I got so hard feeling her slam her pelvis into my ass and i couldn’t hide it. she said she just wanted to see how it felt to be me and then saw my erection and said wow you really liked that hugh? and then came the anal play she got so into playing with my ass she used to tie me up face down and put toys in me and then finally one day she got a strap on and tried to fuck me but the one she got was to long and hurt so she had to hold her hand around the base and couldn’t pound me like she did when she wasn’t wearing one. She ended up leaving to finish her masters out of state and i havn’t had any since. I am trying to get my current girl into it but she has barely licked or fingered my ass. she has never experimented before and i got her into being tied up choking me and tying me up. I’m still trying to figure out how i’m gona get her to fuck me with a strap on but i’ll figure it out. any women out there have any advice on how to get her into it?
Me and my fella were talking about dildos and butt plugs the other day. then he mentioned getting a strap on. I said “you really want one?” and he replied saying yes, then you would have some control. I think we maybe getting a strap on soon!
well i wish my gf wud strap up more often! I love feeling her in control and inside me for a change.
Sometimes it can be sore, but then we just do something else and put the toy away for another time!
Im a fella and the wife and i do this. I must admit i felt a bit ‘gay’ at first but after a while them feelings stopped. My wife says she really enjoys doing it coz it makes her feel in control, and i love the feeling, theres no way to really describe it! We started off with a finger at first, leading to me trying her dildos, then eventually i bought her a strap on. We dont do it that often, maybe once a month but when we do its fantastic!!!
Most guys who are comfortable with their sexuality want to explore new experiences and, although at first, may feel a bit awkward doing this, will soon end up loving it!
Next time your down there giving him a blowjob start rubbing his balls and gradually get lower and lower to the ass entrance. if by the time your gentally rubbing his there he doesnt complain just very slowly and softly ease it in, he will love it, just give it a go!
Not weird at all, in fact im jealous. If my man only knew how much i want it and dream of it all the time.
Im so glad there are other people out there that have done this. This is a totally new experience for me. Last night me and my boyfriend got a bit adventurous, we got in the 69 position and he was licking me out while i was licking his balls and penis. I then started playing with him back entrance. He seemed to really like it. So i decided to get some lube out and stick a finger in and he loved this. So I carried on and then decided to get my vibrator. All of a suden he got on all fours and asked me to put the vibrator in him. I was abit dubious of doing this all the way, but he absolutley loved it. I then began to enjoy doing it to him. I never in my wildest of dreams thought i would ever do this to my boyfriend. But it was amazing. He moved to the spooning position then on his back, wow I have never seen a guy have such an orgasm. It really turned me on. He then did the same to me but not as much as it was my first time. He then confinded in me and admitted hes done it to himself before, but has always wanted a girl to put a dildo in him. After reading all of your messages, I now want to try a strap on.Thanks all for putting my mind at ease. I though it was really wierd for a guy to do this, but its obviously not. Thanks
Caitlin,
you sound more homophobic than men,If he trusts you.To do what he does to you.Provided your anal.What is wrong with role play ?
evangeline.
beg him to ass fuck you.opening the door to role play
Again..Ying And Yang..can be so much fun to role play with regular partners
Holly,
sorry b/f is so prudish
My girl talked me into it to and I love it. I have bin doing it for years and to this day never wanted to be with a guy. Not that I have any problems with bi or gay people but its just not my thing. One thing I have to say is the feeling of it is out of this world and I will never stop.
Ok, I secretly want to do my husband in the ass, but I know he will be totally against it. It’s a dark fantasy of mine as we have talked about it in the past and he has had a finger up there but nothing more. How do I get him to open up to it? I LOVE anal, and would love to do him but don’t want to wierd him out about it. any suggestions?
Good to be back on this site. ( 1 yr ago was the last time i was on here) but i cant help but get so turned on with some of these stories. But here i am 1 yr later and i still cant get my boyfriend to let me f— him in that tight a$$ of his. Just looking at his juicy a$$ makes me want to run and take a bite of it. Its so beautiful i wish i knew how i could get him to open up and let me in;)
my wife used to do me back there and i loved it and still do but as we got older she doesn’t like doing it anymore and i still want her to do me. whats a guy to do? cheat? do it to myself i just want it done.