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.
I think it’s best for us just to ignore James. He’s probably some flavor of religious conservative, as evidenced by his early mention of a married couple(which contradicted his viewpoint). And he probably wandered in here and is trying to spread his idea of morality. But scientific thinking clearly is not his forte. Not once in his bizarre analogy of the soldier did he mention PTSD. Frankly, his posts read like a trailer for “Reefer Madness”. Ooooooh fellas, don’t discover the forbidden, devilish pleasure which is anal play! Even if it doesn’t turn you gay, you’ll morph into a homo-erotic fiend with no self-control!! Puh-lease. James, you’d be a better fit in a Creation Science blog. If we ignore him, maybe he’ll just go away. I’ve said my piece, and now that’s what I’m going to do.
Elizabeth.
About men lusting, I am a man, and all men that look at a woman they like lust. It would be very boorish for a guy to show an erection and act in a rude manner, but men and women know how to act “subtly” and the message is delivered clearly.
A man that is straight, and is playing with cross dressing for his GF or in private to “feel” the clothes on his skin will not find this subtle messages alluring, unless, off course, we were talking about a real homosexual man.
You say you would be offended at a guy that would show a boner at you, I understand. That is not what I mean, the sbutle messages played between men and women tell one and the other the state of arrousal he/she is in w/o resorting to vulgarity. Yet, these messages are clear.
Only Colline and her boy friend can respond to the questions I submitted, so please let people speak for themselves.
About the gay issue you are submitting, I said clearly we do not know if the person is gay or not, but what you do not seem to want to understand is that the risk in this practice is all on the side of the man. The woman has nothing but a new experience to enjoy . The guy is the one that will have to deal with the issues, hence my call for caution.
About women and strap ons in real life, again, I am on the side of preventing catastrophies, unlike what you seem to go for, which is to throw people off a cliff for your amusement. You want to make men believe there are a lot of women practicing this strap on over men deal. That is not true at all. Go to any regular dating site and post something like that, I am a guy looking for a woman to use a strap on with me. Or go to a party and openly disclose to others that you want a woman to use a strap on over you.
Most women would think the guy is feminine at least, or has homosexual tendencies. I am not sayiong this to mean that all men that are submitted to strap on sex are gay, not at all, but what I mean to say is that it will be very, very difficult to find a woman that will be a GF and a strap on partner as well. There are plenty of dominatrixes and sex for money girls out there that would do it, but it will be very difficult for that guy to be able to satisfy his newly acquired desire.
About my comments on Collines relationship, I am a human being and before trying to throw people off a cliff for entertainment, I try to safe people from committing a mistake that can ruin their lives. It is good advise to try to instill caution and to make people think about the consecuences of their acts before they engage in those practices, something it apears you think is un necessary. You seem to think that a guy going from cross dressing in the privacy of his home, progressing to doing it outdoors , putting at risk so many things in his life, warrants no caution whatsoever.
We are talking about human beings, we are not dealing with pets here.
Nikki – use lots and lots and lots of lube. Too much is nearly enough. We use a lube that is made specifically for anal play. Have him shower first and make sure he’s got enough fiber in his diet… unless you don’t mind rather uh… awkward moments. Sometimes it is easier to start with fingers, rather than just jumping to dildos, but that’s up to you guys. Some guys do orgasm without a hardon (or so I hear), but mine prefers hand stimulation with it… Ask your guy what he prefers. My guy and I have never had any angle issues, but if it’s uncomfortable for your guy in a certain position or something – he should let you know during the act. And while I have no idea what it actually feels like, I doubt he’s going to never want to have “regular” sex again… or even less often. My guy says it’s awesome, but sex in general is awesome. It’s just a different trick.
James, darling, in case you missed it, earlier today we mustered up the strength to argue back. You can check it out here:
https://www.emandlo.com/2009/07/strap-on-sex-wont-turn-you-gay-if-you-arent-already/
James – so, are all women sexual lust objects for men, then? Because that’s exactly what it sounds like you’re saying. See, I’m a woman, and if some random guy got a boner because he saw me in some normal dress in a mall and acted like it was okay – I would be upset and offended. Because I am a woman, a person, NOT some walking, breathing sex toy, regardless of what I’m wearing.
You know what else offends me? The sexist, homophobic garbage you are spewing. People don’t “catch” gay, and people don’t “turn” gay. They are gay, or they aren’t gay. And realizing that certain nerve endings feel good when they are stimulated isn’t going to make some sudden attraction to other men occur.
Also – do single guys sit around talking about how they miss specific sexual acts with each other? Because, see, I’ve seen/heard the “Dude, I just wanna get laid” conversations… and they usually don’t have random “Man, I really miss having a girlfriend because none of these one nighters will (do reverse cowgirl/tie me up/have anal sex with me/whatever his favorite act is)” Most of the guys I know don’t actually discuss what kind of sex they like with each other – regardless of what kind of sex it is. With the possible exception of BJs.
As I said on Emandlo’s refutation – It is not nearly as rare as you assume to find a woman who enjoys strap on play. I’m talking in real life, not online. Stop making dumba**, sexist assumptions about women that you are in no way qualified to make. I’m actually pretty sure quite a few women I know would relish the opportunity to be on the other side of the equation for once. But because of men like YOU who perpetuate this unintelligent idea that there is something homosexual about ass play – they are too worried of what their men would think to bring it up. So if a guy gets addicted or something – hell, I’ll tell him a few names of women who would love to give it a go.
And finally – Stop trying to advise that poor woman Colline. Unless you have various degrees in psychology and counseling – you are in no way qualified to decide whether he is secretly gay, or if he just wants to play dress up. And if he does just want to play dress up – you are again, in no way, qualified to decide whether or not this is good for his psyche or their relationship. If Colline is worried as to what this means for her relationship she should be advised to talk to HIM about it, rather than just cutting off something that her man enjoys without a discussion.
Colline.
I think you are playing with fire here. With all due respect, I think there are 2 posibilities:
1) Your husband is secretly gay.
2) Your husband is not gay but is feminine at least.
If he is gay, you will find out soon. If he is not, just cross dressing, I wonder what happens in his mind, and in your mind, when you both get confronted by a horny guy that finds himself turned on by your husband and gets a boner while looking at him.
Will your husband blush?, will he like the advances? will he like the fact that he makes men horny? Or would he get upset and offended?
About you, will you enjoy looking at men getting horny at your husband dressed as a girl? Would yopu enjoy looking at your husband being treated as a girl by these men?
Would you accept and enjoy looking at your husband acting feminine while becoming the object of sexual desires by men?
Like I said before, if he is gay, he will do this with you or alone. If he is not, you are not helping him in supporting him in this adventure.
One thing is a man that says he enjoys the feel of feminine cloths on his skin, but it is another to go in public, and become the sexual object and the lust of men.
Are you ready to see that in front of you?
I couldn’t disagree with either James or Emandlo, and to Nicki – I would not penetrate his back hole in case of scratching and hygiene issues and my husband thinks it going too far, so I stick to simple finger massaging which I’m sure most men would enjoy without feeling feminised. I do think there is too much stigma attached to all of us about being different. We are still evolving as creatures, for instance, why are men compelled to wear shirts and ties and trousers to be ‘Normal’, and men wearing skirts shunned as crazy. It all seems a bit ridiculous when a woman can wear a shirt and slacks without any stigma. We have discussed this in far more depth than this and we think that there may be a predisposition for my husband to cross dress, but you get the picture of what we are going through, but we are happily married and he says he wont jeopardise that if I get afraid he will stop.
I offered to see if he really does have an issue and we went to the City early Saturday to a ‘Makeover Salon’ and we spent the whole day with my Husband dressed as a woman. I must say it was weird to see my husband turned out as a woman, especially one as sweet natured and attractive, but I still love him and after a nervous walk around the park we found a quiet restaurant and I gradually got used to this soft spoken new, “Will you call me Sandra just for today,” ‘creature’. “It feels great in a dress sweetheart,” he told me, “But I feel so scared that people will see me as a stupid guy looking ridiculous in drag. Should we just go home?”
I had to tell him he looked real good and not to worry as no one had stared at all. We decided to spend the rest of the afternoon at the movies just to relax for a while well away from the crowds and maybe do some shopping later, as we planned earlier. Since we had come this far. Sandra felt better after the crowd free afternoon movie, and afterwards we had a great time shopping, trying on different outfits. Yes we decided to buy some ‘Naughty nightie stuff garters and all, just as planned. I had a great time having someone so close to share something I love doing, and in a mad moment said, “Lets have a pedicure,” which he loved having for the first time. The little Philippine girl gave Sandra the full treatment pink fingernails, toenails, massage and all, while I was nearby enjoying a pedicure. I was shocked to find she had her ears pierced while she was at it and she giggled about having an ‘Orgasm’ during her calf and foot massage. We had to go to buy some fresh cotton panties and change in the washrooms in the Mall. We used the train and taxi to go home, and although Sandra was a new person to me I must say I felt traumatised but excited by the whole thing. I’m not sure I could do it again but I believe my husband satisfied his curiosity and we both enjoyed having some adventure in out lives.
I am glad I found a discussion for this topic. My boyfriend and me are very close and have been thinking about exploring new things in our sex life (which is already very good). I have been warming up to the idea of perhaps using a strap-on with him, because he is eager to have the p-spot stimulated during sex. My main concern is: is there anything I need to know before I actually do this? I plan on maybe buying a small dildo and some lube, but I am not sure if I’ll be doing him the right way. Should I expect him to orgasm differently (without a hard-on)? Should I avoid certain angles? Is it so wonderful that, if we only do it once in a while, he’ll prefer it to regular sex? Any tips from the ladies who do this or the guys who enjoy it would be great.
You all need to check out the “Strap less- Strap on”. It’s called “Share”, and you can find it at Vibrator warehouse.com. This thing is built for two. First it goes in her, then she puts it in you. AMAZING!!!
My girlfriend LOVES having anal sex w/ me. She can’t wait to put her face in my bum and use her toung. Then brings out her strap on and gives it to me in multiple positions. Sometimes I climb on top and ride her like she does me… Her favorite is to lay me back on the edge of the bed w/ a pillow under my rear (for better positioning) hook my thighs and pound me till she climaxes. We both get our it’s fantastic. We have the most amazing sex life!
Ladies… just do it! Guy’s… let them!
Last month, my wife bought a strapon. When she said me i became a bit angry. But didnt show my feelings. I told her about my feelings and thoughts. I said that is not for me. All men are not same. Some like some not. I told that ‘I dont wanna strapon. I dont wanna anus play too. It hurts my honor who is a woman playing with my anus. I’ve respected you for 2 years. So I want your respect . It comes me weird. Yes I have sex with your anus but thats not same.’
Sorry James, it’s a beautiful Friday afternoon and we just can’t be bothered to argue back. All we will say is that nerve endings aren’t straight or gay; people are. And that’s our final answer.
No Emandlo, not at all.
I bring back the example about the nice young man that signs into the army to cost his university education.
Not all, but many soldiers get affected negatively by war scenes and experiences.
A nice young man that has never used a gun and is a city dweller , after seasons of weapons traning and actual combat, this guy will get the experience of killing another human being.
He will desentitize his mind from what means to kill and use weapons.
When he comes home, ( some off course, not all of them ) he might use that experience, (or his mind will drive him in that direction), to get involved in crime. This is what I mean by taking a path that was not within your options prior to a life changing event.
Had he not gone to war, he might had stayed clear and oblivious to crime and all its consequences.
Now, unlike your statement, this does not mean that the soldier and all soldiers, and all men as a human race are secret criminals. It takes other things into account, and not necesarily genetic issues. You might not be genetically predisposed to become a criminal, but the stress and the trauma of being in that situation might make you weaker and easy prey to fall in a life of crime, not because of being an innate criminal, but because of being confused, weak and mind disturbed.
Once you kill one man on the streets, once you organize and materialize a hold up, you are a criminal, there is no way back.
With the strap on issue, I see parallel issues. Not all men will go all the way to become gay men. I do not think so, but in the same way a couple years in war zone can change you and lead you to a life of crime given the right conditions ( mental trauma, confusion, stress, financial stress…added to the weapons training and toughness of mind instilled at the army ), a man that begins playing with strap ons, and as in the case of Collin’s boy friend, playfull cross dressing, that man might end up moving up the ladder of the unconventional.
I am not saying that a straight man that gets done w a strap on will become gay ( unless he is really gay, closeted homosexual or a feminine guy learning he likes that ) … what I mean is that that man, once alone, w/o the GF that used to bend him over, that man will still crave being penetrated.
Who is this man going to talk about his deisre to be penetrated? to his straight friends?, I do not think so. To his female friends? unless these are strap on girls, usually girls do not find this attractive nor the thought ot bending over the man they think of as a real man is found to be alluring.
So it will take time and effort to find another woman like that. This is were I think the forking of roads happens. Will he talk to hiomosexual guys about the issue, not because he is homosexual, but because they have an issue in common?
Will he some day allow a man to penetrate him under the premisse that if that happens, he still would not consider himself homosexual, because he does not like men, all that man is doing is penetrating the other guy, it could be a strap on.
All I can see is that a straight man playing with strap ons is playing with fire, with his life, he might end up at a place he never intended nor wanted to take.
You want to take that risk? do it. All I am saying is that it is a ride with no return. It is a step ride. Once you are used to being penetrated, you will never go back from that. Desensitization opens options that once before were considered imposible.
The guy in question might not become gay because he was a secret gay man, he might become gay because he needed to satisfy a need ( penetration ) that in a distant past begun as a risky experiment with a girl that once asked him to bend over ( or perhaps he asked her, it was his deisre to try it.)
That is my message, think before you take that boat, you might not like where it will lead you upon.
So what you’re saying, James, is that every man is secretly gay inside and it’s only the “defense mechanisms” of consistent homophobia and vigilant narrow-mindedness that keep him straight? We finally understand why this country is so full of bigots!
I think you lost your boyfriend at some point, but gained a new girlfriend.
This is what I mean by playing with fire. Someone said that you can not “catch” a gay virus. I agree, but in the same way a normal citizen could end up becoming a criminal after a few years in a war zone, becoming de sentitized to guns, killing, shooting humans, by the same way a guy can become de sentitized by playing cross dressing or getting submitted with a strap on. Once the defense mechanisms are gone, the person is open to several other roads that previously were not part of his road map.
We met a year ago, he is a couple of inches smaller in our bare feet. He wears a pony tail which he shakes out when we’re at home allone. He was very sexy from the start and we both love kissing. Then my boyfriend of 5mnths started rolling over still keeping penetration, so that I was on top between his legs and fucking him with his legs apart, so I became the dominant partner for weeks. Then he told me no one had ever done that before and how much he loved being on the bottom. He said he wanted to find out what it was like for a girl wearing a nightie and having her panties taken down and I agreed to try it by swapping clothes. He loved it and always likes to go to bed dressed as a woman with me dressed in pajamas. I wouldn’t mind doing this occasionally but now he has shaved all his body hair off and started using make up to bed. He has now suggested both of us try wearing see through nighties, with fancy nylons, a garter belt and high heels, around the house before going to bed. Although I think it could be fun I’m getting a bit worried about feminising him. He has never mentioned ‘Strap ons’ but he does use a syringe thing with water and olive oil to clean his bottom out before bed and likes being fingered and kissed after I take his panties down. has anyone experienced this and where do you think it will end.