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.
My girlfriend is and has always been strongly against anthing anal. No matter any subtle hints or serious conversations about it, she always says no. Not only do I want to do her in the back, but I also wouldnt mind her doing me in the back every now and then with a strap-on. Any suggestions or ways anyone thinks I could get her just to try it??
okay, now i just think you’re an idiot.
you actually ranted about being sick of your boyfriend always wanting to come on your face, always asking about threesomes, how tiresome it all becomes…
Only to harass your boyfriend into ass fucking him?
Now who’s the object?
No kidding you only want things on ‘your terms’.
I bet you still bitch when he wants to blow his load on your face you hypocritical douche.
Where can i find a girl that wants to play like this?
feels great and i want more 😉
Joe, Cheshire UK
I wish more girls were into strapons. Can all you girls who are into it, tell your girlfriends how fun it is and convince them that it is OK to do to their husbands. To many women are afraid their man is gay, when ITS GOT NOTHING TO DO WITH THAT! It has everything to do with the incredible sensation of having our g-spot rubbed just right and exploding. I found out with my ex-gf that I actually love the sensation of her behind me. It is amazing. But I am a bit to embarrassed to be able to bring that up again with a new gf, because I know she wouldn’t be into it.
Dear James, you say:- 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.
Colline:-“We don’t dress sexy or to attract attention, but it could be flattering for ’Sandra’s’ ego to feel reassured that she is attractively ’Passable’ dressed en-femme especially by a ’Wolf whistle’, etc.”
J.Will your husband blush?,
C.“Yes, Sandra does.”
J.will he like advances?
C.“Yes and no, it is flattering to know you’re attractive but it is potentially dangerous and makes Sandra very nervous and unsure.”
J.will he like the fact that he makes men horny?
C.’Like‘. “Not really, flattering and amusing maybe. You must understand we do not dress provocatively.”
J.Or would he get upset and offended?
C.“Amused, and definitely entertained if the approach was passive. Offended and afraid, only if too confronted, especially aggressively or persistently. This has not and will not happen.”
J.About you, will you enjoy looking at men getting horny at your husband dressed as a girl?
C.“Do men really get that horny just looking at women? Again you try to push our buttons by your somewhat extreme sexism. To try to answer you. Only if I could stop laughing at something so absurd. If they became serious I might be afraid or even angry or jealous. I assure you this is not going to happen.”
J.Would you enjoy looking at your husband being treated as a girl by these men?
C.“I would be pleased to see Sandra enjoy herself as a ‘Woman’ as long as she does not lead men on, or try to start a relationship, but I feel sure that he, as/she would never be so stupid.”
J.Would you accept and enjoy looking at your husband acting feminine while becoming the object of sexual desires by men?
C.“Yes, I would accept and be relieved and pleased to see Sandra so well accepted, but this is potentially very dangerous ground, so we do not seek male company – This is where you don’t seem to comprehend the lines are currently drawn, and so obviously must be for safety reasons. If Sandra ever desired a man sexually, he- the man you are so determined to bring into your equation, would have to be fully aware of her male ‘Attributes‘, and comfortable in accepting her limitations. Again we do not seek to be sexual, in any case, I do not believe my husband would ever use anal sex as we would both be afraid of hygiene issues, of doing serious internal damage and of incredibly serious internal infections occurring.”
J.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.
C.“Not helping! I must disagree, I now firmly believe that all men need some escape from this extinct ‘Macho’ stance, born from prehistoric times when men had to fight each other for woman. Men have buried their emotional side at puberty. Men are clearly the same soft ‘Pink Bipeds’ as women but most men have evolved into either ‘Red Necks’, or those so often business suited, or other uniform robots, incapable of crying, hugging each other, or being genuinely comforting or sympathetic, which is alien to our evolution as intelligent beings. We think the current uniformed, ‘Macho Male’ will be dead and gone, in a few hundred years, and we‘ll all either be wearing a practical ‘Thobe and Gutra‘ type of dress code just like the Saudi‘ Princes, or all be wearing ‘whatever we like’ to express our personalities regardless of sexual orientations. I think, I hope, the latter……”
J.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.
J.Are you ready to see that in front of you?
C.“Again you try to make a point by creating a highly sexual question, but dressed as Sandra, she would not wish to attract attention and would never be dressed so aggressively sexual, as a ‘Tart’ etc. Sandra’s – our focus is on smart casual clothing, to blend in with normal women out on a shopping expedition, and never in an overtly sexual manner. For example handbags are extremely useful but not the least sexy. I wonder why you don’t see any men brave enough to carry one! Why do you suppose you are so afraid of being so easily seen as ‘Femme’, are you all cowards or what? Why does it take such a lot of courage for a man to carry something so useful as a handbag – never mind being seen in a store looking for suitable and also highly practical women’s tights and underwear, but to get off my soap box and try to answer your question.
I think Sandra is amazingly attractive dressed as a young woman, I have caught men looking, it is part of being a woman and also I find her desirable and sexy. So to your question. Messing around, or ‘Flirting’ with an attractive male is a fantasy of many women and I must accept it could well be a thrill for Sandra to show some leg and tease someone in a safe setting, but it must be someone safe, or otherwise friendly and certainly not someone unknown ‘Macho’male from a bar or other public ‘Pick-up’, which would be unacceptably dangerous for any intelligent women never mind a newbie cross dresser. Don’t you agree?
Surely you can now see how invalid some of your arguments are! Although to try to be fair to your arguments, if cross dressing is the only way a homosexual guy can ‘Come on’ to another guy that would have to be a cross dresser who could submit to oral or anal sex which while acceptable between homo males, would surely be far too much of a shock to most flirting males who expecting a woman, only to find something other than a woman’s equipment tucked away, could create a very nasty incident. This must be why homo men wishing to attract men do not pass themselves off as women. So cross dressing as a woman for the sexual purposes you suppose is not the valid argument you suggest. Probably more common are two cross dressers getting together for fun and games, but my husband seems very happy with me so far and I hope for a long time ahead.
Thank you for your letters James. Anything you can tell me about men’s desires in this arena would be well accepted and well read. I thank you for your ideas which have provoked much thought and have been helpful in spite of disagreements. I wondered if all men were dressed more feminine, and became much more sensitive in bed would the lesbian population diminish? My husband is not the same man while cross dressed. He becomes more like me. Sensitive, extrovert, giggly, emotional, focussed on peoples feelings, more caring, and so much more fun to go shopping with, which as every woman knows is far more important than the sex that James sees as key to everything. We are spending some time on Sandra’s voice and mannerisms and we are hopeful this is improving. She slips into her role so easily but her conversation seems a little too soft to me, so at the moment I do all the talking while we are out together. No one else seems to notice anything odd but it is strange for me to hear her soft gentle voice, I find strangely off kilter..….Sandra wants a tape recorder but a friend says don’t it as it will make him too self-conscious…..end – for now….
Holy shit.
Reading this, I realised I was in an INCREDIBLY similar situation.
I’ve always wanted to perform anal actions on my boyfriend, but he’s always said the EXACT same things yours has.
I finally convinced him in a similar way, but we haven’t yet.
Haha, I hope it turns out like the end of yours.
My wife is 6’2″ 190 lbs. strong, athletic and a farm girl, I on the other hand am 5’9″ 165 lbs. and from the city. My wife took me over her knee on our honeymoon for my first bare bottomed spanking and have received many, many more. On my 50th b’day she spanked me. On her 50th she spanked me then bent me over and rode me to our mutual satisfaction. Usually when she is in one of her moods she will lay me on my back on our bed, enter me and cream me till I lose control the whole time she tells me if I’m not a good little boy and do what she says she will turn me over her knee out in the backyard so all of the neighbors can see for themselves who wears the pants (and who doesn’t) in our house.
What a lucky fella — I would love my wife ( or some other lady) to take me with a strao-on — It is my fantasy
What a lucky fella you man is — I would loved my wife to give me a good rogering with a Strap-On — or some other lady for that matter — I fantasise about it often
Colline – I fully believe that you should participate as long as you feel comfortable. And like I said, my advice is not to randomly put the brakes on this activity with your husband, like some others on here – because it would likely cause him to feel alienated and ashamed. From your comments, I seriously doubt, even in discomfort, that you would like for your husband to feel that way. I know that my guy and I keep an open communication about sex, including things which may make either of us feel uncomfortable. My guy is submissive – rather than feminine (which, btw, is not the same thing) – but there are some acts that he enjoys that make me uncomfortable. Because he loves me, and he is a healthy person with healthy sexual expression, he can (and does) very easily decide that he can forego those particular pleasures for my comfort. While I have never met your husband, I seriously doubt he wants to go so far as to make you uncomfortable. So, when you get to a point that you do not want to go any farther – let him know. And keep up a discussion as to how your adventures together make both of you feel.
Dear James, I accept my partner is a feminine man who enjoys cross dressing. If he does take feminizing further I will support him as long as he is faithful and respectful of my feelings. I accept I had a crush on a girl once so I am a little ‘Butch’ and part of me enjoys having a ‘Girlfriend’ to play with and enjoy shopping with. There is no doubt we have awakened a sleeping Trans Gender issue perhaps in us both. We only met a little over a year ago, are newly married and I was already aware of his cross dressing issue as my boyfriend – my first letter clearly shows. I love his gentleness and femme side and I have accepted now that he needs to release feminine feelings that have been bottled up for years in order to be content. I am sure he is not attracted to men. I do wonder if all men have been indoctrinated at a young age to strike a ‘Macho’ pose to avoid being ridiculed and picked on at school etc., and dressing femme releases them from that burden. My husband feels like a burden has been lifted when dressed/transformed as Sandra. The fact that men act Macho in the company of other men, always masking their emotions, suppressing any show of softness, never crying etc, and have evolved an almost uniform dress code, thus suppressing any femme attributes. This would suggest all men have a suppressed femme side, that is the truth of it. These hidden emotions are surely not healthy. I had hoped to discuss men’s hidden needs rather than labelling people or categorising people. We are all different to a degree but not so very different. I do worry if there is some brake I need to put on and say “I am uncomfortable, no more, we stop here”, but at what point would it be necessary. We are really enjoying what we are doing now, so tender and sensitive, like two lesbians when making love.
James – Look, I called you sexist because your statements were. You said that because that poster’s guy dressed up as a woman, he became a sexual object for the men that saw him. That statement has some pretty heavy implications – specifically, that women, in general, are sex objects, regardless of the situation they are in. I realize that you explain that you meant a man might desire her husband in a sexual way – which is different, I suppose, but… for me at least, if I am not in a situation where I am looking to attract a man, if some random guy starts subtly trying to convey that he wants to screw me – I’m going to be offended. You have absolutely no idea as to what this woman’s husband is wanting by cross dressing in public. I didn’t try to throw her off a cliff, because I said she needs to talk to HIM not YOU.
And people in general have called you homophobic because, sir, when you act like a man realizing his homosexual desires or deciding to experiment with other men is the end of his life. You know, like he was being thrown off a cliff. You act like if a man decides to experiment with his sexuality, he will never find a woman who loves him. People have called you homophobic because you mention that a married couple is fine in this situation because the wife will have to “live with what she has created”. Do YOU see the inflammatory language you are using there? The things you are saying make it sound like you believe homosexuality or bisexual desires, at least in men, are completely disgusting.
You are making generalising statements about women’s sexual desires that you cannot possibly know (well, I’m guessing you’re a man, I’ve never met a woman named James). And then, making generalizing statements about women who enjoy this type of sexual act. I’m sorry, but because I enjoy some SD play and the occassional strap on fun, I’m a prostitute? Yes, I know you did not say that in so many words, but by saying that “real” women never want to do this, that sounds like what you’re saying. The women on this site seem to be normal, well adjusted women. Not sex fiends who charge men to do them with a strap on. Oh – and related to that – um, post an ad on any “normal dating site” that claims you want ANY specific sex act, and you are probably not going to get many replies. That’s kind of a red flag that screams “he’ll do you and never call you again”.
And – to end on – I read every single response on this page in whole. Including yours. Heck, I even just went back and re-read them… and still have the same opinion of you. And yes, I fully see where you don’t label people… you just accuse them (me) of enjoying ruining people’s lives for my own personal entertainment. Yeah… That’s what I like to do… I’m just sadistic like that.
James-
Just because we disagree doesn’t mean we don’t understand.
That is funny Dave. I am non religious 100%. But that is ok, I did my part, I hope the ones that read my posts and want to take the advise will benefit from it.
Those that do not want to read any opinions that are not what they profess can ignore it.
I now all the jargon, anything that calls for caution is turned as anti gay, or anything that I say you want to make it look like I said a guy will turn gay.
I suggest you read my post not in part, but completely, and perhaps you need to read those posts several times, because the statements you are making are false, contrary to what I wrote, and seem reactive.
Religious, creationist, anti gay, homophobic, you and Elizabeth seem to like labeling those you do not agree with.
I am not going to go that route….not worth my time, I am here to help people, not to defend a point of view with labeling and miscrontruction of other’s postings.
You’re probably right Dave. I apologize to everyone else for losing my head. I was just more than a little offended at James’ positing that women, in general, are sexual objects for the pleasure of men and just went off. It really just encouraged more sexist, offensive remarks. Guess I should go back to pushing people off cliffs! 😉