That’s how we started and it has lead to pegging, love it now, wish we had started sooner
3 Likes
+1 for regret. This is something we recently tried, failed and is definitely a “never again” from both parties. Maybe we didn’t research it enough, picked the wrong toy, tried it when too drunk possibly, or need to invest in preparation who knows.
We watched some porn and it looked a doddle. Me (Mr) love the look of an empowering woman yielding a strap on and Mrs Hue was game with an evil glint in her eye. Love honey order placed. Quick giggle at the toy when it arrived and nothing more said. Come to the night and Mrs Hue looked stunning in her crotchless LH strap on knickers with the strapless strap on inserted, but it didn’t go to plan. Despite lube, It didn’t fit, it didn’t feel right and hurt so much I genuinely thought she had it in for me.
I have never tried anything up my bum, although I don’t mind a tickle and I think my anaotomy was largely the problem, I wash thoroughly and a finger is about as much as I’m ever fitting up there without investing considerable time that I don’t want to do. The toy in question seemed to stick to me when it did get in a bit and it didn’t offer pleasure for her despite the rabbit ears and g spot shaping. Eventually I tapped out after the second position change and ten minutes of hell.
Mrs Hue has stated never ever again, I feel ashamed and the toy haunts us both.
1 Like
That’s a shame but from your descriptions on your post I think you were very over ambitious. Strapless strap-ons are definitely not the easiest things to use and choosing pegging as your first anal penetration was brave bordering on foolhardy as I guess you now realise.
Anal penetration of any sort requires practice and a gentle progression from smaller objects to larger ones.
Hopefully with the passage of time you may try again but with a lot more practice and preparation.
4 Likes
I agree with @rockstar, it sounds like yous really went for it and were a little too eager and ambitious with your choice of toy. If you bought it from LH, don’t forget their refund policy. I used this with a harness, but it would work with the knickers depending on the size of the O ring, this one needs 1.25".
I commend the jumping right into it attitude that you both have. I think if you can laugh about it and see it as an experiment that went a wee bit wrong, you could maybe try again but much slower. Do you even enjoy anal? Have you experimented enough to know?
3 Likes
My partner is nonbinary but born with a penis and I’m trans masculine so it was a bit of a no brainer for us to try some pegging. They definitely have to be in the right mood for it as they are my dominant so it takes some persuading for them be the bottom 
it was more of a service thing for me than a power thing but above all was the gender euphoria it almost made me cry of happiness the first time which would have been embarrassing. I felt like I was finally in the right body. My partner also enjoyed it a lot more than I expected I don’t think I’ve ever seen them like that before even with plugs or beads. It was amazing for both of us and we’ve done it again a few times since. We used the BASICS strap on which we love but maybe we will progress onto something a bit more realistic in the future. 
2 Likes
it takes time and practice to stretch everything not a straight in there thing. we made that mistake (him to me) a few years ago and put me off anal for years. Recently, gradual gentle stretch and increase and now can take him or dildo with pleasure.
recommend a step back and gentle try again, also once through entry one, you have to breathe and consciously relax entry 2 further in otherwise it will really hurt.
we are struggling to wrestle a p spot plug into my hubby’s tight little arse at present.
5 Likes
Ask him
Its always good to communicate… he might have the inner desire.
I like both…
But then im greedy
2 Likes
Since I started this post I have done it a few times and he loves it as well - you are correct it’s good to talk but better to be kinky 
6 Likes
Oh no… ALWAYS be kinky
2 Likes
Give it time. I didn’t want a penis either until I did and once I opened that can of worms I was upset that I missed 27 years of that amazing feeling. I’m divorced now and definitely miss the pegging however now I get the real thing and nobody’s feelings get hurt and theres no jealousies
2 Likes
Love to be pegged by OH especially when she is in her kinky mode I’ve also been pegged by a female friend of ours with OH blessing and she was also present and have took the cock of our trans friend again with OH present she has also told me should I ever want to do it again with Christine on our own I can as long as we capture it on film so we can watch it together again when we’re in bed
5 Likes
I’ll share a funny/But not depending on perspective comment for you. I met Ms.Anony randomly. And by randomly I mean “I still don’t quite understand how but too good to question randomly.” She was married for way too long to a piece of work of a “man.” She was unhappy. She was in a one sided open marriage at his insistence. Queue how I met her. In the TL;DR version.
One of the very first conversations she and I ever had was unsurprisingly sexual. She is very very timid, and shy. So this was cute to me. “Would you ever let me put something in you?” Was her question.
Having previously had the conversation about her “no choice, no voice, no power,” feeling in her marriage. I said sure. There’s nothing that will make me question my sexuality and I’ll let you do anything to me if it will help you find the strength that you feel was taken from you. I then went and bought her the biggest Doc Johnson at…(I forget the name, having a brain fart moment. One of the biggest sex shops in CA.)
3 years later. She has a voice. A choice. Power, when we both decide it’s appropriate. And now I know what a “real dick” looks like. And feels like (In a purely and only sex toy way). Now she has a bigger dick than I do is the bottom line, (a collection of them honestly at this point). The first thing I bought her was as long as my Forearm and the thickest in the store. I’m 6’3 with abnormally long arms is all I can say.
As for me? Well. I’m only attracted to femininity. That’s not going to change. In some ways if it did it would be easier for both of us since she’s always been Bi. (Yes, a Woman’s dick is exactly that to me. A woman’s dick, even though I’ve never experienced one…yet). But, I’m now much more on the gender questioning spectrum, not sexual attraction, and identify at least privately (or in safe spaces), and or under clothes, as non-binary.
Best thing that’s ever happened to me, even if I was wrong in my initial statement. I’m liberated now wearing nail polish on my toes/shaving (face) to toe, learning how to self feminize, taking better care of my skin, crossdressing “in secret and private,” with a new found high heel fetish, all with her help and ever so shy guidance. It’s brought us so much closer and I now understand some of the struggles she goes through for me much more intimately.
Her husband? Who would never let her put anything anywhere near him to the point I suspect rampant homophobia because he knows? Offered to let her do whatever she wanted to him in front of both of their kids as a bargaining tool to get her to stay with him years ago. (But exactly six days after she and I had our first vacation together for…5 days.) She never told him a single thing about me or what we’ve done (with regard to her pegging me, that is). He’s only ever had the courage to face me once, since, and it wasn’t by his choice or with his knowledge beforehand, is all I will say on that topic.
I think there are three types of “heterosexual men” in this world, at least in my mind. Those that are afraid that they will like it too much, and overcompensate in the various ways they are known for overcompensating, not limited to rampant homophobia and aggression towards women.
Those that are “open to it in theory,” even if reserved initially, to being at the very least, non hypocritical. Who are willing to allow their female partners to make them feel what they make their partners feel.
Non-Hypocritical. Penetrated. Vulnerable. Afraid. Excited. Open. Willing. Equal.
And maybe potentially the third group are those who are hesitantly willing to try it and simply don’t like it. But, given the nature and placement of the prostate I submit those men will eventually realize they might like it when they are left alone due to vanilla, or…are unable to maintain an erection and that’s the only way they will get a release.
The first group. Well. I’m pretty sure that with regards to the negative overcompensatory behavior, that everyone on this forum has the same opinion of those individuals.
The second group, well. Maybe I’m biased. Or just lucky to be a part of that group. Because I love the look on her face when she comes out with something longer than my forearm strapped around her waist. The demeanor change. The confidence boost. Everything. And I love a challenge, so I keep buying her bigger and bigger ones.
But if your OH is in the second group in your mind. Trust me. Not all of us in the second group are the same. Even with as much as I knew I liked it, and as open minded to it as I was, coupled with my “I love a challenge, and the only competitor is myself attitude,” well I was still insecure about it for a very long time. I got hung up on the “what does this mean,” aspect for far too long.
So now that this ridiculously long post seems to be wrapping up. What is your take away?
If he’s hesitant but opening up. Don’t give up on him. Understand that it’s literally the core principle of what toxic masculinity has taught men like both he and I, that are being questioned. And have patience. Start small. Negotiate. “I’ll let you…, if you let me…touch the rim” etc. Or maybe just let your tongue wander a little if you’re going down on him for him to realize there’s a whole world of sensory pleasure down there he may have mistakenly taken off the table that he might want to consider putting back on the table, very very slowly.
I hope this un-solicited, long winded as usual 
, advice from the other side of the…(insert name of insertion pun here), has helped you to not lose hope. Or gives you a perspective into what he’s potentially thinking. Maybe helps you clarify which type of the three types of heterosexual men (in my mind’s definition), that he classifies as (in your mind) and how to proceed in getting what you want as a result.
But, from this side of the receiving end, as a Dom. There’s something primally sexy about the role reversal of the power dynamic inversion of being pegged by a submissive woman, as a dominant partner, that is simply “right,” in my book, that just makes sense. Don’t give up on it.
1 Like
@Anony thank you for that. I’m definitely not giving up on him. Recently we have been having a lot of long about sex in our relationship and what we both want moving forwards. This is especially important as we are getting married next you.
He has opened up about finding sex painful due to a tight forskin, that he is now finally seeing the doctor about after some gentle encouragement.
The man is starting to open up and last night was asking me about toys for me and a few did interest him. He also for the first time in his life had a sex toy used on him, a small clit vibrator as it was the only thing that would work for what he wanted that I owned. He very much enjoyed having it used on his dick. I also very much enjoyed what followed.
Last night especially showed me he is starting to open up and he knows that I want to try butt stuff on him I’m not going to force him. For now his ass remains off limits but I will be shopping for a vibrator for him.
3 Likes
Send him a photo of you wearing the strap on in a seductive position looking hot.
Itll either let you know his position on it or hell be home shortly after.
I personally would love a picture or two of my mrs wearing one
4 Likes
Right now it would be a definite no for him @Bigiain. He is coming around to having toys used on him so hope for the future.
4 Likes
Not to hijack this thread but from me (him) I don’t fancy all the practicing in a busy home. I doubt we will find the time and it has definatly left a scar.
We have tried anal me to her a handful of times. She’s not really into anything more than a tickle now but it all happened uneventfully and I think that led us to a false sense of preliminary activities needed 
.
Anal for me hasn’t happened before and the whole idea only came from her cuddling me from behind and the feel of her pubic mound pressed on me tickled both our fancies. Love honey were great and refunded the toy, in reality we wanted rid of it but they didn’t want it neither. I think it will never get used again. But least we can say we have it a go 
2 Likes
strapless are too much hastle, get a proper harness. realistic i found is more comfortable when inside compared to non realistic as the material tends to be softer. i think if your questioning sexuality based on the toy used or the act in general your either not ready or not mature enough for that type of play.
5 Likes
I sometimes get pegged by the wife but one stumbling block appears to be the comfortability of the harness on the wearer/wife.
She uses the harness from the https://www.lovehoney.co.uk/sex-toys/strap-ons/strap-on-kits/p/lovehoney-advanced-unisex-strap-on-harness-kit-with-7-inch-g-spot-dildo/a30701g52006.html but finds that the harness doesn’t provide any padding between the dildo and her body resulting in some discomfort for her.
Any recommendations for better, more comfortable harnesses?
We use a harness like this,
, and pair it with this,
for the base of the dildo As she finds a rather comfortable
I just wanted to add to this thread because some of the comments have worried me a bit… It’s perfectly ok for a man (or anyone) not to want to try anal and they shouldn’t be judged for their choice. My husband isn’t interested and asked me not to mention it again. It doesn’t mean that he’s homophobic or thinks it would make him gay. He just isn’t interested and doesn’t like the idea of it. That’s fine with me, it’s his body and his choice. No one should feel they have to try something if they don’t want to regardless of gender or anatomy. I’m a bit concerned that, if people were critisising a woman for not trying anal then we would be in uproar but some posts are coming close to critisising men who chose not to and that doesn’t sit well with me. Sorry to be negative but I hope you can see where I’m coming from.
9 Likes