In the honest first time thing, it took us about 3-4 times to learn a good position, get the harness at the correct angle and not keep popping out every 2 minutes.
It was amazing, but there was a learning curve
Our first time was after we had started anal sex adventures with my wife. We had prepared very well with butt plugs and lube however the first time was a bit painful for her. She summed up the experience by saying that I should try it. From that chance remark I started to think about it. Occasionally we share a bath and the next time we did she washed and fingered my bum which was nice. A few more times and we were into me having the butt plugs inserted. Then the time came to get a strap on and my wife ordered one and surprised me one evening when she came down from the bedroom suitably fitted up and ordered me upstairs. We took it slowly and went with our selection of butt plugs and lube before she said that it was time to penetrate me. I won’t say it was a great first experience as it did hurt a little, probably because I couldn’t relax but it was enjoyable and left me wanting to try it again. From then on we have learned to relax and we now both enjoy anal sex and it has become part of our sex play as well as PIV and masturbation.
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@daisy0211 Love this post and all the stories, thank you for sharing. My wife and I have talked about doing this, we’ve purchased a strap on harness and a slim dildo, and I’ve given myself a prostate orgasm once, but we have yet to take the plunge.
I think my biggest concern is cleanliness. I have an anal douche and I’ve used that the few times I’ve done anything with myself, but I’m just so worried that we’ll work our way up to this and then something “yucky” might happen that kills the mood or any chance of us doing it more than the one time.
I think in another thread someone said that it’s just something that may inevitably happen and is part of the price you pay to do it. Would you say that’s accurate? Any other suggestions for either easing the concern or mitigating it? I’ve gone as far as using latex gloves and even a condom on the vibrator that I used on myself in the past, but worry that it’s a bit overkill. I also want my wife to feel comfortable so if she’d rather use gloves or something I’m totally fine with that as I don’t think she’d want to just put her finger inside me.
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We’ve hardly ever encountered any mess, and on the rare occasion - it’s at the end when we’re done playing so it’s no big deal.
Having kids, we’re used to having to deal with 
anyway I guess!
But like I said, it rarely happens and we don’t even douche neither.
My hubby doesn’t mind fingering my arse but if I finger his, I always use a condom just to be on the safe side 
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Got to be honest, I’ve never had any problems with cleanliness as long as I’ve prepped beforehand by going to the bathroom, making sure everything is clean. There’s loads of guides online on how to reduce the risk of encountering any poop
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@Cupc8kes that’s a relief to hear! We also have kids, so I think maybe I’ve just had my fill of dealing with that stuff during the day-to-day and want to keep it and anything kid related very much out of our love life 
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@Happypantycouple good to know. I just worry because I think it would be a real mood killer and probably result in us not wanting to do much of that stuff again. Guess I’ll go read some guides.
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Update - Our planned day for attempting pegging went haywire with some family stuff. But we are away this weekend for a romantic trip so fingers crossed things play out better then! 
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So we are back from our hotel stay which was very successful! The first night was Kinky but mainly focusing on me, then the second was for him. I checked with him through the day that he still wanted to try pegging and he was apprehensive, but still said yes.
We had a bottle of bubbly while relaxing, and he put in the smallest plug and at 15 mins intervals he changed to a bigger one. I put the harness on and attached the smallest dildo of the set, and used plenty of lube (too much, I ended up having to wipe it off my hands as I went overboard!)
Hubby decided we would start with him on his back on a half deflated wedge. I gently guided the end in, and took it as slow as I humanly could. The look on his face was worth it. That position managed to hit his prostate and he was moaning away and his eyes were rolling. For a bloke who rarely makes a sound during sex that was such a turn on for me! I picked up the pace a little bit, but only managed it for a few minutes as my muscles cramped. I’ve a new found respect for the ‘humper’ in a session!
He rolled over and we attempted doggy, but he really wasn’t a fan of that angle so that didn’t last long. I then laid down and he went into cow(boy). This position also was amazing for him. He took all of the didlo and was proper grinding on it which was glorious, especially as he was pressing the bullet in the harness into my clit.
After a while he said it was getting too much and that we should stop and consider the first try a success. He wasn’t sore at all, and he’s now a lot more at ease about trying again, so I would say it was a resounding success!
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So happy to hear your expirance went well!!! Do you have anything tips or things that didnt work so well for you or suggestions for next time to make it better ?
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That’s great @WelshDragonette! What a brilliant weekend. I often wonder about the consistent effort required to thrust and whether I could keep going 
Hopefully I’ll find out one day 
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@Spennymack personally next time, I will be testing position BEFORE putting the dildo in the harness. It will just save deflating/inflating a wedge with a dildo wobbling around hubby in a slightly daunting manner
Hubby said you just need to make sure you are as relaxed as humanly possible, and that you like using the plugs beforehand to gear you up to it. He said he should have kept the last plug in for less time as it got uncomfortable, but luckily he got back in the zone quickly
Great to know thank you !!! We have used dildos and such quiet abit and tons of plugs !!! I’m not worried and I’m sure I will absalutly love it once tried was just curious on your expirance and the dos and don’t haha thank you very much !!! I don’t own a wedge but we do own the full liberator collection bassicly minus the wedge ( because same shape came with our chairs )
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Hiya, sorry it’s been a while but in case you still want to hear back, here’s just a little update/reply
Thankfully we haven’t encountered ‘mess’ during our play, but I think it’s because we both like to be prepared but also because I don’t think it’s something that comes with the territory if you do prepare.
My partner always douches before play, he has a quite basic (but still v.good quality) kit that he uses until he is comfortable. And we only ever do pegging when he is 100% comfortable as it wouldn’t be enjoyable for him if not, and I don’t want that.
I have therefore never felt the need to use gloves or condoms when doing manual/finger prostate massage, or when using the strap on (we have progressed to an 8inch dildo now, and have still never encountered mess), but that is because my partner and I have laid everything out on the table and we both understand each other’s POV. He told me he would be fine with me using gloves or condoms if I want, I told him that I’m fine without if he douches. He will also check in to make sure there’s no mess, just so he is put at ease.
Please let me know if I can help any more, I will try to check in more frequently now I’ve seen that this has recieved a lot more replies from last time I checked.
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I’m so glad your experience went well! I hope my story helped you, and/or helped you and your partner open up a discussion.
My partner and I have had a few more experiences and played around with different dildos and harnesses. I have a very comfortable harness now, and my partner bought himself an 8inch dildo (greedy) which he enjoys with a lot of pleasure.
Before he bought the now favourite toy, we did also try a dildo which he used to use for self play, with the thought that if he enjoyed it by himself then it would work for pegging. We tried it and it wasn’t a great fit (‘it didn’t quite hit that itch, ya know’), so we accepted it and agreed that we will try something different next time. Talking (my partner and I have a conversation after every experience, what to do more/less off, what never to do again, thoughts, feelings etc), accepting that some things may not be the best fit and being open to trying different things (harness, toys, positions) has worked so well for us, so I suggest it to everyone (not just with pegging but with all sexual experiences)
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I absolutely agree with @Cupc8kes that, especially for the first few times, that a harness with removable dildo attachment is best. Your wife can find a harness that fits her best, and you can find a dildo that you get the most pleasure out of. The first few times unfortunately, unless you’re extremely lucky, won’t be perfect but that’s the joy of a healthy sexual relationship: try and if it doesn’t work, talk about it, find a different option and try again.
My partner and I have tried 3 different dildos, 2 harnesses and 3 different positions, with the intention to try more 
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Hey @WelshDragonette , and congrats on you and your partner for taking the plunge (if you’ll pardon the pun!).
My and Sexterminatrix’s first foray into pegging was to try the cowgirl thing with me on top, as like most people I was a bit wary about things going too deep, too quick. I can’t say it was the best experience I’ve ever had, although it was pleasurable in its own way, so you could say it was hit-and-miss, for the most part.
Second time around, I determined that I wasn’t going to mess around half-heartedly. We had by that time purchased a sex bench, and I got securely strapped into that while my wife used a strapless strapon and basically had complete access to all of my bits. Now THAT was a night to remember! She had already come twice before she had even penetrated me, watching me “struggle” against the straps while she lubed herself up for me, and it just got better from there. I had also placed a long mirror underneath the bench so that I could watch her pegging me, which also allowed her to see my facial expressions as she pleasured me vigorously. Best night ever!
Third time, we dispensed with setting up the bench, and she pegged me on the dining room table which turned out was the perfect height for us. We still giggle to ourselves when we have guests and they happen to be sitting where she did me, which then sets up subsequent sessions.
We’ve done it quite a few times since, and while it’s not every time, I’m always delighted when she is in the mood to “make me her b*tch” haha. We love it for the exchange of power, and that I can give myself completely and utterly to my wife in such a physical manner that transcends mere words. For some it’s the mere sensations, which are great of course, but for me it’s my demonstration of complete devotion to her that brings me back for more, time and time again.
Best of luck with it, and I hope it works out as enjoyable for you both as it did for us. 
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My first time was a large amount of hubris. I thought oh, I’m an experienced bisexual guy, I’ve done this before with an actual dick, it’ll be no different. And then the realization set in that most straps are larger than average, and a strap never climaxes, so it just keeps going, and going, and going… safe to say my ego took a hit.
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He prostate orgasmed for the first time ever this morning 
safe to say I’m proud of myself, and beyond ecstatic that it finally happened 
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Hi Daisy - great story and something ive been trying to get my wife fully into for ages. I think finally its going to happen, but part of the big turn off for us both has been “poo” we tried a while ago using a small ( 5 inch ) slim silicon dildo and whilst it was enjoyable, with some rolling eyes on my part - when we remove the dildo there was the nasty stuff on the end.
Silly question but hows does one douch effectively? clearly i didnt and i wonder what your experience was?
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