Our first time went quite clumsy, we had bought a strapless strap, but it didn’t went very well with that one. Or it slipped out of her or me. So not a big fan of the strapless ones.
So we both another strapon with harness, what went way better, I can say the rest is history she can do me now quite hard with a large dildo we both love it and enjoying every minute of it.
Hi @daisy0211, what a great story. Me and my OH tried pegging a long time ago on a whim and like many others above it didn’t go great - we’d done plenty of anal on her but the most I had taken was a finger so was a bit of a mistake to go straight to a strap-on! Thus after the first time it was left alone for some time until recently when the topic was bought up during a bit of kinky play and we both agreed we wanted to try again but this time work our way up to it. We bought a couple of plugs for me to practice on and also a beginner’s strap on kit from LH. After plenty of talking and practice we seem to be getting the hang of it although we only seem to able to do it from behind - we can’t seem to get missionary right without any discomfort yet but I’m sure we’ll get there 
Morale of the story as repeated numerous times take it slow and build up to it, don’t just rush into it on a whim 
I personally have not had the best of luck with anal douching . I let my back side tell me if anal play is a good idea . Ideally shortly after a good movement that in itself was a clean operation . If I enter myself with a shorter tee plug or a prostarate massager it is usually a clean playtime . When riding a 7" to 9" toy , the risk of a bit of a mess goes up . Butt some times a man has a craving and rolls the dice . If one really wants to make sure you could go with the enema . You need to set a fair amount of time for this and pre planning may or may not distract from play time .
We purchased this as a couple about 12 months ago and yet to still use it
Not from wanting , just other things take over or gentle anal play.
I’m not interested in douching, or asking my wife to douche. Sh*t happens. We’re adults. I’m not saying rolling in poo is my kink (it definitely ain’t) but if I can’t handle it, I’m not asking for anal.
Best preventative methods to prevent clingy poo is a healthy diet with plenty of fiber to pull it all out together. Even so, it still happens. I’d say I only have Klingons 10% of the time, and I honestly can’t remember the last time there was any issue on my wife’s end with anal play.
Re:Pegging, we have a Doc Johnson (I think) slim 5" harness kit that’s been the main one. We did get a strapless to try out, but it was too big for me to take and we haven’t gotten back up to it. I’ve recently got a slightly larger slim dildo - it’s the Lovehoney black silicone 5" and it’s maybe close to an inch girthier than the slim we have. I’ve done a little self-play with it, but haven’t yet tried it with the harness. Pegging isn’t a regular part of our routine, maybe a couple times a year, but it’s great fun. I enjoy it every time, but my wife has to be in the right sort of dominant mood to be interested in giving at all (without the mental piece it just doesn’t do much for her).
we use this kit, its great for preparing for anal. Sometimes anal penetration can encourage a movement of stuff thats high up in the sigmoid, this kit helps to get things moving beforehand. Unfortunately its out of stock here though.
I am not the one to ask about douching, unfortunately. Although from what my partner has told me it is a lot of time and certainly a confidence/comfort thing, more than just reducing the chance of encountering something.
And even after douching, we have encountered stuff back there on one occassion.
Morale of the story, do what makes you feel most comfortable before pegging. Whether thats douching, not douching, using toys etc
So finally after years of it being a fantasy and just something we talk about we tried pegging last night during our crazy marathon post wedding f**king…
Total fail.
Harness wasn’t sitting great, dildo really high, couldn’t get into a good position to get it in…
When she did get it in and got a few thrusts it felt really good, but it was so awkward we gave up.
We will keep trying and I’m sure it’ll be something we will both enjoy, but gonna take some time, experimenting and practice.
@WeeDavie as everyone has said, practice makes perfect. At least you have tried and weren’t completely put off by it. Bit of communication and practice and I’m sure you’ll get to where you want to be. Good luck on your adventure 
We bought this one, the black dildo is great for a first go, reassuringly small! However I switched it out for the red one pretty quickly as I wanted more sensation.
Second time (after much playing with plugs) tried with a bigger dildo still (this one)in the cowboy position and it rocked my world! The shape of this one is great, slim at the top but thickens deliciously as you go further down/in….
Try cowboy, her laying on the bed and you straddling. Or use pillows to get your alignment better. Keep trying, it’s worth it!
It takes time and practice; also it really helps for the receiver to have practiced solo to figure out size/shape of toys and angle. The first time we did it it was pretty meh, but we’ve worked on it and really enjoy it now.
Sometimes it also helps to insert the dildo then attach it to the harness, at least it’s helped us and avoided some odd thrusting!
This is my first post.
I am eagerly awaiting the arrival of a LH strap on.
I brought it up with my wife, really not sure how she would respond, but was pleasantly surprised to hear that she has always wanted to try pegging.
I’ve used a few butt plugs and my new LH anal beads, but I’m definitely ready to up my game!
Other than don’t rush, and full communication… Are there any little tricks or tips to help ensure a good experience?
Or any surprises to expect?
There’s a few threads on this, I’ll leave it to the regulars to do the linking!
My quick points
Get clean with a bath and nice and relaxed
Allow time to get psychologically and physically ready, no rush, take it slow.
Lube
Lube
Manage expectations and make it about fun
Keep talking to each other, the difference in angle can make a huge difference.
Even if clean, be prepared for mess
If you can, both of you practice alone to check fit and comfort
The first time may not be magical for you, that’s OK. It’s a learning experience for both.
Also, lube. Keep applying before and even during.
Tips!
Go slow at first and communicate how you want it. If you really want her to f**k you hard tell her. Let her know that she is in control, it’s a real turn on for my wife.
Lube lube and more lube
Positions.
Lie on your back and lift your legs to make access easier for your partner. It’s also a turn on to surrender your body to her. From this position she can finish you off by hand and still be thrusting in your ass.
Doggy style can be fun but more difficult for your partner to finish you off.
Spooning is also fun when you want slow relaxed thrusts rather than a hard time.
That’s great! Thanks so much for advice, and linking to the other replies on this topic.
I’m hoping the first time goes smooth as a tube of lube. But I know that’s not likely!
Now I just need that package to arrive!
Thanks to all 
Try using it in your/partners hands first not strapped on?
It’s my birthday soon but last week we had some time together, she suggested that we go upstairs and she would make me cum, don’t need to ask twice. It’s the time of the month but she is never that heavy anymore but we don’t have PIV when this is the case. We were naked apart from her knickers, kissing and licking each other’s pierced nipples. I get very turned on by this. In the heat of the moment I suggested that we try a strap on on me again. This happened years ago, which I loved, but her not so much. She said she did not like having a cock and came out with the whole gay thing. As the years have gone by I have slowly introduced anal dildos to our play which she uses on me now and again. Love this. To my surprise of my asking she said ok. Wow I was buzzing. Got out the kit which I had brought for the special occasion.
Trou down and strap up with these unisex harness briefs. Discreet enough to wear all day, immediate pegging, packing or strap-on play can be yours at any given moment, simply slip a dildo into the comfortable yet stylish briefs and let the fun begin.
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With a flared base, curved shaft, semi-realistic head and a smooth silicone finish, this dildo is built to please and has one wish only: to seek out your G-spot or P-spot and show off its world-renowned intimate massage skills. Get ready for…
Knickers came off. I helped her put it on, she looked amazing which I told her. We got on bed and she rimmed me from behind until I had to get her to stop. She I very good at it.
I was shaking with excitement at this point.
She laid down and I got on top. It went in with ease, but I struggled to ride it with my short legs. I couldn’t get in to a rhythm which I was annoyed with. We are both medium build.
I asked her to fuck me from behind for my birthday, to my delight she got up. I turned dildo round so it was pointing down whilst she was standing up. I inserted a bullet vibrator in the pocket of the pants for her. I wanted her to get something out of it as well. I assumed the position on all fours on the bed and she stood behind me.
I was so excited that it was about to happen after all these years.
Then it happened. She entered me, thrusting slow at first, god it felt good. I was screaming with delight. Good job I had closed the bedroom windows. I was really loud. She started to get quicker and deeper. Really giving it some. I thought I might pass out. I was getting light headed. I started to stroke my soft cock and I could feel it building. It didn’t take long and I came on to some tissues I had laid underneath my cock. There was loads of it. I didn’t have to wank too much but I couldn’t take any more. I really wanted a hands free orgasm.
I got her pants off and we lay on the bed together. I was a right mess. Breathing heavy and light headed I needed to calm down.
When I did, I started to lick her nipples but she got all defensive and told me to stop and told me she had already cum. I was really surprised and excited as she usually takes ages to cum from a vibrator.
I think she really liked it but was reluctant to admit it.
Birthday is soon so hopefully we have turned a corner on this at last.