Tonight we are planning to break out the strapless strap on, I’ve had a few things in my ass before, but this will be the first time Mrs-toysrus will be in charge, so for the guys who enjoy regular pegging fun, what positions would you recommend?
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I’d recommend a position you are both comfortable with and can maintain as you don’t want to be thinking about how being uncomfortable or off balance or whatever. There is no reason why you can’t try a few different positions in one session though, although I would recommend not trying more than 2 or 3 to start with unless you are really struggling to find one that works.
You being on top might be a good one to start with (cowgirl but cowboy?). This will allow you control of the speed, movement, depth etc and will also help her if she isn’t used to using a strap on. Getting a good thrusting motion and controlling something you have no feeling of isn’t always the easiest thing to do to start with and as you are using a strapless strap on, keeping it in is a factor. By laying on her back, gravity isn’t working against her in the same way as if she were on top or on her knees etc. You can do most of the moving to start and as you both become more comfortable she can join in. You will also get good access to her body as a bonus.
If her being in control is the biggest draw, spooning would be another good option. Penetration from behind has more of a being “taken” feel and will give her more control over movement than you on top but it will be easier to keep the toy in place than an upright position.
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I can’t recommend any positions as you’re doing my ultimate fantasy that may never come true, but hope you both have a fantastic time and relish the experience.
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@Calie some great advice there thank you, I will hopefully be able to report back tomorrow
@Northseaguy you should never say never, 3 months ago I would have said the same thing, but I got the courage up and said that it’s something I wanted to try, I originally suggested a double ended dildo, but while looking through the lovehoney site, she saw a blue posable one with a bullet, so she gets fun from it too, how’s it gonna go? I will hopefully let you know tomorrow!
Good advice, too much pressure will kill the fun in a heartbeat. When starting anything that gives you control is best as there’s not always a great deal of physical feedback for the giver.
Cowboy or reverse is a good one and a good workout all at the same time as giving a good view.
Doggy is also a good choice, you can always back up to give a bit more control. Angles can make a huge difference too so be prepared to move around and as ever keep talking.
Spooning is also a good way to ease into things as well as being intimate and easy access!
Good luck to you both and hope you have fun.
Just dont go at it like they do in porn. Take it slow and intimate. If something doesnt feel right then stop and sort it out. Every experience will teach something to make the next one better
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I’d love to know how it goes.
I’m planning to give it a go with one of these ones
Although the DOTD look pretty good too!
I always imagined that, as the female, I would be pegging him.
I never even thought about doing it the other way round 
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My main concern is cleanliness, but I’ve got something to give me a good clean out first! We also have other toys that will enhance the fun for her too, so hopefully I’ll achieve a p spot orgasm, it’s gonna be a looooong old night! 
Doggy, (more submissive), cowgirl (boy) (more control for you) and face to face with my hips on a wedge cushion (P spot stimulation).
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I’m thinking either doggy or with me on my back so she can play with me too
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If you have a wand she could use it on herself or use it on the dildo so you both get some of the vibrations lol
We’ve done this twice. Second time was missionary which was alot more intimate and made communication easier.
Hello, I actually pegged one of my guy friends for the first time a few weeks ago and we tended to stick with doggy as it was a easy enough position for me angle wise and he said for him it felt the best as I could get the deepest.
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@zombifiedguy the strap on has a built in bullet amd we will probably use the vibrating butt plug on her too
@monkey169 I want to achieve a handsfree cum so don’t really want her stroking me for the first time
@Sophie01 I’m thinking doggy is the way to go for the first time
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When we used to do a lot of pegging i usually lay on my back with my legs up and bent at the knees
I used to relax more that way
The other favourite for us is doggy, she really goes for it in that position
I don’t think we ever done any other positions
Just take it slow and work out what’s comfortable for you both, and have fun
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Might be worth a bit of pre Play or a mid sized plug for A good ten minutes to help get you ready and clean you out prior. Not sure if this was part of your clean out plan anyways. Best to give it a few goes as the first time may not be what you imagined straight away.
I honestly wouldn’t stress it too much if you are experienced with anal play. Probably the easiest position for beginners is doggy, but you might also like cowgirl as this puts you in charge and let’s you decide the pace.
But most importantly, have fun! This is my biggest fetish and I totally love what it does to me!
As mentioned above, doggy feels submissive, more so if you stretch your hands out in front with your forehead touching the sheet.
Cowgirl provides you with control over depth of thrust and you also have the benefit of eye contact and your OH can grasp your old chap as you rise up and down.
We have found starting with the former and ending with the latter works for us.
Just one word of caution over size, go easy at first. I am reminded of a review of dildos by the comedian Jenny Eclair. She reported that the largest one she tried rearranged her internal organs which she realised when a kidney popped out of her ear.
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Hey lots of great help here, I’ve been trying to get the OH to peg me but it’s not happening at the moment, discussing more anal play at present.
I ended up getting really drunk and fell asleep, so it didn’t happen! There’s always tonight!
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