Good evening all and hope your all well. I’m looking for some helpful advice and finely built up the courage to put it up on here and ask for help. So here goes!!! I’m really interested in trying anal play. Id like someone to do me with a beginners strap on. Long story short. When I was with my ex (she was not the most open to trying different things) she did try and succeeded to put the p spot toy for beginners in my ass and I really enjoyed it. However she couldn’t say the same. Since this I’ve wanted to explore more but am now single and no one to help me achieve my new wishes. Any advice on how I could approach this if I get a new partner? Thank you
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Welcome to the forum, you really do hit the ground running, there have been many excellent threads already made and commented on throughout the forum on the art of pegging. Make a cup of tea and just type the keyword in to the search function and time will just slip by while you might become quite inspired.
While I entirely agree that this pursuits is best done with a partner, it is possible to be done alone. With the right length P massager or suction cup dildo it can be accomplished when attaching it to any smooth surface. @rockstar is a great source of knowledge as are many of the people here.
One example of lone play and for someone practiced in the art of self pegging, is for use in the bath or shower. After training your ass with increasing sized butt plugs which is a whole lot of fun in itself. Sticking something like this (there are also many other options ) to the bath or shower wall while masturbating
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While my first foray into all manner of small play was with my wife, some of the advancements in it have come as a result of taking the time to practice alone and/or self-directed small play together (i.e. using my P-vibe while we masturbate together. So I will say, be emboldened to embrace the journey on your own. The more comfortable you are to this play alone, the more comfortable you might be with a partner!
@Pussymuncher86 - you need to get yourself on a dating app - there are many people out there that would love to meet you and also accommodate your sexual needs
Otherwise you could always visit a local sex worker / dominatrix - I have in the past worked with my friend who is a dominatrix and pegging is quite popular for men to ask and she is very good at giving satisfaction- but this can be expensive
I’d try be openly from the off if you get into chats with someone and the sexy topic arises about what sort of things you both enjoy and want to explore more… that way it’ll sort the bland from the adventurous before it gets in too deep 
While pegging/strap on is really best enjoyed with a partner where there’s a lot more at play than just purely anal pleasure, as JGood mentioned there is plenty of anal play/pleasure you can do solo in the meantime! (while on the search for a new partner)
I actually explored anal play mostly while I was single with prostate vibrators, butt plugs, and dildos! These can all give you anal/p-spot pleasure on your own, with dildos giving you the closest thing to a pegging experience - such as suction cupping a dildo onto a wall or floor and backing up against it or riding it 
There are lots of non-phallic dildos/suction cup dildo options out there as well if you are not interested in a realistic/phallic one.
When I first met my now wife, I was already deep into anal play . I didn’t bring it up right away but after a few dates or couple of weeks, she wasn’t into it prior but was open to exploring it with me after she got used to the idea, and now she loves pegging me!! If you are looking for a potentially long-term partner, bringing it up on the first date or two may be too soon but also don’t wait too long to bring it up either - only to find out you are not sexually compatible (i.e. one very adventurous, one very vanilla). However, if looking for something more short term, hookup, or fwb then definitely bring it up towards the start!
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Hey!
My advice is to learn your own body on your own before inviting another person join in.
That way you’ll know what you like and what you don’t, and what actually brings you the most pleasure.
Solo anal play is brilliant when you have the time. Don’t rush it. You need to give yourself a good few hours for self appreciation .
Gentle but thorough douche will help you avoid you worrying about “ick” moments. They happen occasionally. Have a towel underneath you. No biggie.
Avoid stimulating your d**k too much when you start feeling positive vibes from your prostate.
The wonderful thing about the prostate is you can have multiple orgasms once your brain acclimatises to it…provided you don’t jerk off to completion. That’s game over for a couple of hours at least.
Some prefer the feeling of direct prostate stimulation, and others prefer the stretch, others depth.
And give your butt a rest for a few days after play. It’s all too easy to go at it again the next day and regret it. The most pleasurable rear stimulation is where there’s been no play for a couple of days.
Good luck on your voyage of self discovery. 
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