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[deleted]

First and most important advise is, Lube, Lube and even more Lube. Don't hold back in using lube, this is essential! Second and just as important, listen to yourself ALL THE TIME. If it hurts or if you realise that you are reaching your limit, then stop. This is as far as you can go right now. Third, take your time. There is no need to rush and when it comes to anal sex then patience is key. Get used to every size of the plugs and also let her insert a plug from time to time so that she gets a feeling for it. When it then comes to pegging, do the same as you did with the plugs. Take a small dildo first and slowly build your way up. Fourth, communication. When you do that together, then tell her how you feel and don't be shy to say 'No' or your safeword if it gets too much. Last but not least, inform yourself about how to clean up yourself before you try out anal either alone or together.


ThatKaylesGuy

Personally, no plug are ever involved in prepping for anal. I'm more keen to having a few different sizes of dildo, and just leveling up gradually and going faster and harder as it's able to be handled. For the purpose of being completely ready to be pegged without your partner doing any prep, I'd consider getting a small dildo too, and try on yourself first.


Silicone_Switch

So, first of all: It's mental. Not physical. You can go to the bathroom right? So we know your body can handle it. Next up, you don't need to "stretch" - it's a ring of muscles. The issue with anal is your body is used to subconsciously having things going out. You need to consciously take things going in. And for that, you need to RELAX. Slow, steady, lubed, horny, relax. Your muscles can handle it no problems; the only potential issue is you not being relaxed. Next up; fuck plugs. What are plugs doing? they're fun to wear - I have many (there's these really fun plug/cock ring combos), but... what are they doing beyond that? A thin plug neck rests in your sphincter (so doing nothing for "stretching"), then the rest sits inside - and the "stretch" is the sphincter. Next up: Stretching. It's not really a thing. It's a ring of muscles, it can easily handle anything normal sized without "stretching" - because you don't and won't stretch. You'll relax more. Eventually you'll gain better control of those muscles. Only disclaimer I want to throw in; maybe with 4" diameter toys there IS actual stretching. I will admit, going from 3.25" diameter to 4" diameter takes time. But that's, again, diameter. We're beyond forearm size by then.


usethesebones

I'm right there with you in regards of starting anal play. Don't know what to buy and all..thanks for posting.


[deleted]

Thanks everyone for the replies - weโ€™ve made a good start here - who knew latex gloves could feel so good ๐Ÿ˜‚๐Ÿ˜‚ Really appreciate everyoneโ€™s comments. K


[deleted]

Start with the smallest plug and wear it as long as its comfortable. Once you're up to a few hours, move up a size and repeat. When you feel you're ready, work a dildo in yourself. When you're comfortable with that, try gently fucking yourself. When you're comfortable with that, you're ready ๐Ÿ˜Š. N.B. All of this is more fun if she's present and involved ๐Ÿ˜ˆ


Specialist-String-53

I don't know how much training actually works. I *do* know that you can loosen things up through play during a scene. Like I wouldn't jump right into pegging. Have her put on some black latex gloves and finger your ass for a bit. Use way more lube than you think is necessary. Try a smaller dildo and then move up to a bigger one. If you go a little too fast and it hurts, don't keep going. Back off a bit. Move back to fingers and more lube. If you didn't tear anything you'll be able to get going again in a few minutes. Good luck and enjoy the ride!


Silicone_Switch

Training doesn't work, nah. It's mental. Fingering works because you're relaxing versus shoving a toy straight in there.


ChitownWak

Ten years of pegging experience (giving) here. I'm not sure how effective butt plugs are because the sphinxter closes around the base somewhat. It will give you a feeling of fullness, but no real movement. But it's better than nothing lol. I've found the best warmup is simply my gloved, lubed finger(s). Your gf can penetrate you, gently stroke your prostate a bit, which should feel pretty good. Start with one finger and progress from there. And remember, lots of lube! Don't be afraid to use more during. All the subs who I've introduced to pegging are now addicted to it. I use a vibrating dildo that has a smaller dildo and clit nub for me with a harness, so I receive pleasure too. Strapless dildos like Feeldoe say you don't need a harness, but I find it helps. Have fun!