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Holiday-Awareness-35

Are you relaxed? Like really relaxed? If you feel any pressure to bottom, even from yourself, it will make it harder to relax and bottom. Try playing solo after a bath or when there's not potential pressure to bottom and take it slow. The 4th plug might just be a bit too big (for now). Try "gripping" and holding the 3rd plug for 5 seconds, relax for 10 and repeat. This can help with moving up a size. Also, breathe out when inserting as that helps relax too. Good luck!


[deleted]

you may just not be relaxed. Try telling him to only stick the head in and to slowly but a little fast like 3/10 speed going in and out. Use a lot of lube. Maybe you’re not mentally into it. It’s supposed to not feel great at first. Be careful with poppers.


ginandpoetry

Relaxation is key! That being said, you also need to be eased into it. Take your time. Use fingers or toys first. Lube is also your best friend. Some lubes will work better than others for different people. Go slow and build up to it throughout foreplay then when it comes time for the act your body will be ready. You need to walk before you run. The need and want can sometimes add to the frustration and then in turn the pain.


AnonymousFoxxxxy

It's pretty unlikely you're just too small, sphincters can stretch pretty much as much as they need to as long as they relax. If all else fails try poppers.


OdorousRafflesia

I had the same problem just starting out. If you really are just tight, like I was (or still am if I don't have regular sex), there might not be all that much you can do besides power through it. I had copious lube, poppers, and foreplay, but sex was distinctly uncomfortable for the first 5 times, with each time lasting about 20 - 30 minutes. However, after regular bottoming, it became A LOT more pleasurable going forward. Sometimes you gotta embrace your inner Shia LaBeouf and just do it.


V_Ster

I feel like if you can take 3rd of a 4 set of buttplugs, you should try use those then attempt anal play. It will be a nicer attempt than fingers and dick. I am in a similar situation and fingers is not the same as buttplugs/cock. You may also be using a lube which isnt helping. Trying using different types of lube after different sessions