Trying to enjoy bottoming

So I would definitely consider myself a top and up until now had no interest in bottoming and the only experience I had was extremely unpleasant. Recently though I’ve become curious about bottoming as my boyfriend is vers and I would like to know what all this fuss is about bottoming lol. We’ve tried to have sex twice and I also have a few toys that I can use on my own time, I have plenty of lube, poppers that I’ll use occasionally and each time I’ve cleaned out really well. The issue I’m facing is that every time I try it feels very uncomfortable, yesterday I used a prostate massager which was probably the most comfortable thing I’ve used and actually seemed pleasurable sometimes but if I use anything larger like a butt plug a dildo or my BF’s dick it is very uncomfortable and feel like I need to go to the bathroom and the feeling doesn’t go away. I have tried to stretch myself open to try and relax my ass more but it hasn’t really been working.

Is there anything that I can do differently to try to loosen myself up/make it feel good? I want to be able to feel pleasure instead of constant discomfort and have my ass loosen so I can actually take something.


  1. You’re gonna get that feeling, try different positions or a different lube. What lube are you using? You’re putting something big in where you are used to only having as a one way path so naturally your body is gonna give you the feeling of “oh there’s a big thing there I need to get rid of it.” When he’s pushing in it’s good if you push out like when you shit. Don’t strain tho, straining is bad an can tear you inside.

  2. You may also have an allergy to the lube or toys you’re using (such as a latex allergy). Try coconut oil and a silicone toy.

  3. i am allergic to gun oil. Next day my eyes are shut and sore.
    I use menpowder. Also that powder vets use, mix with water and from 1/2 a kilo you make 16 liters of lube

  4. I’d keep experimenting on your own before you have to start worrying about a partner’s fun too. Some guys need to work up to larger objects like an actual dick, and some guys just never really enjoy it. It’s an involuntary clenching reaction and you need to teach your body that it won’t hurt. Getting used to it alone with no pressure is the best way.

  5. I’m in the same boat/same scenario with my boyfriend. Honestly for me when I take an edible I’m way more into bottoming lol. We’re long distance until August so about once a week I try to play with an anal plug training kit (small to large plugs). I’d been doing this before our last visit a week ago and it honestly helped a lot, but was still uncomfortable. Definitely all about being relaxed and enough lube. definitely a thicker lube is what I try to use either way. Let your bf try fingering you or using a plug for a little bit before. And it’s does get better with time (or so I’m told). Cheers!

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