How to bring up anal after previous bad experience

Sex Tips & Talk
1

I keep bottling it when it comes to asking my partner for anal sex.

We attempted anal sex probably about 3-4 years ago now with pretty much no research or knowledge other than watching it in porn movies… needless to say it didnt go well. We tried to go from a couple of fingers straight to his cock and it hurt (and I bled) it upset my oh and put him off anal.

Fast forward a couple of years and it popped up in conversation, I got really turned on and told him I was very much happy to try again as long as we took our time and got more knowledgeable but I could tell he was still nervous about it so didn’t push it.

I did some research on anal toys and how to stretch myself etc and told him just how wrong we went last time and he seemed back on board and excited at the prospect of anal sex again.

I bought the beginners anal kit from LH and we have had lots of fun with that! Vaginal sex with a butt plug in my ass is wonderful for both of us! But that’s pretty much as far as we’ve got together and I’m not sure how to move on or even if he’s gone off the idea again as conversation doesn’t seem to go there anymore.

I bought a 6” dildo to see if I could work up to taking that and I enjoy regular solo anal sessions with it now but I haven’t told oh about those and now I’m not sure how to in case he sees it as me keeping stuff from him.

I would love to bring anal into our sex life and I do long to take his cock in my ass but I also don’t want to make him feel uncomfortable or like he can’t satisfy a need of mine as I respect him completely. I just think the thing holding him back is still his fear of hurting me but that’s not going to happen. If we did decide to try again I’d get an 8” dildo to continue stretching.

I just feel stuck and unsure if it’s even worth trying to bring it up again. Our sex life isn’t bad but I know we could open so many more (back)doors (literally… :see_no_evil_monkey::rofl:)

Do I risk it? How do I drop it in conversation? Or just keep it as solo play?

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When did you last have something in your sexy ass and what was it?
2

Just have an open and honest conversation … im sure hed be up for it

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3

Definitely back an open and honest conversation. If he’s anything like either of my partners, you’ll be in for a fun night!

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4

You need to discuss together @Playtime1

Anal can be amazing for both parties but you need to go with care and build up to taking his penis

I feel the blood was the biggest issue - no one wants to see that

But just approach it and let us know

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5

I’d say it isn’t a bad thing you’ve been keeping from him… see it more as training sessions you’ve been doing to prepare yourself for him to try anal again on you :slightly_smiling_face:

Perhaps say you’ve been practicing with the dildo of late and you think you’re finally ready for him to try again.

6

When I originally brought up anal to my OH (boyfriend at the time) and told him I played with dildos in my bum already he was just really turned on by the thought of it. So appreciate we didn’t have the bad experience part, but I’d be surprised if he is annoyed. Plus it sounds like you are well prepared this time and that will likely be of comfort to him.