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… )
Do I risk it? How do I drop it in conversation? Or just keep it as solo play?
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
Perhaps say you’ve been practicing with the dildo of late and you think you’re finally ready for him to try again.
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.
Thank you for the replies of advice. I do agree that we need more open, honest conversation, it’s just not something that happens much so I am going to make a real effort to instigate more conversations about our sexual wants and needs but gradually.
Yesterday OH was clearly horny and started play fighting me which (handily) usually leads to us being on the bed and by that point I was also very horny. We had great sex! Halfway through I asked him to grab the butt plug and put it in me, he did and its just makes such a difference. He switched to doggy to finish, the feeling as he was thrusting against the butt plug was very nice
Afterwards I asked him if he enjoyed it and he said yes, he likes the extra pressure and tightness. I made sure to tell him just how much I enjoyed it and how I love the feeling of my ass being full.
In a few days I’ll tell him about the dildo and see if we can play with that together next time I think once he sees how much I like that in my ass he’ll be more open to trying anal again hopefully
As others have said, if anal is something you wish to explore with your partner, just have an open honest conversation and communicate your desires. Preferably do this in a casual moment and not right when having sex as not to make him feel pressured.
I’m regards to using the dildo, keep at it. Anal masturbation solo is the best approach to learning your body and how it responds to penetration and stimulation. Over time you train your brain to desire anal penetration, making insertion easier. Work your way up slowly until ready to try and take his penis. Always go slow at first and lots and lots of lube.
I’m sure he would likely be thrilled to learn of your solo practice and telling him may even lead to opening the idea of him using the dildo anally on you. This could be an intimate opportunity to introduce some new play and communicate to him what you like and how to stimulate you.
Move at a pace comfortable to both of you, communicate, and be open to exploration. After all sex is all about having fun together. Best of luck!
Thank you so much @Cumalot82 this is really useful and reassuring to read
I’ve found it hard to initiate the conversation because we just don’t talk about sex very often other than in the moment but I did take the bull by the horns later in the day after our most recent intimate session and we discussed how it felt for each other and I let him know how much I enjoyed it so that’s progress and I’m definitely going to push myself to start these conversations more.
I think your right about training your brain to desire anal penetration as there’s a definite increase in my desire for it and I do find it easier to relax as anus for the initial insertion now. Question, how do I know when I’m ready to move up to the next size dildo and how much should I increase by? I know its not big but have been comfortably taking the 6” (3.5” girth) for some time now so maybe I need to make a purchase. Also how often is often enough? I currently use my dildo 1-2 times a week.
I’m in no rush but I am really hoping he’ll be happy when I tell him of my solo anal play and as you say it would be just perfect if he was willing to use the dildo on me as he’ll be able to see how far I’ve come and how comfortable and happy I am in these sessions. We need to replace those bad memories with positive ones for him. I think if we can get to that stage then he’d most likely get as exciting about the prospect of anal sex again as he originally was 3-4 years back.
In regards to when to move up in size for a dildo, that’s only something you can decide. The one thing to understand is that there are two anal sphincters. Your outer sphincter you can control. The inner sphincter you can’t. That’s why building arousal and being highly relaxed is so important in enjoying pleasurable penetration as your inner sphincter will be more accepting of a toy or penis when relaxed. If you are tense, your asshole will naturally tight making penetration more difficult.
You can go up in size if you wish, don’t increase to much at once and just take it slow. I believe you previously mentioned you purchased an anal training kit. Have you been able to take the largest butt plug? If not, then I would start here, slowly introducing larger plugs in the kit and see what you can comfortably insert.
As for how frequently to play to train your asshole, again fully up to you. I would not worry as much about frequency, rather just key in on what you are feeling and how your anus responds during playtime. Remember it’s a journey, not a race. It’s all about learning your own body and having fun exploring.
One more thing. As I previously mentioned, id suggest you and even your husband look up the Pleasure Mechanics Speaking of Sex podcast. They have a great episode discussing their approach to anal sex. They discuss basic anatomy and discuss play leading to penetration from the view that anal sex is to prioritize the pleasure of the receiver versus the giver. They emphasize that anal is all about giving pleasure to the person receiving and not something they are to endure for the pleasure of the giver. Hearing this philosophy and knowing your excitement to explore and take it slow may help him open up.
Also the episode emphasizes that anal is not all about racing toward penetration. External anal touch can be just as pleasurable and can be as far as you go at first.
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I think once he sees how much I like that in my ass he’ll be more open to trying anal again hopefully 