Grace: My name is Grace, and I’m 27 years old. I’ve been in a relationship with my boyfriend for about a year. I have a strong preference for anal sex over vaginal, but he prefers vaginal and only engages in anal to make me happy, as he doesn’t particularly enjoy it himself.

We occasionally watch porn together, and I find myself really attracted to group sex scenes, especially those involving double anal penetration. These scenes make me incredibly aroused, and I often imagine myself in such scenarios. However, he’s not comfortable with these types of scenes.

In private, I’ve experimented with anal toys and really enjoy them. For a longer period now, I have been fantasizing about trying double anal with him using a toy, but also with another man involved. This desire has become something that I feel needs to be part of my life, and I’m struggling to reconcile this with my current relationship dynamics.

I’m unsure how to approach this with my boyfriend, given his preferences and discomfort with certain types of content. I’m starting to feel like this might be a deal-breaker for me, and I’m considering two options: either ending the relationship to find someone more compatible with my desires, or possibly building a secret life where I can explore these fantasies without his knowledge.

I’m torn between honesty and the potential consequences, and the desire to fulfill my needs without hurting him. Could you provide some guidance on how to navigate this situation, or how to communicate these desires with my partner in a way that respects both of our feelings and boundaries?

I’m sorry to hear that your partner doesn’t share your preference for anal. What leads him to prefer vaginal over anal? Does he not get as much physical pleasure from anal, or does he dislike the idea of anal sex? If he doesn’t like anal at all, you may have a hard time convincing him. If he prefers more sensation, though, it’s possible that starting to do double anal with him would be more pleasurable for him.

I encourage honesty and finding compatible partners over dishonesty and cheating, so if you are unsatisfied, you should be very clear with him that you want to be anal only and to start doing double anal, and ask him if he’s willing to try while also working to make it more pleasurable for him. If, for example, he wants more spontaneity that can be harder with anal, making the effort to stay clean and ready for anal at all times through diet, cleaning daily if needed, and wearing a butt plug when not having sex can make that much easier.

If he’s not interested in trying to go anal only or having double anal, you may need to end the relationship and find a partner who will be compatible with you sexually and who obsessively wants anal only with you as well, and wants to stretch your ass with his cock and a dildo, and eventually two cocks. I highly recommend pursuing the anal only lifestyle, double anal, and ultimately going double anal only.

Abby: Hi, I’ve been anal only with my boyfriend for two and a half years now, and it’s been great, we do it every few days if not every day sometimes, and we have been exploring stretching a lot too. We use some bigger toys, which helps make frequent anal easy since my boyfriend is quite large, both girthy and long. We have also incorporated some other guys into our sex life, mostly spitroasting and them running a train on my ass. My boyfriend wants us to start having double anal sex and I would love to as well but I was wondering if you had any advice for how to do it safely given his size.

Thanks for reaching out, it’s so good to hear that you’ve been having a good anal only experience and are now looking to advance things to double anal. I know it can be intimidating if you have a large partner already, but it’s well worth it to start doing double anal or even going to double anal only.

Since you already play with toys regularly, I encourage starting to go to toys larger than your partner when masturbating, and then starting to have sex with him with a smaller dildo alongside his cock. You can work up from there to a dildo similar in size to him or the partners you plan on having double anal sex with, until it’s easy and comfortable to do so regularly. I’d encourage starting out doing this at least once a week, and increasing from there.

Similar to getting started with anal, advancing to DAP is just about gradual progress and going slowly enough at first that things don’t hurt. If you stick with that, you’ll be just fine and you’ll be taking two cocks up your ass in no time! From there, I recommend exploring the idea of going double anal only, even if just sticking with your boyfriend and a dildo every time you have sex at first, and then swapping that dildo for another guy when available.

Good luck, you’re going to love it!