Message: Boyfriend Insecure About DAP
Rafael: Hello, thank you for your blog. It has a lot of useful information and interesting user messages. I’m a gay male, mid-30s, bottom exclusive. After reading your double anal article, I wanted to try it out. My first attempt with dildos wasn’t successful, it felt awkward and difficult to achieve penetration, so I decided to change tactics.
I presented your blog to my boyfriend, let’s call him John, and he liked reading it as much as I did.
Then, I suggested John to use one of my dildos along with his penis. He accepted and we tried the next day. I was pushed to my limits and it was a bit painful, a similar pain that I felt when I was new to anal.
John was very helpful and patient, he gave me all the time I wanted, even if it meant only oral for the night. After many tries, I managed to take both John and the dildo at the same time.And I have to say you are right. The feeling was incredibly intense! I was stretched to my limits but in a good way. I’m used to having prostate orgasms and didn’t have one that time but the effects were as powerful in different ways. I’ve heard about a type of anal orgasm that is focused on the sphincter and rectum, maybe it was that.
After that night, I wanted to go for the true double anal experience but there were problems. John and I are monogamous, we’ve been together for more than 5 years and we’ve never cheated on each other.
When I suggested having another man for double anal, John was uncomfortable. We talked a lot about it and I think he’s feeling insecure about his size since I enjoyed DAP a little bit too much. He even commented about the size of one of my dildos, something he never did before.Here’s the thing, I love John. He’s a great partner and amazing in bed. I often have prostate orgasms with him. I’m now feeling guilty. Our life outside the bedroom is going strong but the sex now is less intense. There wasn’t another double anal night ever since my suggestion. I kinda don’t know what to do and want to hear your opinion about this.
It’s great that you were able to experience DAP together—even using a dildo, that’s a huge milestone, especially as a first time. The fact that it triggered something new in you doesn’t mean you’ve outgrown what you have, or that you don’t enjoy sex with your partner. Double anal is a type of stimulation that can’t be replicated with just one penis or dildo, it’s a unique sensation and experience that requires multiple dildos, partners, or a combination thereof.
It also makes perfect sense that John might feel insecure or hesitant. When a partner sees you crave something that they alone can’t physically give, it can stir up feelings of inadequacy—even if they’re totally unfounded. That doesn’t mean he isn’t enough. It means he’s human. The best thing you can do now is help him feel chosen again. Let him know how much that DAP night meant because it was with him, not in spite of it. Remind him how you trust him to take you to your edge safely, and how no toy or fantasy can replace the connection you have.
As for involving another man—it’s okay that the idea was hard for him. But it doesn’t have to be off the table forever. You’ve already laid the foundation by being honest. What matters now is showing him that this isn’t about replacing or comparing—it’s about exploring something you want to share. You can keep the door open gently. Maybe frame it less as “bringing someone in” and more as “experiencing something together that we couldn’t otherwise do.” Let him feel like it’s an adventure you’re inviting him on—not a compromise he has to make.
In the meantime, you don’t have to give up DAP entirely. Keep training. Try dual toys again now that you’ve done it with him. Keep your body open and engaged. And most of all, keep celebrating what you and John already have. This doesn’t have to be a roadblock—it can be the beginning of something even deeper between you.
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