Message: Birthday Present Advice
Lilly: Hey everyone, I wanted to get some advice on something new I’m thinking about.
I first found out about anal when I was 16 and with my first boyfriend. Since then, anal sex became kind of my go-to because it was easier sometimes than dealing with condoms or the pill. I’m 23 now and currently with my boyfriend, who’s 28. We’ve been together for almost 9 months.
Sometimes we watch porn together, mostly group sex. It really turns me on. I love to watch it with him and don’t like watching it alone either. Usually, I ask him to search for something rougher, and we stumbled upon some scenes with double anal that I find insanely hot. I think he’s noticed that too.
Recently, during one of those scenes, we started talking, we were joking about DAP and we got somehow to a point he asked if I would ever consider trying double anal with one of his friends as a birthday present for him. I asked him if he was serious and I told him I’d need to think about it.
Honestly, I don’t want to chicken out because this is something I really want to try and I also would like to make him this birthday gift. But I’ve never done double anal play with a dildo or anything, and his birthday is coming up soon. I’m worried I might not have enough time to train and prepare.
So, here are my questions:
1) Since I do anal regularly, how hard is it to train for double anal play quickly?
2) If I do try it but I’m not 100% prepared physically (I can see myself so eager to try it, that I go hard on them and not feel any signals my body might be giving), am I at risk of permanent damage?
3) Also, could doing something like this ruin my relationship or affect how people see me?
Anyone who’s been down this path or has tips, please share. I want to do this safely but also don’t want to miss out on something hot just because I’m scared or overly cautious.
Thanks so much for sharing and reaching out, it sounds like you have a wonderful opportunity to explore a shared fantasy. I would suggest not going too fast with this plan, though, and making sure that you’re actually ready for it first!
Doing anal regularly is a great first step, it means your anus is likely well-conditioned and in a good place to stretch open more pretty quickly and easily without injury. You still want to avoid going about it too quickly and listening to your body, though.
I strongly suggest trying it first with two dildos, or with your boyfriend and a dildo to ease into it, and do that half a dozen times or so at least until you’re comfortable doing it without discomfort/injury, and then try introducing another partner into the mix.
There’s always a chance of relationship strain when introducing new partners, so you should discuss this thoroughly before trying it in reality to make sure you both actually want it and are on the same page and how to deal with potential jealousy before it arises. You may find that you really want to stick with his cock and a dildo instead.
For more specifics, check out our Guide to Double Anal Sex.