Dear Daddy: I tried anal but it hurt, any advice?

Hey daddy. I've been seeing someone and we tried anal for the first time. It really hurt me and we had to stop. I feel really guilty about it. Do you have any advice?

There are a lot of reasons why anal sex can hurt but it’s important to note that it doesn’t hurt just because it’s anal. There’s always discomfort when something soft is invaded be it a rectum or a vagina and both come with a whole array of ‘things that can go wrong’ both mentally and physically. The difficulty for us is that thanks to porn we have a mythology about bottoming and that takes a bit to demystify and put back where it belongs: as a tool in the toy box of fun.

Step one of unpacking and dismantling it is to bust up the ‘urban myth’ party that crowds the bedroom when the topic of anal sex comes into play. Just because you are gay doesn’t mean you HAVE to bottom or top. Enjoyment of receiving anal penetration doesn’t make you a bottom. In fact the sooner you throw out as much of that kind of garbage as you can the happier you will be.
Step two is untangling your pleasure from your expectations and phobias as much as your concept of ‘masc’ or ‘femme’ having any relationship to position in sex. We get this sexual activity all tied up with ‘being a guy’ and really that all needs to go. I know first hand that the ‘ultimate guy’ whimpers like a bitch in heat just like anyone else when the sex is right so don’t let your curiosity about anal sex even touch your sense of masculinity. They aren’t even related in reality and only appear to be culturally because that’s the media stereotype.
Step three is divesting yourself of the additional baggage of shame, guilt or embarrassment. You have no reason to feel badly about the first time being a ‘problem’. NO matter what people say, that first time isn’t the cleanest, photo friendly event. My first time as a bottom? 10.5 inches and shaped like a mallet. He wasn’t patient, wasn’t kind and didn’t prepare me. I bled and it hurt.  I assumed he knew what he was doing and would be gentle. Lesson learned and soon after I was the one in control as the bottom. I figured out, on my own, how things worked and what was needed to keep from hurting.

Remember: It’s not YOUR job to make sure sex doesn’t hurt or feels good. It is, in fact, a shared responsibility between you and whomever you are with. Unless your trying to ram it in, there’s another party doing the pushing and they need to have helped to prep and during sex itself.  You are only permitted to take full responsibility when you’re by yourself.

Step four is education. Sex hurts the first time. And then the second and third and so on because you’re asking your body to endure an invasion in sensitive places. Even after years of regular sex the first few moments have uncomfortable, even slightly painful, things that happen but with practice and experience you discover that once you get used to it you can really enjoy yourself.
Now comes the real ‘education’. This is a ‘master post’ that provides instruction on safe, sane, and effective anal sex preparation and performance. Even experienced tops can learn a few things from this and after you have read them you should share and discuss these things with your ‘top’. https://dirtydaddythings.tumblr.com/post/142951303327/dear-daddy-first-time-top
It’s a lot to read but think of it this way: You now have the opportunity to go into this prepared, with proper expectations and a clue and those three things make a difference on your end. If you can get your ‘top’ to study along with you, the experience for both of you will be that much sweeter.

Any dog can hump but a real ‘man’ knows how to do it right.