Note: there’s some graphic shit (sometimes literally) in here.
The first time I ever considered having anal, I was absolutely turned off. Really, the closest I had come to it was having a finger jammed up my butt by surprise during sex. I was drunk and pretended to like it.
My ex used to bring it up all the time. He claimed he was just kidding, but I always suspected that deep down inside, he desperately wanted to backdoor me. We never went through with it, though. I guess I never fully trusted him. Seriously, it takes an outstanding level of trust (not necessarily commitment or love, but trust) to let someone ram it in your ass for the first time.
Years later, I met my current boyfriend. One day, we found ourselves on his couch, a little bit tipsy. We’d been dating for two or three months and were totally hot for each other. I think we were in the midst of a sloppy make out session. You know, the ones that start off with watching TV all innocently but end up in dry humping so hard that your underwear is chafing your vag. We couldn’t have sex because I was ragging it so he proposed anal. You’d figure he’d rather deal with a bloody cunt than a shitty asshole, but whatever.
So, I ran to the bathroom, took in a deep breath and shoved a soapy finger in my bum hole. It came out clean. Thank God; I could just imagine getting crap on my boyfriend’s penis after only 2 months of dating. How mortifying would that be?
The trick is to start slow. I mean, you can’t expect to slap on some lube and just shove it in. No, it’s more like chug half a bottle of cheap wine and then it’s one finger at a time until your hole gets more and more dilated (gross, I know).
After a bit more fingering, he’ll be like, “Are you ready?” That’s when, in your best pseudo-porn star voice, you whisper, “Do it.” Then you shut your eyes real tight and stop breathing for what seems like forever. Of course, that may be your initial reaction, but not breathing and clenching your muscles is actually the worst thing you can do. You need to stay calm and relaxed to allow for a smoother insertion. It wasn’t so bad for me. I didn’t bleed, but you might.
Once he’s balls deep, you’ll start feeling like you’re taking a reverse shit. You’ll immediately pull back, half expecting a turd to come sliding out. Thankfully, there should be nothing. Once he sticks it in again, it’ll be kinda hard to enjoy yourself, as the whole time you’ll be paranoid you might poop.
The experience doesn’t feel particularly good or bad. I mean, there’s a specific sensation, but I’m not sure how to describe it. I don’t know if I’d ever be able to cum from it, so to make things a little more enjoyable, I suggest having a vibrator handy.
If you don’t own a vibe and you’re fed up because anal isn’t providing you with that climax build-up you’re looking for, you can switch from ass to vag, but do it carefully. If for some reason you aren’t using a condom (which you most definitely should), he needs to wash his dick really well. If you are using a condom, he’ll need to get a new one. It might kill the moment but the last thing you want is to inadvertently get poop particles in your twat; that’ll almost surely make for a nasty infection.
So in all, I’ve done anal three times. Once, there were some brown smears on the condom. If that happens to you, don’t freak out, it’s normal. You can’t honestly expect the dick to come out clean every single time. Plus, the guy knows what he’s getting himself into and probably half-expects it. He’s sticking his dick in a shit tunnel, come on.
My advice to you is this: if you’re curious, try it. It hurts, but the pain is tolerable. Just remember to use a lot of lube, and none of that scented crap or “tingling sensation” stuff (take it from me, it burns). If you aren’t ready, don’t allow yourself to get pressured into it. Not everyone is interested in getting butt fucked (hi, Melissa), and that’s fine. Sexual limitations are personal, and you should define them at your own pace, rather than someone else’s or a porno’s.