6 Things I Wish I Knew Before Losing My Anal Virginity

Lube can only take you so far

Stop me if you’ve heard this one before, but I had anal sex because my boyfriend wanted to.

It wasn’t my first relationship, but it was the first one that felt like real grown up love.

He wasn’t just a guy who gave me butterflies — though yeah, he definitely gave me some. He was also someone I could really talk to, who made me feel seen.

I didn’t just enjoy spending time with him — there was some real potential there.

And the sex — holy hell the sex.

By the time we were together, I had been with a few guys. Boyfriends, a few hookups — the usual stuff.

But none of them treated me the way he did. He touched me in ways that felt tender, loving, sexy, and dirty all at once.

I don’t know if it was great sex. Maybe it wasn’t. But it was definitely the best I had ever experienced until that point.

When he slept with me, it didn’t just feel good — it also made me feel good about myself. It made me feel cute and desired. I loved him, but I also loved the way I felt about myself when I was with him.

I was desperate to hold on to those feelings. So even after the relationship took a dark turn, I did everything I could to keep him.

And that’s where my virgin butt comes into the story. Because at some point, he became obsessed with banging it.

My feelings about anal sex were kind of complicated.

The idea of it really turned me on. It was naughty, taboo, and dirty — all things that excited the hell out of me.

And I really didn’t hate the way he wanted my butt so badly. That the thought of claiming it drove him so wild made me feel hot.

But I just wasn’t ready to take anal sex out of the fantasy realm. The thought of actually going through with it still made me more nervous than excited.

I knew I’d get there at some point. I absolutely wanted to be someone’s butt banging cutie. It would just take me some time.

Unfortunately, that’s the one thing he refused to give me.

He tried to convince me to give up my ass every time we were together. When I turned him down, he’d start heaping on the guilt.

He did two things in particular that really got to me.

The first was questioning my love for him. He’d repeatedly tell me that I obviously didn’t love him because I wouldn’t give him everything.

That hurt, because it’s the one thing I knew for sure. I had zero doubts about my love for him and did everything to show him how I felt. Well, except for the one thing he insisted would actually convince him.

His other tactic hurt me even more, though. When I didn’t give him what he wanted, he’d ice me out completely. He’d ignore me, leave me sitting on his bed while he sat at his desk typing out messages to other people.

All the warm affection and loving touches he used to give me were gone. And I was desperate enough to get them back that I gave in and agreed to let him have his way with me.

I still wasn’t ready — you can’t get ready with that much pressure. But I told myself to be brave. It’s just butt stuff. People do it and apparently enjoy it. How bad could it be?

Well, it can be absolutely terrible. Thankfully, it wasn’t that bad for me.

But it wasn’t great either.

It took some time. It took some work. But soon enough, I was on my knees and he was inside me.

It felt fine. Uncomfortable, but tolerable. Not the hot, pleasurable experience I hoped it would be. But still something I could put up with if it made him happy.

And honestly, I was kind of into it.

I know that’s all kinds of messed up because I was being pressured and manipulated. But toxic relationships are like that — your sense of what you want and need get all twisted up.

It’s not really the anal sex I was into, though. It’s everything that came with it.

It’s how he touched and kissed me after we did it. It’s the fact that he cuddled me instead of ignoring me. It’s finally feeling like he was mine instead of worrying that I was losing him.

And even though I didn’t love the anal sex we were having, I loved being the girl who did butt stuff. I wasn’t just having sex — I was being a bad girl and I just loved that.

Luckily, that relationship didn’t last much longer. I never stopped clinging to him, but he eventually lost interest in me. Even letting him have complete and total access to my body wasn’t enough to keep him

That breakup shattered my heart. But it also meant I could meet new people, sleep with other guys, and finally get to explore anal sex the right way — for me, not just for some dude.

Over the years, I learned a lot more about anal and all the reasons my first time kind of sucked. These are the things I wish I had known back then.

That Initial Discomfort Is B.S.

The first time my boyfriend did it to me, he kept reassuring me. He told me to just take it, because once he was in all the way it would start to feel better.

And he was right, I suppose. Taking it did hurt, but only at first. Once he was in and thrusting, it was much more comfortable.

I still thought the initial discomfort was a thing once I started having good, horny, enthusiastic anal sex. Because it always ended with a powerful orgasm — and started with one really uncomfortable thrust.

And I kept coming across people who confirmed it. They said basically the same thing my boyfriend had told me. That it hurts at first, but if you just suck it up buttercup it’ll be worth it.

I know better now, though.

It took me years and years to finally learn how to have amazing anal sex. Not just anal that gives me an orgasm, but that actually feels great the whole way through.

I was sure there had to be an uncomfortable first thrust because I thought I was doing everything right and it still felt bad. But I wasn’t doing it right — I still hadn’t figured out all the steps that make anal feel fantastic.

It took me more than ten whole damn years to finally learn all of those. So, let me tell you that the initial discomfort doesn’t have to be a thing. I don’t put up with anymore, and you definitely shouldn’t either.

Anal Foreplay Is a Thing

As far as I knew, there were two things that would make anal sex feel good. One was calming your nerves so you can just chill out and take it. The other was using lube — and plenty of it.

My boyfriend had the lube, and it was up to me to relax as best as I could.

But being cool as a cucumber wasn’t the only thing I needed. I also needed some proper foreplay.

Good anal foreplay starts with all the basic stuff to get you in the mood.

I don’t know if you’ve ever given in after a guy pesters you for some action, but let me tell you that you’re not exactly horned up at that point. And guys who push your boundaries don’t tend to put much work into getting you there, either.

There was no long, handsy makeout session for me. No sweet, loving dirty talk. No hand sliding into my pants to get me off and get me going.

It was basically me offering my butt and him taking it.

Then there’s the foreplay that’s specifically for prepping you for some backdoor action.

I didn’t get any of that either. He didn’t give me an incredibly intimate massage to get me comfortable with the sensation. He didn’t use his tongue like an eager anal fiend. He sure as heck didn’t have a sensible buttplug handy so I could start off with something easier than his shaft.

Nope. He had lube. That’s it.

Maybe he didn’t know any better. I sure as hell didn’t. And I still don’t see enough people talking about anal foreplay. But having anal sex without a good amount of it is just asking for a bad time, no matter how much lube you’ve got.

You Can Train for It

I hadn’t heard of anal training either.

Again, I thought it was all about having lots of lube and twice as much courage. But no, you can actually train your butt to be better at taking penetration.

There are a lot of subtle things your body has to do for anal to feel good. Most of it has to do with relaxing the right muscles. But that’s not easy when your reflex is to clench and tighten.

Before you take anything big like a dick or do anything intense like getting banged, you should practice with something a lot more manageable.

Using fingers first is a good option. Playing with buttplugs is even better. Ideally, you’ll get used to having something resting in you before you take some hard thrusting.

And it didn’t even occur to me that I could explore anal on my own first. Doing lots of solo buttstuff would’ve been the perfect way to go at my own pace, get comfortable with that kind of stimulation, and get lots more anal confidence.

Plus, it would’ve been pleasurable and taught me what good anal is like. That way, I would’ve known that the uncomfortable experience I got didn’t feel the way it should.

There Are Way Better Lubes

I don’t remember what kind of lube my boyfriend used, but it looked kind of cheap. I’m pretty sure he just grabbed whatever was on sale next to the condoms.

I was grateful he had it. It was way better than relying on spit.

I assumed whatever lube he got would be as good as any other. But it’s not. There’s a pretty big difference between cheap lube and the good stuff. And that’s a difference you can really feel when something’s going in your butt.

You can use some basic water-based lube for anal sex, but I don’t recommend it. A long-lasting, super slick silicone lube is going to be a whole lot better. And there are amazing water-based lubes designed for anal sex. They’re thick, slick, and work like a charm.

If I had known about those back then, I would’ve probably insisted that he buy a bottle before giving him my butt.

The anal would’ve probably still been so-so at best. But it would’ve been easier and more comfortable for sure.

Taking It Doesn’t Mean Being Passive

Taking it in the rear sounds really passive doesn’t it? Like you’re just supposed to lie there and let it happen. Or in my case, get on your hands and knees and wait for it to be over.

But being on the receiving end of some anal action isn’t like that. It shouldn’t be, anyway.

Because there are so many things you can do to make it so much better.

The biggest one is bearing down. You’ve got to work the muscles below your waist to fully relax them. Learning that completely changed anal sex for me. It made it so much easier, way more comfortable, and even more pleasurable than before.

Positions matter, too.

My first time having bad anal sex was in the doggy position. The first time I had great anal sex, it happened while spooning. I don’t think that’s a coincidence. Doggy and missionary anal are tough positions to pull off. Spooning with your knees up or going face down, bum up are better for beginners — they’re perfect for helping your body relax and open up.

Then there’s the fact that you can take charge of the penetration.

My boyfriend was the one with the dick. He clearly wanted this anal action way more than I did. Plus, he had done it with his ex-girlfriend so he had some experience.

Letting him take control seemed like the natural choice.

But it was my butt on the line, so I should’ve been the one doing it. I should’ve been trying different positions and shifting my body around until it felt right. I should’ve reached back, held his shaft, and guided him. I should’ve backed up onto his dick instead of letting him push it in.

He could take over once things got going. But I should’ve had way more control over the insertion.

You Need to Want It — And Want It Bad

I wasn’t ready to have anal sex at all.

I didn’t know enough about it. I hadn’t practiced at all. It wasn’t really my idea to begin with. Just a whole mess of reasons why I should’ve kept turning my boyfriend down.

I went through with it for all sorts of reasons. And one of them is that I figured I was as ready as I’d ever be.

If I could muster up the courage to tell him to go ahead and have his way with me, that should be enough. Can’t be much more ready than that.

But being ready to try it is nothing. I should’ve waited until I really, truly wanted it. Until I was downright horny for it.

That’s really the only way to enjoy anal sex.

It’s why every single bad anal story I’ve ever heard starts the same way — with a guy who really wants to do it and a girl who’s just being a good sport.

If you’re essentially having anal sex as a favor, you really shouldn’t be doing it at all. And you definitely shouldn’t if it’s your first time.

My first time doing it should’ve been after I got screwed so good that I got the urge to experience him in a brand new way.

It should’ve happened because I’d been fantasizing about getting my backside plowed and couldn’t get it out of my mind until it actually happened.

At the very least, I should’ve been feeling frisky, super horned up, and eager to blow his mind by being his dirty girl.

That’s not how it went down. I never got to feel an intense desire for it. I never got to daydream about it until I just had to have it.

My boyfriend never let me get there. He made anal sex feel like an obligation instead of a fun experiment. He made me feel like I owed it to him instead of treating me so well that I’d beg him to give it to me. He gave me so much anal anxiety that I couldn’t even get hot to the idea of it anymore.

And I should’ve never agreed to it because of that. Ready schmeady — anal is only fun for when you’re breathlessly horny for it.

Give Yourself a First Time You Won’t Regret

If there’s one thing I really wish I had known, it’s that it’s always okay to say no.

I was a major people pleaser, and that made me extra susceptible to my boyfriend’s manipulation tactics. I barely had any boundaries, and I didn’t feel right about enforcing the few that I did put up.

But even if I had said yes to him right from the jump, I think it would’ve gone more or less the same way. Same discomfort, same lack of pleasure, same physical struggles.

Because on top of barely understanding consent, I also knew next to nothing about anal sex.

And I’m really glad that all that anal ignorance didn’t turn me off of it completely. Even after such a bad start, I never totally gave up on anal.

You just can’t keep a dirty girl down, I guess.

Less than a year after that relationship was over, I still wasn’t having incredible anal sex. I was still making mistakes with my butt. But I was at least having hot, arousing, orgasmic anal — and having it on my terms.

It took me a long time to learn how to treat my butt right, and that’s not cool. Everyone who wants to try anal should at least have a good chance of enjoying it. And that starts with knowing that it takes a lot more than a bottle of cheap lube.

This post contains affiliate links to buttplugs and great lubes. If you click on one and treat yourself to anything from the site, I earn a small commission and you’ll be ready for amazing anal!

If you liked this article, you should totally check out the Welcome to the Anal Laser Light Show (Weird Sex Toys, Sex Dreams, and Dual Dicking) episode of my dirty and intimate sex podcast, Pillow Talk With Emma Austin!

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