First Time Bottoming? Tips From Your Fairy Gay Godmother 

Bottoming isn’t everything you see in porn. From the chiseled bodies to the abundant exclamations of “Fuck!!”, ok that last one happens in real life, but still. For your first time bottoming, you’ve probably got a ton of misconceptions. Whether you think anal sex is clean and easy-breezy or if you think you can just wing it, you need to think again.

Penetrative anal sex can take a lot from both the giver and the receiver. You need to set some expectations, especially if this is your first time ever (or even if it has been a long time). You’re going to want to prepare beforehand and learn the anatomy of what’s going on down there.

My first time bottoming a real dick was with a guy who liked that I was a virgin, he told me he’d make it special. Honestly, still felt like a virgin after, but with more daddy issues somehow. He busted his nut basically on entry and went soft so fast I barely felt a thing. Girl, you will get through this. If I made it through a ‘romantic’ minute of sex on a mattress on the floor of his bachelor pad, you can make it through your first time too.

Only, your fairly gay godmother is here to help.

I’m going to give you some advice on how to make your first time go smoother and with a lot less embarrassment than being trapped at a mountainside condo full of disappointment. Seriously, cabs don’t go back to the city from where I was.

First up, what is bottoming?

If you don’t know, maybe you’ve never watched porn, or you’re new to gay culture, the bottom is the one receiving the cock in their ass. Blunt, I know, but sometimes you just have to lay out the facts. The bottom can change throughout your fuck session or it can always be you, seriously, I don’t judge. 

Some guys will only bottom for their entire life. Others, like me, are vers, meaning I like both the giving and receiving of penetration. The giver is often referred to as a top. This doesn’t mean that only one of you is getting head unless that’s your thing, top, bottom, and vers only refer to the sexual preferences that gay men have around anal penetrative sex.

You might find out that bottoming is not all it’s hyped up to be and end up topping. Maybe you’re no stranger to gay sex, but you’ve never bottomed before. Either way, I’m going to lay out some big pieces of advice below.

Why would you bottom?

Well, this one is simple for me: because it feels fucking great. On a serious note though, men don’t have vulvas, no vagina, nothing of the sort so we’re left with limited options. Sure a blow job feels good, but sometimes you want something more intimate, and maybe involving less teeth. Enter the anus, pun intended. Your anus can stretch far more than you’d think possible and accommodates a cock perfectly.

Also, and probably the most important note, your prostate is located 2-3 inches inside your rectum. Once you’ve experienced a prostate orgasm you won’t want to bother cumming without something in your hole ever again. Seriously, it feels that good.

Sometimes bottoming can be so pleasurable that you feel his cock inside you hours later. That’s when you know for sure that you’ve been dicked-down. And yas bitch, does it ever feel good.

Cleanliness is next to Hole-iness

You’ve probably heard of rimming before, but in case you haven’t, it’s the pleasurable licking of your partner’s delicious booty-hole. Now I say delicious in reference to a fresh clean showered booty because you literally can get pink-eye from an unclean hole. This is basic hygiene and really all it takes to have a hole that is ready to be served to your hungry man is a little soap and water. It’s easy enough really.

You can take it a step further with douching. And no, that’s not getting fucked raw-dog by a douchebag, I mean using an anal douche to clean any “unwanted” bits out of your rectum. I’m referring to shit, feces, poop, whatever you call it, it’s not fun having caca on your cock. There is a down-side though, frequent douching or use of enemas can damage the anus, making sex less pleasurable down the road. I think it’s worth the risk, but everything in moderation, don’t douche every day if you aren’t getting fucked, there’s just no point.

I’m not bottom shaming here, poop is normal, everyone’s gotta go, but the sight and smell can really put a damper on things. Understandably you’re fucking a poop-chute, but the gays have found ways around this predicament. From ridiculous pornstar diets to the clear running waters of a well-douched hole. It can be one of the first things you do to prepare for anal penetration.

Of course, there’s always the next level, which is a coffee scrub, or similar. It’ll leave your hole smelling fresh for hours, plus it boosts sensitivity thanks to mild exfoliation. Just a final heads up, I’ve been fucking for years, I still sometimes pull out with some poop on my dick. But it’s not the end of the world. Shit happens, and in the case of gay sex, you can take that literally.

Go solo, first

My biggest piece of advice is to explore, explore, explore. Finger your hole on your own, try and find your prostate and pleasure yourself. See what the sensation feels like. This way you’re getting used to the feeling of having something inside you, plus a finger is manageable and the perfect size and maneuverable enough to hit that spot just right.

Next, I’d buy a reasonable sized dildo, find one similar sized to your dick or by the ‘Average Joe’ models most companies sell. The perfect dildo usually has some flexibility to the shaft.

Can’t afford a dildo? Buy an English cucumber for like $2.00. You can use a peeler to trim down the size of it and explore with a kitchen vegetable if you’re looking for a cheap alternative. Honestly, we’ve all used something in our kitchen for sex, just remember to throw it out.

Lube, lube, and probably more lube.

The best hole is a lubed hole. Lubrication goes a long way with anal sex as your rectum won’t get ‘wet’ like a vagina. There’s not much in the way of natural lubrication back there, so bring along plenty of your own. Avoid using certain lubes based on any allergies you or your man may have. Silicone lube lasts a long time, but can feel gunky, and will absolutely destroy certain toys. 

My favorite lubes are water or oil-based and I have a penchant for spit. Spit, however, takes practice to get used to and I don’t recommend trying to spit fuck as a beginner. Buy some quality lube online and get ready to experience some new sensations.

Lube can seriously make all the difference between bad sex and a fantastic ass pounding. It’s all in the quality and slick nature of the lube. It’ll help his cock slide into your hole or help you play a little easier with toys. Either way, it’s worth investing in the lube that you like, so try out a few different ones to really get a feel for your favorite.

Try some more unique toys

There are a ton of anal toys on the market. From butt plugs to vibrators, there’s something for every hole. I recommend a vibrating prostate massager that penetrates deep enough to enjoy solo or with a partner. It’s a great way to loosen your hole and will have you dripping precum in no time at all. 

After trying a massager you could try a butt plug. These will get you used to the sensation of fullness inside your hole, but won’t give you the constant stretch of your rectum that a dildo might. It’s a great way to practice enduring the sensation, plus they can even be remote controlled. You might consider giving your man the control and letting him drive you wild!

RELAX

Seriously, this is like the words from Rupaul, just chill. Relaxing your hole will be a different sensation at first, after all, you’re used to keeping things inside and not letting much in or out. So, this experience is going to be challenging for some.

Take deep breaths when your hole is being penetrated and once the head of the toy or his cock is inside you, take it slow for a second. Get used to the sensation of fullness and stretching before you take the whole toy or cock because you don’t want to have to cut things short (but if you do, that’s totally OK).

Go slow, take your time, the bonus here is building sexual desire as you’re easing into the pleasure. You’ll want to take that toy or cock.

Now that your ready

Take all of these practices to the bedroom, toys, lube, douching, the whole lot. Your first time riding a real cock is bound to be awkward, but I’ve got guidance here as well. Remember how my first time went? Well, at least I was in control and on top, which is key.

You’ll want to be riding ‘cowgirl’ so that you’re controlling how much penetration is happening and how fast things are moving. If you get topped doggy-style, he’s in control and might go too forcefully before you’ve relaxed. So stay in control at first, and ensure you’re getting pleasure out of everything before getting faster or rougher.

On that note, I’m gonna leave you to it! 

Bottoming is an intense experience that’s not for everyone. Some gay couples don’t even have penetrative sex and opt for mutual pleasures like BJs or masturbation. Just remember, this is your hole doing the work, stay in control and try the things you’ve practiced on your own.

Happy Bottoming!