Shameless Bottoming

A beginners Guide To Back Door Pleasure

Sex is a taboo subject for some reason. People are so embarrassed and scared of speaking openly about it when (for the most part) everyone takes part in it. So when it comes to other kinds of sex such as oral or anal, peoples' heads seem to just implode. When considering trying anal for the first time, it can be incredibly scary. There is a lot of stigma and misinformation around anal sex, that could easily be solved with simple education, but the mainstream is too prude to even admit anal sex is becoming more and more common.

The term ‘shameless’ is often used negatively to describe someone who feels no shame or regret for their actions, that should otherwise be seen as shameful. In this instance, I’m using it to show resilience in the face of adversity. Whilst a lot of people still look down on anal sex as a dirty, queer and unnatural act (which is all BS by the way) we can be proud taking part of it regardless! I myself am a proud bottom. I am no longer embarrassed by it despite other peoples views. If practiced properly and carefully, anal sex can be an intimate, pleasurable and incredibly fun experience that I would highly recommend. So the point here is that shouldn’t be ashamed of enjoying anal sex. Whether you’re a top, a bottom, verse or you’re not interested in it at all! There should be no shame in your interests or kinks. Sex is there to be enjoyed.

Now, that’s the mini pep talk over, let’s get into the part you’re all here for! Today I'm going to be talking you through some simple tips for prepping for, and enjoying anal sex, safely! I am no sexpert however, so I am linking other articles with more detail throughout this piece.

Start small - When starting out with anal sex (especially after the unrealistic expectations set by porn) it’s easy to want to go full throttle. Don’t, it will really hurt. Anal sex is a process that you need to build up to. You can start with your finger and maybe build up to 2. Start maybe with a butt plug and build up from there. You are not going to simply get on all fours and ride a 9 incher like a cowboy, it won’t happen. So be patient, build up to it, and most importantly listen to your body. Your first time also isn’t likely to be amazing, especially if your expectations are high. But it’s like muscle memory, the more you do it the more your butt with adjust and in time it will be more and more natural, trust me.

Mess may happen - When you’re treating something as an entrance that is also an exit, there is a chance that you may meet some oncoming traffic along the way. Both the top and the bottom in this scenario must be prepared for this inevitability as it can happen. Of course it can be embarrassing, no one wants that to happen but sometimes it just does and that’s ok. But here’s a couple of hints:

At the end of the day, there are pros and cons to everything, benefits and risks. But if you’re going to take part in anal sex just make sure you do the research and you’re as physically and emotional prepped as you can be!

Communication is key - Anal can hurt, periodt. If you don’t communicate effectively, especially if the hammer isn’t listening to the nail, it can be painful. Firstly, it’s important to have the conversation about anal before actually doing it, no matter what sexuality the relationship is. Don’t just spring it on someone, have an open and honest conversation about it first. Secondly, during sex it’s important for both (or all) parties to be mindful, careful and to check in. I’m not saying to ask “are you ok?” Every ten seconds, it can be kind of a mood killer, but if you can see one person is struggling, stop and check if they’re ok to continue, it’s just courteous.

The wetter the better - When it comes to anal, lube is your best friend. The anus doesn’t self-lubricate like the vagina, and so lube is necessary to make the movement more enjoyable for all involved. In this instance, the bottom knows best. If the bottom says there isn’t enough lube, there is not enough lube. Don’t argue it, it’s their butt. Here’s a great piece to help you with what lube will work best for you (

Analingus can be a great way to get you started - To those who are unfamiliar with anal sex, or anything butt related, Analingus (also known as rimming) is that act of running ones tongue around one someones butthole. Now if you haven’t come across this concept before, it’s likely to sound very odd. But trust me, it’s one of the best feelings. The entrance has many sensitive nerve endings, so even the subtlest of movements can be very pleasurable. This is the butt alternative of ‘eating out’ and can be a great way to get the butt lubed up before sex. This is not recommended as a substitute for lube, as saliva dries up. But, it can be used in addition too, and can feel amazing (after a wash of course). So if you’re not quite ready for the full thing yet, maybe give this a ago!

Use a towel - Sex can generally be a messy experience, especially anal. I always remember seeing this meme years ago (see image on the right) and I didn’t get it. I wasn’t aware that it was common for people having anal sex to lay a towel down. But, now after a 2 year relationship it seems weird if I haven’t put one down! It’s just a great back-up, especially if you’re worried about mess, to catch any accidents and avoid having to wash the bed every time you want some sexy time.

Relax - If you’re tense during anal sex, it’ll be obvious. Your sphincter will close up and refuse entry, making it even more painful. Relaxing your body and relaxing your muscles will make the gradual entry process easier and therefore more enjoyable. Of course the first time can be tense for you, you’re putting something up your ass. But, if you just breathe and relax your body and muscles, it’ll make the process that much smoother.

Appreciate and enjoy your butt - This is my final piece of advice, appreciate your body! For me, insecurity makes sex hard to enjoy. Holding my stomach in, tensing muscles, posing etc. Again, the damage of porn is that we have to look immaculate during sex at all times, in reality that isn’t the case. Don’t be afraid for people to see you at your ‘ugliest’. I know it’s easier said than done, but the more you accept and appreciate your body, the more confident you will feel. I’m at a place now where I love my butt, it’s not muscley nor is it firm, but I like it for what it is.Having that mindset (along with a jockstrap or a thong) gives me the confidence to feel like the best bottom in the world.

Anyway, this has been a deep (pardon the pun) and long (and again lol) article, but anal sex isn’t something that should be just jumped into, nor should you feel pressured to do so! I hope this article has been helpful for you and may make your experiences that little bit more enjoyable! Feel free to follow the incredible @bybobbybox on socials too. This is not a collaboration with him, I just love his work!

Love ya!




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