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Why and How to Practice Before Your First Time Bottoming as a Gay, Bi or Pan Man: A Beginner's Guide

Aubergine In Peach
Getting yourself prepared will help make your first time great

As part of our Complete Guide to Bottoming for Beginners, see below for why practice is important, skip ahead to How to Practice for your first time bottoming, what beginner male dildo to get, and how to use a dildo. Other posts in the series you can such as our complete anal douching guide can also be found on our blog.

P.S. If you enjoy this, come say hey on IG (@TheAgeGapGuys) or TikTok (@AgeGapGays), where we have fun promoting awareness of diverse relationships. Follows very welcome!

Why Practice Is Important Before Bottoming For the First Time

Imagine a gymnast doing the splits, and how they slide down to the floor with effortless ease. Now you try.

If you did, unless you're a super-splits-Suzie, you'll have found that you could relax so far down to the ground, but your tight muscles stopped you getting further.

The same principles apply to bottoming!!

Practice Makes Perfect

As with doing the splits; learning to take something like a penis up your bum takes practice. Whilst it won't take you the months and months it takes most to learn the splits, it might take a little time before you're able to put big enough things in your bum to make your first time having sex with a man a comfortable and fun experience.

Practice doesn't mean grabbing the biggest thing and learning to force it up there. It means starting small, and gradually working your way up to bigger things. Fortunately your rectum is actually quite well shaped to take an average to above average penis (se the anatomy section on our Complete Guide to Douching to help explain more), so a lot of this practice is to do with your sphincter ... but in perhaps a different way to what you think....

Relax Don't Force

Unless you're looking to put some fairly girthy things up your bum - which we wouldn't advise for a beginner - getting ready for a man's penis up your bum is about learning to relaxing your bum hole, not stretching it.

I'm sure that - as we all have at times - you've done a poo when you've gone, "Wow!" that's huge!! Well passing that poop not only shows you the elasticity of your anal sphincter, but also that you can already fit a penis up there!! With the diameter of the average man's penis at approximately 1.5 inches, there's no need for any bum stretching.

Whilst your bum is used to relaxing when you go to the loo, it's only for a second or so at a time. You need to learn to keep your bum hole relaxed when something - like a man's d*ck- is going in and out of it, and you're potentially moving (e.g. thrusting your hips).

How Do I Practice Bottoming Before Anal Sex?

Starting with our objectives, you want to:

Be able to relax your bum enough to comfortably take a man's penis, for a sustained period of time, whilst undertaking sexual movements e.g. thrusting/being thrusted in a pleasurable way.

Most men have been conditioned that their bum is only for things going out, not in. Alongside the concerns many have about what being gay means for their life and how people view them (but this isn't the time to go into that), it can mean we can be scared of our bum. Whether you are or not, firstly remember that men of all sexualities can like having things up their bum - it's where the male G-spot is after all!! - and it means nothing about you as a person. For some this

Preparation and Getting Clean

We won't go into this in detail, but if you're going to practice bottoming, you'll likely want to get yourself clean down there. To help with this we've provided a complete guide on how to douche here.

Start With a Finger of Fun First

Before you go out to the adult toy shop, it's a good idea to start with just using your fingers to begin with. Not only are your fingers thin so most easily able to be put in your bum, but you'll be able to explore the inside of your ass.

Learning what feels pleasurable is important as a bottom to make sure you enjoy gay sex as much as possible. For any that want to top at some point too this has a secondary benefit of helping you make sure the person bottoming for you has a great time.

Note - make sure you've got short nails for this, however try to avoid cutting them just beforehand or then can have sharp edges that can damage your anus and rectum.

Liquid Silk Anal Lube Lubricant Gay Sex
Our recommended water based lube

Lube Up

We recommend water based lubes like Liquid Silk (our fave) or ID Lubeas though they may need reapplying after a while, they don't damage silicone toys (which silicone lubes can) that you're likely to use down the line. They are also best bought from gay sex shops as they will be specifically for your anus and not vaginas.

Please don't just use spit. You'll find out it dries quickly and you'll find your fingers can get stuck and be painful to remove. Moisturiser or lotions can also sting/burn and be bad for your rectum so are also best to avoid.

How to Relax Your Sphincter and Explore Your Bum with Your Fingers

Ok, so it's time to put something up there. Hooray!! But there's no rush. Put on some relaxing music, set the scene and just chill for a few moments. Start with a bit of lube on your finger and just rub your hole. There are thousands of nerve endings there so it'll likely feel nice (though not for everyone). Just teasing round this area can be both pleasurable and also help your bum to start relaxing.

After a little bit of finger rimming, start to put a little more pressure on your anus. If your muscles are relaxed they will soften and will gradually let your finger pass by the external and the internal sphincter muscles - which go on for about an inch/2.5cm. Take this slowly as if you push hard too soon you'll tighten up and can find a fairly intense pain and you'll need to stop (this is more common when putting larger things up there though). Gradually work shallower and deeper with a well lubricated finger, and you'll gradually find that after a little pressure on your hand, your finger suddenly slips inside. Depending on how slowly you've worked up to this, it can come with a slight feeling of a release of pressure on your finger.

Note: You might find this all very arousing and it's perfectly fine to masturbate whilst fingering yourself. Be conscious however that this usually makes your arse tighten a bit, so is best to stop while working up to the next stage.

Gay Peach Bottom
Treat your peach nicely ; P

Once inside, take a second to just feel the sensations. Feel the control you have over your bum hole, and gradually explore your rectum. Rubbing the walls with a light come hither motion or starting to move your finger in and out, you'll likely start to feel different pleasurable sensations. Around the second joint on your knuckle on the 'ceiling of your rectum', you may find your prostate and G-spot. Try rubbing and stimulating this in different ways and you might feel some intense sensations that you haven't felt before.

After playing for a while with your bum relaxed, you may want to slowly insert a second finger (with plenty of lube). There's no problem if this is too much for you, or if you just prefer the sensation of one finger, or even if you struggle to get one finger in! There's no rush

Note: At each stage of this, you may find your bum tense up and clench. That's perfectly natural and can happen sometimes even when you're a bottoming pro. Just pause for a second to let yourself relax again, and maybe ease back to the step you were doing before before working back up to the stage you got tight at.

Choosing a Male Anal Sex Toys For Beginners

Ok so you've got used to the feeling of your fingers in your butt, and you're feeling ready to explore sex toys. This is a great way of getting prepared to bottom, as you can get used to relaxing your bum with something more substantial inside you.

As you can see from the graphics we've made below, firstly the size of the average male penis isn't perhaps as big or as thick as you'd think. Whilst to a degree this is country and ethnicity dependant, the global average is sitting at 5.1-5.5 inches long and 1.5 inches thick.

Recommended Beginner Male Dildo Length Butt Plug for Starter Anal Sex
You don't need to start off big to be able to bottom

Because of this, you don't need a toy that's particularly big to be able to accommodate the majority of men. When you consider the lower part of you rectum is around 6 inches, your bum is well prepared for most guys you'll bottom for.

A trip to the sex shop or online adult store can be quite intimidating. You're confronted by loads of enormous dildos and butt plugs of all shapes, sizes, colours and function. Because of this it can be easy to get carried away and go for something 8 or 9 inches long and 3+ inches thick. That's the most common size so it must be normal, right? As you can see from the graph we've made below, they tend to be way bigger than the average male penis size in both length and thickness.

As you become a more experienced bottom, you might want to explore bigger sex toys, but right now, you likely won't be able to get them in your virgin bum without pain or potentially injury (I had this exact experience of getting a toy that was too big, that to this day sits as an unused waste of money in the sex drawer).

Different Small to Extra Large Dildo and Butt Plug Sizes Graph Chart
You can see for your first time bottoming, you don't need huge toys

As key beginner male dildo recommendations:

  1. Buy one, don't try homemade (they're unsafe). You can get them discretely online if needed.

  2. Start small. You can always work up to bigger sizes if you want

  3. Don't get too thick. As a beginner you likely won't be able to relax enough to use it.

  4. Always get a flared end so you don't lose it up there and need an awkward trip to the doctors. Suction cups can be useful to practice squatting or kneeling positions.

  5. Dildo or butt plug, your choice. A note though, once in, butt plugs can be tricky to remove if you are new to relaxing your anal sphincter.

apart from that, take your pick!!

How to Practice Anal Sex with a Dildo

banana with lube poured on
Always use plenty of lube - we recommend water based

So you've bought your lube and got used to relaxing your bum enough to take a couple of fingers; huzzah!! All that's left from our objectives for you to be ready for your first time bottoming is to get used to enjoy something more man sized and the motions of sex. You've bought your first appropriately sized dildo (remember, 8 or 9 inches is not needed!!), so let's get to it

1. Start with Fingering

If it's going to take something bigger than your fingers, it needs to work up to it. Take your time, and enjoy it (if you've skipped to this part you cna look at our advice here).

2. Grab the Lube. No, more than that.

When you can comfortably take a few fingers, you're ready for a dildo. Firstly make sure there's plenty of lube on it - as going in dry can not only be painful but damage your anus and rectum. Pop a towel underneath you so you don't have to worry about messy sheets.

3. Get in position

We'd recommend on your back with your legs up, as this is a good way to have your bum nice and relaxed. For first time anal sex we often recommend getting on top so you're in control of the pace of insertion, but as you're using a toy you're in total control here you can save that for later (or not, your call).

4. Ease it in

Just like when inserting your fingers into your a*se, slowly put and remove pressure on your hole, gradually increasing the pressure as the dildo enters your bum.

As the dildo passes through the inner sphincter and into your rectum, you'll likely find a decrease in pressure as your a*rse 'accepts' it, and it slips in a bit further by itself. If you're using a butt plug, you'll get it pulled in as your hole then clenches around the smaller section.

Pro tip: As masturbating typically tightens your bum hole, we'd recommend holding of tickling the pickle when you're applying pressure and trying to insert the sex toy.

5. Take a moment

If you're using a butt plug, mission accomplished!! It's in! If you're using a dildo, the party's just getting started. But first, with the head of it in, just take a second to relax and feel the new sensations and enjoy the experience.

Pro Tip: Make sure to keep hold of it though, as your bum will naturally try and push the dildo out your hole if you let go (no biggie though, you can just pop it back in!).

6. Start slow

Now you can start pulling and pushing the dildo in and out your bum. Start with small motions and gradually work up to inserting as much of the toy as you feel comfortable (you don't have to put it all in). Build up to a rhythm and pace that you find enjoyable, and feel free to masturbate while you do.

Pro tip: Make sure it's still well lubed, as some will come off inside your bum. Reapply liberally where necessary.

7. Play with Positions and get some movement going

Whether it's this time or another time, feel free to play with different positions, and use the suction cup on your toy if you want to (always attach to something solid like a door or wall to avoid mishaps). When you're used to the feeling of a toy, experiment by starting to move your hips and weight around to help the motion (always in a straight forward and back motion - we don't want any broken penises please!!).

8. When You're Done, Clean Your Toys

When you're all finished up, make sure you clean and store your toys properly. How to clean them depends on the material so follow the guidance on the packaging.

How to use a dildo for beginners
Follow these tips and you'll be in great shape for your first time bottoming!

Summary of 9 Tips for Practicing Anal sex with a dildo:

  1. Use plenty of lube. Dry toys can end up injuring your anus and rectum.

  2. Start with fingering (with lube not spit) first and work up to a dildo or butt plug.

  3. Lying on your back with your legs up can help you relax more easily.

  4. Slowly pulse pressing the dildo against the outer sphincter (entrance to your bum), gradually increasing pressure.

  5. Take a moment when you pass the inner sphincter

  6. Gradually start in and out motions with the toy, increasing depth as you wish

  7. Play with positions as you wish

  8. When comfortable, start to practice thrusting your hips and moving our weight (always aligned to the toy - we don't want any breakages!)

  9. After you're done, make sure you clean and store your toys appropriately, depending on their material.

Now you're ready for your first time bottoming!! You've worked up from never having anything in your bum, to fingering, to enjoying man sized sex toys in an active way. Looking back at our objectives, you've nailed them all!!

Be able to relax your bum enough to comfortably take a man's penis, for a sustained period of time, whilst undertaking sexual movements e.g. thrusting/being thrusted in a pleasurable way.

All that's left now is to find a guy for your first bottoming experience as a gay, bi, pan or poly man.

We really hope this has helped you feel ready as a bottom. Drop us a message on Instagram @TheAgeGapGuys and let us know how you've got on!!


x The Age Gap Guys x


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