Welcome to your first step in making sure your first time having anal sex with a man goes great!! That you're taking time to look into it first is a great start
There's a fair bit go through. To make it digestible for you we've split this into the before (below), during your first time bottoming, and after your first time as a bottom. We've even got tips for you on other useful areas like a complete guide to douching and a detailed look at what toys are best to practice with. So as you can see you're in great hands.
Part 1: Before Your First Time Bottoming
Your first time going well isn't just about the deed itself. There's a lot you can do beforehand to get yourself ready for your first time of bottoming, both physically and emotionally. We've split this out, so unless you want to jump ahead to the emotional side....in the words of Dua Lipa, let's get physical.
Get Physically Ready for Bottoming as a Gay, Bi, or Poly Man
Tip 1: Practice with Fingers and Toys
You want to be able to physically get something going in and out your bum not just pain free (trust, it can be a unique and intense pain) but in an enjoyable way for you and your partner. To do this it's really important your first time with a man isn't your first time popping something up your butt.
By putting some lube on your fingers and toys and having an explore down there, you'll crucially learn to relax your bum enough to let something in - which is hard to do on command. You'll also get comfortable with the feeling of having something inside you - it'll likely feel very strange to begin with. Some may have the fantasy of 'I want the first time to be another man's touch' which is fine, but just don't expect to be able to go all the way, as it'll most likely simply not work and be a frustrating experience. So why not just relax and have some fun as you explore and learn about your body in this new way?
N.B. If you wanted more info on this, we've gone into how to practice and what toys are recommended in a separate article - why and how to practice before anal sex.
2. Increase Your Flexibility and Strength for Sex Positions
Sex between men is epic. You're gonna love it (...unless you don't, which is cool too). However whilst a penis and a bum fit just as marvellously as a penis and a vagina, their locations on your body mean that a bit of flexibility is required for the jigsaw pieces to slot together.
We go into recommended positions in our During Your First time Bottoming section, but to get yourself physically ready for some common gay sex positions, here are a few stretches and exercises you can do if you're able to (N.B. Always consult your doc before undertaking new exercise regimes):
Straddle position = a quad and calf stretch to stop cramp. If you wanted to try squatting on your man (more advanced and trickier), practice pulsing a deep sumo squat hold (vid is just a general sumo squat, so just hold at the bottom and bounce a few inches up and down). Start at 30 secs and work up to 2-3 mins if you can (it's harder than it sounds).
On your back legs up position = Practice lying on your back and bringing your knees up in line with your chin, or even up over your head. A pilates leg rollover can be a useful exercise for this.
Doggy Style position = Getting a little bend in your back can help straighten your rectum for easier entry for your partner, so the Happy Cat pose in Yoga is a good one to master. Getting your legs a bit wider can help entry and fit when you have a height difference, so a yoga frog pose can be great to help loosen up those sitting-at-a-desk-all-day hips.
Get Emotionally Ready for Bottoming as a Gay, Bi, or Pan Person
3. Check in With Yourself
Whether you think you've found the one, or just a one, it might be worth taking a step back for a second.
It can be easy when an opportunity for D arises to want to jump on it (so to speak). It may be worth just taking a moment to pause before you hop into bed to make sure you're ready for losing your virginity. It can feel like everyone else is doing it, you're going through a horny phase and are excited, or you're getting pressure from the person you've been chatting to / messaging. However just remember there is absolutely no rush for you to do anything. It's your body and you can take that step when you're ready.
4. Feel all the feels
Depending on your personal situation you'll likely feel all different kinds of emotions surrounding this. Excitement at being with a man; fear of liking it and having to confront your sexuality; impatience at wanting to get on with it; scared of whether your life will change, shame of your attractions, etc. None of these are right or wrong, but they have all been felt be thousands of others. The main thing is to let yourself feel these feelings and not judge yourself for that. Repressing these emotions won't help you work through them in the long run.
This isn't to say you necessarily need to have all feelings resolved fully - for example it can take some years to accept they're gay (I definitely had a few phases of different levels of self acceptance that took years). However being self aware can help you better manage the emotions you're experiencing, and assess whether you're ready for the step you're about to take.
5. Make sure it's with the right guy, but don't expect them to be Mr Right
Your first time isn't something worth overly stressing about, but netiehr should it be treated flippantly. You only pop your bum cherry once and if it's a negative experience, it can put people off exploring again. (After J's first partner, he decided he'd 'go back to women' because of the negative experience. Fortunately after a few years of subsequent celibacy he returned to guys!!).
As such you want to make sure that you're not just ready to bottom, but that you find the right guy to do it with. If you find a guy that you date and take that step together with that's great, but we also know the lowest hanging fruit to pick is now on hookup apps. They're free and have loads of guys on there looking for sex.
This is perfectly fine to do as well, just bear in mind that your first time with someone can bring up some deep emotions. They're likely to be just looking for sex and not anything long term, so try to guard yourself from getting too head over heels with for the man that takes your anal virginity. Easier said than done, but just be prepared there may be feelings afterwards to feel as well as before and during.
6. Don't stress about what bottoming says about you.
Particularly in some cultures and countries, some still believe the stereotype that being a bottom makes you more feminine, as you're 'taking the role of a woman' in sex.
This is of course utter nonsense. This perspective is gradually departing as the world opens its eyes more to the gradients of sexuality and preferences that exist. This can however tinge how people see the idea of bottoming and worry about what it says about them. Well DO. NOT. WORRY!! Regardless of being feminine not being a bad thing, whether you like being on top, bottom, both, sometimes one, or even neither, it doesn't matter. Someone putting their nob in you doesn't change the person you are in any way. So don't stress about the stereotypes and judgement, enjoy this exploration, and be happy.
Click here for Part 2 - Tips for During your First Time Bottoming to Make it a Good Experience
Hope you enjoyed part 1. You're well on your way for your first time anal sex as a bottom.
Love,
@AgeGapGuys