Question: I self-identify as a versatile 19-year-old gay male and often have casual sex. However, I have only topped before and prefer only oral sex and not anything more. I have tried to bottom a few times, but did not feel comfy.  How can I make bottoming less painful? I really want to bottom. How can I make it more pleasurable?

1. Ensure that bottoming is really your top thing and not something you are pressurised into.

Among younger gay person, there can be a lot of sexual pressure to experiment being a top, bottom or versatile. In fact, taking turns into either seems to be more common among the younger gay persons. However, remember, you do not always need to fit-in any of these three categories nor need to change your sexual penchant for any partner. Some gay men are not into anal and it is perfectly normal. Sexual experimentation is healthy, and if you are curious and excited about bottoming, there are tips to make it safer and satisfying that it is a pleasurable experience.

2. Do some preparation work when you are relaxed.. and (generally) alone

Easing yourself with anal penetration through solo-safer-sex can make you more confident and the sex more pleasurable when you shall eventually do it with a partner. When you are showering or in bed, try inserting your fingers slowly to see what feels good. Start with one then work your way up to two, three… using lube will make things smoother and more comfortable. If you have sex toys such as dildo, vibrator or butt plug, these can help too. However, remember to pay attention to your pain threshold, and stop if it really hurts or you start to bleed. Experimenting solo-anal-sex for the first times, remember to be relaxed, breathe deeply and be in a situation that your parents or siblings will not disturb you. Just do not get too overwhelmed, and be at ease until you are ready to try again. Practice makes perfect!

3. Be trusting towards your partner

Whether it is someone with whom you have settled or a new casual, you need to feel trusting and safe being with that person. This helps in communicating with them and help them to help you both have an enjoyable experience. Feel at ease to let them know that it is your first time, or if you are anxious, or if you want to go slow so as to adjust with each pace, trust, or his member.

4. Engage in any preparations that will give you confidence and make you comfortable

This can be anything from cleaning yourself (and pooping anything left), grooming, establishing the atmosphere (wine, candles, essence…) or some drug (if it is legal). Chemsex helps even if it has its risks.

5. Fore-playing or anal play to ease yourself and your partner

Be into foreplay or any other anal play first. It an be anything to kissing, sucking, caressing, rimming, fingering, pinching the nipples.. well anything that can help you get relaxed and aroused.

6. Lube it up and condomise (.. always)

Water-based lubricants are available from NGOs and the pharmacy and it works well. Silicone-based lube might be more preferable since it keeps the lubrication longer than the water-based lubricants. Also, ensure that the lube is compatible with the condom. Oil-based lube and products can break down latex condoms and make them less effective. Also you might try condoms with textures, flavours, and so much more. However, some persons are into bareback, rough-sex, and kinky fantasies. Do not feel pressurised to use lube and condoms if you do not feel like and you and your partner(s) are HIV- and STI-free. Sex and sexiness should not be judgmental.

7. Be in control

As it might be your first time and you could be concerned about pain, you (the one bottoming) should be the one in control to guide the trusts and penetration depths. Best positions are either your partner lying down on his back and you easing yourself down on his penis or your partner on his knees with his penis erect and you on your fours and pushing yourself back towards his penis. Remember that you can take it slow, ensure that you are at ease and you do not need to take all of his penis at the first time. Relax and breathe.. heavy breathing might be sexy too.

8. Stop if it really hurts 

Another reason why you want to be the one in control of the pace of thrusts and depth of penetration is if it hurts. It is normal to feel some pain, pressure and bleeding.. and you might feel like pooping or farting. However if it is uncomfortable, STOP! You do not want to be bleeding or it to hurt down there when you are pooping.

9. It is okay if bottoming is not your thing

Whether you are young, old, inexperienced or skilled, there is nothing wrong or alien about a gay person not bottoming. There are many gay or not gay person out there who do not bottom. The more you try bottoming, the more comfortable it shall become. However, if you realise that bottoming is not your thing or you do not feel satisfied, remember that you should not feel pressurised to engage in any sexual act that you are not comfortable with.

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