Dear KD: I Desperately Need Help With My Bottoming

Dear KD: I Desperately Need Help With My Bottoming

Hello guys. I just want to pour my heart out about stuff I’ve been going through.

First, I struggled with accepting the fact that I’m gay. I am also effeminate and super attracted to guys. Like, I’d see a hot guy and my body would start shaking like I’m having a seizure.

Bottoming has been hard for me, to be honest. I fumbled a lot with my limited knowledge of gay sex when I first started being sexually active. I would go for a hookup and I would make a mess of it. Getting penetrated was stressful. I’m so fucking tight that even the pinky finger can’t enter my ass without me gasping with pain.

I fell in love with a guy and he was so big, like 10 inches or so. The first time we tried to have sex, it was a disaster. I eventually had to jerk him off. He didn’t blame me though, and this made me feel better. After that day, he invited me over to his place to spend the night. We chilled and we both smoked ‘skunk’ and got so fucking high. And lo and behold, we had sex with such ease. I took all of him with absolutely no pain. The kind of joy I felt as I felt his dick pounding inside me, almost as though it could get to my chest and throat, was indescribable. For once, I had a good bottoming experience. Safe to say, I thoroughly enjoyed the sex; it is in fact the best I’ve ever had till date.

We tried to have sex again like two months later, because he was serving in a different state from where I was staying. We met and I didn’t want to get high. We tried. There were lots of lube available. Lots! There was pain but we managed to get through with it. I found some enjoyment in it.

I should point out that all this sex I was having – or trying to have – was raw.

Eventually, we ended things. And I met someone else on twitter. We soon got together and the sex was difficult as usual. The second time we tried to have sex, he ran out of lube and decided to use hair cream. The sensation of his dick inside me was weird and peppery. I told him to stop when I couldn’t take it, and I left his house. My ass was on fire and I was having a hard time pooping, and when I told my friend about it, he told me to clean up properly and then sit on hot water. I was so miserable. ??

A month later, I got a painful bump in my ass. I was confused by it. This was a first for me. I thought it was piles and started taking herbs for it. It didn’t heal. I told my grandmother about it, because I’d once heard her talk about a cousin who had piles and his ass came out because of it. Weird story, I know. So I told her I had piles and she instructed someone to make some herbs for me, plus a cream which she asked me to rub on it. She also told me to stay away from ingesting any sugary stuff, because I am a sweet-tooth.

Two weeks after, and still no change. So then, I told a friend who works at an LGBT clinic, and he invited me over and linked me to a doctor. I was examined and informed that I had warts. Until that day, I’d never heard of the word “warts”. I asked him what that was and he explained it to me. he also told me that before treatment, I’d have to get tested.

I was not worried about my status because I hadn’t been very sexually active. The naïve me thought that a positive HIV status was only guaranteed if you have a lot of sexual partners, and I could count on one hand how many guys I’d been with.

The test came out however and I was positive. I was devastated and I left the hospital immediately, needing time to process the news.

However, I came back the next day to commence treatment. I took my antiretroviral medication, and then I was treated for the warts. It was painful as hell and I was knocked out for several minutes after the session. It didn’t go after that first time. The warts came back and I ended up having four cryotherapy treatments. It was hell!

And in all this time, for over a year, I stayed off sex. I relieved myself by masturbating, and was regularly turning guys down because I just wasn’t ready.

I got undetectable in my first four months after starting my antiretroviral therapy, and my fourth wart treatment went well, better than the other three. But with it, I was wart-free. And with my undetectable HIV status, I was ready to try having sex again.

But I still had a big issue with bottoming. I asked a friend over, and this guy had a really small dick, like 4 inches, and he still couldn’t penetrate me. After him was another guy, and the sex was a mess. We were of course having protected sex, not that the sex part was even happening.

I got a dildo to practise with, and still I couldn’t get it to go inside me. I got poppers, hoping to drug my way through the dildo practice session, and that didn’t work.

I am frustrated as fuck. Like, I am tired! I need a man to fuck me! I need my ass to open up so I can enjoy life! I’m always lying to my friends about hooking up and being a hoe and all that, when I haven’t been getting any action. It’s been nearly two years now and all I have been able to do to get sexual satisfaction is by masturbating.

I AM TIRED!!! ???

Dear KDians, please help me! What do I do?! ????

Submitted by Daniel Rose

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  1. Sim
    January 10, 07:37 Reply

    Sincerely I really have no great understanding of how this things works. As a Dr, I know the anatomy is the same, blood/nerve supplies same but act of dick reception is different. Maybe it’s not u thing, I have tried and failed and given up

  2. Francis
    January 10, 07:43 Reply

    If bottoming isn’t for you don’t force it. Anal is not do or die. Please don’t goan harm yourself because you want to experience what others are “enjoying”. Stay away from “drugs”. Find some other sexual activity that gives you immense pleasure.

    Just as you’re lying to your friends about being a hoe and shit, they could be lying to you about being pros in the sack. Most people be lying and hyping themselves to look good. Just like miserable married people claiming to be happy on the Gram.

    Do you man. ?

  3. trystham
    January 10, 08:47 Reply

    I hate that u had to get HIV just after two sexual partners. It breaks my heart because you seem the kind of person who loves stability and would give your all to your chosen partner who unfortunately is a bastard.
    That said, I don’t know about needing drugs to loosen your muscles. That sounds just terrible and impairs ur sense of judgment. I do know about loving dick and wanting to have it filling up your arse. Hair cream though???

  4. Tristan
    January 10, 10:00 Reply

    Hi Danny. Here is what I have for you.

    Don’t get tired yet.Relax and use lube. Lots and lots of lube, and then some more lube. As pleasurable as anal sex can be, it can also hurt like nothing else on earth if you get it wrong. And if that isn’t bad enough, you can also end up doing some real damage to your rectum if you aren’t careful.

    In order for anal sex to be safe, you must be sober and lucid so you can pay attention to the signs that your body is giving you. You should expect to feel a minimal amount of discomfort since your rectum isn’t made to lubricate and stretch the way a vagina is, but if it there is any real pain it’s a sign that you need to stop and regroup.

    Your relaxation and comfort is an absolute must. You won’t get anything past your sphincter if you are clenching those muscles, at least not without extreme pain and severe damage. Take deep breaths and release the tension down there. In order for this part to work, you need to trust your partner and have total confidence that he’ll allow you to set the pace.

    Talk to him before you even begin, and let him know that you need to be in control. Find a position where you are comfortable and where gravity will not work to drive his dick into you. Ask him to refrain from pushing his dick into you, instead of allowing you to back yourself on to him; it’s the best way to ensure that he won’t move too deep too fast.

    Most of the resistance during vaginal sex is felt during the initial penetration, but your rectum needs gradual stretching all the way in. Rock back and forth on his penis, allowing it to enter a millimeter more each time. If you move too fast it will hurt, and if it hurts, you will clench – and that will only increase your pain to the point where you need to give up.

    You may never feel comfortable taking his entire length, and that’s okay – your partner can still enjoy the activity. Once you have taken him in as far as you want – with those little rocking motions – you can gradually increase the pace or even allow him to take over control – but only if you trust him to respect your request not to push in any deeper than you’ll allow, and to follow the tempo you’ve set.

    Before his dick even approaches your ass, you will need to ask him to finger you while applying lube. Think about how much lubrication you’d need to shove a tennis ball through a keyhole, and then double that. Make sure you get the lube inside you, all around your anus, and on the entire length of his dick.

    Ask him to use his fingers to periodically apply more around your hole, both while you are rocking your way onto him and once you start going at it. He will likely have a hard time understanding just how much lube you need, and how frequently you’ll need it reapplied, so make sure that he knows what to do whenever you say “more lube”. He might be worried that it will get too slippery, so go ahead and reassure him that not even a swimming pool full of lube could take away the very tight friction of anal sex.

    It sounds complicated, I know, but it will get easier when you learn to relax and figure out your limits. You can have very pleasurable receptive anal sex, but it’s one of those things that you have to get right. You know how some foods can still be pretty good even if they’re bad? Anal sex is not like that.

    Good luck.

  5. E
    January 10, 13:06 Reply

    To Trystham, HIV is a disease, not God’s ‘justice’ for promiscuity. People that don’t want stability and whatever else you said don’t ‘deserve’ it any more. Seriously? Your comment is cavalier and foolish. It’s like telling a girl you’re only sorry she got raped because she’s a ‘good girl’.
    To the OP, you seem like someone that will need a good bit of foreplay, at least initially. Try making out and heavy petting for starters, then have the guy rim and/or finger you to get you mentally prepared to be penetrated. Do some more making out, then ask the top to ease the tip in. Do that for a little bit, then ride it for a few minutes, while still making out. After that, you should progressively be more receptive to the D. Anal arousal is a thing, and it’s different from being hard. Your penile muscles tense when aroused, but your anal muscles do the opposite. The two arousals can co-occur but not as a necessity.
    Finally, the more you bottom, the more used your muscles will be to the sensation, and the easier you’ll find it to relax.

    • trystham
      January 10, 21:30 Reply

      I really couldn’t care less about ppl who don’t want stability, but are hell bent on abusing the naiveté of their very trusting partners, enough to not use protection in their philandering. They can die for all I care.??

  6. Dickson Clement
    January 10, 21:59 Reply

    West Africa college of Tops have their entrance exams in march, here in Lagos. You may likely get all the study materials here and prepare to write!

  7. Dimkpa
    January 13, 12:07 Reply

    Here is the secret to bottoming.

    The anus was designed to push things out not take in. In its resting state, there is a muscle that pulls the lower end forwards creating a kink that keeps it shut.

    When you want to poop, you push down and this muscle, the pubococcygeus (look it up) relaxes and the anus and rectum align letting things drop.

    Have you never looked at a hard long poo some bigger than your average dick (you know the type), and wondered how it comes out so easily? It is because the stars are in alignment.

    Likewise, when you want to overcome the BDE in, do the same thing you do while dropping poop.


    It is that simple. When the D is coming push out like you’re going to welcome it, think MEET AND GREET. That is the way to absorb the BDE. People often say relax but are never specific as to what needs to relax.
    This is it boys.

    A lot of guys get scared and try to run away from a dick, NO! Stop that break dance! You need to be bold and, say it… PUSH OUT TO TAKE IN! Push until something happens. A woman pushes to get a baby out, we on the other hand need to push to let our babies in. I can’t emphasize it enough.

    This my boys is, the secret to bottoming.
    Go forth and conquer!!!

  8. Babji
    November 12, 17:28 Reply

    I have never laughed like I have laughed today, Nigerians have become PhD’s in anal sex

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