I’ve made a sex friend who’s 30M and we see each other once a week. He usually likes when I’m only blowing him (which I love too), but he says that he’s still eager to fuck me. Problem, we tried 3 times and his dick just hurts too much when it’s in me. We tried everything : Lube, condoms, anal plugs, going very slowly. But it still hurts as much as the first time. He seems quite disappointed each times I tell him to pull out (though he understands that I’m not doing this on purpose). Maybe it’s the size of his dick (he’s like 8 inches), but he says it’s because I’m too anxious and can’t relax (which is quite true). Maybe my ass is just too tight. Maybe it’s because I’m not really attracted to anal at the first place, I wanted to try just to see if it FEELS good but I only feel pain, so I must not like it…Though I want to like it. Do you have any advice or explanation to all of this ?

16 comments

  1. If taking your time and using more lube doesn’t fix your issues he might just be too big for you.

  2. It’s hard to change first impressions of anal. My suggestion would be use smaller toys or an inflatable plug even a decent time . Make sure your releasing as he goes in and don’t have any roids or tears from before or something down there . Try different angles and getting head while intaking it see if it helps . Let us know if you manage to get the ohhh woah moment finally.

  3. This might sound like a joke but have you tried finger but Hole, jokes aside you might want to try some forplay before insertion and like Lübe up, there are anal Lubes with cooling and pain releaving properties also (toung but hole,) a rimjob before hand might also help relaxing your sphincter

    , first times you have anal sex you will most likely feel weird pain like it feels like pooping in reverse but it gets better each time

    And remember enema and for him to take a shower to keep everything clean unless you enjoy scat, people like what people like I don’t judge

  4. It’s normal to hurt and it’s normal if you don’t like it, men are more likely to enjoy anal because of the prostate, and the nerves involved but it’s possible for one not enjoy it.
    First yes the size of your friend can be an issue for a first try.
    Did you do some finger play to find if you really like anal?
    And it’s normal for you to be nervous and to contract its something that’s more for the painful side unlike vaginal sex.
    If you do like anal by fingering and prostate stimulation, if you can try with a small dildo or a round object, a rollon deodorant may do the trick but still be a bit for the large so use lub and a condom on it.
    I hope you can enjoy sex with your friend and that I could help in some way.

  8. My part and I have been dabbling in anal play more lately.

    It took some time, about a month (twice a week) to go from small butt plug to a medium sized toy. Your fwb is a bit on the larger side so I would probably say you need a few more seasons to get to that point but relaxing the mussels down there, using lube and practice (on your own with toys) will help you get to a pleasurable place. This can not be rushed.

  10. I had a discussion with a bi guy I’m friends with some years ago to something of this effect and I’ll try pass on what we realised. At 18 he’d been with guys before but hadn’t done anal and when the option came up he kind of felt like he had to be into it (because he’s a self professed Twink and that’s what he’s supposed to be into, right /s) and he felt that he couldn’t really be into guys if he didn’t like anal because that’s what every bit of media around gay sex btwn men focuses on. But he’s just not into it. He’s now in a long term relationship with a guy and he’s been lucky enough that his bf isn’t super into it either, he’s still into guys even if not into anal.

    Take Stephen fry, he’s a well known gay man who has admitted to never trying anal sex because he doesn’t want to (in his documentary Out There).

    This guy is 30 and (assumedly) an established person in the community, so yeah you might feel like doing what he wants is what gives you street cred, but it sounds like he’s just a horny ass dude who went for a young inexperienced gay guy and doesn’t want to admit that you _absolutely_ just might not like anal. Or maybe you do and you’d only enjoy topping but he doesn’t want to give you that option because that’s not what he wants. Maybe ask him if you can try that with him (even if you’re shy I know it’s hard), which you should absolutely feel comfortable doing if it’s an equal partnership.

    Or as some people mentioned it could be a size thing. Overall he should be able to make you orgasm with his fingers first before even trying anal tbh

  11. What always helps me is doing anal in missionary even though the initial “getting it in” part can be difficult in this position

  12. You’re gonna need ass play first, maybe practice in the bath with a dildo first that’s what I did

  13. Sounds like his cock is too big for your ass. You’ve done nothing wrong.

  14. Alright I’m upset with your partner with the outsize dick, which he knows (no gay dude with a eight inch dick doesn’t know by the time they are thirty) is a lot for an experienced bottom, being so damn eager to get it inside you. He needs to be following the campsite rule and be a decent human being here. Kid, you don’t need to accept this kind of pressure and his performative disappointment is not a sign of a good partner. Do with it what you will, but look after yourself.

    Anyway, slow way down. Get a series of dildos that go from small to his width, and work up over weeks. Some numbing lube could help with the toys (but don’t use it during partnered sex because you want to feel if there is pain). There should also be plenty of foreplay (tongue and fingers and warming on your hole).

    Ugh, this 30M dude…

  15. I would recommend that you get a dildo a try anal on your own. You will realise that maybe it will take 10-15 minutes to relax enough to slide it in.

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