Have settled comfortably into an FWB situation with a woman who is pretty filthy, very much likes it rough and VERY much loves anything involving her arse, but hasn’t been able to actually have anal sex.
For my part, her ass is flawless and I’m enthusiastic to say the least but experience aside I/we haven’t been able to get her past the pain barrier.
Any particular advice there? Neither of us really wanna be buying a load of hardware or anything.
She can wear a fairly small plug for hours and some pretty vigorous other stuff but nope, once the tip breaches the wall, it hurts and so abort mission.
Any ideas? Thanks! |
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Pain in the body's way of telling you not to do something. My advice would be leave it. Other people might recommend numbing lube but if you need to numb an area in order to have sex I'd suggest that's not a great idea either. |
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Start as slow as you think is sensible, and then go half as slow again.
Use as much lube as you think is needed, and then double it.
It can feel a little clinical to begin with, and your partner has to do their best to relax. You can absolutely feel their muscles relax or tighten around your fingers, so be sure to stop if you feel the latter.
Build up slowly, and you'll probably be fine. There shouldn't really be any pain involved. |
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Thanks for the replies, the pain isn’t severe just uncomfortable (having experimented with putting things up my own chutney I can relate).
She can take quite a kicking with fingers though, and goes totally wild for it, which is why I’m a little perplexed. I’m not tiny tim but it’s not like I’m throwing a log in there either.
Will persevere. Certainly isn’t getting in the way and it’s a mutual venture, obviously if she wants to abandon the idea that’s the end of it. |
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"Get a wand and use that on her clit while teasing her arse. She'll be able to focus her mind on that rather than the big sting the other end! Once she's over that I swear, she'll love it  "
I'm going to agree with this, on the basis that I don't usually do anal on a woman unless she's had an orgasm first? I find everything is far more relaxed, and 'receptive' thereafter....
Unless she's an anal lover, and asks for it straight away
And; lots and lots of lube! If she's ok with fingers and plugs up there already, it shouldn't be too long before she'll take your cock |
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Need working up to it and don't hurt at all! Plus a bit of lube! This 1 fwb I had one time just stuck it in with no working up to it no lube I nearly hit the ceiling! Same man worked up to it used plenty of lube used butt plugs and was very relaxed (have a vid in my gallery Oct 2021 I think) and not even any after pain! And I have only had bum sex about 5 times in my life! X |
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Lots of lube (at least 300% more than you thought you needed) and lots of foreplay with fingers. Once you’ve relaxed her for half an hour or more gradually inserting more fingers (and adding more lube as you go) then try it.
Put towels down. |
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By (user no longer on site) 41 weeks ago
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It sounds like based on a few painful starts that she is perhaps tensed up anticipating pain?? You have to be pretty relaxed for anal, or it can be painful |
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By (user no longer on site) 41 weeks ago
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I have to totally agree with the wand, only time I’ve ever enjoyed or climataxed from anal was the times I used a wand. Anal specified lube and take it slow after lots of foreplay like others have mentioned. An old FB couldn’t take pegging without p@ppers (but not something I’d personally use myself) I don’t recommend alcohol with anal, then again I don’t drink ever |
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By (user no longer on site) 41 weeks ago
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Also what position are you trying??
Maybe have her lie on her back with her legs in the air /around your neck and slip into her, a bit like anal missionary... I'm sure it has a proper name  |
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"Also what position are you trying??
Maybe have her lie on her back with her legs in the air /around your neck and slip into her, a bit like anal missionary... I'm sure it has a proper name "
Hotlisted |
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"I much prefer pussy (and so have all my partners) so I'm coming at this as a novice, but could it be more of a psychological barrier rather than a physical one? Just a thought. K"
This is something I think may be an issue. Some Wally just tried jamming it in once (consensually but perhaps not wisely so) and she was injured from it.
Plus she really does have a tight ass and cums really hard when I’m tonguing it. Earlier on I popped a small vibe in there while I was fucking her and Christ alive, she looked like she was being possessed and electrocuted at the same time. Like a seizure.
I may need to abandon this in truth, I have a feeling that despite our relationship being platonic that she may be conscious of disappointing me. |
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"Also what position are you trying??
Maybe have her lie on her back with her legs in the air /around your neck and slip into her, a bit like anal missionary... I'm sure it has a proper name "
I’ve seen success with this on other anal-curious but inexperienced girls.
This is possibly my fault as the girl in question looks fucking flawless on all fours with her back arched and that’s also how she wants me to fuck her hardest. Yoga teacher and gym manager  |
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"I have to totally agree with the wand, only time I’ve ever enjoyed or climataxed from anal was the times I used a wand. Anal specified lube and take it slow after lots of foreplay like others have mentioned. An old FB couldn’t take pegging without p@ppers (but not something I’d personally use myself) I don’t recommend alcohol with anal, then again I don’t drink ever"
If I had p*ppers I’d probably just end up sniffing them every few minutes. Aging raver, some habits never die. |
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By (user no longer on site) 41 weeks ago
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"I have to totally agree with the wand, only time I’ve ever enjoyed or climataxed from anal was the times I used a wand. Anal specified lube and take it slow after lots of foreplay like others have mentioned. An old FB couldn’t take pegging without p@ppers (but not something I’d personally use myself) I don’t recommend alcohol with anal, then again I don’t drink ever
If I had p*ppers I’d probably just end up sniffing them every few minutes. Aging raver, some habits never die. "
Ha, have to admit not something I’ve ever tried! Best of luck OP, remember position is your biggest challenge, not many women enjoy anal from behind it’s just too painful |
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Sounds like a psychological barrier, if she’s ok with fingers and toys and penetration in general.
There’s also the slight barrier that penetration can always hurt for the first 30 seconds or so as the muscles relax. Once past that it may get easier.
Don’t use numbing agents.
Try having her ride you and be in total control, it may give her the confidence to go further.
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Sounds like she may be putting pressure on herself to do it, making her perhaps anxious about it. Combined with the fact she's had a bad experience already.. I'd say either take a break from trying, or accept that it's just one of those things. Focus on enjoying other interests that you share  |
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By *indergirlWoman 41 weeks ago
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"I much prefer pussy (and so have all my partners) so I'm coming at this as a novice, but could it be more of a psychological barrier rather than a physical one? Just a thought. K
This is something I think may be an issue. Some Wally just tried jamming it in once (consensually but perhaps not wisely so) and she was injured from it.
Plus she really does have a tight ass and cums really hard when I’m tonguing it. Earlier on I popped a small vibe in there while I was fucking her and Christ alive, she looked like she was being possessed and electrocuted at the same time. Like a seizure.
I may need to abandon this in truth, I have a feeling that despite our relationship being platonic that she may be conscious of disappointing me. "
This happened to me many years ago and it now takes a lot of trust and patience to do it (because sometimes i want to), the mental barrier is the hardest to fight sometimes |
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"I much prefer pussy (and so have all my partners) so I'm coming at this as a novice, but could it be more of a psychological barrier rather than a physical one? Just a thought. K
This is something I think may be an issue. Some Wally just tried jamming it in once (consensually but perhaps not wisely so) and she was injured from it.
Plus she really does have a tight ass and cums really hard when I’m tonguing it. Earlier on I popped a small vibe in there while I was fucking her and Christ alive, she looked like she was being possessed and electrocuted at the same time. Like a seizure.
I may need to abandon this in truth, I have a feeling that despite our relationship being platonic that she may be conscious of disappointing me. "
Maybe the old injury is what is hurting, scar tissue doesn't stretch and if it rips that's a a&e trip, maybe stick to fingers and plugs if they are the ones that don't hurt. |
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