No.331461 [Last50 Posts]
Hi /cuteboys/, I come to you in need of advice for my boyfriend and I.
We've been in a LDR for over a year now, we've met up a few times and I love him to bits, he's 100% cuteboy husbando material and we're very open and comfortable sexually.
Through all this, we both fantasize heavily about anal, especially since he likes chastity. But everytime we want to try it, either it hurts him or he panics and loses any kind of desire for it - even though a few hours later he'll be fantasizing about it again.
We've talked about it at length, I really don't NEED anal in our relationship anyway but he keeps trying to use plugs, fingering etc to try and "train" himself because he really wants it to happen.
Any advice from seasoned subs for my qt bf?
____________________________
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No.331462
off-topic but the best of luck to your LDR, I hope from the bottom of my heart it works out
and honestly really not any advice to give besides "play with your butt more"
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No.331463
>>331462
Thanks, we have serious plans for moving in together and everything, we both appreciate the feeling! <3
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No.331474
>>331461
ruh roh you have one of "those" types.
get him high on pop and you'll be able to finally do it.
all consensual of course
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No.331484
>>331474
bad idea - pop can cause strokes because of the blood pressure drop.
there was an ebook - think the title was something like "how to bottom like a pornstar"
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No.331485
Use lots of lube and finger him before sticking your cock in. If you can fit three or four fingers without hurting him, he can take your dick.
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No.331487
The only thing that comes to mind is prepare more. In the great words of Tormund Giantsbane. Use fingers, plugs, and lots of lube. Go slow and gentle.
My first time with my ex-bf I wanted to do things too fast and it ended up hurting. Not a huge amount but enough to be uncomfortable the day after. The reason why I wanted to do it so fast is cringy so I won't bother you with the details. From that experience I learned about the importance of preparation. Now I always make sure to take my time with it, even when just playing with myself. Buttstuff just requires a fair bit of patience, foreplay and a lot of lubricant (and maybe some experience) to get just right. That's the nature of the beast.
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No.331634
He may be nervous actually. I'm the same way, some slight pain and stretching is too be expected when trying to get a good angle, but the thing that actually worries me the most is not being clean enough back there and having something gross happen. No one should have to go through that bullshit.
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No.331655
>>331461
Does he understand that he needs to push "out"?
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No.331657
>>331461
How long are you trying? Are you starting with a pinky? Also, I can take fingers and my dildo easily, but I still can't use even a fairly small plug.
>>331655
Dude what? I never do that.
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No.331659
>>331657
The muscle that widens the sphincter is mentally tied, in humans, to the idea of "pushing out" (for obvious reasons). If you can simply relax it at will that's great, but for people who can't, that is the most common reason why
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No.331668
>>331655
do this if you want your bf to prolapse
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No.331676
>>331668
Is it considered prolapse if I can push the inside out a little bit? It never does it on its own, but I've always been able to push a little of it out for as long as I can remember.
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No.331677
>>331676
ummm… yea man sounds like prolapse to me
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No.331679
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No.331685
>>331485
Thanks for the advice Admin <3 I'll be sure to do that.
>>331487
I'll be sure to take it slow, he's reading this thread anyway so hopefully it'll work. Thanks!
>>331634
Yeah he's probably very nervous. I think he's just afraid to mess up in some way too :c Cleanliness also plays a part in it most likely so we'll have to take care of that. Thanks for the answer!
>>331655
Well I don't necessarily want him to prolapse, heh, but thanks for the advice anyway
>>331657
Not too long, he tends to lock up once we try, I think, so he won't be too responsive to trying much. and the worst part is before we met irl he used those plugs quite a bit, but now it looks like he's afraid he'll hurt himself so even that he had trouble with :c I'll definitely try the pinky though, and thanks for the answer<3
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No.331687
Anal is fucking disgusting, there are so many better things to do in bed, also thigh sex > anal, just saying.
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No.331690
>>331687
why do people like you bother posting?
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No.331691
>>331690
Go beg on the streets or steal you gypo scum
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No.331692
>>331691
called you out on being a retard and you jumped at the opportunity to prove it - you are so pathetic it's embarrassing to talk to you
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No.331728
>>331685
>he won't be too responsive to trying much
So you're not taking the time? Why do people keep asking how to do anal and then taking common sense as some kind of new information?
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No.331773
Never had any kind of issues such as those and the first guy I was with was quite huge.
Try to do it in a comfortable position, where your bf's legs are spread so it slides in much more easier and causes less strain on the anus.
>>331685
If you took a shit a few hours ago and finger a bit the worst thing you can get is a slight bit of residue of shiit that wasn't cleaned properly and stuck around. Remove that in the shower and you're almost always good to go. If there's a lot of poo you need to take a dump first.
Idk how you can struggle taking a dick in there when pluggs are much, much thicker (thus harder to take in).
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No.331848
>>331728
We are taking our time quite a bit, but it hasn't helped so far.
>>331773
Well he can't take his plugs in much now, he fingers to try and get used to the feeling again but otherwise he definitely hasn't taken anything as large as my dick in quite some time.
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No.332761
If you're still around, OP:
One thing that's helped me a lot was finding out how to massage my prostate from outside. Usually by massaging the taint, you can gently massage the prostate and induce an aroused state that makes it easier to insert. It can take quite a while to get aroused enough to loosen up if one is really tight, but it helps a lot on the pain and discomfort.
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No.332877
It sounds to me mostly like he's subconsciously worried about making a mess. What he needs to do is learn to disassociate the feeling of anal play from the feeling of taking a shit. It's similar to how a boy's first ejaculations can feel like peeing. This isn't an easy process and takes time.
First of all, plugs are useless. The anus doesn't need to be "stretched" to be able to have anal sex. The tightness is entirely based on the mental state. Even a man who has not so much as put one finger up himself can be fisted while under general anesthesia, and most guys drop logs thicker than the average penis on the daily. No, his being tight and hurting is completely because of his mind. You can't physically train the anus to be stretched because it's already been "trained" nearly every day since birth.
First of all, he needs to spend time by himself just exploring his ass. Take a shit, use a small enema to clean out, wait a half-hour or so, then play. Something I used to do about a decade ago when I started to get more serious about anal play, was take several small, smooth river rocks and push them into myself, then push them out like I was shitting them out. I wouldn't recommend this to an amateur (could get hurt) but a set of anal beads should do the same thing while being safer. Just put them inside, and then instead of pulling them out, push them out in a squatting position exactly the same as when taking a shit. What is important is for him to realize that he can experience almost the same sensations as shitting without it actually being shit. Look away, push out the beads, then reach down and grab them. Feel them. Notice how they aren't dirty and don't have a bad smell. Do this several times and only focus on the pleasure. It helps create a psychological separation between the act of shitting and the physical feelings. It also allows for a better voluntary control of the muscles down there. He can also use dildos on himself and his fingers of course. The most important thing is he does this by himself as part of masturbation; it's his body and he needs to understand it on his own, because the other problem is actually you.
The second thing is to remove the expectation. If he goes into a sex act with you expecting that you want to have anal sex, it makes him nervous. He feels that he will disappoint you if he can't do it; it's like the bottom's version of erectile dysfunction. The real issue here is that you've only met "a few times" and probably every time have tried to have sex with no success. So just… don't try it. Tell him that you don't want to do it this time. Remove the expectation. You can please his butt with your fingers, your tongue, or with toys; maybe rub your penis against his hole and don't attempt to penetrate him. He needs to subconsciously realize that penetrative anal sex can be fun, but it's not a requirement; the sex won't be "bad" just because it doesn't happen. Both of you can still cuddle and kiss and cum and really love each other without it.
It might take a long time, and it might never happen. Coming to peace with this will increase the chances that it will happen.
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No.333604
>>331461
>>332877
A lot of this is true in my experience.
Usually anal isn't all that messy. As long as I shit beforehand it doesn't make too much of a mess.
I think a lot of it might be a mental block. Anal is one of the most vulnerable feelings in the world. It's basically impossible to feel like you're in control when you're being fucked in the ass. It makes me feel really submissive, even slutty, like I'd do anything for cock, even take it in the ass (which culturally we have come to associate with humiliation).
I think solo exploration might be the way to go. Buy him a dildo and have him play with it. Honestly the feeling of vulnerability never really goes away but you can become comfortable with it through experience.
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No.333848
>>333604
>Honestly the feeling of vulnerability never really goes away
that's why its so fun
>>332877
Personally I found plugs to be helpful in training my ass and my psyche into not only getting used to it but learning how to really enjoy it. It's just really satisfying and leaves you feeling zen afterwards. Prior to this I was one of those "it's never gonna happen, stay outta my ass" guys
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No.334140
>>332877
>>333604
Hi! Thanks for the replies, I'm bf in question and I think these sum up quite well why this is hard for me, when I am alone and finger myself it is often fine but together, trying to do this is hard for me because I have very little control and I'm afraid of it hurting or it not being like I want it to.
Follow-up question: is there any nice dildos that any of y'all could recommend? I don't know what to search for to be honest.
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No.334190
>>334140
Beaded plugs/anal beads to get used to the feeling of submitting slowly. Honestly it's really satisfying if you enjoy being a bottom and it helps you to get a handle on what it's like. Try to find some medical grade siliconeFor health reasons butt plug sets to sort of help with loosening yourself up. Water based lubricants as well for silicone toys. Then you can go from there. This is what I've done and I'm kind of addicted to anal play now
I am NOT recommending these sites/products specifically, because I just looked them up but these are the kinds of toys I'm talking about
https://www.etsy.com/listing/507242664/silicone-anal-butt-plug-dildo-4-bump?ga_order=most_relevant&ga_search_type=all&ga_view_type=gallery&ga_search_query=Silicone%20Butt%20Plug&ref=sr_gallery_14
https://www.pinkcherry.ca/mood-double-naughty-silicone-plug-in-black
https://www.pinkcherry.ca/renegade-silicone-anal-trainer-kit-in-black
https://www.etsy.com/listing/521049961/silicone-anal-butt-plug-one-bump?ga_order=most_relevant&ga_search_type=all&ga_view_type=gallery&ga_search_query=Silicone%20Butt%20Plug&ref=sr_gallery_16
And then you can just google anal beads I'm sure you prob know what they are, again not recommending these specifically just saying this is what you want to look for as a beginner. Anal really should be enjoyable for you so if you start doing it and think "I don't like this I don't want that there" maybe it's not or you. Just be gentle and slow and try to enjoy the moment. Maybe your bf can help with inserting toys and you can make it an experience together
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No.334213
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No.334277
>>334190
Hi, these look alright for plugs, I have some and I do find with them but they're silicone similar to this so I'm not sure if I'm keen on that, they get discoloured and dirty after a while, I'm familiar with toys yes, more thinking of specifically getting a dildo to get used to the shape and fullness so that's why I'm hesitant on plugs
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No.334279
>>334277
>>334190
Follow-up, how about glass items like this: https://www.etsy.com/uk/listing/453932418/classic-glass-dildo-luxury-glass?ref=shop_review
It looks great and the idea of glass is quite appealing but I'm not sure if it's a good idea
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No.334593
>>333604
>It's basically impossible to feel like you're in control when you're being fucked in the ass
I think it's a mental state, there's lots of power bottoms out there. I really being in charge and watching guys melt in ecstasy beneath me.
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No.342025
>>332877
>>333604
Well i got this one rather large butt plug and i never was able to get past the widest point
:c
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No.357246
>>342025
I know the feeling. I have one that's like 1.75 inch diameter, and that's not an issue, but the 3.5 inch one is impossible. I can't squeeze the last 3/4th's inch thickness in, mostly for fear of tearing/not being able to remove it.
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No.358025
>>334140
For dildos, you should go for silicone and avoid PVC/plastics
Remember to do an enema before, whilst you can douche/syringe, i would recommend just taking of a shower head and use that.
With anal in general, it will almost always be uncomfortable in the beginning, so buy loads of lube in the beginning and start breaking your anus in little by little. Wearing buttplugs will help getting your anus stretched further.
It's okay for it to be slightly painful in the beginning, but when it hurts too much, stop, and especially if the pain is a stinging pain.
Practice in private first, working yourself up to at least 4 fingers.
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No.358176
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No.358177
>>358176
Drugs for degenerates, ignore him and avoid them.
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No.358181
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No.358183
>tfw /cuteboy/ top with no /cuteboy/ bf and only have women interested in me
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No.358213
>>358183
At least you have women after you. It sucks to have no one.
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No.358214
>>358183
Sometimes I get a bit nervous when I can't tell if the webm is of an actual 13-year-old.
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No.358218
>>358216
t.420blazeitfagit
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No.358228
>>358183
I volunteer.
>>358214
That makes it hotter, tbh.
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No.358234
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No.365843
Well it's been forever and a half so I thought I'd give an update, if anyone remotely cares.
Since making this thread boyfriend and I met up once, but it was at his place and with his parents around he got really stressed and it was impossible to do anything, which was a real bummer for both of us.
But he's been fingering everytime we lewd talk for the past few months, he's feeling much more confident, and I've recently been keeping him on a strict diet of wearing a plug if he wants to cum. He's finally been enjoying fingering more lately, and the more comfortable the better.
We're meeting up for Christmas, it'll be at my place, with no one but the two of us all week, and I'm hoping we can (finally) make this happen. Two years without getting to have sex would be a little rough. Thanks for all the nice words, homos <3
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No.365848
>>331677
Ya' well, you're kinda wrong. Prolapse is when it's all fallen out and has to be put back surgically. A rectal prolapse looks like you shit a cartoon bee hive. 15 years working in the ER, seen it a few times.
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No.365849
>>333604
>>333604
Dildo would be a better trainer than a butt plug.
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No.366104
>>331461
You're just a pervert that is talking about this online to get your dick hard. Nice LARP faggot.
If you are in a relationship you should not be discussing this type of shit to a bunch of perverts. But since this is a LARP have fun you fucking faggots.
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No.366144
>>366104
I'm not sure why you'd say that, I posted this months ago and I just now gave an update, seems a bit far-fetched if I'm making this up, especially since nothing particularly sexy was discussed on here… Believe it or not, some people have relationships lmao.
I don't think you know what LARP means.
>>365849
Yeah that's what we've been doing
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No.370535
Great success! :3 Thanks for all the tips, anons. Have a lewd cutie to celebrate.
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No.370590
>>331474
no, do not use poppers
sounds like your bf is just nervous, have you tried toys on him yourself? plenty of lube, get him to open a bit
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No.379196
>>331659
Thank you. This helped me for when I use my toys.
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No.388845
>>331461
I mean if he's attempting to "train" himself then he's kinda on the right track for his part of the deal
the thing about it that's gunna be hard for you is that sex is exciting so people instinctively want to get the ball moving but you kinda have to take your time with butt stuff…especially in the beginning if they aren't used to it
lots of fucking lube jesus
there's never enough lube
fingering is good but clean toys are nice because they don't have salt, dirt or finger nails which are potential problems
light rimming is also good to prepare them as it relaxes the muscles, feels good and puts everyone at ease while DOING something, going back to what I said earlier about having to fight the urge to just slip it on in
good luck
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No.405899
So what if you crave anal and your luck is shit because of having an anal fissure? Letting it heal helps, then practicing with fingers, condoms, and live is nice. I assume it'll be a long time away from finally getting to take a dick.
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No.405930
>>331474
Yes, sniff what basically amounts to modified sulfur. 10/10 advise. Not. Do you even know how that shit is made?
The side effects of that stuff are pretty bad, and generally using drugs for anal is stupid. It hurts for a reason. You would not want to harm your bfs tight butt for any reason, because that would make it less pleasurable for both of you.
>>331485
Admin here gets it. Lots of lube, and fingering will feel good for the bottom if you do it right. Bonus if you hit and massage the prostate u.u
>>331634
It can happen but if you clean it up well it won't. Both parties should understand that it can happen though, so there is less embarrassment in the worst case scenario. If he knows you won't be judgemental about that, it will help him.
>>333604
I concur, taking it up the ass is the manliest thing you can do. Most men are afraid of it. It takes a certain degree of mental strength to be able to do it. The tops are the true bottoms here :^)
>>405899
Don't do anything until it's healed. Else it will only take longer.
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