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Penetrating a difficult hole


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I've had hot times from a top forcing his way in and hurting before I adjust. But recovering from anal tearing is never fun, especially if you have to resort to mostly liquids for several days to give your hole a rest. 

Foreplay and lube are invaluable. Holes can accomplish miracles if you give them a chance to. Foreplay can be rimming, fingering, toys, all sorts of fun ideas. Lube can be lubricant products, or spit, or throat slime, or whatever else slicks your cock and helps glide into the hole. 

Not only that, but foreplay just makes for better sex. I have a friend who complains about when guys skip straight to the main activity of the encounter because it skips a lot of things that get him in the mood and make the encounter great for him, and it's like walking into a movie three fourths of the way through. 

And also yeah, big fan of poppers. Poppers do wonders to negate my gag reflex and relax my hole

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18 hours ago, Bimarried001 said:

From a bottom’s perspective, the thing to do is to ease it in. Tops don’t realize that once they get that cock in we will adjust. But forcing it in may feel good to the top but it will take the bottom some time to adjust to the pain. 
 

I’ve had guys force it in me so I know. 

I've had guys force it in me too, usually when I'm bound and gagged for some rough sex. The sudden pain of his forced entry is off the scale , but like all good things it eventually comes to an end. Finding sadistic Tops isn't as easy as it was when I was a few decades younger & still had a bubble butt. 

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Just push in and out slow and use lots of lube. That is how it worked the first time for me. just go in a little deeper each time depends what the Bottom can tolerate until you get all the way in. never go fast or be in a hurry.

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On 4/18/2024 at 9:55 AM, topblkmale said:

 

find a better (loose) bottom

 

OR, find a more considerate top.  Reminds me of a time when I was in a sling, and this guy just started to ram his cock into me.  I yelled, "EASY!"  He was smart enough and considerate enough to slow down until I could get the head of his cock into me.  Then, it went fine.

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Being a bit on the thick side, I've learned that the time invested in relaxing the Hole always pays exponential dividends.  That can be anything from quiet "breed-talk" to more tongue in the Hole, and occasionally that doesn't work.  On those occasions, I just tell the bottom to take a few more loads off other Cocks, and then come find me.  

I try never to make it a "personal" thing - more of an "engineering" thing.  

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I find that I often need to"start small" and work up to bigger cocks. At bathhouses and sex parties, I usually try to find a less endowed top to breed me early on and then I'm ready. I think of it like an appetizer. As the night goes on, I'll beat cumdump for anyone with any size.

If I'm hosting an anon guy at home who wants a quick hatd breeding session, I'll work my ass open before he gets there so when he finds me ass-up I'm ready to take any size cock.

If a guy is too big and has to start slow to open me (hopefully with tongue and fingers) he usually find that that it's worth it once he starts to really fuck my very willing ass.

Edited by Eastvillagefun
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As a bottom who closes up after about five minutes but if you give me one minute I can get toys bigger than 99% of dicks in there be patient opening him up. The guy will probably open up more quickly than you think if you use a few fingers.

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15 hours ago, barefucker44 said:

Agree.  Take time to open up your hole until the top can fuck freely and breed when he is ready

Barefucker44 open me up like that and then ride me hard and long...

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These are all good suggestions- my two cents for the top, first pull out and add more lube then start easing back in and take a few minutes to get to full depth and power. While you do that you should tell the bottom that you are going to use more lube but that he better shut up and take it or you are gonna make it worse. You don’t have to mean it but it’s hot to hear 

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On 4/18/2024 at 12:25 PM, Bokkierob said:

grip his shoulders and force it deep

I will never pass up the opportunity to force cunt. I just love it. In any case, coitus interruptus is a grave offence. I do not pull out. At most, I stop pushing while the pain of the initial violation subsides and his anus adjusts to my girth. That's just basic training at the minimum level of suffering I require.

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On 4/18/2024 at 9:55 AM, topblkmale said:

 

find a better (loose) bottom

 

This but also… 

I will usually get him to breathe slowly and deeply to let me in. I’ll go in an inch and hold. Tell him to breathe deep. Breathe deep with him. Lead by example. In slow….  Hold breath…. Out slow…. Push in another inch and hold. Repeat until I’m all the way inside, and then stay in. 
 

Then do that thing where I’ll be balls deep and flex my cock so it’s rock hard, then unflex. Flex, unflex. Get him used to having me in him. Then very slowly, I’ll start to pull out just an inch. Then back to balls deep. Then pull out two inches, and back to balls deep. 
 

Very slowly work up to actual fucking. 
 

But I’m only gonna go to all this trouble with a special bottom. Someone I’m really excited to breed. Someone who I traveled to. Someone I have a powerful chemistry with. 
 

if I’m at a bathhouse or a fuckparty, I’ll just find a better looser hole. 

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i'm pretty much total bottom and  fucked  a guy once in 15 years. Maybe about a year ago a guy approached me on Squirt. A sweet university student from Iran stating he wanted to be fucked for the first time.  Despite being bottom, i find a guys ass is the most visually beautiful part of his body, and his was no exception.  And he really felt like the real thing, a virgin and a babe in the woods. i didn't want his first experience to be a bad one, so i ended up picking him up at university housing and bringing him to my place.  

As noted, i'm very bottom wired. i get hard as a rock when a Top wants to penetrate and breed me, but i stay soft at the prospect of having my penis used, especially for fucking.  So i told him i might not be able to perform and i popped a viagra before picking him up.  i did manage to get hard enough to penetrate him, but he was so tight, even after rimming and fingering him for quite some time while i was sucking him. i laid him on his back, used a liberal amount of lube. He never complained of pain, but the whole time i was trying to get in without hurting him, he had his eyes shut and was pushing back against me with his legs. He was fighting it and begging for it at the same time. i managed to  get about half way in, but i couldn't stay hard enough to penetrate his fighting hole. Well, that and it was just super tight.  i sucked him off and he was really happy with his first experience, he hits me up regularly. i haven't hooked with him again, but we remain friends.  He's a totally sweet guy. i'm just not top.

As for my own hole?  It sometimes hurts if a Guy just shoves in without lube or is exceptionally large, but i don't have an ass pucker anymore, i have a slash that has been molded by a few thousand Tops to receive cock. i can squeeze and milk with my inner muscles, but access is not an issue, and i never squeeze when a Man is entering me. If He wants to penetrate me, i want Him and am open. i think that's a big part of it, if a bottom is nervous or inexperienced and clench, their hole will naturally tighten. Part of opening is in the head, not in the hole. 

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Man, people saying to find a "better" bottom- that being looser in your book-

Know what I'm just going to delete that even if it is deserved. Some tops. Just damn.

Edited by ObjectPersona
I will be nicer than is deserved
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On 4/18/2024 at 1:15 PM, FelchingPisser said:

Pull out and rim him until he is begging for it.

I work really hard to have a loose, easy entry hole so this is often a problem for me.

But this suggestion is what will open that bottom 99% of the time.

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