Getting A Tight Hole Ready For Thick Cock

thickforsure

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Hey guys,
I am looking for some tips on how to get a tight asshole ready for my very thick cock. I don't mind spending a lot of time getting him ready. I'm just wondering if there are some tips. So far he has only been able to take the tip, and I have a hard time maintaining a hard on if it takes too long for me to get it in.
Any advice would be greatly appreciated.
Cheers
 

Infernal

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Patience, lots of lube, and a relaxed, comfortable environment. If you can't stay hard, then try not to get hard until you're ready to penetrate him. Take it slow, and make sure he's comfortable. You could also spend time getting him ready, then lay back and let him sit on you. That way he can control the speed and depth.
 

51arledge

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I am so turned on by rimming my FB that staying hard is not an issue at all!
He typically gives me some oral attention for my cock first and then I will blow him for a bit before he goes into doggy position. I could tongue that hole for a long time, but then I start with a finger now that his hole has lots of my saliva on it/in it. One finger for a bit, and then 2, then my tongue---and beard!-- pretty soon he's begging for my dick. We use a lot of lube to get started because I'm also thick, but when I do the first couple of strokes nice and slow, he's soon ready for pounding.
 
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Brodie888

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Get a series of progressively larger butt plugs. Start with the thinnest and as he relaxes, increase the girth. He should be ready after that.

Lube is key, use more than you think.

Press the tip of your cock on his hole, tell him to clench his hole as tight as he can for 5 seconds and then relax. When he relaxes your cock should slide in an inch before he tightens against you. At this point you MUST stop moving. Repeat process until you are all the way in.

Once you are all the way in, grind your cock inside him for a while, then start with 1 inch thrusts before increasing to full thrusts. In the early stage, avoid pulling out. After 5 mins or so you probably can pull out to reapply more lube.

The best position to do this process is for him to be on top so he can control when to stop moving when he feels his hole is about to spasm. Once he's got to the full length thrusting stage, it should be safe to change position.
 

DiomedesXVI

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I’ve dealt with this. Guy really wanted me to pound his ass. First time we tried, he couldn’t get even my head in cause it hurt so much. And we had prepped for a while before that.

He was headed back out of town though so we wouldn’t get another chance until a couple of months later. He had the idea to buy a dildo nearer to my girth measurements (I have 6.5 girth but if very very very aroused I’m hitting 7 girth). So he got a 6 inch girth dildo and used it often just to practice (my guess is 30 minutes a couple times a week since there wasn’t a huge rush).

When we met again 2 and a half months later, we tried again to fit my fat cock inside his ass. It still took prepping and patience but I got the tip in, let him adjust to its width a moment then slowly slid more and more of my length into him. I stopped a couple of times to let him adjust, but eventually I was able to slide my whole length and girth deep deep inside him. I gave him the thing he’d long waited for and to this day he still considers it the best sex he has ever had.

So my advice: get a similarly sized dildo and have him practice with it. You can even make it a fun erotic playtime thing. Fit the routine in among jerking, sucking, and rimming each other, making a moment where you just drill his ass with a dildo.
 

steel33

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I went a different route. I hooked up with a couple of guys that I really like and both were very thick, way more than I've been with before. I prepped for over 2 hours for our meet and this included.dildo play to prep me for the size. I didn't expect that I was I was undersold on their girth. As a bottom it made me even more horny to be with these guys. The thicker of the 2 tried to very slowly enter me and we were doing a good job. I don't know what happened but it started to hurt like hell, I'm guessing he was in at least 3/4s of the way. I was not leaving without this. They did have poppers, neither was using them but they did say they might help. I did do a little small of them, got a tiny head rush and the 1st guy tried it again. It felt amazing as he slid into me, I'm getting chills right now. That was all I needed. We continued for well over an hour. I was in no way in any discomfort that day or the next after getting pounded that long.
I didn't like the chemical smell at all but for what I got I would definitely do it again.
 

DiomedesXVI

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I went a different route. I hooked up with a couple of guys that I really like and both were very thick, way more than I've been with before. I prepped for over 2 hours for our meet and this included.dildo play to prep me for the size. I didn't expect that I was I was undersold on their girth. As a bottom it made me even more horny to be with these guys. The thicker of the 2 tried to very slowly enter me and we were doing a good job. I don't know what happened but it started to hurt like hell, I'm guessing he was in at least 3/4s of the way. I was not leaving without this. They did have poppers, neither was using them but they did say they might help. I did do a little small of them, got a tiny head rush and the 1st guy tried it again. It felt amazing as he slid into me, I'm getting chills right now. That was all I needed. We continued for well over an hour. I was in no way in any discomfort that day or the next after getting pounded that long.
I didn't like the chemical smell at all but for what I got I would definitely do it again.
I’m not a fan of poppers myself, the smell is off-putting and some guys are complete popperheads where it seems like they are loopy the entire time.

A guy I met up with twice did poppers the entire time I was pounding his hole, he was exactly as loopy as I described. My cock is girthy as fuck, almost every guy’s hole is tight for my dick, but this guy was huffing so many poppers during me fucking him that his hole was actually a bit loose for my dick. It was a terrible lay, perhaps the worst lay I’ve ever had. Like I get he might not have wanted to hurt from taking my girth, but there’s a level of moderation that one should use.

Most guys are able to grit through the initial pain my girth causes if they really want my dick deep in them. And no guys who have ever gritted through it have ever regretted it haha.
 

chrisrobin

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Hey guys,
I am looking for some tips on how to get a tight asshole ready for my very thick cock. I don't mind spending a lot of time getting him ready. I'm just wondering if there are some tips. So far he has only been able to take the tip, and I have a hard time maintaining a hard on if it takes too long for me to get it in.
Any advice would be greatly appreciated.
Cheers
If he's a bf then he can also help by taking a daily dose of castor oil - this lubricates the anal linings and make penetration easier, muscles relax and he'll enjoy it.
Example
Make a circle with you thumb and forefinger then poke the idex finger of the other hand in like fucking.
Then lubricate the circle you formed with a little olive oil and see how easy the fucking finger slides sensuously.