Penetrating a difficult hole

[cumnutte]

I have a tight hole but I tell tops not to worry and just go for it.  Yes it sometimes hurts but I know it's only going to be for the first 30 thrusts or so, that also helps relax things.

The main bummer about having a tight hole is that only a truly stiff dick has a chance.  At the bathhouse near me, many of the guys can't get hard enough, so I end up sucking out many more loads then get shot into me. 

[Nikba]

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

When you’r fucking a dude for the first time and he’s struggling to take your cock and you’re only half-way in, what do you do? Pull out, keep pushing or grip his shoulders and force it deep up his hole. 

A lot has to do with chemistry between the two, many cases bottom needed more fore playing, feeling his ass, caressing his back, legs, feeling all his entire body, soft kissing his neck, back, rubbing his tits. Whispering, telling him how sexy and beautiful his body while caressing and kissing. At the meantime, poking in-out slowly and be persistent . Once the bottom relax and muscles ring loosing up, it all game….. it works every time with new or seldom bottom. I always prepare my guy with good rimming, playing with fingers and lot of lubricant…… 

[ccmmss]

Chemistry is right.... the top can build some sort of level of trust with the bottom.... once he is in.... normally it continues!

[Iker80]

Just fuck at the depth he'll take. You can feel when your dick is hitting resistance and read the guys physical response. You'll know how deep is his limit. Most the time he'll relax and you'll find you're going deeper as the fuck goes on. Some guys are like this and it gets better the more they're topped, and some are always like this and need opening up every time. It doesn't matter to me if I don't get my full dick inside him, it still feels great and I like making my bottom feel good so I stay in the depth he can manage. Main thing is my dick goes in him and I'm happy with that.

[Bokkierob]

On 5/19/2024 at 10:23 AM, Nikba said:

A lot has to do with chemistry between the two, many cases bottom needed more fore playing, feeling his ass, caressing his back, legs, feeling all his entire body, soft kissing his neck, back, rubbing his tits. Whispering, telling him how sexy and beautiful his body while caressing and kissing. At the meantime, poking in-out slowly and be persistent . Once the bottom relax and muscles ring loosing up, it all game….. it works every time with new or seldom bottom. I always prepare my guy with good rimming, playing with fingers and lot of lubricant…… 

Exactly, the bottom must be prepared for his fucking. Yes, a good deep rimming gets his asshole excited and ready for my cock. During penetration I never ASK my bottom if he’s ok or if it hurts - I read his physical cues. I TELL him his ass feels amazing, I TELL him I’m ready to force another inch of my hard meat up his hole. I also TELL him that my cock is only going to go deeper up his ass and will only stop when I’ve got every inch of my shaft inside him and my balls are pressed against his. I make him understand that his job is to milk my cock and I must be deep in him. I find most if not all bottoms react well to being ordered to take my meat

[TomOnHisKnees]

The first time I got fucked my friend put me into position(on my knees bent over a hay bale).

After lubing himself he would poke at my hole.Each time he poked it would pucker up.He did this till I got used to him poking me there.

He positioned the tip at my hole and started rubbing my shoulders.Then my back.Then my hips then back up to my shoulders.

Then he grabbed my shoulders and asked"Are you ready?"

As soon as I told him yes he pushed 4 inches of his 8 inch cock in me.

I remember screaming out loud from the pain but I didn't want him to stop.

He slowly worked the rest of his cock into my ass till he was balls deep.

He held himself there while he rubbed my shoulders some more.

Then he started fucking me real slow.

He would pull out till only the tip was still in me then slowly push himself all the way in.

It still hurt but I knew the first time would.

After about 10 minutes of slow fucking I felt his thrusts become erratic.He was breathing and moaning real loud.

His hands gripped my hips and I heard him yell those two beautiful words"I'M CUMMING!"

Then he began flooding my ass with cum.

I couldn't actually feel his cum shoot in my but I could feel his cock spasm in me as he came.

I remember feeling empty when he pulled out of my ass.

Then he slapped my bottom and told me"I'm going to love fucking that ass."

He left me there with my bare ass still bent over the hay bale.

[cman102]

On 5/14/2024 at 1:26 AM, ObjectPersona said:

Don't take your impotence out on bottoms.

Lol late but its not impotence - it doesn't feel good to have fuck a hole that constricts your dick. Its not pleasurable for me but apparently I hit a nerve with you

[KindaBasic]

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

When you’r fucking a dude for the first time and he’s struggling to take your cock and you’re only half-way in, what do you do? Pull out, keep pushing or grip his shoulders and force it deep up his hole. 

As they old joke goes, What’s the definition of Irish Foreplay? Brace yourself, Brigitte!

[Sharpshooter13]

1) more lube more lube more lube

2) poppers. they really help.

3) take your time and ease it in.  easy does it at the beginning. ramming it in is never the answer. place your head on his hole, and keep it there for a few seconds, then very gently press it in, verbally communicating to him 'I'm going to fuck you now' or "here it comes" so he can really relax.

5) once partially in, up to halfway, just let it sit as his hole acclimates. then ask if he's good, and gently insert the second half of your dick. once all the way in, let it 'marinate' as he adjusts to your size.  If you are big, you can do two steps forwards and one step back, increasing gradually how deep you go.  This gives him time to adjust to your length and girth.

4) learn where the actual hole is. many guys will press it into the edge or even no where near.  aiming dead center helps a lot to relax the first sphincter.

5) bottom needs to take deep breaths and push out, and he also 'want it' and not be scared of it.  eating him out can really help with this. also being intimate: making out, caressing, ear nibbles, cuddling can help. hard to do in some scenarios, but you can at least rim him.  even words of encouragement can help "your hole is so hot" "you're being such a good boy"