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Have u ever penetrate a boy but cant go in?

BlaAnima2

By BlaAnima2
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BlaAnima2 Newbie

BlaAnima2

Posted
Posted

I have 2 experience with this and totally embarrass and 1 time nearly fail but eventually success

 

I try to penetrate the boy but it was too dark and unable to find the hole, as I cant see and really a bit 'not wanting' to touch that area of him to find it, then I try again to put in but fail, then he lead my bird to his hole and I was still unable to penetrate it as it is too tight

 

then the same happen for the second boy which led him saying "I bj for you better"

 

anyone experience such embarrassment before? How to solve this kind of issue, imagine if he is a virgin how do I put inside? Any tips?

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Guest See in the dark

Guest See in the dark

Posted
Posted
4 hours ago, BlaAnima2 said:

I have 2 experience with this and totally embarrass and 1 time nearly fail but eventually success

 

I try to penetrate the boy but it was too dark and unable to find the hole, as I cant see and really a bit 'not wanting' to touch that area of him to find it, then I try again to put in but fail, then he lead my bird to his hole and I was still unable to penetrate it as it is too tight

 

then the same happen for the second boy which led him saying "I bj for you better"

 

anyone experience such embarrassment before? How to solve this kind of issue, imagine if he is a virgin how do I put inside? Any tips?

Invest on a pair of night vision goggle so that you can see/find the hole in the darkness.

 

How-Night-Vision-Goggles-Work-2.jpg

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Guest Guest

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1 hour ago, Guest See in the dark said:

Invest on a pair of night vision goggle so that you can see/find the hole in the darkness.

 

How-Night-Vision-Goggles-Work-2.jpg

Instead of helping or guiding him,  u passed such a insensitive and brainless remark. Remember you were inexperience once. 

 

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upshot Rising Star

upshot

Posted
Posted

"Have u ever penetrate a boy but cant go in?"

 

heheh so you penetrated already or not or TRIED TO penetrate but can't go in? hahahahah..

 

sorry just can not resist.

** Comments are my opinions, same as yours. It's not a 'Be-All-and-End-All' view. Intent's to thought-provoke, validate, reiterate and yes, even correct. Opinion to consider but agree to disagree. I don't enjoy conflicted exchanges, empty bravado or egoistical chest pounding. It's never personal, tribalistic or with malice. Frank by nature, means, I never bend the truth. Views are to broaden understanding - Updated: Nov 2021.

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BlaAnima2 Newbie

BlaAnima2

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50 minutes ago, Guest first-timer said:

I know how it feels :(

 

My bf says my dick is simply too big to enter him :( 

 

Hi same case here

but i am not sure mine is big it just that 2 boys saying mine is too big for them.

 

i am currently learning to do it with hope of success. Scare to do it to a virgin.

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Guest Guest

Guest Guest

Posted
Posted
On 19/07/2016 at 1:30 AM, BlaAnima2 said:

 

 

I try to penetrate the boy but it was too dark and unable to find the hole, as I cant see and really a bit 'not wanting' to touch that area of him to find it, then I try again to put in but fail, then he lead my bird to his hole and I was still unable to penetrate it as it is too tight

 

 

 

if u are top how come u will not want to touch the asshole?

if the boy is not cute enough you wouldnt even wanna fuck him right

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cutejack Grand Master

cutejack

Posted
Posted

Not every top like to touch the hole.initially i was like that.could b still beginning stage or bi maybe.nothing to paiseh la.asshole not meant for fuvking mah.many times happen to me. An expert told me no man says he is lousy in fucking.actually survey shows from penetration to ejaculation is only takes about 2-7mins.

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Guest guest

Guest guest

Posted
Posted

I tried topping a guy.

My dick become soft when trying to enter him. even when I manage to stuff my dick inside the ass, I can't get the stimulation to get hard.

Ever since then I become a btm

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analogous Newbie

analogous

Posted
Posted
On 7/19/2016 at 1:30 AM, BlaAnima2 said:

I have 2 experience with this and totally embarrass and 1 time nearly fail but eventually success

 

I try to penetrate the boy but it was too dark and unable to find the hole, as I cant see and really a bit 'not wanting' to touch that area of him to find it, then I try again to put in but fail, then he lead my bird to his hole and I was still unable to penetrate it as it is too tight

 

then the same happen for the second boy which led him saying "I bj for you better"

 

This is my advice as a bottom.

 

Was your dick semi-soft when you tried to fuck him? If that's the case you could be too nervous. So calm down and do more foreplay first. Maybe you were not horny enough.

 

It also could be that the bottom, don't know how to loosen up for the initial penetration. He probably unintentionally clenched his asshole and making it difficult for your dick to enter. So use more lube! Or spank ass... like really spank it. Make sure he feels the pain of the slap. This will cause his ass to tense up and immediately relax afterwards. Spank his ass a few times and at the same time try to fuck him.

 

You guys can also try different positions.

 

You guys are in the dark, if you don't want to touch his asshole, then ask him to guide your dick to his asshole using his own hand.

 

If I know that my man is struggling to enter me, I would kiss him, lick and fondle his nipples, hug him, grab more lube, grab his dick and guide it to my asshole. I'm not going to waste my effort of douching so he has to fuck me no matter what!!!

That awkward moment when you say goodbye and then walk in the same direction...

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cutejack Grand Master

cutejack

Posted
Posted (edited)
13 hours ago, analogous said:

 

This is my advice as a bottom.

 

Was your dick semi-soft when you tried to fuck him? If that's the case you could be too nervous. So calm down and do more foreplay first. Maybe you were not horny enough.

 

It also could be that the bottom, don't know how to loosen up for the initial penetration. He probably unintentionally clenched his asshole and making it difficult for your dick to enter. So use more lube! Or spank ass... like really spank it. Make sure he feels the pain of the slap. This will cause his ass to tense up and immediately relax afterwards. Spank his ass a few times and at the same time try to fuck him.

 

You guys can also try different positions.

 

You guys are in the dark, if you don't want to touch his asshole, then ask him to guide your dick to his asshole using his own hand.

 

If I know that my man is struggling to enter me, I would kiss him, lick and fondle his nipples, hug him, grab more lube, grab his dick and guide it to my asshole. I'm not going to waste my effort of douching so he has to fuck me no matter what!!!

If every btm like u all tops can successfully enter.true enough.ever once i go soft while entering.a btm where he qyickly turn n lick n suck my balls till my cock got hard n i did what he wanted.both parties should be spontaneous n know what to do without expecting other party to initiate.

Edited by cutejack
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Guest Mengyee

Guest Mengyee

Posted
Posted

Aiyo! Tjis afternoon i managed to hookup with a poly guy. I’m his first time and it was difficult to get in. He ended up just sucking me. How to deflower him?

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Guest 72%dark

Guest 72%dark

Posted
Posted
  1. If you’re a top and you wanna do anal, then first of all get over any squeamishness about the anus. If your bottom isn’t experienced or the conscientious type, then politely ask him to clean and prep himself before the session, or even help him to do so. And even if not, bear in mind that you can always wash up afterward, it’s not that big a deal. So for goodness sake, don’t fail to find the bottom’s hole just because you feel squeamish about feeling about ‘down there’. (Ironic that some tops think they’re the manly ones when they don’t even dare touch an asshole. lolz)
  2. Make sure you’re fully hard. If you can’t manage that on your own, use something to help you get and stay hard.
  3. Choose a suitable position. Missionary is actually not the easiest position for anal sex because the anus is closer to the back of the body, not the front like a vagina; that’s why the bottom’s legs have to be brought up so high and the butt arched upward (using a pillow to prop up the butt helps). If you can’t manage that, try doggy instead; the anus is positioned for easier access from the back.
  4. The outer sphincter, that ring of muscle around the opening of the anus, is the main barrier to entry. If a bottom is “tight”, it’s mainly due to this. This is where preparation is absolutely essential. It involves inserting a lubricated object like a finger or a buttplug to ‘loosen’ the sphincter a little and get it accustomed to a large object entering. Without this step it’s still possible to push something in if you use enough force, but obviously that’s what causes pain and possibly even injury. So don’t skip this step! Lube up the hole, then gently and patiently stretch it open a little before attempting to insert your cock.
  5. If you can get your cockhead past the sphincter but it still feels difficult to push in deeper, it means you’re not using enough lube! In my experience this is the number one mistake that many tops make – they underestimate the amount of lube needed inside/along the anal passage to make for a smooth (and painless) entry. Many tops just apply a tiny squirt to the rim of the anus and rub some on their cock, but this is not enough if the bottom’s ass is tight and/or the top’s cock is big. Ideally lube should be applied to the inside of the anus as well; sticking the whole length of a finger in helps. Especially if you’re using a water-based lubricant, you need to apply more as it does dry up over time.
  6. Once you’re in (this is just optional advice), it’s usually more pleasant for the bottom if you start with slow and long strokes before you gradually increase your speed and force. Only the hardcore power bottoms out there will appreciate it hard and fast right from the get go.
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mantin30 Community Regular

mantin30

Posted
Posted
On ‎19‎/‎7‎/‎2016 at 1:30 AM, BlaAnima2 said:

I have 2 experience with this and totally embarrass and 1 time nearly fail but eventually success

 

I try to penetrate the boy but it was too dark and unable to find the hole, as I cant see and really a bit 'not wanting' to touch that area of him to find it, then I try again to put in but fail, then he lead my bird to his hole and I was still unable to penetrate it as it is too tight

 

then the same happen for the second boy which led him saying "I bj for you better"

 

anyone experience such embarrassment before? How to solve this kind of issue, imagine if he is a virgin how do I put inside? Any tips?

I might be wrong but when you mentioned you didnt want to touch that area of him to find it, I think you did not lube him. that was my very first mistake. must use your finger with lubricant and lubricate all the way inside.

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MalayBoy95 Explorer

MalayBoy95

Posted
Posted (edited)

I was first fucked by a white daddy with a huge dick. At first it was really agonizing, and that's on top of the fact that I've played with a big dildo before so it shouldn't be problem but it did. What I did after the first unsuccessful attempt was to go to the toilet, clean the area again and try again a second time and it went in pretty much completely. I guess what I was trying to imply was that attempting anal is partly a mental process where the bottom has to relax both his anus as well as his thought. If he's too tense no matter if you have a big or small dick it will never work out. If all else fails, try smaller objects first such as your fingers and slowly work your way up. Lube works wonders too, use plenty of it.

 

Oh! And like what the guy above said, only penetrate with an erect dick. If you're flaccid or it's a semi it will never be able to penetrate!

Edited by MalayBoy95
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Rice60640 Enthusiast

Rice60640

Posted
Posted
3 hours ago, 72%dark said:
  1. If you’re a top and you wanna do anal, then first of all get over any squeamishness about the anus. If your bottom isn’t experienced or the conscientious type, then politely ask him to clean and prep himself before the session, or even help him to do so. And even if not, bear in mind that you can always wash up afterward, it’s not that big a deal. So for goodness sake, don’t fail to find the bottom’s hole just because you feel squeamish about feeling about ‘down there’. (Ironic that some tops think they’re the manly ones when they don’t even dare touch an asshole. lolz)
  2. Make sure you’re fully hard. If you can’t manage that on your own, use something to help you get and stay hard.
  3. Choose a suitable position. Missionary is actually not the easiest position for anal sex because the anus is closer to the back of the body, not the front like a vagina; that’s why the bottom’s legs have to be brought up so high and the butt arched upward (using a pillow to prop up the butt helps). If you can’t manage that, try doggy instead; the anus is positioned for easier access from the back.
  4. The outer sphincter, that ring of muscle around the opening of the anus, is the main barrier to entry. If a bottom is “tight”, it’s mainly due to this. This is where preparation is absolutely essential. It involves inserting a lubricated object like a finger or a buttplug to ‘loosen’ the sphincter a little and get it accustomed to a large object entering. Without this step it’s still possible to push something in if you use enough force, but obviously that’s what causes pain and possibly even injury. So don’t skip this step! Lube up the hole, then gently and patiently stretch it open a little before attempting to insert your cock.
  5. If you can get your cockhead past the sphincter but it still feels difficult to push in deeper, it means you’re not using enough lube! In my experience this is the number one mistake that many tops make – they underestimate the amount of lube needed inside/along the anal passage to make for a smooth (and painless) entry. Many tops just apply a tiny squirt to the rim of the anus and rub some on their cock, but this is not enough if the bottom’s ass is tight and/or the top’s cock is big. Ideally lube should be applied to the inside of the anus as well; sticking the whole length of a finger in helps. Especially if you’re using a water-based lubricant, you need to apply more as it does dry up over time.
  6. Once you’re in (this is just optional advice), it’s usually more pleasant for the bottom if you start with slow and long strokes before you gradually increase your speed and force. Only the hardcore power bottoms out there will appreciate it hard and fast right from the get go.

What he said!  OMG trying to penetrate without foreplay or loosening the hole with fingers will turn your bottoms off bottoming forever. The pain is bad. You want to top and you are squeamish about finger a hole?

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Ben Ben Ben Newbie

Ben Ben Ben

Posted
Posted
2 hours ago, MalayBoy95 said:

I was first fucked by a white daddy with a huge dick. At first it was really agonizing, and that's on top of the fact that I've played with a big dildo before so it shouldn't be problem but it did. What I did after the first unsuccessful attempt was to go to the toilet, clean the area again and try again a second time and it went in pretty much completely. I guess what I was trying to imply was that attempting anal is partly a mental process where the bottom has to relax both his anus as well as his thought. If he's too tense no matter if you have a big or small dick it will never work out. If all else fails, try smaller objects first such as your fingers and slowly work your way up. Lube works wonders too, use plenty of it.

 

Oh! And like what the guy above said, only penetrate with an erect dick. If you're flaccid or it's a semi it will never be able to penetrate!

I can’t imagine a thick cucumber in an ass hole. How can a small ass hole accommodate such as big thick cucumber? 

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Guest Guest

Guest Guest

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Posted
On 15/08/2016 at 9:54 PM, Guest guest said:

I tried topping a guy.

My dick become soft when trying to enter him. 

 

I m having such problem too.

I m eventually very hard at first during e foreplay, kissing, cuddle, hug n tossing on bed before e fuck. But when ready to enter e hole my dick started turning soft (not totally soft like flaccid, juz not so hard as previous) n was not hard enuff to push in. 

Any other haf such problem too.

Anyone can advice on such problem? 

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Rice60640 Enthusiast

Rice60640

Posted
Posted (edited)
13 hours ago, Guest Guest said:

 

I m having such problem too.

I m eventually very hard at first during e foreplay, kissing, cuddle, hug n tossing on bed before e fuck. But when ready to enter e hole my dick started turning soft (not totally soft like flaccid, juz not so hard as previous) n was not hard enuff to push in. 

Any other haf such problem too.

Anyone can advice on such problem? 

Wear a cock ring to prevent blood flow back too quickly. Don’t rely on medication unless you absolutely have to; I.e cannot even get hard. 

Edited by Rice60640
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Guest Above Average Dick

Guest Above Average Dick

Posted
Posted

I agree with 72% and some of the others. If you want to top, you MUST take a role in helping the bottom get comfortable, and then you will both enjoy the sex. If you are in a hurry, and just want to enter him and cum quickly and leave, it will not be a pleasant time for either of you. I will repeat what has been posted above that you MUST use lube, and you should also finger the bottom for a while if needed, my recommendation is to put a condom over your finger while fingering him, so that if there is any mess, the amount which gets on your hand will be minimal.

 

Due to having a well above-average-dick, both in length and thickness, I often have difficulty inserting it into the bottom if we haven't spent enough time getting his hole ready. It can be a bit frustrating, but the mature thing for me to do is continue with the foreplay and helping him relax, or I don't deserve to fuck him. That means to do more kissing, hugging, massaging, rubbing, wanking, fingering, and even rimming if necessary. If you take your time and make sure the bottom's hole is properly prepped, the sex is so much better, so make it part of your routine.

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Ben Ben Ben Newbie

Ben Ben Ben

Posted
Posted
8 minutes ago, Guest Above Average Dick said:

I agree with 72% and some of the others. If you want to top, you MUST take a role in helping the bottom get comfortable, and then you will both enjoy the sex. If you are in a hurry, and just want to enter him and cum quickly and leave, it will not be a pleasant time for either of you. I will repeat what has been posted above that you MUST use lube, and you should also finger the bottom for a while if needed, my recommendation is to put a condom over your finger while fingering him, so that if there is any mess, the amount which gets on your hand will be minimal.

 

Due to having a well above-average-dick, both in length and thickness, I often have difficulty inserting it into the bottom if we haven't spent enough time getting his hole ready. It can be a bit frustrating, but the mature thing for me to do is continue with the foreplay and helping him relax, or I don't deserve to fuck him. That means to do more kissing, hugging, massaging, rubbing, wanking, fingering, and even rimming if necessary. If you take your time and make sure the bottom's hole is properly prepped, the sex is so much better, so make it part of your routine.

You are so understanding.

understanging TOP is very charming and atttractive! 

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