Does it really get easier?

[Kratos Aurion]

Hi, total newb here with a newb question. I'm a 27 year old guy who just recently started exploring this side, all my experiences were with women but last march i met a guy who is an exclusive top, and i gave him my first time. All i can remember was it was hell all throughout. We have done it a total 4 times but it hasn't gotten easier for me. Will it really get better? It is really uncomfortable for me but at the same time i like that he enjoys me.

 

[notN2pussy]

I would guess poor prep and maybe a fast moving or big top. Try different position?

 

[Dave NoCal]

Not all men are wired to be natural bottoms. Some come to like it with practice, particularly with toys. Others not.

 

[Nakedinpa]

When I first tried bottoming it was pure hell. Now I absolutely love it and have even cum hands free while being topped. One reason for this is who the top is. Some tops are more considerate and more experienced. A good top will help get you ready for this great experience- physically and psychologically. When they enter you it is pure pleasure. Also you can never have too much lube. Use lots of it and it will make it easier. Of course, your job is to relax and not expect it too hurt. If you expect pain you'll only exacerbate it. Try practicing alone with a dildo and see how that feels.

 

[Brodie888]

There's two parts to this equation.

One part is knowing how your own body works sexually and the other part is your partner knowing how your body works sexually.

I would suggest giving yourself lots of anal masturbation time to figure out what you like and how to relax your anal muscles to perform sexually. Once you know what you like and how to get to that point, you can use that with someone else. Things you need to know are how to douche, what/how much/how often you need lube, how to get your hole to relax enough to take a cock, where your prostate is and how to stimulate it.

On the other side of the equation you have good tops and then you have bad tops. If you are going through hell during sex, then I'd suggest your friend needs a few lessons on how to train a new bottom. It just sounds like he's skipping the foreplay and just jamming it in your ass. Which may be possible for an experienced bottom but everyone has to start somewhere.

 

[Kratos Aurion]

Thanks for the tips guys. Yes, we have been using lots of lube. I haven't really tried toys in fear that i might get too loose for him to enjoy. I tried the whole push out when he enters but it is still hella painful.As far as positions go, I do feel like being on my back is a lot better than doggy. However, when he gets too deep it feels like I'm going to take a leak and that can be uncomfortable. Haha, how do i know if my prostate is being stimulated? Will i just know?

 

[Andrue]

Try this position:

HE lies down on his back and YOU put his cock into your ass. This way you completely control how fast and deep you take it. His job at that point is simply to give you that complete control.

Some tops may not care for that role at all, in which case you point out “My hole, my rules - at least until I can take it easily.”

This will help you to feel a bit more relaxed and unclench your hole since you know nothing is going in unexpectedly or too fast or rough.

If you think you’re using enough lube, use a bit more.

And get lots of foreplay in there: fingers teasing, poking, slowly relaxing & stretching that tight muscle ring. There's no extra Brownie points for jumping on the "main prize" right off the bat.

 

[Andrue]

So Pup Amp at "Watts The Safeword" just happens to have published a YouTube video about using a butt plug which could help you get that hole relaxed or at least used to getting things in.

I would highly recommend you get yourself a butt plug or two (or three) of varying sizes and practice with them on your own, and probably along with your dude before his actual dick goes in.

And no, you won't get "too stretched out".

So check out the vid:

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[502855]

My first time being penetrated anally was absolute hell too! A poor top, not enough lube and zero foreplay. It hurt so bad I didn’t attempt it again for six years and I lost a lot of confidence around sex and my sexuality.

The advice above is bang on. You need to play with yourself and practice anal stimulation and penetration solo to get to know your body. Whether you realize or not, because of the pain and discomfort involved, you are tensing up this area every time you have sex. The only way through this is to train your body and mind to know that penetration doesn’t equal pain.

Standard buttplugs and didos will not make you “too loose” for a partner. This can only potentially happen if you graduate to epic sizes and fisting.... and you seem a long way from that right now.

Play with yourself, use lots of lube, find your prostate and get to know what that stimulation feels like.

Foreplay can make a big difference. Your partner can rim and stroke your hole, gently insert a finger, graduate to two or three (or use a dildo) while sucking your cock and kissing you. Ideally this can get you to a place where you are begging to be penetrated, can’t wait to be fucked.

If your partner doesn’t like that type of foreplay, then you need to prep yourself. Try inserting a butt plug ahead of sex with your partner to loosen and lube you up ahead of time.

Being on top like Andreu suggested is also a good idea. Either facing your partner or not, it helps with the psychological aspects of control and being penetrated. You can always shift positions once you get going.

Bottoming is amazing... but you do need to have confidence in your body and be able to discuss what is happening in the moment with your partner.

Have you discussed any of this with him?

 

[Brodie888]

Thanks for the tips guys. Yes, we have been using lots of lube. I haven't really tried toys in fear that i might get too loose for him to enjoy. I tried the whole push out when he enters but it is still hella painful.As far as positions go, I do feel like being on my back is a lot better than doggy. However, when he gets too deep it feels like I'm going to take a leak and that can be uncomfortable. Haha, how do i know if my prostate is being stimulated? Will i just know?

A better way is to start with one finger then two then three so you give your ass a shallow gradient it needs to get used to.

An almost fool proof way to get him in is to mount him, press his cock firmly on your hole and hold it there. Contract your hole as tight as you can for 5 seconds then completely relax. As you relax, you should feel your hole give way and allow you to slide his cock in about an inch before your hole clenches tight and stops him going further. He has to keep completely still at this point and not pull out and wait till you are ready to go deeper. Repeat the process until he's completely in.

Once he's in, start with short slow one inch thrusts and gradually build to longer faster strokes.

If you stick your thumb up your ass, you should feel this round half walnut shell lump through your rectal wall almost directly behind the base of your penis. If you press on this while you cum, it will feel amazing.

The feeling of needing to pee is just you pressing on your bladder through your rectal wall. You don't really need to pee, just ignore it.

As suggested by others, being on top to start is best. After a few minutes you can swap when you feel you can take more.

 

[Kratos Aurion]

A better way is to start with one finger then two then three so you give your ass a shallow gradient it needs to get used to.

An almost fool proof way to get him in is to mount him, press his cock firmly on your hole and hold it there. Contract your hole as tight as you can for 5 seconds then completely relax. As you relax, you should feel your hole give way and allow you to slide his cock in about an inch before your hole clenches tight and stops him going further. He has to keep completely still at this point and not pull out and wait till you are ready to go deeper. Repeat the process until he's completely in.

Once he's in, start with short slow one inch thrusts and gradually build to longer faster strokes.

If you stick your thumb up your ass, you should feel this round half walnut shell lump through your rectal wall almost directly behind the base of your penis. If you press on this while you cum, it will feel amazing.

The feeling of needing to pee is just you pressing on your bladder through your rectal wall. You don't really need to pee, just ignore it.

As suggested by others, being on top to start is best. After a few minutes you can swap when you feel you can take more.

Again, thanks! I'm meeting him again tonight and thanks to you guys I think I'm more ready. I haven't invested on a butt plug yet (maybe soon) but i tried stretching up to three fingers like you guys said.

In terms of being on top, i briefly discussed it with him and it's a no. He says he likes being in control.

Well, we'll see how it goes this time.

 

[Silbot.]

The above suggestions are great. Stay open minded. You two may simply not be a match sexually (i.e., you may be more comfortable on top), or it's possible that anal isn't really your thing and you should stick with oral, j/o, and get into other things. I'm leery of anyone who won't flip for their partner's comfort, especially when there is a discrepancy with respect to experience, but I hope it works out for you!

 

[cockydude2018]

It's obvious that you are expecting pain, so you freeze up, tense up, tighten up. Invest in a moderately thin (but long) size dildo and get comfortable with it. If you enjoy it, move to a larger, girthier one. Work ass play into your jacking play. And if you're into poppers, they can make the experience VERY enjoyable!

 

[Brodie888]

Again, thanks! I'm meeting him again tonight and thanks to you guys I think I'm more ready. I haven't invested on a butt plug yet (maybe soon) but i tried stretching up to three fingers like you guys said.

In terms of being on top, i briefly discussed it with him and it's a no. He says he likes being in control.

Well, we'll see how it goes this time.

If that's his attitude and he doesn't make any effort to make sex pleasurable for you, I'd suggest you find a new play friend.

 

[keenobserver]

If that's his attitude and he doesn't make any effort to make sex pleasurable for you, I'd suggest you find a new play friend.

AMEN, AMEN, AMEN! You're not asking him to bottom, for Christ sake, you're asking for an opportunity to make intimacy more pleasurable for yourself, but by extension him too. His refusal is a massive red flag.

 

[Curiousguyonthedl]

So Pup Amp at "Watts The Safeword" just happens to have published a YouTube video about using a butt plug which could help you get that hole relaxed or at least used to getting things in.

I would highly recommend you get yourself a butt plug or two (or three) of varying sizes and practice with them on your own, and probably along with your dude before his actual dick goes in.

And no, you won't get "too stretched out".

So check out the vid:

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Accept third party cookies

I only have experience with playing with my ass, I haven’t been with a dude yet, but that’s about to change. I absolutely love playing with butt plugs. They feel incredible when fully inserted in my butt. I’m pretty sure once I get an opportunity to take a dick I’ll have no issue in getting penetrated. If your tight definitely try some butt plugs.

 

[Kratos Aurion]

If that's his attitude and he doesn't make any effort to make sex pleasurable for you, I'd suggest you find a new play friend.

Thing is... i'm incredibly attracted to him though. Letting him go would be very hard for me.

To update, we met last night and with the tips I got here It was a lot better. I stretched before and I adjusted to his you know what sooner. I mean, the first attempt to enter was still really bad but he pulls out if i ask him to. Overall I'd say it was easier this time, he'd still hit some areas that get uncomfortable but I get used to it faster.

 

[Luvthetasteofcum]

Thing is... i'm incredibly attracted to him though. Letting him go would be very hard for me.

To update, we met last night and with the tips I got here It was a lot better. I stretched before and I adjusted to his you know what sooner. I mean, the first attempt to enter was still really bad but he pulls out if i ask him to. Overall I'd say it was easier this time, he'd still hit some areas that get uncomfortable but I get used to it faster.

When you say get used to it do you mean like he just starts pumping away and you become numb to it? For me it’s always really painful for penetration...but everyone I’ve been with has been slow for me at first. After a few minutes and I open up I start asking for them to go harder. It’s still difficult for me to get them thrusting deep because it feels like they hit a wall. I think my inner muscle tenses up and makes it hard for deep thrusts. I feel your pain man. Just make sure he isn’t being too rough.

 

[Brodie888]

Thing is... i'm incredibly attracted to him though. Letting him go would be very hard for me.

To update, we met last night and with the tips I got here It was a lot better. I stretched before and I adjusted to his you know what sooner. I mean, the first attempt to enter was still really bad but he pulls out if i ask him to. Overall I'd say it was easier this time, he'd still hit some areas that get uncomfortable but I get used to it faster.

If you are happy then that's fine. It's was just that your friend's reasoning for not letting you start on top was a massive red flag.

Rather than pulling out, holding still until the pain subsides is much better. Otherwise you take a few steps back in the opening up process.

 

[Kratos Aurion]

When you say get used to it do you mean like he just starts pumping away and you become numb to it? For me it’s always really painful for penetration...but everyone I’ve been with has been slow for me at first. After a few minutes and I open up I start asking for them to go harder. It’s still difficult for me to get them thrusting deep because it feels like they hit a wall. I think my inner muscle tenses up and makes it hard for deep thrusts. I feel your pain man. Just make sure he isn’t being too rough.

Deep thrusts to me are hard to explain lol. He'll do one and I get caught off guard and gasp a little. It's not necessarily pain but I can't really explain it.... a weird intense feeling.