For the gay guys. How can I make it easier?

9 Sep 2013

How can I reduce the discomfort of anal play? I use a good quality lube and try to go slowly but sometimes even small sized items are uncomfortable. Is there anything I can do to to stretch myself a little? Can anyone help me please?

9 Sep 2013

Im not a guy but I think I can help haha, basically try with fingers first! Wear a glove or something if you want, just rub the outside of it to relax it and then when your ready try and push one in! If that hurts play with yourself to relax then try a bit again, keep doing this until its comfortable with one finger and then work from there smile

9 Sep 2013

Quote by Shemale_lover
Im not a guy but I think I can help haha, basically try with fingers first! Wear a glove or something if you want, just rub the outside of it to relax it and then when your ready try and push one in! If that hurts play with yourself to relax then try a bit again, keep doing this until its comfortable with one finger and then work from there

Thanks lover. I have been trying to gently and gradually loosen myself with some success but next time I try I am as tight as ever. I start off with 1 finger, then 2 then increase from there. It does take a long time to get myself loose enough to get anything more substantial in though.

9 Sep 2013

Hi Martb40,

I'm also not gay but do enjoy some anal pleasure from time to time. When I introduce anal sex to a new bedpartner I always go very very slow and let them get used to the idea at all and then the size. But after some experimenting I found that in the cases I've been presented with its usually between the ears.
My last girlfriend loved anal stimulation and we've tried various things. At some point we bought a new buttplug and she thought it was huge and would never fit. One night a while later I let her put on a blindfold and made her relax on the bed. Took care of the seen, fresh sheets, good temperature et cetra. I started to gently touch her all over her body, kiss her everywhere.. All the while she had to stay silent on the bed.. until she was craving for some penetration or any other serious stimulation.
I started to go down on her.. well to detailed already anyway.. used one finger for her rectum and one for her pussy. Get her wet and ready. Then(while she was still blindfolded) I lubed up the new buttplug and while stimulating her pussy and clit started to work it inside. She never knew it was the big one until I later during sex took of the blindfold and she saw it in the mirror.

Same goes for myself.. I always started small but when we got some new stuff and she came back from a business trip we tried them on me. I hadn't been stimulated anally for months but within no time I could take 4.5 cm in diameter(the biggest I've ever had) just because I was very relaxed and eager.

My point is.. mindset and full relaxation of the body and mind make more possible then you think. As soon as you think something will be to big you're rectum will react and make it to big.

In my experience anyway. Hope this helps you.

9 Sep 2013

Quote by DutchMike88
Hi Martb40,

I'm also not gay but do enjoy some anal pleasure from time to time. When I introduce anal sex to a new bedpartner I always go very very slow and let them get used to the idea at all and then the size. But after some experimenting I found that in the cases I've been presented with its usually between the ears.
My last girlfriend loved anal stimulation and we've tried various things. At some point we bought a new buttplug and she thought it was huge and would never fit. One night a while later I let her put on a blindfold and made her relax on the bed. Took care of the seen, fresh sheets, good temperature et cetra. I started to gently touch her all over her body, kiss her everywhere.. All the while she had to stay silent on the bed.. until she was craving for some penetration or any other serious stimulation.
I started to go down on her.. well to detailed already anyway.. used one finger for her rectum and one for her pussy. Get her wet and ready. Then(while she was still blindfolded) I lubed up the new buttplug and while stimulating her pussy and clit started to work it inside. She never knew it was the big one until I later during sex took of the blindfold and she saw it in the mirror.

Same goes for myself.. I always started small but when we got some new stuff and she came back from a business trip we tried them on me. I hadn't been stimulated anally for months but within no time I could take 4.5 cm in diameter(the biggest I've ever had) just because I was very relaxed and eager.

My point is.. mindset and full relaxation of the body and mind make more possible then you think. As soon as you think something will be to big you're rectum will react and make it to big.

In my experience anyway. Hope this helps you.

Thank you Mike. I will try to relax a bit more and take things slowly. I have been doing that though. Maybe I should try to have my partner try to insert it for me!

10 Sep 2013

Try to relax fully if you think it's going to hurt then you subconciously with tighten yourself up. Already your using a lube which is always a good thing.

10 Sep 2013

Quote by kylie_kained
Try to relax fully if you think it's going to hurt then you subconciously with tighten yourself up. Already your using a lube which is always a good thing.

Thanks Kylie. I've been relaxing as much as possible. I've even had some success. It just makes me uncomfortable or a couple of days after I've been playing. I would like to have a little more permanent give if you know what I mean.

11 Sep 2013

Ok guys. Thanks for the help. I've been doing a little experimenting with your suggestions and I think I have it almost cracked, so to speak. Lots of lube, then 1 finger, then 2 fingers. Here's where it important. A tapered glass dildo slides in very easily and gives that little bit of stretch to relax the sphincter muscle. After that I found that I could get some of my wife's sizable dildo's in my ass with some degree of comfort. The most positive aspect of this is that there is little or no lingering discomfort now, though there was a little blood when I was done experimenting. Nothing much though. I guess there is only so much stretching you can do even with the best preperation! Thank you all for your suggestions.

11 Sep 2013

I'm not a guy, but I can give you one tip that helped me immensely when being introduced to anal play was help your body to associate it with pleasure. When I was first getting used to it, my Master would talk with me to keep me relaxed, but at the same time have me play with my clit a bit while stretching/preparing so that my body became conditioned to associate anal play with pleasure and for the most part that makes things much easier and enjoyable.

For a guy, I'm going to go out on a limb and assume that the same thing can be done, but I could be completely wrong. I do hope that this helps some for you, though. Best of luck smile

12 Sep 2013

Quote by Crows_kitten
I'm not a guy, but I can give you one tip that helped me immensely when being introduced to anal play was help your body to associate it with pleasure. When I was first getting used to it, my Master would talk with me to keep me relaxed, but at the same time have me play with my clit a bit while stretching/preparing so that my body became conditioned to associate anal play with pleasure and for the most part that makes things much easier and enjoyable.

For a guy, I'm going to go out on a limb and assume that the same thing can be done, but I could be completely wrong. I do hope that this helps some for you, though. Best of luck

Thanks Kitten. Every little helps. I haven't tried the pleasure part, usually because I don't seem to have enough hands lol. But I guess when I bring my partner into the equation it will become easier. I think there was a real breakthrough today as I finally relaxed enough to insert something without pain. Thanks again for your help.

1 Oct 2013

I am a gay bottom and love the feeling of a hard cock in me, rubbing and creasing my prostate… so believe me when I tell you that the key to anal sex is to relax and use lots of lube to allow the cock or dildo to slide in. Start small like with fingers and gradually increase length and girth.

1 Oct 2013

Quote by TonyZ
I am a gay bottom and love the feeling of a hard cock in me, rubbing and creasing my prostate… so believe me when I tell you that the key to anal sex is to relax and use lots of lube to allow the cock or dildo to slide in. Start small like with fingers and gradually increase length and girth.

Thank you for the advice. Much appreciated!

2 Oct 2013

Quote by martb40
How can I reduce the discomfort of anal play? I use a good quality lube and try to go slowly but sometimes even small sized items are uncomfortable. Is there anything I can do to to stretch myself a little? Can anyone help me please?

I know it may seem strange but when you're lubed push your sphincter out, that actually relaxes the muscles and allows easier entry. However, as a gay guy, I would recommend a cock with a good looking man attached to it. Lol

2 Oct 2013

Quote by dpw

I know it may seem strange but when you're lubed push your sphincter out, that actually relaxes the muscles and allows easier entry. However, as a gay guy, I would recommend a cock with a good looking man attached to it. Lol

LOL DPW. I don't think the man is necessary in my case but thank you for the advice.

2 Oct 2013

Easier? What happened to HARDER?

2 Oct 2013

Quote by dpw

I know it may seem strange but when you're lubed push your sphincter out, that actually relaxes the muscles and allows easier entry. However, as a gay guy, I would recommend a cock with a good looking man attached to it. Lol

Yes, pushing out your sphincter works because as you let it go it has to return to its original state "sucking in" the intruding object, but the down side is that it may cause prolapse... I would rather you work on breathing exercises until it becomes natural, and just breath in as you are inserting the dildo in. For me though, dpw's recommendation of finding a hot man attached to a hard dick works wonders ;))

2 Oct 2013

Quote by TonyZ

Yes, pushing out your sphincter works because as you let it go it has to return to its original state "sucking in" the intruding object, but the down side is that it may cause prolapse... I would rather you work on breathing exercises until it becomes natural, and just breath in as you are inserting the dildo in. For me though, dpw's recommendation of finding a hot man attached to a hard dick works wonders ;))

Thank you once again. Do not want a prolapse.

3 Oct 2013

Quote by malebox
Easier? What happened to HARDER?

Right now ....harder is not an option. Still recovering from bigger. Harder would be just too much lol.

10 Mar 2021

Warm water enemas help you relax but also clean you out

10 Mar 2021

Quote by sissyboycindy
Warm water enemas help you relax but also clean you out

Yes, I have started to use enema's also, which of themselves are not unpleasant. They definitely clean you out lol.

22 Mar 2021

Smoke pot, lots of pot.

23 Mar 2021

You could also use something like lidocaine gel, it'll ease the discomfort rather quickly ?

Curiosity is one of those insatiable passions that grow by gratification.

18 Apr 2025

Finger yourself first then gradually use more than one finger 2 or 3. When you get comfortable using 3 fingers use a dildo

23 May 2025

The past few weeks I’ve been doing a lot more anal play on myself than in quite a few years. I’ve got a new toy that’s given me a couple of prostate orgasms, something I haven't had in many years.

I’ve also been slipping a finger inside my asshole whenever I have the chance. In the shower, sometimes when I’m just in the bathroom, whenever. Feels so damn good, and reminds me I’ve gotta get an actual warm, throbbing, spurting penis in me someday.

But to the topic, with the finger I can feel what my sphincter is doing, when it’s contracting and when it’s loosening. The feedback is helping me learn to control it a little, and as a result I’m getting better at relaxing and letting the toy in too. So yeah, getting to know how your hole really works is probably key.

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6 Jul 2025

For me, I've always had butt plugs, small to large. Lube and patience. I know that no matter how lose it may get, a break in action and it will tighten and need to be worked back loose. There have been times I let it slip, and I tighten. Then I get a call from a well-endowed man asking for a date. Immediately, I'm working my ass with my plugs because the pain is real. My favorite activity is to blow the plug out and put it back in. It goes back in much easier each time. Then I work a bigger plug in, and I begin to blow it out. One of my favorite things is to sit on a towel in my office chair. I lean forward onto my desk, and I push it out. It stays in my crack, yet out of my hole. When I sit up, my hole goes back over it. Ultimately, your lover's experience takes over from there. Sometimes it would seem you have the entire tube of lube in your hole and his cock it covered in it. But it can still be painful going in. He may have to pull out and apply more lube. I make sure to always have plenty of lube. And make sure it is anal lube.