How do I prepare for anal sex?

dacoach44 · Jan 29, 2017

I have a gay lover who likes my ass, and I am new to this. I am 72, he is about 5" and medium girth. He tried the other nite, but it was sorta painful (duh) and altho I play with a prostate massager, I couldnt take all of him. You guys got advice for me on how to stretch out and get ready for date night? I had some lube, of course.

Carnevil9 · Jan 31, 2017

Have him start with a finger or two, and work up to his dick when you feel ready for it.

dacoach44 · Jan 31, 2017

Carnevil9 said:
Have him start with a finger or two, and work up to his dick when you feel ready for it.

Yes, I do have an enema bulb, will flush out first. I also have a few toys, thanks.

HisGreedySlut · Jan 31, 2017

Agree with the advice to start with finger massage to relax the muscles. Rimming is a nice way to relax them too if you're into that.

If your prostate massager isn't close to his girth, that's probably the issue.

Also, you may have already done so, but we always lube both ways - both my ass and his cock for extra easy entry.

Make sure you're mentally relaxed too - and that he is prepared to go as slowly as you need so that it's enjoyable for both of you.

Good luck & have fun!!!

dacoach44 · Jan 31, 2017

Thanks.

HisGreedySlut said:
Agree with the advice to start with finger massage to relax the muscles. Rimming is a nice way to relax them too if you're into that.

If your prostate massager isn't close to his girth, that's probably the issue.

Also, you may have already done so, but we always lube both ways - both my ass and his cock for extra easy entry.

Make sure you're mentally relaxed too - and that he is prepared to go as slowly as you need so that it's enjoyable for both of you.

Good luck & have fun!!!

He is considerate, for sure. Nice man. I do have several toys with which to play and get ready. I will get my ass flushed out good so wont feel stupid about him and his fingers fucking me.

box13 · Feb 1, 2017

A toy that's nearly the size, with some taper, would help.

It may help if the toy is warmed in hot water first.

Go to what you're comfortable with, then stop. Over time you'll relax and be able to accept more.

You have to be the one to relax and push back, adjust the angle, determine when it's right to go more, etc. That area is good at reflexive tightening, and that will work against you and cause pain. Especially if you're nervous.

Take time.

I enjoy using my fingers, but I don't actually enjoy the feeling of them. So that may or may not work for you.

A lot of stories are written as "it hurt and I cried and there was blood...but it's just what I needed". I suspect that the people who are writing them have absolutely no idea what that feels like for real, or what the explanation to medical staff is like. Most fantasies are not what they're cracked up to be.

dacoach44 · Feb 2, 2017

Thanks, pard.

box13 said:
A toy that's nearly the size, with some taper, would help.

It may help if the toy is warmed in hot water first.

Go to what you're comfortable with, then stop. Over time you'll relax and be able to accept more.

You have to be the one to relax and push back, adjust the angle, determine when it's right to go more, etc. That area is good at reflexive tightening, and that will work against you and cause pain. Especially if you're nervous.

Take time.

I enjoy using my fingers, but I don't actually enjoy the feeling of them. So that may or may not work for you.

A lot of stories are written as "it hurt and I cried and there was blood...but it's just what I needed". I suspect that the people who are writing them have absolutely no idea what that feels like for real, or what the explanation to medical staff is like. Most fantasies are not what they're cracked up to be.

I have several toys; some vibrate. Date is Monday. I have been sitting at PC with diffo toys in. No problems. His cock isnt too big. He is a gentle guy; gay for some time. Plan for now: is a 2 hour drive to the date. I wear an easy plug. Then, at his place, I am gonna dress up femme. I will lube up, and have him help with bra, nylons, garter belt, etc. I will put in the bigger plug as I dress and femme up for sex. I have been dating sissies for 3 years; they got it figgered for sure. Thanks.

dacoach44 · Feb 4, 2017

Hmmmmmmmm

hobbnobb77 said:
a bottle of wine, a couple of joints, and long slow foreplay. You WILL be ready to take him all the way.

Maybe so. Havent had a joint in years. He has about 6", medium thickness of cock. He got a couple of inches in last week, but we hadnt planned it. This date will be WELL planned with lube, plugs, syringe, etc.

yukonnights · Feb 5, 2017

And don't overlook the fact that he can use the various size toys on you during foreplay. I think if he does this enough you will be ready and begging him when the time is right. I wish you a wonderful and meaningful experience :rose:

dacoach44 · Feb 5, 2017

Yasssssss

yukonnights said:
And don't overlook the fact that he can use the various size toys on you during foreplay. I think if he does this enough you will be ready and begging him when the time is right. I wish you a wonderful and meaningful experience

Good idea; have Daddy get my cunt ready with toys. I will do a 15 minute syringe cleanout.

yukonnights · Feb 5, 2017

dacoach44 said:
Good idea; have Daddy get my cunt ready with toys. I will do a 15 minute syringe cleanout.

Just make it a natural part of lovemaking and foreplay...I bet he just slips right in when the time is perfect.

dacoach44 · Feb 5, 2017

We see

yukonnights said:
Just make it a natural part of lovemaking and foreplay...I bet he just slips right in when the time is perfect.

I will sure as hell do my part. I want this to work. I think the chance to get fucked by a nice man is rare.

Lascivity · Feb 15, 2017

Not to toot my own horn, but I wrote a whole guide to this (see my sig if you're interested). Advice given in this thread is pretty spot on though. And take it slow! You'll enjoy it so much more if you're both ready for it and you put in some prep.

dacoach44 · Feb 15, 2017

Thanks for advice

Lascivity said:
Not to toot my own horn, but I wrote a whole guide to this (see my sig if you're interested). Advice given in this thread is pretty spot on though. And take it slow! You'll enjoy it so much more if you're both ready for it and you put in some prep.

My Lit pals have been lots o help. My first time I wasnt expecting it. You know how love strikes! But second was OK, and this is 3rd. He doesnt want me to cowgirl, so I am SOOO obedient, and will do mish. Just check on your profile?

dacoach44 · Feb 15, 2017

Thanks, nice article.

dacoach44 said:
My Lit pals have been lots o help. My first time I wasnt expecting it. You know how love strikes! But second was OK, and this is 3rd. He doesnt want me to cowgirl, so I am SOOO obedient, and will do mish. Just check on your profile?

Just read it, makes perfect sense. Thanks so much.

rushman1uk · Feb 20, 2017

How did it go Dacoach? I love a good cock once in a while & know how you feel when you can't get your boy inside you.

mya91 · Feb 22, 2017

Carnevil9 said:
Have him start with a finger or two, and work up to his dick when you feel ready for it.

How do I prepare for anal sex?

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