First anal

MickeyLee

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My hub wants me to try anal, but I'm not really certain at all about wanting to try it.

Do you like any or have you tried any kind of anal stimulation?

I suggest starting with a finger or a toy before diving into the deep end of booty sex bay.
 
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Livinnudie84

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We did try stimulation and I thought a good bit of lube before. He tried putting it in and it felt like he was trying to shove his hand up there.
I kind of mentioned trying it again so we did get some smaller plugs, I just havent got into wanting to try it again.
 
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MickeyLee

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We did try stimulation and I thought a good bit of lube before. He tried putting it in and it felt like he was trying to shove his hand up there.
I kind of mentioned trying it again so we did get some smaller plugs, I just havent got into wanting to try it again.

Booty loving might not be your thing, nothing wrong with that. :)
 
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Not everyone is going to enjoy ass play. No matter how much lube, how relaxed, whatever. It's not like all men (bisexual, gay, straight, or other) enjoy things up their ass. Women aren't obligated to like anal either.

In any case, I had an awful, painful, and bloody introduction to anal. I swore it off for years. I explored it on my own at a later point by myself, and eventually felt comfortable opening ass play from a solo thing to being with my partner. Prep includes being mindful of what I eat before hand for a day ish and enemas too.

I've introduced a few males in the past to ass play, but I don't pressure people into things. I enjoy needles pushed through my flesh, but that's not everyone's thing, either.
 
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My first encounter with anal sex was not remotely fun either. I did since try it again - not with the same person - and end up quite liking it. Once every few months I crave anal, but my partner is not interested. It's something we have tried together, but he's just not that into it. I know I've posted this before, but when I first brought up the subject he laughed and said that some people were just contrary, and "why would you?, there's a vagina right next to it". He has indicated that he might be willing to try it again in future, but I haven't bothered to try to persuade him yet because it's just not something he is interested in, and anyway his dick is too big. Even though we have tried it before I am still slightly put off by the size of his penis.
 

Scarletbegonia

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My early experience was a rape by instrumentation moment.
Beer bottle.
I’m so lucky it didn’t break.
Filed charges, got laughed out of the police station.

Fast forward 20odd years.
I’m dating a wonderful guy, 16 years my senior.
He asks, conversationally, in a string of flirting emails if I’ve ever done anal.
Not willingly, I reply.
He immediately apologizes, and says he doesn’t want to bring up bad memories. But does throw the “I’d be slow and gentle line.”

This gives me time to intellectualize the idea. Something that works in his favor.

Six months later, we are having a great play date. He’s about to go on tour.
We have been engaging in anal play both ways, and he’s using his fingers.
He said, I can’t wait to have my dick in your ass.
I said, what are you waiting for?

He froze. I thought I broke him.
I look at him...he’s in a stunned daze. It was hilarious.
I kissed him and said again, what are you waiting for?

He came to, flipped me over, ate me like groceries and went so slow and carefully.

It’s on the menu.
I loved it, 80 percent. The rest was meh.
 

towhead5

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I should point out that I was more willing to try fisting than anal. And that scared me.
We are still getting there. Great journey.
I’m really sorry your first time was so bad! I’m glad your next experience was better
 

AlteredEgo

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No one has ever forced anal on me. The most aggressive anal partner goaded me into pushing past the pain I was experiencing when I expressed that I was thinking about tapping out, suggesting he was too big. It initially felt like trying to fuck a mountain. I had been way out of practice. He and I had done a lot of prep. He'd talked me through my usually solo enema routine, something that had excited us both. He'd eaten me vaginally and anally like I was the first meal after a long fast. He'd fucked my vagina until I was high and delirious. He'd denied me orgasm, over and over, and worked me into a state of horny desperation. I don't remember what he said, I just remember renewed determination to make it work, and that the reward was bliss.

He did literally turn out to be a sociopath, unfortunately, or I'd probably be up under him right now. Statistically, sociopaths are more skilled sexually, and that held true for him. That was probably the best I ever got it. Now, what I need is a genuinely nice man who fucks like a sociopath but loves like an angel.