Anal Sex + Prior Injury

Pizda

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Hey yall, first post here, with a question you guys might be able to answer!

A little background: my best friend and I have been on-and-off FWB's for many years (proof that having sex with your best friend doesn't always end in disaster!), except for the past 3 years when she was in a monogamous relationship with another guy. Anyway, about 3 months ago, she broke up with him, and once again my homegirl is in my arms.

Now, we've been throwing around the idea of anal sex. Personally, I love it. I've done it multiple times in the past without any difficulty despite my girth. She loves it (and I love it!) when I eat out her ass and when I finger it.

My friend, however, has a little problem: the only time she had anal sex with this past boyfriend, it felt good WHILE it was happening... but the next day, she found herself in agonizing pain. Turns out he injured her by doing it wrong and she actually had to have surgery.

What we're worried about is that my 6"-round penis will possibly tear her wound back open, even if we go slow and use lots of lube. Her boyfriend was of average size, and everything I've read on the internet about anal sex after anal fissure surgery seems to be geared toward average-sized guys... so that's why I came to you folks.

Do you think this will be a problem? Do you think we should go ahead? Or should we not risk me tearing her up again? My friend really wants to be able to have a good anal experience, and her anus looks so tempting and inviting to me :(
 

mikeyinbrooklyn

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Work up to it. Start with finger(s), thin dildo, etc. Lots of lube. After each "level" have her see if she has any discomfort the next morning. In a week or two you should have your answer. It's cool that you're into both the anal and wanting to do it in a positive way with her. Hope she's able, and I hope it's awesome.
 

Pizda

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Work up to it. Start with finger(s), thin dildo, etc. Lots of lube. After each "level" have her see if she has any discomfort the next morning. In a week or two you should have your answer.

So basically... do what I would do within a night, but across the next couple of weeks? That's an interesting idea... we might try that. Thankfully she has a thin dildo and an average-sized vibrator, so we DO have the tools....

It's cool that you're into both the anal and wanting to do it in a positive way with her. Hope she's able, and I hope it's awesome.

Yeah man, she's my best friend, how could I not?! And at the end of the day, it's half about her! (Why we don't date, well, that's another story altogether... but needless to say, we're both team players when it comes to our bedroom follies!)
 

Pizda

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STEP 1:

Well, first day we tried 2 fingers instead of one. I ate out her ass for about 5 minutes or so, thoroughly and passionately (Her anus is adorable, rimming her is one of my favorite things to do when we hang out)... Then I lubed up my usual finger... and then lubed up a second finger... Stuck it in, began fingering her... she asked for me to go faster... so I did... "Faster!" she said... and I started ramming her as hard as possible with my lube-soaked fingers.

Her verdict? "Pretty hot, actually... the feeling of being stretched out was kinda cool. I gotta admit though, it was a little, uh... intense."

We're gonna repeat it again and see if it'll be a little more genuinely pleasurable, not just on a psychological level... if so, we're gonna work up to her little dildo. *fingers crossed!*
 

Pizda

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I broke up with someone I loved because of anal sex issues years ago! I had to face the reality that some asses are just too small for some large cocks! I think it is the first law of physics!:biggrin1:

Hmmmm... well, my friend's butthole does seem noticeably tight... Perhaps from the surgery? Or maybe it's just all in my head because it's her...

But still, I've had anal sex with 6 people, and it's never been an issue once the groove gets going... Nobody has ever been injured by me, although one female friend of mine who is a total anal freak described me as "a bit of a challenge" when we had anal together... And none of those 6 people seemed to have noticeably tighter/looser anuses than one another.

We'll see what happens with the next 2-finger butt-fingering session; as she said, things were "kinda intense", and I don't want things to go from "intense" to "painful"!
 

mikeyinbrooklyn

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I broke up with someone I loved because of anal sex issues years ago! I had to face the reality that some asses are just too small for some large cocks! I think it is the first law of physics!:biggrin1:

That's so sad! I'm mostly a bottom, and I've never had one that I couldn't accomodate with a little hard work. But I wonder what I would do if I truly loved someone, but we weren't able to make it work sexually. I'd like to think that love would conquer all, but practicalities are important. By the way, your cock is huge. Not too huge, but huge.
 

basque9

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That's so sad! I'm mostly a bottom, and I've never had one that I couldn't accomodate with a little hard work. But I wonder what I would do if I truly loved someone, but we weren't able to make it work sexually. I'd like to think that love would conquer all, but practicalities are important. By the way, your cock is huge. Not too huge, but huge.

It was a traumatic decision, mikey! The guy had endured considerable pain silently for almost a year. Korean War had arrived and that gave me a way to end our love affair.

After the war, I met the final love of my long life , the guy I spent almost 45 years with and predictably, he was never able to take my cock anally.
Fortunately, I was given freedom to occasionally mate with a few men who loved and even obsessed over anal sex with my cock!:cool:
 
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Pizda

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the guy I spent almost 45 years with and predictably, he was never able to take my cock anally.

I was given freedom to occasionally mate with a few men who loved and even obsessed over anal sex with my cock!

Well, I guess that's evidence that some people are in fact tighter than others... My friend actually suggested that she may HAVE actually gotten tighter because of the surgery... She says she might call her doctor soon before we go to the next level.
 

Pizda

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Well, here's a tragic update:

My buddy talked to her doctor about it, just to be safe. The doc said that with the way her surgery healed, that while anal sex isn't out of the question per se... he'd rather her not, uh, stretch it with a man my size.

So until we get a second opinion, it looks like it's a no-go :(
 

mikeyinbrooklyn

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Well, here's a tragic update:

My buddy talked to her doctor about it, just to be safe. The doc said that with the way her surgery healed, that while anal sex isn't out of the question per se... he'd rather her not, uh, stretch it with a man my size.

So until we get a second opinion, it looks like it's a no-go :(

Sorry to hear that, but I would bear a few things in mind.
First, there are still lots of fun you can have in the bed department. And work hard not to let her feel guilty about it. Emphasize how much she does make you happy, in and out of bed. Don't dwell on what can't be done. Pizda, you seem like a very good lover, to be this concerned about her. Happy fucking.