Anal sex with girlfriend

LegacyUser

Sex life with girlfriend is quite good. Has improved a lot since we first started doing it but getting somewhat repetitive. Shes no problems with trying new positions or oral, though shes not great at it. When we see each other we'd always have sex that night, sometimes in morning and sometimes just spontaneously so no frequency issues.

Anyway I really want to have anal sex with her, I wouldn't expect it every time or even regularly, maybe once every month or two.

Now, my penis is a bit above average in size. I don't know much about the techicalities with anal, only did it once when I was a teenager, it only lasted a few seconds before it was too sore for her and we stopped. Wasn't a serious relationship so only tried it the once. If I did it with my girlfriend I'd use a lot of lube, not sure about a condom - would that make it more comfortable for her or worse?

Can you go in all the way or should you only shove it in a bit?

Her anus looks tiny, if we only did it occasionally would it damage her in any way? I don't want to leave her streched/incontinent or anything. Ive seen what porngirls look like afterwards but those girls are prob doing it all day with guys much bigger than me.

Looking for advice on approaching or even if I should approach it. My instincts tell me she wouldn't be into it. I wouldn't pressure her but knowing I want something sexually is pressure in itself I reckon.

She's only had one other partner and that was a one night stand when we were on a break(there's no ill feeling about that by the way) so shes pretty much learned everything in bed from our sex life. I remember the first time I went to do her doggy style she seemed to panic a bit, reckon she didn't think you could do it that way and thought I was going to do anal.

I do finger her anus a bit during sex sometimes, I like doing it, she never encourages it, just doesn't object. We only really communicate physically about sex, I find talking about it kind of kills the mood, but this is obviously something that needs to be discussed beforehand.

Another thing was I was giving her a massage last week and when I was doing her bum some of the oil went in between her cheeks. I went back to massaging her shoulders etc and my penis slipped in between them, I didn't shove it or anytihng but she seemed uncomfortable and turned around fairly quickly.

Anyway they're my reasons for thinking I should just forget about it, so how would girls feel about being asked/doing it?

Or guys, have you asked? did they mind?

Is there any suggestions for how I could assess if she'd be up for it before asking directly?

LegacyUser

I did it before with an ex of mine. he was trying to hint at me by suggesting physically, like rub it in the area if you know what i mean! she'll get the message.
although i think she seems uncomfortable from your description of her reaction.

Nevyn

There are plenty of adult sites out there with how to guides I suggest you go look at them and start with knocking those stupid myths about stretching and anal incontinence right out of your head.