My 28 year old wife always said her asshole was off limits and would stop me anytime I got near it.
Recently, she's been having some redness down there and I've been putting ointment on it. She admitted she like it when I did this. So, when we would masturbate together, I started rubbing her asshole.
She came hard when I did this and would cum multiple times. A couple weeks ago, I wound up going for it and partially put my thumb in and she really seemed to enjoy it and had an intense orgasm.
Last night was the first time we actually had vaginal sex. We started of with a little mutual touching and foreplay then switched to missionary. She had a couple good orgasms when I sucked on her hard nipples and lightly bit them. Shortly after that, she asked if I wanted her to flip over for doggy.
Doggy for her is extremely rare, so I of course said yes. I started fucking her and decided to see if she'd let me rub her asshole. Every time in doggy, she tells me to avoid it, but not this time.
It was already lubed up, so I started rubbing it and she was clearly enjoying it. I could feel her anus open and close a bit with my thumb on it, so I moved my hand and could see her asshole blinking at me. I decided to go for it. I put my thumb in a little bit and she came. I started going in and out and also kinda rimming it with my thumb. I went a little deeper and started going in rhythm with my dick in her pussy.
I wound up cumming but still stayed hard because it was so fucking hot and managed to get her another orgasm.
I'm hoping she'll let me fuck her ass one of these days.