I have always loved looking and feeling kelly's ass since we started dating those many years ago. While I never tried to push the issue of anal play (be it rimming, fingering, toys or penetration ), I occasionally hinted at it to gauge her interest. When we got engaged I came right out and asked if she would be interested in trying anal. She was a bit repulsed and I was disappointed but life moved on.
A few years into our marriage, I started doing this thing where when I was horny in the morning, I would spoon her and rub myself against her ass. We actually enjoyed the closeness and intimacy of my chest pressed against her back, my penis rubbing better her cheeks and my hands free to roam up and down the front of her body, but usually busy fingering her. The only gotcha was a little too much friction when I was rubbing against her so one day I applied a little bit of lube to the shaft of my penis which definately made things better for both of us.
One morning while in this position, I slid my face down her back, kissing my way down, and with her still on her side I started to treat her to an oral session. We used a pillow between her knees to prop her open a bit easier. Every now and then I peeked at her crinkled brown eye and debated the pros and cons of giving it a lick (regarding her response ) . When she started to have her o, I decided to go for it and I gently licked the outside of her anus for about 10 seconds, running my tongue in a circle around her hole and right before I stopped, I pressed the tip of my tongue against her clenched asshole which seemed to have the added response of her orgasm lasing a tad bit longer.
I made my way back up behind her, applied a bit more lube to my cock and rubbed against her ass again only instead of my penis facing up, I pointed it down towards our feet. My head would rub against her starfish when I pulled back and against the opening to her pussy when I pushed down. We routinely had sex in the spoon position but never with this degree of foreplay or style. We ended up having sex normally, I didn't even ask but I did notice that she would push back against me when the head of my penis rubbed against her anus.
Fast forward a year, same setup with us spooning and me pointing down so that I would rub against both her holes, I whispered in her ear how I loved how her ass felt. She had loved this new version of spooning and mentioned that she liked the additional stimulation. Taking that as an opportunity, I spent a bit more time rubbing the head of my cock against her asshole without seeming like I was trying to push the head in. In fact that's exactly what I was attempting. I then pulled my hips back and took ahold of my cock as if I was going to try to insert myself in her pussy but instead I pressed the head against her anus and applied just a smidge of pressure while rubbing the head around her ass. When she pressed back against me I knew it was ok.
So without saying anything, I lubed up my finger and slid it inside of her ass. I fingered her for a few minutes and eventually got a 2nd finger inside. I asked if she was ok and she just asked me to go slow. After a few minutes with the two fingers, I slid them out, reapplied some lube to my cock and against pushed the head against her asshole. I reached my hand around and played with her clit and finally popped the head of my cock inside her ass. We went real slow for about 10 minutes and sometimes we just laid there so should could relax. Finally my patience paid off and I had sunk about 3/4 of my cock inside of her ass without a single "ouch" or "stop".
I went real slow with me withdrawing my cock almost to the head and then slowing pushing back inside, each time getting a little deeper. On the 7th or 8th stroke like that she let out a gasp and moan and said I could go a little bit faster. From there on out I made love to my wife's ass for the next few minutes, alternating between long slow strokes and faster half strokes. Eventually it was too much and I told her I was going to cum. Her response was to push back harder against me which finally allowed me to sink 100% of my cock inside of her ass. That was the final straw and I unloaded there in her ass. She met me with a small orgasm of her own.
We laid there spent and I asked if she was ok. She said she was a little sore but that she actually really enjoyed it after she was able to relax. While it's not a routine play in our sexual life today, it is something we do on occasion and now that she knows how to relax, we often do it doggy or reverse cowgirl when we do indulge in anal. She is very receptive to rimming now and that's a very standard addition to me performing oral sex on her. She also enjoys having a small egg vibrator inserted anally when we do doggy, cowgirl/reverse cowgirl or even missionary.