With a lot of encouragement, and a few trial runs, my then-girlfriend agreed to allow me inside her ass without a condom. We'd tried anal a few times with a condom, and we'd both enjoyed the experience very much, but she was self-conscious about cleanliness, and the thought of me going bareback both excited and disturbed her.
We showered together, and worked up a real lather cleaning my cock and her ass, and I began rimming her as the hot water streamed down her body. She leaned over, back curved so that her butt stuck out, and splayed her arms on the wall under the showerhead. I spread her cheeks for best access, and slid my tongue around and around and as far into her as I could. She began to thrust her ass at my tongue, moaning loudly.
Then I slowly added a finger to my work, gently probing while I licked, but running water wasn't a very good lubricant. She straightened up, turned around, and grabbed my hard cock, then said that she was ready, and she really, really wanted me inside her ass...NOW!
We towelled off quickly, and jumped together onto the bed, with me on top. She started to push her hips up so that my cock slid between her cheeks, and she pushed back against it as I ground up against her ass. Reluctantly, I slid down and off her, and reached for the lube, and she was almost shivering with anticipation as I ran my fingers lightly up the backs of her legs to her delicious ass. She arched her back, and jutted out her butt as I massaged her cheeks, gradually working the kneading until I was running my thumbs up her ass crack, and spreading her cheeks. Gawd! I loooooove the look of a woman's ass, jutting up and out, spread and inviting, exposing her anus and the glory of her pussy. Yum!
I flipped the cap on the lube, and poured a more than generous portion into my other hand, then warmed it, and ran the slick palms of my hands several times down her crack to lube up the area, then went back to massaging and worshipping her scrumptious ass (she loved that), then concentrated more on her anus with my thumbs, until I was running them in small circles along the rim and dipping slightly inside. Again, she started to moan, and grabbed a pillow (mine, of course), and jammed it under her lube-soaked hips. I uncapped the lube again, and this time allowed a small stream to run from the top of her ass, down between her cheeks and across the one thumb still gliding around her anus.
I'd managed to work her ass enough by now that my thumb slid in pretty easily with the extra lube, and before long, I was fucking her with my thumb, then my index and middle finger, and finally added a third after a bit more lube and a few minutes of slow-but-steady work.
She was gasping and sighing and moaning and groaning with pleasure now, and I slid both thumbs inside her asshole and swirled them around while spreading her cheeks with my fingers before removing them and admiring the sight of her open hole, which slowly closed.
"Fuck me! Fuck me in the ass NOW! Shove that cock up my ass!" she screamed, and I didn't waste any time lubing my cock, then slowly sliding the head inside. Wow! What a different feeling when there isn't any latex between you and your loved one's ass! She grunted and gasped, but kept up a hoarse dribble of "fuckmefuckmefuckmefuckme FUCKMEFUCKMEFUCKME!" as I thrust slowly ever deeper.
It seemed like ages, but was likely no more than a minute or two, but soon I was jerking and groaning and filling her ass with spurt after spurt of hot cum, and I rested for awhile with my cock still buried in her ass while she murmured sweet nothings close to my ear about how good my cum felt in her ass, and how great my hard cock felt inside her, and how glad she was that we had done this.
After catching my breath, though still hard as a rock and turned on like crazy, I slowly pulled out of her and slid back to admire the view of her open asshole and her gorgeous ass. As it slowly closed, she must have tried to force out the cum for my added enjoyment, because there were a few...um...noises...then a glistening ooze of my cum slid slowly out and down across her pussy. I was in heaven! My cum went between her pussy lips, and dripped down onto the (my!) pillow, and all I could do was exclaim at the sight and thank her profusely.
Then we hopped back in the shower to clean up...and start on a long night of wild and passionate sex!
Yup, Anal Cream Pies...a favourite memory of mine!