We had spent the whole day in a teasing mood after some good sex the night prior, in which I orgasmed while on top and the orgasm lasted all the way through him cumming. The sun was shining hard and I kept mentioning that I wanted to go for a slutty walk.
We first went to our favorite trail, which was unusually busy with people. So there wasn't a whole lot of sluttiness and I only got a few seconds of flashing my boobs. Then we drove over to our second favorite trail - although it's a trail we rarely do because it's a much more challenging walk - and I spent the whole drive with my boobs out. I was signaling to him hard that I needed to be a naughty girl!
We spent much of the walk being non-naughty. Then we found a little spot down near the river and as I was standing looking out over the water, he grabbed my hand and put it in his open zipper. Discovering his cock already hardening was the best and I quickly squatted down in front of him to take his cock between my lips as the water flowed behind us. It was only a minute of cock sucking but I was thoroughly awoken and drenched by it!
I walked much of the way back with my boobs out, enjoying the sunshine and the slightest breeze caressing my nipples. The whole thing, tame as it was, had me absolutely throbbing for the rest of the day and there were still so many hours until the house quieted down enough that it could be time for sex.
Shortly after midnight, I went for a quick shower and asked him what I should wear when I was done. "As little as possible", he said. So I put on my hole-y fishnet dress, a pair of knee high socks and my hair in braids. We still had a bit of time, so I got a back rub that turned into an ass rub with some anal teasing before we finally went to bed.
I started on my knees, bent over with my head on the bed. He was harder than he has been lately and didn't take long to be immediately thrusting into me. He kept running his hand over my asshole and teasing me with his thumb just slightly penetrating it. Then he laid down beside me and motioned for me to get on top of him. I was all too happy to oblige.
It started off slow, as it always does when I'm on top. His hands were absolutely everywhere and they were moving so quickly it felt like he had more than two working. They'd be on my ass, then my boobs, then one on my neck, one on my ass, down the back of my legs. Just a constant swirl of his hands everywhere while I slowly and sensually grinded atop him, passionately kissing him.
I sat back, digging my hands into his chest and quickly rocked back and forth on his cock and he was gasping with every movement. I was soaking and the room was filled with the sound of my wet pussy and our shared panting breaths. I leaned forward to kiss him and he slid out of me, covered in my wetness. I reached behind me and began guiding his cock into my ass.
While it went in easily, the sensation was utterly terrible! There was pinching, there was tightness in a bad way, there was awkwardness everytime I tried to move and as much as I wanted to try and push past it, I just couldn't. I wiped him off and slid him back in my slippery pussy. I needed a minute to catch my breath and spent a few minutes playfully teasing him. He could tell I was a touch disappointed that the go at anal wasn't more successful - he's always telling me "one day, I want you to ride me with my cock in your ass", and while I've technically done it before, it's never happened for long and it definitely doesn't happen often - and so, sensing this disappointment whispered in my ear, "You kinda wish I would lay you down and fuck you in the ass, don't you?". I continued slowly teasing him, slowly lifting myself almost completely off his cock before slowly sliding myself back down onto him deeply, "Yes but I make no guarantees that we'll be successful".
I laid down on my stomach and knowing that it always helps when things feel a little pinchy, I bent my one leg up high beside me while the other stayed straight. I was more on my side than on my stomach and my boobs felt so good plumped up by the bed. He first entered my pussy and I stuck my fingers in my mouth before moving them to my asshole. I slid one finger in, then two. He asked, "Are you fingering your ass while I'm fucking you?". I moaned, "Mm hmm". "Good girl!", he said.
I moved my hand to his cock, pulled it out of my pussy and slid all the wetness over my asshole before beginning to work him into me. There was a moment when I thought it wasn't going to happen but once he pushed past that part, it felt so amazingly good. He asked if I liked it and all I could get out was a deep "mmm". I asked if he liked it, did it feel good for him, a string of questions begging for reassurance that this was what he wanted. While I don't remember his exact responses, my response to them was, "Fuck my tight slutty asshole harder, Daddy". Adorably, he asked, "Are you sure?".
When I answered in the affirmative, he grunted, "Do you want me to destroy that ass?" and I reached back and lifted my ass cheek and moaned, "Yes Daddy, destroy this whore!". And he put his hands where mine had been and I moved my hands to his chest and he began thrusting harder. "More! Harder! Fuck my ass harder! Yes, deeper! Give it to me!", I panted frantically, gripping at any part of his flesh I could reach. I could feel his leg pushing into my clit and he was thrusting as hard as he could. When I began pushing back against him, our bodies in a perfect rhythm, he said "I'm gonna cum" and I braced myself for the forceful thrusts that would come next.
As he began to cum, the sensation of fullness was immediate and he began whispering, "Oh my god! Oh my god! Oh my god!", on repeat. He never, seriously never, says that during sex. He just kept thrusting and filling me with cum, those three words constantly. It felt like it lasted so long and I was positively cooing beneath him. When the last spurt had finally left him, he bent down and kissed me, "Such a good girl!", all I could moan was "Mm hmm".
I told him to not move while I worked him out of my ass. It happened so much easier than I thought it would and for that I was grateful. Generally, the rougher he is, the harder it is to get him out without some kind of discomfort. I couldn't believe I hadn't cum being that I was so close, so often. I laid down and went to work on my clit and he shuffled low enough to get a finger expertly placed in my pussy. The first jolt of my orgasm was intense and I let out a loud moan before my whole body tightened up into a little ball as the orgasm gently coursed through me.
We had a smoke in bed as he gushed about how good I did and how impressed he was. I kept saying I couldn't believe how good it felt. He said, "Every time we have anal, it's amazing but this time was *amazing* amazing", extreme emphasis on that first amazing. I laid down and he moved up behind me, wrapped his arm around me and kissed my shoulder. "I love you so much". It was literally seconds before we both drifted off to sleep!