In the fourth episode of The Valerie Rayne Show, Valerie Rayne looks back on two of her favorite stories of what she considers to be the kinkiest sex she has!
Features readings from Valerie Rayne Writes of the posts
Let Me Tell You About Last Night - 11/05/2025 and
Let Me Tell You About Last Night - 05/11/2026, in which Valerie Rayne recounts two of her favorite anal sexperiences in detail.
Transcript
Episode 4 Transcript
Ep. 4: Valerie Rayne Reminisces
[Theme Song]
Hey there!
I'm Valerie Rayne, a 39-year-old wannabe kinkster, blog-a-holic, mom of six and adult content creator and in episode 4 of The Valerie Rayne Show, we're looking back at two of my favorite anal sexperiences. Some of you may know that in the past, I used to say "The moon, the stars and all the planets have to align for me to be able to have anal sex" but I'm happy to say that that is no longer true! It took many many years for us to finally get to the point where every anal sex session isn't a serious struggle and I thought it would be fun to reminisce on what I consider to be the kinkiest sex I have.
As always, I invite you to engage and interact with me and my content on any platforms you follow me on and highly encourage you to check me out on BlueSky, @valerierayne13, to get all my sexy thoughts and content updates in real time.
0Thanks to shark week, it had been about 10 days since The Boyfriend and I had last had sex and let me tell you, I was feral! Even though there's been no real reason for it (might be a lie) and even though he's been sweet and cuddly and attentive, I've just felt this wall between us. It happens often, especially when we're nearing the 2-weeks-without-sex mark but this one, I think, goes a little deeper than that.
And when that wall starts to go up, I get slightly more feral because I know sex will likely shatter the bricks that have been built. It's a moment for us to reconnect without thoughts of kids and work and life and blah! And the lie... I've been working hard to step up my content game - still not anywhere near where I wanna be but spending more time and thought on it all. And while he's so supportive and encouraging and incredible about it (he'll pick my outfits with me, help me make editing decisions, give me time and space and free reign to make and do), he's just not into it. I've always said:
0Sometimes I wish The Boyfriend was a bit more of a pervert. I want him to be a fan on my fansites and leave dirty comments on everything. But that's so not in his personality. So one day, I hope a subscriber will fill that hole š
And sometimes, not gonna lie, it bothers me a bit. He's out there making his nature/hiking/camping content and I definitely don't care about that but you bet your ass I'm watching every single one of his videos! Whereas here I am, showing full booty hole to the internet and I've got tons of content out there that he's never seen, doesn't even know about! Literally, when we first started dating he said something about "love to watch girls masturbate", but guess how many of the 80+ masturbation videos I've made that he's seen?!?
Anyways, so not the point... So last night...
I just recently re-signed up for Chaturbate and am working on using up my "new" tag as much as possible. So I went for a bath and did a 3 or 4 hour livestream. When I got out, I decided it was dress up time because I knew that chances were high I was getting sex being that shark week was over. I picked out my favorite dress, put on a thong he'd never seen before and a bra-like thing to really push my boobs up for him. I felt like I looked hot and while he reacted, it's just never enough.
So we head to bed and almost immediately he rolls me onto my stomach. No kisses, no arousing touches, just roll over and basically starts going for it. I think he squeezed my ass a couple times and then slid his dick between my legs. Of course, I'm always wet and ready to go which is great but also sucks sometimes when I feel like I want to be coaxed and brought to some sort of peak of arousal.
After awhile of fucking me roughly from behind, he rolled me halfway to the side so that my leg was up beside me. Finally I got a kiss and my hands all over his body, which felt so good. I definitely got more into things and when he gently put his hand around my neck and slammed himself into me, I responded by grabbing him and pulling him deeper and putting my hand on his and forcing him to be a little rougher on my throat. After awhile, he laid down and invited me to crawl on top of him, which I did enthusiastically. I knew he wanted boobs in his face! As usual, this was probably the least rough part of the night and he wanted lots of grinding. He threw my hand behind me and I wasn't sure if he wanted my hand on my ass or his balls or what, so I cupped his balls and gently pressed on his asshole with my finger. He seemed to enjoy this.
After I had throughly exhausted my legs, I laid down beside him and he mounted me. I was soaking wet and he kept slipping out of me and his cock was rubbing against my ass. Of course this spawned anal teasing, which is mostly just dirty talking about anal while sliding his cock around in my wetness. Couple strokes in my pussy, pop out and let his dick slide around my ass area and then back into my pussy. He kept asking, "How many times have you wished my cock would just slide into your tight ass?", knowing full well that it was every single time he slid around that area. The teasing, the talking, the hands, all of it had me grinding and moaning, so it was no surprise when I came, digging my nails into his arm while my orgasm coursed through me. He stayed perfectly still so he could feel my pussy throb around him.
One thing that I really really love about our sex is how well we communicate during it but still keep it sexy, even when it doesn't sound that way. He said something along the lines of, "I really want to roll you over and stick it in your ass!" and I said, "I want that too but I don't know if I'll be able...". "You've said that before and then took it like such a good girl, you want me to try don't you?", he whispered in my ear. "Yes, but I don't know Daddy. I just get this feeling it's gonna fail.", I confessed. We exchanged some more words and did our classic dirty talk about what would happen if I was letting another guy fuck me in the ass. "You'd let him be so rough, wouldn't you?", he asked, "I'd be saying no but I'd want him to just take it!". Back and forth, we just kept egging each other on when suddenly he said, "You remember your safeword, don't you?". When I nodded, he said, "Roll over!", and immediately dismounted to let me roll.
Normally, he struggles to get the angle right and goes in too high or something, so I always have to reach back and help - which is probably a huge turn on him for him. However, he managed to get the right angle immediately and slid the tip in way easier than I was expecting. But with my legs together, I was getting this very intense pinching sensation every time he moved and while he wanted to just be the rough guy who takes it while I'm squirming and ow-ing, he's just not that kinda guy. I told him to let me lift one leg up to give us more room and it fixed the problem entirely. "You'd let him fuck you harder, wouldn't you?", he growled and I moaned and said "Yes, Daddy!". "What would you say to him?", "I'd tell him to fuck me harder, deeper!", I panted. "Mmm, say it to me!", he moaned as he grabbed my hair in his hand and yanked my head back. "Fuck me harder Daddy. Fuck my ass so deep!", I growled and he began thrusting harder and faster.
"Oh my god, you're so deep Daddy!", I gasped and then as is typical during anal, I just started muttering "Please", over and over again. I never know for sure what I'm saying it for or what I want or why it's what I say, it just comes out on repeat. The way that he says, "Please what?", gets me so excited, to which I often just keep repeating "Please". "You like being a slut for Daddy, don't you good girl?" - ugh, just thinking about him saying it makes me wet all over again! "Please what?", he repeats. At this point, I am a puddle, a big wet sloppy puddle - both physically and mentally. I just start moaning and growling, "Fuck me so hard in my tight little ass Daddy. Give it to me! Fill my ass with your cum! Yes Daddy, deeper. Fuck me!" - I literally have no control over the words coming out of my mouth, it just pours and pours and he absolutely loves it! I say things that often make me feel bashful afterwards and he always comforts me about how hot it was.
"I'm gonna cum in that tight ass!", he whispers and I start moaning, "Yes! Oh my god! Please Daddy! Yes!". He seemed to cum for a long time before collapsing on top of me. This part is usually the worst part of the whole experience for me. Not only is he heavy as hell when he does this collapsing but the process of getting him out of my ass is the absolute worst! He has to go really slow and pay close attention to every little "stop" and "wait", as I try to relax and I normally have to reach back and guide him out so that he comes out at exactly the same angle he went in and it's just such an unsexy moment usually. However, after his massive orgasm, he was quickly softening and just slowly slid out naturally. It was a much more pleasurable experience than normal.
We moved into our own spots and I immediately went to work on my second orgasm. I thought for sure he would just fall asleep on me with how hard and long he worked but instead he started rubbing his hands everywhere. He kept sweeping his hand along my neck and then down my boobs and along the bottom of my ribs. The motion of it was driving me absolutely wild and I kept moving my body to meet his hand. When I finally came, which probably only took 5 minutes but felt like hours, it was incredibly intense and I curled up into a little ball, every muscle so tense. The final wave of my orgasm jolted out of me and I kicked out my legs before collapsing into him. "Kiss me now!", he demanded and we exchanged a sweet and gentle kiss. I think it took us all of 2 minutes to fall asleep!!!
0We 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!
Well folks, that's all for this episode of The Valerie Rayne Show. Thanks so much for listening and I hope you enjoyed!
[Theme Song]
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