Anal Renaissance
Reclaiming pleasure in my bootyhole.
I have only flown Southwest Airlines once in my life. I had a client fly me out to Chicago for an overnight booking and I didn’t have an airline preference yet. At the time, I thought any airline but Frontier or Spirit would work. I had priority at check in so I was like A10 or something (IYKNK) which was nice, almost felt like business class. However the check in for my return opened while I was ON the flight there, so when I went to check in for the return hours later I had a horrible position, which meant I would have to argue with a strange woman trying to hold a seat for someone behind me. I didn't know this at the time of our appointment or I would have never suggested he put it in my butt. The flight back felt like Frontier after all, and even though I enjoyed the date, I felt like I had given promo anal to someone.
This was the summer of my Anal Redemption Tour™ where I was determined to enjoy butt sex after some not-so-positive anal bottoming. This is an important distinction, because I love topping, and the only not-so-positive anal sex experience I have had on that side of the dick was when a man brought one in that was the size of my thigh and wanted me to fuck him with it. Now as an Aquarius, I have a tendency to exaggerate things, but I need you to really understand that it still stands as both the longest and the thickest single dong dildo I have ever strapped into. This was during the Ashton Kutcher days and I remember him pulling it out of the bag and my mouth agape waiting for the camera man to knock on the door, that is how big it was.
“Is that going to fit?” was all I managed to stammer out, trying to play it cool and professional. I was definitely still in my baby Domme era and this moment stands out as the one where my hoe card was actually pulled, because I immediately started questioning all that I was doing with my life. He was so cocky and proud that it would that it allowed me to borrow a little bit of his confidence and with a little work, a lot of noise, some weird faces and copious amounts of lube, I got in there. I fucked him as good as I could, while simultaneously masking what can only be described as some weird combination of curiosity and terror. I grew up a lot during that session, both professionally and sadistically.
The first time I allowed someone to penetrate my booty hole I didn’t have an iota of the confidence he had about it fitting. I kept tensing up and arching my back like a shitting dog, which made the task almost impossible. The lube kept drying out and beading up on me and we went through a whole bottle. It still wasn't enough. If porn is really the worst place for sex education, then power bottoms are the worst teachers of anal sex and everything I knew about it at the time was from on of those two sources.
So there I was, butt tooted in the air for about .001 seconds, reflexively tucking my tailbone every time his head tapped on my little star anise, and wincing from pain once the tip popped all the way in. A few strokes of those shenanigans and I was tapping out. I tried a few more times before I finally decided, yeah… some shit just ain’t for me.
Things shifted the summer of my Anal Redemption Tour™. I was armed with education and silicone lube, which is a game changer in the butthole. I was too crunchy-organic-hippy to use silicone on or in my body before and had allowed my healthy lifestyle to wreak unnecessary havoc on my asshole. I got a lot more practice topping and learned a lot about types of lube and lasting time. I was able to test some lubes on my long runs while training for marathons, and if they stopped me from chaffing on a 2-hour run, I knew they would last a during anal.
There was more to it than just lube though. Taking topping seriously allowed me to learn about positions — doggy style is really a pro-level anal sex position, not for amateurs, whereas happy baby looks a lot more intimidating than it is. Side lying is a great entry way but for me, riding it allowed a sense of control over how much dick was going inside. This was necessary for me to be able to relax that sphincter muscle that was trying to keep me from a good time. I also needed to slow down, and invite some warm up touch specific to the ass. Having my taint massaged and my anus licked actually helped to relax me more than anything else, and getting a first orgasm out of the way almost guaranteed a better anal experience.
Most importantly, this tour marked a new level of both choice and pleasure. All the anal sex I had this summer, was something that I decided to propose and only if it felt right and all the cards were aligned. Silicon lube on deck, intimate connection on point and I have already had an orgasm from you eating my ass? That might be the moment I ask if you are down.
Which brings us that hotel room on Michigan Avenue, fresh off a non-stop SWA flight and into a 12-hour date. After showering together — to both get the travel off of me and ensure his level of cleanliness met my standard — we roll ourselves up into the most playful, passionate lovemaking session I have had in a while. He was much larger than his height led me to believe, and he seemed determined to fuck any ideas I had about short men right on out of me. One of the things I miss about GFE sex work is how much they would try to impress me and how hard they would work to try to get an orgasm out of me. It was somewhere between my third and fourth orgasm that I decided, I want to try this size. I rolled over into happy baby, and he obliged.
My next orgasm didn’t take much time at all. He was slow and deliberate with his entry, and hugged my legs keeping a rhythmic, steady stroke. He stayed locked in to my eyes until his rolled back in his head, letting me know this was ending. This might have been my sex-villain origin story, because when you get a good anal orgasm, it is like a dragon that you chase for years to come.
At dinner I enjoyed the sensation of a good stretch and some generic conversation, but the sex afterwards felt vanilla in comparison. I had already leveled up in my mind, as it was my first time inviting myself to such a well endowed plugging and there was really no turning back. Southwest Airlines never saw me again, after that trip and while I still prefer to either top or be penetrated vaginally, I am a sucker for a slow sex session that lands us in my darkest hole.
Author’s note: If you are a power bottom reading this, thinking “you didn’t clean out first??” I receive that judgement and I also will answer yes and no. I am a bidet girl, so it is always mildly edible, and on working nights I made it moreso than usual. My risk aware sex work meant always covered for this type of play.