Confession: I have failed to have anal sex for the past year or so.
How? you may ask. Despite consistently trying and having frequent orgasms from taking it in the ass pre-2017? I don’t know. I just know every time I have tried since the summer of 2016 when my partner left to go back to university, that it hurts so badly that I want to pass out. Yes, I use lube (I even bought some fancy organic brand), yes, I ease into it and yes, I really really do want it. I want to be a good anal slut and it’s just so fucking hard.
Fast forward to April 28, 2018. I know I sound super dramatic, but trust me, this was probably the most amazing, beautiful and transcendent sexual experience I have ever, and probably will ever have. This may be because I was very, very, irrevocably stoned, but regardless of why, I felt like I finally understood religion.
I hadn’t planned on having anal that fateful Saturday night – it sort of just spontaneously happened, which is odd considering I pencil in every single event of my life in my Google Calendar. However, I should’ve known the night would be magical because it started with me having the last Chicago Express bus all to myself, much to the driver’s chagrin.
I decided to pop half an edible before leaving my dorm, thinking I might as well get personally lit since my partying plans fell apart and I have to commute all the way down to the South Side to get major dicking. And boy, was I STONED. I was snapping selfies with the pink teddy bear filter to my partner (let’s call him L*) when I realized that my eyes were half shut – and it hasn’t been this bad since my double eyelid surgery.
Fast forward to the juicy bits.
I don’t remember the fine details of the night very well, but I’m going to give it a shot. I arrived to the intersection of Mies van der Rohe and Pearson (the Intercampus stop for the Chicago Express) stoned as shit and confused. I do remember slowly becoming less coherent and more confused by sentence syntaxes as the night progressed, saying phrases such as “Man, that was a Buddhist experience,” “I’m so fuckinggggg stoneeeeddd” (about 25 times), “Damnnnnnn that was goooooood,” “Fuck, fuck, fuck that hurts” and probably just some “mdhmslej ?? gdjd mmmm.”
Let me set the scene real quick. The room was nice and dark, the only source of light coming from several candles burning quietly around the room. The luxurious and calming scent of the “Grandma’s Kitchen” candle helps me settle into bed. I’m feeling like I have lost the ability to feel things. L’s playlist is, to say the least, bangin’. I’m not a big fan of music during sex, but the combo of RnB, rap, hip-hop, indie and chillstep just gets me. So I’m in my own little daze, and now comes the anal.
One finger was fine, as I’ve gotten used to it from a year of anal prep and failing to actually do the deed. Two fingers – a little screamy inside. I somehow, very conveniently, lost both of my small plugs, so I brought an adorable black tail plug to use for the night. However, the plug is huge, and I was afraid. Thankfully, L was very gentle and eased the tail in. My asshole was on fire. I squirmed, I squealed, I prayed to God. It maybe helped that his room is filled with crucifixes and Catholic paraphernalia. Maybe someone was listening. Anyway, I was barely conscious and all I could hear and register was him telling me to breathe.
And lo and behold, suddenly it stopped hurting. Maybe it was the breathing, maybe it was the praying, but it probably was time and the weed. Or all of the above. Then, it was time for the dick. (Cue Les Mis soundtrack) (But not literally that would be hella weird).
It was horrifying at first, and then some. I thought I was going to pass out from the pain. It felt like I was being torn apart, I was lightheaded and I couldn’t breathe. Mind you, I have 13 piercings and enjoy painplay. But this was too much. I begged him to stop (Note: We’re in a dom/sub relationship so begging is part of the deal. It’s not creepy). Thankfully, this man is no quitter, unlike my other partners who were clearly too kind to be supposed sadist masters. He encouraged me to breathe, gently peppered my back with kisses and I believe I told him eventually that it was okay. But it may have come out more like “I’m mmmmmk.”
Slowly, but surely, it stopped hurting again. I was able to breathe consistently and just focus on the feeling of the pillow under my cheek. He started to thrust very, very gently. The intense burning pain and the desire to shit violently all over his bed came in waves, but by the time he flipped me over after what felt like the entirety of Mao Zedong’s Long March, it actually felt good!
So, why did I make you read this recounting of my anal experience, you may ask? Because it was truly, genuinely and intensely transcendent. I can’t find a better word to describe it. The intense adrenaline rush of the pain and the subsequent acceptance of it was subdued by the weed, music and calming scents. I felt so intensely connected to him. I did not know where my large intestine began and his dick ended. I’ve only known L for less than a week now, but wow, humanity is beautiful. This must be the kind of good shit that tantric sex is supposed to bring you. I felt Intimacy with a capital I. It was beautiful and spiritual, and the next morning, when the sun streamed into the room, I felt like a changed woman. I left with a spring in my step and the Spotify playlist “Soak Up the Sun” blasting.
Since that life- and game-changing Saturday, we’ve had anal a few more times (the time we had anal next Wednesday I definitely have to write about in the future because it truly is everyone’s nightmare come true), and each time has been equally painful. But I’d like to think I’m improving.
Send love, thoughts and prayers to your beloved Mistress in her continuing journey to reclaim painal slut status. I’m thinking of buying L a cake in the shape of a butt that says “Congratulassions on reclaiming this hole.” What do you guys think?
Note: If you enjoy these specific experience articles, I’m thinking of making various series so you can follow along as my sex-ships develop (and maybe dramatically burn down). Comment, email or send me a Google Form response to let me know how you like these!