Is That a Thing? · Kinky Dungeon

Is That a Thing? – That Other Hole

Yes, I am going to talk about anal sex here. Song of choice while writing this: Head Like A Hole by Nine Inch Nails. *giggle*

My first time ever having anal sex was also my first brush with a sadist. Sounds downright scary right? In retrospect, it could have turned into a disaster. I was reckless and way too bold for my own good, young and stupid. I was also very lucky that nothing bad happened to me. Boys and girls, do not do as I did. Okay, enough lecturing. Let’s move on with the story.

I was 25. It was my birthday. I went out to celebrate. Simply put, I was on a hunt. I did find something I liked, two young guys, barely 19-year-olds. Both were cute, one of them was gorgeous. I thought it was a really good idea to have my first threesome on my birthday. And that I did. The sex wasn’t really that memorable, but then one of the guys proposed trying anal. I was like why the hell not, let’s pop that cherry of mine too. There really wasn’t any proper lube, just some oil. It did not feel good. It hurt like a motherfucker. I count that as karma from it not hurting at all when I lost my vaginal virginity. But what made that night a fond memory was when the other guy was popping my cherry from behind and I was hurting, I grabbed onto the gorgeous guy’s arms hard. Then our eyes locked, we had a moment. My face and my eyes were no doubt showing all the agony I was experiencing. He stared into my eyes with a peculiar look. It was a mix of curiosity, excitement, lust and satisfaction. I would never forget his eyes and his intense stare, it was the gleam of a sadist. He got off on my pain, and the masochist in me was awaken for the first time. After that, I couldn’t remember the pain anymore, only that moment with him mattered. I sometimes still wonder how he is doing now, whether he is exploring his beautiful sadist side or not.

For a few more times I have had anal with other guys before I met my ex when I was 26. He loved anal. He made me hate anal. He must be the most impatient man on earth when it comes to anal sex. He was almost always too eager to get it on, not doing enough preparation opening me up. We had been together 4.5 years, we had anal sex probably 4-5 times during that time. I became one of those girls who only gave head when it was the man’s birthday. Only in my case it was anal sex. My ex made me hate anal so much, that even after we broke up and I decided to start my journey down the rabbit hole that is BDSM, I purposefully stayed away from Doms who listed anal sex as one of their fetishes.

Thank God that my Dom didn’t bother to keep his fetish list up to date when we first met. So He kinda slip through under the radar, and when I realized how big of an anal fetishist He was, it was already too late for me, I was already deeply under His Domly spell. So I gladly went on training. Both my Dom and I were on our summer vacation, it made anal training much easier. He was away for a week or so. During that time I got anal plugs in different sizes, I played with them every day according to His long-distance orders. Now that I think about it, it was actually quite impressive. He practically made me fall in love with anal sex within ten days while he wasn’t even in town. After those ten days, I was so ready to beg on my knees for Him to grant me anal sex. Never could I imagine that I would crave anal sex so badly like I do these days.

The first time He asked me in which hole I would like him inside of me, I answered “whichever Sir desires”, and I meant it. All of me belong to Him. He chose anal that time, and I couldn’t be happier. The second time he asked me that, I just straight out answered “anal, please Sir”. I’m not sure which answer He prefers, but at the second time I wanted anal too badly to answer anything else.

UPDATE: I checked from my Dom, about which answer He prefers. He told me to answer honestly. He would then decide to take whatever He wants or grant me my wish. Way to make your little slut melt and panties wet, Sir. 😉


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