Darlings, if you thought August was sweaty, September has been an absolute deluge. I’ve barely had time to reapply my lipstick between sessions, let alone polish the boots. The culprit? Pegtember
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Yes, that’s what I’m calling it. Some months the universe just decides every submissive within a fifty mile radius needs their prostate rearranged by a woman in latex. The dungeon has been running hotter than a sauna full of remorseful CEOs. I’ve gone through more lube than a mid budget porn shoot, and my hips are filing formal complaints. But a Mistress does not complain… she simply adjusts her harness and keeps swinging.
Here are three of this month’s standout specimens. Different flavours of slave, different flavours of pegging. All of them left walking like they’d just discovered religion. Or lost it.
1. The “I Only Came for a Taste” Corporate Softboy Sweet, soft spoken, still wearing his wedding ring like a nervous tell. Thought he wanted “a little light pegging, nothing too intense.” Cute.
I had him on his back, knees to chest, while I slowly worked a thick, curved silicone cock into him with the kind of patience usually reserved for roasting a joint of beef. Every time he whimpered “Mistress, it’s too much,” I simply smiled, leaned in, and whispered, “Then why is your cock leaking all over your stomach like a broken fountain?”
He came untouched. Twice. Then cried a bit. Then asked if he could book next week.
Type of pegging: Slow, deep, almost tender… until it isn’t. The kind that makes a man realise he’s been starving for something he didn’t know how to ask for.
2. The Bratty Painslut Who Thinks He’s In Charge This one arrived with a smirk and a list of “hard limits” that somehow didn’t include “getting his prostate pounded until he forgets his own name.” Classic.
I had him face down, ass up, wrists cuffed to the far ends of the bench, while I used a ridged, heavy harness that made a wet thwack every time I bottomed out. He kept trying to top from the bottom (“Harder, Mistress… no, wait, not that hard”). So I stopped, pulled almost all the way out, and waited until he was begging in that delicious, broken voice. Then I gave him exactly what he’d asked for.
He came so hard he left a puddle. Then he thanked me. Then he tried to negotiate a discount. I made him clean the floor with his tongue instead.
Type of pegging: Mean. Relentless. The kind that turns cocky little shits into grateful, dripping messes.
3. The Quiet, Intense One Who Barely Speaks Tall, dark eyed, the sort who looks like he reads philosophy and has complicated feelings about his mother. Barely said a word beyond “Yes, Mistress” and “Please.”
I put him on all fours, slow fucked him with a long, smooth toy that hit that perfect spot every single stroke, and simply held him there… deep, steady, relentless pressure while I stroked his hair and told him what a good, open, eager hole he was being. No theatrics. Just ownership.
He shook for a full minute when he finally came, silent except for this wrecked little gasp. Then he kissed my boots like they were holy relics.
Type of pegging: Deep, rhythmic, almost meditative. The kind that doesn’t just fuck the body… it rearranges the soul a little.
So there you have it, my filthy little diary entries from Pegtember to September. My straps are tired, my wrists are strong, and the waiting list is getting longer than my patience for men who still think “no homo” applies once the dildo is inside them.
If you’re reading this and shifting in your seat… good. You know where to find me. Bring lube. And manners.
Mistress Eve
Still the one holding the harness