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May 27 2026
This is the story of how, over the last 9 days my life has shifted from single and emotionally unavailable to online cuck sub with a side of sultry humiliation. I met Mistress after posting a personal ad. It was the first time as a submissive, acknowledging my lifelong known, but ignored cuck tendencies and desires.
Having chatting for a day or two, we quickly established the beginning of a dynamic where Mistress and I can vicariously live and play out our cuckold fantasies. Me taking on the role of small-dicked cuck, denied gratification and freedom, making up for my inadequacies by constantly scouting for and sourcing, virile, hard cock for my Mistress’s pleasure. Mistress being the smirking Cuckoldress, relishing my embarrassment and embellishing it with subtlety and wit, unapologetic in her desires and single minded in exploring them.
The dynamic started in earnest, a week ago today when I was allowed my last full and free orgasms. I was instructed to come at least twice, so that every drop after then would be solely derived by desire for my Mistress. I pledged myself to be pussy free, loyal, attentive and obedient to make up for my manhood and Mistress offered to keep tight controls on my future orgasms as reward.
The week so far has been an utter whirlwind of tension and suspense, long late night discussions around our interest in the kink, gently prodding and exploring of our likes and roles. Daily underwear checks in safe but risqué settings and exchanging content that we both find appealing. Of course I have been on a strict hands off policy bar one night of highly restrictive stimulation (the square centimetre under my cock head while thinking about a literotica story series I had shared). While Mistress has had no such limitations. We both seem to enjoy this asymmetry and I believe it’s a cornerstone to our dynamic.
And that brings us to last night, the eve of my first week of not coming for Mistress. A ruin was mused for being such a good boy and an easy slut all week, before being taken away and instead I was allowed some guided stimulation of my small cock. A few sessions of mindfulness and centering myself started us off. Stroking my cock for a period of time through my underwear, then massaging my already full balls for the same timed period, sending clips of my task. I then sent snaps, tracing the tiny outline of my cock, defining its limitations and boundaries on Mistress’s request with my little finger for scale. I was then told to repeat the steps, but with my coconut oil lube, complete with snaps.
The intensity then increased. I was tasked to find a picture of a man with a big, hard dick, while staying hard and turned on myself. I was told to increase the speed of my stroking and browse multiple cocks, looking for the physique Mistress prefers. My cheeks flushed with the gravity of the moment. After this it’s stops being fantasy, and in the act of a fulfilling my instruction, I mentally became a cuck for the first time in earnest. Taking pleasure and pride in searching for and finding a suitable cock for Mistress’s pleasure. Browsing many, big, hard erections while I held and stroked my own small one was emasculating to say the least.
After I had sent two amazing examples we discussed them for a bit before Mistress brought the evening to a crescendo. I was instructed to edge for a total of three times. I was to film each one and mistress gave me a scenario before each edge to concentrate on. The first was to imagine one of the cocks, the bigger of the two I sent, coming all over Mistress’s tits, while I knelt nearby, eagerly awaiting my duty to lick and clean it off. The second edge was while imagining the other cock, the fatter one, getting ready to satisfy my Mistress and I was to go down on her and get her ready for some extraordinary girth. The final edge was to think about how I no longer own my cock, that I have given all control to Mistress and what that means in reality for a cuck like me. Being the last edge of a long night tease so far, this one took me the longest, as I self affirmed with each stroke that my pleasure and my cock no longer belonged to me.
These three edges to me represent a somewhat unholy trinity of our cuck philosophy or perhaps the direction of our dynamic.
1: Sourcing men, and providing service for Mistress and her guest during encounters. 2: Preperation and cleanup of Mistress and her Guest 3: Relinquishing ownership and autonomy of my own pleasure and sexual organs to Mistress’s wants and desires
By far the most erotic edge for me was the first one. Hot off the humiliation of googling big, hard cock, browsing the results while stroking, coupled with the thought of being present in the room specifically only to lick clean another man’s come off my mistress’s tits, at her insistence nearly sent me over the edge. But more than that, it marked a significant mental shift, from wanting to be a cuck, to acting, thinking and feeling like one.
Through all of this my Mistress was elegant and classy, perverted but controlled, powerful, yet gentle. A calm control instilling in me a desire to follow her lead always. I hope to be sharing more as our journey progresses.
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