My First Real DD Roleplay Failed Because Of My Inexperience

Anonymous Cherry Cub #865 · General Confessions

I've been working as a bartender at this cozy little pub for about six months now. It's a place where people come to unwind, meet new friends over drinks, and yes, sometimes share their kinks in low whispers or through discreet nods. I never thought it would happen to me, but recently, something shifted inside of me, I started having fantasies about Dominant/submissive dynamics. I know it sounds strange for someone like me, who's always been very independent and confident behind the bar, but there was this draw, a yearning even, that kept pushing me toward exploring these feelings in real life. A few weeks back, a regular customer came into the pub, let’s call him Jack. We’ve exchanged pleasantries before, but nothing more than your typical friendly chat. This time, though, something was different. He asked if I’d ever been interested in BDSM play, specifically DD (Domme/dominant and little or sub). At first, I laughed it off and said no way, not my thing at all. But later that night, when I went home, the conversation kept nagging at me. Why had he felt comfortable asking such a personal question? Was there something about him that made me consider it? Over the next few weeks, we started chatting more, always around these lines of interest. He asked if I was willing to try an evening out as a DD roleplay once everything opened up for us again post-lockdown restrictions. My mind raced with possibilities but also doubts. Was this really what I wanted? Could I actually do it? The day finally came and we arranged to meet in the early hours of the morning when no one was around at the pub. Jack arrived dressed formally, trench coat, slicked-back hair, and had a certain air about him that made me feel nervous yet excited all at once. When he gave me his instructions as my Domme for the evening, I felt like an imposter trying to act out something beyond my reach. I was meant to be in control, but every command felt forced and clumsy. Jack tried to guide me through it gently, offering feedback on how to improve, but seeing myself from his perspective made clear just how inexperienced and unpolished I truly am. By the end of that night, we both knew the roleplay hadn't gone as planned. It was a failed attempt at something much bigger than either of us were ready for, or maybe it was a realization that I needed more preparation before taking on such a serious dynamic in real life. Despite everything, there’s an inkling of hope left, maybe if we continue working together and learning from this experience, one day I’ll be able to take on the role with confidence.