I mentioned in a recent blog how I enjoyed setting challenges for my submissives – and how it gave me a sense of controlling them outside the dungeon.

Well… A week or two ago I came across a Fetlife group called Humiliation, Tasks and Challenges For The Aspiring Submissive (And Ideas For The Dominants Who Love Them) where submissives ask for humiliating tasks to be set for them. And something about one of the posts by fuck_slut, or perhaps it was their rather fetching pictures, caught my attention.

So I messaged them and set them a task, at the end of which they posted pictures of the results and a long and detailed report – which with their permission (and their Mistress’s permission) I am including below.

Think of this as a guest post. Maybe I’ll do more in the future…

Ms Emilie

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Challenge accepted

I recently had the fortune of being approached by the lovey MsEmilieOxford. She asked if I was interested in completing a task for her, per a request for humiliation that I had posted on FetLife. Of course I was intrigued, and pending the approval of my Mistress, PoisonDatura, I was excited to find out more about what could be in store for me.

MsEmilie issued her request: I was to go to a Victoria's Secret and purchase lingerie, expressly communicating that this was clothing for me. Despite having enjoyed wearing women's things for some time, I had never purchased them by myself or for myself in a retail setting, and certainly not without a fabricated cover story. The task simultaneously excited me and scared me to death. My imagination was quickly consumed with images of sales women laughing, my boss with pink slip in hand, friends and family disowning me for being a cross dressing freak.

I ran the proposition past my Mistress, and honestly a part of me hoped she would deny the request. Comfort zones are by nature comfortable. However, she was entertained by the idea, and wanted her little slut to execute the task for her amusement.

Flash forward a week. The concept of the task continued to thrill and terrify me, but I finally made the decision that I would clear my afternoon at work, and complete what was asked of me.

Anxiety consumed me as I approached the store. I honestly got within ten feet of the door and had to abort. I walked around, got some water. Breathe. And then it struck me. I am going to decide what happens in this situation. If I go in there a nervous, awkward wreck, the interaction will be awkward. I have overcome much more challenging summits in my life. I am beautiful, and I feel beautiful wearing scandalous lingerie.

With my bolstered courage, I walked into the store. Despite my pep talk, my stomach was still in knots. On the surface, I made eye contact, I smiled, I did all of the things that a natural introvert learns to do in an extrovert's career, but I was trembling inside.

And then it happened. A petite blonde sales associate approached me.

"What can I help you with?" A smile across her face. All I could think was how she began with an open ended question. Her sales manager would be proud.

"I'm looking for a present," I replied. Chicken shit.

"Do you know her size?" She countered, certainly not the first time she has helped a man find something for a partner.

I couldn't believe I had choked. I knew in my head that I didn't have to come clean to anyone, after all, it was just me in the store. I could leave, I could lie. But in the end I did not want to disappoint myself, much less Ms Emilie or Ms Datura.

I’m not sure that it is possible for skin to sublimate. If one can actually blush enough for blood to vaporize the tissue from within a capillary, but I felt it was happening to me. But at the same time, I knew this was my chance. If I fucked it up, the odds of me ever doing this again were slim to none.

"I am the present." I said with tone that was orders of magnitude more confident than I felt. "The present is me wearing the lingerie for my mistress." I don't know how the words ever arranged themselves, but they did. The pivotal moment. Everything that I had worked myself up about, was surely about to happen. The levy was set to break.

But instead, she simply replied, "Ok, do you know what size you need?". I did not anticipate her smile, but found it utterly contagious.

"Probably an A cup at best," as I looked down at my slender, male frame. I responded with a grin, a million pounds of fret had been solvated by her acceptance to help me.

She proceeded to measure my chest, and asked what I liked. It was then that the levy did indeed burst. But it was not the catastrophe that I had imagined, it was me, waxing poetic of adoring straps, the negative spaces of cut outs how sheer fabric creates something for the imagination to resolve, but it never makes it work too hard. I collected armfuls of things as we chatted about design and fabrics.

We were able to find a number of things that I really liked. Unfortunately a bra that I fancied was not available in anything smaller than a D cup, which I knew I could obviously not fill. She apologized for not having what I wanted after a radio chat with the often referenced but never observed "back room". No worries, there were plenty of other things that caught my eye.

I meandered about on my own for a bit. So many fragrances, athletic wear, Pink. Certainly not my pursuit, but I wanted to turn every stone. In any case, I made my way back to the register eventually. And just as I was piling my things onto the counter, she came flying up behind me.

"Oh, thank goodness, I thought you left. I found your bra! It was mixed in the wrong drawer," as she handed it to me.

My smile an impossible width. "Thank you so much!"

"You're very welcome!" As she returned a glorious grin. I just melted.

In the end, I am very proud of myself for completing what was asked of me. Have I done more challenging things in my life? Certainly. But this was squarely outside my personal comfort zone. Something that I have never done before, due to self consciousness, fear, etc. What began as a quest for humiliation became instead a tremendously empowering and an absolutely positive experience for me. The second I realized that the shame was only in my head, and that there is absolutely nothing humiliating about wanting to be and feel beautiful, the task that once seemed insurmountable, became a molehill.

Thank you so much for the nudge MsEmilieOxford and Ms Datura for knowing exactly what I needed. I greatly appreciate it.