Caroline

Mistress Caroline popped my kinky cherry today and it went better than I would have ever dared to imagine.

Prior to the meeting I had sent her details about my likes, my experience and my fantasies.

I wanted to be turned into a slutty female version, be used and lead around in public.

We arranged the times and financials. And both went out to prepare for the evening. She went shopping to find proper outfits and I went to find some fitting footwear. I was so excited and nervous the whole day, my knees were wobbly.
At her place I was met by a stunning Mistress. She had chosen lingerie, that had a hard time keeping in her gorgeous breasts and some platform heels for herself.
She had me undress and we took a shower. It was immediately clear, she was not afraid of close physical contact.

While enjoying some red wine, we found the right outfit. In her intimate and erotic way she dressed me and laid a stunning piece of art on my face. She gave me a few queues on how to behave like a diva and had me practice a bit.

She got out her strap on, had me kneel in front of her and I tried my best to impress her with my blow job.
We moved on to my butt. She gave me the strap on to suck on while she would work increasing toys into my butt. We had hoped I could stretched enough to get her fist all the way inside me. She really put in an effort to make it happen, but my ass was too tight, as I had reached the limit of what my ass could tolerate. We stopped.

During the play my makeup and wig got messed up, so she quickly fixed that and prepared for a stroll in public.

I have never been out in view of others while dolled up, but this part has been a fantasy of mine for a while. Through the make up, her presence and a bit of wine. She gave me the confidence to go out. She changed her outfit, to fit in in public and match my look.

We went for a walk along the coast, while drinking a couple of gin and tonics, each time she would would go in to bar and fetch them for us while she had me wait outside in the open. I didn't have the courage to go inside and interact with people up close, even though she suggested flirting with some guys. At the last bar she posed me in the middle of a wide open space with people all around and passing me, as well as being in full headlights of the cars at a nearby pickup point. I think she took a little longer inside on purpose, so I began to speculate if she had left me out here in the open by myself, I was sweating through the heat, the wig, my excitement and nervousness, it was blissful. At some point she came back with drinks, everything was good. We had a nice chat on our way back. We finished with a shower, were she toke of my makeup.

Throughout the session and the whole day, she was engaged and as excited as I was. She empathized with my nervousness and my level of experience and adjusted every part of the day accordingly.

Thank you Mistress Caroline, it was a magical evening I will not forget any time soon.