Note: This story is a continuation of the previous three and will be best understood if those are read prior.
1
I proudly reached the ground without breaking my neck. It was my first time walking any distance or down stairs in high heels, and I could see why they are despised by many women. My pulse raced with anticipation, unsure of what twisted mix of degradation and abuse Za'ana was in the mood to dish out tonight. She was especially sweet and affectionate earlier today in public, once her hangover had disappeared, touching my face, encouraging me to smack her ass, kissing frequently, looking at me with those mesmerizing brown eyes. On several occasions, she whispered into my ear, with that Russian-French accent I had grown to love, how good my cock felt in her ass and that she couldn't wait for another night with her 'very nazz-tee guy'.
I hoped I had assembled my clothes how she wanted for tonight's activities. In addition to the black leather heels, I wore a tight but stretchy white, long-sleeved turtleneck top, thin enough to reveal a flattened black lace bra underneath. My tiny, pleated, red and gray plaid wool skirt barely covered my naked ass and hanging balls, and left a gap of hairy, bare leg before the wide elastic band of the white thigh-high stockings began. My dick was growing a little already, as I felt especially filthy-minded, as I did when I had worn the garter belt. Compounded by the humiliation of wearing ill-fitting female clothing, and knowing how ridiculous I must have appeared, there was something about having my legs and body covered but dick and ass exposed or under a short skirt that I liked; I wasn't sure why. Back when I was younger, at home alone in my room with the door locked, I wore a t-shirt or hoodie and boots but nothing else if I was in a horny mood. That was probably one reason my dick loved it when I jerked off with only a shirt on in front of her that very first time in Rodanthe, even though I was embarrassed. This night I felt like I was ready for anything, whether it was wallowing in her stinking shit, or having my freshly emptied and lubricated asshole pounded by her dildo. I was already craving it, despite the fact that I could still feel the effects of her recent violations. People in chat rooms said anal gets addicting, and they were right.
My girlfriend, as she called herself for the first time earlier today, was waiting for me, sitting on the pastel yellow blanket sideways on one hip, her legs curled up, sipping a plastic cup of wine. After our fourth day in the sun, her flawless skin had taken on a luxurious, exotic dark bronze hue, which contrasted with her sexy white smile and framed her stunning eyes. Behind her was the view of the cove, darkened but dotted with lights from distant boats and buildings. Next to her was the carton of food and one of her gym bags. Za'ana's clothing continued the naughty schoolgirl theme, with her dark but sun streaked hair in ponytails on the sides of her head above her ears, tied with long pink ribbons. She wore a white dress shirt, and the outline of a white bra was visible beneath in the moonlight. The shirttails were not tucked in and the lower buttons were undone, revealing her sculpted abs and navel, which was sometimes hidden by her long, striped necktie. A short, dark green pleated skirt flowed around her hips. The Middle Eastern beauty's long legs were covered in sheer dark blue stockings, which led the eye down to her feet, tucked into burgundy leather loafers.
She kissed me as I sat down and we sat close while nibbling on our fancy sandwiches, fruit, and cheese, talking quietly. In the middle of me thanking her again for the vacation, I spilled some wine on the blanket.
"Don't worry. I tipped the housekeeper fifty euros to overlook anything that might be ruined or go missing." Za'ana said with a grin.
We had nearly finished our food when her mood suddenly turned sour.
"Now, it's time to find out what the fuck you're doing in those clothes, Robert." The Middle Eastern beauty asked angrily, her widened eyes catching the light from the cabin behind me. Her pony tails and ribbons flowed with the breeze, in contrast with her serious expression.
I sat dumfounded at the unexpected statement. My pulse began to race.
"I left out one of your shirts and a pair of shorts for you, didn't you see them? You could have come out here dressed like a man, ripped open these stockings, and
fucked
me like a man! Are you stupid?"
"I saw the others, but I...thought this is what you wanted..." Again she was messing with my brain. I had never been given any choice before and it was obvious she had wanted me to wear this stuff, but I played along. Still, the thought of missing the chance to slide my dick into her without the theatrics lingered in my mind.
"How do you know the girl's clothes were not for me to wear on another night? You had a choice and just
chose
to dress like a little girl, didn't you? You sick bastard!" She slapped my cheek.
"I'm trying to please you...um..." I stammered, my face stinging.
"Well I see you've made your decision, pervert. If you want to look like a fucking little girl, you should act like one!" She said angrily, a moonlit scowl on her face, reaching into the carton of food.
She handed me two oranges, and pointed at my chest, indicating where the fruit was to go. I reached up underneath my top and stuffed them into the empty cups of bra that tightly stretched around my ribcage. I had wondered why the bra was a C cup tonight, up until now, she had given me smaller sizes to wear. The weight against my chest felt weird.
"Here, you need some nipples," she said, pulling two grapes out of a bunch and handing them to me.
I slipped the grapes into the bra as well, and tried to line them up so each side would match. I felt strange as I looked down at the bizarre transformation. Suddenly a wig appeared, retrieved from Za'ana's gym bag. It was blonde, almost shoulder length, with large curls that swept away from the front and smelled of hairspray. The purpose of putting me in the lingerie up until tonight, seemed to be for my embarrassment, not an actual imitation of a woman in nearly full dress. I slipped the wig onto my head, and the hair tickled my neck. She ignored my annoyed expression as she reached into her skirt pocket and retrieved a tube of lipstick.
"Stick your lips out like this," she said, then made a pouting expression.
I did as she said and felt stupid as she dragged the soft, waxy red stick across my lips and around in a circle twice, applying what seemed like way too much, at least compared to what rubbed off of the few girls I had kissed previously.
She commented in French with a condescending tone and made kissing motions at me, then laughed. "It was embarrassing going through customs with the box containing the strap-on cock I purchased for you, and I almost didn't pack the wig," Za'ana said, referring to the sloppy imitation of a Farrah hairstyle clinging to my head. But I'm glad I did, because now I get to watch you
prance