Updated: Nov 29, 2021
For my “First Reward” my Captain decided to steal me away for a 24-hour escapade somewhere in the City. I was told what to pack, from no underwear, to high heels, the shortest dresses, a few toys, wine bottles, in case the establishment could not serve us alcohol due to Covid, etc.
I was to be ready a few hours later, and would have to prove every once awhile my nakedness. I packed obediently, excited of the idea of being s
poiled by my Captain. I put a light and airy electric blue dress and inserted one of my new Kegel balls gently inside me. We jumped into the car and after a fifteen-minute drive, we made our first stop… A very discreet sex shop, I had no idea even existed, having driven through that street hundreds of times. It felt warm and slightly humid outside or was it just me. We rang the doorbell and waited a little before being allowed in. It was a small but very classy little shop, which looked more like a layout type of boutique. The Captain knew exactly what he wanted and said you must choose a dildo which you can attach on any surface. I stared at him with massive eyes, and felt my pussy swell up like a plump peach. There were only two, so it wasn’t a complex choice. I chose the purple vibrating one with its smooth silicone surface, slightly bent, not too impressive, and which can be used attached to a wall for example, or even to a harness. We left delighted with our new acquisition. Now ready for the second and final destination. Less than half an hour later we arrived at the bottom of a steep driveway, in a fancy and quiet sought-after neighborhood where only high-end properties with lavishing cars were to be found. The gates to mystery were hence revealed… We drove up and were quickly met by a butler who showed us around this boutique hotel which only had us and another guest to entertain. With its six rooms, one knew this was a place that offered complete privacy and where ones every whim would be adhered to. Nestled below a hilltop, overlooking the ocean entangling with the misty sky of the day, the view on every side was quite unique. The house used to be privately owned and you really felt it, as if you were entering someone’s lifelong residence, with walls covered in paintings, multiple collections of vases and all sorts of objects from travels abroad. Imposing fireplaces were to be found in nearly every corner together with numerous pianos, completely out of tune. Chandeliers decorated the ceilings and it all felt very surreal, as if I had gone back a century. We received a brief tour of the gardens and the swimming area, followed by the living rooms, before ascending the majestic center spiral staircase, that lead us to the second floor. An entire corner apartment was set up for us. I felt like I had entered a reading room from one of the Bronte sisters. Another piano was to be found in the corner, with views of the garden and naturally the ocean. We then walked through the bedroom and towards the bathroom. An iPad with private link to your butler was sitting on the living room table. We languished with delight, soaking in our new surroundings for one day and one night. I immediately took possession of the iPad and ordered a few nibbles with a few G’s & T’s. Once the butler had vanished, just as I was unwrapping my new dildo, I felt my Kegel ball slip between my legs. Oops… Perfect timing to test our new toy! No, not yet… The Captain had drafted a new spreadsheet detailing tasks I was to perform during this escapade. And for every task completed to satisfaction, I would earn points which would in return be transformed into financial investments. With great curiosity, I placed my reading glasses on my nose and carefully reviewed the list. It went from titty flashing in front of the butler, to walking naked in the stairway, or even showing my pussy to guests by the pool etc. Those were the kind of cheeky assignments the Captain wished to test that day. Seeking my limits… and how far would I be willing to go… The weather was gorgeous and you could feel sun’s warmth penetrating the room. The Captain was eager to take as many pictures as possible to immortalize the commencement of our new relationship. I got into action, and immediately enjoyed all the attention I was getting from my Captain. I posed in every corner of the living room and aroused him instantly, fingering myself as often as I could. I would rub my breasts on his penis, trapped and set to explode through his jeans. The pleasure of seeing him this way is always a triumph. We decided to slip to the pool before things would get out of hand and we would probably not leave the room until the next morning. I ambled with lightness in my teeny Brazilian flagged bikini leaving a good nipple showing down the staircase, enjoying my first real attempt at exhibiting part of my body other than topless on a beach in the South of France. The butler could only but notice my nipple showing, and attired in yellow and green, I could not be missed. He probably felt a little uneasy each time he had to bring us drinks by the pool, I on the contrary felt amazing! There was only one other guest, unfortunately, that would not benefit my assignment, and he was sitting on the other side of the hotel, clearly not wanting to be disturbed. It was an easy setting and I thought I would remove my two-piece bikini and stroll around naked, dipping in the pool, walking sneakily around the lounge, then walking back up the staircase, stopping every once a while for a picture, caressing myself and feeling very free and liberated doing so. The Captain was hardly unable to contain his delight of seeing me jumping like a gazelle about the mansion. The door of our room slammed shut, I had no time to turn around that the Captain had removed his swim shorts and I got thrown to my knees and was swallowing his cock. He had to pull out otherwise he would come in no time. He relaxed, took another drink, and lay amused on the bed, while I took my out my new dildo and was urged to stick it on the window overlooking the gardens. I obeyed my Captain and played heavily with my new toy, aroused by the whole scene. I first adapted it nicely to my height and then finding a comfortable position to play and tease. I masturbated at the same time and offered a show as I had never done before. The Captain eventually came towards me and continued where he had left off. Still glued to my window, I placed his cock in my mouth and sucked on it until we both came with such eagerness. Anyone in the garden that would have looked up at that moment would see me fucking the window. We dozed for a while then awoke by the knock on the door… It was time for our couple’s massage. An hour of pure relaxation, which was followed by a quick dip in the Victorian bathtub, washing each other and giggling as I toyed with the shower head. All dressed for the occasion, we dined in the majestic dining room, classical music playing in the background and the fireplace alight. Once I had finished my last spoonful of desert, I was pressed to get back to the room and put some leather on. Leather leggings and leather bustier with a pair of open-toed boots to prolong my legs. I posed in and on the piano and mused around our space, sipping wine, dancing and relishing the exuberance of the moment. We made love that night and the following morning, before heading back to our “lives” until the next time. I posed in and on the piano and mused around our space, sipping wine, dancing and relishing the exuberance of the moment. We made love that night and the following morning, before heading back to our “lives” until the next time. I felt proud of myself, I felt feminine and powerful, especially dressed in leather. This may be just a tiny step into something that will not continue to be this “easy”, it was still a first step… Denuding myself with such ease (unfortunately, or fortunately for me, there was only one other guest which made it not too demanding to wander around an empty hotel naked even though I did not earn all the points I could have, had I opened our room entirely naked to the butler) and floating about, loving my new window experience, I felt like I was shining. I enjoyed every request the Captain made and feel we have both so much to offer to one another. It is a power game, definitely, but it is a game where the submissive is already a powerful and strong person to the core
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