Gina made it to my room yesterday around seven at night, and the surprise I’ve been waiting for finally arrived an hour before her estimated arrival. The delivery wasn’t any different from when I used room service to order food, and instead of a cart with a tray full of food, a hot pink duffle bag sat squarely on top. The handles had pink fur to carry from as the delivery woman paused from the sudden sight of me.
My ignoring her to snatch the bag and close the door shut probably made it even weirder in hindsight as I unzipped the bag open, spreading all of the contents across the newly replaced bedsheets.
The first item to catch my attention was the skimpy-looking article of clothing that fell out, covering everything else. I raised it up with both hands and found a one-piece type of tutu with a short skirt and frills along the edge. It was the same blaring hot pink as the duffle bag and something that could easily be spotted from far off in the distance.
The sight of a slip of paper caught my attention as I set the one piece aside, picking up the folded paper. Opening it showed a list of typed instructions, my guess Gina’s words to follow for the night.
“Put on the dress and wig, extra points for doing a good job with the make-up. After that, set up my strap-on harness for use and place the following items in this exact order on the bed.” I paused at the strap-on part, sifting through the items for the harness and the connecting dildo.
The size was thankfully smaller than my own but made me understand the source of said soreness lingering in my ass. The first item starting on the right was a small whip followed by rope and then a buttplug attached to a realistic looking fox tail with fur and all. Touching each item was enough to know that all of them were magically imbued. As to their purpose and alterations I wouldn’t know until Gina’s unique mana signature was pumped through them. The last object was a metallic rectangular container. Opening it, showed a variety of pills sectioned off into seven different partitions.
The first section on the left started out with the least amount of pills ranging to five horse sized pills on the other end of the container. My guess was each set was expected to be taken for each day until the end of the one week duration. My thoughts ran amok over the ungodly concoction that was prepared for me. I checked the clock on the wall to reaffirm her approaching arrival. I pushed those thoughts to the back of my mind as I made due with the remaining forty minutes to dress up like she instructed.
I undressed and only realized til now that it wasn’t just my pubic hair that was shaved clean, but my entire body. Not a single hair other than what was sitting on top of my head could be found. Taking a look at the hot pink tutu and doing my best to put it on, turned out easier than expected. It might have been due to the fact that the underwear part was completely missing, leading to an exposed groin and butt. The only thing offering any cover to my chastity cage was the short fluffy skirt that barely concealed it when held down with a hand.
I sighed not knowing what to think and moved onto the assortment of make-up that was provided. I set it onto the bathroom counter using the mirror as the only guidance for my first time ever applying any kind of make-up. Of course she picked out a matching hot pink and thick kind of lip gloss to put on. They made my lips look full and plastic from the amount of shine they were giving off. Next was the mascara as I tried my best to visualize and mimic Gina’s own work. I ended it with a blush that closely matched my skin tone and called it quits. Any more and I’d turn into a clown, the exact opposite of receiving her praise.
The last bit to the whole wardrobe change was the realistic wig. It was black with brown highlights weaved in, flowing straight down to the nape of my butt. It was surprising to find out that everything fit to a tee with the mirror showing myself as a skinny crossdresser. My wide shoulders and muscles were the things that stood out, making the entire get up look utterly ridiculous.
I found myself with some spare time and went back to the bed after assembling the strap-on harness. There was something else typed on the sheet of paper that I didn’t get to read and went back to it.
“Unlock the front door and grab a glass of water on your way back to the bed. Use it to take the first batch of pills inside of the metal container. They aren’t harmful to your body and there’s no chance of them messing with your memory.” I immediately bulked at the thought, from having already experienced one of her pills that placed kastamonu escort me into this crazy predicament. I went to unlock the front door and set the glass of water on the countertop beside the bed. I looked back down at the paper after grabbing the pill case. The last sentence was like she could read my mind.
“If you want to be rewarded, you will follow each and every one of my simple instructions before I arrive.” To make matters worse the sound of the front door opened, following my rushed attempt to down the pills with water as if to hide the evidence. I then thought about a major flaw in her plan though a bit too late. There was no way she could tell if I actually took them or flushed them down the toilet.
“Beautiful…, You’ve outdone yourself. Really gunning for that sweet release aren’t you?” Any and all reflection dissipated with the sound of her endearing yet humiliating words. Her attire made it obvious she came straight here directly from the office. Just looking at her in those four-inch heels was all it took to tighten my throbbing penis against its cage. “Good boy, it looks like you even gulped down the medication.” Her choice of words startled me.
“What kind of medication did you make me take?”
“I didn’t make you do anything.” Gina stated as she unbuttoned her skirt, letting it fall to the floor as she retrieved the strap-on harness. “You did so of your own volition, in hopes for a special reward. Don’t worry about the medication, it’ll be a sweet surprise that will present itself in due course.” Gina finished looping the harness through her legs and securing it firmly against her waist.
“Now lie back on the bed. Let’s get a better look at your caged manhood.” I stopped myself from asking more questions on the slight chance it ruined the mood I so desperately sought to create. I laid on my back while still lifting my head to keep an eye on what she planned to do next.
She leaned over with one knee on the bed, still wearing her heels and close enough to inspect my chastity with one hand from the side. I wished to feel her delicate fingers only for the cage to fully block all possible touch. Her grasp turned it into a tugging sensation that had me attempting to get hard nonetheless. Her touch got to the point where it caused an internal erection to occur with my penis being forced back into my lower abdomen.
The feeling wasn’t ideal but it was more than manageable, to ignore the aching pressure. “It’s so cute and perfectly out of the way. Are you really sure you want to have it released from the cage?” Her teasing tone, insinuated the possibility of keeping it locked up for the entire night.
“Yes, I’m sure I don’t want the chastity on, any more or ever again. Please take it off.” My rebuttal was instant and filled with urgent revision.
“Do your best to please me then.” Gina sighed then moved on to commenting on my make-up and long hair. “Have you crossdressed before, your make-up is impeccable. Simple and nearly better than my own. And that wig fits you so perfectly!” There were no words on my end as she placed a hand on the wig after sifting through the long strands running along the side of my arms.
“Since it suits you so well, let’s make it a bit more permanent.” I squinted at her meaning and didn’t act until it was too late. A trace of magic coursed through her fingers, intertwining into strands that attached the wig to my actual hair. A quick tug in disbelief at the hair resting by my hands was enough to test her words. It should have been enough to slightly displace the wig, but ended up pulling my head in the same direction as a result.
“What the-…” I stopped myself from cursing and knew it was only as permanent as scissors, deciding it best to let it slide. Thankfully Gina seemed to be self absorbed into her planning and didn’t seem to catch it.
“Good now get off the bed and onto your knees.” She backed away and stood up, pointing at the spot in front of her. “Looks similar doesn’t it?” She was talking about the strap-on my eyes were glued to, as it transformed into a spitting image of my very own penis when fully erect. The magic she imbued into the dildo allowed for a simple thought to shapeshift it into her exact mental image.
I acted a step ahead of her and did what I figured she wanted me to do, taking the cloned dildo into my hands and placing the tip into my mouth. It was kind of disturbing to know that she memorized my seven inch penis down to the minute veins and detailed texture.
“I didn’t know you were such a slut for cocks, even if it’s modeled after your own.” I knew she was aiming to get a rouse out of escort kastamonu me, and set my focus to lathering it up with saliva. It was easy to see the direction she was going with all of this and all I could do was lessen the damage. Something I’d need to be on top of throughout the coming week. “That’s enough, get yourself on the balcony’s edge with both hands on the railing.” She ordered me and I saw her go to retrieve the whip and rope on the bed before opening the balcony window to step through.
The chilly wind was enough to cause my bare legs to shiver. We were on the fourth floor and placing my hands on the railing allowed anyone that was looking in this direction the ability to see my helpless penis.
Hearing her enter gave me a short reprieve as my mind went back to what she had in store for me. “Why are we doing this out here?” I asked in the softest and most calm tone possible.
“Remember that favor we’re going to return to the others. Well consider this our payback. Plus you were curious about the reason for your soreness.” She stopped there and used her hand to push back my questioned stare to face back forward. It was a good view of the swimming pool below with a couple of late night people having fun goofing around. The view extended to several other outdoor activities and I came to the quick conclusion between the putt-putt golf and bbq grill parties that things were extremely lively tonight. I knew a single sound would have a high chance of garnering the attention of those enjoying their time below.
“Looks like we chose the perfect time to enact our revenge, don’t you think?” Peering from over my shoulder, her hand set the short length of one-foot rope on my left wrist. It was another one of her magic items as it instantly grew in length. First securing my wrists to the railing, then swirling around the rest of my body and down to my feet. The pressure of the rope was strong enough to dictate my posture and stance.
Not only did it bind my arms to the railing, but it forcefully spread my thighs and feet apart, bending and arching my back out and ass up. It lowered me into the most compromising position, accurately judging the perfect entry for Gina’s strap-on.
“I can’t move… Stop it, everyone will see us.” The tension holding me in place made it so that I couldn’t even turn my head back to look at her.
“I would hope so, that is today’s objective and part of the revenge plan.” I could hear the evil smirk even without seeing her face as she surprised me with placing the cold and dried up tip of the copied dildo against my rear entrance. “Since you’ve been such a good little sissy, I’ll use some spit.” Gina carried on with spitting into her cupped hand. The only way I could tell she was lathering the entire length of her strap-on was the brushing of her wet fingers hitting against my bottom.
“Here’s a bonus chance to get out of chastity for the remainder of the night. All it takes is your loudest moan from being impaled in the ass.” She teased the tip of the dildo against the rim of my opening, prodding ever so slightly with her words. “Gotta be quick though, your window ends after my first thrust.” She didn’t give me much time to mull over a possible decision as the hordes of people down below made me reflexively hold in the moan.
Gina inserted the full length of my seven inches into my butthole without a shred of warning. It wasn’t until her third thrust that I let loose an uncontrolled moan. “I guess you like being caged.” Gina’s laugh was louder than my subtle moan. All I could do was ride the wave of pounding as I regreted my inability to act quickly.
She started settling into a rhythmic fuck as she grabbed a handful of my long hair, pulling on it hard enough to jerk my head back against the tensed rope. It only added to her speed as it caused me to let out a sharp yelp in return. I wanted to do everything possible to cover my mouth with a hand, only to be denied and stuck in this embarrassing spread open position.
My eyes lulled to the front covered in a heavy glaze as she said something. “Our first victims, aren’t you happy?” She snickered and kept up with the steady pace, using my hair as extra leverage to thrust harder. My attention shifted down to the group of people enjoying a bbq. A guy was pointing up at us, with his head turning back and forth to the others in his company to grab their attention.
I closed my eyes, hoping they couldn’t see me if mine were closed, only to hear a mix between excited wooing and shocked words. I wanted to keep my eyes closed forever at this rate, scared to witness their reactions. That was my game kastamonu escort bayan plan until a sharp sting slapped against my right ass cheek. Opening my eyes wide as a result and releasing my first loud noise.
“See if only you made that sound at the very beginning.” Gina used the short whip with her free hand. It felt more than a normal whip, one that coursed through my entire body from the point of contact. Her second strike confirmed it as the jolt of electrocution spasmed throughout my muscles. My entire body went slack with the rope being the only thing holding me up at this point.
I opened my eyes to see every single person, even the ones swimming in the pool stop and stare at me, being mindlessly fucked. The ones with family hurried away after realizing the show wasn’t going to end any time soon. The others that didn’t mind, stuck around and even cheered on.
The pain from each strike of the whip made me forego how I might seem to the public as I rode each spasm to the point that my anus went numb, no longer able to feel the penetrating strap-on.
A pause from the whipping allowed me to catch my breath and take in all of the rowdy noises surrounding us. “This seems to be the extent of your pathetic penis.” The size and swelling of my anal cavity widened with her statement. The strap-on mirrored after my erection grew in thickness and length. Growing from the girth of a golf ball to that of a baseball all while tacking on several inches to the length. “How’s it feel to be fucked by a real cock. You understand my reason for locking up your pathetic dick now don’t you?” Each exacting thrust down to the base had me moaning in tune. The numbness went away with the sensation of fullness filling out my insides.
Between all of the pain from my hair being used as a handle and the newly enhanced strap-on together with well-timed whips, had my penis as limp as could be, flailing about from the pounding motion. It created a strange feeling never felt before, as my entire body exploded with pleasure. Only after the intense wave of bliss did I feel the liquid dripping from the chastity cage’s pee hole.
I experienced my very first prostate orgasm, entirely different from a normal ejaculation. Instead of shooting out a thick stream of cum, it merely dribbled slowly onto the balacony’s floor like a leaky water faucet. The most disturbing revelation though was the fact that my arousal levels didn’t plummet like a usual masturbation session would have achieved. I stayed at a high level of arousal as if I’d never cummed in the first place.
“Is it true that guys can cum multiple times like a girl from prostate stimulation?” Gina definitely knew the answer and said so as a means to mess with me as she picked up the pace again. “No need to answer, I’ll find out soon enough.” Again with her laughter, she was thoroughly enjoying the spectacle she was in charge of.
The second climax turned into a hazy blur as several minutes seemed to pass as she brought me to the same blissful plateau as before, this time with my cock offering a bit more umph in shooting a load far enough to fly through and past the railing. My penis became hard throughout the constant thrusting once she eased off of the continuous whipping and hurt from the constant struggle against the hard plastic cage.
I could feel the gaping in my ass that memorized the size of Gina’s strap-on as she pulled out for the very first time. The rope surprised me by giving way and releasing my hands from the top of the railing. The feeling of freedom was short lived as it spun me against my will, into a kneeling position on both of my knees.
It placed me in a perfect side view for all of the onlookers as Gina moved to my front. She timed a whipping and a hand around my head together with the forceful insertion of her strap-on into my mouth. Taking advantage of my yelling cry to offer me the taste of my ass after being rammed into oblivion.
I immediately gagged on the thick dong as the smell was enough to make me want to vomit. That seemed to be her aim as she thrusted back and forth three more times as if to act like a toilet’s plunger. The sudden removal of her strap-on from my mouth, caused an onslaught of yellowish bile to erupt forth. Luckily, forgetting to eat anything today ended up saving me in a way.
“Aw, poor thing… You’ll get used to it in time, trust me.” Gina caressed the scalp of my head with her soft fingers. “Now say goodbye to our crowd, so we can continue the fun inside, on a comfy bed.” With a snap of her finger, the rope re-adjusted my position to standing tall before our entire audience, granting me control over my left arm. I couldn’t stand the many sets of eyes burning a hole into me as I raised my hand into a waving gesture, wanting to speed up the process to escape the humiliation. She kept me in the same position even after their roaring cheers and name-calling, only releasing me once she made it back into my room.