The Weekend Sissy

I smiled reading the message Chris sent, seeing his name light up my phone always put a slight blush on my face. Sending a sassy, flirty response, I returned to finishing dinner, unable to stop my imagination taking root. It was always the same when I got the message about getting together for a weekend.

About three years ago, I met a group of friends by chance on a night out. Wearing a beautiful tight, red dress, I happily flirted with them all evening, before they took a slightly tipsy sissy home with them to be completely ravaged. The next morning they said goodbye to me, my number in each of their phones, walking out with my body and tongue coated in their cum. I still got excited little shivers thinking about it.

A few months later, I got a message from all of them, saying they had rented a cottage for the long weekend, wondering if I'd like to repeat our night of passion. I couldn't say yes fast enough, spending three days under their control. Very soon it became a tradition, getting a message or two once in a while, requesting my...services. The answer was always, excitably, yes.

After dinner I made my way to the bathroom. I had a few days before they'd be there to pick me up, the large station wagon we'd all pile into for the road trip. But I liked to be prepared, putting myself the wonderfully frustrating mindset that came hand in hand with denial. Nothing pushed me into girl mode faster than locking up my eager, desperate, little clit.

Systematically, I sugared my entire body, soothing my skin with a warm shower and lotion. Already I could feel myself delving into Rory, that feminine, submissive, bratty persona I had become far too comfortable wearing these past several years. Walking over to my kinky drawer, I giggled as I took out the pink, tiny cage. The smallest one I had, held in place by matching straps, I quickly snuck my clit inside before it knew what was happening. In no time at all, that familiar straining began, my hands rubbing over the prison that would encase me until we returned.

I moved to my closet, taking out a beautiful lace bodysuit. Light pink, offering little in coverage, I bit my lip with excitement as it slid up my smooth legs. Sitting perfectly on my shoulders, pulled in between my cheeks, I looked down at the fabric hugging my clit, exposed completely. Exactly what it was meant to do. Slipping into my favourite pink stiletto's, I spent an embarrassing amount of time admiring myself in front of the mirror. Satisfied with the look, I snapped off a few pics and videos to those wonderful boys, ensuring they knew I was ready to be their good girl.

They flooded me with messages, making me blush and giggle as I read them. Kevin, Jerome, Duncan, and of course, Chris. Four wonderful men, each of which I enjoyed serving and sharing their company, practically drooling over my now feminised form. I sat down on the edge of my bed with legs crossed, my clit straining from all the wanted attention. Eyes wide with excitement, I chatted with them all for a little while, before one by one they drifted off to sleep.

Well, all of them except for Chris.

Lying in bed, rubbing my legs together, I chatted back and forth with a permanent blush on my face. I loved being with all those men, but Chris was...well different. We connected immediately over the first year, both as friends and sexual partners. Being with him just felt right, simple, intoxicating, and easy. I whimpered as I ran fingers along my neck, remembering all the times it had felt the grip of his hands, or the touch of his lips.

He requested several pictures of me over the course of the night, feeling the aching need already surging inside of me. I tried twice to entice him to come over and fuck me, but he just kept up his torment, watching as I fell effortlessly into the role that suited me most: their sissy slut. When he finally told me to go to sleep I pouted, unsure how that was possible with my clit straining away underneath my bodysuit, already falling into a desperate mindset.

Friday was too far away!

Two nights and three days later, I stood in the main room of my tiny apartment, brimming with excitement. Bags packed with an assortment of outfits I knew they liked, shoes, toys, and everything else I'd need to ensure I was the perfect sissy for all their needs. I was wrapped in my giant coat, hiding the lingerie I had chosen for the journey, the last decision I'd be making until they brought me back home.

Always one for subtly, my door was flung open by Duncan, his giant frame and massive shoulders filling just about all of it. He saw me immediately, a big giant grin on his stupid, lovable face.

"THERE'S OUR GIRL!" he bellowed, that voice of his echoing off the walls. Blushing, I tried to get him to shut the door, but he picked me up in his arms, my sensibility chased away as I wrapped my arms around his thick neck, kissing him. I squealed as he put me over his shoulder so effortlessly, his hand finding its way up my coat. "Okay I've got her."

"Put Rory down, Duncan. We all want to say hello moron." I giggled once more as he slowly let me return to my heels, pretending to glare at him as he did so. Truthfully though, it was impossible to ever be mad at Duncan. Kevin, who had chastised his large friend, grinned as he saw me, planting a tiny kiss on my lips. He was more of a fighter than a lover, leaving the 'gushy stuff' as he called it, to the others. I blushed as he pulled away, knowing I'd see the more aggressive side of him soon enough...

Jerome tackled me in a similar fashion to Duncan, although his was far less extreme being closer to my size. Still, I always loved being tossed around by those two, making me feel small and girly. That wasn't easy for someone who was 185cm...without heels! Smiling, leaving a tiny smooch on my cheek, Jerome let me go to face the final member of their crew, already wearing his knowing, infuriating smirk spread across his face.

Chris walked up, a finger placed underneath my chin while I whimpered, breath temporarily stolen from me. Those piercing eyes taking me in, holding me captive, watching as I squirmed underneath their dominant capabilities. Even after all this time, I couldn't escape the power this man held over me. Nor did I want to. Leaning in, he planted a tender, light kiss on my lips, listening to the tiny moans I had no control over leaving my body, whispering right against my skin.

"Hello, baby girl." I swear I felt a tiny bit of cum leave my poor cage.

Kevin rolled his eyes at his friend's greeting, gathering all of my bags. "Shall we go then? It's a bit of a drive." Duncan cheered, picking me up in his arms once more.

"Then it is a good thing we have some road trip entertainment!" Shaken out of my submissive haze, I squealed as he carried me out of the apartment, kicking my heels in a half-hearted protest. With no intention of letting go, I was carried out to the car, placed in the very back row of seats. My special spot.

As Chris started the car and drove off, the other three all turned back with a hunger in their eyes. Oh how I missed that look directed at me. "I think," Chris said, eyeing the mirror when he could, "it is time for you to lose the coat, Rory." I blushed, staring into each of their eyes, slowly pulling on the belt tightly encasing me. With all the dramatic flare I could muster half-sitting in a low ceiling vehicle, I flung the coat open to reveal my chosen outfit.

"Fuck me..." Always the poet with words, Kevin's jaw dropped. I giggled, running my hands up and down the black stockings on my legs, garter straps holding them tightly in place against me. A body corset, the deepest black I could find, hugged my waist as snug as I dared without losing breath, leaving my nipples and chest exposed. My silk panties, with see-through sides, perfectly showed off my caged clit, outlined for all four of them to see, as well as the wet patch that their introductions had forced out of me.

Smiling, I shrugged off the coat fully, handing it to Jerome, the three speechless men still eyeing me up and down. Rubbing my legs together, my hand running up and down my body as I moaned with anticipation, I drank in the moment. Savouring just how eager they were for me, to have me, use me, own me. There was no other feeling in the world I found that could match it. I bit my lip, staring with wide eyes, hoping to entice one of them to begin our weekend fun.

It worked like a charm, Kevin practically climbing over Duncan in a rush to the backseat, shouting "Dibs!" as he did so. Duncan, still locked in a bit of a daze, and Jerome holding my coat, scowled as Kevin shot them a grin. Grumbling, they turned around in their seats, occasionally turning their necks just slightly enough for a peak. Chris simply drove on through the city, his smirk returned to his face, eyes lingering a bit longer than they probably should have in the rear view mirror.

My focus, however, went to Kevin. I pushed him into a seat, happily sitting in his lap with a smile, legs stretched and laid out to the side. Arms wrapped around his neck, I moaned as my tongue found its way to his, my clit a constant ache since the 'kidnapping'. Kevin groaned underneath me, one hand holding my waist, while the other ran up and down my nylons, sending shivers all through my body.

I giggled against his lips, feeling the cock growing beneath me. Staring into his eyes, I rubbed my ass against him, watching that hunger intensify as he intently watched, both of us locked on to one another. Gripping my hair, I moaned hard as he pulled me back, his voice turned into a deep growl.

"Enough teasing me you little slut." I giggled, my body responding immediately to that deep, serious voice of his.

"But I'm having fun..." I let loose another giggle, knowing I was about to be put in my place. Kevin's grip tightened, turning me so I laid across the back seats, my face now resting against his crotch. Smiling, submitting that my teasing game was finally at an end, I looked up at him while I dug out his hard, ready cock. Stroking it with one hand, I set to work kissing and licking his balls, before running my tongue up and down the entirety of his staff.

Eyes rolling back, an appreciative groan escaping his lips, Kevin held me in place while I played with him. My hands and mouth swapped position, holding his lower shaft and balls, the head of his cock disappearing past my lips. I switched to my knees, my ass high in the air, exposed to other drivers and the rest of the car, bobbing my head up and down with vigor. Three days of wearing my cage had pushed me into a frenzied mood, and I funneled all of that frustrated energy into pleasing him.

Kevin ran a hand down my back to rest on my ass, squeezing and gripping each cheek how he pleased. I whimpered with each touch, the plug in my ass shifting every time he played with me, tickling my g-spot, sending tiny pulses through my body. Moaning around his cock, feeling more and more of him in my throat, I could only try to ignore that desperate plea inside my head, begging to cum.

Groaning, Kevin grabbed my head with two hands, shoving me down to the base of his cock. Breath stolen from me, I whimpered as he came, filling my mouth and throat while I locked my lips around him. The entire time his orgasm flooded my mouth, I felt my clit aching, screaming from the injustice. Carefully, feeling the final twitch of his cock, his iron grip relenting, I slowly raised my lips to the tip, breathing deeply through my nostrils.

Sucking and swallowing, I made sure not to spill a drop before releasing his cock from my lips. Running my tongue up and down, I cleaned him to the best of my abilities, feeling him twitch as I got close to his tip, still sensitive after cumming. With a smile, I rested back on my knees, giggling as I caught my breath. Kevin did the same, collapsing in his seat, cock beginning to wane.

"Fuck me, I missed your mouth Rory." I grinned, gloating from the compliment, watching as he put his cock away once more. Recovering slightly, he looked at me and laughed, spotting just how wet my panties were. "I guess you missed us as well, you little slut." I burned with shame, Duncan and Jerome joining in. I tried to protest as Kevin demanded my panties, but I turned an even deeper shade of red as I stripped them down my legs, my leaking clit exposed to the car.

"Someone is excited to be our little fuck toy, isn't she?" I looked away, only able to nod at Jerome, the heat on my face almost unbearable. I desperately needed to be fucked. Now. But as Kevin and Jerome switched places, once more finding myself with my ass high in the air, I knew my need would be ignored and postponed for quite some time. So I did the only thing I could, the only thing that took my mind off the aching torment between my legs even slightly.

I was their obedient, dutiful, submissive little fuck toy.

By the time we arrived at the cottage Friday night, it was already dark thankfully, as neither my coat nor my panties were returned to me. Both Duncan and Chris had made their way to the backseat with me, swapping over drivers halfway there, the mixture of all their cum heavy on my tongue. For the last hour I had sat on Chris' lap, whimpering as I leant against him, his fingers slowly rubbing and circling on my clit and nipples. Each time my clitty leaked with excitement, I would lick his fingers clean, only to have more drained out of me from his constant touch.

Walking into the cottage we all stretched and sighed, the drive slightly longer than we thought. I immediately found myself kneeling in the living room, waiting excitedly as I watched Chris unpack my collar. Thin metal, with a simple hoop at the front to lead me around by, I softly moaned as I heard it connect behind my neck, the key tightening it shut, knowing it wouldn't be re-opened until we left. If an entire car ride of being teased mercilessly, used as their little sissy toy didn't let me know I belonged to these four men, my signature collar certainly sealed my fate.

Letting the metal rest against my neck, Chris gently planted a kiss on my cheek, whispering right into my ear. "There, a much better look for our good girl." I blushed, feeling shivers course through my body from his voice, clit aching once more as I knelt firmly in place, waiting. Out of the corner of my eye staring down at the carpet, I saw Kevin unpacking a series of metal bars from one of their bags, instantly whimpering with excitement.

The four men laughed at my response, thoroughly amused at how aroused my denial made me. I watched him disappear into my room for the weekend, soon following behind as Jerome clipped a leash to my collar. Kevin was in the one corner setting up the three bar prison I knew and loved, a simple triangle that kept me bent over and exposed. However tonight held other challenges it seemed, as I was brought up on the bed, arms pulled between my knees and clamped shut in a spreader bar.

I huffed, trying to blow a tiny strand of hair out of my eyes, the boys never really liking when I wore wigs. Just my natural, longer on top classic fade, which I styled slightly more feminine. Soon my mind was pulled away though as strong hands gripped and rubbed my ass, plug and clit now firmly planted in the air, on display as their eager little fuck toy. I whined with excitement, literally shaking with the need to be fucked.

However my hopes of begging for such an event to occur were short-lived, as Jerome wrapped a ball gag around my head, growling around the new obstacle in my mouth. He had a...thing for gags, often listening to me moan for hours through a series of different ones in his collection. In fact, Jerome was who had taught me years ago how to overcome my gag reflex, my mouth held open in a variety of ways while he trained my throat.

The door left open, knowing my constant stream of noises would be floating around the cottage, I whimpered as hands returned to my ass, playfully pushing and pulling on my plug. Jerome had stripped down completely, his cock rubbing in between my cheeks, my face half buried in the mattress as I whined, pleading wordlessly for him to fuck me.

Taking pity on the depraved, denied sissy, Jerome gently pulled out my plug, his fingers spreading lube in and around my hole. Gripping both of my ass cheeks, he planted his feet on either side of me, sliding his big cock all the way down until I felt him bottom out. Eyes rolled back, my clit tingling with anticipation, I groaned in appreciation. This was what I was made for. Reduced to their toy, their pet, used how they saw fit. Each time I was dragged on one of their weekends I felt myself wish for these moments to last forever.

But my imagination of such a wondrous thought was shattered, as Jerome pulled out and began fucking me. Hard. As excited for the weekend as I was, he pumped that energy into me, methodically thrusting in and out while my brain melted around him. I drooled, moaned, whined, whimpered, and squealed with delight through each movement. It didn't take long before I knew his cock was going to force an orgasm out of me. One that I desperately needed.

Hearing my eager moaning increase, Jerome spanked my ass while he fucked me, bouncing in his palm as I was taken. "Going to cum already, Rory? You are such a slut, baby girl." I nodded, eyes rolled back as his beautiful cock hummed inside of me, rubbing my g-spot in just the right way, feeling that build-up grow, and deepen. I couldn't hold out, desperately denied and teased for days, my body screaming at me to give in.

Quivering, my legs and ass shaking from effort, I felt the first orgasm of the evening fucked out of my eager little hole. Stuck in place, I simply let go, allowing myself to cum hard while Jerome's cock never faltered. Leaking out of my cage, my poor clit bounced back and forth, covering myself and the bed in cum. Barely able to breathe or think, I gave up on trying, relenting to the control of my owners.

"Well, that didn't take long." I heard Chris from the door, unable to make my eyes function currently, yet I knew that signature smirk was spread across his face. Jerome joined in his chuckle, hearing his breath quicken, feeling the cock pumping in and out of me thicken and tense. With a deep, sexy groan, pushing as deep as he could into me, I moaned happily as I was filled with cum.

Both recovering from our orgasms, I sighed happily as Jerome collapsed against my back, planting kisses up and down my sweaty body. "Fuck, Rory. Fuck. It has been far too long, baby girl." I giggled, wiggling my ass against him in appreciation, always having such kind words for me. Unbuckling the gag, I stretched my jaw as I moaned, his cock slowly leaving my ass.

Left empty, I pouted, my desire to be fucked far from sated. Thankfully I didn't have to wait long, Kevin strolling in soon afterwards, cock already hard and ready to fuck me. Freed from my gag, I moaned loudly as he slid into me, the air filled with him spanking my ass nice and red, pulling my hair back as he vigorously used my body. Faster than I would have liked, my ass stinging angrily from his palms, I listened to him cum, feeling his twitching body against me.

Duncan used his strong arms to lift me off the bed, moving my body against his giant cock as he used my well fucked hole. I never got over how small he made me feel, a toy in his control as I was fucked like a fleshlight for his amusement. After filling my asshole with his cum, feeling it dripping down my leg, Duncan gently placed me back on the bed, now exhausted and smiling. I heard the door close, leaving me bound and exposed, a toy that had fulfilled its purpose.

A few hours later I was awoken from a much needed nap, a gentle hand rubbing my sore muscles. The spreader bar was unlocked, allowing me to stretch and moan with appreciation, feeling the bed sink down beside me as I laid back. Barely able to make out Chris in the darkness, a small plate of snacks offered to me which I hungrily devoured.