[Commission] A Ticklish Sissy Trophy

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A commission for ! Thank you so much for your order! They also paid a little extra for a bit of story, so enjoy that below!

I'm sure this is pretty obvious, but this picture is a bit too lewd for Deviantart, so it's super-duper censored! Find the full, uncensored version on my Tumblr or HF.

(All characters are portrayed as 18+ regardless of original depictions).

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“11:30 PM. Marlborough Park. Meet me at the marble statue in the centre.”

Calum’s delicate fingers danced across the surface of the thin, lined paper once more, tracing every little fold and imperfection as if trying to commit them to memory. He read it again. A second time. A third time, letting his eyes sheepishly drift up to confirm his surroundings once more, as if the little marble bust had somehow moved while he was looking away. Frigid night air stung at his face and sent its shivering messengers through his body, eliciting a little squeak.

“Oi, there you are. Didn’t keep you waiting, did I?” A voice broke through the darkness, interrupting the droning choir of crickets. Calum jumped a little in surprise, clutching the note to his chest as he tried to steady his heartbeat. He scrambled from his seat, concrete scraping as he pivoted on his heel to face his interlocutor.

The woman stood at least a head taller than him, light brown hair rolling down her back and hugging her lithe body. A pair of bright blue eyes seemed to pierce the night from behind a pair of slim, black glasses. A warm smile played at the corners of her pale lips.

“O-Oh, Jessica. I should have expected you were the one who took it…” Calum’s voice came out meekly, struggling to find its way through the air. Jessica raised an eyebrow, chuckling to herself under her breath.

“Really now, it’s rude to make assumptions. Especially when I so graciously called you here in order to return this to you,” she teased, fishing around in the little black handbag fastened to her hip. Her fingers eventually closed around the smooth casing of a smartphone, pulling it out into the light. “See? I even kept it in tip-top condition! You should really be thanking me, Calum, dear,” she cooed.

“Why would I thank you for stealing my phone? L-Listen, I don’t know what you want with me, just give it back, okay?” Calum pleaded, making a lunge for the device. Jessica shuffled out of the way, holding the phone out at arm’s length.

“Whoa there, let’s not get hasty, now! We’re gonna play a game, okay? That’s all. Don’t even have the courtesy to indulge a bored lady?” Jessica tapped her foot, ensuring she kept the phone out of Calum’s reach. “C’mon, it’ll be fun. We’ll even put stakes on it. You win, and I give you your phone back! See, generous! Besides, if you don’t participate, I’ll just have to keep this as payment, instead. I wonder what secrets I’ll find on here when I get it unlocked,” she threatened, puffing out her chest proudly.

Calum retreated a little, scanning the empty plaza with nervous eyes. Figured that this had to be made difficult. He took in a deep breath, biting his lip nervously.

“F-Fine. What’s the catch? What do I have to lose?”

“If you fail the game, I’ll make you my slave!” 

Silence. Calum blinked a few times, staring at her with disbelief as his mind struggled to catch up with her words.

“Are you taking this seriously? Listen, I just want my phone back. Whatever this game is, I’ll do it.”

“You’re doubting me? How could I take this anything but seriously? Tsk, tsk. So you agree to play, then?”

“Y-Yeah, yeah, whatever. What are we doing?

Jessica pumped her fist triumphantly, slipping the phone back into her bag, seeming to take pleasure in the little metallic click that signalled its closing.

“Awesome!” She exclaimed, cracking her knuckles and taking a step forward. “Well then, strip.”

Calum thanked his lucky stars that he wasn’t drinking something when she said that. Even still the sudden demand caused him to somehow choke on his own spit, eliciting a fit of coughing.

“I-I’m sorry…?” He sputtered out, clenching a fist to his chest.

“Hm? Was I not clear? Ditch the clothes. We’re walking to my place. You’re walking naked. If anyone sees you, you lose. Simple, right?”

“Y-Yeah, no, there are countless things wrong with that.”

“Well, yeah. That’s kind of the point. Why do you think I’m doing this, sweetheart?”

Calum clicked his tongue against the roof of his mouth, weighing the options in his head. His fingers brushed up against each other, lightly fidgeting around as he thought. Calum softly chewed the inside of his cheek as he peered up at Jessica, the smug grin plastered across her pallid countenance seeming to thump up against his chest, granted impunity by the tiny device in her handbag.

“F_Fine… I’ll do it…” Calum muttered under his breath, his heart threatening murder as his face began to gain heat. A silent understanding bubbled up between the two, Jessica remaining silent but urging him onwards with her gaze.

Calum grit his teeth as a pair of shaky hands reached down towards his shirt, slowly yanking it upwards to peel it from his body, revealing the smooth, well-formed curves underneath. His face burned as Jessica arched an eyebrow.

“Ooh, well isn’t that cute? C’mon now, don’t keep me waiting!” Jessica urged, motioning with her hand to move forward. Calum could feel his gut tying itself up as sheer humiliation began to seep into his being, spreading through his body and dusting his cheeks a bright red. His nipples began to harden as a midnight breeze caressed his bare skin, tenderly stimulating his nerves and causing his body to break out into shivers.

“D-Do I really have to—“ Calum began to complain, pursing his lips and cutting himself off as Jessica sent a piercing glare his way. With trembling fingers he began to unbuckle his pants. He let them fall limply to the ground, shyly stepping out of each leg to leave him standing in his underwear. His toes curled in his shoes as he began to pull those down, too, shimmying down his knees and around his ankles before stepping out of them as well.

“Snrk!”

His head jolted towards Jessica as a little chuckle escaped her lips, Calum’s face blushing furiously at this exposure.

“Aww… Look at it! It’s so small and cute! Should I even call that a penis?” She mocked, giggling to herself. Calum moved his hands down to cover himself up, but the effort was quickly thwarted by Jessica strongly gripping his arms and pulling them from his privates. “And you’re all shaved, too! What’s up with you? Such a petite, girly body, such a cute little dick—I’m almost reluctant to call you a man!”

Jessica began to exert a little more pressure, keeping Calum’s wrists tightly in her grasp. Calum drew in a breath and tried to struggle, but found Jessica able to effortlessly hold her own and overpower him. “C’mon, let’s get those shoes off of you, too!” Jessica exclaimed as she began to forcefully lead Calum backwards, slowly but surely pushing him down onto the park bench.

“L-Jessica, what are you? S-Stop!” Calum began to plead, squirming around fruitlessly under her grasp. Jessica cackled in response, running a hand down his thigh.

“Hey, hey, quiet down! What if somebody heard you and came to investigate?” Her hand drifted all the way down to his shin, moving to his shoes. “C’mon, let’s get these things off too, then you’ll be just like a proper slave should!”

“H-Hold on, you weren’t serious about that, right? B-Besides, I haven’t bee—nhh! S-Stop! Y-You can just leave those on, I’m already naked!” he begged, face brighter than the sun as he wriggled around on the bench, frosted wood stinging his skin. Jessica used one hand to keep him held down, the other one beginning to worm its way into the heel of his shoe, slowly prying it from his foot.

“What are you whining about, hmm? You’ve already lost—so as per the rules, you belong to me, now, right? I saw you naked, therefore, you lose. That was the bet,” she explained casually as she popped his left shoe off, and then his right.

“Th-That’s not fair! Y-You didn’t--! I didn’t have a—mhhf!” Jessica moved the hand pinning him down to his mouth, clamping it over Calum’s lips and applying enough force to keep his head down. “Whhffh!” He whined as she began to peel his socks off, his feet squirming and curling to get away.

“Hush up, will you, slave? Oh my goodness, look at these little cuties!” Jessica fawned as she pulled his socks off, exposing Calum’s bare feet. His heart sped up rapidly as he felt the cool air brushing up against his soles, embarrassment piercing his very essence as he felt Jessica’s lecherous gaze upon his delicate arches. His toes curled in shame, feet wiggling around helplessly as Jessica wrapped a strong arm around his ankles.

“Oh my goodness, they’re so small! I never thought I’d see a man with feet so little and girly! Aren’t you embarrassed to have such petite little soles? Ooh, I bet these toes would look lovely painted a nice feminine pink!” She exclaimed, casually running a finger across Calum’s pale, pillow-soft sole.

“H-Hihi!” A small giggle erupted from Calum’s muffled lips, little jolts of lightning shooting through his nerves as he felt the finger dragging against the sole of his foot. Jessica’s ears perked up, her hand lifting from his mouth to once again pin him down from the chest.

“Oh, was that a little bit of laughter I heard? Is the little slave ticklish?” She teased, adding another finger, gently dancing up and down his arches and tickling the surface with their perfectly shaped fingernails.

“H-Hhahhaha s-stohohop!” Calum began to plead, his body beginning to squirm around frantically as the unbearable, tingly little touches sent jolts of ticklish glee through his nerves. A little flurry of laughter erupted from his lips, overriding any attempts at rational speech.

“Ooh, he is! Come on, now, are you trying to attract attention? It’s almost like you want to be seen, you naughty pervert,” she cooed in a singsong voice, bringing down the full assault of all five fingers upon Calum’s poor, helpless peds. She let then rake up and down each sole, alternating back and forth before making little waterfall motions with her fingers to lightly dust them.

“N-Nohohoho! P-Plehahahashe, nohohot my fheheheet! STOHAHAHAHAHAPHH!” Calum’s voice spiked an octave, his uncontrollable laughter beginning to rise up to hysterics as little tears began to form in the corners of his eyes.  A finger slipped in-between his toes, teasing that spot for a little while before moving back to the balls of his feet and down again to the vulnerable flesh of his soles. “HAHAHAHAAHHA! N-NOHOHO, PHEHELEASSHEHE STOHOHOHOP!”

Jessica kept up the assault for a good ten minutes, letting Calum’s laughter form a pleasant little symphony. Taking in a long, satisfied sigh, Jessica slowly let her fingers begin to stop, her ginger touch gradually leaving his feet and letting Calum pull in breath after exhausted breath. She wasted no time spinning him around onto his stomach, letting her hand playfully swat his bare ass.

“Yep! I’ve decided!” She declared proudly. “There’s no way I could think of you as a guy. From now on you’re going to be my little sissy slut, alright?” she explained, punctuating it with another slap to his ass. She climbed atop his weakly struggling form, straddling him to keep him in place and reaching into her handbag. “I think I’ll make you a nice little trophy! You’ll be a lovely wall decoration, darling. It’s not as if a whore like you has much use to me other than your firm ass, you cute little clitty, and those adorable little feet of yours, anyway! I’ll get you a nice wig, too, so you can look all pretty, just like a good little sissy slut should!”

A sense of profound hopelessness began to well up in Calum’s chest as the severity of the situation began to set in. He could hear Jessica fiddling with something on top of him, but despite putting all of his strength into wiggling and struggling, she still held fast. His heart raced as a sense of helpless panic began to wash over him, stifled by the sudden addition of a cloth pressed to his nose.

The surprise of it all sent a great whiff of it right into his nostrils, the chemical coating the rag both bitter and cloyingly sweet. His head began to feel a little funny as he took it in, the world blurring just a tad. Another smell. It was intoxicating. Irresistible. No matter what he did, he couldn’t stop himself from taking another smell as the world gradually began to fade to black.

“There we go, darling. That’s a good girl. You and me are going to have a lot of fun now, aren’t we…?”