The Kissogram Part 4

 

Joe stood by the bar feeling the true weight of the kind of transformation the best part of a grand could buy. Penny and Deanna had spared no expense getting him ready for the Valentine's Ball. In spite of the fact the addictive red lipstick had fallen in their laps free of charge, they had truly bought into the philosophy of spending big to make it big. The incident with the car seemed long forgotten and they seemed completely fixated on making as much money as possible, only even bringing it up whenever Joe needed a bit of extra motivation to play along.

Firstly, they had taken him to a salon at the mall and somehow the least humiliating part of his day turned out to be standing nude but for a pair of paper briefs while he was sprayed with jets of fake tanning cream. Once it had dried, he was led to a seat where Penny and Deanna were waiting with a pair of excited beauticians. They chattered gleefully as they threaded in hair extensions and applied thick makeup that morphed his features beyond recognition – leaving only his lips bare to be painted red later on. He never heard them mention it being permanent, but regular makeup wasn't supposed to hurt as it was applied, right? When they had finished, he looked more like Malibu Barbie than regular old Joe. The outfit the girls selected didn't help that either – a glittering mini-skirt and matching tube top, chosen after plenty of other outfits had been trialled, of course... When Joe had questioned the large cup size, they brought out their coup de gras – huge breast forms that the salon girls helped blend into his new skin tone. Once in place, they were heavy and made balancing on stilettos extremely difficult. Joe was feeling the weight of his transformation, that was for sure.

The Valentine's Ball was heaving with people – mostly young men all hoping to get some quality time with the guest of honour. As with the fair, a long line formed in front of him next to the bar and guy after guy handed over cash to his sister before pulling the helpless Joe, startled and off-balance from the heavy breastplate, into a long deep kiss. The prices had doubled since the fair and the men wanted their money's worth, yet he still seemed to find the same punters coming back again and again.

“Hey there, Babe!” A tall young man stood at the front of the line. Joe's red-lined mouth dropped open. It wasn't the first punter of the night he had known but this was the captain of the school basketball team – a guy who had taken great pleasure pushing him around over the years. And now here he was, ready to make out with him. Joe felt a familiar fear creep into his stomach as the man looked him deep in the eyes. For a moment, he was sure he recognised him. And then, like the others, he handed Penny the cash and hooked an arm around him to pull him into a tight kiss – with the added bonus of a hand that crept up under his skirt and onto his pantied ass. Joe's eyes shot wide and suddenly he was looking right at the guy. He saw his pupils dilate as he tasted something he clearly enjoyed and Joe was pulled in even closer to the taller boy's body. Something hardened against his hip as a hungry tongue invaded his mouth. And then the man pulled away – still panting like a wolf. “Oh yeah!” He licked some of the transferred lipstick from his bottom lip and grinned, pulling out his wallet. “I'll give you another $200 right now if you take a trip with me to the restroom and transfer some of that lipstick to another part of my body...if you catch my drift!” Before Joe could even flinch, Penny snatched the cash and pushed him into the man's waiting arms.

The Kissogram Part 3

 

Penny and Deanna knew the lipstick was no Golden Goose. With no discernable markings or branding visible, there was no hope of getting any more of the mysterious cosmetic. When it was gone, it would be gone for good, and so, they knew they needed to cash in while they could. Every touch up and reapplication onto Joe's exhausted lips was a step closer to the final gold egg. They knew they needed to go big.

“This time with feeling!” Penny waved her arms like a movie director. “This is going viral...Instagram, tiktok...hell, I will put this on OnlyFemmes if I have to... Whatever gets the punters into Friday's Valentine's club night!” She glared at her brother who stood like a rabbit in the headlights in front of the camera tripod. Joe stared back glumly with what resembled a sullen pout. The threat of reporting his drunken collision with his sister's car still hung above his head like a guillotine. How else would the girls have made him subject himself to another makeover? This time he was a blonde with big floppy lace bunny ears. Deanna had managed to stuff him into an old Halloween costume – a black catsuit in matching lace that squeezed him all over. The material irritated his freshly shaven skins and he kept rubbing himself like a cat in heat. His lips were not red now, of course. The girls didn't dare waste any of the precious lipstick on something like this, but they were a glossy pink that plumped them out as if they had been stung by a bee. “Alright...action!” Penny called out, before adding. “Go get 'em, girl!”

“Hey, you!” Joe muttered, leaning in close to the camera lens. He couldn't believe he was doing this. After practising under the girls' instruction half the afternoon, his voice actually sounded soft and somewhat feminine. There was no audience other than the two girls and yet the performative nature of what he was doing almost made this worse than being kissed by a hundred guys. Almost... He looked up to see Penny making a waving motion with her hand indicating he should keep going. “Yes, you!” He continued his script. “Whether you're lonely, or just looking for something a bit extra, come find me at Friday night's Valentine's ball. I'll be by the bar all night where you can come give me a little kiss – for a small donation of course.” Joe blushed as he heard Deanna make a lude comment under her breath about the kinds of donation he could expect. Not wanting to start from the top, Joe cleared his throat and kept going. “Just one smooch with me and I will make your dreams come true. I will be a hookup you'll never forget and I know you'll come back for more. Come find me on Friday night, I will rock your world.” He finished by pushing out his lips as Penny has showed him.

“And cut!” His sister declared. “That will bring the boys in for sure! And the lipstick with keep them coming! With the money we made from the fair, we can give you a proper transformation that will drive them wild!” Joe visibly shrank at the idea his makeover could somehow get even more extreme. “Deanna, make sure that video is seen by everyone we know!” Penny barked out orders. “Oh, and put it on Joe's school network. Let's see how popular we can make my dear brother amongst his peers!”

The Kissogram Part 2

 

Deanna had eventually calmed down after five glasses of water and ten minutes of Penny shaking her and calling her gross for snogging her feminised brother. Her struggling had made it very clear that Deanna was more than willing to go much further with Joe were Penny not there to snap her out of it. Whatever was in the mysterious red lipstick Deanna had found in her purse was extremely powerful, and in spite of his arousal from being set upon by the hot blonde friend of his older sister, Joe was immediately alert to the fact he should lick his lips at his own peril. Meanwhile, the cogs of revenge in Penny's head began to whir to life as ideas for how to turn this to her advantage began to form. She smiled at a particularly mean one that would not only punish Joe, but also raise the money she need to repair her car.

Penny and Deanna switched gears. The goal was no longer creating the most humiliating version of Joe they could muster – it was to make him presentable. They didn't want people to point and laugh. They wanted them to see a pretty girl. They wanted people to queue with cash in hand to see the hottest version of Joe they could they could muster – their new goal was to make him kissable.

Joe watched in horror as his reflection in his sister's bedroom mirror slowly changed from a silly feminised joke to that of an anime-esque beauty. Deanna had left for an hour and returned with a huge bubblegum pink wig and a garish bejewelled choker that read 'Princess'. The girls had laughed hysterically as they took his transformation to the next level, layering on spades of makeup and dressing him in a sheer black dress with faux-pearl beads. Penny had even brought out a piercing gun she had swiped from a previous job and now he had earrings to match his choker. The final touch had once more been the lipstick but this time Penny had applied it, holding it at arm's length as if it might explode. Nonetheless, she layered it on extra-thick.

It wasn't just that Joe's stall was popular at the Valentine's fair – it may as well have been the only attraction there. Guys were queueing around the block, their wallets clutched excited as they waited for a taste of the intoxicating beauty that Penny and Deanna had dubbed 'Aphrodite'. Two bucks bought five seconds but ten got punters a whole minute of locked lips and most were not sparing their cash. Joe tried to imagine he was somewhere else as man after man grabbed him around the waist and pulled him in close. His mouth was sore and he was sure he had seen some of these guys at least three times now. Some of them were pushing their tongues deep inside his mouth as Deanna stood alongside them with a stopwatch in hand. Those were the ones that seemed to be coming back again and again, as if Joe was a bad habit they just couldn't kick. Whenever the red lipstick became smeared around his face from the kissing Penny would be on hand with a wet-wipe and a reapplication. By the evening, the stall had made almost two grand.

“Well, I did say red was for whores...” Penny smirked at her exhausted brother as she folded the cash into her purse. “I guess that makes me your pimp. But don't worry, Deanna and I have an idea to take this new career of yours to the next level!”

My Girlfriend's Roommate

 8/25

“You told your parents I’m gay?!” Billy gaped incredulously at his girlfriend across the couch. “Are you kidding me?!” He and Amanda had been together a little more than six months and he had just moved permanently into her studio apartment.

“It’s the only way they would let you live here,” Amanda protested. “They still pay the rent, you know? A gay roommate is the perfect way to stop them asking questions. Besides, they are being nice,” She nodded to the half-open envelope in Billy’s hand. “They got you a gift.”

“Did you see what they got me?” He held up a Birthday card with a voucher poking out. “It is a Drag Queen pampering and photoshoot experience day. Looks expensive! I am not sure if I should be offended on behalf of my apparent gay alter-ego, or flattered they want to spend this kind of money on me. It’s almost a shame it is going to be wasted.”

“Oh, you’re doing the shoot!” Amanda frowned. “How else am I going to keep up that you are my roommate if they don’t see pictures? Come on, Billy…” she batted her eyelashes, “I will make it worth it!”

It was three weeks later and Billy had spent the last two hours in a makeup chair being transformed by a larger-than-life character named Josephine - staring into a huge mirror framed with old fashioned lightbulbs and postcards from someone called Isabella as the face that glared back was reshaped and sculpted with countless products. When Josephine was finished, he didn’t even recognise himself from beneath the soft pink lips, frosty eye makeup and curly blonde wig.

He tried to act relaxed as Josephine squeezed him into an enormous dress that looked like a wedding cake and fastened the corset at the back so excruciatingly tight that he could no longer bend enough to see his stilettoed feet. His whole body tingled from the fresh removal of its hair and his face was heavy and stiff, yet he determinedly attempted to adopt a carefree camp demeanour as the artist who had turned him from a scruffy boy in his early twenties into something akin to a Disney princess readied her camera. Billy stuck his hands on his hips and adopted what he thought was a bratty pout.

“Oh, relax, Sweetheart!” Josephine rolled her eyes. “Your acting skills are wasted on me… I know you aren’t gay!” Billy tried to breathe out but the corset continued to clamp his chest. “The Jacksons know you aren’t gay too!”

“Then why…” He blinked as she snapped a photo.

“Why the shoot?” Josephine shot another. “They do this with all Amanda’s boyfriends. I assume it is ammunition for if you ever do anything to hurt her – that or some kind of test. It’s fine by me . Repeat customers keep me in business.” She smiled – confusion looked so sweet on him when he was trussed up like a cupcake. “Okay, so this is his how this will go… They will see the photos and remark how wonderful you look – how vivacious…alive…etc…etc. And so, you will get another voucher at Christmas, or when you get a new job, or just because they are feeling ‘generous’. Trust me, we will be seeing a lot of each other if you want to continue seeing a lot of Amanda. Speaking of which, we still have a few hours of today left. Let’s try out some more looks. I have some shoes that will match your eyes perfectly…”

Neighbourhood Watch

 

“Remind me because I think I'm going giddy in my old age, but why do you shave their heads first?” Martha looked over the paraphernalia sprawled across Molly's kitchen table. Over the decades, the two women had shared many meals here, but now it was home to a cut-throat razor in a bowl of foamy water, a mug of tea with a saucer of freshly pruned leaves and of course, a make-up bag of epic proportions.

“Oh Martha...” Molly smiled sweetly at her dear friend. “Why, it's to help the wigs stick longer of course. The glue just sets so much better to the scalp than it does to hair. Besides, they could just cut that off, couldn't they?” She turned back to her project and gave the blank-faced boy a knowing look as she continued to work her pencil around his painted lips.

“Of course, silly me...” Martha chuckled as she admired her friend's work. “Wait, I know this one. Leo, isn't it? My granddaughter says he's a right nasty piece of work. Always taking money off the neighbourhood kids. Probably shoplifts too.”

“Oh, he's money motivated alright,” Molly sighed. “All I had to do was offer him money to cut my grass and you could practically see the dollar signs in his eyes. Probably had designs on my purse when my back was turned too. I know his sort. Plenty of them have come through this kitchen, as you know. A mug of my home-grown tea certainly made him more obedient.”

“He'll have a shock when he wakes up!” Martha reached over to stroke the bead necklace wrapped around the boy's neck. Her hand moved to the faux-fur jacket and then the shimmering twenties style ballgown. “Oh Molly, don't you remember when we used to dress up like this?”

“Oh, he's awake already,” Molly sat back so Martha could get a good look at Leo's vacant gaze. His eyes stared out lifelessly from behind layers upon layers of cosmetics and his bottom lip hung open as if weighed down by the pink gloss. “Can't you see the look in his eyes? My tea doesn't put you to sleep. It just makes you compliant. Leo here is aware of everything but can do nothing. Hence the wide-eyed 'dying on the inside' look. I'm just finishing up and then I'll send him off home. By the time he regains control, half the neighbourhood will have seen him.”

“Do you think he will learn his lesson?”

“I'm not sure it matters,” Molly put the pencil back it her giant makeup bag. “After his parade home no one is going to take him seriously as a bully ever again. Besides, like I said, the glue sets really nicely to the scalp, the makeup is my permanent stuff and there's always this little trick...” The old woman pulled out a tube of glue from a fold in her apron and squeezed it liberally over the zippers on the back of dress and the fronts of the high-heeled shoes housing Leo's feet. “He'll still be in this dress by the time he gets to our age,” she joked. “Won't look half as good though...”

Double Dipping (a Liza story)

 13/25

Half way. As always, the full Aiko set is on my index page.

If at first you don't succeed, try, try again. However, if you pass with flying colours first time round, double down on that biatch! That's what Liza had always thought anyway. So when the second parcel of Aiko's candy arrived, she already knew exactly what she was going to do with it. Much to her brother's dismay, she only put aside a small pack of the heart shaped treats to manage his cravings, though what he didn't know was that Liza had begun to experiment with melting the candy down and re-setting it, cutting it with regular sugar and flavoured sherbet. She would be slipping him weaker and weaker doses of the potent sweets until she was sure he would be climbing into her dresses and slapping on her makeup for nothing more than a placebo.

The vast majority of Liza's new order was reserved for her second target – Glenn, her ex. He wasn't the worst guy in the world as far as ex-boyfriends go – more boring than anything malicious. He had wanted to take things slow – to hold hands and watch the clouds in the sky when what Liza really wanted was for him to try to get in her panties. Well, now he was in her panties...and her skirt...and her tube top...and her stockings, platform shoes and about ten pounds of cosmetics.

She had got him with some trap chewing gum and then once he was nicely trussed up in some breast forms she had found online, she switched to some of her homemade candyfloss, which he had begun to gobble with such desperation that he didn't notice the surprise on Liza's face on spotting the tattoos etched on the skin of her supposed goody-two-shoes ex beau. If you had let me see these when I wanted to, you wouldn't be in this pretty little mess, she thought to herself.

Two hours later, Glenn was shuffling home the best he could on the massive platform shoes his feet were crammed into. He felt weirdly grateful for the fluffy ball of candyfloss in his fist as he could use it to hide behind as people passed. If only he could stop eating it... He knew he shouldn't, he knew it was what was driving the craving that has been leveraged against him to get him into this ridiculous outfit but he just couldn't stop himself. It was the only thing suppressing the itch than ran from beneath the wig Liza had glued to his scalp, down his spine under the bra-strap holding his breast forms in and down the backs of this stockinged legs all the way to his painted toe nails. And for what? Acting like a gentleman? He certainly didn't look like a gentleman. He didn't exactly look like a 'lady' either but that was neither here nor there...

Liza watched from a distance snapping photographs for her new blog. Her brother's photoshoot had attracted some online attention but she needed more. She needed enough of a buzz that Aiko couldn't help but notice her. The next order from Akio's webstore would need to be much bigger if see was going to get the followers she wanted. Speaking of followers...Glenn was starting to attract the gazes of some of the neighborhood boys. Good, she thought, if they like what they see, they should have no objection to joining him.

Fangirl (a Liza story)

 4/25

I've been really blown away by the warm welcome I've received since I started capping. I wasn't sure if people would still be interested but its been amazing how many views and comments I've got. It is infectious and motivating and while I still have 5 or 6 caps to finish writing for this season, I've already started pencilling in ideas for season 5. Thank you so much.

Today we have the resumption of Aiko's story, courtesy of a new friend. As always, all my Aiko stories are listed in order on my story index tab.

Liza refreshed the webpage despairingly but once the pixels had finally reloaded, the same blog post remained at the top of the screen. It was futile. Aiko hadn't posted anything new in nearly four years, it was foolish to think she may have posted in the last four seconds. Oh, how she missed the stories and pictures of candy addicted boys squirming in humiliation under pink petticoats and stockings, but there had been nothing in so long – not even a goodbye. Even Aiko's usually inseparable best-friend, Nishi, seemed to have transformed her online presence into some kind of seedy webcam girl. It made her so sad.

She scrolled down the page and noticed a link she had never seen before. Allowing her cursor to hover above the word, she pondered the possibilities. If Aiko's blog was inactive then surely this was inactive too, right? Probably, but...what if it wasn't? Then that would mean...she had to know. Her heart pounding, Liza double-clicked on Aiko's webstore...

When the package eventually arrived with its Japan postmark, Liza felt overwhelmed with surprise and relief. Her older brother Shaun was the obvious test candidate for the goodies inside and even though she was not yet blessed with the tremendous assortment of kawaii outfits and accessories that Aiko had seemed to have at endless disposal, she more than enjoyed watching him strut and pout in selections from her own wardrobe. Getting him hooked on the candies had been easy. She had just left the heart shaped sweets in a bowl on her desk. Shaun was always sneaking around and going in her room and before long he had come knocking on her door glistening with sweaty regret.

“Please, please let me have another one already!” Shaun was trembling and fidgeting with the ruffles of his dress. Despite being two years older, in the last hour the balance of their relationship and shifted forever and Liza knew that from that day forward he would always struggle to meet her eye.

“Stop messing!” Liza looked out from behind her camera, “or we will need to change your outfit again. Believe it or not, I don't want your makeup over all my clothes.” Shaun looked stung and rubbed his stockinged knees together in an attempt to suppress his raging hunger for more candy and the wrathful tongue of his little sister. Liza felt a pang of sympathy. “Just one more pose, okay?” Almost automatically, Shaun bent his knees and pushed his butt out while pursing his glossy lips over his shoulder. “Perfect!” She snapped off a picture and reached into her pocket for the candy hearts, finding it empty. “Oh dear, they're all gone. I am afraid you will have to wait until my restock arrives. That is, if I deem that you have been well-enough behaved. After all, I have big plans for these candies.” Shaun nodded and tottered demurely out the bedroom as Liza flicked through the plunders of their photoshoot on her camera. “Big plans, indeed,” she smiled. They wouldn't be enough to catch Aiko's attention, but they were a start. If she was going to bring back Aiko, there was going to be many more prissy projects left in her wake. Maybe she should have ordered more candy...

Rescue Package

 3/25

I have been toying with the idea of a sadistic lawyer as a recurring character since forever. Maybe this will be the beginning...

Saul couldn't be blamed for feeling a little outnumbered as he faced off against his ex-wife across the boardroom table. An army of lawyers flanked her on both sides while he sat alone, barely able to afford the suit he was wearing let alone legal council. He recognised the woman to his left as Alice, the scheming bitch he had watched grind her teeth during divorce proceedings as Saul and his lawyer had successfully managed to use his wife's desperation for sole custody of their children to ensure he kept everything else; the car, the house, the multi-million dollar company they had built together from the ground up... Well, Alice sure wasn't grinding her teeth today.

“Please,” he begged his wife while trying to push Alice's wide grin from his peripheral vision, “I need this. Without a bail out, creditors are going to take everything from me. They're going to take my house. Do you understand that? I'm going to be out on the street.”

“Like you took everything from my client, you mean?” Alice hissed. “LoanRanger was always her company. You were just dead weight. Just look what has happened since – you have run yourself out of business and my client has single-handedly come back even stronger with a bigger better company.”

“Please,” Saul whimpered, sweat pouring from his brow. “I need this. I will do anything.”

Alice's smile broadened. “Look, Mr. Clegg, my client isn't going to buy back in so you can destroy things all over again. If she comes back, she will be in charge. She will well and truly be wearing the trousers.” His ex-wife gave her a questioning look and Alice whispered in her ear, eliciting a sharp giggle. “There will be conditions,” Alice removed a pen from her blouse.

“Anything!” Relief flooded through Saul's body...

It was next to that same conference table a month later, Saul felt the opposite of relief as he watched Alice lead a team of Japanese investors into the boardroom. Each one stopped and looked at him admiringly. Saul shuddered as their eyes danced across his freshly surgically enhanced breasts stuffed painfully into a tight leather corset. A short pudgy man stopped and stroked his hair delicately as if it were a harp, frowning on realising in was synthetic and implanted directly into the scandalously dressed secretary's scalp. Saul blushed with humiliation and averted his gaze causing him to miss the source of a stinging slap to his pantied ass that sent ripples of pain across where his manhood was tucked securely between his cheeks. Still staring at his feet, wishing the floor to swallow him, Saul heard a cough. He looked up and realised a man was waiting for him to pull out a chair.

“Allow me!” Alice entered the room and plunged her thumb on a keyfob. Saul yelped as a rumble jolted through his ass from the buttplug lodged there. He squealed and minced to the corner as the men took their seats. “How about I put this here?” Alice placed they keyfob in the center of the table and winked at Saul. “If anyone needs anything, just buzz!”

Dolled Up Part 1

She's Hardcore! Part 1

Whatever Happened to Ben? (Flashback Friday)

Ben is from Maybe he's Born with it...'

Imagine That!

This. Is. Spa-Tan!!

Postcards From Nishi (an Aiko Story)

Sissy Versus Sissy Part 3

Whatever Happened to Jason? (Flashback Friday)

To celebrate my one year anniversary of posting caps, a flashback of my very first and very worst series

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Tricks of the Trade Part 2

Tricks of the Trade Part 1

Copycat

When in Rome...

Finally... Thankyou for being patient. Hopefully, I will be back to daily caption from now on.

This caption is part of a larger set of trades I will be doing with one of my favorite captioners hahaprincess