Being Her Valentine Part 3

 

“You really thought a couple of sisters as close as us wouldn't compare Valentine's cards?” Sara cackled gleefully. “You really are a silly sissy...a silly piggy sissy!!” She watched Michael reach up behind his head to where the ballgag was fastened – it was clear he wanted to remove it so he could respond. “What do you think you're doing?” He paused in place. “I wasn't asking you a question. I was stating a fact. You are a pathetic two-timing piggy sissy waste of DNA!” She snorted another fit of giggles as Michael averted his gaze from her. “Right, Steph?”

“Right!” Steph agreed, standing alongside her sister with her arms crossed. She wasn't taking the same level of pleasure from Michael's predicament as Sara but it stung in a different way. He saw the hurt in her eyes, and spite, and a cold need for vengeance. She had been the one he tried to cheat on after all. Sara's taunting was humiliating, but Steph's hollow intensity scared him. What had he been thinking?!

“Hey Mom,” Sara called to Sophia, who had been watching on from the other side of the room since they had dragged Michael back into the house. “What do you think we should do with this bitch? Say, I'm surprised the stupid sissy didn't send you a card too. He's clearly always had the hots for you too. All that pathetic grovelling whenever Steph brought him over for Sunday dinner. Yes, Mrs.. No, Mrs... Three bags full, Mrs...”

“Is it true?!” Steph had a fire in her voice and Michael looked up at her timidly from his position on his knees. The ballgag they had stuffed in his mouth was sucking in his cheeks awkwardly. There was no dignity in the world that could possibly be salvaged from this situation. “All this time... playing house with me... running around after my little sister... and you still thought the sun shone out of my Mom's ass? Well, let's see shall we?! Mom, get over here!”

“Yeah, Mom...” Sara laughed sharing a look with her sister and catching on with her plan. “Come here! Come help us show this piggy sissy what really shines out of your ass!” Sophia stared back tentatively then glanced at the kneeling Michael, who somehow managed to look confused in spite of the ballgag and layers of makeup.

“You girls...” Sophia smiled at her daughters and shook her head. “If I can't say 'no' to you, what chance did this cretin stand? Come on then... Let's do this!” She walked across the room and Michael looked around nervously as Steph and Sara positioned themselves either side of him. Sophia stopped in front of him, turned around and hiked her skirt up so he was face-to-ass with her g-string parted cheeks. Before he could react, the three women acted with impressive coordination. Sophia pulled down her panties and bent over and Steph and Sara each grabbed the back of his head and firmly pressed it forward. Michael's world went black. “Hold him tight, girls!” Sophia hollered. “With that gag, our little piggy will have no choice but to breathe me in!”

Being Her Valentine Part 2

 

“Come on, Steph. Please let me in!” Michael thumped his fists against the glass. “I know I said I would do whatever you wanted, but there is no reason to torture me. I just want to fix our relationship!” He let his hands fall to his sides as his girlfriend continued to stare at him impassively from the other side of the sliding door. He wasn't even sure she could hear him. However, if he continued to shout, he sure would attract the attention of their neighbours. Michael looked around at the multiple houses with direct lines of sight into their yard where he was pleading. What would he look like to them? He surveyed himself in his reflection in the glass door. He really did look like a piggy sissy in the heavy makeup and blonde wig – completely naked except for the hot pink bra and panties. “Come on, Steph!” He begged. “I'm...I'm...” His mind raced. “I'm so cold!” But Steph simply turned around and left her position at the window.

“If you're so cold, put this on!” The door was open just a second but it was long enough for Steph to yell her command and hurl the pink satin dress at him. Michael just stood there dumbly, unfolding it. It had an old-fashioned cut, somewhere between a maid's dress and a babydoll with big poofy sleeves and sown in stockings. He could tell it would be tight but he really was cold and he didn't want to stand around in the bright pink underwear waiting for one of his neighbours to glance out the window. Reluctantly, he pulled the dress over his head and the stockings up his legs. Raising his arms to the watching Steph in a sarcastic pose, he turned and sat down on the decking. Maybe if he made it seem like this didn't bother him, she would end it sooner. He raised his eyebrows and folded his hands in his lap.

“Michael! What in the hell are you doing out here?!” His heart leapt in his chest at the sight of the older woman whose eyes looked like they might pop out of her skull. “And what on earth are you wearing?!” Sophia was Steph's Mom and despite being a good 25 years older, still shared the same elegant good looks. As she blinked more times than any human Michael had ever seen, he felt a wave of fresh shame wash over him at being discovered like this. “You look like a...like a...total sissy!”

“Hey, Mom! I have your car keys!” Michael heard a fresh voice calling from the other side of the fence. The gate through which Sophia had entered the yard swung open once more and the owner of the voice entered. “Hey, Mom – any idea why Steph told us to come round the back...” The new woman stopped mid sentence and her jaw dropped open. Where Sophia was attractive, her youngest daughter, Sara, was stunningly beautiful. She possessed Steph's sharp angular features but retained a youthful mischief her older sister had lost a few years back. It had been why Michael had sent her the Valentine's card. Sara's mouth closed into an evil grin and suddenly he knew exactly what was happening. “I see my sister didn't waste any time punishing you for trying to two-time us...”

Being Her Valentine Part 1

“That's it, Michael. Paint it on nice and thick.” Steph instructed. “Come on. Just like I showed you. Just like you promised!” Michael squinted at the tiny brush in his hand, concentrating on the tiny grains of powder on its end before allowing his vision to unfocus to the round makeup mirror with the illuminated edge. He almost didn't recognise the face that gazed back, caked with different shades of colour and framed by the bangs of the blonde wig. “What are you waiting for? Slather it on you piggy sissy!”

“Piggy?” Michael lowered the brush and turned his head towards his girlfriend. That was the second time she had called him that now. The first time he had assumed she was being playful, just getting into character – he had even liked it. It had been authoritative...demanding. But this time there was an edge to it.

“That's right!” Steph smirked coldly. “In your Valentine's Day card to me you said you would do anything to be the man I wanted. You said you would change. Well, I am taking you up on that offer! I am showing you how to be the man I want!” She appeared to grow impatient with Michael's continued hesitance, and took the brush from his hand and proceeded to paint his eyelids with rock-solid precision. “And what I want is a Piggy Sissy!”

“Ah...” Michael's glossy red lower lip dropped open. His pride, at least what was left of it didn't appreciate Steph talking to him like that, but other parts of his anatomy did. She seemed to notice the stirring within the satin of his panties and snorted cruelly. Michael lowered his head and sat in shameful silence. He truly wanted to reignite the passion in their relationship, and he had meant every word of his pledge in the Valentine's card to Steph. By saying he would do whatever she wanted from him, his intention was to put the ball in her court. He just never thought this would be the game she would ask him to play. She had read the card in silence, her lips pursed, before folding it carefully and leaving the room. When she had returned, she was carrying her makeup box in one hand and a bright pink bra in the other. Nevertheless, he had swallowed hard and told himself – 'If this is what it takes to save our relationship so be it.'

“Almost done, Piggy!” Steph declared after several more minutes of painting his face with the brush. “There...” She smiled warmly for the first time since reading the card. “Now for phase two. Come...” She put the brush down and walked from the room. Michael's heart lept in his chest. Was she taking him to the bedroom? Was this what she wanted from him? To satisfy some kink she had been hiding? He followed her through the house with a mix of confusion and disappointment as she passed the staircase leading to their bedroom. “Look out there!” She opened the sliding door at the back of the house and stared off into the yard. Michael followed her gaze, moving closer to get a better look...until suddenly, Steph shifted her weight and shoved him with both hands over the threshold. He turned in horror just in time to see her lock the door with a loud click.

 

Sssshhh

 25/25

'Ooooohhh...he's perfect!' squealed Alice, looking down at their project. 'Wait! What am I even saying? He? She! She's fantastic! She's everything we were hoping for! She'll make a wonderful maid for our party.'

Georgina beamed with pride from her sorority sister's praise. 'Nice little loophole, don't you think? Now, no girls from outside the sisterhood need to be at our party and no-one needs to know we let any but the most alpha boys in campus come within five feet of us. Besides, I doubt any of those mousy little things from Beta-Beta-Beta could fill out a dress as well as this one! I even packaged her up in case she had the idea of making a run for it!'

Sean cowered beneath the duo of manic girls. The wig had only been on his head thirty seconds and it was already itching. He just prayed they were joking about the glue. Combined with the figure hugging frilly dress and the fishnet stockings, he felt like he was being squeezed all over. Still, none of it compared to their eyes on him, their satisfied mocking stares. And that was without the ropes Georgina had tied around his ankles and wrists – she had even bound his shoulders. Who hid she think he was? Houdini?!

Alice snapped a picture with her smart phone. 'Think I'm gonna use that to copy her makeup,' she grinned. 'It's a bit slutty, but I can make slutty work.' She winked at Sean in a way that made something stir inside his satin panties and his glossy pink bottom lip dropped open. 'Now, my dear maid,' she beckoned, 'show us how you're going to greet our guests.'

'Please,' Sean grunted in disbelief. What the hell was she expecting while he was tied up like this?! 'Please let me go.'

'Not ladylike at all,' Alice shook her head with disappointment. 'That won't fool even the dumbest of your fratboy pals.'

'It was what I suspected,' Georgina shrugged,' that's why I got that.' She pointed at Sean's neck and he nervously looped a finger around the leather choker, pulling the heart-shaped ring away from his Adam's apple. Georgina didn't hesitate. She stepped forward and pulled it forcefully over his chin. The hoop sunk between his plump lips and he instinctively fastened his teeth around it to stop it going deeper, not realising until it was too late that was exactly where it was intended to go.

'Urrggghh,' he moaned.

'Perfect,' nodded Alice once more, 'now you sound as tarty as you look. 'Say,' she eyed Sean's now open mouth, 'you're looking a little exposed there...let's make that forced little dentist's smile a surprise for them!' She reached for a roll of tape and slapped a piece over his mouth. "It might take those fratboys a little time to find that sweet O of yours, but don't worry, they will want to explore your pretty mouth before long. I hope they play nice with you."

'Oh, don't worry,' Georgina's eyes twinkled, 'I'm sure you'll get a taste for them in no time...'

Spoils of War Part 3

 

“Hush, my dear brother... It's over now!” Alyssa smiled warmly, circling her bed. “The battle is won. The war is over. All that remains is the victory parade.” Robert was kneeling in the centre of her duvet in something of a PTSD haze. The quiet of the sorority house bedroom was in stark contrast to the stadium packed with tens of thousands of screaming fans where the Epsilon-Zeta girls of Beaverhole had dragged him along in full uniform as an honorary member of their cheer squad. He had been forced into clumsy high kicks between plays and to sit with the rest of the cheerleaders on the bench behind the bemused players. He had even appeared on the big screen at one point. His parents had seen him, he realised with a sinking dread,

And yet, the beast had been conquered, the game had been won, and the rival sorority had reluctantly handed their hostage back to his sister's clan. So, why was he still trussed up in velvet and nylon and painted like a sissy?! Robert turned his head to one side to gaze out the window and felt the long locks of his wig brush across his heavily made-up cheek. After all that had passed he still felt miles from freedom.

After the game had ended in victory, Alyssa and her friends had carried Robert on their shoulders back to the sorority house. He was soon naked once more as they stripped him of the Beaverhole uniform to throw on a small fire. His sister had to bat away a gleeful college girl who was enjoying Robert's perfectly smooth skin a little too much, and then she dropped the bomb that his ordeal was far from over as the girls were planning to parade their trophy at the college's victory party. All the girls mucked in to transform him once more, and by now Robert found that most of the resistance had gone out of him. He obeyed meekly as they produced a velvety party dress with long nylon sleeves and bejewelled choker, and demanded he dress himself. It was still slightly better than being nude in front of two dozen girls, and definitely better than being dressed as a cheerleader in front of the entire town. And still, his mind raced at the thought of what the sorority had planned for him, their new mascot, at their victory parade.

“Those Beaverhole girls are so dumb!” Alyssa smirked as she continued to admire her work, touching up Robert's make-up and rearranging bits of hair. “You know we told them this could be an annual thing?! Like we compete to win you as a trophy every Valentine's game. That's how we got them to agree to hand you over. I hate to say it, but you'll be long gone before the rematch next year.”

“What?!” Robert's face went pale. Suddenly the parade seemed like the least of his problems. “No, Alyssa, I won't be...” He stammered. “I didn't tell you... We were supposed to tell you this weekend... I got offered a place at Seabrook. I will be starting here in the fall. I'm going to be here for the next four years...” His heart pounded as he realised just how far from freedom he really was...

Spoils of War Part 2

 I was tempted to leave this as a bit of an Easter egg, but Beaverhole and the Epsilon-Zeta sorority are from the caption universe of my own friend B-Rex - someone who has influenced my captioning style more than anyone else over the last 12 years. B-Rex isn't currently posting but I highly recommend you go check out Degraded Damsels and see how much I have managed to rip off as my own ideas 

About a dozen girls crowded around Robert as he lay prone on the floor – their excitement evident in their rapid giggled whispers to one another. 'It's a guy!' 'It's a sissy!' 'It's some kind of pet!' 'Probably a boyfriend who got caught cheating!' 'It's pathetic!' 'It's probably their mascot!'

“It's a trophy!” The crowd parted to allow a stubby butch girl with an air of leadership into the centre right in front of Robert. “And it's ours! Those Seabrook bitches think they are so much better than us! They think their boys are going to crush our team in the big Valentines Homecoming game tomorrow! Well, were going to show them! Were going to show them that Beaverhole is not a town to be messed with, and we sure as hell are going to show them that Epsilon-Zeta is a sorority to be feared. And we are going to start by making an example of their little mascot here!”

Robert very quickly came to understand that the short masculine girl was named Lynn and was the leader of the Epsilon-Zeta sorority, a prominent house from his sister's college's rival school and opponents in tomorrow's Homecoming game. He could also tell that the other girls feared her like a drill sergeant as they moved obediently to her barked orders. For the second time in three hours, Robert was stripped naked in front of a room full of girls, and to his dismay, his member was still feeling the effects of his forced ice-cold shower – something that amused the encroaching sorority.

“He's completely smooth!” Chuckled one of the girls running her hand up his leg – an experience Robert might have enjoyed under other circumstances. Another girl lifted him under his armpits as hands slapped as his bare ass and one girl even pinched at his testicles. He was turned to face some approaching girls and when he saw what they were carrying, he began to struggle.

They overpowered him easily, of course, and within no time they had stuffed him into the Beaverhole cheer uniform complete with matching spandex spanks and sheer pantyhose. One of the girls had sat on his chest while another glammed up his makeup and replaced his wig with one with long wavy highlights. They were turning him into one of them, Robert realised in horror, and when they finally released their grip on him, he scrambled backwards on all fours until his back was pressed against the wall.

“Here! You'll need these!” Lynn threw a pair of pompoms at his feet. “Cheerleading isn't my thing, but the girls here will show you our routine!” Over the next hour, Robert was forced through an exhausting regimen of high-kicks, clumsy cartwheels and waved pompoms. His mistakes were mercilessly corrected by the team of girls and a sinking dread formed in his stomach at the sight of Lynn filming every moment of it. Just when he thought his lungs would explode, they left him a sweaty humiliated mess on the floor. Five minutes later, Lynn reappeared holding her phone. “It's official! Those bitches at Seabrook saw our video and agreed terms. Whichever college wins the Homecoming game tomorrow gets to keep their little mascot here as their own!”

Spoils of War Part 1

 

Robert lay on the leather sofa in the communal area of the sorority house feeling utterly pathetic. He should be loving this. All around him, college girls in various states of undress weaved excitedly. Uncupped boobs poked through vest tops with panties peeking from below. Towels were wrapped around heads of girls still wet from the shower. Skin was on show everywhere he looked. This was why he came. He should be in heaven. And yet...

The last few hours felt like a fever dream. It was the weekend of the big homecoming game and Robert's sister Alyssa was one of the star cheerleaders. Their parents had planned to drive up with Robert on game day to watch the big contest and their daughter perform, but Robert had convinced them to let him come a day early to hang out. In reality, Alyssa had told him about the epic slumber parties she and the rest of the sorority girls had the night before a bit game and he wanted to try to catch a glimpse of some sexy sorority shenanigans. Things had gone well at first. He had popped a few beers with the help of a fake ID and then crept through the darkness of the evening to one of the sorority house's ground floor windows. The party had been in full flow. Girls were dancing in their underwear and sipping colourful drinks. He had even seen a flash of side boob on a beautiful red-headed girl. That's where things started to go wrong. A group of girls returning with a stack of pizzas spotted him and before Robert could run, he was kicked swiftly in the groin.

“How is our guest of honour enjoying herself?” Alyssa was standing at the end of the sofa with a mocking grin on her face. Robert instinctively hugged the stuffed bear the girls had given him, cursing how pitiful he must have looked. She can see right up the dress I'm wearing, he realised, and shifted his knees up to his belly defensively. This only succeeded in showing her his pantied butt. The girls had done a number on him alright... Before he had even recovered from the pain and indignity of being booted in the crotch, five girls had removed him of his clothing and he was fully naked before he had even been dragged into the house. It was like they had done this before, so prepared and regimented were they for his arrival. Two had held him down, while another three had smothered his body with what he later found out to be hair removal cream. He had watched the last of his body hair trickle down the drain as a laughing girl had showered him with ice-cold water that shrank his cock to the size of his little toe. He had been been putty in their hands after that – a toy to be be powdered and painted and dressed as they wished. Not a boy – a doll... And now a distraction, a piece of furniture that they occasionally stopped to giggle at as they continued with their party. He should have been in heaven...but he was in a kind of sissy hell – one being conducted by his sister, Alyssa.

Suddenly, there was a crash of breaking glass, and a few seconds later everything went black. High-pitched squealing surrounded him as frightened girls ran around in a frenzy. Eventually, they trailed off as the sorority sisters sought refuge in their bedrooms, leaving Robert alone in the darkness of the communal area. “Hey!” He heard a female voice very close to him and a bright light was shone directly in his eyes. “I've got one. Quick! Let's grab her and get out of here!” Robert felt three sets of hands grab the smooth skin of his arms and legs and begin to drag him away.