A Sissy Cheerleader

“Don’t you think you’re taking this a little too seriously, Ben?”

“It’s just for a laugh, but you know how competitive I get. Come on, Alice, will you help me or not?”

“Fine. I’ll feminise you so you’re unrecognisable, but you’re crazy, do you know that?”

“I know!” The siblings laughed. Ben couldn’t have been more excited.

When his amateur football team announced they were attending their annual charity Halloween party dressed as cheerleaders, Ben saw an opportunity he never imagined getting.

The 22-year-old was 5ft 8” and slim, with very short blonde hair and blue eyes. He played on the wing for the team and was a pretty boy who attracted his fair share of girls, but Ben was also secretly a sissy — not a very convincing one.

He was awful at styling wigs and dreadful at doing makeup. Living at home with his mum and older sister, he never had the time to practise seriously. So he’d slap on something quick to remove and spend the rest of his free sissy time in lingerie, dresses, and heels, celebrating his limited freedom.

Once he got his big sister to help him, all he had to do next was order his costume. A week later — after creating the smoothest and most moisturised body possible — Ben was ready to free his inner gurl. He couldn’t wait to see the outcome once his sister had finished with him.

“Are you ready for me, Alice?” Ben knocked on her bedroom door.

“Sure, come in, Ben!”

Alice had her brother sit in front of her vanity unit to begin feminising his face. She plucked his eyebrows and nose hair before applying foundation evenly. After concealing all his blemishes, she added blush for colour and then defined his new eyebrows.

Ben sat perfectly still, excited, chatting to his sister about makeup. Alice thought he was simply making conversation, when in reality she was giving her brother a tutorial.

“Now, remain still and don’t blink. I’m going to put these fake lashes on.”

Ben felt his average dicklette twitch. Then it hardened as his sister continued to enhance his eyes with eyeshadow and eyeliner. He almost came in his pants when she finished with mascara and lipstick.

“There you go… you look like a real girl.” Alice was mighty proud of her ability to transform her brother into a convincing girl.

“Thanks, Alice. You did great. I’ll come back when I’m changed so you can do my hair and nails,” he laughed, pretending it was all a joke for Halloween and not the perfect excuse to dress up as a sissy slut.

Ben returned to his bedroom, closed the door, and took off his clothes. He stretched a C-cup breast plate over his chest. The look and feel of a pair of boobs, even if they were fake, felt unbelievably sexy.

He pulled the white knee-length socks up his smooth legs and slipped into a pair of pristine white cheer shoes. Man, this is exciting, Ben grinned to himself as he pulled on the cute pink-and-white cheerleader costume dress.

It hemmed at mid-thigh, exposing a couple of inches of flesh above his knees. He stood in front of his wardrobe mirror and pulled the long blonde wig over his head. Staring at his reflection, Ben thought he looked amazing.

“Hello, Bethan,” he whispered, adjusting the cheer dress around his firm rubber breasts. The nipples protruded hard and very visible, as if they were real. Turning to the side, the amateur footballer’s firm buttocks looked inviting to any would-be groper.

Ben flicked the synthetic blonde strands behind his shoulders and looked at the word ‘Squad’ written across the small mounds on his chest. He had wanted the cheer costume that said ‘Sissy’, but that would have been too obvious. He then went to pay his sister another visit. It was time for Bethan to have her hair done.

“Wow!” Alice gasped. “What did you do with my brother?” The siblings laughed as Ben sat down in front of the vanity unit again, excited to have his hair styled like a cheerleader by a real girl who knew how.

Alice suggested a high ponytail — a classic and popular choice for cheerleaders. She prepared the wig, gathered and secured the hair at the crown to create a sleek, lifted ponytail, then added a big pink bow and glued a set of sexy French nails onto her brother’s fingertips.

“I can’t believe what a great job you’ve done, Alice.” Ben was mesmerised by the finished look.

“You better be careful tonight. You might get mistaken for a real girl,” Alice laughed.

There was one last thing Ben needed to do. It would be the biggest rush of all. He could explain away the great lengths he went to in order to pass as a real cheerleader — he was known among his teammates for never doing things by half — but if they discovered the final piece of the jigsaw, the game would be up.

Ben returned to his bedroom for the final time, locked his clit in a pink chastity cage, and hid the key in his wallet inside the small girly bag he hung over his shoulder. Just in case of an emergency.

Arriving at the football club, excitedly nervous, Ben prepared himself for the inevitable onslaught from his friends. He had to endure over ten minutes of jovial abuse for taking the fancy-dress party so seriously. He lied and said it was his sister’s idea.

The girlfriends of his teammates laughed too, giving Ben (and Alice, in her absence) very high praise for his makeover. Everybody got to feel his prominent rubber boobs and nipples.

The secret sissy lapped it up, constantly pulling down on the hem of the cheer costume, fearful somebody might try to lift it for a jokey peek.

Nobody did, much to Ben’s relief, and very quickly the charity party got going. All the football team were dressed as cheerleaders, while everyone else came as vampires, witches, and the like, raising money for a good cause on Halloween.

A couple of hours later, everybody was merry, some very drunk. Ben was tipsy and having a great time being in public as his alter ego. His favourite part of the night was sneaking off to the disabled toilets to freshen up his makeup and feel his breasts.

When Ben returned to the bar, a much older man named Charlie approached him and bought them drinks. Charlie was dressed as Count Dracula. He sat on the board of the amateur league and was one of the charity event organisers. In his early fifties, tall and balding with a flabby gut, he took Ben to one side and complimented his costume.

“Uh… thanks,” Ben said, surprised. The two didn’t really know each other.

“What’s your name, sweetie?” Charlie asked quietly, revealing a scary set of fangs with a lecherous grin across his chubby face.

“I’m Ben,” the young footballer replied, beginning to quiver. Charlie had clearly had one too many.

The older man chuckled before leaning in and whispering, “I know why you really went to so much effort, sweetie.” Ben felt a hand slide under the back of his cheer dress and cup his chastity.

“What’s your other name?” Charlie removed his hand and took a swig from his pint.

Ben looked up at the man who had just molested him, horrified. He blushed so hard underneath the makeup. The sexual assault left him open-mouthed and speechless. Then Charlie took their drinks and put them down on a nearby table.

Paralysed by fear, Ben did nothing as the sinister Dracula led the pretty cheerleader out of the function room.

“Where are you taking me?” Ben panicked.

Charlie was betting everything that his instincts were right about the best-looking cheerleader on the football team.

“Relax,” he smirked, escorting Ben towards the changing rooms.

“No, seriously,” Ben’s voice cracked. “Where are you taking me?”

Charlie stopped them outside the men’s changing room, then chuckled at the women’s changing room opposite.

“I think in there would be more appropriate for you. Relax, I’m not going to hurt you.” Charlie pulled Ben into the female changing room and locked the door.

The only thing preventing Ben from becoming aggressive and fighting back was the fact that Charlie had seen right through him. The older man knew what was hidden between his young, toned legs, just a few inches above the hemline inside the cheer dress.

“What do you want?” Ben muttered as Charlie pressed the cute cheerleader back against the door.

“I know a real sissy when I see one. Admit it and I won’t tell a soul.” Charlie breathed, driven by lust and desire. It had been a while since he had felt his cock inside a tight sissy.

“This is insane!” Ben protested, but he couldn’t ignore his racing heart and his own heightened arousal.

“Relax, sweetie. I’m not going to force you, but I know a curious sissy when I see one. Admit it. Your secret is safe with me.”

“Wwww… what?” Ben could feel Charlie’s hot, aroused breath on his face.

“What’s your name?” Dracula sighed, inhaling the scent of Alice’s stolen sweet perfume. “Mmm, you’re so sexy.”

“B… B… Bethan,” Ben finally submitted. Saying his inner gurl’s name brought a sudden release of energy. Freedom.

“Mmm, such a cute name for such a cute little sissy.” Charlie unzipped his black trousers and fished out his hairy, fat cock.

“Have you experienced cock yet, Bethan?”

“No,” Ben muttered, knowing he was about to.

“Mmm, a virgin sissy. But you’ve always wanted to know how it feels to get fucked like a girl, haven’t you, Bethan?”

As Charlie put his hands on Ben’s shoulders and pressed down firmly, the young footballer truly became Bethan. A transition took place as he was pushed to his knees and confronted with his ultimate fantasy.

Sucking and fucking his dildo at home had prepared him for this moment. Unexpected as it was, Ben opened his mouth and surrendered to both his inner gurl and the much older man.

“Ohhhhhhhhhh…” Charlie groaned, feeding his cock into Bethan’s mouth. She closed her red lips around the thick shaft, closed her eyes, and sucked while he began to thrust in and out. “Oh yes.”

Charlie tilted his head back and groaned up at the changing room ceiling. His eyes closed as he held the back of Bethan’s head and began to slowly fuck her face, forcing more and more of his fat cock down her throat.

Bethan helplessly did what she could. She grew into her first blowjob the longer she sucked and gagged on a real man’s cock. It brought her a sense of belonging, and she placed her hands on Charlie’s trouser-covered buttocks, digging her false nails into the fabric.

Charlie knew she was his sissy now. He opened his eyes and looked down at the pretty blonde hair with its big pink bow bobbing along his cock. He continued thrusting his hips until he almost blew a big, salty load down her throat.

“Stand up, Bethan. I want you against the wall,” Charlie instructed.

Bethan got to her feet and walked over to the wall. She placed her hands out, spread her legs, and pushed her arse back, trembling with fear and excitement — scared it would hurt, excited to finally feel what a girl feels.

Charlie looked at the sissy cheerleader, who appeared ever so feminine. This will feel like I’m fucking a real girl up the arse, he thought, staring greedily at the firm backside on offer.

“Oh, that’s a lovely, cute butt you have on you, Bethan,” he said, raising the cheer dress and stroking the smoothest pair of buttocks he’d ever seen. “Very nice indeed,” he added, stepping back and looking at the chastity cage dangling between her legs.

“Do you have a condom?” the cheer sissy quivered.

“Don’t worry, Bethan. I’ll pull out in time. I promise I won’t knock you up,” Charlie gave a dirty chuckle.

“Seriously,” she fretted. “I’ve never done this with a guy before.”

“Calm yourself. I’m married and clean as a whistle. Now shut your whining while I get you ready for your first cock.”

Charlie slobbered all over his fingers and began greasing Bethan’s very tight, puckered virgin hole. He added plenty of saliva before managing to get his fat index finger inside.

Bethan groaned and began to push back, swaying her hips to the instant pleasure. She’d fingered herself on many occasions and regularly slipped a small five-inch dildo up there, but this felt different.

“Mmm, what a tight girl you are, Bethan. Daddy is going to give you something you’ll never forget, sweetie.”

“Oh fuck!” she gasped as Charlie pulled his finger out and began pressing the engorged head of his cock into her.

“Mmm. Hold still. I like to take my time getting it in.”

Bethan pressed the palms of her hands against the wall. Her fingers tensed, showing off her sexy French nails, while Charlie slowly started pushing his fat cock in and out.

“Oh fuck! It’s too big! It’s too big!” Bethan panted.

“Relax, sweetie. Daddy’s almost in.”

Charlie grabbed Bethan’s hips and pushed into her a little more assertively, penetrating deeper. She gasped and slapped the wall with her left hand, moaning in pain and pleasure.

“You like that?” Charlie sighed, squeezing every fat inch inside her virgin hole.

Bethan didn’t reply — she couldn’t. Instead, she grimaced in pain while her clit released tiny droplets of sissy juice. She spread her legs a little further apart.

“Mmm, that’s my girl,” Charlie groaned, pulling his cock back before sliding it forwards again.

As Bethan was slowly fucked and gently broken in, she couldn’t believe how easily she had been led astray. How easily she had been sniffed out and coerced into submitting to a fat old man. Not how she had imagined her first time.

Charlie couldn’t believe it either. He was balls-deep inside the tightest sissy he’d ever had the pleasure of fucking. He too was surprised how easy it was to entice such a pretty little thing into doing what she was told.

He had known the moment he saw her laughing with her teammates that this was no crossdressing for a laugh. The hair and makeup were too precise and perfect. Not to mention the breast plate, false nails, and eyelashes. The others had simply borrowed their girlfriends’ bras and filled them with socks.

But it was the way Bethan acted when she thought nobody was looking that really gave her away. She checked herself over at every opportunity, making sure she remained immaculately pretty. And she did — particularly every time she returned from the toilet.

Charlie had kept a close eye on the pretty cheerleader, eventually catching a glimpse up her cheer dress. The sissy lover smirked and bided his time before making his move. He felt he had nothing to lose and everything to gain.

The older man reached for the zip at the back of the cheer dress and pulled it down. He tried to slip it down her arms to free her cute rubber tits. Bethan helped him, needing to get fucked like a real girl.

“Mmm, cute little titties,” Charlie chuckled, placing his hands over them as he drove his cock right up inside her.

He then pulled Bethan upright, squeezing her silicone tits, thrusting a little harder and faster. As he grunted and groaned, she whimpered and gasped. They were at opposite ends of the pleasure spectrum, but equally enjoying each other.

Then Bethan felt something unexpected. It can’t be, she thought. But it was. An orgasm was building. As she tried to wrap her head around it, her first ever sissygasm suddenly took over her slender body.

“Uhh! Uhh! Uhh! Yes! I’m cumming!” she cried out as sissy juice poured from her cage onto the female changing room floor.

“Mmm! Fuck, that’s hot, Bethan!” Charlie triumphed. “Cum on my fat cock, sweetie! Tell Daddy how much you love his cock.”

Charlie didn’t slow down. In fact, he fucked her tight sissy-cunt even harder, pounding into her with vigour. His pubic bone slammed into her smooth arse as he almost tore her tits off her body.

“I love your cock, Daddy! Uh! Uh!” Bethan wailed, experiencing the best orgasm of her life.

“Ohhhh! Yes!” Charlie groaned, about to cum himself. He shoved his cock all the way in and fucked Bethan with short, sharp thrusts. “Here comes your first load, sweetie!”

Bethan was slammed up against the wall, face and tits pressed hard against the cold surface, while Charlie emptied his balls deep inside his latest sissy conquest. Usually he found them online, but the convincing ones — the experienced, super-submissive sissies — didn’t go for men like him.

He pulled out and put his spent cock back inside his pants. Damn, that was amazing, he thought. Meanwhile, Bethan was left feeling confused and dirty. Her hole was painfully stretched and leaking sperm, but she couldn’t deny it felt good.

How do I go back to the party as if this didn’t happen? she thought. Then Charlie zipped up her cheer dress and turned her around to face him.

“Are you okay, Bethan?” Charlie asked with sincerity.

“Hmm,” she replied, unsure.

“Don’t be embarrassed or ashamed. You were amazing and you’ll get used to it,” Charlie told her.

“Thanks, but I’m not sure about that,” Bethan muttered meekly, fixing the cheer dress as it was before. She went over to the mirrors and saw her makeup had been disturbed by the heat and sweat on her face.

“I’ll leave you to freshen up. Don’t be embarrassed. I saw how much you enjoyed it, and you came,” he smiled, before unlocking the door and slipping back to the party.

Bethan tried to freshen up but only made her makeup worse. With her body broken and her mind all over the place, she sneaked out the side entrance of the club and called a taxi.

The driver thought she was a girl — a shy girl whispering her address from the back seat. It gave Bethan a confidence boost, having a man flirting with her.

When she got home, she quietly went to her bedroom. Alice came in uninvited, asking how the party went. Back in reality, Ben remained standing to make sure his sister didn’t catch sight of the chastity.

“Was it as good as you thought it would be?” she smiled wryly.

“It was just a party,” he shrugged.

Alice sauntered over and stroked the long blonde ponytail. “But did you feel liberated, Bethan?”

“Huh?” Ben gasped. “How do you know?”

Alice kissed her brother, pretending he was a real girl. “I’ve always known. Goodnight, Bethan. Let me know when you want me to do your hair and makeup again… or if you ever fancy a bit of girl-on-girl action.”