Simon waited as the two girls got ready. Both were passionate believers in sexual and gender equality and had decided to attend the Pride march as an angel and a devil, with Helen as the angel. Helen had lectured Simon extensively on the topic. He now realised his old views were outdated and unfit for modern society. It had been sobering to realise that someone less than half his age could completely change his beliefs.
Finally, the two girls emerged, giggling, from Helen's room. Simon was instantly hard. Helen wore a skimpy white dress that barely covered her bum with a pair of pink, gauzy wings and a silver tinsel halo. Her push-up bra accentuated her massive boobs. Tiny dark-haired Caro looked fabulous in a clingy black dress and sported a pair of pointed devil's horns.
Both girls wore high heels that matched their dresses. Simon's dick strained against his undies. He could hardly wait to fuck buxom young Helen later and hoped she'd let him fuck her tight arse as well. She was such a marvellously dirty girl, and Simon loved that she sometimes allowed him to violate her arse. But more than anything else, he wanted to fuck her tiny nubile friend, and he imagined Caro's lithe body riding his cock, and her gazing lustfully into his eyes. Hopefully, this would be his lucky day.
To fit the theme of the Pride march, both girls had plastered rainbow stickers on their exposed arms and legs. Helen lifted the hem of her dress, showing off her lacy white panties, and Simon saw she had a rainbow sticker attached to each of her arse cheeks.
The March started in a large square just a few minutes from the apartment. Helen and Caro walked on either side of him. Simon put an arm around both girls, pulling them close. He groped Helen's fantastic boobs, then tentatively felt Caro's flat chest. She didn't even flinch, so Simon tweaked a nipple. Perhaps he would get to fuck her.
As always, the parade was raucous, and they all imbibed freely from the bottles of spirits that circulated freely amongst the crowd. Simon fended off several approaches from scantily clad men. The encounter when a muscular black man approached him, wearing just a posing pouch and chaps, was typical.
The black man walked beside him for a few paces, then grabbed Simon's enormous dick.
"How about it, big boy," the young black man said. "Do you want to stuff that monster in my arse? I'd love it if you did."
As with previous encounters, Simon smiled and gestured towards Helen and Caro, who cavorted ahead of him, hand-in-hand, indiscriminately kissing people in the parade.
"My heavenly mistress forbids," he intoned solemnly, "as does her fiendish lover."
The black man smiled and slid a business card into Simon's trousers.
"That's a truly impressive cock, so if you ever change your mind, call me," he said as he fondled Simon's dick before melting into the crowd.
Thirty minutes later, they were roaring drunk and enjoying the parade when the skies darkened, and the heavens opened. They persevered for another ten minutes, but the rain was cold and persistent, and they were soon soaked through. Simon was freezing, and although the crowd was still noisy and having fun, marching in the cold rain was no longer enjoyable. He was relieved when Helen spoke.
"Let's get out of this damned rain," she said. "I'm freezing my arse off."
Caro laughed. "Don't use words like that, Angel," she said. One hand stroked her fake horns. "That's my territory. Let's go home out of this hellish storm."
They left the parade and ran down a side street to shelter under a tree. Luckily a taxi passed within minutes. Helen stuck out a hand and hailed it.
They tumbled into the cab, soaked through but giggling. A few minutes later, the cab decanted them onto the street in front of their flat. Simon supported the two drenched girls up the stairs. Helen fumbled briefly with the lock and almost fell over when the door flew open.
"It's been fun, and it's way too early to call it a day," Helen said, "but let's dry off first."
Caro nodded. "Good idea, I'm freezing," she said and drunkenly meandered into her room, leaving her door open.
Simon let Helen lead him by the hand into her room. She took her arms out of the loops that attached the purple fairy wings to her back, unzipped her white dress and let it fall to the floor.
Simon fetched a towel from her bathroom and dried Helen's fabulous body, lingering over her enormous breasts. Helen giggled as he did so, even as she kissed him. Soon she was dry, apart from her long blond hair, which still dripped water. Simon ran one hand over her warm skin, unbuttoning his shirt with the other.
Simon saw the lustful look on her face and smiled.
"Does my perfect angel want me to fuck her?" Simon asked.
Helen reached down, unzipped his jeans, and grabbed his rigid cock. "Do angels do that?" she asked with a leering grin.
"Or are you a little devil?" Simon asked jokingly. He handed Helen her wings. "You'd better wear your angel wings, or I won't be able to tell."
Simon quickly undressed as Helen undid her bra, releasing her magnificent boobs, and then she put her arms back through the loops of the gauzy fairy wings. She pushed her shoulders back and put her hands on her hips, showing off her perfect tits.
"Am I an angel?" she asked, her gaze fixed on Simon's erection. "Or will you treat me like the devil I am?"
Simon looked her up and down, his gaze lingering on her chest. She looked incredible wearing just tiny white panties and heels, adorned with the silver tinsel halo and pink fairy wings. The rainbow Pride stickers still plastered her smooth skin, and her boobs looked fabulous. He marvelled that this vision of loveliness worshipped his cock and allowed him to screw her.
"Angels need to be treated like the devil occasionally," he said.
Simon pulled Helen close and kissed her deeply, their tongues entwined. He wormed a hand inside her white panties and ran one finger up and down her moist, shaved slit. Though she was damp, Simon decided she needed warming up.
He pushed her back against the white iron bedstead, pulled her panties partway down, and knelt in front of her. He knew she was becoming excited; juices already oozed from her pussy when he pushed one finger inside her. He hooked it and started working it in and out as he tongued her clitoris.
She moaned when he finger-fucked her hard and fast with two hooked fingers. Her minge now felt dripping wet.
"Just fuck me, please," Helen implored him.
That was music to his ears. Simon stood and put his two wet fingers to Helen's mouth. She greedily sucked them clean.
"Turn around and bend over," he ordered.
Helen's white panties were halfway down her thighs. She turned, leaned forward, and gripped the rail of the white bedstead to support herself. She looked back at Simon over her shoulder. The gauzy pink wings excited Simon further.
Helen ran a finger along her bum crack. "How devilish are you feeling?" she asked.
Simon just grinned. He looked at the perfect starfish of her arsehole and the moist slit of her pussy and knew he was going to fuck both. Simon spat on his fingers and rubbed them on his cock for extra lubrication. Helen moaned when he ran his helmet between her lovely bum and her pussy, teasing her, so she didn't know which orifice was his target.
Her pussy bore the brunt of his first assault when he slammed his monstrous dick balls-deep into her tight wet minge in one mighty thrust. Helen moaned in ecstasy.
She wriggled her bum against him. "God, that feels good," she said. "I love your cock."
He put his hands on her hips and fucked her hard. His dick pistoned smoothly in and out of her tight dripping cunt. Helen started to moan and pant, spurring Simon to greater efforts. He was rewarded when she shrieked, and her pussy clenched around his dick as she came, and a small dribble of juices ran from her cunt.
Helen sighed contentedly, "Only your monster makes me come that quickly," Helen said.
He was glad she liked it a bit rough, but he had another orifice to fuck, so he restrained himself and slowed to a gentle pace to prevent himself from coming too soon. He laughed.
"I'm not finished with you yet," he said.
She giggled. "Glad to hear that. Coming just once is never enough."
Simon reached for the lube and squirted some onto one hand. He worked two oily fingers into Helen's perfect arsehole as he shafted her pussy. Helen moaned with each deep stroke, and he knew from experience it wouldn't take long for his mammoth dick to make her come when he pounded her tight arse.
"Is my angel ready for a good butt fucking?" he asked.
Helen giggled again. "You know I am," she said. "Ruin my angelic arse with your demonic weapon."
He pulled his massive member out of her pussy, rubbed some lube onto it, and slowly eased it into her tight sphincter. As always, her bum hole clenched tightly around his shaft, and it took several slow insistent thrusts before he worked himself hilt-deep into her incredible bottom. Helen squealed with delight when he pulled out and slowly rammed his monstrous dick back into her arse.
"I've been a very naughty angel," she said. "Punish my arse."
Simon fucked her slowly with long deep strokes until his mammoth cock slid smoothly in and out of Helen's bum. He sped up, and his hands pulled her hips back onto his dick. Helen's moans became louder and more urgent.
"Yes … I've been evil … punish me."
Simon smiled when Helen shrieked joyously as he repeatedly rammed his dick balls-deep into her arse. He felt her sphincter clench tightly around his cock as she came for the second time; her pussy juices wet his groin and dripped down both their legs. He loved that he could make her come so quickly.
Helen's climax drove Simon over the edge, and he spurted a massive load of cum deep inside her arse. He kept his rigid pole firmly embedded in Helen's bum until their shuddering subsided.
"You'd think our Devil would love this, wouldn't you?" Simon asked Helen.
Helen had told him many times that Caro was reluctant and had never had anything in her arse, but he was hopeful.
"Let's ask her," Helen said. "Her arse deserves to feel you inside it."
Simon let Helen lead him naked into the lounge. Helen walked towards the open door into Caro's room.
"Come on out, you little devil," Helen said. "We've got something to show you."
Caro came into view, still wearing the skimpy devil's outfit. She stared at Simon's massive wet cock.
Caro giggled. "Is that all?" she asked, eyes still fixed on Simon's rigid member. "I've seen huge wet cocks before."
Simon watched his cum slowly oozing from Helen's arse and dribbling down her legs. He was surprised when Helen turned her arse towards Caro, bent over at the waist, and spread her arse cheeks.
"Look what Simon did to me," Helen chanted in a silly sing-song voice.
Caro gasped when she saw Helen's red-rimmed gaping arse hole dripping with cum. She tried to run past Helen and escape back to her room, but Helen caught her arm.
"Look what Simon did to me," she repeated in that same silly sing-song voice.
Caro glanced at Helen's gaping arse. She opened her mouth to speak. No words came out. Instead, she shook her head and fixed her gaze greedily on his mammoth erection, still wet with lube and fresh from Helen's gaping arse.
Simon was overjoyed his dream of fucking Caro would be partially fulfilled. At the very least, Caro would suck his cock. He waggled his rigid pole with one hand.
"Can the Devil suck cock better than my tarnished angel?" he asked.
Caro glanced again at Helen's arse, then back at his slimy cock. She hesitated a moment, then laughed. "Oh yes," she said. "This devil can take anything."
Simon took Caro's tiny hand and led her into Helen's room. He leaned back against the white bedstead.
"Show me what the devil can do," he said.
Caro squatted in front of him and looked at him with wide blue eyes. "I'm going to make you come," she promised.
Caro licked her lips and grasped his bum with both hands. She opened her mouth wide, looked up, again catching his gaze with her huge eyes, and slowly leaned towards him. His massive pole crept into her warm mouth, gliding over her tongue. He felt his glans touch the back of her mouth. Caro didn't hesitate but continued to inhale his erection, and he felt it slide down her throat.
Caro paused when her nose pressed against his groin, and then she started to suck his cock. Her cat-like eyes never left his face as she bobbed backwards and forwards, sucking hard on his dick.
Helen stood behind Caro and raised her from her squatting pose. She lifted Caro's skimpy black dress, rucking it untidily around her waist. She pulled down Caro's black lacy panties, which fell and draped around Caro's ankles. She was now bent over at the waist with her arse naked and Simon's monstrous dick down her throat.
Helen's hands ran gently over Caro's body and lightly caressed her arse. Helen spread Caro's bum cheeks with her hands and thrust her head between them, obviously tonguing her arsehole. Caro continued sucking him unperturbed, her head bobbing, sliding his dick repeatedly down her warm throat. Helen gestured at Caro's arse.
"This little Devil needs a tail," Helen said.
Simon reached behind himself and passed Helen the lube. She oiled her fingers, and when Helen stuck a lubricated finger in Caro's arse, Simon heard a muffled squeal. Caro tried to pull away from his dick, but his hands were behind her head, preventing her from pulling back. After a moment, with Helen's finger firmly embedded in her arse, Caro relaxed and started to suck his dick again.
Simon loved the feeling of Caro's warm mouth enveloping his dick and watched in anticipation as Helen fingered Caro's virgin arse. It looked as if he might actually get to fuck it. A second finger joined the first inside Caro's bum, and Helen started slowly working them in and out. Caro kept sucking him even when Helen was finger-fucking her with two fingers rammed as far as they'd go into her sphincter.
Helen pulled her invasive fingers out of Caro's tight sphincter and gently stroked her bum cheeks.
"Relax," she said. "If you clench up like that, the plug will hurt when I push it in."
Caro mumbled something inaudible with Simon's dick still far down her throat, then resumed sucking his mammoth cock. Helen picked up a tail plug: a long sinuous tail with a bulbous silver insert. The tail was black and red, barbed, and matched the devil's horns that Caro still wore. Helen dripped some lube onto the shiny silver toy and worked more lube into Caro's arse with her fingers.
Caro flinched when Helen pushed the butt plug against her tight sphincter. Helen looked up at Simon.
"She's got such a tiny arsehole," Helen said. "It's going to be a very tight fit."
Simon grinned to himself. He'd violated Helen's virgin arsehole, and now he hoped he was about to destroy her best friend's perfect bum. Caro was a tiny girl, so he already expected her bum to be tight; the tighter, the better, he thought.
When Helen started to push the plug further into Caro's back passage, Caro closed her eyes and screwed up her face, but she didn't try to pull away. Simon briefly felt Caro's teeth press painfully against his cock.
When Helen finally pushed the widest part of the butt plug past her sphincter, Caro gasped, pulled back from Simon's dick, and stood straight. She reached back between her legs with one hand, feeling where the plug invaded her bum and craned her neck to see her new appendage.
"Now you've got a tail, like a proper devil. It looks fabulous," Helen said. "How does it feel?"
Caro looked thoughtful. She wiggled her bum and tugged at the tail with one hand.
"Strange," she said. "My arse keeps clenching around it."
After a short pause, she smiled broadly. "It's revolting, but I think I like it."
Simon watched her walk over to the floor-length mirror, turn her bum towards the mirror, and look at her reflection over her shoulder.
Finally, she nodded. "I like that it matches my horns," she said. "It makes me feel like a dirty whore, but it is so sexy."
Simon was dying to fuck her with the toy in her arse. "Do you want me to fuck you?" Simon asked.
Caro turned to face him and looked lustfully at the massive cock that had so recently occupied her mouth.
"I love being filled by huge cocks," she said. "Show me what it feels like being fucked by that monster when my arse is full like this."
Helen sat on the bed, her gauzy pink wings visible behind her. When Caro perched on the edge of the bed and leaned backwards, she was cradled by Helen, with her head nestled between Helen's impressive boobs and high enough to see what Simon was doing. Caro's legs were spread wide, providing a great view of her neatly trimmed pussy and the tail that dangled from her arse.
"Lift your legs," he said. "I want them over my shoulders."
Caro complied, and he helped her position herself. He ran his dick up and down her slit and then placed his dick at her entrance, parting her labia but not entering her.
He looked at Helen, who gazed over the top of Caro's head at his dick and grinned.
"I'm going to ruin your best friend."
He lowered his gaze and fixed his eyes on Caro's face. Her eyes were wide, and her lips parted slightly in anticipation. She is truly gorgeous, he thought. Simon remembered that she'd never had a plug...