I wrote this over a year ago, never dreaming I’d find my own special Roland pervert! And real-Roland is an improvement over fictional-Roland because he’s rich! He’s also much more kind than fictional-Roland.
Chapter 1
The sun was emerging from behind the clouds when Roland pulled back the curtain. Roland was gorgeous – he had black hair that rippled down to curls below his broad shoulders, olive skin and large deep-set dark eyes over high cheekbones. His full lips curved in a soft smile. Today was a special day. Chastity White would arrive from Mississippi at any moment, and Roland would be babysitting her for six days. Chastity was twenty, but her dad was very overprotective of his only child and would never dream of leaving her alone at home while he was on tour preaching. Chastity’s mom was a missionary and wouldn’t be home for months. For six days and seven nights, Chastity would know only this suburban two-bedroom house. Roland smirked in anticipation of what was to come. He had plans for her.
A soft knock made itself heard. Roland smirked again as he calmly strolled over to the door, unlocked it, and saw her for the first time in months. Her blue eyes widened and she smiled instantly, a child’s smile. She was beautiful, even without make-up and dressed in frumpy clothing as always, her long blonde hair hanging loosely over her shoulders, a gold cross dangling from her neck. Chastity had porcelain skin, a great figure and a kid’s fringe, her breasts hidden by a pink mohair sweater, legs encased in loose high-waisted jeans. She was wearing pink sneakers that looked new.
.Roland’s eye was drawn, as always, to the cheap red ring on her ring finger. It looked out of place, especially as Chastity usually wore quality. But Roland was one of the few people in the UK who understood the significance of the little plastic circle: it was an abstinence ring, a promise ring, and it meant that Chastity had taken a public vow of abstinence, a sacred oath to God not to have sex until the plastic ring was exchanged for a gold ring on her wedding day – and that night, Chastity would fuck. Her years or even decades of inhibition would be rewarded, and she would mate like a rabid whore, all the years of sexual repression having spawned the most depraved urges.
“Oh Roland! How sweet of you to have me,” she squealed, beaming and smiling her pristine, sincere smile that made Roland picture all the other things he would make her do with her mouth, her innocent, pure lips that had never even touched alcohol or coffee. And yes, he was going to have her.
“The pleasure’s all mine, babe. C’mon, I’ll take your stuff upstairs, would you like a bite to eat? I can whip up some pasta.”
“Thank you, Roland,” she replied in her soft, breathy little voice, “You really are too kind.”
The pasta was cooking nicely. Roland pulled out his mortar and pestle, grinding four laxative tablets into a yellow powder. His heart was pounding; he was almost shaking with terror or ecstasy, he couldn’t tell which. He sprinkled the powder into the saucepan, adding spices and plenty of salt and pepper. Next, Roland poured out the lemonade and laced Chastity’s with diuretics. The water in the saucepan was starting to boil. With trembling fingers he turned off the cooker, took the lemonades to the table, and a few minutes later called out to Chastity that lunch was ready. Was that really his voice, sounding so controlled, so calm? Chastity ambled into the kitchen, even her walk was oh so prim and proper. But all that was about to change! Soon she would be embarrassed, her whiter-than-white cheeks flaming red as she uncontrollably pissed in her prissy Southern jeans.
Roland felt his cock stiffening as she sat down in her still-dry jeans, completely trusting in him. Roland had a large package, and his lovely, thick member was slowly standing to attention. His penis was gorgeous, all shiny pink and veined, and Roland could picture it as he rubbed its head through his black jeans. He wanted to take it all hot in his hand and reassure it that it would have some action soon. Soon, he whispered to his hard-on, soon. Be patient.
“How was your flight?” he asked, marvelling at how light and airy his voice was.
Chastity twined some pasta around her fork. “Oh, it was fine, quite pleasant, really. I prayed for daddy’s mission to go well, it will, of course, but I always pray.”
“Yeah, I’m pretty sure it’ll go well. Your dad’s a really respected preacher, isn’t he? And it’s the Lord’s will, baby.”
They ate in companiable silence for a while. Roland was pitching a large tent in his jeans. When was she going to wet herself? The tension was almost unbearable.
“So, how’s life?” he said vaguely. Chastity toyed with her fork before pouting, “I don’t regret not going to college. It was the right decision, you know how much I’ve always wanted to be a missionary like mummy and daddy. I don’t need any qualifications for that. And someone else got to go to college in my place when I turned my place down.”
“Chastity, you’re a beautiful intelligent girl. You made the choice that’s right for you, and your gossipy friends can’t tell you what’s right for you. You’ll be a great missionary, I know it.”
Their eyes met, and she gently squeezed his wrist. Then a look of fear came into her face.
“Oh no, I have to pee!” she squealed, jumping up. She took two steps, crossed her legs and leaned forward. Suddenly something inside her slipped out of her control. her bladder let loose the muscle that was holding back her piss. Chastity peed her pants. She grabbed her crotch but it was too late – her mouth had gone dry and her pants had gone wet. A flood of piss poured into her panties as her bladder instantly deflated. Chastity gasped out loud – she had completely lost control. She piddled. She widdled. She peed and she weed. She was really doing it. She was peeing her panties. Warm piss flooded her thin cotton panties, seeping over her bottom. She squealed and clutched the front of her jeans, desperately trying to regain control of her rapidly emptying bladder. But it was too late. Chastity’s pants were completely drenched. She blushed bright red as she saw a damp blotch blooming over her lap. Roland was getting a full view of her peeing accident! “Ohhhhhh…oh no- no, no…” Chastity whimpered, clasping her crotch as the wet spot spread. “Oooh…oooops… I’m wetting my pants, I’m doing a pee in my panties!” The spot on her lap dampened into a soaked patch. She crossed her legs and looked down at her drenched jeans. She watched in silent horror as the soaked blotch spread across her lap and the inside of her leg darkened. Chastity bent further, squeezing her legs together to keep the hot urine from streaming out, but the piss continued pouring out of her deflating bladder. Chastity closed her eyes in shame. She felt wee trickling down her thighs. She crossed her legs. She even crossed her fingers. Frantically she twisted her hands in her lap. Her deflating bladder was letting her wee all pour out in a warm rush. She got that warm feeling down below. she just stood there wetting her pants all the way through. She began to cry with embarrassment, the terrible humiliation of losing control of her pee while a boy was watching every squirt. The huge torrent of hot pent-up pee unleashed all over herself, she was emptying my bladder all down her legs. Warm wet wee was going down her legs. She just couldn’t stop peeing. She started to cry as she realised she had completely lost control; she was going to keep wetting herself until her bladder was completely empty and there was nothing she could do about it. She was wet through. So warm. All wet. Swamping her jeans, the splattering down her legs becoming a stream, now a deluge. She stumbled away from Roland, trying to get to a bathroom, but Roland was prepared. Not for nothing had he spent the past two weeks feverishly scribbling his plans for her, The Seven Nights. Roland gripped her wrist. “Naughty sissygirls who go peepee in their panties don’t get to go to the big girls’ bathroom. They have to pee their pants…not that you’re able to stop pissing yourself anyway.”
Chastity was still sobbing and peeing right into her panties. Squirts of pee spurted into her sneakers. Then she heard the drip, drip, drip. Chastity was dripping on the linoleum. How embarrassing! She was peeing right through her jeans! The drips became a trickle, then a stream of yellow piss splashing onto the floor. Then – oh the shame – she made a puddle. She made a yellow puddle on the floor like a naughty little girl. Roland’s eyes were watching the piss spraying out of her. Her pee was on display for him to see. “Nonononono…oh no I’m pissing the floor! I’m making a puddle! I’m making a pee-puddle underneath me!” Slowly it pooled underneath her. She couldn’t believe she was standing in Roland’s kitchen relieving herself in her knickers right in front of him. She pressed her hands into her crotch, doubling over and slowly sinking into a half-crouch. “No, please…not a puddle…” She just went piiiiisssshhhh, all over her pants, her jeans, the floor. Chastity could actually feel the pish running down her legs and splattering noisily all over the linoleum. Her trainers were filled with wee. She was pissing into her trainers, just standing in Roland’s kitchen with a steaming yellow puddle spreading round her sneakers. She knew she was a naughty girl, making a puddle of pee. Gradually, the last trickles drained out of her now empty bladder. Chastity found herself standing in a puddle, wet at both ends and wearing pissed-in jeans.
“Oh dear,” Chastity gasped, “I wet myself.”
“‘oh dear, I wet myself’? You just peed your pants and you’re saying, ‘oh dear I wet myself?’ Yes,” said Roland, “You just went wee-wee in your pants. Why did liddle Chastity wet her panties?”
Chastity’s face burned with shame. She just looked down at her drenched jeans and trainers full of pee. She looked at the puddle she’d made. Chastity was very aware that her knickers were wringing wet.
“Naughty widdle girls who go peepee deserve a spanking,” Roland announced. “Chastity, I’m going to spank you until your rear cheeks are as red as your front cheeks.”
Chastity’s hands flew to her damp behind. Her sobbing got louder. “No, Roland, please no! Not my butt! Please don’t spank my ass, I’ve never been spanked!”
Roland held her wrist as he moved his chair and sat. “You peed your panties like a little girl, so you’re getting spanked over my knee just like a little girl. Maybe that’ll teach you not to make lemonade in your knickers.”
He placed a tea towel over his lap so her piss wouldn’t get on his clothes.
“Please don’t spank me, I’ll never wet myself again, I promise!” she wailed, one hand hiding the sodden patch on the front of her jeans, the other protecting her backside . Roland patted her bum. “You won’t be able to sit on your arse when I’m finished giving it a good, old-fashioned bottom warming.” Chastity gulped. Her wet jeans suddenly felt very thin. “I’m so sorry, please not on my butt, it’ll be so embarrassing if you put me over your knee and smack my bottom.”
Roland looked into her blue eyes all wet with tears of humiliation. They were twin pools of terror, begging him not to spank her.
“You have totally pissed yourself. Your little ass needs a warm lesson across my knee.”
Roland pulled the crying girl over his lap. Chastity went scarlet as she realised that she was over someone’s knee about to be spanked. Her bottom was tingling with anticipation of the smacks it was going to receive. Roland pulled off a pink sneaker and tipped the piss out of it. Chastity flushed with embarrassment as a pint of Chastity-pee poured onto the floor. Roland removed her other shoe and emptied the piddle out of it too. Then he raised his large hand and brought it crashing down on her trembling rear end.
“Oweee! My bummy!” she squealed, before another smack landed on the curve of her butt. Roland grinned as he gave the quivering rump another short, sharp shock to remind Chastity not to go pissing herself. Roland gave Chastity a hard smack on her butt and heard a whimper of pain. This was certainly going to be an education for Chastity’s bottom.
“Ow!” she yelped, “Roland -“. but Roland couldn’t have cared less. He delivered a flurry of spanks to the seat of her jeans, every stinging smack sending a fiery message to Chastity’s ass. Hard slaps rained down upon her jeans-clad butt, then a volley of firm smacks landed on her now stinging backside in quick succession.
“Roland! Please! I’m sorry!” Chastity sobbed. Roland swatted her bum over and over, until Chastity felt truly sorry for herself. She was sobbing and crying as Roland reached for an old wooden hairbrush, brought it down hard on Chastity’s trembling behind, and administered a sound bottom beating to her denim-clad ass, delivering a series of botty-trembling swats to the seat of her jeans. Roland didn’t let up, he knew he was warming her backside considerably. Soon Chastity was feeling very warm and tingly. Roland surveyed his target, then rapidly gave the undercurve of her butt his full attention. He finished it off with several whacks, right on the centre of her seat. When it was over, a sobbing Chastity was sporting a very well-spanked derriere. And she knew it. Her ass hurt.
“I’ll never wet myself again, I promise!” Chastity wailed. Roland spanked hard and fast and her hand flew back to clutch her throbbing sit-upon, but Roland caught it. Then he pulled down her wet jeans, exposing her even wetter pants. Chastity’s face cheeks turned as red as her ass. Roland was getting a full view of her dripping panties! Her pee-soaked underwear was exposed. He smirked as he gave Chastity a botty-swelling paddling to the seat of her dripping panties. He pelted her rump with the brush, spanking her soundly over her knickers. Her sorry ass was really getting it. Roland warmed up her derriere good and proper, and Chastity could feel her butt getting hotter with every smack.
Roland peeled off the undies, smirking at the sight of Chastity’s rosy red cheeks. Chastity gasped out loud – a man was seeing her bare backside! This wasn’t supposed to happen until her wedding night, yet he was getting an unparalleled, rosy view of her bouncing full moon.
“No, please no, not on my bare butt!” Chastity pleaded, but Roland was intent on teaching her naughty ass a hard lesson. Roland’s brush tickled her ass a warm, rosy red. Chastity cried with pain and embarrassment. Here she was, getting her bare bottom spanked for wetting herself. Worse, her naked ass was being exposed to a boy. What would her daddy say?
Roland delivered a series of short, sharp shocks to Chastity’s reddening rear end, confident that it would be a long while before she contemplated going to the bathroom in her pants again. He was intent on building a fire in her ass that she wouldn’t soon forget. Again and again the brush landed on her swelling bottom, and Chastity was bawling like a baby, wishing she could hold her burning butt. Roland grinned at the bright red glow of Chastity’s cheeks. Her naughty backside looked like a red traffic light. Chastity howled as Roland turned his attention to her sizzling sit-spots, making sure Chastity’s rear was nicely roasted. Chastity squirmed as he paid special attention to her sit-spots, peppering her tender bummy with solid smacks. The brush gave her sit spots another fiery tickle, and her bottom blazed with heat. He was paying special attention to where Chastity sat, because she sure wasn’t going to be sitting down anytime soon. Roland was going to roast her rear for her. He gave several whacks to the centre of her heating hiney, then Roland unleashed his brush all over Chastity’s upturned butt, turning it fire-engine red. The now scarlet-bottomed girl was crying hard; all she could think of was reaching back to comfort her flaming ass. It felt like her bum was actually on fire.
“Please, I’ll be good, I’ll be good!” she wailed.
“Oh, you will,” smirked Roland, as he firmly applied the brush, “I’m quite sure you’ll be a very good girl, at least until you can sit on your sitting area.”
Roland laid down his brush and took a ping-pong paddle to Chastity’s tail, watching her well-chastised arse rapidly blush a deep, dark red.
“Aaaaahhh! Owwww!” Chastity shrieked, kicking her legs up and down and squirming on Roland’s lap. Roland kept her pinned across his lap, receiving her punishment. She was bucking and screaming as he soundly thrashed her backside. Roland smacked the last vestiges of mischief out of her bum while she hissed with pain. Then he put the paddle on the table and spanked Chastity’s bared bum with his hand. He spanked hard and fast, eliciting more frenzied bawling from the chastised pants wetter. Roland slapped his handprints all over her swollen red ass. Then, proudly, Roland surveyed his handiwork. Chastity’s half moons were no longer the same colour and size as they had been before the spanking. This was one girl who wouldn’t dare take another piss in her pants.
Chastity was still bawling hysterically; she just lay over Roland’s lap, completely exhausted, tears coursing down her face. Gradually, her legs stopped kicking. Roland found the sight of her glowing red ass very comical. Chastity reached back and clasped her red bumcheeks and howled.
Chastity stood up very slowly, both hands clasping her throbbing ass. She rubbed and rubbed her stinging hiney, but it still tingled and felt very warm indeed. She had been transformed into a spanked, hot-bottomed little girl. She didn’t feel twenty, she felt like a spanked little girl who’d just gotten a bare bottom spanking over a man’s knee. Chastity cried as she hopped around the kitchen rubbing her throbbing asscheeks. “I’m sorry, Roland,” she sobbed, “I’ll never wet myself again, not ever!” Very gently, Chastity cupped her aching arse, giving her bright red bum a loving squeeze. She cradled her dark red sit-spots.
A few minutes later, Chastity was standing in the corner rubbing her naked, colourful bum. Her wet pants and jeans had been pulled down to her ankles and her freshly spanked derriere was on full display. Her tomato-hued ass was covered in strawberry-coloured handprints, sit-spots as red as a pair of cherries. Roland took another photograph. Chastity exhibiting her red, spanked behind was literally the picture of humiliation. Her head was hung in shame, fingers soothing the blaze in her rear.
He enjoyed the view for a few more minutes before leaving the room, letting her change in privacy. He’d picked the outfit – his house, his rules, he’d told her. There were pink, full-brief, childish-looking knickers, a white miniskirt, and a pink frilly kid’s top. Chastity emerged from the room, her breasts bursting out of the little top and her red ass hanging out of the skirt. Her face cheeks were as red as her ass cheeks. How shameful to have wet her pants in front of a boy and then been spanked over his lap – on her bare bottom! The reddened bottom that even now was on view, thanks to the tiny skirt.
“My, my,” smirked Roland, “Who thought you were such a bad little slut? Look, your butt is saying hello under your skirt; look at your boobs! I thought a spanking would have taught you better.”
Diary of a VirginWhore 