Becoming the Milf Whore Nextdoor
Bdsm Story

Becoming the Milf Whore Nextdoor

by Li11ian 18 min read 4.8 (9,400 views)
milf whore bdsm spaning rough used curvy old man
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It took Jackie's feelings much longer to stop hurting than her bottom. By the next morning, she had stopped noticing the tightness in her skin as she moved. In the shower, she could still see a pink hue to her once-white ass cheeks.

Later, she used extra moisturizer on them and spent a few minutes after her shower massaging the cool cream into her bottom. Watching her pink cheeks in the wardrobe mirror as she stood naked in her bedroom. Gentle working the cream into her pink peachy bum.

Each time she felt her bottom tingle, she was reminded of the spanking Bill had given her. No, not given, paid for. She felt humiliated, that she would allow herself to be used like that for money. But she also felt a tingle of excitement deep inside. She had enjoyed it, and perhaps that is what hurt and embarrassed her most.

This cycle would continue for the next few weeks. Something would trigger her, she would think of Bill's little home office and become aroused. Then the guilt would rush up inside her. Sometimes it was so bad she almost felt nauseous. How could she do such a thing?

The end result though was that today, after work, she could pop to the bank. Pay in the cash Bill gave her. And pay the rent. She turned to face the mirror. Studying her soft, curvy, little egg timer shaped body. Remembering Bill's reaction to her, that flutter in her tummy building again.

"Not so firm and perky anymore eh?" she asked the empty room. She took hold of her little pot belly and shook it. Then her hands moved up to her breasts. Placing her hands flat above her nipples she lifted them. Remembering how they used to stand, so firm and proud. But twenty-odd years, three kids, and years of breastfeeding had seen to that. She let them go and the large pale globes fell back into place. Bouncing and swaying just above her little belly.

Suddenly, she saw herself, standing naked before the desk in Bill's little office. The chair nearby was waiting for her. She felt her nipples harden, and a subtle pulsing sensation between her thighs.

"Shit," Jackie swore, closing the wardrobe door. Trying to convince herself that was a one-off. But deep down inside, she knew it would happen again. But for now, at least, her head was ruling her loins. She dressed, walked to the bus stop, and headed in to work.

Bill next door on the other hand. He had no such doubts. Sure, he felt guilty, he was a married man after all. But his was a sexless marriage now, and he was already trying to figure out a way to get Jackie up to his little home office again. He didn't see much of her over the following days. And when he did see her, it was from a distance or they were unable to talk.

A few weeks passed. The weather was getting warmer and Bill spent more and more time in the garden. Partly because his garden was immaculate, and he wanted to keep it that way. But also, he wanted to allow Jackie to talk to him. If she wanted to.

Jackie felt a trickle of sweat run down her back as she opened her front door. It was too warm for her. The man-made fibers in her tight work uniform didn't help. The walk from the bus stop in the afternoon sun was just the icing on the cake. She kicked off her shoes and walked to the kitchen, calling her son's names as she went. She knew they wouldn't be in, but just in case.

By the time she reached the kitchen, her skirt was already unfastened and halfway down her legs. She threw it in the washing machine. Followed by her blouse, tights, bra, and panties. She set the machine on a short wash and stood up, stretching her back and running her hands under her hot wet under-bosom. Taking that bra off was such a relief. Then she spotted Bill in his garden, just the other side of the fence.

Ducking down behind the kitchen counter. She couldn't help giggling to herself. She got back up slowly, checking where Bill was and staying more or less out of sight. He turned and glanced at her house. But didn't seem to notice her. She watched the old man for a moment and a naughty idea crept into her head. She half dismissed it but stayed hidden. She watched him a moment longer, and then she sprinted from her kitchen and went upstairs.

Jackie got straight into the shower, eager to wash off the day's grime. She was well aware of the frosted bathroom window. Just above the bath, she was showering in. Overlooked the side of Bill's house, and his garden. That idea made its way into her head again. Almost getting caught naked in her kitchen had made Jackie a little giddy, like the naughty teenager she used to be. The shower felt so good, and as she moved her hands over her body she became more aroused. Jackie allowed her mind to wander and her desire began to influence her reason.

It was that time of the month again, rent was due in a week or so. She had the money, just about. But there would be no room for any little treats. She had been hoping to pick up a cheap bottle of red for herself this weekend. She knew a way to get a little extra cash though, she thought. By selling herself to the dirty old man next door. Jackie giggled to herself, picturing some two-bit hooker in a sleazy American cop drama.

She stepped back from the spray of water and began soaping herself. The sun shone in through the window. Outside she could see the blurred shadowy images of the house next door, and Bill in his garden. Jackie stepped back a little further so that she filled the window. She had no idea if he could see her, but that didn't make it any less exciting.

The ball was rolling now, gathering momentum, she wasn't going to be able to stop it. She stepped from the shower feeling rejuvenated and horny. She wrapped a towel around her hair and walked, naked and wet, into her son's room. The water on her skin drained the heat from her as it evaporated, cooling her down at last. She peeked from the window. Bill was sat in his garden, facing the side of her house. Almost as if he was waiting for her.

Jackie went to her bedroom, toweling her hair dry as she went. She swept her damp hair back into a thick, bushy ponytail then searched her knicker drawer for her sexiest panties. Embarrassingly, she didn't have any. So she just took the smallest newest pair of white cotton panties she had and put them on.

She took a little white sun dress from the wardrobe and pulled it on over her head. The elasticated top hugged her chest. It showed far more cleavage than she was usually comfortable with. Then the dress filled out in generous loose pleats to her knees. She had got the dress thinking it would hide her plump little body. But then she realised one good gust of wind would lift it and display everything.

Jackie juggled her breasts into the struggling cups and teased the puffed sleeves down off her shoulders. In another cupboard, there was a pair of little white mules she had never got to wear before either. She scuffed her feet into them and checked the result in the mirror.

The little three-inch heels made her feel quite dressed up. The dress accentuated her breasts, not that they needed it, but also hinted at easy access due to its light, floaty nature.

Feeling suitably enticing, Jackie went back to her son's room. Bill was still sitting by his little bistro table, apparently reading. With butterflies in her belly, she headed downstairs. The wash had finished, so she emptied the machine into a basket, grabbed the pegs, and went outside.

The door closed behind her with a loud thump, and her heels made little tapping noises as she crossed the flags to her lawn. Jackie hadn't even made it to the washing line before Bill's head appeared above the fence. She put her laundry down and turned to face him. Raising one hand to shade her eyes from the afternoon sun as he approached the fence.

"Hello Bill, how are you?" she asked, trying to be as cool as possible. But her heart was racing, and the look on his face told her the dress was working. She couldn't help but smile, a broad beaming smile of excitement. As her heels sank into her lawn. The wind blew her little dress around, and the old guy next door admired her rack.

"I'm fine thank you Jackie, you're looking well. Hope your bottom isn't still sore?" Bill replied with a naughty grin.

"I take it Pam's not in?" Jackie said and pulled her tongue at him before taking her work skirt from the basket and hanging it on the line.

"What makes you say that?" Bill asked. She continued hanging clothes out. Bending forward to take them from the basket, making sure her boobs were in clear view. Then raising her arms to hang each item, with the warm breeze tugging at her dress.

"You wouldn't be saying things like that to me if she was around." Jackie giggled in response as she worked. Bill watched her, mesmerized. Each time she bent her large heavy breasts pushed at the front of her dress, revealing even more of themselves. Each time she stretched up, her dress lifted to her thighs and the breeze threatened to expose that soft round peachy bum underneath.

"Yeah, umm," Bill gathered himself, "Pam is out this evening, crochet tonight I think."

"Oh, so you have a nice quiet evening to yourself?" Jackie asked, then tried to encourage him, "Got anything interesting planned?" Her uniform, bra, and knickers were on the line now, Jackie approached the fence in front of Bill. She wasn't tall enough to rest her arms on top like Bill did. So she placed her right hand on a nearby post. Bent her right knee and put her left hand on her hip. Then pushed her chest out.

"Umm, well I was err," Bill struggled for the words, gazing down at her breasts. "I was just wondering if everything is alright with you. I mean, you know." She knew exactly what he meant. He was hoping she was skint again this month.

"You mean, can I pay the rent?" she asked bluntly?

"Well, yes, because if you need anything?" Jackie wasn't very good at this teasing and flirting thing. She had run out of ideas and ways to hint at him. She just wanted him to come out with it now. Because she still couldn't bring herself to offer. She wanted to, but something inside her took her voice whenever she thought of doing so.

"Why don't you just ask me, Bill?" Jackie said suddenly, the sunny smile fading into a timid lip chew as her self-confidence evaporated. She looked up at Bill, her big green eyes wide and somewhat fearful. Not of what Bill wanted to do with her, but of the fact she was out here, looking for it. She couldn't hold his stare and looked down at her painted toes. There was an uncomfortable silence.

"Do you want another fifty quid?" Bill asked suddenly.

"Yes," Jackie answered in a little whisper. There was no response from Bill. She didn't know if he had heard her or not. Maybe he was just teasing her, making her struggle just as she had tried to do to him. She lifted her eyes to his and said. "Yes please."

"Put your stuff away and come round then," Bill instructed, his confidence growing now that it was clear who wanted what. Jackie threw her laundry basket and pegs back in her kitchen, and made her way to the side gate. Bill was waiting there for her and held his gate open as he had done before. Jackie could feel her legs trembling as she stood in Bill's kitchen. He closed and locked the door behind himself, then turned to face her.

"Shall we?" he asked, and gestured to the hallway with an open hand. Jackie tried to calm her nerves. It was even worse than the first time now. She wrung her trembling hands together, rooted to the spot.

"Umm, I don't suppose you have anything to drink?" she asked weakly.

"Of course, sorry yes, what would you like? Brandy, Bourbon, Vodka?" He offered.

"Do you have any coke?" Jackie asked.

"Um yes I have," he said, and took a can from the fridge nearby.

"Bourbon then please," she said, "with just a splash of coke."

"Sure, won't be a second," Bill replied and left the room. Jackie eyed the back door, her nerve wavering. The first time could have been put down to experimentation or naivety. This time though, she knew exactly what she was doing. Was she really willing to perform a sexual act, for money? She noticed the key had gone from the back door. She crossed the room and tentatively tried the handle, it was locked. There was no easy escape that way. Bill reappeared with a full tumbler in his hand and offered it to her. Jackie took the glass, and a big swig as she moved away from the door.

"Fuck," she coughed as the spirit hit her throat, it was much stronger than she expected. But the liquor hit the spot.

"Sorry, too strong?" Bill asked. Jackie shook her head, and quickly drained the glass. Gasping as the strong alcohol warmed her insides and bolstered her courage.

"Thank you," she said, and feeling a little braver added, "same deal as last time?"

"Upstairs in my office please Jackie, if you don't mind." He spoke in an unusual tone as he nodded his agreement, and gestured to the hallway again. Jackie followed his instruction and went upstairs, with Bill close behind. She went into his dark little home office and stood before his desk.

The old man followed her in and closed the door firmly behind them. Then he walked behind Jackie. Stopping to place the small wooden chair in the middle of the open space again. Then went behind his desk and sat down on the large leather chair. Jackie glanced around the room, it looked different somehow. There was less clutter, and the desk was almost empty.

"Now then Jackie, when you are ready," Bill said in that voice again and gestured to the chair. Corporal punishment had been banned in schools by the time she attended. But she had been subject to enough lectures before being given a detention, to recognise that tone. She could tell from his expression that the dirty old bastard was loving every second of it. Without so much as a second thought, she found herself playing along.

"Yes Sir." She said and turned to face the back of the chair. She bent forward, her tummy enveloping the wooden slats as he hands came to rest on the seat. Again, she wrapped her fingers around the edge of the seat and waited. Bill got quickly to his feet, moved around the table, by the window, and approached her from behind.

"Five twenty-three," he said, confirming the start time. Then he quickly lifted her dress, folding it carefully over her back until her soft round bottom and little white knickers were exposed. The folds of the dress slid up her back as she leaned forward. Gathering around her chest leaving her waist and little belly on display as well.

"Oh god," Bill mumbled under his breath as he gazed down on her cotton-clad backside. The thin material was caught between her cheeks. And her panties didn't quite come high enough on her hips to cover all of the crease. An inch or so of her ass showed above them. Merging into her back with a little Y shape and two dimples. Bill steadied himself and turned back to the chair behind his desk. He sat down and looked Jackie over as she bent over the little chair in his den.

"Are you quite comfortable there Jackie?" He asked.

"Umm, no, not especially." She giggled in reply.

"Well," Bill continued in his headmaster's tone. "This is the second time I have had you in this position. I'm beginning to think you like it?"

"Ye, yes Sir." Jackie flicked her ponytail to one side and looked at Bill.

"Yes Sir?" he repeated, "so you do like it?"

"No Sir, I meant it is the second time."

"I know it's the second time girl, I asked you if you enjoyed it, didn't I? He said, pretending to get angry.

"Yes Sir."

"Yes Sir again, so you do enjoy it. You like to be dragged into my office, exposed, punished, and humiliated do you?" There was a moment's silence, Jackie could hear her heart beating. She was not playing along anymore, this question seemed real. Her answer was on the tip of her tongue, but she couldn't bring herself to say it. Suddenly Bill hopped from his seat, rounded the desk, and landed his open hand on her big soft bottom with a loud crack.

"Aaaah fuck." Jackie squealed, taken by surprise. But she kept hold of the seat.

"Answer me girl," Bill pressed, "you enjoy it don't you, it excites you?"

"Ye, yes sir." Jackie blurted out, then squealed again as Bill began spanking her bottom through her panties. First one cheek then the other, alternating again and again. Not so hard but quickly, again and again, his hand met her soft cheek with a loud snap. Jackie wriggled and squirmed on the back of the chair. Even lifting a foot up to her thigh as the stinging on her bottom grew more and more intense.

"There, feel better now?" Bill asked breathlessly, pacing to and fro behind her. For what seemed an age Jackie couldn't speak. Her bottom was tingling, and throbbing, and felt red hot. She could feel her pussy pulsing in response, making her wriggle even more.

"I asked you a question girl." Bill insisted and approached her, bending down to look into her big green watery eyes.

"Yes Sir." Jackie whimpered her desperate, needy eyes locked on his.

"Good girl," Bill whispered, suddenly out of character. Then he moved behind her again and slipped his fingers into the waistband of her panties. He slowly eased them down, enjoying every inch of Jackie's hot red bottom being exposed. He squatted behind her as the white cotton slipped to her thighs.

Jackie's large pink cheeks separated as she bent forward, just enough to expose the tight little bud of her asshole. Bill resisted the urge to push his face between those cheeks and drive his tongue into that little pink delight. Instead, he got to his feet. Adjusted his pants to accommodate his now rock-hard cock, and gently held her hot red cheeks in both hands.

The room was quiet but for the tik of the clock and the soft panting and occasional sniff from slightly tearful Jackie. Bill looked at the clock. Shit, four of the five minutes gone. He gave Jackie's bottom one last caress, before laying into her again. He moved his hand upward this time to catch and lift her soft cheeks. Mesmerized by the way they jiggled and squirmed as he spanked her. His open hand caught the backs of Jackie's thighs as she fought the urge to stand harder and harder. Snap, snap, snap, again and again, Bill spanked her poor red bottom until at last, with a squeal, Jackie stood up.

"Aaahh fuck, fuck," She whimpered as she danced around the room holding her bottom. Bill quietly made his way back to his chair. Jackie slowly calmed down, she stopped moving about the room and wiped her eyes. Then she looked at Bill. He had a naughty grin on his face like he had just won a bet and it was time for Jackie to pay. She turned and looked at the clock on the wall.

"Was the time up?" Jackie asked in a breathless whisper.

"Not quite," Bill said.

"So, so we have to start again?" she asked. She wasn't ready to stop yet. But her bottom was on fire. She could feel herself getting wet between her thighs as she moved and thoughts of having him inside her filled her head.

"You do believe me don't you Jackie? I don't want you to think I would lie to you, there honestly was another twenty seconds or so to go."

"Yes, I believe you." She replied she could see the sincerity on his face. "But, I..."

"It's ok," Bill interrupted her. "We can stop there, it was close enough." There was a long silence, Jackie struggled with her desire, her propriety, her confidence. She wanted sex, it had been so long. But to be paid for it? Was she really going to offer herself to this old guy for money? Her head was telling her to leave, but her body refused to act.

"I don't want to," Jackie said in a whisper.

"Sorry?" Bill asked leaning forward.

"I don't want to stop," Jackie said a little louder, finding her voice and expressing her true desires. Then she reached down and gathered the hem of her dress in her hands. Bill watched her intently, quietly, not wanting to distract her in case she changed her mind. Jackie raised her arms, lifting her dress off over her head. She dropped it on the floor by the chair and stood before Bill's desk totally naked but for the little white mules.

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