My Last Morning With Me
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Gregory saw her early one evening when he was headed to his car. She wore a white, button-down blouse, a slim, black skirt just below the knee, and a pair of black, heeled, Mary-Janes. Her hair was in a long, red braid. He stopped to watch her pass and his eyes followed her down the street. Legs with promise. An ass that he wanted to expose and explore.
He shook his head as she continued on her way. He wondered briefly if she was an office worker. Then, he continued down in the sidewalk the opposite direction and went to his car
#
Three days later, he saw her pass again. She wore all of the same clothes but this time she was rolling up a maroon apron. He recognized it and knew where she worked. On an impulse, he followed her. She went to the bus stop one block over. He passed her by and made a loop to his car
Gregory told himself to let this one go but he couldn't get that auburn braid out of his head.
#
Gregory stood in front of the building every day the following week to see when she passed. Monday, Thursday, and Friday. The following Monday, he took a chance and waited in his car just behind her bus stop. When she got on a bus in the evening, he followed it until she got off. He parked and watched her. She checked her mail. When she went inside, he looked at the name on her box. A. Pyley.
A, what? Amy? Ashley? Amanda? Anne?
But he did learn that she lived in apartment three twenty. It was stenciled on the door of her mail box with her name. And that in the parking space for apartment three twenty, there was a car that clearly hadn't been on the road in some months. One tire was flat. The registration sticker was out of date.
When he drove out of her neighborhood, he only wished that he had gotten a peek at which apartment window was hers.
#
On Thursday, he decided to have lunch in the little bistro down the street. The one where she worked. While he waited for the hostess to seat the couple ahead of him, he scanned the room.
There she was, hurrying from table to table. She had a little, impersonal smile that she flashed from time to time as she took an order at one table and delivered food to another. He amused himself by imagining what she would be like to fuck. He liked to fancy her a little hesitant, a little resistant, but taking it anyway because it felt so goddam good--
"Booth or table?" the hostess asked, interrupting his thoughts.
He nodded to a little corner table in what looked like her section. "May I sit there?" He didn't offer an explanation.
"Certainly," the hostess said, grabbing a menu and leading him.
He had the start of a hard-on and he kind of liked it. He sat with his back to the wall and opened the book he brought as a decoy. He watched the rest of the staff, too, noticing that most of the other female servers wore much shorter skirts. They opened a button or two more on their blouses. They mostly wore sneakers, though. He preferred the Mary-Janes.
It took her less than three minutes to get to him; it was a good sign. Gregory loved efficiency.
"Hi," she said. "I'm Alice and I'll be your server today. Is there something that I can get you to drink?" Her voice reminded him of a songbird: throaty and sweet. He could imagine her moan.
"Water, no ice."
He didn't actually have anything against ice; he just wanted to know how well she listened. She nodded and bustled away. He watched her legs over his book.
She was back in minutes with a glass of water with no ice. Efficient and able to listen.
"Are you ready for me to take your order?" she asked.
It was on the tip of his tongue to ask her if she was ready to take his orders but he controlled himself. "The Cobb Salad. No bread."
She wrote it down and glanced over her pad at him. She had the longest eyelashes he had ever seen. He wondered if she could even wear sunglasses with eyelashes that long.
"Red wine vinaigrette, okay?" she asked.
"Yes, but on the side."
"I'll get your order right in. Let me know if you need anything while you wait." She gave him one of those little, impersonal smiles.
Overall, his experiment was a success. She filled his water glass twice, using a spoon to keep the ice from the pitcher from falling into his glass. She didn't bring bread. The dressing was on the side. And when she bent at the waist to pick up someone's dropped fork, Gregory's partial erection became full-blown. His mind became a kaleidoscope of the things he wanted to do to her.
"Any dessert for you?" she asked when she picked up his plate. "Or would you like your check?"
He had a quick flash of her licking meringue off of his dick. "My check, please."
She laid the bill holder on the table next to him, gave him another of those impersonal smiles, and said, "I'll be right back to get that."
It was fifteen dollars. He left a fifty in the bill holder and was gone before she came back.
#
On Friday, he stood in front of the building, waiting for her to pass, his briefcase strategically on the sidewalk beside him. She always skirted close to the buildings so when she was near him, he slid his briefcase out in front of her with his foot to make her stumble.
Once she regained her balance, she flushed and turned. "Oh, I'm so sorry," she said, looking at the briefcase. "That looks expensive. I hope I didn't scuff it."
"It's fine," he said. "It's old."
She glanced up at him, noticing him for the first time. Her eyebrows drew together and there was a little wrinkle between them. "I served you yesterday."
"You did."
"You left me a huge tip. Do you know you left me a fifty and not a twenty?"
"That was on purpose."
If anything, she looked even more confused. "Um... well, thank you."
Seeing her off-balance was titillating. He couldn't help but press his advantage. "You know how you could get another big tip out of me?"
"I... no."
"Wear a shorter skirt on Monday."
"I'm sorry?"
"On Monday, when you come to work, wear a shorter skirt."
She flushed and backed away a step. Her expression became guarded. What she didn't do was look outraged or affronted. "I don't have one," she finally said.
He looked her up and down, knowing that he was making her uncomfortable. But, she hadn't fled yet and that was a very good sign. "That's a shame. I can be very generous when I'm motivated to be."
Then, he politely nodded at her, like they had been discussing the weather, bent down to pick up his briefcase, and gave her a little impersonal smile of his own. He turned to walk to his car, leaving her standing there, staring after him.
#
On Monday, Alice's skirt was at least two inches above the knee. Gregory saw her while he waited to be seated, long before she noticed him. His table was open, so he requested it again. He watched her zipping around with very large platters.
It was almost ten minutes before she got to his table but he forgave her when she looked up from her pad, flushed pink, and backed half a step away. It was a lesson in psychology. She liked the way he made her a sexual object, but didn't like that she liked it.
She looked nervous and that was proved out when her mouth went on automatic. "Hi. I'm..."
"Alice," he interrupted. "I know. I'd like water. No ice."
"I'll be right back with that." Her voice shook a little.
Her legs were magnificent: long and muscular, like a dancer. This skirt was a little tighter than her other one, undercupping her ass. High. Round. Shapely.
She came back right away with his glass but she kept the table between them when she placed it. "What would you like?" she asked softly, her pen poised over her pad.
"Come around here. Stand next to my chair."
"I'm sorry?"
"You asked what I would like. I would like for you to stand next to my chair."
"I didn't mean..."
"I know what you meant."
She hesitated and he knew that this was a pivotal moment. She might just decide that this was a bunch of sexually harassing bullshit. Or she might decide that it was worth the money to be sexually harassed. Or, maybe she liked what he was doing, just a little bit. He kind of hoped for the second option with just a touch of the third.
She glanced around. She smoothed her skirt down, but she couldn't make it longer. Finally, she took the two steps required to stand next to his chair. Seeing that hesitation was better than seeing her in a short skirt.
"What can I get you?" she asked. Her voice was a mix of breathy want and fearfulness.
"Cobb Salad. No bread."
"Red wine vinaigrette on the side?"
"Good memory."
"I'll get that right in for you."
He hadn't had so much fun in years. He opened his book and watched her over it. She glanced his way almost anxiously every now and again but he noticed that her flush hadn't receded. When his salad came, she stood next to his chair, like he had told her to. She placed it in front of him.
"Can I get you anything else?"
He let his hand slip off of his lap He brought his fingers lightly to the back of her knee. She stiffened and he watched her carefully. She didn't object; she did flush deeper. He drew a soft thumb over the back of her leg at the lowest part of her thigh, and then removed his hand.
"Not right now, Alice. Thank you."
She backed away a step before she turned to go. He saw a shine of sweat on her forehead. Then, she hurried away faster than usual.
He ate slowly, taking his time. She filled his water glass twice, always standing next to his chair. He didn't touch her again but he enjoyed her nervousness that he would. When he was done, she took his plate.
"Would you like dessert or your check?" she asked.
"I don't think what I want for dessert is on the menu," he said. "So, I'll just take the check."
She pulled the bill holder out of her apron and left it on the table. He waited for her to walk away and then he put two fifties and a slip of paper with his phone number on it inside it. Then, he tucked his book under his arm and left.
#
She made him wait three days. Three days of imagining what he was going to do to her when he finally got his hands on her. He never had any doubt that he would get his hands on her.
He answered when she finally did call and put her on speakerphone. "Hello, Alice."
"I have no idea why I'm calling you."
Gregory knew. She was horny and broke. "Maybe because you'd like another good tip?"
"Maybe because I'd like you to leave me alone." There was just the tiniest hint of nasty in her throaty voice.
He had to admit, she had spirit. However, he couldn't have the back-talk. "Very well, Alice. It's too bad that we couldn't work something out."
He hung up on her and laid the phone down. It was less than a minute later before she called back. He let it ring for a while before he answered and put her back on speaker.
"So, shall I assume that you don't want me to leave you alone?" Gregory answered.
"Yes," she said softly, clearly humbled. His dick responded like she was talking directly to it.
"Good. I'm going to punish you for that, just so you're aware. Both for talking back and for making me wait three days to hear back from you."
"How?" Again, her voice was that perfect mix of breathless worry.
He unzipped his pants and stroked himself slowly, not wanting to climax but enjoying the lazy pleasure. Besides, his plans were for her to give him his next orgasm.
"And spoil the surprise?" he asked. "You work tomorrow. When is your break?"
"I have one from one to one-thirty."
"At one-ten, go into the family bathroom. Don't lock the door and take off your shirt and bra."
"I can't. That's where I work."
"You can and you will. And when I get there, you're going to suck my cock." He heard her sharp intake of breath and his dick ached for him to pick up the pace. Instead, he tucked himself away again. "I'll see you tomorrow, Alice."
Then he hung up the phone. She didn't call back this time.
#
Gregory watched Alice through the window of the bistro starting at about quarter to one. She had the same section, so he planned on getting the same table. She was wearing the shorter skirt again, which was promising. Still, she didn't know yet what her punishment was going to be; this might be the thing that finally pushed her too far.
At one o'clock, another girl started taking care of her tables. At five after, Gregory entered the restaurant and smiled at the hostess. "I'd like a table but I'd like to use the restroom first."
"Your usual table?" she asked. It was a casual question but her tone made him think that she was flirting with him. Idly, he wondered if he could get her on her knees, too. He decided that the answer was probably yes and probably easily so he dismissed the thought as being unsporting.
"Please," he said.
While the hostess spoke to the server, Gregory went back to the family bathroom. Just before he opened the door, another waitress stopped him. "I think there's someone in there."
"Really?" Gregory said. He knocked, imagining Alice's fear. It was delectable. There wasn't any answer. He popped the door open and poked his head inside. Alice's was topless and her eyes were huge. Her shirt and bra were draped over the sink and she covered her breasts with her arms. He left the door ajar and turned back to the woman. "Nobody in here," he said.
"My mistake," she replied, headed back to the dining room.
Gregory let himself inside and locked the door. "Don't cover yourself," he told her, keeping his voice very low. She took her arms away so slowly, it was almost a striptease. He realized he had been focusing too much on her ass. Her tits were amazing, too.
"We only have about fifteen minutes," he said, "so listen very carefully." He reached into his pocket and pulled out a small butt plug and a tiny tube of lube. Her eyes widened even further so he knew she recognized the little device. "This is your punishment," he told her. "You're going to wear this all day for me."
Her eyes flickered back and forth between his face and the butt plug. "I haven't..."
"At all?" he asked.
"At all."
"Well, then it's worth a little something extra when I fuck you there." She hesitated. "Yes or no?" he pushed, knowing that the time limit was on his side.
Her eyes went back and forth from the plug to his face. "Yes," she finally whispered.
"Come here," he said. She obeyed slowly. "Bend over at the waist and hold your ankles." He noticed that she did it effortlessly, her flexibility noticeable.
He slid her skirt up over her hips. She wore pink panties with a frilly edge. And her ass was everything he hoped it would be. He wanted the view of being behind her while he fucked her but there wasn't time for such fantasies right now. He slipped her panties down only as far as he needed to, and squeezed a little lubrication onto his finger. He rubbed it over he anus and her whole body shuddered. He could have come from that alone.
He put much more lubrication on the plug and more on her anus. Then, being a little rough, he forced the teardrop past the muscles and resistance until it was buried. He listened for her response. A grunt was bad; a gasp was better; a moan was the best. She gave a soft moan and he knew he had her. He twisted it gently and she moaned again. Then, he pulled up her panties and pulled down her skirt.
"There," he said. "Now get on your knees."
She flushed but obeyed. He didn't open his slacks or do anything to help her. Fumbling the slightest bit, she got his fly open and his pants partway down. When she pulled down his boxer briefs, his erection slapped her in the cheek. He didn't plan it but he did repeat it on her other cheek, leaving a smear of precum on both sides.
She hesitated, her lips inches from his dick. She looked up at him with those big brown eyes and miles of lashes, like she hoped he might have mercy on her. He checked his watch very deliberately.
"Ten minutes, Alice."
She took a long, deep breath and licked the tip of his cock. It was all he could do to stay stoic. Then she took him in her mouth. It was satisfaction beyond every other feeling. And it wasn't just the warm, wet envelope around his cock. It was knowing that he could probably get her to do anything he wanted her to. She wanted the money and she wanted the debasement. She was fucking perfect.
She barely managed half of his length but her tongue was enthusiastic enough to make up for it. Gregory wasn't trying to make this last. But he did want to do one thing before he finished.
"Look at me," he ordered.
She did, those big brown eyes still so innocent. He put a hand on the back of her head and slowly pulled her head until his cock was at the back of her mouth. Then he pulled just a little harder until his tip got a little squeeze from her throat. Her eyes watered and that was what he really wanted--those eyelashes in wet spikes because she choked on his cock.
He took his hand away and she resumed, trying to take him deeper. It didn't take more than a minute longer before he felt that tingle. He pulled his cock out of her mouth, working himself roughly, her saliva a nice lubrication. She made a move, like she was going to stand but he put a restraining hand on her bare shoulder. She froze, her breath still coming fast. He left a hand on her, just in case she had other ideas.
He hadn't ejaculated since he first saw Alice so he had quite a load to get rid of. When he came, he did it on her tits. There were ropes of the stuff splashing on her chest and dripping down to her navel. Her lips were agape; her eyes were wide; he relished how much he had shocked her.
"Clean me off," he said. Again, she moved to stand and again he stopped her. "With your tongue, Alice."
She flushed but obliged. And her enthusiasm made him wonder just how dripping wet those cute, little, pink panties were.
"Very nice," he finally said. She stopped and he helped her to her feet. After all, it was the gentlemanly thing to do. "I'm leaving. You have about five minutes. Lock the door behind me and..." He smiled at her. "...don't forget to wash your hands."
She looked stunned, which was a tremendous turn-on. So was knowing that his plug was still in her ass and probably would be all day, like he told her to. So was knowing that in ten minutes, she would be out in the dining room waiting on him, probably horny as hell if her tongue-work on his cock was any indication.
He turned and left, waiting a moment to hear the click of the lock. Then he went to his table and sat down. A young woman took his coffee order but it was Alice that brought it. She looked almost the same as she ever did with the exception of a little muss to her braid. He thought he noticed a little tightness to her walk, but that could have been his imagination.
And the most arousing thing was that she didn't seem one iota less frightened.
"Cobb Salad?" she asked in a low voice, standing next to his chair. "Red wine vinaigrette on the side?"
"No, I only came here for dessert today." He saw her pen tremble. "Coconut cream pie."
"I'll get that for you."
He finished his coffee, so she had to come back to refill it once. He took his time with the pie, but even so, he only sat there twenty-five minutes.
"Can I get you anything else," she asked in a voice that was almost husky.
"Not now, Alice. Just the check."
She returned with the five dollar check. He put three hundred dollars in cash in it and a note. It read:
You have something that belongs to me. I would like it returned in the condition in which it was received this evening at seven.
Underneath there was an address.
#
She was nine minutes late, and she knocked on the door of his house so softly that he easily could have missed it if he hadn't been listening for it.
He opened the door and looked at her sternly. "You've made me wait again."
"I had to take a bus," she said. "It was a longer walk from the stop than I thought."
She lifted those big eyes to him and her lower lids held tears. It was the most luscious thing that Gregory had ever seen.
"I'm barely done punishing you for one thing and I have to punish you for another." He said it like a dare and opened the door wider.
"How do you want to punish me?" she asked.
"I'm going to spank you." She backed away a step. "Non-negotiable, Alice." She backed away another step. He shrugged and started to close the door.
"Wait."
He waited.
"Can I come in, please?"
"Are you sure?"
"Yes. Please."
He opened the door again and she entered. They went to his living room, all brown leather and dark wood. He turned to face her and she shrank back. It did as much for the blood flow to his groin as the thought of her butt plug.
"Face the wall," he told her and watched as she obeyed. "Bend over at the waist and put your palms flat against the wall." It was an enticing sight, her body parallel to the floor and her arms outstretched to brace her. He slid her skirt up over her hips as he had in the bathroom. He found a tiny hole in those pretty, pink panties, worked his finger into it, and used it to rip them from waist to leg. She gasped but braced against the pull when the fabric came away from her body. The entire crotch was soaked. He bundled them so the wet part was on the outside and tucked them into a pocket.
"You were nine minutes late. I'm going to strike you nine times. Count."
The first slap was stinging and just to the left cheek. "Oh, God," she gasped.
He knew what was happening. Every time he struck, she tensed. Every time she tensed, she squeezed the plug. It was hard to make his voice stern.
"Count, Alice."
"One," she huffed.
He struck her again, this time on the right cheek. A stinging, reddening slap.
"Two." It was like a moan.
His next blow was much harder and was across the middle of her ass. It certainly jarred the plug. She jumped but then she arched like a cat. His arousal was getting painful in his pants.
"Three."
The blows got ever harder, making his palm burn, making her skin red. Her throaty voice got throatier. Her ass rose to meet his hand. It was like she was begging him to hit her harder so he did. Again and again.
"Eight," she counted, her voice a breathy, needy sob.
With his last blow he knew his hand would be sore in the morning. And so would her ass. For days, probably. It was a perfect color and he knew he hadn't left a single bruise. That might come later.
"Nine." She sounded relived.
"There now," he said. "You're forgiven for making me wait tonight. And...." He pulled on the butt plug just a little. She made a mouthwatering, little sound. "I've also forgiven you for making me wait for three days and talking back to me. I'm happy to take this out but..." he pulled again and her back arched. "I would love to fuck you with it in."
"Oh, Jesus," she moaned.
"Yes?" he asked, reaching around to stroke the coppery hair between her legs as he tugged at the butt plug. Her hair was soaked. It was so wet, it wasn't even curly anymore.
"Please."
He left the wet pubic hair alone and, instead, wrapped that long, copper braid around his hand and pulled her head back. "You can beg better than that."
She moaned in that sweet throaty way. "You're not a nice man," she gasped. "I don’t trust you. I don't like you even a little bit. But I want you to take me so badly, I'm going to lose my mind. Please fuck me."
She couldn't have made him harder if she had professed undying love. "Say, 'I'm your personal whore'," he told her.
She managed a sideways look back at him, even with his grip on her hair. He raised an eyebrow at her.
"I'm... I'm your personal whore."
"Tell me that this pussy belongs to me," he said. He left the butt plug alone and slipped his fingers along her slit, pushing two fingers into her. She contracted around him in a pulsing way. He withdrew his hand and opened his pants, releasing his cock. It was already hard.
"My pussy belongs to you." There was a bit more conviction there and it made him harder.
"Beg for my cock." He slid his fingers back along her wetness, slipping them into her and out of her, the moisture dripping over the back of his hand. She was so ready. He pulled his fingers out of her and worked her clit a little roughly. Her hips twitched.
"Fuck... fuck," she gasped. "Please. I need your cock."
The anticipation was so bad it was all he could do to not just drive himself into her right away. "Say that again," he demanded.
"I need your cock."
He let go of her and took her panties out of his pocket. "Open your mouth," he said. When she did, he pushed the damp wad inside. She closed her eyes and it was like her eyelashes brushed her cheek.
Then, he went behind her and rolled on a condom. It was exactly the view of her he'd been wanting, except next time, she'd be naked. He thrust himself into her hard and fast, actually making it more than halfway before her tightness stopped him. He pulled out and did it again, this time buried to his balls. The third time, he twisted her butt plug and she moaned through her panties. If being in her mouth was satisfying, this was utterly fulfilling.
He found a rhythm of twisting and thrusting. Before long she arched her back and pushed herself against him, her throaty moans making him harder. He wondered if he should just come. Leave her wanting. Leave her needy.
For once in his life, he decided to play fair.
He pounded into her even a little harder. Her arms braced solidly against the wall and her legs slid a little wider. He brought his other hand between her legs, pounding her, coring her ass, and touching her until her whole body seemed to vibrate.
"You know," he managed, "you really shouldn't charge me for this one. You're having too much fun."
He took a break from the plug and slapped her ass hard. She tightened around him and he knew she was about to come. His fingers flew; she gave a long, low moan that vaguely sounded like, "Oh, fuck," through the panties. Her body stiffened and tightened. In one, swift, decisive move, he pulled out her butt plug.
She clamped down on him so hard that it took him by surprise. She cried out--really yelled, in spite of her gag, in a surprised and delighted way--and moved in a way that wasn’t premediated. He fought the pleasure and the tingle, but it was like she was gripping him with a hot, wet hand. She cried out again around the panties, pushing herself back against him.
He couldn't hold out; her orgasm pulsed around him in a way he had never felt. He fucked her as hard as he could until he tightened, stiffened, and released. It was utter fucking gratification. He had never been so pleased with himself. He thrust as long as he had enough stiffness to do so. Then, he withdrew and took off the condom, discarding it.
He watched her pant through the panties, not moving from her bent and exposed position.
"Stand up," he told her. She jumped a little before she obeyed. "Open your mouth," he said. She obeyed and he plucked the panties out.
She wore the most amusing mix of distress, satisfaction, and fear. It made him want to see how far he could push her. He imagined the used butt plug in her mouth as a gag...or maybe a bigger one. He imagined coming in that gorgeous hair.
He met her eyes. "Would you like cash now, or would you like for me to add it to your next tip?" What he was really asking was, do you want to end this here, or are you up for another go?
She flushed, still out of breath. "Add it to my next tip, please."
"I like that answer, Alice."
He walked her to the door but instead of opening it for her, he gripped her braid again and pulled her head back until his lips were near her ear. "Don't wear panties on Monday. Understand?"
A breath seemed to escape her before she answered with a trembling voice. "Yes."
"Good girl," he said, letting go of her hair. "Now go home and sleep well."
She gave him another of those fearful looks, this time mixed with confusion. He knew that it was best to be sparing with the praise, but she deserved it this night. And there was all the time in the world for more chastisement.
Anastasia
- 23.10.2021
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- Money
