Delivery for Jess

I hope you enjoy this story, my first for Literotica. If the subject matter - mainly Femdom - is not your thing, please move on and read more of the thousands of wonderful stories on this site. If you do enjoy a, fairly light, Femdom theme, then please read on, and let me know how well, or badly, I have written. Constructive criticism is always appreciated!

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Delivery for Jess.

Dan Green was having a great day. At 53 years old and fairly fit, he enjoyed his job, especially when he didn't have too much to do. The weather was warm and sunny and he was almost finished his work as a delivery driver, and it was only 14:30.

"One stop left" he thought to himself, "66 The Curve," a house he hadn't been to before, but he knew where it was -- one of those older houses that had the front doors round the back. He had already planned in his head how the rest of his day was going to go; back to the depot, straight home, masturbate, Shower and then relax on the patio with a beer or two. Dan smiled. Life, today, was good.

Counting down the houses to stop outside the right one, Dan noted it was one on the end of a row with an alley down the side between the hedges. He stopped as close as he could and went round to the back of the van. "Darn," he thought "three parcels. I'll try to take them all in one go, save coming back." Collecting the parcels from the back of the van, he had a long thin box, a little bag and a shorter but squarer box. "I can take the long one under my right arm, grab the bag and get the other under my left. No problem." He managed to slam the door and auto-locked it.

It was only when Dan started to squeeze through between the hedges he realised the parcels were heavier, and trickier to carry, than he had first thought. He kept going getting faster, with shorter steps, hoping to get to the gate before they slid out of his arms.

Dan made it to the gate and, looking for how it opened, noticed a young woman in the back garden. She had seen him and was walking across the back lawn.

"Wow" thought Dan, staring at her. Long black wavy hair, framing a very attractive face, tight red skirt and a black mesh top with a black half cup bra underneath, holding, what looked to Dan, like a pair of large full breasts. Her legs looked great too, a bit of muscle rippling as she strolled across. Dan was staring so much he hadn't noticed she was talking to him. "Sorry, I didn't catch that" he said.

"I said, I will take them from here" she replied, reaching over the low level gate.

"It's OK" said Dan, still staring at her breasts "I can bring them through." The woman looked at him, not smiling at all at his continuing gazing at her breasts and took the biggest of the three parcels over her shoulder. Dan was surprised because that was the heaviest of the three, and he felt a bit of a fraud with the two lighter ones.

She marched up the path ahead of Dan and placed the long box against the back door frame of the house, and turning, said to Dan "You're early, I thought you were not due until after 3pm and on the app it said we were your last stop."

"Yes, you are" replied Dan, depositing the two boxes on a table in the back yard. As he turned he saw the woman had crouched down to inspect the box she had carried, giving him a view directly up her skirt, revealing a pair of light blue lacy panties, which looked like they were more lace than material. Turning back round, the woman caught Dan staring again. That pissed her off once more with him regarding her as just a body in skimpy clothing. He needed to be taught a lesson.

"Are you finished now?" she said, forcing a smile onto her face, "Can I get you a cold drink? It's early and I am sure you are hot." It was probably the heat and not just the embarrassment at being caught staring twice that had made Dan's face red!

"I need to get back" Dan replied, while still staring at the really sexy looking woman.

"Nonsense," she replied "you have finished and I am sure you have time for a drink."

Dan was wavering -- the woman was indeed gorgeous, very sexy looking and seemingly not upset by his staring. "OK, OK," Dan said "I would be delighted."

I bet you would, thought the woman.

"I know you can't have a beer, what would you like?" she said. "We have Coke, Orange, Water and probably a can of something else in the fridge."

"Anything will do" replied Dan. As the woman turned to the fridge, she glanced back and, YES, sure enough he was staring at her ass in the tight skirt. Fuck this, she thought, I am doing something about his attitude.

Handing over a can of Pepsi, the woman said "Here you go, by the way my name is Jess. Those parcels are for me -- a new bookcase. Would you be good enough to take them through to the 2^nd room on the left, that's my bedroom."

"Of course" Dan replied, "I'll take the long one first and then come back for the others."

Jess smiled to herself. She was confident she had read this guy right and would be able to correct his behaviour once she got him into her room.

Selecting a wooden spoon from her utensils jar, she placed it down underneath the back of her skirt waistband, the tightness holding it in place, and followed Dan through to her room. He was still putting the boxes down at the side of her bed, and rested them against the wall, in the corner. As he turned back, Jess was right in front of him, smiling. "Do you REALLY have to go? It would be nice to get to know you better!" Dan looked at her, looked at the bed, and back at her again.

Now, Dan was used to seeing lots of women on his routes, and in this weather, some wearing extremely skimpy clothing -- it was a perk of the job at this time of year, and made up for the crappy winter weather. He was not used to a really sexy woman who appeared to be coming on to him offering what sounded like a better option than his own plans. "If you put it like that, I would be very happy to accept" Dan said, smiling back at her, again looking her up and down, undressing her with his gaze. This didn't happen to people like him, he thought. She could not be more than 25 at the most, and was, very, very sexy indeed. He liked long, black, wavy hair, and the way Jess wore it, was beautiful.

Still pretending to be happy with Dan's attitude, Jess pushed him down onto the bed, and giggled as she fell on top of him. Twisting herself round, she whispered in Dan's ear "are you up for a bit of fun?"

Dan, still in wonderland about the speed things were going, asked "What do you mean?"

"Take your trousers and boxers off" she said with a glint in her eye "I think this might be an afternoon of fun." Dan hurried to take them both off and then laid face down on the bed again, Jess returning to her place on his back. Smiling broadly, Jess brought her hands back out from under the pillow where she kept her "man-acles" and dangled the metal cuffs in front of his face "How about these?" she asked, arching her eyebrow, "it will be so much fun and who knows where it might go!"

Dan looked at the cuffs - they looked very realistic - and then at Jess' face which was studying him intently. "Oh, OK then. Never tried them before, but, hey.. What's the worst that can happen?" What indeed, mused Jess!

"Are you ok with this?" Jess checked again, and moved to place Dan's left wrist in the cuff.

"Yes, I'll trust you. You seem like a trustworthy girl." Jess arched her eyebrow again as the cuff closed, and she moved Dans right arm around his body placing his wrist next to the restrained one.

"Last chance" called Jess. "No?, ok, here we go." The cuff closed on Dan's right wrist and he was restrained, hands behind his back, with Jess perched on his ass.

"Now then" said Jess, "what do we do now? I saw you gawking at my tits when I came to the gate, then you were looking at my crotch when I crouched down, and then you were staring at my ass when I was getting you a drink from the fridge. Do you think I enjoy being stared at like that -- do you think ANY woman would? I think you need to be taught a lesson, naughty boy." Dan tried to look round to see if Jess was being serious or joking about. She sounded annoyed.

A sharp spank on his left ass cheek made him jump. It wasn't hard, but enough to make him think. Another spank, this time on his right cheek brought a sharp cry "Careful, that hurt a bit!" Jess ignored the little outburst and spanked the left again. Again and again she alternated spanks to each ass cheek, slowly bringing a pink tinge to both. Dan had got into it now and was gently moaning, trying to twist out of the grip her legs held onto his sides. Jess was facing Dan's ass and while spanking his ass, she was moving slightly further up his torso with each hit. Soon she was sitting squarely on his shoulders and twisted to smile down at Dan.

As Dan looked up, he caught Jess looking at him; there was a glint in her eye he hadn't seen up to now. "I think you are enjoying this more than me" he said.

"Oh, I sure am" she replied, "and I think it's time to start your punishment for ogling me."

"Come on down here" said Dan "we can have a nice cuddle. You have spanked my ass enough." Jess grinned, but did not move.

Slowly she drew the wooden spoon out of her waistband letting Dan see it as she brought it up to her chest, moved her body round to face his feet again, and with a sharp lash whacked his left cheek again.

"OW!, OW!" Dan reacted immediately trying to twist from the grip her legs held onto his body. "That hurt. I thought you had punished me already, and we could relax with each other." Jess looked down at him, smiled, and turned back to smite his other ass cheek. "OW!, fuck me, that hurt too."

"Stop whining" Jess countered, "I have barely touched you. Do you not think you deserve a proper punishment?" Dan went silent, sulking, as he thought his afternoon would turn out better than this.

Jess had been smacking the spoon on Dan's ass for a few minutes and there was a nice colour on his cheeks. It was time for her to ramp it up a bit. Spinning round on Dan's back, Jess backed up a bit then slid her hands under his body feeling under his shirt for his nipples. A sharp retort to her firm grip told her she had found them. Dan yelped and started moaning again. "Come on, whiner, stop the fake crying, you are enjoying this aren't you? Don't you like a bit of nipple play?" Jess' fingers kept up their grip on Dan's nipples, twisting but not with great force.

Dan was in two minds now - he was enjoying the attention, and the slaps and hits on his ass were not painful any more, just a sort of warm feeling which wasn't bad at all. This wasn't going as he thought, but there was no denying that, in his brain at least, he was not unhappy with how things were progressing.

He had tried domination games with his wife when they had been married, and he did prefer when she dommed him, to him domming her. It wasn't a big part of the marriage and he had not had chance to explore further as she preferred being dommed by him and did not want to be the one in charge. He was having trouble understanding where Jess was coming from though. Was she annoyed with him, as she professed, or was she just playing with him.

"Have you learned your lesson," asked Jess, "or do I need to continue? It is really annoying to just be ogled and leered at by men."

Jess was still twisting his nipples, just keeping his interest, so Dan decided to see if she would increase his pain to a level where it would turn him on even more.

Trying to buck her off his back, Dan twisted on the bed and attempted to roll over. "Oh no you don't," exclaimed Jess, riding his back as he tried to twist from under her. "I haven't finished with you yet. Do you think I am playing, or am I serious?" Dan knew his next response would determine where this went. Jess pressed her hands onto his shoulders keeping him face down on the bed, awaiting his response with anticipation.

Dan was confused how he wanted this to progress. He thought he was onto a good thing which then turned into a bit of female domination, but he was still not sure how far she was capable of punishing him. He had to admit she was a gorgeous young lady, he would love to fuck her at any time - given the chance - and he was no longer hurting. BUT, she had led him, in his mind, into this situation under the pretence of wanting sex with him.

"I don't want you to stop, but am not sure what you want." he said "I didn't mean to ogle you, but you are so gorgeous, I couldn't help it. But what you are doing is not turning me on, if that is your plan."

"Whoa, hang on! You think I am doing this to turn YOU on, to have you fuck me, so that I can have an enjoyable time with you? NO, NO, NO, that's not the plan! You ogled me, You don't get to dictate how things move on. Did I give you that impression? Let me clear this up for you. I was planning on just teaching you a little lesson, but that has just got much more serious, because I really don't think you understand how demeaning it is for women to be just candy for men to ogle."

Pressing down harder on Dan's back, Jess scooted forward until she was sitting on the back of his neck, forcing his face down into the bed cover. Spinning round again, she manoeuvred herself so her knees were pressing on Dan's biceps, holding them immobile by his sides. Reaching to her left, to her bedside table, she retrieved her hairbrush and laid it on his back between her spread thighs. "Now, if you want to scream, please do!" Jess said "I think the neighbours are at work, and we are the only people in here, so there is nobody coming to help you. I don't think you are going to enjoy what's coming!"

Dan realised, at last, that she was serious, a view reinforced when a searing pain erupted on his left ass cheek. "OOOOOOOOWWW, FUCK, FUCK," Jess heard as Dan woke up to her recommencing his punishment. "That fucking hurts, a lot." Although Dan's speech was muffled by his head being rammed down in the covers, Jess understood every word, and smiled at the intended reaction he gave out.

"Right, lets get this done." shouted Jess, removing her mesh t-shirt. Dan would have been delighted to be able to see as more of her fantastic body was revealed, but in his current position that was denied to him.

Jess brought the hairbrush down again, this time on Dan's right buttock with as much force as she could muster. "OWWW!" yelled Dan, "please stop."

"Nope, not happening." she replied and laid down another stroke on his left buttock.

On and on she went, laying down stroke after stroke on Dan's unprotected ass, with his protestations growing louder. After 5 mins, his ass was reddening up nicely, after 10 mins it was starting to glow red, and then, after 15 mins of continuous spanking, and Jess' arm beginning to ache, Dan's ass was bright red all over. His yells and protests had subsided into tears and crying after only a few minutes, and he was now sobbing into the bedsheets.

"Stay!" was all Jess said, as she dismounted his back and stood at the bedside, flexing her arm to give the ache some relief. As she was about to go to the kitchen to get herself a drink, she heard a quiet voice say "Thank you, Miss."

"What?" Jess stopped.

"I was wrong to ogle you like I did, and you were right to punish me like that," Dan continued, "and, although it hurt so, so much I appreciate you for doing it. I have been guilty of ogling women and I now see it was wrong. Please would you forgive me?"

"I think you need to do more, before I can forgive you." replied Jess, "How much do you want forgiveness?"

Dan considered his reply, as his brain could think of nothing to offer. "What can I do?" he asked.

"That depends on how much you want to offer" Jess replied "I will only forgive you if you show me you really are sorry - if you choose to accept serving me in any way I see fit."

Dan was taken aback, and, although his ass still stung a bit, reminding him what Jess was capable of, the opportunity to serve a beautiful young lady, with, let's be true, a fantastic looking body, seemed more like a priviledge than a punishment. "I don't want to be bargaining with you," Dan countered "but how far are you prepared to go - what does "any way you see fit" really mean?"

"That's down to how well you learn." Jess replied, an enigmatic smile on her face, "How much you can take to please me, and if you REALLY are trying to prove you can change." Jess stepped forward and undid the cuffs on his wrists. "On your knees!"

Dan rubbed his wrists to relieve some of the pain whilst considering his position, gazing first at Jess, then at the floor. "Come with me!" she said, stepping aside to allow him to leave the room, "Lead on, I want to see that bright red ass leading the way!" Dan moved forward to the door. "Left and then right into the living room," Jess called helpfully, "and stop by the sofa. I will be there momentarily."

How far should she take this, Jess mused? She knew what she was going to do, but did she want an older man as a submissive - not really! Hmmm. Would Mom want him - again probably not, even though she was a forceful woman, more direct and, maybe even more sadistic than Jess, which just left her younger sister, Molly, who was only 22 and who, Jess thought, showed no signs of being either dominant, nor submissive. Not sure she would even know what to do with a submissive!

Jess removed her skirt and shoes leaving her in just bra and panties. "No" she said to herself, "lets see how well he can keep his eyes to himself." and removed her bra. Her bra-less tits held up beautifully, a perfect 34D with larger than average nipples, a few shades darker than her breasts. Looking in the wardrobe mirror, she decided she looked fabulous, far too good for the old man in the living room. "Still," she muttered to herself, "I need to make him understand, and naked will be quicker!"

Dan was waiting in the living room, wondering where she was, whilst looking round the room. It was not a big room, and the furniture was not new, but there was some style to the decor. He was waiting by the sofa with his ass to the door, and, thankfully, could not be seen by anyone outside as the windows were either too high, or beyond the furnishings. All this kneeling was not great for his knees, he thought to himself, but before he could either sit or stand, he heard Jess come into the room behind him.

"I think I did a nice job there." she said, staring at the semi-naked man in front of her. "Shirt off!" Dan obeyed and was now down to just his socks.

"Right, this is how it works," Jess started. "You took up the last 30 mins or so of my time, so you need to make it up to me."

"Are you married?" Dan replied in the negative.

"Girlfriend?" again a no from Dan.

"Boyfriend?" Jess giggled. Again a no.

"So, nobody at home waiting for you to come home? "

"Just the dog!" Dan replied.

"SmartAss!" she thought, but smiled.

"I need to rewind after that little workout, and guess who volunteered to help me do just that?"

"I guess that would be me" replied Dan, turning his head to look at her as he spoke.

When he saw her, his brain couldn't believe what his eyes were seeing; she was naked, well nearly. "Eyes front and down." Jess called out.

Dan managed to look away from the absolute Goddess behind him. In just her bra, her tits had looked fantastic, now, naked, the image was burned into his brain, and it was even better than he had thought it could possibly have been. Dan felt his penis getting hard.

Jess walked round the near naked man and took a seat on the sofa, setting up the cushions behind her so she was comfortable, but sitting somewhat upright. Dan kept his eyes down and could only see her feet - rather nice, shapely feet he thought - nails painted a light blue which, he remembered, matched her panties.