Amy Is In Need Of Some Help

Disclaimer: All characters are 18 or above in all my stories even if age isn't strictly written out! (people with apartments, cars etc are assumed by logic to be above 18)

Amy was sitting at home, a bit worried. The last couple of months had been tough, the bills were piling up and they did not match up really to her income. Unsure on how to get by right now she knew better times were soon coming but she had to get there somehow. She sighed, trying to cheer herself up as she soon would get a visit from a friend and she didn't want to burden him with all her troubles.

As she got up she went by the mirror, smiling a little. At least she was quite pleased with herself in that regard, not as fit or slim as she had been in her early 20's but that was no surprise as she was getting closer to her 40's. But still, her brown eyes glittered most of the time, her dark hair was well kept and shining. But something she was quite proud of was her cleavage, she thanked her mom for gifting her with such a big and nice pair of breasts. Some women don't like it when men in particular have trouble looking them in the eyes, Amy didn't mind. On the contrary she often wore clothes with cleavage to tease and get some attention and smiled (and laughed on the inside) when she noticed that they had such troubles keeping focus. Sure, she wasn't as slim but her breasts had grown larger as she herself added on a few years so that was just a bonus.

While not slim she had curves, something also drew some attention and she most of the time dressed herself in a skirt or a dress to enhance that look. It made her feel at ease and she enjoyed playing on the feminine side of things.

while she was standing in front of the mirror her friend, Jack, rang the doorbell and she hurried to open. He was a couple of years younger but taller than her. His hair was somewhere in between long and short, some wild curls but they were there on purpose. His blue eyes met hers and he gave her a hug as he always does. He was, as stated, taller than her but also larger. Not in the sense of just big but she could feel that he was rather strong and well kept, as he took pride in working out quite a few times per week and keeping himself in better shape than most his age.

"So how are things?" he asked as they were going to the kitchen to grab a cup of coffee. He, of course, could not quite keep his eyes away from her cleavage and when she walked in front of him his eyes went down to her butt and then he stared a bit more openly when she couldn't see it.

"Well, honestly, it's a bit tough. You know, getting things to add up at the end of the month" she sighed, wondered why she really was telling him. She didn't plan to but she felt so relaxed in his presence.

"Oh? financial problems are never fun, that can make you stay awake at night.." he replied with a look of sympathy

"Yeah, I mean things will get better pretty soon, I just have to get there!" Amy said with a wry smiled

Jack took a sip of coffee and looked at her "No way of getting some extra income? Get an extra shift or two?" he asked

She shook her head and sighed "no, wouldn't really make that much of a difference as I need the money within a week or two. Was thinking of trying to find anything to sell or so to get cash directly but not sure where to begin" she looked down, fingering her cup before taking a bit long sip.

"Mm, not easy doing that either especially when there are things you might not want to part with but instead selling them because you HAVE to" Jack said softly, thinking as he was trying to come up with a solution for his friend.

"Yeah, sadly I'm not that young or good looking or I could have sold kisses! Those are easy" Amy laughed, trying to cheer up the conversation as she felt she had brought him down so much which was not her intent.

"Oh, don't say that! You're pretty, beautiful and those who say otherwise are plain wrong!" Jack laughed back, realizing what she was doing and tried to follow and bring the conversation to a more fun place.

"Nah you're just saying that to be nice" Amy sighed, not quite in a good spot yet but still in a sad, negative mood

Jack pulled up a 5-dollar bill, put it on the table with the intent of giving it to her regardless just to help out but in an effort to make her feel better he said "Here's how much I would pay for a 5 minuter make-out session so see, you're wrong I'm not just saying it to be nice!" He said with a smile and pushed it over to her.

Amy stared at it, she WAS desperate for money and well Jack wasn't bad looking quite the opposite. Kissing him wouldn't be a problem at all and well, if it would get her the money that would be a big help. Not much money but clearly more than none! So she took out her phone, set the time for 5 minuter, took the money and said "OK, you got a deal, 5 minutes starts now.." and she pressed 'start' on the phone. Jack stared at her for a couple of seconds before he realized that she was serious and moved over and quickly started making out.

He put his had on the side of her head, their lips met, his tongue slowly went into her mouth finding hers. Rather quickly he took charge, kissing her deeply like he had just bought the right to it. Which he indeed had and even though Amy felt weird, she knew it was wrong but she still couldn't help but enjoy it. Thinking that someone thought she was good enough to actually pay to get kisses from, when she wouldn't have minded kissing him for free. She knew it should have made her feel bad but instead it made her feel powerful, well she had to let him get what he paid for or it would be rude and not part of the deal.

After 5 intense minutes the timer made a sound and they broke it off, panting and both smiling, enjoying it their own way. Amy felt like a winner and Jack got to make out with her, triggering his dominant side in a way he hadn't thought of before.

"So.. "he said, breathing hard, licking his lips and clearly wanting more pulling out a 10 dollar bill "this one for making out with your tits for 5 minuter" pushing it towards Amy, more slowly and teasing her, making sure she knew he could take it back. She was staring at it, twice as much as what she got before but then he demanded more. Her hand crept towards it and then quickly grabbing it.

"Ok, 5 minutes!" Amy said and with a shaking hand fixing the timer again, starting it and this time Jack didn't waste any time. He pulled her into his lap, pulling down her top and snatching her breasts out of the bra, starting to kiss them, fondle them. He buried his face in between them, nibbling at her nipples and kissing them all over. He was less gentle and more demanding this time than when it was the make-out session. Not that she really minded, it was turning her on, it made her feel good AND she got some money.

As he was having his way with her breasts his cock twitching, growing and making a huge bulge in his pants and she could feel it. It made her nervous but at the same time it turned her own, that good looking guy like him would get so horny by giving her pleasure was what was going through her mind. He on the other hand was turned on by the dominant aspect of it, he felt like he owned her for this period of time, that he had all the rights in the world to play with her big, beautiful tits and that turned him on like crazy.

After the 5 minutes had passed she moved away, covering her tits again but she was breathing hard, panting this time as she was quite turned on by the treatment. He was grinning from ear to ear and breathing equally hard if not deeper.

"So, that was not so bad was it?" Jack smiled at her and finished his now cold coffee

"No, not at all" Amy purred, thinking that she enjoyed it AND got some money and clearly he enjoyed it thoroughly. She could easily live with the fact that he acted like he was entitled to touch her, after all she did agree to it and somehow she also enjoyed how demanding and dominant he was.

Jack was thinking, looking at her, now studying her body rather openly "Are you all set now? Have you.. earned.. enough to get you by"

Amy was thinking, even though it was a nice addition but not really and she shook her head "No, it's better but doesn't cover it all the way" she sighed a bit and intentionally heaved her chest making her breast get more focus hoping for something more.

Jack wondered how desperate she was, or how willing she was to act desperate rather so in order to see if she would catch on to a little role play he pulled out a 50 dollar bill showing it to her without putting it on the table.

"Would this get you there?" he said with a bit teasing voice and a grin to his face.

The face on Amy was either showing an act of desperation or it was the face of true desperation "Yes.." she whispered, staring at it with big eyes "what.. uhm, do you want for that..?" she kept her voice lower than before and she kept her eyes focused on it.

"A spanking, 20 slaps on your naked butt. And you get it once we're done, you can stop whenever you want but if it's less than 20 it's no deal" he looked her straight in her eyes while showing her the money. He had wanted to see her ass naked for quite some time and he WAS in a dominant mood.

She licked her lips and swallowed then nodded "I'm not sure I can keep still, and I'm not so used to being spanked so I might whimper.." she confessed. Hearing that Jack laughed "as long as that doesn't cost me extra, I don't mind" he replied with a wink.

She blushed a little, she was still excited but this was more than making out and she got up when he motioned for her, taking her hand and bending her over the table. "Now let me see what I just bought" he said and now she clearly heard the difference in his voice, from her gentle, kind and calm friend to someone who was in charge and expected his commands to be followed. It made her nervous but at the same time it turned her on. She knew he wouldn't hurt her for real and stop if she asked him to. She slowly hiked up her skirt, revealing her butt in just a small black thong. She paused a little,even though much of her was exposed she wasn't quite naked. "All of it.." he said and she quickly pulled down her thong just below her butt cheeks.

He started caressing her skin, gently, softly, warming her up for a little bit. Or he was just taking the opportunity to touch her a bit extra before saying "Now start counting, if you loose track that's on you, if you try to cheat and count quicker there will be no money" and without giving her a chance to reply the first slap landed and she yelped out a "ONE!" and then the second landed on her other butt cheek "TWO!" and a third "THREE!" she was breather quicker now and she felt the skin stinging and the sensation of his hands were still upon her skin as the next slap landed.

He kept going until 10 slaps have landed before he paused and caressed her ass, gently, softly almost like he was comforting her. She was breathing quick, the last couple of slaps made her whimper and grasp the side of the table hard. Her noises just turned him on more, when she noticed she let them out louder. It turned her on that he liked it and in a way when she told herself that she owed it to him since he bought her it just turned her on even more.

"Now, get ready for the second half" he said in a low, calm voice and at once started again. Harder this time, the first landing on her right butt cheek "11!" she cried out, "12!" as the next landed on her left. He was hitting harder now, wanting get more of a reaction from her and he knew he just had some slaps left.

"16!" she cried out and her right foot left the floor, "17!" followed just after and she almost raised up when she felt a hand between her shoulder blades keeping her bent over. "Ssscchhh, it's almost over.. just a few more. Don't ruin this now" he said in a voice pretending to be nice. "18!" she panted out, breathing so hard now "19!".

He took a little break, savoring the moment, seeing how she was nervous to get one more but wanting it to be over, looking back at him while he admired he now red and warm ass, his creation. Then he gave her the final slap "20!" she breathed out a huge sigh of relief. He kept stroking her now warm, red and stinging butt cheeks and it felt good. She was whimpering, panting but somehow it also felt good. She had endured it, she had earned it. After a few minutes he pulled up her thong and let her skirt down, she was almost disappointed but it was the term they had agreed upon.

Once she raised herself up he handed her the money, gave her a kiss on her left cheek and whispered "you did good". Those words tingled in her spine, not only did she get money it also made her feel good. She had gone from the feeling of being in power to a submissive state but she didn't mind, on the contrary it was a nice change. And she had noticed something in Jack that she didn't knew was there. Jack on the other hand enjoyed the feeling of being in charge, of not having to feel bad for it since they agreed upon it.

"Now you might be set for a bit" he whispered in her ear as he kissed the other cheek "and thank you for the coffee, you can let me know if you need some more..help in the future" he said with a grin. Amy couldn't help but blush and giggle a little. Well blushing on the outside and giggle on the inside, she had some dignity left at least! But still she could hardly get a word out as he gave her a hug before leaving, her ass still felt like it was on fire reminding her of what had happened.

Jack on the other hand thoroughly enjoyed the feeling, smiling as he hoped she would ask for help soon again.