Amy is in Need of Some Help Ch. 02

Disclaimer: All characters are 18 or above! Characters without specific age are all assumed to be adults.

It's been about a month since Amy got some financial help from Jack as well as a bit of a fun time. She couldn't help but think back on the occasion with a bit of a smile and a warm feeling. Yes, she HAD needed the money but she also enjoyed the way she got it. Sure she wasn't supposed to like it, she knew it wasn't the sort of thing that good girls do but perhaps that's why she liked it so much? It was rather taboo, which made it kinky and she got to feel like a bad girl. The last part always made her giggle and grin and wished she would get to experience it again.

The money had helped of course, without it it would have been hard to get proper food at the end of the month but more than that it had helped her mood. Today it was getting near the end of the month again and although it wasn't as bad as last time she knew it was going to be tough and she felt a bit low. Jack DID say that she could let him know if she ever needed help again and.. well.. she did, in more way than one. Perhaps she should send him a message and see if he would like to stop by again? It was still early in the morning on a Sunday, she had just showered but not quite put all her clothes on, just a pair of white thong and a bathrobe so when she walked by the mirror she did feel a bit naughty texting him while not quite dressed. Yes, she did need something to make her feel good and this was most likely what she needed. If he was in the mood for it, that is.

She grabbed her phone and started writing: "Hi! So you said I could always reach out to you if I ever needed some help again. And well, uhm, I have not quite gotten everything in order again so I was wondering if you'd like some.. coffee.. again? Perhaps today if you're free?". She looked at it several times, nervous before she hit 'send'. Her hands trembled a bit while putting the phone away, biting her lower lip in anticipation wondering what the reply would be. If there would even be one. It didn't take long before the screen lit up and she'd gotten her reply. She snatched up the phone quickly almost dropping it as she wanted to see straight away what he'd written. "Oh, sad to hear that it' all OK with you yet. I'm in a bit of a hurry but I can drop by within 5-10 minutes for a quick coffee and we'll see what kind of help we can sort out..;)". The last smilie made Amy giggle and she could feel a nice, warm tingle going up her spine. Sure, he was in a hurry but that was ok, actually that just made it more fun as it would be even more naughty or so she hoped.

Amy quickly ran into the bedroom to get some more clothes on, although she contemplated for a brief moment to stay in just a bathrobe and thong but she finally made up her mind to put on a rather short white skirt, light blue almost see-through top with quite a cleavage, keep her white thong and put on a white push-up bra to make her breasts look bigger and be in focus. She had hardly put on just a little bit of make up when the doorbell rang and Jack was standing outside.

"Hi!" Amy said with a smile and gave him a hug and offered him to come inside "Let me put on some coffee" she offered as he stepped inside.

"That sounds great, I can't stay for too long though but I do have time for some coffee" he replied with a bit of a grin and his eyes did not stay away from her cleavage, not that he even tried to keep them away. Amy could feel his gaze and had it been earlier she would perhaps have not been too happy but now she enjoyed it, somehow she got back into the same feeling she had last time just before Jack left.

"That's ok, a quick coffee is better than none right?" she replied and walk ahead of him into the kitchen knowing that he would probably have a keen eye on her behind so she made her hips sway a little extra to encourage him. Even though she couldn't see it Jacks eyes were staring at her butt when she walked in front of him, remembering how he had treated it last time. How red and warm he had made it and he couldn't help but lick his lips a bit thinking of how he would like to do that again, and push her further in case she were in need of money again.

As Jack sat down Amy poured them both some coffee, making sure to bend over a bit to expose her cleavage a bit extra hoping it would make him in the mood for some more fun as last time. Somehow she felt the need to be bought, sure she did need the money but more than that the feeling she had of not being in control and being submissive like she had been was something new and exciting. The whole time afterward she had not stopped thinking of it, sure she didn't get physical sexual release but the excitement and the turn on was something else.

As she sat down again she licked her lips nervously, not entirely sure how to being or what to say but after a second or two she thought oh what the heck "So, uhm, you said that I could call you again if I ever needed some more help and well, this month is still a bit difficult so well I.. uh... thought that.." she trailed off a bit looking flustered and blushing some and looking down into her coffee cup.

Jack grinned, sensing he had the upper hand now and that was a position he enjoyed so he slowly took a sip of his coffee and let her be nervous a bit more, letting it build up and perhaps make her a bit more desperate and easy to lead into some entertaining and enjoyable games.

"Yes, you are right, I did say that and I'm glad you reached out. Last time we both seemed to have gotten what we needed out of it so perhaps we can come to some kind of arrangement this time as well.." he smiled a devilish smile, looking at her confident while raising his cup watching her.

"Yes, I had hoped so" she said in a bit more quiet voice, a bit more like a whisper as she felt herself ease into the role and at the same time she felt a warm and nice tingle go down her spine, giving her goose bumps all over her body.

"Well, I must admit that I enjoyed it last time and it was money well spent. I think we can come to a nice agreement today as well even though I'm a bit short on time" Jack replied, finish off his coffee, leaning back in the chair and slowly taking out some money, showing Amy a 10 dollar bill. "Now I don't know how much you are in need of this time but this might be a start at least" and as he held it up he looked at her reactions, trying to gaze how much he can stretch it and how far he could push her today.

Amy bit her lower lip, nodding slowly "yes.. yes it certainly is a good start although I would need more in the end" she said slowly swallowing, wondering what he would require for it.

"Then come over here, this one should give me at least five minutes with your breasts" he said, moving in his chair to make room for her to sit in his lap. She got up on slightly shaky legs but walked over to him and easing herself down into his lap. Pulling down her top and bra to expose her breasts and then starting the time on her phone, putting her arms on his shoulders, breathing "5 minutes".

Jack didn't waste any time, instead he put his hands on your breasts, starting to kiss them, fondle them, licking her nipples at first to get them to react to his whims. As he kept going he got more and more intense, breathing harder as he kissed every inch of her and she could feel her body reacting as well. Soft moans escaped her lips which encouraged him even more. He suddenly grabbed her arms, put them behind her back and held her hands there with one of his, forcing her to expose herself even more and show her that he liked to be in command. His mood for being in control had taken over so with his free hand and his mouth he kept exploring, using her breasts for his pleasure. Which, as it turned out, also meant her pleasure both the fact that he took control and the physical sensation. She leaned her head back, gasping, her body shivering as he had his way with her.

When the alarm sounded he slowly stopped, she didn't quite wanted him to but it was part of the game (besides, she DID needed the money so..). She fixed her clothes, put her breasts away while still seated in his lap both of them breathing hard. "I.. hope that was.. worth it" she breathed heavily, looking at him while he gave her a big grin "oh yes it was, best spent money since last time" Jack replied as he took up another 10 dollar bill.

"Now, even though that was very nice I want something different for this one. 5 minutes making out while I fondle your ass" he waved the money in front of her as to tease her, tempt her with it. She just grinned, grabbed her phone, showing him that she put the timer on and whispered in his ear "You'll have to pull up the skirt yourself, this is a self service place" and she gave him a kiss on the side of his neck as she felt his hands grab her skirts and pulled it up rather harshly.

He started fondling her butt, groping it, his eyes a bit closed, biting his lower lip and drawing a deep breath and clearly enjoying it. Both the fact that he had her butt in his hands but also that he was so entitled to it. He looked at her, she had her arms around his neck waiting for him to tell her what to do, his eyes half open "kiss me" he breathed "and use your tongue" he added in a voice that gave not much room for questions. She did as he told her and as she did he grabbed her ass even harder pulling her towards him.

She could feel him pulling up her skirt, exposing her a bit more, with one hand and the other started giving her some gentle spanks making her moan and whimper into the kisses. Jack enjoyed that sensation, he enjoyed it a lot so he kept at it. Not as hard or as frequent as last time when he spanked her ass red, warm and really sensitive. Instead he wanted to feel the reactions while making her kiss him, that he controlled it.

When the five minutes were up Amy felt her butt cheeks being a bit warm, although not as much as last time for sure but she could still feel a bit of a tingle in them. She hadn't been spanked that much before and she had never really enjoyed the thought but now, this was something very different. It turned her on so much, perhaps it wasn't the spanking in itself? or was it? Perhaps, she thought to herself, she shouldn't think too much on it instead just savor the sensation. She liked it, he liked it and so what's the harm? None, she purred to herself.

"Sooo... " Jack said slowly "are you set for now or do you need some more.. help?" he finished off, clearly hoping that she would need some more aid. He kept his hands on her hips, fingers lingering on the top of her butt cheeks still under the skirt while he looked up at her.

"I, well, it does help quite a bit but if I'm going to have some proper food the last couple of days.." she trailed off, reluctant to ask it out loud she leaned in close to his ear knowing that he would enjoy to hear her beg and sound desperate. Or she thought at least, he seemed to like that and heck why not give it to him? "please, I would really need about 50 more to be completely set. I'll promise to make it worth it, just name what you want" she whispered.

She could hear Jack draw a deep breath, she had been right, he got off on that feeling and she seemed to have hit the spot. That made her feel good, made her feel proud of herself, it wasn't so much that she manipulated her or he used her. They both got what they wanted so it was more a mutual situation.

"50 you say? For that I will have quite a bit more, I'll get to give your ass a bit of a different massage" he said as he took away one hand from her to pull out a 50 dollar bill. She couldn't help it but she missed the feeling of his hand. She saw the money, it was just what she needed, staring at it and nodding slowly "I'll toss in another 10 if those tits come out again" he said and without a vocal answer Amy pulled down her top and bra again, showing her breasts just in front of his face.

Before she could had time to start the timer his face and one hand was giving her breasts some proper attention, making her hands shake so she could hardly get the timer working and she could her his moans while he kissed, fondled and groped her breasts as well as her butt cheeks. She stroked his head while he gave her body his full attention. To think that she got payed for this, it was clearly a win-win for her right now.

Jack moved his hand on her butt towards the crack, making his finger start exploring in between them, one finger got under her thong and her eyes popped open. He had said massaging her ass in a different way, she had thought it would mean more spanking but he had a different notion.

"I don't, I mean, I.. usually, do..I mean" she started to stutter, Jack shut her up by putting one hand behind her head, pulling it towards his mouth and kiss her deep while the hand on her ass kept moving in between her butt cheeks.

Finally his finger found it's goal, her tight butthole. He started to massage it, gently and he thoroughly enjoyed the control and sensation of making her do this. It was almost a bit taboo and that was the good part, it was not quite normal, not really forbidden but still something extra. She closed her eyes and kept kissing him, she started to suck on his tongue to keep distracted as she now really felt like she was at his mercy. It wasn't bad, it was exciting but at the same time just enough scary to be thrilling.

The tip of his finger started to find its way inside and she let out a bit of a mix of a whimper and moan, her mouth a bit open still with his tongue inside meeting hers. She could feel how hard he was from treating her this way. The spanking last time was something he had enjoyed very, very much. This was something even better apparently. It wasn't bad for her, although she normally didn't like things going in there but somehow this wasn't bad. It was even.. exciting she dared to admit to herself. Not the physical sensation but the situation. She decided to act a bit more, giving him more of what he seamed to like. She leaned close to his ear again, moaning, whimpering and whispered "But that's.. that's my ass, I don't do anal" but she made not physical motion to try to get away, letting him have his way. He moaned back, pushing his finger a bit deeper "mmm, you do now" and it was almost a growl that came out.

That sound came a few seconds before the alarm went off, the time was up. A feeling of disappointment came over her, quite a bit to her surprise as she had been treated in this way. Jack slowly took his hands off her, giving her a kiss on her lips. "Mmm, that was something special. I hope you are set for a bit now as I have to go" he gave her a big grin. She took her time to put her breasts back into her bra and top and got off of his lap. "Yeah, I should be fine for a bit now" she said, her cheeks burning red but not only from blushing but also being very, very turned on.

As Jack was about to go out the door he paused a second, looked at her "I hope you know by now that you can always reach out if you need help again" and gave her the biggest grin he could manage. She came closer, gave him a hug and whispered in his ear "of course, I hope you are pleased enough so that you want to hire me again" and when she said those words that moan that was almost a growl passed over Jacks lips and she knew this was not the last time.