Tipping

This story depicts mature sex, if this is not to your liking, please visit some of my other submissions, otherwise, I hope you enjoy it.

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"Can I take your drinks order?" a soft female voice on his shoulder made Kieran spin around.

He came face to face with the largest chest he had seen in a very long time. His eyes paused before they looked up to see the young waitress smiling at him. Being an early developer meant that Chelsea had gotten used to men staring at her tits, at least he had the good manners to look abashed and adjusted his eyeline accordingly. "Errr yeah" came his stuttered reply "Two beers and a zero cola please."

She turned on her heels and went to get their order but Kieran couldn't take his eyes off her amazingly round butt. She was maybe 5 5 in height and carrying her weight perfectly. Her silhouette, while not slender, tapered beautifully to fleshy full rounded hips, the black skirt was short atop black tights/pantyhose but it was that tight black top with a plunging neckline that Kieran couldn't shake from his mind's eye. His two lunch companions were continuing their jovial banter without him as he appeared to be in a world of his own just remembering how full, round and tempting they looked.

There was that voice again, "There you go gentlemen. Are you ready to order food yet or would you like some more time?" Kieran sat there shaking his head trying to clear it but said "Yes, I think we are ready" and the three read off their preferences with Kieran going last. The food was served promptly and additional drinks were ordered which were also delivered promptly. Kieran had excused himself from the table and made his way to the toilet when he spotted the young waitress in a side alcove preparing a pile of serviettes "Hello. I just wanted to thank you for the very efficient service today and I feel I need to apologise for my earlier reaction when we first met. I can't imagine how much you have to go through" as he inclined his head down to her chest.

Chelsea smiled and replied, "Thank you for the compliment, it's always nice to serve well-mannered guests and as for that, well least said, soonest mended."

On the way back from the toilets the girl was still alone in the alcove so Kieran stepped up to her and said, "I'll make sure there is a suitable tip to apologise. I hope it's alright, I'll pay you cash so that you don't have to declare it to the rest of your team, your boss or the taxman." He then pulled a wallet out of his pocket and produced several notes from the pile.

"Thank you" she bowed slightly sounding gracious adding "It all helps, especially this time of the year."

Kieran was enjoying being in the presence of such a beautiful young woman let alone that magnificent chest. From a young age, he had always been a breast man but those in front of him defied description they were so full and round. This was the point when inspiration struck, "Would I be correct in saying you are only paid the regional minimum wage?"

Chelsea nodded "Yes, it's the best I can do at the moment. Beggars can't be choosers."

Kieran pondered for a moment before committing himself "Look I'm a businessman and people around here know me for my no-nonsense approach to business. I appreciate I'm significantly older but I have a proposition for you that I will pay you a year's wage in cash in one hit. Interested?"

Chelsea was flabbergasted "Hell yes" was her instant reply but then her gaze changed to scepticism "What would I have to do? I'm not going to do anything illegal am I?"

Kieran smiled back at her; she was on the hook. "No, it wouldn't be anything illegal. It might stretch some morals a little but I can assure you it is legal."

Her suspicion remained "It can't be anything regular for that kind of money."

Kieran was taking heart that she hadn't said 'No.' Let me turn it around and ask, "What would you be willing to do for that kind of money? Think of the bills it could pay?"

'What wouldn't I do for that kind of money' Chelsea contemplated, 'What is he after?' and so she asked, "What would I have to do for that money then? You are the no-nonsense guy."

Kieran smiled, he was enjoying the cut and thrust of the negotiation, "Okay I'll spell it out blatantly. I want to fuck you." Chelsea's jaw dropped at his flat delivery, as she was momentarily speechless Kieran pressed on "I think you are an amazingly sexy young woman. It's a bit of an ask but I work on the assumption of 'if you don't ask, you don't get.'" He held his hand up defensively as he concluded "I'm sorry if you think I have insulted you, I merely wanted a good time and appreciate I'm considerably older than I would need to sweeten the deal with the unsavoury topic of money. I will offend you no further, leave you with the generous tip hopefully to make amends for the offence and wish you well."

Chelsea watched him turn and retreat away from the alcove. 'How did she feel? I should feel insulted but that amount of money, blimey!' She remained riveted to the spot until a colleague came around the corner jolting her out of her reverie. Despite already personally handing her a handsome tip, Kieran's party still left a generous tip on the table to be shared with the staff.

After the other two had started towards the exit and thanked a number of staff for the service Kieran deliberately held back to whisper to Chelsea "Thank you and I hope I didn't offend you earlier." He didn't wait for a response and made off towards his two associates. Chelsea got on with the rest of her shift, albeit in a bit of a haze, and made her way home after collecting her share of the tips. She only had a one-bed studio apartment in the seedier side of town to get back to so she stopped off at a convenience store to purchase a cheap bottle of vodka to take back with her. The proposition troubled her more than she realised once she was alone with just her thoughts for company and her sleep that night was certainly disturbed and patchy. Her colleagues noticed how distracted she was and a few even asked if she was okay.

A week to the day Chelsea was on shift again and she found Kieran sitting at the same table but alone this time "Hello" he greeted her as she came up to the table. "This is a very pleasant surprise for me. I'd like a zero cola to drink but haven't made my mind up on food yet."

Chelsea greeted him with a distracted "Hello, I'll do that for you right away." As she retreated towards the bar Kieran couldn't help but watch her beautifully curved bubble butt which was once again accentuated by the uniform they provided.

She came back a few minutes later with his drink and Kieran read out his order. Before she could step away, he sheepishly asked "I'm so glad you are so professional. I hope my improper proposal last week didn't offend you. It still stands by the way."

"Errr... errr, no... it didn't" replied a flustered Chelsea before turning and taking his order to the kitchen.

Kieran enjoyed his solo lunch and made his way to the toilet in his usual manner. On the way back Chelsea was returning from waiting on another table and Kieran halted his path so she could enter the alcove in front of him. He was about to proceed back to his table when he heard a faint "Errr, could... could I have... a word with you" Chelsea asked.

Kieran took a step back towards the alcove and replied "Of course, what can I do for you?"

"Well," she began but then paused, "it's about last week," Kieran said nothing at this point but responded with a questioning raised eyebrow and waiting for her to continue. She was looking down at the floor but Kieran could see her cheeks colour up "I don't want you thinking I do this very often but... well... how do I say this... Your offer last week, well I'm a little short of funds at the moment, well always if I'm being honest and my apartment can best be described as scuzzy" she trailed off at this point.

Rather than continue to let her squirm Kieran saved her blushes by responding, "You were wondering if I were serious last week?" She now looked up into his face with her deep brown eyes which seemed almost pleading and so he continued "Yes, I was and am serious, I think you are amazingly beautiful and sexy but know young ladies your age rarely go with men my age out of free will. Look if you are in Financial dire straits then I could always give you another generous tip without you having to betray your pride; I'm not that heartless. I'm Kieran by the way and you are?" He held his hand out to shake.

She followed suit nervously stating, "I'm Chelsea." She let go of his hand and looked down at her feet once more as she mumbled: "I can't accept charity, that would be worse on my pride but I'm desperate and so... I'll do it." Kieran was floored at this point, assuming last week's proposal was dead in the water. She then looked up with a determination in her expression "I want it understood I'm doing this to get out of my crummy apartment, I don't want you thinking I do this sort of thing, like ever." Kieran held his hands up in defence but before he could respond she continued "I'm not doing any rough stuff, no cuffs or ropes or gags and definitely no spanking am I understood?"

The response was a little shocked at the turn of expression "Err, absolutely, I'm not into that kinky shit either. In an attempt to set some boundaries, can I ask if you do anal?"

Chelsea raised her voice slightly when she responded immediately "Absolutely not."

"Okay, okay; message received, I'm pleased to say my conscience is absolved slightly. I didn't want to feel like I was taking advantage of you but it sounds like it will actually be empowering for you and so I promise to help where I can find better lodgings; I have some contacts that might turn something up. I'll state from the outset that I will treat you with the utmost respect at all times. You are a precious work of art. Does that calm your concerns?"

Chelsea had visibly relaxed at this point as she replied "It does thank you. I think you are very nice, certainly very generous but I too don't want to feel that I'm taking advantage of you but we appear to have reached an equilibrium. When and where would this take place?"

Kieran winced at her clinical tone, "You state when, might I suggest at the end of a shift perhaps? The where can be arranged at either my place, my office or on neutral ground at a hotel which I'm happy to fund. It really is up to you to dictate the things that make this the most acceptable for you. I want it understood how much of an honour this would be for me, you are majestic."

"Let me think about it and I'll come to see you at your table" Chelsea stated.

Kieran half turned to leave but then stepped back saying in a low voice "I really can't thank you enough for doing this."

Chelsea watched his back as he went back to his seat. 'Could I do this to just anyone?' She debated 'But then our interactions have been very different than with any other customer. Above all I can kiss goodbye to that horrid apartment and even more scuzzy area.'

Chelsea made sure that she was the one to serve Kieran for the remainder of his visit and when it came time to settle the bill, he left a healthy tip after she had confirmed "I finish at 4:30 tomorrow, book a hotel and send me the details, here is my number. I will be leaving details of where I will be so no funny business."

Kieran smirked at that last comment and replied "Smart girl, I like that but rest assured you will be in completely safe hands, I like being served by you and wouldn't want anything to jeopardise that. I see a bright future ahead for you. Here is my business card, during your break, I'd spend some time doing some checks about me and my company. It will reassure you that I'm legit and above all I'm a man of my word. I suggest you bring a change of clothes; I'm thinking of taking you out for dinner so you can be on the receiving end for a change."

During the afternoon Chelsea received a link to the hotel he had chosen and was pleased to see he had booked an upscale one although she still rang them during her break to make sure the booking was above board -- it was. The allotted time arrived and she made her way up to the room number Kieran had sent her. She knocked and the door was answered straight away. Kieran was on the phone and he beckoned her in while he finished up. "Do you mind if I jump in the shower? I could do with washing the shift out of my hair."

"Of course, it's that way" Kieran pointed but then bashfully asked "The screen is clear, would you mind if I watched? You are truly amazing and it would be a turn-on to see you in all your glory. No funny stuff I assure you, I just want to watch and admire."

Chelsea looked at him aghast but then concluded 'He's going to see me naked sooner or later' and so shrugged as she said "Okay if that is what you want. I don't want to get all clinical about it but we did agree a price."

Kieran jumped up and headed towards his briefcase, extracting a bulging envelope "I thought cash would be best. The taxman takes enough out of me and my business and so don't see why he deserves a further cut. I suggest you count it."

Chelsea leafed through the various notes in the envelope, looked up and smiled at him "It looks all in order. Something tells me you wouldn't scrimp on such things somehow." She placed the envelope at the bottom of her overnight bag and then extracted her toilet bag and headed to the bathroom. Kieran followed a few steps behind and held the door open while she removed her outer clothing. His trousers tented at the prospect of seeing this particular young lady in the raw and he wasn't disappointed.

She looked good in her underwear even if it had seen better days and he made a mental note 'I'll make sure she gets some new stuff. She was certainly worth the expense.' Chelsea performed the requisite clean but on seeing Kieran's rapt attention decided to give him his money's worth by performing the same routine but looking in his direction. He saw her looking and smiled back saying "You look amazing" he stepped forward to hand her two large bath towels and while she did that job -- making sure he was given a good show again -- Kieran fetched and held up a white dressing gown, helping her put it on once she was dry. He stepped back into the bedroom and offered "Can I get you a drink from the mini-bar?"

"Mmmm, yes please, Vodka and Coke." Chelsea asked. She was warming to the man even if the situation could still yet go south; she wouldn't let her guard down fully.

She noticed him pour two measures of the same drink and offered "I'm sure this is still feeling a little strange for you, I know it is for me. To make sure I haven't drugged the drink, I'll let you choose your drink and I'll take the other." Once she had done that, he made sure to show him taking a drink before she did the same. He patted the edge of the bed next to him and as Chelsea sat, he began "You'll find in the envelope a business card of someone I've had dealings with, he's waiting for your call to see if there is a nicer pad in a nicer neighbourhood that might interest you if you were serious about finding somewhere new."

"Wow, I wasn't expecting that" Chelsea replied.

Kieran looked apologetic as he said "I said I was a man of my word. You are a very special individual who deserves a hand-up in life. I don't know your back story but can guess it isn't good to have ended up here. Assuming we get on well tonight I have some other things to offer you if you'll let me help you. It implies no commitment from you by the way, that money is yours to take and you need never speak of this again, I know I won't divulge the details to another living soul. This remains between the two of us." This was all panning out better than she could have hoped but his words about her back story struck a raw nerve. She ducked her head down and her shoulders began to shake as she started to cry. He reached over and put his arm around her saying nothing for a while but eventually said "If you want to talk, I'm happy doing that. By the same token, if this is all getting too much pressure for you, we can end it here with no bad feelings."

Chelsea remained quiet for some time before wiping her nose with the long sleeve of the bathrobe as she said "I'm sorry about that. I didn't mean to put a downer on events." She drew in a deep breath and asked, "Where would you like to start then?" She opened the front of her dressing gown to display her beautiful, full breasts "Should I give you a blowjob or something?"

Kieran chuckled as he replied, "I have no idea how you start these things either although there is something I'd really, really like to do." Chelsea sat staring quizzically back at him waiting for him to continue. "I'd like you to remove your dressing gown, lie back on the bed with your head on the pillows and then opened your lovely legs. I particularly like licking pussy, would you mind?"

In fairness Chelsea was a little floored, she had assumed she'd be making all the moves to earn her money. She slowly removed the gown and scrambled her arms and legs to position herself as he had requested. With him seeing her in the shower she had gotten over the initial uncomfortableness of him seeing her, especially when he had been so complimentary about how she looked. She rearranged the pillows so she could easily see as Kieran wriggled up the bed between her outspread legs. His focus was purely on her sparse hair pussy as he ran an experimental finger along the lips and up to her enflamed clitoris. It wasn't the largest he had come across but it stood proud, waiting for his attention.

Craning his neck forward Kieran engaged his tongue along the soft furrow to swirl his tongue around her clit and then down her splayed labia. Chelsea was far from a virgin but this man was being so gentle compared to her previous experiences. The sensations shooting around her nervous system started as small tingles but as he stuck at his task for a good twenty minutes the sensations intensified until she was humping her pelvis up and down to intensify the contact. She was thrashing her head from side to side as her hands clamped the back of his head to push down against her pussy until finally she went rigid and came.

Kieran was still cleaning her juices from his lower face as she stirred slowly, her vision still not fully clearing "My god" she gasped, "I thought I was the one meant to be looking after you?"

He smiled up at her and chuckled as he said "You were, you're delicious. How do you fancy going for dinner across the road and then we can take our time in the room afterwards?"

"Err, yeah, if that's what you want" Chelsea replied still not fully recovered but went along with Kieran's plan. It was actually nice to be on the receiving end of good service although Chelsea couldn't hold back commenting on what the young waitress ought to be doing. Kieran tried to get her to open up but something was still holding her back so he didn't push the matter. He picked the tab up for the meal even if Chelsea did offer.

When they got back to the room Chelsea pushed Kieran backwards and settled down between his legs kneeling, she announced "Now I get to return the favour" as she pulled his zipper down and freed up his dick. It was a pleasant surprise as she expected maybe he was lacking in that department if he had to proposition young waitresses, maybe, just maybe, he truly was enamoured with her looks and body after all. She went to town using all the tricks she had picked up over the years but her next surprise came when he pulled her up to the bed when she was only halfway through.

"That can wait, I need to sample that delicious pussy" he announced as he arranged her once again lying back in the middle of the bed. Chelsea was actually looking forward to this -- it had ceased to be a business transaction after she saw his reaction to her naked body in the shower. He knelt but it was Chelsea who reached down and positioned the spongy head of his dick at the entrance to her pussy. She looked up into his blue eyes at the exact time as he pushed forward and entered her she fluttered her eyelids reacting to his movements.