A man distributes his lottery winnings, his own special way
John Roberts sat in his truck outside the diner/coffee shop. He was waiting on his first real prospect. This was an idea months in the making, and he was a combination of confidence and nervousness, mostly the latter. The clock showed he was still a few minutes early, and it gave him time to reflect on how he got here.
It all started when he became the “luckiest sum-bitch in the room,” by winning the Powerball lottery. It was very unlike John to play, which made the win even more improbable. After Uncle Sam (taxes) got his part, he was still left with more than $600 million. It was just a crazy amount, and what happened next really spoke poorly of people around him.
First, his ex-wife whom he had divorced for cheating on him with his then-best friend tried (unsuccessfully) to claim part of it, even though the divorce had been final for a year. Next, it was family him never knew him had expecting a handout, then friends asking for a handout. It was just too much. His lawyer suggested John form a ‘blind’ corporation and change his name, which he promptly did. John also bought a home in a gated community thru his company, and proceeded to simply hide for a time.
During this time, John was not idle. He setup a very nice weight lifting room, and hired a personal trainer, followed by a nutritionist. John even paid them extra to come to his home to both educate him in his diet and for training, and most importantly to also not ask questions. Not only that, John underwent the knife, and changed his looks. The idea was never to be an Adonis, but rather to simply blend in. After 18 months, he doubted his ex or his own family would recognize him.
John next took half the winnings and invested them with a firm in nice, safe, investments. John took a small chunk of the remaining, and bought a gorgeous beach home right on the Gulf, after selling the other home in which he had originally hid. He also purchased an extremely nice, new truck. Though he kept the old one so as not to draw attention. Taking what amounted to about a quarter of his remaining winnings, John hired another firm to make much riskier trades. One of those was crypto-currency and the upshot was that John had nearly his lottery winnings all over again!
As you might imagine, during this theme John was nothing if not lonely. Yes, he considered prostitutes, ‘sugar daddy’ sites, and the like, but after his interactions with the general public, he was more than a bit gun-shy. So it was that one day John found himself watching porn, and the idea was born. He was watching one those channels wherein a woman supposedly answers an ad for modeling or the like, and is convinced to do porn. Of course, it’s all ***********ed and totally fake, but it did plant a seed. Were there not ***********ed whores, but rather actual women in dire need of cash, and if so, could they be convinced to spend a few days with him, enjoying their bodies?
The more John thought about it, the more he liked it. He paid a visit to the realtor that sold him the beach house, and he helped him find a nice apartment in the state capitol, about an hour plus away. John was in a good neighborhood, just a bit upscale, without being too pretentious. From there John took a look around, and began to conduct his search. He had a plan. What he needed to find the right lady or ladies, like single mothers or college students with lots of debt. Basically, women that were desperate for a way out.
John spent several weeks going any place he could think of to find a match. Finally, it paid off when John was in a small, family owned roadside restaurant on the outskirts of the city. He had been out every day this week and was about to give up hope. John was finishing his meal when he overheard two women talking in the back about how the tips here were horrible. One of the two girls said that she had to come up with at least a grand to pay for her car, plus she was already behind on her rent and the landlord was threatening to kick her out if she didn't pay.
This was the opportunity John had hunted so hard for, and it was so close. And better yet, the girl with the money woes was his waitress! Actually it would be more correct to refer to her as a lady. Her name tag said ‘Kaitlyn’. John knew she must be at least 21, as the place served alcohol. She was a stunner, brunette hair, and a wide smile with an amazing body with D cup breasts, a nice ass, dazzling eyes and a nice smile.
John looked at her for a moment and answered, "No, I’m am good, thank you. The food was delicious, and your service was great." The girl smiled, pulled out his bill and said, "he’ll be you cashier when you're ready."
John nodded and she walked away. The bill was only $20. He had already planned a way to get her alone to talk to her. John took a pen and wrote down his phone number on a hundred-dollar bill and wrote, "Call me." John put the $120 dollars down and walked out quickly. Now, he had to wait for her to call, if she would call. If not, he hoped he could come back tomorrow and not appear creepy.
John was at the apartment, questioning the whole idea, when his phone started ringing. He took a deep breath and relaxed his nerves. Picking up his phone, he heard Kaitlyn’s voice, "Hi." He answered, "Hello." The girl on the other end sound nervous. "This is Kaitlyn, from the restaurant. The one you give the big tip to. He wanted to call and say thank you for that."
John knew he had her. Otherwise, there was no was way she would call him. He asked Kaitlyn if she was free right now and if he could meet her for some coffee at the local coffee house that was open. He wanted to talk to her about something. Kaitlyn thought for a minute. She didn't want to meet him alone but she would be safe at a public place with people around here if he was a creep. Kaitlyn agreed and John said he will be waiting there for her.
And that brought us to this moment. John snapped out of his daze when he saw Kaitlyn pull into the parking lot in a car that appeared to be on its last legs. He didn't know how much it would take to get her to agree to what he wanted. So, he had ample cash with him in several envelopes. Being tall and muscular, he felt rather safe, despite having all this cash on hand. And unlike the video, that was a onetime thing, he wanted someone long term for the moment until he could get more girls.
John stepped out and met her beside his truck, and he and Kaitlyn went in and had a seat. Kaitlyn sat down in the seat across from him. She was of course nervous, but was reassured that they were in a large public place. Also, he at least did not seem to be a creep, so her plight had brought her here, and she could at least hear what he had to say. "So why did you leave him such a huge tip? And what did you want to talk about?"
John looked at Kaitlyn and asked, "So you want some coffee?"
"No, thank you."
"Ok, he will come clean with you. He overheard your conversation with your friend today, at the restaurant and wanted to help you out."
Kaitlyn stared at John. No one ever helps anyone out for free. "What do you want from me?"
“You are right, in a sense. But how really it all depends on you. Humor me for a moment and tell me, to ‘set the table straight,’ as it were, how much do you really need?".
Kaitlyn calculated everything she was late on - paying her rent, car payment & bills, not to mention the pawnshop, and then have some left over for food. She wasn’t surprised by the question, but she marveled that she was actually considering it
John saw her thinking about everything "So how much to get you all caught up on everything and have a little left for you?"
Kaitlyn looked up, then down, thinking about the figure in her head. She took a deep breath and looked at John. "$2500 to pay off everything, she finally spat out" to earn that much.
John looked at Kaitlyn sitting there, and let her response hang in the air for a moment. He knew he almost had her, just a little push and she was going to be his. Glancing around, he reached into his pocket and pulled out an envelope containing $3000 in hundreds. He counted out $1000 dollars and put it in front of Kaitlyn. John knew that peoplee were greedy. If you pull $1000 and only give $100, they will do anything to get the rest of it. Kaitlyn was no different.
Kaitlyn sat and stared, partly mesmerized. She couldn’t believe what she had just witnessed, but also could not see any other way out. He had just handed her nearly half what she asked for, and it was apparent he had a lot more. She found herself transfixed.
“No, I’m not a drug dealer or in the mafia,” he answered with a smile.
Kaitlyn knew if she could set the tables right, as per this man, she wouldn't have to pawn her items only to go to sleep hungry anymore. Her upbringing had been very hard, and for the first time, she was seeing a large amount of cash, there for the taking. She picked up the $1000 and held it tight in her hand and looked around quickly.
John saw the nervous look on Kaitlyn's face after she picked up the money and quickly put it under the table. He asked her if it would be OK to go to his truck, ironically right outside their window, and talk in private. She would stay on her side, nothing odd, just talk, and for that he would pay her $100. She nodded. He paid her tab, and held the door for her on the way out. After they walked the short distance to John's car, Kaitlyn was impressed with it. She’d never been in such a luxurious vehicle before. Again he held the door, and handed her $100 before going to his side and getting in. Now, with more privacy, he could finally talk to her without anyone overhearing them.
Kaitlyn feeling safer in the car. She started counting the money she had in her hand, $1100 total, and looked at John. "What do I have to do for this?" she asked.
"What are you willing to do for it is the question," John said. His plan was working perfectly.
He counted out and put down another $500 next to her, which she quickly picked up.
Kaitlyn looked at the money and then to John, "stop playing games with me and tell me straight.
What do you want?"
"Look, I just got out of a messy divorce, & I hate going out to bars and clubs. So, seeing as how you need money and I need some company, let's make a deal. How much will you need for the next three weeks, for anything I want?"
Kaitlyn looked at the money in her hand and back at John. "John, I am not a prostitute you can give money to for sex."
John responded "I know a prostitute would only ask for $100 or $200. You have $1600 in your hand. So how much will it take?"
John put another $400 next to Kaitlyn and she quickly picked it up to. "So what do you say?"
"John don't think John can do it for this much."
“OK, tell you what. Earlier you said $2500, and you’re almost there. How about I offer $3000? You could be out of all debt and have money left over for just three weeks of your time. You’ll never beat that offer.”
Kaitlyn looked at the money in disbelief. She never had this much money in her hand before in her life. It was the key her getting back on her feet. "I….I…I don't know. He’ll feel cheap and won't be able to look at myself in the mirror if I do this.” she said.
John knew she was trying to get more money out of him. But he also knew that $3000 was almost too generous. He shook his head and looked at Kaitlyn and reached out his hand and he said, "Sorry, that's more than fair. If it's not enough for you, sorry to waste your time. Can I have the money back?"
Kaitlyn clinched the money tightly in her hand not wanting to give it up. It was the answer to all her problems. Kaitlyn knew that chances like this don't come along every day, and if she had to let John use her body for a few weeks to pay off her debts and have cash left for herself, in the end it was a good deal and if she played it right, no one need know.
Looking at Kaitlyn, John knew he needed to something to make her think of it differently than letting him have sex with her for money. "Okay, let's think of it as a job."
Kaitlyn looked at John, and said, "Ok, what do John have to do in this job?"
John smiled, thinking ‘she’s in the boat.’ And he said, "One, Sex is definitely going to be part of it. From the start, you’re mine.”
Two, we’re going to go by an adult store to pick up some things for you to wear, and a toy or two. You will have to be OK with that, and you will have to be into the sex, you can’t simply lay there.”
"Three, there are bonuses. What do you think?
Kaitlyn look at John, a little confused. She knew she would need to have sex with him, and she had used toys once or twice before. But what would she have to do for the bonuses?
"Tell me what he have to do and how much are the bonuses," she asked.
John smiled. "It's simple. The amount of money depends on the act.” For example, if you cook for me, I’ll pay you an extra $100. A few meals and you’re taking $300-400 total, easy.”
Kaitlyn like the sound of that. It was easy "Ok, that sounds good. But he also need to know that you have protection? I mean, I’m on birth control, but he know nothing about you.”
“I have not had sex in nearly two years. And before then, it was only with one woman, so you’re safe, and at this level of generosity, well, I think my intent is clear.”
She took a moment to process that. Then with a sigh of resignation, she said “Umm...OK. What else?"
John looked at Kaitlyn with a kinky smile. "Now for the real fun part. So normal sex is included - blowjobs, swallowing, doggy, light use of toys, and so on. But for any special thing, you'll a bonus depending on what it is. If you don't like anal, but let him do it you get a bonus. BDSM is a bonus for sure. If you bring in a friend for a threesome, that’s a big one. The more special it is the more money you get."
Kaitlyn thought about it. “You’ve really thought a lot about this, haven’t you?”
“Yes I have” he popped back in a definitive manner.
His prompt response brought an unexpected smile to her lips. He was tall, fit, and not weird or a psycho. She couldn’t believe she was actually considering this, and that she was a bit piqued, "How much is it for a threesome?"
"Again it all depends on the girl. If she is as attractive as you, and as active as I hope you’ll both be, that could be $400 or $600, depending on whether you find her or I find her”
She couldn’t believe it, but she found herself shockingly on board. "When do you want to start?" Kaitlyn asked, already knowing his answer.
"Now," John said and looked at her. "Let's go to your place. He’ll follow you," he said. Then he added "Give him the money. I’ll give you a third each week, starting today, bonuses at end of week".
Kaitlyn knew what he said was for his own good to protect him from her running away with the money. She gave him the money and got into her car. He followed her to her apartment. On the way, she told herself to just think of it as a job, go with it, and live in the moment. On the way, she called her boss to tell him she could not be in for several days, due to a positive COVID result. She knew that would actually buy her closer to two weeks, and truth was, she needed a rest.
The apartment was a bit disheveled. She explained that she had a roommate who would be back later that day. Kaitlyn took his hand and lead him to her bedroom, remembering to live in the moment. She pushed him onto her bed and slowly started stripping of her clothes, wishing she had nicer underwear for him.
John looked on as every article of clothing left the body of this gorgeous woman. Kaitlyn stood in front of John in her mismatched cotton underwear. It was tattered and he knew he would have to fix that. She reached behind her and unhooked her bra and let it fall to the floor, and then hooked her thumbs into the elastic of her panties and pushed them down in one quick movement. John got his first look at her naked. She had long brunette hair, dazzling blue eyes, nice D cup breasts with large nipples, a flat belly and an amazing ass. She had a large amount of pubic hair, which was not to his liking, but again, he knew he could fix that.
Now it was Kaitlyn's turn to see John as he stood up and undressed. She had to admit he was attractive, though obviously much older than her. He was tall and muscular and had a large, very thick dick that was hard and ready to go. At least physically, he was better than she’d had in a while. Nudging him to step back and sit on the bed, Kaitlyn slowly got between his legs, licked John and took the head of his cock into her mouth. He let out a moan.
Kaitlyn had not had sex in a long time. As such, she thought she might as well enjoy herself, and started working up and down John's cock. Sucking and licking each time she would come up and back down. She worked her tongue in circles around the head of the cock. She was good at what she did, and she knew it. She also ran her lips along the side of his big thing while playing with his balls, and this man most definitely reacted.
It had only been about five minutes, but it had been a long time for John as well, and he felt the pressure start to build. "Whoa, I’m going to cum," he said, as he felt the wave rush forward and his cum rush through his cock. John liked that she immediately pulled back, only letting his cock head in her mouth as the first blast of cum shot out.
Kaitlyn took the first blast in her mouth as it hit the back of her throat and tried to swallow it down she pulled his cock out of her mouth as the second shoot come out hitting her face and eye. Aiming that stiffy down while sitting up, Kaitlyn's face and chest were covered in John's hot cum. She got up to clean herself off and quickly returned.
It was good, and he knew it. But wow did John ever want more. By the time she came back with a warm washcloth and cleaned him off, he was basically ready to go again. He led her to the bed, laying Kaitlyn on her back and got on top of her. Reaching out his hands he squeezed her breasts and suckled her tight nipples, getting a good feel of them. Kaitlyn let out soft moans as he pulled her nipples.
As much as John enjoyed eating a good pussy, and intended do that very thing with her, he knew that he wasn't going to go down there until Kaitlyn shaved. He rubbed his leaking cock on her slit, lined himself up, and slowly, he pushed the head of his cock into her, enjoying watching her face change as he did so.
Kaitlyn moaned as John entered her slowly. She was tight but he slid in with no difficulty. After slowly working into Kaitlyn. This man was now buried all the way into her, and it felt great, damn his hide. He pulled out and back in to her again, then again. She moaned loudly as her body yielded to him, and she wrapped her legs around this man to keep that fat cock buried inside her.
John started going a little faster as Kaitlyn loosened up slightly. He could tell she was enjoying it. She began making little whimpering noises. She squinted her eyes, looked up, and began uttering incomplete words. “I..I’m..I….” In response he kept at it, thrusting in even harder. After several minutes of him working in and out of her, his new fuck toy locked her legs and he felt her pussy tightened around his cock, then pulse as she screamed and shook.
After her orgasm, John slowly pulled out of her. He could have had enjoyed the moment, but his mind had other ideas. Firmly yet gently, he turned her around. Kaitlyn got on her hands and knees, with her ass wavering in the air at John. He looked down at her dripping wet pussy ready to be taken. John slowly pushed into her. Grabbing her hips, he started pumping in and out of her. It felt incredible and he was intending to get every penny out of this ass. In fact he spread her ample ass cheeks so he could get deeper and a better look at himself fucking her.
He started going faster in her, enjoying the feeling of owning this gorgeous twat. Slamming into her faster and faster, John knew he was about to cum. He pulled out and rolled her over, coating her stomach and bush with several good ropes of cum.. After he was done he turned and fell next to Kaitlyn.
After catching his breath, John got up and grabbed the money for Kaitlyn. Walking back to bed he handed her the $1000 and lay there relaxing and getting ready for round two. John was going to get his money's worth out of her and tonight was only the start. After such a wonderful fuck, John felt his body relaxing, and he knew he was going to close his eyes, if just for a bit. Looking over, he saw Kaitlyn was happily counting her money. As he lay there slipping off, he thought about how many other girls were out there like Kaitlyn waiting for him.
A short time later, John woke up to Kaitlyn sucking his dick. It was a good view to wake up to. He smiled to himself; it had been a good night. It had been nearly two years since the last time he had been with a woman. Having a gorgeous young college girl was an excellent way to get back into it.
John looked down as he saw Kaitlyn's head bobbing up and down, taking as much as she possibly could. The warmth of her mouth was incredible. John felt the tingling in his cock that said he would soon cum.
John could tell that Kaitlyn was no stranger at sucking a good cock. So he laid back and enjoyed the wonderful feeling of it all. Kaitlyn slowly bobbed her head up and down and played with John's balls as she licked and sucked every inch of John's cock.
"I’m close, Kaitlyn. I’m going to!" He announced, his breath puffing. He grabbed her by her hair and pumped her head on his cock, while Kaitlyn picked up her pace. With a groan that was nearly a roar.
As the first rope of cum shot out and into the back of Kaitlyn's mouth, she quickly pulled out his cock as the second shot hit her right between the eyes on her nose and forehead. After several more hot ropes of cum John was finally done. Kaitlyn sucked every last drop out of John and was now using his cock to rubbing in all the hot cum on her face. Kaitlyn intended to earn as much as she could, having decided to just live in the moment.
"I’m going to go take a shower." Kaitlyn smiled at John as she got up and headed to the bathroom.
John checked his phone and did some research on the shop that he wanted to go to and made some calls as Kaitlyn come back out with a towel wrapped around her.
"What are your plans for the day?" John asked Kaitlyn as she started the female ritual of moisturizing and dressing up.
"he have a morning class. I'll be done by noon." She replied.
"I want to take you shopping to get a couple of things after your class. Text me when you are finishing up." He told her.
John went home to get cleaned up and start looking for better furniture in the apartment he had leased. It did come furnished, but those furnishings had a real bachelor look to them, and he wanted better. He didn't want any females he met this way to see his home, lest they become classic gold diggers. He noted two places that offered entire rooms, and checked their hours before showering. As he was having a cup of coffee, he got a text from Kaitlyn. Her classes would be over soon, and he knew where she would be waiting.
As she got in the truck, he was impressed with how she looked. Kaitlyn had a classic look to her with tight jeans and an old rock concert t-shirt with vans on.
"Where are we going?" She asked once she had greeted him.
"He told you today morning. To do some shopping." He said. "And to have lunch."
On the way to the restaurant, Kaitlyn asked, "John, how does the bonus system work and how much is for what?"
"That depends on what you want to do."
Kaitlyn thought it over. She and he former roommate, now a waitress, had talked about having a threesome before if they ever found the right guy. Kaitlyn knew that she could talk her best friend into it if she tried, but she would have to save that for later when she needed the money.
She needed something she could do alone and right now. There was only one thing that came to her mind, something that she was always scared to try. Kaitlyn looked at John and asked, "How much are you willing to pay for his first time doing anal?"
John looked at her and tried to hide his excitement. He had asked his ex-wife many times before to try anal but it was something she wasn't into and always said no to the idea.
"I need some time to think it over." He told Kaitlyn as he pulled into the restaurant where they were to have their lunch.
As they sat down at their table and ordered their drinks, John looked around and asked her, "Are you serious about your offer?"
Kaitlyn nodded, "What do you think of the offer, John?" She didn't know what the going price was for someone's anal virginity. Looking at him, she thought he didn't look like some rich millionaire so she couldn't ask for a lot.
"How does a thousand sound?"
John thought about it for a minute. He could get something his ex had always denied him. Her asking price wasn't a lot, and he had the money, but he didn't want her to expect a high price every time, nor did he want to reveal that he was a billionaire.
John looked at Kaitlyn, "That's high. Would you be willing to go down to $500?"
"It's something that he have always been scared to do, and he need the extra money, so how about $700?"
John simply smiled and said, “That’ll work.” Then added, “I know he said end of week, but to build trust, he can pay that after. But you can’t stop halfway through. Has to be complete or no bonus…and a hurt butt.”
Again, that rueful smile with a little chuckle. She nodded. "Please be gentle the first time doing it.”
"I’m going to want to shave you. Well partly at least, to his liking. Does $200 for that sound fair?" He asked her. He had in mind a specific design of sorts.
Kaitlyn had gotten waxed before and liked how she felt after and didn't mind getting it done again, so a grand total for today’ activities sounded fair. “You could tie him up during the shaving for an additional $100. But again you have to be gentle down there. Trust issues.”
John nodded, fully understanding what she was doing. But really, he expected it, mostly because this was how he set it up. And he had to admit, he liked it. They were cruising down the boulevard as they talked, but he had to smile at Kaitlyn’s reaction to him pulling into the sex shop. He intended to enjoy his time with his fuck-toy, and that meant a stop here.
Kaitlyn was surprised as she walked into her first adult sex shop. The shop had everything from toys, sexy lingerie to costumes. This man directed her to carry a basket, and he wasted no time in getting quite a few items. They included a big bottle of lube, a butt plug, small and large vibrators. She had never been in one of these places, and it was hard not bluch, especially as saw what he was going to be using on her.
John stopped and was looked at something that caught his eye.
"Which one do you prefer?" He turned to Kaitlyn and held up two collars: an all-black leather one and a pink one with fake diamonds and a long leather leash.
"That one." Kaitlyn pointed to the pink one, and he dropped it with the other items and with a pair of pink fuzzy handcuffs. Curiously he also added an odd, stiff triangular pillow, a water soluble marker of some type, and one of those ball shavers for men.
As they walked around, they stopped at the mannequins that were displaying several sexy outfits. They looked amazing. There was a very sex see-through lace bra and thong thigh-high stockings with a garter belt and high-heeled shoes in black, red, and white.
"Could you show us the red and white outfit in Kaitlyn's size?" John asked the woman working at the store, pointing towards Kaitlyn.
"Sure, sir." The woman beamed.
After getting Kaitlyn's measurements, she came out with the two outfits and their matching shoes.
"Pick out some lingerie," John told Kaitlyn. He ‘helped’ as well, choosing a few thongs for her to wear, and he sneaked some items in as well, telling her not to pay attention to them. Yeah, right.
After paying for everything, John took her to the leased apartment. Dropping a cushion on the floor, he said “kneel”, and she did so. Taking the leash, he attached it round her neck, taking care to make sure it was properly snug without being too tight. Helping her back to her feet, he said “Get that last outfit that we purchased. You know the one. Take it with you and go shower, change into it, then come back here and resume the kneeling position.” He then nonchalantly turned and flipped on the TV.
After 30 minutes, Kaitlyn came out of the bathroom in her new all-white outfit. White satin and lace bra and panties with matching garters and hose. The bra was open, showing her pink areolas and eraser pink nipples, and she must have understood the intent, as she wore the panties over the garter straps. John looked at her and was amazed at how sexy she looked in it, especially kneeling that like that. Worth ever penny, he thought to himself.
"White was an appropriate choice since I’m going to lose his anal virginity soon," Kaitlyn told him. She smiled, seeing his reaction to her dressed like this.
"It is, isn't it." He said as he turned towards her. At his motion, she stood and stepped over to him, turning so that he could view her properly. She liked that this man, though obviously older, was entranced by her.
"Turn around." He motioned with his finger. Her juicy ass looked perfect. Reaching out John placed his hands on her ass and slowly rubbed them up and down before giving her a hard squeeze. He then handcuffed Kaitlyn's hands behind her back and turned her around. Attaching the leash to the collar, he led Kaitlyn to the bedroom. Without being told, she knelt on a pillow similar to the one in the den.
John smiled at her as he undressed. His fuck toy was just as he preferred her, and his stiff cock most certainly showed it. He put his cock to her lips, and she opened her mouth. He slid his cock into her open mouth and slowly worked it in and out of her. Her tongue and the warmth of her mouth was incredible.
John grabbed her head and started to go faster. With every stroke, he was forcing his cock deeper into her mouth. Kaitlyn closed her eyes tightly as he was going deeper into her. Kaitlyn's eyes started to turn red, and she was beginning to choke and cough as he was pushing down her throat. Tears started running down her cheeks.
Holding on tightly, John kept pushing in and out of her. She finally couldn't take anymore and tried pulling away from him. But John continued his relentless assault on her. Finally, he stopped and pulled out of her mouth. Kaitlyn immediately hunched over and started wheezing and coughing.
John gave her a moment to catch her breath. When she looked up at him, he pulled the leash, letting her know that she had to stand up. Pushing her firmly against the wall, he kissed her deeply, while tugging and pulling on her nipples. He also rubbed his stiff cock on her satin panties, and liked the way she moaned. It told him that he was the one in control, again just as he liked it.
John then uncuffed on hand only and lay his fuck-toy back on the bed. Taking a bit of soft coil rope he re-cuffed her and tied her hands over her head. He then stripped off her white panties, and ran his hands thru her her thick pubic hair, smiling. “My my, someone is enjoying this” he said, dipping his fingers down and into her wetness.
Kaitlyn had to admit that she enjoyed being dominated like this, no man had ever done that to her. She was surprised she enjoyed it so much. Even when she thought she would vomit from his dick being thrust in her mouth like that, there was an odd sensation that excited her. She was living in the moment and realizing how much she enjoyed that.
From the nightstand this man reached over and retrieved a small bag. He did this while nibbling and suckling a nipple, and it made her moan. ‘Mercy this feels incredible.’ She thought. From the bag, he produced the marker, the shaver, a towel, and a small ‘bullet’ type vibrator. ‘???’ Kaitlyn again understood, and lifted her hips to allow the folded towel to be placed under her.
His touch now greatly excited her, and it was all she could do to keep from orgasm. This damn man first used the shaver to greatly thin her pubes. He did this slowly, occasionally teasing her sli and the around her clit with the tiny vibrator. She was panting when he finally stopped, and just above her clit drew a…heart shape?
John thought it was coming out just right. Removing the guard, he flipped the little shaver edge-on and proceeded to remove the hair outside the marked area. In between each step he continued to tease her with the vibrator. Now a bit of cleanup work with the rotary razor, and he was done. His fuck-toy was panting loudly now and looking at his desperately, making him smile yet again. Control achieved.
Putting all the items back in the bag and removing the towel, John said “PERFECT. Just what what he was looking for!” Sliding one hand up her inner thigh he added “Now for being such a good girl…” and thrust two fingers into Kaitlyn’s sopping wet pussy. With his thumb he barely had time to run her swollen red clit more than a few times before she arched her back and had a massive, convulsive, screaming orgasm, her pussy clamping around his fingers.
All the pent up lust of this encounter made Kaitlyn have what was hands down one of her most intense orgasms ever. The orgasm seemed to roll for some time, but what was even more intesnse was that, after she finally relaxed, this man then took what apparently were a pair of long sashes that he had staged on either side of the bed, and bound her knees up and out, forcing (Not that he needed to) her sex to be open to him.
John lined up his cock and pushed into his fuck-toy, slowly working in and out. He started with a steady rhythm. Above her in missionary, he braced with one arm with playing with her nipples with the other, and alternated back and forth. His fuck-toy was squinting and twisting her head. Looking down at his dick sliding in and out, he saw it was quickly getting covered in Kaitlyn's juices. It had a shiny coat on it, and a white ring of cream was starting to form around the base of his cock and her lips.
Soon the room was filled with the sound of both of their moans of pleasure as her man’s dick slid in and out of a very wet Kaitlyn. As more and more of Kaitlyn's cream gathered around his dick, she arched her back and let out a scream as her pussy clamped down tightly onto his cock. The feeling of being bound like this was like no other, and a second orgasm rocked her. After she relaxed, this man pulled out and had Kaitlyn roll over the large triangular pillow beside her.
Her hips were now higher than her head, and she was in doggy style. She felt him run his hands over her ass and give her a nice squeeze, then spread her ass cheeks apart. She was sure it was to access her butthole. He then grabbed the lube and the butt plug from the bag. He applied a small amount to her and the plug.
"Relax. When you feel it on your anus, push back, almost like you’re in the bathroom" He told her as he slowly started to work the plug into her tight little hole. John’s fuck-toy yelped, twisted, and moaned, but he like that she did as she was told, and after several failed attempts, John finally got it into place, looking at the pink diamond at the end of the plug with a smile. John reached back and gave her a playful slap on her ass.
He then took hold of his cock and pushed it back into her sopping we sex. As he grabbed the leash and pulled it back, he started moving forward and backward into her. John placed his hands on her hips and started to move faster and faster. Kaitlyn was moaning louder every time he would bottom out inside her. The plug made her want to tighten, and he was thick, so it was mildly painful as he plunged into her, but it was pain she was enjoying.
John started to feel the tingling sensation as his balls started to get tighter. The view of the red rose butt plug moving as he pounded his fuck-toy was too much, and he slammed into her one last time as he started to flood her. Fuck-toy locked up in response to John cumming inside her, and her twitching and yelpls told him he’d pushed her into a third mini orgasm. Looking down, John saw a mixture of both their juices had slowly started leaking out of her.
Releasing her from her bonds, this man removed the pillow and they both lay there next to each other breathing heavily trying to catch their breath, looks of satisfaction on both their faces. After laying there for several minutes, Kaitlyn got up and headed to the bathroom to get cleaned up. As she was wiping away the last bits of cum leaking out of her, she thanked God for birth control. She came back into the room holding a bottle of water for John.
They lay there for a time, basking in the good feeling. John was thankful that while she was cleaning herself, he had the presence of mind to pop a blue pill. Not that he would normally need it, but this was turning into an exceptional day.
"You never told him what you did for a living," Kaitlyn said.
“No, he never did. Like he said, not a drug dealer, not anything illegal. he pay a premium to avoid questions.” Giving her a smirk a nudge he whispered “in the moment.” And rubbed her nipple.
Kaitlyn said, "he have to admit, this has been so far above his expectations, it isn’t funny. You definitely know how to hit a girl in the right spots. But between your ‘generosity’ and your stamina, he find it hard to buy that this is your fulltime place."
“been looking for better, he will admit.” John replied. Wanting to change the topic, John asked "Are you ready to go again?" He asked her.
"How do you want him?" Kaitlyn asked.
"Doggy would be the best way to go."
So she got on all fours on the bed. Although the triangular pillow was there, she was at the moment off it. She had her curisotu again piqued as this man attached some straps to the pillow…then a vibrator with a large mushroom head. Seeing it excited her. With that sexy ass waving in the air, John grabbed the bottle of lube and put a generous amount all over his cock.
Reaching out, John pulled out the butt plug from Kaitlyn and set it down next to them. Looking down at her little, pink asshole slowly closing back up, John smiled to himself. He was finally going to check one off the bucket list. And a gorgeous woman, at that..
John placed the tip of his cock to her asshole and slowly started rubbing it up and down to get it ready for him. John had a little trouble getting the tip in at first, due to her being nervous and keeping her asshole tightly closed.
But finally, after she had relaxed, John quickly slid in a quarter of the way into her. He stopped to give her time after hearing the scream as he entered.
Kaitlyn's eyes had closed tight as she felt him enter her backdoor. She pushed back as before but the pain wa very much there, as this man was much thicker than the plug. She clenched her teeth and held the bedsheets tight in her hands from the discomfort she was in.
Her ring did not only open to him though, but she found that it accepted the thicker part of him as well. Despite her pain and the shriek she let out, she was still good with it. The pain and discomfort slowly started to fade. Opening her eyes and looking up at him, she took a deep breath and gave him a slow nod to let him know to continue.
After getting the nod, John knew she was ready for him to continue. He slowly pushed into her an inch at a time. John was now halfway into her as he pulled back slowly so that only the tip was left in her, and then pushed back in her. He kept doing this until he was all the way inside of her. It felt incredible.
John stopped once again to give her time to adjust to his size after seeing the look of pain and discomfort on her face. Standing there buried deep inside of her, John loved the feeling. He so owned this piece of ass.
"God, you're so tight." He groaned. He could feel every muscle working and moving around his cock. Unlike her pussy that had loosened up the wetter she had got, this would stay tight for him. John slowly started to pull out and push back into her. After several minutes, Kaitlyn started to moan in pleasure. He took this as a signal to pick up his speed. A little faster with every thrust. " You ok?" He asked her.
Kaitlyn nodded.
John then buried himself deep inside her and, flipping on the Hitachi vibrator attached to the pillow, he pulled that back and into her. As he changed to grinding circles, he heard the wetness of his fuck-toy on the vibrator. Her annular ring was now squeezing the base of his shaft, so he knew he could do this for some time.
Kaitlyn had gone from pain to lustlfu pleasure, and when she fund herself pushed against the vibrator, she couldn’t help it. She had one more orgasm. It wasn’t as loud or convulsive as the others due to her being tired, but it was intense just the same.
John grabbed her hips and thrust into her faster and faster. He made this fuck-toy cum yet again, and he was nearing his limit as well. With force, he gave her ass cheeks several hard smacks that got a scream out of her each time. John reached out and took hold of her long hair in his hand and pulled back on it lifting and pulling her head back. He then moved his free hand and reached under her to cup her breast and give it a good squeeze as he thrust into her.
John released her hair and breast and grabbed her arms next, and pulled them back. Kaitlyn was now only on her knees, barely balancing, as he started going full speed slamming into her. John knew he couldn't go anymore, the blue pill had done it’s magic. He slammed deep into her several more times before he dumped his load in her, replacing the plug once his sofetening cock slid out
He then released her and let her fall on the bed. "I’m going to go take a shower now, but when he get out, you are to towel dry him, and then we’ll get dressed" John said, leaving her lying on the bed.
John liked how this gorgeous woman toweled him off, kissing his dick, then helped him dress. Only then was she allowed to dress herself, and she seemed fine with that. John could smell that she was cooking something delicious. John sat down at the table just as she placed the food down. As they ate, he noticed she had a funny look on her face every time she would move.
John looked at her and asked what was so funny. Kaitlyn looked up at him with a small smile and a scrunch of her nose. "It's funny how every time he move, he can feel your cum moving around inside of him. It's a new feeling."
This got a laugh out of him. After their meal, he asked her how her first anal experience had been.
"It was good. he don't think he would have liked it as much as he did. he'll definitely do it again."
On the way back over to her apartment, John liked that she flipped up the center console and snuggled up to him. He was very much getting his money’s worth. At her place, John handed her an envelope with $1000 dollars. “When you get inside, remove the plug. he’ll text you our next play date.
John stopped at the grocery store near Kaitlyn's apartment to pick up some items that he was out of at home. Walking around and picking up what he needed, John saw a Latin woman a couple of years younger than him. She looked pretty, but he could tell she had been working long hours and was stressed out. Walking past her, he heard her talking on her phone. She was getting angry.
"We can't afford it right now! I’m having a hard enough time just paying the bills." She was telling someone on the phone angrily. "We'll talk about it later."
Getting a good look at her, he saw that she was skinny but had the biggest ass he had seen in a long time. Walking around the store and getting the last items he needed, John ended up standing behind the woman that he had seen earlier. She turned her head and smiled at him.
As she was to pay for her grocery, her card was declined. She looked in her bag for cash but didn't have any.
"I’m so sorry. he'll have to go and get the money from home." She told the cashier.
"Add her items to his tab. he'll pay for them." John stepped up and announced.
The woman looked at him.
"You didn't need to do that."
John smiled at her, "It's no problem, really."
After John got done paying, they both walked out together. As she got to her somewhat dilapated car, John stopped her.
"Do you have a minute to chat?" He asked her. "he have something he’d like to discuss."