Rich Bitch Games: Naked Lunch

Dani felt anxious as she pulled up to the hotel. This would be her sixth time pulling this little stunt, but even then it always made her anxious before the excitement set in. She stepped out of the car and took the ticket from the confused valet. Danielle probably seemed a contradiction to him-hot blonde driving the cobalt blue Mustang convertible yet wearing sweat pants, a sweatshirt, and flip-flops on this warm summer day. Her lips curled in a playful smile as she headed into the hotel.

See, the 20 year old Dani was a tease in the worst possible kind of way. Her and her friends all came from families of considerable wealth, and they were bored. Rich, bored, and hot was always a dangerous combination and these girls clearly decided that they were going to take advantage of their situations to have some fun.

In her case, Dani spent a lot of time online in adult chat rooms. She would seek out guys locally, or at least local enough to have some fun with. It wasn't just any guys though, she had specific targets she was looking for in her victims. They had to be at least twice her age and married-the older and unhappier they were the better. She'd tease them along with pictures (suggestive, but never nude) until they were begging to meet her.

Once she had them to this point she'd pop them over to her kik account. When the idea of a meet came up Danielle offered what amounted to the perfect bait for these married, unhappy, desperate older guys. She always suggested a lunch date that took place in a hotel room. Dani would show up and immediately strip upon entering the room, eating lunch completely naked with them. If the conversation and the like worked out enough then they'd get to play, if not, they got to eat lunch with a naked 20 year old who would do a few last poses for them before she left.

The real devious part of the plan was that she never intended to play. She chose her words carefully in that she might if things were right. One of the conditions of the game her and her friends played is anything promised had to be performed. Having that "if" condition in there saved her a lot of headache, even if it teased many guys.

Granted Dani didn't just tease through online chats. The girl had a profile or two on sex themed social networking sites. Again only fully clothed pictures with the occasional tease, but even with her "friends" there she teased-emailed coupons for everything from a blow job, to over the knee spankings, to anal sex. By the rules she'd have to perform any of them if she ever met the guys, but all of them were far enough away that it was never a concern that she'd have to live with.

You probably don't need any help to see where this is going. Dani had no clue what was about to befall her as she knocked on the door of the hotel room. It opened a moment later and the portly older guy, who looked every bit his fifty years of age, opened the door wearing only the hotel bathrobe. "Courtney?" he asked.

Dani nodded and pushed past him entering the room. The girl wasn't dumb enough to use her real name, so she had adopted the persona of Courtney Jones for some of these little meetings. 'Courtney' was having her fifth lunch, and was about to be five for five with leaving guys excruciatingly disappointed.

The petite blonde quickly shed her flip-flops before reaching down and pulling the sweatshirt off. She was of course naked underneath the sweatshirt, and the portly man was probably stunned to see that she wasn't wearing a shirt or a bra. When 'Courtney' came to have a naked lunch, she came prepared.

Before she even looked back at the man, before he could even comment her sweatshirt was on the floor quickly followed by the sweatpants, which she had left intentionally baggy enough that just untiing the drawstring would allow them to fall to the ground. From the backside, from the man's view she had an impeccable body-slightly tanned save for only a small line where she obviously wore a thong, a tiny, tight looking ass, and perfectly smooth legs.

Dani walked over to the table that had been set up and already had some food on it. That was another obvious requirement of the naked lunch, food had to already be delivered and it would be served by the guy. The twenty-year-old couldn't help but smile at the table. It was her first time in this hotel and so she didn't expect the in-room table to be made of see-through glass. 'Well played Simon' she thought as she turned to sit in the chair.

Simon for his part was grinning from ear to ear. Courtney was certainly a hottie in his eyes. He thought he was in heaven when he saw her tight, firm looking ass, but as she sat down some of the most perfect tits he had ever seen came into view. A b-cup or a c-cup, they hung just naturally, jiggly enough to make him wonder if the girl had ever really worn a bra. They were just slightly tanned like the rest of her skin except for that perfect little tanline. Smallish nipples that were already at attention certainly got his attention.

"A drink?"

She nodded. She had told him to have some champagne. Her specific request was a $200 bottle that was of course nothing to her, but a bit biting to these guys she liked to play catch and release with. She was the cat, and these guys were the unwitting mice in her life.

The lunch conversation was non-existent. Simon wasn't all that attractive, and all he seemed to be able to do was mutter out a few words here and there, mostly about the food. The food was at least pretty good, one of the better manicotti Dani had eaten in a long time. But even in trying to be a little titillating and trying to get something going she found herself quickly bored by this guy.

Mercifully, they were both done eating after only fifteen minutes. She hadn't even asked for a refill of her champagne, it was a clear sign to herself of how badly she just wanted to get out of there. Dani stood up to finally give the guy a full frontal view of her body, and Simon's eyes immediately darted to her shy little bare pussy.

"So, obviously you didn't really talk during the lunch, so yeah, I don't feel like playing is the best thing for us. But in interest of fairness, is there any way you want to see me before I leave?" she asked him in her best cooing voice, hoping the combination of her body and voice would leave this guy just so stunned (and hard) that his brain wouldn't work.

"Cou... Cou... Could you turn around and bend over?" he stammered out after a moment, just when Dani thought she might be home free.

She smiled her warmest fake smile at him, "Of course I can." And she turned around and bent over to show off her ass and her pussy from behind.

"Now can you reach back and spread your ass?"

Dani rolled her eyes as she again sweetly said, "Of course." After the first two guys had requested this of her, she had to go figure out where it came from, and a series of casting couch videos was her only guess as to why every single guy had requested to see her like this. After thirty seconds though she stopped and stood back upright before turning to him.

"Well, thanks for lunch Simon. I'm sorry it didn't work out like I think we both hoped it would."

When she looked at Simon he was standing and grinning, holding a printed piece of paper in his hand. She reached out for the paper and recognized it immediately. It was a message she had sent to this guy named Derek who lived in upstate New York, promising that he'd get to fuck her in the ass if he ever got her naked in person.

"Uh, how did you get this Simon? This is for Derek, see?"

Simon couldn't help but grin to her. "It's okay Danielle, my real name is Derek. Simon is only my middle name."

She shook her head at that. "Yeah that doesn't apply to..." her voice trailed off before she looked at him again. "Wait, what did you say?"

"Oh, you mean calling you by your real name Danielle Aubrey Abernathy, instead of your fake name Courtney?"

The smile quickly was wiped from Dani's face as her full name was said. "How?"

The portly man's grin became even wider. "I don't think that matters. What really matters is I know who you are, I know who your dad is, and I have the whole lunch on camera." He pointed over to one of the lights that had a little camera mounted to the wall above it via suction cup.

"I wonder how daddy would feel if he knew what his little princess got up to online?"

Dani gulped, she knew she was in trouble. Her stepdad's sterling reputation was very important to him. Video of his privileged step-daughter slutting it up would destroy him, and she knew from talks that he gave her when she was younger that anything she did to ruin the reputation would be met with being cut off completely. It was why he gladly paid the interest on her unlimited credit cards. They were in her name and if she ever fucked up to the point she'd be left with nothing but a giant pile of debt. And of course since she wasn't his real daughter, his remorse would probably be non-existent.

"What do you want?" Dani asked meekly, knowing that she wasn't in much of a position to argue with the man.

Simon (or Derek, she didn't know what to really call him now) just grinned. "Honor the coupon."

Dani gulped again as a horrified look came over her face. "Please, please, not that, I'll do anything else. Please?" she started to plead with the guy.

Anal sex wasn't something that Dani or any of her friends had ever experienced. Why would she, when you're rich and you're hot you don't need to take it up the ass for any guy. She was the one in control, why would she submit to anyone like that? Her and her friends would hang out sitting at the mall and laughing, looking at the women and girls who walked by and taking their guesses on who took it up the butt, and who really needed to.

The guy shook his head at her. "Nope, I want to see your ass swallowing my cock like you teasingly swallowed that manicotti. Now, unless we're gonna have a problem, you should bend over the bed, or the table and we can get started."

The last time Dani wanted to cry was when she was 8 and her stepdad didn't want to buy her a seventh pony. She needed one for each day of the week after all. However, that stupid situation paled in comparison with where she was at now. Dani walked over to the bed and bent over it, burying her face into the comforter as she let out a little sob.

"Spread your ass again girl!" This was a command, a very different place from the seemingly meek guy who just a few minutes ago could barely ask her to bend over. Dani realized that she had gotten played and wanted to sob even more.

She heard the man come up behind her and out of the corner of her eyes she saw his robe fall to the floor. He waited a long moment before finally stepping close enough that she could just tell he was there. That's when she realized it. She may not have ever had, or intended to have anal sex, but she knew all about it. "Wait, what about lube?"

Simon laughed. "The coupon doesn't say anything about lube, just says I get to fuck you in the ass." Dani was truly fearful now. "However, if you'd like to remedy that and provide some lubrication of your own with one of your other holes, I wouldn't mind."

'Well played,' she thought. Not only was he gonna get her virgin ass, but he also conned a blowjob out of her. She nodded and meekly said, "Okay," before she slipped from being bent over the bed to getting on her knees.

"Oh no, not on your knees girl."

Dani looked up at him, both confused and repulsed. She didn't understand what he had meant by not on her knees, but at the same time she finally got to see his body, and portly didn't quite describe it. Simon was obese, and seeing fold upon fold of fat layering over itself almost made her want to puke. The scarier thing for her was when her eyes finally looked away from the fat and saw the rather large throbbing cock that she was about to take in her mouth and her ass.

"Oh, I'm just thinking of that lovely little meme you have as one of the pictures on your profile page. Good girls bend at the knees, bad girls bend at the waist. And face it Danielle, you've been a very bad girl."

She was mentally cursing herself now. Dani stood up from the floor and looked at him, giving him those puppy dog eyes as she pleaded to avoid this humiliation, this degradation.

"Well?" is all he said in response.

Dani sighed and bent over at the waist as he stepped forward until his cock started to rub against her face. She started to reach up with a hand and he slapped it away. "Mouth only Danielle."

Another sigh escaped her lips before she parted them for the massive piece of meat as she leaned forward. As her mouth stretched around it she quickly started to realize that this was the largest cock she had ever taken.

She was surprised when she felt his hands on her head, grabbing her hair in a fist. She couldn't move her head but that didn't matter as he started to thrust his hips, pushing further into her mouth. Here she was, a girl who had always been in control, especially where sex was concerned, and she could do nothing but try to cover the cock in her mouth with as much saliva as possible while he fucked it in and out.

Dani was spared too long of an indignity of this when he pulled out after what seemed like no time at all. "I think a change of plans are called for," he told her as he released her hair, allowing her to stand back upright. She was relieved, maybe he wouldn't take her ass after all.

He grinned and grabbed her hand and led her around the side of the bed from where she was just standing. "Bend over and spread your ass again," he commanded as he walked away. Knowing she had no real choice she did as the dominant man said.

Simon for his part moved over and grabbed the camera that he had mounted to the wall with the suction cup. He brought it over and put it on the wall that was opposite her, just a foot above the bed.

Any relief Dani may have had at the initial "change of plans" was gone as she realized that the camera would be trained on her face the entire time. She was living out what those broke girls did in the videos she saw online. She buried her face in the comforter.

"It's live streaming already to a server online Danielle, so don't think about trying anything funny with the camera, except to look up at it."

Dani couldn't believe the situation she found herself in as the man moved around behind her. Her hot little ass was about to be fucked by a guy 2 ½ times her age and probably three times her weight.

She felt him place something that was probably made from plastic on her back before she felt a hand pressing into the small of her back, pushing her into the bed even more. The moment was upon her, she felt his large cockhead at her asshole.

"Danielle?" he said, the same dominant tone in his voice.

"Yes," she heard herself say meekly, not even sure the sound came from her lips.

"Beg for this."

Dani whimpered. "Please fuck my ass."

She heard a sigh from behind her. "Make me believe it you little whore, make me believe you're my willing little buttfuck buddy."

More whimpering, and a deep breath. "Please Simon, please fuck my ass. My ass needs to be punished for messing with you, please punish it with your giant cock."

"Not perfect, but if you insist," he said and he pressed forward.

That first pressure for Dani was excruciating. She was convinced that she wouldn't open for him, or that he was tearing her apart, or both at the same time. The agony seemed to go on for an eternity before she swore she heard a plop sound as her rosebud contracted, the head of his cock stretching her tightest hole wider than she thought possible.

Her hands let go of her ass and reached forward and grabbed at the comforter as she buried her face in it, trying hard not to cry aloud from the pain. Simon however was nice and he just stood there, waiting. The longer she kept breathing, the more her body acclimated to the intrusion.

When she pulled her head out of the comforter and looked up he spoke again. "Good, now that you're used to it we can really start."

A hand reached forward to her blonde hair and grabbed it, and in doing so the cock sunk further into her ass. Dani's face cringed in pain, but as the stiff rod made its way deeper inside, she noticed it didn't hurt as much as the initial intrusion.

"I think I can keep my head up without your help," she said to him, almost arrogantly, trying to reclaim some control over the situation.

"Very well, that will make this easier," he said as he released her hair and both his hands moved to her hips. He pulled her back into him as he pressed forward. More cringing from Dani's face for the camera, but she only put her head down for a second to catch a breath as the cock sank deeper into her tightest passage.

The intense burning felt like it was hours, but finally she felt him stop, and felt the mass that was his stomach laying on her back. "See, you took the whole thing in your ass, swallowed it whole just like I wanted."

"Does that mean you can take it out now?" she asked hopefully, but already knowing the answer.

Much to her surprise he did start to withdraw, and as he did so she felt a strange combination of relief and emptiness. Of course he didn't remove himself completely from her (she didn't know that she would regret that more if he had), but with most of his length out of her he pushed back in, and quickly built up a good steady rhythm.

Dani was surprised by how quickly things went from him just getting into her ass to him fucking her ass as though it were her pussy. The friction around her tightest hole was hurting her a lot, but the stimulation also had her wet. Could she be enjoying some small part of this, she wondered to herself.

He slowed for a moment to speak to her. "If you can push yourself up off the bed enough that we can see your perky little tits bounce as your ass takes its punishment, I'll even reward you."

With that he was back to fucking her ass at full speed. Dani had to think, trying to figure out if this was an actual reward, or if it was just another part of the setup. She finally pushed herself off the bed and onto her forearms, still standing but almost as if she was taking him doggy style. She immediately noticed that a little bit of the pressure on her ass was gone. Maybe that was the reward?

The girl would find out a moment later that it wasn't the case, as the plastic thing was removed from her back and thrown onto the bed in front of her. It was a small, purple, mini-hitachi wand.

"Go ahead and get yourself off. I can't be the only one to have any enjoyment from this."

Dani could imagine the smug grin on his face as he said it. Part of her didn't want to give him the satisfaction. She knew immediately that it was part of the game. Making her cum while getting fucked in the ass would be humiliating. But he probably knew the same thing she did-if she didn't cum now she would go home and probably cum as soon as she possibly could.

A war was being waged in her mind while the large cock sawed in and out of her rectum. Which was worse, the humiliation of cumming while getting buttfucked against her will, or the pain and pleasure she felt now. At least with using the toy she could maybe distract herself as the assault on her ass continued.

Her right hand almost instinctively reached out for the wand and turned it on before reaching underneath herself. It was self-preservation, she'd rather try and focus on the pleasure than the pain and humiliation she was feeling too. The moment the wand touched her clit, Dani felt herself overwhelmed.

Dani let out a loud moan of pleasure, which was actually a surprise for her. She was never the type who was loud in bed, whether with someone or by herself. So the fact that this ugly fat man abusing her ass had gotten her to make as many sounds as she had was quite stunning to her. But the massive jolt of pleasure she felt through her body, and especially the pleasure mixed with the pain in her ass was unlike anything she had ever felt before.