Ben the Bored Billionaire

All Characters engaging in sex are 18 years or older. This is a work of FICTION. Any resemblance to real persons is coincidental.This story will contain anal, cum play, and light fetish play. If you like this story, please Vote, Comment and let me know what you liked, and look forward too many more stories from me. A big thanks to s0rethr0at for the editing.

Ben woke up to Beth sucking his dick. It was a good view to wake up to. He smiled to himself; it had been a good night, as well. It had been 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.

Ben looked down as he saw Beth’s head bobbing up and down, taking as much as she possibly could.

Ben could tell that Beth was no stranger at sucking a good cock. So he laid back and enjoyed the wonderful feeling of it all.

Beth slowly bobbed her head up and down and played with Ben’s balls as she licked and sucked every inch of Ben’s cock. Ben felt the tingling in his cock that said he would soon come.

“I’m close, Beth. I’m going to come!” He announced, his breath puffing.

He grabbed her by her hair and moved her head frantically on his cock, while Beth picked up her pace. As the first rope of cum shot out and into the back of Beth’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 Ben was finally done. Beth sucked every last drop out of Ben and was now using his cock to rubbing in all the hot cum on her face.

“I’m going to go take a shower.” Beth smiled at Ben as she got up and headed to the bathroom.

Ben checked his phone and did some research on the shop that he wanted to go to and made some calls as Beth come back out with a towel wrapped around her.

“What are your plans for the day?” Ben asked Beth as she started the female ritual of moisturizing and dressing up.

“I 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. Call me when you got home later.” He told her.

Ben went home to get cleaned up and start looking for an apartment in the City. He didn’t want any of the girls he met to know who he was or where he lived. And he wanted to have a place ready in case he needed to bring any of the girls to his place. After looking online, he had found two promising places. With a quick call, Ben had made an appointment to see both before Beth would be done with her classes.

The first apartment was nice, but Ben didn’t like the neighborhood it was in, and the second was the same.

“Do you have anywhere that’s nicer and in a better area?” Ben asked the realtor at the second place.

“Yes, actually. I do.” She replied, beaming.

She took Ben to a new apartment building and showed him several model apartment.

“You have several new apartments to pick from. There’s the one-bedroom apartment, and then there’s also the four-bedroom on the top floor.” The realtor informed him.

Ben quality picked the model apartment on the top floor and asked if all the furniture come with the apartment.

The realtor made some call’s and informed Ben that if he was willing to pay for the furniture he could have it as is. Ben pulled out his Credit card and quickly paid for everything. The realtor told him that his new apartment would be ready in two days for him to move in to.

Ben headed over to Beth’s apartment after getting her call. As Ben pulled up, he saw Beth standing outside, and he was impressed with how she looked. Beth 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.

“I told you today morning. To do some shopping.” He said. “And to have lunch.”

On the way to the restaurant, Beth asked, “Ben, how does the bonus system work and how much is for what?”

“That depends on what you want to do.”

Beth thought it over. She and her best friend had talked about having a threesome before if they ever found the right guy. Beth 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. Beth looked at Ben and asked, “How much are you willing to pay for my first time doing anal?”

Ben 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 Beth as he pulled into the restaurant where they were to have their lunch.

As they sat down at their table and ordered their drinks, Ben looked around and asked her, “Are you serious about your offer?”

Beth nodded, “What do you think of the offer, Ben?”

“Tell me a price so that I can negotiate from there.” He told her.

Beth didn’t know what to say. 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?”

Ben 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.

Ben looked at Beth, “That’s high. Would you be willing to go down to $500?”

“It’s something that I have always been scared to do, and I need the extra money, so how about $800?”

Ben was willing to pay a lot more than that, but he didn’t want her to know that.

“I can work with that.”

Ben looked at Beth and informed her, “Any bonuses you want will only be paid on completion of the act, and if you stop midway, there won’t be a bonus.”

She nodded. “Please be gentle the first time doing it,” She told him timidly.

“Would you be willing to get a wax?” He asked her. He liked his girls to be smooth and clean.

Beth had gotten it done many times before and liked how she felt after and didn’t mind getting it done again, but she didn’t have the money to keep getting it done. She wanted to see if she could get something out of doing it.

“I don’t like getting waxed. It’s too painful.” She told him. “But if you could convince me, I’d be willing to do it for you. Of course, you’ll have to pay for it.”

“Okay, fine. I’ll pay for it.” He said and gave her a hundred dollars for getting it done.

“Can you do three? It’s really painful.”

“If you get a full Brazilian wax, I’ll do three. Do you know somewhere you can get it done after we eat?”

“I do. I’ll book an appointment.” Beth called a place she knew that did it and got an appointment one hour from then.

After eating, they head off to the salon for Beth’s appointment. Ben sat there and stared as Beth was instructed into several awkward positions.

She let out small, painful screams as she was waxed smooth in every nook and cranny. He’d never known what women had to go through to get waxed. Beth deserved every penny for getting it done for him, he thought.

After 30 minutes, she was finally done. Ben got his first good look at Beth’s smooth little pussy, and he couldn’t wait to get back to her apartment to have a taste.

Beth got off the table and ran her hands over her smooth pussy and a finger between her wet lips and loved how she felt.

“Like what you’re seeing?” Beth teased him. Standing there for Ben’s viewing pleasure, she knew that he appeared off her new look.

Getting into his truck, Ben handed her three hundred dollars as promised. Ben was so hard after seeing Beth playing with herself, but he knew that she needed a couple of hours before she could have sex. Ben quickly drove to the store he wanted to go to next and parked in the parking garage away from other cars.

“Get in the back seat.” He told Beth.

When she had gotten there, he joined her there. He pulled down his pants showing Beth his hard cock. She knew right away what he wanted, and she wasted no time giving it to him.

Beth pulled her hair in a quick ponytail and grabbed his cock at the base. She gave him a long lick from bottom to top and took the head of his cock into her waiting mouth. Beth started running her tongue around his cock head and slowly worked her way down. Ben sat back, looking down at her working her magic. Beth started bobbing her head up and down quickly.

Pulling out, she reached down and started suckling on his balls, one at first and then moving to the other, working her tongue as she sucked. After finally releasing him, she looked up and slapped her face with his cock several times.

“Do you like that?” She asked him, her eyes sensual.

Ben only nodded and told her, “Don’t stop, baby.”

Beth started back on his cock, sucking and licking. She knew how to get a man to cum quickly. She quickly had a rhythm going with her head bobbing up and down, and her hand was moving up and down in a twisting motion. As she worked her magic, Ben was in pure bliss.

“I’m getting close!” Ben told Beth after several minutes. Which only made her pick up her rhythm.

Ben felt his balls get tight and felt the first rope of hot cum shoot through his cock and into her mouth. Beth felt the first shot hit the back of her throat, and she kept sucking as the second and third filled her mouth. Ben let out a soft grunt as he finished coming. Beth slowly pulled back and sat upright and opened her mouth to show him that it was full of his hot seed, and in one shoot took it down her throat and opened again to show it was all gone. She then gave him one last lick to make sure that she got every last drop.

********************

Beth was surprised as she walked into her first adult sex shop. The shop had everything from toys, sexy lingerie to costumes. As they walked to the toys section, Ben started grabbed items. A big bottle of lube, a butt plug, small and large vibrators. Beth got a basket, and Ben dropped all the items into it. Beth quietly followed Ben around as he put more items into the basket.

Ben stopped and was looked at something that caught his eye.

“Which one do you prefer?” He turned to Beth and held up two collars: an all-black leather one and a pink one with fake diamonds and a long leather leash.

“That one.” Beth pointed to the pink one, and he dropped it with the other items and with a pair of pink fuzzy handcuffs.

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 Beth’s size?” Ben asked the woman working at the store, pointing towards Beth.

“Sure, sir.” The woman beamed.

After getting Beth’s measurements, she came out with the two outfits and their matching shoes.

“Pick out some lingerie,” Ben told Beth.

After paying for everything, they started to make their way back to Beth’s apartment.

“Relax while I’ll take a shower. I’ll be done soon.” Beth told Ben and walked to her bedroom that had an attached bathroom.

After 30 minutes, Beth came out of the bathroom in her new all-white outfit. Ben looked at her and was amazed at how sexy she looked in it.

“White was an appropriate choice since I’m going to lose my anal virginity soon,” Beth told him.

“It is, isn’t it.”

Ben walked up to Beth and looked her up and down.

“Turn around.” He motioned with his finger. Her juicy ass looked perfect. Reaching out Ben placed his hands on her ass and slowly rubbed them up and down before giving her a hard squeeze.

Ben handcuffed Beth’s hands behind her back and turned her around. He put on the pink collar. Grabbing the leash, he led Beth to the bedroom.

Ben got undressed and turned back to Beth, pointing down. She did as she was told. Ben 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.

Ben grabbed her head and started to go faster. With every stroke, he was forcing his cock deeper into her mouth. Beth closed her eyes tightly as he was going deeper into her. Beth’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, Ben kept pushing in and out of her. She finally couldn’t take anymore and tried pulling away from him. But Ben continued his assault on her. Finally, he stopped and pulled out of her mouth. Beth immediately hunched over and started wheezing and coughing.

Ben 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 Beth on her back on the bed, he reached down and pulled off her white panties. Ben rubbed his hand over her smooth pussy, noticing Beth was already very wet.

Ben lined up his cock and pushed into her halfway, slowly working in and out. He started with a steady rhythm. Looking down at his dick sliding in and out, he saw it was quickly getting covered in Beth’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 his dick slid in and out of a very wet Beth. As more and more of Beth’s cream gathered around his dick, she arched her back and let out a scream as her pussy clamped down tightly onto his cock.

After Beth had finally relaxed, Ben pulled out and had Beth bend over into doggy style. Ben ran his hands over her ass and gave her a nice squeeze, and spread her ass cheeks apart to get a good view of her little pink asshole. Ben grabbed the lube and the butt plug from the bag. He applied a small amount to her and the plug.

“Relax.” He told her as he slowly started to work the plug into her tight little hole.

After several failed attempts, Ben finally got it into place, looking at the pink diamond at the end of the plug with a smile. Ben reached back and gave her a playful slap on her ass. He then took hold of his cock and pushed it back into her. As he grabbed the leash and pulled it back, he started moving forward and backward into her.

Ben placed his hands on her hips and started to move faster and faster. Beth was moaning louder every time he would bottom out into her. She was quickly working into her second orgasm. Ben was getting closer to his own and didn’t know how much longer he would last.

Ben started to feel the tingling sensation as his ball started to get tighter. He slammed into her one last time as he started to flood her with his seed. Beth locked up as she felt Ben cumming inside her, which pushed her over the top and into her orgasm. Looking down, Ben saw a mixture of both their juices had slowly started leaking out of her.

They 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, Beth 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 Ben.

As they both laid in bed talking about their past.

“You never told me what you did for a living,” Beth said.

Ben started to get uneasy when she asked that.

Then she asked, “Where do you live?”

Wanting to change the topic quickly, Ben turned to Beth.

“Are you ready to go again?” He asked her.

“How do you want me?” Beth asked.

“Doggy would be the best way to go.”

So she got on all fours with her ass waving around in the air. Ben grabbed the bottle of lube and put a generous amount all over his cock.

Reaching out, Ben pulled out the butt plug from Beth and set it down next to them. Looking down at her little, pink asshole slowly closing back up, Ben smiled to himself. He was finally going to get what his ex and every girlfriend had denied him.

Ben placed the tip of his cock to her asshole and slowly started rubbing it up and down to get it ready for him. Ben 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, Ben quickly slid in a quarter of the way into her. He stopped to give her time after hearing the scream as he entered.

Beth’s eyes had closed tight as she felt him enter her backdoor. She clenched her teeth and held the bedsheets tight in her hands from the discomfort she was in. Then the pain and discomfort slowly started to fade. Opening her eyes and looking up at him, she gave him a slow nod to let him know to continue.

After getting the nod, Ben knew she was ready for him to continue. He slowly pushed into her an inch at a time. Ben was now halfway into her as he pulled back slowly so that only the tip was left in her and pushed back in her. He kept doing this until he was all the way inside of her.

Ben 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, Ben loved the feeling.

“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.

Ben slowly started to pull out and push back into her. After several minutes, Beth 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.

Beth nodded and told him, “You can go faster if you like.”

Ben grabbed her hips and thrust into her faster and faster, reaching back, he gave her ass cheeks several hard smacks that got a scream out of her each time. Ben 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.

Ben released her hair and breast and grabbed her arms next, and pulled them back. Beth was now only on her knees as he started going full speed slamming into her. Ben knew he couldn’t last much longer. He slammed deep into her several more times before he started to cum deep into her.

After he finished shooting several hot loads of cum into her. Ben slowly pulled out, looking on in amazement. He could see deep inside of her as she was starting to close up. Ben quickly grabbed the butt plug and inserted it back in place to hold his seed inside her ass.

“I’m going to go take a shower now,” Ben informed Beth when they were lying on the bed after the vigorous anal sex.

******************

Ben got out of the slower and walked into her bedroom. Getting dressed, he could smell that she was cooking something delicious. Ben 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.

Ben looked at her and asked what was so funny. Beth looked up at him with a small smile and a scrunch of her nose. “It’s funny how every time I move, I can feel your cum moving around inside of me. 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. I don’t think I would have liked it as much as I did. I’ll definitely do it again.”

Ben got up and pulled out the 800 dollars. He set them down at the table.

“There. Now, I have to go.” Say his goodbye to Beth, he headed out the door.