Drop the Towel - Taing a Ris

***All characters are over 18 and are fictional. Any resemblance to any real-life persons or situations is purely coincidental.

AUTHORS NOTE: I had a few other ideas after my first Drop the Towel story using the same theme. I'm not going to make too many stories about this, but maybe a small anthology about it.

.....

Before Ian left the house, he texted his friend Nick that he would be coming over with the rest of the money he owed him. He also apologized for coming so early in the morning but he had a busy day ahead of him and wanted to get this one detail out of the way before he got to them. Recently, Ian had won three thousand dollars from his bookie on a couple of college football games. The teams he picked had such longshot odds of winning, even his bookie thought was a stupid bet for him to take, but he couldn't help taking the risk. As his father used to say, "no risk, no reward." But he knew his father was talking more about taking a risk in life, not gambling, something he would never approve of.

He owed Nick a lot of money for some work he had done on his car a few months ago. He was already being given the friend's discount and was willing to take payments for it in cash. Ian was going through some money trouble at the time, some of it from his gambling, but mostly because the company he worked for cut his hours so he was being paid less these days. His car was breaking down, and he needed it to get around, especially to do some rideshare driving on the side for extra income. Nick owned an auto repair shop and helped him out with it by keeping the cost of the repairs as low as he could. Ian made his payments regularly and had $1500 left to pay him back, which Ian wanted to pay back right away before he got the urge to gamble it all away on another longshot.

When he was only a few minutes away from Nick's house he got a call from Nick and put him on the speaker so he could drive without distractions. After they said good morning to each other, Ian explained about the money he had won and wanted to pay him back what's left of what he owed him.

"Can you do this later or tomorrow?" Nick asked. "I'm not at the house right now; there was an emergency at my shop. Can you come later or tomorrow?"

"What's the emergency? It's Saturday, I thought your shop was closed on the weekends."

Nick explained how he got a call early this morning about how a couple of people had broken into the shop. They thought they cut the alarm not realizing that they actually set it off and the police came and arrested them before they got away. Now, he had to go to his shop to assess any damage they caused and file a police report.

"I'm sorry about your shop. But I'm very close to your house, can't I just leave the money in the mailbox?"

"I'd rather you didn't," said Nick. "This burglary got me spooked and I don't want to leave your money out in the open like that. But I do have a lady friend at the house right now, her name is Sandy. She was there when I got the call from the police and will be sticking around for a while. She can let you in and you can wait around until I come back. I should be back in about an hour or so."

"Now when you say 'lady friend', do you mean girlfriend?"

Nick had a little laugh. "No, Sandy is just a woman who I like to call on from time to time, that's all you need to know."

"You don't have to say any more. I think I got the picture."

Nick was known to be a big player among their group of friends. He had a new girl almost every other week, sometimes two at a time. He even had a few women around who were just friends with benefits. Ian didn't think that really worked outside of the movies, but Nick proved it was possible with the right person.

A few years ago, he became a legend with their friends when he was seeing three women at once for six months before they found out about each other. Afterwards, two of them stuck around a little longer because that's apparently how good he was with women.

"But she must be something more than just a 'lady friend' if you're letting her shower and do her laundry there."

"It was a little more complicated than that," Nick replied.

Nick explained how usually when Sandy sleeps over, she takes a quick shower, have some coffee with him and leaves. But last night while they were sleeping, Nick's basset hound, Bowser, named after the Super Mario Bros. villain, came into the bedroom and slept on Sandy's clothes that she left by the bed. When they woke up after getting the call about the break-in, they discovered how Bowser had drooled all over her clothes. Nick felt bad about what Bowser had done, so while he went off to deal with the police, he told her she could wash her clothes there and just lock the door behind her when she leaves. She had been over his place enough times that she earned his trust to be left alone at his place.

Ian completely understood how Bowser's drooling can be a nuisance. Last year, he slipped on a puddle of his saliva in Nick's kitchen and banged his head against the refrigerator. He didn't hit his head that bad, but the side of his head was sore for the rest of the day.

"Alright, I don't mind waiting around your place until you come back," said Ian.

"Cool, I'll call her now so she'll know you're coming and won't be surprised."

Ian made it to Nick's house a few minutes later. He parked on the curb in front of the house behind a blue Hyundai which he's assuming belongs to Nick's lady friend. He got out of the car, walked up to the house and rang the doorbell. A moment later, the door opened, and he was stunned by the beautiful woman he was seeing. She was in her mid-twenties, about 5'8", with bright blue eyes and long, dirty blonde hair, but what surprised Ian the most was how she was standing there with a towel wrapped around her body. He could tell that she had just gotten out of the shower not long ago from how wet her hair looked and the towel looked a little damp as well. The towel was kind of short and it showed plenty of her perfect legs and plenty of her cleavage on top. He guessed she was somewhere in the high C or low D cup range.

He realized he was staring at her a little too long and forced himself to finally say something.

"Hi, you must be Sandy," said Ian.

"You must be Ian, please come in," she said, letting him walk past her before closing the door. "I have some coffee brewing, you want some?"

"I would love some. Thank you."

As soon as he came in, he was greeted by Bowser, who jumped up on Ian's legs, and he petted his head a little. The dog then went over to Sandy, who bent down to rub the back of his head with both hands.

"You're a little drool machine, but you're such a cute little doggie," she said in a cutesy tone that some people give to dogs they like.

Bowser jumped up at Sandy, putting his paws on her chest, and when it came down, he almost took her towel off. Ian got excited at the chance to see Sandy, but she quickly fixed up her towel and laughed at the situation.

"He's such a little troublemaker," she said.

"Yes, he is," said Ian.

Ian followed her to the kitchen and got a good look at her from behind. He mouthed the word 'damn' as he stared at her. He couldn't believe how lucky Nick was with women that he could get himself a girl like this to be his fuck buddy.

"Sorry for the way I look right now," she said. "I know this looks kind of awkward."

"It's not a problem," said Ian. Meaning he had no problem hanging around a beautiful woman in a towel that's barely covering her body.

As she made them both a cup of coffee, she wanted to explain her appearance, but Ian told her that Nick explained what Bowser did to her clothes. She said she held no hard feelings toward Bowser for it and she still loved the silly mutt, as she called him. Sandy did explain how, after she washed her clothes and put them in the dryer, she realized she had plenty of time to take a shower. She had gotten Nick's call as she got out of the shower about Ian coming over and had to quickly dry herself off before he arrived. She had just gotten the towel wrapped around her body when Ian rang the doorbell, and she had to run to answer the door.

"So, now I'm just waiting around until my clothes are dry, and then I'm out of here," she said.

"At least you have some company now while you wait."

"Cheers to that," she said, and they both clanked their coffee cups together.

As he drank his coffee, he couldn't stop staring at Sandy in that towel. It was just one piece of cloth away from her being fully naked. She didn't seem to notice him ogling her as she continued to talk. She was saying something about going to college, but he could barely pay attention to what she was saying. All he could think about was how she might look naked. He was really excited when Bowser almost pulled her towel off, and now the idea of what she looked like naked was all he could think about.

He suddenly remembered a story he read on the internet about a situation similar to this. There was a guy who went over to his buddy's house and was greeted at the door by his buddy's new girlfriend while she was wrapped in a towel. The guy took a big chance and told the woman he'd give her $100 if she would drop the towel. She took the money from him, dropped the towel, and let him see her hot, naked body. Later, she found out from her boyfriend about how a friend of his was stopping by to give him the $100 that he owed him. He wasn't sure if the story was true or not, but it was still funny to think about.

Ian realized how he was in the exact same situation. He was there to give Nick some money he owed him, and now there was this sexy woman in a towel. Seeing her standing there like this he couldn't help thinking how maybe he could try the same exact thing with her. Nick already made it clear that she wasn't his girlfriend, just someone he enjoyed casual sex with, so it wouldn't be like he was doing this with a woman whom Nick had deep feelings for. Even if she told Nick what he offered her, he probably wouldn't care. Even if Nick did somehow think it was wrong for him to try that, he wouldn't be mad at him for too long about it.

There was also the chance Sandy would already know about the towel story and realize that the money he was offering her was actually supposed to go to Nick. He was beginning to like Sandy, but he couldn't help thinking how it would be a clever way to see her naked.

He decided to go for it. As always, he figured the risk was worth the reward. The worst-case scenario he could think of was that she would slap him in the face and he wouldn't blame her if she did. He was used to women slapping him in the face by now; he realized he could be a dick sometimes but he just couldn't help himself.

"Sandy, I need to ask you something, and I want you to keep an open mind about what I'm going to ask."

""What is it?" she asked.

Ian reached into his pocket, where he had Nick's money, pulled out only one of the large bills that was there, and held it up in his hand.

"I'll give you $100 to drop the towel," he said.

Sandy's eyes widened to show how stunned she was by Ian's request. Seeing her expression made Ian think he had made a big mistake.

"Sure."

"Really?" he asked.

"Why not? It's a hundred dollars just to see me naked; easy money."

He hoped for a yes, but even he was surprised by how casual she was about accepting his offer. But he didn't question it; he just handed her the money, and she put it down on the kitchen counter since she had nowhere else to put it. She immediately dropped the towel and just stood there in front of him, with her hands on her hips and giving him a big smile. He could see that she liked to work out; her pussy was shaved, she had a thin waist, and best of all, she had large, perfectly round tits. She slowly turned around for him so he could get a look at her perfect ass as well.

"Damn," was all Ian could say.

"You approve?" she asked.

"What man wouldn't approve of this?" he replied. "You're like one of those A.I. art images come to life."

"Thank you," she replied. "I never got that kind of compliment before; it sounds kind of nice."

Something came over Ian as he reached into his pocket and took out another two hundred dollars this time. It was another big risk he was taking, but he needed to try.

"Maybe I'm asking for too much, but I'll give you another $200 if you let me feel your breasts," he said.

"OK," she said. "Only for three minutes, no more than that."

Ian couldn't believe his luck. Despite his confidence in the situation, he was prepared for her to be offended by this kind of offer. It was one thing to pay to see her naked; it was another to ask to pay to feel up her tits. But he was happy to see that she was very willing to go along with this for the money.

He gave her the money, and she put it with the other hundred she had on the kitchen counter. He then reached out his hands, eager to feel those beautiful mounds of flesh, but she stopped him by grabbing both of his hands.

"Be gentle," she said. "And hands only; don't try to put your mouth on them, or anything else you may be thinking about doing."

"Understood."

"And I do know some martial arts if you try anything with me; don't try to test me on that."

"I promise, I'm not that kind of guy."

She let go of his hands, and he grabbed both of her breasts. He gave them both gentle squeezes and slightly pinching the nipples; they were big, soft, and had the perfect texture to them. He had his hands on plenty of women's tits before, mostly from strippers he got lap dances from, but this was indeed the best pair he ever felt.

"Wow, these are amazing," he said.

"Yeah, they are awesome," she replied with a smug smile.

"Are these real? They feel too perfect to be real."

Sandy laughed. "It's funny how often I get asked that. But I assure you, they're one hundred percent all natural."

Sandy was using the clock on the oven to keep track of how long Ian had been playing with her tits. She liked the way he was feeling her up and thought the ridiculous grin he had was very funny. When Ian's time was up, she made him take his hands off of her. Ian was disappointed that it was over, but he agreed to the time limit and had to abide by it.

Sandy picked up her towel and was about to wrap it back around her before Ian stopped her. He was about to go one step further in this venture, something he was sure she would say no to this time, but again, all he could think about was how the risk was worth the reward.

"Ok, I may be going overboard with this one, but I have one more offer for you," he said.

"Go on," she said.

Ian took a moment to prepare his offer to her. He assumed this insane venture of his was probably stemming from his gambling addiction, but despite knowing this, he was still going to go for it. He took out the remaining money he had to give Nick and held it up in front of her.

"This is $1,200," he said. "All yours if you let me fuck you."

Sandy grabbed the money and combined it with the other $300 she had just earned from him.

"Let's use his spare bedroom," she said. "I'm not comfortable using Nick's bedroom for this."

Ian couldn't believe what was happening to him. Even during his best win streaks, he never felt this lucky.

Sandy picked up her towel, and he followed her upstairs. He was glad that she was walking in front of him so she wouldn't see how giddy he was behaving. He had been with many women before, but he was never as excited to have sex with someone as he was right now.

Before they got to the spare bedroom, she needed to make a quick stop in Nick's bedroom. There, she threw away the towel in the laundry basket in Nick's master bathroom, picked up her purse that she had left there and put the money inside of it. She took the purse with her as she left the room and Ian followed her the rest of the way to the bedroom.

Bowser had followed them into the room and barked at them a few times. Sandy grabbed him by the collar and made him leave the room.

"Not this time, buddy," she said to the dog. "You have caused enough trouble for me already."

She got the dog out of the room and closed the door behind her. When she turned around to face Ian, he tried to kiss her, but she stopped him.

"No kissing," she said very assertively. ""Just straight sex, no funny business. Alright?"

"No problem," said Ian. Not getting to kiss he was disappointing, but he understood that she probably didn't want to make it too intimate.

She put her purse on the nightstand and took out a condom. She asked if he wanted to put it on or if he wanted her to do it for him. Ian was surprised by this question and said he'd like her to put the condom on; it had been a while since a woman had done this for him, and he thought it might be fun to see.

She got down on her knees and began to unwrap it as Ian quickly dropped his pants. His large dick sprang to action, nearly hitting her face, but it didn't seem to bother her. Sandy put the condom on his dick very quickly, making Ian wonder how often she did this and why it made her put it on him so fast. He stopped asking himself questions like that when Sandy opened her mouth wide and took his dick into her mouth.

"Damn," said Ian.

She left it in her mouth for a moment. She wanted him to enjoy the feeling of her warm mouth engulfing his dick. She started bobbing her head, slowly at first, to get him slightly warmed up. Her lips were perfectly sealed around the shaft while her tongue massaged it every time it entered her mouth. She then slowly increased her speed as she grabbed his balls with one hand and began massaging them. Ian put his hand on the back of her head, hoping to control the motion of her oral skills, but she swatted his hand away. She had done this enough times that she didn't need any help giving a good blowjob.

When she was sure he was ready, she stopped the blowjob and stood back up. She then went to bed and lied down on her back. She looked at Ian with a lustful look and signaled for him to come to her with her finger, as if she were a queen giving an order to her servant. He may be paying her for sex, but she was showing that she was in control of the situation here.

Ian removed the rest of his clothing and got on the bed with her. He got on top of her and again tried to kiss her, but she turned her head just in time.

"I told you, no kissing," she reminded him. "I don't even let Nick kiss me."

"I'm sorry. It won't happen again."

He thought that sounded a little unusual since she and Nick were fuck buddies, but he figured it was a way to make it less personable between them and keep it just about sex.

He started kissing her neck, something he was sure she would let him do. She began moaning as he did this, so he kept going. Soon, he began to move downward on her body, kissing her along the way. He stopped at her breasts, where he spent plenty of time kissing them and sucking on her nipples. Sandy was used to this by now; every man she had ever been with liked to play with her big tits before they wanted to fuck. Some were good at it, and it turned her on, while others just slobbered all over them. Ian was somewhere in between. He was doing alright with her breasts but she was starting to get bored with him just staying there. After a while, Ian moved one of his hands to her pussy and began fingering her, which she really liked and finally began to enjoy herself.

When he was finally done, he moved back up on her body, and she showed that she was ready for him as she opened her legs for him. Without hesitation, Ian pushed his dick into her tight, wet pussy.

"Oh, that feels so good," she whispered into his ear.

He left it in there for a moment, enjoying the sensation of how her pussy felt around his dick. Although Ian had his share of pussy before, this one felt especially perfect around his dick. Even Sandy was enjoying the first moment of Ian entering her body. It didn't matter how many men she had been with; she always loved the feeling of having a new dick inside of her.