Bossman's List

by Ashlee Price

  Well screw it, she thought. She was going to do it. She looked at Natasha and pointed to him. Natasha nodded her head. Sylvia got up and walked towards him, she knew the people that were sitting at the table across from the bar. She made sure that he had a good view and then she slowly bent over the table and started to talk to the boys. Her double D breasts looked great in the shirt she had chosen and gave her the desired cleavage. She made sure he was looking and then stood straight up again and said good bye to the boys at the table. She walked around it, in his direction. She watched him as she slowly walked by, and she ran her fingers along the table top in front of him. She did not stop however; she went in to the ladies room instead. Teasing was something she loved to do.

  When she came back out, she saw that he was watching her. Her friends were just about ready to leave. She wasn’t going to go with them, but she walked them outside. When they were headed to the door, she turned back, met his eyes and gave him a little wink.

  Sylvia got out side and said good bye to her friends. Then she picked the only vehicle in the lot that didn’t look like it belonged to an old lady, and she leaned against it. Turned out she had picked the right car. About fifteen minutes later, the hottie from inside strolled out the door and right up to the car she was leaning against.

  “Want to go for a walk? I know a great spot.” She asked him innocently.

  He didn’t reply to her, he simply leaned over and opened the passenger side door for her to get in. He came around the other side and started up the car. Sylvia directed him where to go and a short while later they pulled on to a dead end road with a quarry at the end. This was the spot that most high school kids came to make out. She was hoping for a little more than that.

  She unbuckled herself and climbed out of the car.

  “Where are you going?” The guy asked from inside the car. His voice was deep and rough and it made Sylvia quiver.

  “Going for a walk, what do you think?” She was teasing him, and she knew he liked it.

  He got out of the car and followed her. She walked to the edge where she could look down in to the quarry, if it wasn’t dark outside. He joined her there, looking in the same direction as her. She turned toward him and took one finger and slid it down the front of his shirt. She could feel the hard muscles under the fabric. He shivered as her finger got closer to the top of his jeans. She stopped there and lightly traced a figure eight, right above the button of his jeans.

  He couldn’t contain himself any longer; he bent down and picked her up by the back of her legs. She wrapped them around his waist and her arms around his neck. He pulled her head down and kissed her; slowly at first and then the pace picked up. She opened her mouth slightly and his tongue shot in. He tasted so good. He started walking towards the car; slowly because he wasn’t paying attention to where he was stepping. They finally reached it and her back pressed against the passenger side door.

  Once he had her against the door, he held her there with his torso and his hands started to explore. The reached behind her and up her shirt as far as he could go. Then he travelled downwards and grabber her ass. He grabbed it so hard she broke the kiss and gasped. She looked at him for a minute and then kissed him even harder. He pulled away from the door slightly and pulled the handle. The door opened and she fell in to the front seat. Luckily, the car was older and the front seat was a bench style seat. As soon as her back was on the fabric, he started to pull her jeans off. He took them and her underwear all in one go. He pulled hers and his shirt off at the same time. Then he leaned down and kissed her some more. His hand ran down her chest, scooped in to her bra and squeezed her nipple. She moaned. His hand started to move south again, grazing over her stomach and in between her legs. He massaged for a minute, and then pushed a single finger inside of her. He broke the kiss and spoke.

  “You’re so tight; I want to be inside you.” His voice was even huskier than before and he was breathing hard.

  “Get inside me then.” Her voice was full of grovel too.

  Without another word, he stood up, spread her legs a little more, rolled a condom on and gently pushed inside of her. He was big, but Sylvia took all of him. When he was all the way in, he moaned quietly. Then he started to pump, very slow at first; getting used to her tightness. Then he picked up the tempo. She angled her body so that every pump hit just the right spot. Their breathing was both hard and she couldn’t help but moan every time he filled her up.

  She wanted to switch positions; it was her turn to be in control. “Sit down.” She told him.

  He pulled out of her and he did as he was told. Once he was sitting, she climbed on top of him. She lowered herself on to his erection and he filled her up again. She placed her hands on the back of the seat and started to move. She was in control of the pace and the movement and she moved just right so that he hit her right where she needed it. She took one hand off of the seat back and stuck two fingers in her mouth. He watched her suck on them and moaned as she pulled them out. She reached down and started to touch herself as she rode him.

  He must have liked it because he couldn’t keep his eyes off of her. His hands were on her sides, moving with her rhythm. This is what her curves are so good for.

  Sylvia felt the beginning of an orgasm, so she moved her hips a little faster. Between the penetration and her fingers, she knew she was in for a good one. Finally she was pushed over the edge and she felt herself gripping on to him inside of her, and that pushed him over the edge too. They fell together and enjoyed the ride.

  When the waves of pleasure had finally stopped washing over her, Sylvia lifted off of him and replaced her clothes, he did the same. He drove her back to the restaurant, kissed her hard one last time and she got out of the car.

  She watched him drive away as she was calling her dad to come and pick her up.

  ~

  The next morning, Sylvia got up, packed her bags, and they all loaded in the car. Her, her mother and her father were following Richard to the cottage. He had been there a few times when Brian had been home over the years.

  It didn’t take too long to get there, about a half hour or so. They pulled in to a long driveway and parked in front of the giant cottage. Sylvia was expecting a little shack, but what this was, was a mansion. It was two stories high, with a giant deck on the main floor and a balcony to match on the second. The whole house was made of wood, and the windows and doors all looked to be brand new. There was a trail that led down to a private beach where a kayak and a paddle boat sat. Sylvia got out of the car and started to explore. She walked down to the beach to take a look, then she came back up to the house and went around the back. That was where she found the hot tub.

  No matter how much she didn’t want to go to the cottage, she was glad she did. The hot tub made it worthwhile. She could not wait to change in to her bathing suit and take a long soak.

  By the time she was done looking around the back, she could hear that Brian must have joined everyone else in the front yard. She followed the path, and as she came around the house she saw the back of him.

  “Ah, there you are Sylvia. Do you remember Brian?” her father introduced her as she walked up.

  Brian turned around to greet her and they both stopped in their tracks. He was the guy from the restaurant. The one she had flirted with and winked at and rode in his car. She could feel her cheeks flare bright red. She knew she had to say something so her parents didn’t think something was up.

  “Um, no I do not. It’s nice to meet you Brian.” She looked at him and he was smiling.

  “It’s very nice to see you again Sylvia.” He smiled at her again, a very sexy smile, and then turned back to the conversation with her parents and Richard.

  He wanted her again. No way that he didn’t. It sucked that her parents were there though, how was she supposed to get close to him with her dad there? Maybe that would make it more fun, she thought to herself, tease him a little more.

  Brian led them all in to the house and she
started to explore again. The kitchen was huge, all brand new stainless steel appliances and a huge dining table. The living room was big as well; there was a very comfortable looking sectional couch and a couple of big chairs. There was a huge TV, which looked like it had a couple of different game consoles hooked up.

  She toured around the rest of the house; there were two bedrooms on the main floor, which would be for her parents and Brian. There were also two bedrooms upstairs; one for her and one for Richard. She told him she didn’t mind having Sophie sleep in her room. After checking out the upstairs, she went to the main floor and spent the day out on the little beach with her parents, Rich and Sophie and Brian. When she went in to use the washroom, and found a door she hadn’t opened yet. It was a set of stairs going down. She followed them and saw that it went to another living room typed space. There was a leather couch, a computer and a whole wall made of windows. There was a patio door in the middle and she stepped out. It was the access to the hot tub.

  Sylvia flew upstairs and was going to get ready for a hot tub soak but was cut off by her mother who had just come inside.

  “Sylvie, can you help me with dinner please?” She asked. Brian had stocked the whole house with food so all they had to do was cook it. Her mother loved to cook.

  “Yep sure I can help you mom.” She loved to cook too.

  The two women made steak, baked potatoes, mixed vegetables and Sylvia even found the ingredients to make chocolate chip cookies. They all ate so much that no one wanted to move after dinner. They had eaten late, and Sophie was falling asleep at the table.

  “I’m going to go and put her to bed.” Richard said as he got up from the table.

  Sylvia watched him walk away and go up the stairs. She was one lucky girl to be in a cottage with two such attractive men for the weekend. She would never get tired of looking at them.

  After dinner was cleaned up, everyone went and sat in the family room and Brian put on a movie. Sylvia sat on the couch beside Brian and her father. It was hard to not reach out and touch Brian; he was so close to her. She got a chill while watching the movie and he got up and fetched a blanket for her. He threw it over her and then climbed under himself. A few minutes later, she felt the blanket move and his hand was on her leg, massaging slowly. She looked around the room to see if anyone had noticed, they were all paying attention to the movie.

  About half way through watching, Sylvia’s mother got up to pee; pregnant ladies can’t seem to go more than an hour without needing a bathroom break. A few minutes later she called out to her husband.

  “Luke! Luke!” she yelled.

  Her father was up out of that seat within seconds. “What, what’s the matter?”

  “My water just broke, I’m sorry Brian for the mess, and I’m sorry Luke for making you leave early but I think this baby is coming.” Her mother sounded distressed.

  When everyone else in the room heard that, they were all up and out of their seats too. Everyone scrambled around. Sylvia’s father rushed around to find the baby bag, had they even packed it? Richard went to see if Sophie had woken up with all of the commotion, Sylvia was helping her mother get to the car, and Brian was holding the door for them.

  “Sylvie, I want you to stay here. I don’t want you to worry.” Her mother said to her in between contractions. “Your father will come back for you, okay?”

  “Yes that’s fine mom, whatever you want. Someone has to clean up your mess, and I don’t think those guys would be able to do it.” She pointed her thumb behind her to where Brian and Rich were standing. Her mother laughed. They had finally had reached the car and as soon as the door was shut, her father took off towards the hospital.

  The three of them; Sylvia, Brian and Richard all stood in the driveway and watched them go. They stood there still even after they were out of sight.

  “Well that was exciting.” Richard said.

  “Yeah, I’d say so.” Sylvia agreed.

  “It was a little too exciting for me. I need a beer.”

  Brian turned towards the house and started walking. Sylvia and Richard followed.

  They got in the house and Brian took two beers out of the fridge. He passed one to Richard and then twisted the top on his own. Sylvia sat on one of the stools at the breakfast nook. Brian took a long swig of his beer and then looked at Sylvia.

  “Do you want one?” He asked.

  “Sure.” Brian handed her one and she twisted her top off too. She took a sip, it didn’t taste all that great but it was cold refreshing. She took another sip. Before she knew it, it was gone. Brian passed her another.

  The three of them sat in the kitchen and drank beer for a while. Eventually someone took out a deck of cards and they started to play. First they played rummy, but as the beer went down, the game changed.

  They started to play poker. They didn’t have any chips, so it was decided they would play strip poker. It was Sylvia’s idea, and the men both agreed. If it weren’t for the beer, she wasn’t sure if they would. She knew if she was alone with Brian he definitely would, but with Richard there she would think he would be more conserved, but they both agreed to play.

  Within the first half an hour, Sylvia was already topless and she had lost her socks and shorts. She sat at the table in only her bra and under wear. Brian too had to remove his shirt, and Richard was fully clothed, he was good at poker.

  “I got nothing.” She said to them at the end of a hand, and threw her cards on the table.

  “Looks like you’re losing another piece of clothing.” Richard said with a smirk.

  Sylvia undid her bra and flung it over her shoulder. Brian and Richard took a minute to stare, and then they went back to the game.

  She was dealt two aces, Richard flipped up a queen, an ace and a three. This was a good hand. She bet two pieces of clothing, both men matched her. Richard then flipped a seven, that didn’t add anything to her hand. The last card he flipped up was another queen. She had a full house; finally a good hand.

  “Show your cards boys.” She smiled sexily at them.

  Richard didn’t have anything, and Brian had two pairs.

  “Two pieces of clothing, take them off.”

  Richard took his socks and his shirt off, Brian his socks and jeans. This was getting a little more exciting she thought.

  The next hand she didn’t have anything good, but she didn’t want to fold. She lost another piece of clothing and so did Richard. He stood up and pulled his shorts off; Sylvia noticed that Brian watched him carefully as he did. It never occurred to her, but maybe he was bisexual.

  It was her turn to take her clothes off, but she only had one piece left. She stood up, turned around and said, “Looks like you boys have me beat. I think I’m going to call it a night.” She pulled her panties down her legs and flung them on to the table. Then she walked up the stairs and got in to bed.

  Everyone all slept great that night.

  ~

  The next day, everyone seemed to be in a good mood. They had heard from Sylvia’s parents and her mother was doing well, there was no baby yet but they kept her because they suspect there will be soon. Brian made everyone breakfast, and then they all headed outside. The sun was already shining and it was going to be a beautiful day. Sylvia took Sophie out on the paddle boat, she took a swing at the kayak and she even did some fishing with Richard. She made sure that she wore her favourite bikini all day.

  At supper time, she made everyone up a giant pot of chili. Sophie was so tired she went to bed right after eating. Sylvia cleaned up the dishes and headed to the shower. The hot water felt good on her skin, it reminded her about the hot tub. With all of the commotion, she had forgotten about it.

  She rushed out of the shower and in to another bathing suit. This one was red and white striped. She threw on a dress and sweater over top in case it was chilly. She basically ran down the stairs and in to the main part of the house. She stopped for a minute when she didn’t see anyone. Brian and Richard were nowhere to be fou
nd.

  She went out the front door and looked around on the deck. No sign of them. She went down the stairs and looked across to the beach. It was dark but she didn’t see a light or anything. Then she heard a voice. It was Richards. She followed the path that led to the back. She was as quiet as she could be, she didn’t want them to hear her. She poked her head around the house and could see that the men’s shorts were on the ground. They were naked together in the hot tub.

  She listened carefully to what they were talking about.

  “Oh yeah, she’s hot for sure.” That was Richard.

  “She’s just as good as you think she would be.” Brian almost purred the sentence.

  “I can’t believe you had sex with our best friend’s daughter.”

  “Hey, I didn’t know it was her. Last time I saw her she was eleven, and you basically made her strip last night. Man she got hot.”

  “She really did. I fantasize about her every time she baby sits. I can’t help it. It sucks that she’s Luke’s little girl.” Richard sounded genuinely disappointed.

  They were talking about her. They were talking about how they both wanted her. Sylvia was ecstatic. She knew what she had to do; if they wanted her, they could have her. She wanted both of them, at the same time. She didn’t care if they were her father’s friends, he didn’t need to know. She had already had one, now it was time for both. This was like a dream come true for her.

  She took a deep breath and stepped out of the shadows and started walking towards the hot tub. Both men watched her get closer but didn’t say anything. The only thing she heard was the soft music playing and the sound of the water in the tub. She got to where the pile of clothes was and added hers to it. She stripped them off slowly, piece by piece. First the sweater came off, and then the dress. She made sure that both men were watching her. Then she turned around and slowly pulled the string that was holding her bikini top on and pulled it over her head. Staying turned around; she grabbed the waist of her bottoms and slowly ran them down her legs, successfully giving both men a great view of her ass.