Wingmom Ch. 01

Sydney drove home in a state of mixed anger and frustration. She and her husband had been meant to spend a romantic weekend alone together. They had been planning it for over a month. Everything had been taken care of. Craig had the weekend off from work, and she had the weekend off from her own usual commitments. She was even going to miss one of her best friend's first yoga classes. Craig's son Kyle was watching the house and the dogs, so everything was set.

Everything had been planned to a tee. They drove up to the cabin together. They spent an afternoon sitting in the sun together. It felt just like when they first got married. Sydney could tell Craig was indulging her a bit, but she didn't care. It felt good to her. They had a nice romantic dinner, which she had spent two hours preparing. After dinner they moved into the living room. They started off slow, and things were beginning to heat up, when Craig got a phone call.

Sydney expected him to ignore it, as they had planned. He had promised that he would spend the weekend just with her. They were supposed to shut out the whole outside world. But he answered the phone. Sydney could hear him yelling at someone, and it didn't take long for her to know that her romantic weekend which she had spent so much time preparing for, was over before it even started.

Craig apologized profusely, and Sydney believed that he meant it. But that didn't change how she felt. Craig had a cab pick him up, and take him straight to the airport. Sydney spent that night alone at the cabin. She cried herself to sleep, wishing that her husband was still the man he had been when they met. She had known for a long time that he took his work more seriously than their marriage, and this just proved the point.

In the morning, Sydney cleaned up, packed up, and left, alone. The whole drive back home she thought about her marriage, and what to do to fix it. She missed having a partner to share things with. But more than that, she missed having a partner to share sex with. She had always had a healthy sexual libido. She was a good, honest woman, and she had never cheated, nor would she ever want to. But they simply didn't have sex anymore. It had been months. This was supposed to be the weekend where they would make up for lost time. Instead, she was left frustrated, and hornier than ever.

When she pulled into the driveway of their home, everything looked normal. She walked into the house still thinking about what had happened, and then stopped in her tracks as she stepped inside. Right away it was clear that Kyle had not expected anyone to come home early. There were empty beer bottles all over the place, and two empty pizza boxes with half eaten crusts lying around. It didn't look like he had thrown a party, but it did look like he had spent the night drinking with friends.

Sydney called out, preparing to yell at Kyle for making such a mess of their house. When he didn't answer, she started up the stairs to his room. She knocked on his door, but he didn't answer. She thought she could vaguely hear the sound of his shower running. She knocked again, waited for an answer that didn't come, and then opened the door. Kyle's room was even more of a mess than downstairs. There were more empty beer bottles, as well as a dirty two-foot bong on his desk. Sydney walked into the room, looking around at all the mess.

Kyle's room was usually a mess, but this was a different level. She walked over piles of clothes to get to his bed. There were even more empty bottles on his nightstand. Sydney noticed a small container next to the bottles, and picked it up. She hadn't smoked, nor even seen weed since college, but the smell was unmistakable. She put the container back, trying to control her rage. She knew that she was more angry at Craig than Kyle. But Craig was away, so Kyle would have to take the brunt of her anger. Just as she was trying to decide what to do about Kyle's little party, she noticed the trashcan in the corner. She walked over to it, hoping her eyes were deceiving her.

She bent down, and looked in the bin, and then stood up straight. Her eyes went wide, and for a moment her anger disappeared entirely. She took a moment to regain her composure, and then bent down again. Inside the trash bin, were several used condoms. Sydney knew that Kyle was probably sexually active. He was nineteen after all, and quite attractive. He didn't really speak about girls with Sydney, but she wouldn't expect him to. She had only been his stepmother for six years, and she was only twelve years older than him.

But now she knew that she would have to ask him some questions. Kyle being sexually active wasn't a problem, and wouldn't be anything Sydney would need to address. But what she saw in the trash bin was quite concerning. There wasn't just one used condom, but four. First Sydney wondered if Kyle had been having sex with other men. The thought lingered until she remembered that he was definitely attracted to women. She had known him long enough to know that. But that seemed to imply that Kyle had been having sex with a woman, and another man, or more than one man. The idea of Kyle and his friends all having sex with one girl horrified Sydney. He seemed like too good of a kid to do something like that.

As Sydney stared down at the condoms in the bin, she slowly registered that they were rather large, much larger than most. She didn't want to touch them, but she did want to get a better look. She looked around for a moment, and saw a pencil on the desk. She took it, and bent down over the trash bin. She carefully picked up one of the condoms with the pencil, and held it up. It was very clearly soiled. She could see a good deal of white semen inside it, and some of it dripped out as she held it up. She turned her face away in disgust, but then looked back. The size of the condom was shocking. She had seen many used condoms in her time, but none had ever looked like this. She took a moment to measure it with her eyes, and judged it to be at least eight or nine inches, possibly more.

She dropped the condom back in the trash, and picked up another. This one was also soiled, and just as long. She checked all four of the condoms, and was surprised to see that they were all the same size. That made her a little bit relieved, as it seemed that they had all been used by the same person. But that meant that either Kyle was having sex with a very large man, or he himself was a very large man.

Sydney sat down on Kyle's bed, her anger completely forgotten. Now she was trying to figure out what was going on. Craig was not anywhere near as large as whomever had soiled those condoms. He wasn't as small as some men Sydney had been with in college, but he wasn't large either. She had only been with one large man in her life, back in college, and she still thought about it sometimes. That guy had been a real jerk, but the sex had been the best she ever had.

As she sat on the bed, her mind going over quite a lot, she heard the shower turn off in the bathroom. A moment later she heard Kyle getting out and drying off. Sydney took a moment to think about what to do next, and decided to just confront Kyle straight away.

"Kyle!" She shouted out in a stern voice. She heard a crash from the bathroom, and then fumbling around. The bathroom door opened a moment later, and Kyle's head poked out, with wide frightened eyes.

"Oh shit," Kyle said when he saw his stepmom sitting on his bed, looking pissed. "Uh, hey Sydney. What are you doing here? I thought you wouldn't be home until Monday."

"That was the plan," Sydney said, crossing her arms as she frowned at Kyle. "But your father got a call from work. He flew out last night."

"Oh, uh, sorry," Kyle said. "I know you had a whole weekend planned."

"Yes, I did," Sydney said, feeling the anger perk up again at the mention of her lost weekend. "I see you had some plans of your own."

"Um, ya, sorry," Kyle said sheepishly. He stepped out of the bathroom, with a towel wrapped around his waist. Sydney's eyes fell to the towel for a moment, and she noticed the vague outline of something rather large. She quickly brought her eyes back up to Kyle's face. Luckily he wasn't looking at her, but rather staring at the floor in embarrassment. "We didn't break anything. And nobody drank and drove."

"Well that's good," Sydney said, glad to hear that Kyle had been at least somewhat responsible in that regard. "How many people did you have over?"

"Just five," Kyle said. "It was just Chris and Mike, and then some girls from school."

"And what happened with these girls?" Sydney asked, already afraid of the answer.

"What do you mean?" Kyle asked, looking confused.

"I saw what's in your trash bin Kyle," Sydney said, and Kyle's eyes went wide, and his cheeks went red. "Did you and your friends all have sex with these girls?"

"No," Kyle said quickly. "I mean, maybe, but definitely not together. Chris took one of the girls home with him, and I think Mike struck out with the other one. And then, uh, me and one of the girls had sex. But we used protection."

"Yes, I saw that," Sydney said, and Kyle turned even redder. "But there were four condoms in there Kyle. Who else was having sex here?"

"No one," Kyle muttered, not meeting her eye. "Just me and Amber."

"Kyle, your father and I were only gone for one night," Sydney said. "Are you saying that you had sex with this girl four times in one night?"

"Uh, ya," Kyle said awkwardly, still staring at the floor. Sydney had been about to say something else, but she stopped. That last piece of information caught her off guard. What Kyle was saying, was that not only had all of those very large condoms belonged to him, but he had gone four times in one night. Sydney couldn't remember Craig ever going more than twice in a night, and that only when they first were dating.

"Kyle, I'm not going to be mad," Sydney said, trying to remain calm. "But I need you to tell me the truth. It wasn't just you having sex here was it?"

"Yes it was, I promise," Kyle insisted. Sydney had known Kyle for a long time, and he didn't sound like he was lying.

"Where did you get those condoms?" Sydney asked. "I've never seen ones like that before."

"I had to order them online," Kyle confessed. "I tried buying some from a gas station, but, uh, they, uh, didn't work."

"What do you mean they didn't work?" Sydney asked.

"Well, um, they didn't really fit," Kyle admitted. "So I had to buy special ones online."

Sydney didn't know what to say to that. The condoms had looked much larger than any she had ever seen before. But what Kyle was saying, basically meant that he had a huge dick, and could go four times in a night. That would make him something of a sexual dynamo. That seemed unlikely, based on Sydney's sex life with his father. But she didn't know what other explanation there was.

"Ok," Sydney said slowly, trying to catch up to all this new information about her stepson. She was also beginning to remember just how horny she was. She had prepared herself for a weekend of amazing sex with her husband, and hadn't gotten any of it. Now it seemed as though Kyle had gotten it instead, and some very lucky girl as well. "So, you just had sex with this, Amber?"

"Ya, we've been dating for a few weeks now," Kyle said. "Since you guys were supposed to be out all weekend, I figured we could finally, uh, do it."

"So you hadn't had sex with her before last night?" Sydney asked.

"No," Kyle said.

"Well, um, how did it go?" Sydney asked. She was no longer angry, but she was extremely curious. She found herself wanting much more details than would be appropriate.

"Uh, great," Kyle said awkwardly. "I mean, I definitely had a great time."

"And Amber," Sydney went on. "She had a good time too?"

"Ya. I mean, I think so," Kyle nodded. "We did it a few times anyway."

"Yes, I saw that," Sydney chuckled awkwardly, and glanced nervously at the bin full of used condoms. "I thought maybe you and your friends had all slept with the same girl."

"No!" Kyle practically shouted. "It was just me and Amber, I promise."

"Well, that's good," Sydney said. "It's ok for you to be having sex, as long as you're being safe, and respectful. Which it seems like you were."

"Ya, nothing bad happened," Kyle said. He looked totally uncomfortable at the topic of conversation.

"Ok then," Sydney said. "Why don't you go get dressed, and then clean up the house."

"Sure thing," Kyle nodded, sounding relived. He got up and hurried back into the bathroom. Sydney heard him moving around in there, and she got up and went back to the trash bin. She picked up one of the condoms with the pencil again, and stared at it. It looked bigger than any penis she had ever seen, and there was clearly a large amount of semen in it. Without meaning to, Sydney got a whiff of it. It smelled unexpectedly intoxicating, and for a moment she closed her eyes, imagining a giant cock spewing thick jets of cum. A loud noise came from the bathroom, and she quickly dropped the condom back in the bin. She hurried back to the bed, and sat down just as Kyle reemerged, fully dressed now.

"I'll clean it all up," Kyle said, beginning to pick up empty beer bottles. "You don't have to help."

"Oh, I won't," Sydney laughed. "This is your mess; you clean it all up. And consider yourself lucky that your father didn't see all this."

"Ya. Uh, you're not going to tell him, are you?" Kyle asked nervously.

"I don't see any need to," Sydney said. "You were just having fun with your friends. As long as no one was drinking and driving, and you were just with Amber, then you really didn't do anything wrong. And I'm sure you would have cleaned up before we got back."

"I would have," Kyle nodded.

"Ok, well, clean up," Sydney said. "I'll go make some breakfast."

"Ok, thanks," Kyle said, letting out a sigh of relief. "And, uh, I'm really sorry your weekend got screwed up."

"Thank you Kyle," Sydney said. "I'm glad at least one of us got to have a fun romantic night."

"Uh, ya, thanks," Kyle said awkwardly. "And, uh, I'm, uh, sorry," he finished, and then hurriedly went about cleaning up his mess. When he came to the bin with the soiled condoms, he just picked up the whole bin, and took it in the bathroom. Sydney waited a moment longer, and then left his room. She still felt angry and disappointed with Craig, but now her mind was elsewhere.

She couldn't stop thinking about what she had seen. The condoms were huge, and there had been four of them. And it looked like there had been a lot of semen in each one. Sydney knew she shouldn't be thinking about her stepson in a sexual way, but now she couldn't stop it. Kyle was clearly quite the young man. She had already found him to be an attractive young man. He was tall, and handsome, and in very good shape. But now he seemed much more manly than before. The sheer knowledge that he was packing some serious heat, and knew how to use it, changed her whole outlook of him.

Sydney was only thirty-one, and still in the sexual prime of her life. When she had married a man more than twenty years older than her, she had known that their sex life wouldn't last forever. When she first started dating Craig, their sex life had been great. He took her on nicer dates than any of the guys her age could. And then they would go back to his large fancy house, and have great sex. Kyle was just a little kid back then, and seemed to be glad to have a new mother figure. His own mom had left when he was only five.

When Sydney married Craig, they began having sex less often. But that didn't seem odd. From what she had been told by other married women, that was quite normal. But as the years went on, they did it even less. Once Craig reached his fifties, he didn't seem to want to do it more than once a month at most. And that seemed to be more for her than for him.

Sydney found herself feeling hornier than she ever had in her life. She didn't want to do it every day, and she didn't want to sleep around with other men. She just wanted to do it every once in a while. And it had become such a rare event that she thought about it more than she ever had. She knew that as she got older she would want it less as well. But she wasn't old yet. She also knew that she wouldn't look the way she looked forever. It felt like a complete waste to not be having any sex at all when she looked as good as she did.

And now, in the midst of all that, on top of her disappointing weekend, she was finding out much more about her stepson than she ever expected to. She had always liked Kyle. And as she became his stepmom, she grew to love him. He was a good kid. He was smart, and kind. He did well in school, and was always respectful. He was also quite an athlete. He had always played sports, but as he got older, he got good at them. And in playing sports, he got in very good shape.

Kyle would often walk around the house without a shirt on. Sydney wouldn't stare, but she certainly noticed how strong and manly his chest and arms looked. She knew that he was a very handsome young man, and that the girls his age must find him hot. But Sydney hadn't really thought about it beyond that. She valued being a good stepmother, and she didn't want to think about Kyle in any kind of inappropriate way. But now that didn't seem possible anymore. He could no longer just be a good looking kid, who had a manly physique. Now that she knew he had a huge cock, she found herself having thoughts she knew she shouldn't be having, and tried to push them away.

As Sydney moved around the kitchen, cooking breakfast, Kyle walked in. He began cleaning up what mess he had left in the kitchen as she continued cooking.

"Hey, Sydney," Kyle said slowly. "Can, uh, can I ask you a big favor?"

"What sort of favor?" Sydney responded. She didn't want to let him get away with too much, considering he had trashed the house in one night while they were gone.

"Well, um," Kyle began, and then took an uncomfortable pause. "Uh, I was wondering if, well, if Amber could come over tonight. I told her she could when she left this morning. But that was before, uh, well, before you came back."

"You want to have her over for dinner?" Sydney asked. It seemed obvious that Kyle wanted to sleep with this girl again, but Sydney wanted to check.

"Sure," Kyle nodded. "And then, um, maybe she can sleep over?"

"Four times last night wasn't enough?" Sydney laughed, and then looked over to see Kyle blushing a deep red.

"No, I, it, uh," Kyle stammered. "We, uh. Well, like I said, it was our first time together. And it went really well. And, uh, we thought we would get to do it again tonight."

"But I ruined it by coming home early," Sydney finished for him.

"No," Kyle said quickly. "It's not like that. I just..."

"Yes it is," Sydney chuckled. "Yes Kyle, you can invite Amber over tonight. I'd like to meet her. Just because my weekend got screwed up doesn't mean yours has to too."

"Ok, thanks Sydney, I really appreciate it," Kyle said earnestly. They ate breakfast together, and then went their separate ways for the day. Kyle went out, presumably with his friends. Sydney went to her friend's yoga class, which she now didn't have to miss. It was only women in the class, so she got to vent her frustrations about her husband leaving her high and dry to the other ladies. They were all quite sympathetic. Sydney wanted to tell them about what she had found when she came home, but she refrained.

After yoga, she stopped off at the market, and got food to make dinner. She decided that she would help Kyle out. She would give him and his new girlfriend the date night that she had been planning for herself. For some reason, the thought of helping them set the mood, and then having sex again, made Sydney oddly excited. She wondered if they would do it with her in the house. And if they would do it as much as they had the night before. Would she be able to hear them?