Pleasing My Sister-in-Law

The day after my family and I returned from Las Vegas, I sent my oldest daughter off to school, my wife went to work, and I stayed home with my two younger daughters. Mondays were my typical day off from work, so it was nice to have a day to relax, unpack, and put things away from the trip.

I was debating most of the morning about messaging Jessica. But what to say? And what if Jack saw it? I thought about different ways to get in contact with her or finding out some way to see what Jack could see of hers, but before I could figure it out, Jessica sent me a message on Facebook.

"Hey, what is your work schedule like? Just trying to figure out when is a safe time to contact you," the message read. I sent her back a message with my work schedule and told her pretty much any time was a good time to message me. I said I was worried about contacting her and Jack finding out.

"No text messages. He reads all of those. But he doesn't have access to my Facebook, and I delete them ASAP anyway. As long as it's during the day, I'll find some time to respond. I can't make the same promise after I leave work, however," she said back.

"Are you sure about this? I enjoyed the weekend, but I don't want us to get caught," I asked her.

"Yes, I am. I would like at least one more time with you. But if you don't want to, I understand," she said. I told her I did want more, and she said, "So, I guess we just have to figure out when."

I told her I couldn't wait, and we spent the rest of the day talking about different scenarios to get us alone. Early that afternoon, I received a text from Kourtney, my wife's sister.

"Hey, so I know you slept with Jessica over the weekend. And I know that you were checking me out in the hot tub. So, I just want to know...when is my turn? Or do I need to tell my sister?" The text said.

I responded back, "No need to tell anybody because you're right on both accounts. I just want to know two things. Why do you want to cheat on your husband? And when?"

Kourtney texted back to say, "I have a very high sex drive. And Gary can't keep up with it. He has low testosterone and a low libido. He knows this, and we've kind of come to terms with it. I get to sleep around, and he gets me to take care of him. I still love him very much, so I won't leave him. But I do things like this to keep myself happy."

None of that surprised me about Gary. For the nearly eight years that they've been married, I think he's been unemployed for half of them. They live with Kourtney and my wife's parents in their basement, and he's usually sitting on his couch playing video games. I texted back to say, "Damn, so I'm not the first?"

She laughed in her text as she said, "Nope. Well, first in the family. So, what are your plans this weekend? Maybe I can help get Kathy and the kids out of the house."

I told her that I had inventory that Saturday, plus two of my kids had soccer games, but I wasn't sure about plans after that. She told me not to make any plans but to stay home, and she'd figure out the rest.

A few days later, my wife told me that after our daughter's soccer games, her mom had invited them to some kid event in another city. Kourtney was going to go with them, and I was free to do some yard work, like I told her I was hoping to do.

I wasn't sure how Kourtney was going to end up at my house, but I figured it out when my wife texted me Saturday morning to tell me that Kourtney had other plans come up, wasn't going with them, and her dad was instead. I texted Kourtney to ask what her other plans were, and she simply said, "You."

After inventory ended, the soccer games were done, and I helped my wife change the kids and sent them off. I was left waiting at my house for Kourtney. My dick was starting to grow in my pants as I thought about her, remembering the swimsuit she had on the previous weekend and the other views of her body I had seen.

I thought back to before my wife and I were married and we were at her parents house. We are members of the LDS church, and it was a general conference weekend. General conference is where all the leaders of the church come together in Salt Lake City and, over the course of two days and five two-hour sessions, talk to the members of the church. The majority of us just stay home and watch it on TV.

Kourtney, at the time, was nineteen years old, fresh out of high school, and still a believer in the church. Her and Jack, her older brother, had gotten tickets to the morning session of the conference, while everybody else in the family stayed home to watch it.

I was down in the basement, sitting in a chair with my future wife, when Kourtney and Jack came home. Kourtney's bedroom was in the basement, and when she came downstairs, for some reason, she pulled her dress off over her head that she wore to conference and threw it in the laundry room before going into her room. She didn't see me and Kathy sitting there, but I did see her body in just her bra and panties.

I was thinking of that when she knocked on the door before letting herself inside. I greeted her at the top of the stairs as she came up them, and she gave me a quick hug.

Kourtney was nearly six feet tall, with black hair going down her back, almost to her butt, and tan skin, thanks to her Native American ancestry. Did I mention that she was adopted? She ran cross country in high school and kept her athletic body afterwards, playing rugby and ultimate frisbee during her twenties. Out of the three sisters in the family, she definitely had the best body and knew how to dress fashionable. But, today, she just had on a pair of black leggings and a red and teal long-sleeve shirt. Her black hair was pulled back into a ponytail.

As she sat down in the living room, she said, "So, why are you cheating on my sister?"

I laughed and said, "Because I'm an idiot? I don't know. I like sex."

"Have you ever fantasized about me?" I told her I had, and she said, "Good, because I've fantasized about you. Now, let me see that cock that Jessica was bragging about."

Kourtney stood up from the couch and walked towards where I was sitting. She kneeled on the floor in front of me and reached forward. I lifted my butt off the seat as she pulled my pants and underwear down, and my semi-hard cock flopped out.

Kourtney wrapped her hand around me, rubbing my shaft up and down, and pulled it towards her mouth. She held my cock straight up, stuck out her tongue, and licked from the bottom of the shaft up to my tip before wrapping her lips around my head and starting to suck on it while her hand continued to rub my shaft. I quickly grew to my full six-inch length, her fingers having to loosen their grip as I grew thicker in her hand.

Kourtney started to bob her head up and down my cock while I leaned back on the couch, enjoying the amazing feeling. After a few minutes, Kourtney let go of me and stood up. I watched as she pulled her shirt off over her head, leaving her in a tan-padded push-up bra. She had maybe a B-cup-sized chest. But my eyes were drawn to her butt as Kourtney turned around, pulled her leggings down, and shook her well-shaped ass at me. I reached out and spanked one of her exposed cheeks, watching as the black string from her thing disappeared in between her cheeks.

When she stood back up from pulling off her leggings and turned around, she said, "Am I going too fast for you? Jessica wasn't kidding about your cock."

I pulled my shirt off and kicked off my pants, holding my arms out for Kourtney as she climbed onto my lap. I started to kiss her skin around her upper body and neck and said, "How about we get these clothes off you, then we can move a little bit slower?"

"I'm just warning you; as soon as my panties are off, your cock is going in," Kourtney said, wrapping her arms around my neck, and she started to grind her hips on my lap. Still kissing her neck, I reached around her back, unhooked her bra, and pulled it down her arms. Kourtney shook it off, tossing it down to the ground, and continued to roll her hips back and forth.

I moved down to her breasts, noting that they were the same tan skin color as the rest of her body. I had always wondered about them. I took them both in my palms, squeezing them, before leaning forward and licking her right nipple, taking it in my mouth and sucking it while I rubbed her left nipple in my fingers.

I kissed her to her left breast, giving that nipple the same treatment before I heard Kourtney say, "Fuck it, I need you in me."

I let go of her breasts as she stood up, pulled her thong down, and climbed back onto me. I barely got a glimpse of her shaved pussy before she was pulling my cock inside her and sliding down my shaft. As Kourtney started to rock her hips back and forth on top of me, she wrapped her arms around my neck again and leaned down to passionately kiss me.

Our tongues slipping into each other's mouths, I moved my hands down to her butt, gripping her cheeks in my palms and squeezing them as she rode me. Kourtney finally broke the kiss, leaning her forehead against mine as she opened her mouth and started to moan. "Spank me," she commanded, and I did.

"You like it rough?" I asked her.

"The rougher, the better," she told me. "Pull my hair, spank me; hell, I might have to bring my handcuffs over next time."

Kourtney sat up straighter on me, and my hands moved her hips as she started to bounce on my cock harder and faster. "Tell me what else you like," I told her.

"Cum on my face and my tits. Shower sex is hot. Doggy style while my hair is being pulled. I love to have my hands tied behind my back and be face-fucked," she said in between moans. "I bet my sister doesn't like any of that."

I told her she didn't as I started to push my hips up into her. "I didn't think so. Too bad; your cock is made for it. Good hell!" Kourtney said her riding was almost out of control.

"I'm getting close," I said, feeling her pussy sliding up and down my shaft.

"Me too," she said. "Bend me over and finish in me that way."

Kourtney stood up from me and moved to the side as I stood up too. She grabbed onto the back of the couch, spread her legs wide, and bent over slightly. I stood behind her, my cock easily slipping back into her wet pussy, and I grabbed her hips as I started to pound into her over and over.

I felt her pussy clenching around my cock as she orgasmed. Kourtney was pushing her body back against mine until my own orgasm hit and I pushed deep inside her, causing us both to collapse onto the couch, Kourtney landing on her knees with me still in her. I used my grip on her hips to move her body back and forth, using her well-luped pussy to milk the cum from my cock.

When I was done, I pulled out of her, twisting around to sit on the couch. Kourtney did the same after she caught her breath and said, "Alright, that wasn't bad for your first time with me."

"Wasn't bad?" I asked with a laugh. "I guess next time I'll have to face fuck you before I finish in you."

"Now you're talking," Kourtney said as she started to get dressed.

A few days later, on my day off, Jessica sent me a message that said, "I heard that you finally got to please Kourtney."

I told her that I had, but I still wanted her, and she replied back, "Don't worry, I'm not jealous or anything. Me and Kourtney have been talking about ways to get us all together."

"You mean, like a threesome?" I asked her.

"No, not really. More like, you take turns with the both of us, but neither one of us is really interested in being with a girl," Jessica said back.

"That would be awesome if we could make it work," I said.

"I'm pretty sure we have a good idea to make it work; we just need to finalize some details first. But I'm hoping I can get you all to myself soon," Jessica said.

"I hope so too," I said. Jessica asked me what I was up to that day, and I said, "Nothing really. I'm trying to get the girls down for a nap right now."

"What are you going to do while they nap? Danny alone time?" She asked with a winking emoji.

"If you want the truth, probably. Want to help?" I said back.

"I so would if I were close," she said.

"Still can. Just send me a picture of you." I replied.

"Naked? That would be hard; I do work at a school," Jessica reminded me.

"Naked, fully clothed, down your shirt, just send me something that you think would get me going," I told her.

I didn't receive anything back from Jessica, and I eventually sent her a message telling her that she didn't have to and that I went too far and apologized for it. I got my daughters down for a nap and went to turn on a movie when my phone went off.

I opened up Facebook Messenger to see a picture of Jessica in the school bathroom, standing in front of a mirror. She had her brown hair pulled back into a ponytail, a lanyard with her picture ID on it around her neck, and she had pulled up her shirt to show me her C-cup-sized breasts inside a red bra. The message also said, "How far can you go with this?"

I sent back a message that said, "Almost all the way."

In response, Jessica sent another picture, this time with her bra pulled up and her breasts exposed, and said, "Now?"

I replied back, "All the way."

"Good. Sorry, it took a minute. I had to sneak away from everybody. Have fun!"

A few days later, as I was working away at my wholesale job, Kourtney texted me to ask what time I was off and what I was doing after work. I told her, "I get off at two and am going to get my kids afterwards. Why?"

She replied back, "I'm home alone and want to give you a blowjob. Got time before you pick up the girls?" I told her I did, and she said, "Cool, see you soon!"

Right before I got off work, Kourtney texted me again to let myself in and that she would be downstairs in her room. Luckily, her parents house, where she lived, was only a few minutes away, and before too long, I was walking down the stairs. When I walked into her room, I saw Kourtney sitting down on her couch, playing a video game, wearing only a towel around her skinny body.

She sat her controller down, standing up to greet me. As she walked towards me, she let the towel drop, showing me her naked body underneath. Her black hair was wet, like she just got out of the shower. I wrapped my arms around her body, pulling her close to me and kissing her lips.

Ending the kiss, Kourtney squatted down, undoing the button on my jeans as she did so. I said, "Well, I could get used to this."

Kourtney laughed as she pulled my cock out and said, "I can't believe it's happening. I just got lucky that the one day I got off this week, Gary was going to his mom's house and job searching all day."

Kourtney wrapped her hand around my shaft, jacking me off until I was at my full six-inch length. She put me in her mouth, bobbing her head up and down, taking me down in her throat, and moving her hand down to my balls. She gently squeezed both of them while blowing me.

Taking me out of her mouth, Kourtney said, "Do you know what I was really hoping for today?"

"What's that?" I asked.

Kourtney looked up at me with her brown eyes and said, "For you to fuck my throat and cum down it."

I grabbed onto the sides of Kourtney's head, bringing her back to my cock. She eagerly opened her mouth and let me slide my cock into it. I felt little resistance as I pushed down her throat and held Kourtney in place with her nose in my groin.

Still holding onto her head, I started to thrust my hips back and forth, sliding my thick cock in and out of her mouth. Kourtney was staring up at me as I pounded her mouth. I let go of the sides of her head, moving one of my hands to the back of it and using it to push her head down as I thrust my hips.

Slowing down a bit, I reached down with my other hand, grabbing Kourtney's breasts, switching from one to the other, and pinching her nipples.

Feeling my orgasm starting to build up, I stood back up straight, kept one hand on the back of Kourtney's head, and slid my cock in and out of her throat until I felt it twitching. I pushed Kourtney all the way to my groin as cum erupted out of the end of my cock. After the first few squirts, I started to slowly pump my cock in and out, looking down at her to see a mixture of her spit and my cum spilling out the sides of her mouth.

When I was done, I let go of her head and pulled my cock out of her mouth. Kourtney sat back on her legs and wiped her mouth clean. I told her, "We need to do this more often after I get off work."

Kourtney laughed as she stood up, grabbing her towel off the floor and using it to clean off my cock. She said, "We got lucky today. Until Gary finds a job, I make no promises. But, after Jessica told me she sent you a picture of her tits to jack off to, I knew I had to one up her somehow."

"One up?" I asked. "You two having some kind of competition about me?"

"Maybe?" Kourtney said, helping me pull up my pants. "Are you complaining?"

"Not at all. Keep it up, and I can't wait to see what's next," I said as I wrapped my arms around Kourtney's naked body and pulled her close to me. I gave her a quick, passionate kiss before saying that I had to leave. Kourtney walked me to the basement stairs, telling me thanks for coming as I left her house.

Jessica messaged me the next day while I was at work and said, "So, you hooked up with Kourtney again? It looks like I'm falling behind."

I laughed as I sent her one back, saying, "I wouldn't say a blowjob is hooking up. And I also wouldn't say you're falling behind. We'll find some time together soon."

"I hope so. If I'm just sending pictures and Kourtney is giving you blowjobs, she's going to win!" Jessica's return message read.

"I still know why you're competing with each other. Is there a prize?" I said.

Jessica replied back, "Just your cock every time one of us gets it."

Me and Jessica continued to talk throughout that day and the next, trying to figure out a way for us to get together. Unfortunately, we weren't able to that weekend or the next, which was Halloween weekend. As November came and Thanksgiving drew nearer, we were throwing out any idea one of us could think of, even wondering about sneaking away after Thanksgiving dinner with the family.

On Thanksgiving day, we had planned to go to my in-laws house along with the rest of my wife's siblings and their families. I asked both Jessica and Kourtney if they would be able to behave around everyone. They both said they could. I told them that I guess I would be the only one wishing we could sneak away, but they both said they wanted to as well.

Jessica and her husband brought the turkey, while my wife and I provided the ham. We showed up early so my wife could help cook the side dishes. When Jessica and Jack got there, we all said hello as Jessica walked up to my wife and asked her something. My wife turned to me and said, "Hey, Danny, Jessica is wanting to know if we could go get a game from our house? Do you want to do that?" I asked what game, and after they told me, I started to get up to leave.

"Can I go with you?" Jessica asked. "Maybe see if you have any other games we want to play." I said sure, and we grabbed our coats, walking out the door together after saying good-bye to everybody. As we left, I saw Kourtney smirking.

Getting into my van, I turned to Jessica and said, "Really? You want to see what games we have?"

Jessica, sitting in the passenger seat, leaned towards me and said, "Hey, it got us some alone time, right?" I mentioned that it couldn't be for very long, and Jessica, putting her hand on my groin, said, "Guess I better get you ready now."

Jessica started to rub my cock through the jeans I had on. I started to grow harder and looked over at her while I waited at a red light to turn left. That day, she had on a salmon-colored plain shirt with a white long-sleeved shirt under it. With the way she was leaning, her shirts were falling open, giving me a look down at her C-cup-sized breasts in a white bra. She saw me looking and pushed her loose brown hair out of the way.