Pleasing My Sister-in-Law

The day after Thanksgiving, despite my oldest daughter not having school and the other two not having to go to daycare, I was still up early with them, getting breakfast ready.

Jessica had sent me a message shortly after I woke up that read, "Are you up? What time does Kathy leave for work?"

I sent her back what time Kathy left, and she messaged, "Alright. Don't let your kids look at your phone after that. I'll have a little surprise for you."

After saying goodbye to my wife, I hurried to make my own breakfast. While I was eating my bowl of cereal, Jessica sent me a picture, and I opened up the message. She was standing in her bathroom, her brown hair down and loose around her pretty face. All she had on was a white, spaghetti-string top, that her C-cup-sized breasts were attempting to push out of, and gray shorts that barely covered her groin.

Along with the picture, she wrote, "Can you sneak away from your kids for a bit? Let me know when."

I finished my breakfast, cleaned up my daughters’ bowls, and sat my girls in the living room with the TV remotes, telling them that I would be back in a few. Going into my room, I let Jessica know I was alone, and she replied, "Cool, I'll send you a video on Marco Polo."

Marco Polo was an app the family used to send videos back and forth, mostly if it was harder to say than a text, but not enough for a phone call. Or just to show the grandparents what the grandkids were up to.

I lay down on my bed as I turned on the live video she was sending me. Once she knew I was there, she moved into her bedroom and set the phone down somewhere, backing up a few steps so I could see her entire body.

She started by turning around, bending over slightly, and shaking her ass at the phone. She then put her hands on the bottom of her tank-top, and pulled it up over her head. She turned back around, cupping her breasts in her hands, and squeezed them, bending over again. She moved her fingers to her nipples, showing me as she pinched and rubbed them.

Jessica then hooked her fingers into the waistband of her shorts and pulled them down. She kicked them off her feet, standing up straight with her hands on her hips and her legs slightly apart. She said, "I'm sorry, it's not in person. But here I am, completely naked. What do you think? Turned on? Want to see me?"

She ended the video by bending over and giving me a great view of her breasts. I quickly started my own video back at her, showing the outline of my hard cock in the pajama pants I was wearing. I said, "You're beautiful; yes, I'm turned on, and yes, I would love to see more," and ended the video.

When Jessica started hers back up, she was lying on her bed, her phone raised above her head, and she was using her free hand to play with her breasts again. She said, "Show me that cock of yours, and I'll let you watch me play with myself."

I pulled my pajamas down, and my hard, thick, six-inch-long cock popped out. I started the video by wrapping my hand around my shaft, rubbing up and down, and saying, "If you were here, my cock could be between your tits, instead of your hand. Or your hand could take the place of mine."

In her next video, as I continued to rub myself, she flipped the view, showing me her hairy pussy. She was using her free hand to rub it, and said, "That sounds amazing. Your cock is the perfect size to fit between my tits. But if I were there, I would want to be riding you."

Jessica moved the phone down, giving me a view as she started to slide her finger in and out of her pussy. "Gosh, I wish this was your cock again. Are you jacking off while you watch me?" She said that, and she ended the video.

I sent her back a video of me jacking off, telling her I was jacking off and that I was wishing she was here, too. Her next video was more of the same, with her rubbing her clit, pinching her breasts, and fingering her pussy. She asked me, "Are you close? I don't want to miss seeing you cum."

I was getting close, and I turned back on the video, rubbing my cock up and down, telling her I wanted to fuck her. I almost lost my phone when I started to orgasm, a rope of cum hitting the phone, and a few more sailing past and landing on me or the bed. I ended the video by saying, "Next time, your mouth better be over my cock."

She was very vigorously rubbing her clit, had her knees up, and her back was starting to arch. I could just see her face; she had her eyes closed and was panting and moaning heavily. "Oh God, yes, Danny!" Jessica moaned out as she orgasmed, her legs closing around her hand and pressing it more into herself, and her back and hips coming fully off the bed.

As she came down from it and spread open her legs again, she showed me the juice trailing from her hand to her pussy. She played with it, rubbing her clit with her wet fingers, then brought the phone back up to her face. She smiled, and said, "That was nice. By the way, I'm home alone all day. If you want, I can keep sending you stuff all day long."

I told her that would be amazing, and I started to clean myself up. Jessica kept the video rolling while she also got up, put back on her tank-top and shorts, and pulled her hair back into a ponytail. She said, "And if you want to see my tits or something, just say so." She ended the video by blowing a kiss at the screen.

The rest of the day, me and Jessica spent chatting about random things. I did, an hour after we masturbated for each other, ask to see her tits. Along with continuing our conversation, she sent a picture of herself pulling up her tank-top.

I said to her afterwards, "I never would have pictured you being this way. Jack seriously doesn't know what he's missing out on. Do you really like to show your body off that much? Do you masturbate a lot?"

"I never really was this way until earlier this year, when I first cheated on Jack. I always felt this sexual need, but didn't know how to fulfill it. But, yeah, ever since then, I have loved showing off my body and seeing how the guy reacts to it. And yeah, I've masturbated a ton. I always have; honestly, that's not a new thing. But you are the first person to watch me," she replied back.

"Wow, I feel honored," I said. "Do you have any toys? Or just use your fingers?"

"Just my fingers. I've thought about getting a little toy, but I haven't yet," she told me.

"Well, Christmas is coming up. It's too bad I didn't draw your name," I said, with a laugh.

"Oh geez, I could only imagine what everybody would say if you gave me a dildo," her next message said.

After I made my girls some lunch, I laid the younger two down for a nap, let the oldest put on her headphones and get distracted by her tablet, and then told Jessica I was getting horny again. As I lay on my bed, my phone went off a bunch, with Jessica sending me picture after picture of her, completely naked, in different poses. She told me to put them to good use and to let her see when I was done, which I gladly did.

That Monday, while I was at home again with the kids, Kourtney sent me a text saying, "So, you fucked Jessica on Thanksgiving, and you two spent the whole next day trading nudes back and forth? Where's mine?"

I laughed and sent one back, saying, "I could be asking you the same question. Is that all she told you we did?"

"No," Kourtney's next text started. "She told me about the Marco Polo videos. I'm so shocked she filmed herself doing something like that."

"I was too. Have you ever taken a video of yourself? Alone or with somebody?" I asked her.

"Once. It was the last time I would sleep with this one guy. He was getting too into me. I told him it was over, and he said he would pay me $1000 if he could record me blowing him for twenty seconds. Easy money," she told me. Before I could respond, she sent another text saying, "Want to see it?"

I told her yes and waited while she found the video and sent it to me. Making sure I was alone, I opened up the short clip to see Kourtney completely naked and kneeling on her knees. She had her long brown hair pulled back, and her hand was wrapped around some guy's shaft. He didn't look to be more than four inches long, and her hand easily fit over his shaft. That didn't stop Kourtney from working her magic, blowing him with her mouth at the same time her hand rubbed his shaft.

I watched as the guy slid his cock in and out of her mouth until the video ended, not realizing it had started to replay. When I finally did, I said to her, "Damn, that made me hard!"

"Good," Kourtney replied back. "When are you going to come and fuck me?"

"You tell me. When is Gary going to be gone again?"

"Good question. I'll try to work something out," Kourtney said.

Unfortunately, try as we might, neither Jessica nor Kourtney were able to get away for the next few weeks. With Christmas coming up, we were busy with a different event almost every night and going to Christmas parties every weekend.

The Saturday before Christmas was our family Christmas party. Unlike Thanksgiving, I didn't think there would be any chance to sneak away with Jessica or Kourtney, as much as I told them both that that would be the perfect Christmas present. Our party was full of food, a present exchange, and games.

As the night wore down, Katie and her new husband were the first to leave. Jessica and Jack left shortly after them, Jessica giving me a look that nearly made me fall over, glancing down at my groin and licking her lips. With them gone, my family was the last there, along with Kourtney and Gary, who lived there, along with my in-laws. I could see Kourtney trying to figure something out, but she wasn't having much luck.

With the kids starting to get tired, we started to pack up our stuff to make the short drive home. There were a few items that needed to go down to my in-laws’ basement, and Kourtney asked if I could help her carry them down. I said I would and watched as she quickly said goodbye to my daughters and my wife and started to walk downstairs. I grabbed the items she had asked me to, and started to follow her, admiring her ass in the black sweat pants she had on.

Once in the basement, Kourtney led me into the storage area that was next to hers and Gary's room. After setting the items down, Kourtney wrapped her arms around my neck, pulling me in for a kiss. As our tongues pushed past our lips to wrestle together, my hands came down to her butt, giving it a nice squeeze.

We both knew the kiss couldn't last long, and ended it with us both wanting more. I went to follow Kourtney out of the storage room, but she stopped just before the door. She hooked her fingers into her sweatpants and yanked them down to her ankles, revealing a blue thong going into her ass.

She bent over, sticking her ass out, and moved until her ass was on my groin. She moved it back and forth a few times before standing up and pulling her pants back up, giving me a sexy smile as she opened the door and left the storage room.

The next week was, of course, New Year’s, and on the First, Kourtney texted me to say, "Do you have any plans this Friday?"

I told her I didn't and asked why.

She said, "Because I'm going to invite you to a game night with me and my friends. At least, that's what I'm going to tell Kathy. In reality, me, you, and Jessica are going to get a hotel room and spend the night fucking. You down?"

"All night? How are we pulling this off with your husbands?" I asked, my cock growing in my pants at what she was proposing.

"We're telling them it's a girls’ night. And if Kathy ever asks about it, Gary won't care. Jessica is pretty confident she can think of something for Jack. And yes, as long as possible," she said.

"Who is paying for the hotel?" I asked next.

"Me. This is the idea me and Jessica have been thinking of for a while, and we went back and forth on it. I finally decided it might be the only way we can do this, and I said I would pay," Kourtney told me. "Are you down?"

"Of course," I said.

"I figured you would be. I'll text Kathy to see if she thinks you'd be interested in a game night. I know what kind of games she doesn't like, so I'll mention those so she doesn't want to be involved. Once she answers, I'll still text you so you can bring it up with her if she doesn't. And I'll book the hotel for this Friday," Kourtney said.

Later that day, my wife did ask me if Kourtney texted me about having a game night and encouraged me to go.

That Friday, as I anxiously tried to focus on my work, I started to message Jessica, and she was just as excited as I was. After she told me she had kept daydreaming about that night, I asked what she was most excited for.

She replied back, "Probably just being with you and not having to worry about being caught or rushing. What about you? I'm sure you're excited to have two girls that both want you."

"I'm just hoping I can keep up with both of you! I'm excited for that as well. Speaking of two girls, how are you feeling about them? Are you going to be OK seeing Kourtney naked and seeing me and her fuck?" I asked Jessica.

"Yeah, I think so. I actually went and bought a dildo, so I'm bringing that to play with while you two do your thing," Jessica told me.

"If you're playing with a dildo, I might have a hard time focusing on Kourtney," I said.

"Whatever," Jessica replied.

I asked Kourtney the same question about seeing Jessica naked, and she said, "Actually, I'm excited for it. I don't want to do anything with her, but I can appreciate how beautiful she is and admire her body." I asked if she knew about Jessica's dildo, and Kourtney replied back, "Yeah, she asked me what kind I use. I'm bringing mine too."

Kourtney had told me earlier that she was going to pick me up at six PM that night, and she was right on the dot. I gave my wife and kids a hug goodbye before walking out the door, walking over to Kourtney's car, and resisting the urge to kiss her as I got in.

As she started to drive, she said, "Jessica just called me. Jack is running late, so she won't be joining us for at least an hour."

"Oh no. What are we ever going to do while we wait?" I said, moving my hand over to Kourtney's thigh and grabbing it.

"I told her that I guess it means that I get your first orgasm of the night," Kourtney said, spreading her legs a bit as she drove.

I moved my hand closer to her groin, and asked, "And what did Jessica think about that?"

I rubbed Kourtney's groin through the tight jeans she had on, and she said, "She said as long as she gets the last."

Kourtney had checked in earlier that day and gotten our room key, so when we arrived at the hotel, we quickly walked through the lobby; Kourtney surprising me by grabbing my hand, getting into the elevator. She again surprised me by wrapping her arms around my neck and kissing me while the elevator took us up two floors. When the doors opened, she stopped kissing me, again grabbing my hand and leading me to the room she had booked.

Once in the room, I went and sat on the edge of the bed and took a good look at Kourtney. Her long, brown hair, pulled back into a ponytail, went down to her lower back. Her eyes and her smile lit up her pretty face. Nearly six feet tall, her jeans fit tight against her long legs, and she was taking off her winter jacket to reveal a green, low-cut shirt that showed off her B-cup-sized breasts.

I continued to watch her as she walked towards me, wrapping her arms around my neck as she straddled my lap on the bed. We started to kiss again, and I wrapped my arms around her athletic body. I rubbed her back, going under her shirt and feeling her skin, as Kourtney started to roll her hips back and forth, rubbing her groin against mine.

I grabbed onto her ass as our tongues swirled together. I was growing hard in my jeans, and Kourtney could feel it, pressing her body down harder on me. When it started to become uncomfortable, I reached down between us, giving myself some relief by unbuttoning and unzipping my jeans. After that, with us still kissing, I moved my hands up and under Kourtney's shirt, going to her bra-covered breasts and squeezing them.

Kourtney briefly stopped our kiss to pull her shirt off, tossing it to the floor. I started to kiss Kourtney's neck as she reached behind herself, unclasped her bra, and pulled it off, exposing her B-cup-sized breasts and dime-sized nipples. I moved one of my hands up, taking her left breast, and squeezing. Moving my mouth down to her right breast, I took her nipple into my mouth, running my tongue across and sucking on it. I kissed over to her left breast, kissing, licking, and sucking that nipple.

Kourtney started to run her fingers through my brown, messy hair. "Fuck yes, Danny, suck on my tits," Kourtney said. "God, your cock feels so huge right now."

As I switched breasts again, I said, "Why don't you see how huge it is?"

I let go of her breasts, as Kourtney got off me and kneeled on the floor in between my legs. She quickly pulled my jeans and underwear off, and they joined her clothes on the floor. Kourtney then took my hard, thick, six-inch-long cock in her hand, rubbing the shaft up and down, and started to lick the pre-cum off my tip. She then opened her mouth as wide as possible, held my cock straight up, and engulfed everything down her throat.

I placed my hand on the back of her head, helping to hold her in place. She started to bob her head up and down my shaft, her hand working in rhythm with her head, and I leaned back a bit on the bed, using my arms to support myself.

"Oh yes. Your mouth feels great," I said, as she slowly blew me.

Taking her mouth off me, Kourtney asked, "Who gives a better blowjob? Me or Jessica?"

"Both of you are amazing at them," I said.

"Can I tell you a secret?" Kourtney said, her hand still working my shaft. I told her, of course, and she said, "I'm excited to watch you two fuck. Every time I've thought about it for the last week, I get wet."

Kourtney went back to sucking and licking the tip of my cock as her hand rubbed the shaft, and I said, "Really now? Why does that turn you on so much?"

Kourtney shrugged her shoulders as she continued to blow me.

I said, "Are you wet from thinking about it now?"

Kourtney nodded her head yes and I started to pull up on her head. She released my cock and stood up. I kissed her tan stomach as I unbuttoned her jeans and pulled them off. Kourtney had on a pink thong with white lace on the edges of it and I could feel the warmth coming from it.

I hooked my fingers into the waistband of her thong and pulled it down her long, tanned legs, where she kicked it off into the pile of clothes. I quickly pulled off my shirt, leaving us both completely naked. Wrapping my arms around her waist, I pulled her forward until her shaved pussy was at my mouth, and I licked around the wet edges of it. I briefly tongue-fucked her, Kourtney was moaning above me, until the weight of her pushing into me caused me to collapse onto the bed.

Grabbing onto Kourtney, we started to kiss again, shifting around until her body was under mine at the top of the bed. Her hand reached down, expertly guiding the tip of my cock inside her waiting pussy, and she let go as I finished pushing inside her. Breaking the kiss, I pushed myself above Kourtney, placing my hands on both sides of her head to hold myself up, and started to rock my body back and forth, sliding my thick cock in and out of her.

Kourtney had her legs spread around me and up in the air, with her arms above her head. She closed her eyes and opened her mouth, little moans coming out every time I pushed deep inside her. "Yes. Oh yes. Fuck me, Danny. Don't stop. Yes!" Kourtney said, in between moans.

I pounded into her as hard and quickly as I could. With my arms giving out, I fell on top of Kourtney and wrapped my arms around her neck. As I was jackhammering my cock into her, Kourtney wrapped her arms and legs around me, rocking her body with mine. I could feel her nipples rubbing against my chest as I fucked her, and I could hear her moans right next to my ear as she started to beg for me to cum inside her.