Pleasing my Sister-in-law ch. 08

The day after I helped Jessica pack up her things from her old house, the rest of the family gathered together for our monthly family dinner. Just like the one the month before, Jack didn’t say much about the on-going divorce but did mention that he was glad that some of the family were still being friendly towards Jessica. He didn’t mention any names, but he did look at me and Kourtney as he said it.

After we ate dinner that night, we went to sit in the living room and watch the kids play together. My wife, Kathy, and I sat on one end of the sectional couch my in-laws had, next to her youngest sister, Katie, and her husband, Kyle. My in-laws sat on the other end of the couch, next to Jack, their son. Kourtney, the second oldest in the family next to my wife, was on the floor, playing with my three daughters and Jack’s son. Gary, Kourtney’s husband, said he wasn’t feeling well and went downstairs to their room after eating dinner.

After playing with the kids for a while and the adults starting to run out of things to talk about, Kourtney asked if anybody wanted to play a game, and we all said yes. She asked if I would help her bring up some games, and I said yes. Following Kourtney down the stairs, I kept my eyes on her butt, with her butt cheeks nearly hanging out of her short shorts.

When we got into the storage area with all the games, I shut the door behind us and whispered, “Thanks for the view going down the stairs.”

Kourtney smiled at me and said, “You’re welcome; I figured you would enjoy it.”

As Kourtney started to look for some games, I walked up behind her, put my hands on her hips, and pressed my groin against hers. Rubbing my semi-hard cock through my shorts and onto her butt, I said, “It made me wonder if you have anything on under them.”

Kourtney pushed back against me and said, “Why don’t you find out?”

Taking the invitation, I moved my hands around to the front of her groin and slipped one of them inside. I felt the fabric of the underwear she had on, rubbed her pussy through, and said, “Damn, I was hoping for nothing.”

Kourtney finished grabbing some games and sitting them on a pile of stuff next to us. She turned in my arms, my hand moving around to her butt, her arms wrapped around my neck, and she leaned in to kiss me. As my hand squeezed her exposed butt where her thong didn’t cover, our lips briefly touched before we heard the door opening, and we jumped away from each other.

Katie, the youngest sister, was standing there. She looked at us, my hands still by Kourtney’s groin and Kourtney’s arms by my neck, and said, “What are you two doing down here?”

Kourtney quickly said, “Just grabbing some games.”

Katie looked confused as she said, “With the door shut? And I thought I heard Danny say…Nevermind. I was coming down to tell you that Kyle has had a long day, so we’re going to go home.”

Kourtney grabbed the games, and we all walked back upstairs. After saying goodbye to Kyle and Katie, the rest of the adults, minus my mother-in-law, played a couple games before ending the night and going home.

That Thursday, while working out at the gym with Jessica and Kourtney, we told Jessica about us almost getting caught, and Jessica said, “You better be careful. If Katie finds out, she might want in on it too.”

“Wouldn’t surprise me,” Kourtney said. Jessica asked why, and Kourtney told her, “She already had a massive crush on Danny. Always has. And she’s told me that Kyle is very basic with sex when he does want it. Or it’s super quick, and he falls asleep right afterwards.”

“I swear there’s something wrong with him,” Jessica said.

“Yeah, it’s called too much weed,” I responded.

Jessica laughed before saying, “And she’s cheated before. It is almost too good of a perfect storm if she does find out.”

After our workout was done, Jessica joined me in the backseat of my car. We were cuddling together, touching each other, and kissing softly and slowly. In between kisses, Jessica asked, “Have you and Kourtney had sex yet after working out?” I told her we hadn’t and asked why. Jessica responded, “Because I wanted to have something to brag to Kourtney about.”

With that, she started to pull down my shorts, my semi-hard cock popping out, and intensely kissed me while her hand jacked me off. At the same time, I pulled her shorts and underwear down, exposing her pussy that I started to rub, feeling how wet she already was.

Jessica climbed onto my lap, forcing me to sit back in the seat. Still kissing me, she reached between us and pulled my cock into her pussy. Letting go of it, she put her hands on the seat behind me and started rolling her hips, sliding my cock in and out of her.

With her brown hair pulled back into a ponytail, Jessica had on a gray tank top that I slid my hands up, rubbing the skin of her lower back. Finally ending the kiss, she leaned her forehead against mine, her mouth open, moaning as she rode me. She started going faster and faster, moaning louder and louder, making the car rock around us.

I glanced outside to make sure nobody was coming, but I looked back at her when I saw Jessica reach for the bottom of her tank top. She pulled it up over her breasts before pulling her black bra down and exposing her C-cup-sized breasts. She grabbed them, squeezing them as she said, “Oh yes, yes! I’m coming, Danny!”

Jessica grabbed my hands, bringing them up to her breasts and making me squeeze them. As I did so, I felt her pussy clenching around my cock, and my moans joined hers as I began to orgasm, pushing up out of the seat as I filled her with my cum.

As we came down from our orgasms, Jessica pulled her clothes back on and said, “The more we do this, the more I do want to rent an apartment next door.”

I laughed and agreed with her as I got out of the car, joining Jessica in the front seats. As I drove to her car, Jessica asked me, “If I stopped having sex with you, would you still be my friend?” I told her, of course, and asked why. She responded back, “Just making sure. I don’t want either one to stop.”

“Me either,” I said, giving Jessica a hug and a kiss before she got out of my car.

The next day, after work was over, dinner was done, and we had put the kids to bed, I was relaxing on the couch with my wife when her phone rang. I could tell from the ring tone that it was Kourtney, and I was wondering why she was calling so late. I heard Kathy say, “I’ll send Danny. You two are morons.” I was wondering where I was being sent and why when she hung up the phone, looked at me, and said, “Kourtney and Katie are at some bar called Funk and Dive, are too drunk to drive home, and both of their husbands are apparently already asleep. Do you want to go save your sister-in-laws?”

I laughed as my phone went off. I looked at the text to see Kourtney saying, “Are you coming?” I showed it to my wife, who just laughed and said, “Guess you better go get them. I’m going to bed.”

I kissed her goodnight before throwing on some shoes and leaving the house, texting Kourtney that I was on my way. When I arrived at the little hold in the wall bar, Kourtney and Katie were both outside, giggling with each other, and I jumped into my car. Kourtney was in the front, and Katie was in the back. Kourtney gave me a quick hug, telling me thank you, as I started to drive.

Katie was clearly more wasted than Kourtney was, but I was more concerned about Kourtney, who had her hand on my leg. The girls continued their conversation from when I had picked them up, and I listened in. Kourtney was saying, “Yeah, I don’t know why; I just get super horny when I drink.”

“Not me. It makes me want to sleep,” Katie said.

“I’m so horny, I can’t wait to drop you off. As soon as we do, Danny’s dick is coming out, and I’m blowing him,” Kourtney said.

“What?” Me and Katie both said it at the same time.

“I mean, I meant to say I would do that if Gary had picked us up like he was supposed to,” Kourtney said, removing her hand from my leg.

“Right,” said Katie.

“So, what is the biggest dick you’ve had?” Kourtney asked Katie.

“Like, eight inches? But it didn’t feel that great. I think seven inches, but not so thick, is perfect. But, when I want it in my ass, I prefer something smaller,” Katie told her.

“Really? Do you guys have to talk about this now?” I said, pretending to be annoyed.

The girls continued to talk, changing the subject to Katie’s husband, Kyle. But, as I pulled up to Katie’s house and she got out of the car, Kourtney yelled out, “If you ever want the best cock I’ve ever had, give Danny a call!” Katie turned around at her door to stare at Kourtney, and I was hoping that she didn’t hear her as I drove away.

“I really hope she didn’t hear that,” I said.

“Whatever. She wants to fuck you. You want to fuck her. It’s perfect!” Kourtney said, moving her hand back to my groin.

I pushed her away and said, “Sorry, not when you’re drunk. And that may be true, but the more people that know about this, the bigger the chance we get caught or told on.”

Kourtney grabbed my hand, bringing it up to her chest, and placed it on one of her breasts. She made me squeeze it before saying, “Come on, just let me blow you. I’m so horny. And I want to thank you for coming to get me. I’m not as drunk as Katie was. I only had three beers and one shot.”

She put her hand back on my groin, rubbing my semi-hard cock through the basketball shorts I had on. Knowing that she wasn’t going to give up and thinking that a blowjob did sound good, I pulled into an empty parking lot, moved to a hidden corner, and shut off the lights to the call.

Kourtney said, “I knew it!” And she slipped her hand into my shorts. She wrapped it around my growing cock as she started to kiss my neck and used her other hand to pull my shorts and underwear down, exposing my cock. When I was at my full six-inch-long length, she leaned over the center console, taking me in her mouth, and began to bob her head up and down my shaft.

I leaned my head against the back of the seat, looking down to see Kourtney, her brown hair pulled back into a ponytail, her hand wrapped around my shaft to hold it up, and eagerly sucking my cock. She alternated between moving fast and slow, her hand taking the place of her mouth on my shaft as she swirled her tongue around my tip, before going back to deep throated me.

I felt my orgasm building up, pushed my hips out of the seat, and started to cum without warning Kourtney. She moaned around my cock as she felt the warm cum hitting the back of her throat, pushing her head all the way down as she swallowed every drop that came out.

When I was done, she sat up in her seat and licked her lips clean. I looked over at her and said, “Show me your tits.”

Kourtney smiled and lifted up the shirt she was wearing, pulling her black bra up too, and flashed me her B-cup-sized breasts. She moved from side to side as I stared at them before pulling her shirt back down when I pulled my shorts back on. As I put the car back into drive and started to pull out of the parking lot, Kourtney leaned her head against my shoulder, kissed my cheek, and asked, “Was it worth it?”

I smiled and said, “Of course.”

I was nervous the next few days that Katie was going to say something either to me or my wife about what Kourtney was saying. By Tuesday of the next week, I had finally convinced myself that Katie either didn’t hear it, didn’t care, or didn’t remember it. That was, until Katie texted me while I was at work that day and said, “I’ve been wondering for a few days now how to bring this up, but I just need to come right out and say it. Are you sleeping with Kourtney?”

I asked why she would even think something like that, and she said, “Let’s see, Kourtney said she wanted to suck your dick, yelled out how perfect your cock is, and last Sunday, I’m pretty sure I heard you talking about her wearing underwear or not.”

“Do you really think I would cheat on Kathy?” I asked her.

“I really don’t care if you do or not. If you are, that’s your own choice, but I’m not going to be the reason she goes through what I went through,” she responded back.

“So, if I were sleeping with Kourtney, what would it matter?” I asked her.

“Because, if you didn’t get it from the conversation I was having with Kourtney, I don’t like sex with Kyle as much as I hoped I would. So, if you are, I was going to blackmail you into sleeping with me,” Katie told me.

“Well, too bad. I’m not sleeping with her. I don’t know what you heard on Sunday, and Kourtney was just drunk on Friday,” I said.

Katie ended the conversation there, but I wasn’t convinced that she believed me. I immediately texted Kourtney about it, and she said, “Why are you resisting her? Just fuck her and be done.”

“Because the more people that know, the bigger of a risk it is,” I replied back.

That Thursday, Jessica texted me to say, “Hey, I won’t be at the gym tonight, but is there anyway that me and you can talk? I just had my first court date with Jack and need somebody.”

I told her, of course, and made plans to call her later. I finally got a chance to call her while I waited for Kourtney at the gym. Jessica told me how the court date went, how the judge said everything would go, the counseling they would have to go to to determine a custody agreement, and what they each had to submit before the judge would make a final ruling about everything.

“So, the next court date is set for May tenth, which is the day that I have the campsite reserved for. I definitely think that I want you to come now if you want to,” Jessica said.

“Of course. I’ll put it on my calendar,” I told her.

“Good, that’ll give me something else to look forward to,” Jessica said before we hung up.

Walking into the gym with Kourtney, I said, “I’m still not very happy about what you said to Katie.”

“Yeah? Maybe some hate fucking tonight?” Kourtney said it with a devilish smile on her face.

“Nah, you would like that too much. I’m thinking either nothing at all, or I’m just going to fuck your face,” I told her, spanking her ass as I held the door open for her to walk through.

I rode the stationary bike for the first little bit of my workout, and when I was done, I went to find Kourtney and see what she was up to. I found her on a treadmill, doing a slow jog. I walked up in front of her, and she lowered her headphones and said, “Yes?”

“I just wanted to tell you to make sure not to work your legs too much. You’ll be doing lots of squatting later,” I said before walking off.

When we were done at the gym, we both showered and changed clothes before leaving. The gym we went to was actually on the third floor of a building with a couple of other businesses below it. Attached to the building was a giant parking garage, with doors leading to it from every floor. I knew that not a lot of people used the second-floor entrance to the parking garage, so I grabbed Kourtney’s hand and led her to the stairs.

She asked what we were doing since we normally just walked to the garage right from the gym. I told her, “Just go with it.”

Once in the stairwell leading down to the second floor, I grabbed onto Kourtney and pushed her up against the wall. I was already hard in my shorts, and, after kissing her passionately, I pushed her down to a squatting position. With one hand on her head, I pulled my shorts down just enough for my cock to pop out.

Kourtney opened up her mouth wide as I pushed my tip past her lips. Still holding her head, I started thrusting back and forth quickly, Kourtney barely able to stop her head from hitting the wall as I shoved my thick cock down her throat over and over.

Kourtney was moaning around my shaft, clearly enjoying me face-fucking her. I looked down to see her stick her hand down her shorts, rubbing her clit. Her other hand was behind her, and she was using it to brace herself against the wall as I continued to use her to blow me.

With the risk of getting caught increasing, my orgasm was building up, and, just like last week, I didn’t warn Kourtney as I came, pushing myself deep down her throat and my cum exploding out of my cock. As I pumped everything I had into her, I pushed her head up against the wall, slowly sliding my cock in and out of her mouth until I was sure I was done. When I was, I pulled my shorts back up over my cock as I helped Kourtney back up to her feet.

Leaving the stairwell and walking to the parking garage, Kourtney said, “Holy shit, I’m so fucking wet right now.”

“Yeah? What do you want to do about it?” I asked.

“Jump in the backseat of my car and fuck your lights out,” she responded. Unfortunately, before we could, my wife called and asked when I was coming home. One of the kids was having problems that she needed my help with. Me and Kourtney had to settle for a short make-out session before she got in her car and I got in mine.

As I drove away, I texted Kourtney to say, “I guess a good face fucking and not getting what you want is a good enough punishment for telling Katie.”

Kourtney sent back, saying, “Maybe a face fuck in public is what I wanted?”

“Whatever. I really am worried about Katie. I need you to try to convince her nothing is going on if she tries to ask you about it,” I said.

“And if I don’t?” Kourtney responded.

“Then no more of this cock that you like so much,” I said.

“Fine. But you better hate fuck me next time, like you said earlier,” Kourtney said.

That Saturday, I was finally able to get some yardwork done. The wife and kids were gone again for the day, I had my headphones in, and I was going to town on the lawn. I had heard my text alert go off a few times but ignored it. I did finally stop the lawnmower when the Ring doorbell alarm went off in my headphones. I looked at the camera to see Jessica standing there, with her car in the driveway and her phone in her hand.

I walked over to my garage, opened the door to it, and called out to Jessica, saying, “Hey, what are you doing here? Everything ok?”

She came up to me, greeting me with a hug, and said, “Yeah, of course. I texted you a few times before I called Kathy. My parents are digging up their garden, and I was going to see if I could borrow your tiller. Kathy said you would be home and to just come get it.”

“Oh yeah, of course. Sorry, I just got busy with the lawn and didn’t look at my phone. It’s in the shed,” I said, and I started to walk back through the garage to my backyard with Jessica behind me. We made small talk as we walked to the shed. Once in there, I showed her the tiller and how to use it. As she looked at it, I said, “So, is that all that you came over for?”

Jessica said, “Well, it was until I found out you were alone. But I don’t want to take you away from your lawn again.”

I said, “I’ll gladly take a break for you.”

Taking the tiller with me, Jessica followed me back to the garage and then into my house. Jessica that day had her brown hair loose around her pretty face, had on blue jean shorts that went to her knees, a plain pink shirt with a pocket on her left breast, and blue and pink Nike shoes that she immediately kicked off inside my house. Her clothes were tight against her body, showing off her C-cup-sized breasts, her wide hips, big butt, and athletic legs.

Once inside, I wrapped my arms around her body and lifted her up. Jessica wrapped her arms and legs around me and started to kiss my lips as I walked us out of the kitchen. In between kisses, I said, “Bedroom or living room?”

Jessica replied, “Wherever is closer?”

I maneuvered us to the living room, laying Jessica down on the couch with me on top. I moved my hand up, sliding it under her shirt, and cupped her breast in my palm. I was growing hard in my shorts and began to move on top of her, rubbing our groins together.

Breaking the kiss, Jessica pulled my shirt up and over my head, and I quickly returned the favor. We sat up a bit as I reached behind her, unhooked her bra, and threw it to the floor. I kissed her neck as we laid back down, moving down to her chest and finally to her breasts. I started to kiss her left breast, all around it and the nipple, while I squeezed her right breast. As I licked her nipple, making it grow hard, I rubbed the other nipple with my fingers.

Jessica moaned, running her fingers through my shaggy brown hair as I switched between her breasts, alternating between sucking and licking with my mouth and rubbing and squeezing with my hands.

Feeling her starting to push her hips up into me, I kissed down from her chest, over her flat stomach, and to her groin. There were three buttons on the jeans that I quickly unsnapped, and we both pushed up off the couch enough that I could pull her pants and underwear down and off. Going back to her groin, I licked around her hairy, wet pussy, darting my tongue in and out of it. I licked up and down, all around it, sucking a little on her clit, until she said, “As good as that feels, your cock would feel even better.”

I kissed back up her groin, her stomach, her chest, and her neck, and finally kissed her lips again as she reached between us and pulled and kicked my shorts and underwear off. She wrapped her small hand around my six-inch-long, thick cock and slowly rubbed up and down while pulling my tip into her waiting pussy. She let go as I finished pushing in deep.

We ended the kiss again as I began to thrust in and out of her, slowly at first, but picking up speed and going harder and faster as I pounded into her over and over. I had my hands on both sides of her, pushing up over her, looking down at her, and watching her breasts bounce as I fucked her. She had her legs spread wide, her arms around her side, her eyes closed, and her mouth open as she moaned every time my cock pushed deep inside her.

“Yes. Danny. Oh yes. Harder,” Jessica moaned. “You feel so good. Yes please! Danny! Oh baby!” She started to push her hips up, getting me as deep as she could at the angle we were at.

Needing to adjust, I stood up off her, my cock sliding out with a cock. Breathing deep, Jessica said, “Do you want me to ride you or bend over the couch?” I said to bend over, and she got up on her feet before sliding down to the ground. She had her knees on the floor and her upper body and head resting against the seat of the couch.

I quickly got behind her, kneeling down on my knees, lined my cock back up with her pussy, and easily slipped back into her. I placed my hands on her hips and started to thrust my own hips back and forth, sliding my cock back and forth inside her. I pulled out to the tip before pushing all the way back inside her over and over, harder and faster.

Jessica placed her hands on the seat of the couch, using them to push herself up slightly and push back against me as I pounded into her over and over. I rubbed her back and her butt, and reached around to squeeze her breasts with my hands as I slammed my cock into her.

Her arms finally gave out, and she laid on the couch, her head turned to the right so she could breathe and moan. I told her I was close, and she said, “Yes. Give me your cum.” With that, I pushed in as deep as I could and orgasmed. Feeling the cum shooting out of my cock, I held tight onto Jessica’s hips, my cock pulsating as I finished.

I slipped out of her, resting on the floor as I caught my breath. Jessica slowly moved down next to me, resting her head against my chest, and said, “That was nice.”

“I’m sorry that you didn’t finish,” I said. “I can keep going if you want.”

“No, it’s OK. I actually haven’t had Liam the last couple of nights, so I’ve been masturbating every night. Sometimes twice a night,” she replied back.

“Damn,” I said. “That sounds like something I would have liked to see.”

“Jack still hasn’t told me if he’s bringing Liam back tonight or not. If he doesn’t, I’ll send you a video,” Jessica said as she got dressed again.

I got dressed as well and walked Jessica outside. I loaded the tiller into her car and gave her a hug and said goodbye.

I went back to my yard care and actually looked at my phone when I heard it go off two times. The first text was from Jessica, and it said, “I gave my parents the tiller to use and showed them how to. They both kept giving me weird looks, and my dad didn’t say much. It wasn’t until I got inside that my sister saw me and said, I smell like sex, and my hair looks like it too.”

Before I could reply to it, I saw another text from Katie. I took a deep breath as I read it. “Hey, Danny. I know that you and Kourtney are sleeping together. I don’t know why, and I don’t care either. I just want a turn. That’s it.”

Leave a Comment