📚 pleasing my sister-in-law Part 9 of 44
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Pleasing My Sister-in-Law

Pleasing My Sister-in-Law

by Pooer87
19 min read
4.6 (12900 views)
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I took a screenshot of Katie's text and sent it off to Kourtney, asking her if she had said anything to Katie. I texted Katie, asking why she thought that.

Going back to Jessica's text, I reread and kind of laughed at her going out for a tiller and coming back smelling and looking like she just had sex. I asked her, "Are you worried about your parents finding out? And how does your sister know what sex smells like?"

My phone went off a few minutes later, with messages from all three girls. Kourtney's came through first and said, "I promise that I didn't say anything. I don't know where she's coming from."

Katie's said, "I was at the gym on Thursday. I don't know how you two didn't see me."

"I doubt my parents will say anything. It's none of their business what I do, and they never really liked to talk about sex. That's a good question about my sister," Jessica's text said.

I told Jessica that I was glad she came over before texting Katie back and saying, "So? I can't go to the gym with Kourtney? What does that prove?"

"Besides you two disappearing into the stairwell for ten minutes? Kissing each other by her car? I saw it all," Katie said.

Shit.

"Just come clean. I'm not going to tell Kathy. Like I said, all I want is a turn," Katie said.

"Fine. You caught us. When?" I texted her back before sending Kourtney a text to tell her how Katie found out.

"You tell me. How do you and Kourtney find the time?" Katie asked back.

I told her how me and Kourtney usually just hooked up when we could; it just depended on what was going on. We switched up our conversation to talking about what she liked and didn't like in bed and what she expected from it.

I opted to stay home from the gym that Thursday, much to the disappointment of Jessica. Instead, I spent the night with my wife, Kathy. After getting the kids to bed early, we chatted in bed for a few minutes before we started to make out.

Three years younger than me, I met her when she was just out of high school while we both worked at a local grocery store. She was five feet, nine inches tall, just like me; she had brown curly hair and double D breasts. She was slightly overweight, but that was just fine for me. With the prettiest face I've ever seen and the friendliest and most caring personality, I fell in love quick.

Ten years into our marriage, our sex routine was set in stone. As we kissed, my hand went up her shirt, grabbing and squeezing her breasts. Her hand trailed down to my underwear, wrapping around my shaft, and rubbing as I grew hard. We stripped each other naked, my hand going down to her groin and fingering her while my mouth went to her nipples.

I could never get Kathy off from just using my fingers, no matter what I did down there, so as soon as she was wet enough, she was pulling my cock inside her, and I was thrusting into her as quick and hard as I could.

Our favorite position, however, was with Kathy on top. She loved to ride my six-inch-long, thick cock, and it was one of the few ways we found that could make her orgasm. I loved it because I could hold her breasts in my hands, squeezing them, sucking and licking her nipples, and rubbing them with my fingers.

After she got herself off, she moved, so she was kneeling on her hands and knees. I kneeled behind her, sliding my cock back into her wet pussy. As I placed my hands on her hips and pounded into her, my mind started to wonder, and I imagined I was fucking Jessica. Then Kourtney. And finally, I pictured having Katie under me, making her moan.

My mind went blank as I orgasmed, pushing deep into my wife as I filled her with my cum. When I was done, we cuddled together in bed before falling asleep.

That Saturday was my middle daughter's birthday. We opted not to have a big birthday party and instead, just invited the grandparents over for dinner, and told everybody they could stop by throughout the day if they wanted to.

Shortly after lunch, my wife took our two oldest daughters out to go do some shopping. I stayed home with our youngest daughter, who was taking a nap. I was lying on the couch, playing a game on the Nintendo Switch while a movie played on the TV. There was a light knock on the door, and I jumped off the couch as the door opened.

I saw Katie walking in as she said, "Hello? Danny?"

I said hello, getting up and walking to the door, before saying, "Kathy took the birthday girl out if you're here to see her."

Katie replied back, "Yeah, I called her first. She said it should be only a half hour or so if I wanted to come hang out."

"You're always welcome to do that," I said, going back to the couch. Katie followed me, sitting down on the other side of the sectional couch from me, and pulled out her phone. Looking at her, I saw her blonde hair that was pulled back into a ponytail. She normally liked to dye it different colors, but she had been letting her natural blonde come through lately.

Standing a few inches shorter than me at five feet, seven inches tall, I had watched Katie grow from the very young twelve year-old she was when I first started to date Kathy to the twenty-seven-year-old woman she is now. I had watched her learn to drive, graduate high school, debate going on a mission or not, get married, get divorced, and the tailspin her mental health took from it.

She was the only biological daughter of my in-laws, with Kathy and Kourtney both being adopted. Her face was a lot like her mom's, skinny, but Katie had bright blue, beautiful eyes. Her smile could light up a room, and she really had a careful personality when she wasn't down in the dumps. As much as I didn't like her current husband, I cared for Katie and was glad she was happy with him.

"So, what should we do while we wait?" I asked her.

"I don't know. I bet if I were Kourtney, you two would be making out by now," she responded back.

"Maybe. Why aren't we?" I said it with a laugh.

"Because I would want more, and we don't have time for that. Plus, we're not totally alone," Katie said before going back to her phone.

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"True, but she's asleep. But I agree. It would be hard to stop," I said.

"Do you even want to have sex with me? Or only because I caught you?" She asked me.

"What do you think?" I asked her.

"I don't know. You're like a big brother to me. Yeah, I've had a crush on you before, and I'm the one who keeps bringing it up. I've just had so many bad experiences with guys that I don't want to make you feel like I'm using you," she said.

"So, why even bring it up then? Why potentially ruin what you have with Kyle? Why risk the chance of having another bad experience with a guy, especially one you think of as a big brother?" I asked.

"Because I miss good sex. And I figure if Kourtney is sleeping with you, you must be good at it," she confessed to me.

"Kyle isn't good at sex?" I said it with a smirk on my face.

"Not really. I mean, it's decent. He gets me off when he can, but gets frustrated when he can't. And he doesn't last very long. He never initiates it either," Katie told me. "Ethan, my first husband, was amazing at it. I never should have cheated on him. I was a moron."

"What about the other guys you slept with?" I asked.

"None of them were that great. They mostly just cared about themselves," she told me, standing up from the couch and going into the kitchen.

I followed behind her as she walked up to the sliding door that led to the deck and the backyard. Causing her to jump a little, I wrapped my arms around her waist and pulled my body close to hers.

I whispered in her ear, "Well, just so you know, when we do fuck, my number one goal is to please you." I put my lips on her neck and started to kiss it, leaving soft kisses all over it. Katie leaned her head backwards, and I kissed up to her lips, leaving a small, delicate, but quick and passionate kiss on them.

"Should I stop?" I said.

"No," Katie breathed out. Her hands interlocked with mine as I began to kiss her neck again, every once in a while going back up to kiss her lips. I turned us back around and started to walk us towards the couch. I unhooked my fingers from hers and moved my hand up to cup her breast through the gray shirt she had on.

Katie's weight had fluctuated through the years. She was super skinny as a teenager; she put on some weight after getting married the first time, lost it, regained it, and lost it again. Her stomach wasn't super flat, but she wasn't overweight by any means. She had B-cup-sized breasts, bordering on a C-cup, and I squeezed both of them in turn. The shirt she was wearing was low-cut, showing off the top of her cleavage. As I kissed her neck, I slipped my hand into her shirt, under her bra, and cupped her breast in my hand.

Katie let out a moan before twisting her head down to meet my lips, kissing me as she pressed her butt into my groin. When we finally got to the couch, I pulled my hand out of her shirt and helped her lay down. As she did, her shirt rode up, showing me her stomach, and I glanced down at her groin, wondering what she had on under the blue jeans she was wearing.

Seeing me looking at her groin, Katie said, "You should probably keep those on unless you want to get in trouble."

I laid down on the couch next to her, kissing her neck again, and started to rub her groin through her jeans. In between kisses, I said, "We can keep them on, but I wouldn't mind a little bit more access.

"Better hurry," she said, and I kissed her lips as I undid her pants. I pulled them apart and pushed them down enough to show me a pair of black underwear. I couldn't tell if it was a thong or not, but I figured out that it wasn't when I placed my hand on it and started to rub her pussy through it. I moved it to the side, revealing a hint of hair, and began to rub her pussy lips, and she started to get wet.

We continued to kiss as I rubbed her pussy. Katie reached her hand down between us and grabbed at my semi-hard cock through the shorts I was wearing. Briefly breaking the kiss, she said, "Wow," and slipped her hand inside my shorts. She went back to kissing me as she wrapped her hand around my shaft, making it grow harder and thicker.

We continued like this, making out, her hand rubbing my cock, and my hand rubbing her pussy, until we heard the garage door start to open. I immediately jumped off the couch and adjusted my cock in my shorts while Katie buttoned her jeans back up and sat up on the couch. I ran outside to help my wife and kids inside with the items they bought at the store.

Late that night, laying in bed after everybody else had left and Kathy and the kids were asleep, Katie sent me a text that said, "Random question, and I'm sure you're asleep by now, but how big are you? It felt huge!"

"I'm like six inches, I believe," I texted her back.

"But you're so thick! I'm wet just thinking about it," she responded.

"Yeah? Glad we at least did a little something today?" I said.

"Hell yes. But I was still so horny when I got home. I thought about you tonight when me and Kyle did it," she said.

"That's hot. Hopefully you can feel it inside you soon," I said before falling asleep.

That Monday, Jessica texted me and said, "Hey, on Thursday, I have an appointment to go see an apartment next to the gym. Do you want to tag along with me? It's an hour before the gym, but maybe we can see if Kourtney wants to come too? Or we just go to the gym early?"

I texted her back, "Yeah, that would be fun. And I'm sure we could find some way to fill the time before Kourtney comes."

"Yes, we could. I would like that, actually. I just might not want to work out afterwards," she said.

"This is true!" I texted back.

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Meeting Jessica at the apartment building next to the gym on Thursday, I gave her a hug as she said, "Did Kourtney text you too?" I said no, and Jessica said, "She's not coming tonight. Her and Gary are going on a date instead."

"Oh, well, good for them," I said as we walked into the building and Jessica went to talk to the manager. When the manager went to grab the apartment key, Jessica said, "Also, my parents are gone for the night."

"Oh yeah?" I said, looking into Jessica's eyes.

"Yes. You know, if we wanted a bed instead of a car," she said while smiling.

"Or we could just skip the gym and go right there," I said as we started to follow the manager to the apartment. Jessica didn't take very long to view the two-bedroom apartment, examining every room and making a few comments. She asked the manager about availability, and they discussed it for a few minutes before Jessica said she might be back the next day to sign paperwork.

We left the apartment building and walked to our cars. I followed Jessica to her parents house; my boner starting to grow already. When we arrived there, Jessica led me inside and right to her room. Shutting the door behind me, I wrapped my arms around Jessica, and she did the same to me.

Standing five feet tall, with her brown hair that went just past her shoulders pulled back into a ponytail, she had on a black shirt that stretched tight against her C-cup-sized breasts and black and white basketball shorts. She rested her head against my chest as we held each other tight for a few minutes.

I looked down at her as she looked up at me. My blue eyes looked into her hazel eyes as we began to kiss, our hands starting to move on each other's bodies. I grabbed the bottom of her shirt and pulled it up and over her head, leaving her in a black bra that I quickly unhooked and discarded. I brought my hand up and placed it on her breast as we moved towards her bed.

I broke the kiss, leaning down to suck on her nipples as Jessica lowered my shorts and underwear. She wrapped her hand around my shaft, rubbing my cock to its full six-inch length. I switched back and forth between her breasts, squeezing them with my hands while sucking her nipples and licking them with my mouth and tongue.

I let go of her breasts when Jessica sat down on her bed. She opened her mouth up and flicked her tongue against the tip of my cock before taking me inside her mouth and bobbing her head up and down the first few inches of my thick cock.

I put my hand on the back of her head, helping to guide her up and down as I enjoyed the feeling. Jessica wrapped her hand around the lower part of my shaft, rubbing it up and down as she was unable to fit my entire cock into her mouth.

As much as I was enjoying the blowjob, I knew we didn't have all night, so I started to push Jessica more onto the bed. She let go of my cock and scooted back onto the bed. I quickly pulled off my shirt, leaving me completely naked, before joining her on the bed. Jessica spread her legs wide as I laid on top of her, my hard cock pressing against her still-covered groin and her nipples pushing against my chest.

Our lips met again, kissing passionately, and I started to rock back and forth on her. After a few minutes of kissing her lips, I kissed down to her neck, her chest, licked her nipples again, then her stomach, before I reached her groin. I pulled her shorts and underwear down in one pull and threw them off the bed.

I continued to leave kisses all over her body as I moved back up. Once I reached her lips, Jessica reached between us and pulled my hard, thick cock into her wet pussy. I pushed in as far as I could go after she let go, letting us both enjoy the feeling of me filling up her insides as we kissed, our tongues swirling together.

We ended the kiss, and Jessica moaned as I started to thrust my cock in and out of her. I put my hands on the bed on both sides of her, pushing myself above her as I fucked her, giving myself a good angle to pull my cock out to its tip before pushing back inside her.

"Yes. Yes. Oh yes, Danny, give me that big cock of yours!" Jessica moaned out as I thrust in and out of her, over and over. I saw her breasts bouncing and stared at them as I pounded my cock into her. "Let me ride you!" Jessica said, and I rolled off her, watching as she climbed on top of me. My cock easily slipped back inside her, and she kissed me deeply, her breasts rubbing against my chest as she started rolling her hips back and forth.

I reached my arms around her, taking her ass in my hands, and held onto it as I pushed my hips up, taking my cock even deeper into her as she moved her hips down. Breaking the kiss, Jessica pushed herself up above me, using her hands on the bed to hold herself steady as she rode me, bouncing her thick ass on me.

I moved my arms in between us, cupping her breasts in my hands and squeezing them. I took my thumb and index finger and used them to rub both of her nipples before leading them, one at a time, to my mouth. I sucked them, licked them, and made Jessica moan as I did so.

I laid my head back on the pillow, still holding onto Jessica's breasts, as she started to bounce harder and faster on my cock. Her moans were getting louder and more frequent, culminating in her throwing her head back as she climaxed. Her pussy clenched down on my cock, causing me to orgasm as well. I squeezed her breasts hard as I came, pushing my hips up and sending my cum deep inside her.

"Oh yes!" Jessica yelled out as she felt me finishing inside her. "Danny! Yes! Oh God!"

Still rolling her hips back and forth on top of me, Jessica leaned down, our lips meeting to kiss again. I wrapped my arms around her body, pushing our naked skin tight against each other. My cock slipped out of her as I went limp, and Jessica rolled off me, cuddling up next to me in my arm.

She started to laugh, and when I asked what was so funny, she said, "I've had this bedroom since I was ten years old. My mom kept it basically the same when I went on my mission and left the bed and dresser in it when I got married. I never would have thought, in a million years, that I would have sex with a married man--that's not my husband--in the bed I grew up in."

I laughed too and said, "As weird as it sounds, I was actually wondering if I was lucky enough to be the first man that's not in your family or Jack that's been in here."

"Oh crap, you might actually be. I was never allowed to have boys in here when I was growing up," Jessica said, causing us both to laugh again.

"That was definitely better than going to the gym," I said. I placed my free hand behind my head to support it, and I pulled her naked body closer to mine with the hand I had wrapped around her. We spent the next half hour or so kissing and touching each other before I said that I had to go.

"Is it bad if I don't want you to go?" Jessica said, looking at me with sad, puppy dog eyes.

"No, because I don't want to go either. But, in a couple of weeks, we'll have lots of time together while camping," I said, pulling my clothes back on.

"I know. I can't wait. I just hope the kids cooperate," Jessica said, sitting naked in her bed.

"I think they will. Elle keeps asking if she and Liam can sleep in a tent by themselves," I said.

"So does Liam, so hopefully it works," she said. She got out of bed, put a shirt on, and put on some underwear before walking me to the front door and giving me a hug and a kiss goodbye.

The next Thursday at the gym, we were unable to do anything as Gary, Kourtney's husband, joined us. All four of us went out to get some food afterwards, and we unfortunately had to depart from each other without a hug or a kiss, leaving me and Jessica disappointed, but we made up for it with a lot of texting that night and the next day.

That Sunday, my father-in-law was giving a talk and singing in church, and the entire family was invited. Katie, Kyle, Kourtney, Gary, Jack, and Liam, plus my wife and kids, were all there, taking up an entire bench in the chapel. Kourtney was in a form-fitting dress that ended just above her knees, and she gave me a sly smile when she caught me looking. She sent me a text saying, "Just so you know, I'm not wearing anything under this."

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