πŸ“š pleasing my sister-in-law Part 38 of 44
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EROTIC COUPLINGS

Pleasing My Sister-in-Law

Pleasing My Sister-in-Law

by Pooer87
20 min read
4.72 (4500 views)
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Note: hi everybody, before you read this chapter, if you haven't done so already, I highly suggest that you read chapters 5 and 6 of the Building a New Life in Chicago series. They can both be found on my profile. Thanks for reading!

"Oh, my God! This is so good!" I said, taking a bite of the deep dish pizza in front of me. After an exciting morning with Kourtney and Jessica, Kourtney had taken us to a famous Chicago-style pizza restaurant called Lou's, where we had ordered a Malnati Chicago Classic.

"Way better than that frozen stuff we had last night, isn't it?" Kourtney laughed as she also took a bite.

"Umm, yes, definitely," I said, taking another bite, Jessica nodding her head next to me.

We were sitting in a dark corner booth of the restaurant, Jessica in the center with me and Kourtney on the sides. I looked over at the two women, remembering how just a few hours ago, they were on their knees, giving me a blowjob at the same time.

Kourtney wasn't kidding about wearing the same clothes she had on during the blowjob. The white tank top that very clearly showed off her B-cup-sized breasts, was covered by a thin flannel shirt that she had only done up the first few buttons. Over her pink thong, she had put on the smallest pair of jean shorts I had ever seen, her buttcheeks poking out the bottom of them. She kept her brown hair in the pigtails they had been in, along with the red lipstick on her face.

Jessica, my girlfriend, went a little more modest. With her bigger breasts, she did put on a bra, along with a tight-fitting t-shirt. Her shorts were a little longer than Kourtney's and weren't as tight either. Her brown hair was still braided in a ponytail, and her face was just as cute as ever, with the red lipstick highlighting her lips.

"So, was there anywhere else you two wanted to go to today?" Kourtney asked us.

"Yeah, there's a few more sights I want to see," Jessica said, and she and Kourtney started to talk about them. Jessica finally looked at me and asked, "What about you, Danny?"

I laughed and said, "Honestly, I'm cool with going wherever. The only sight I really want to see today is you two laying on Kourtney's bed, if I'm being honest."

"I know, and we'll spend plenty of time there too. I think we're just going to see two more places, and neither one will take long," Jessica said.

We finished up the pizza and paid as we left the restaurant. The first location was just around the corner and was a quick visit with some pictures taken before we left. The second location was an outdoor mall that Jessica wanted to shop at and required a drive across town.

Once there, we quickly went to a few shops, doing some window shopping, and left them without buying anything. On our walk to the third store, Jessica was out in front of us, on the phone with her son, while me and Kourtney trailed behind her.

"Is it bad if all I want to do is run up, grab her ass, and kiss her?" Kourtney asked me, under her breath, so no one else would hear.

"Hopefully not, because I've been thinking about the same thing with you. And her. Both of you," I said.

"I'm not going to lie; I've been horny all day," Kourtney said. "I think I would moan loudly if you grabbed my ass."

Glancing around, I took a sidestep closer to Kourtney and wrapped my arm around her waist. "Let's find out," I said as I lowered my arm down until my hand was resting on her ass. Kourtney bit her lower lip as I felt the skin of her asscheek poking out the bottom of her shorts. I cupped it with my fingers, squeezed with my hand, and Kourtney had to fake cough to stifle her moan.

"Fuck me," she whispered.

Jessica hung up the phone and stepped back to be with us. "Really? Can't keep your hands off her? In front of your girlfriend?" She said it with a laugh.

In response, I wrapped my other arm around her waist, lowered my hand down, and squeezed her buttcheeks, causing Jessica to let out a low moan and make Kourtney giggle.

I saw something in a store window that caught my eye and went over to look at it. When I went back to Kourtney and Jessica, they wrapped their arms around each other's waists and started to walk away from me. I admired their butts as they walked before catching up to them and saying, "Really? Here? In front of your boyfriend?"

At the next store we went to, as Kourtney looked at some pants, I walked up next to Jessica and said, "So, Kourtney told me that she's been horny all day."

"Oh yeah?" Jessica asked, giving me a quizzical look.

"And those shorts of hers look like they could give some pretty easy access," I said, looking over at Kourtney.

"Yes, they do," Jessica said, also looking at Kourtney. "But do you really want to try something in this crowded mall?"

"No, probably wouldn't be a smart idea. Two bad there wasn't someplace that two people could go that nobody else is supposed to look in and could maybe get away with at a touch," I said.

"Yeah, that is too bad," Jessica agreed, smiling as she started to have the same thoughts I was having.

"There's a pretty little dress over there. Maybe see if Kourtney could help you try it on?" I suggested it, and Jessica walked over to grab it.

I watched as she walked over to a worker at the store with a pile of clothes in her hands and asked, "Hey, do you have a changing room here?" The employee pointed her to the back of the store and said, "I don't have anybody working back there right now, so just bring me whatever you don't want to buy."

Jessica thanked her and walked to the back, giving me a wink as she did. Unsure of her plan, I went over by Kourtney and waited. A few minutes later, I heard Jessica calling Kourtney's name. We looked over at her, poking her head out from the changing room, her arm up against her chest to hold the dress up. "Can you give me a quick hand with this dress?" Jessica asked, and Kourtney walked over to her.

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I moved closer as well, trying to hear what was happening and to block anybody else from coming over. It was only a few minutes before I could hear Kourtney quietly moaning inside the closed-off changing room. I stepped closer, trying to imagine what was happening in there, and could feel my cock growing in the shorts I had on.

"Oh, Jessica, yes!" I heard Kourtney moaning. She started to say something else but was stopped, either by Jessica's hand or her mouth. In my mind, they were wildly making out while Jessica fingered her. A few minutes later, I heard the unmistakable moan of Kourtney's as she had an orgasm. "Fuck," I heard her say from behind the closed door.

A few moments later, I stepped back as I heard the door opening. Jessica and Kourtney both stepped out, Kourtney looking very pleased while Jessica was in a yellow dress. Jessica smiled as she brought her hand up to her mouth, a tiny hint of Kourtney's juices on her fingers, and sucked it off. "So, how do you like the dress?" She asked me, slowly spinning around in it.

"It's super cute," I told her.

"I think I'm going to buy it," Jessica said, turning to go back into the changing room after having Kourtney unzip the back of it.

As Jessica closed the door, Kourtney walked next to me and asked, "Did you guys plan that?"

I smiled and said, "What happened? That took a while to zip up a dress."

"Oh, so you had nothing to do with me being ambushed in there?" Kourtney said.

"I don't know what you're talking about. What happened?" I asked.

"Oh, Jessica just pushed me up against the wall, kissed me, and fingered me until I came," Kourtney said.

"Oh, now that you mention it, I did hear you moaning," I said with a smile.

"It was your idea, wasn't it?" She said.

"I may have hinted it, but she's the one who did it," I told her.

Jessica came out a few minutes later and gave most of the clothes to the cashier, only buying the dress and a pair of jeans. We browsed a few more stores before deciding to call it a day and head back to Kourtney's apartment.

Once there, I helped the girls take their shopping bags inside and went to the bathroom while they sat down in the living room. When I came out of the bathroom, I saw that Kourtney was kicking back on the couch, her flannel shirt unbuttoned, her nipples visible through her tank top, with her legs propped up on a coffee table, spread slightly open. Jessica was looking at something on her phone, stopping to look at me when I said, "Alright, Kourtney, Jessica got to take advantage of you earlier at the mall. It's my turn now. I've been here for three days and haven't cum inside your pussy yet. Let's go."

Kourtney started to get up off the couch as I grabbed her hand and helped to pull her up. Jessica adjusted to lay down on the couch and said, "Have fun. Let me know when you're done."

I walked Kourtney into her bedroom, where I started to kiss her as I pulled her flannel shirt off. She returned the kiss, helping me to pull her tiny jean shorts down her long, tan legs. After her shorts were off, I put one of my hands on her hips while moving the other hand up to her breast. I squeezed her B-cup-sized breast, feeling her hard nipple against my palm.

Kourtney broke the kiss, moaning as I leaned down and sucked her nipple into my mouth. At the same time, she put her hand on my groin and started to rub my semi-hard cock through my shorts. I pushed her back gently and made her sit on the bed, standing back up straight in front of her.

As she watched me, I pulled my shorts and underwear down, kicking them behind me. I wrapped my hand around the bottom of my shaft, rubbing up and down, while I put my other hand on the back of Kourtney's head. I gently guided her head towards my cock, and she opened her mouth as I pushed the tip of my cock against her lips.

Still holding onto the back of her head, I started to thrust my hips back and forth, sliding my cock down her throat, back out to it's tip, and back down her throat. I started going harder and faster, slamming my cock into her mouth over and over.

I pulled my cock out of her mouth, a trail of spit and pre-cum mixed together, going from my cock to her lips. I leaned down, grabbing onto Kourtney's long legs, forcing her to lay down on the bed as I pulled her legs up. I was still standing on the floor as Kourtney scooted forward on the bed, so her butt was just barely on it. She wrapped her legs around me as I reached forward with one hand and pulled her thong to the side. My hand was back around my cock as I guided it into her clean, shaven pussy.

I let go of my cock as I pushed inside her. Kourtney moaned, feeling my cock fill her up. I put both of my hands on her hips and started to thrust in and out. Going nice and slow, making sure she got my full length, I reached up with one hand and grabbed her breasts, alternating between them. I squeezed her soft flesh, rubbed her nipples, and pinched them before I started to fuck her harder and faster.

As I went hard and fast into her, I grabbed her legs and brought them up to rest on my shoulders. "Oh, fuck, that feels good," Kourtney moaned as I pounded into her. I slammed into her, feeling my orgasm building up. My head tilted back as I moved my hands off her legs and back to her hips.

Her legs slipped off my shoulders as I pushed her down into the bed, holding her down as I started to orgasm. My cock was deep inside her as cum shot out, her hips trying to push up to pump more out of me. I grunted and groaned as I felt the cum shooting out of me. As I finished, I laid down on her, passionately kissing her lips.

Ending the kiss, Kourtney said, "Holy fuck, I've missed you." I laughed, and she said, "Seriously, I've been wanting that all weekend."

I kissed her again as I stood up, and she said, "What do you think Jessica is doing?"

I said that I would go see and turned to leave the bedroom. Entering the living room, I saw Jessica's shorts laying on the floor, and she was on the couch. Her thong was pulled to the side as she rubbed a finger in and out of her wet pussy. "Are you done?" She asked me.

"Yeah, I just came inside her," I told her.

"I want to see," Jessica said, standing up off the couch. I followed behind her as she went into the bedroom. Kourtney was still lying on the bed, her legs spread open, and my cum was dribbling out of her pussy. I watched as Jessica kneeled on the floor in front of Kourtney, in between her legs, and used her tongue to lick my cum out of her pussy.

"Fuck," Kourtney moaned, sitting up and seeing Jessica between her legs. "I was not expecting that."

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"Me either," I said.

Jessica gave her pussy a few more licks before she stood up, crawled onto the bed, and leaned over Kourtney. She slowly lowered herself down until their lips met, and she started to kiss Kourtney. Kourtney gladly returned the kiss, opening up her mouth to invite Jessica's cum-covered tongue inside. The girls continued to make out; Kourtney's hands roamed all over Jessica's body, grabbing her ass, squeezing her breasts, and up and down her sides.

I sat down on the bed, watching the two beautiful women as they kissed, rubbing their bodies against each other, until Jessica broke the kiss, looked at me, and said, "Do you want to help me please her?"

I nodded my head yes as Jessica moved down, taking Kourtney's right breast in her hand and licking her nipple. I did the same thing with her left breast, taking it in my hand and licking the nipple with my tongue before I wrapped my lips around it and sucked it into my mouth. Kourtney moaned as both of her nipples were being sucked on.

Out of the corner of my eye, I saw Jessica moving her hand down to Kourtney's groin, and I moved mine down as well. Jessica had a finger sliding in and out of Kourtney's wet, clean-shaven pussy, so I opted to rub her clit. Kourtney was telling us how good it felt. Me and Jessica looked up at each other, leaned forward over Kourtney's chest, and began to kiss.

"Oh fuck," Kourtney moaned, her eyes rolling into the back of her head. I felt her legs clamping shut around mine and Jessica's hands and heard the familiar moan escaping her lips as she came. Me and Jessica continued to kiss, our tongues swirling together as I rubbed Kourtney's clit and Jessica fingered her.

When Kourtney came down from her orgasm, me and Jessica ended our kiss. Jessica brought her hand up to my mouth, and I sucked off Kourtney's juices from them.

"She tastes good, doesn't she?" Jessica said with a smile.

"Yes, she does," I replied back. "Your turn now."

All three of us adjusted in the bed, pulling off the rest of our clothes as we did so. Kourtney instantly had Jessica's right breast in her hand, and her lips were over the nipple, sucking it into her mouth. I did the same thing with Jessica's left breast, flicking my tongue against her nipple and squeezing her C-cup-sized breast with my hand.

This time, I was the first to move my hand down to her groin. Jessica had a tiny hint of hair around her pussy that I felt on my hand as I slipped a finger inside her. Kourtney soon joined me, but instead of rubbing Jessica's clit, she put her hand on top of mine and controlled the speed with which my finger went in and out of her.

"Oh, yes," Jessica moaned, her hands on the back of mine and Kourtney's heads, forcing us down until her breasts. "God, that feels good."

After a few minutes of pleasuring Jessica, me and Kourtney both looked up at each other. We shared a brief kiss before Kourtney started to move down Jessica's body. I kept my finger inside her as I looked at Jessica, laying with her head on a pillow, eyes shut, and small moans coming from her mouth. I turned my head in the other direction to watch as Kourtney climbed in between Jessica's legs, licked her vagina around my hand, and kissed her clit.

I removed my hand and sat back as Kourtney started to lick Jessica's pussy, Jessica moaning even louder as Kourtney's tongue touched her.

I was starting to grow hard again, so I grabbed Jessica's hand and led it to my cock. She wrapped her hand around my shaft and started to rub up and down. As she jacked me off, I leaned down again, kissing and licking her nipples. Moving up some, I kissed Jessica's lips as I finished growing to my full six inches.

I sat up on the bed, kneeling on my calfs, and moved forward until my cock was at Jessica's mouth. She turned her head towards me, opened her mouth, and wrapped her lips around my tip as I slid inside her. She could only take the first few inches of me in, moaning around my cock as I thrust it in and out of her mouth.

As I face-fucked my girlfriend, I looked down at Kourtney, watching as her tongue darted in and out of Jessica's pussy. She had brought her hand up and was rubbing Jessica's clit at the same time. Kourtney had her legs bent, her ass in the air, and was slowly moving it side to side as she ate out Jessica.

I pulled my cock out of Jessica's mouth and moved on the bed until I was behind Kourtney. I lined my cock up with her pussy again and easily slid inside her. I put my hands on her hips and started to thrust my hips back and forth, sliding my hard, thick cock in and out of her. I heard Kourtney moaning as she continued to tongue-fuck Jessica.

"How does it feel?" Jessica asked me, looking up at me.

"To be fucking Kourtney while she eats you out?" I answered back. "It's amazing."

"I want to taste her on your cock when you're done," Jessica said with a smile.

"Oh fuck," Kourtney said, listening to us talk as I slammed my cock into her and she licked at Jessica's pussy. I ran my hands up and down Kourtney's back, hips, and sides. Bringing my hands back to her butt, I squeezed her ass, raised one of my hands up, and down sharply on her buttcheeks. As I spanked her over and over, Kourtney yelped in pain and pleasure.

Kourtney stopped eating out Jessica as I pounded into her, having to lay her head down on the bed, moaning every time my cock filled her up. Jessica scooted up and out from underneath Kourtney and came up next to me. I leaned down, kissing Jessica, as I fucked Kourtney. I moved my hands off Kourtney, over to Jessica, and up to her chest, where I squeezed her C-cup-sized breasts.

Kourtney started to push back against me as Jessica ended the kiss, and spanked Kourtney's ass. Jessica put her hands on Kourtney's hips and started to help move her body back and forth, sliding my cock in and out of her pussy.

"Oh, fuck, I'm coming!" Kourtney moaned loudly, as I felt her pussy clenching around my cock, squeezing it tight as she orgasmed.

I quickly pulled out of Kourtney and turned to Jessica. As Kourtney fell flat on the bed, Jessica leaned down, using her tongue to lick the pre-cum and juices off the tip of my cock. She wrapped her lips around my tip and took the first few inches of my shaft in her mouth, bobbing her head up and down.

As Kourtney recovered on the bed, I pulled my cock out of Jessica's mouth and laid down next to Kourtney. Jessica grabbed onto my cock, held it straight up in the air as she straddled my lap, inserted the tip into her pussy, and slid down my shaft. We both moaned as she started to rock her hips back and forth. I moved my hands up and grabbed at her breasts, giving them a few squeezes before using my fingers to pinch her nipples.

I looked over to see Kourtney watching me as Jessica rode me. "You OK over there?" I asked her.

Kourtney laughed, adjusting so she was more on her side, and said, "I'm amazing. It's so much fun to watch you two fuck."

I reached over, putting my hand on Kourtney's face and pulling it over to mine. We started to kiss, our tongues quickly swirling together, as I moved my hand down to Kourtney's breasts. I squeezed them, one at a time, before using my fingers to rub and pinch her nipples.

Ending the kiss as Jessica bounced on my cock, I watched as Kourtney sat up on the bed. She turned to face towards Jessica, making her slow down her bouncing as Kourtney leaned down to suck on Jessica's nipples. I watched as Kourtney, her long brown hair dangling in two pigtails behind her, switched between Jessica's breasts, licking and sucking on her nipples.

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