Pleasing My Sister-in-Law

As I reread Jack's text, asking me if I was dating his ex-wife, Jessica texted me to tell me that she was home. I quickly texted her back that I was glad she was safe, and then sent her a screenshot of Jack's text and asked if she told him.

She told me no and that she was curious why he would ask me. I texted Jack back to say, "Why would you think that?"

He responded back by saying, "Well, that response pretty much confirms it."

"Me and her are friends," I said back.

"Right. That's why she was texting you on Sunday and why I found her car at your apartment later that day," he said in return.

"That's low, man; why would you go looking for her? And why do you even know where I live?" I said, relaying to Jessica what Jack was saying.

"Don't worry about it. She's the mother to my child, and I have a right to know what she's doing," Jack said.

Feeling myself starting to get angry, I typed out a response to him before deleting it and deciding not to engage with him anymore. When my phone went off again, thinking it was Jessica, instead I found a text from Jack. It said, "I really don't care if you two are friends, dating, or whatever you want to call it. I was just being curious.  If she is going to date again, I'm glad it's somebody that Liam already knows and Jessica trusts."

I asked Jack if he was going to tell anybody else and then asked Jessica, "So, do you really consider me your boyfriend? Or what?"

Jessica asked if she could call me later to talk about it, and I said yes. I didn't hear from Jack again and figured I would deal with it later if he told anybody.

When Jessica called me that night, she asked, "So, what would you think if I did consider you my boyfriend?"

I laughed and said, "It would make me happy."

"I have been thinking about it a lot. We talk so much, visit each other when we can, and care about each other. Really, the only obstacle in the way, besides the distance thing, would be you and Kourtney," Jessica said.

"And I've told you before that you say the word, and I'll never do anything with Kourtney again," I said.

"Maybe I'm waiting for you to make that decision and tell me that I'm the only girl for you," Jessica said.

I paused for a few seconds, thinking about that, before she said, "I'm just kidding. I'm the one who told you to keep sleeping with her anyway. I more just mean, if I did start calling you my boyfriend, what will she think?"

"Oh. I don't know. I guess we could ask her," I suggested.

"Or, we could just consider ourselves to be officially in a relationship, and she'll eventually find out," Jessica said.

"I like the sound of that," I said, and Jessica agreed.

A few days later, I received a text from Kourtney, asking if I wanted to get some food with her that night. I told her yes, and we agreed to meet at a restaurant after she got off work.

I arrived at the restaurant ten minutes before Kourtney, and I was talking on the phone with Jessica. I had already told her what I was doing that night, and when I told her I was at the restaurant, she said, "So, what's the chance this night of yours ends up with you and Kourtney back at your apartment?"

I laughed and said, "Probably pretty good. Why do you ask?"

"Just curious. Just thinking about you having sex gets me going. Knowing when you're actually doing it, it gets wet," she said.

"Oh yeah? And what would happen if you got a picture while me and Kourtney were together?" I asked her.

"I guess you'll just have to find out," Jessica said, making us both laugh. When I saw Kourtney pull up in her car a few minutes later, I got out of mine, said goodbye to Jessica, and walked up to Kourtney, wrapping my arms around her in a hug when I reached her.

We walked into the restaurant and were quickly seated at a table. We ordered some drinks while talking about our day and looking over the menu. After the waiter took our food and walked away, Kourtney looked at me and said, "So, I actually did have something that I wanted to talk to you about tonight. Well, two things."

"Ok," I said, waiting to hear what she said.

"Jack called me the other day. He asked if I still talked to you or Jessica. He then asked if I knew that you and Jessica were dating," Kourtney said. I asked what she told him, and she said, "I told him that it was none of his business if I still talked to you or her, and it was none of his business if you two were dating."

"Yeah, he caught Jessica texting me on Sunday. And then he somehow found out where I lived and saw Jessica's car at my apartment. He texted me about it on Monday, but I never really gave him an answer," I explained to Kourtney.

"He's so strange. Like, even if he did know, what is he going to do about it?" Kourtney said, taking a drink from her glass afterwards.

"Probably try to cause more family drama that nobody wants," I said.

"Right? So, the other thing, and, Danny, I don't need any answer today or any time soon, but I would appreciate it if you at least thought about it," she started. She went on to say, "So, I got accepted to the dentist college in Chicago."

"That's awesome! Congratulations," I said.

"Thanks. So, I'll be moving there next summer to start school in the fall. Of course, the original plan was to move there with Gary, get jobs, and support each other until I finish dental school, then decide where we want to live forever. But, now that we're divorced, I need to figure something else out," Kourtney said as I looked into her hazel eyes.

I gulped down a drink and said, "I think I know where this is going."

"Will you at least think about it? You're really the only person I trust and want to be around. Like I said, I don't need any answers now or any time soon. I know you have the whole thing with Jessica, and your kids are here, so it would be extremely hard. I keep thinking about it too--how hard it will be to leave everyone," she said.

"Yeah, it wouldn't be easy," I said.

"But I think we could make it work. I would help pay for everything, no matter how long it would take you to find a job or something to do there. I would even make sure to put money away so you could fly back here to see your kids. And I almost hate to say this, but it would be so true that I would be completely free to use for you. Whenever you wanted to fuck or a blowjob, or whatever, any time, any place," Kourtney said, her eyes pleading with me.

I took another drink before Kourtney said, "I'm sorry, Danny, that was a lot. I really don't expect you to come, and I wouldn't hate you if you didn't. But will you at least think about it?"

I told her that I would, right before our food was served. We enjoyed the dinner and conversation before paying and leaving the restaurant. Walking out to our cars, I said, "So, do you want to go back to my place?"

"And do what?" She asked me, leaning up against her car. I smiled at her and looked her body up and down until she said, "Of course. Let's go."

Back at my apartment, we were standing in my bedroom, our arms wrapped around each other as we made out. Kourtney's scrubs and jacket had been discarded right inside the door; my shirt and pants lay next to my bedroom door. Kourtney ended the kiss, and I watched as the six foot-tall, tan-skinned, fit woman, clothed in only a black, padded sports bra and black underwear, kneeled on the floor in front of me. She pulled my underwear down and off my legs, my semi-hard cock flopping out in front of her face. She used her tongue to lick all around it before wrapping her lips around the tip.

As I grew harder, she used a hair tie she had on her wrist to pull her long brown hair back into a ponytail before she started bobbing her head up and down my shaft. She brought up one of her hands, grabbing and squeezing my balls, as she deep throated me over and over. I could feel her tongue running on the underside of my cock as she buried her nose in my groin, holding herself still for a few seconds, before moving back up to my tip, where she swirled her tongue around it, before sliding back down.

Not wanting my legs to give out, I moved back towards the bed, with Kourtney moving along with me to keep sucking my cock. She briefly took her mouth off me, her hand taking its place, as I sat down. She kept her hand going up and down my shaft and resumed blowing me with her mouth as I put my hand on the back of her head, helping to guide her.

After a few minutes, Kourtney again took me out of her mouth, moving up so my cock was against her bra as she jacked me off and said, "Maybe I'll try to convince you to move to Chicago by giving you a blowjob every night until I move, since you seem to enjoy them so much."

"I do enjoy them. I also enjoy you riding me," I said as I started to pull up on Kourtney's head. She climbed onto the bed, pulling her underwear off, as I scooted up to the top of the bed, laying my head down on my pillows. I watched as she took my hard, six-inch-long, thick cock in her hand, kneeled above it, and inserted the tip into her wet, clean-shaven pussy before letting go and sliding down it.

I put my hands on her hips as she started to roll them back and forth, sliding my cock in and out of her. As she got into a steady rhythm, I moved my hands up and put them on her bra-covered chest. The bra had a zipper in the front that I quickly undid, and then I used my hands to push the bra to the side so I could squeeze her naked breasts. Kourtney finished taking the bra off, tossing it to the floor, as I used my thumb and index fingers to rub and pinch both of her nipples.

She started to bounce harder and faster on my cock, but I kept my grip on her breasts, squeezing them as she rode me. When I finally moved my hands back down to her hips, Kourtney quickly got me out of her, spun around, and slid back down my cock, with her back to me now.

I moved my hands to her ass, spanking and grabbing it, as she kept riding my cock up and down. "It's too bad I don't have my toys with me," she said as she bounced on me. I asked why, and she said, "Because it feels so good to have something in my ass when I'm riding like this."

Instead of saying something, I moved my right hand over to the middle of her ass, and pressed my thumb against her hole, putting pressure on her entrance there. "Oh my God!" Kourtney yelled out as I put more pressure on her ass. She started to cum, her pussy clenching around my cock, juices flowing out of her as she bounced wildly on my cock. I pushed my thumb into her ass, causing Kourtney to scream again, sitting up straight on my cock.

When her orgasm was done, she fell over; my thumb popped out of her ass, but she kept slowly rocking her hips back and forth. I grabbed onto her hips, pulled her off me, and flipped her over so she was lying down on the bed. With a smile on her face, Kourtney watched as I lifted her legs up and spread them apart before stepping between them and sliding my cock back into her.

Still holding one of her legs up, I started to thrust back and forth, my cock pistoning in and out of her wet pussy. With her still loudly moaning, I was going harder and faster until my orgasm exploded out of me. I pushed in deep as cum shot out of my cock, mixing with Kourtney's as we enjoyed the feeling.

When I was done, I pumped in and out of her a few more times until I pulled, a mix of our juices trailing from her vagina to my cock. Kourtney looked down and said, "Fuck, it's been a while since I've had a creme pie." I laughed as I watched my cum spill out of her before handing her a tissue to clean up with.

We laid in my bed together, cuddling naked, for another hour until Kourtney said that she had to go. I watched her as she got dressed. After putting on her scrub top, she asked, "So, what are you doing Saturday night? Hanging out with Jessica?"

"No, she has Liam for the weekend. Probably nothing. Why?" I asked her back.

"One of my coworkers is throwing a Halloween party, and I was going to ask if you wanted to come with me," she said, sitting back down on my bed.

"Really? A party? And you want me to dress up?" I said.

"I'm dressing up as a slutty cheerleader. And if you don't come, I know that one of my male co-workers will gladly take me home with him," she said, teasing me. "And you don't have to dress up. Just come with me, eat some food, and then we'll come back here and fuck all night long."

I sat up, kissed her, and said that I would go.

The weather had finally started to cool off by that Saturday night. I threw on some jeans and a hoodie before Kourtney came to pick me up for her co-workers party that night. I got into her car, leaning over the center console to give her a hug and a kiss before she drove us away from my apartment. She had put on a black leather long jacket over her costume, but I could see that her long, tan legs were bare, with a pair of white and pink athletic shoes on her feet.

When we arrived at her coworkers house that was hosting the party, we walked hand-in-hand up to the door, where Kourtney knocked and waited. I was quickly introduced to everybody there, turned down the alcohol when it was handed to me, and watched Kourtney take a shot before she disappeared with a group of friends.

I was talking to the guys that she worked with, trying to figure out who had a crush on her, when Kourtney came and found me a few minutes later. She had taken off her jacket, and I watched all of the guys eyes move up and down her body when they saw her costume.

She had on a pink pleated mini-skirt that barely covered her groin, a white and pink crop top that showed a large portion of her B-cup-sized breasts, and the word "cheer" printed across it. She had her brown hair tied back into two pigtails and smiled at us all as she greeted us.

Wondering if I could get a reaction out of one of the guys staring at her, I reached down and took Kourtney's hand in mine. One guy watched me do it and bit his lip. As the conversation drifted away from me and Kourtney, I leaned over and whispered in her ear, "Is the guy with the blonde hair the one that you think would take you home?"

"Derek? Yeah, that's him. He hasn't taken his eyes off me since I got here," she whispered back.

"So, it would be rude of me to tease you in front of him?" I said as I turned towards Kourtney, my back to Derek. I lowered my head down and started to kiss the exposed skin of Kourtney's neck, while moving my hands to her skirt.

"He's watching your every move," Kourtney said.

"Do you have a thong on?" I asked her, and she said yes. I turned us around so Kourtney's back was to Derek. Grabbing the bottom of her pink skirt, I made eye contact with Derek as I lifted it up, flashing Kourtney's ass and thong at him. I felt her move her hips from side to side before grabbing the skirt from me and pulling it down. Without looking back behind her, Kourtney started to push me out of the living room we were in, into the kitchen, and eventually out the back door of the house onto a patio.

"What did he do?" She asked me as we found a couple chairs to sit down on.

"His mouth fell open, and then he nodded his head, yes," I told her.

"That's awesome. That actually turned me on a bit," she said.

"Ready to go back to my place, then?" I asked her, but she said no. We spent the next few hours mingling with her co-workers and eating some food. Kourtney had a few more shots, and I could tell she was getting horny with how she kept pushing her body against mine.

As the party started to wind down, the few that remained were standing in the kitchen around the island, separating it from the dining room, when one of her co-workers, whose name I learned was Abby, asked, "So, Kourtney, what is yours and Danny's relationship? I've heard you talk about him a lot, but you've also said that you're single."

Kourtney laughed and said, "We're just friends. He used to be married to my sister."

Somebody else asked, "You're friends with your sister's ex? That's crazy."

Kourtney took another shot and laughed again. Looking at me with her hazel eyes, she said, "Well, we're friends who happen to enjoy each other naked and fuck a lot."

Everybody that was there laughed, and somebody asked, "Is that why you're dressed like that? Ready to go home and fuck?"

Kourtney looked at them, at Derek, then at me, and said, "We might not even make it back to his place."

We left a few minutes later, saying goodbye to everybody and walking out to Kourtney's car. She asked if I wanted to drive since she had been drinking, and I said yes. After I climbed into the driver's seat and started the car, Kourtney leaned over the center console, grabbed my head with her hands, and turned me towards her. Her lips met mine, aggressively kissing me and pushing her tongue into my mouth.

I returned the kiss as her hands went down to my pants. She quickly unbuttoned my jeans and fished my semi-hard cock out of them, wrapping her hand around the shaft and rubbing it up and down.

When I was at my full six-inch length, Kourtney broke the kiss and moved down so her head was over my cock. She stuck her tongue out, licking the pre-cum off my tip, before opening her mouth wide and taking me deep into her throat. I moaned as she started to bob her head up and down the full length of my shaft, keeping her hand wrapped around the base to hold me straight up.

"Shit," I said as I saw the door to the house open up. "Derek and Abby are leaving." Kourtney glanced up at them for a second before going back down and blowing me. I watched as Abby went one direction, heading away from the car, but saw Derek walking right towards us. He made eye contact with me, a confused look on his face, until he looked down and saw Kourtney's head moving up and down in my lap.

He shook his head as he walked past, mouthing to me, "Lucky man." I heard him get in his car, start it, and drive off before Kourtney sat back up in her seat. She looked at me, her hand still on my shaft, and said, "Did he see?" I told her that he did, and she said, "Oh, good. Let's go back to your place now."

"That's just mean," I said as I backed the car out of the driveway and drove back home.

At the first stoplight we came to, Kourtney finally let go of my cock. I looked over as she shifted in her seat and watched as she pulled her thong off her long legs. She moved the skirt up enough to expose her wet, clean-shaven pussy, and began to rub her fingers up and down her lips. "I don't know why, but drinking makes me so horny," she said as she slid a finger inside herself, pulling it out covered in her juices.

She stuck a finger in her mouth and sucked off her juices before going back to fingering her pussy. "Are you going to fuck me in my cheerleader uniform? Or take it off?" She asked as she played with herself.

"I'm going to start by fucking you in it, but I can't promise you'll be wearing it again," I told her as I tried to keep my eyes on the road, stealing glances at her.

"Derek tried to get me to go home with him," she said.

"Oh yeah? And what did you tell him?" I asked her.

"He actually made me laugh because he said if I agreed to go with him, he would convince Abby to take you home," she said.

"Really? Damn! You should have said yes," I told her with a laugh.

Kourtney had almost brought herself to an orgasm when I parked at my apartment complex. I asked if she wanted to finish, but she said, "No, I want you in me," and we both walked quickly into my apartment. As I shut and locked the door behind us, I said, "Go lay on the bed."

I followed Kourtney to my bedroom, watching as she lay down on the edge of the bed, her feet dangling off the end. I stripped off my clothes, my cock still rock hard, and stepped up in between her legs, pushing her skirt up to her waist. As she pushed her hips forward towards me, my cock easily slipped into her wet pussy, causing us both to moan. I grabbed her hips and started thrusting back and forth, over and over, causing Kourtney to move up on the bed, before pulling her back down towards me every time.