Pleasing My Sister-in-Law

I was at work the next day after me and Jessica had our latest night together when my wife sent me a text saying, "Hey, Alissa and Jennifer want to have a girls night tonight with all of us spending the night at Alissa's. Do we have plans?"

"None that I know of," I texted back. "Are you taking the kids?"

"Yes, they are all coming. What are you going to do with the house to yourself?" She said.

I told Kathy that I would probably not do anything but play video games. After texting her that, I sent one to Jessica that said, "Hey, what are you doing tonight? Kathy and the kids are going to Kathy's friend's house for the night, and I'll be home all alone."

"I'll text Jack and see if he can take Liam," Jessica texted back.

Unfortunately, Jessica texted a little later to say that Jack couldn't take Liam, and neither could her parents. "I'm sorry, Danny; a full night with you would have been amazing. Maybe you should text Kourtney?"

I told her that was a good idea and sent Kourtney a text saying, "Hey, what are you doing tonight and tomorrow morning? What's the chances of you coming over, letting me fuck you tonight, and covering you with my cum tomorrow?"

"Umm, that sounds amazing," Kourtney texted back. "Where will Kathy and the girls be?"

"At Kathy's friends house for a girls night. And spending the night there too," I told her.

"Hell yes. When do you want me to come over? Any special requests about what to wear? I heard what you had Katie wear last week," Kourtney said.

"Oh, she told you about that? I'll think of something. Gary won't mind you going for the night or asking any questions?" I asked her.

"Nope. I just texted him that I was going to spend the night at a friend's house, and he said to have fun. More game playing for him without me there to distract him," Kourtney said.

"I don't know about him some days. You can come distract me whenever you want," I told her before our discussion shifted to what she should wear that night.

I made Kourtney wait an hour after Kathy left with the kids. First, for me to eat, and second, just to make sure nothing else happened. Luckily, she only lived a few minutes away, so I didn't have to wait long once I told her to come over. When she walked in my door, she had her long brown hair pulled up into a bun on top of her head. Wearing a white shirt and red and black shorts, she was carrying a backpack that she pulled off her shoulders after she gave me a hug.

"Gary didn't ask any questions about the bag?" I asked her as we sat down on the couch.

"Nope. Well, yes. He saw me packing it and he asked if I was getting paid for tonight. When I told him no, he said that was good, for some reason. I guess he's OK with me sleeping around, but he doesn't want it to look like I'm a ho," Kourtney told me with a laugh.

I laughed too and said, "I wonder what he would think if he knew it was me you've been sleeping with."

"Let's not find out," Kourtney said. "Want me to go change?" I said sure and watched as she grabbed her bag again and walked into the bathroom.

When she came out about ten minutes later, she had completely transformed. Her brown hair was loose now, ending around her lower back, and was swooped back onto the back of her head, keeping it out of her face. She had put on a blue dress with two spaghetti strings holding it on her shoulders. It had a deep V cut in the front, showing off the cleavage of her B-cup-sized breasts, and it flowed down to her ankles, with a slit cut out on one side where she had her left leg poking out. The dress had a flower print design on it, but I barely noticed it as she spun around for me.

"God, you're beautiful," I said as Kourtney joined me on the couch.

"Thanks," she said. "Want me to tell you what happened last time I wore this dress?" I said yes, and she went on, "Me and Gary were at a New Year's Eve party. One guy there couldn't keep his eyes off me, so I flashed him my tits and rubbed his groin when he asked me to dance with him. He took me into another room, pushed me up against the wall, lifted up my dress, and fucked me. He came in my pussy, and I had to leave my thong off the rest of the night. When we got home that night, I rode Gary like crazy; I was so fucking horny."

"I thought you hadn't been with any other guys since we started sleeping together." I asked her.

"That was the only one. And I was wishing it was you. He kind of looked like you, but his dick wasn't as thick," Kourtney said, leaning up against me and starting to rub my cheek.

"Well, I can't wait to give you another good fucking in that dress," I said, wrapping my arm around her.

"Let's get to it then," Kourtney said, starting to kiss my lips. I kissed her back as she climbed onto my lap, moving my hands down to her buttocks and squeezing them as she started to grind on my groin. I started to kiss her neck, softly sucking her tan skin into my mouth before letting go, as I grew hard in the shorts I had on. Feeling my cock attempting to push through her dress, Kourtney pushed her groin harder against mine until I finally said, "Why don't you get on your knees and work your magic?"

Kourtney smiled as she slid off my lap and down onto the ground. I lifted up my hips as she pulled my shorts and underwear down, my semi-hard cock popping out and smacking her in the forehead. She immediately, without using her hands, opened up her big mouth, took my cock in it, and started bobbing her head up and down as I finished growing to my full six-inch length.

"How many times do you think my cock will be in your mouth between tonight and tomorrow?" I asked her, and Kourtney shrugged her shoulders, still not using her hands. "How many loads can you take? I'm hoping for at least three or four. One in your pussy, one on your face and tits, and maybe one in your ass. Can you handle that?"

Kourtney finally wrapped her hand around my shaft and took me out of her mouth. She looked up at me with her hazel eyes and said, "I can handle it all. I want it all. And I brought my handcuffs and blindfold, if you really want to take control of me."

She then went back to blowing me, moving her mouth up and down my entire shift with my hand following behind it. I leaned back on the couch, enjoying the feeling of her lips wrapped around my cock, when I heard my phone go off. I took a glance at it to make sure it wasn't my wife, but it was Jessica instead. "Hey, I wish I was with you tonight. Did Kourtney come over?"

I told her that Kourtney was over at my house, and Jessica said, "I'm jealous. Liam fell asleep early, and I'm horny."

"We should have just had you bring him over. You could be blowing me away with Kourtney right now," I told her.

"Is it weird if I want to see?" Jessica texted me back.

Kourtney opened her eyes as she blew me and asked who I was talking to. I told her, "It's Jessica. She's horny and wants to see you blowing me." She quickly put my cock back in her mouth as I snapped a couple of pictures, sending two of them to Jessica. The first was with my cock half out of Kourtney's mouth, and the second was all the way down her throat.

After seeing the pictures, Jessica said, "Yeah, I wish I was there. Have fun! I'm going to put these pictures to good use."

I looked down at Kourtney and said, "Get up here and ride me." Kourtney used her tongue to lick from the bottom of my shaft up to my tip before she stood up from the floor. I watched as she hiked her dress up to her waist, revealing that she wasn't wearing any underwear, and climbed back onto my lap. With one hand holding her dress, she reached down with her other hand and slid my cock inside her wet, clean-shaven pussy.

She let go of both my cock and her dress at the same time, wrapping her arms around my neck, and started to roll her hips back and forth on top of me. We shared a brief but very passionate kiss before she started to bounce harder and faster, riding my cock with her fit body.

I reached forward with my hands, pulling the front of her dress down just enough that I could pull both of her B-cup-sized breasts out of it. I took both of her breasts in my hands, squeezing them and rubbing her nipples, before leaning forward and sucking her left nipple into my mouth. I flicked with my tongue a few times before moving over to her right nipple, licking all around it with my tongue, sucking it into my mouth, and flicking it with my tongue.

As Kourtney continued to ride me, sliding my cock in and out of her pussy, I kept alternating between her breasts, sucking on one nipple while rubbing the other with my fingers. I moved my free hand down to her butt, spanking it before grabbing her cheeks and squeezing them, using my grip on them to pull her closer to me.

Wanting to adjust, I started to stand up, with Kourtney wrapping her long legs around me and attempting to still bounce on my cock. When I slipped out of her, Kourtney put her legs on the floor, and her dress fell back down to her ankles. I moved us so that she was facing the couch with me behind her and told her to bend over. Kourtney grabbed onto the back of the couch, sticking her ass out into the air for me.

I moved her dress back up to her waist, pulled my hand back, and spanked Kourtney's butt before I stood behind her and easily slipped my cock back into her pussy. I grabbed onto her hips as I started to thrust back and forth, sliding my thick cock in and out of her.

"Yes. Yes. Give me that big fucking cock of yours. Fuck me, Danny! Harder!" Kourtney moaned as I slammed into her over and over. I spanked her ass a few more times before she started to beg for my cum. I wrapped my arms around her skinny waist and thrusted my cock in and out of her as hard and fast as I could until my orgasm hit. Feeling the cum erupting out of the tip of my cock, I held myself still as I filled her up, finally letting go when I was done.

I sat down on the couch next to where Kourtney was leaning over it. Her brown hair was covering her face as she caught her breath. When she finally did and turned around to sit down next to me, she said, "That's number one."

I laughed and said, "Are you ready for number two?"

"Always," Kourtney said, leaning over to kiss me. "Do you want me to stay in this dress?"

"Nah. You can take it off for now. How about just a thong?" I told her. I watched as Kourtney stood up, grabbed the bottom of the dress, and pulled it up and over her head. She felt my cum leaking out of her pussy and said, "I'm going to run to the bathroom. My thongs are in the front pocket of my backpack. Do you want to pick one out for me?"

When Kourtney came back out a few minutes later, I handed her a pink lace thong. It was see-through around the vagina, with a string going up the buttocks, and fit her body perfectly. She pulled it on for me and twirled around before sitting down next to me. I had already put back on my underwear but left my shirt off, and she rested her naked upper body against mine as she sat down.

Only about thirty minutes had passed. Kourtney had arrived at my house. With the night still young, we moved to the dining room table, pulled out a deck of cards, and sat down to play a few games. With Kourtney's breasts out in the open, I lost far more than I won, which made Kourtney happy.

After I lost to her in a couple games of speed, Kourtney excused herself and went to the bathroom. I watched her ass sway in her thong as she walked away and was intently staring at her tits when she came back. Sitting back down at the table across from me, Kourtney asked, "Are my tits distracting you?"

I laughed and said, "Maybe? I kind of want to see them covered in my cum."

"Oh, me too. Are you close to being ready yet?" She asked me, and I said I was getting there. "Back to the couch?"

I watched as she stood up from the table and started to walk back to the living room. I got up behind her, fished my cock out of my underwear, and walked towards her. I put my hands on her shoulders, got her to stop walking, and turned her around to face me. As she started to ask what I was doing, I pushed her down onto her knees, where her face became level with my hard cock. Holding onto her head with one hand, I grabbed my cock with my other hand, lined it up with her mouth, and pushed forward, Kourtney opening her mouth up as I did so.

Still holding onto her head, I started to thrust my hips back and forth, making Kourtney gag on my thick cock as I shoved it down her throat, holding it still while pushing her head forward with my hand, before letting go and repeating the process.

I pulled my cock out of her mouth, wrapped my hand around it again, and rubbed the tip of it all over Kourtney's face, coating her with her own saliva and my pre-cum. I slapped her cheeks with my shaft a few times before sliding back into her mouth and going back to face-fucking her. After a few more thrusts, I pulled out again and said, "Go lay down on the couch."

Kourtney did as I did, and I went and climbed on top of her. I lowered my cock down so it rested between her breasts. Kourtney pushed them together, but they barely covered my cock. I still started to move up and down above her, sliding my cock between her breasts.

Moving back up to her mouth, I pushed my tip past her lips, and she started to bob her head up and down my shaft as I held myself above her. I told her that I was getting close and pulled out of my mouth. I moved so that my cock was back above her breasts and looked down as Kourtney took it in her hand, rubbing up and down.

With a loud grunt and a groin, I started to orgasm. The first rope of cum fell out of my cock, landing on Kourtney's left breast, quickly followed by a second onto her right breast as she pointed my cock at it. She pumped my shaft up and down, squeezing out all of my cum, aiming it so it covered her breasts.

When I was done, I moved off the couch and sat down on the ottoman next to it. I watched as Kourtney used her hands to rub my cum all over her breasts and then sucked it off her fingers with her mouth. She smiled at me and said, "So, how do they look covered in your cum?"

"Amazing. I'm tempted to tell you to keep it on there until I'm ready again, and I'll cover your face next," I told her.

"Can I tell you a secret?" She asked, and I said, of course. "That's my dream. To be covered in a guy's cum everywhere."

"I would want to make that dream come true for you, but your pussy is just so nice to come in," I said.

"Yes, it is. Maybe one day I'll get my dream," Kourtney said as she got up off the couch, going into the bathroom to clean herself up again. When she came back out, she joined me again on the couch, cuddling up in my arm, and I turned the TV on to some random TV show.

After the first episode ended and the second started, Kourtney put her hand on my groin, rubbing a little, and said, "Do you think you have one more in you tonight?"

I said, "Of course. I might just need some coaxing to get hard again."

"Like what?" she asked me.

"How about we go in the bedroom and we can play with your toys?" I suggested.

"Oh, you saw those too?" She said, and I said that I did, as we both stood up. Kourtney reached into her backpack and pulled out a dildo and a vibrator. I followed her into the room, and we both laid down on the bed. Kourtney laid down on her back, and I moved next to her, almost on top but just to the side, and we began to kiss.

Kourtney wrapped her arms around my neck as I put one of my hands on her flat stomach and rubbed it, slowly making my way up to her breasts. As we kissed passionately, our tongues swirling together, I rubbed both of her nipples, squeezing her breasts one at a time, switching back and forth to make sure they both received the same amount of care.

I then moved my hand back down her stomach and onto her thong, where I rubbed her pussy through it. I stopped kissing her lips and moved down to her neck, then to her breasts. I began to lick around her nipple with my tongue, sucking it softly into my mouth. At the same time, I moved her thong to the side and slid my finger up and down the slit of Kourtney's pussy lips. I pushed my finger inside her, sliding it in and out as Kourtney began to moan.

I licked and sucked both of her nipples before looking up at her and saying, "So, what do you like to play with more? The dildo or the vibrator?"

"Both at the same time, honestly," Kourtney said.

"Show me," I said as I sat up on the bed and handed the toys to Kourtney.

I watched Kourtney pull the thong down her long, tan legs and throw it at my face. I grabbed it in my hand and gave it a little sniff before tossing it onto the floor, making Kourtney laugh as she laid back down. She took the black, seven-inch-long, and thick dildo in her hand, rubbing the tip of it up and down her pussy. She briefly stuck the tip of it inside her before pulling it out, bringing it up to her mouth, and making eye contact with me while she sucked her juices off it.

She then brought it back down to her groin. With one hand holding the dildo, she used her other hand to spread her pussy lips before she pushed the dildo back inside herself. Kourtney let out a moan as she filled herself up and started to slide the dildo in and out.

After she got up to a steady rhythm with the dildo, she grabbed the vibrator with her free hand, clicked it on, and put it up against her clit, moaning as she did so. She began to rub it around as it vibrated against her clit, moaning as she continued to fuck herself with the dildo.

"Do you like to watch me play with myself?" She asked me. I told her I did, and she said, "Good. Hopefully it makes you hard again."

I could feel myself starting to stir in my underwear, and I told her it was working. She continued to rub the vibrator on her clit while sliding the dildo in and out of her. I pulled my underwear off while I watched her, and she eyed my cock as I wrapped my hand around it, slowly rubbing it up and down, trying to grow harder and harder.

"I can't wait to have that big, hard cock inside me," Kourtney said.

"How bad do you want it?" I asked her.

"So fucking bad. You fucking my face and my tits earlier made me so horny. I've been craving your cock ever since," she said.

I was nearly at my full six inches and said, "As soon as you cum, you can have it. What position do you want?" I moved up to lay down next to her. My now-hard cock pointed straight up in the air as I continued to stroke myself. Kourtney never took her eyes off it as she masturbated with her toys.

"I don't even care at this point; I just want your cock," Kourtney moaned out.

"It's ready for you," I said as I got up and kneeled in front of her. Kourtney was staring at my cock when she finally started to come. She threw the dildo off the bed as the vibrator did its job on her clit. As she arched her back off the bed, I moved forward and quickly slid my cock inside her pussy, pushing her back down on the bed as I pushed in deep.

Kourtney dropped the toy as I grabbed her hands, pinned her arms above her head, and started to thrust in and out of her. "Oh yes. Yes! Harder!" Kourtney moaned as her body squirmed under mine. I pushed in as hard and deep as I could, over and over, our bodies smacking together as I pounded her pussy with my cock.

I pulled out of her and used my grip on her hands to pull Kourtney up. I put one of my hands on her hip and started to push her over. Getting my hint, Kourtney rolled onto her stomach, then up onto her hands and knees. I kneeled behind her, lined my cock up with the entrance to her pussy, and slowly pushed back inside her. I placed my hands on her hips and, while holding myself still, started to move her body back and forth, sliding her up and down on my cock.

Kourtney again got the hint and started to move her own body, slamming her ass back into me. I raised my hand and spanked her ass a few times as she came back towards me before I stopped her from moving and started to thrust my cock into her on my own.