Pleasing My Sister-in-Law

I reread Jessica's text to make sure I read it correctly, and then texted back to ask if she was sure. She replied back, "Of course. And it's not some weird kind of test. If you two want to sleep together, then do it. It'll hopefully keep you from wandering when I'm not around, and it sounds like she needs a friend."

I texted her back that if she ever changed her mind, just to say so, and she said that she would. Changing subjects, we immediately started talking about when we could get together again.

At the same time, I texted Kourtney and said, "Hey, I am back home at my apartment now. I hope you're doing OK."

"I'm doing good. Did you have a good weekend with Jessica?" She replied back, and I told her, "I did. It was good to see her and catch up with her. Are you doing anything after work today?"

"Probably just going home. Why?" She asked me.

"Because I want to make up for not being around this weekend," I said.

"And how do you want to make up for it?" She asked.

"Either taking you out to dinner or you coming here and fucking you silly," I replied back.

"Both sound good. I'll see you when I get home," she texted me.

I took Kourtney out to a little hole-in-the-wall Mexican place that night. She worked as a dental hygienist and came straight to my apartment, still wearing her gray and pink scrubs, with her long, brown hair pulled back into a ponytail. As we ate, she asked, "So, what did you and Jessica do this weekend?"

"We just hung out. We went out to lunch and a movie one night and dinner the next. We spent a lot of time just talking," I told her.

"That's it?" Kourtney asked, raising her eyebrows.

With a smirk on my face, I said, "We may have fucked once or twice." Kourtney raised her eyebrows again, and I said, "Once or twice a day, I mean."

"That's what I thought. So, are you two a couple now?" Kourtney asked as she took a bite of food.

"No, not officially. She did ask if I wouldn't sleep around, but we both know that it's smarter if we take some time and not rush things," I explained to her.

"And so the first thing you do is get home and invite me over?" Kourtney questioned me.

"Well, yeah. Jessica did say that you're exempt from that. She figures that it'll keep me from sleeping around and that you need a friend," I said.

Kourtney laughed and said, "Well, she's not wrong. Hopefully on both accounts."

I opened up the passenger door to my car after we finished eating and watched as Kourtney sat down in the seat and closed the door. I walked over to the driver's side and got in, turning on the car as Kourtney said, "Thank you for dinner, Danny."

"Of course," I said. "My pleasure."

"I know you said you were going to take me back to your place afterwards and fuck me silly, but how about I repay the dinner first?" I asked how as I pulled out of the parking lot and glanced over as Kourtney reached out for my groin with her hand. She started to rub my cock through the pants I had on, and I slowly grew hard at her touch. As I pulled up to the first stop light, Kourtney undid the button on my jeans, reached into them, and fished my semi-hard cock out of my boxers.

Looking around at the cars near us, Kourtney unbuckled her seat belt as I started to drive, leaned over the center console, and began to lick my tip. When I grew to my full six-inch length, Kourtney wrapped her lips around my tip and slid her mouth down my shaft, bottoming out with her nose in my groin. As I continued to drive, Kourtney bobbed her head up and down my cock, moaning around it as she did so.

I pulled into my apartment complex parking lot a short time later, found a spot close to my apartment, and parked my car in it. I looked down at Kourtney, still blowing me, and said, "As good as this feels, we should take it inside."

Kourtney licked the pre-cum off my cock before sitting up in her seat. She tucked my thick cock back into my boxers and said, "Better hurry before that gets too uncomfortable." I pulled my pants back on before getting out of the car and walking to my apartment. As I went to unlock the door, Kourtney stood behind me, wrapped her arms around my body, and rubbed my hard cock through my pants.

As soon as we were inside, Kourtney was pulling my pants and underwear down, and I helped to kick them off as she wrapped her hand around my shaft, rubbing it up and down. I wrapped my arms around her skinny, fit waist and pulled her close to kiss her lips. We walked each other to my bedroom, where Kourtney sat down on the edge of the bed. She opened her mouth up to take my cock back on it, sliding up and down the shaft.

I pulled my shirt off before I placed my hand on the back of Kourtney's head and took the top of her ponytail in it. I moaned and asked, "Do you like sucking my cock?" Kourtney nodded her head yes, and I asked, "How about when I do this?"

I tugged back on her ponytail to get Kourtney to stop moving her head and started to thrust my hips back and forth, sliding my cock in and out of her mouth. Down her throat I went, back out to her lips, and before slamming back down her throat, she went over and over.

I could hear Kourtney gagging around my cock as I face-fucked her and looked down to see her eyes begging me for more. I pulled my cock out of her mouth, grabbed it with my hand, and moved it all over her face before slapping her cheeks with my tip and shaft. "Do you like it when I fuck your face with my thick cock?" I asked as I kept sliding my cock all over her face.

"I like your cock everywhere," Kourtney moaned out.

"Then strip for me," I told her as I climbed onto the bed and laid down in the center of it. I wrapped my hand around the shaft of my cock and started to slowly rub up and down as I watched Kourtney stand up. She first peeled her scrub top off, leaving her in a black tank top. Her pants were next, revealing a black thong. She then removed her tanktop and black sports bra, squeezing her B-cup-sized breasts afterwards. Before climbing back onto the bed, she pulled the thong down her long, tan legs.

As she got closer to me, she leaned down to kiss me, lying on my side. I reached out for her groin, rubbing my fingers on her clean-shaven pussy. I pushed a finger inside her, causing Kourtney to moan into my mouth. I pulled and pushed my finger in and out of her as our tongues swirled together in our mouths. Kourtney climbed more onto me, swinging her leg over the side of me and leaning down until her breasts were pushing into my chest.

I removed my hand from her groin, moving it to her butt instead, as Kourtney reached between us and pulled the tip of my cock into her pussy. She slowly lowered herself down my shaft until I was buried deep in her. I grabbed her ass, squeezing her cheeks with both hands, as she slowly rocked her hips back and forth.

We both ended the kiss as she got more into it. Kourtney, propping herself up with her forearms next to my head, looked into my blue eyes with her hazel eyes and said, "Do you like fucking my pussy or my mouth more?"

I laughed and said, "How can I choose? I love how they both feel. I love the look on your face as I fuck it, but I also love your moans when I'm in your pussy."

Kourtney sat up more on me, using her hips to bounce up and down. I reached up, taking her breasts in my hands and squeezing a handful of them as Kourtney moaned louder. I used my fingers to pinch and rub her nipples before Kourtney sat up straight on my cock. I squeezed her breasts again as she rode me before moving my hands down to her hips.

After helping her hold steady and bounce on my cock for a few minutes, I moved one of my hands over to her groin and found her clit just above her clean-shaven pussy. I pressed my thumb on it, rubbing it in a circular motion, as Kourtney got louder and louder, bouncing on my cock harder and faster. I felt her pussy clenching around my cock as she came, her juices washing over it as Kourtney lost her balance and fell on top of me.

Her lips found mine, and we made out as she continued to rise and lower her hips. Ending the kiss, Kourtney rested her body on mine, her mouth next to my ear, with her hips barely moving up and down. I moved my hands to her butt, lifted my legs so they were bent on the bed, and started to thrust my hips up and down.

"Oh God, Danny. Fuck me," Kourtney moaned into my ear. I pushed her up off me, but when she went to lay down on her back, I grabbed her ponytail and moved her to her hands and knees. I kneeled behind her, grabbed my cock in my hand, and ran it up and down her ass cheek. "Are you going to stick it in my ass?" Kourtney asked me as I teased her with my cock.

Before I answered, I inserted the tip of my cock into her pussy. I let go of it with my hand and pushed it as I said, "Nope, not today." I grabbed onto her hips and started thrusting back and forth, making Kourtney moan as I pushed deep inside her. Over and over, harder and faster, I slammed into the beautiful, tall, skinny, fit woman that used to be my sister-in-law.

I reached forward with one of my arms and wrapped my fingers around the end of her ponytail. I slowly yanked back on it as I continued to pound her with my cock. I pulled back farther on it until Kourtney started to sit up on the bed, keeping her knees down but coming up until her upper body was touching mine. I reached around with my free hand and grabbed at her breasts, squeezing them and rubbing her nipples with my fingers.

"Oh, Danny, fuck me! Yes! Fucking play with my tits. Oh fuck, oh fuck, fuck!" Kourtney yelled out.

Kourtney tilted her head back until my mouth was next to her ear, and I said, "Is this what you wanted all weekend?"

"God yes," she said.

"Tell me," I said.

"I wanted your cock all weekend. I wanted it to slam into me. I wanted to suck it. I wanted to worship it," she said.

"Jessica was asking me if I wished that she let me cum on her like you let me cum on you," I told her.

"Did you cum on her?" Kourtney asked back.

"No, but I'm wondering about covering your face tonight and sending her a picture of it," I said. "Or, do you want it inside you? Your pussy? Mouth? Ass?"

"Oh God. Just give it to me. I don't care," Kourtney moaned out as I continued to pound into her. I let go of her breasts and used my grip on her hair to push her down onto the bed, back onto her hands. I kept the pressure on her hair, just enough so she could feel it and keep her head up, as I felt my orgasm beginning inside my body.

I told her I was close, but I wanted to hear her beg for it. "Oh fuck, Danny. Give me your cum. I need it. I crave it. Make my body yours. Fucking give it to me!" She yelled out until I pushed deep inside her, and my cock exploded, shooting stream after stream into her pussy.

I continued to pump in and out of her, pushing my cum deep into her, then pulling slowly out of her, a trail of cum extending from her pussy to her cock. Kourtney had her head down on the bed as I moved over to it. I reached down with my hands and took her head in them, lifting her up until her face was even on my cock. I rubbed her lips, cheeks, and nose over my cum-covered cock, spreading it around her face, until she opened up her mouth, stuck out her tongue, and licked it off me.

I laid next to Kourtney, who rolled over onto her back. "I think I'm leaking," she said with a laugh before looking down at her groin. I watched as she stood up from the bed and went into the bathroom. When she came out a few minutes later, she laid back down next to me, gave me a kiss on the cheek, and said, "Does this feel different to you?"

I asked what she meant, and she said, "Having sex now that we're both divorced.  No longer cheating or having to worry about being caught. Or does it feel the same to you?"

"I don't know. Aren't you worried about Kathy finding out?" I asked her.

"Yes and no. She doesn't trust me at all any more. I would like to fix our relationship. She doesn't hate me, by any means. But there is definitely something different about how she acts around me."

"Do you blame her?"

"No, not at all. I just hope that she can trust me again one day," Kourtney said.

"If she finds out you're still sleeping with me, it's just going to make it worse," I said.

"I know. But, why deny myself the pleasure?" She said this before rolling over and grabbing her phone. "I want to stay here all night, but I should probably get home. I'm surprised my mom hasn't called and asked where I'm not."

"I couldn't imagine having a thirty-year-old daughter living with me and calling and asking where she's at," I said as Kourtney got off the bed.

"Yeah, well, you know my mom," Kourtney said as she started to get dressed.

"Man, watching you pull on your scrubs reminds me that I need to get my teeth cleaned," I told her.

"If you want, I can schedule you an appointment next Monday," she said. "I can do it right before or after my lunch break, and we can go to lunch together if you want."

"Can we get the office to ourselves so that I can pull your scrubs down and fuck you? Because that's all I'm going to be thinking about," I said as I got up off the bed.

We wrapped our arms around each other as she finished getting dressed. Laying her head on my shoulder, she said, "Maybe. I'll see what times are available tomorrow and let you know."

"Seriously?" I asked as we let go and walked to the door.

"Yes. That's actually been a dream of mine. I might be able to time it so that you come in right as we're closing. I'll tell the doctor that you're family, and that's the only time you can come in. He trusts me enough to let me work in there alone, so he'll do his exam first, leave, then let me clean. And whatever else we want to do," she said before wrapping her arms around me again.

I moved my hands down to her butt as we hugged and squeezed her cheeks. "Oh, I think we'll find plenty to do," I said before we shared a goodbye kiss and Kourtney left my apartment. I walked over to my window, watching her climb into her car and drive off.

I spent the rest of the week texting Jessica non-stop. We called each other a few times, mainly at night, right before falling asleep. I kept telling her how nice it was to have somebody to talk to on a regular basis, and she agreed. She told me that she was hoping for a longer phone call on Friday after her son had fallen asleep, but wouldn't tell me why.

That night, I was sitting on my couch, playing a video game, waiting for Jessica to call me. She had texted me an hour before that she was getting Liam down and was excited to talk to me for a longer period of time. When she finally called, I noticed that it was a video call, so I sat my controller down and answered it.

As the video came on, I saw that Jessica was sitting in her bed. With her brown hair pulled back into a ponytail and a beautiful smile on her face as we both said hello, she was wearing a black tank top that showed off her C-cup-sized breasts and what appeared to be black and red shorts, barely visible as her five-foot-tall body sat crossed-legged on the bed.

"I hope you're OK with the video call and that I'm not interrupting anything," she said.

"I'll never mind a chance to see your beautiful face," I told her. "And you'll never interrupt me."

"What if I called while Kourtney was over?" She asked with a laugh.

I had told her about Kourtney coming over the previous Monday, and she hadn't stopped teasing me about it since. "I guess that would be a different story. I still might answer and let you listen to her moan," I replied back.

"I might just enjoy that," she said. We talked about how our day had gone, how work was, and plans for the weekend for the next little bit. When the conversation started to die down, Jessica said, "So, I did have another reason for doing a video call." I asked her what it was, and she said, "I've been horny all week and haven't been able to get last weekend out of my mind. And since we couldn't see each other this weekend, I had to think of the next best thing."

I was already moving to my bed as Jessica got a little shy on the phone. I asked her what the next best thing would be, and she asked, "Would it be weird if we masturbated over the phone together?"

I laughed and said, "No more weird than sending pictures back and forth or doing it over Marco Polo, like we've done before."

"I guess since you're moving to your bed, you want to do it?" Jessica said, and I replied back, "Jessica, I haven't stopped staring at your chest since you called me. And now you're telling me that I get to see them? I'm already growing hard."

"Show me," Jessica said, and I flipped the camera around as I laid down on my bed. I had already taken my pajama bottoms off, leaving me in just a t-shirt and boxers. The tip of my semi-hard cock was poking out through the hole in them, and I pulled my boxers down to expose myself. I watched Jessica's eyes on the phone light up as I wrapped my hand around my cock and rubbed it to its full six-inch length.

"God, I wish you were here," Jessica said, and I asked what she would do if I were. "I would have my hand and my lips around your cock. Blowing you and making you moan until you finished in my mouth. Here, let me help."

I watched on the phone as Jessica pulled her tank top up and over her head, tossing it to the floor. While holding her phone with one hand, she used her free hand to squeeze both of her breasts and rub her nipples with her fingers. I told her that did help, but I wanted more. She flipped the camera around, showing me her legs spread open, and moved her hand down to rub her groin through her shorts. She then hooked her fingers into the top of the shorts and pulled them down, showing her pussy off to the camera.

She ran her fingers through the little bit of hair around her vagina and rubbed the outside of her pussy lips. I kept my hand on my cock, slowly moving it up and down, as she inserted a finger inside herself and started pulling it in and out. "I wish this was your tongue. Or your cock," I heard her say.

"So do I," I replied back, picking up my speed on my cock as I rubbed it up and down. Seeing me go faster, Jessica did the same to herself and started to alternate between fingering her pussy and rubbing her clit. "I'm just thinking about how nice being inside your pussy is. Me making you moan as I pound my cock into you."

"Oh God," Jessica moaned as she played with herself, and I kept talking dirty to her.

Watching her slide her finger in and out, I said, "Next time we're together, it's going to be sex all the time. We won't ever put clothes on, and I'm never taking my hands off your body."

"Oh God, I want that so bad," Jessica said, rubbing her clit fast and furious. I asked if she was close, and she said yes.

"Move your camera so I can see your face," I told her. "I love to see it as you come."

Jessica flipped the camera back around and moved it down. She angled it so I could see both her face and her hand as she rubbed her clit. I told her that I was getting close too and watched as Jessica, her back arching off the bed, her eyes straining to stay open and on my cock, dropped her phone, moaning out, "I'm cumming. Oh Danny, I'm cumming!"

She picked up the phone a minute later, holding it up to her face, and asked, "Did I miss you coming?"

"No, but I'm almost there," I answered. "As hot as that was to watch you finish, will you show me your tits?"

Jessica smiled before flipping her phone camera around and showing me her breasts. I watched as she squeezed them, pinched her nipples, and said, "Cum for me, baby. Let me watch that cum shoot out of your cock."

"God, I never thought I would hear you say those words," I told her as I stroked my shaft.

"Me either. But, here we are, and I'm begging you to cum. I almost wish it was on me. I would rather it be in me. But, could you imagine covering my tits right now with your cum?" Hearing her say that sent me over the edge as my orgasm finally hit. The first rope of cum shot out of my tip, flying past my head. The second somehow landed on my phone's camera as I heard Jessica say, "Oh yes. There it is." The rest I pumped out slowly, and it landed on my groin and stomach.