Pleasing my Sister-in-law ch. 04

Kourtney was the first to talk and said, “So, Danny, I’m guessing this is a dream come true for you, right?”

I was lying in a hotel room bed. Two of my sister-in-laws, Kourtney and Jessica, were on either side of me. Kourtney just jacked me off, so I finished on Jessica’s breasts, and then we watched as she licked my cum off them. They had put on some clothes—just a thong and a tank top—and were still cuddling up next to me.

I told her it was a dream, and she said, “So, what would you like us to do next while we wait for your cock to recover?”

I thought about it for a moment, but before I could answer, Jessica said, “Unless he has another idea, why don’t we pull out our dildos? With me never using one, maybe I could learn some tips from watching you.”

I told them I liked that idea, and all three of us got up off the beds. The girls had their bags sitting next to each other, and I watched as they both bent over to retrieve the dildos. Admiring their asses as they were bent over, I compared the two. Kourtney’s, in a pink thong, was fit, athletic, and beautiful, with her Native American heritage giving her tan skin all over.

Jessica’s butt was a little bit thicker but still fit. With her wide hips, all I could think about was fucking her doggy style.

They came back to the bed with their dildos, sitting next to each other and comparing them. I sat down in a chair next to the bed so I could watch. Kourtney’s was black, thick, and had to be seven inches long. Jessica’s was a lot smaller, not very thick, and pink. Kourtney said, “You’ll love that one. I have one just like it and use it a lot.”

The girls laid down on the bed, pulled their thongs off, and me and Jessica watched as Kourtney spread her legs, lifting her knees up, and reached down with her arms to her pussy. With one hand, she rubbed her pussy, making sure she was still wet, then started to rub the tip of the dildo on her pussy. When it was wet enough, she spread her lips open, inserted the tip of the dildo, and moaned as she pushed it inside her.

“Wow,” Jessica said as Kourtney started to fuck herself with the dildo. Jessica matched Kourtney’s stance, lying flat on her back, knees up, and her legs spread. She moved her dildo up and down her pussy lips, getting it wet, then inserted it into her pussy. She let out a little moan as she pushed it all the way before pulling it back out. Soon enough, both girls were masturbating with their dildos, eyes closed, and moans coming out of their mouths as I watched.

Kourtney used her free hand to pull up her tank top, exposing her B-cup-sized breasts again. As she continued to fuck herself, she pinched her nipples, rolling them around in her fingers, and squeezed her breasts. She then reached back down with her hand and started to rub her clit, making a circular motion in it, until her back arched off the bed, her eyes opened, and she moaned loudly through another orgasm.

Hearing Kourtney orgasm, Jessica stopped playing with herself and watched Kourtney as she continued to slide the dildo in and out. Seeing Jessica watching her, Kourtney said, “Need some help?”

Jessica laughed and said, “I don’t even know what to say. This feels good, but you sound like you just went to heaven.”

Kourtney pulled the wet dildo out of her pussy with a pop and placed it on the table next to the bed. She watched Jessica play with herself for a moment, then said, “Here, do this.” I watched as Kourtney put her hand on Jessica’s and started moving the dildo in and out at different speeds, then said, “Now, pull up your shirt and pinch your tits.”

Kourtney let go of Jessica’s hand and helped her pull up her tank top. Jessica took her B-cup-sized breasts in her free hand, squeezing them and pinching her nipples. Still watching her, Kourtney said, “Now, when you feel like you’re getting close, reach down and start to rub your clit. I like to do it with two fingers on top and just make a circle with them. I know others that go up and down on it, and some just orgasm as soon as they touch it.”

Jessica nodded her head and did as Kourtney instructed. It took her a few seconds to find her clit under her hairy bush, but as soon as she started to rub it, with the dildo still going in and out of her wet pussy, she had a massive orgasm. Her pussy clenched around the dildo, forcing it out as her body shook. 

Watching Jessica come down from it, Kourtney said, “There you go.”

Jessica said, “Sorry, Danny, but knowing that, who needs a man?”

Kourtney laughed and said, “As good as that can feel, it’s still nothing compared to a man with a thick cock pounding into you.”

The two girls pulled their tank tops back down and their thongs back up. Still sitting on the chair next to the bed, I asked Jessica to join me. She sat on my lap and wrapped her arms around my neck, leaning in to kiss me as I wrapped my arms around her body.

Our tongues swirled together as I placed one of my hands on her butt, gently squeezing and massaging it. I heard Kourtney get up and go somewhere, but I was too lost in kissing Jessica to see where or what she was doing. Jessica was moving her groin on top of mine, almost like she was begging my cock to get hard again. She pressed her upper body against mine, and I could feel her big breasts pushing against my chest through our clothes.

We continued to kiss, me moving down to kiss her neck, sucking on her ear lobes, her exposed chest, and anywhere else I could reach, before going back to her lips as we passionately kissed. Both of my hands were on her butt now, lightly spanking her cheeks and using my grip on them to pull her into me.

After what felt like an eternity but was probably just a couple of minutes, we finally stopped kissing. I wrapped my arms around Jessica’s waist as she continued to rock her hips back and forth slowly on me, and we leaned our foreheads against each other.

Panting deeply, Jessica said, “That was hot.”

“Yeah, it was,” Kourtney said behind us, making me and Jessica jump a little.

“Shoot, sorry, Kourtney, we kind of got caught up there,” Jessica said, turning to see Kourtney sitting on the bed, eating a bag of chips. “Oh, that looks good. Anybody getting hungry, or is it just me?”

Me and Kourtney both said we were hungry, and Kourtney said, “The restaurant downstairs sells pizza. I was thinking maybe one of us could run down there and get one.”

“I can do it. Not that you and Danny need any more alone time, but I could use a quick break,” Jessica said, climbing off my lap. She walked over to her bag and clothes, pulling back on her jeans and boots, and putting her jacket on over her tank top. She waved bye to us after finding out what kind of pizza to get.

With Jessica gone, Kourtney came and climbed onto my lap, and we repeated what me and Jessica had just done, but Kourtney took off our shirts so our naked chests could press against each other. As we passionately made out, my hands roamed all over her skinny, fit body, squeezing her butt cheeks and her breasts, while my lips kissed hers, her neck, and everywhere else above her chest.

My cock was finally starting to grow again as Kourtney rubbed her groin on top of it. But, before it could finish growing, Jessica came back with our pizza, and Kourtney got off me, putting her tank top back on.

Jessica passed us each a slice of pizza, and we sat down and talked and ate. “I still can’t believe we’re doing this,” she said, sitting on the bed next to Kourtney.

“Right? Like, I’ve done this lots, but never with somebody I’ve known as good or long as you two, and never with another girl. It feels so good, so naughty, and so much fun,” Kourtney said.

“Seriously. I don’t want this night to end,” I told the girls.

We continued to talk as we ate, each of us eating a couple of slices, then cleaning up when we were done. Sitting back down in the chair next to the bed, the girls sat across from me, and we discussed what we each wanted for the rest of the night.

“So, I guess the main question we need to answer is, How long until Danny is ready again?” Jessica asked, glancing down at my groin.

Kourtney said, “He was starting to grow when we were making out, so I don’t think it’ll take much.”

“Nah, it won’t,” I told them then. “But I’m sure there’s something you two can do to help.” Then she asked what it was, and I said, “Kiss each other? Take off your tank tops and play with your tits? Something like that might help.”

The girls laughed, and Jessica said, “We told you, neither one of us was interested in stuff like that.”

She was immediately shocked when Kourtney said, “Actually, I would kiss you. And I’ve already touched your tits once, and I would do it again.”

“Wait, really”? Jessica asked her.

“Yes. And if you close your eyes, I wonder if you would be able to tell a difference between me and Danny,” Kourtney told her.

Jessica shrugged her shoulders and said, “If it gets Danny hard again, let’s try it.”

I sat up a bit in my chair and watched as the two girls leaned into each other. Kourtney placed her hand on Jessica’s face, pulling it towards her, and turned her head slightly to the left. As they both closed their eyes, their lips came into contact for the first time, and they shared a brief kiss before backing off for a split second. Going back into each other, Kourtney was attempting to make out, and Jessica’s hesitation quickly faded away, and they were kissing passionately in front of me.

As they kissed, Kourtney brought her free hand up and onto Jessica’s breasts, cupping them through her shirt. Jessica moved her hands down to the bottom of Kourtney’s tank top and started to pull up on it. They briefly broke their kiss, and Kourtney quickly took off Jessica’s tank top, leaving both girls naked besides their thongs as they continued to kiss for a few seconds longer.

Ending the kiss, Jessica let out a soft “Wow” as they leaned their foreheads together.

Kourtney laughed and said, “No kidding.”

They smiled and looked over at me, with Kourtney saying, “How was that? Get the job done?”

I said I was close and watched as Kourtney grabbed Jessica’s hand and brought it up to her breasts. Kourtney put Jessica’s hand on her right breast, right in front of me, and let go, letting Jessica squeeze her breast and rub her nipples. I saw Kourtney start to shift her body as Jessica rubbed her nipples and finally said, “Why don’t you two lay down and let me join?”

Both girls lay down on the bed and scooted up to the top of it. I climbed over Jessica to lay down in the middle of them, but I was on my stomach and they were on their backs. I first kissed Kourtney, my hands going to squeeze her breasts, before shifting over and kissing Jessica. While kissing Jessica, I moved my hand down Kourtney, over her flat stomach, and under her thong, instantly feeling her wet and warm pussy on my hand.

I inserted a finger into Kourtney’s pussy at the same time that my tongue slipped into Jessica’s mouth. I fingered Kourtney, pulling my finger in and out, being restrained by her thong, and listening to her moan next to me.

I stopped kissing Jessica and shifted over to Kourtney. I pulled my hand out of her panties and moved my other hand to Jessica. I traced down from her chest to her stomach and slipped my hand into her thong. As I started to kiss Kourtney, I slid my finger into Jessica’s wet pussy. Jessica moaned as I fingered her and made out with Kourtney.

Ending my kiss with Kourtney, I said, “Why don’t you take your thong off?”

While Kourtney bent down to pull her thong off her long legs, I moved back over to Jessica. Keeping my hand inside her thong and my finger inside her pussy, I leaned over her breasts and started to lick around her nipples, flicking my tongue around them, before sucking one of them in my mouth. I played with it for a second before moving to her other breast and giving that nipple the same treatment.

As I played with Jessica’s breasts, I heard Kourtney ask, “Should I take off Jessica’s thong?” I nodded my head, yes, and felt Jessica lift her back off the bed as Kourtney reached up and pulled Jessica’s thong down her legs. Having more room now, I was able to pull my finger out of her farther before pushing it back in.

Still playing with her nipples, I felt Kourtney reaching into my underwear and wrapping her hand around my semi-hard cock. Her other hand worked to pull my underwear down as she stroked me, eventually freeing my cock.

I kissed Jessica’s lips again, then asked her, “Are you ready?” She nodded yes, and I moved over, Kourtney letting go of my cock as I climbed on top of Jessica and settled in between her legs.

I reached down between us, grabbed my cock, and slid the tip of it into Jessica’s pussy. I let go, moving my hands up and placing them next to Jessica’s head on the bed, and pushed my cock the rest of the way into her. As I filled her with my thick, six-inch-long cock, Jessica moaned loudly.

I started to thrust my hips back and forth, going harder and faster, as Jessica moaned under me. I felt Kourtney get up off the bed as I pounded into Jessica over and over. I opened my eyes, looking down at Jessica’s breasts as they bounced wildly. Looking up at her face, I saw her eyes closed and her mouth slightly open as she moaned every time I buried my cock in her.

I saw movement out of the corner of my eye, and I looked over to see Kourtney sitting in the chair next to the bed. Her legs were spread open; she had grabbed her black dildo and was fucking herself with it as she watched me fuck Jessica.

I made eye contact with Kourtney as she slid the dildo in and out of her pussy. I smiled at her and said, “You like watching me fuck your sister-in-law?”

“Fuck yes, I do,” Kourtney told me.

“What do you like about it?” I asked. “My hard cock pounding into her? Her moans? Our groins slapping against each other?”

“All of it,” Kourtney responded. “The way her tits are bouncing as you fuck her.”

“Oh god!” Jessica moaned, wrapping her legs and arms around me as her pussy clenched around my cock and an orgasm washed over her body. I continued to jackhammer my cock into her over and over, harder and faster, as her entire body shook from the intensity of the orgasm.

When she was done, she moved her legs and arms from around my body and pushed me off, saying, “Sorry, that was intense! I need a break.”

I looked over at Kourtney and said, “Get up here and get on your hands and knees.” Kourtney did as I instructed, taking Jessica’s place as she got up off the bed. Kourtney got onto her hands and knees in front of me, and I swatted her butt cheeks with the palm of my hand, getting a yelp and a moan from Kourtney.

I kneeled behind her, admiring her fit butt and her engorged pussy lips in between her legs, and wrapped my hand around my cock. I teased the entrance to Kourtney’s butt with my tip before sliding it down and letting go as I inserted the tip of my cock into her pussy.

I placed my hands on Kourtney’s hips and pushed my six-inch-long, thick cock into her all the way. Holding myself in place for a few seconds, I slowly pulled back out to my tip before pushing back in slowly. I kept this up, in and out, building up my speed, until I was thrusting into and out of her at a steady pace.

I reached forward with one of my hands, taking Kourtney’s brown hair in it, and pulled back on it, causing Kourtney to lift her head off the bed and arch her back as I pounded into her. “Fuck yes, pull my hair. Harder!” Kourtney yelled out.

I yanked back harder on her hair, causing her to lift her hands off the bed. I reached around with my free hand, grabbing at her breasts, squeezing them, and rolling her nipples around in my fingers as I continued to pound into her over and over.

I looked over at Jessica, sitting on the chair next to the bed. She had grabbed Kourtney’s thick, seven-inch-long black dildo and was rubbing the tip of it against her clit. Kourtney saw her playing with it and said, “Are you going to try to take all of that in you?”

Jessica eyed it and said, “I don’t know. It’s bigger than anything I’ve ever had.”

“It’s not that much bigger than Danny is. I bet you’re wet enough to take it. If you want, it has a base on it, so you can sit it on the floor and lower yourself on it,” Kourtney instructed her.

As I slammed my cock into Kourtney over and over, I let go of her hair, letting Kourtney fall back onto the bed, and I slowed down a bit so we could watch as Jessica slid the first couple of inches of the dildo inside her, stretching out her pussy.

Instead of going in farther, Jessica pulled the dildo out and sat it on the ground. She sat on her knees just above the dildo, held onto it with one hand, and slowly inserted it into her pussy. Still fucking Kourtney, we both watched as Jessica slowly lowered herself into the seven-inch-long, thick dildo. Jessica moaned as it filled and stretched her, and the dildo disappeared inside her.

When it was all the way in, Kourtney asked her how it felt, and Jessica said, “It feels good, but I don’t know how long I could take it for. Honestly, I think Danny has the perfect dick size.”

Kourtney moaned out, “I agree,” as I picked up my pace, slamming into her over and over. Kourtney laid her head on the bed, one eye on Jessica, as she slowly raised and lowered herself on the dildo a few times before standing up. Jessica walked back to the chair after grabbing her own, smaller dildo and started to play with it while she watched me fuck Kourtney.

I felt Kourtney reach down with one of her hands and start to rub her clit as I pounded into her. She quickly brought herself to an orgasm, her legs nearly giving out, and I held her up from collapsing on the bed. 

After slamming into her a few more times as she finished orgasming, I pulled out of Kourtney, letting her fall onto the bed on her stomach. I stood up from the bed and walked over to Jessica while saying, “Do you want to taste Kourtney’s cum on my cock?” She nodded her head yes, and I said, “Open your mouth.”

Jessica sat up in the chair, her hand still sliding her dildo in and out of her pussy, and opened her mouth. I placed my hands on her head, holding her in place, and slid my cock into her mouth, bringing her nose to my groin. I felt her tongue moving around my cock as I started to pull out to my tip before pushing back down her throat. I kept thrusting my hips in and out, face-fucking Jessica, as she fucked herself with her dildo.

Pulling out of Jessica’s mouth, I asked her, “Where do you want me to finish? Your mouth or your pussy?”

Jessica looked up at me with lust filling her eyes and said, “My pussy.”

I helped her out of the chair as she dropped the dildo and moved her over to the bed. Kourtney scooted over as Jessica laid down, and I climbed on top of her. Sliding my cock back into her again, I was quickly pounding into her over and over.

I told her I was getting close, and both girls were begging me to finish. Kourtney was encouraging as she rubbed her clit next to me, and Jessica was under me, her moans filling the hotel room. As I felt my cock start to erupt, I pushed in deep to Jessica, the cum shooting out of my cock. I felt the insides of her pussy as they started to milk my cock, and I slowly pumped in and out of her before going limp.

As I pulled out of Jessica, I laid down between the two girls again. Jessica moved over and kissed my lips while saying, “Thank you.” I kissed her back and told her any time.

All three of us were laying down, not talking, just enjoying the after-sex feel. Jessica was the first to move, getting up off the bed and going over to her clothes. Kourtney asked her what time it was, and Jessica told her, “Almost eleven. Are you two going to stay all night?”

Kourtney rolled over next to me and said, “I wish. But only if you could stay too.”

As Jessica pulled on her clothes, she said, “I wish I could, but I don’t think I could take anymore.”

Me and Kourtney got up off the bed, both of us giving Jessica a hug and me giving her a passionate kiss, before Jessica opened the door and left. Turning back to Kourtney, I said, “I got to be honest. As much fun as this has been, I don’t know if I have any more in me either.”

“I know,” Kourtney said, walking over and hugging me with her naked body. “We can go if you want. Or, we can stay for another hour and just hang out. Your choice.”

She let go of me, turned around, and started to walk away. Putting one leg in front of the other, she was swaying her ass back and forth seductively. I watched as she picked up her thong off the floor, slipped her feet into it, and slowly stood up, pulling the thong up her long, tan legs.

Before she could grab any other clothes, I walked over to her, wrapped my arms around her waist, and pulled us both down onto the bed. We would spend the next hour kissing, touching each other’s bodies, and talking. Around midnight, we finally got dressed and left the hotel, with Kourtney dropping off the room key at the front desk and getting a curious look from the hotel clerk.

We walked out to Kourtney’s car, hand in hand, climbing in and driving off. Making the short drive back to my house, as we pulled into my neighborhood, Kourtney said, “Kathy is asleep, right?” I told her that my wife had been asleep for a couple hours and asked why.

Pulling her car into my driveway, Kourtney said, “Because I want to prove you wrong.” Before I could ask what about, Kourtney took off her seat belt, put her hand on my groin, leaned over the center console, and started to kiss me. Slipping her tongue into my mouth, Kourtney started to unzip my jeans, expertly pulling my semi-hard cock out of my pants.

Breaking our kiss, Kourtney looked down at my cock and said, “See? I knew you would have at least one more in you.” She started to kiss me again as her hand wrapped around my shaft and rubbed it up and down. I wrapped one of my arms around Kourtney’s body, bringing it down to her ass and resting my hand on it. With my other hand, I used it to open her winter jacket and squeeze her breasts through the green shirt she had on.

Kourtney adjusted in her seat as I grew harder in her hand, and I felt her shirt falling open. I slipped my hand inside the low-cut top of the shirt, moving it under her bra, and started to rub her nipples in my fingers. Kourtney was now moving her hand up and down the full length of my six-inch-long, thick shaft and ended the kiss to say, “I know you like to play with my tits, but you need to move your hand so I can blow you.”

I quickly removed my hand and watched as Kourtney leaned over, holding my cock with her hand at the base straight up, opened her mouth up wide, and swallowed my cock in one motion. She held herself in place, running her tongue around my cock inside her mouth, before starting to bob her head up and down with her hand following behind it.

I leaned my head back in the seat, enjoying the feeling of Kourtney’s lips wrapped around my cock. She was amazing at blowjobs, knowing when to go fast and when to slow, taking her mouth off, and using just her tongue to lick all over the shaft. She liked to just suck on the tip while her hand worked the shaft.

At one point, she laid her head down on my legs, her hand moving up and down, her brown hair brushed back over her shoulder, and said, “Next time we’re able to do this, I want you to fuck me in the shower. I want your cock in my ass, and when you’re done, I want you to cover me with your cum. My face, my tits, everywhere. I was so jealous when you came on Jessica today. I wish it was me.”

I opened my eyes as she talked and looked down at her. “You know, I could cover your face today.”

She smiled up at me and said, “As nice as that would be, I don’t want cum to accidentally get on my car. But, do you think we can make that happen?”

I told her, “I will do whatever you want me to do.”

“That’s what I thought,” she said as she once again wrapped her lips around my tip, flicking at it with her tongue before going back to bobbing her head up and down. I placed my hand on the back of her head, more to help guide her and pace her as she continued to blow me.

She once again took her mouth off and said, “I could blow you all night. I don’t know what it is about your cock, but, like Jessica said earlier, it is just perfect. The way it fills my mouth and how it feels in my throat. It’s just right.”

“Do you know what could make this more perfect?” I asked her. When she asked what, I said, “If you were naked. You think my cock is perfect; I think your body is. Fuck, looking at you is such a turn-on.”

She smiled and said, “Do you prefer my body over Jessica’s?”

I laughed and said, “You couldn’t make me choose. When you were both lying in bed, naked or not, my eyes couldn’t focus because they were moving from one to the next and back.”

Kourtney once again swallowed my cock whole, quickly bobbing her head up and down. She shifted how she was lying, so I could see the back of her head instead of her face. At the same time, she pulled her left arm out of her jacket sleeve, grabbed my hand, and placed it on her breast. I was quick to slide my hand into her shirt, placing it on her breast and massaging it while rubbing her nipple with my palm.

As I pinched and rubbed her nipple with my fingers, Kourtney pulled my underwear down more and exposed my balls. She gently took them in her hand and massaged them while continuing to bob her head up and down my shaft. She was moaning around my cock, causing it to vibrate as she took me deep into her throat over and over.

I felt my orgasm starting to build up and told Kourtney I was close. I grabbed her breast, holding it in my palm while she leaned up some, getting directly above my cock. She kept her mouth right at the tip of my cock while her hand worked my shaft. She felt my cock pulsating in her hand when I came and instantly deep throated me, working to swallow my cum as it shot out of my cock.

She made eye contact with me as I came, and when I was done, she took me out of her mouth and used her tongue to clean off my tip and my shaft before sitting back up in her chair. I pulled my underwear and pants back on while she slipped her arm back into her jacket sleeve. I leaned over the center console, wrapping my arms around her neck, and pulled her close for a hug and a kiss before getting out of her car and going into my house.

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