Pleasing My Sister-in-Law

In the weeks that followed me, Kourtney, and Jessica getting together at a hotel for a night of fun, I had conversations with both girls about how much fun it was and what we all enjoyed about it. Jessica came right out and said that, while she didn't mind it happening at the time, she couldn't see herself doing something with another woman involved ever again.

When I asked Kourtney about it, she said the opposite and that she would do something with another woman. I told her that if she finds one, she should let me know.

Surprising me one day, Jessica sent me a message that said, "I heard Kourtney blew you in her car after our night at the hotel." I told her that she did, and she said, "It made me remember the night I blew you in the backseat of my car while we were in Vegas."

I responded back to her, "So, let's have a repeat of it." When she asked how and when, I said, "I don't know, but let's start thinking of some ideas. I'm sure it's going to be something spontaneous and last-minute, but maybe we could figure something else out too."

We spent the next little bit throwing out ideas to each other. I wanted her to show up at my house at midnight or come to my work before everybody else got in. She wanted me to come to her house after her husband left for work or to rent us another hotel room. As we talked, our ideas got crazy and wild, but nothing concrete was put in place.

Although she had only been lukewarm to the idea, Jessica surprised me the following Friday when she messaged me to say, "Hey, so the high school I work at has an away basketball game tonight that will probably keep me out pretty late. What do you think the chances are that Kathy will be asleep and I could sneak over?"

I told her it would depend on how late it was, but we could try and see. The rest of the day, she spent telling me how she couldn't stop thinking of my cock, wanted it in her mouth, and really wanted that night to work.

My wife ended up falling asleep early that night, along with our kids. With the way our house was set up, the main floor being the living room, kitchen, and bedrooms, we had turned the basement into a play area, and I went down there a few times a week to play video games. As my wife fell asleep, I told her that I was going down there, to which she told me not to stay up too late. After she was asleep, I messaged Jessica that I wanted to give it a try.

She messaged back and said that she was on her way and was about twenty minutes away. We quickly made plans about what to do when she got there, and I settled down next to the window to wait for her.

Seeing her car coming down the road, I watched as she pulled to the side of my driveway, parking in a gravel area next to the garage. I quickly made sure that everybody was asleep in the house, stuck out the back door, and walked to her car.

Climbing into the passenger seat, Jessica, with a giant smile on her face, whispered, "Hey, I can't believe we're doing this! It's so dangerous!"

"I know," I said. "It's insane. As much as I want it to last, we better make it quick."

I looked over at Jessica and saw that she had her brown hair pulled back into a ponytail. She was wearing a black jacket that she took off and threw into the backseat to reveal a green polo with the name and logo of the high school she worked at. Jessica's job was an athletic trainer for all of their sports teams, so she was often gone from home at night a lot, a fact that we had talked about helping us get some time together.

The polo was stretched out over her C-cup breasts, and when she saw me looking at them, she said, "You probably won't be able to touch them during the blowjob like you did to Kourtney, but I figured you could still squeeze them through my shirt if you want."

I laughed and said, "I can't believe they let you wear that at a high school. I wonder how boys say they're hurt just so you'll get close to them."

"Probably a lot of them. I've caught a few staring. And I'm sure they've all dreamed of what I'm about to do to you."

Jessica slipped her hand inside the pajama bottoms I was wearing and wrapped her hand around my already hard cock. Looking up at me, she said, "That was quick. Must be excited."

"I've been resisting the urge to jack off for the last hour and started to get hard as soon as I sat down," I told her.

She had another giant smile on her pretty face as she pulled my PJs down enough to be able to pull my six-inch-long, thick cock out. Keeping her hand wrapped around it, she leaned over the center console of the car, wrapped her lips around my tip, and started bobbing her head up and down my shaft.

Jessica had a little trouble getting me all the way down her throat, so she settled on her mouth working the first few inches of my cock and her hand working the rest of it. The double stimulation felt great, especially when she would pause at the top of my cock and swirl her tongue around the tip of it. I reached under her, using my hand to grab at and squeeze her breasts. I don't know how much pleasure she could feel from it, but she started to moan around my cock.

As she kept blowing me, bobbing her head up and down, I looked down at her body. Being only five feet tall, she was able to kneel on the driver's seat, and I could see her polo riding up her back and showing a little hint of skin on her back and wide hips. I moved my hand from her breasts and over to the exposed skin of her lower back. I could just make out a hint of the underwear she had on and trace it with my fingers before rubbing her back.

As Jessica felt me touching her back, she leaned forward in the seat more, getting a little bit more of me in her mouth. I slipped my hand inside her pants and underwear and squeezed her buttcheeks, which caused Jessica to moan even louder around my cock.

I had to remove my hand from her pants when my orgasm started to build up and my hips started to push up, trying to get my cock deeper into her. I warned her that I was close, and she used her hand on the full length of my cock, leaving her mouth at the tip. When I started to cum, she pumped up and down, shooting my cum to the back of her mouth.

As I finished, Jessica sat up in her seat and surprised me when she grabbed her phone and turned on the camera. She opened her mouth to show the camera the cum that was in her mouth and took a picture of herself before swallowing the cum. Seeing my puzzled look on my face, she said, "It's for Kourtney. I'm going to send it to her and make her jealous."

I laughed as I pulled my pajamas back up and said, "I wish I could return the favor."

"Me too, but you need to get inside before Kathy wakes up. Maybe when I get home, I'll send you a picture of my tits since you didn't get to touch them tonight," she told me.

I told her that only if she wanted to before giving her a hug and a kiss and leaving the car. I quickly walked back inside my house, made sure everybody was still asleep, and went back to playing my game. When Jessica arrived home twenty minutes later, she sent me a message asking if I was still awake, and I told her I was. She then said, "Alright, give me a few minutes, and I'll have something special for you."

I was just expecting a picture of her bare breasts, so I was shocked when the next message I received was a video. I opened it up to see Jessica, completely naked, sitting in her bathroom. She had pulled her ponytail out, so her brown hair was loose around her face. Her C-cup-sized breasts were exposed, her nipples were already hard, and she was sitting with her legs spread. She moved the camera down to show me that she was sliding her dildo in and out of her hairy pussy.

The video was a minute long, and it ended after she had an orgasm, using her free arm to cover her mouth as she came and her legs squeezing shut around her hand and dildo. Along with the video, she wrote, "I was so horny when I got home; I just had to play with myself! Thank you for letting me come tonight."

I responded back, "I think I should be thanking you. A blowjob and that video just made this night amazing."

We talked a few minutes longer that night before going to sleep. I had a dream that night that I fucked Jessica in her own bed and wanted to tell her about it. But, with it being the weekend, I had to wait until Monday to make sure her husband didn't see it. That Monday morning, I typed out everything I could remember about the dream and sent it to her.

"OMG! I can't believe you had a dream about me. That's so hot! I'm wet after reading it. We're going to have to make that dream come true!" She responded back. I told her that I really wish we could, and she said, "Actually, I was going to talk to you about that today. Jack is going out of town this weekend. And my parents have been begging to watch my son. If we can find a way to get you free, we could do it," was what Jessica wrote back to me.

"That would be great! Hopefully, I can get away. Did you send the picture to Kourtney? What did she say?" I asked her.

"Yeah, I did that night so she could see it when she woke up. She said she was jealous," Jessica responded.

Unfortunately, I couldn't get away that weekend, and we couldn't find any time for the next month. Kourtney did manage to sneak over to my house once, while my wife and kids were at her house, but, unfortunately, she was on her period, and she could only give me a blowjob.

One Tuesday night, my wife answered her phone, and I heard her mention my name and that she would ask me about it. When she hung up, she said, "So, that was Jessica. She wanted to know what we were doing this weekend. I guess she had a street team event up in Pocatello, and Jack can't go with her. So, she was asking if one of us wanted to go. It'll be around $500, but one of us would be gone all weekend. I told her I'd ask you since you know more about cars than I do."

Jessica, in addition to working as an athletic trainer for the high school, had been working as a member of the Ford Street Team since high school. They would go around to different fairs and other events, set up a bunch of new cars, and let people test drive them.

"She said that they just need somebody to hand flyers out to people at the booth and direct them where to go--nothing too difficult. Are you wanting to go? We could use the money." My wife finished telling me. We talked it over some more, trying to decide if my wife could handle the kids for a couple of days. We finally decided that the money would be nice, and I called Jessica to get the rest of the details and tell her I would do it.

The fair in Pocatello was that Saturday and Sunday. We would drive up there Friday, be at the fair all day Saturday, a few hours on Sunday, and drive home that Sunday night. Jessica did warn me that with the late notice of it, we would have to share a hotel room, but it did have two beds. Oh darn.

That Friday, Jessica came to my house just after six p.m. to pick me up for the two-hour drive to Pocatello. After saying goodbye to my wife and kids, I put a bag full of clothes and other necessities in the backseat of her SUV and climbed into the passenger seat next to her.

We made small talk as Jessica drove to the freeway, but as soon as she got onto the freeway, she said, "So, what should we do tonight? Should we get some food before we check into the hotel? Or after? I'm down for whatever."

"We should probably get it before. We never know what could happen once we get to the hotel," I said.

"True. We have a long day tomorrow, so we should be sure to get plenty of rest tonight," she said.

"Definitely. By the way, I was going to tell you, if you're getting ready and don't feel comfortable with me there, just say so, and I can go down to the lobby for a little bit," I said.

"Oh, thanks, Danny. I appreciate that. I feel comfortable enough around you to know that you won't try anything inappropriate," Jessica said with a little laugh.

"Oh yeah? Like what inappropriate things? I want to make sure I don't cross any lines," I asked.

"You know what I mean. Looking, touching, or anything that you shouldn't do," she told.

"Oh, so I shouldn't look at your butt?" I asked, and she said no. "Or try to sneak a peek as you get out of the shower?" She said no again. "I can't watch you get dressed or undressed."

"No, Danny, that would be totally inappropriate," Jessica responded.

"No, being totally inappropriate would be stripping you naked, fucking your tits, giving me a blowjob, and finishing in your pussy. And really totally inappropriate would be doing it all weekend," I said.

Jessica laughed again and said, "You have no idea how excited I've been the last couple of days. I can't believe this is actually happening and that it worked." I asked what worked, and she said, "Getting you to come. When Jack said that he had to go into work tomorrow and couldn't come with me, I asked about getting a replacement, and you were the first person he suggested. I figured I would ask Kathy too, so she didn't get suspicious that I was asking you, but she said I should ask you as soon as I said what I needed."

"So, are we actually going to do any work tomorrow?" I asked.

"As much as I would like to stay in the hotel room with you all weekend, we do need to do the full shifts at the fair to get paid. But we still have the nights to ourselves," she told me.

"Having a few nights with you will be worth the long day," I said.

"I hope so. I have a few surprises for you too," she said. I asked like what, and she said, "You'll see. Let's just say that me and Kourtney went shopping this week."

We stopped at a drive-through for some food as we arrived in Pocatello before going to check in at our hotel. I helped Jessica bring her bags up to our room, where we quickly ate our food. Both of us were thinking about what was to come.

As we cleaned up our dinner, I looked over at Jessica. It was still chilly outside, just being early March, so she was wearing a red University of Utah sweater that hid her C-cup-size breasts. Her brown hair that went down past her shoulders was pulled into a messy bun on the back of her hair. Around her wide hips and thick butt, she had on blue skinny jeans. She saw me looking and said, "You look like you have something on your mind."

"You're on my mind," I told the five-foot-tall girl as we both stood up, me nearly eight inches taller than her.

She moved her hand up, brushing some of my shaggy brown hair out of my eyes, and said, "What about me?"

"I was just debating how to get you how I want you," I told her as we got closer to each other.

"And how do you want me?" She asked me.

"Naked, on your back, with my cock in you," I said.

"And how are you going to get me like that?" She asked.

"That's what I'm debating on. Pretty sure I'm going to start to kiss her, slowly pull off our clothes, make you cum, get your hair out of that bun, then lay you on the bed, and make love to you the rest of the night," I said as I wrapped my arms around her.

"That sounds nice," Jessica said, resting her head on my chest. "What's the alternative that you're debating?"

"Pulling your pants down, pushing you up against the bed, and fucking you fast and hard," I said as I started to rub her back and brush my hands against her butt.

"So, a lot like what happened when I first joined you and Kourtney? That sounds nice too, but just so you know, you'll only see one of the surprises I have for you when you take off my shirt," she teased me.

"The first option it is then," I said, kissing her forehead. Jessica looked up at me with a smile on her face as I leaned down and started to kiss her. Leaning up on her tippy toes to kiss me back, we slowly made our way to the bed. I broke the kiss to pull my shirt off over my head, then leaned down to start kissing her neck while tugging on her sweatshirt. Once I had her sweater off, Jessica pulled off the white shirt she had on under it.

All of the bras I've seen Jessica wear so far have been pretty plain. White or black, and a full, padded cup covering her entire breasts. This bra was different. It was red. It only covered the lower half of her breasts. It wasn't padded, and the upper part of it was a see-through lace material.

Jessica saw my eyes go wide at the sight and said, "What do you think?"

"It's hot," I told her, bringing my arms up her side to cup her breasts and squeeze them.

"Me and Kourtney thought so too," Jessica said, letting out a soft moan.

"So hot that I might just keep it on longer," I told her as I leaned down to kiss the exposed skin on her upper breasts. I wrapped my arms around her now-naked waist, picked her up, and gently sat her down on the bed. I went back to kissing her lips while my hands went down to her jeans. I unzipped them, and she lifted her hips off the bed while I pulled them down. I ended the kiss and kneeled on the floor to finish pulling her jeans off.

I quickly got her underwear off and started to kiss her inner thighs. Jessica moaned as I brushed past her pussy. I noticed that she trimmed down the hair around it, as the lips of her pussy were more exposed. I started to lick the outside of it with my tongue before running my tongue up and down the little slit of her mound. I stuck my tongue in her, gently probing around. I looked up to see Jessica, resting on her hands but looking down at me.

I darted my tongue in and out of her and brought one of my hands up to join it. I used my fingers to rub her clit, getting it enlarged, then switched and used my finger inside her pussy, pulling them in and out, while I wrapped my lips around her clip, sucking on it and running my tongue across it. It didn't take very long before Jessica was moaning that she was coming, her arms giving out on the bed as she arched her back, forcing her groin into my face, and covered my mouth with her juices.

I stood up from the floor, used my shirt to wipe my face, and looked down at Jessica. Her upper body was lying flat on the bed, breathing heavily, her chest going up and down as she did, her feet still on the floor with her legs spread, and her wet pussy exposed. I was hard in my pants, and I made eye contact with Jessica as I undid my pants and lowered them down my legs. She was eyeing my cock in my underwear, licking her lips when I exposed it.

I grabbed onto Jessica's legs, lifting them off the floor. I held onto the right leg, and she kept the left leg up, and I stepped closer to her until my cock was touching her groin. With my free hand, I wrapped it around my shaft and put the tip of my six-inch-long, thick cock into her. Letting go of myself and again grabbing her leg, I pushed in deep.

"Oh my God!" Jessica screamed as I bottomed out inside her. I asked if she was OK, and she said, "Yes, I've just never felt that before. I feel like you're bigger and deeper than you've ever been."

I just smiled as I pulled out to my tip before pushing back in. Still holding onto her legs, her feet resting on my shoulders, I worked up to a steady pace of slamming into her over and over. I watched as she closed her eyes, her mouth open so she could moan, her fingers grabbing at the bed sheets, and her breasts bouncing in sync inside the bra.

"Yes. Yes. Oh, my god. Danny, this is amazing!" Jessica continued to loudly moan as my cock repeatedly pushed deep inside her.

When I couldn't stand any more, I pulled out of Jessica and let go of her legs. I climbed up onto the bed with her, kissing her lips again as we shifted over so we were both in the center of the bed. With me in between her legs, my cock easily slipped back inside her, and I resumed pounding into her over and over.

"Do you want me to ride you?" Jessica asked me.

I started to nod my head yes, but quickly switched to shaking it no. My orgasm hit without any warning as I moaned loudly, pushed in deep, and filled her with my cum. I leaned down, kissing Jessica passionately, as I pumped my cock in and out of her, cum shooting out with every thrust in.