Pleasing My Sister-in-Law

"I don't know." Jessica said, wiping a tear out of her eye. "All I could think about was you and being with you."

My heart skipped a beat, and thoughts of running away and spending the rest of my life with Jessica filled my mind. Raising a family, growing old, everything. I must have had a confused look on my face because Jessica said, "I mean, to sleep with tonight. I got a call after you guys left, and, with my high school work done for the year, the Ford Street Team is asking if I can spend next week up in Wyoming going to two different events. It's a lot of money, so I said yes. But, now, I'm going to miss our little get-together next week."

Trying to think through what she just said, I just said, "Oh."

"Oh?" Jessica questioned me.

"Yeah. Sorry, for some reason, when I saw you wiping at your eye, I thought maybe you were thinking something else. That's awesome, but I will miss you next week," I said as we started to walk towards Jessica's apartment building.

"What? Did you think I meant that I wanted you to leave Kathy, move in with me, and be mine forever?" Jessica said it with a laugh. I laughed too as we got to the door of her building and gave Jessica a hug and a kiss goodbye.

Once I got home, my phone went off with a text message from Jessica. It read, "Hey, all that I said about wanting you to run away with me... I hope you know that I would never expect that or ask it of you. But I can always dream."

That Sunday, I was sitting on my living room couch with my wife, Kathy. The kids were asleep, and we were enjoying a rare quiet night together, cuddling together and watching a TV show. When the show ended, Kathy leaned up, kissed my cheek, and said, "Now what? Kids are asleep, and it's still early."

I smiled down at her and said, "I'm sure we could find something fun to do," and I started to kiss her lips. I brushed her brown curly hair out of her face as we kissed, and she adjusted up so that she was no longer laying on the couch and was now sitting on it. I moved my hand from around her back to her front and cupped one of her double-D breasts with it.

I started to kiss her neck as she said, "Those would be more fun to play with if my shirt was off."

I said, "Your shirt would be easier to get off if you were on my lap."

Kathy got hit and climbed onto my lap with her legs straddling me. As we kissed, I pulled her shirt and bra up and off over her head, freeing her breasts. I cupped them both in my hands, squeezing them, before leaning my head down and licking around her left nipple. I rubbed the right nipple with my fingers as I licked and sucked her left nipple, before switching and doing the same to the right nipple.

I was growing hard in my pants, and Kathy started to rock back and forth on them. She moaned out, "Are we going to make it to the bedroom?"

I laughed and said, "Nope, let's just do it here."

Kathy said OK, standing up off me and pulling her pants and underwear down and off as I pulled mine off, leaving us both naked. Kathy took my hard, six-inch-long cock in her hand, rubbing it up and down a few times before she climbed back onto my lap and slid it into her wet, hairy pussy.

She started to roll her wide hips on top of me as she pulled my shirt off me, saying, "You don't need this anymore." She wrapped her arms around my neck as she rode me, pressing her breasts and nipples into my chest.

I kissed her neck and placed my hands on her butt, helping to hold her to me. Kathy was moaning in my ear, telling me how good it felt, as I pushed my hips up, pushing my cock deeper inside her. She started to bounce harder and faster, pushing me down into the couch, moaning louder as she orgasmed.

Falling on top of me, she said, "Oh my gosh, I hope I didn't wake the kids. I need to get off. Do you want to stay in here?"

I told her yes and helped her down to the floor. I leaned her upper body over the ottoman in front of the couch, kneeled behind her, and slid my cock back inside her.

"Oh, this is new," Kathy said as I started to thrust in and out of her. As much as I loved her and enjoyed sex with her, as I was pounding my cock in and out of her, my mind started to drift, and I started to think of having Jessica in the same position. Then I thought of Kourtney, picturing her fit ass with my thick cock in it.

I was trying to put my focus back on Kathy, but instead my mind went to her youngest sister, Katie. I thought of having her naked body under mine, and I could instantly feel my orgasm building up. As I remembered how Katie moaned the one time I had fucked her, I started to orgasm, pushing deep inside Kathy and sending my cum into her pussy.

"Oh, baby, that felt good," Kathy said as I finished. I helped her to her feet, we grabbed our clothes, and we walked to the bedroom, kissing the whole way.

The next day, I texted Jessica in the morning as she left for Wyoming, telling her that I hoped she had fun, to call me if she needed anything, and that I would miss her. She texted me that she would miss me too and couldn't wait to get back.

For some reason, I couldn't stop thinking about Katie that day. After a few hours, I sent her a text to see how she was doing. She responded back, "Hey! I'm OK. I'm going through a lot at work, but it's all good."

"Are you working today?" I asked her.

"Not until later this afternoon. Why?" She responded back.

"Just curious. What about tomorrow?" I said.

"I'm off all day tomorrow and the rest of the week. They've only been working me Sundays and Mondays," she texted back.

"That sucks. But it might work in our favor. Kyle still working during the day?" I said.

"Yes, he usually works until six every night. Why?" She said.

"Because I'm going to come over to your house after work one of these days and fuck you," I finally said.

"Oh, that sounds awesome. Just say when," she said.

Thursday was my wife's day off from her work, and I texted her during the day that I was going to work a couple hours of overtime that day and not go to the gym that night. I hated to lie to her, but I also really wanted to fuck Katie. I texted Katie that I would be over that day, and she said she was really excited. We spent the rest of the day texting, and by the time I got off work, she said that she was soaking wet.

As I drove to Katie's house after getting off work, I was already starting to grow hard in my shorts. I had given her some specific instructions that I wanted her to do for me, and she had agreed to them.

She opened up the front door to her house, hiding behind it as I walked in. I said hi to her as I walked past, and she told me how to get to the bedroom and waited for me to call her. Once I sat down on her bed, I told her she could come in and let out a "Wow" when she walked in.

Since I had last seen her, Katie had dyed her blonde hair a dark red color. She had a bit of a curl to it today, leaving it loose around her head but pinned behind her ears.

She was wearing a black spaghetti-string tank top with no bra, the cleavage of her C-cup-sized breasts sticking out the top of it. It was tight around her body, almost like it was a size too small, and showed her midriff off. I told her to spin around, and she slowly did so, showing me the black thong I had chosen for her to wear. Her butt wasn't as fit as Kourtney's or Jessica's because Katie had a little bit of meat on her body, but it looked good in the thong.

After she turned back around to face me, I said, "Now, come blow me."

Katie walked towards where I sat on the edge of the bed, kneeling down on her knees in front of me between my legs. She reached up with her hand, rubbing my cock through my shorts, feeling how hard it already was. I lifted my hips up as she pulled my shorts and underwear down, watching as she moved out of the way as she pulled them off my legs.

She wrapped her hand around my thick, six-inch-long cock, rubbing up and down my shaft as she opened up her mouth and sucked the tip of it into it. She swirled her tongue around the tip before slowly sliding her mouth down the shaft of my cock, her hand going down right in front of it. Looking up at me with her gorgeous blue eyes, Katie moved her head and hand back up to the tip of my cock, then back down, working up to a steady rhythm of bobbing her head up and down, with her hand following at the same time.

"You know," I started to say. "I know we agreed that this would be a one-time thing, but I might need another blowjob like this one day. You're fucking amazing."

Katie smiled and moaned around my cock. She picked up the pace of her hand, switching up her mouth, teasing my tip more before deep throating me. After a few minutes, I said, "Alright, stand up and strip for me." Katie kissed the tip of my cock as she took me out of her mouth, then licked off the pre-cum before standing up off the floor.

I watched as she pulled her tanktop off, revealing her C-cup-sized breasts to me. I wrapped my arms around her waist, pulling her on top of me, and said, "Actually, leave the thong on for now." I leaned forward, using my tongue to lick around her left nipple, then her right nipple. I moved my hands down to her butt, gripping her cheeks on them, and started to move her body back and forth, rubbing our groins together.

"Oh fuck, I love how big you feel," Katie said as her pussy pushed against my cock. "I really want you in my ass." I continued to suck and lick her nipples, only pausing when I spun us around to lay Katie down on the bed. I quickly pulled my shirt off before lying back down on her, kissing her lips as I pushed my cock into her thong. After the kiss ended, I kissed down to her neck, then her chest and her stomach, ending with my face in front of her groin. I used my fingers to move her thong to the side, exposing her clean-shaven, wet pussy to me.

I ran my tongue up the slit between her pussy lips, tasting her juices for the first time, before I pushed my tongue past them and inside. I licked around her insides, causing Katie to moan above me, darting my tongue in and out of her before finding her clit with my mouth. I briefly swirled my tongue around it, sucked it into my mouth for a few seconds, then kissed my way back up her body. Her stomach, both nipples, and all around her neck got kisses before I ended up back at her mouth. I pushed my tongue past her lips, passionately making out with her.

As we kissed, Katie reached between us with her hands. She used one hand to move her thong out of the way while the other hand wrapped around my cock and pulled the tip of it into her wet pussy. As she let go and brought her arms back up to above her head, I pushed in with my hips, sliding my cock inside her tight pussy.

We ended the kiss as I started to pull back out of her, then pushed in. Like her blowjob, I worked up to a steady pace, thrusting my hips in and out of her and slamming my cock into her pussy over and over. "Oh, fuck yes, this is amazing!" Katie moaned out. "Fuck, you feel so fucking good!"

I started going harder and faster, placing my hands on both sides of her and pushing myself above her as I pounded my cock into her. I looked down at her, her breasts swaying, her mouth open, her eyes closed. I used my hands, one at a time, to grab and squeeze the breast closest to it, using my fingers to pinch her nipples, making Katie moan louder.

"You like my cock in you?" I asked her.

"Oh yes. It's even better than I had dreamed of," Katie responded.

"Do you want to ride it?" I asked, and Katie said yes. I got off her and laid down on the bed as she threw her leg over me, her hand reaching down to slide my cock back into her. She put her hands on my chest as she started to bounce up and down, harder and faster, saying "fuck" every time my cock pushed deep inside her.

I was encouraging her to go harder and faster, spanking her ass and reaching past her arms to pinch her nipples. As I grabbed both of her breasts, squeezing them with my hands, Katie threw her head back, yelling, "I'm coming! Holy fuck! Oh yes!" Her already tight pussy got even tighter as it clenched around my cock, and she had to get off me as she orgasmed, falling down on the bed next to me.

Katie was lying flat on the bed, catching her breath, but I didn't give her any time as I quickly climbed on top of her. Spreading her legs open, I could see her juices coming out of her pussy as I lined my cock back up with it. Sliding inside, Katie let out another moan as I filled her up again. I was practically sitting on her as I thrust back and forth slowly, enjoying the feeling of her tight pussy.

Placing her hands under her head as she rested prone on the bed, Katie looked back at me and said, "What do I have to do to get your big cock inside my ass?"

I smiled at her and said, "If I'm this tight in your pussy, how tight is your ass going to be?"

"That's what I want to find out. Cum in my ass today, and I'll never turn you down for a blowjob," she said back. As I continued to pound her pussy, I spanked her ass again before she said, "There's lube in the drawer next to us. And I was wearing a butt plug most of the day, so I should be ready for you. And I'm wetter than I've ever been before. Please, just stick it in my ass!"

I reached over to the drawer as my cock slipped out of her pussy. I pulled it up to find an assortment of different sex toys, lube, butt plugs, and, I'm pretty sure, a few bags of weed. I grabbed one of the bottles of lube out, squirted some on my hand, and rubbed it up and down my shaft. Katie grabbed the bottle from me, got some of the lube on her hand, and rubbed it around her asshole, including sliding her finger inside it.

When we were both ready, Katie laid back down, reaching behind herself with her arms, and she used her hands to pull her butt cheeks apart so that I could see the hole she wanted me in. I kneeled behind her as she put her knees up on the bed, lined my tip up at her ass, and slowly started to push in.

After my tip broke through her, Katie let go, saying, "Oh fuck." Every inch I pushed farther in, she kept saying, "Fuck. Oh fuck. Fuck. Fuck. Oh, fuck yes."

Once I was all the way in, I held myself in place, feeling the incredible tightness of her ass as my cock filled it, and asked if she was OK. Katie responded, "Yeah. It hurts a bit. But it also feels good. Just go slow at the start."

I slowly pulled out to my tip before pushing back in, with Katie letting out a long moan as I did so. I continued to slowly push and pull in and out of her ass, trying to go just a little harder and a little faster each time, until I felt like I was at a decent speed. With how tight it was, I knew it was going to last long, and I asked her, "Are you sure you want me to finish in her?"

"Yes," Katie said. "If you're close, you can go as hard as you want. I can take it."

With that blessing, I put my hands on her hips and started thrusting as hard and fast as I could, with Katie nearly screaming as I did so. When my orgasm started, I pushed her down on the bed, my cock going as deep as it could in her ass, and yelled out, "Oh fuck yes," as the cum erupted out of the end of my cock. I stopped moving as cum shot out until I finished coming and started to go limp inside her.

When I pulled out of her, I got up and went to find a bathroom, cleaning my cock off in it. Going back into the bedroom, I found Katie sitting up on the bed with a satisfied look on her face. As I grabbed my clothes, I said, "You look happy."

"Yes. I am. That was honestly so amazing. Did you enjoy it?" She asked me, getting up off the bed.

"Of course," I said, wrapping my arms around her waist and pulling her naked body toward me. "It was great. And now, every time I see your ass, I'm going to think of how my cock felt inside it."

We shared another kiss before I left her house. Sitting behind the wheel of my car for the first time since this all started, a wave of guilt hit me. But I wasn't feeling it for my wife. Instead, it was for not doing this with Jessica.

I sent Jessica a text as soon as I got home that day, telling her how much I missed. She sent back that she missed me too and wished she could see me when she got home on Sunday. I told her I was hoping for that too.

Instead, I ended up having to wait until that Thursday. As soon as me and Jessica saw each other at the gym, we hugged and kissed, holding each other's hands as we walked around the gym. With us not being able to focus on anything, Kourtney finally looked at me and Jessica and said, "You know, just because me and Danny waited thirty minutes last time doesn't mean you should do it. You can go back to the apartment and fuck; I promise I won't tell."

Me and Jessica laughed and said OK before saying goodbye to Kourtney and leaving the gym. We quickly walked across the street to her apartment building, holding hands as we made our way up the elevator and into her apartment. Once there, we wrapped our arms around each other in an intimate embrace, holding close and tight.

After a few minutes and us telling each other how much we missed each other, Jessica looked up at me and I looked down at her. We grazed into our eyes before moving our heads until our lips met and we began to kiss. I moved my hands down to her butt, grabbing onto her cheeks through the running shorts she had on and lifting her up. She wrapped her legs around me as we continued to kiss, and I walked us into her bedroom.

Once there, I sat Jessica back down on the floor, and she ended the kiss by sitting on the edge of the bed. Pulling me close to her, Jessica grabbed onto my shorts and pulled them and my underwear down to my ankles, where I kicked them off. I took off my shirt while Jessica wrapped her small hand around my growing cock and began to rub it up and down.

"I think I dreamed of your cock every night while I was gone," Jessica said, licking her lips.

I looked down at the beautiful girl. She had her brown hair in a braided ponytail, going down her back. Wearing a blue workout shirt with a low cut to it, I glanced down at the cleavage of her C-cup-sized breasts before going back to looking at her face. Jessica opened up her mouth as I finished growing to my six-inch-long length and wrapped her lips around the tip of my cock.

She slid down my shaft the few inches she could get into her mouth, using her hand on the rest of my shaft. She bobbed her head up and down a few times before taking me out of her mouth and saying, "Does it make you sad that I can't deep throat you like Kourtney can?"

"Hell no. This still feels just as good," I told her.

"Whatever. I know how much you enjoy having your entire dick sucked. But I can do something Kourtney can't," she said. I asked what that was and watched as Jessica let go of my cock and took off her shirt and bra. She sat up a little straighter on the bed, placed the tip of my cock at the top of her breasts, and used her hands to pull her breasts apart. As my cock fell between them, she pushed them closed, covering my shaft with them.

Jessica started to move her body up and down, sliding my cock between her breasts. "You're right; Kourtney could never do this," I said.

"Does it feel good?" Jessica asked me, and I told her it did. "Good," she said, making her bed squeak as she bounced on it, jacking me off with her breasts.

After a few minutes of my cock between her breasts, I started to pull up on Jessica's arms, and she stood up off the bed. I kneeled down on the floor in front of her, pulling off her shorts and underwear, before we both climbed onto the bed. I laid down on top of her, us kissing again, feeling her breasts against my kiss. My cock was trying to slip inside her pussy, but I started to move down before it could.

I stopped at her breasts, sucking and licking, pinching and rubbing her nipples as she moaned. I kissed down her flat stomach until I got to her groin. I slide my tongue up and down the slit of her pussy lips, darting my tongue in and out, while using my fingers to rub her clit.