Pleasing My Sister-in-Law

The Friday after I had taken Hannah's virginity, I was on the phone with Kourtney as she got ready to go watch a friend that she met sing at a local music venue. We were on a video call as she showed me different outfits she was thinking about watching.

As I watched her change, going from a blouse with a bra to pulling off her bra and blouse and putting on a dress, to no dress, back to a bra and a shirt, she kept the same black thong on, and I could feel my cock growing as I checked out her body.

"I think you look great in whatever you put on," I told her. "Personally, no shirt or bra and no dress are working for me. Just stay in the black thong and only that."

"Oh yeah? Is it turning you on to watch me change? You're supposed to be helping me pick out an outfit," Kourtney said as she looked through her closet.

"I know! But I can't help it when you're showing off your hot body," I said. "You must really like this guy if you're this freaked out about what to wear, and you're going to hear him sing."

"It's not a guy. Her name is Rachel. And, yes, I think I really do like her," Kourtney said, once again putting on another dress and looking at herself in the mirror.

"Huh!" I exclaimed, deep in thought.

"Huh, what? Am I not allowed to like women?" Kourtney asked as she pulled the dress off.

"No, you definitely are. Me and Jessica have just been...nevermind. Kourtney, you look great in everything. Just be yourself, and she'll fall in love with you," I told her.

I watched as she put on a black, spaghetti-string dress with a floral print on it that ended just below her knees with no bra on. "That's the one!" I said. "You look amazing in it."

Kourtney spun around in it, told me thanks and that she missed me, and hung up the phone.

I was still turned on from watching her change clothes so much and seeing her breasts and nipples, so I found some pictures and videos I had of Kourtney on my phone, pulled down my shorts, and jacked off while thinking about her with another woman.

Later that night, I was lying in bed with Jessica, telling her about my phone call with Kourtney.

"I told you she's into women now!" Jessica said, sitting up in the bed. I looked over at my girlfriend, beautiful as always, with her brown hair pulled up into a messy bun on top of her head, wearing an old white t-shirt with no bra on underneath, and a pair of pink running shorts.

Jessica rolled over onto her side as we talked, and I put my arm over her, resting it on her stomach. I pushed my body close to hers and started to kiss her neck as she melted into me. As I kissed her neck, I moved my hand up and grabbed at her breasts, squeezing both of them through her shirt. She pushed her butt into my groin, grinding it slowly.

She took a deep breath and let it out as I moved my lips over her neck, up her face, and to her lips. She kissed me back as I slipped my hand into her shirt, going back up to her breasts and squeezing them again, this time feeling her nipples against my palms.

As we made out, Jessica rolled onto her back and moaned into my mouth as I pinched and rubbed her nipples with my fingers. I pulled my hand out of her shirt and moved it down her stomach to her groin. I rubbed her vagina through her shorts, feeling the warmth coming off it. The shorts were short enough that I was able to sneak my finger through the side of them to rub her pussy. As she moaned again, I slipped a finger inside her and started to pull it in and out.

Jessica ended the kiss, moaning again, and said, "Hmm, that feels so good." I went back to kissing her neck as I fingered her, and Jessica reached down and started to rub my cock through my pajamas. Her hand quickly slipped into them, wrapped around my shaft, and rubbed up and down as I grew to my full six inches.

"When was the last time I gave you a blowjob?" She asked as she stared into my blue eyes.

"Last week," I answered her back.

She started to move, rolling over and crawling down the bed as she said, "So, it's been too long."

I lifted up my hips so she could pull my pajamas down, and my hard, thick, six-inch-long cock popped out and flopped down on my groin. After she pulled my pajamas off my feet and tossed them to the floor, she grabbed my cock with her hands, held it up, and used her tongue to lick up and down my shaft. She wrapped her lips around my tip, sucking it in and swirling her tongue around it. As I watched her, she slid her mouth down the first few inches of my shaft until she felt the resistance at the back of her throat and moved back up to my tip, repeating this movement over and over.

Jessica's hands had been holding my cock up, but she moved one to my balls, holding them and softly squeezing as she bobbed her head up and down. With her other hand still on my shaft, she slowly moved it up and down on the lower half of it.

I pulled my shirt off as I watched her blowing me, her brown hair flopping around the top of her head as she moved up and down. I laid my head down on my pillow, closed my eyes, and enjoyed the feeling of her lips wrapped around me.

After a few minutes, I felt her lips come off my cock and Jessica start to move. I opened my eyes to see her pulling her shorts off, and she straddled my lap. She held my cock up with one hand while she opened up her pussy with the other, only letting go when my tip was inside her. We both moaned as she lowered herself down my shaft, and she started to roll her hips back and forth on top of me, sliding my cock in and out of her.

"Sorry, I wanted you inside me," she said with a smile.

"Don't be sorry," I said. "I'll never say no."

Jessica started to bounce her hips up and down as she sat up a little straighter on me. At the same time, I moved both of my hands under her shirt, up her stomach, over her breasts, and squeezed them at the same time. As I squeezed her breasts over and over, Jessica reached down for the bottom of her shirt and pulled it up and over her head.

With her breasts now exposed, I pulled her down until her right nipple was next to my mouth. I licked all around it, flicked it with my tongue, and wrapped my lips around it to suck it into my mouth. I rubbed her left nipple with my fingers before I moved my mouth over to that one and sucked and licked it. As Jessica continued to bounce her hips on my cock, I pushed her breasts together, put my face in the middle, and rubbed up and down.

"Next time you sleep with Hannah, are you going to have her ride you?" She randomly asked me.

"If there is a next time, I'll do whatever she wants," I said as I went back to squeezing her breasts.

"She keeps talking about it. Don't be surprised; she calls you this weekend when I'm out of town," Jessica said.

"I'll be waiting for it," I said.

"Did you talk to Kourtney about us coming to visit?" She asked.

"No, I didn't. She was so worried about her date that I didn't dare bring it up," I said.

"Do you miss sleeping with her?" Jessica said, sitting up straight on my cock again.

"Of course," I said.

"What position do you miss most with her?" She asked.

"How about I show you?" I responded, getting a moan and a yes from Jessica. With my help, she got off my groin, and I guided her down onto her hands and knees.

As I kneeled behind her, she said, "I knew it." I grabbed my cock in my hand, moved it up and down her ass, and rubbed her pussy. I teased her by putting the tip of my cock by the entrance to her butt and gave her just a little bit of pressure until she said, "Hey, now!"

I laughed a little before lowering my cock down, pushing the tip into her pussy, and letting go before sliding all the way inside her. As I started to thrust my hips back and forth, Jessica said, "I know you miss doing Kourtney in the ass, but today isn't the day for me."

I put my hands on her hips as I pounded into her, going harder and faster with every thrust of my hips. I looked over her naked body, with her head bowing down, listening to her moan as I slammed my thick cock into her.

"Oh yes, Danny, harder, baby!" I heard her say as I looked down at my cock, covered in a mix of our juices, sliding in and out of her pussy. I moved one of my hands to her buttcheek and squeezed it, gave it a light spank, and squeezed it again before giving the same treatment to the other buttcheek. Jessica moaned louder every time I touched her ass and started to push back into me.

"Oh my God! I'm so close. Don't stop!" Jessica continued to moan. I reached forward with my hand, pulled her hair out of the messy bun it was in, wrapped my hand around it, and pulled back slowly, making Jessica raise her head up. "Harder!"

At her command, I yanked back on her hair, pulling Jessica's hands off the bed along with her upper body. At the same time, her body let go, and she had a massive orgasm. Her pussy clenched around my cock, and her body started to thrust back and forth as she moaned. "Oh yes! Oh my God," I heard her say as she pressed back into me.

When she was done, I let go of her hair, and she fell back to her bed, breathing deeply as I continued to slam into her. "Oh my God, baby, keep going. If I were Kourtney, where would you want to finish?" She asked me, lying prone on the bed as I slammed my cock into her still.

"Everywhere. Your tits, your face, inside your pussy or inside your ass," I told her.

"Oh my God! I'll take it wherever!" Jessica moaned out.

Feeling it building up, I pulled out of her and helped her roll over. I grabbed her head and held it up as she sat up. With my other hand, I wrapped it around my cock and rubbed it up and down, pointing it at her mouth. Jessica opened her mouth up, stuck out her tongue, and stared up at me with her hazel eyes as I started to cum, the first few drops landing on her tongue. I moved my cock around, with the next few streams of cum shooting out and landing on her cheeks, nose, and forehead.

Feeling myself almost done, I slid my cock into her mouth as she wrapped her lips around it and finished sucking me dry. When I was done, I sat back on the bed, breathing deeply and staring at my girlfriend covered in my cum. She asked what I was looking at, and I said, "You. Covered in my cum. I'm still in shock at any of this."

Jessica laughed as she got up and walked to the bathroom to clean herself up. She came back to the bed, we got dressed, and we snuggled and kissed until we fell asleep.

The next morning, I said goodbye to Jessica as she left to go on a trip with one of the athletic teams from the university she worked at. I texted Kourtney after Jessica left, both to tell her that I and Jessica wanted to come visit and to see how her date went the night before.

It was a few hours before she texted me back to say, "The date went amazing. She's such a good singer. It was fun to hear her sing in front of people." I asked if that was all they did, and Kourtney said, "No, we went back to my apartment afterwards and had some fun."

"What kind of fun?" I inquire, generally curious how far they had gone, and imagine filling my mind of Kourtney with another female.

"She ate me out and made me cum," Kourtney responded.

"That's hot," I told her.

"Yes, it was. You have no idea," Kourtney said.

"So, are you two a couple now?" I asked her.

"I have no idea. She said she doesn't like hookups with females, but I don't feel we've really talked about what we are. I was in such bliss last night that I couldn't even think about it. I guess I should figure that out before you and Jessica come. When are you guys thinking about coming?" Kourtney texted back.

I agreed with her, and we spent the next little bit chatting about when we should come before going back to her night with her new friend.

I didn't hear from Hannah that day, but I did early the next morning when I received a text from her that said, "You'll never guess what I did." I asked what it was, and she quickly sent me two more messages.

"I bought a thong."

"And I'm wearing it to church."

I laughed as I read her texts and sent one back, saying, "Yeah, I never would have guessed that."

"Do you want to see it?" She asked me, and I said that I would love to see it. My phone beeped twice when I received two pictures, and I quickly looked at both of them.

In the first picture, Hannah was at her house, wearing a black bra and a plain black thong. She had her brown hair loose and was turned backwards, showing off her ass in a mirror in her room as she took the photo over her shoulder. In the second picture, Hannah was in the bathroom of her church. She had put on a black blouse with red flowers and a black skirt. She had pulled her skirt up, turning slightly to the side, showing the side of her buttcheek as she again took the picture in the mirror of the bathroom.

"I can't believe I just did that. How does it look?" She asked me.

"I can't either. Lucky for you, you didn't get caught. It looks great, but I would like to see it in person," I responded back.

"I was hoping you would say that. I'll be over after church," Hannah said, and I instantly felt my cock growing.

I waited nearly two hours for Hannah's church to end, for her to text me that she was on her way, and I met her at the door after she knocked on it. I let her into my apartment and gave her a quick hug.

She had pulled her brown hair back into a ponytail and was only an inch shorter than me, with a pair of high heels on. She sat down on my couch and looked up at me as I said, "So, anybody catch you with your naughty underwear on?"

Hannah laughed and said, "No, but it was so nerve-wracking. We had Sunday school today, and any time a guy said hi to me or walked my way, I got nervous. I sat in the back and kept my hands in my lap the entire time."

I laughed as I sat down next to her and said, "Were you turned on at all?"

"Kind of? Especially when it got closer to church ending and I knew I was coming over here," Hannah told me.

"Good," I said, sitting down next to her and grabbing her hands with mine. I leaned into her, using my head to tilt hers to the side, and began to kiss her neck. Hannah moaned as I kissed her, and I let go of her hands, instead beginning to rub her groin with my palm as Hannah spread her legs.

"We should move to my bed," I told her, helping her off the couch as I stood up. Hannah went to take off her heels, but I told her to keep them on, drawing a confused look from Hannah before I said, "It's hot."

Once there, I wrapped my arms around her thin, fit waist and started to kiss her lips. She returned my kiss as she wrapped my arms around my neck. I moved my hands down to her butt and squeezed her cheeks through the skirt before leading her to the bed and sitting her down on it.

After she sat down, we ended the kiss and unwrapped our arms from each other. I went to kiss her neck again and used my hand to grab the bottom of her skirt and pull it up. When it was up enough, I slipped my arm inside it and up to her groin, feeling the warmth coming from her vagina as I got closer and closer. I kissed her lips again as I rubbed her vagina before breaking the kiss and kneeling on the floor in front of her.

I pushed her skirt up more until it was bunched up on her hips. I examined her groin and saw a little tuft of hair poking out from her thong. I kissed her inner thigh on both of her legs, getting a moan from Hannah. I brought one of my hands up and slipped it inside her thong as I continued to kiss her groin. I felt her wet pussy with my fingers and slowly rubbed up and down her slit before inserting a finger into her.

I pulled and pushed my finger in and out a few times, and Hannah asked, "Are you going to keep all my clothes on?"

"Nope," I told her, continuing to finger her. You'll be mostly naked soon enough," I told her as I pulled my finger out of her, used it to pull her thong to the side, and started to dart my tongue in and out of her.

As I tongue-fucked her, I felt Hannah leaning back on her elbows, moaning at the pleasure I was giving her. I could feel my cock straining in my shorts, and I finally pulled my tongue out and stood up. I went right back to kissing her lips with mine while I put one hand on her vagina and used my other hand to pull my shorts and underwear down.

I grabbed her hand with mine and brought it over to my cock, where she wrapped her hand around my hard, thick, six-inch-long cock. She started to rub up and down as I ended the kiss and asked, "Do you like to taste yourself on my lips?"

"Yes," Hannah breathlessly moaned.

"How would you like to taste yourself on my cock?" I asked.

"I'll do whatever you want or say," she told me.

With that, I reached down to Hannah's shirt and pulled it up and off her head. She let go of my cock as I did so and helped me take off her bra as well. I helped her to lay down on the bed as I picked her feet up, stepped forward, and used one hand to guide my cock into her waiting pussy as she held her thong to the side.

"Oh my gosh," Hannah moaned as I pushed deep inside her. "This feels completely different from the last time."

I started to slowly pull out and push back in, letting Hannah get used to my size and me to her tightness, and said, "Different positions can hit differently inside you. How long can you stay today?"

"As long as I need to. Why?" Hannah asked, closing her eyes as I picked up my speed.

"Because I'm going to pull out of you in a few minutes, cum down your throat, play with your body until I'm horny again, then fuck you until you beg me to stop," I told her as I picked up my speed, grabbed onto her hips, and pulled her body closer to me.

"Oh my gosh," Hannah moaned, and I felt her pussy clenching around my cock, squeezing it even tighter as she started to orgasm.

I had to quickly pull out of her, as I knew I was too close. I climbed up onto the bed, kneeling over her face, wrapping my hand around my cock, and pushing my tip past her lips and into her mouth. I started to rub my shaft up and down as she closed her lips around my tip and started to suck.

"I'm cumming," I warned her as the first shot of cum came out of my tip, and she worked quickly to swallow it and the rest that followed. I moved my cock up and down, feeling her tongue on the underside of it as I orgasmed.

When I was done, I stood up off the bed and looked at my girlfriend's sister on it. Her C-cup-sized breasts exposed, my cum leaking out of her mouth, her skirt pushed up to her hips with her thong still revealing her pussy, she had lowered her legs back down, her feet with the high heels resting on the floor.

"So, how did you taste on my cock?" I asked her.

I watched as she wiped the cum off her lips and said, "Honestly, you came so fast, I barely had time to taste myself."

"Damn, I guess we'll just have to try again later," I said with a laugh.

"How long until you're ready again?" She asked me.

"If I'm playing with your body, not long," I said. "Can I ask you a weird question?" She asked what it was, and I said, "Can I take a picture of you now and send it to Jessica and tell her what we just did?"

I stared at her nearly naked body, my cock dripping onto the floor, as I waited for her answer.