Pleasing My Sister-in-Law

Mid-October in Utah is normally a cold affair, but this year, it was much warmer. It had been two weeks since I drove up to Boise and spent the weekend with Jessica. I was walking out of my lawyer's office, having signed the official divorce papers, and popped down on a bench on the sidewalk just outside of his office.

I pulled out a phone and sent both Jessica and Kourtney a text, telling them it was official and asking who wanted to celebrate that night.

Jessica responded first by saying, "I would be there if I didn't have a basketball game to go to tomorrow morning."

Kourtney responded a short time later and said, "What do you have in mind?"

I sat back on the bench with a smile on my face and texted her back, "You, naked, moaning my name."

My smile faded when Kourtney texted back, "Damn, I was hoping you meant dinner or something like that. It's that time of month for me."

I shrugged my shoulders and said, "Dinner would be great too. Do you just want to come to my house after you get off work?"

"I'll go home and change first, then come get you," she responded. I told her that that sounded great, sent another text to Jessica, put my phone in my pocket, and got up to walk to my car.

Later that night, after me and Kourtney enjoyed a meal at a local Chinese restaurant, we were back at my apartment. I was sitting on my couch, my legs spread open, my pants and underwear on the floor, and watching Kourtney as she kneeled between my legs.

She had taken her shirt and bra off, having let me play with her B-cup-sized breasts as we made out before she kneeled on the floor. Her brown hair was pulled back into a ponytail, her hand wrapped around the base of my cock, and her lips wrapped around my tip as her tongue swirled around it. She looked up at me with her hazel eyes as she slid her mouth down my shaft, swallowing my cock whole.

I moaned as she started bobbing her head up and down, closing my eyes and leaning my head back on the coach. Kourtney moaned around my cock as she moved her mouth up and down it. She had her hand wrapped around the bottom of it, sliding up and down it with her mouth. Her other hand was on my balls, softly squeezing and massaging them.

I heard my phone ringing on the end table next to me and glanced over at it to see that Jessica was calling me. I picked up the phone, thought about answering it, but instead declined the call. I quickly texted Jessica, saying that I would call her later.

Kourtney watched me as I put the phone back down. She took her mouth off my cock but kept her hands going on it and asked, "Was that Jessica?" I told her it was, and she said, "You should have answered. I would have kept quiet."

"Yeah, right," I said.

Kourtney smiled before opening her mouth up and wrapping her lips around my cock again. She deep throated me a few more times before going back to just licking my tip while her hand made a circular motion going up and down my shaft. I told her I was getting close, and Kourtney took her lips off my tip, leaving her mouth open, and aimed my cock towards it as she jacked me off.

I grunted and moaned as the first bit of cum shot out of my cock, landing on Kourtney's tongue. She pumped the next few shots into her mouth before taking my cock back in, sliding down my shaft, and swallowing my cum right down her throat. When I was done, she licked my shaft and tip clean before sitting back on her legs. As I caught my breath, she said, "There you go; your first blowjob as an official single man."

"Well, first since before I started dating Kathy," I told her. I pulled up my pants and underwear as I watched Kourtney stand up and grab her clothes. She pulled her bra and shirt back on before sitting down next to me on the couch.

We talked for a few minutes before she said, "I guess that I should go so that you can call Jessica before she falls asleep."

She stood up from the couch, and I followed her to my apartment door. We hugged and kissed before saying goodbye. I sat down on the couch, opening up my blinds, and watched Kourtney walk to her car as I texted Jessica to make sure she was still awake. She said she was, and I quickly pressed the button to call her.

"Hello, there. Have fun with Kourtney?" I heard what Jessica said when she answered the phone.

"How did you know I was with Kourtney?" I asked her, laughing.

Jessica laughed too and said, "Because that's the only reason I could think of that you wouldn't answer my call."

"You caught me," I said.

"Is she still there?" She asked me.

"No, just a quick blowjob tonight," I said.

"You poor boy. Hey, so I might be coming to Utah this weekend," she told me.

"Really?" I said, my mind getting excited at possibly seeing her.

"Yeah. My mom, dad, and sister are all speaking in church on Sunday and just told me about it," Jessica said.

"Oh yeah? So why the might be coming down?" I asked her.

"Well, I just need to figure a few things out. Mom and Dad said I could stay at their house Saturday night. I'm waiting for an answer from Jack if I can pick up Liam either Sunday and take him to church with me or if I can just get him Monday instead of meeting him halfway between there and Boise," she explained.

"I mean, both of those make more sense, but we know how Jack is. Is that all you're waiting for?" I asked.

"No. If I don't get Liam on Sunday, or if Jack still wants him that night, I was going to see if I could spend the night with you, she said.

"Well, that's easy. Of course, you can. Hell, spend the night here on Saturday too," I said with a laugh.

"I thought about that too. But I won't be able to leave here until late Saturday night. And by the time I get there, I'll probably just want to go to sleep. If I see you, however, I'm going to want to do more, stay up too late, and probably miss church the next day. So, we might just have to wait until Sunday," Jessica said, making my heart flutter.

"Makes sense. Well, I hope you do come down, and hopefully I do get to see you," I told her. We talked for a little bit longer before Jessica had to go to sleep, and we hung up after saying goodbye.

Saturday afternoon, Jessica texted me to say, "Hey, sorry, I haven't said anything all day. I have been busy with back-to-back games. So, I am coming down tonight. Jack said he'll bring Liam to my parents church, but he wants him back afterwards, and I can pick him up on Monday. So, I'm thinking maybe I'll just drive to your place after I drop Liam off, and I can stay there all night if you still want me too."

I told her that that would be great, and I couldn't wait to see her.

Late that night, Jessica texted and asked if I was still awake. I told her that I was and answered the phone when she called me a second later. "Sorry," I heard her say, followed by, "My parents have been giving me the third degree since I got here, and I needed somebody to talk to."

I asked what about, and she said, "Everything. Why I'm not wearing my garments. Why I'm not going to church. If the divorce was really necessary, my dad even asked me if I'm having sex up in Boise outside of marriage, and my mom about flipped when I told her I was spending tomorrow night with a friend instead of at their house."

"Wow, Jess," I said. "That sucks. I'm sorry they're treating you like that."

"That's the weird part; it doesn't even feel like they're treating me badly. I can tell that they're doing it because they care, but they are disappointed in what is going on in my life," Jessica responded.

"So, what did you tell your dad about having sex outside of marriage?" I asked with a laugh.

"I told him it was none of his business, to which he said that's as good as a confession. And the whole time, all I was thinking about was what me and you will be doing tomorrow and how I wanted it tonight too," Jessica told me.

"Speaking of tomorrow, I think you should stay in your church clothes when you come over here," I said. Jessica laughed and asked why, and I said, "Because the thought of you going to church with your parents, then coming to my apartment and getting fucked in the same dress or skirt turns me on."

"I think I can do that. Do you prefer a skirt or a dress?" She asked me. I told her either one, and she said, "Maybe I'll send you a couple of pictures tomorrow morning and let you pick." We said goodbye a little bit after that, but continued to text until we fell asleep.

I woke up the next morning to my phone buzzing. I grabbed it to see a few messages from Jessica and opened it up to see that they were pictures. In the first picture, she was wearing a white shirt that was tight against her C-cup-sized breasts, a red jacket that went past her waist, a black belt around her waist, and a gray skirt that ended just below her knees. In the second picture, she had put on a white dress that had a floral design print all over it. It went down to her ankles, didn't show off her body like the skirt did, and she had put on a dull green overcoat that went down to her knees.

"What do you think? My mom bought me the dress yesterday, because she wasn't sure what I would bring. She actually told me she was worried I would dress immodestly for church," Jessica explained to me.

"You look absolutely beautiful in both of them," I told her.

"Thank you," she replied back. "But, what one should I wear?"

"I guess it comes down to a few questions. What do you have under them? What one is easier for me to get into? Do you want to get fucked in a dress your mom bought you? And, most importantly, what one is most comfortable for you to wear?" I texted back to her.

Jessica sent back a laughing emoji and said, "You'll have to wait to see what's under them, but it's the same for both. The skirt moves pretty freely, but the dress is tighter than it looks. I just want you in me, and the skirt is probably more comfortable."

"In that case, wear the skirt," I said.

Jessica said OK, and we kept talking as she continued to get ready. I was starting to talk dirty to her when she said, "So, Jack just texted me. He said that since his church is before my parents, he'll just bring Liam right to me instead of me picking him up. And he might hang out during my parents ward, and take Liam back home with him, so I don't have to worry about dropping him off afterwards. Ugh!"

"That's bullshit," I said.

"I'm not actually that mad about him being the one to drive Liam around, because he deserves the time with him, and he's being nice to let him come today. I'm more mad that he wants to stay," Jessica said.

Jessica's parents church started their first meeting at 10:30 and it was about twenty-five minutes later when I heard from Jessica again. She said, "So, not only is Jack staying but he's sitting on the same bench with me and Liam."

"Are you serious?" I asked her.

"Yeah. He brought Liam inside the building, found out that my parents and sister were sitting up on the stand, and asked if he could sit with me and Liam. And before I could answer, he went into the chapel and found us a bench," she replied back.

"Damn, that kind of ruins my plans," I said.

"What plans?" she asked.

"To tell you how excited I am for you to be here, to kiss you and hug you. And bend you over my couch and pound into you over and over," I said.

"God, me too. My car is already packed, so once I say goodbye to everybody here, I can drive straight to your place," Jessica said.

"Good. I'm debating what to do first. Make you give me a blowjob or take you to my couch. I'm thinking couch so that I can take care of you and make you forget about Jack," I said.

"Tell me how you're going to do that," she said. I continued to talk dirty to Jessica, telling her everything I wanted to do to her. Shortly before the church meeting ended, she said, "I'm pretty sure Jack is trying to read my messages. He keeps glancing over at me."

I laughed and said, "You should accidentally flash him the text about me railing into you from behind while you scream my name."

A few minutes later, she said, "Funny enough, he just asked who I was talking to, and when I didn't answer, he said, I can see the name on your phone and asked if it was a new boyfriend." I asked what she told him back, and she said, "I panicked and said that it was. I'm wondering if he'll put two and two together about your name."

"Oh, I would love to see his reaction if he does," I told her back.

About ten minutes later, Jessica texted that she had just said goodbye to everybody and was on her way over. I anxiously waited for her, my cock starting to grow hard in my shorts at the thought of what was to come. When I saw her car pulling up next to my apartment, I walked outside to greet her, wrapping my arm around her waist, and leaned down to kiss her while taking her bag from her. We held hands as we walked back to my apartment.

Once inside, I sat her bag down and shut the door behind us. I wrapped my arms around her waist and picked her up. Jessica wrapped her legs around my body as I carried her the short distance to my bedroom, and we began to kiss. Placing my hands on her butt, I moved her up and down, rubbing our groins together. Hitting against the bed, I stopped the kiss and sat Jessica down on the bed.

I grabbed onto her legs as she laid back on the bed, spreading her legs wide. With one hand, I reached forward and started to rub her vagina through the underwear she had on. With my other hand, I pulled my shorts and underwear down. I used my fingers that were rubbing her pussy to move her underwear to the side as I stepped closer to her. I glanced up at Jessica's face and saw that she was looking down, trying to see me, but her skirt was blocking the way.

Still watching her face, I inserted the tip of my cock into her wet, hairy pussy and let go. I pushed in deep as she moaned loudly, her eyes rolling into the back of her head. Grabbing onto her legs, I started thrusting back and forth, sliding my hard, thick, six-inch-long cock in and out of her.

I reached forward with one of my hands and started squeezing Jessica's breasts through her shirt. She moaned as I did so, "Oh God. Yes please. Harder."

I laughed and said, "What do you think your family would be thinking if they knew what you were doing now?"

Jessica shook her head and said, "You mean going to a guy's house after church, having sex while still in my church clothes, and that sex being good enough to say, Oh God? My mom would pass out, and my dad would never speak to me."

I asked her, "What about your sister?"

"She would probably be jealous," Jessica said.

I picked up my pace, slamming into her over and over. I put my arms and hands under her legs, lifting her hips up off the bed as I fucked her harder and faster. Sensing my orgasm coming, I pushed in as deep as I could and grunted as the cum erupted out of my cock. I pumped in and out of her, filling her up with my cum.

When I was done, I pulled out of her and sat her legs back down. I laid down on the bed next to her, panting to catch my breath. Jessica sat up and kissed my cheek before saying, "You know, that was fast enough and good enough; next time I go to church, maybe I'll invite you along and we can sneak somewhere for a quicky."

I looked over at her and said, "You want to fuck in a church while people are around?"

"Is that bad? It would be so hot. I was actually thinking about it today; if it was you there instead of Jack. Just sneaking off to an empty room, barricading the door, and letting you do your thing before going back to the meeting like nothing happened. It made me wet thinking about it."

I shook my head, laughing, and said, "Let's do it."

We kissed a little bit more before falling asleep and taking a short nap together.

When we woke up, Jessica looked at me and said, "I'm hungry. What are you making me for lunch?"

I laughed and said, "What do you want?"

"Whatever. Let's go out somewhere. I want a burger," Jessica said.

"Oh, now you want me to buy you food? What do I get out of it?" I said, teasing her.

"I'll give you a blowjob when we get back," she said seductively.

"You would do that anyway," I told her.

"Dang, that's true. What do you want?" She said this, sitting up on the bed and leaning over me.

I thought about it for a moment before smiling and saying, "I want you to dress your skimpiest when we go out, a blowjob when we get back, and I get to pick what clothes you wear the rest of the day."

"How about just the last two? I don't really have anything skimpy that wouldn't get me in trouble in public," she countered, and I agreed to it. Jessica jumped up off the bed and dug through her bag until she found a pair of black leggings. I watched as she took off her skirt, showing me her ass in a black thong, before pulling the leggings on. She brushed her hair out quickly as I got myself ready, and we left.

We found a burger joint nearby, and both of us ordered a cheeseburger with fries and a shake. As we ate, I asked her, "So, why did you say that your sister would be jealous if she knew what we were doing today?"

Jessica laughed and said, "Because she's a twenty-five year-old virgin who is horny and obsessed with sex."

I raised my eyebrows and said, "Do I even want to know how you know that?"

"While me and you were texting last night, and after my parents had fallen asleep, she came into my room and started asking me a bunch of questions. Like, is sex as bad as we're taught it is in the church? How did I feel when I cheated? Have I done it since my divorce? Do I feel guilty? Stuff like that," Jessica explained.

"What did you tell her?" I asked back, genuinely curious and not at all thinking about what her sister looked like.

"The truth, mostly. I told her sex is great. I did feel a little guilty at first, but it quickly went away," Jessica started to say.

"Wait, sorry, does she know about me? Or did you've cheated with another guy?" I asked.

"No, she doesn't know about you. I did tell her that there is another guy and that I've been with him since I've been divorced. I told her, honestly, she needs to wait to find the right guy, and how happy I was to save myself until marriage," Jessica finished.

"Damn," I said.

"What? Should I have said something else?" Jessica asked with a smile on her face.

"Yeah, you should have told her that I'd help her out if she's really that curious," I said with a laugh and a smile.

Jessica laughed too before throwing a napkin at me, and we changed subjects. After lunch, we headed back to my apartment, where Jessica said, "So, what do you want me to wear?"

I laughed and said, "Honestly, just wear whatever you want. Ideally, something revealing and small. Like booty shorts and a tanktop."

She gave me a kiss before turning and going into my bedroom, where her bag was. I sat down on my couch, turned on the TV, and scrolled on my phone. I looked up a few minutes later when I heard Jessica ask, "How's this?"

She had pulled her brown hair back into a ponytail, taken off her white shirt, leaving her in just a black bra with some lace around the top of it, and exchanged her pants for a pair of pink shorts that barely covered her groin. I smiled and said, "Beautiful, like always."

She walked towards me and said, "And, I believe, I owe you a blowjob, correct?"

"I wouldn't say owe, but I'll never turn one down," I said as I put my phone down and watched as Jessica kneeled on the floor in front of me. I lifted my hips off the couch as she pulled my shorts and underwear down to my ankle. My semi-hard cock flopped out, and Jessica wrapped her small hand around it, rubbing up and down, and flicked her tongue against my tip.

When I finished growing to my full six inches, she opened up her mouth, wrapped her lips around me, and slid down the first few inches. She started to bob her head up and down my shaft, her hand rubbing the lower half that her mouth couldn't get in. I told her how good it felt, staring down at her.