📚 pleasing my sister-in-law Part 33 of 44
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EROTIC COUPLINGS

Pleasing My Sister-in-Law

Pleasing My Sister-in-Law

by Pooer87
19 min read
4.54 (3100 views)
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I was sitting on the edge of my bed, wearing a white dress shirt and red tie, plus black slacks. I could just see Jessica as she was finishing her hair in the bathroom, with her back to me.

"Does it feel weird getting ready for church?" I asked her.

"A little bit," she said. "But I'm excited to hear my dad speak, no matter what I'm feeling about church and religion."

As disappointed as Jessica's parents had been with her about her divorce, moving out, and moving in with me, plus both of us going away from the church, we had been working lately on repairing our relationship with them. We had had dinner with them a few days ago, and they had invited us to go to church that Sunday to hear her dad speak. Jessica, wanting to be supportive, said yes.

I smiled as she turned around and came back into the bedroom. Standing five feet tall, she had her brown hair curled and loose around her face. She wore a cream colored dress that would be considered immodest by the Church of Jesus Christ of Latter-day Saints standards. A two-inch strap held it on her shoulders, but most of her shoulders and all of her arms were bare. It did cover all of her C-cup-sized breasts, but it was tight against her chest and stomach before opening up at her waist and ending just above her knees. She had debated wearing heels but went with a pair of flats instead.

She told me that she was ready, grabbing a light black jacket just in case, and we left the apartment, hand in hand. When we arrived at the church, we walked in, with Jessica getting a look from her mom and dad regarding her dress choice. We said hi to them and to her brother and sister. It had been two weeks since I went to the movies with Hannah, Jessica's sister, and she greeted me with a little hug.

We moved into the chapel, taking a seat in the pew behind Jessica's family, with her dad going up to sit on the stand. As the meeting started, Jessica opened up her phone and started typing something. She leaned the phone over so I could see the message that said, "Doesn't Hannah look super cute today?"

I nodded my head yes and whispered in her ear, "But not as cute as you are."

Jessica silently giggled and typed on her phone, "What would you do if I said I was super horny right now?"

I pulled out my phone and typed out, "I guess it depends. Do you want to wait until we get home?"

"What if I didn't?" She typed back for me to read. I just shook my head with a smile on my face. The conductor of the meeting was reading off some news, and Jessica typed on her phone, "If Dad goes last to talk, I know a hidden spot we can sneak off to. Just don't make it obvious." She finished by telling me where the secret spot was.

The meeting moved into its sacrament phase, which involves the young men passing out bread and water after saying a prayer over them. As we waited for the bread and water, Jessica had her hand on my upper leg, her fingers brushing against my semi-hard cock in my slacks.

After they were done, the conductor read that the meeting would progress, with two speakers first, a music number, and then finishing up with Jessica's dad. As he sat down and the first speaker stood up, Jessica whispered to me, loud enough for her mom to hear that she had to go to the bathroom and get up to leave. A few minutes later, I leaned forward and asked her brother where the men's room was. He quickly whispered directions to me, and I got up and left the meeting hall, awkwardly trying to hide my hard cock by placing my hands in front of my groin.

I followed Jessica's directions to her hidden room, shutting and locking the door behind me. Jessica was already in there and walked towards me. We began to kiss as we moved away from the window, her hands fumbling at my groin to undo my belt and my pants before going into them and wrapping around my cock. I had my hands under her dress as we made out, one hand squeezing her ass through her underwear while I rubbed her vagina with the other hand.

Ending the kiss, Jessica said, "We need to hurry." She turned around, placing her hands up against the wall and spreading her legs as I pulled her underwear down. I pushed her dress up just enough to expose her ass and vagina, stepped forward, and slid my hard, thick, six-inch-long cock into her. I grabbed onto her hips as I started to thrust my hips back and forth.

Jessica had her head down, trying her best not to moan, as I pounded into her. I kept one eye on the door, just waiting for somebody to walk past. I felt my phone vibrate in my pocket but ignored it as I slammed into Jessica over and over, hard and fast. The only sounds in the room were my groin hitting against her ass and her muffled moans. I moved one of my hands up and around her, squeezing her breasts through her dress, before going back down to her hip.

Jessica started to push back against me, and I knew I was getting close. I leaned over her, biting my lip, and felt my orgasm hit. I pushed in deep, holding myself there, but using Jessica's body to pump my cock, milking out the cum as it filled her up.

When I was done, I pulled out of her and tried to catch my breath. I found a box of tissues and cleaned off my cock before pulling my slacks back up. Jessica did the same, wiping off her vagina and pulling her underwear back up to her groin.

We left the room after a kiss and making sure the hallway was clear, with Jessica going into a nearby bathroom and me walking back to the chapel. I checked my phone to see a text from Hannah that said, "My mom thinks you two are going to do something naughty."

I laughed and texted her back, "I don't know what you're talking about."

As I entered the chapel, Jessica caught up to me, and we walked in together, going back to sit behind Hannah, her mom, and her brother. Hannah texted me to say, "Seriously, did you two just go and do it?"

"Maybe. Maybe not. It can be hard to resist a pretty girl in a dress," I replied back.

"What is that supposed to mean?" She asked me as her dad got up to begin his talk.

"Come to my apartment later, and I'll show you," I told her.

After the meeting ended, we talked for a few minutes with her family before they went to their next class. Me and Jessica left the building, holding hands, and got into her car. As we turned it on, I told Jessica what Hannah had texted me, and she said, "Yeah, she texted me too. I told her that it was so much better than listening to the other two talk."

Hannah had texted me again when I got back to my apartment and asked, "Really? You think I want to lose my virginity to my sister's boyfriend on a Sunday after church while wearing my dress?"

I laughed and said, "Well, if it's not like that, how do you want to lose it?"

She replied back, "On my wedding night, after a romantic courtship, a beautiful wedding, and to the man I love."

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Before I could respond, she said, "And if it's not like that, I want it to be more romantic than, Hey, I slept with your sister during church; come to my place and I'll show you what I did to her."

"How about after a date at your favorite restaurant? The guy brings you some flowers, makes you laugh and smile the entire night, you go back to his place after dinner, one thing leads to another, and you lose it to him there." I said to her.

"In this scenario, is this guy you?" She asked me.

"Who better to lose your virginity to than a guy that makes your sister want to get up in the middle of church to go fuck?" I asked her back.

"You've got a point," she said before she stopped responding to me.

By this time, I had stripped out of my church clothes and was standing in the bedroom in just my boxers. Jessica had immediately pulled off her dress and underwear as soon as we got home and was using the toilet. When she saw me standing in the bedroom, she said, "If you want to stay like that all day, I would be just fine with it." I told her I had some other plans that involved even less clothes, making Jessica giggle.

A few weeks passed, and me and Jessica woke up early on a Saturday morning to go on a hike. As we started the hike, Jessica asked me if I had heard from Kourtney lately. I told her it had been a couple of days and asked why. "She texted me a pretty revealing picture last night and said that she had been thinking about me. I just thought it was a little strange that she's thinking about me and not you while dressed like this."

I was walking in front of Jessica and turned as she held up the picture of Kourtney on her phone. She was wearing a white crop top with a push-up bra that made her B-cup-sized breasts seem bigger than they really are. With her black hair loose around her face, she had on a pink thong, one I had seen and taken off her a few times, and was at least smiling as she took the picture.

I asked Jessica, "So, what did you tell her after she sent the picture?"

"I told her that she looked hot, and I missed her too," Jessica told me.

"You aren't kidding," I said. "I wonder what she was up to getting dressed like that."

"I don't know. I'll have to text her later and see if I can find out," she said.

The trail we were on was wide at some points, letting us walk while holding hands. When it was narrow, I started to let Jessica go first. With her brown hair pulled back into a ponytail, she had put on a hat that day. Wearing a gray shirt with the sleeves rolled up, she debated between jean shorts and spandex shorts. I had finally convinced her to wear the spandex, and she had picked a black pair with a pink strip on each side. I admired both her butt and her legs as she climbed up the trail in front of me.

We hadn't seen anybody else on the trail until we reached the top of it, where two couples were hanging out. We said hi to them before finding a rock to sit on, pulling out a snack, and drinking some water.

"You know, Kourtney told me about the hike you and her went on," Jessica said out of the blue, quiet enough that the other people couldn't hear her.

"What about it?" I asked her.

"She told me how she gave you a blowjob, and you fingered her and made her walk down the mountain with her thong soaked," she said.

"We can wait for these people to leave and do the same thing," I said, already feeling myself growing hard in my shorts.

Jessica giggled and said, "That's not why I brought that up." I asked why she had, and she answered, "Because I figured it was on your mind."

"Why do you think I pushed you so hard to wear spandex? They're easier to get into than the jeans would have been," I told her as I put my hand on her upper thigh and started to rub.

"I knew I could feel your eyes on the back of my head as we walked," Jessica said.

"I almost tripped a few times, looking at your ass. More than once, I reached out for it," I told her.

"What was stopping you?" She asked.

"The rocks I would trip over as I started to reach out," I said, making her laugh and do a fake cough as I brushed my fingers over her groin. She glanced backwards at the people behind us and said, "So, if they weren't here, would you be trying something?"

"Probably. Would you let me?" I asked her.

"Do you really think I could say no to you?" She replied back as I rubbed her vagina through her shorts.

I moved my hand down a little bit more, using my fingers to pull up on her spandex. I slipped my fingers inside it and felt her bare pussy, with a little bit of wetness to it and a touch of hair just above it. I rubbed her lips as she got wetter and wetter, moving her butt on the rock and spreading her legs as we kept an eye on the other people.

Jessica stuffed a granola bar into her mouth to stop her moans as I slipped my finger inside her wet pussy. I slowly and softly pulled it in and out of her, watching as she closed her eyes and tilted her head back. I smiled as I felt the inside of her vagina with my finger, going in and out.

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I kept it up until the people finally left. Jessica watched them go, waited a few more minutes, and finally moaned loudly before leaning down, and our lips met in a passionate embrace. I pulled her shorts over even more, getting my finger deeper into her and being able to rub her clit.

As our tongues swirled together, Jessica moaned into my mouth as her hips lifted up off the rock, trying to get my finger deeper into her. She ended the kiss, resting her chin on my shoulder and moaning into my ear as I fingered her. I wrapped my free arm around her waist, pulling her closer to me and holding her up as her orgasm started.

Jessica moaned loudly before biting down on my shoulder to hold her moans in. I felt her pussy clenching around my finger, her legs trying to clamp around my arm as she came, her body rocking back and forth. We kissed again, passionate and forceful, as she came. When she was done, her body settled back down on the rock, my finger still going in and out of her vagina, and she opened up her hazel eyes to look into mine and said, "Oh, my God, Danny."

I kissed her again as her hand moved on top of my groin and started to rub my cock through my shorts. I finally pulled my hand out of her groin as she slipped her hand into my shorts and wrapped it around my growing cock. Just as I was adjusting to give her more room, we heard talking coming from the trail and quickly jumped apart.

We turned around as a father and two young kids entered the clearing at the top of the trail. I made eye contact with him and nodded my head, as did he. They took in the sights at the top of the mountain as me and Jessica sat on our rock. I was still hard, and Jessica was attempting to hide her still-exposed groin. I was hoping they would turn to leave when the father took off his backpack and told his kids he would start getting their picnic ready.

Me and Jessica shared a knowing glance before we started to get up, doing our best to adjust ourselves, putting our backpacks back on, and leaving the clearing. When we could no longer hear them talking, we burst out laughing with Jessica, saying, "That was so close."

"I know! I'm pretty sure he knew that he walked in on it," I said.

"Definitely. I am glad it wasn't a few seconds later, or I would have had your dick in my mouth," Jessica said.

We walked on for a bit, hand in hand, still laughing. I finally asked her, "So, how does it feel to walk with wet underwear?"

"Probably better than it feels to walk with a boner. How is that going anyway?" She asked me, glancing down at my groin.

I laughed and said, "It probably doesn't help that I'm going to do something that will prolong it."

As she asked what that was, I stepped behind her, the trail narrowing down around us, and wrapped my arms around her waist. I leaned down and started to kiss Jessica's neck, which caused her to stop walking, and I pushed my groin into her ass.

"Oh, Danny," Jessica moaned as I brought my hands up and put my palms on her breasts. I squeezed her breasts over her shirt as she pushed back into me. She turned her head, and we kissed for a few minutes. I finally ended the kiss, took a step backwards, and said, "I think we need to get home."

"I don't know if I can wait that long," Jessica responded as she reached back and rubbed my cock.

We made good time back down the trail, managing to keep our hands away from each other. Back at our car, we quickly climbed in and started to drive away. As I drove, Jessica said, "Kourtney finally texted me back. She said that she had a good time last night and was super hungover and horny, and she sent me a nude selfie," showing me her phone with the naked picture of Kourtney as I drove.

I saw her typing something on her phone as I focused on driving. When we got back to our apartment, I let Jessica take a quick shower first as I cleaned up our hydropacks, then took one myself. When I came out, Jessica said, "So, I texted Kourtney back and said that it's too bad that you're not there to help her out. She just responded, and all she said was or you. Isn't it weird how she is acting? Pictures to me, including a nude one, saying she misses me, and now saying that I could help her out?"

"I mean, it's not too weird. She was always talking about having another threesome, and constantly mentioning how hot you are," I told her.

"That's true," Jessica said, laying back on our bed. After the shower, she had only put on a red tank top and a pair of white underwear. She looked at her phone for a second as I checked out her body, then at me, and said, "We should send her a picture while I ride you today."

I smiled and said, "Sounds good to me." I was still naked as I climbed onto the bed, leaned down, and started to kiss her. Jessica put her phone down, wrapped her arms around my neck, pulled me down on top of her, and returned the kiss. I moved one of my hands to her breast, squeezing it and rubbing her nipple through her tank top.

As I started to grow hard on top of her, I pulled her breast out of her tank top, continuing to squeeze it and rub her nipple. Breaking the kiss, I moved down, licked around her nipple, and sucked it into my mouth. She moaned my name again, and I looked up at her to say, "So, just before we were interrupted today, I think you said you were just about to give me a blowjob, right?"

Jessica giggled and pushed me off her. I rolled onto my back as she moved down the bed, taking my cock in her hand, and rubbing it up and down as I grew to my full six inches.

Looking up at me, she leaned down, stuck her tongue out, and ran it up the full length of my shaft, swirling it around the tip, then back down the other side, repeating the process two more times before she wrapped her lips around my tip. She softly sucked me into her mouth before sliding down the first few inches. Holding herself there, she rubbed up and down the lower portion with her hand, before starting to bob her head up and down.

I watched her as she blew me and said, "Probably a good thing we didn't start this up on the mountain. I would have had a hard time stopping."

Jessica continued to bob her head up and down, her hand working the lower portion as well. She briefly took her mouth off me, pulled her tank top off, and went back to work as I told her how good it felt. After a few minutes, I adjusted how I was lying so that I could reach down and squeeze her breasts as they swayed under her. I then softly spanked her ass and placed my hand on her vagina, sliding my hand into her underwear.

Jessica moaned around my cock as I slid my finger into her wet pussy, sliding it in and out a few times before she pulled her mouth off my cock and sat up in the bed. I watched as she pulled her underwear off and tossed them to the floor, straddled my groin with her legs, inserted the tip of my cock into her wet pussy, and slid down my shaft. She placed her hands on my chest and started to roll her hips back and forth as she started to moan.

I reached around her arms, taking her breasts in my hands, and started to squeeze them. I used my fingers to rub and pinch her nipples, listening to Jessica moan every time she bottomed out on my cock. She finally took her hands off me, leaning down closer to me as she propped herself up on the bed. We kissed for a few minutes as her hips bounced up and down, before I ended the kiss and used my grip on her breasts to bring them to my mouth. I licked and sucked on both nipples, paying equal attention to both.

I laid my head down on the pillows when Jessica started to sit up more on me, moving my hands off her breasts and down to her hips. She looked down at me and asked, "Do you think Kourtney has slept with anybody since she moved to Chicago?"

"With the way she was dressed last night, I'm sure that was her goal," I said.

"Do you wish she was riding you right now?" Jessica asked me.

"Right now? No. Do I wish she was laying next to me and playing with herself, waiting her turn? Yes," I responded back.

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