Car Ride with My Sister-In-Law

My name is Charles (34) and my wife's name is Lily (31) - we have been happily married for 8 years. Jessica (18) is Lily's younger sister. Since my in-laws were getting older, and my wife and I had no kids of our own yet, they would typically ask us to help Jessica out whenever she needed it. Their family was blessed with amazing genes, parents and daughters alike were beautiful. Lily would typically get daily compliments from girls, and hard glances from other guys when we walked in public. She was naturally sexy, long legs, 32C chest, with a skinny waist. She was one of those girls that could curl into your arms perfectly. Yes, definitely happily married.

Jessica looked just like Lily did when she was younger, and judging by stories from my wife, Jessica would get similar treatment in public too. Fortunately, both Jessica and Lily were humble and really down to earth. My wife and I would often take Jessica to run errands, tutor her in classes, give her rides to her friend's house, etc. The three of us had a very close relationship; Lily was the funny one, Jessica was the smart one, and of course I was the lucky one. 

Three months ago, my wife's younger sister Jessica graduated high school with honors as we proudly cheered from the audience. And so, today was the day - Jessica was finally moving to college. Since we had a larger SUV, my wife volunteered us to drive her up and help settle her in. We had everything planned out, we would pick her up at 7am, load up the car by 8am, and make the five hour drive upstate to arrive in the afternoon to unpack. I stayed up late last night for work, and Lily agreed to drive so I could catch some shuteye. 

When we arrived at Jessica's parents house, we saw Lily's parents and Jessica waiting for us outside. Lily gasped at the amount of stuff that Jessica was bringing, while I did my best not to gawk at Jessica. It was a very hot day - Jessica was wearing her hair tied up, and a white summer dress that was backless and had spaghetti thin straps extending over her shoulders, the length of the dress stopping about mid-thigh, showing off her beautiful legs. She was the spitting image of my wife when we first met, so young and innocent, with her infectious smile. It was difficult not to stare, and it took all my effort to avert my gaze toward the boxes awaiting us on the driveway. 

Jessica's belongings consisted of a 55" TV, minifridge, microwave, and about eight boxes. We began our creative packing process and finally ended having to fold the second and third row seats down in order to fit all the boxes. The TV was squeezed between the driver and passenger side seats in the front. This left only two seats in the SUV - one for the driver and one for the passenger. Since I was exhausted, I offered to take a Lyft back home while Lily and Jessica could head up together. 

"But what about the ride back? I'm not sure I can make such a long trip on my own." Lily stated.

"Well, there's nothing we can do... there's only two seats available," I replied.

"What if you drive Jessica up?" 

"I don't think I have the energy to make two five hour trips today, I was planning to take a nap on the way up..."

Jessica's mother inserted herself and said "Well Charles, what if Jessica sat on your lap while Lily drove? Jessica's not that heavy and you're family, would that be okay?"

Jessica quickly glanced at me and blushed, then turned to her mom, "Mom!! We can't do that."

I smiled at Jessica. I had to decide quickly, and it's not an easy thing to turn down your in-laws. I'm sure Jessica was light as a feather too. "Sure, I would be okay with that. Lily, are you okay with that too?"

"Yea, that's fine with me, just let me know if either of you are uncomfortable."

"Wait, but..." Jessica stammered.

"Let's just go, if things get uncomfortable, we'll just make Charles drive and we can share the seat," Lily replied.

"Ok, fine..." Jessica glanced quickly at me again, "Sorry if I'm too heavy, I'll try not to move too much."

And so, we said our goodbyes to the parents, and began getting in the car.

"Let me get in first," I said. I noticed that the TV was completely blocking my view of Lily, so the space here felt even smaller. I quickly got comfortable and moved the seat as far back as I could. Jessica nervously looked at how tight it would be, as she began getting in. I glanced again at her summer dress, as it clung evenly around her firm body. Good thing I just wore my gym shorts and a loose t-shirt. As she lifted herself up, she tried to modestly grab her dress and pull it tight against her butt before sitting on my lap. She placed her legs on top of mine, so that my knees were against the back of hers. This put her ass directly on top of my cock, which was already growing against my will. The fabric of her dress was thin, and I could feel the slight crack of her ass. The physical contact and warmth from her body against mine immediately sent waves through me, but I tried my best not to react. I buckled us in and placed my hands to the side, while she placed hers on her lap to try to hold her dress down. As she leaned back against me, I got to see her bare back, which pressed against my chest. 

"You guys settled in?" Lily asked.

"Just about, are you okay Jessica?" I responded, as I closed the passenger door.

"Yea, I'm good to go, thanks for driving me Lily. And thanks Charles for letting me sit here... hope it's not too uncomfortable for you."

Lily began driving away as we waved to her parents. Jessica was light as a feather, and despite being so fit, she still felt soft everywhere. Her body naturally melted into mine as she leaned back. I tried to close my eyes to get some sleep, but her smell was so intoxicating. I could feel every breathe she took as our bodies rocked steadily with the car. She leaned her head back against my shoulder, and closed her eyes too. Because of our positions, her exposed neck was right next to my face. I turned a little and, due to the proximity, could feel the warmth from her neck on my mouth. 

All my senses were now on high and I was wide awake. I became acutely aware of the shape of her body against mine. The cut of her summer dress allowed me a birdseye view of her perfect cleavage, and I could tell she wasn't wearing a bra. I could almost see the faint outline of a nipple near the top of her dress.

Jessica adjusted to try to get more comfortable and I could feel the crack of her ass lightly trace my cock. I know she didn't intend for it to do so, she was just too innocent. Plus, she and I didn't have that kind of relationship; she looked at me like her older brother. How could I betray her trust?

So I tried to focus and closed my eyes to get some sleep. It had been about ten minutes, but the warmth and softness of her body against mine was too distracting. As she relaxed more, her body melted into mine; the closeness felt amazing. The bumpy motion from the highway was creating this awkward friction between her ass and me. My cock was getting harder and pushing up along her crack toward her pussy. Luckily the tension in my shorts was keeping my cock from pressing fully into her crack, otherwise, I'm sure she would feel it. I needed some distraction or I would go crazy.

"Lily, you there? Could you turn up the music? I can't reach the radio," I asked.

"Yea sure Charles, aren't you tired? Is Jessica asleep?"

"I think so, but I'm having trouble dozing off... just needed some noise, you know? Little louder please."

"Ok, sounds good, don't be afraid to wake Jessica up if you need to stretch or anything." 

I could barely hear Lily over the music, so I just reached over the TV and lightly placed my hand on top of her head in thanks.

I tried to focus on the dance music, but honestly, it was getting me even more riled up. I closed my eyes, but that only accentuated my other senses. With the beat of the song, my head being a little foggy from exhaustion, and the warm ass grinding against my body, it kind of felt like I was at a club. I opened my eyes and immediately noticed her long perfectly smooth legs. Her hands had fallen to either side and the thin dress she was down holding in place was now riding high up on her thigh. Her left dress strap had also fallen off her shoulder, making her perfect cleavage even deeper. My cock was almost completely hard, and the pressure buildup felt like I could explode.

"Jessica, are you awake?" I whispered. 

No response but the soft, steady, up and down of her chest.

Shit, man, she's your sister-in-law! I tried to gently readjust myself so my cock wasn't pressed so closely along her pussy. It already took all my will power not to grab her juicy tits with one hand, hoist her up with the other, and fuck her right here. I closed my eyes again. After a few more minutes of this, all the friction, body heat, and pressure added up, and I couldn't think straight anymore. My body started acting on its own.

First, I glanced again toward Lily to make sure we couldn't see eachother. Second, I looked at Jessica to make sure she was asleep. By her steady breathing motion, I knew that she was. I gently set my right hand on her right thigh. God, her skin was so soft. I lightly wrapped my left arm around her skinny waist and pulled her tight against my body. Jessica stirred slightly, and I quickly relaxed my grip around her waist. She relaxed again and slumped her body against me. I held this position with my arm around her waist, and my hand on her right thigh for awhile, just enjoying the feel of my wife's younger sister pressed against me. I used my left hand to softly massage along her flat stomach, slowly rising higher and higher until I reached her underboob. 

My cock was rock hard now. I couldn't think clearly anymore, and Jessica was no longer Jessica to me, but some hot teenage girl sitting on my lap half naked. My hand slowly inched up and pressed lightly against her right tit. I could feel the softness fill my palm against the thin fabric of her dress; she was about the same size as my wife, except Jessica's tits were younger and firmer. I squeezed lightly and my cock twitched against her pussy. Her spot was so warm, and maybe I was imagining it, but it also felt slightly damp down there. My right hand began sliding her dress up until I could see her pink panties peeking out. I could see the long bulge of my cock sticking straight out between her legs, pressed against the bottom of her panties. 

This was escalating so fast, but I didn't care. My hot wife was sitting less than two feet away from me, and I was feeling up her hot younger sister, who was asleep on my lap.

I needed to figure out a way to get my shorts off - the pressure buildup was just too much. Glancing again at Jessica, I wrapped my left arm around her waist again, and pushed up with my legs so that I was partially off the seat. Using my right hand, I pulled my shorts down past my knees, freeing my fully erect cock. I ran my hand along her smooth leg and slid her dress up to fully reveal her panties before sitting us back down on the seat. My bare cock pointed forward, with my shaft pressing against her panties along her slit. It felt so good. If I just leaned her forward a bit... my cock would be pointing straight into her opening. Only her thin panties was separating my cock from rubbing right against her pussy. If I just slid her panties to the side...

I hesitated though, and instead I reached under and used my right hand to push my bare cock up, gently using it to massage her pussy. Despite her panties blocking me, it still felt amazing.

My left hand continued massaging her right boob, and my right hand was rubbing my cock head against her pussy. I felt her wetness seeping through her panties, and at the same time, Jessica began stirring and breathing harder. I heart a soft moan from her throat, as her head rolled on my shoulder. She was now breathing directly on my neck. My hands froze, my left hand still pressed against her tit through her dress, and my right hand released my cock. The wet stain on her panties was very noticeable. After a couple seconds, I gently used my right hand to cup her pussy to feel the moisture, in hopes of calming her down a bit. How would I explain this situation if she wakes up? How would she react? 

When her breathing slowed back down a bit, I reached my left hand slowly through the top of her dress to cup her juicy tit directly in my hand. My God, the skin on skin felt so good. Her nipple was already hard, and I gently massaged her tit. My cock twitched against the back of my hand, which was still cupping her pussy. I used my right hand to slowly trace the outline of her slit over her panties; I could feel more wetness through the fabric. I spread my legs a little, which caused her legs to open some more, to give me easier access. I pulled aside her panties to reveal her cleanly shaven pussy. It was so wet... just like my wife. I pressed my shaft along her pussy lips - it felt so soft. Jessica moaned again, and her breathing quickened. My gorgeous loving wife was right next to me, hidden from view, and here I was groping my hot sleeping sister-in-law, inches from fucking her. 

I gently parted her pussy lips and pressed the tip of my cock against her entrance. It was so wet, I knew it would slide right in with even a small nudge. I continued to massage her slit. While squeezing her boob with my other hand, just as I was about to give it a test, I suddenly felt Jessica's body tighten against me. I looked over at her and her eyes were open and shocked. 

"Charles, what are you doing??"

Instinctively, she clamped her legs shut, grabbed my arms and tried to get off. Unfortunately though, because of her forward motion, my cock which was already right at her entrance, slid easily into her pussy a couple inches.

"Ohh my God, what??" Her breathing was heavy. Luckily the music was loud and Lily couldn't hear her sister.

"Jess, I'm so sorry..." but I could hardly focus on talking as it took everything in me not to thrust all the way in.

Jessica continued to struggle, but this only caused more motion and friction of my cock in her pussy.

I placed my hands on her smooth legs, and gently pushed them back open.

"Please Charles, you're married to my sister... aren't we family? What are you doing??"

"Jess, you're so beautiful, I didn't mean for this to happen. Please stop moving so much... you're riling me up even more," I said with strain in my voice.

"Charles!!" Jessica screamed. My penis flinched deeper into her pussy.

"Are you guys okay over there? Do you need me to turn the music down?" Lily loudly asked.

Jessica and I both froze. I squeezed her tightly against me, realizing now that both of her dress straps had fallen over her shoulders, exposing her tits. I looked at Jessica, lustfully, silently begging her not to say anything. Jessica looked at me, not knowing what to do. I was her brother-in-law after all; I'd watch her grow up, and now she looked at my one hand that was cupping her breast, and looked at my long penis halfway up her vagina. If she said anything at all, my marriage would be over - there would be no way out, and I think Jessica realized that too.

And so, after what seemed like an eternity, Jessica replied, "Sorry Lily, I was just having a dream and Charles woke me up."

"Ah, okay. Charles, aren't you tired? Why don't you both get some sleep before our next stop?" Lily asked.

"Yea, just trying to get comfortable, I'm sure both of us will be able to get some rest soon," I replied while looking at Jessica. 

Jessica sobbed quietly as she looked around at her predicament. Her breathing was still heavy, and I could tell she was conflicted. She squeezed my arms and quietly whispered to me, "I've never had sex before. It's so big, Charles, please don't. We can still stop, right?"

I softly kissed the side of her neck, and whispered, "Jess, thank you for not saying anything. You're so beautiful. Just let me push all the way in once, then I'll pull out. Is that okay?" I could barely think straight, it was so hard to wait for a response, and it felt like I would explode at any motion. 

Lily closed her eyes, and replied, "...Ok, fine Charles, but only because I love you like family. Please make it quick..."

That was all I needed. I continued squeezing her tit, and with my other hand, rubbed her clit above my cock. I slowly thrust up my remaining length, enjoying every second, pushing against any resistance from her virgin pussy, and finally my entire cock was inside my sister-in-law. This feeling is like the first time I fucked my wife over ten years ago: pure bliss. My cock pulsed while I held my full length inside her, completely filling her void. Jessica moaned loudly as I continued kissing her neck and playing with her clit. She arched her toned smooth back against my chest, causing my cock to push harder into her pussy. 

Testing my luck, I pulled my cock out a few inches and thrust back in, gauging her reaction while continuing to tease her neck with my tongue, and play with her nipple. She began to take deeper breathes, moaning and panting at the same time. She opened her toned legs and rested them outside my legs, and she curled both her feet around each of my ankles. With her back arched, her right hand reached up to hold the back of my head. We were now completely intertwined with each other.

"Charles, please, this is so wrong. You said you would pull out, right?"

Her words were asking one thing, but her body was telling a completely different story. I answered with another three quick thrusts, to which she responded with the sexiest moan I had ever heard. 

"Jess, look at me."

As she opened her eyes and turned towards me, I kissed her on the mouth. Our lips opened and our tongues met. Electricity shot down my body and I quickly began fucking sister-in-law hard. We closed our eyes and began kissing with a new found passion. Her legs were still wrapped around mine, and she moved her hands and grabbed mine. I continued playing with her bare tits, while rubbing her clit with the other hand - thrusting my cock in and out the whole time. Our tongues danced around each other, and I had never felt a stronger emotion than I did right now. This was heaven.

I began fucking her harder and harder, in and out. I felt the pressure building up and I knew I was going to finish any second. Jessica's eyes suddenly opened and she stifled a scream into my mouth. I felt her clit swell up and her pussy tighten. Her juices started spilling out. Her legs squeezed mine and she arched her back even harder against my chest. Her orgasm was overwhelming her and she tried to pull away but I pressed my mouth firmly onto hers, and she kissed back. With that, I squeezed her tits hard, and I fully pushed my cock into her pussy and shot out the strongest wave of cum I've ever released. We were both squeezing each other and screaming into our mouths, our tongues still pressing together. I continued to fuck my sister-in-law and my cock throbbed, as I shot loads and loads of cum deep into Jessica. 

When we both finished, I held onto her tight and kissed her neck lightly. We cuddled together for a few minutes. Jessica looked at me, with a mix of innocence, lust, and love. My cock was still hard, deep inside her, but she wasn't fighting it at all. She kissed me on the forehead. She began pulling her dress straps back up over her shoulder. I sadly looked one last time at her gorgeous tits, and gave them a quick squeeze before her dress covered them. Jessica smiled at that.

"Thank you, Jess. That was amazing..." I said.

"You're welcome. My sister is a lucky girl," Jessica replied.

"I think I'm the lucky one..."

Jessica smiled at me again, as she fixed her dress and pulled the front back down to cover her thighs. I made no move to pull up my shorts: my cock was still deep inside her pussy, twitching slightly. 

My wife hadn't said a thing this whole time. Four hours left until we arrive. 

"I'm going to try to sleep, Charles. I hope you don't get any funny ideas again..." she winked as she gave my legs a quick squeeze. She relaxed her body and put her head on my shoulder again, just like when we started the trip. Except this time, my shorts were already off and my cock was already deep inside Jessica's pussy.

Staring down at her cleavage, I placed my hands on Jessica's smooth legs, and blood started rushing to my cock once again.