Ashley 5 – Family Vacation

My name is Ashley just before the end of the summer my mother, father, brother, and I went for a family vacation. The night before our family vacation my brother Ryan and I had a night filled with oral sex. Ever since my mother found out that I was getting curious about sex at the beginning of the summer, she has been encouraging me to experiment with Ryan. Ryan and I have passed the experimentation phase, but we are still learning and teaching each other. Given our parents reactions when spying on us they seemed to be as happy with the arrangement as Ryan and me. The night started with him going down on me. I came so many times I became too sensitive so we switched places. I swallowed at least three loads of cum before he became too tired for a fourth. All the while anytime we got tired and slowed down we could hear our parents down stairs also having sex. This started us going again. It was a long and passionate night, but eventually I collapsed on my bed and Ryan headed to his room to crash. Our parents had gone quiet a short time before we did. We didn’t know where we were going for the vacation, but we did know our mom had mentioned getting an early start. Luckily we had retired to my bedroom very early and were able to get in a few hours of sleep before it was time to get up the next day.

Dad had let us know that we would be in the car a while so I decided to go with cute and sexy, but comfortable. I had on a pleated wrap around skirt. It was long enough to not flash everyone, but loose enough that if we happened to get an opportunity for a quickie it could be pushed out of the way without taking it off. For my top I went with a snug shirt that was low cut enough to get stares, but not so low to go from cute to slut. I headed down stairs where Ryan was loading the car. It looked like he might have planned to torture me too. He was wearing a tight athletic shirt that did a great job of showing off his chest and arms. He had jean shorts just loose enough that I could probably slide my hand in his waistband.

Once the car was loaded Ryan and I sat in back with our parents in the front and my dad driving. The first hour or two in the car was ok, a little flirting between Ryan and I, but that was pretty much it. We couldn’t do too much with our parents up front. The radio was on low for background noise so we could talk in softer voices without being heard up front, but if we wanted to have a conversation with our parents we didn’t have to shout. The few stops we made along the way one of our parents was always around so as much as I wanted to touch Ryan I didn’t dare do it. I knew my mom would be ok with it at home, but I didn’t know how she would feel about it in public where we could be seen and caught. Things didn’t really get interesting until the last stop before we left the interstate. My dad came out of gas station convenience store with a foam cooler. When he got to the car he looked over everything and said he didn’t plan the packing very well. The back of the car was full of our luggage so there wasn’t any place to put the cooler. He suggested I sit on Ryan’s lap and we could set the cooler in the back seat. He said we could stay off the interstate at this point and take it easy since I wouldn’t be able to have a seat belt. Ryan and I agreed and we piled back into the car.

The roads weren’t as well maintained as the interstate so there were a lot more bumps and rough parts. It didn’t take long before I felt Ryan get hard under me. I decided to torture him a little by grinding on him a little more than necessary drawing a few soft groans from him as we travelled. Every once in a while our route would take us off the paved roads onto a dirt road. They were my favorite. They say don’t be in such a rush to reach your destination that you forget to enjoy the trip, and I was definitely enjoying the ride.

Eventually Ryan couldn’t take it anymore. He whispered into my ear and asked me to help him take my panties off. He must have seen the look of panic in my eyes as I looked back at him over my shoulder because then he whispered not to worry that my skirt was perfect for hiding anything we did. Just then we hit a small pot hole and he ground into me. The fear melted away into excitement of getting away with it while our parents were right there. Ryan and I were behind dad so we mostly just had to be careful mom didn’t see. I felt Ryan hook his thumb around the waist band of my panties with his right hand. He hid his hand under my skirt. The back of my skirt had slowly worked its way out from under me so I was sitting directly on Ryan’s shorts with just my panties between us. It was harder for me to hide my hand under my skirt so I took the left side slipping my thumb under my waistband where my body hid me from mom’s view. On the next bump I lifted up slightly and we both pushed my panties down so they were just under the edge of my skirt. Then we hit another dirt road and we easily hid the movement of quickly sliding them out under my skirt, past my knees and down to my ankles. I stepped out of them and pushed them slightly under my dad’s seat. Then if we made another stop they would be out of view if anyone happened to look in the back.

The denim of his shorts wasn’t exactly soft, but it wasn’t uncomfortable either. With his left hand he reached under my skirt and around me. I spread my legs a little to allow him access and he began sliding his finger up and down the length of my pussy. He gently slid the tip of his middle finger in me and explored till he found my clit. Then he made small circles the way he had watched me do it when I masturbated. It felt good and was extremely exciting with the risk. He whispered in my ear again and asked me to lean forward and ask dad how close we were getting. I sighed in discontent as he pulled his hand from under my skirt. I started leaning forward and I could swear I heard the soft metallic sound of a zipper. I grinned at the brassiness of Ryan and asked my dad if we were getting close, he said it would probably still be a little over an hour on back roads. I slid back onto Ryan’s lap and he casually held the back of my skirt so it didn’t get trapped beneath me. I felt the skin of his hard cock slid between my ass and lay ridged against my pussy. It was heaven. We tried maneuvering a bit to line him up with me, but it was very difficult since he wasn’t small. Even with the bumps it was very hard to be subtle. We had almost given up when we finally came to another dirt road.

I’m sure if anyone had been paying attention my final bounce was a little high to be believed, but our parents seemed to be talking up front and not paying much attention. He finally slid into me. I was extremely wet from fooling around to this point and judging by the smear of pre-cum across my backside between the two of us there was plenty of lubrication for him to stretch me open and slide in. As he slid in I closed my eyes and lifted my chin breathing out deeply with relief at finally having him inside me. I realized where I was and quickly dropped my chin back down and opened my eyes to see if anyone noticed. I thought I caught a glimpse of my dad’s gaze in the rearview mirror, but I wasn’t sure. We were still on the dirt road and the vibrations traveled up the car into Ryan’s cock and into me. It felt really good, but eventually we ran out of dirt road and returned to pavement. We moved as much as we could without drawing attention. It was difficult to not lose myself and just start riding him, but I kept control of myself. I silently thanked my cheer coach for all the workouts that left my legs strong and able to support me for long periods without getting tired.

Ryan and I had been having sex in the backseat for probably ten or fifteen minutes. It was slow, deep, and felt really good. Then Ryan spoke up and I froze. “Hey dad,” my eyes shot to the rearview mirror, “could you put down the sun visor so we can get a good view of what mom is doing?”

I could only see my dad’s eyes in the mirror, I first read surprise, then the way his eyes scrunched I was guessing he started grinning. He glanced over at mom drawing my attention to her. I couldn’t hear what she said, but looked like she said “sure.” Her sun visor was down, her eyes were just out of view but I could see her mouth which twitched up into a smirk. I was getting even more confused and feeling Ryan’s cock in me was definitely having an effect on my cognitive speed. That’s when I noticed moms arm intertwined with dad’s on the arm rest. Looking closer I could see her arm wrapped behind dad’s, but it didn’t cross back up onto the arm rest, instead it looked like it went into dad’s seat. Her arm was also moving very slightly, but rhythmically. That’s when my brain finally started catching up. I thought my mom might have been giving my dad a hand job in the front seat. I looked back to her visor and the mirror and the fact that dad did not having his visor down also clued me in that the sun was in the wrong place for her visor to be any use. Looking back at the rearview mirror and my dad, I shouldn’t have been able to see his eyes, maybe one of them, but mostly the side of his head. Our parents had been watching us from the front seat since dad suggested I sit on Ryan’s lap.

The thought process seemed to take forever, but only seconds had passed. My dad reached up and lowered his sun visor. I saw my mom’s hand come into view sliding up and down the length of my dad’s cock. As her hand came to the top her thumb and index finger came together rubbing the tip of my dad’s head. The strokes were long and smooth. Then Ryan called back up to the front that it was perfect. My dad let go of the mirror and returned it to the arm rest. Ryan put his hands on my hips, lifted me, and thrust back up into me. I automatically ground down trying to get more of him inside me with a grown of pleasure. Then I let out a deep breath realizing that I’d been holding it since Ryan called out.

I began lifting myself higher before grinding down onto Ryan. I started letting sounds escape my throat as I stared at my mom’s hand working my dad’s cock. It was unreal. With all pretenses gone mom shifted in her seat so she could watch Ryan and I in the back without the mirror and sped up her stroking.

After several minutes Ryan said, “This is so fucking hot, I’ve got my dick deep in my sister while watching my mom give my dad and hand job.”

My mom responded, “You’re telling me. I’m about to have an orgasm and I haven’t even been touched yet.”

“Well don’t let us stop you,” said Ryan. My mom looked into my eyes with a devious smile. She used her free hand to unfasten her seat belt and her pants. She slid her hand down the front and let out a deep breath briefly closing her eyes.

I came. Hard. It was even better than the pool. My legs completely gave out, luckily Ryan had no trouble supporting me and continuing his slow deep thrusts into me. Both he and my dad were grunting and I loved the sound. Dad had turned off the radio so the grunts, deep breathing, sounds of mom’s stroking and fingers with Ryan sinking into me were all incredible music to me.

My dad said, “Oh god yeah, honey I’m going to cum really soon.” Mom stretched across the arm rest. We couldn’t see her take dad into her mouth, but we could see her head bobbing up and down on him. Dad’s eyes roamed between the road, us in the backseat, and his lap. Considering everything going on he did a really good job keeping us on the road, though it helped that we had the road to ourselves. It wasn’t long before the deep grunts started with slow heavy breathing. It was clear he was cumming in mom’s mouth. He seemed to go off for a significant amount of time and we could hear mom slurping and swallowing even in the back. When she finally sat up she made an “mmm” sound and licked her lips. This set me off again for my second orgasm. Hearing my moans and my grinding brought her attention back to Ryan and me. She lay back against the passenger door. We could see her hand moving quickly as she masturbated.

She commented on how hot Ryan and I looked. I got my legs back under me and with Ryan keeping a firm grip at my waist we were able to pick up speed. With my left hand I grabbed the back of dad’s seat for balance. With my right hand I took my right breast in my hand under my shirt.

Mom let out the hottest moan as she climaxed. She trembled and grabbed at the back of her seat as she rode out her orgasm. I felt another on the way, but I could feel Ryan’s cock swelling inside me as he finally lost control. I felt jet after jet of hot cum shooting up inside me filling me completely. I was so close, I let go of the back of the seat to lift the front of my skirt. I let go of my breast and moved my hand down to my pussy. I sat fully down on Ryan’s cock grinding into him while I stimulated my clit with my fingers. My third orgasm hit me and I closed my eyes riding out wave after wave of heat, pleasure, and shaking as tingling spread through my body. I collapsed back onto Ryan, his cock and cum still filling me.

My world was still spinning as I heard dad in the front say that we were almost there and needed to make ourselves presentable. He suggested we turn the cooler sideways so I could buckle into the middle seat. At that I gave him a “seriously” look in the rearview mirror. Yep, set up again. Not that I minded though.

I leaned forward and stretch for my panties under the front seat. I slid them on my legs, avoiding raising myself until I had to allowing Ryan’s cock to slide out of me. I put my panties the rest of the way on quickly trying to capture as much of Ryan’s cum in my panties as possible. Ryan had only let down his zipper to let his cock out so I wanted to avoid too much running out of me onto his shorts if possible, and I also enjoyed wearing clothes covered in his cum, so win-win. I was mostly successful. I didn’t think anyone would notice the small bit left on the front of Ryan’s shorts. I pulled down my skirt and straighten out my shirt. While I slid off Ryan’s lap Ryan got himself back into his shorts and fastened them. My mom got her pants fastened, then leaned back over the console to help my dad back into his pants. She commented that he was getting hard again and hated having to put him away. From my new vantage point I could see that she couldn’t help but give the head of his cock a lick before fastening him back up.

We all got situated a few miles before we entered a little town. We stopped for gas and at a small building where dad picked up the key to a cabin my parents rented for the vacation. We all got out and stretched our legs a bit. Dad said the cabin was just ten minutes outside town. By the time we piled back into the car for the last stretch it had aired out a little, but there was no denying the smell of sex in the air. I was worried that it would be awkward when we all got back together, but everything seemed quite normal. We made small talk about plans for the week, a few laughs. It also felt like no one was trying to avoid talking about what had happened. Dad had even cracked a joke about the smell of sex in the car that everyone got a good laugh over.

We pulled up in front of a modest story and a half cabin. It was situated on a small lake out back. We started unloading the car and taking a look around. There was a loft area overlooking the living space on the main floor with two king sized beds and a decent sized bathroom with a roomy multi-head shower. There were stairs running up one wall to the loft. Opposite the wall with the stairs was a kitchen area and small island. Under the loft sat a dining table and two rooms. One turned out to be a pantry, the other a large full bathroom. There was a TV but by the way it was situated compared to the seating in the living area, you could tell it got little use by anyone staying there. To the back of the cabin was a set of French doors that led to a large deck complete with lounge chair style sitting area and a grill. There was a small beach leading into the water. Mom said it is a private beach. There were two other cabins on the lake. Bends in the shoreline kept the other cabins out of sight unless you were a good distance out on the water.

I got a chance to ask mom about the sleeping arrangements. She just said that the car was a good test to see how everyone would feel about being openly sexual around each other and everyone seemed quite comfortable with it. So if she and dad felt like having sex, they would. She also said if Ryan and I felt the same way, we were certainly welcome to as well. Knowing mom’s interest in watching I was sure she was hoping we felt like it often.

As I carried things upstairs I always had Dad or Ryan following me up with something. I suspected they were following me up to catch glimpses of my still damp panties. I confirmed this by walking to the edge of the balcony several times to ask questions over the rail to one or the other downstairs. The rails were far enough apart to give a good view and by the tightening of their pants I was getting the reaction I was looking for and enjoyed the attention. I was also enjoying watching them carry the heavy items from the car as their arms tightened and you could see their muscles working. Although it wasn’t very hot Ryan took off his shirt as he unloaded the car, probably his version of standing at the edge of the balcony in a skirt. I also spotted Ryan and dad checking out mom’s ass as she moved about the cabin. I saw why mom wasn’t upset by dad’s interest in me as Ryan’s interest in mom excited me.

It didn’t take very long to unpack the car. We were finishing up with mom and dad upstairs getting things put away and I had just finished organizing the island that separated the kitchen from the living space. My back was to the living space when Ryan pressed up behind me and whispered in my ear that he wanted me so bad right then. I whispered back, “so take me.” He lifted my skirt and took ahold of my panties pulling them down. He went to his knees with them and I stepped one leg out of them spreading my legs. He gave my pussy a lick to be sure I was wet enough, which wasn’t a problem. I’m sure he tasted the two of us from earlier and seemed to enjoy it as he stuck his tongue deep inside me several more times before standing. As he stood I heard the metallic sound of his zipper once again along with a large movement that was him unfastening the button as well. I felt his hot cock press against my ass as I leaned back forward pushing back into him. I braised my hands on the counter and smiled with a big grin at what I knew was coming next.

I felt his cock slide the length of my pussy spreading my wetness the length of his cock as he felt his way to my opening.