A Trip to up North

There we were on the roughly 2 hour trip to my grandparents house for the weekend. It was a warm June evening and the sky was clear. We left about an hour before sunset which would get us there a little after dark which isn't too bad. Way outside of any after work traffic. I had lacrosse practice after school which allowed me to ride with Jennifer, my sister and her best friend Michelle who traveled with us regularly. Our brother Jeremy had already gone up with our parents right after school.

My sister and I were pretty close. We talked about just about everything under the sun from school to sports to video games and even received some advice for some of the crushes I've had over the years. She was a best friend to me and we had always gotten along so riding with her and Michelle would be a blast!

One crush she was unaware of though, was my lifelong crush on Michelle. Well, to me, she was unaware of it. I don't think I was too good at hiding it. I'd been caught staring a few times, romantacising about her and was guilty of always being around when she was there.

We were about an hour into our drive as the sun was setting and I finally saw one, the first car to pass us with one headlight out. I finally had my chance!

"SEX" I yelled more confidently than anything I've done in my life.

The first time I've ever yelled it with the full intent of playing the game. Jennifer didn't even cross my mind as she was driving and always a very innocent woman. Sex scenes in movies made her blush. I was way too interested in Michelle to even care what my sister thought or whatever happened.

Michelle had been my sister Jennifer's best friend for basically her whole life. They're both 19 and are going away to school this fall. with me being a year younger, it made for getting along with them pretty easy.

She was a varsity volleyball player in every aspect and then some. She was about 6 foot tall, long toned legs, a round and toned bubble butt and a nice set of curvy hips. Mounted directly above that was a muscular stomach framed nicely along the top by a rather busty set of 34 D breasts. She had a slightly longer neck topped with a very cute face, a little button nose and a set of gorgeous brown eyes silhouetted by a very lush head of brown slightly curly hair.

She was absolutely gorgeous and a common guest in some very nice dreams and thoughts I've had from time to time. She was very well endowed and I had noticed what boobs were spending days at the community pool with her.

I'm more surprised I had yelled that out loud at the sight of the first car in the dusk light as we traveled down the highway. The game until this point had just been practice. Actively watching out for cars with only one headlight. Each one yelled meant another point in my column. But now I was fixing to play in the majors. Each one yelled out by me would mean one less article of clothing for Michelle if she would bite at the competition.

"Haha" she laughed. "Do you really want to play that game?"

"Yes Ma'am!"

"Fine, first point to Jack." She said sarcastically.

"No, I mean we really play. How the game is meant to be played."

With that she leaned forward to turn around to look at me in the back seat, "You're gonna lose".

As she turned back facing forward, she slid her left hand down to her waist and unclicked her seat belt. Her left hand transitioned to the bottom hem of her grey top.

Michelle was wearing a pair of dark, slim blue jeans that hugged her legs nicely. Below she had on a pair of white Adidas shoes with the black logo contrasting with the white frantic and standing out against the dark lightly flared bottom of the jeans. I had admired the fit of the bottoms as she threw her bag in the trunk as I was walking outside.

The only thing that looked better than her bubble butt bent over was the view getting into the car. Overlapping the tops of her blue jeans was a tight and thin fit medium grey spaghetti strap tank top. The straps thin and allow the top to dip down just enough to show a handsome amount of the top of her cleavage. It was very evident that she was wearing a push-up bra that really shelved the gals up higher.

As she climbed in the car with me in the back seat behind the driver seat, she leaned in to put her water bottle in the cup holder. As she did, a great view of the grey shirt straining to contain her cleavage really pushing up and chest trying to escape through the neckline of the shirt. It was beautiful.

Snapping back to the current moment, she had grabbed her shirt and began to lift it up along her side. As the shirt sliding up exposed her stomach, my heart stopped as a sliver of deep red began to show. The red of her bra contrasted greatly with her slightly pale skin. As the shirt climbed, the whole side of her left cup was now exposed as she finished pulling the shirt over the top of her head. She shook her head to fluff her hair and then turned around in her seat to look at me and set her shirt by her feet.

As she returned her hand to her lap, she passed over her knee and put her right hand on the center console as her other arm was pinched at her side. The result was her looking back at me with her arms pushing her chest together in one of the most beautiful sights. She had a slight grin on her face as my eyes locked on her brown eyes. After a second my eyes veered down to her smile and then to her neck. What I saw was the 34D breasts pushing up and out of the top of the beautiful red cups of her smooth silk push up bra. They were pushed together creating a long and narrow line of cleavage as she pushed up with her right arm allowing them to almost spill out completely. She laughed and then turned around right after both of my hands slid into my lap.

"Are you seriously going to play? And starting there?!" Jennifer blurted out looking over at Michelle.

"Please, he doesn't stand a chance. His eyes won't be anywhere else for the next hour with these girls on display," she laughed.

She was right. I was already hard.

"Sex" broke the silence a few minutes later as Michelle called.

Off went my shoes.

Michelle and Jennifer had begun talking about the end of the school year and their respective schools for the fall. About 15 minutes went by before I saw my next chance. "SEX!" I yelled, interrupting them.

Michelle removed her shoes.

Another 5 minutes goes by, now interrupting their conversation about their summer plans with their 2 other friends and their trip to Virginia, I confidently state "sex."

Michelle tosses her socks back at me.

As I was lost in thought and their conversation continued about lord know what, Michelle got me with one mid sentence and before I could take one off, she called "Sex" another time. 2 cars on the opposite side of the road, each with one headlight. What are the odds?

My socks had just come off and I pulled my t-shirt over my head and tossed it over her shoulder into her lap.

"Sex!" Michelle yelled confidently. Three in a row.

My jeans were the only piece available to be removed. I was suddenly terrified and hesitated. Michelle had turned around to look at me and laughed.

"What are you, chicken? You started this game!"

I was scared. It was hard and I was not ready to show that off yet, I was just hoping to see Michelle in a bra and maybe topless. I had never thought what would happen if she would take the lead!

"I'll only continue if everyone plays" I stated as a last ditch effort to get the game to pause. I already saw what I had wanted. Michelle had already given me a grand show right off the bat showing off the girls and a few other times as she turned around and pushed them together. She knew she was driving me crazy and she was trying to get me back. But luckily I had a way out. Jennifer was driving and also my older sister. The only way my pants were coming off is if she agreed to play a strip game with her friend and brother while she drives and I strongly doubted that would happen.

"I'll play" I heard quietly from the front seat.

My stomach dropped. My heart rate skyrocketed. Michelle laughed and said "she's in, take them off!"

"She's already 3 rounds behind, she's gotta go first then!"

Jennifer told Michelle to grab the wheel as I saw Jennifer pull her white t-shirt over her head. She tossed it behind her seat and right on to my lap. I grabbed the shirt as she took the wheel back.

My eyes shifted from the shirt in my hands to the back of her seat and then to the skin of her right shoulder and the black strap of her bra. I leaned a little more to the right and was able to see her neck and the side of her face. She was in and now sitting 2 feet away from me in a bra.

Jennifer and Michelle were different. While Michelle was incredibly athletic, Jennifer was more of an intellectual and helped Michelle with homework. Jennifer was only about 5'6" and right on the line between thin and curvy. A line she handled very well. She was a very cute girl, she wore glasses and wore jeans and t-shirts a lot. Occasionally she would dress up for a date here or there or a school dance but you would typically find her in a ponytail.

I had never really noticed much else or paid too much attention to my sister's physical attributes, but she has long, dark brown hair, a rather fair complexion, big brown eyes and a cute shy look to her. During this past summer there were a few times we had gone swimming and she had worn a conservative bikini, she had a nice little kaboose on her, nowhere near the bubble butt Michelle had, but it was nice and toned. She didn't show them off much but you could tell she was probably a 32 C and very good at keeping that private. But for the first time, she was in a bra in front of me and I was interested.

"Quit staring at your sister's chest and own up! Your turn" Michelle said jokingly.

I snapped out of it and leaned back to my seat. I unclicked my seatbelt and unbuttoned my jeans and then slid them down and off. Michelle getting a great initial view of the tent now camped out in my boxers. Once the jeans were on the floor, my hands quickly returned to my groin.

Michelle chuckled quickly "wow, you're not too much of Jennifer's 'little brother' any more, are you?"

"I guess at least you like the view"

As she was turned, I saw a car out the windshield with only one headlight.

"SEX" I yelled. Now I am nervous... Michelle had either the bra or pants to choose from. She quickly decided on the latter. She unbuttoned her jeans and lifted her butt off the seat and started pushing them down. Each inch exposing the matching red color of her bra on the slightly lacy panties. From what I could tell, they were boyshorts. She finished pulling her bottoms off around her feet. Michelle is now sitting there In her matching push-up bra and boy shorts.

Jennifer opted for the easy removal of her sandals which ended up in the seat next to me as she threw them over her shoulder and kept driving.

"Sex" I heard called from the front seat as I began to panic. I realized it was my sister who called it and thought about Michelle in her bra and how either that was coming off or how she'd be removing her matching red panties. My sister's best friend and a huge crush I've had since I was a kid is going to be half naked in front of me. And then it hit me, as a result, I too, would have to remove an article and I froze. I was rock hard back here and there's a beautiful girl in the front seat who is highly competitive. My boxers were coming off, unless...

"These are only coming off if someone takes them off" I shouted quickly. At first hopefully prompting Michelle to remove hers first but I heard something I didn't expect.

"I'd love to give you a hand but I'm driving, '' Jennifer laughed from the driver's seat. She gave me a quick playful look in the mirror and it was speechless. Did she just joke about removing my underwear for me and actually mean it? Would she have actually done it? What does that black bra look like on her?! So many questions buzzing through my head quickly.

"I'll go back there and take care of it for you," Michelle exclaimed, snapping the questions out of my head. The last question rang in my head as Michelle turned around in her seat to look at me.

"I doubt that" I snapped back.

She responded by reaching down and unbuckling her seat belt and told me to move over behind her seat. I did as instructed. As I did, she slowly pulled her knees on to her seat and leaned for the gap between the seats.

If I had thought the first glimpse of her in her bra was amazing, that had nothing on this. As she reached for the seat to my left, her girls were on full display. Each breast testing the capacity of the red bra. Both bouncing lightly with each bump of the road. They were both pouring out of the bra as she made her way back. As she moved more into the seat next to me, my eyes traced along the curve of her back as the red of her panties came into view. As she climbed, she really arched her back to stick her ass up in the air and really pushed her chest forward. As a result, the red fabric clung to her ass and showed the entire curve ending with a perfect view of her lower cheeks sticking out of the bottoms and framing the sliver of red between her legs. She paused in this position facing directly away from me and her ass slowly moving toward the back of the car no more than a foot away.

Once her hips met the seat, she turned around and sat on the seat behind Jennifer and looked at me and then the boxers containing my rock hard cock.

She quickly leaned forward and grabbed the side of my boxers and tried to yank them down but while sitting on them, I grabbed and kept the waist band firmly in place.

"You have to remove something too!" I nervously joked.

"I will if you will"

"I will if you go first"

She paused for a moment and then turned her back to me. Her hands slid up her sides and behind her back as she reached the clasp and unhooked it. The two ends fell away from each other as her hands now slid the straps off her shoulder and she tossed the bra at me.

She returned her arms and hands to her front and crossed them across her chest and turned around. She gave me a quick smile and smirk and then lowered her arms.

I watch in astonishment as her arms felland slowly released her breasts. I stared and swallowed hard as her 34D's lay undressed in front of me. Both as perky as can be and each nipple slightly stiff and both staring me in the eyes.

For a moment it almost looked like I was zooming in on them but then I quickly realized what was happening.

Michelle leaned forward quickly and grabbed the hem of my boxers and pulled the front down. In doing so, my cock sprang out and collided with her arm. My warm erection met the cool touch of her wrist. Her hands remained on the hem of my boxers and right next to my staff. I was in awe, Michelle was sitting in front of me, leaning forward, topless, with her hands on my groin and my hard cock out.

It seemed like eternity but in reality it was just a couple seconds. She then asked "Are you going to let me remove them all the way or do you just want to say you lose now?"

I quickly fumbled my hands to my side and pushed myself up off the seat. Michelle leaned more forward, now her head only a foot away from my chest and another foot from my groin. She adjusted her hands which placed one firmly against my dick as she slowly pulled the boxers down to my knees. When she got to my knees I found the courage to make a move and I pushed my pelvis forward and launched my member up toward her face. I got close but didn't make contact. She quickly swung her hand up to her face to protect herself and ended up wrapping her hand around my shaft. She then looked at it and then myself as I lowered my hips back down to the seat.

She laughed for a second, slid her hand the length of the shaft as she let it fall back in place. She then sat back up in her seat. "See, that wasn't so hard, was it?"

"How hard?" Jennifer's voice came from the front seat as she turned around quickly and met my glance. She then quickly directed her gaze down to my groin, "looks like it was pretty hard to me".

When she had turned, she had exposed more of her chest in the black bra she was wearing and I was able to see some of her cleavage. Now that I was in this vantage point, I was able to see more of my sister's exposed body. Suddenly and briefly I had forgotten about Michelle and was thinking of the beautiful young woman in the driver's seat who was one call away from being in only her underwear.

I felt the cool touch of Michelle's fingers against my leg again as she lightly caressed it "that was a pretty big twitch there. Did you see something you liked?" Michelle asked as my gaze centered back on her. I watched her eyes, smile and exposed chest as she lightly ran her fingers along my thigh.

Just then I felt the car jerk just a little and Michelle pulled her hand back to herself.

My eyes jumped to the front of the car to see why we quickly corrected our course. It didn't look like anything directly in front of us but in the distance I saw headlights. It looked like 2 cars but I couldn't be sure. And then I saw it.

"Sex" I called as I saw the car with one headlight.

Finally, I got to call and I didn't have anything else to take off! And both of them did! Michelle only had one item left and it was coming off! Jennifer had a few left and one was coming off! My eyes went from the road to Michelle sitting next to me and then to Jennifer in the front seat. And then back to Michelle as she rolled her eyes and pushed her hips forward.

I watched as her thumbs hooked into the tops of her panties at her waist. She then slowly pushed her hands down and slid them down her long legs. As this happened I was now able to see the curve of her ass without the fabric and it was glorious! She had a very subtle tan line from her time at the pool over the summer. Her ass from the side looked fantastic! My eyes ventured toward the front as I noticed just the slightest bit of pubic hair. It looked like she kept it just shy of shaved and very clean. Due to the way she was sitting, I wasn't able to see much more. I could feel my member twitch as she slowly lowered her hips back down to a sitting position. As her butt made contact with the seat I was hit in the face by something thrown from the front seat.

I was now sitting in the same seat that Jennifer was throwing her items and this last one hit me square in the face.

As it fell, I realized what it was. The black fabric of her bra was laying in my lap on top of my hard cock. My sister's bra was laying on my cock. Jennifer had skipped the normal route with pants next and went straight for the bra... my cock twitched as my eyes went from her bra on my lap to her in the front seat. No more black strap, no more side of her bra visible. Just skin. Just bare skin. I leaned forward slightly and was able to get a quick side profile of my sister's right breast. My eyes traced the outline of her milky white skin in the dimly lit car. My eyes could make out the entire side of her perky breast. I felt myself twitch again. My gaze was fixed. Nothing could break me from it. I turned my body, putting my leg on the seat to my left. This gave me a better view of the front seat.

From this position I could see Jennifer topless in the front seat and as I gazed to the left, Michelle was completely naked. My eyes were glued. I couldn't let my eyes close on such a sight in front of me. My sister's breasts were out, and she willingly did it and was aware I could see them. I had almost forgotten about Michelle as we merged to get off the highway. We neared the light and Jennifer turned to face us in the back seat. As she did, her left arm came across her body and pushed her chest together. My dick twitched at the sight of my sister's nice perky tits pressed and her eyes meeting mine, then looking toward Michelle.