Road Trip With The Babysitter

It's funny how little things you see, hear or, smell trigger memories. I was driving home from work today and was reminded of one of the best sexual experiences of my teens.

It was the end of a very bad week for me and finally Friday came. Only marginally better than the previous four days, I was still in a cranky mood during the drive home. I live outside of a large Midwestern city so once I clear the burbs the highway opens up and I tend to relax. As usual I kicked the cruise up to just below eighty and started to ease into my seat. I opened the sunroof, tuned in the local alternative station and began to let the bad week slip my mind.

I was almost at ease when I came up on the red car. I put on my turn signal and moved to the left to pass. As I eased up next to him the dumbass began to drift into my lane. I swerved and began to utter some rather explicit names when I saw the head of a cute blonde pop up out of his lap. A stray streamer of his cum still stuck to her lips.

He mouthed the word, "sorry." All I could do was smile, nod, and mouth back, "it's cool." We shared a knowing look and I sped back up and my mind began to remember a day much like this, about 12 years ago.

My friend Marv and I got tickets to the biggest music festival, Lollapalooza. The only draw back was it was about four hours away and it was on a school day. We were so close to graduation that we felt we had earned a day off. Our parents weren't as sure. They didn't really trust us driving to St. Louis by ourselves, let alone skipping a day of school.

We beg and pleaded and finally came to a compromise, we could go if we were chaperoned.

We didn't like it, but agreed anyway. We had no idea who they would find as a suitable chaperone. With just a couple of weeks before the trip my mom came home with the news. Her boss's daughter and her friend would take us. There was just one catch, we were not allowed to drive home that night. All parents thought that we would be too tired, and didn't want us risking the drive home.

Marv and I had to come up with the extra money to pay for our hotel room and the trip was set. Trust me we did not want to spend all day driving with 2 college girls who felt compelled to baby sit us and would tattle back to her daddy, my mom's boss, any indiscretions that may occur. We're we ever way off.

Marv and I waited outside my house around five the morning of the trip. The headlights of the Lexus nearly blinded us as it pulled into the driveway. Our "babysitters" Leah and Darcy got out and introduced themselves. I hope to this day I didn't look as stupid as Marv did when we first saw the girls. I'm pretty sure that I did though. Leah was probably five foot five, 105 to 110 pounds, with long black hair and the brightest blue eyes. Darcy was a little taller maybe five foot nine, with medium length brunette hair, and hazel eyes.

Both girls had awesome bodies with Darcy having a major advantage in chest size. Both girls were dressed in shorts and t-shirts and tennis shoes. Leah finally spoke and said," I'm Leah and this is Darcy. My dad said that we could use his car. He seems to think it's a little more reliable than mine." I just nodded and stood there. Almost oblivious that Marv was still there he spoke," Umm, you ready to go?"

His words broke my daze and we all climbed into the car. We made small talk as we drove and I was being to think this wasn't going to be too bad. We all agreed that our parents had pretty much arranged this and nobody wanted to be babysat, or the babysitter. We also decided that once we got to the festival we would all split up, do as we wanted, and meet back at our hotel rooms.

About an hour into the drive Leah said that she was getting tired and wondered if someone else would drive. Marv agreed and we pulled off at the next exit. We switched around so Marv was driving, I was behind him with Leah in the bac with me, and Darcy in the passengers seat. Leah dozed off shortly after we began driving again and I soon followed.

The sun was coming up and the sheer brightness woke me. I started to ask what time it was until I noticed Darcy's head in Marv's lap. She was sucking his hard cock and doing a damn good job from what I could see. Marv looked into the rearview mirror and our eyes met. He grinned and I smirked back at him. He looked down and mumbled something and I felt a hand creeping up the inside of the leg of my shorts. Darcy's slender fingers nimbly moved into my boxers and began to stroke me to life.

I couldn't believe what was going on. My best friend and I were getting done st the same time by the same hot girl. Soon I saw Marv tense and Darcy's bobbing head stayed firmly planted in his lap. She finally came up and looked at me. "He was dozing off so I thought I would keep him awake," she said almost as it was a clinical recipe for drowsiness. I just smiled and shook my head. "However now I'm horny and could really use some help getting off. You game?" she asked me.

"Sure, Whatever it takes to keep you from dozing off,"I replied with a smart assed tone. Darcy then spun around and climbed into the backseat with me. This woke Leah and it took her a sec to realize what was going on. Once the sleepiness made way to clearer thoughts Leah climbed up front and muttered,"hoe" as she scrambled past Darcy.

Darcy didn't waste anytime, she pulled my cock out and sucked me deep into her throat. Soon I was fully hard and lodged in her throat. I reached down and undid her shorts. My hand slipped inside her tight panties to find a neatly trimmed bush and a soaking wet pussy. I slid a finger passed her swollen lips and began to explore her damp folds. I added a second digit and Darcy began to fuck herself on my hand. Soon she had enough of that. She released my hardon from her lips and pulled herself off of my fingers.

Darcy made me lay down in the seat and she climbed on top and drove my aching cock deep inside her. Keep in mind that I was only eighteen, in all my sexual adventures to date I was the one in control. Darcy began riding me as she strummed her clit. I started to thrust into her, but it was disrupting her rhythm and she took control. She rocked her weight forward pinning me down. She began bouncing up and down fucking me. Soon her pace quickened and she began to moan.

I had only seen this in pornos that friends had smuggled from parents or older brothers. I soon witnessed firsthand a woman having an orgasm. Darcy tensed, then moaned one last deep moan and I felt my cock suddenly growing wetter as her juices flooded me.

Something in my eyes must have alerted Darcy I was going to come because she jumped off of me and took me in her mouth as I exploded. She swallowed every drop. I had never experienced this because girls in my high school barley sucked dick and when they did you'd damn near have to put a gun to their head to get them to swallow.

She giggled as I slumped deep into the leather seats. Leah became the first to speak," well so much for being good and not acting like little sluts, huh Darce?" She looked at me and continued," Mike, please don't say a word to your mom. If this gets back to my dad he'll kill me."

"Leah, what do you think I'm going to do? 'Hey mom on the way to St. Louis you boss's daughter's best friend blew Marv and fucked me silly," I asked.

"You keep being a smart ass and that'll be the only piece of ass you get on this trip," she retorted.

I didn't press the issue any further, but Leah's words kept me wondering what else was she insinuating. We rode the rest of the way in silence, I was hoping that I hadn't pissed Leah off ruining my chance at cracking her panties.

We finally arrived in St. Louis. We pulled over and Leah once again took over driving. We all started watching the streets trying to find our way to the hotel Leah's dad had booked us rooms at. Well all of us except Darcy. She was making lewd comments about guys we passed and making suggestive motions with her tongue and mouth. Leah scolded her, but never told her to quit. We located the hotel and found a parking place.

We checked in and Leah acted as her father would have expected, very professional and polite. She was just about to have the keys to our rooms when the desk clerk informed her that being that because neither Marv our I were 21 that Darcy and her would each have to share a room with one of each of us. Darcy's eyes lit up, Leah shot her a dirty look and said, "This will be fine, we're all adults. We can do this with no problem. Mike and I will take one room, Darce you and Marv in the other," Leah said seeming very parental all of a sudden.

We went up stairs and adjourned to our separate rooms. The concert started in about 3 hours and we had the desk arrange a cab ride to and from. Leah seemed stressed about the room sharing arrangement, but that lessened when we found that the rooms shared a patio that looked over the pool and hot tub area. I ran back down to the car and grabbed our bags and brought them up. Leah found this to be chivalrous, but assumed there was a hidden agenda behind my intentions.

I claimed the bed closest to the sliding door that lead to the patio. Leah still acted standoffish as she laid out her clothes before heading to the shower. I sensed that she wanted the room to herself to get ready so I walked out onto our patio and started to walk in to Marv and Darcy's room when I noticed through a small opening in the drapes a quite funny site.

Darcy had Marv butt assed naked on his hands and knees. She stood behind him spanking him. I almost fell off the short drop to the pool deck, I was laughing so hard. To this day I have never mentioned that I saw that(oops guess I just did.....sorry Marv). I walked back into my room and laid on my bed and flipped on the tv.

I was flipping through the channels when the bathroom door opened and Leah stepped out wearing only a towel. There was defiantly an awkward moment as I stared at her wet body. Her dark, wet hair clung to het body in long shiny strands and I began to think very naughty thoughts. I jumped up and told her I'd wait out on the patio and she could have the room to get ready. She said I didn't have to if I promised I could be good and just sit on the bed and watch tv.

I did as I was asked, but I couldn't help stealing a glance every now and then. Her breasts while not as large as Darcy's were topped with the most delicious looking nipples. Her entire body was trim and toned. Her muscles were evident, but not overwhelming like that of a body builder. Her pussy was entirely bare of any kind of hair. Her moist pink lips were puffy and I just longed to be able to touch or lick them.

Every time Leah would look up I would look back at the tv and try to pretend that I was engrossed in the program on the boob tube. Eventually she was dressed in a pair of tight shorts, an even tighter tank top sans a bra. She took her towel and began drying her hair as she sat on her bed. "Big fan of cooking?" she asked. At first I didn't understand then as I began to really pay attention to the tv I discovered I had stopped flipping channels on some cable access channel that was featuring two women teaching cooking to a small in studio audience.

I was busted. I started to stammer an excuse, but Leah just smiled and went into the bathroom to brush her hair. I lay on the bed feeling confused. Leah had to know that I would look, yet she wasn't upset when I did. Her earlier words rang through my head,"You keep being a smart ass and that'll be the only piece of ass you get on this trip." What was the game she was playing.

The time passed slowly and finally it was time to go. We piled into the cab that the hotel had called for us and rode over to the show. At the gate we agreed to meet back at midnight or 15 minutes after the last act concluded whichever came first. Marv and I drifted from stage to stage watching numerous bands, and occasionally ran into Leah and Darcy.

The final act of the night was The Red Hot Chili Peppers on the main stage. Marv and I crowded the stage early so we could get as close as we could. About 10 minutes before the Chili Peppers were scheduled to take the stage there was a little uprising from the crowd behind us. We turned and saw Darcy letting some guy do shots off of her bare tits. Marv smiled and I just shook my head. Leah made eye contact with me and motioned for me to save them spots up near the stage.

After Darcy's shot service the girls made their way through the huge crowd to us. "Hi sweetie," Darcy said as she hugged Marv. She whispered something in his ear that made him smile ear to ear. Leah grabbed my arm and pulled me to her. I could smell the beer and shots on her breath. "Stay close to me, I don't wanna lose track of you tonight," she said then giggled as she pulled me to her for a tight hug.

Soon we heard the distinctive notes rolling off Dave Navarro's guitar and our attention became focused on the stage. We had a great time with the girls as we watched one of the most amazing alternative bands ever. Leah would grind her ass into me every now and then, or dance behind me her hard nipples poking into my back. The girls somehow convinced guys around us to buy them beers which usually ended up with me or Marv drinking them. Soon I had a good buzz going, but it as anything must come to and end.

We made our way to the front gates and found a pay phone. Leah called the hotel and had our ride sent over. Darcy flirted and teased a lot of the guys that walked by as we were standing at the pay phone. Soon a guy approached her and asked if she wanted to party. She said no but told him we were looking for some beer. They chatted for a little bit then she followed the guy to his car. We found out later that she went to the car and the guy and his friends gave her all the beer left in their cooler for letting them grope and fondle her tits. The deal clincher was getting the cooler for letting one guy the nipples of her perky melons.

Our cab arrived and the driver told us that we had to either put the cooler up front or leave it. We threw it up front meaning all 4 of us had to cram into the back seat. We piled in with Marv in the middle, Darcy behind the driver, me behind the passengers seat, and Leah half on my lap half on Marv's. We rode this way and every now and then Darcy and Leah would share a look then giggle. I took it for drunkenness, but it turned out to be some kinda unspoken conversation between the two of them.

Once we were clear of the exiting traffic the girls calmed down and we all sat in silence. I could smell the wonderful scent of Leah's hair as she rest back against my chest. She must have sensed my attraction because I soon felt her taking my hand and holding it tightly in hers. Slowly she began to move my hand to her inner thigh. It was so soft and smooth that I began to slightly stroke my fingers up and down. Leah wiggled slightly and her breathing began to quicken as my fingers explored the hem of her shorts. I could feel the blood beginning to fill my limp member. This could be the ending to a perfect evening.

I was just beginning to get bolder and allow my fingers to work up the leg of Leah's shorts when we arrived at our hotel. We filed out grabbing our cooler and headed up to our rooms. Once inside Darcy suggested we sit on the balcony and drink the beer she worked so hard to get. I wanted to stay in and go to bed possibly having Leah join me, but I agreed to hang out and have a few beers.

We had been sitting there about a half hour or so talking about the concert when Leah commented that the pool was empty. It was almost one in the morning and the pool closed at eleven, according to the sign in the lobby. Darcy immediately took the hint and scurried over the railing to the short drop to the pool deck. Marv started to make a comment about not having swim trunks when he noticed Darcy stripping down to nothing. Leah was halfway over the rail when I jumped from my lounge chair to follow.

I climbed over the rail and dropped to the cold concrete of the pool deck just in time to see Leah's naked body dive into the cool water. I quickly removed my clothes leaving them by the balcony just in case we should have to make a quick dash for the room. I ran to the pool and dove in head first.

It was hard to make out much in the dark, the parking lot lights barely lit up the water. I began to swim towards the nearest figure I saw, and as I approached I realized it was Darcy. She turned to me and reached out and grabbed my cock under the water. "Hey your not Marv," she said in an almost whisper.

"Leah is over there and if you hurry she'll probably fuck you blind. She gets really horny when she drinks." I needed no other hints or suggestions. I swam to where Leah was resting against the ladder that led out of the deep end of the pool. I started to say hi when she pulled me to her and began to kiss me passionately. Our tongues met and probed each others mouths. Her hands began to roam all over my body as did mine over hers. We were like to people who been deprived of some necessity of life. We explore each others bodies with our hands and mouths.

This hurried animal like approach soon quit as my mouth descended on her hardened nipples. I licked and sucked at them, her soft moans urging me on. Leah moved back so that she was now sitting on the top step of the ladder, out of the water from the waist up. I kissed my way down her stomach and took a deep breath as I went under the waters surface and began to lick her pussy. I swirled my tongue in and out and licked up and down her labia stopping only to come up for air as needed.

I had just come up for the fourth time when we heard Darcy cry out in an obvious explosive orgasm. Many of the lights in the pool side rooms came on. Leah began to hurriedly climb the ladder and make a run for the room. We must have been on the same brainwave because I was right behind her.

We ran to the balcony, and after placing my hands on Leah's beautiful ass as I boosted her up to the railing, I tossed my clothes up to her and climbed up. Being the quick thinker she was, she grabbed some towels from the room to cover up with in case a security guard came to check things out.

Marv and Darcy scrambled up to the balcony just as Leah returned with the towels. Leah shot a quick look to Darcy and sat on the lounge chair with me. Marv followed Leah's suit and grabbed some towels from their room and returned just in time for Darcy to hand him the last beer from the cooler.

We sat there just chatting when Leah began to stroke me slowly. I had gone somewhat limp in all the action. It was dark and nobody but me could tell what she was doing. I was just getting back to full attention when the door to the pool area opened. A flashlight lit its way around and we all ducked behind the railing of our balcony to watch as a security guard checked the pool area. "Well I guess we should take our party inside," Darcy whispered. She giggled quietly and waited for approval of her idea. The security guard left and Leah finally replied. "It's a long drive back, and its getting late. I'm going to finish this beer then crash for the night."

"Well then I guess I'm going to take this boy in and fuck him silly then," Darcy retorted taking Marv's hand and pulling him up. "Night,"he muttered to no one in general as he followed her into the room.

The door had barely closed when Leah pushed me back onto the lounge and began to kiss me. Her hand resumed stroking me bringing me to full erection. "I thought they'd never leave," she said as she pulled away. I could only make out her silhouette as we lay there, so I was taken by surprise when I felt her warm mouth engulf the head of my dick. It felt incredible. I hadn't been with too many girls and Leah was doing things to me with her mouth that I had never experienced before. Her tongue licked my shaft as her head bobbed up and down my rigid pole. She held the base of my dick with her hand occasionally stroking it in rhythm to her bobbing.