Teen
2008-12-18

Topic: Our First night on the IslandSpring Break; Part 1(Detailing a trip down to the islands with 5 young girls. )
“TRUTH OR DARE”
 
It had been close to a decade since I’d last been too the Bahamas.   The first time I flew down with three of my college buddies for Spring Break and we spent a long weekend chasing tail and drinking beer on the beach.   It was an enjoyable trip and we created some good memories but I’ve always said that if I went back, it would be with single women instead of single guys.
 
After nine years without returning I’d almost given up hope that I would have another opportunity but luck passed my way and I was recruited by my niece to be a chaperon for a her week long vacation down to the islands.   My niece, Chloe, had been planning a trip with her closest friends down to the Grand Bahama Island and my brother had agreed to be one of the chaperons.   Three days before they flew out his law firm pushed an important suit onto his desk and he was put in a position where he had to back out of escorting the girls.   All the other parents were too busy or simply weren’t able to change their schedule on such short notice so he reached out to me to take his place so the trip wouldn’t have to be canceled.   I spend a lot of time at my brother’s house and had meet Chloe’s friends plenty of times in the past.   I didn’t want to them to have to cancel their plans just because their parents were too busy and since my schedule was flexible, I agreed to get join them and travel with the girls on their trip.
 
The next few days moved quickly and before I knew it I was driving a rental SUV down the streets of the Bahamas with five high school girls crammed into the backseats.   We had rented a car upon arrival and my role of chaperone expanded to chauffeur right away.   We landed rather late but still made time for dinner before we headed to our hotel. While in the car after dinner I found myself looking into the rearview mirror at the young girls more then I thought I would have.   Their ages ranged from 17 down to 15 but all were sexually mature and their bodies showed it.   Brandy, the eldest of the girls, caught me looking at her and waved toward the mirror before returning to her “Beer, Patrick,” one of the girls screamed from the back and I shot my eyes back to the road.

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     The exclamation was to remind me of a promise I’d made earlier in the evening so I found a package store and let Brandy exit the car.   The other girls waited with baited breath as they watched their friend walk into the store and peruse the beer selection.   The car exploded in screams when Brandy exited the package store with two cases of beer in hand.   Once she got back into the car she handed out a few cans and the giddy revelry went silent as they all popped their beverages and began throttling the cold Brandy leaned forward and kissed me on the cheek.   “Thanks Patrick.   You’re the best. ”
 

I was the best though that wasn’t the reason I stopped.   Earlier in the evening I’d lost a bet to them and they’re reward was to get a chance to buy some beer after dinner.   I didn’t think they could do it since none of the girls were old enough but Brandy had a fake ID that I agreed looked legitimate so I decided to make good on my promise.   It never occurred to me that she would be successful but we were in the islands and the laws seemed to work different here. Watching her exit the package store with two cases of cold beer and a huge smile across her face was quite a sight to take in.   Good for her I thought; time for them to make some great memories.
 
The other chaperon on the trip was Mrs. Celia Lane, the mother of Chloe’s friend Mallory.   She had surprised me, but apparently none of the girls, by getting drunk over dinner on expensive wine.

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    She had held her own against the first few glasses but by the time the check came she was very much gone to the reality around her.  
 
When we got to the hotel I reached over to the passenger seat and woke Mrs. Lane.   She had been passed out since we left dinner but did well getting out of the car and up to the room before landing hard against the bed once in her room.   Mallory and I pulled the comforter over her mother and stepped out of the room turning the light off behind us.  
 
When we returned to the living room the other girls had already changed into their pajamas and formed a circle on the floor between the couches.   They were starting in on their third or forth beer and a few looked the slightest bit tipsy from the alcohol.   I stood back in the kitchen overlooking the island bar that separated me from the girls and took in a beautiful view of the young girls in their sleepwear.   I opened a beer of my Brandy Chandler, or Bran-Chan as she was known in the circle of girls, looked a few years older then her friends but in my opinion still shouldn’t be passing for drinking age.   She caught me looking at her as she gossiped in the floor and puckered her lips in an exaggerated kiss towards me.   I could already tell that she was a practiced flirt and didn’t mind trying to work her spell on an older man.   My being a chaperon didn’t seem to dissuade her from treating me like any other guy she was attracted to.   I worked my lips closer together in the smallest of kisses and returned her gesture.
 
She had changed from her jeans into a small pair of white shorts that had slits up the side exposing more of her legs then should be acceptable and sported a mock football jersey specifically cut below her tits to expose her midsection.   The jersey was crimson in color and as she moved back and forth in her seat I could see that she was wearing a white sports bra underneath it to hold her titties in place.

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“Let’s play ‘Truth or Dare’ bitches,” Mallory said when she reentered the living room.   After putting her mom to sleep she had gone into the master suite and changed clothes.   She bounded past the girls on the floor and brushed against me on her way to the refrigerator to score another cold beer.   “We’re going to play Truth or Dare no matter what you whores say,” she explained to the room crassly.   When she passed back by me she slapped my ass with the palm of her hand. “You want to play too, Patrick?  Could be
Mallory was 16 and on the cheerleading squad at school with my Chloe.   I’d been lucky enough to see her in her cheer outfits before and had been excited to find out what she would wear to sleep in given that the other girls dressed so meagerly.   She came out dressed in a baggie white tee shirt that had its sleeves removed creating two huge holes in the fabric that ran from her shoulders to the top of her hips.   The holes were immense and her entire side was exposed.   When she lifted her arm to drink her beer I could see that she was not wearing a bra and the side of her boob jumped into my line of sight.   She wasn’t wearing any shorts either.   The white shirt was baggie and I believe she thought it hung low in the back to cover her full ass.   Luckily for me she was mistaken and the bottom of the shirt ended half way down her ass.   I could see that she was wearing little blue panties that clung to the side of her ass and worked down to a point between her legs.   As she walked away the shirt began to ride further up her back and her panties worked themselves almost completely into view.

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   “I’ll let you girls have your fun tonight,” I told Mallory as I readjusted myself behind the island. “I brought a nice book and am going to read it on the patio until it’s time to turn in.   But have fun. ”  And with that I walked past the circle of hens and exited onto the balcony overlooking the It took me twenty minutes to move my focus off the images of Mallory’s tits and ass that I had lodged in my mind from earlier.   She had a full B cup and the holes cut in the side of her shirt had given a pleasant view of her exposed flesh and the upward curving of her breast. Though I hadn’t bee able to see her entire front, the side of her boob had teased me as much as her panties had.   The images stuck in my mind and I wasn’t able to concentrate on the book.   Eventually I put it down and turned around to look back through the atrium door that separated me from the Their game of ‘Truth or Dare’ was apparently moving along nicely and to my pleasure, drunkenly.   The Dare was on Madison Baker, who was sitting on the floor between my niece Chloe and Mallory.   After she was given her directions she grabbed her long black hair and pulled it over her shoulder as she leaned toward Chloe to her right.   Both girls moved in with hesitation but slowly locked lips with the other and began to make out.   The remaining girls started to hoot and laugh as Madison and Chloe continued to kiss each other unrelentingly.   After thirty seconds I hear Brandy call time and the girls broke their kiss and threw their hands up in victory.   Madison went next and demanded that Brandy play the next two rounds without her shirt on.   I watched through the glass panel door as she pulled her football jersey over her head and then slowly pealed off her sports bra to the giggles of the girls around her.

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    She was the most developed of the girls and her breasts seemed much larger then the C cup I’d originally speculated.

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  Both breasts sat high on her chest and had small pink areolas surrounding her obviously erect nipples.
 

Brandy then challenged Amanda, the youngest girl in the group, to simulate fallacio on a banana from the kitchen.   She was only fifteen and seemed a little hesitant around the older girls but to her credit got up and gave a mock blowjob to the piece of fruit like she was going to win a The game continued on and I watched in amusement as each girl chose dare over truth and the sexual conduct spiraled out of control.   It was amusing to watch and the erotic nature of the show made my dick jumped up and down with each new challenge.   After watching for longer then I should have I realized that continuing to watch the young girls would end up putting me in a bad situation.   Since getting laid was out of the question and jerking off on the third floor balcony didn’t seem like a good idea, I sat back down in my chair and tried to distract myself with my book. About the time I finished the first chapter the door behind me opened and Amanda stepped out onto the balcony.   She was wearing the same pair of light blue hip-hugger underwear I had seen smile at me from underneath Mallory’s shirt earlier in the evening.   The panties were no longer covered by a baggie shirt and I could see the full outline of the low cut underwear pulled tight across the little girls mound.   For her shirt she was wearing Brandy Chandler’s football jersey that I’d seen dropped to the floor in the middle of the room when Brandy was forced to go topless.   The football jersey was mesh and cut off to fall just below her tits. As Amanda closed the door behind her I watched from my chair as her small breasts shifted beneath the mesh shirt and I could see the shine of bare skin through the holes and realized she wasn’t wearing anything under it.   Her nipples stood at attention in the cool night air and supported the full weight of the jersey that fell in front of them.   “I have to touch your dick,” she said bluntly with a small hint of “How’s “We’re playing Truth or Dare and they said I have to ask to touch your dick.

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    Is that ‘Fuck it,’ I thought.   ‘I’m on vacation’.   “Do actually have to touch my dick or just ask to touch it,” I asked She acted confused and shrugged her shoulders.   “I don’t know.   I think I have to touch it or they’ll make me go again.   Going again is always “Well nothings free,” I told her.   “If you can find it, you can touch it. ”  I got up out of the chair and stood in front of her.   The small girl heard what I had told her but didn’t offer any response other then a blank stare and a finger to push her bangs back behind her ear.   She wore it short and blond and it fell just below her ears in the back.   So far on the trip I’d caught her pulling the ends into her mouth to chew on when she got nervous. I watched her as she thought things over and kept her eyes down staring at my shorts.   When she offered no movement I asked, “have you ever seen a cock “Only once.   It was a first date and the guy pulled it out in the movie theater.   I got to touch it but he, ya know, before we could do anything I smiled at her story and reached out a hand to push her bangs back behind her ear since the wind had dislodged it.

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    “Well that’s not going to happen here,” I assured her. “Unzip my pants and reach inside. ”  Taking her hand in mine, I opened her palm and guided it down until she was running her fingers against the crotch of my pants and outlining my growing dick with her She ran the tips of her fingers around my pants and smiled as she felt it push back.   Remembering her instructions she reached her right hand out and took hold of the top of my pants while grabbing the zipper with her left hand.   After the zipper was drawn she reached into my pants, past my boxers and grabbed my semi hard dick.   Her eyes opened broadly as she gripped the shaft of my penis and pulled it out through the opening.   She kept hold as my dick tumbled free and feel out into the night air.   My now throbbing member was even with her exposed bellybutton and I pushed forward slightly and tapped her abs with the head of my dick.   She jumped back slightly with a laugh but never lost her “You’re a virgin then,” I stated as her eyes lust for my now erect Her head tilted up towards me but her eyes stayed fixed and she started to explore my erection with her fingers.   “Yeah. I let a girl at camp last summer go down there but I’ve never had, you know, one of “What are you waiting “It’s not that I’m waiting or anything.   Ya know, the time just hasn’t come yet.   I’ll know when it’s time and I’ll be ready. ”  She moved her grip away from my dick and began to explore my balls with her fingertips.   “How… how long is it? Seven maybe? Seven “Try “Eight? Is it “Bingo,” I said.

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Topic: One of the girls gets explored sexually. She moved another hand out and was working her fingertips through the thin hair around the base of my dick while she continued to probe by balls with the other.   She was captivated by the meat staring up at her and didn’t know how to respond.   I would have gladly bent her over the rail and fucked her tight snatch if she were to ask but she didn’t seem ready for that just yet even though her panties were telling a different story.   The light blue cotton undies she had borrowed from Mallory during their games were turning a deeper shade of blue as her pussy dripped its sex onto the fabric.
 
“I’m gonna go back inside,” she blurted out as she regained composure and pushed past me.  
 
The atrium door opened to a roaring cheer when Amanda reentered the hotel and I turned to watch her little ass prance back inside.   Mallory and Chloe had been standing next to the door watching us through the glass panes and slapped Amanda on her tail as she reentered the living room.  
 
“Alright girls,” I said as I tried to shove my erection back into my pants. “It’s time for bed. ”
 
“Penis,” Chloe screamed and pointed down at my dick!
 
The girls all laughed and Madison jumped up and started shaking her ass right in front of the doorway at me.   They were drunk and just having fun so I told them they could stay up for another fifteen minutes but then would have to try and go to sleep.   They agreed after a short dispute and I return to the balcony to read my book and try not to reflect on the fact that I had just had my dick exposed to five high school girls.
 
It took less then twenty minutes for the girls to calm down and climb into their beds.   When I reentered the hotel the living room was empty except for the beer cans scattered about on the floor.

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    I flipped off the interior lights and headed toward my bedroom.
 
Mrs. Celia Lane and I were sharing the third bedroom because it was stocked with two twin beds and seemed the more sensible sleeping arrangements given the fact that the other two rooms had king size beds.   When I enter the room Mrs. Lane was still sound asleep and hadn’t moved an inch since Mallory and I had put her down.   I flicked the lights on and off a number of times to see if she would wake but she offered no reaction and I felt certain that she was out until morning.  
 
The bed slept well for a twin and I was looking forward to getting a few hours of rest before sunrise.   After throwing my shoes into the corner I stripped down to my boxers, climbed under the covers and passed out.
 
“Patrick,” someone whispered into my ear.   “Patrick. Are you awake. ”
 
I didn’t know if I’d been asleep for five hours or five minutes but I opened my eyes and saw a figure knelling down by the side of the bed speaking to me.   “I’m up,” I said more from reaction then from truth.  
 
“Good,” the voice replied as my covers were pulled back off of me.   “I had a bad dream and need to sleep with someone.

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   And by someone, I mean you. ”
 
It was Brandy Chandler voice and I felt the heat of her body slide in next to me as I broke fully from my sleep.   Her arm reached out across my chest as she pulled the top sheet and comforter back up and pressed close to me on the small twin bed.   My mind raced back to the small white shorts she was wearing earlier in the evening and the exposed young tits I had seen when she took her jersey and sports bra off.   
 
“Brandy,” I stammered as I tried to understand what I was waking up to.

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  “Are you sure? It’s just that. . . ” I continued to grasp for words as she began to work her hand over my chest and maneuver her lips toward my ear.
 
“No Patrick,” she purred.   “I dreamed that someone besides me got to be next to you tonight and got real upset.   I saw you watching us play Truth or Dare tonight and I really enjoyed knowing you watched me from the balcony when I took my shirt off. ” She let the tip of her tongue glide into my ear and reached further down my chest and let her fingers creep beneath the elastic band of my boxers. “What were you thinking about when you saw me take my top off Patrick?  Hmm.   I bet you were thinking about putting your dick between my tits and cumming all over my chest.

 

    Was that it?”  She then reached down into my boxers and ran her fingers across the shaft of my dick.
 
Though she was unbelievable hot and had a body that I could only dream about exploring, I was the chaperone on her trip and any kind of sexual relationship would be off limits.   When I had watched them in the car I knew those were the rules and when I had allowed Amanda to feel my pecker on the balcony I still knew where to draw the line, but once this young girl shoved her hand down my boxers the rules didn’t seem to apply anymore. Whatever the line is and wherever it was, it had been crossed and this girl was going to get fucked.   
 
Taking control of the girl, I moved my arm out around her side and pulled her to a seated position directly on top of me.   She groaned when I repositioned her because her asshole fell directly onto the tip of my penis.   I had gone rock hard once she started to push her fingers along my dick and stood at full mast once she was mounted me.    Her long brown hair fell down over her shoulders, cupped around her face and covered the top of her breast though her nipples remained exposed.   
 
Reaching up, I took a handful of her hair and pulled her head down toward me so I could reposition her lower body.   When I released her hair my dick was perfectly positioned underneath her cunt and she fell back onto it with a wave of pleasure as the head of my dick squeezed into the tight folds of her pussy.   Her eyes closed as she took in the head of my dick and began to move her pelvis up and down until she had taken half my cock into her moist cunt.    She was as wet as if we’d been having sex for an hour and my mind began to wonder what part of Truth of Dare game I’d missed that had gotten her so moist.   She rocked her hips off and on me but the tightness of her pussy wouldn’t allow her to accept more then half my dick.   She worked what length she could take into her hole like a metronome at double speed.  
 
“Fuck,” she mumbled as I pushed inside.

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    “Fuck, fuck,” she stated again growing louder.   Her volume increased with each thrust and I began to worry she would wake Mrs. Lane who was only one bed away.   Reminding her of the surroundings, I reached out with my hand and popped Brandy across the cheek and pushed my thumb into her open mouth.   She sucked it in and began working it like a cock in a second hole.   Her panting continued but her chants of ‘fuck’ subsided as long as I continued to give her something to suck on.
 
While we fucked I became captivated on her tits.   They were swinging directly in front of my face so I reached out with my tongue and sucked one of nipples into my mouth.   I did my best to ensure the breast would develop a red scared hickey as I pulled it deep past my teeth and worked the nipple back and forth with my tongue while sucking hard.
 
I felt her pussy continue to leak down the sides of dick and the juices began to pool on the sheets beneath me.   Time marched past as I worked deep inside her over and over again with my tool and eventually brought her to a shivering orgasm.   She bit down hard on my finger and began to buck her legs hard as the orgasm hit her pussy and her body seized up.   Her moans grew loud again and she thrust down on me harder and harder as the waves of her orgasm broke over her body.  
 
Her body began to relax as the pleasure subsided and she released my thumb and replaced it with her own lower lip.   Her hips continued up and down as I worked my member between her tight lips but her pace slowed considerably cumming.

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My own orgasm was approaching but her ass was still too far into the air for my liking and she hadn’t yet made an attempt to bring herself completely down onto my entire cock.   Over and over she brought her wet slit back down onto my eight inches working toward her second orgasm but she never seemed to take me completely in.   Each time she would stop a few inches short of the base of my dick and push back off.  

I dug my fingers deep into her ass cheeks as she worked her cunt on me and I waited until I felt her pull her pussy completely off my dick then moved my own ass down into the mattress.   When she dropped her hole back down I pulled her ass toward me and thrust upward digging deeper into her pussy then she had been allowing.

FUCK,” she screamed as her cunt landed and swallowed my entire shaft.   She threw her head down and bit into my shoulder as my full hard-on broke deep into her tight snatch and ended somewhere beyond what she had considered her limit.  

The expletives continued as she closed her mouth around my shoulder to shield the volume of her cries.   I let her off my dick slightly but brought her back down a second and third time making sure she took all of me in with each thrust.   Her pussy began to exploded female cum all over my balls in her second orgasm as I stretched her pussy lips to the limit.   She bounced up and down on me while keeping her face buried into my shoulder and tears began to develop in her eyes due to the pain.

Her tears hit wet against my shoulder and I continued to bury my full length between her legs.   After a few more thrusts, that should have broken the poor girl open, I began to feel an orgasm develop in my balls and my thrusts became more concentrated.   “Oh you little bitch,” I whispered into her ear. “I’m gonna cum all in you.

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  ”
 
Wait,” she screamed as she removed her teeth from my shoulder and tried to break away from my grasp. “I’ve got to be down,” she started without finishing.  
 
Struggling against my strength she worked her cunt up and off of my dick.   She pushed herself further down the bed until I felt her lips wrap around my cock and begin to suck on my knob.   Her hand grabbed hold of my shaft and began to work the fluids from her twat up and down with a stiff grip.   I’d reached my apex once she put her lips around my head and I felt the cum explode from deep inside the base of my crotch and out into the mouth of the young high school girl who seemed aching to receiving it.  

She backed her head away from my dick once my cum began to flow and she showered her face in jism that shot from my penis.   Some landed on her chin but most fell directly across her face as she turned her head back and forth along the line of fire.   When I ran out of strength and the remaining cum simply leaked out of the head of my dick into my bellybutton, Brandy leaned down and sucked the pool off my chest and turned back toward me with cream covering her face.   “Patrick,” she started.   “my pussy fucking hurts but that was the best sex I have ever experience. I’m going to have to sleep with an ice pack between my legs tonight. ”
 
I could have told her that.
 
After a few seconds of silence she slid off of me and stood at the foot of the bed.   Her pajamas were scattered about and she picked them up one at a time as she backed towards the door.

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    “We are going to do this again before the week is over,” she whispered as she reached behind her back and gripped the door handle.   I nodded in agreement and watched her naked form begin to glow as the light from the hallway took over the outline of her body.
 
She blew me a kiss and winked as she slowly turned and my mind began to swim with the exploits I was going to experience over the next few days.   I stayed in my bliss until I hear Brandy scream down the hallway at the top of her lungs, “I win bitches!”

Our hotel suite exploded with cheers of “Hell yeah”, “you slut,” and a chorus “Wooo!”  Mallory and Chloe rounded the corner into the hallway first and fell to the floor with laughter when they saw the mess I’d left on Brandy’s face.   Amanda and Madison follow close behind but reacted more with awe when they saw my cum dripping from Brandy’s face and down to her chest.
 
I stood up and walked over to the door as Amanda grabbed Brandy’s head and began to work it in a circle as she examined the lines of cream I’d left across her face.
 
“Good night girls,” I said as I closed the door to the five girls and locked it from the inside.  
 
            “Good night Patrick,” the girls screamed back in unison!
 
            “Can’t wait to see you all in the morning,” I whispered to the closed door as I turned and walked back toward my bed.
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