Story Name / Genre: "Island Paradise" (Part 21 of 30) -
M/F, F/F & just about everything else _____________________________________________________________
After five erotic-filled weeks on the island with this group of ladies, things were starting to come into focus.
My devotion for Pamela - and hers for me - was steadfast and strong, and would not change. Never. Sensing this, Lindsay and Amy - each of whom I had already been strongly linked to in the recent past - accepted this as fact, and were happy for Pamela and I. Both of them wished they could be in Pamela's shoes, but there was no ill-will involved.
Thus, Lindsay and Amy began to explore other avenues of future fulfillment. As a result, Trish did not like the fact that Amy was trying her best to convince Lindsay to move to Los Angeles with her - so the two of them could begin a long (and profitable) career in the porn industry.
Amy was a slut, of course - and after being on the island for several weeks, she claimed the best way for her to make her money from now on was to get paid for having sex. That was where the porn industry could come into focus for her.
Lindsay, the possible slut-in-training, was intrigued by Amy's ideas. Though Trish wanted Lindsay to move to Canada with her - so they could be together - the tender and sweet 18-year-old was strongly considering Amy's Los Angeles idea.
Amy wanted a partner - or a sidekick - to break into the porn business with. Who better than Lindsay? However, Trish was absolutely enamored with Lindsay - like everyone else here - and wanted the little blonde for herself.
Could there be a tug of war between Amy and Trish?
Although Lisa and Torrie did some spectacular things together when it came to sex, their emotions for one another ran only skin-deep. That was unfortunate.
It was rather obvious to me that after five weeks on the island, Lisa and Torrie did not love each other. It wasn't that either were upset or didn't get along together. Their feelings simply were not strong enough for a bona-fide and passionate love to develop. They continued to have some wild and memorable romps when it came to sex, though.
Lindsay and Trish were still an item... but for how long? Amy the slut was filling Lindsay's young, fertile mind with all sorts of ideas. Amy informed her that she could make a whole lot of money in those adult films where there was a college-girl/school-girl theme involved.
I don't know about you - but just the mere thought of the sweet teen in pig-tails and a plaid skirt made me hard...
Of course, an easy solution to this love triangle would be for Trish to move to Los Angeles and get into porn with both Amy and Lindsay. That way, Trish would not have to be apart from Lindsay. They could be together all the time.
It sure did seem simple, but unfortunately, Trish had no ideas of venturing into porn. She was openly talking about the possibility of using her "island earnings" toward opening her own fitness center, in her hometown of Toronto. Trish was a definite "exercise babe", and would probably be real successful in owning and operating her own health club.
Speaking of money, Torrie planned on using hers to go out and party upon returning home. That was her spoken idea, at least... which told me she really had no clue on how to spend either $50,000 or $500,000. Who can blame her?
Lisa had turned out to be the most happy-go-lucky girl on the island. She was always very cheerful and upbeat, and had a smile and friendly word or two for everyone who passed by. Her good-natured attitude had even rubbed off on me (a bit).
As for Christina, she had really settled into her "maid" role, and truly thought of herself as the real assistant housekeeper. That was excellent, because Louisa - the actual maid - was old (75), and could not handle a heavy workload all by herself. Christina was a major help for her.
It had been two weeks since Pamela had her first taste of the voyeur room. Though she detested the idea at first, now it seemed as though the 25-year-old stripper spent more time spying on her fellow women than even I did.
Pamela admitted that secretly watching her friends was a big turn-on, but still insisted that it was wrong and made feel her most uncomfortable. She was perched somewhere between acceptance and denial on the subject.
Soon, I believed Pamela would buckle to that forbidden lust and simply accept the fact that she was a voyeur. I spoke from plenty of personal experience, you know.
I could feel guilty myself for eavesdropping on all the girls in their private moments as I too, knew it was wrong. However, I accepted long ago that "watching" was one thing which really turned me on. I could not fight it, no matter how wrong doing it in secrecy was. So I just gave in...
Five weeks down... and five weeks to go. It was about this time when I realized my time with all the ladies on the island would be running out soon. I needed to enjoy things.
"Just what do you think Torrie wants for her birthday tomorrow?" I asked Lindsay as the two of us lounged together upon the bed in my personal suite. Tonight, it was little Lindsay's turn in the rotation to spend the evening with me. Tomorrow, of course, would be Torrie's 26th birthday.
"I think she wants about 15 or 20 guys to show up," Lindsay replied, sneering at her own words. "Of course all of us want that too. We want to be gang-banged again, just like on Amy's birthday. But with more guys..."
Such a sweet and innocent-looking girl Lindsay was... hearing her talk nasty like this really turned me on. "I'm not sure you could handle a lot of guys, Lindsay. You're so small and frail; seems like too many would bust you in half."
"I can handle whatever you throw at me," the 18-year-old responded in a confident tone. "If you want me to do 20 guys at once, I can do that... it won't be a problem."
My eyes grew big at her words. "20 guys at once? Are you warming yourself up for your possible career in porn?"
Lindsay frowned for a moment as her lips twitched about. She looked deeply into my eyes and said, "That's something I wanted to talk to you about tonight, Jeremy. You know... get your opinion." Her expression did not look good.
Offering a smile, I put an arm around the petite blonde's shoulder and snugged her close against me. "Is there something wrong, dear? Talk to me..."
"It's just, I don't know what to do," she responded. "Amy wants me to get into porn with her after we leave the island next month. I would love that but I also love Trish. She wants me to go to Canada and live with her."
"You're a popular little thing," I said, smiling warmly.
"Yeah..." she returned, before pausing for a few seconds. "But I don't know which to choose. I'd love to get into porn - have sex with so many people. But I also love Trish, and I care for her very deeply."
"Can't you have both?" I countered. "You could live with Trish in Canada yet commute to Los Angeles once or twice a month to make your movies. That's a good idea."
"Trish doesn't want me in porn," Lindsay replied. "It is a good idea but not one that will work out. I really have to choose one or the other, you know. She does not want to live in Los Angeles, either. Trish's home is in Toronto. She wants me to move there with her."
"What do you want more?" I asked her, getting to the real point. "A career in porn or a life of love with Trish?"
"I don't know!" the teen-ager returned, almost whining. "I care about Trish so much but Amy... the things she does to me during sex. She drives me insane! I can only imagine what it would be like with a group of skilled porn stars. I wonder how they would make me feel?"
"It's not my place, sweetheart, to tell you who to choose between Amy and Trish," I informed her. "But I will say just from knowing you these past five weeks, I think you would be happy either way. You obviously love Trish and want to be with her. But you also love sex and want to experience more of it. Porn is a good place for that."
"I don't know if I would be a good porn star," Lindsay said, frowning. "I don't have the body for it."
I smiled at the blonde while my eyes ventured downward, toward her smallish-sized breasts and frail, tiny waist. The 18-year-old was so sweet and irresistable! If she wanted a career in porn, Lindsay would make a great deal of money... no matter how insecure she felt about herself.
"You don't need Pamela's or Trish's breasts to be a porn star, honey," I told her, trying my best to sound sincere. "You look absolutely fabulous the way you are."
"That's what Amy says," Lindsay countered. "She says if they put a schoolgirl uniform or a cheerleader outfit on me, I would be a super-star." My cock immediately begin to stir at those words. "She said 40 and 50 year old men would camp in front of their TV and constantly whack off to me."
"I can think of a 27 year old who would do the same," I told her in an uneven tone, pointing a thumb toward myself. "Constantly whacking off to you while you're on TV... that would be fun. I'd like to try that sometime..." (cough)
"You think Amy is right?"
"Yeah, I do," was my response for her. "I really do. I think you're the sweetest little thing I've ever seen in my life. You're 18 but you look 15. Put on a school uniform, or dress up like a cheerleader. Older men love that." I paused and said, "Of course... in those type of movies, you would be having sex with older guys. 40, 50, maybe even 60 year old men. That's the idea of those type of movies. They are for older men who find girls your age attractive."
"I wouldn't mind having sex with older men," Lindsay said in a sweet tone. "I absolutely adore them as it is."
"They would adore you too, honey."
She giggled before saying, "I've never been in one of those schoolgirl uniforms but I do have plenty of experience as a cheerleader. In fact, I brought my uniform with me." As my eyes nearly exploded in both lust and desire, Lindsay reached over and retrieved the small shopping bag she had carried into my suite with her. She held it up before me and said, "Would you like me to put it on for you, Jeremy?"
After a few seconds of silence - during which time I collected the strength to reply to her - I finally said, "Yes, baby... I would. Please do. PLEASE..."
Lindsay giggled at my reaction before she sprung up from the bed. "I'll be back in a minute," the 18-year-old said, turning and carrying the bag into the adjacent restroom with her. When she closed the door, I took my cock out of my shorts and began stroking it immediately.
What can I say about Lindsay which hasn't already been said? She was a total sweetheart, through and through. The 18-year-old was everything which a young lady her age should be. Lindsay was sweet, kind and curteous. She was charming, and seemingly so wholesome, innocent and purely delectable. She was a walking, wet-dream-come-true.
Best of all, Lindsay was turning into an insatiable little hellcat who eventually would have no sexual limits.
The thought about what it would be like if Lindsay got into porn popped into my mind. What if the sweet, little thing became an instant star? Or a mega-star? What if, before things were said and done... Lindsay would turn out to be the most popular woman in the history of adult films?
What would that do for me, personally? Thanks to the island and my stash of hidden cameras, I would plenty of "before she was a star" footage of Lindsay.
Let's see... I had Lindsay's first-ever daisy-chain. The first time taking a dildo, both traditionally and in double penetration. The first time she had ever been verbally humiliated and degraded during a sexual encounter.
A first time for mostly everything, really. Lindsay taking my cock in her ass. Big orgy encounters with all her fellow women. Masturbation. Even her first time getting gang-banged by a group of over-anxious men.
In just five weeks of being on the island, I had plenty of Lindsay's "firsts" captured forever on videotape. I had five more weeks to collect more of them, as well as her "seconds" and "thirds". If she would go on to become a world-famous porn star, I could look back on these tapes in the future and remember "what she was like back then".
I could also make a hefty profit off of those tapes as well, but that did not interest me. I had no plans or inclinations to sell or loan out any of my "Island footage". That would be wrong to do.
"Do you like my uniform?" Those sweet-sounding words broke me out of my quiet reverie and inner thoughts. When I looked up and focused upon Lindsay, my jaw dropped. She was the cheerleader of my dreams...
The little goddess wore a long-sleeved white blouse with a green sweater-vest buttoned down her front over top of it. The sweater-vest was a tight fit, of course, and showed off Lindsay's taut, lithe curves in a very enticing manner. The vest also bore a high school's name and emblem, so I figured the uniform was from Lindsay's days as a varsity cheerleader.
The skirt she wore was green-and-white with knife-like pleats all around it. The skirt was made of very light cotton, so it flipped and bounced about easily as she stepped closer to me. It was also a very short and low-cut.
Underneath the little skirt, a pair of white cheerleader panties could barely be seen. From what I saw, they looked purely intoxicating. Lindsay's outfit was topped off with green socks which were rolled down to her little ankles, and a pair of white athletic sneakers.
"Oh God..." I moaned when noticing that Lindsay had styled her long-flowing blonde hair into two bushy pig-tails for me.
"Were you thinking about me?" the enchantress giggled as she eyed my hand as it gripped my cock.
I pulled my hand away and offered her a sheepish grin. During my thoughts about Lindsay and her possible foray into porn, I somehow forgot that I had been stroking.
"Were you whacking off, thinking of me in my cheerleader uniform?" Lindsay was becoming bolder. Though she still had a little insecurity about her smallish frame, it was obvious Lindsay knew she had me right where she wanted me. "I brought it along in case you wanted to see me in it."
"Yes honey, I was thinking about you," I responded. "You look even better than I thought you would." I paused, gulped my throat and then said, "Will you model it for me? Please?"
Lindsay giggled and turned around slowly, offering me a full and luscious view of her uniform and slender figure.
"You're gonna make a lot of money if you get into porn," I told her in all seriousness, gripping my cock and starting to pump it some more.
Wow... What was more tempting? That sweet-cheeks face, her killer smile, or her overall good personality? How about that taut, little body of hers, stashed away in the uniform? Were her tiny panties the most tempting for me?
No... it had to be the pig-tails. They did nothing but make Lindsay appear even MORE sweet and innocent. Amazing...
A girl who looked like this - it was right out of my deepest, darkest fantasies. A cheerleader slut who wanted nothing more than to stuff herself full my willing cock...
"You like it that much?" Lindsay asked, twirling around once more. In the process, her little skirt flew upwards, offering me an even more scintillating view of her panties.
"Oh yes... I do," was my response.
She giggled once more before bluntly saying, "Why don't you fuck me in my cheerleading uniform, then?"
"Oh yeah..." I growled at the mere idea, my eyes bulging as I openly rubbed the throbbing erection between my legs. Lindsay giggled at my reaction, before lifting her little skirt up and taking a seat upon my lap. She wrapped both arms around my neck and then offered me a heat-filled kiss.
Soon, one of her hands ventured downward and found the cock which she had been personally responsible for making so hard. Lindsay took it into her hand and began with a strong, brisk stroking, as our tongue-filled kiss continued. I moaned in rapture upon the cheerleader sweetheart, holding her close to me in a warm, tight embrace.
I moved both hands down her slender back and waist, and squeezed her firm, taut ass. Lindsay squealed with delight in the process, before I lifted the back of her skirt and tucked it into the waistband of her panties. The teen-ager squirmed and writhed about in response as I then began to grope and maul her sweet ass with both hands.
"Will you fuck me in my uniform?" she asked once our kiss was broken, her breathing a bit labored.
"Of course I will," I told her, nearly consumed with lust. "It is something that you obviously want, dear. I know it is something that I want."
"I don't know why," Lindsay mused. "It's just when I was in high school, there was this one older teacher I liked a lot. I always had fantasies of him fucking me after class, or after cheerleading practice, especially in my uniform. You know what they say about cheerleaders and how slutty they can be. I always wanted to be a cheerleader like that."
"Why weren't you, sweetheart?" I asked, leaning forward and peppering her neck with a tender kiss. "I think your teacher would have appreciated you seducing him."
"Oh... I could never do anything like that," the blonde returned, shaking the thought off. "I guess I really did not start to develop any confidence until arriving here on the island. I've always been insecure about my body. I always had the fear people would laugh at me."
I shook my head while squeezing her smallish breasts through her sweater-vest and blouse at the same time. "There is no reason for you to feel insecure, honey. I have said it before and will say it again - you are the sweetest little thing I have ever seen in my entire life. You don't need to change a single thing about yourself."
"Guys my age are after the girls with big breasts," the 18-year-old said, her lip curled. "I really can't blame them though, because I'm attracted to girls with big breasts too. That's why I like Pamela, Amy, Torrie, and Trish."
"Guys your age do not know what they want," I told her. "They are just too immature to know what is good for them." I am 27, sweetheart. When a guy gets to be about 25 or so, he starts to notice girls your age, or those in college - moreso than ever before. I think it will only get worse for me as I get older. You are so young and fresh-looking that it's almost criminal for me to feel the way I do about you."
Lindsay giggled at my words before saying, "Does young and fresh-looking involve us girls with small breasts?"
"Of course it does," I told her, grinning, while taking her breasts into my hands and squeezing them gently. "That is a big part of it."
"I see that all the other girls here like me," Lindsay said. "I really did not know what to expect when coming to the island, you know." She giggled and added, "I thought if I won the $500,000, I could get breast implants."
My eyes simply bugged-out at those words. "Lindsay honey, PLEASE tell me you're not going to use the money for that. You are absolutely PERFECT the way you are."
"Oh no, not anymore," she told me, giggling. "I see how everyone likes me now. Maybe it was just getting away from guys my own age. Amy was telling me about how girls with my type of body can make big money in porn. And I remember how those guys you brought to the island, how they liked me too. I still wish I had a better body but I'm not going to worry about it anymore. I'm just going to use it to my advantage! Lindsay the sweet 'lil schoolgirl burns up the porn screen!"
"Suck my cock, honey," I begged her. "I'm going to cum here in a second if you keep talking like that..."
Lindsay offered me yet another youthful-sounding giggle before she reclined forward on the bed. Laying upon her stomach, she reached out with her right hand and grasped my cock as I sat on the bed, my legs outstretched. She inched closer to me, then opened her lips and took my cock into her warm, velvety mouth.
I tossed my head back and sighed in response, the hot sensations swirling throughout me. Lindsay held the base of my cock with her hand and frigged away as her head gently bobbed back-and-forth upon it. All the while, the little goddess kept her eyes glued to mine, staring at me with an excited, lustful gleam.
Still sighing out my pleasure, I brought my hands to Lindsay's head and gently caressed her scalp. I ran my hands through her silky hair, then grabbed each of her blonde, bushy pig-tails and held onto them like handlebars. Lindsay giggled and sneered in response as she continued sucking my cock in her own sweet way.
I managed to pull away from her, however, and then stand up before her. I had an idea in mind...
"Lay on the bed, Lindsay - on your back," I instructed her. Of course, she complied with my request. "Get close to the side of the bed, and turn your face toward me." I nearly blew my load as she did so; the way Lindsay looked in her cheerleading outfit was making me think nervous things.
With Lindsay on her back, her face turned toward me near the upper corner of the bed, she suddenly realized what my idea was. "You're going to fuck my mouth?" she asked in an excited tone, her eyes focused upon my bulging erection.
"Yes I am," I told her, gripping my cock. "I'm going to fuck your mouth standing up while you lay on the bed." I stepped closer to her and said, "Open up, baby. I've got something big and nasty for you..."
Lindsay snickered and then gasped as I jammed my cock hard and deep into her throat. I held onto one of her bushy pig-tails once again while starting to thrust my hips back-and-forth.
Lindsay gagged and choked for a short moment, but managed to take the full length of my cock into her mouth with every forward thrust as her pretty blue eyes begged me for more. That is just what she got, too.
Using the sight of the 18-year-old in her cheerleading uniform, it was all the motivation I needed as I began to thoroughly pump and pound Lindsay's mouth and throat with all of the strength within my body.
She screamed in the process, but that did not deter me from my objective. I wanted to ram my cock so far down her throat that it would come out of her pussy...
Perhaps that was a bit far-fetched, of course, but it was still a nice goal. Lindsay seemed to have similar thoughts in mind as the look on her face continued begging me for more. She enjoyed the rough treatment I was giving to her throat and mouth. A cheerleader slut in heat, it seemed...
I grunted and growled in wild passion as I pumped my way in-and-out of her wondrous throat. Now holding onto both of her pig-tails, I yanked them slightly (not wanting to hurt her) as the hard thrusting action continued.
Soon, I felt the pleasure within me reach its boiling point. A second or two later, I screamed out in pure lust while withdrawing my cock from her mouth. My eyes closed and head tossed back, I gripped my cock and let out another wild scream before the explosion within me occured.
I missed seeing the first two heavy cum-shots. But upon turning my attention back to Lindsay, I at least noticed where they landed. One was splattered all over her neck while there was a second, long glob of cum all over the front of her sweater-vest.
With another one or two spurts left in me, I aimed for Lindsay's open mouth and extended tongue, and let her have it. A thick strand of sperm landed upon her tongue and chin, followed by another upon her nose. She swallowed the load on her tongue down, then wiped her nose and chin clean, and sucked the remainder down as well.
"You came all over my vest," Lindsay snickered in a peculiar tone, glaring at me as I took a step back. "I wanted it all in my mouth." She used her fingers to gather up some of the excess fluid upon her vest, then licked them dry once again.
Needing a moment to catch my breath, I took another step back and grinned at her. "Get used to that, Lindsay... if you get into porn. Cheerleader, schoolgirl outfits... guys cumming all over what you wear. It's a big fetish for older guys to see someone like you in these situations."
"I think I will get into porn with Amy," the teen-ager said. "I love Trish but I think I'd love wild sex more. I'm too young to be committed to one person." She paused and then said, "Do you think it would be a big fetish for guys to watch me get fucked in the ass... while I have my cheerleader uniform on?"
I almost passed out with those words, knowing what she was leading up to. After a short pause, I settled myself down and replied, "Yes Lindsay... a BIG fetish."
The cheerleader slut giggled with desire as she suddenly sprung up from the bed and spun around, her back to me. With the back of her skirt still tucked into the waistband of her panties, Lindsay leaned over and placed both hands upon the bed... jutting her ass toward me in the process.
I nearly came again - that quickly - but somehow managed to stave it off while fumbling around in the nearby drawer for a tube of anal lubricant. I found one, then quickly smeared it all over my shaft. Lindsay wanted my cock in her ass... and I was not about to disappoint her.
The little tease wiggled her hips in anticipation as I got behind her, shoving my pelvis hard upon her outstretched ass. I didn't want one part of her uniform to come off - even her panties. So, I had to reach forward and pull them aside, barely exposing her tight, puckered anus for me.
It was all the daylight I needed too, as I then fisted my cock and drove it hard and deep into her.
Lindsay threw her head back and screamed in arousal as I began to hump and thrust my way into her. Wasting no time, I grabbed her taut hips and held on tight as I slammed myself into her. Soon, I joined the parade of screams as both of us were making a lot of noise.
Keeping a wide base with her thighs spread apart, Lindsay was now completely bent over the waist. Her body shook and shimmered as I hammered away at her, her shoulders perched upon the bed with her face turned to the side. Her mouth was now open and her eyes were about to explode, as she let out a series of loud, animalisitic growls and screams.
My fascination with those two blonde, bushy pig-tails continued as I then reached out and grasped both of them. I grunted loudly as I stroked her ass, while also holding onto her pig-tails from behind.
Not a word was said - there were only screams. Lindsay's body reached a fever pitch, then the blonde rumbled out as she was overcome with a powerful orgasm. Lindsay fell to her knees upon the floor, but I somehow managed to go down with her and keep my cock embedded within her anus.
As her orgasm progressed, I pumped her ass some more. I wanted to get every last ounce of pleasure out of this as I could, before my cock erupted within her. When I used my right hand to slap her ass, I then lost control of myself.
One more forward stroke later, I was pumping my thick and gooey seed into the 18-year-old's bowels. Both of us moaned and growled together as my body experienced the wondrous joy of sweet orgasm. I kept my cock in her for a long time, until I was positive that all of its cum had been deposited into her. Only then, did I finally pull out.
After smoothing her little skirt back down and into place, I patted Lindsay on the ass while moving up and offering her neck a series of short nibbles and kisses. Both of us had been thoroughly satisfied tonight.
Before Lindsay and I fell asleep together that evening, my thoughts drifted to the voyeur room. You could bet your bottom dollar that the tapes were rolling, and everything which happened between Lindsay and I was captured on film.
Better yet, however, was that I had a little "helper" in the voyeur room. Pamela was in there... and she promised me earlier that she would "direct" the film for the evening. Meaning, of course - Pamela would use only the best camera angles as she videotaped my heated encounter with Lindsay.
I wondered to myself if by watching Lindsay and yours truly get off together, Pamela had gotten off herself... Then, I smiled. Of course she had!
<<<- End of Part 21 ->>>
NOTE: This story has been extended from 25 to 30 chapters.
---------------------------------------- Find every chapter of this story updated and archived at:
ftp://ftp.asstr.org/pub/Authors/HighlanderJM/
Reader feedback (HighlanderJM@hotmail.com) is appreciated!
--> Contact me on MSN Messenger for chat: HighlanderJM