Chloe's Sex Lessons Ch. 01

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Chloe loses her virginity.
3.4k words
4.23
74.9k
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Part 1 of the 17 part series

Updated 09/22/2022
Created 01/05/2010
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Chloe Ashley Anderson grew up on a farm in northern Minnesota close to the Canadian border; about as far north as you can go in the United States without getting into Alaska. Chloe attended a traditional one room rural schoolhouse before getting into high school and thus had little interaction with her peers. Even when she actually got into high school, she had virtually no friends. Chloe was born big and was always big for her age. She was already 5'9" (175 cm) tall when she was just nine years old on her way to finish off at 6'2" (188 cm) tall when she became fully grown. Because of her height and because as a young girl Chloe was not particularly attractive, she was shunned by her few schoolmates.

As her reputation as a drab girl persisted Chloe's peers did not notice what a gorgeous female Chloe was developing into. By the time of her senior year in high school Chloe's bra size was 40" DD which was proportionally magnificently perfect for her height and body frame. She was a little bit overweight but most of her extra weight was in her ass. This meant her ass was spectacularly rounded and prominently jiggled when she walked. She herself thought that she had a fat ass, but it was absolutely attractive and mouth-watering to any male who appreciates the female derrière. Her hair had achieved an unbelievably natural light golden blonde color that would make any red blooded American male's mouth drool. Her face achieved such character of beauty that she would have instantly been rated a favorite at any beauty pageant no matter the number of contestants. However, despite such beauty Chloe's acquaintances were oblivious of her pulchritude. As she had no close personal friends and discounting her family's expected bias Chloe actually had no idea how gorgeous she really was. Since she had had no dates while in high school her own impression was that she was nothing special and thus if she could attract any man to actually marry her, she would feel most fortunate.

With such an attitude Chloe concentrated on her academic studies forgetting about a social life. As she diligently applied herself, she was able to bolster her high school curriculum with advanced college level courses. Thus, after scoring exceptionally high in her SATs, she won a full academic scholarship to attend University of Minnesota in the Aerospace Engineering program, certainly not a typical female college pursuit. Her family was certainly happy for her since although not poverty stricken, they could not afford to provide a college education for Chloe especially since there were seven other children in the family. As for Chloe she was certainly excited as her future seemed to be assured. She saw that she could by continued application of academic studies eventually lead a comfortable life as a university professor or she could opt for a more luxurious lifestyle by entering into the private sector and secure a high profile high paying position in the aerospace industry. Not a bad outcome for a relatively poor farm girl from the sticks of Nowhere, USA.

However, the most attractive feature of the University of Minnesota scholarship for Chloe was the opportunity to participate in a more sophisticated and exciting lifestyle. Although a virgin she nevertheless was not ignorant of sex. Her extra school studies necessitated she utilize the internet and by such usage she discovered porn sites. By her occasional visits to the various porn sites, she became savvier of sex than a typical virgin. As a result, Chloe had been for quite some time looking forward to losing her virginity. Although believing herself not to be particularly attractive, she was certain that given the more opportunity within the vast campus setting not to mention the metropolitan area of the twin cities itself, she would have no trouble in finally experiencing sex.

With such happy thoughts Chloe eagerly set out for Minneapolis to start her new adult life. She first acquired through campus housing a two bedroom basement apartment which was surprisingly spacious and perfect for studying (spare bedroom) as well as entertaining an occasional visitor (master bedroom; hopefully). Her bedroom was so large that she indulged herself by obtaining a king size bed. You never know was Chloe's motto.

Next Chloe had an appointment with Mrs Reynolds who was her academic advisor. After planning Chloe's course of studies and establishing her class schedule Mrs Reynolds had an interesting proposition. The school's football team consisted of players who in reality were sub par students and thus were usually enrolled in the easiest and least challenging courses; Mickey Mouse courses if you will. However now and then a player will opt to choose a demanding course to ensure obtaining a worthwhile degree. It just so happened that the team's quarterback Dexter Randall Hamilton, who preferred to be called Randy, had chosen to take a mathematics course this semester. To ensure Randy would successfully complete such a course the University was prepared to offer a tutor at no expense to him in accordance with his scholarship. Although Randy was already in his junior year, his chosen course was introductory, and its subject contents Chloe had already completed an accelerated course she had taken while in high school so that she was qualified to be Randy's tutor. Chloe did not hesitate to accept such offer. After all the extra income would certainly be welcome and although not expecting to entice the stud quarterback to her bed it had to be useful to know him which should pave the way for snagging some player on the team to be her first lover. Upon Chloe's acceptance Mrs Reynolds set up an appointment for the two of them to meet at the library to commence the tutoring.

When Chloe met Randy her mouth almost visibly dropped. What a hunk! Randy was 6'4" (193 cm) tall a most welcome attribute considering her own size. Chloe's height was an intimidating factor to most males which in turn caused her not to be able to date while she was in high school. He had blonde hair not much different in color than hers and he was all muscle without any hint of flab throughout his impressive body. As her panties were getting wet just at the sight of him Chloe thought that if this were the man to claim her virginity, she could not have envisioned a happier prospect.

For Randy's part he was most pleasantly surprised. When advised by Mrs Reynolds that he was to have a female tutor he imagined the stereotypical female nerd. That is dirty brown unattractive hair done in pig-tails; thick round eyeglasses; unappealing freckles; flat chest; and a rectangular body. He first suspected that Mrs Reynolds was playing a joke on him since such a luscious babe like Chloe could not possibly be as smart as he would need for successful studying. However, after introductions and the two started their first study session it quickly became apparent that Chloe would indeed be truly beneficial to him in his academic endeavors. After the study session was over and quite satisfied with the outcome Randy suggested they relax at a nearby bar and get to personally know each other better. Chloe quickly accepted as to her mind every moment in his presence was simply like being in heaven.

They traveled to the bar in Randy's car, a Jaguar, (Chloe had walked to the library). While drinking some beers Chloe learned that Randy was from Texas and from a relatively well to do family- not extravagantly rich but still very well off. He was the only child his parents had. Although a star player in high school he was not offered a scholarship to the University of Texas which was his first desire, so he settled for UM. Knowing that his chances to getting into the NFL were slim at best Randy had followed a respectable course of studies such that he might end up getting into an MBA program or possibly into law school. 'Wow', thought Chloe, 'not just a dumb run of the mill jock but Randy was actually a man of substance that a girl could be proud of'. When it was Chloe's turn to reveal herself, Randy was astounded to learn that she had had no sexual experience.

For her part Chloe was uninhibited as a result of her alcohol consumption that she confessed never having had a date while in high school, and thus was still a virgin. "You mean to tell me you still are a virgin?" Randy exclaimed in true astonishment.

Chloe blushed and replied, "Yes it is true. I know I am not much to look at, but I hope to change my status soon. I am sure there is some guy around here I can lure to relieve me of my virginity."

Randy wondered how Chloe got the idea that she was unattractive but not to look at a gift horse in the mouth, he said: "I just have an idea. I am truly grateful and indebted to your help in my academic studies, so I think it is only fair that I return the favor in kind. How about I undertake giving lessons to you for your study of sex? I am somewhat experienced so that I believe I am qualified to be your tutor in this course of study."

"Really!" gushed Chloe already a bit inebriated such that all her inhibitions, what little of it she had, had disappeared and thus did not contemplate how outrageous and bold was Randy's statement. "I cannot think of a more generous offer and so I accept. When and how do we begin?"

A little startled by the ease of acceptance, Randy nevertheless was quick to take advantage so he said, "Well obviously the first lesson has to be the loss of your cherry which can be undertaken right away whereas other lessons can be scheduled later under mutual convenience. So, what say we go to my apartment in order to rid yourself of your troublesome virginity?"

"Lead the way big boy" was Chloe's only response. Randy could not help but wonder how lucky he was to score with such a gorgeous babe without hardly any effort on his part. Of course, being the starting quarterback on a major college football team meant he was used to getting almost any girl he wanted. Still every female until Chloe always offered some resistance and played at least a little hard to get even when it was an obvious pretense. There was a female need to preserve a sense of dignity to avoid being labeled a slut. Thus, Randy had a little lingering doubt creeping into his mind. A girl so easy was not normal so maybe she was a wacko despite being obviously intelligent given that she was in the aerospace engineering program.

As to Chloe all she was just thinking was how lucky she was to have a stud like Randy want her. Since she never had a date nor even yet kissed a boy, she was not knowledgeable about normal angst between the sexes in dealing with each other. All she knew was that based on her viewing of porn, sex seemed like an enjoyable activity that she was eager to experience. She had not had any close female friends and did not have a close relationship with her mother because there were seven siblings all younger than her, who demanded their mother's attention. Thus, Chloe had not developed any female wiles that most boys her age were used to. She was unconcerned about proper interaction between the sexes to ensure that the female avoid being labeled a slut or a whore. She knew what she wanted, and she was determined to achieve her goals notwithstanding society's strictures.

Randy's apartment was quite close to the bar well within easy walking distance. That was a good thing since Randy did not want to risk any DUIs that could jeopardize his scholarship. As soon as the couple was inside his apartment, to Randy's surprise, Chloe grabbed him and started kissing. Since Chloe was almost as tall as Randy, she had no trouble initiating the kiss, but her inexperience was quite obvious although her passion and determination was to be congratulated.

"Whoa! Slow down take it easy. This is your first time why not savor it and get the full enjoyment", protested Randy as he stopped the kissing while amazed by the aggressiveness of Chloe.

"Sorry yes you are right I forgot you are the teacher, but I wanted to get to the meat of the lesson without delay but from now on I'll do what you say," replied Chloe with excitement and her voice had become husky and sultry as she realized she was about to experience her first sexual act. Her lowered voice and her woman's scent were having a hardening effect on Randy's cock.

"Good" was all Randy said as he resumed kissing her. This time their kissing was slow and languorous. Chloe's lips were big but soft and as sweet a pair of lips as Randy had ever tasted. Their mutual breathing also slowed down as their kisses intensified. Soon Chloe's lips instinctively parted and Randy was able to penetrate with his tongue. When his tongue met hers, an audible deep moan escaped from Chloe's voice. Their tongues soon were engaged in a frantic duel that left Chloe breathless as her nipples hardened and felt like pebbles. Meanwhile Randy was fully aroused just from the kissing and his hard cock was pressing hard against her thigh. Instinctively and probably in self defense, Chloe reached for his cock. As soon as Randy felt her hand on his cock, he could sense he was leaking fluid and he knew it wasn't urine. 'God' thought Randy, 'she is driving me crazy if I can't get myself under control I'm going to cum before my cock gets anywhere near her cunt.'

Randy stopped the kiss and commanded, "Take off your sweater." As Chloe had succumbed to a heavy sexual daze, she had momentarily lost the power to speak. She silently bent down and removed her sweater. Tossing the sweater aside she turned her back to Randy to invite him to remove her bra and being no dummy Randy did just that. As Chloe then faced Randy, he got his first glimpse at her beautiful breasts. Randy actually gasped as he thought he had never seen a better rack than Chloe's. They were BIG but not unsightly big. They were perfectly pear shaped. The areolae on her breasts covered almost half the area of each tit and were a most unusual deep reddish color unlike the typical pink of most girls he had known. Her nipples like the rest of her were big and as a result of her excitement were unnaturally swollen. The uniqueness of her areolae and her engorged nipples were the best eye candy he had ever witnessed. "My God Chloe those are the most gorgeous tits I have ever seen" Randy uttered as he started feeling and massaging them.

Having recovered her power to speak Chloe giggled and said, "Why thank you kind sir- I am glad you like them."

With that Randy started to lick her nipples and then sucking them alternating each boob in rhythm. Pure pleasure coursed throughout her body and Chloe started moaning rather loudly. All of a sudden Randy sucked into his mouth an entire nipple and as much of the surrounding area as he could manage and started nipping with his teeth. Shots of pain with each nip intermixed with the pleasure Chloe was receiving. She started babbling out loud and rather loudly at that, "Yes! Yes! Oh God! Oh God! Suck my tits! Suck my tits, Randy! Good boy! Oh! Oh! Oh!" Chloe sensed that she was sounding foolish and stupid, but she could not help herself as the pleasure sensations were overcoming her.

Suddenly Randy stopped and said while pointing to the bedroom: "Enough. Take the rest of your clothes off and get yourself onto the bed." In her eagerness Chloe almost tripped as she in effect ran to the bedroom and got naked just under the speed of light. Innocent as she was, she nevertheless had no inhibitions and thus had no shame. All her thoughts were devoted to anticipation of the pleasure that she imagined awaited her. Randy also wasted no time in getting himself naked and quickly joined Chloe in his bed.

Wordlessly Randy resumed kissing her and Chloe responded enthusiastically. Randy aroused Chloe even further by also kissing her neck and ears hitting all her erotic spots. By this time Chloe was completely lost to the pleasures and she was moaning without let up while stroking his body. The passion that Chloe was exhibiting caused Randy to wonder if she was as innocent as she had claimed but such doubts were dismissed as he realized there was no reason for Chloe to lie. As he finally touched her vagina for the first time he was astonished to feel how drenched her pussy hair was from her female juices- obviously she was truly ready to receive him virgin or not.

Ever the gentleman Randy said, "I don't know if you know this Chloe, but the first time a girl has sex it hurts like the devil but the pain will soon go away and then you will no longer have pain whenever you have sex"

By this time Chloe was almost delirious in her passion that she just gasped, "I don't care- just do what you are going to do to me and hurry."

Without further ado Randy assumed the missionary position and started entering her cunt. Considering Chloe was a virgin Randy expected her to be somewhat tight but still as big as she was he thought she should nevertheless be able to easily accommodate his cock. To his surprise Chloe's cunt hole proved to be smaller than he had anticipated and it was a struggle to push his enormous cock in. Finally he could feel the tearing of her hymen and his cock then completely filled her. Chloe let out an agonizing loud scream of pain that made Randy cringe. Instinctively Randy started to withdraw with the intention of alleviating her pain but Chloe wrapped her legs around the back of his knees and held on tightly while crying: "Stop! Please don't move just stay still for a moment." Randy naturally complied as he saw a couple of tears form in each of her eyes.

'God', thought Chloe, 'this hurts so much.' But despite the pain of the rupturing of her hymen, she knew she wanted this. Wanted him so deep inside her that she could never forget what it felt like to be fucked by him. She wanted him devouring her, wanted him possessing her.

After a moment or two the pain miraculously dissipated. Chloe released a huge breath of air and said, "OK Randy start- don't stop now just fuck me and fuck me hard"

Randy started pumping away. With the pain gone Chloe only felt pure unadulterated pleasure. The pleasure continuously increased in its intensity as Randy's cock kept moving in her cunt. Chloe again started moaning and her body was involuntarily moving in rhythm with Randy's thrusts. As the speed of their fucking accelerated their bodies became sticky with the sweat from their exertions. Finally as Chloe was starting to see stars and fireworks and began feeling that she was floating out of her body she could not help herself but started screaming very loudly: "Oh fuck! Oh shit! Fuck me Randy! Don't Stop! Ahhhh! I'm going to die"

Obviously Chloe was orgasming and her screams prompted Randy to reciprocate in kind as he shouted "Shit Chloe I'm cumming! Here's my cum! Oh shit! Oh fuck..." And Randy was cumming as he felt burst after burst of semen leave his cock. It was without a doubt the most euphoric moment in his life that he had experienced. It was without doubt the best lay he had ever experienced and he marveled that this was so even though Chloe indeed had been a virgin. If there had been any doubt of her virginity, her blood all smeared on her thighs as well as on his cock dismissed such doubt. At this point Randy noticed that Chloe's body had completely relaxed since Chloe had fainted!

However, before Randy could become too worried Chloe woke from her swoon with a huge smile on her face. Wrapping her arms around him she started kissing him on his lips and cheeks and said, "Oh thank you Randy. Thank you for fucking me. Thank you for getting rid of my virginity. It was a trip. Can we fuck again?" And so that was how Chloe Ashley Anderson lost her cherry.

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Marklynda2Marklynda2over 1 year ago

You've set the bar high on your first offering!

I try to read an author's first posted story upon finding them on Literotica. I must say this story has all the hallmarks of being a captivatingly epic tale. It is truly well thought out and written with great characterization, background, angst and a sensitive treatment of an innocent's entry into womanhood. I appreciate your and your Muse's imagination (memories?) and abilities to bring it to your story. Thank you for sharing your vision and talents.

BodingtonBodingtonover 11 years agoAuthor
Explanation?

There is no doubt that the feedback dated 12/19/12 by Mr/Ms Anonymous is cryptic. I wonder if Mr/Ms Anonymous would care to elaborate?

AnonymousAnonymousover 11 years ago

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