Nightmare to Fairy Tale by Jaelyn Petrove
by ahorsewithnoname
Copyright© 2024 by ahorsewithnoname
Erotica Sex Story: From high school virgin and despised by her parents and siblings to superstar MIT student and then beyond, this rollercoaster ride, told in the form of an autobiography, involves lots of sexual interludes and exploration along with interweaving real-world Boston-area events to pull the reader deep inside.
Caution: This Erotica Sex Story contains strong sexual content, including Ma/Fa mt/ft Fa/ft Consensual Romantic Lesbian Heterosexual Fiction Historical School Workplace Group Sex First Masturbation Oral Sex Sex Toys Voyeurism .
Being a girl and growing up with three older brothers and indifferent parents made for an excruciatingly painful childhood. Oh, not that they were excessively cruel or hurtful, because they weren’t. Instead, it was the expectations that were handed down from one to the other, until it got to me, the youngest child. I was the female, the weak link, the non-athlete, the one without a penis, so there were no expectations for me other than to grow up, find a suitable husband, get married, and produce children.
I learned from a young age that both of my parents loved my older brothers more than me. It was never openly said to me, and I was not told that I was an oops baby, but one evening, the night before Christmas when both of them were downstairs in the living room wrapping presents, I had snuck down the staircase and eavesdropped. What I heard shaped the woman I became.
“Overpriced pieces of plastic,” stated my father with utter disgust, wrapping the smartphone’s glittery case, “it’s bordering on criminal what they charge for this junk and that we have to waste our money on it when she won’t appreciate it.”
Mother was placing some clothing in a box and then started to wrap it.
“Are those the...” and Father let the sentence trail off, his brow furrowed with mild irritation.
“Yes. Although she barely needs them, poor thing.” She put the wrapped box down and hefted up her breasts slightly in both hands, father keenly watching her as she did so. “She certainly didn’t inherit my genes.” Father chuckled. I almost gasped aloud as I heard them making fun of my small, almost non-existent boobs. Instantly I could feel wetness forming in the corners of my eyes. At my age, most high school girls had A or B cups. Not me. My brothers called them mosquito bites.
“You aren’t going to have her open that in front of the boys, are you?”
“No, certainly not,” said Mother, moving the box to the side and away from the other packages. She would eventually give it to me upstairs, in my room.
“Good, because we don’t need to fuel their imaginations and their cocks.” Mother laughed at Father’s crude comment, then reached over and put her hand on his arm, getting his attention.
“What say we finish up here and then we can go have a more detailed discussion about cocks, or, rather, a certain cock?” With that, she moved her hand from his arm to the front of his trousers and gently squeezed.
I had seen and heard too much, and silently moved back up the carpeted steps, then down the hallway to my room where I crawled into bed, pulled the covers up high, and cried myself to sleep.
I realized a couple of things that night. First, saying “I love you” doesn’t mean that you truly love someone. Second, I had to get away, far away, from my so-called family.
I spent every possible minute advancing my education. I worked tirelessly, foregoing friends, dates, and extracurricular activities. If it was something that I could do during my time at school, I’d do it. Otherwise, I was at home, in my room, studying. I was relentless. I’d break for dinner, I’d do my assigned chores, and I’d attend church, grudgingly because I had no choice, but beyond that, I fought every attempt to pry me from my work desk. Math and science were my favorites, but I excelled in all subjects.
My mother’s sister lived three houses down, so, when it came time for the annual family vacation, I balked and argued that I should be allowed to stay home with my aunt so close. I won. They didn’t want me to go anyway. When they were gone, did I throw parties, invite boys over, get drunk? No. I did spend slightly more time on the bottom floor, for a change of pace, but it was all spent reading. I didn’t have a television in my room and only used the internet for research. During the summer, I was able to get through many novels in under a day, but some of the longer, more complicated ones would take two, like, Don Quixote, War and Peace, and of course The Lord of the Rings. I never owned a book, but made excellent use of the library, although sometimes I had to read books online.
For birthdays and holidays, all I asked for was cash for college. Clothing was, well, they had to clothe me. But I took every scrap of cash and saved it. I knew I would need it early in my senior year. I babysat for money as long as I could study too.
Late in my junior year, things had changed somewhat. I grew tits, for example. B-cup, and, on a slender frame like mine, they stood out. I did nothing to enhance them or my looks. No make-up, only jeans and T-shirts, and a jacket during cooler weather. Sneakers, non-brand name, were fine for me as were non-brand name jeans and all clothes. I really didn’t want the attention.
During the summer before my senior year, the family went away for two weeks, thankfully. By this time in my life, I had developed a slightly mild interest in sex. I wasn’t an idiot. I knew what my clit was and where it was located, and once every week or so when that itch would develop into a slight frenzy, I’d take care of things. Almost clinical, as I didn’t want to get too involved.
But I also realized that I needed to find out a few things before college, so, I hatched a plan. Joey was a year younger than me and lived in the neighborhood. He was half a nerd, half a jock, but not much of an athlete. He tried. Anyway, on the second day of the vacation, I saw him walking to the field for soccer. I called out to him and met him halfway up the driveway. We were friendly, but not friends.
“Hey Joey, my Dad asked if I could find someone to mow the lawn while they were away. Something you could do today after soccer?” I was wearing a tighter t-shirt, and my breasts were making a good show of themselves.
“Um, yeah, sure, uh Jaelyn, I can be over around 2?” His eyes were surreptitiously moving back and forth from my tits to my eyes.
“The mower is in the backyard.” I smiled and turned, letting him watch my ass twitch as I went back into the house.
Right before 2 p.m. the side gate opened and Joey entered. I was lying out by the pool, wearing a modest bikini. His eyes kinda’ popped as I stood and pointed to the shed, indicating the location of the mower. As he walked over I put some lotion on and then went back to laying on the lounge chair.
It took less than an hour for him to finish both the back and front yards. After putting the mower away, he came over to me. I had been in the pool and was now lying on my belly, but I had left my top untied so I wouldn’t get string marks across my back. Or that could be my excuse.
“Hey, Jaelyn? I’m, uh, done.”
“Oh, okay,” I said, turning over and getting up. Joey’s eyes, now quite wide with abject shock, were fixated on my breasts and hard nipples. “The money’s in the house, come with me,” and I walked ahead of him, nervous, but determined.
I looked around the kitchen while he stood there, not sure what to think, I’m sure. I couldn’t find the money. That’s because there was no money. I was going to pay him out of the money that they left me for food and incidentals. But this was part of my plan, to not be able to find the money.
“I’m sorry, I can’t find where they left it. My Dad will have to pay you when they get back, but, um, shoot, I feel bad, so let me do something for you since you did such a good job,” and with that, I pulled the string on my bottoms, and they fell. I was totally nude standing before this 16-year-old boy.
“Oh shit!” he said, his eyes quite wide again as he looked right at my kitty. I had trimmed it nicely, in the shape of a heart.
“Oh! You ... you don’t like? You think I’m ... ugly.” With that, I put one hand in front of my kitty, and the other I used to try and cover my breasts.
“No! No! Jaelyn, fuck, you’re gorgeous!” Joey took a couple of steps forward to sorta’ emphasize his words, which helped me.
“Really?” I was back to a sweet smile and moved my hands to his shoulders as I stepped forward and leaned in to kiss him.
It was a fairly quick kiss on the lips, both of us pulling back just a few inches and looking into each other’s eyes. Then he kissed me, his arms moving around my back and pulling me close. I wiggled my tongue a bit and slipped it inside his mouth, taking his soft moan as a good sign.
I pulled back slowly and looked into his eyes. “Promise to be gentle with me?” He nodded, and I smiled again, then slowly knelt in front of him. Pretty sure I heard him mention the Lord as I did that.
First, it was the belt, then the zipper, and finally, I tugged the jeans and boxers down toward his knees. As I figured, his cock bounced straight up and saluted me. I didn’t have anything to compare it to, but, it looked nice, not small, not too big, but I had a plan and didn’t have time to admire it too much.
Again, I heard God invoked as I took hold of it in my right hand and tilted it toward my mouth, which I moved forward to engulf half of it. My mouth was watering so it helped. My kitty was wet too! I started moving my mouth back and forth, and sucked too, along with moving my tongue around. Not positive I was doing great, but, I heard an “Oh fuck” and later a “Yesssss” so I just continued. Then I remembered something and moved my other hand up to gently squeeze and rub his ball sack. I guess that was the trigger as I heard a God reference and then felt his cock pulse and he began shooting his cum.
I was prepared and wanted this, wanted to experience it, so I eagerly continued fellating him, bobbing my head back and forth to coax as much boy seed out of him as possible. I saved it, wasn’t easy, but when he stopped throbbing in my mouth, I got back up, and then with us looking at each other, I swallowed. Then I had a little burp and giggled a bit, using my finger to push a little cum that had escaped back into my mouth.
Joey was nonplussed, staggering a bit. I helped steady him, didn’t want him tripping over his clothes. “Jaelyn, wow, uh, that was fucking amazing!”
I smiled shyly. Reaching down, I touched the dark ringlets of hair surrounding my kitty and then brought my fingers up. They were coated with my wetness and his eyes were laser-focused on them.
“Do, do you, do you think you could, you know, do something to me?” I asked shyly, my voice low.
“Oh hell yes,” he said and started to look around. I didn’t want to do this on the kitchen counter so I helped him out of his clothes, and playfully licked his cock once while down there, then led him upstairs to my bedroom.
Laying back on the bed, I had my knees bent, but my legs closed. He was standing right near the bed. Slowly, I parted my legs.
Yes, Joey got religion again, calling upon God. I just wanted his fingers and tongue, and true to his word, he came through. I came too.
I can’t say if he was any good at dining at the Y because it was my first time experiencing it, but I can say that it felt incredible. His mouth and tongue moved everywhere, fast, slow, inside me, licking my clit, probing, sucking, even his fingers got into the act. I encouraged him to suck on my clit until I orgasmed very hard.
Once I caught my breath, we again connected with our eyes, and I glanced and saw that his cock was again very hard. I looked at his eyes, back to his cock, and then back to his eyes, and nodded with that shy smile.
Joey crawled between my legs and up my body, kissing me. I got to taste my kitty on his lips and tongue and then he looked at me.
“Um, Jaelyn? I’ve uh, uh, well, this is--” and I cut him off.
“It’s my first time too, Joey. Let’s learn together, okay?” My timid smile gave him all the confidence he needed. I took hold of his cock, aimed it at kitty, and it slid right inside. I was so wet that there was no pain and he went deep. I’d taken care of my cherry long before. I’d love to say that it was romantic and tenderhearted; but no. It was pretty fast actually, even though he’d recently orgasmed. I’m guessing maybe five minutes, pretty hard and deep, but at least I had one orgasm before he finished. I had him pull out and shoot all over my tits. He loved that. I think he was not sure what to do or say but did thank me and said I was beautiful. And he said not to bother my Dad about the lawn money. Then he quickly put on his clothes and left.
In late August, I used the money that I had collected to pay for college applications. I applied to a dozen different schools, but as I found out, I didn’t need to do that. With a 4.0 average and an almost perfect SAT score, I got accepted by all the schools. Who knew? Then it was a matter of paying for college.
Yes, you are correct if you assumed that my loving parents wanted to contribute zero dollars to my education. There was no reason for a girl like me to want to go to college. I could get a job locally, find a guy, get married, and manufacture some kids. Wal-Mart was hiring, my parents told me.
Hitchhiking the Massachusetts Turnpike may not be the smartest way to get from Bumfuck to Cambridge, but in my case, it was the only option. I was lucky and got a ride after about ten minutes of waiting, and wouldn’t you know it, it was a couple heading back to Harvard! That was pure luck on my part since it was close to MIT.
Amy. Her name was Amy Swanson, and she was youngish and ambitious and had a great personality. She was the Assistant Director of Admissions, and I earned an interview with her and not one of the first-level interviewers because of my grades, test scores, and I guess my application essay. I wrote a somewhat scathing rebuke of Rousseau’s Discourse on the Origin of Inequality. When she wasn’t looking at me I snuck a peek and saw “Wow!” handwritten across the top.
“You hitchhiked here?” She was incredulous, asking if my parents drove me. I nodded; I was kind of embarrassed. She asked why and while honesty was always my choice, I hesitated in throwing my family under the bus. Not that I cared about them, I just didn’t want to look poorly in her eyes. I shrugged.
Then I found out that I was expected to stay overnight for a second interview, campus tour, appointment with financial aid, and so on. She could see the distress written hard across my face.
“Jaelyn? It’s okay, you can talk to me.” I couldn’t help it. The stress of travel, the enormity of the institution, and now this ... it was too much. I burst into tears. I tried to curb it, but it was full-boat hysteria. She came around the desk and moved me to the sofa and hugged me and told me it would be okay, just breathe, relax, take whatever time I needed. She was comforting, and eventually, the heaves stopped. I’d never had a panic attack, and that’s what she called it.
I felt like I had blown the interview, so I thanked her and started to gather up my stuff.
“Jaelyn? We’re not done here.” I looked at Amy, incredulous. She wiped away a little water that was forming at the corner of my eyes again and asked me to sit down. The interview continued.
We talked for at least an hour, right through lunch. She buzzed her assistant and told her to reschedule her afternoon meeting, then gathered me up and took me to lunch. We simply talked nonstop and I told her everything, just unloading all of it, my aspirations included.
“So,” she began, paying for our lunch with her Gold card, “you have no hotel for tonight, and, from what you’ve told me, I suspect you don’t have the cash to pay for one, true? I don’t see an overnight bag with you, so you probably don’t have proper attire for tomorrow?”
I blushed and stammered.
“I’m not judging you, Jaelyn, honest.” I simply nodded and looked down.
“Okay then, you’ll stay with me tonight. We’ll need to stop back at my office, and then ... what?” She could see me welling up a bit.
“You’re just, you’re, uh, you’re just really nice. Pretty too.” After I’d said that, I really blushed; what was I thinking?
She smiled and touched my face with her hand, then got up and we left, heading back to campus.
Later that evening we sat on her sofa in a beautiful off-campus apartment, drinking white wine. She knew I was underage but said it didn’t matter since we were in her place. She opened two bottles and allowed me to have some from each.
My clothes were in the wash, though she said that she was going to loan me a dress for tomorrow since we appeared to be about the same size. I was wearing a luxurious bathrobe. She had changed into one too, I suspect to make me feel less awkward about my lack of clothing.
The conversation wafted from serious stuff to flippant comments about movies and other nonsense. We covered poverty, the glass ceiling in some companies for women, wealth and how it applied to medical care around the world, and also how progressively worse just about each movie sequel turned out. Then it abruptly turned to sex.
“So, Jaelyn, do you have a boyfriend?”
I thought of Joey, but shook my head, pouring myself a third glass. Amy persisted.
“Have you gone on dates?” Again I shook my head, this one with a bit of a blush from embarrassment at having so little of a social life. “No, I’ve mostly worked hard on my education.”
“Virgin?” I blinked. She smiled and knew she had me.
“Oh? Do tell, do tell!”
I blushed further, not believing that I was going to spill the beans about Joey. But, I did. I suspect that the wine helped. When I finished I realized that I’d been talking a mile a minute and was parched, so, more wine, of course.
“Joey sounded nice. Most first times are wham bam thank you ma’am, so it was great to hear you managed a couple of orgasms too.” She finished her third glass, and poured more for both of us. “So, have you been with a girl?”
I nearly spewed the sip of wine that I had just taken. I shook my head, my cheeks crimson. “But, I’m not, I just don’t know...” and stopped talking.
I didn’t realize what had happened until I saw her staring. I followed her eyes and saw that my robe had parted when I’d nearly spit out the wine, and my kitty was on display!
“Old school, I see,” she said, her voice a little gravelly. “Nice bush.” I bet my ears were red by this time as well as the rest of my face. I started to cover up. “Don’t.”
I looked over. She’d parted her legs, revealing her bush, red, like the hair on her head.
I just stared. And, I felt butterflies take flight in my tummy. My head was spinning a bit, and pounding, but not in a bad way. I must have been staring for ten seconds when she slowly stood up, her robe falling off her, revealing her nakedness. She was stunning, with a peaches and cream complexion, and freckles, and now she was walking toward me.
She leaned down, and gave me a gentle kiss, barely brushing my lips. My eyes had closed, but when she didn’t continue the kiss, they opened, and I whimpered my need. She kissed me again, and this time our tongues danced playfully.
Then Amy knelt in front of me. My hands were partially concealing my privates, but she was looking into my eyes, not between my legs.
“Jaelyn,” she began, but I stopped her.
“Jae. Please, call me Jae.” I spoke very softly, and she smiled. “No one calls me Jae. I’d like you to.”
“Jae, if you say no, I’ll stop, I promise.” My eyes must have been pretty wide open at this point. “But I hope you don’t.” Amy licked her lips after she said that, and I got a shiver, and knew I was wet with desire.
The difference between what I experienced with Amy that evening, and what Joey and I experienced, could be found in the dictionary as an example of polar opposites. With Joey, it was rough, raw, and almost haphazard, like a drag race. With Amy, I soared to heights I never knew existed and learned more that night about my own body, and some about hers, than in my previous 17 years. And Amy tasted as good as she was beautiful.
The dress she loaned me was perfect, conservative but not dowdy, and exactly what I needed. The day went by very fast, possibly because my mind was awhirl from the previous night’s encounter. That morning, when I awoke and looked over at her, sleeping, I felt a hunger within me. It wasn’t just sexual, it was far deeper. I now know that it was me, falling in love with someone who spent more time talking with me in less than a full day than my entire family did in the past year.
Since it was a Friday, I stayed another night, and then the weekend. What I didn’t realize at the time was that Amy too had begun falling in love with me. Nor did I have a clue as to the extent of her reach, due to her family. Both of her parents were professors; her mother was the Department Chair for Applied Sciences, and her father was the chair of MIT Indigenous Communities Fellowship program. They were both powerhouses within the university, and as I found out later, she got them to pull some strings for her, well, for me.
A week later, I was enrolled at MIT. I had plenty of high school credits, more than the Commonwealth needed for granting a diploma, so a couple of calls were made, and that was that. Being only a couple of weeks behind wasn’t terrible, but getting adjusted to campus life was somewhat of a shock. Of course, Amy didn’t throw me to the sharks, so to speak. I received introductions to all of my instructors, and it was obvious that they held Amy’s family in high regard.
My parents were glad to have me gone I am sure, though my Dad mumbled something about still getting a deduction for me on next year’s tax return. Amy had borrowed an SUV to drive me home to gather all my belongings which didn’t even fill it. I hugged my Mom, shook my Dad’s hand, and mumbled goodbyes to my brothers who were busy playing a video game. None were attending college but they all had jobs. Wal-Mart was always hiring.
Officially, I was renting the upstairs attic at Amy’s house. Unofficially, uh, I was spending the night in her king-sized bed.
Amy was insatiable. She was such a professional during the day, dressed impeccably, her mannerisms were not stiff, starchy, or in any way snooty. She was very personable, always a smile and a good word for a visitor, and when she and I were together socially, I was a student, and she was staff.
At night, however, when the doors were locked, and the shades were down, it was as if she had found a veritable feast between my slender legs. Inevitably, between her lips, tongue, and fingers, and a toy she called The Wand, she would drive me sexually insane with at least a half-dozen heart-thumping orgasms before I’d either pass out or be begging for a reprieve. Sometimes, she’d coax one more out of me, giggling as I’d soar off the orgasm cliff once again. Most times I’d be so brain-dead that she’d crawl up next to me and we’d kiss for a bit, and then once I’d marginally recovered, her eyes would ask permission. With consent, which I always gave, she’d move up and straddle my head, gently lowering her kitty to my lips so that I could reciprocate the oral pleasure she’d given me in the position so most loved.
For the next two years, I could hardly fathom how little I had learned in high school. Sure, my reading of the classics had helped educate me, but here at MIT, I was no longer the smartest person I knew, in fact, far from it. That took some getting used to, and, some disappointments along the way.
Amy was the one constant in my life. Gradually she pulled me from my shell to where I could socialize like a normal human being, and not be waiting for the inevitable knifing like at home. My knowledge soared, both in and out of the classrooms. One evening, Amy and I were having dinner with a friend of hers who she’d graduated MIT with and was in town from the West Coast. After food and drinks, we ended up back at Amy’s house, more drinking ensued, and then I experienced my first threesome. Having this wonderful lady between my legs, devouring me, while Amy was crouched over my face, well, words are hard to find to describe my levels of pleasure. Later, when Amy donned a strap-on and fucked me doggy style while I serviced her friend orally, it was yet another amazing experience.
In my senior year, Amy said something that shocked me. We were laying in bed late one night after she’d pulled several orgasms from me. She told me that she wanted me to go out on some dates with a guy! At first I laughed, then, I balked, not sure if she was even serious, but, she was very serious. She kept pressing and I finally broke into tears, sure that she was trying to end things with me.
“Jae, my sweet, sweet Jae,” she said, pulling me into her arms and hugging me as I shook with tears. “I love you, and I will always love you. I simply want you to experience everything, and that includes guys. They can be ... fun, at times.” She smiled warmly and kissed my lips.
I pulled myself together. “But, I don’t even know if I like guys like that!” She giggled.
“You like it when I have Big Ben join us!” I blushed a bit and started giggling too. Big Ben, as we called him, was the strap-on. “And your experience with Joey wasn’t bad, right?”
“Yeah, but Ben is you, not a real guy with a real...”
“Cock?” she said, and I nodded, not sure what to say.
“Jae, I don’t want you to go out and fall in love with some guy. I just want you to go out and get fucked and then come home and tell me all about it.” I was wide-eyed with surprise!
“Or,” she said, casually taking some wetness from my kitty and tracing one of my nipples with it, “you could bring him back here.” I stared at her, even more surprised. “And then afterward I could join in.”
My mouth flew open in utter shock. “What? You like...” and this time she just waited on me. “Cock?” I said, I’m sure I was blushing again.
She licked the wetness off my nipple and then moved her mouth up near my ear, and whispered, “I would love nothing better than to see you doggy style, getting your sweet pussy pounded by some big cock while your face was buried in my pussy! And when that stud was ready to shoot, he could cum in my mouth and then I’d swap it back and forth with you. And yes, I’ve fucked my share of guys, and given my share of blowjobs too, girl!” Her smile always dazzled me.
I almost came from her words, and did cum shortly thereafter as she once again went down on me and engaged the Wand too.
It took a few weeks for me to gather enough courage to go out on a date. Amy and I would look together and try and figure out a good guy for me to target. Eventually, we settled on Evan. He was a freshman, good-looking, not at all overly enamored with himself, more of a nerd than anything. He kind of reminded me of me, actually, in a way. It wasn’t as if we both weren’t busy with lots of other things, school, events, her family, and so on. So, there wasn’t a rush.
One day I approached Evan while he was sitting in the cafeteria for an early dinner. I sat down at the same table, opposite and one seat up from him. When he looked up I smiled and just went about my business, but noticed that he was staring a little bit. I’d made sure that before I walked in my nipples were standing at attention from some pinching in the bathroom before I’d sat down.
While I ate, I pulled out a somewhat crumpled note along with a pencil and began to study it. It looked like this:
Zpvs ebsf jt up csjoh ipnf b sboepn hvz zpv’wf ofwfs nfu cfgpsf boe hfu ijn up xbudi uif tuvqje spn-dpn uibu J ibwf tfu jo uif EWE qmbzfs. Uif ljuuz jt vq up bmnptu gjguz epmmbst jg zpv mptf!
I pretended to work at it a bit, then tossed my pencil down in disgust. Evan looked over.
“Problems?” he asked.
“Oh, sorry, didn’t mean to disturb you.” I smiled. “It’s my roommate. We are playing this long game of Truth or Dare and she sometimes gives me my dares in code. I can’t get a handle on this one.” I looked all frustrated, a pretty girl who didn’t have a clue.
“May I?” he asked, putting his hand out.
Come into my lair said the spider to the fly, I thought to myself. I handed him the paper.
ROT13 was similar to a code base that was developed in Caesar’s time in ancient Rome. Letters were ROTated by 13 places. In this case, this was ROT1, much easier, and it took nerdy Evan only sixty seconds to unravel the mystery. He pulled a pencil from behind his ear and began deciphering it. When done, he had a big smile on his face and handed the paper back to me.
Your dare is to bring home a random guy you’ve never met before and get him to watch the stupid rom-com that I have set in the DVD player. The kitty is up to almost fifty dollars if you lose!
“Hey, thank you so much!” I gushed. Then my face fell.
“What’s wrong?” Evan noticed and showed his concern. This was going so well that I began to think that I might look into the Thespian Club here on campus, that I might have a career in acting.
“I’m, oh, crap, I’m going to lose this bet because I waited all day to get the message figured out. There’s no time to just find some random guy to bring home to watch a movie. Ugh! Fifty dollars too!”
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