Virginity Lost on Vacation

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Chubby Canadian cutie deflowered by handsome black guy.
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RetroFan
RetroFan
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INTRODUCTION & DISCLAIMER - In 1999, overweight but pretty Abbey Rosen from Toronto takes a vacation to South Africa for a safari. This horrifies her very traditional Jewish mother, who firmly believes that Abbey should be looking for the right man to marry and start a family with rather than jetting off on vacation and into the dangers of the African bush. Abbey stands her ground despite her mother's many attempts to guilt her out of the trip and is rewarded when she meets David, a handsome and charming young black guy who works as a tour guide and has quite a liking for fat white girls. Abbey's virginity - still intact at the age of 25 - probably won't be returning to Canada with her.

All characters and situations in this story are fictional, with any similarity to real persons living or dead coincidental and unintentional. Only characters over the age of 18 engage in sexual activity. Please enjoy your trip back to 1999 and 'Virginity Lost on Vacation'.

*

From the time I emerged into the world in 1974, I was always the 'fat girl'. This was the case at the Toronto elementary, junior high and high schools I attended, at Jewish classes I attended after school, at our synagogue, in the neighborhood, at college, at work and even at home. My mother Esther and my father Tom were always slim, and my older sister Hannah and younger sister Rebecca likewise also slim. None of my grandparents were overweight, nor any of my aunts, uncles and cousins save for my father's youngest sister, and this was only when she got married, started having kids and took the adage of eating for two a little too literally. Prior to this my aunt was slim. Me, I was overweight through childhood, my teenage years and as a young adult. By the time I reached the age of 25 in the spring of 1999, I weighed 90 kilograms -- 198 pounds for our friends south of the Canadian border who haven't converted to metric -- and when barefoot stood at just 160 centimeters in height. Again, for those who don't use metric, that is five feet two inches tall.

Some fat kids have a few problems growing up. They get teased and bullied because of their weight, withdraw into themselves or sometimes become bullies themselves. Not me. From my earliest years, I always had an outgoing, bubbly personality and always saw the positives in things. I always had lots of friends both Jewish and non-Jewish, and an active social life. I was always a chatty sort of girl and I almost always felt happy when I woke up in the morning, whether this be a cold, snowy day in the middle of the Canadian winter, a sunny summer's day with the sun shining brightly over Lake Ontario, or a mild day in the spring or fall.

When I found out my height and weight and subsequent BMI of 35 courtesy of my doctor making me stand on the much-feared scales in his office, barefoot and dressed in my white D-cup bra and my white, full-brief panties I saw the positive -- at least I was still less than 200 pounds. Even when the doctor was giving me one of his lectures about healthy eating and required weight loss, I tuned out thinking of this positive rather than his stern directive of "Abbey Rosen -- you must lose weight."

I never let my weight bother me, and never allowed it to impede me or how I dress. I never let the fact that I was overweight stop me from wearing short skirts and dresses, long figure-hugging skirts and dresses, leggings, shorts and even a bikini. Okay, maybe the bikini was that one step too far for a young woman of my figure, but hey, being from Toronto it's not like I would wear it every day. Well I guess I could have, but in the middle of winter I doubt even my body so well insulated by blubber could have survived hypothermia. And believe it or not -- my doctor did not -- I actually did aerobics at the gym. I admit I was more like a small elephant to the other girls' slim flamingo or muscular lioness physiques, but I did try and always had fun.

At times I had tried to lose weight but my love of ice-cream, cakes, cookies, doughnuts, muffins, waffles, potato chips and French fries always bit me on my considerable ass and it was back to square one. And when it was that time of the month, keeping myself away from chocolate was mission impossible. At least being a Jewish girl I never had any kilojoule (or calorie) laden meats such as bacon, ham or salami, or deep-fried seafood. Had I not been Jewish and eaten such treats, I would probably have weighed close to 300 pounds. However, if it wasn't myself bringing my diets undone, my relationship with my mother played a significant role in keeping my weight on.

My mother and I always loved each other very much, but she often tended to be critical of me and frequently said, "Abbey, you would be as pretty as your sisters if you would only lose some weight." True, Hannah, Rebecca and I always looked similar facially, with the same long dark brown hair and brown eyes, but while I thought my thinner sisters were attractive, I never believed it about myself. However, one day when I was in college I walked by a construction site and overheard what some of the guys were saying about me.

One guy said, "She's pretty, but it's a shame she's so fat," and his friend said, "Yeah, she's about the best looking fat girl I've ever seen." A third man offered, "I wouldn't mind kissing that fat ass of hers, but it would take me all night." I was too amazed that the guys thought me pretty despite my weight problem to be offended, but then I was never one to easily take offense. One time, I got onto the crowded train and a guy jumped up, saying that a girl in my condition needed a seat more than he did. I thought it better to smile and thank at him before sitting down, rather than say that I was not pregnant and make him feel bad.

Mom, when not reminding me that I needed to lose weight, would take offense at my refusal of her food when I visited her and Dad for a family get-together. One time, I refused a second piece of her baked cheesecake for the simple reason that I was full, and she became all huffy and turned on the guilt, saying she had worked so hard on making it, and that she wouldn't have wasted her day preparing food that I wasn't going to eat. So of course, I ended up having another large slice, with double-thick cream and chocolate sauce, and at Mom's insistence took the rest of the leftover cheesecake home to eat at my leisure. It lasted as long as breakfast the next morning.

If I had submitted a movie comedy screen-play, sitcom pilot or novel about my family to a production company or publisher, my rejection letter might have read something like, "Dear Miss Rosen, while your ideas have potential, we feel that the mother character was a little too much of a Jewish Mother stereotype and therefore we regret to inform you that your submission was unsuccessful." However, one meeting with my mother and they would have seen that Mom definitely corresponded to the Jewish mother stereotype, and then some.

When not criticizing me about my weight or enabling my weight problems by feeding me high calorie foods, Mom would also be critical of me for talking too much. Admittedly Mom was not alone in that, other family members, friends, colleagues and other people would say I talked way too much for my own good, but Mom had this habit too.

Unfortunately, Mom's favorite subject matter when talking too much to too many people were personal things about me. I don't really think people wanted to hear about my menstrual cycle, my toilet habits such as spending too long in the bathroom, the intricate details of the really bad flu I had in spring or that I had missed my cousin's bridal shower because I was sick with diarrhea, but Mom obviously found the need to share these details and more with her friends and our relatives.

One thing Mom, and to a lesser extent Dad were obsessed with for all three of us girls was that we find the right boy -- the right Jewish boy -- get married, and produce grandchildren. With my sisters, this was no problem. Hannah met her future husband in high school, they married after college and had a son and daughter. Likewise, Rebecca had also met her serious boyfriend in high school and they were in their final years of college with plans to marry.

At the other end of the scale there was me. I had plenty of friends who were boys, but no boyfriends. In my senior year of high school, when I was aged 18, Mom and Dad were spending a lot of time with their friends Mr. and Mrs. Cohen, who were well connected with our synagogue and had an 18-year-old son named Warren.

Warren like me was not dating anyone, but unlike me he wasn't fat. In fact he was the opposite, skinny as a pencil and with big glasses and lank, dark brown hair. As was the case with my mother, had I written Warren into a screenplay or novel, it would have been rejected as he was too much of a Jewish stereotype, this time the Jewish nerd. However, Warren was a bigger nerd than any author could come up with.

It didn't take me long to see why Mom and Dad and the Cohen's were arranging things so that Warren and I were spending so much time together. I was the fat daughter who couldn't get a date, Warren the skinny nerd who a girl wouldn't date even for a million dollars. By putting us together more often, both sets of parents were hoping that we would find love together, and they would not have a single overweight daughter or nerdy son who was left on the shelf. It was like a farm or a zoo where animals are placed together as part of a breeding program. Not that our parents obviously wanted us to have sex at that stage; they wanted us to date, fall in love and get married, when we would then have sex to produce the desired grandchildren.

While I was wise to the plan, there was no way I was going to say anything about it, and there was also no way was I going to date Warren, not that he had asked me out. He was such a geek, completely obsessed with science fiction. I liked some science fiction, but did not really appreciate having my head talked off for hours about it. When not reading or watching science fiction created by other people, Warren would write his own science fiction in a spiral notebook. He let me read some of it once. An author or screenwriter would not be a profitable career for Warren.

However, when spending time with Warren I kept noticing that he was looking at me in a creepy way. First it was at my breasts, although with such large boobs, it was hard not to notice them. Even if I was skinny, I would still have large breasts. Okay, so Warren liked to stare at my tits. He was an 18-year-old guy, I was an 18-year-old girl who obviously had boobs. Big deal.

One Sunday evening the Cohen family were visiting for dinner, and I went upstairs while wearing a short navy blue pleated skirt and could not help noticing that Warren had positioned himself discretely at the foot of the stairs so he could look upwards at my chubby legs and up my skirt at my white cotton panties. I said nothing about Warren up-skirting me as it would have been too awkward.

A few weeks after this, I was wearing stirrup pants when Warren and his parents were over, and I bent over and could not miss the fact that Warren was staring at the fat cheeks of my bottom through the tight fabric of the stirrup pant leggings, the elastic of my panty lines and the shape of my vagina evident. Again, I did not call him out on this, and ignored his voyeurism.

Then the next weekend, I was wearing jeans a bit tight for me when we went to Mr. and Mrs. Cohen's house for lunch. I had my period, and was wearing a maxi-pad. I bent over without thinking to scratch an itch on my foot, and saw Warren's eyes go wide as he again checked out my ass but and instead saw far more than he intended, namely the shape of my pad between my legs. While I was embarrassed on one hand, on the other it felt kind of hot that he had seen something so personal and feminine. I blamed my hormones being out of balance.

I graduated high school, it was summer, and Mom and Dad were going to spend two weeks at the Cohen's cabin by the lake. I thought I would get out of it given I had a summer job at the supermarket but unfortunately my manager was a friend of my parents, so I had two weeks leave. My parents and Mr. and Mrs. Cohen must have been perturbed that Warren and I were not dating yet, and the two weeks in summer was the last ditch attempt for the captive breeding program to work. So it was two weeks at the cabin with Mom, Dad, Rebecca, Mr. and Mrs. Cohen and Warren. Hooray!

Again, I felt Warren's eyes all over my chubby little body, checking out my big boobs through my tee-shirt and my fat bottom through my tight denim shorts. One day, I changed my panties and placed my used underpants in the laundry bag on top of my other dirty clothes, and went out for a walk in the woods with my younger sister. When I got back, I found my dirty clothes out of order. The panties I had changed out of were to one side, screwed up in a ball. I reached into the bag and picked up my panties -- white cotton full brief panties with pink roses on them. I always wore cotton, full brief panties for two reasons. Firstly, being such a big girl, they were comfortable around the fat cheeks of my bottom and my pubic area. Secondly, between my legs the cotton absorbed the feminine dampness from my vagina, leaving me feeling fresh and comfortable all day.

Holding my panties in my hand, I asked myself the question; had Warren been fooling around with my panties? Had he taken them out of the bag and touched the soft cotton that concealed my pubic hair, my vulva and the cheeks of my fat bottom? Had he stroked the double cotton saddle that had rested against my vagina? Had Warren put my underpants to his nose, and smelled the musty feminine scent of my pussy? I looked at the creamy snatch stains I had left on my panties, and imagined the nerdy Warren smelling them.

The thought of Warren inhaling the smell of my vagina on my dirty panties made me feel violated in one way, yet at the same time, turned on that he found me sexy. A guy -- albeit a skinny nerd I was not interested in - found fat Abbey Rosen sexy. Between my legs, I felt my clitoris tingle and my vagina moisten. The following day, my dirty clothes bag was again out of order when Warren was left alone in the cabin, and again I felt the strange sense of violation combined with excitement as my denim shorts rode the panties I was wearing up into my vagina and ass crack.

Suspecting what Warren was doing with my panties, I became more aware of his voyeurism around me over the coming days. Getting up early to go to the bathroom one morning, my chubby little figure barefoot and wearing a white tee-shirt over white panties, I passed Warren while he was going to the kitchen to get a drink of water, and he could hardly keep from staring at my tits straining at the fabric of my shirt, my broad backside, or at my fat legs almost completely exposed.

He also seemed to hang out near the bathroom whenever I went to the toilet or had a shower, and while I had that same feeling of violation as I felt when I realized he was smelling my panties, I also felt strangely turned on. Behind the closed and locked bathroom door when I sat on the toilet with my panties down around my ankles, I would look down at my pubic hair and further down to my lowered panties and feet, thinking about how the nerd outside the door was getting turned on by fantasizing about me doing such private and personal things on the toilet. My vagina would get wet and tingle, and I would squirm my fat bare bottom on the toilet seat from these sensations. Whenever I got toilet tissue to clean myself, I would feel my toilet paper sticking to my aroused pussy, before I dragged it backwards to wipe my bottom.

It was the same when I was in the shower. I would think about Warren listening to the water running and imagining me naked under it, my boobs, my fat ass and my pubic hair covered in soap, further soap running down my chubby legs to my bare feet, with my toes clenching and unclenching on the tiles as my pussy responded to these thoughts by getting wet and tingly. As I used a washcloth to cleanse myself between the cheeks of my ass and around my anus I got more and more turned on, and even though I used a lot of water to wash my vulva, my towel would always end up with some pussy dampness on it after I dried between my legs after my shower.

Once again, I found my dirty panties were out of place in my laundry bag, and that one pair -- those I had been wearing the day before -- was missing. When Warren said he was going for a walk, I decided to do some voyeurism of my own and discretely followed him from the cabin. I stayed concealed and observed him go into a clearing and remove from his pocket my missing panties.

Warren held them up in his hands, admiring my white cotton undies and then lowered his face into the crotch, sniffing my feminine scent. He moved his nose to the back panel, to where the panties would have gone between the cheeks of my fat bottom and made contact with my anus. Again I watched Warren inhale the smell my vagina had left on my panties, then unzipping his pants and producing a very small, thin, circumcised penis and beginning to jerk off.

Observing Warren from behind a tree, I again felt violated, turned on and having seen Warren's unimpressive penis, highly amused at the same time. I bit my lip to keep from laughing, and in the panties I was wearing I felt my vagina getting tingly and wet. Warren reached orgasm, spraying semen everywhere and I made haste for the cabin, not giving away what I saw and finding that my missing panties miraculously returned to my dirty clothes bag some time during that day.

That night, my parents and the Cohen's went out with my younger sister, saying to Warren and myself, "Why don't you kids watch a video?" I had more on my mind than a video, however. Warren's voyeurism of me was getting me hot, and as an 18-year-old girl, was keen to experience sex for the first time. Warren might have been be a nerd with a small penis, but I knew I wanted one thing -- a penis in my vagina. And as Warren was so turned on by me in spite of my size, he could provide this.

Sitting barefoot on the couch next to Warren, I was wearing a pair of jeans that showed off my fat bottom and a shirt that displayed the shape of my big teenage tits, and I began to discretely flirt with him, adjusting my bra and my panties. Unfortunately, I made the mistake of mentioning science fiction to him and that was it. I was treated to a two hour monologue about Warren's favorite subject, and between my legs my vagina went back to sleep and my plans of getting Warren into bed to fuck me out the window. No, just no, he was too much of a geek. And my mother said I talked too much!

My parents and Warren's parents seemed disappointed that their fat teenage daughter who talked too much for her own good and skinny, sci-fi obsessed nerd of a son failed to find romance with each other, and the idea seemed to fizzle out after that. I saw Warren that summer when I was working in the supermarket and saw him checking out my tits and my ass in the blue dress that was the supermarket uniform, but nothing more came of the parental plans for Warren and me to date.

The summer came and went, I went off to college, graduated several years later and became an accountant, got a good job in a Toronto bank and eventually my own apartment. I was happy enough with my life -- I liked my well-paid job and spending time with my friends and family, but after reaching the age of 25 in the spring of 1999, things around me were changing.

My female friends were getting serious with boyfriends, one getting engaged and the other married. I was still a virgin, with no boyfriend and having never been on a proper date. My vagina was completely virginal. The only thing to have gone up there was my fingers when I masturbated either in bed at night or in the shower or bath, and I had never even used a tampon. Mom had never liked them -- I think one of her cousins had got toxic shock from using them years earlier - so she incessantly lectured myself and my sisters about how bad they were, and how we must avoid using them at all costs. Sometimes I regretted not shutting Warren up in the cabin that night seven years earlier, pulling down my jeans and panties and thrusting my hairy pussy at him and telling him outright to fuck me, but then would remember what a dork he was and think no, I made the right decision.

RetroFan
RetroFan
678 Followers