Chronicles of the Unpretty

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A life in the day of the beautifully challenged.
3.4k words
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Part 1 of the 2 part series

Updated 10/29/2022
Created 08/04/2010
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c8er2u
c8er2u
180 Followers

Author's note: This is for a dear friend of mine, you know who you are so I don't gotta call you out. To everyone else, I hope you enjoy this quick story as it unfolds, comment comment comment! Thanks in advance for the love!

C8ER2U

*

Wednesday February 06th 2008

So this is my first time keeping a journal, and I've decided to pull an Anne Frank and name you, my journal. I'm naming you because I don't want to feel like I'm having a one way conversation here. I would like to feel like I'm talking to an old friend. So, journal of mine, I dub thee Isabella.

Why Isabella you ask? Because that's the name I've always wished I could have had. Ever since I was a child I would fantasize about the name I'd have if I had a regular girl name; the name I'd have if my parents weren't cheapskates. Instead I was named Ryan. Ryan Lynn Shein. Yes, Isabella I'm aware that I have a man's name, and to answer your question before you ask, I loathe it.

See, when my mom got pregnant, she was living in Arizona. She was a travelling nurse and my father was a lawyer who'd just passed the bar. Neither was in a position to afford hospital expenses, so they did the only thing they could do: move back to Canada for a bit. On account of the free health care and stuff. Both of my parents are Canadian, and well, if you really wanna get technical, so am I, but I like to think if myself as a child of the world. I lived in so many damn places I really don't know where to call home.

I'm getting off topic here though, so back to what I was saying. Well, they'd done one ultrasound before they left, and it was only because my mom talked her friend into doing the ultrasound for her, and she hadn't quite graduated ultrasound school or whatever, so they were taking a chance, but who's complaining when it's free? Anyway, they do the ultrasound and there I am in the womb, except this dumbass mistakes the umbilical cord for a penis, and tells 'em I'm a boy.

So they go runnin round town, tellin everyone who'll listen about their son, and how they've picked out a name for him and everything. Ryan James Shein; James for my paternal grandfather and Ryan for my mom's younger brother who died at the age of seven from small pox, or rickets, or the German measles or something along those lines. They tell everyone the name, they start receiving gifts with the name Ryan monogrammed into them. I even got a sterling silver rattle with the name "Ryan" engraved into it.

I just want you to understand just how committed my parents were to my name. And I was lucky too! Because my father was pushing for some Jewish name like Ishmael, or Habakkuk. I thank GOD my mom put her foot down on that one. I mean Ryan's bad, but Habakkuk is a bully magnet. I'm pretty sure it literally translates to "Kick my ass" in Hebrew.

Well you can imagine the surprise, in a hospital room in Nova Scotia when they pull me out and instead of dangly bits between my legs; they find the old hot dog bun. You know, without the wiener? Well my dad almost fainted, especially when he went in the waiting room and saw the barrage of gifts, all with the name Ryan covering everything. My uncle even set up a trust fund for his nephew. They had my passport information already filled out, all kinds of plans set up for me. Only problem was the fact that I was in fact female. And instead of coming to their senses and renaming me, they just switched the middle name around and kept the Ryan. Why they didn't switch the first name is completely beyond me, I secretly think it's because they had my mom on some pretty heavy drugs when she delivered and I think she was too high to notice I was female. Who really knows?

Anyway, I really want to start us off on the right foot okay? I don't want any false pretenses with us Isabella; I really want us to be completely honest with each other. So I have to tell you now, right up front who and what I am okay? I don't want you to think I'm something I'm not.

I'll start off first with what I am not. And that is pretty. I am painfully average in every way. Nothing special about my looks at all. I've got regular eyes, not especially light eyes or anything, no really long lashes, no special shape or anything, just ordinary eyeballs. My nose, is just plain, not too big, not too small, or pointy, just a regular old nose. It wouldn't be called a button nose or anything, it's not particularly cute; it's just a nose. Plain and simple. My lips, should be my saving grace, my father has nicely shaped, full lips but me? My lips, like the rest of me, are painfully ordinary. Not full, not thin, just lips. That's it.

Also, just so you know, it doesn't get any better. It's not like I'm a buttaface or anything. I happen to think I carry my beautifully challenged nature with grace actually. I don't wear makeup, not because I don't know how to use it, but because I don't want to be one of those women who rely on makeup to make them pretty. Because at some point, you gotta wash it all off and I'd rather not try and fool someone into thinking I'm something I'm not. So make up is reserved for those few occasions when there is no avoiding its application. Like weddings, funerals, and all other expensive events in between.

Another thing about me is I'm tall. Not freakishly tall, where my arms are like twice as long as my legs, but I'm tall. I have no clue how tall, because I've stopped measuring; I just know I'm not 5'5. My body itself is another topic. Oh, by the way, I'm currently sitting on my back deck, looking up at about a billion gorgeous stars, drinking some fantastic white wine and listening to George Benson. Just thought you'd like to know that.

So one morning I'm getting in the shower, and I'm soaping up a bit and I look down between my tits and I realize I can't see my vag anymore. I'm completely baffled by this because I'm sure it was there yesterday, but sure enough I poke this thing that has taken up residence on my midsection and I realize that it is a firmly attached layer of fat that has obstructed my view of what used to live below. I'm shocked and appalled. I slap it, which was a horrible idea because I'm in the shower, and I'm wet, and it fucking hurt! But you know what I think hurt more was the fact that like poking jello, it jiggled. For a long fucking time, it wiggled and shook and I think it even sent shocks down my thighs because I'm pretty sure they shook too.

I decided that it was time to evict my unwanted guests from my body. I got out of the shower, and dressed in my black pencil skirt and black silk blouse with the tailored black jacket. I'm usually not this dark in my wardrobe, but when one comes to the realization that they are fat, who wants to wear anything colorfull? Even at the age of 32 I'm still worried about being called kool-aid. So that very day on my lunch break I went downstairs to the 5th floor in my building, which just so happened to have a gym. As soon as I walked in though, I thought about leaving. I looked around at all the people sweating and grunting and I turned tail. I looked over at the reception desk and saw the twin supermodel bots, batteries sold separately, behind it looking like blond, spray tanned barbies and I decided that I didn't care what anyone thought about me being here. Fuck em!

I walked directly up behind the reception desk and between the two of them. They look at me like I'm crazy, but like I said, fuck em! So I undo my jacket and grab a hold of the offending layer of fat and I say,

"I want this gone! Yesterday!"

They look disgusted, but at the risk of sounding repetitive, fuck em!

$250.00 and a three year contract later, I had a membership and a personal trainer that I will be meeting tomorrow at six pm. I've decided to change my life; to be a different person from now on. I've decided to stop giving a fuck about what other people think of me, and worry about what I think of me. Because apparently, I haven't thought much of myself. I'm hoping Isabella, that with time and effort we can change that.

Thursday February 07th 2008

I hate that gym. Who the fuck told me to join a fucking gym in the first fucking place? First of all Isabella, it's all stuffy office types in there. I am without a doubt the fattest person to walk in there and I know I told you all that stuff just yesterday, about how I was gonna say "fuck it!" and just do my own thing but it's a different story when you're there! And you're fat! And everyone else is just flying through their workout and I can barely keep myself upright on the treadmill!

I hate that place! And I think the reason why I hate the place as much as I do is because my personal trainer is gorgeous. He's gorgeous. He wasn't at all bulky like I expected him to be. I actually expected him to be one of those no neck, Hercules, steroids for breakfast types. What I saw was a God. He was tall, taller than I am and that's really all that matters, lean and definitely trim but cut the hell up. I mean he had a shirt on, one of those underarmor tees but my God, it showed all his hard work.

So here I am, in my four year old rocawear velor sweat suit ready to work out, trying my damnedest not to look too fat in it, and this sexy, gorgeous, beautiful specimen of a man smiles and says,

"You're gonna hate me by the end of today, but hopefully you'll be back tomorrow!"

And he says this, in the deepest, sexiest British accent I've ever heard which is complexly surprising because I've always been one of those women who strongly believed that the English accent is the gayest accent ever. And I'm still trying to figure out what his nationality is. I mean he looks almost middle eastern, but between you and me, I always had this sort of stereotypical image of them being extremely hairy, and generally unattractive. I mean, that just sounds bad, now that I'm reading it back, but I've never been attracted to anyone other than a black dude before and this kinda caught me off guard to be honest.

Anyway, back to the workout from hell. The first thing he wants to do is gage my fitness level, and although I've already informed everyone of my sedentary lifestyle, I guess he needed to see it all for himself.

Now Isabella my dear friend I want you to picture an overweight, maybe a bit more than slightly unattractive black woman trying to run on a treadmill when the farthest she's ever run is about a block. Oh, and imagine her sex on a stick trainer standing directly in front of said treadmill looking every bit disappointed. Can you see her? Can you see her pathetic attempt at running? Awkwardly slapping her feet against the revolving track? Yeah, well that's right about the time that this woman, who you've probably guessed is me, fell. And I don't mean I tripped a bit. I mean I full out, ass over tea kettle, fell, landed directly on my face.

So when I came to, on the dirty floor of the gym, Mr. wonderful and his legion of barbies were standing over me. My trainer, aka Mr. wonderful, had a completely worried look on his face. The legion of barbies, however, had that familiar look of disgust. It was then that I realized that my entire nasty midsection had been exposed during my fall from grace and I was currently 'letting it all hang out.'

So was that enough, you ask? Did I throw in the towel and quit? Hell fuckin naw! What I did was get my black ass up off that floor, fixed my clothing, and I gave him everything. I ran, crunched, squatted, lunged, punched, kicked, tucked and rolled. And now, I'm lying in a bed of ice praying that it will numb the pain that I feel everywhere but my eyelids. Although, I'm sure that if Mr. wonderful could've strapped weights to those too, they'd be in the same condition.

Anyway, thanks for listening Isabella. I know it's not exactly what you were expecting from me, or maybe it was. Who knows right? Well, this is Ryan Shein, signing off. I'mma try not to overdose on ibuprofen, and hit the hay.

Thursday February 14th 2008

Today is valentines day. The one day we all agreed to set aside and commercially celebrate our love for one another by buying edible underwear and strawberry flavoured lubricant. I am celebrating this wonderful day by working out until I can't feel anything from my ankles to my chin.

It's been a week of hardcore workouts and I must say, I'm starting to get accustomed to the atmosphere at the gym. I've once again adopted the 'fuck em' standpoint, especially since everyone there has already seen the worst of me. I really have no option of shame anymore. I mean I could have left that day and never came back, but to be honest I'm a cheap, tight fisted bitch who doesn't part with money easily. I've decided to treat this foray into athleticism as an investment.

So, instead of having a romantic candlelit dinner eating more calories than I could afford, drinks afterwards, and delicious passionate sex to burn off said calories, I'm settling for a salad with steamed chicken, 2 hours at the gym to burn the calories I've already long consumed, and sex with my vibrator. Sounds eventful huh?

February 14th 2008

I've made a friend. And on valentines day of all days! I was only gonna do the journal thing once a day but today turned out to be a double whammy day Isabella. Aren't you glad?

So I walk into the gym and it's surprisingly not empty. I fully expected tumbleweeds to blow by as I'm doing my lonely bicep curls but there were actually people there. I went directly to the elliptical machines, as I'd decided the treadmills weren't for me and began my workout. I started my mp3 player and put on my motivation music. The first song on the play list was work by Ciara. I don't know what it is about that song but it really makes me kick my ass in gear and go to work!

Now, I'm just going at my own pace, trying to breathe so my muscles don't cramp up on me and I notice that the machine next to mine was about to be occupied. And I'm waiting for this guy to grab the spray bottle and wipe the machine down, but he doesn't. he just hops on and gets to it.

Isabella, I know what your thinking. We're "supposed" to wipe down the machine after we use it but let's be real here, not everyone does! Now, I don't want you thinking I'm obsessive compulsive or something, but I have been known to wipe down the condiments at restaurants. I'm just saying, you don't know where they been right?

Anyway he hops on and gets to work and honestly, I'm a little grossed out but I try and return to my workout. So after a few minutes of working out side by side, I notice him looking at me. Also my elliptical decides it's time to backwards. I strongly dislike going backwards; It hurts. This fact must be written all over my face because he looks at me and says,

"It'll only be for five minutes!"

Now I actually look over at him, and the first thing that comes to my mind is "schmuck." Don't ask me why. He's this long, lanky, string bean of a man with really light brown hair that's beginning to go slick with sweat. He's smiling and I notice he's got his hand extended out to me.

"I'm Peter, most people call me Pete," he says. I just stare at his hand. I kept seeing those green germs from the Lysol commercial swimming around on it. So I say,

"I would shake your hand Pete but I'm dripping with sweat."

He says it's okay and on the inside I'm sagging with relief because I've avoided contamination. So I just smile back and continue with my workout. Well over an hour later when I'm headed for the locker rooms smelling like an old sneaker, he stops me.

"Hey, you never gave me your name," he says. Now with both of us standing in front of each other, I realize we're exactly the same height. I'm looking directly into his eyes. I don't know why, but it makes me uncomfortable. I mean I'm used to being the tallest woman in a crowd by now, but I just didn't like being the same height as this guy. Isn't that absurd?

Anyway, completely without thinking, I reach my hand out and say, "Ryan Shein." He shakes it, and I immediately remember the green germs now writhing on both our hands. Don't worry, as soon as I left him I washed my hands with antibacterial soap. But back to my new found friendship. When I told him my name, he looked a bit confused.

"Do you mean the Ryan Shein? Editor in chief at New York weekly?" he asked.

And I tell him yes, we're one in the same. He actually admits that he assumed I was a man, which is refreshing because most people who find out who I am just try and pretend they knew I was female all along. So we get to talking, and I find out he's actually a fan of my magazine, reads it faithfully and enjoyed my article from a few years back on the GDP. I also find out he's an investment banker, he works on wall street, he's divorced for almost a year and had just recently lost 20 lbs. It seems I had misjudged this guy. He was definitely no schmuck.

"Do you mind if I ask you a personal question?" he asked.

I say go ahead, but inside I'm a little worried what he's gonna ask me. I pray to God he's not gonna ask about my treadmill incident.

Instead he says, "Are you Jewish?"

I breathe a sigh of relief and say, "Yeah, I am."

I tell him about my parents, how my father is half Jewish and he passed the torch onto me, although I haven't been to temple since MC Hammer was hot. He tells me he's Jewish as well, and had always wanted to become a rabbi when he grew up but somehow ended up working on wall street.

Isn't it funny how that happens Isabella? When I was a kid I wanted to be a cartographer. Because my parents moved around so much, I felt like a could draw a map like nothing. Instead I became a magazine editor.

Anywho, Pete and I parted ways eventually but I must say it's just so frickin nice to meet someone of intellect and worth. There was definitely no sexual attraction, but the conversation was so easy. I enjoyed it so much I'm excited to get back to the gym and chat with my new friend again.

Well Isabella, I hate to love you and leave you, but I have a date with my very handsome vibrator. ;)

c8er2u
c8er2u
180 Followers
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17 Comments
AnonymousAnonymousover 8 years ago
In many ways I can relate...

Although I'm not Jewish, not an editor, never met the nice guy (unless you mean the toothless or front tooth missing boogerbear type) who strikes up a DECENT conversation (not conversation starter--got any kids or you single ain't you?) without a vibrator, living in the 'hood, I really can relate. The only difference is I have a seductive name without the attitude to cover it.

Yes, I come to Literotica alot to fulfill that relationship need. Yes, I know this is sad...lol.

swear_toobobswear_toobobabout 10 years ago
Omg....

I have to say this has just become my favorite story ever... Story of my life except I probably would have given up on the gym.

Jai_n_lia0612Jai_n_lia0612over 11 years ago
hilarious

you had me laughing for a full 5 minutes. that is a hard feat for that alone you get 5 stars. the story also happens to be so true to life that you have to love it. keep up the good work.

brownskinnedcutiebrownskinnedcutieover 11 years ago

I like Ryan, I do hope that she improve her feelings of self-worth.

NightpleasureNightpleasureover 12 years ago

I also like the way the story is going. Please finish it.

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