Chronicles of the Unpretty Ch. 02

Story Info
A life in the day of the beautifully challenged.
3k words
4.68
11.5k
17
Story does not have any tags

Part 2 of the 2 part series

Updated 10/29/2022
Created 08/04/2010
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
c8er2u
c8er2u
180 Followers

March 7th 2008

So I must apologize, I've been neglecting you Isabella! It's harder than I thought to keep a journal! I assumed I'd be able to just empty the contents of my mind at the end of each day directly into word form for you but you know, a lot of the time when I get home I'm too damn tired to pick up a fork let alone a pen!

Speaking of forks, after careful consideration I've ended our love affair. We've had a toxic relationship for some time now, and I just had to come to the realization that maybe we're not such a good fit for each other. Maybe I should try out the salad fork for a while, maybe we'll be a better fit right?

In other related news, I've lost 7.4 pounds! And hell yeah I'm including the .4 because I worked damn hard for it! Mr. wonderful and I have a love/hate relationship. I love him before and after the workouts but during? I want to rip his face off! Yesterday, he tried to kill me. He sincerely wanted to kill me. Wanted me to stop breathing all together.

He somehow swindled me into the treadmill again, (don't ask me how, just know there were dimples involved) and he had that thing up so high there were almost sparks from were the top of my thighs were rubbing together. I swear, when I got off I nearly clocked him upside his head but the man ran up and hugged me! Snatched me up, and swung me around! Told me he was proud of me, for not quitting when it got hard.

If it wasn't for that accent and the sudden butterflies in my stomach he would have been struck! Have I told you how sexy that accent is? If not I'll tell you again. It's sticky panties, say that one more time even though I heard you quite clearly, star of my masturbatory fantasies, sexy. I mean it's so sexy that instead of getting angry, I smiled. I actually smiled through the cramping in both of my legs. It was worth the pain and the stink eye from the supermodel bots. So I waved him goodbye and promptly limped home.

I even dragged Hector's ass down to the gym and, wait now, have I told you about Hector? I can't believe I haven't told you about him, he's only my other half! First of all, his name is pronounced Heck-tah, a true new Yorker. He was the first person I saw when I walked into the 9th school I'd attend since kindergarten and I instantly fell in love. He had curly hair, hazel eyes and dimples. Can you tell I have a thing for dimples? Anyway, I was completely enamoured with him and he knew it.

From the very first time we spoke to each other, we were inseparable. He took me to Coney Island and the Brooklyn zoo, he taught me how to swear in Spanish, also taught me those key words to know if someone was talking shit about me in Spanish so I'd be able to cuss them out. We did everything together, he was my best friend, and on my 16th birthday, he gave me a red rose, (which I still have to this day) and asked me if we could go steady, as if we weren't already. At least in my mind. We were high school sweethearts; kisses between classes, holding hands in the hallway, he even carried my books when he walked me home.

I was completely dumfounded, because I knew full well there were much prettier girls in that school, prettier ones that would have sold their left tit to be in my shoes. I saw them staring at us, with puzzled looks on their faces trying to understand what he saw in the dark-skinned girl with the country accent. He told me later that it was because I was like a breath of fresh air, and also because I was about the only girl who loved Janet Jackson as much as he did. And not because she was a Jackson; because we both wanted to be a part of the rhythm nation so bad it hurt.

I wanted to have sex with Hector so bad it hurt. I was a teenage girl with a boyfriend who looked like he could have been Davante sway's Hispanic cousin. I wanted nothing more than to do all the freaky dirty things my teenage mind could dream up while my sexy boyfriend spoke Spanish in my ear.

So I devised a plan to seduce him which consisted of me blatantly throwing myself at him. He ducked and dodged me. I didn't understand, if he was my boyfriend, and he loved me like he said he did, thought I was as beautiful as he said, why wouldn't the boy fuck me? All we ever did was kiss, and every once in a while cop a feel in a dark movie theatre. (All of which was done by me) I needed more and Hector refused to give it to me quoting Janet Jackson saying "Lets wait a while," well damnit my body WANTED to go too far!

He asked me to wait. He said he wanted it to be special, and what was more special than prom? I grudgingly agreed to wait until prom. Even though it was two years away, I agreed to wait because I loved him and I wanted to respect his wishes as well as my own. He said he needed time, that he wasn't ready yet and just because I was, I didn't want to push him away. I really and truly loved him with all my heart.

So when prom time finally rolled around, I scoured the city and found the perfect dress. It was sexy, in an early 90's prom kinda way. The dress itself didn't matter because I didn't plan on staying in it too long. Damn teenage hormones!

It was what... 1994? Damn I'm getting old! Anyway, he comes and picks me up and tells me I look amazing. I couldn't care less about taking pictures but my parents forced me to pose for a few before we left. Prom was good, but all I remember is counting down the moments until it was over! I guess Hector was too. So when the time came, we had this hotel room that his older cousin booked for us in Jamaica Queens. It was near his house and I was gonna stay over afterwards. So I'm there, and I'm in the bathroom. Got the damn dress off and now I'm wearing my very sexy light blue French cut silk panties (that I got at JC Penny in the women's section) with the matching blue bra. You remember that Isabella? When everything was cut high up to your bellybutton? Well I was tall so it didn't quite reach my belly button. I just had a little bit of thickness to me too. Not fat or nothing, just thick! So I'm in this bathroom right? And I'm talking to myself, telling me in the mirror that I am the sexiest thing walking. In fact I'm pretty sure at one point I busted out singing 2 live crew, you know, "You ain't nothing but a hoochie mama!"

So when I finally emerged from the bathroom, and tried my best to strike a pose in my sexy lingerie I was praying he wouldn't laugh. What I found was a fully dressed, right down to the shoes Hector. I remember I asked him why he still had his clothes on, while I clung to the last vestiges of my modesty. And do you know what he told me Isabella?

He said, and I'm quoting him here, "Because I'm gay. Now put your clothes on and let's go home. There's a .Barbra Walters special on Dreamgirls and we're gonna miss it!"

Now you know how they say, hindsight is 20/20 right? Looking back I don't know how I DIDN'T know. He loved all the same things I loved, it was always me trying my damndest to seduce him, his nails always seemed manicured, hell he was waaaaay prettier than I was, I should've seen the signs!

Alas, I was just too happy that a boy that looked like he did was even interested in me; a girl that looked the way I did. So I ignored all the telltale signs and was his beard for two years. I put my dress back on that night and I went home, to my house and I cut off all contact with Hector. As much as I knew he couldn't change who he loved the betrayal still hurt me deep. Right at a crucial time in my life too, when I was still trying to validate myself as a woman. I ended up loosing my virginity a year later in college to an economics student who was so happy to see real live tits he didn't care that they belonged to the Amazon black chick on campus.

It wasn't until I think, six years later? I was walking on 5th, just got finished my shift when I spotted him and his partner. They were walking hand in hand, window shopping. I didn't know how I'd feel when I saw him again. Would I be angry, jealous? I didn't expect to miss him so much! He was my best and only friend at the time and when I saw him looking up in the Saks display window I ran to him and hugged him tight. He later described it as being hit by a linebacker, but that's neither here nor there!

We cried, both of us, he introduced me to his boyfriend Paolo who was an art dealer in Europe. I went back to their Upper East Side loft with them where they fed me bottle after bottle of wine. And when we were all good and drunk, Hector confessed that he still carries the guilt from that night with him. That he was so insensitive and callous. He said he lost the best friend he ever had that night and he never ever got over the emptiness.

I apologized for letting my own agenda cloud my judgement. I told him I should have never pressured him into anything he didn't want to do. I knew he only went there that night for me and when he left that hotel room, he left it his whole self. Without any disguises just as his gay self. I told him I was proud of him and that I loved him, then and now.

It was a real tear jerker. You should have been there! Poor Paolo probably had no idea what to do!

Anyway, we were once again inseparable and to this day, I barely make a decision without my Hecah! He is my gay other half. So I had to bring him down for a complimentary workout and if he just so happened to bump into me, while I was working out with my living walking manifestation of sex trainer? Just a plus!

So when I introduced him to my sexpot trainer, he leans over to me and says, "Fuck him! Fuck him right now against the exercise bikes or so help me, I will!"

Let's just say Hector joined the gym later that week.

March 18th 2008

I think I was just on a date. Has it really been that long since I was on one, that I wouldn't even recognize it? I mean It was harmless, a dinner with a friend. Or so I thought. Pete and I had been meeting up and working out together once or twice a week. (I'm trying to get every dollar I can out of this personal trainer thing! It's fucking expensive!) It's paying off though, I have to say. It's not necessarily showing up on the scale, but my clothes just don't fit me the way they used to and I'm starting to think I may have a waistline again. In the near future that is.

So we've been working out together, sweating and stinking and at first it was just a, "Hey, you wanna go grab a protein shake after?" which then turned into, "I know this really great deli over on such and such a street," which then leaves us at, "We should grab dinner sometime, I know a great low cal restaurant!" and boom! I'm on a date without even knowing it!

The thing is Pete and I have such great conversations! Intellectual conversations I haven't had in eons! It seems being Editor in Chief of a prestigious magazine at such a young age causes a bit of intimidation to where no one really wants to disagree with you. I can't tell you how refreshing it was to talk to Pete over my grilled turkey breast which was actually very tasty, and have him disagree with me! Not only that, but offer a valid point!

The thing was I was still thinking this was a casual dinner with a casual friend. I didn't pick up on the fact that Pete was wearing his "good" sweater, which brings out the green of his eyes or whatever. I just thought we were just friends! So when he walked me to my brownstone, and leaned in for the kiss on my front step, I had to pull a matrix to dodge him.

"Whoa dere partner! What the hell was that?"

He looked sheepish and more than a little embarrassed. He fumbled an apology, something about his stomach hurting because the shellfish was off and left. I, on the other hand, went inside and agonized over the fact that I embarrassed him.

Am I doing to Peter what Hector did to me all those years ago? Did I just effectively tell him I'm gay and dream girls are on? Even though it's been decades since it's happened and we've all moved on past it, the hurt of it is still there. I know I'm probably exaggerating all this. Right? It's not like he's a teenage girl just trying to build her self esteem and I just crushed it.

But.

He did just go through a divorce. A fairly nasty divorce, with his battleaxe of an ex wife. If that doesn't give the old self esteem a good blow, I don't know what will. Oh God I feel terrible! I'm a horrible, mean and terrible person who doesn't deserve a man!

Isabella, I'm going to go cry myself to sleep. Not even empty calories can console me!

March 19th 2008

Wow.

That's all I can say.

First off let me just explain that I was exceptionally drunk last night, and I don't know who THAT was that wrote that deluded and psychotic journal entry, but it wasn't the woman holding the pen now! What the hell was that last part? About empty calories consoling me? I'll have you know that there used to be a pint of Ben & Jerry's in my freezer and a bottle of Belvedere hidden on my wine rack. I'll let you draw your own conclusion.

Second, I called Pete first thing this morning and we sorted everything out. He's just a little lonely since ending his marriage and I happened to be there for him. He apologized for taking things too far and I apologized for being insensitive and then we decided to meet up on Tuesday to work out together.

Alls well that ends well.

P.S. I have a juicy tidbit for you! So I went to my morning workout with Mr. Sexy this morning and today when he put me on the treadmill, he hopped on beside me. Now, I know what you're thinking; big fucking deal. Man on a treadmill, not that significant right?

Wrong!

Mr. sexy trainer in all of his sexy glory, hopped on that treadmill wearing basketball shorts okay? And not just that, he must've been wearing some pretty loose boxers because his glorious... package? Shall we say? Was bouncing against his thighs in a way that almost had me trippin. Again.

Now, not only was the object of my desire flopping back and forth between his thighs, I knew he knew it was flopping against his thighs. The same way a woman knows when she wore the wrong bra to the gym, them titties are gonna try and come out soon as you hit that treadmill! They're gonna wanna greet the public!

So now I look up at him because I realize I've been crotch watching for longer than I realize and not only did he catch me looking, he smiled at me! Did you hear me? I said he smiled at me! What the hell does that mean? I mean it's not like he didn't see me sprawled out on the gym floor with my gut out. There's absolutely no way he's remotely close to being attracted to me either. Believe me, I know from experience; when that too good to be true guy is suddenly interested in you? He's gay! Run for cover girl, because there's nothing worse than finding out that for the entire time you thought you were in a relationship, you were just his beard!

Okay, reading that last paragraph back I realize I sounded a bit cynical. Just because one guy turned out to be gay, doesn't mean that every attractive man I meet is too. I'm just trying to learn from my mistakes and make better decisions in the future. Isn't that what you're supposed to do? I mean imagine, the next super attractive guy that approaches you. (I don't know about you, but it happens to me all the time!) Aren't you supposed to go into dating with your eyes wide open? Completely aware of possible homosexual tendencies? Or should I let life happen the way it's supposed to happen, and if it turns out Mr. Sexy is gay than so be it, on to the next? Listen to me! I'm actually weighing out Mr. Sexy's sexual orientation as if it'll change something. So he smiled at me! Big fucking deal!

God I hope my gym guy isn't Gay!

c8er2u
c8er2u
180 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
8 Comments
AnonymousAnonymousover 8 years ago
I commented on the last story today....

I think you bring a refreshing way of looking at a budding relationship filled with humor and delight.

I do hope there are more Isabella entries. They are absolutely hilarious.

chocojojo16chocojojo16almost 11 years ago
LOVED IT!!!

OK i really like it was funny, cute, just amazing but can you PLEASE finish this story and Hurricane please? i beg of you thanks

AnonymousAnonymousabout 11 years ago
Awesome

Too freakin funny. Love her. More please.

brownskinnedcutiebrownskinnedcutieover 11 years ago

This story is hilarious, I love how Ryan writes in her journal like she's having a conversation. I do hope that Mr. Sexy is interested in her in a romantic sense. I feel so bad for Pete, his wife didn't deserve him. I love the way that you write, you have an amazing talent.

AnonymousAnonymousover 11 years ago
Wow

You are hilarious. I have a blast reading your work and I'm asking myself why I've never found you before. Thanks for the update and I can't wait to read the next.

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

The Long Weekend Watch us rock it out.in Interracial Love
Wanna Play? It all started with a game of Monopoly.in Interracial Love
Match Met Ch. 01 Fiesty white man and black woman clash.in Interracial Love
Secret Lover A office attraction grows into more.in Interracial Love
Ian's Trap A offer that cannot be refused.in Interracial Love
More Stories