The Edge of the Friendzone [closed]

asetikish

Literotica Guru
Joined
Sep 2, 2013
Posts
1,205
I just finished the last of the research work I have for one of the lawyers in the firm. Sometimes I think I do more work than these pedigreed men and women do, but I don't get paid as much. It doesn't matter that I'm the best paralegal they have. All the benefit they give me is unlimited leaves. They know I don't abuse it. Besides, I don't nearly have as much stress as they do, which is why they always hold parties that I never attend to.

As I'm about to drop off the documents, I notice a letter on my desk. I open it reading:

Hey Jen,

There'll be a party tonight. I'd like you to be my date for the evening. Call me.

--Jack


I stare at the letter in my hands. Is this some joke? I know I'm not the type to get invited to dates. Not with the way I dorkily dress, the lack of makeup in my face, and the ugly glasses. I groan. Maybe it's another one of those pranks they used to pull on me in high school and college. or maybe this guy really wants a huge favor. Either way, I'm incensed and the only thing I can think of is to talk to my best friend and drag you off to lunch somewhere far from the office.
 
I sat there at my desk and stared at the computer screen. Work was slow as I was not getting a lot of work as an IT for large business. Usually the phone was always ringing and I had to fix easy problems for over paid idiots that didn't know better. I yawned as I pocked my cellphone up and looked to it to see that it was after 1pm. "Damn... time is not moving... maybe I should call my bestie." I ran my hand through my shaggy brown hair and smiled. I hot the speed dial on my phone as he heard it ring, I put it on speed dial as I look up some pervy stuff on the net.

I smiled as I heard you pick the phone. "Bout time lazy, what you up too? Was thinking of punching out and getting out of here, want to grab a bite?" I knew you amd I alwaus thought on the se page, it was why we were best friends of course. Like I knew that you knew I was a big time pervert, always watching porn and going to strip clubs. But I loved how you liked that about me.

"So what do you think, bugers, pizza? Jen, you ok?" I waited for an answer.
 
I smile as I hear your voice...and then scrunch up my nose as I hear the tone. You're watching porn again. Nothing I can do about that, really. But sometimes, I wonder why on earth you spend time on that when you have real girls to do that with. Real, actual girlfriends who go out with you and, I'm sure, have a fun romp with you.

And honestly, as much as I don't mind you having that kind of hobby, I don't like how it often steals your attention. At least, at lunch, you have no way of getting your daily perv fix. Not especially when someone as ugly as I am is in front of you. Yep. I'll be able to tell you all my problems without worrying that you're thinking with your dick.

"Pizza. Definitely pizza. You know the old place." I sigh. "I'll tell you all about it only if you get your ass out of your porn. Seriously. Isn't it too early for that?"
 
"Aww come on Jen, you know it is how I pass the time. Jeez, not like you care what I do?" I grin as I start to pack my belongings up and punch out on the computer. I make the call and head out to my car.

I love hanging out with my best friend, she is such a jewel in the rough, she hides herself in baggy clothes and thick glasses, but underneath all of that I knew you were such a hottie. I stole glances when I could at your place when you went to change, I knew you had a killer body. I could not stop grinning as I drove to the pizza parlor where I knew she was there already.

I parked my car and saw your car parked already, so I walked inside the pizza place and saw you there, sitting in our usual booth.

"Hey, Jen, whats up cutiepie!" I said that as I hugged you, pressing my body to yours. "Are you doing ok? You sounded like you were a little stressed over the phone, I can tell, I am your best friend after all. Now spill it."

I look to you as I toss a napkin at you playfully.
 
I sigh as you hug me. You always know how to make an entrance. Comforting me when I'm like a headless chicken running around. Like now.

I growl snatching the napkin before it hits me. "You big bully!" I stick a tongue out at you. I ordered the usual and I wait for the waiter to leave us with our pizza before tossing the note to you.

"Do you, or do you not think this is another prank?" You know exactly what happened to me in high school. I thought someone actually liked me. Turned out it was a bet about who could pop my cherry. Turned out, the guy lost. Though I have no idea what happened to him after. He just disappeared. "Or maybe it's a prelude to a huge favor? You know, making me feel good because such a hottie is taking me out and then asking a big favor?"

I take a bite out of the pizza. "Tell me honestly. Prick or no?"
 
I look at you as you tell me that, I could still remember the pain and heartache you went through during that whole ordeal. I shake my head as I put red pepper and parmasean cheese on my pizza.

"Jen, all these guys want is to see what you look like under all those clothes, it is really plain to see that you are a hottie. Face it."

I take a bite of my pizza as I savor the taste of it.

"Mmm so good..." I shake my head and look to you. "I say, prick... don't fall for these wolves in sheeps clothing." I look you right in the eyes, my crimson brown eyes showing you that I really care. "I don't want to see you hurt, and I don't want to have to go to your office and beat up a lawyer, just cause he was trying to get you in bed." I thought of what you looked like under your clothes and was one to think like the other guys.

"Good call Jen on the pizza, its really good and hits the spot, are you going back to work after this? I called it a day, it was really boring and they are paying me no matter what, so might as well take advantage of it."

I laugh as I take a sip of my cherry coke.
 
I burst out laughing. Me? A hottie? You sure know how to make me laugh. And around you, I hold nothing back. Even the rare snort that comes out when I laugh so hard.

The sincerity in your voice as you give me advice makes me smile. "Thanks, Dave. You're always the big brother I can count on." I leave out the constant thought that runs through my head. A hot, pervy big brother who rubbed on me. It's your fault that I now have a secret stash of toys in my drawer. A stash that not even you know of yet.

"You're so lazy!" I reach over and pinch your cheek. "You do know that you can rise higher if you just go the extra mile right? They already know you're really good." I sigh, taking another bite off the pizza. "I have to back to the office. Give stuff over that I've finished. Legal work is never done. And besides, I have to give a response to this letter. What do I say? I've always been turning the company parties down. Should I do so again? Or do you want to come with me?"
 
That snort you had when you laughed hard was so cute, always brought a smile to my face every time I heard it. I laughed with you, but I looked to you.

"One, I am not lazy, I just know how to get my work done at my own pace and two... the boss thinks I am lazy... aww hell!" I put my head to the table and sighed.

I than thought about what you said and I rubbed my cheek that you pinched.

"Hey... hands off the goods Jen, damage my pretty looks, and you might mess up my chance for a grade A lap dance tonight... jeez. You always work too much Jen, you need to relax, too much stress will kill yeah."

I put my hand on yours.

"If you want to go to that party, I will go with you, if that is what you want."

I smile at you.
 
"Oh? Who's going to give you a lap dance?" I grin. "Besides, I'm used to you looking so ugly every time you sleep over. Unshaven, bug eyes and morning breath." I chuckle. Unshaven and bug eyes really make you look so cute...and I really don't know that you have any morning breath. I've never been that close when I watch you sleep.

"Alright. If you want me to unwind, I'll go to that party with you." I've never been to a party with you before. Not in proms and dances. I always sit them out and find out the next day that you have a new girlfriend.

Why that annoyed me, I have no idea.
 
"Well, I am glad that you pick me up from the strip clubs, so I will let that one go... just think if you don't pick me up, than I would have to stay there drunk... you wouldn't want that now would you Jen?"

I grin at her.

"Well, if her name is Cherry and she loves grinding on me... but I would rather go to the party with you Jen."

I grin at you and clean my hands and wipe my mouth. I finish my cherry coke and burp.

"That hit the spot... ahhh.." I chuckle as I get up from the booth, I walk with you to your car. "Are you going to pick me up?"

I look to you and smile. That usually meant he wanted to drink though...
 
Cherry. You always bring that name up. Does she really exist and is she your favorite stripper? I don't know, but I already hate her. And yes, if leaving you drunk meant leaving you with a slut like her, I don't like it one bit.

Really, we have no shame when we're together. There's absolutely nothing that could disgust us about one another anymore. I mean, I used to think that your perversion was disgusting, but I've come to accept that as a part of you. That includes your drinking, laziness and your tendency to pick up girls, who for some reason can't resist your charms. But that doesn't mean I don't try to push you into the better person than you could be.

"Dave, you know I'm not going to pick you up no matter how much better my car is than yours." I roll my eyes to stick the jab in. "And I know that look. You want a drink. Tell you what, I'll submit what's left of my work, tell Jack I already have a plus one. And you take a little bit of extra load that you can finish and meet me at my place. I still have that beer from our company outing in Amsterdam. One. Last. Bottle." I poke at your chest with my finger emphasizing every word.

"Oh, and the party is a an evening penthouse pool party. Wear something nice." I roll my eyes knowing that you are going to ask about bikini-clad women there. "Yes, there are going to be scantily clad models and some people in the office who would like to go for a dip. It's a pool party after all. And yes, you can swim if you like."

I kiss your cheek like I always do. "See you later." I hop in my car and head back to work, giving the documents to all the lawyers and then going to Jack's tiny office to reject his offer.

"Jen, Jen, Jen..." He shakes his head at me. "You could have had all this if you didn't reject me. Your one shot at landing a hot guy with a six-figure salary in your bed, but your loss. Just introduce me to the loser you're taking."

My teeth almost grind together. I can take people talking shit about me, but never about my best friend. "I'm sorry, but my date is hotter than you and he's not an asshole." I turn away but stop myself and turn back to him. "Oh and for dissing him like that, good luck on researching the Steiner case all on your own. Or maybe some other paralegal would be good enough to help you. Especially when your deadline is in three days and all the info you need is with me."

Stalking out, I return to my car and drive home unable to believe what I've just done. I told Jack off. Jack. One of the biggest rising stars in the company and the number one guy in the paralegals' "guys I'd sleep with" list. I told him off just because I was so pissed off that he was such an asshole to David.

The question that bothered me, though, is I never asked you about your salary. Jack could use that to get at you. Oh well, not that I care about how much you make. I just hope you're not going to be bothered by that either if he slaps you with it.
 
I laugh with you at your crack about my car. I never really care about material things too much, things like cars and clothes didnt really care for. I had what I needed in life, porn, video games and my best friend. Not in that order, but that is all that mattered. I had no family, no other friends to worry about. I smile at you as we are walking to our cars. "So I will see you in a bit than?" I wave as I see you drive off, I drive home and hop in the shower to get cleaned up, the whole time I am thinking of how nt to make you look bad. I sigh as I take my blue dress shirt and charcoal gray jeans and put them on, I bring a bag with my board shorts and a towel. I look around and see my cat Ruby laying on the floor. I smile and feed her dinner as I leave to head to your place.

I pull up at your place and walk up to the door and knock softly.
 
I'm lounging about my home when I hear you knock, still in my layers of work clothes that give me no shape at all--well, oval was a shape. I open the door with a smile and with one look at how nicely you've cleaned up, I know you haven't taken the extra workload I urged you to do.

"Well, no beer for you, lazy bones." I shake my head. "That one last bottle is reserved for a special occasion and this isn't it. Shall we?"
 
I give you the shocked look and shake my head, "Jennifer, come on... I can't do work if there is nothing to fix. Besides, I had to go home and shower and shave, since you think I am so lazy... jeez." I grin as I walk inside of your place. "Whats the hurry, we still have a hour or two before the party starts, are you going to go in that? Why don't you go and change, put something on that will "wow" the crowd, come on." I smile as I say that, encouraging you to open up and come out of your shell.
 
I shrug and let you in. "Alright, fine. For all your effort, I'll be honest with you this once. You look panty-dropping hot. And that isn't sarcasm. At least not today. Still no beer though."

I slump beside you on the couch. "I don't have anything to change into. Do you really think that I have something nice stashed in my closet? Besides, there's no point in wowing anyone." You look at me with that stare that says you're not going to budge and I sigh. "Fine. Look in my closet. I'm telling you, what you see me wear now, they're all similar in my closet. Although I do have that ugly, frilly maid of honor dress from my sister's wedding, but yeah. Nothing else." I nudge my glasses up to prevent them from falling off my nose.
 
"Panty droppin hot huh?" I laugh as you say that. "So are your panties going to drop?" I grin as I say that and look to you. I stand up and start to head to your bedroom. "Well, instead of wearing 20 layers of clothing, we can always just wear one... how about that?"

I walk into your bedroom, I did not hear you behind me, I went and opened your closet to see plain and boring clothes. "Jeez... you don't buy anything sexy do you?" I pulled through the clothes hanging and than went to your dresser, opening the drawers, I did find a treasure though... "Panties..." I drooled for a second as I found a soft pair and I looked behind me to make sure you were not in the room, I stuffed the pair down my pants into my boxer briefs. I grin and laugh on the inside, spank time later tonight... I thought to myself.

"So, I guess we might have to go with your maid of honor dress, what do you think?" I lay out some other choice outfits, skirt and tight top, long skirt, dress shirt. "So what do you think, fancy, or comfy?" He wondered what she would choose.
 
I let you in my room as I roll my eyes. Sure it was my fault that I used the wrong word. I knew you were going to pounce on the innuendo. "Don't get any funny ideas in there!" I call out as I get two cans of soda.

Entering my room, you already have several sets of clothes laid out. "Hell no to the frilly stuff! Are you kidding me?" I toss you the soda. "Comfy always wins." I look at the items you laid out and picked out the dress shirt and long skirt. "At least they don't reveal my ugly, fat body." I've had enough of those skinny cheerleaders telling me how fat I am then squeezing my boobs.

High school really sucked.

"Now get out. I need to change." I am almost pushing you out the door. I shut the door and change out of layers of clothing into the ones you picked for me. Without all the layers, my breasts, hips and ass popped out accentuating my small waist, and there was no more guessing where my trso ended and my legs began. I have long legs, though one could only guess their shape.

I look at myself in the mirror and blanch at how ugly I must look. Good thing I have my glasses on to hide behind in.

I finally emerge from the door and look at you. "Well?"
 
The way her soft panties felt against my cock felt good, I was growing hard in my pants. I did not want to freak my best friend out though. I had feelings for you, but just did not want to ruin our long frienship. I knew you did not like certain things about me. "Cone on now Jen, don't be like that." I left the room as you wanted to change, I always wanted to see you naked. "Jen we are best friends, why can't I be in the same room, oh, are you bringing a bikini? We should pick one out for you, two piece, something sexy."

I have only caught glimpses of your sexy body, I knew you had a large bust, and your ass was a tight apple shape. Your legs were long and sexy, I just never understood why you never come out of your shell. Show off the goods you have.

I see you in the dress shirt and long skirt, I smile at you. "You look so beautiful Jennifer. You can stop a man in there tracks and take there breath away." I can feel my heart racing a little. I love how the dress shirt trained a little to contain your large breasts.

"Wow... I don't know how I am going to keep all the guys off of you, might have to bring a bat..." I say that smiling at you.
 
I scrunch my face and give you a slap on your arm. "Oh, stop it! You're really embarrassing me." And true enough, my face starts flushing. "And no. You know I don't have a bikini. I do have a rash guard and shorts though. I could wear them underneath. The clothes will cover them well enough." I shake my head. No, maybe I'm not going to swim with all those on. I'll just be a laughingstock again.

I don't really notice you staring at my body. To me, it just feels as if you're looking at me like any other ordinary day: with a hint of your all-encompassing lechery. Like you can't look at a girl without thinking about her tits.

I grab your arm, my soft breast molding to your arm. "Come on, before you get any more ideas. And no, I'm not swimming tonight." My voice drops a little lower. "Not in front of all of them."
 
I felt you press your boobs into my arm and I moaned on the inside, as the soft skin molded around my arm, they really were heaven made. I looked to your breasts and than to your eyes and grinned, had a pervert look in my eyes. "Than you Jen, that will be saved in the spank bank..." I laughed as I looked to you, my best friend.

"Aww come on, we can always get one on the way, something sexy, something... revealing."

I smile as I look you over. But I hear what you say about swimming and I get a sad pouty face. "Awww, please don't make me swim alone... I might get attacked by the hot females there..."

I grin at you. "Come on, grow some balls, have some fun Jen, we only get one life to live, lets make the most of it, just pretend it is just you and me." I take your hand in mine and hold it.
 
I look at you incredulously. "Really, David! If it's just the two of us, why not? But you know how fat and ugly I am. I'll only make people laugh." But you get that look on your face again telling me that there's no way I'm not going to swim. I sigh.

I take out the car keys and drag you over to my car. "I want you to give me one really good reason why I shouldn't be going back there and getting my version of a two-piece. Because the office isn't going to let me live it down when they see scantily-clad flubber in the pool."
 
As I held your hand I led you over to your full mirror and stood beside you. "Really? Fat and ugly? Why are you so hard on yourself? You are beautiful, and deep down you know it. I a fool for..." I didn't finish my sentence for not wanting to make this an uncomfortable night. "I mean, come on you know you look really hot, all the men are going to be all over you tonight." I had a sad look on my face as I thought about you being with them and leaving me alone.

I shake my head and smile at you. "So you will swim? Oh Jennifer you are my best friend, that is why. I love you Jennifer and I will not let you get hurt. Is that reason enough?" I look to you as we stand at your car. "So you are going to drive" I grin at you as you unlock the car so I can get in. "So lets hit up that strip mall, and you can model some bikinis for me..." I was still grinning at you
 
You got me. for some reason, you really know exactly what to say to me to convince me to make you do what you want. Sometimes, it's annoying, but I've learned to live with it. After all, you're my best friend. I've come to accept all the good and bad things about you.

I sigh and drive us over to the strip mall feeling really anxious. "You do know you're bullying me into this, right?" I say as I park the car. "And you'll be paying for this, you hear me, Dave?"
 
"Jen, my bestie, I would never bully you, I would only lead you down the right road and together, me by your side, encouraging you, helping you." I smile at you. I take my wallet out and hold it up. "Of course I got it, I get to choose what bikini you wear, you can't say no and you have to wear it." I grin at her evily. I was going to pick the most sexy, revealing one I could find.

"Come on Jen, lets go!" I say that with excitement, I get out of the car and wait for you to come out and lock the doors, when I hear the beep, I take your hand and we run into the mall and quickly to a summer shop.

"Here we are Jen, I am going to go pick out a few, you go try them on. And yes, you have to show me what you look like in them."

I run to the racks, searching for the right one, I grab them left and right, looking and putting back, looking and putting back. I find three, a red one, a white one and a green polka dot one, all thong bikinis. I grin as I bring them for you to try on. "here you go Jen." I could not wait to see you in them, I had my phone ready to snap shots.
 
Back
Top