Confessions - Monday 5/19/14

Monday 5/19/14

Dear Diary,
It was a long weekend of debating with myself. I picked up my phone ready to call Tyler every hour, but then I would remember that I am his boss, not his girlfriend. How can I do this to myself, think about a man I am supposed to mentor?
“Good morning.” He says walking in with a mischievous smile that calls out to me, a look that makes me want to push him back on my desk and rip his pants down and find that cock of his and savor every part of it. “Did you have a good weekend? I didn't hear from you, so I assume you managed without me?”
“You know what Tyler, I can manage without you. The only thing I need you to do is to get the presentation ready to go and help me load it into my car.”
“Sure, I assume you need me to go with you?” He asks looking me over with suspicious intent.
My mind suddenly dives into a daydream of ripping through his clothes, tearing through mine and fucking him until the next dawn. I snap myself back into reality and notice his knowing smile. Sigh. Who am I kidding, I am not going to be satisfied until I fuck him. “Fine, you can go but it better go well, otherwise, I won’t be in any mood to deal with you.”
“Understood.” He acknowledges with a lick of his luscious lips.
Tyler was a huge help in the presentation. He kept me on track; had everything organized so I never missed a thing in the presentation. He spoke up only when I needed him to, but otherwise stayed out of my way and let me do my thing. I stood up in front of those men and women and as always with slight nausea, a mix of nervousness and anxiousness. I love it, but mostly I love that moment you know you have your client, you know they are interested in everything you have to say. That’s when I get in the groove and seduce them into agreeing with everything I have to say. Men are easy and women aren't much harder especially when you have an assistant like Tyler stretching out in front of them to hand out materials for them to review. He nods with a smile to each of them and without even realizing they blush. As one woman said to me before she left, “Your presentation was excellent and he smells heavenly too.”  I wonder if she heard a word I said, but it really doesn't matter, I got a sign off to proceed as I wish too.
Tyler and I gather our things and pile back into my car in silence. I don’t dare look his way, I can feel his eyes on me as I sit trying to decide where to go next. What do I want to do? Where do I want to go with him?
“I know a great place for lunch.” Tyler suggests.
“Oh, and where’s that?” I ask feeling my hands begin to twitch with excitement.
“My place, it’s down the street from here. I’m a great cook or there is a great deli on the way, which is probably a better idea, because we really have nothing more than beer and some ketchup packets.”
“Do they have hoagies?” I ask not expecting much more than the laugh I do receive.
Tyler directs me where to park and we do actually get some lunch to take up to his apartment. As I follow him up to the fifth floor of his place, I begin to get even more nervous than I was for the presentation. Do I expect to go at him right away, or eat first, or do I wait for him? I have no idea how this should work. He opens the door and I walk in holding my laughter at the sight of the place. It is clearly a college student’s apartment. Old furniture, video games arranged randomly near the sofa and lighted up beer signs to illuminate the place.
“Well this is it, not much, but it works for two college guys who just need a place to sleep once in a while.”
“You have a roommate?” I ask concerned.
“Yeah, Trey, but don’t worry he’s working on a new art project of his, he won’t be back until late tonight I assure you.”
“An art student and you’re a business student? Not a typical roommate match.”
“No, not usually but we are both athletes and were forced to live in the same athletic dorm. A horribly outdated place. I caught Trey one night painting a new design on a wall of the place and instead of turning him in I helped him. We have been friends ever since. They call us TnT, apart we are dangerous enough, but together we are … explosive, you could say. He is actually the one I want to start a new company with, he is amazingly talented and with his art abilities and my business savvy, along with our sales advantages, I think we can have a very successful company.”
“Sales advantages?”
Tyler turns to me with a wink, “Yeah, we both are good at …”
“Oh, I see. And so are you selling me? Because I am starting to think I should go right now.”
“Before you eat your lunch, surely not.” Looking him over I feel the sweat begin to drip down between my breasts, I have never felt so unsure before. “We don’t have any sort of laundry in this building, so you might want to take your dress off before you eat, so you don’t get anything on it.” He undoes his tie and begins unbuttoning his shirt, “You can have my shirt if you want to stay covered.” He says pulling his shirt off and showing off his masculine chest and every muscle that has been built up perfectly for swimming. “Here you go.” He holds it out waiting for me to reach out and take it. I eye it for a time before slowly reaching out and taking hold of it. He doesn't release it, instead he pulls it back to him and me along with it. “You were incredible in that presentation. You commanded their attention. I was absolutely …” He says rubbing his hand down my side and breathing slowly along my neck as if he’s searching for just the right place. “…aroused by every word you spoke.” His lips touch my neck lightly. “Although I find it difficult not to get hard when I’m around you.” I feel down his bare chest and meet his abundant erection pressing firmly on his busting pants. “I loved seeing your tits the other day. I dreamed about them …” Tyler touches my breast feeling around it until the edge of my nipple pokes through my dress, “Ah there it is, that beautiful, pink nipple. Let me lick it, please?” The back of my dress slowly begins to unzip, I remove it off my shoulders and push it down before freeing my lace bra from my body. Tyler breathes out fully as he takes hold of my tits, squeezing them and rubbing them with his thumbs. I watch has his tongue touches the tip of my nipple and then licks all around it. He looks up at me briefly as he begins sucking and kissing. I close my eyes and he quickly takes advantage and turns me around holding my back to his chest as he continues fondling my breasts. His erection is freed, I don’t know how I missed that happening, but it is surely out of his pants, I can feel it against me. My dress slides to the floor allowing him to poke in between my legs, letting it rub against my pussy, making it tingling wet. A reach of his hand down underneath my panties and he groans at the satisfaction he finds. “I can make you wetter. I can make your pussy throb and come all over itself.” Inhaling deep I grip his arm spreading my legs to allow him more access. “Oh Baby, not that way. Let me show you.” He takes hold of me and bends me forward onto a coffee table as he sits down behind me pulling my panties off me and spreading my legs, “Bend over a little more, Baby, I want it in my face.” He says gripping my ass and pushing it up and apart before thrusting his tongue into me. I hold tight to the edge of the table bending over more and more to allow him all the access he needs to eat me the way he wants. His tongue swirls around my pussy, tasting my clit and working around his fingers that feel inside of me. I glance in between my legs admiring the fully erect cock waiting for me until I have to scream out. I come so hard I can feel it draining past his mouth and down my legs. He licks up what he can before smacking my ass and standing up behind me. “Stay just like that. Yeah, right there…” His dick slides in tight, pulsating and reaching the depths of me easily. I can barely hold my balance as he pounds into me, his balls smacking my ass in steady rhythm. It feels so good, all I want to do is collapse but he won’t let me. He jerks my body into the sofa and lets me get on my knees for him. I bury my pleasure filled screams into the cushion, gripping his hand holding my hips in place. My pussy begins to swell, heating up with every stroke he makes. The moment my cum touches his cock he explodes, releasing into me with a roar of satisfaction. I roll over onto my side gasping for breath when I notice him walking around naked and preparing a place for our lunch. He reaches out with a hand to me, and helps me up. “You can’t eat your lunch laying down.” Breathless I finger my food watching him out from the corner of my eye. “You were tense.”
“It was an important presentation.”
“Is that what it was?” I nod. “Well, I’m glad I could help you then.” Tyler scoots towards me, and kisses me. I enjoy it so much I pull him back to me and forget about lunch for a while.
It shouldn't feel this good. I know every second I spend with him, I am only falling deeper into trouble, but trouble has never felt so good.

Tuesday 5/20/14

Oh Diary, how can I begin to explain my emotions? We returned to work today and continued our day as we would any other day, except now, the sexual tension that has been between us is more than just tension, it is a desperate desire to do it all again. As we prepare our next presentation, Tyler’s hand brushes against my ass and I can do no more than breathe. I crave him, I dream about being bent over in front of him. Instead of asking him to help me put the presentation board up on the wall, I squeeze in front of him and hold it up pushing my ass against him and rubbing his cock to attention.
“That’s not fair.” He whispers against my neck.
“I don’t know what you mean?”
“If you’re going to purposely get it hard and excited then it’s your duty to calm it down again.”
“Oh yeah?”
He leans over and pulls the blinds on my office, shutting off the world to us. “Yeah.” He says stepping back from me and unbuttoning his pants. I turn as he unzips and pulls out his erection. “You want it?” I get on my knees, taking hold of him and instantly licking the tip clean of its pre-cum before wrapping my mouth around him. He gasps, fisting my hair. “Fuck that feels good.”
I suck him proudly, enjoying controlling him and causing him to stutter his appreciation for my efforts. I lean back looking up at him, “You like that?” He nods. “How about this?” I lick between his balls and his dick and all the way to the tip before handling the whole big hardened cock in my mouth. His cum sprays instantly and I drink up of every bit. Sitting back with a laugh as he falls to the floor holding himself breathless. “Did you like that Baby?” He nods. “Me too. Let’s do it again tomorrow.”
Tyler sits up zipping up his pants and takes hold of my face kissing me deeply, “I got a better idea for tomorrow; it is after all Wednesday. How about you sit on me instead?”
“On your lap or on your face?” I smile.
Tyler plays with my hair smiling, “You’re the boss, I’ll let you decide.”          

Friday 5/ 23/14

It is unfortunate that Tyler was called to help my boss the last two days. I have had to deal with eyeing him from afar, but he is supposed to finish up his obligations with Mr. Monroe today. I can hardly wait.
“You Bitch!” Kim yells at me as she pushes my door closed.
“What the hell is your problem?”
“Harris has decided to take a two week vacation to explore other opportunities he has been offered. He challenged me, and now he knows I can do nothing about it, because I didn't fire him on the spot.” I try hard to fight my laugh but a smile slips out anyway as I shrug my shoulders. “You did this, I know you did.”
“I had nothing to do with it actually. I assume it is because you don’t take him seriously enough. You treat him like nothing, when he does all the work.”
“That’s not true, I have helped him grow and he has learned everything he knows from me.”
“Then why be upset Kim, just a get a new intern and teach them?”
She stands in front of my desk with her hands on her hips swearing under her breath. “You know I don’t have time to train someone properly. I need Harris and you’re going to get him back for me.”
“And why would I do anything to help you? You’re the Bitch that stole my clients.”
I only showed them options, and they figured out that I was the better option. Something I am sure Tyler will conclude too.” I look up at her confused. “He’s a hottie for sure, I would love to get him into bed. Of course, once there I might just have to talk him into changing teams and working for me only.”
“You can’t sleep with the interns, Kim.”
“No? So you’re not sleeping with him? Bullshit. I’ll fuck your whole career up unless you get Harris back for me, I promise you. I am not just an ex model Illana, I am also excellent at seducing men, especially ones who are looking for a way to the top.”
“Get out of my office!” I yell at her.
She leaves with a sinister smile. I am not sure what to do, but I won’t let her have Tyler. As I sit and struggle with my thoughts, I think it best to go and talk to Tyler. I find him cornered by Kim. She touches his chest and smiles provocatively at him before sighing deeply, “Okay, so I will see you Saturday night.” She walks away from him and notices me with a wave of her fingers.
Tyler approaches me with a shrug, “You’re going out with Kim on Saturday?”
“No, she’s having a party with a lot of big connections for me to meet. She invited me and some other interns so she could introduce us.”
“No she isn't, she is trying to get you into bed.” I snap.
He cocks his head at me, “Are you jealous?”
“No, I’m pissed that you can’t see through her games.”
“Her games? Okay, well, I can do what I want first of all, and if you don’t like it then you need to tell me a good reason why I shouldn't go.”
“Because she is a lying conniving Bitch.”
“Illana, I know that, but at the same time I am still a guy who is looking to make a name for myself in this industry and if I ever want to have an opportunity to build a successful business after I graduate, then I need to take advantage of every opportunity I can and this seems like a good one. I didn't say I would fuck her, I only want to use her to meet the people I need to.” Tyler says starting to walk away, but I grab his arm and pull him back. I stare hard at him trying to think of something to say that will make him understand my position on this matter, but I can think of nothing. “If you don’t want me to go Illana, then you need to give me a reason, if you don’t have one, then you’re going have to trust me to be smart enough to handle her. I’m loyal to you, I promise.”
“She thinks we are sleeping together.”

“Half this company is sleeping with each other, the other half is wishing they were sleeping with the other half. It’s not unusual, it’s pretty typical around here I have noticed. Hell Mr. Monroe is sleeping with his assistant, why do you think she got a two week vacation in the middle of a project? Because she is getting a new boob job paid for by him.” My eyebrows raise as the shock of it all begins to become clear. “Yeah, you really need to come out of your office more.” Tyler scoots me back to my office and shuts the door. He wraps his arms around me and kisses me. “We aren't doing anything new Illana, but I’m loving every moment with you and I am not about to screw that up. You have to trust me. Besides maybe I can find out some more dirt on her?” He smiles trying to reassure me with another kiss before he leaves me feeling lost and suddenly very alone. 


  1. Holy crap you need to make these a tad longer LOL I'm so not liking Kim and I have a sick feeling Tyler is playing Illana. God I hope not

  2. I hope Tyler is not trying to sleep with Kim an Ilana at the same time or maybe she can have a threesome with this roommate since they work well together. Love this but it's too damn short!


Dear Diary

Dear Diary
Illana's Confessions