Kelly's Diary 187 - School Administrator
Copyright© 2025 by Kelly85
Chapter 5: How Bad Did I Want the Job?
Incest Sex Story: Chapter 5: How Bad Did I Want the Job? - Life can be like a roller-coaster sometimes, full of climbs and drops, sudden turns and gut-wrenching twists. All my life I'd wanted nothing more than to be a teacher and then it seemed all my hopes and dreams were crushed. When an opportunity arose, who could blame me for comprising my principles so long as it led to me doing what I'd always dreamed of - teaching.
Caution: This Incest Sex Story contains strong sexual content, including Ma/Fa Consensual True Story Cheating Incest Father Daughter Exhibitionism Oral Sex
It was a few minutes after noon when I drove up to the hotel and searched frantically for a parking spot. The “after church” lunch crowd was already there in force and so I ended up way out in back before I finally found a place to squeeze into. Turning off the ignition, as late as I was I sat there for a moment with both hands firmly gripping the steering wheel, eyes closed as I prayed and try to prepare myself for what I assumed was about to happen.
It’s funny how the same actions and events can have totally different results, simply because of the circumstances involved. Had I been here to meet some husband from church, perhaps cheating on his wife and anxious to do about anything to spend the afternoon with me, I would have been excited and wet with anticipation. Yet here I was, basically about to do exactly just that, yet somehow I felt more anxious than excited, dirty instead of slutty, resigned versus horny. Definitely NOT excepted and wet.
For a girl who prided herself on being a slut, I certainly wasn’t feeling very good about myself now. Maybe it was because this job meant so much to me. I’d dreamed for most of my life of being a teacher, worked hard in school, sacrificed so much to achieve my goal and now, just as I was about to reach it, I found myself having to use my body instead of my credentials to realize my dream. Had it been any other job or position I wouldn’t have hesitated a bit to use every “asset” I had - hey, why not use what you got? This was special though, this was about me becoming a teacher based on my credentials and skills, not my looks and sexual skills.
Yet in the end, what option did I have? Sure, I could get all high and mighty and claim I was sticking to my morals. That would mean walking away from this job and waiting for who knows how long before something else opened up. The last thing I wanted was to spend another school year stripping and modeling lingerie while I watched kids going off to school, knowing I wasn’t in front of the class teaching them. I mean, like I was 24 now and not getting any younger. It was time to get my career started. Besides, it wasn’t like Mr. Eisenberg was all that bad. He WAS pretty good looking and I was sure he would be extremely discreet as he had far more to lose than I did if any of this ever became public knowledge.
I bowed my head, said a final quick prayer, and took a deep breath. Letting it out slowly, I put my head back and opened my eyes, filled with a new determination. If this was what it took, a few hours of letting some pervert have his way with me, then what was the big deal anyway? No matter what happened, by the time I ate supper it would all be over and the job would be mine. If anything, on the bright side I figured my job security would be pretty good considering the “goods” I would have on Mr. Eisenberg after today!
Stepping out of my car, I tried to pull my hem down as my dress had ridded up to my waist as I drove. It was then I noticed a family walking by, the parents with the standard issue two kids, a boy and girl that looked to be in their young teens. I couldn’t help but smile as the mother turned the boy’s head from me as he must have noticed my brief “flash” as I stepped out of my car. Boy ... if looks could kill, hers would have melted me down on the spot! The husband was eyeing me as well so I just grinned at him and clutched my purse as I followed them into the hotel lobby.
The restaurant was off to one side and I was about to head down the hall when I heard someone calling my name. I looked and there seated in the lobby, was Mr. Eisenberg. He was getting to his feet and gesturing for me to come over to him.
“Hello Miss Wells, glad to see you showed up. I wasn’t sure after out last interview if you really wanted the position or not.”
Yeah right, like there was any doubt. His eyes were running up and down my body, noticeably pausing as he took in my boobs and legs. God, what a perv! But then, a girl doesn’t wear a dress like the one I had on unless she WANTS a guy to do just what he was doing! After all, what was the point of dressing like a slut if nobody noticed?
“So shall we go have lunch now?” I suggested, gesturing with my hand towards the restaurant entrance where people were lining up to be seated.
Although I’d never eaten brunch here, I’d heard it was good and judging from the crowd, the rumors were apparently true. We would probably have to wait a half hour or so just to be seated.
“Well ... I wanted to talk to you about that,” he said slowly, barely audible even though I was right up next to him now. “I’m not so sure it’s a good idea for the two of us to be seen together in public - especially dressed the way you are. Not that I don’t like it of course. It does a fine job of showing off ... your ‘credentials’, you know what I mean?”
My eyes narrowed at him, as if I was surprised by what he was saying. Sheesh, back to those horrible lines again. Couldn’t he say anything without using such tired old crappy cliches? Actually, what WOULD have surprised me the most would have been if we actually DID have lunch in public like this. Odds were SOMEONE would see us and then the gossip would start. I’m sure the last thing he needed was someone asking his wife why he was seeing a new teacher at a Sunday brunch - a teacher wearing the sluttiest dress in the room.
“But I thought we were going to do my final interview?” I asked, pretending to not know where he was going with this. Like, I would have to have been a totally idiot not to know already.
“Well, I just thought we could do it somewhere ... more private,” he suggested. Then he finally came out with it and said, “I booked a room where we can do your interview without drawing too much attention. Is that OK with you?”
Shrugging, I tried to look as if I had to make a decision but in reality, this was all going exactly the way I’d expected. I mean if you think a guy invites you to a hotel for an interview where you are expected to show “how bad” you want a job just to have a discussion over lunch, then you’re too dumb to be teaching!
“Sounds good to me, I’m sure you’ll be impressed,” I replied with a naughty little smile. It was just enough to let him know I was “in” on his plans, even if he hadn’t come right out and stated them.
“Great, let’s get going then.”
I followed him to the elevators as he looked around to make sure nobody was watching us. For him, the was probably the most “dangerous” moment where someone might see him getting into the elevator with me. It would be awfully hard to explain to his wife, that was for sure! As it was, we entered the elevator alone and he pressed the button for our floor. Neither of us said a word as it took us up and the doors opened again. Mr. Eisenberg led me down the hall to the room, never even looking at me as he opened the door and walked in with me trailing close behind like a puppy dog.
As I stepped inside the room, I could see it was your standard issue Holiday Inn - two double beds, a TV mounted to the dresser with a small round table and two chairs next to it. It was pretty warm and stuffy so he turned on the AC unit under the window. It was pretty loud but I could feel the blast of cool air almost immediately.
Mr. Eisenberg turned and stood there across the room from me, both of us quiet as we waited for the other to make the first move. If there was one thing I was sure of though, HE was going to be the one to initiate anything. It was bad enough I was essentially whoring myself out for a job. The least he could do is leave me with no option so I wouldn’t have to wonder forever afterwards if I could’ve possibly gotten by without doing what I knew I would likely have to do.
“Well, well Miss Wells, so here we are.”
I stood there silently, smiling at him to try to put him at ease but otherwise waiting for him to continue.
“I think we both know what this ‘interview’ is really all about, don’t we,” he said quietly, more a statement than a question. I just nodded slightly and waited for more.
“I just want you to know I’ve never done anything like this before,” he said, suddenly looking a little unsure of himself.
“So why now then?” I asked softly, “We can stop now ... nothing has happened yet.”
Mr. Eisenberg sighed and I could see the struggle that was within him. In a way, I could sympathize with him. I’d been in similar situations before where it all seemed so hot and wild to talk about something and even fantasize about it; but when it came to the actual DOING of it, that’s when the reality sank in.
“Maybe we should forget about all of this,” he said, “I don’t know what I was thinking.”
Suddenly I felt this surge of anger. Damn him anyway. He’d put me through all this and now he was going to chicken out, I just knew it. Odds were he would then find some excuse not to hire me and then it would be my word against his as to why he’d changed his mind - and who would believe me over him, especially if he revealed anything about why I’d left in the first place.
“How bad do you want the job?”
Yes, that was the question he had left me with in his office and now I was ready to show him. Indeed, I wanted the job and I wanted it BAD - so bad I’d resigned to whoring myself to get it. Now this idiot thought he could just change his mind and back out of the deal? Noooooo, I don’t think so.
One thing about this pink dress, it not only didn’t hide very much, but it barely stayed on me so when I wanted to take it off, all it took was a quick shake of my upper body to let the straps fall off my shoulders and the whole thing would slip down to the floor. That’s exactly what I did now - a little shake and the next thing he knew I was standing there totally naked in front of him. Well, not TOTALLY if you count my jewelry and heels but close enough. His eyes bugged out and his mouth dropped open like a fish out of water before he caught himself and took a deep breath.
“Now Mr. Eisenberg, you told me in your office that you wanted me to prove how much I wanted the position ... so what do you think?”
“Miss Well...” he stammered, “please put your dress back on. I’m serious ... please stop right now.”
“Oh come now Mr. Eisenberg,” I purred as I put one bare leg up on the bed and cupped my naked crotch with my hand, “I saw how you looked at me. I bet you’ve been dreaming all week of seeing me like this, haven’t you?”
It was like he was frozen place, unable to move. I knew his brain was telling him to leave the room, FAST, before he did something he could never undo. At the same time, I saw the unmistakable signs of an erection starting to form under his suit pants and I knew what was happening. It was a classic struggle between the big head and little head. I knew well that as the little head grew in size and strength, it would soon overwhelm the big head.
It was like I was a mercenary supplying arms to the resistance. All I had to do was help his dick gain control and he would be mine. It was just too easy, like shooting fish in a barrel as I knew exactly what to do.
“My pussy’s so hot right now ... it’s soooooo wet,” I teased him naughtily, “It wants YOU Mr. Eisenberg ... don’t you want it?”
Oh he wanted it, that was obvious. Like what man wouldn’t want a 24 year-old pussy as the girl played with herself in front of him? From the family pictures I’d seen in his office, it wasn’t like his wife was all that frumpy, but I bet she’d never looked like I did right now and odds were she never masturbated in front of him either - as I started to do for him.
“Mmmmmmm, it’s so wet Mr. Eisenberg, I’ve been thinking all week about you ... about you and me ... about you fucking me.”
He visibly winced when I said “fucking me”, as if I’d exposed his secret desires. I WAS wet - and getting wetter by the minute, but it wasn’t so much my finger that I now had pressed inside my pussy that was turning me on ... it was his eyes fixated on my bare crotch as I did it that had me going. Oh yeah, he wanted me ... he wanted me bad. It was time to get him involved a little more...
Putting my leg back down, I put my finger that had been in m pussy up to my mouth and licked my pussy wetness from it before putting it in my mouth and sucking off the rest. He looked so turned on and I knew he was ready for the next thing I had in mind for him. Moving up close to him, I reached down and started unbuckling his belt. His hands instantly went over mine, trying to stop me with a half-hearted effort.
“This has to stop now Miss Wells ... now!” he burst out.
The fervor of his words weren’t exactly matched by the strength in his hands. As big as he was compared to me, he could have easily stopped me had he REALLY wanted to but instead I was able to push him aside and soon his belt was undone. Next was the button and the zipper as his hands hung limply to his side, making no further effort to stop me. I pulled his pants down, together with his white jockey shorts, to his ankles. His dick was maybe half to three-quarters erect by now and it stuck out past the tails of his dress shirt, the head poking out like a gopher checking out the area before emerging from his hole.
I kneeled in front of him and grabbed his dick with my hand. Mmmmmmm, it felt so warm! He wasn’t exactly steel rod hard yet but the promise of near-future stiffness was definitely there. I looked up at him and our eyes met.
“You asked me how much I wanted the job Mr. Eisenberg,” I told him in a husky whisper, “Now I’m going to show you ... and then you’re going to give me the job.”
He looked like he wanted to say something, maybe protest a little but it was too late for him now, he was mine My hand on his dick may as well have been around his neck. He knew I was about to suck his dick and at this moment there was nothing more in the world that he wanted other than to feel my lips caressing his cock, my tongue playing over his shaft as I took his stiff cock in my mouth.
“Oh my god,” he whimpered, almost choking on his words as I took his dick in my mouth and began to work on it with my lips and tongue, “That feels incredible ... so good.”
His words were like music to my ears. If there’s one thing I love to do, it’s suck dick and to hear a man tell me how much he enjoys it, how good I am at sucking him ... well who doesn’t like to be complimented on their skills? Actually, he seemed even more appreciative than I would have expected this early on and suddenly a thought struck me!
“Doesn’t your wife suck your dick Mr. Eisenberg?” I asked, stroking his now wet dick as I looked up at him quizzically.
“Hell no, she never has ... she says oral sex is dirty, sinful,” he gasped. His hips were making little mini-thrusts, as if he was trying to hint at me to take it back in my mouth again.
“So you’ve NEVER had a BJ before?” I asked in incredulously. He just shook his head as if he was too embarrassed to answer. Wow, a BJ virgin! Now this I hadn’t expected.
Back to his dick I went with a renewed determination to make his first blowjob a memorable one - as if it wouldn’t be no matter HOW I sucked him. It amazed me in this day and age that a man his age had never had his dick sucked, not even as a teenager. Like, there are so many different parties these days where girls do BJs for fun that I don’t see how any boy can NOT get blown if he really wants it.
Although Mr. Eisenberg wasn’t THAT old, I wasn’t sure what his recovery time would be so I didn’t want him to cum after just a BJ. Yet at the same time, I wanted him to enjoy it as much as possible. I wanted him to see what a good BJ I could give. Who knows, maybe someday he might get another and I didn’t want him to think it was better than mine!
His dick was full grown now, as stiff as it was going to get. His crotch had this thick musky odor that a man gets when he is really horny and turned on. My hand cupped his hairy balls, softly rolling them between my fingers as my other hand rubbed my pussy. I always loved to touch myself while I blew a cock - like getting a “two-fer”.
As I said, as much as I enjoyed sucking his dick, I didn’t want to spend all afternoon waiting for it to get hard again so I stopped short of him cumming. When I dropped his dick out of my mouth and stood up, he seemed almost heart- broken as no doubt he had been imagining himself cumming in my mouth. Well, not today - at least not yet. His sadness melted, though, when he heard my next words.
“So your wife hates oral sex, huh?”
He just nodded with a frown on his face.
“So you’ve never tasted a pussy before?”
“Well, not directly,” he stuttered. I figured that meant he must have tasted it on his fingers or something like that after he’d touched her pussy.
“Didn’t any of the other girls you dated suck your dick?”
My wife and I saved ourselves for marriage,” he replied, a note of pride seeping into his voice.
Why people felt proud about foregoing sex before marriage was beyond me but hey, it that’s what he wanted then I respected him for it. Still, that meant I was only the second girl he’d had sex with! Cool!
“Well, I want you to lick my pussy now Mr. Eisenberg,” I said in a soft but demanding tone, “I want to feel your tongue on my hot wet cunt.”
Much as I usually steer away from the “c” word, it seemed to turn him on for me to be a little more “dirty” for him. No doubt his wife never even called hers a pussy in front of him, let alone a cunt.
He didn’t say a word as I stepped back to the bed. I pulled off the comforter (who knows WHAT I son those filthy things!) and laid back against the pillows, lifting my knees so my feet were flat on the bed with my feet spread far apart do my pussy was on full display for him. He just stood at the edge of the bed, staring at me as I started to play with myself again for him.
“You like my little pussy Mr. Eisenberg?” I asked him in my best “little girl” voice. “I bet it’s tighter than your wife’s. Does she shave her pussy like mine?”
He didn’t answer, instead he just watched as I used both hand to touch myself, opening my pussy, spreading my lips apart as I toyed with my clit and used two fingers inside of me to masturbate for him. God, I was so damn horny by now! Really, I would’ve much rather he just got down and fucked me now instead of an amateurish pussy licking but then whole point of doing all this was to demonstrate to him how bad I wanted the job, not my own personal satisfaction. Hopefully he liked the look of my “credentials”!
“Lick my cunt Mr. Eisenberg,” I invited him. Mmmmmmm, I was so close to having my own orgasm by now that it wouldn’t take much to set me off now - even a first- timer would be enough. Now if he would just hurry and get to it!
Mr. Eisenberg was still half-dressed so first he took off his shoes and socks, followed by his blue tie, white dress shirt and white cotton t-shirt. Now he was nude and I have to say, not bad looking ... not bad at all! The thing that most interested me, his dick, was still ramrod hard as it pointed upward without any assistance. God was he horny as well! Working his way onto the bed, Mr. Eisenberg got between my legs and laid down on his elbows with his lower legs and feet hanging off the end of the bed. He started to caress my inner thighs, a part of me that LOVES to be softly touched!
“You have the most sensational legs Miss Wells,” he complimented me.
By now I’d had enough of this “Miss Wells” thing so I corrected him, telling him to call me Kelly.
“That’s my wife’s name - Miss Kelly,” he explained, his eyes suddenly looking up as if he was worried something would come down from heaven and strike him down.
Ahhhhhh ... so THAT was why he kept calling me that. It was one thing to have sex with another women for the first time, but to have it with a girl whose name was the same as his wife’s was undoubtedly a little weird for him. Well, at least he didn’t have to worry about calling out my name should he fantasize about me the next time he and his wife had sex! Guess it also made it easy for him to keep track of the names of the girls he had fucked.
Without further discussion, he lowered his head to my crotch and tentatively reached out with his tongue to touch my pussy. Fortunately, he manage to hit my hyper-sensitive clit dead-on the first time, making me jump just a little as it sent out a jolt of electricity throughout my body.