What a Long, Strange Trip It's Been

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There are many twists and turns on the road to love.
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kurrginatorX
kurrginatorX
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This is a Valentine's Day Contest entry. To vote, please click the stars at the end of the story. Thank you.

**********************

Sunday evening I emailed Mrs. Sherman, my English instructor, with the following message:

Mrs. Sherman,

I know I have no right to ask this, but I need an extra week for my project. I have had one terrible incident after the other between familial problems and work-related issues. May I schedule an appointment where we can discuss the possibility of extended time? Thank you for any consideration you may give this request,

Alan Maldonado

I checked my email before going to bed. She had responded with

Alan,

Be in my office at seven-thirty sharp tomorrow morning.

Professor Edna Sherman

I'd make sure I was.

7:29 I was standing at her door. She arrived at precisely seven-thirty. We entered, and then she locked the door before taking her seat. I remained standing as protocol dictated one should never sit until the invitation to do so was given. She never gave it.

"Tell me about these setbacks," she said to me.

I explained them all to her, finishing with, "I know it sounds crazy, even made up, but I promise you I'm telling the truth."

"Mmm-hmmm," she said a bit sarcastically. Then, "Give me your thesis and an overview of your topic of discussion."

"My paper is titled 'Stephen King: Master Pontificator or Master Plagiarist?' I will show where King has stolen the plots of the majority of his works from other established writers."

"I'm wondering just how well your oral presentation is going to be," she said as she studied me. "Practice it on me."

"Well, that's why I'm here, Mrs. Sherman. I haven't written it yet. I need more time."

"You dear, silly boy," she said with a laugh. "Come here." I rounded her desk and stood before her. She lifted her skirt, exposing her seventy-plus year-old pussy to me. "Oral presentation. Now." I just stared at her, not believing what she was asking of me. "You either get on your knees right now and give me your oral presentation, or you get no extended time and I give you an F. Understand?"

That was all the motivation I needed. I slowly dropped to my knees as she scrunched down in her seat. "Don't be shy," I heard her say. I moved in and placed my mouth on her clit and began to suck it. Her pussy sure was hairy, but at least it was soft. I knew if I didn't fully commit to this that I would fail her class for sure, so I treated it like any twenty-year-old pussy I had eaten in my life. I really got into it, and not because I was turned on by any means, but because I was working for the grade. Well, the extension that would allow me the A.

I moved my hands around her legs and began to grind my face into her. "Oh!" she exclaimed. "You're really enjoying yourself down there, aren't you?" If that's what she wanted to think, so be it. I moved from her clit, which I was surprised to see was fully erect and about an inch long, to deep inside her pussy and licked her cream from her. In all actuality, it wasn't bad in any kind of way. I lapped at it for a few minutes before moving back to her clit once more. "Yes," she said to me. "That's it, Alan." Her legs began to tremble, then she began emitting a noise like an old Model A trying to sputter to life. "Uh-p-p-p-p-p-p-p-p-p. Uh-p-p-p-p-p-p-p-p-p," then her legs clenched around my head as she loudly sputtered, "Pah-p-p-p-p-p-p-p-p-p!" She jerked a few times, then she went limp.

I continued licking her juices from her for about a minute longer, then I pulled back. "What are you doing?" Mrs. Sherman asked me.

"Well, I thought that since you—"

"Oh, no-no-no-no-no," she said as she shook her head. "You still have miles to go before you sleep, dear boy, but you have provided me with the opportunity to change things up a little." She then threw her left leg onto her desk and cocked her right one out more before scrunching down even further. "Here. This should grant you all the access you need."

Quickly, albeit resignedly, I once again moved in and took her clit into my mouth. It felt hard as a bullet against my tongue, and every time I lashed at it she would give a small, quirky jerk. I moved down to her slit and began licking as far into her as I could. The thought then crossed my mind, If you're trying to get her to give you the extra time, why not go the extra mile? It was elementary, as far as I was concerned.

I slid my tongue down even further and began licking her asshole. "Oh, dear me!" she exclaimed. "This is unexpected, but much appreciated." She picked up her phone and dialed, then said, "This is Edna. Would you come to my office, please? Oh, and you will need to use your key. Okay. Bye." She then said to me, "Someone is about to walk through that door. You don't stop until I tell you to, understand?"

I nodded my head as I continued to lick her puckered asshole.

The door opened, closed, and I heard the latch go back into the lock position. "What have we here?" I knew the voice, but I just couldn't place it.

"Please, have a seat," Mrs. Sherman told her guest. "I have a student who is petitioning for more time on his project. He—Oooooh!—He's giving a very convincing argument."

"And you summoned me because ...?"

"Well, with you being the final authority now, I thought it best that you review his case, should I recommend he be given the time."

"Where are your thoughts right now?"

"I ... I ..." and then the Model A trying to sputter to life again. "Uh-p-p-p-p-p-p-p-p-p. Uh-p-p-p-p-p-p-p-p-p," and then her leg came crashing down on the back of my neck. She twisted as she sputtered, "Pah-p-p-p-p-p-p-p-p-p!" and it felt as if she were going to rip my head clean off my shoulders. She jerked a few times, then melted into her chair.

"So, I take it you recommend he be given the extra time?"

"Yes. Yes. Oh, Lord, yes," Mrs. Sherman said with a laugh.

"Who is it?"

"Alan Maldonado," Mrs. Sherman answered.

At her revealing of my identity, I raised my head to confirm what I already knew. The other woman in the room was Professor Lillian Ibanex. I had taken a class of hers a few years ago. In secret, we students called her "Ms. Ironbox" on account of she was co cold and exacting. She didn't believe in second chances back then. If my fate now rested in her hands, I knew I was already doomed.

Of her, she was not an unattractive woman. She had long, blonde hair, a pretty face, I'd say she was 5'6 and a buck-sixty, and if my measurement radar was still working properly, she was 38-28-40. Really, not bad at all as she had curves in all the right places. It was just her ugly soul that made her someone I would not want to be with, current circumstances excluded, of course.

"Have him come to me," Ms. Ibanex said. I stood to walk over, and without the benefit of even acknowledging me, she directed to Mrs. Sherman, "He's standing. Why the hell is he standing?"

"Alan," Mrs. Sherman said, "you will show Ms. Ibanex the proper respect she deserves. Now, get back on your knees and crawl to her."

I eyed Ms. Ironbox for a few seconds, then did as I was told. I really needed this extension, and if there was any hope of her giving it to me, I had to play the game. As I rounded the desk, ol' Ironbox lifted her skirt to reveal her plump pussy. Already naked? I asked myself. Shit, they planned this out. Last night, probably. Bitches. Even still, I continued to make my way to her on my hands and knees.

"How did the new lesson plans work out this semester?" Ironbox asked Mrs. Sherman as she absently spanked her pussy three times. I guess that was her way of telling me to get to work. As I moved in, I was just thankful that she was a shaver. There was something else, though. Ol' Ironbox had a tattoo of Tinkerbell on her pubis. Tink's wand came to rest directly above the clit and Pixie Dust flew from the tip of the wand. I'll be honest in saying it was a bit of a turn-on. I didn't think Ironbox capable of such a playful nature.

I moved in and placed my tongue at her slit and immediately I smelled green apples. It was either a lotion or a bath oil, but regardless, it smelled and tasted nice. I ran my tongue up to her clit and took it in my mouth. As I sucked it, I breathed in deeply, enjoying her permeating scent.

She continued to speak with Mrs. Sherman as if I weren't even there. I mean, looking past me when I stood was one thing, but I was really working her clit over pretty good and she gave no indication that I was even remotely making a dent. Did she truly have an iron box? Was mine an exercise in futility? I refused to accept that. I pressed my tongue as hard as I could on her clit and flicked it as fast as I could. "Oh, there it is," she said with a small jerk. So, that was it, eh? She needed it hard and fast. I continued to give her just that.

I was so intent on bringing her to orgasm that I had blocked everything else out. Oh, I'd catch snippets of conversation, such as, "Well, you know he's retiring next year," and "... wasn't even there when it began." Finally, though, something was said and done that did get my attention. Ironbox was talking and she said, "We'll be downsizing next year, and—UHN!—we ... We're going to be adding a few more classes to—UHH!—to each instructors workload that ... that ... Oh, shit! Here it comes!" She grabbed the back of my head and held me in place as she thrust her pussy upward. I remained latched to her clit, though, and continued to suck it as hard and fast as I had been. Finally, she relaxed her grip on me and came to a completely relaxed state. "Wow," she said with a laugh. "I really needed that."

I wasn't going to make the mistake of coming off her like I did with Mrs. Sherman, so I just slid my tongue inside her and licked at her thick cum. I then heard Mrs. Sherman say, "You should get him to lick your backside, Lillian. He's quite adept."

Ironbox looked down at me and asked, "Are you? Are you an accomplished little ass eater?" I nodded my head. She placed a hand on my forehead and shoved me back. She then threw her legs over the arms of the chair and held them in place even as she wiggled down. "Well, what are you waiting for?" she asked me. "Get to work." I lightly separated her ass cheeks and began licking her anus. She shoved my head away once again as she said, "When I tell you to eat my ass, I mean for you to eat it like you mean it. Do you understand me?"

"Yes, ma'am," I said.

As I made to move in once again, she stopped me and said, "Edna, get behind him." Mrs. Sherman did as she was told. Ironbox then said to me, "Peel my ass cheeks back as far as they will go, and then do your damnedest to fit your tongue up it. You got me?"

"Yes, ma'am," I said, and did so.

Just as my tongue touched her anus, she said to Mrs. Sherman, "Shove his face as far into my ass

as you can." When Mrs. Sherman did this, I felt my tongue bounce off Ironbox's rubbery anal tissue before coming to rest dead center of the sphincter. I pushed with all my might, just as hard as Mrs. Sherman was pushing my head, and I actually felt my tongue pierce her. She apparently felt it, too, as she jerked a little. "That's it. That's it. Get on up in there," and I did my best to. I was rolling my tongue. My eyes had been closed, but I opened them to find Ironbox rubbing her clit as I did everything in my power to tongue-fuck her tight and tiny asshole. "Oh, fuck," she said as she continued to masturbate, then she once again grabbed me by the hair and immersed my face into her pussy. I didn't even go for her clit this time, though. I just tongue-fucked her pussy until she cried out and her warm cum filled my mouth.

I remained in that position, slowly licking up her cum. She finally pushed me away, then composed herself. She then said to Mrs. Sherman, "You may apprise Mr. Maldonado that we will contact him with our determination concerning his case." Mrs. Sherman did so, and then she dismissed me.

I waited outside her office door, though, and not so much to speak with Mrs. Sherman, but Ms. Ironbox. A few minutes later the door opened. She saw me and said, "Why are you still here?" as she made her way to her office. I followed her in and locked the door behind me.

"I need to discuss two things with you," I said. "The first is that I really need to know right now if I have the extra time or not. If I do, then I can go home and start work on the project. If not? Well ...?"

"You have the extra time."

"Thank you," I said. "Now, for number two. Um ... I was thinking that maybe it would be a good idea if I were to meet with you every morning for ... um ... status updates?" When I said that last part, I inclined my head toward her crotch.

She studied me for a few seconds, then asked, "Have you offered to do this with Mrs. Sherman?"

"No, ma'am," I answered. "She said you were the final authority, so I figured you needed to be the only one I should report to."

She continued to study me, then said, "Why don't you come over here and show me what you have in mind?"

I immediately dropped to my knees and crawled to her. By the time I reached her, she had thrown a leg over her desk and lifted her skirt. I wrapped my arms around her hips, pulled her forward a bit, then began eating her pussy once more. She shoved my head back like she had done earlier. "Oh, you're going to have to do much better than that. I want details."

"Slap me," I said.

"What?" Disbelief dripped from the word.

"Slap me," I repeated.

She stared at me for all of ten seconds, then she brought her hand across my face. It wasn't hard enough to hurt me, just sting a little. I quickly shot my mouth to her clit and gave her the pressurized force I knew she desired. She had taken my hair in her fist and was mushing my face into her pussy as I ate her. Just then, the door handle jiggled. "Shit. Crawl under my desk," she said. "Quickly."

I did, and she had just enough time to position herself dead center when the door opened. "Oh, Ms. Ibanex. I didn't realize you were here." I recognized the voice immediately. It was Robin, Ms. Ibanex's secretary. "I would have knocked if I had known."

"You weren't at your desk when I arrived," Ironbox told her.

"Oh. Yes. I was delivering something to Mr. Worthem's office."

"What do you need from me?" Ms. Ibanex asked.

"Oh. These are the files you asked me to have ready for you yesterday?" Robin answered as she stepped forward and handed them to her. "I'm going to the vending machines. Can I get you anything? Soda? Chips?"

"I'm fine, Robin. Thank you." Then the door opened, closed, and there was silence. Ms. Ibanex pushed her chair out a little, then placed both her feet on her desk. "Come on. We haven't much time." I immersed my face into her pussy once more. She was cumming two minutes later. She pushed herself out further, allowing me the room to crawl out and stand. As I did, she said, "Let that be a lesson to us both about how dangerous it can be to conduct these interviews here." She wrote on a piece of paper, then passed it to me. It was an address. Her address. "Do you know where that is?"

"Yes."

"Be there tonight at nine o'clock sharp. Not eight fifty-nine, and not nine-oh-one. In fact, let me see your phone." I handed it to her. She pulled hers out and watched them for about twenty seconds, then said, "They are synchronous. The very moment 8:59:59 turns into 9:00:00, I want you knocking on the door. Understand?"

"Yes, ma'am."

"I don't care if you have to get there thirty minutes early to ensure this. Nine sharp."

"Yes, ma'am." I then turned and left her office.

On the other side of the door sat Robin. Immediately upon seeing me, she said, "Where did you

come from?"

"Well, Robin, when a mommy and daddy love each other very much..."

She burst into laughter, loud, full, and unrelenting for twenty seconds. I liked Robin. She was one of the first people outside of students that I met when I first began my Freshman year, and in the four years since, she had always been a wellspring of knowledge and assistance whenever I needed it. As she composed herself, she said, "No. I didn't see you go in."

"Oh, I came up the back steps. I saw you heading down the hall." I pointed at her drink. "Buying that, I'm sure."

"Yeah. Okay." She then leaned in close and asked, "Is everything okay? Meeting with the Dean isn't always a good thing."

"Yeah, everything's fine. Just discussing my final grades. You're probably looking at this graduation's Valedictorian."

"Congratulations," she said as she stood and hugged me. She began to pull away, then stopped and breathed in deeply. "What is that? It smells so familiar."

My heart damn near stopped. Did she recognize the smell from Ms. Ibanex? I couldn't chance it. I didn't want to say, "Green apples and pussy juice," so I opted for, "Something my sister had lying around. Green apples and cucumber melon, I think. I really can't remember." It was a lie, of course. I don't even have a sister. Whatever works, though. Right?

She sniffed again, said, "So familiar," then took her seat.

"Oh! I forgot to tell Ms. Ibanex something. Be right back." I knocked, and when the order to enter was given, I did. I made sure the door was closed all the way, then approached her desk and whispered, "Robin questioned me about the green apple smell. If you have any cologne, it might be a good idea to douse yourself with some."

She immediately pulled a tiny pump bottle from her purse and pressed it three times. "Thank you, Alan." It was the most sincere thing I had ever heard her say. I nodded and made my way to the door, and she stopped me. "About tonight?"

"Yes?"

"Be prepared, for today was just a taste of what I have in store for you."

I didn't say a word. I left her office, said my good-byes to Robin, and made my way home to begin my paper.

The truth of the matter was that I had already read all the books, King's and the other authors', and even made notations. All I needed to do was put together my bibliography and type a ten-or-more page paper that fluidly exposed King for the charlatan he is, which a part of me hated to do. Before I began this task, he was one of my favorite authors. As well-read as I am, though, I was pissed to find out that he was ripping off other authors and nothing was being said about it. Well, I was going to say something, and King fans wouldn't like the end result.

I got home around nine-thirty and began the bibliography, which I finished at two. I watched some TV in an attempt to clear my mind a little, but that didn't work. You see, even as I was building the bibliography my mind kept turning to Ms. Ibanex, to that cute little Tinkerbell tattoo and the green apple smell and taste of her pussy and ass, and finally to me submitting myself to her. Why did I do it? I hated her, didn't I? The more I thought about it, though, the more I began to reconsider.

I wasn't any good in getting back to work, so I killed time as I waited to get my shower in preparation for tonight. Finally, at seven, I did. I was really horny, but I resisted the urge to jerk off. I kept replaying in my mind me eating her pussy and ass. Oh, her ass. I wanted it so badly. I had to stop. My nuts began to hurt.

I arrived at Ms. Ibanex's at 8:58:27. I immediately made my way to the door and watched my phone to ensure I met her demand. I saw movement from the corner of my eye. She had peeped out of the blinds to see me standing there. I continued to wait at the door, phone in my hand, and finally it was 8:59:58, 8:59:59—I raised my hand to knock—9:00:00. I moved my hand toward the door, but I stopped abruptly. I looked at my clock again. 9:00:01, 9:00:02, 9:00:03, 9:00:04, 9:00:05, and then the rap-rap-rap of my knuckles against wood.

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