Ms. Morgan's Dilemma

I looked down at my paper and sighed. It had come back from my professor all covered in red ink. A B! I would never get into University of Chicago Law with these kinds of grades! But, drastic times called for drastic measures. Fortunately, my Classics of Political Thought professor was kind of cute, in a dorky sort of way. I could do this, I thought. I looked him up and down appraisingly, appreciating his black curly hair, a little scruffy and needing a trim, his blue eyes behind dark-rimmed glasses, his physique which spoke of long days in the library instead of in the gym. He's older, maybe about 38, I thought, but still totally doable. I felt a little moisture between my legs and crossed them under the table and started to fidget. Yes, definitely doable.

At the end of class, he looked over the twelve of us sitting there and said, "As always, I will be in my office during office hours tomorrow, 2-4, and I'm sure none of you will avail yourselves of me, as always." He smiled self-deprecatingly and shuffled some papers as we all laughed and walked out.

Tomorrow, I thought. Tomorrow, I will put my plan into action.

That night, I came back from my room after taking a long shower so I could shave all the things that didn't tend to get shaved, since I had no boyfriend. My roommate had just returned home and was lying on her bed reading a book and eating an apple.

"Hey Mandy, can you help me figure out an outfit to seduce my professor?" I asked, opening up my closet. She choked on her apple and then started laughing.

"Let me see, Christa, do you want to go classic schoolgirl or more femme fatale?"

"I don't know, what do you think?"

She looked inside my closet, a dubious expression on her face. "Well, your wardrobe definitely lends itself more toward schoolgirl, unfortunately, and not even sexy schoolgirl..."

The next afternoon, I headed across the quad, wearing significantly more makeup than I was used to wearing, a (borrowed) white tank top under a half-unbuttoned white shirt, and a black skirt that my roommate had me roll at the top to make shorter, a trick she had learned by reading a book about Catholic schoolgirls. My long blonde hair blew free around my face instead of my usual ponytail. Mandy had also tried to talk me into pigtails, choking back giggles the whole time, but even I knew that was a little too on the nose. But she had helped me put on "just a little" makeup, smearing my face with her foundation and mascara and pink lip gloss. And, looking in the mirror before leaving, I noticed how nice I looked. She had adjusted the straps of my bra to give me more cleavage, which subtly peeked out from underneath the shirt.

As I paced along, I felt worried and wet at the same time. I hoped Dr. Smyth thought I looked sexy enough to fuck me.

I knocked on his door and then poked my head in, talking in what I thought was an unusually babyish voice, "Professor Smyth, can I talk to you about my paper grade?" I shut the door carefully behind me, making sure it latched then flopped down on the chair across from him, being careful not to keep my knees together. "I need an A, or, at minimum, an A-, in order to achieve my long-term goals."

As I sat across his desk from him, in his office lined with books, he seemed to be stifling a laugh, or maybe just a cough, but nothing in his voice betrayed him as he responded, "I see. Well, Ms. Morgan, you always can rewrite your paper, incorporating the suggestions I made, to bump your grade up to a B+."

My face burned. This was really not going to plan. I glanced up and caught him looking down my shirt. Got him!

He caught me catching him and blushed, a little. "You look different today, Ms. Morgan. Do you have a summer job interview after this or something? If so, I'd suggest buttoning your shirt up a little further."

Caught off guard, I stammered, "Uh, no, nothing like that..."

He then stood up from behind his desk and walked around to stand over me. "And your skirt is far too short. You need to be more diligent about keeping your legs crossed in a skirt like that. You know, I've seen your underwear five times since you've come in here!"

He pulled me to my feet. "And your bra is clearly visible through that white shirt!" He turned me to face him, my back toward the desk. "And those shoes are more suitable for going out to a club than visiting a professor in his office."

Mortified, I looked down and took a step back. He quickly took a step forward, backing me up until my butt hit his desk, his chest flush against mine. He chuckled. "Ms. Morgan, I believe you're trying to seduce me." My mouth gaped open as I looked up into his intent blue eyes for just a second before he leaned in and kissed me deeply. Our tongues touched as he started untucking my shirt from my skirt and unbuttoning it. He started kissing down my neck as he pulled the shirt off my shoulders and flung it across the room.

He leaned down to me, kissing down my chest and tugging my tank top out of the way to expose my bra. "Leopard-skin? Really. So unoriginal." He pulled my bra down, freeing my breasts. My nipples hardened immediately. "You really want this, don't you?"

I nodded, wordless, my pussy dripping.

"Good." He pulled away, leaving me cold, and sat down in the chair. "Now take off your skirt." He watched intently, smirking at my struggles to unfasten the rolled waistband. "Matching leopard-print panties, isn't that sweet? Seems unlike you, Ms. Morgan. Did you borrow them?"

"No, they were a gift from my ex-boyfriend..."

"You might as well take it all off. Did he ever get a chance to see you wear them?"

I nodded, peeling the tank top off, then unhooking the bra and pulling it down my arms. "But then he laughed and said I looked ridiculous in them."

"And then you broke up with him, right? I mean, there's not a sexy bone in your body, really, but there's no need to be mean about it." He unzipped his pants and pulled his cock out and started stroking it.

"No, he dumped me for my best friend." I pulled down my panties, showing my bare pussy.

"Oh, I'm sorry about that. I have something here that'll cheer you up, though." And at that, he stood back up, turned me around and bent me over the desk and was inside me before I had registered what he was doing.

He felt a lot bigger than what I was accustomed to, which hurt at first.

"Oh, fuck, you're so tight, Ms. Morgan," he moaned, as he grabbed my hips and pushed deeper inside of me. "He at least fucked you before he dumped you, right?"

"Yes," I moaned. Professor Smyth's big cock inside of me was starting to feel amazing. "He couldn't make me cum, though."

"Oh, I'll make you cum, though, all over my big cock. Would you like that?"

"Yeah..." My ex had never made me feel this way. The only time I had come close was when I touched myself. I felt his hands grip my hips, then I felt his fingers pull my ass cheeks apart. He teased my butthole, lightly running one finger over the rim, and around and around, before sliding it just barely inside my ass.

"Have you ever been fucked in the ass before, Ms. Morgan?" He pushed his finger further into my ass.

"No..." I had never thought of anal as particularly pleasurable. My ex had asked for me to let him stick it in my ass a few times, but I had alway said no, not seeing how it could be enjoyable for me. But Professor Smyth's finger felt so good in my ass that I was definitely changing my mind.

"Oh... You'll like it, don't worry." He suddenly pulled out of my pussy, causing me to groan in sudden emptiness. I heard him walk over to the other side of the desk, pull open a drawer and rustle around. He returned behind me and I suddenly felt something cold on my asshole as he squeezed something out of a bottle. "This is lube. I'm going to get your little asshole ready for my big cock." I felt him rubbing his finger all around my asshole before he stuck it in, slowly stretching my ass with his finger. I groaned in discomfort, feeling a strange mixture of pain and pleasure. Could it be that I was getting off to some degree on the pain? That was not something that I had ever thought to be possible, outside of the bad erotica my ex-boyfriend made me read in the hopes that I would let him fuck me in the ass.

I felt a little more pressure as he slid another finger inside me. "I need you to relax, Ms. Morgan... I know that relaxing goes against your Type-A control freak tendencies, but do your best." He chuckled and I groaned again, suddenly feeling very vulnerable, and started to struggle.

"Okay, relax, honey. I'm sorry, that was rude." He leaned over me, warming my back with his chest, and brushed my hair over one shoulder to fan out over his desk before nibbling on the nape of my neck. I shivered as he breathed in my ear, then whispered, "I think you're ready now. Stay right where you are."

He pulled away, removing his fingers from my ass, and I heard him open and squeeze the lube bottle again. I felt some pressure against my asshole, and then some more pressure as just the tip of his cock slid inside me.

"Oooh... ow..." I moaned.

"Don't worry, I won't go in any further until you're ready. Now, I want you to reach between your legs and start rubbing your clit for me."

Dazed, I did as he told me, feeling how wet my pussy had made his desk beneath me. The pain receded as I rubbed, and I started liking the feeling of him inside my ass. Wanting more of him. I pushed back against him a little, and felt him slide into me further.

He moaned. "Yeah, take me in, Ms. Morgan." I pushed back more, rubbing my clit like mad. "Oh fuck, this is definitely a virgin ass. Cum for me, Ms. Morgan. Cum on my big cock, all the way inside that tight ass."

He started thrusting, further and further inside me, and I started screaming, cumming harder than I had ever before, shaking and trembling beneath him. He groaned, louder, and I felt him squirt his seed deep inside my ass.

We breathed hard for a minute, his cock still inside me, my hand still on my clit, before he chuckled. "So, yes, Ms. Morgan, if you rewrite that paper for me, I might raise your grade to a B+."