I pull off my oversized T-shirt and shimmy out of my panties.
Totally naked, above and below.
That’s what I’ll write under
What were you wearing?
in the journal.
Next I fold the pillow and wrap it in the towel. I always get very juicy when I’m doing it for the professor. I stretch out on the bed and push the pillow between my legs, resting on my elbows to allow for good access to my breasts, which
dangle like cones of white wisteria, tinted tender pink at the tips.
The professor will love that. He specializes in the Romantic poets and is partial to natural imagery.
I note the time on the clock above my bed, then cross my arms and begin to caress my breasts, my right hand cupping the left tit, my left hand stroking the right. My nipples feel soft and satiny and more sensitive than when I’m lying on my back, my usual position for self-pleasuring. I push my hips into the pillow, grimacing at the nubby texture of the towel against my tender slit. Maybe this isn’t the answer after all?
Think, Tina, think. The rest will come.
It’s the professor’s voice, smooth and deep, guiding me ever onward to new achievements.
I close my eyes and think.
A man steps from the melting red shadows behind my eyelids and stands at the bottom of my bed. His gaze is fixed on my naked ass. I can feel it, as bright and hot as a spotlight. I squirm involuntarily and that sweet, achy sensation of longing floods my belly. What is he thinking and feeling as he watches a horny slut masturbate just for him?
I begin to hump the pillow with slow, rhythmic thrusts. I can make out the man’s face more clearly now—the lush, curly brown hair, the wire-rim Russian Revolutionary glasses. He is young—only two years older than I am and not even tenured yet—but he has enough of a snotty academic air that I yearn to rub away at that smug composure with every jerk of my hips. I want him so jealous of this pillow that he’ll start begging me to let him take its place between my legs.
I pause mid-thrust and sigh. The sensation still isn’t intense enough to bring me off. It might work if I could use my fingers to spread my labia and get direct friction on my clit, but of course, the assignment specifically forbids it.
I know you have it in you, Tina. Push a little harder. Show me how naughty you are deep inside
.
“Yes, Professor,” I whisper, into the air. I do want him to see me; not just my flesh, but my darker, deeper places.
The room shifts; the morning light filtering through the curtains turns to a harsh fluorescent buzz. Steel prison bars bisect the room, and my bed becomes a cot covered with a rough, gray blanket. I’m still humping a pillow, my bare buttocks aimed straight at the bars, but the audience has expanded tenfold. A carefully selected squad of prisoners has been brought here to watch an oversexed girl get herself off without using her hands. It’s not clear if this is a reward or a punishment for these hardened criminals. I know the guards are sadists. They’ve told me that if I don’t come this way in twenty minutes, the whole crew of correctional officers will get to fuck me on the sagging sofa in their employee lounge in ascending order of cock size. They warned me with a leer that the biggest one, Harry the Horse, has a dick that would put a baseball bat to shame.
The stakes are definitely higher now.
I rock my hips faster against the damp towel. The prisoners’ eyes bore into my flesh. They’re bad guys, lifers. They haven’t had a woman in decades, and their soft howls of frustration ricochet off the concrete walls. With a fearful glance over my shoulder, I see their huge, swollen cocks are protruding from their flies. Some pump themselves frantically, heedless of the grinning guard. One pushes himself through the bars, fucking the air, as if he can enter me that way if he tries hard enough.
“Boys, you’ve got five minutes to finish your business, then it’s back to your cells,” the guard barks. Then his voice turns to sugar with a touch of poison. “You, too, sweetheart. Five minutes or you know what we’ve got waiting for you.”
“I’ve seen enough assholes in this joint. Make her flip over and show us her cunt,” a hoarse voice grumbles.
I hear the crack of a fist landing on flesh, a bellow of pain.
“What you see is what you get,” the guard growls.
The men moan and grunt like beasts as they hurry to empty their balls. My head is bursting with lewd sounds, the rasp of dick flesh being rubbed in spit-moistened fists, the rhythmic knocking of hips against the bars that keep me cruelly out of their reach.
One man stands back, eyes narrowed, arms crossed, his fly firmly zipped. He is watching me, but he’s also watching them watching me. It’s the professor. Even in this place, as far away from twining ivy as you can get, he’s still the one in control.
My nipples are as hard as little pebbles now. When I flick them with my fingers, electric jolts jump straight to my pussy. I’m gyrating like a stripper, sliding my cunt down over the pillow, then jerking back up, like my ass is tethered to a spring. Though I’m usually quiet when I masturbate, I realize I’m making sounds, too: deep grunts and harsh bellows to harmonize with the
bang-bang
of the headboard against the wall. But I’m going to make it in time. I can feel the orgasm begin to grow, a throbbing knot in my gut. And the prisoners are right there with me. With a collective groan, they shoot their wads through the bars, spraying my ass with a sizzling fountain of spunk. The odor fills my nostrils, hay mixed with something harsh and tinny; the nastiest, naughtiest smell on earth. It’s all I need to push me over the edge. I ride the pillow like a bucking bronco, screaming myself hoarse as I climax, each contraction harder and sweeter than ever before.
As the spasms fade to a flutter, I check the clock. Length of session: twenty minutes from start to finish. I collapse facedown on the bed and listen to my pounding heart. So far, so good, but this is just the beginning. It’s never really over until the professor gives me my grade.
“Isn’t that Professor Perkins over there? And you’ve got his table, Tina. Lucky bitch.”
Pam and I had a lot in common. We were both education majors with a minor in English lit; we both worked weekends at Chez Jacqueline. Of course, she was twenty-one. I was eight years older and far too worldly-wise to gush over an attractive young assistant professor.
“Those must be his parents,” I said, eyeing the other members of his party: a slim, well-dressed older woman and a gray-haired guy who looked more or less like the professor with thirty years on him. Chez Jackie’s was the best restaurant in town and we often waited on our teachers and their families. I was curious to see how Perkins would act when he was off duty. In class he was affable but no-nonsense—forget about getting an extension on a paper from him.
To my surprise he was positively charming in the candlelit glow of the dining room. He remembered my name and introduced me to his folks with a jaunty, “Tina’s without question my best student this semester.”
“I know Pam gave you a free dessert when you said that to her last week, Professor, but I’m a tougher nut to crack.” I grinned at his dad, who winked back.
“Damn. Because this time it’s actually true,” Professor Perkins joined right in.
Mom smiled, too, and did a little back-and-forth glance between her son and me that made it clear the professor wasn’t currently attached, but Mom was hoping he might find a nice girl soon and she might possibly be yours truly. Which almost made me laugh out loud because I was far too busy getting my life back together to waste time lusting after my professor. Okay, so I did occasionally let my mind wander during class. I’d picture the professor naked and try to guess what his cock looked like erect. Long and slender or thick and florid? Ramrod straight or curved to the left as any P.C. professor’s should be? Once or twice I even imagined what it would be like to ride him and watch his face as he came. But I did that with every professor, including the old silver-beards and—during really boring lectures—even a few of the women.
But I should’ve remembered that Mom always knows best.
I was heading back to the kitchen with a tray of dirty plates when Professor Perkins stepped out of the hallway by the restrooms.
“Excuse me, I know you’re busy,” he stammered. “But I wanted to let you know I turned in the final grades for your class yesterday.”
My stomach did a somersault. Why would he look so nervous unless he had bad news? Yet I’d gotten an
A
on the midterm and very complimentary comments on the final paper:
Your argument is tight and compelling, the writing smooth and flowing—a true pleasure to read
.
The professor smiled as if he read my thoughts. “Don’t worry, you did very well. I mentioned it because I’m now ethically allowed to ask if you’d like to get together for coffee or something.”
Could it be that while I was fantasizing about Professor Perkins naked, he was returning the favor? Maybe I’d get to see what his cock looked like after all.
“Thanks, Professor. Actually, a bunch of us usually go over to the tapas place for a drink after work around eleven. You’re welcome to join us tonight—if your mom and dad give you permission.”
He blushed—I was starting to like this shy suitor side of him—but recovered quickly and gave me a grin. “I’m sure I can talk them into relaxing my curfew tonight. After all, there’s no school tomorrow. See you later, then, Tina.”
I had to admit I felt a little thrill as I watched him stride back to his doting parents. Professor Perkins had me in his power all semester. Now I was turning the tables.
Or so I thought.
Assignment #5: Go to the woman-friendly adult store south of campus. Ask a saleswoman for advice on anal toys. Confess your level of experience—beginner, dabbler, veteran ready for a challenge? Purchase the item she recommends as well as a bottle of lubricant. When you return home, insert the toy in your anus and masturbate. Record the experience in your Masturbation Journal, following the usual guidelines. Your last assignment earned
A
for the journal entry, which was nicely paced with evocative imagery. However, I gave you a
B-
for practical execution. The point of these exercises is for you to attempt something you haven’t tried before. I expect you to obey this rule in the future. If you accumulate enough demerits, it will be necessary to discipline you appropriately. Sincerely, Professor Pervert.
Ah, yes, Assignment #5. That’s why I’m here in this strange pose: sitting on my bed with my back against the headboard, my legs spread wide. It’s the only position that lets me keep the butt plug in place while I diddle myself.
Naturally, I bought the beginner’s size, a flesh-colored silicone gadget about the size of my ring finger with a bulge in the middle like a swollen knuckle. The bottom flares out into a rectangular base to keep the device from slipping all the way inside. That’s what the butch-looking saleswoman at the sex store explained to me. Fortunately, buying the thing was not as embarrassing as I had feared. The woman was so nonchalant, it was like we were discussing lipstick instead of anal sex toys. That is, except at the very end when she handed me the brown paper bag and said, “Enjoy!” with a big grin as if she could see exactly what I’d be doing with my purchase before the afternoon was through. I blushed beet red and rushed out of the store.
To be honest, I probably do make as lewd a picture as anyone could imagine. I’m dressed in the scarlet waist cincher and thigh-highs I bought for Assignment #3, which only accentuate all the bare, juicy parts of me. The air brushes my exposed pussy like cool fingertips, and my nipples are standing out stiff and red. Yet I can’t say I’m all that turned on by the assignment so far. For one thing, I’m not sure I bought the right size plug. It was definitely a challenge pushing it inside me—I was poking the slippery, lubed-up thing around my butt crack for a full minute—but now that it’s there, I can hardly feel it. I’m more excited by the idea that I did this naughty thing just for the professor.
Not that he’s here to see me. Yet.
I close my eyes and take a deep breath. Suddenly the summer sunlight fades to a single green-shaded lamp glowing in the autumn dusk. I’m sitting on a leather sofa in the same slutty getup, legs open, asshole impaled on a strange little silicone bowling pin. Across from me sits the professor in a wingback chair, flanked by tall bookcases jammed with erudite tomes. With his eyes alone he issues the command:
Touch yourself, Tina
.
For me
.
My hand dips between my legs. I start to strum. My finger makes a rude clicking sound in the wet folds, and I blush, knowing he hears and sees it all.
“Are you enjoying this?” he asks, his voice as soft as a silk scarf trailing over naked flesh.
“Yes, Professor,” I admit shyly.
“Just ‘yes?’ That’s a vague answer,” he snaps. “I want you to be specific about what you find enjoyable. Is it that X-rated toy you shoved up your ass so greedily or the fact that I’m watching you masturbate?”
My throat constricts with shame, but I manage to croak out an answer. “Both, Professor.”
“Indeed? I must say I’m enjoying myself as well. But I think we’re both disappointed you bought the small one. Next time I want you to get one of the long, fat monsters that made you cringe when you saw them on the shelf. While you’re at it, get yourself a big dildo—with veins and a suction cup that sticks to a chair so you can ride it. And another one for your mouth, too. You’d like that, wouldn’t you, to be all filled up in every empty, aching hole?”