Instructing Emily

by Lyla Sinclair

  “Are you saying you were hot for teacher?”

  I laughed, grateful for the stress relief. “Yes.” I winced.

  “So, I spent all last night questioning my teaching methods—since an A student couldn’t earn a B in my classes—going over my tests and other students’ grades and looking up your records…when you could have just told me this yesterday?” I didn’t answer. Was he angry with me? I wasn’t sure.

  “Did you study the material last night?”

  “Yes.” I didn’t add that it had been awfully hard to study obscure art history facts when I was trying to imagine what he had in mind for me and my trench coat.

  “You know, I’ve decided it wouldn’t be fair to simply give you a second chance when the rest of the class got it right the first time.” My heart sank. “Unless we added another challenge. Do you remember that cable game show where contestants had to answer questions while being distracted in some way?”

  “Yes.” Was he going to shoot water in my face or give me electrical shocks or…?

  “I think you need to learn to overcome distraction, Emily. Lie down on the couch.” Full of excitement and trepidation, I walked over and lay down on his blue patterned sofa. He dragged the chair I’d sat on toward me until it was only inches away and sat down.

  I stopped breathing as he placed his fingers on the belt of my trench and pulled at the knot. Some days in class, I’d had such graphic daydreams about those fingers I’d come to with a damp brow and wet panties.

  When the belt was untied, he started on my buttons. I couldn’t take my eyes off his hands.

  “So, Emily…who led the Der Blaue Reiter movement?” OMG! He was going to quiz me while undressing me? I couldn’t possibly—

  “Emily?”

  Movement…movement. All I could think of was the movement of Professor Kendall’s hand on the button over my navel. Focus. It was a trick question because the movement sounded German, but the painter was Russian.

  “Wassily Kandinsky?”

  “Correct. Number two…” My coat was now completely unbuttoned. He placed a finger on my collarbone and ran it down my skin, pushing the edges of the coat aside.

  The contrast between the cool air of his office and the warmth of his digit caused a pleasure shiver to wiggle down my spine. His finger stopped at my bikini line.

  I was glad I’d worn the trench now. I’d gotten damp just thinking about him on the way over. Now the wetness was flooding my pussy and I wouldn’t have wanted to mess up his nice couch.

  “What period do megaliths date from?” he asked. He pulled my coat open and my nipples instantly hardened. All I could think of was how much I wanted those hands on my breasts. Luckily, this question wasn’t difficult.

  “The Neolithic Period,” I answered. I hoped the rest were like that.

  “Good, but perhaps I’m not challenging you enough.” Damn!

  He stood and pulled open the drawer in a wooden cabinet next to the couch. He brought out a miniature stapler and held it near my breast. Surely he wasn’t going to staple my nipples!

  “Don’t worry, it’s not loaded.” He lowered himself back into the chair. “But isn’t there something exquisite about cold steel on usually covered body parts?” He positioned the stapler so that it sandwiched one of my nipples. The chill of the metal caused me to take in a sharp breath. “Who is credited with innovating the subject matter of landscapes?” He pressed the stapler together repeatedly, causing it to nibble.

  Electricity shot through me from nipple to crotch.

  “Mmmmm…” I moaned.

  “Is that your final answer?”

  He moved the stapler to my other nipple. My clit jumped. I wanted to ask him for some attention farther south.

  “Emily?”

  “Hmm? Oh…no…um…Gi-Gi-Giorgione.” Had I developed a stutter?

  “Well done. Maybe cold metal isn’t enough of a distraction. Maybe something that feels more…natural.”

  Oh yes! A hand, a finger…dare I wish for a cock?

  He reached back into the drawer and removed a bag. He pulled plastic off something and I realized it was a thick-handled artist’s paintbrush. I watched as he popped open a tube. Was he going to paint me? But when he squirted it onto the brush, I realized it was lubricant.

  “I bought this especially for you on my way here this morning,” he said. “In case you actually wore the trench.” He stroked my nipples with the brush, smoothing away the cold of the steel. He had obviously purchased that warming kind of lubricant. “Has anyone ever told you that your breasts are perfectly symmetrical?” No one had ever told me that, but it wasn’t exactly a typical pickup line.

  “Lovely,” he said as he “painted” figure eights on my breasts and tickled my nipples with the hairs of the brush. My eyes fell closed. He trailed the brush down my stomach until it circled my bellybutton. It was the most heavenly torture. When it reached an especially sensitive spot halfway between my navel and crotch, my hips bucked upward and I made an odd sound deep in my throat. I needed more.

  “Ah…I think you’re trying to tell me something,” he said as he applied extra lube to the brush. He moved onto the couch next to me, his hip squeezed against my thigh, and my temperature increased a couple hundred degrees. I wished he’d take off some of his own clothing, but instead he grasped my right leg in one hand and moved it up to rest on his shoulder. Pulling my left leg up, he propped my calf on the back of the couch. I was spread open wide for him. My clit felt eager and vulnerable at the same time.

  He moved the paintbrush toward me so slowly, I was in agony waiting. The soft bristles paused just above my clit. I pushed my hips up—as best I could with my legs in that position—and brush finally met clit.

  The sensation was incredible.

  “Oh…God…yes!” I cried out as he swirled the gooey softness around inside my lips, tracing a line around my clit. Finally he went directly to ground zero and stroked lightly from clit to entrance, creating the most fabulous little zings. Just a bit more and I might be able to come.

  “What painter is best known for The Swing?” What? Were we still doing that? Did he really expect me to continue the test in this position while experiencing the most exquisite sensations I’d ever had?

  “Emily?”

  Apparently he did.

  “It…I don’t kn—”

  “Think.”

  Ohhhh! He’d cruelly dipped the brush into my already soaked opening. The same opening that had been dying to be filled by him for six years.

  He swirled the brush around in circles as he repeated the question. Somehow the answer came to me.

  “Fragonard!” I blurted out loudly. At this point it seemed strange to be calling out the name of some other man.

  “Fabulous. Just one more answer and you’ll have passed your first test.” He moved my leg off him and pushed the other down so my thighs were together again. My crotch moaned in bitter disappointment. “Roll over,” he said.

  After I complied he pulled the bottom of my trench coat up just high enough to expose my rear end. I couldn’t see him well now, so I wasn’t sure what he was doing.

  Suddenly he grabbed my ankles and pulled me backward until my ass was humped up over one arm of the couch.

  “What—?”

  “It’s okay. I think you and your lovely bottom will like this.” His hands caressed my butt cheeks. I relaxed into the warmth, imagining him massaging my entire body and then making love to me on his couch.

  But I was surprised when he slowly spread my cheeks apart. My little hole contracted from the unexpected cool air. Then the brush was on me again, but this time sliding from the top of the cleft of my bottom down to just below my hole and back again.

  All the muscles in the vicinity flexed. I groaned. I’d never known that area was so sensitive. He seemed to be holding me open with a thumb and forefinger while he painted with the other hand.

  “Do you like that, Emily?”

  “Yes,” I whisp
ered, surprised. “I guess I do.”

  “Okay, last question. Who led Fauvism?”

  “It was—”

  He zeroed in on my tight little hole, wiggling the gooey brush around on it as if trying to gain entrance.

  Oh… I’d had no idea how good that sort of thing would feel. The tingles shot down to my pussy and caused everything in the area to tighten and pulse. I was desperate for more from him.

  “Henri Matisse,” I said, just to get the damn test over with.

  “Excellent. You’ve passed. I have a reward for you.” I immediately felt what had to be the other end of the thick paintbrush, equally gooey, wiggling on the outside of my hole. It contracted, but surprisingly seemed to want more. My crotch throbbed, needing similar attention. I tried desperately to move my hand down to help, but the couch arm was in the way.

  “Please, I …” I had no idea what I was asking for other than some sort of release.

  As the brush handle slipped just inside my tiny hole, Professor Kendall released my cheeks and used that hand to go in from underneath and work my clit. The electrical pulses ping-ponged back and forth between my ass, where the tip of the brush was gently wiggling, and my clit, which he teased and swirled in the most phenomenal way.

  The sensations were incredible. I moaned and groaned and made little pleading noises in my throat.

  I wanted it to go on forever, yet I had to have relief. “Please let me come,” I pleaded. “Just a little faster.”

  He didn’t change the speed or rhythm at all. I was like a balloon that needed to burst. “Tell me the truth first,” he said as he wiggled both the brush and his finger.

  “Anything.” I hoped there might be an orgasm in sight if I answered correctly.

  He applied a tiny bit of extra pressure. “Have you ever had anything up your ass?”

  “No,” I said truthfully. “Never.”

  “And do you like what I’m doing now?”

  “Yes! Please!”

  He chuckled then wiggled the handle a bit faster. That almost did it. I convulsed momentarily, but he stopped and my orgasm melted away. The frustration had me on the verge of anger but this was so amazingly, fabulously miserable, how could I be angry?

  “I can’t take any more. You’re torturing me,” I whined.

  “But there are so many more exquisite tortures I could devise for you, Miss Brooks.”

  For a moment I wondered what they could be, but I couldn’t concentrate on anything else with the heat and pressure building inside me. He was taunting me with his finger again, swirling and pausing, swirling and pausing. Desperate for release, I began struggling to reposition myself so I could touch my pussy.

  “Be still,” he commanded in a low but firm voice, so I stopped moving.

  Finally he added pressure and speed on my clit while he slid the brush in and out more quickly. A jolt, more intense than the others, shot through me and I began to shudder. He swirled and prodded for less than five more seconds and my clit exploded.

  I shrieked like a madwoman as I came.

  He continued pressing there with his fingers as he wiggled the brush slightly, causing the mini-tremors to continue for at least a full minute. I realized my ass was throbbing, squeezing the tip of the brush as my orgasm slowed. Then my body went completely limp.

  Professor Kendall gently removed the paintbrush and I dragged myself forward to curl up on the couch, feeling incapacitated.

  “It seems you’ve overcome your distraction problem quite well,” he said as he stepped into the adjoining bathroom to wash the lube off his hands. “You got every answer right, under some very trying circumstances.”

  He spoke to me in a professional tone, as though we hadn’t just shared those incredibly intimate experiences. Wait— had we just shared them? Or had I simply been molested by his art supplies? I was the one lying here mostly naked. He was completely clothed. We hadn’t really shared anything. I pulled my coat closed and sat up, disappointed at his distant demeanor.

  He went to his desk and began typing while I buttoned up. “I’m sending you an email with tonight’s study materials.”

  So, that was really it? No mutual touching? No lovemaking? Not even a freaking kiss?

  The doorknob jiggled, followed by a knock. I checked my buttons and smoothed down my hair as Professor Kendall went to the door. It was a little late for other appointments, wasn’t it?

  “Hey, Mark, ready for The Cattlemen’s? I’m starving. I may go for the sixteen-ounce tonight,” Professor Bradley—the other young male professor on campus—said as he strolled in. He stopped short and looked down at me. Kendall didn’t have the decency to look uncomfortable.

  “Have we had a change of plans?” Professor Bradley asked.

  “No, I’ll meet you at the car in five minutes,” Kendall replied.

  As the other professor left, my disappointment morphed into anger. Now I knew for certain he had just planned to toy with me while waiting for his supper date.

  “Well, I guess I’ll be going,” I said, attempting to sound unaffected. I started for the door.

  “Okay, I’ll see you tomorrow night at eight,” he said. “No raincoat necessary but wear that skirt you had on the other day, if you’d like…the short one.” As I walked out, my feelings were completely jumbled. How could I be appropriately angry when there was a promise of more…well…anything with him

  tomorrow night? At the very least I’d had a monumental orgasm with his help. Oh, and I’d aced the test. I’d almost forgotten about that part.

  When he made the skirt request, I’d been torn between falling down on my knees and thanking him for inviting me back into his super-hot presence, and childishly asking, “Why don’t you ask your date Bradley to wear the skirt?” As relaxed as my muscles were that night while I lounged on my bed with my laptop, trying to study his notes, I still got a case of hammer-heart every time I thought about what was to happen the next night. Would he get naked with me this time?

  Would he make love to me? Or at least fuck me? I’d thought I was in love with him for six years, but at this point I’d take one night of hot sex if that’s all that was in the cards.

  I set my computer aside and ran my hands over my breasts, circling the nipples through my oversized t-shirt. Before I knew it, I was caressing my crotch through my sweatpants. I saw Professor Kendall’s dark eyes, heard his raspy chuckle, remembered how he dared to lube up a paintbrush and—

  I heard my roommate coming in the front door, calling my name.

  Tomorrow night would have to be soon enough.

  Chapter Two

  Okay, I really had given it some thought.

  I wasn’t a bimbo to be toyed with and told what to wear. I was about to get my master’s degree and had an impressive job waiting for me. So what was I doing walking through the same hall again in that tiny skirt and some heels he hadn’t even asked me to wear this time? I could have gone to his office in a turtleneck and slacks and said,

  “Hello, Professor. I’m here for the makeup test you promised me.” He’d probably get the message that I hadn’t appreciated his antics last time and deliver the test in a more professional manner.

  But of course, there were a couple of problems with that scenario. One was that my burning desire for him hadn’t gone away, even with his somewhat impersonal treatment of me—if you can call sticking things into another person’s orifices impersonal. The second was that he had given me a kind of kinky pleasure I hadn’t realized I was into, not to mention my best orgasm ever. Was it because it was him? Or was it the shocking acts themselves?

  Regardless, maybe being with him once more would get the jerk out of my system for good—I’d started thinking of him as a jerk when I realized he didn’t want to fuck me in his office. That still stung.

  This time, after he called out for me to enter, I found him lounging on his office couch, hands behind his head like he didn’t have a care in the world. I wished I could feel like that. My legs were going a
ll shaky at the thought of what he might have in store for me. Was he going to ask me to unzip his pants and straddle him on the couch?

  I imagined myself riding him, his hard cock sliding in and out of me at my will. That was the contact I’d yearned for forever, or so it seemed.

  “Are you ready?” he asked without a real greeting. “I cleared off a spot on the desk for you.”

  The desk? “Um…yes…I guess so,” I said. The area of the desk he pointed to was not nearly enough space for us to make love on. Disappointment settled in.

  “Then lie down there. Facedown.” I looked at him questioningly. “Just your chest and stomach,” he clarified as he stood up from the couch.

  I positioned myself chest down on his desk, my high-heeled feet on the floor, bottom sticking out toward him. He sat on the edge next to me, resting his hand on my barely skirted ass.

  “Were you glad you came yesterday, Emily?”

  I could feel the heat of his palm through my skirt and underwear. “Yes.”

  “What was better? The fact that you got a hundred on your test or the fact that I brought you to climax?”

  “You,” I said simply. I was too nervous about what he had planned for me to be eloquent.

  “That’s what I wanted to hear.” He lifted my skirt out of the way. His fingers slipped under the waistband of my panties. He slid the bikinis down slowly. I had a happy thought that he would soon be fucking me from behind. The panties stopped midthigh and stayed there.

  I’m not sure which I was aware of first, the loud whack or the stinging feeling on one of my ass cheeks. I gasped out an “Ow!” Then he repeated the motion on the other cheek. As much as it hurt, I was also aware of my clit wiggling its approval both times.

  “What was the artist Cimabue’s nickname?”

  Oh great. This was part of tonight’s tes— Ouch! He swatted my bottom again. How was I supposed to answer questions with him smacking away while my crotch egged him on with its twinges and zings?

  “Could you repeat the question, please?”

  “Sure,” he said as he delivered another swat. “You know, your ass is turning the most beautiful shade of magenta right now. I asked you about Cimabue’s nickname.”