Diary of a Horny Student Ch. 26

I fished out my hard cock and began stroking.

I opened the second photo. Deep shadows cupped her thick thighs, and her camera peered deep between them at her swollen, freshly-fucked pussy. A thick rivulet of white traveled out from between her lips. Mike's cum.

My stroking stopped. I knew then exactly what I was feeling, looking at a photo of her sweet pussy dripping with another man's semen. It was jealousy.

She had sent me a picture similar to this before, but this time the thought of another man's cum pumped into her wasn't arousing, it was unnerving. I knew I had no right to feel this way, she wasn't my girlfriend, and the fact that I fucked her made me out to be the asshole, not Mike, but even so, my hormone-adled brain wouldn't let me get past the fact that he got to fuck her tonight instead of me. It was a base, unevolved jealousy that I had no idea how to deal with at the time.

My desire to jerk off had faded, but I didn't want to leave the poor girl hanging, so I gave my cock a few more strokes, made sure a thick bead of precum dripped down the tip, and snapped a photo. I sent it back to her with the caption "I'm literally drooling," and then tucked myself back into my shorts, shut my computer down for the night, and headed to bed with full balls and a heavy conscience.

Lying in bed, trying to stop the spinning thoughts long enough to fall asleep, the voices drifted down from upstairs once again. I could have sworn one of them sounded like Tara.

When I got to work Tuesday, all thoughts of Kerri, or anyone else for that matter, were gone from my mind, replaced by images of the skirt, boots, and fishnets Letty was wearing--the same ones she wore the last time I "stayed late." I was sensing a pattern. She wanted me to spend the day knowing exactly what I was in for, and each click and clack of her stilettos on the tile floor tingled my nerves.

She said nothing to me as the day went on, save for a dispassionate work request or instruction or two, and as the store began to close up for the night, each co-worker leaving the store felt like seconds ticking off a timer, with Gina's "good luck tonight" and wink signaling time had run out.

I locked the door behind her, and turned back toward the empty store. It was deathly quiet. The click clack of Letty's boots broke the silence, and I saw her lean out from her office door.

"Leave your phone at the desk." She said nothing more, disappearing back into her office. I did as I was instructed, and made my way after her.

Her office was dimly lit, and she stood, waiting for me, by the corner of her desk. She stood straight and tall, arms crossed over her chest, a long riding crop held in one hand.

Uh oh.

"Shut the door behind you and come over here."

I did as I was told and moved toward the center of the room, nervous and excited.

"Take off your shirt."

I obliged, stripping off the garment and tossing it nearby.

Letty walked over towards me slowly.

She took the flail end of the crop and ran it slowly down my cheek and neck, stopping at my chest. She took a deep breath that almost felt like excitement, but before I could calculate what the emotion was, a sharp sting spread through my body as she snapped the crop against my chest with a loud slap.

"Ah!" I shouted, and backed away, "what the fuck was that for?"

"Because I was under the impression we had an agreement about what goes on in this building Mr. Miller," she said coldly, "and when I tell you to do something, you are to do it...and answer me accordingly."

She sauntered towards me again, placing her hand on the sore impact point that was beginning to turn red. She rubbed it softly. Almost tenderly.

"Unless you no longer wish to abide by that agreement, in which case you are free to go." Her fingers felt nice as they circled my chest. "Do you wish to stay? And suffer the consequences for breaking the rules?"

She looked up at me with her ice-blue eyes, her thin, painted lips seductively slightly parted as she waited for my response.

"Yes," I began, excited and terrified for what the night would bring, "...mistress."

I thought I saw a smile try to pull at her lips ever so briefly.

"Good boy." She leaned in, and my hair stood up on end as I felt her lips kiss the sore spot on my chest, before backing away and returning to her place by the desk. Her lips--that small moment of tenderness--set my body on fire.

"Take off the rest of your clothes," she said, her eyes never leaving mine.

"Yes mistress." I did as she requested, quickly stripping off my pants, my underwear and my socks. I was left totally nude, standing in the middle of my boss' office.

Letty slowly sauntered over to me, this time carrying a length of thick ribbon.

"Hands behind your back," she commanded, and I obeyed with the correct verbal response as well. I felt her breath on the back of my neck as she wrapped the ribbon around my wrists, binding them together. After giving it a test for security, she circled me, running the end of the riding crop over my body gently, sending tingles across my bare skin. Stopping in front of me, her eyes traced their way down, coming to rest on my cock that was beginning to swell in nervous excitement.

I felt her glide the end of her riding crop up the inside of my thigh. She slid it over my balls before resting the tip firmly beneath my thickening shaft, lifting it slightly for her own inspection.

"So," she said, weighing my meat with her implement, "you think just because you have a cock like this, it means you don't have to follow the rules?"

I was flooded by nerves and hormones that I didn't even register the compliment she just paid me. I was too worried about the riding crop, one she had already used very willingly to inflict pain on me, playing around with my most sensitive area.

"No, mistress!" I blurted out, not realizing there really was no right answer.

"No, you don't have to follow the rules?" She said, her tone intensifying. "You think this cock entitles you to make trouble for everyone you work with? You think it makes you special?" I started to stumble through a response, trying to mitigate her growing ire, but a quick whoosh and a firm, stinging slap of the crop to my thigh shut me up. "Speak plainly!" she commanded.

"Yes mistress," I croaked. "I didn't mean to make trouble, I swear."

"You were neglectful, weren't you?" she said, circling the tip of the crop around my reddened skin.

"Yes, mistress!"

"You were inconsiderate, weren't you?"

"Yes, mistress!" I practically cried, before following up with "It will never happen again, mistress, I swear!"

She looked my body over once more, and then stepped back toward the end of her desk.

"On your knees." she said, her back to me.

"Yes, mistress," I obliged, and lowered to the floor. Letty kept her back to me, and I watched her intently, waiting for her next request or command. She put her crop down on her desk. I couldn't see her hands, but they seemed to be busy at the front of her shirt. It was only a moment longer before she spread the shirt wide, and slipped it down off her shoulders, sliding it off her arms, folded it, and placed it neatly on her desk. Her lithe back was wrapped in some sort of black corest or bustier, its drawstrings tied tightly in crisscrosses and bows descending her back.

I felt the blood surge to my cock.

Her hands then moved to the skirt she was wearing. Her hips cocked to the side as she unfastened it. I took a deep breath in as she unwrapped herself, revealing a perfect, pert ass that rested atop two, pale, toned legs. Her tall stiletto boots gave way to dark stockings that reached up to her mid-thigh, held in place by a black garter straps that reached up to the bottom of her corset. Her perfect ass cheeks were bare, with no fabric to speak of splitting them.

...she wasn't wearing panties.

I imagined her walking around the store all day pantiless, presenting the outward appearance of a total professional, when really beneath her sensible skirt she was prepared for debauchery. I wanted so badly to stroke my cock as it began to rise, but my hands were otherwise occupied. It was a beautiful torture.

After folding her skirt and placing it on top of her blouse, Letty picked up her riding crop and slowly turned to face me. Her body was on full display now, the corset that hugged her body accented by silver rivets that climbed up toward her breasts, breasts which were held up by the garment and pushed together in a delicious display of cleavage, despite their modest size.

As she walked back towards me my eyes fell to her swaying hips, and soon her bare pussy, accented by a tasteful tuft of hair just above the lips, was inches from my face. My mouth began to water, and my cock strained upward, hard and tight, from between my thighs. Letty's hand came down to my head, and gently ran her perfectly manicured fingers through my hair. It was tender and sweet, and did nothing to quench the thirst I was feeling.

"I'm going to use your mouth until I'm satisfied. Do you understand?"

"Yes, mistress," I yelped, desperate to give her what she wanted.

Her hand cupped the back of my head, and guided me toward the promised land.

My nose pushed into her tuft of hair, and quickly my mouth felt the warm flesh of her lips. They were warm. They were slick. They were wet. Letty's pussy was wet for me. My tongue snaked out, desperate to taste her arousal, and as the tip began to lap at her creamy nectar, I felt her stiffen up and gasp slightly.

I sighed deeply at her involuntary pleasure response. Emotion of any kind was at a premium with Letty, and this small, almost imperceptible break in her stoicism fueled me. Now, just like last time, with her hand on the back of my head, I began to kiss and lick at her swollen lips firmly and wetly. My cock strained outward almost painfully as I worked, a desperate monument to how much I wanted to please her.

Once again she made no sound, but the sharp intakes and exhales of breath through her nose told the story of her building pleasure. My tongue rolled over her pearl of a clit, undulated and pitched up, pushing into her tight, wet pussy. She tasted so sweet, so right, and I could feel her body beginning to boil as I stoked her flame.

Then for a second, and only for a second, she lost her composure, and I heard a sharp moan slip from her throat. A crack in her armor. This only intensified my efforts, wanting to capitalize on the sensation I was giving her, but a sharp tug pulled at my scalp as her tender hand turned to a tight fist around my hair, and pulled me back, disconnecting me from her sweet, commanding sex. My mouth was covered in a sheen of her juices, a long, thick strand connecting my chin to her pussy.

She pulled my hair hard, tipping my head back even further. There was a wildness to her eyes now, but she never seemed out of control. Her other hand came down to my face, gathered some of the juice smeared all over me with her thumb, and pushed it into my mouth. My lips instinctually closed around it and I began to suck, rolling my tongue around it as I did.

She didn't even have to ask.

Popping her thumb out of my mouth, I felt her hand in my hair grip hard again in readjustment. My cock flared. Looking down at me with her icy eyes, her breasts starting to heave slightly in her corset, she commanded "open your mouth and stick out your tongue."

"Yes, mistress," I gasped, and did as she asked.

Holding my head firmly, she took a step forward and pushed her wet pussy forcefully into my face, dropping her lips right onto my tongue. I felt her hand in my hair regrip again, and then her hips started to move. Thrusting. Grinding. Firm. Deliberate. the sweetness of her juices poured into my mouth as my boss began to fuck my face.

This wasn't like the last time. Last time she wanted me to give her pleasure, this time she wanted nothing more than to take it. Each hard thrust into me was accompanied by a sharp exhale through her nose as she used my mouth like a common sex toy. I should have been insulted. I should have felt degraded. The only thing I felt was extreme arousal.

I held my tongue as still as possible as she ground her clit into me. The sharp nasal exhales became faster, and I could tell she was getting close. Suddenly her hips began to tremble. She steadied herself on my face with her other hand, gripping my head tightly with both. I looked upward at the woman currently owning me, her eyes closed, lost in the sensation.

Her mouth hung open for a quick gasp, then another. Then a third. Then a moan escaped her throat as before, and I knew this was it: she was cumming.

That small display of weakness would be all I got tonight though, as she stiffened up, pursed her lips tightly, and rode out the rest of her orgasm through sharp nasal breaths.

Watching this woman cum was intoxicating. She needed to be in control at all times, even in orgasm, and something about it aroused me greatly. I saw it as a challenge. She may be the one making the rules and calling the shots, but right then and there I made it my goal to not leave for college without making her scream.

A long, deep exhale signaled the end of her pleasure, accompanying the release of the death grip on my head like some sort of hydraulic piston lowering. Her fingers loosened in my hair, and she stepped back, disconnecting herself from my sore, used jaw.

She took a moment to admire her handiwork, and it's true, I was quite a sight, I'm sure: naked, on my knees, hands tied behind my back, messed up hair, a river of saliva and pussy juice streaked down from my mouth to my pubic bone, all while my cock stood at a straining, intense attention.

Letty's eyes took in my erection, then ticked back up to mine. "Stand."

"Yes, mistress," I said, struggling to my feet. She directed me to rest myself on her desk, and after giving her the appropriate response I rested my butt on the lip of her desk. Letty's eyes went back to my cock, sticking out swollen and hard.

She ran the tip of her riding crop over my balls, and teased my length up and down. "That looks uncomfortable," she said with an almost imperceptible smirk, "is that for me?"

"Yes, mistress," I gasped, "all for you."

"I see," she said, echoing her words from last time.

Letty stepped towards me, and sidled up to me close. I wasn't sure what to do--she pressed her body into mine in a way she never had before. It was almost romantic.

One hand drifted down and cupped my full balls. I let out a deep, pleasureful exhale; her hand felt euphoric on my desperate, swollen stones.

"Are these for me too?" she said, rolling them around in her fingers.

"Yes, mistress."

"Have you emptied them since the last time we were together?"

"Yes, mistress."

Her hand slid up, and I let out an involuntary moan when I felt her long fingers wrap around my shaft. She squeezed firmly, testing my hardness. I held my breath. And then her hand began to slowly stroke along my length.

"Oh my god," I whispered as she began jerking me off at a painstakingly slow pace.

"Was it by yourself? Or with a lover?"

"B-both, mistress," I stuttered, the sensations she was sending through my body putting me in almost a trance-like state.

"I see," she said in an uncharacteristically syrupy tone, "who was she?"

"My friend's...girlfriend." I barely got the words out. I don't know why I told her that, but clearly her hand on my cock was better than any truth serum.

"How very naughty of you," she dripped, stroking me still, "did you fuck her?"

"Yes, mistress," I said, beginning to shake.

"And where did she take your seed?" Her hand was sending me careening toward the edge. I could feel her hard nipples pressed into my arm.

"Inside her," I choked out, barely hanging on, "and...and..." images of Kerri flashed in my mind. "...on her face."

"Did you like it?" She whispered deep into my soul, "did you like fucking your friend's girlfriend?" her hand sped up, driving me, pulling me. "Did you like it when she emptied your balls in her pussy and on her face?"

My body began to vibrate. Thick precum began to drip down my shaft and over Letty's fingers. I felt the well inside me bubble and start to rush toward the surface.

"Y-yes, mistress!"

"Then you don't need me to make you cum, then, do you?" She said with the icy, authoritarian tone she had when I arrived, disappearing her hand from my throbbing cock and shifting her body away from me just as I was about to explode.

My hands were tied behind my back. There was no possible way for me to finish myself off. I almost screamed.

"Please, mistress--PLEASE!" I cried, but Letty said nothing. She picked up her skirt and began to put it back on as I huffed and heaved in denial of my orgasm. She then followed suit with her blouse, silently buttoning it up as my breath began to calm down.

Letty moved to the chair behind her desk, sat, and began looking at documents and papers as I stood there naked and wet, huffing breath, my hands still tied behind my back. It began to dawn on me that this really was it. She was not going to give me any release.

This was so much worse than last time.

I stood there, my body cooling down, my arousal giving way to self conscious awkwardness. My cock began to deflate, and soon hung flaccid between my legs. Looking up at my soft member, Letty finally reached over, pulled the ribbon around my wrists and untied me.

"Put your clothes back on." She said dispassionately, going back to her papers, "clean up the floor and then you may leave."

"Y-yes mistress," I said in a daze. I stumbled my way into my clothes, then wiped up the bodily fluids we had spilt on the floor.

I stood in silence, waiting for her to acknowledge me. Finally, she looked up at me, almost as though she had forgotten I was even there.

"Well go then!" she said with a shooing motion, then went back to her papers.

"Yes, mistress," I said quietly, turning for the door. I needed to get to the car immediately. I needed to finish the job, and I didn't think I could make it home first.

"And Tim?" She called to me. I turned back and looked at those icy blue eyes once more. "I better not catch you pleasuring yourself in the parking lot on my way out."

"Yes, mistress," I groaned once more and made my way out of Letty's office.

I replayed the events in my mind at light speed as I walked toward the exit of the building. I couldn't believe the crashing waves of pleasure, pain, and frustration she sent through me, all at once. My body was still vibrating. I thought about her pussy on my tongue, her fingers on my cock...and then something gave me pause.

I was too shattered to take stock of it at the time, but now I remembered that when she turned away from me, after she took her hand off of me...she raised it up to her mouth and licked her fingers. She didn't want me to see it, but I knew what she had done: she licked my precum off of her fingers.

I felt the blood start to surge back to my cock. I needed to get out of there fast.

Hustling to the car, I peeled out of the parking lot, and headed to the nearest secluded place I could think of--The Spot. The vibrations of the drive, and the thoughts of Letty licking my precum off her hand, sent my cock skyrocketing back to hardness. I parked in a dark, isolated section of the Spot and practically tore my pants open.

I was hard as iron, but I needed something to put me over the edge, so I pulled out my phone and scrolled through one of the many images I took of Kerri covered in my semen. They were undeniably hot, but something kept me scrolling past them until I landed on a video.

I hit play, and started desperately stroking my painfully hard cock as moving images lit up my screen. Images of my cock appearing and disappearing between the soft pillowy lips of Steph. I stroked along in time, my eyes locked on hers, and pretty soon I heard my past self prepare her for what was coming next. I watched her pull her lips off my slick cock and command "Do it, baby, cum for me -- I want it all over me!"