Diary of a Horny Student Ch. 29

Note: This is definitely the most fantastical chapter to date I would say, and features some rougher sex than usual, so I put it under the BDSM category. I'm sure it's pretty weak sauce for people who are into that stuff, but I wanted to make sure everyone knew what they were getting.

If it's not your thing, we'll hopefully see you back for chapter 30, and thanks for enjoying the series!

29

"Hey, Tim, are you actually gonna do some work today or are you just gonna sulk?"

I heard Gina's voice, but I didn't hear her words. It was mostly just indistinct noises and hums. I was sleepwalking my way through most things lately, trying to just keep my head down and not think about sex, love, the future, anything. It wasn't a great solution to my problems, but it was an easy one.

After that night in Kerri's garage, fucking her on the hood of her father's expensive car, only a few yards from her unsuspecting boyfriend Mike, I decided I was done. Kerri and I had an explosive affair, but I was starting to feel used. I felt used, and I felt bad. Mike was my friend, and I was fucking his girlfriend behind his back. I never thought I'd ever be the kind of person to do something like that, but at that age, it's the hormones driving the ship, not your head. I was trying to change that.

I felt used, and I felt dumb, and I didn't want to feel either, so my decision was to not feel anything at all. I stopped replying to Kerri's salacious emails, no matter how many lewd pictures she included as incentives, and just drifted into the mental ether.

No Kerri, no Christine, No Steph.

No Tara.

No point.

"TIM!" Gina shouted, finally breaking my trance.

"Huh? What, what's up?"

"Jesus, what is with you lately, dude?" she said, shoving a box of copy paper into my chest. "You've been on Mars for weeks, and I can't keep covering for you with Letty!"

My mind drifted to Letty. She was my boss, but she was also my mistress. She had been having me come in after hours for "training" in order to teach more how to be a better "employee," lately. It was a glorious torture that left my jaw and cock deliciously sore from pleasuring her, but also my balls full and blue.

She had yet allowed me to cum in her presence. She told me I couldn't until I started thinking with my head and not my dick. I so desperately wanted to, but I didn't know how. I needed guidance. I needed Letty, but even those workplace rendezvous had seemed to taper off recently. I chalked it up to just being another part of my depressing--

"Wait, covering for me? What do you mean?"

"I've been covering for you with Letty to make sure she doesn't fire your ass!" Gina said with gusto. "I love slacking as much as the next person, but you--you've just been on another planet lately, and I didn't want to see you get kicked out of here."

"Why would you do that?" I said, asking about the reason for her kindness, but also internally cursing her for denying me time with Letty.

"Because you've clearly got stuff going on, Tim, and I've...been there. Everybody needs a hand sometimes even if they won't admit it." She said with a kindness to her voice, before the edge came back and she issued a stern "now get your ass to work!" and poked me hard and headed off.

"Thanks, Gina," I said weakly, "I owe you one."

"Two, Tim--you owe me two. And it's gonna be a doozy when I finally charge that tab." she said walking off, not turning back at me.

My eyes drifted down to her plump ass swaying hypnotically beneath her slacks. I couldn't help but wonder what that debt would be. Then, in the distance of the store I saw Letty, our boss, and I began to get slightly mad. Mad that Gina's courtesy had saved me from after hours meet ups with Letty. Mad that she had denied me Letty's sweet torture.

I walked toward her. No one but me knew what she had hiding under the unflattering work outfit she wore every day. How perfect and tight her body was. How supple her tits were. How gloriously tight her pussy was. I needed it.

Crossing right in front of her, making sure she could see, I dumped the paper I was carrying all over the floor. I just kept walking, leaving the papers cast all over the tile.

Letty stopped.

"Excuse me, Mr. Miller," she said curtly.

"Hmm?" I responded dismissively.

"Are you going to pick that up?"

"What if I don't?"

Letty stared at me over the rims of her glasses.

I reached over to the nearest shelf and, without leaving her gaze, knocked a package of pens onto the floor.

"Pick that up right now, and then you will be seeing me after work for training tomo--"

"Tonight." I asserted, cutting her off.

Her piercing blue eyes stared right through me. I could tell she sensed the desperation behind my eyes.

"Tonight. Now clean it up."

"Yes, Mistress," I whispered so only she could hear. Her eyes went wide, then shifted to either side to make sure no one else was around to hear.

She straightened her shirt and continued on her way. I dropped to my knees and began doing what she asked.

A few hours later I'd find myself on my knees again, once more doing exactly as she instructed, only this time I'd be nude, rock hard, and drenched from chin to chest in the juice from her pussy.

Letty leaned back against the desk in her office, trying not to reveal how flustered she was after the orgasm I just gave her, but I could tell. The nipples on her exposed breasts were like diamonds, and the pale, smooth skin on the flat of her chest was flushed crimson. Her pussy was swollen, wide, and creamy.

I sucked the remnants of her thick, sweet juice off my fingers and felt a smirk pull at my lips. God, this woman tasted good.

Straightening herself out, Letty reached for her riding crop and placed the flat whip end under my chin.

"Stand." she said, her breath still a little shaky.

"Yes, Mistress." I said, and did as I was told.

She stood back and examined me. Unlike previous times, Letty was completely nude save for her white button down blouse, which hung open, parted to the sides by her perky breasts. She shifted her weight. Her hips rolled. My cock flexed. Her eyebrow went up.

"Tell me," she said, running the crop over my body, "why did you force my hand today? Why did you want me to punish you?"

"Because I deserve it, Mistress." I said, the thoughts of Kerri and Mike flooding back to me

"Why?"

"I was having an affair with my friend's girlfriend, Mistress. And I ended it."

"Why?" she said, taking my balls into her hand. "Didn't you enjoy your friend's girlfriend draining your balls behind his back?"

"I did, Mistress," I groaned as she rolled them back and forth, "but it was wrong. It wasn't worth it, and it needed to end before someone got really hurt."

"I see," she said, grasping my cock and stroking slowly. "So you came to me because you needed someone to fuck?"

"No, Mistress," I said truthfully, "I came to you because I felt guilty. I needed...penance."

"I see," she said, beginning to stroke me more deliberately before leaning in to whisper in my ear "I can give you penance."

A shiver went through my body.

Letty moved toward her desk, guiding me by my cock. She sat up onto the lip. Spreading her long, toned legs wide, she guided my tip to her still-dripping opening.

"Fuck me until I tell you to stop. DO NOT CUM under ANY circumstances."

"Please, Mistress," I groaned.

"That is your penance."

Another shiver ran through me.

"Yes, Mistress."

Letty's legs closed around me, pulling me, and I pushed, entering the silky embrace of my boss's wet, vice-like pussy.

We both gasped as I bottomed out inside her. Her scalding center enveloped me completely, squeezing, sheathing my hard, straining cock.

I braced myself on the edge of the desk, my legs feeling momentarily weak.

"Fuck me." she said sternly.

My eyes were closed, I was still adjusting to the amazing sensations encompassing my cock, taking in the feeling when I felt a mild slap on the side of my face. My eyes flew open.

"Fuck me," she said through lusty eyes, "or the next one will be harder."

I looked down at my boss, my cock inside her, and realized that reclined back on her desk, allowing me to fuck her was the most submissive she had ever been with me. My cock throbbed inside her. "Yes, Mistress," I gasped. I began to thrust.

Pure sensation coursed through my body as I began slipping in and out of her. She was so, so tight, but she was so, so wet.

"Yes. Fuck me." She said through wavering voice, "HARDER."

"Yes, Mistress," I groaned and began to thrust harder. The feeling of her tight pussy racing along the length of my cock was electric. I felt her heels pulling at my back, asking for even more.

"HARDER." She grabbed my hair tightly.

"Yes, Mistress," I obliged and drove harder into her. Her perky tits jiggled violently. The desk began to shake and stutter as I drove my whole body into her

"Yes," she said through gritted teeth, "yes, that's it...that's it..." Her eyes drifted shut and her tight lipped expression began to slacken and hang open.

"Fuck..." I croaked as the fire began to boil inside me. My cock was vibrating, I was sweating profusely. I could feel my orgasm beginning to rear its head. I closed my eyes.

A slap came across my face, harder this time.

"Don't you DARE cum, Mr. Miller!" Letty asserted, her crystal eyes piercing through me now. "Don't. You. DARE."

"Yes, Mistress," I croaked again. I didn't want to disappoint her, truly. I only wanted to cum if she thought I deserved it. The thought made my cock surge harder.

I gripped Letty's thighs with my arms, adjusting my angle and stability, and began to drive myself into her like a mad man.

"Yes...yes...." she groaned as I threw my whole weight into fucking her.

I cried out, the sensations inside me getting harder to deny. The spring coiling tighter and tighter.

"Yes...fuck me...fuck me..." she had never been this open with me before. Her eyes drifted closed again, her mouth went slack "Don't you cum...don't you cum..."

"I won't, Mistress, I won't." Sweat dripped off my face, splattering in droplets onto her bouncing tits.

"Don't you...don't you..." the flush on her chest returned. Her mouth hung open fully. I felt her hand tighten in my hair, and her whole body tense up. Her heels pulled me deep into her, as deep as I could go, and the walls of her molten pussy began to spasm around my desperate cock.

My desperate cock that was practically on fire. It took every ounce of my strength not to explode into this woman's amazing body, but somehow I managed to control myself.

She made no sound at first, seemingly holding every sensation in as tightly as she held my cock, until finally, a loud, expressive "UNNNHHH" echoed in the office and her whole body relaxed.

Her breath returned, heavy and quick. Her eyes opened. There was something different in her eyes; the iciness was momentarily gone, replaced with a certain euphoric glaze. Letty may have been a harsh mistress, and an icy boss, but good God she was a gorgeous woman.

"Did you cum?" she said, the words practically dripping from her lips

"No, Mistress," I said through gasps, still holding my orgasm at bay.

"Good boy, Mr. Miller," she said with a slight smirk and gently pushed me off of her.

"Thank you, Mistress." It was torture to have to leave her pussy.

"You've done everything I've asked of you, Mr. Miller. It's quite admirable." She looked down at my cock, painted with her thick, creamy cum. "And I know the state you must be in. But your penance isn't over yet."

My whole body was vibrating from how blue my balls were, but somehow I loved it. Somehow I knew I needed it.

"You did the right thing, ending your affair, but you must continue to do the right thing." She walked toward me and cupped her hand around my swollen balls. "Until further notice, these belong exclusively to me, in or out of this building. You will not empty them, alone or otherwise, until I give you permission, do you understand?"

I was too overtaken by the command to speak.

"Do you understand, Mr. Miller?" she exclaimed, squeezing my balls enough to remind me she was there

"Yes, Mistress," I yelped, "I understand."

"Good," she said, letting go of my balls and making her way toward her clothes. "You may go."

Still vibrating, I floated through getting dressed and began to make my leave.

"Tim," Letty called to me as I reached the door, "If you do as I say, it'll be worth it, trust me." there was a duskiness to those last two words that I felt in my loins. "And if you don't...I'll know."

She waved me off and I hustled to my car. I hit the gas and got home as quickly as possible, tumbled up to my bedroom and whipped out my straining cock and--

I stopped.

I wanted so badly to cum, but I also wanted to please her. I needed to prove to her, and to myself, that I had control. So I did what she instructed. There would be no cumming of any kind until she told me I could. I put my cock back into my pants, and tried to focus on anything else as I fell asleep.

***

The first few days were torture.

I felt like my balls were constantly boiling, like my skin was electric, and the faintest stimulation, visual or otherwise, would cause my cock to get ragingly erect. I didn't think I was going to be able to do what my Mistress wanted me to, but I was committed to trying my best. Then, like a cresting wave, suddenly I felt calm, more focused, and the desperate need to shoot my load receded into the back of my mind.

"You know I gotta say, I don't know what's gotten into you," I heard Gina say as she approached my table in the break room, "but you seem like a different person lately. What're you, looking for a career in office supply stacking or something?"

"No, not at all," I chuckled, "I just...re-prioritized things. Cleared my head."

"I see," Gina said, suspiciously.

I heard the click clack of stiletto heels, and all of a sudden my resolve was fading. Letty entered the break room and approached Gina and I. She was wearing the tight skirt she always wore on days when I had to stay late for "training." I felt my cock start to thicken--did this mean today was the day?

"Mr. Miller," she said, peering over her glasses at some paperwork on a clipboard, "I've been looking over your recent work these last few weeks and I have to say I am impressed. Punctuality is greatly improved, your focus has been excellent, and your overall productivity is stellar." She flashed her icy blue eyes at me over the lip of the clipboard. "Keep it up."

Oh, it was up, alright.

"Thank you M--Letty." I felt sweat on my neck as I almost blew the whole game. She started off, the click clacking of her stilettos returning, and suddenly I felt slightly panicked. "Is there anything else? Anything you...need me to do?" I said, desperately hoping for an invitation to stay late.

She paused for a moment, then shook her head with a "no, that'll be all," and continued on.

I felt my breath come back to me and my spirits dip.

"Are you ok? Gina asked.

"Yeah, I'm fine, just...want to do my best, you know?"

"Mmhmm," she hummed sarcastically. There was a silence. Gina idly picked at her coffee cake with her fork. "Hey listen, Tim...remember that favor you owe me?"

"Sure," I said, taking a sip of my coffee

"I think I'm gonna be calling it in. Tonight. If you're free."

"I seem to have nothing but time lately. What exactly is this favor?" I said inquisitively,

A smirk pulled at her lips and her eyes narrowed. "I need you to come to work with me tonight, at my other job."

"That's your favor? You need me to help you out at your other job?"

"Yes."

I tried to sigh as discreetly as possible. I was happy to help, but I wasn't exactly looking forward to spending my night cleaning rooms or...whatever else...at a retirement home.

"Yeah, no problem. Whatever you need."

"Excellent," Gina smiled, and then bounced off

I sighed for real this time. Well at least I wouldn't have to worry about being horny tonight.

***

"Hey, Shelly, this is Tim, he's gonna be helping me out tonight," Gina said to the security guard behind the desk at the main entrance to the retirement home.

"Ooh, he's a handsome one," the big, black woman offered back, "why don't you send him up here to help ME out when you're done with him?" We all laughed. I noted how her large breasts pressed against the fabric of her uniform. I felt a stir in my pants.

It seemed strange to me to just walk a total stranger into a place like this with no pushback, but I guess it wasn't the first time.

"This place doesn't seem so bad," I said, trying to make small talk as we walked the quiet halls. It was a nice-looking establishment, as nice as any retirement home could really be. There wasn't another soul in sight.

"Yeah, it's ok," Gina said, "it's an easy job and they're very good to me. Very accommodating." she waved me over to a door toward the end of a long hallway.

"This the janitor's closet?" I asked

"Not exactly." She keyed the lock and pushed open the door to reveal a fully furnished room unit. Bed, couch, kitchen, it was all there, and it was all liveable. "I work the night shift, so they let me stay here overnight whenever I want."

"Oh wow, that's pretty nice," I admired.

"Yeah, I'd rather be here than at home, honestly. At least it's quiet here. Make yourself at home while I go get ready." Gina moved off toward the back bedroom.

I wandered around idly, looking at the amenities. Quiet was right. This seemed like a cool place to hang out, but then I noticed something that seemed a little off. There was clearly a separate bedroom, as Gina had just gone into it, but the actual bed was set up right in the center of the room. And what's more, it wasn't a medical bed as I expected, but a normal bed with a rather ornate metal frame. Very odd for a retirement home. In front of the bed was a table with a computer on it. And a camera.

"Hey, what's this computer for?"

"That's what I need your help with," she called out from the back room.

"You need me for tech support? I thought you were like a janitor or something--needed me to help you clean floors."

"No, it's much more interesting than that," Gina said, walking out of the back room in a pink, silk robe. "You see, my job here is pretty easy, and I finish my rounds very quickly, so that gives me plenty of time to explore other...entrepreneurial endeavors."

She padded past me toward the computer, booting it up.

"You're an ebay seller?" I said, playing stupid.

"No, Tim," she said with an eye roll, turning back toward me. "Let's just say I'm a...performer. And I have a lot of fans who like to watch me 'perform.'" She slipped the pink robe down off her shoulders and revealed all the curves of her body hugged tightly by lacy black lingerie.

I gulped hard and took in the vision before me: plump breasts held up into beautiful, deep cleavage, belly button ring accenting a soft, flat stomach, flared hips into thick, luscious thighs, legs dipped in sheer nylon.

"So...what do you need me for?" My dumbness now less an act and more a result of being totally dubstruck by Gina's body.

"Well," She said with a slight smirk, slowly sauntering toward me, hips swaying, "I'm usually a solo performer...but I promised my fans special bonuses once I hit certain subscriber milestones...and I just hit my first one. And I thought you'd be the perfect person to help me give them what I owe."

"Oh yeah?" I choked out, "what do you owe?"

"At this milestone, I owe a special video," she dripped, moving inches from my face, "in which I suck on a real, live cock...and take a nice, big load."

"Oh my." I eked out. I could feel myself sweating. My cock strained against the fabric of my pants.