Diary of a Horny Student Ch. 29

"What do you think?" She said, running her fingers up and down my forearm, "do you think you can help me out?" She licked her lips for effect, the little minx.

I wanted to. So badly. I felt the word yes forming at the back of my throat as I took in Gina's palpitating cleavage. She smelled amazing.

But then I thought of Letty. I thought of what my mistress tasked me with. And how desperately I wanted to follow through on what she demanded of me.

"I..." I began, shocking myself that I was even going to say it, "...can't."

"But you owe men one, Tim," Gina said with a pout, "and I can guarantee you won't regret it."

"I can't, really." I was almost shaking.

"Are you sure?" Gina stepped back from me slightly. "You can cum wherever you want, Tim," she said, running her hands over her body, "in my mouth...on my face...on my tits..."

Her hands reached the cups of her lingerie and gently pulled them down, presenting me with two bountiful, luscious, naked breasts. Breasts I desperately wanted to squeeze and suck. Breasts that needed my cum.

"Gina, I can't tell you how much I would love to do exactly what you need me to do...but the truth is I can't. At least not right now. Maybe if in a few weeks--"

"This is a one-time offer, Tim." she said, giving her tits a slight shimmy. It was electric.

But I stayed firm (in more ways than one).

"I'm sorry, Gina. I can't."

Gina paused, staring at me, scanning me. Then with a long sigh she slipped the cups back over her tits and grabbed her robe.

"Fine, Tim," she said, dismissing me with a hand wave, "whatever you want. It's too bad, it would have been a lot of fun."

"I know," I said, my breath slowly returning to normal, "is there anything else I can help you with?"

Gina chuckled. She walked toward me one last time, and gave me a kiss on the cheek. "Goodnight, Tim. I'll see you at work on Monday."

I floated out of the room, down the hall and past Shelly at the desk, barely registering the teasing remark she sent my way as I left the building.

My cock screamed at me the whole drive home. I couldn't believe what I had just done. Or hadn't done for that matter.

Waiting for me in my inbox was a message from Kerri. A photo. Her nude body draped in the backseat of Mike's car, racing stripes of his thick, white cum stretching from her bellybutton to her lips. She was winking.

"Wanna be next?" the text read.

My cock surged again.

I closed the photo and drowned myself in the sheets of my bed.

***

I expected an intense sense of awkwardness that next week at work, but much to my surprise, Gina acted like nothing had changed at all. We still chatted, we still joked, and there was zero mention of her asking to suck my cock on camera for the internet to see.

Not that I wanted to talk about it, that is. I was more than happy to just keep my head down and focus on doing what Letty asked of me, but even though nothing had changed, something definitely had changed. Now whenever I saw the faint shuffle beneath Gina's work shirt, all I could think about was her amazing breasts, and how badly I'd love to suck, lick, or fuck them.

Head down, Tim. Head down.

The week passed without incident, and pretty soon it was Friday. That's when I heard the click clack of Letty's stilettos get louder and louder. That's when I felt the hair stand up on my neck.

"How are you, Tim?" she said cordially as she approached.

"I'm good Letty, how're you?"

There was no response, just a quick, awkward smile.

"Tim you've continued to impress me with your change in attitude as well as your commitment...but I'm going to have to ask you to stay late tonight to help me with something once again."

A chill shot down my back straight into my cock.

"Sure thing, Letty, no problem." I half choked. That quick smile returned and the click clack of her heels got quieter and quieter.

"Good news or bad news?" I heard Gina say approaching from behind.

"Uh...I'm not sure," I managed, "I gotta stay late tonight."

"Ha! Man, you just can't win, can you?" Gina said, slapping me on the back before she continued on. "Don't let her work you too hard!"

I gulped and tried to hide my erect cock as I finished the work for the day.

Closing time rolled around, and I waved to Gina, the last one to leave for the night. Excited, but throat dry, I locked the door behind her, and made my way toward Letty's office.

I stood outside, attempting to collect myself, then I knocked.

"Come in, Tim,"

I pushed open the door. Letty was waiting for me, her slim, lithe body leaned against the lip of her desk. Her white blouse was open just enough to show me the top of her tight cleavage. Her black skirt hugged her hips intimately. Long, fishnetted legs cascaded into those high, stiletto boots. There was a new addition to her outfit tonight though--a black, leather choker of some sort. A collar with a metal hook at its center.

My cock twitched hard as I took in the whole package.

"It's been quite a while since you were last here, hasn't it?" She said, straightening up and taking a confident pose in the middle of the room.

"Yes, Mistress,"

"And I gave you a task to complete didn't I?"

"Yes, Mistress."

"And did you complete it?"

"Yes, Mistress," I said, eagerness forcing itself out with the words.

She tapped the edge of the desk, and I quickly moved over to it, resting my butt on the lip.

"How do I know you're telling me the truth?" she said, circling around me to the rear of the desk. "How do I know you haven't spilled your seed since then?"

"Because I want to please you, Mistress. I wouldn't lie to you."

Letty returned to my sightline, carrying something behind her back that I couldn't see.

"I know you wouldn't," she said with a slight smirk. She gently placed the item she was carrying on the floor in front of me. It was a pillow.

Letty was inches from my face now, staring through me with her icy blue eyes. Her hand fell to my groin. I was rock hard. She felt it. She smirked again.

A knock came from the office door. I froze.

"Who is it?" Letty bellowed.

"It's Gina." Her voice hit me like a cold shower. If she caught us, we could both be in big, big trouble.

"Come in."

My eyes went wide and shot back at Letty who could only smirk. The faint creak of the door whipped my head back toward its origin, and I waited, ready to be outed by Gina.

What I wasn't ready for was to see her standing in the doorway wearing the exact same lingerie outfit she had worn that night the previous week.

"Take your place, Gina," Letty said, the hand on my cock now gesturing to the pillow before me.

Gina smiled and narrowed her smokey eyes.

"Yes, Mistress."

My stomach dropped like a ton of bricks. Gina padded into the office, her full hips swinging, her thick, beautiful cleavage bouncing slightly with each step, stopped in front of me, and lowered her knees to the pillow.

"Wait, the other night...it was a set up?" I said, bouncing my eyes back and forth between the two women

"You needed to be tested, Tim. You did as you were told. You've resisted temptation. You've refocused yourself," Letty said, running her hand across my chest. "And now it's time for your reward. You may proceed, Gina."

A wry, mischievous smile pulled at Gina's lips.

"Thank you, Mistress."

Suddenly it all made sense to me--All the times I had seen Gina waiting outside as we closed up--how could I have been so dumb as to think I was the only person Letty had ever done this with? My mind flashed to Gina on her knees, pleasing Letty the way I had...they way she was about to please me.

Her hands moved up my legs. Fingers lowering the zipper. Gently she reached inside, searching for my cock; it wasn't hard to find. Tips brushed the thick shaft, feeling it. Grasping it. Suddenly the cool air of the office passed over the sensitive skin of my revealed erection.

"Oh my," Gina cooed, taking the time to feel all its length and girth with her hands, inspecting it. "You weren't kidding, Mistress."

She wasn't kidding. Letty wasn't kidding. Letty had told Gina about my cock.

Gina grasped me firmly at the root, causing my desperate hardness to throb. She looked me in the eye, and with a soft smile that said "I'm going to enjoy this," licked her lips, opened her mouth, leaned in, and took the flared head of my cock inside.

I almost screamed.

Slowly but deliberately she began to drag her slick, pillowy lips up and down my shaft, her tongue making a delicious swirl around my tip at the apex of each stroke.

My hands tightened, fingers gripping the edge of the desk like ten tiny vices.

A steady rhythm began to develop, Gina's hair swaying gently as she continuously penetrated her warm, wet mouth with my cock. Little coos and moans vibrated their way up my shaft and into my body. I was buzzing.

"She's very good, isn't she?" Letty dripped into my ear, running a hand across my chest. All I could do was nod in agreement - she WAS very good at this. My mind wandered briefly, wondering how many cocks she had sucked to get this good at it. Had she started in high school? Had she perfected it in college? How many men had had the immense pleasure of looking down and seeing this amazing girl work magic on their cocks? How many in this very office?

I was sweating profusely. The sensations Gina sent coursing through my body were immaculate.

"Don't fight it, Tim," Letty encouraged again, "give Gina what she wants."

I moaned loudly as she took my entire length into her mouth. I felt my head slip into her throat.

"Tell him what you want, Gina."

Gina slipped my cock all the way out of her mouth for the first time since she began.

"I want your cum, Tim."

I groaned again as she enveloped me once more, slipping effortlessly back into her rhythm.

"Ae you going to give it to her, Tim?" Letty said, pressing her perky tits into my arm, "are you going to give Gina all your cum?"

"Y-yes...Mistress..." I barely croaked out

"I bet you've got a lot for her too, don't you? Stored up in those big, full balls..."

"Y-yes...Mistress..."

Gina's pace increased. My body started to shake. My mouth hung open.

"Are you going to cum, Tim? Are you going to cum for us?"

All I could do was nod. The hot coil inside me was drawing tighter and tighter. Pleasure surged through me.

Letty's hand dropped down into Gina's hair, gripping it; it was Letty who was guiding her now. Letty was facefucking Gina with my cock.

"That's it, Tim...cum for us...CUM FOR US."

I let out a loud cry and an "OH, FUCK," and the tight spring of pleasure inside me snapped.

At that very moment Gina's mouth left my cock, replaced by a hand--Letty's hand.

My eyes snapped downward: Gina sat back on her heels, eyes closed, mouth open, arms pressing her generous breasts together into bursting cleavage, as Letty jerked my cock at her face.

A millisecond later, almost a month of pent up sexual frustration unleashed itself all over my sexy co-worker.

The first rope of hot white pleasure ripped out of me in a spiral of joy, leaving a long sticky lash up Gina's cheek, over the bridge of her nose, and up into her hair.

The second came splattering onto her chin and lurching into her open mouth.

More into her mouth.

More across her face.

More splattering down her neck and onto the swell of her tits.

I lost count. My eyes closed. It felt like my whole body was racing out through the head of my cock.

"Yes...yes..." Letty encouraged, stroking me with a continuous pace, directing my juices all over her subordinate.

It felt like forever, but was probably only a matter of moments, but eventually the spurting stopped, and Letty slowed her pace. The final remnants of my cleaned out nuts dripped and ebbed over her fingers.

My breath remained deep and heavy. I opened my eyes and took in the unbelievable sight before me: my co-worker Gina, on her knees, absolutely painted from head to knees in my semen.

"Holy shit...holy shit..." was all I could manage.

Gina smiled, and pushed some of the errant strands into her mouth with her finger.

"Well done, Mr. Miller," Letty said, releasing my cock. She held her cum-streaked hand out to Gina. Gina leaned in and sucked my cum off our boss's fingers. I saw a chill of excitement run through Letty's body. "What do you say, Gina?"

"Thank you, TIm," Gina said between sucks and licks, cleaning off Letty's hand.

"Holy shit" I whispered in refrain.

Her hand now clean, Letty offered it to Gina, who took it, and rose up to her feet.

Letty let go and made her way to her desk to retrieve something.

"Can I get you like...a towel or something?" I weakly offered to Gina. I was still in a state of shock.

"No thank you," she replied with another wry smile, "not yet."

Letty returned from her desk, a long, thing leather leash in her hands. She handed it to Gina, and then opened wide the neck of her blouse.

Gina approached, and clicked the hook end of the leash into the metal fastener on the collar around her boss's neck.

I saw that chill return, but this time something was different. Something changed. It was almost as though I witnessed a transference of power. I wasn't sure exactly what I had witnessed...until Gina spoke.

"Clean me up," she said to Letty with an assertive tone I had never heard anyone use with her before.

Letty nodded her head, and then our boss, the iron-fisted taskmaster, the woman who bent my will and made me happily obey her very command as my Mistress, bent forward and began licking my cum off Gina's chest. Then her neck. Then her face.

Letty's tongue caressed Gina's cheeks, up over her nose, even her forehead, lapping my spent seed off her employee's face and into her own mouth. I watched her throat periodically pulse as she swallowed it down.

Once her face was clean, Letty stepped back, and Gina commanded "open." Letty opened her mouth wide to show she had swallowed everything, to which Gina responded "Good girl."

I was dumbfounded at the display. Everything I thought I knew about our relationships and power dynamics were now completely out the window.

"Come with us, Tim," Gina said, and made her way out of the office, Letty following obediently behind on her lead.

"Yes, ma'am," I said in disbelief, and made my way after them.

Gina led us through the warehouse, down a dark corridor I had never been down, to a door that read "Emergency Only." Pushing the door open, we walked into a dimly-lit room filled with boxes stacked high. I followed the two women down around the corner of the box maze, and was presented with a shock: before me was a queen sized bed nicely made, as well as a nearby-positioned, big, comfy chair and a similarly laid out chez lounge.

"What the fuck?" I whispered.

Gina stopped just before the bed and turned to Letty, who was in the process of removing the last of her clothes.

Flat, tight stomach, perky breasts, round, supple ass, long, toned legs. Letty's body was immaculate. She stood before me fully nude, save for her stiletto boots, and the collar and leash around her neck.

"Tell him," Gina said, giving the leash a very slight yank.

Letty turned toward me.

"Please make yourself comfortable, Tim, and enjoy what follows however you'd like. When you feel so inclined, know that my body is yours to use freely...in whatever manner you want."

Instinctively I began to respond with a "Yes, Mistress," but Gina stopped me before I could finish the word.

"No. There'll be no more of that. Not tonight.

My cock lurched inside my pants. I smiled.

A jerk of the leash sent Letty's attention back to Gina, who was reclining into the thicket of pillows on the bed. Her breasts were shiny from the remnants of my cum and Letty's saliva. Her panties were gone, and her legs butterflied open. Her pussy was wet and waiting.

Letty joined her.

"Please me with your mouth, slut," she said with relish, and gave the leash a yank. Letty fell forward face first between her legs. I saw Gina's expression soften, a smirk pulling at her lips as Letty began to lick her pussy.

I settled myself into the big comfy chair nearby and began to watch.

Gina's eyes drifted closed. She squeezed her breasts, teasing her nipples as Letty began to feast on her.

I couldn't take my eyes off her tits, off the way she pinched the nipples, how she pushed them together and moaned in delight.

Despite having just launched a sizable load onto Gina's face, I felt my cock stir--godbless 18 year old constitution.

I became mesmerized by the two women, my co-worker and our boss, and I mindlessly began rubbing my thickening cock through my pants. I couldn't help but think back to the night I watched Tara and Sarah make love. But this wasn't making love--this was fucking.

"Show Tim your pussy, slut," she moaned at our boss, "show him how wet it makes you to eat me."

Without removing her mouth from Gina's lips, Letty repositioned, sending her tight, perfect ass straight up into the air. I could see plain as day already that her lips were swollen and wide, slick with arousal. I didn't even need her to reach her hand down and spread them with her fingers the way she did.

I rubbed my cock more forcefully. My full hardness returned.

Gina caught me staring and smiled through her pleasure.

"Make me cum, slut," Gina moaned between quickening breaths, "make me cum right now or you'll be punished!"

Letty's fingers left her wetness, and I saw them dip back to join her mouth between Gina's legs. From the way Gina gasped, I could tell those fingers went directly into her pussy.

"Yes...yes..." Gina began to moan. She wrapped her fist around Letty's leash, gripping the back of Letty's head. Her hips rocked and thrust against Letty's face, mouth agape, her breath almost imperceptible. Her free hand shot up and grabbed on to the iron headboard behind her, her eyes closed, lost in the sensation of Letty's licking tongue and penetrating fingers. Her body started to vibrate and shake.

My mouth was dry and my cock was hard.

Gina had been silent, focused on the mounting pleasure, and then her quiet breath turned suddenly to deep, sucking gasps, and with a loud, sharp ejaculation of sound from her mouth, Gina began to cum.

In all my experiences so far, my favorite thing ever was to see a beautiful woman lost in orgasm, and Gina was no exception. Chin tucked deep into her bulging breasts, she held Letty's face tight to her pussy, rolling her hips hard into a slurping tongue and thrusting fingers. I could hear how wet she was.

But more than just the eroticism of Gina's orgasm, seeing my dominant boss Letty, my Mistress, get turned into a subservient slut was conflicting, yet extremely intoxicating. Watching Gina's body explode and writhe as she used Letty's face for her own pleasure, I immediately got envious. I wanted to be a part of it.

I stood up, almost instinctively, just as Gina's orgasm subsided. A satisfied smirk on her face, Gina pulled Letty's face off her pussy by her hair. Letty's face was shimmering with Gina's cum, her breath heavy.

"What do you say, slut?" Gina asked.

"Thank you, Madam." Letty gasped.

Gina looked over at me, standing at the foot of the bed, dumbfounded, not sure what my next move should be, and made the decision for me by tossing Letty's leash in my direction.

I picked it up, felt it in my hand. I followed its length up to the woman on the other end of it.

Letty sat back on her heels, her posture straight and tall, waiting. Her tits were perfect, her nipples hard as diamonds, Gina's cum streaking down her chin and neck. Her icy blue eyes stared directly at me as they had many times before, but now there was something different behind them: desire.

I thought about everything Letty had put me through this summer, at work or after work. I wrapped the lead in my hand.