Gay Virgin Teachers Pet Blackmailed

(All characters are above the age of 18.)

It was summer vacation, but I was stuck on the college campus for summer classes. Out of boredom, when one of my floor mates offered me some weed, I said why not and lit the joint in the common area. It's not like anyone was left during summer break, and I had only seen Caleb, a super attractive graduate student who was also the dorm manager, like twice the entire year.

Except now it was 3, because he stood right in front of me! When did he get here? I hadn't even started smoking yet.

Click. He took a picture of me! "I'll be reporting this. You should know we have a strict no drugs policy in the dorms."

"Wait!!" I jumped up trying to reach his phone, which he easily held high above my reach. I inadvertently pressed my body against his trying to reach his phone. Too bad he had quick reflexes. I pulled back. "I'm a really good student. I swear this is the first time I've ever tried something like this. I'm a straight A student, I'm going to be valedictorian of my class, and I can't get into a top 10 law school if I'm on academic probation because of drugs! If anyone, you should go bust James. He's the one who's passing them out like candy."

"Who's James?" Caleb asked.

"He lives at the end of the hall."

"Well I caught you, not him."

The one time in my life I thought I would try something everyone does, I get caught! I felt my bottom lip start to tremble.

"Tommy, calm down." He put his hand on my shoulder.

"How do you know my name?"

"You're one of the students in my dorm."

"You didn't know James," I pointed out.

He blushed. "Well, you're prettier."

This hot grad student thinks I'm pretty? "Pretty enough to be let off with a spanking and a warning?" I batted my eyelashes at him.

His eyes darkened. "Don't tempt me."

"Caleb, please, I'll do anything! Well, not anything anything, um..." That came out wrong! I was still a virgin with not a lot of sexual experience after all. "Maybe I can help you with something as a favor? Oh! Aren't you the teaching assistant for one of my classes? I guess you're kinda everywhere I am this summer. What if I helped you out in that class or something?"

He seemed to mull it over then smirked. "Fine. I have your cell from the dorm registry. I'll text you instructions the night before."

.......

Caleb: Sit at the front, in front of my desk during lecture tomorrow.

Caleb: That is if you want to be a good student and get into law school.

Okay, that didn't seem like such a big deal. Was he going have me assist him if I'm closer to him?

I told my friends I usually sit with in that lecture that I forgot my contacts so I was going to sit up front today.

I sat at the very left corner of the front row, across from the set up table the teaching assistant - that would be Caleb - sits at. There was only a wall to my left and the rows were curved, so the person to my right would have to look behind to see me. Plus, I was hopeful only nerds sat in the front so the guy seated a few seats down would probably be intently watching the professor. In a large auditorium of over a thousand students at a state school, no one would notice me there.

Caleb arrived a few minutes later.

Caleb: Good boy.

Me: I'm not a dog!

Caleb: If anything, you're a cute, frisky kitty.

Me: Do you need help with anything today?

Caleb: I'll let you know when I want you to do something.

He didn't ask me to do anything at all. I just sat across from him, he looked at me and smiled sometimes, and that was it. It was kind of weird.

......

The second lecture was weirder.

Caleb: Paint your nails the same green as your eyes.

I often painted my nails bright colors. I sat up front again with my favorite green polish.

In class, Caleb: You're looking very cute today.

......

He continued to text his commands the night before each class, but they weren't things that would seem to help him or accomplish anything.

Caleb: Bring a lollipop to suck tomorrow.

In class, Caleb: Ugh. You're sweeter than any candy.

.....

Caleb: Wear that stuff on your lips that make them pink and shiny.

In class, Caleb: Stop licking your lips. I can't focus on grading papers.

Me: I'm not! And if you can't focus, let me sit in the back with my friends.

Caleb: Hmmm, no.

It was annoying but not horrible. I mostly ignored him during class, though I could feel him watching me for the entire hour. It sometimes gave me butterflies in my stomach and I liked seeing his reactions. It's not like I looked forward to it or anything. The summer session was halfway over anyways. I could make it a bit more.

.......

Caleb: Wear a loose shirt.

He texted me an order for the first time during lecture.

Caleb: Slip your shirt off of one shoulder.

I paused. This was new.

Me: I'm not stripping in class!

Caleb: Is that an invitation for after class?

Me: Omg no!!!

Caleb: Just the shoulder.

I looked around and casually slipped my shirt off my left shoulder. I could feel his eyes on me like a heated caress. I brushed a finger down my neck and across my exposed shoulder. His eyes tracked my every movement. Mmmh. I'd never admit it out loud, but I was looking forward to him looking at me each day.

......

Caleb: Wear a black mesh tank top.

I did have one of those, but I only wore it to go clubbing, and it was way too revealing for lecture.

Me: No.

Caleb: Okay.

Me: Thank you... I thought you were serious for a second.

Caleb: No need to thank me. I'm writing an email to the Dean's office with some photo attachments now.

Me: No wait!

Caleb:?

Me: Okay... see you tomorrow.

I wore jeans and a sweatshirt and walked down the left aisle, focused on the ground, when my friends yelled to ask when I'm going to sit with them again.

"Oh uh, I want to focus a little more, so I'm going to sit in the front from now on."

They said they wouldn't join - thank goodness - but commented about what a good student I am. If only.

I hurried and the roughness of the sweatshirt rubbed against my nipples, which was one of my sensitive areas.

When I made it to the bottom, Caleb looked up and frowned at me. My phone buzzed.

Caleb: What are you wearing? That's not what we discussed.

By discussed he means he ordered.

I lifted the hem of my sweatshirt to show I was wearing the black mesh top underneath. Even with the sweatshirt on, I felt naughty. I sat down, feeling warm.

Caleb: Don't hide from me. Take off your sweatshirt. And because you tried to do a work around, make your nipples hard.

What am I supposed to do? Rub them in the middle of class!?

I lifted the sweatshirt off me and tried to sit confidently, hiding my embarrassment. For some reason, I think he enjoyed playing with me just as much as the things he made me do. His predatory grin grew.

Caleb: Hmm your nipples are already hard and begging.

I looked down. The revealing mesh fit right against my body, leaving little to the imagination. I was thin but fit. My abs clenched and my nipples, which I enjoyed stimulating regularly were exposed and peaked.

Me: It's the AC!

He just chuckled.

Caleb: I could get used to this view.

He's taunting me now.

I tried to cross my arms and cover up with my notebook.

Caleb: No hiding.

He gave me a hard look filled with heat, roaming my chest and abdomen.

I settled back in my seat. Class started and I tried to take notes, but my attention kept being pulled back to Caleb. His eyes were glued to me the whole time. He was getting so much enjoyment from staring between my puckered nipples and my probably red face. I tried to keep my breathing even. This could not be happening to me. Some of the nearby students must notice my unprofessional attire, and if they bothered to look more, they'd see my obviously hard nipples too. I felt bare and exposed. I closed my eyes, trying to shut out the world. When I opened my eyes back up, I found Caleb staring right through me, he had an eyebrow quirked.

Caleb: You like this.

It felt like a shock to my body. Of course I didn't, did I?

Caleb: You're not even denying it.

My breath caught. No way. I think my eyes widened, and his eyes were aflame.

Me: No, of course I don't.

Caleb: Are you hard?

I froze.

Caleb: Show me.

My mouth actually dropped open.

He laughed. The professor looked at him, and he smiled apologetically.

Caleb: I'll save that for next time.

......

Why is Caleb texting me on a Friday night? There's no lecture tomorrow.

Caleb: No masturbating over the weekend.

As if! He'd never know.

I arrive earlier than usual to Monday morning lecture, which was a mistake. There's almost no students here yet.

Caleb walks up to my desk. "Up. Follow me."

Um, okay? We exit the lecture hall from the door near by usual seat and enter the small work room used for office hours across the hall.

Caleb locks the door and crowds me against it. "You didn't follow my instructions."

I opened my mouth to reply but he cut me off- "Don't lie to me."

"How do you know?"

"You're way too relaxed. And now you'll get those spankings you asked for."

He's kidding right?

Caleb sat on a leather sofa in the corner and told me to unzip my khakis and lay across him. Hell no. I reached for the door when he sighed and took out his phone, threatening me silently with reporting me.

Fine! I did as he said. It was kind of awkward but the sofa made it so at least I wasn't dangling.

Without warning, he shoved my pants down to my thighs and groaned. "You're wearing a jockstrap?"

I squirmed, "Um yeah, it makes me feel good."

He lifted a strap and let it snap back! I yelped. He held me down.

He caressed one globe then the other firmly with his big hands. "Do you wear other things like pretty panties on this gorgeous bubble butt of yours?"

Yes, yes, I did. I had a whole assortment of them, but he couldn't know. I just wiggled, uncomfortable.

"Mhmmm I'll take that as a yes and keep it mind."

He rubbed and jiggled my ass cheeks to his pleasure then swat! Oh, I thought spanking would hurt, and it did sting a little, but it also shot electricity straight to my dick and hole. Smack smack smack! "Oohhh," I groaned.

His legs were spread wide at first but then he brought his legs together, which sandwiched my now hard on. I could feel his large cock against my hip. I thrust my hips against him, the friction was good.

He spanked my other ass cheek, evening it out.

"Your cheeks are already bright pink, just a little more until they're reddened and ready."

Ready for what? He spanked me thoroughly. Each hit rubbing my hard on against him. In between, he would rub circles over the spots or grip and bounce my butt. I moaned and moaned. Electricity was shooting to my groin and ass. I really wish I had something filling it. Any of my dildos would be so good right now. Or, Caleb's cock?

As if reading my mind, he pulled my cheeks apart, and I could feel his gaze on my hole. I clenched my hole reflexively. He grunted. "You're such a sexy little thing. Wink at me again." I think my face matched my ass cheeks at the moment. I did it again.

"Good boy." His next hit landed right on my hole.

"Ahh!!" I choked and almost came.

He rubbed his fingers around it, teasing. I rocked my hips. I turned my head to look him in the eyes. "Are you going to..."

His cock jerked against me. "You look gorgeous debauched. You're ready." He pulled my pants back up. I hissed as the fabric brushed over my tender ass.

"Time for class."

"Huh?" He was done? He was going to leave me like this?

Lecture was torture. My sore bottom couldn't keep comfortable in any position, but the discomfort only turned me on more. My dick was like steel, and my hole kept clenching, searching for relief that was not available.

Caleb doesn't tell me to do anything for most of class. His eyes flick towards me every once in a while, but he's mostly focused on his work as the professor lectures. Why did he make me like this if he's not going to... I mean, I don't want him to... ugh, but I do! I didn't know what a turn on that'd be.

The next time he looks over, I'm squirming. My phone finally buzzes.

Caleb: We're going to see how naughty you can be.

Caleb: Lean back in your seat right on those red ass cheeks.

i do as he says.

Caleb: Spread your legs.

Caleb: More.

Caleb: Damn. You drive me crazy.

He does the same to me!

But I need more. His hand has been under his desk for the past few texts. I can't see under his desk, but it looks like he's adjusting himself. Or maybe squeezing his dick, so he doesn't come! Honestly, I'm so close.

Caleb: Put your hand on your knee. We're going to pretend it's mine.

Oh wow.

Caleb: Rub circles on your leg lightly. Like how I rubbed around your tight hole.

Caleb has a bead of sweat above his brow. Was this affecting him as much as me? I have his undivided attention. Though I'm being blackmailed and ordered around, I feel so powerful. This is fun!

Caleb: Move to your inner thigh.

Caleb: Inch up slowly.

Caleb: Slower! Don't get ahead of me.

Ugh, I looked up.

Caleb: Your pleading eyes will be my undoing.

I sucked a breath in.

Caleb: Inch up more.

I spread my legs wider. I really needed to touch myself. I didn't even care who sees. I just needed.

Caleb: Okay, start by brushing over your cockhead, beautiful. Smear the precome I know you're dripping.

Yes! Just as I started to move my hand again, the bell rang. Everyone starting moving at once, and I snapped back to reality. No no no what was I doing? I'm so horny right now though.

Caleb clenched his jaw and looked away, glaring at the clock. He looked back at me and mouthed, "Tomorrow."

When I got home, I rubbed rubbed rubbed myself until I came. Then I rubbed some more and came again.

......

Caleb: I dropped a package in front of your dorm room. Put that in you before class tomorrow and wear your favorite panties. And choose dark pants.

I knew not to argue like last time but...

Oh, I was expecting a large butt plug but this was just the size of a finger. It actually looked pretty tame.

The next day, I inserted the little device and wore my favorite lacy baby blue panties with little bows. Oh, it settled right against my prostate. It was kind of nice to have something in me, though it wasn't filling me up. I put a bounce in my step walking to class to feel it rub against me more. No one knew, and it was freeing. I didn't realize it'd be such a turn on to have something in me in public.

Once I sat down in class, I didn't get it. I mean it was nice to feel something against my core, but it really wasn't doing much for me.

Caleb was watching me as usual as I started taking notes.

A few minutes went by, and buzz! I jumped in my seat and yelped! People looked at me and I blushed. A soft vibration started in me. Wait, was the little device a... prostate vibrator? I clenched my legs more. Ohh! I smiled at Caleb. He had his phone out and was pushing buttons. The vibrations changed in speed and duration every once in a while. Mhmmm. I squirmed in my seat. My hard on was uncomfortable in my pants as I felt my orgasm building. He kept changing the intensity. I was building building building. I looked around no one seems to noticed. I can't believe Caleb tricked me into this! But I didn't want to stop. It felt good. I reached down and tried to subtlety rub my dick. Caleb's eyes darkened. I pulled my hand away. Maybe people won't suspect if both of my hands are above the table. I slightly rocked my hips back and forth. So good. He increased the vibrations a level. Stuttered pulsations followed by a stronger long vibration set me off! I bit my lip to hold sound in. A full body shudder overtook me. My cum squirted in my panties.

I orgasmed in class! And I'd never come hands free before! I tried not to make my breathlessness obvious. That was crazy. I loved it.

I texted first.

Me: That was... hot!

Caleb: Put your phone down before you drop it.

Oh um, okay, I was a little hurt. I guess he didn't want to talk.

I placed my phone back on my desk. The vibrator started up again. Oh! He was going to keep going? Oh, I liked this idea!

I was a little sensitive from my orgasm, so he went slow. He built me up again, but then stopped. Huh? I pouted, and he started up again, his eyes bright. He chose really good settings. Always keeping me on my toes. I didn't know what sort of rhythm would come next and that made it more intense. My dick hardened again. He built me up again, and I was close but he slowed to a vibration that wasn't enough. I think I whimpered. I tried to cover my face with my hand casually. I was afraid the guy like 6 seats down would notice something was going on from my facial expressions. Caleb still kept it on the teasing setting, but I needed more. This part of the lecture hall was less busy. Hopefully no one would know, but the thought of getting caught excited me too. No one wanted to sit towards the front or in front of the teaching assistant, who now held my pleasure at his fingertips. I humped back against my seat.

I looked around me, one guy sitting farther away diagonally from me kind of watched me intrigued. Did he know what I was doing? Heat raced up my spine and down into my belly.

The vibrations stopped. I tried to wiggle it against my prostate, but it was so different without the vibrations. My eyes searched for Caleb.

When I looked up at him, his eyes were feral. He held my gaze and set a punishing rhythm. Yeeeess. My head fell back. I was getting weak and my neck wasn't strong enough to hold me up. I rested my head on my hand, elbow on the desk. My unfocused eyes were on Caleb who was soaking in every one of my reactions. My other hand worked hard on over my pants furiously.

My thoughts wandered. Mhmm I just knew Caleb's hard cock was pressed against the zipper of his pants, probably indented by it like mine. And his is bigger than mine, plump and hard. Ah I bet he would take my virgin ass so good. My breathe stuttered.

He slowed down again, and I jerked my legs. Let me come dammit it! His eyes seemed to be glowing even more, on fire. He started again and stopped right when I got close. I was losing it. He brought me to the edge again and again. I was melting!

"Caleb," I shivered. He jerked. One more time he brought me high, paused, then pushed me over. I made a choked sound. Bliss! This is what bliss feels like. I rubbed through my orgasm which seemed to last a long time. I fell back against my seat. Now I understood why he told me to choose dark pants, so when I came in my pants, the wet spots won't be so obvious.

Caleb's eyes were lidded, and he was breathing hard. He lifted his phone up like some kind of commander and pressed buttons on his phone again. Oh no. My hand went to my ass to what? Try to remove the vibrator in the middle of class? He shook his head with an evil grin.

I was so sensitive at this point, his quick hard vibrations were too much. My legs spasmed and I had to clench my hands on the edge the of the desk. He went hard and relentlessly. My soft dick jerked, making a valiant effort to plump back up, but I was spent. Still, my orgasm built so fast, I didn't even know how quickly I could orgasm, when he used a higher level he hadn't yet and omg! I orgasmed again and felt it all over my body! I bit my hand to muffle my moans. Was that a prostate orgasm? Damn.

I was sweating and panting. I didn't know what I looked like or if others could notice in the slightly dim lecture hall the pleasure erupting from my body. He didn't even turn down the vibrations from that level. He kept going. Through my orgasm. Past my orgasm. It was too much. It almost hurt, but it still felt good.