Gay Virgin Teachers Pet Blackmailed Ch. 02

All characters are above the age of 18.

*

Caleb gave me a break for the few days I couldn't walk straight! But it didn't last long...

In class, Caleb: We're going out Friday night. Same rules apply. 11 pm The Drunk Unicorn. Wear black spandex shorts, no underwear, a neon top, studded earrings, black choker necklace, and matching black bracelets on both wrists.

I didn't have a good feeling about this... at least at school or in lecture, it was sort of supervised. I was afraid of what he'd have me do out in public.

******

I showed up at the club. It was dark with extremely loud music with a deep pulsing bass. Colorful lights flashing cut through the darkness, giving glimpses of the atmosphere. My neon yellow top glowed under the special lights.

I looked around for Caleb until I felt a gaze on the back of my neck. I looked behind me at the bar, and he held up two drinks. He looked good. He was wearing a sleeveless top that showed off his muscles and dressed in all black. Gone was the professor look. His hair was styled in an artfully slightly messy way. He looked way too good for someone I knew was going to make me suffer.

He said something, but I couldn't hear over the music, so I stepped closer. He leaned down, his lips brushing my ear, "Drink a shot. No chaser."

I did as he said, as usual. Ugh that burned my throat.

He shouted next to my ear again, "Check your phone throughout the night and be a good boy." As he spoke, his hand snaked down my front and started rubbing my dick through my spandex. I jumped back and looked around. I mean, I did notice that lots of others around us were doing more than that, but it took me by surprise.

He glared at me and grabbed again and pulled me to him by my dick! He stared into my eyes, daring me to move away again. I gulped and stood where I was. He stroked until the bulge at my front was noticeable and my cheeks were flushed. How am I supposed to walk around like this? Everyone is going to think I'm a pervert.

My phone buzzed.

Caleb: Drink another shot.

He was right there! He could've just told me that. I downed another strong burning drink. Maybe it'd give me liquid courage.

Caleb: Go pat the ass of the girl in purple down the bar.

"No!!! Why would I do that?"

"Because I said so."

I was shaking my head.

"How badly do you want to go to law school?"

UGH!

"Come right back to me afterwards."

I very hesitantly walked up to the girl and patted her behind the most gently I could. She jumped and turned around.

"S-sorry I thought you were someone else!" I lied.

She slapped me right across my face.

I apologized again and ran away. I searched for Caleb. He was laughing when I locked eyes with him.

I went back to him with a pout. "Why did you make me do that?"

"Punishment for backing away from my hand earlier."

He means for being surprised when he groped me in public? I sighed.

His hands ran down my chest and under my shirt. I almost stepped back but steeled my body to not move. He started rubbing my nipples. He thumbed them, then rolled them, then pinched them!

"How much longer are you going to grope me in public?"

"Just until they're ready." He kept stimulating my nipples. I was panting, and my cock was completely hard. I leaned against the bar to stay upright. My nipples were engorged and peaked when he finally removed his hands. Only to grab something from his pocket and go back under my shirt.

Something metal just pinched and attached to my right nipple. I jerked. "Ow!"

"Don't worry it's going to feel real good soon." He went to my left nipple, and I tried to shimmy away slightly. Caleb stared me down, and I gulped. He attached that one too. My nipples ached.

Caleb flicked them both. "Oohhh," I groaned. They were so sensitive! A mix of pain and pleasure. S'good.

Caleb sent me on my way. I walked around the club. I'd never been here before. It looked like a hole in the wall place from the outside, but it was huge on the inside. People were dressed up for a good time. Drunks laughing and couples getting dirty on the dance floor and in hidden dark corners. Sometimes someone would bump into me and rubbed against my nipple clamps, but it was so loud, no one heard my whimpers thankfully.

Caleb gave me more orders throughout the night. Drinking more. Bothering the DJ. Drinking more. Flirting with people. Dancing on the dance floor. Man, he got off on telling me what to do. But I have to say, besides the slap I could still feel on my face, I wasn't having a bad time overall. It was actually sort of fun. And the alcohol buzz was helping.

Caleb: Guy in striped shirt has been watching you for a while. Dance with him. Tease him. Make him hard. But don't let him touch you.

My eyes widened. This was a little much. I looked for Caleb who was in his same spot with an evil grin on his face.

Before I could do much else, the guy in the striped shirt approached me. He seemed nice enough. I had a good rhythm in general, and he was actually a good dancer. I brushed my hands over him, and he ran his hands over my body. I kept peeking over at Caleb who never took his eyes off me.

Striped tshirt guy's chest rubbed against mine, and I gasped noticeably. He pulled my shirt tighter across me and asked, "Are your nipples pierced? Damn, that's hot." He brushed against them, and I shouted. They were so sensitive after wearing them for so long! This guy went to town on them. Not giving me a break. The electric shocks to my dick, hole, and rest of my body were weakening my legs. I had to grip his shoulders to keep standing.

More than the objectively attractive guy in front of me, Caleb watching me entranced was really turning me on. I kind of wish I was dancing with him...

The guy in front of me probably assumed I was reacting to him and started kissing me. From the shock of it, I forgot about everything. He was a good kisser, exploring my whole mouth. I opened wider and- I was roughly jerked back.

"Hands off," Caleb glared. "He's mine."

"Sorry, man. I didn't realized he had a boyfriend."

I jumped in, "No, he's not my boyfriend!"

"Sure looks like it," hot guy said before walking away.

Caleb had pulled my back against his front, both arms wrapped around me and his head over my shoulder. I guess he did look pretty possessive.

He turned me around and crashed his lips to mine. "You don't get to kiss anyone else. You're mine." He kissed me again. "This is mine." He groped my butt. "And this is mine." He swiped across my chest. "Mine." He grabbed my hard erection poking up through the spandex. "All of you is mine." He kissed my mouth thoroughly again. I melted, until he squeezed my dick again but a little too hard. Looking me straight in my eyes, he said, "Don't forget it."

I think I forgot how to breathe. He pulled me against him and started moving us to the beat of the music. Once I got my bearings, I ran my hands up his abs and chest and wrapped my arms around his neck.

His fingers traced my pert butt cheeks and ran the length of my crack until he rubbed my hole through the spandex. I pressed up against him, trying to climb his body, and pressing my nipples against his hard body.

His hand came back up and under my spandex. He repeated the same motion. Yesss. He rubbed circles around my entrance then swiped over and over, pushing at my entrance more and more each time, until he popped a finger in. I dug my face into the nook of his neck and moaned. It moved in and out, deeper and deeper each time. He fish hooked and pulled, stretching my ring. Ah ah! His other hand caressed up and down my back, soothing me. He pulled out and before I knew it, returned with two fingers. Pumping in and out.

He was fingering me dry. "It burns, Caleb," I wiggled against him.

"Take it."

He scissored. Then searchingly twisted and OH my beloved prostate! I could feel him smiling in my hair. He knew what he was doing to me.

My legs were weak. My heart pounded louder than the bass of the music. Bodies were writhing around us. He stroked gently over my prostate, and I pushed back on his fingers wanting more. He picked up the pace and stroked faster. He nudged a leg between mine, my erection snug against his thigh and abs. I rutted, humping forward to rub against him and pushing back against his fingers.

Because he was fingering me dry, it still burned, but it burned good. He returned to my prostate, focusing on it intensely, and all discomfort turned to pleasure.

"Come for me," he commanded.

I erupted! Holding onto him for dear life.

"That's a good boy."

My legs were weak but he steered me to the bathroom and pulled me into a stall.

He roughly ripped off my top and peeled off my spandex. My come was still wet on my skin. He ran a hand over the come and my dick. He fondled me, weighing my dick in his hand, and pulled on my balls, like he was checking on his property or something.

Abruptly, he shoved me to the tiled ground, naked. I landed on my knees.

He leaned down to rip off my nipple clamps simultaneously, and I yelled from the pain of blood flow returning. He rubbed them thoroughly, and I couldn't tell if it was helping or not. Finally, they seemed to settle down a bit.

He unzipped his pants and pulled out his impressive cock. Oh he had this throbbing vein I wanted to lick.

"I can't wait any longer," he said as he held my jaw open and thrust into my open waiting mouth. He face fucked me hard. He hit my gag reflex, and I choked. This was the first cock I'd had in my mouth, but I tried to relax my throat. Tears were streaming down my face, spit down my chin. He didn't let up. He pushed in all the way. My breathing cut off, and he grinded into me for what felt like forever with deep grunts. As I started to get dizzy, he pulled back, let me take a few deep breathes and did it again. I swallowed around him, and he shouted. Pumped in and out a few more times then went deep again. I swallowed around him again, and he came, holding me in place as all his cum shot down the back of my throat.

After that was a blur, but I remembered Caleb dropped me off at my dorm room safely and tucked me into bed.

......

A few days later, Caleb: Come to my office hours 30 minutes early and freshly showered tomorrow.

I slipped into Caleb's office the next day, hoping no one saw me, and dropped my school bag next to the door.

"Undress." I slipped off my shirt and pants and put them on his desk folded. I was a little embarrassed just standing there in a pair of silky red panties.

"Did you wear those for me?"

I did think of him while putting them on but... "Um, no?"

"Mhmm." He took my clothes and threw them out of the window! We're on the third floor!

"Don't lie to me."

"What have you done? I can't walk around campus naked!!" I started towards the window, then decided against it. What if someone was able to see me naked from there?

"Don't worry, I bought you new clothes." He pointed to a bag on the couch. When I bent over to look inside, he came up behind me, grabbed my hips and rubbed his erection against my butt.

"You're going to look so good in this. It makes me very excited." He grinded some more.

I pulled out the two pieces. It was a cheerleading outfit. A pleated skirt in our school colors and a crop top. I secretly loved the outfit but didn't want him to know.

"Do you like it? I can't wait to see you in it. I've fantasized about you in something like this since the first time I saw you moving into the dorms."

He pulled back and slapped my ass cheek. I yelped! "Come on, don't keep me waiting." He palmed himself through his pants.

Caleb turned around, probably so it'd be a surprise when the whole outfit came together. "Let me know when you're ready."

It fit like a glove. I looked in the small mirror in the corner. Wow, I looked hot!

"Are you done yet?" He started to turn around.

"Wait! Don't turn around. I... I have a surprise." I shuffled through my backpack and found my to-go makeup bag. I used the eyeliner which really made my eyes pop. I added some glittery eye shadow and matching red lip color.

"Umm okay, I'm ready."

Caleb turned around excitedly and stopped dead in his tracks when he saw me. "Fuck, baby boy, you're gorgeous. You look even better than I imagined. I don't want anyone to see you like this. I'm afraid they'll steal you away from me. But you can't leave me, can you?"

I shook my head. Though, I'd almost forgotten about his blackmail in this moment.

"Turn for me."

I did a twirl for him, slowly bending over then back up, and then sucked my finger with a pop.

"Ugghh you're killing me." He pulled something out of another bag. "Lay over me like I'm going to give you a spanking," he ordered. "Don't look too eager. It's something else." I was a little disappointed.

He chuckled. "Don't worry, this will be good too. Well, at least I''m going to certainly enjoy it."

I laid down across him. I couldn't see what he was doing from that angle. He flipped my skirt up and my panties to the side. I heard the pop of lube. Oh, that was promising. He thrust a finger in me without warning. Ah! That hurt, even with the lube. "Take it, gorgeous." It felt better after a while, and he added another finger then another. I was panting by this point, my erection stiff. He widened his legs, and his arms came around under my hips. Oh yes yes! Touch me! He rubbed me through my panties, the front already wet with my precome. Then he slipped my panties to the side here too and schlick!

"Wha-what was that?" I asked in panic.

"That, gorgeous boy, is a cock ring. I especially chose it for you, and it matches your outfit."

"How long do I have to wear it?"

"Until I say so." Panic crawled up my spine, quickly distracted by his hand pumping my dick. "Keep this nice and hard for me, baby boy." I whimpered.

He returned his attention to my hole, lubing it up nicely. Then his hands were off me for a few minutes as he seemed to be opening and lubing something? While I was relaxed and distracted, he pushed something in me!

"This is your brand new butt plug. It'll keep you nice and open. Alright, you can get off me now. Get up and walk back and forth across the room. Get used to the feeling."

I felt full and achy all at once.

"I've seen you practice the cheerleading dances in the dorm hallway before. Perform for me."

Ummm, how would I do that? The room was spacious, but it was kind of awkward.

Caleb turned on music from loud speakers on his desk. "Start."

It was a little less awkward... I started the dance routines I'd learned and ah the butt plug made some of the moves difficult, not difficult per se, but uh distracting. My cock was still hard, trapped in my panties again, but I felt sexy. I teased him with peaks of it with high kicks and twirls. Caleb watched me so attentively and- oh he pulled out his cock and was stroking it! I did some more provocative moves, now making up my own versions of the routines. I ran my hands up and down my body and across my open midriff. I stuck out my tongue and winked. I shook my booty and dropped low to the ground and back up while licking my lips. Caleb was raptured, his neck muscles bulging, his hand moving so fast over his cock it was a blur.

"Lift your skirt and shake it for me." I did, and he gripped his cock tighter, stroked rougher, and came.

"Damn, baby boy-" he was cut off with a knock to the door.

"Hi Caleb! I'm a little early, but I'm here for office hours. Can I come in?" Some student said through the door.

"I need a few more minutes. We'll start on the hour," Caleb answered in a growly voice.

He approached me like a predator would his pray and reached under my clothes to pump my swollen cock. He went rough and fast. I thought for sure I would come fast, until I remembered the cock ring! Nooooo. He brought me so high, I struggled to keep my sounds in. He pleasured and pleasured me with no end in sight. "Please Caleb?"

"Damn, your eyes are big and lovely." He ignored my pleas and grabbed a pillow out of his backpack and threw it under the desk.

"Sit." I kneeled under the desk. He sat in his usual roller chair and scooted up. I ended up shadowed and in between his legs.

"What am I supposed to do here?"

"Be my cock warmer like a good boy." His desk was a big wooden one that went down all the way to the floor so no one could see me except from Caleb's side. He unzipped his pants and pulled out his cock. He grabbed the back of my head and pulled me down to him. I inhaled him, and he jerked me back. "No, just mouth my dick and keep it in your warm wet mouth."

He called in the students. Quite a few came and went, all the while Caleb answered everyone's questions as if he didn't have a care in the world. Occasionally, I'd reach down to stroke my dick, but after a while, it'd start hurting when I'd get to the point I needed to come but couldn't. Sometimes I shook the butt plug in me or slightly pushed and pulled to see what it felt like, and it felt so good! But I ran into the same problem of the pleasure building to pain and desperation. Sometimes Caleb felt it I think and petted my hair or cheek to calm me down.

I continued to be a good boy for him and keep his cock in my mouth. Sometimes I mouthed down his shaft but mostly I just kept his head and a little more in my mouth. I laid my head against his thigh. With the pillow, my knees didn't hurt. I could almost doze if I wasn't so hard!

I had been lightly sucking on his cock when one of the students started blatantly flirting with Caleb! Wait, where did all the other students go? Caleb wasn't even turning him down, just acting like he missed the student's innuendos and advances. I didn't like that one bit. I sucked harder and started bobbing my head as quietly as I could. I could feel the instant tension in Caleb's legs. His hand discreetly reached down and pulled my hair, boarding on painful. I didn't care. I bobbed deeper. He was starting to lose his composure.

"Is something wrong? Are you okay, Caleb?" The dumbass student said.

"Actually, I don't feel so well all of a sudden. I'm sorry, I'm going to have to cut office hours short."

"No problem! I hope you feel better and see you next week!" He finally left.

Caleb reached down and roughly pulled me out from under the desk. "What was that disobedience?"

"I don't know what you're talking about."

"Where did this attitude come from? I won't tolerate disrespect."

"Disrespect? You're the one flirting with another student while your cock is in my mouth!"

His grip loosened. "Are you... jealous?"

I turned bright red. "Anyways, I should get going too." As I reached the door, he blocked me against it and reached around me to lock the door.

I struggled to get free, and he threw me on the ground! His body flattened me, crushing me really. He undid his tie and used it to tie my hands above my head!

"You got what you wanted. Everyone is gone now. I was going to wait, but it looks like I need to fuck some obedience into you."

He reached under my skirt and into my panties. He started jerking me roughly. It felt so good. If this was punishment, I'll take it any day!

"Look at me." I lifted my eyes to him, my mouth was open and panting. He slapped my hole over my panties.

"Ugh!!" My body jerked. He kept rubbing my dick, but it was starting to hurt again. I couldn't come, so it kept building. I looked down. My cock was swollen, angry, and a deep red. "It's hurting. I need to come!" Caleb ignored me and kept pumping, looking between my face and dick with pleasure, back and forth. I was writhing. No position was comfortable. He finally took his hands off me. I was confused whether his stimulation was good or bad at this point. I was going crazy.

"Up. Hands on the desk."

Getting up was awkward with my hands tied, but Caleb helped me.