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The Making of a Girl [M40M18] [Feminization] [Age Gap]
Author Summary
CuffsAndCufflinks is a male looking for a male in Age Gap
Post Body

On Monday Jason showed up for class thirty minutes early, just like I’d told him. His face was flushed from the cold outside, and his hair was a little ruffled. It was kind of adorable, to be honest.

I could tell he was especially nervous when he walked in. His steps were so rigid and precise, his head down. I usually found his nervous, awkwardness appealing, but I could tell something was on his mind today.

“Good morning, Jason,” I said. “Come on in.”

“Good morning, Sir,” he said meekly.

He came to stand beside my desk. I sat back in my chair and looked up at him.

“How are you feeling about the exam today,” I asked.

“I … uh …”

“Don’t worry about it. After all the extra work we put in over the weekend, I’m confident you’ll pass with flying colors.”

“Thank you, Sir.”

I laughed. “You’re very welcome. I really enjoyed the chance to work with such an … eager student.”

His face turned bright pink, and this time I knew it wasn’t from the cold.

“Say it,” I said.

“Sir?”

“You’ve got something on your mind. Say it.”

“Well … “ he hesitated. “It’s not so much something to say as it is a question …”

“Go on.”

“The other day when you … I mean, when we …”

I started to get an idea where this was going and had to fight to keep from smiling. “When I was fucking your ass?” I interjected.

He flinched at the abruptness of my question, which was good. I needed him to acclimate to the realities of the situation if I was going to get him where I wanted him.

“Uh … yea, Sir. During … did …” he was stuttering so hard. The poor kid was so nervous. “Did you call me a girl?” He finally blurted out.

I did smile then. I was excited to be having this conversation. It was an important step for us. I wanted to hear him say it again. “What?”

“Did you … I mean … I thought I heard you call me a … ‘good girl’”

I stood and stepped closer to him. “Mhm. Does that bother you?”

He stared intensely at his feet, his hair falling forward to cover his eyes. “I uh … I don’t … I mean …”

I took another step forward so we were inches apart. I brushed his hair from his face and tucked it behind his ear. I cupped his chin in my hand and tilted his face up to look him in the eye. “I didn’t mean to upset you,” I said. “I meant it as a compliment. You’re just so pretty. You’re way too pretty to be a boy.”

He didn’t know how to take that. The confusion and shame and a bit of excitement was written all over his face.

“Is that so bad?” I asked. “Does it bother you that I think you’re pretty?”

“I uh …”

“Does the way I treat you not make you feel good?”

“No Sir … I mean, ‘Yes, Sir’ … I mean it does … Sir.”

I leaned down and spoke softly into his ear. “Did you not like having my dick I’m your ass?”

His whole body shuddered as he whispered, “I did, Sir.”

“Then what does it matter? We are both enjoying it … I certainly am enjoying you, Jason.” I took his hand and guided it to my cock so he could feel how hard he made me. “I like the way you make me cum.”

“I … I do too …”

Quietly, and deliberately I said, “Good girl.”

He didn’t respond, but when I glanced down I could see the bulge growing in his pants. His body was already beginning to respond the way I wanted it to.

“Do you like making me cum, Jason?” I asked.

“Yes, Sir,” he breathed.

“Good, because I haven’t seen you in two days and I need to cum badly and I need you to help me with that. Which actually brings us to why I had you come in early. It’s time for your exam.”

He looked up at me, his eyes wide with worry. “Sir?”

I leaned over my desk and opened the drawer, pulling a small, metal object. I held it up for Jason to see. “Do you know what this is?” I asked.

“… Yes, Professor.”

“Have you ever worn a butt plug before?”

“… No, Sir.”

“Mm. Good. This will be a good test for you. In fact, this is your final exam. You’re going to wear this plug until you make me cum.”

His eyes flickered to the clock on the wall. “No,” I said. “There’s not time now. It’ll have to be after the exam.” Panic was etched all over his face. I placed a reassuring hand against his cheek. “Don’t worry. You can do this. I have the utmost confidence that you can handle this for me … and if you do, I don’t give a damn what you put on the paper. All you have to do is sit there and look pretty for me.”

“Ok … ok, Sir.”

I smiled broadly and I could see the excitement he felt in making me happy.

“Good. Now bend over the desk and drop your pants. And hurry before the other students start showing up.”

He hesitated just a moment, but the idea of students coming in to see him taking a plug up his ass must have motivated him. He dropped pants and boxers to his thighs and leaned over the desk, pushing his ass out just a little.

I held the plug out in front of his face and said, “It’s pretty small, as plugs go, but you’re still going to want to make sure it’s good and wet.”

He understood what I meant and opened his mouth. I slid the plug into his mouth and watched him wrap his lips around it. I pulled the plug out of his mouth and a little line of drool dropped onto the desk.

“Lean over more,” I said. “Put your elbows on the desk.”

He obeyed, bending over and letting out a little gasp as I gently slid the plug into his ass.

“Good girl,” I whispered. “Now pull up your pants and take a seat.”

Jason pulled his pants up and shifted kind of awkwardly. Our timing was perfect as he was just sitting down as the students began to wander into the classroom.

It was my favorite exam I’ve ever given. Students sat quietly furiously answering questions, but I only had eyes for one. I watched as he wiggled and squirmed the entire time, just imagining how he felt having the plug move inside him.

He’d look up at me every so often, his eyes yearning for my approval. He wanted so desperately to make me happy. And I loved it. I’d give him a warm smile every time we locked eyes and gave him a reading nod. It was so sweet, the connection we shared in those quiet moments, no one else knowing what he was doing for me - both of us thinking of what he would do for me as soon as the last student left.

The minutes dragged by, but eventually the exam was over. Everyone except Jason had turned in their papers, packed up their bags, and left the room. Finally it was just him and me again.

Jason began packing up his stuff while I closed and locked the classroom door. One corner of the room was tucked away enough that no one peeking through a window could see.

I gestured for Jason to meet me there, and told him to get on his knees once he had. I wasted no time unzipping my pants and pulling out my dick. I let my cock bounce across his face and he opened his mouth and quickly wrapped his lips around my dick.

“Mmm,” I muttered. “That’s it. Suck that dick like a good girl.”

She started sucking me with enthusiasm, bobbing and turning her head, slurping on my cock. She must have spent some time anticipating having my dick in her mouth again because there was a world of difference from the last time.

I hadn’t been lying when I’d said I needed her to make me cum. I’d been dreaming of it since she left my house Saturday night. I grabbed the back of her head and started to thrust.

“Relax your throat,” I growled. I pulled her head down as I thrusted. She gagged when my dick hit her throat, but I didn’t stop. “Relax,” I said again. “I’m going to shove this dick down your throat.”

I felt her force herself to relax as I fucked her mouth. She made the gurgling, slurping noises and I felt her drool run down my balls.

God I love when they give sloppy head.

I held her head tight and slammed my cock down her throat. I held her there as I came down her throat. “Fuck … fuck … fuck …” I panted.

When I pulled my dick from her mouth she fell back, gasping for air. He coughed and a little bit of cum spat out on his lips. I ran my thumb over his lip and pushed it into his mouth. “Swallow it all,” I instructed.

He licked the cum off my thumb, looking up at me for my approval. I smiled down at him. “Excellent. You did so good. I’m proud of you.”

His eye lit up at my words. I started buckling up my pants as Jason got to his feet.

“I’ve got to start getting ready for the next class.So, you’ll have to go to the bathroom to take out the plug … or you can leave it in if you like,” I said wolfishly.

“Yes, Professor,” he said, wiping his mouth.

“When’s the exam for your last class?”

“Tomorrow,” he answered. “4pm.”

“Good. Be at my house by 7. You’ll spend the break with me. I think you’re ready for your next lesson.”

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3 weeks
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Profile updated: 19 hours ago

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a male
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a male
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20 hours ago