tagTransgender & CrossdressersCheaters Never Prosper

Cheaters Never Prosper


"You wanted to see me, Mr. Blake?

I looked up at James Anderson with a hint of anger flaring in my eyes causing him to look down at his feet and take a step back from my desk. He was a smart kid but apparently math was more his thing as he was failing my twelfth grade English class. The boy was slight and pale skinned with fine, delicate features. He often wore a hoodie to conceal his long, blond hair and androgynous body. I'd watched him since he came into high school and seen how badly he got teased and bullied by the alpha males and their pack though I found it hard to be sympathetic after what he'd tried to pull on me.

I had been a bit of a troublemaker when I was young so I knew enough of the tricks kids used and had my own countermeasures in place, like test answer keys with wrong answer hidden in my desk. And James' test perfectly matched the false test. I knew he was under pressure from his parents to do perfectly to get into some Ivy League school his family all went to and he was close to failing my class. But I hadn't expected cheating from the likes of him and that he hadn't even bothered to try to answer one question different from the false answer key was a slap in the face.

"Do you think me an idiot," I growled. I found most teens were used to teachers being polite and disinterested so any anger or enthusiasm threw their young minds. "I expect better from the likes of you, James." I pulled out his test and slammed it down on top of my desk, making him jump.

He looked down at the paper and his eyes widened as he saw the big, red 'F' across the page. The play of confusion and emotion over his face was precious and it was hard not to laugh as I sat there. "I... I don't understand," he stammered.

"I don't understand how you could be so arrogant that you'd put every false answer down from my decoy test key without trying to hide things. Did you think I wouldn't be suspicious if you did get a hundred percent after nearly failing every one, you arrogant little shit?"

His eyes were wide with realization as he glanced up at me before letting his gaze drop back to the table. "I didn't... I don't... please Mr. Blake." He wanted to deny it but he was trapped by his own conceit. "I didn't think you stupid."

I had to resist smiling at that one and the boy's obvious fear, all his intelligence just thrown out the window as he stood in the spotlight. I slowly stood up and walked around my desk, letting my shoes slap loudly on the tile floor, pausing to close the open door to the classroom, the sound of children slamming their locker and heading for their buses silenced finally. It left us in the quiet hush of the room which I could see was wearing on the young man.

"Now, I've not taken this to the principal yet," I started, emphasizing the yet part. "But this is a serious matter, I hope you understand the gravity of the situation, James. If this goes onto your record, you get expelled, you'll be lucky to get into community college. But, there is always the Vocational Technical School, electricians and nurses are quite in demand." I walked over to the boy and settled a hand on his shoulder, the muscles so tight I thought he might snap.

"Please, sir,it won't happen again," he pleaded, daring to glance over at me with his liquid blue eyes. I saw the desperation and fear I'd been hoping for since the boy decided to step into my sights. "I'll do better... I'll do anything... just give me a chance."

I walked behind him and moved to the door that lead into the walk in storage closet letting the door swing open slowly as I turned back to James. I felt a tingle of nervousness as I realized we were at the point of no return and the young man could cause trouble if I wasn't careful. "I want to believe you, James, but your actions have shown me I cannot trust you. So, you need to prove yourself. I'm going to order you to do some things. Refuse, and I take this paper to the principal and you watch your life flushed down the toilet. And don't question, it's as good as a refusal. Do you understand?"


The hint of hope mixed with a smattering of trepidation showed in the boy's features but his sad voice almost made me want to go easier on him. But, then i remembered what he tried to pull one and how little he must think of me and my sympathy evaporated. "First and last chance, in here there's a school uniform from an old school, put everything that's in the box on."

He walked over and looked at the contents before glaring back at me with wide eyes. "But, that's a girls uniform. I can't..."

"First and last chance," I repeated. "I didn't say it would be easy or pleasant." I left him there in the closet to walk back over to the door and lock it quietly, pulling down the small shade over the window. Then, I dimmed the light a little and sat down in my chair behind the desk. After a little while, James tentatively stepped out of the closet, a bright red blush on his pale skin.

He wore a simple white blouse that hung loosely on his slim frame. A pleated blue skirt billowing around his hips and upper thighs was short enough I could see the hint of the pink panties he wore underneath. A pair of gray thigh high socks clung to his lovely legs ending in the black loafers with three inch block heels. His blonde hair was past shoulder length and with it ruffled taking off his clothes and putting on the blouse, it already gave him a feminine appearance. The delicate lines of his face made him seem almost like a porcelain doll standing there.

Motioning him over, I reached into the bottom draw of my desk and pulled out a few things. Taking his chin firmly in my hand, I brushed a little red onto his cheeks to give them a little high light. Then, I opened a tube of pink lipstick and started to apply it to his lovely lips but he balked though a hard stare quieted him so I could finish applying it. Finally, I grabbed a pair of white lace gloves and slipped them on to cover his hands since there was nothing we could do with them today. Sitting there, I ran my fingers through his hair to fluff it up a little and give it a bit more body, finally leaning back to admire how pretty he was standing there with me.

His bright blue eyes were on me as I rose suddenly so I towered over him, my hands falling to his shoulders. "Ok, Jamie," I said, smiling at his new name. "It's time to earn my favor back and we can see about maybe getting you a passing grade eventually." With my fingers curled around his shoulders, I pushed him down to his knees before he knew what was happening. There was something erotic and taboo about seeing him there all dolled up on his knees, the confused look on his face as he stared at my crotch for a moment.

"I don't understand," he said, his voice almost a whisper. He looked up at me with wide eyes and a terrified expression but I know it was fear of accepting what was in his heart. I'd seen enough to know he wanted to wear the clothes in his writing and doodling but was afraid of what it meant. He wouldn't have to fear now, just trust in me and let me lead him to the right place.

With a quick motion of my arm, I slid my hand into his hair and pulled his head back as I leaned down towards him, my eyes blazing as I stared at him. "You don't need to understand, my little slut," he growled, a feral smile on my lips. "You'll do what I tell you and make sure you do your best or you can say goodbye to your life and your future. There's a video camera in the closet that just captured you eagerly putting on girls' clothing, how do you think that will make your senior year go here?"

Holding his hair in one hand, I reached down and unzipped my fly slowly, the sound of the metal against metal loud in the quiet room. Then, I reached in and hauled my half hard cock through the flap in the boxers and let the cool air wash over it as I brought it full you for the young sissy to enjoy. Despite himself, his eyes were staring at it with a mix of dread and fascination, it was probably the first adult cock he'd gotten to see live and up close. Wrapping my fingers around the base, I pulled the kids face close to me until I could smack the head against his cheeks and lips, smiling at his uncertainty.

"Kiss the head," I commanded. "Lick it like you want to, Jamie. Make it all wet and shiny with your mouth like you know you want to, sweetie." I placed the tip at his pink lips so the fluid leaking from the slit would smear over them, giving him a good first taste of what was to come.

Looking up at me and then my member, he puckered his lips and kissed the tip and around the bulbous head. Then, he parted his lips and licked under the head before swirling it around the sensitive head. His breath blew over me as I enjoyed the first ministrations of the boy, watching the curious look in his eyes as he tasted and experienced a man for the first time. He didn't look disgusted when he swallowed down his first taste of the flavor.

"Wrap you hand around the base," I said, pulling my own hand away. "And open you lips." Her gloved hand came up to wrap around the shaft as his lips parted as if his body was already under my command, despite the fear still in his eyes. I could feel him shaking through the hand gently caressing the base. Before he could consider it, I pulled his head towards me so the tip passed through his lovely, pink lips and the head slid over his tongue. Or I should say her tongue as she was quickly becoming my slutty cock sucker.

Her lips and cheeks bulged with the girth of the head in her little mouth and for a moment she considered pulling away but I had a good grip on her hair. I slide my cock in and out of her sweet lips as I feel his tongue trying to tease the underside and his lips wrap tightly around the shaft, even if his face look conflicted. The feeling of her soft lips and slightly grazing of tongue and teeth kept pushing me towards an end that was coming too fast for me. Seeing her pretty face sucking on me with an eagerness she didn't want to admit made it hard to hold back.

"Use your other hand," I told Jamie, my breath coming a little quicker. "Cup and fondle my balls. You want to pass don't you? I know you are a little cocksucker deep inside. I can see your little cock pushing out your skit." And I could see as she knelt there his panty covered cock was tenting the little skirt obscenely, obviously enjoying things deep inside there somewhere.

Her fingers tentatively brushed over my sac and cupped my balls, the lace tickling a little as they settled into place. It was obviously something she'd have to work on as she cupped and kneaded them gently, not really sure what to do. But with her lips sucking like a thirsty girl, it was enough to send me over the edge.

I felt myself pulse inside of her mouth, forcing her lips wider and trapping her tongue. My balls drew up in her hand as the waves of pleasure rippled through me, tingling lightening moving out from my groin up into my head. The first shot exploded against the back of her throat and I heard him struggling with it, trying to pull away from my grip. But I only let him pull back a little so the head was still inside, the next explosion flying across her tongue. I could feel him trying to swallow but saliva mixed with the large load I was giving her dripped out of the corner of her mouth and down her chin. I unloaded more inside of her as she closed her eyes and tried to keep up, forced to swallow quickly until I started to peter out, dripping the last remnants right onto her tongue to savor.

Leaving the head inside for a few moments, I savored the feel of her mouth and her tongue as it swirled around the head on instinct, licking at the tip to get the last dribbles. Finally, I pulled out to let my glistening cock fall from her lips, pink marking the head and base from her enthusiastic lipstick covered mouth. "You are a natural cocksucker," I said, running my hand over her red cheek. "A born slut I see. You just needed to be shown how to handle things

Strange, bright eyes looked up at me then demurely looked away unable to still admit what she was even when it was staring her in the face. Turning away for a moment, I reached into the drawer I'd grabbed the makeup and gloves from, pulling out a length of red silk rope. I wrapped my hand around the little one's arm to help him up, her tongue cleaning the dribble from her lips and chin. He thought it was over and before he could think anything else, I pulled the arm I held behind his back as I pushed him against my desk, bending him over it. Grabbing his other arm, suddenly struggling, I pulled them together and wrapped the rope tightly around his wrist, tying it in a knot that would let me slip it tight.

"Wha... what are yo... you doing," he stammered, trying to turn his head back to look at me.

I didn't answer her at first, instead simply reaching down to grip an ass cheek in each hand, squeezing it and kneading them. His body tried to twist but I had him pinned against the edge of the desk rather nicely with my hips. Bent over, his ass was a fine, feminine shape especially clad in a pair of silky pink panties. Pulling his cheeks apart, I forced more of that material into the valley of his ass which tightened the material around her erection, which brought a breathy grunt.

Slipping my fingers beneath the waistband, I pulled down her panties to just at the bottom of her cheeks, revealing the lovely curve while keeping the rest of him imprisoned in the material. It was a lovely sight as he wiggled on top of the desk so his sexy behind moved so seductively. I reached into the drawer again and started to apply some lube between his cheeks, working it into the tight ring of muscles. It caused a renewed struggle as my free hand pushed down on his shoulders to pin him to the top of the desk while my hips pinned his legs. All he really managed to do was ruby his cheeks against my wet cock so it swelled with anticipation.

"Please... No... I'm not... not into that... please sir." The boy panted and cried out as he realized he couldn't struggle against me and win but didn't want to accept what his body wanted. Even as I rubbed the liquid in, the ring of muscles flexed so my fingers slid in nicely. I grunt and whining moan left him as I moved my fingers in and out until I was satisfied, pulling out so his entrance slammed shut.

Shimming close to him, I placed my cock between his cheeks and slid it through the valley, pressing the mounds of flesh against it. Then, on a back stroke, I aimed it carefully and shoved forward so the head pierced his ass and sunk in until the ring closed around the rim of my helmet.

"Oh, god," he cried, his hands gripping the edge of the desk. "It hurts. Please stop, I don't want this." He didn't struggle too hard though as I left myself sit with just the helmet inside so he could adjust. I gave a good slap to his ass on both cheeks to quiet him down and let him know he was going to take it no matter what. It was time he accepted what he was.

After enough time to let him settle, I began to push into Jamie slowly, pausing to pull back out just a little, then pushed forward with more momentum. I continued with the quick and slow strokes to work my way deeper as the boy's cries and pants turned into something else, biting on his cum stained lower lip. It felt glorious how tight he was wrapped around my cock, it had been some time since I'd had a virgin ass. My hands gripped his hips with each stroke to help pull me forward. He could pretend all he wanted by that ass had a death grip on my dick and wanted all of it deep inside, practically pulling me in with each stroke.

Finally, I felt my crotch grind into his cheeks as my balls brushed against his silken covered ones, the panties tickling my sac a bit. I leaned over him as I settled deep inside, my body draped over his back enjoying the sensual curve and softness of him. Sliding my hand into his hair, I pulled back on the blonde locks so he had to pull his face up which brought his ear to my lips. "Your all mine now, slut," I whispered with a throaty voice. "You will be my bitch and enjoy it. I know you wanted to be my pretty girl so don't you worry, I'll take care of you."

With my hand still in his hair, I began to rock my hips to thrust in and out of him with jackhammer movements, each thrust filling the air with the loud slap of his ass. A feminine, breathy grunt left the boy with each thrust as his struggles seemed to cease. I was thrusting half my length into my student, making him my personal gurl. The tight grip was milking me better than his lips as I thrust into him, the liquid warmth of his lubed tunnel hitting every inch of my questing erection. The boy was staring ahead and something glittered in his unfocused eyes as I fucked him like the slut he was, his stockinged legs brushing against my thighs.

Leaning up, I kept a hold of his long, girlish hair as I got more leverage to pull out farther before slamming into my pet. The full, deep strokes pushed a squeaking gasp from Jamie as the pleated skirt bunched up on her lower back. It was a lovely site to see my cock pull almost out, just an inch or two left in him before plowing back in so I was smashing the base into his cheeks. I soon felt his hips wiggling a little but not trying to get away, only trying to move with the rhythm more. He finally had let himself go and accepted what his body wanted.

The sound of our bodies crashing against one another and our mutual heavy breathing filled the classroom as I fucked my girly student. But already I could feel the orgasm building as I pounded against him, watching his tight ass ripple with each thrust. "Tell me," I growled, pulling the boy back towards me, up off the desk. His back curved as I held his hair like a pony's rein.

"I... I want you," he panted, his eyes glazed with lust. "I want you to cum in my pussy, sir. Fill me up. Make me a woman... make me your woman, sir. I want it all."

Her words were enough to send me over the edge as I thrust deep into Jamie, my cock expanding inside of her, pulsing with the orgasm. My balls twitched against the silky panties as I heard her cry out too. I made short, savage thrust into her ass to milk my dick in her, the tight muscles forcing the juice deep inside. I could feel her tunnel growing slick with my jism as she thrust back at me, moaning as I cried out. Grinding myself against her cheeks, I milked out the last bit before letting myself slowly slip from her tight grip.

As I pulled out, I looked down to see Jamie had cum in her panties like a bad girl. I gave her damp ass a quick swat before grabbing her by the hair and turning her around. Before I could even think about it, she was pressing her lips against mind in a fierce kiss. Her hands were roving over my back and the passion made up for the lack of skill. I was sure though I could teach her a lot in time.

"I see I have my work cut out for me," I murmured. "But I think to make up for insulting me with your cheating and to pull up your grade, you'll need to be doing some intensive extra studying and extra credit. And you'll have to get tutored through the summer so you don't start falling back into old ways."

"Of course sir," he said in a breathy, feminine voice. "I will show you how sorry I am and make you proud."

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