Turning the Teacher Ch. 02

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Matt takes his sexy sub teacher and dresses him up.
4.7k words
4.52
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Part 2 of the 3 part series

Updated 09/22/2022
Created 09/22/2008
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Dave933
Dave933
911 Followers

I woke up early, sunlight pushing through the feeble barrier provided by pale yellow curtains. I was lying on a double bed in a strange room, and for a moment I wondered where I was.

Then it came back to me.

I was at my teacher's house, Mr. Wild. I had found a sordid and sexy video he had starred in before he became a teacher, and used it to blackmail him into becoming my very own sexy cock-slave. I looked over, and he was lying next to me, his face still wearing make-up which was a little dry. His newly-dyed brunette hair surrounded his head on the pillow.

I looked down.

His chest was hairless, right down past the navel, where the sheet covered him. Lower, a stocking-clad leg protruded from under the covers.

I grinned, and gently slipped out from the far side of the bed. I padded through to the bathroom for a slash, and then jumped into the shower for a wash.

Ten minutes later, I was dry, and came back to the bedroom. My teacher was still lying asleep in bed. Even with the overnight makeup, he looked very sexy. I can't deny that a big butch man is damned sexy, but my personal preference is a more androgynous look. Maybe that's because I'm really bi, and I love women's bodies too. Last night, I spent about half the time thinking of him as Mr. Wild, and the other half seeing him as a 'her', the sexy Charlotte.

He was definitely a he at the moment though. There was a definite bulge at his midriff, poking through the thin sheet. I smiled, and went to pick up the video camera set up in the corner of the room. I took out the memory disc, replacing it, and set up the tripod so the camera was looking closely at Mr. Wild. Once it was set up, I went to pick up the still camera, and turned it on, taking a couple of shots.

Gently, I reached out and lifted the cover, pulling it back over his body.

In a few moments, I had revealed his hard cock, a slim white snake coiled up in his naked crotch. Not a whisper of hair was left on his cock and balls, carefully stripped at the spa yesterday. Below the sexy sight of his nude crotch, he still wore the creamy-white stockings from yesterday.

Nice.

I took a few more shots, both at a distance, and right up close. Man, these were good. But I had even sexier pictures in mind.

I reached out, gently taking his semi-hard cock between my fingers, and stroking it back and forth. It quickly grew to a proud but slim six inches, uncut, the glans pressing out through his foreskin like a flower bud.

I stepped back and took a few more pictures of him lying there, the zoomed in close on his stiff cock. I didn't just play with my camera for long. Putting it down, I reached out for the stiff shaft and bent forward, sliding my mouth over the swollen head.

With my hand, I kept stroking the stiff shaft as I swished my tongue around the head of my teacher's cock, savouring the salty taste of his cum. Softly, he moaned, and his legs parted as he rolled onto his back.

I kept the hard shaft in my mouth, teasing the tip with my tongue as I stroked the end with my hand. Resting on my belly, I brought my other hand around, and began to caress his balls. Obviously now awake, Mr. Wild moaned again, and I felt his hands gently rest on the back of my head.

Bobbing back and forth, I momentarily released his cock to wet my forefinger in my mouth before diving back onto the salty treat. A moment later, my wet finger was pressing against his anus.

Mr. Wild's stocking-clad legs parted as wide as they would go, allowing my finger to press deep into his bottom without resistance. I pumped it back and forth as best I could, a little awkwardly due to my position on the bed. Nevertheless, it was obviously pleasant for Mr. Wild, who began groaning with pleasure.

After a couple of minutes, I could feel his anus contracting around my finger, and his cock swell as his orgasm approached. His back arched as his orgasm surged through him, and his cock filled my mouth with jet after jet of warm cum.

I kept my mouth full, letting his cock slide out, and slid along his body, over the heaving chest, and pressed my lips against his.

As he kissed me back, our lips parted, and I let the mouthful of sperm slide from my mouth into his. His eyes bulged, but he took the mouthful obediently, swallowing his sperm without a murmur. I knelt back between his legs, and licked my palm with the last of his slimy sperm, reaching down to transfer it to the hard thick shaft erupting from my crotch.

Mr. Wild stared at me with deep blue eyes, breathing hard. He looked nervous, horny and confused all at once - I loved it! So sexy!

I reached down, pulling his legs up in front of me, pushing them back towards his chest until his ass began to lift off the bed. With his feet now up on my shoulders, I reached down to my cock, placing it at the entrance to his tight butt.

He whimpered, eyes fearful but longing, but didn't move away as I pressed my stiff come-soaked shaft deep into his dark passage. We groaned together, both enjoying the tightness of his anus around my thick shaft.

Mr. Wild lay back and closed his eyes in wanton surrender as I thrust again and again deep into his ass. Pressing against his thighs, I looked down at him, then over at the camera recording his hard fucking.

"Open your eyes," I ordered him. He obeyed me, looking up with eyes bursting with passion, clearly almost delirious with pleasure. I told him to look over to the window, and he finally saw the camera filming his debauchery.

His face fell a little, but he didn't protest. After staring at the camera for several seconds, he just closed his eyes and lay back again, getting lost in the pleasure I was giving him.

I decided to let him enjoy himself a little longer, but after a minute, I pressed him.

"God you're tight!" I said. "I'm loving this. Loving fucking your tight ass. Are you loving it? Tell me if you're loving it..."

His lips parted a moment, as if to speak, but he stopped. I wasn't going to let him away with that!

"Do you want me to stop?" I asked, slowing down my rapid jerks into long slow thrusts in and out of his rectum. "Do you want me to stop fucking you?"

"N...no!" he cried eventually, eyes screwed shut.

"What was that? I didn't hear you."

"NO! Please don't stop!" he cried.

"You want me to keep fucking you?"

"Yes! Please keep fucking me," he gasped, hands clutching at the bed sheets in desperation as he got closer to another climax. I wasn't even touching his cock, now hard again between his thighs and belly.

"Are you my little girl?"

"Yes! I'm your... Your little girl... I'm....aaaaaaah!" he cried out as he came again. I stopped thrusting, but the feeling of his ass contracting around my cock was too much, and I erupted myself, spurting my hot cum deep inside him.

We jerked and bucked together with pleasure, and then held an odd tableau for several seconds, me pressing hard into his ass as I looked down at his helpless features.

Eventually, I pulled out and sat on the edge of the bed, a little out of breath. He was silent.

"I'm going for a shower again," I said. "Get us some breakfast in bed, and then you can have your own shower. And don't forget to shave!"

...

Mr. Wild fixed us a breakfast of coffee, juice and toast with marmalade, eating quietly. He didn't seem ready to make conversation yet, although I would have been happy to. After eating, he went to shower, and I went about choosing him an outfit to wear.

I had brought a bag full of women's clothes that various girlfriends of mine, and my brothers, had left over, as well as stuff I had picked up from charity shops. I had had to guess the right size, and had only managed a couple of pairs of shoes.

I put an outfit out on the bed for Mr. Wild to wear, and turn from Charles Wild, school teacher, into Charlotte Wild, sex kitten and general cock slut.

I left a set of (unfortunately mismatched) bra and knickers, along with fake boobs and stockings. To wear on top, there was a short red skirt and a white blouse, and a small red scarf, like some air stewardesses wear.

I sat back and enjoyed my coffee until Mr. Wild returned from the bathroom freshly showered and shaved.

"I've picked out an outfit for you," I said. "Why not put the underwear on, and then fix your hair?"

"Matt, please..." started Mr. Wild. "Can't you stop? Why make me do this?"

I stood up, walking over to him. "Because I want to. Because it brings me pleasure. Because you don't have a choice."

Actually of course, he did have a choice. He just didn't like it. But the last reason was the real one - the reason I didn't say. Because he was loving it!

He still tried to beg off a little. But I wasn't having any of it.

"Get your ass into that underwear! This weekend, you're MY little girl, and you're gonna dress the part!" I pointed at the bed.

Head down, he walked silently to the bed, and started slipping on the stockings. I watched as the knickers and bra followed, and then told him to sit in front of the mirror and put on makeup. As he did, slowly picking through mascara and eyeliner, I stood behind him, and pulled his hair into a tight plait, fixing it with a red ribbon.

I tossed him the breast padding, and he slipped them into the bra. Once again, 'he' had become a convincing 'she'.

"You look great! Welcome back, Charlotte! Now stay there and look at me in the mirror."

As she did what I said, I raised the camera. After a couple of shots, she burst out "Please Matt, don't take more pictures."

"Why not? You look sexy."

"I'm scared that you'll... That they'll get out."

"They won't. Come over here."

She stood and walked over, somehow more graceful than she had been as a man.

"I promise no-one will see them without your permission," I said seriously. "I'll keep your secret."

She nodded, eyelids batting.

"Now, kneel down."

She blushed, but knelt obediently at my feet. I raised the camera, taking a shot of her upturned face down the length of my body.

"Undo my towel," I ordered. I kept snapping, as she reached out, undoing the towel knotted around my waist.

"Take my cock and suck it." I ordered.

She did what I said, and I photographed the whole thing as she fed my half-hard cock into her mouth. I called her name, and she looked up at me. Her upturned face, mouth full of my cock, made such a sexy picture!

I smiled at her. "This is what you should always be doing. You look so good with my cock in your mouth. For the rest of the weekend, any time you aren't doing something else, whenever the opportunity arises, you should take my cock into your mouth. Understood?"

She nodded, eyes fixed on mine.

"That's good. Now, you can put the rest of your clothes on." I said benevolently.

Charlotte stood, and obediently went to the bed, slipping on the short skirt and blouse. The tiny scarf matched the bow in her hair, and gave her a really jaunty, sexy look. I took a couple more snaps before eventually getting dressed myself.

...

Twenty minutes later, we were well on our way out of town, headed to the city thirty miles away. I had plans for something of a shopping spree, on Charlotte's dime.

...

I knew Charlotte wasn't rich of course, so we couldn't go too upmarket. And I wanted to try and sort out several outfits, rather than just one expensive one. But I knew a street where there were a string of charity shops, the last one specialising in costumes.

After parking, we walked to the shops, Charlotte attracting a few appreciative glances.

The first shop wasn't too good, mostly having just casual clothes in fairly poor condition. But the second shop was much better, and we managed to find a couple of dresses in Charlotte's size, as well as skirts and tops. Then we went to the one specializing in formalwear and costumes.

It was like Aladdin's cave! Row upon row of cocktail dresses, shoes, gowns and silks!

The rest of the morning was enormous fun, and Charlotte finally got into it as I complimented her over and over on her sexy appearance.

We finally got her a total of four full outfits, plus a bikini and grass skirt. The first was a biker-chick outfit, with short leather hotpants, and a half-size leather jacket which just clipped over her false boobs, and left her flat belly exposed. Then we put together a sexy tennis outfit, with a tight white sleeveless T-shirt and short pleated white skirt. We even found some soft white sneakers to go with them. The third thing we picked up was a really sexy little number which was obviously intended as a 'serving maid' outfit. It was made of yellow and white gingham, with a wide open neck that made it look as if the puffed-up shoulders had been pulled down, leaving the top of the chest and the upper arms bare. The rest of the front and back would be covered to the waist, but then the skirt flared out above a wide spray of crinkled petticoats, making it just less than horizontal. The petticoats would conceal, if hardly covering, the very top of Charlotte's long legs. The rest of her legs were exposed, which looked fabulous in the stockings she was wearing.

The last outfit was simple -- just two things, a hat and coat! The hat was a wide-brimmed black mesh with feathers in it, looking elegant on her head. The coat was a three-quarter length (fake) fur coat which looked a million dollars! I got her to try it on after undressing, so she was wearing just underwear beneath it, and I got hard thinking about her walking around in public looking respectable, but decadently indecent underneath!

Once Charlotte was back in her 'air stewardess' outfit, we took the bags back to the car and drove to a café for lunch. I talked softly to hear, teasing her a little about seeing her in the sexy outfits, and she giggled girlishly.

After lunch, we had another part of town to go to, which the locals called 'little soho'. It was where the strip clubs and sex shops were, and it was a sex shop we headed to. I had never been to one, but I'd got a catalogue from one on-line, and had a few ideas about what to buy.

There were a couple of guys in the shop, and they both ogled Charlotte every chance they got.

"That guy's looking at your legs," I said to her, as we were looking at a display of toys. Charlotte turned briefly, and then looked back, blushing.

"Give him a show -- bend over and pick up that box of body paint," I said quietly.

Charlotte's face froze, then she did what I ordered, bending over at the waist to pick up the item, and even staying down for several seconds, pretending to rifle through the display. I glanced at the guy, who was staring at Charlotte's legs, her stockings, and the bottom of her exposed ass-cheeks. He saw me looking, and blanched, but I winked and gave him a thumbs-up.

A few minutes later, I had gathered a small basket of goods which I was keen for Charlotte to use or experience, and had gotten into a conversation with my new friend. He was just in town for the a few days, and was planning to go to a lap-dancing club when they opened that evening. For now, he was just killing time. I pushed him a little.

"So lap-dancing, huh? I guess you like looking at naked women. Did you enjoy looking at my girlfriend's ass?"

He looked a bit freaked out, but answered me "Yeah... yeah"

"Well she hated showing it to you, Mike. She's a shy girl is my Charlotte. Hey, Charlotte, get over here!" I called.

Charlotte came over obediently, holding a box of edible underwear.

"Mike here was checking out your ass earlier," I said breezily. "Why not tell him how much you enjoyed it?"

Charlotte shook her head, biting her lip charmingly. "No...no I didn't" she said in the soft tones she had adopted for the day.

"You didn't? Didn't like showing him your ass?"

She shook her head, looking at the ground.

"That's a shame -- Mike loved it, didn't you Mike?"

"Yeah -- she's real hot!" Mike grinned, clearly amused at the blushing girl.

"Bend over and show Mike again," I said.

"Please...no..." said Charlotte a little desperately.

I didn't reply, simply twirling my hand to gesture at her to turn around. Reluctantly, she did what I said, and then slowly bent at the waist. Her skirt rose up, revealing her stocking-tops. I put one hand on her lower back, turning to face Mike proudly, grinning at him. Mike had a big shit-eating grin on his face, and was fixed on her ass. I knew what he wanted, and pulled the back of her skirt up a little to expose the curves of her buttocks, and the tight thong between them.

The two of them stood in tableau for several seconds, until I dropped the skirt and lifted my hand, letting Charlotte rise. Bright red, she straightened her clothes as I trotted over to the girl behind the counter.

Two minutes later, I was leading the two of them into a back room, both knowing what would happen next. The back room was a storage space, half-filled with boxes, and I sat on one as Mike closed the door behind him, his erection obvious as he turned towards us. Charlotte stood mutely in the middle of the room until I told her to kneel.

I made a 'carry on' motion to Mike, sitting back and taking out my mobile phone. I switched the phone to video-camera mode, and made a short film of what happened next. Mike took out his cock, a good seven-inches, and stood in front of Charlotte. Without being told to, she knelt forward and took the thick shaft into her mouth, reaching out with her hands to grasp the base. Mike's hands came down to Charlotte's head as she bobbed back and forth.

Mike was clearly very turned on, as he didn't last long. In just a few minutes, he grunted and groaned, shooting his load into Charlotte's willing mouth. Charlotte swallowed, milking his cock of every drop, and letting it slide out almost with regret. She held his shrinking cock tenderly and licked it clean before tucking it away into his pants.

Mike excused himself and disappeared pretty quickly, and I helped Charlotte to her feet. She looked at me accusingly, and I smiled at her. It was pretty obvious she had been willing -- I hadn't had to say a word, and Mike hadn't needed to do much persuading!

Back in the main shop, I stood Charlotte in front of the vibrator display, and told her to choose one. Unsurprisingly, she picked a tiny model, barely four inches long, and I said "think again!"

She was still looking at the smaller models though.

"Listen, choose a good one, or I'll choose one. From the back shelf!"

I didn't let her know I was kidding. Those things on the back shelf were actually a bit frightening! And they'd certainly over-stretch Charlotte's nice tight arse. Luckily, Charlotte got the message, and started picking out some a bit more my size.

"Would you like a hand?" came an enquiring voice from behind me.

The shop girl stood behind us, a pleasant smile on her face.

"Are you looking for a dildo or a vibrator" she asked casually. She leaned in closer to me, and whispered into me ear so Charlotte couldn't hear "or would you prefer a butt plug?"

I was taken aback at first, but realized that this girl must see all sorts of people in this shop, and had been more than willing to let us use the back room. She had obviously clocked Charlotte as a man.

"Err -- is there one you'd recommend?" I asked politely, trying not to leer at her. She was a pretty girl; not beautiful, but pretty and well made up.

She smiled, one eyebrow rising.

"Oh they've all got their pluses. I rather like this one as a vibrator -- small enough for my handbag, but surprisingly powerful." She said, licking her lips as she trailed one finger over a short brass-plated phallus. "But there are times for a vibrator, and times for a plain old-fashioned rubber cock. This is my favorite."

She picked up a ten-inch black rubber dong, which was as thick as my wrist, and smiled. Charlotte looked distinctively nervous.

Dave933
Dave933
911 Followers
12