Turning the Teacher

Finally, we had everything I had been looking for, and 'Charlotte' and I loaded back into the car, and I drove us back to the home she owned as Charles Wild. It was mid-afternoon.

"Okay Charlotte, I think you should wear one of your sexy new outfits this afternoon, but I'll let you pick. Tennis girl or Hawaiian beach babe?"

"Um - I think tennis girl," she said softly. 'Her' voice was getting more feminine all the time.

"Okay, so you go and get changed. Don't forget to put your new boobs on, and to keep your butt plug in." I ordered her. Charlotte nodded, and went upstairs with the bags full of stuff.

I turned on the TV, tuning it to the Saturday afternoon Match of the Day, and wandered through to the kitchen to raid the fridge as the familiar music filled the air. I grabbed a beer and picked up the camera from where it lay on the kitchen top went back to the couch in front of the screen, kicking off my shoes.

A few minutes later, Charlotte appeared. She was dressed in her new 'tennis girl' outfit, with a thin tight white top clearly showing the now well-filled bra underneath. Below she wore a pleated white skirt barely a foot long, and her long legs were nude down to the flimsy sandals she wore with white ankle socks. Her hair was in a simple ponytail, held back with a white ribbon, and she had white sweatbands at each wrist. She looked delicious, and I told her so as I took her picture.

"Come on in sweetie," I told her. "Curl up next to me on the couch"

Charlotte came obediently, sitting on the couch next to me. Her skirt came up on her thighs as she sat, exposing her legs high on the thighs. I put my arm around her shoulders, enjoying the feel of 'her' feminine frame as I drank my beer and watched the football. After a few minutes, my beer was empty, and I told her to get me another one, and to get herself a glass of white wine. When she returned with our drinks, and sat sipping her wine, I decided to remind her of some of my earlier orders.

"Hey, why are you just sitting there?" I asked bluntly.

Charlotte looked confused. "I was just having my wine," she said in her soft new voice.

"I thought we agreed this morning what you'd do when you didn't have anything else to do." I said firmly.

I could almost see the cogs turning in her head as she rewound the day. Before we went out shopping, I had told her that when she had nothing else to do, she should suck on my cock. When her gaze dropped to my crotch, I knew that she had remembered.

Charlotte reached out a manicured hand towards my jeans, pulling at the fly. As it popped open, I told her to stop, and finish her wine. She glanced at her full glass, holding perhaps a quarter of a bottle, then glanced at me, and then back at her glass. She raised it to her lips, and drank deeply. With a series of gulps, she drained the wine, and put the glass down to one side. Then she reached for my jeans again, and I lifted up to allow her to pull them down to my ankles. I kicked them off as she gracefully curled her legs up onto the couch, lying down with her head on my lap. My half-erect cock was easily visible through the fly of my shorts, and she took it out, sucking the warm flesh into her mouth hungrily.

I grinned, swigging my beer as my sexy and eager cocksucker sucked and licked at my shaft. I had almost forgotten how good she was at it though, and I was soon getting distracted from the game. It was on a digital box, so I paused the live TV and turned my attention to the slut in my lap.

Charlotte was bobbing up and down on my cock vigorously, running her lips up and down the sides of my stiff prick. I was getting very aroused, and decided to stop her before I came, as I wanted more fun before I did. I decided to get her to put on a show for me and told her to stop and stand up.

"Dance for me." I said, taking my cock in my hand as I watched her. For a moment, she hesitated, pouting, then she began to sway her hips and shuffle her feet. My sweet, not-quite-innocent tennis girl danced in front of me, her skirt flaring out when she twirled.

"Stand in front of me." I told her.

She did what I said, and I told her to stand with her legs apart and show me her ass. She reached behind her and slowly lifted the pleated white skirt, showing the pert ass cheeks bisected by a thin white thong.

"Now pull your panties down slowly, keeping your legs straight," I ordered. She did what I said, leaving the skirt piled up on the small of her back and pushing the panties down her legs. After a moment, her ass was visible, the butt plug gleaming darkly between her cheeks, then her cock and balls were dangling below the spread curves of her ass. She kept pushing until the panties were a tight band just below her knees, where I told her to stop.

"Grind for me - grind your hips. Keep your legs straight, and - yeah, that's it. Really work that ass!"

Following my instruction, Charlotte rotated her hips, her ass flexing back and forth as she did. She let out a small grunt as she did, and I knew that the butt plug was stimulating her rectum.

"Are you enjoying that?" I asked innocently.

"Ah-huh," Charlotte moaned, eagerly assenting to being ordered to display herself in this sexy way. "In that case, I want you to lift your skirt up round your waist and keep it there as you go and bring me back the bag from the sex shop. And bring the digital camcorder from the bedroom."

Charlotte stood up straight, lifting her pleated skirt above her waist, and walked away. Her panties fell as she moved, eventually catching around one ankle as she walked. I watched her flexing buttocks as she ran upstairs. Whilst she was gone, I kicked off my jeans and boxer shorts, leaving me in just a T-shirt, and drank from my beer. My cock was still hard, and I was keeping my hand on it.

A few moments later, she came back. Her frontal appearance was sexy and androgynous, with a pair of full bouncing breasts beneath her short top, but with her skirt lifted she displayed her bobbing cock, smooth and slim above the balls drawn tight up against the base.

"Get down on your knees, sexy" I said after she dropped the bag in front of me. Charlotte handed over the camera, and obeyed eagerly, her knees apart. I opened the camera and started filming my sweet little slut. She was facing me, and I told her to take hold of her cock. She let the dress fall around her waist, taking her sweet cock in one well-manicured hand.

"That's right. Start pumping away on your sweet little cock. Just like that, yes."

I kept the video camera on my submissive schoolteacher as he knelt in front of me, masturbating his/her cock whilst dressed as a sexy girl.

I told her to turn around and bend forwards on hands and knees, taking a long close-up of her well-curved ass before leaning forward and pulling on the butt plug.

With an audible pop, the plug came out, and Charlotte groaned passionately as she felt suddenly empty. I took one of the dildos, and lubricated it with a heating gel, sliding it into her gaping anus, producing another series of low groans from my submissive partner. She kept jerking at her cock though, breathing hard and clearly excited.

"Let go of your cock and take hold of the dildo," I told her, "and then fuck yourself with it."

As her hand came back and took over thrusting the rubber cock in and out of her ass, I hunted out the second dildo, coating this one in a little strawberry lube. I moved up towards her head, and slid it easily between her soft, open lips. Charlotte took this dildo too, sliding it in and out of her mouth, her tongue flickering over the head.

I sat back and admired my work. My schoolteacher, Mr. Wild, had now become a completely submissive, sexy woman, penetrated at both ends by a replica of my own cock. She was half up on her knees, her own cock erupting from her skirt, thrusting one dildo in and out between her pert ass-cheeks and the other between her cherry-red lips. The look on her face was amazing - lust, pain, desperation...

This film was going to be superb! Shame no-one else was going to see it - but I could see myself building up quite a collection...

Charlotte's face began to tighten as she panted around the dildo in her mouth, and her cock began darker pink and swollen. As I zoomed in on her face and cock, it was obvious that she was going to come.

"Take that dildo out of your mouth, Charlotte," I said.

Charlotte slid the rubber phallus out of her mouth with a gasp, panting for air. With the other hand, she was still pumping the second dildo in and out of her ass. I put out a hand to gently stop her with the cock deep inside her.

"Do you want to come, Charlotte?" I said as she groaned hungrily.

"Oh God! Oh God, yes! Please!"

"Were you going to ask my permission?"

"Yes! Yes, please... please, I need to come" she begged, eyes rimmed with desperate tears. "Please let me come."

"Okay, you can start fucking yourself again. Do you like fucking yourself with my cock?"

"Yes... it feels so good... so good to have your cock in my ass..." she moaned.

"Good, because you'll be having the real thing again later," I said. "Now, I want you to make yourself come with the dildo, and to hold your skirt up so we can see your cock as you come."

Half-hunched over, Charlotte pulled the waistband of her short skirt up her midriff, completely baring her buttocks and groin. She leant forward, thrusting the dildo in and out of her hard-working rectum, emitting little groans and grunts.

Finally she came with a loud wail, burying the dildo in her ass, her cock swelling and pulsing as it shot jets of thick spunk into the air. I filmed the whole thing, her come flying nearly two feet from her jerking cock.

She sank down, almost spent, eyes heavy-lidded. Balancing the camera on the arm of the sofa to keep her in frame, I called out to her.

"Charlotte... Charlotte... Hi there! Did you enjoy that?"

"Yes... Yes sir" she half-giggled excitedly.

"You've made quite a mess, Charlotte. Don't you think you should clear it up?"

Charlotte looked down to the laminate wood floor, where the white spray of her come streaked the surface in front of her.

"Lick it up," I ordered.

Charlotte managed one of her increasingly brief moments of rebellion. "Do I have to?"

"Yes. Oh yes, you do. And you'd better do it thoroughly. And whilst you do it, I'll be working behind you, so bend over and put that butt in the air!"

Charlotte sighed, but bent over, lifting her ass and pulling up the little tennis skirt to expose it fully.

Reaching into our shopping case, I brought out an enema bag. As Charlotte began to lick her come off the floor, I picked up the bottle of wine and used it to half-fill the enema bag. It wasn't enough, so I jogged to the kitchen for another bottle to top it up. Then I moved behind my obedient slut, her tongue working away on the hard floor, and told her what I was going to do.

"I'm going to clean you out, little girl. I'm going to give you an enema to make you ready for me to fuck you again," I said as I pulled the dildo from her rectum. She moaned, strands of come sticky between her lips and the floor as her anus gaped at me. I easily slipped the nozzle of the enema bag into her.

"Now clench down on this, we don't want to waste any."

Charlotte's butt-cheeks clenched, and I lifted the enema bag, letting a bottle and a half of wine begin to flow into her bowels. She finished licking the floor, and lifted her head, waiting for me to finish on all fours.

"That feels strange," she said in a somewhat strained voice.

"I know. I've done it once or twice myself. I'd usually just use salty water, but I thought this might be more fun for you - I'm filling you up with wine."

"Wine!" her head snapped round to me. "You're putting wine up my ass!"

"Hey don't worry. I read that the Greeks and Romans used to do it all the time. And in Victorian times, people used to use coffee for enemas. It means that the alcohol or caffeine gets absorbed really quickly. It should be fun!"

Charlotte sighed again. "Oh, Matt..."

She didn't move however, and I turned to grin at the camera, silently recording me giving my cross-dressing teacher a wine enema. I winked at the camera as the enema finished.

"Now you have to clench down tight when I pull out," I said firmly.

Charlotte nodded, and I gently pulled out the nozzle of the bag. Her puckered hole tightened up behind it, and not a drop was lost.

I pulled over a footstool, and told Charlotte to lie on her back, with her legs over the footstool. She got into the position I wanted with some reluctance, feet dangling off the other side of the stool as her butt was lifted into the air.

I told her to gently massage her stomach in an anticlockwise direction, which should help the enema go around her insides. Then I finally reached down and paused the camera. With Charlotte lying there rubbing her stomach, I wandered into the kitchen to find Charlotte's collection of takeout menu's.

I ordered a couple of pizzas, gazing at my sexy schoolteacher, lying on the floor in the other room. As I hung up, I called her over.

"Charlotte - come over here." I said.

Charlotte's head turned slowly towards me, and smiled happily.

"Hi, Matt." She said softly, real warmth in her voice.

"Come over her, Charlotte."

A little awkwardly, she slid her legs off the sides of the footstool, and tottered over to me unsteadily. Her eyes were a little glazed, and I could see that she was already drunk.

Charlotte threw her arms around me, planting her lips to mine in a passionate kiss. Her tongue slid into my mouth, and I felt her breasts pressing against me. Our tongues tangled as we searched each others mouths passionately.

After kissing for a minute, we separated, and she looked puzzled, then uncomfortable.

"I need to go to the bathroom," she announced.

I smiled at her. "Okay, off you go. Then come back down for me. I'll be in the living room."

Charlotte walked carefully, but unsteadily upstairs as I wandered into the living room. After a minute, I heard a deep groan upstairs, and the sound of water splashing. I grinned.

I took off my T-shirt, leaving me naked, and stood in the living room. I opened the double doors into the garden, and stepped outside. Charlotte's house stood alone, and her garden was surrounded by hedges. This was pretty private, which suited me fine. It was a warm evening, and the sun was low in the sky, giving the sky a beautiful pink cast.

Back in the house, Charlotte bounced down the stairs, clearly much more comfortable, smiling broadly.

I picked up the video camera and tripod, fixing the two together, and told her to follow me outside. With my slut on the grass in front of me, I told her to wave and blow me a kiss, which she did with a giggle. I told her to skip around the garden, and she did what I wanted, her short skirt bouncing to show glimpses of her arse, and her dangling cock.

"Come into the middle of the grass, Charlotte - and do a striptease for me." I told her.

Charlotte smiled and sauntered into the middle of the lawn, flicking her hair back over her shoulders. She started to gyrate, turning her hips in circles once more as she reached down to her stomach, which was displayed by her cropped white top. As she started to lift the top, she turned her back, looking over her shoulder teasingly as she started to lift the material up, exposing her upper back, and the straps of her bra. The top came off with a shower of black hair, falling back into her ponytail. She turned slowly and deliberately, stroking her hands across her flat stomach and pert boobs, encased in white silk.

I kept filming as her hands came down to her waistband, slowly pushing her hand down the front of her skirt. The other hand pushed the skirt down at the back, before moving to do the same at the back. As the skirt dropped to her ankles, I saw that she was cupping her cock and balls in one hand, keeping the illusion that she was just an ordinary tennis girl.

She turned away again, moving her hands behind her back to undo her bra, which she stripped off with her back to me. Dancing for a few moments with her bottom towards me, she turned once more.

Now, Charlotte was clearly a man again. Her hard cock stood up stiff in front of him, his balls tight up against the base. The breast-forms looked surprisingly realistic, still glued to his chest, the nipples pink, erect and ready to be sucked. She toyed with one of them with a well-manicured nail.

"Is this what you wanted to see?" 'she' purred at me.

I nodded, starting to place the camera on the tripod.

"Get on all fours facing me," I told him.

My androgynous teacher did what I told him, planting his hands and knees several inches apart on the grass. I focused on him, pulling back slightly so that I would be fully in the shot, and walked around behind him, leaving the camera running.

I stood behind him, curvaceous butt gleaming in the pale evening light. He was naked aside from the breast-forms, hairband, and white sweatbands around his wrists. So sexy - you could still see him as a sexy tennis girl but also as a boy at the same time.

My favorite!

I dropped to my knees behind him, bringing my face down to his ass. There was a fresh smell of wine, and I investigated, one finger sliding into his rectum. The cavern was warm and empty, less tight than it had been just yesterday.

I brought my head down, pressing my tongue to his anus with pleasure, tasting the sharpness of his rectum mixed with the sweet wine as my tongue invaded him. I rimmed him for a couple of minutes, enjoying the groans and moans he made. Under his waist, I toyed with his cock with a free hand, gently stroking his foreskin back and forth over his thin shaft.

Pulling my face back from his ass, I knelt up behind him.

I took my cock, placing the glans at his anus. He pressed back against me, and my cock slid easily into his dark passage. This time we both groaned together, as his tight anus bit down on my own much larger cock.

I started slowly fucking him, sliding my thick-veined shaft in and out, and began talking dirty to him again.

"You like that? You like my cock in your ass?" I asked harshly.

"Yes... Oh, yes, I love it," said Mr. Wild happily. He was so much more active than he had been before - clearly the alcohol had wrecked any remaining inhibitions he had, making him a complete cock-slut. Just the perfect man for me. And the perfect woman, for that matter.

"Tell me how much you like it." I said.

"I ... ah! I love the feel of your stiff hard cock as it... aaah... as it goes in and out of me. I - uh! - I love the feeling of my ass getting stretched around you!"

Mr. Wild panted, but carried on with his own dirty talk. "I love it when you fuck me - I feel so dirty, but so good! So sexy and special... Aaaah!"

His words dried up as I began thrusting in and out with greater force, my own urgency taking over me. I hadn't come earlier, and wanted to come now, deep in his ass.

We began to move as one, and he cried out as he felt my cock begin to swell inside him, stretching his bottom to its limit.

Finally, I came, shooting jets of spunk deep inside his hot bowels. I felt him jerking, his rectum tightening around my shaft, and I knew he had come too even before the cry escaped his lips. We jerked back and forth for over half a minute, each stimulating the other even after orgasm.

Eventually, I withdrew, sitting back on my haunches. Mr. Wild collapsed in front of me, curling up on the grass, naked legs curled up.

As I stood to turn off the camera, I heard the doorbell ring. The delivery guy!

"Quick, get up!" I hissed at him. "Put on your skirt and top, and follow me. Don't bother with underwear."

I ran inside, picking up my T-shirt and shorts and jumping into them. The doorbell rang again, and I ran over.