Mr. Wright

As you may know, I am the Headmaster of The Progressive School For Girls. In the senior year of our school, our girls, just ten of them, are introduced to sexuality and submissiveness. Four other faculty members and I each train two of our seniors throughout their last year. Occasionally, one or two of the girls may have already lost their virginity, but most of them are still virgins when senior year begins.

As Headmaster, I take it upon myself to train two of the most promising of the girls. One of these girls this year, Alyssa, is an especially exciting and challenging case. She began the year quite innocent, but she has a bit of a wild streak in her that is particularly endearing.

We meet with our girls once a week, with each week taking on a new lesson. This is my third meeting with Alyssa, and it is the one where I will take her virginity. Too often, a girl's first fuck ends up being disappointing and frustrating to her. A boy beds her, pushes his penis into her until he blows his load, pulls out, and leaves the girl unfulfilled and often wracked with guilt.

I, and all the faculty, strive hard to ensure that our charges' first fucks are rewarding and very fulfilling.

I prepared my office for Alyssa's impending visit. The sofa in my office is also a convertible bed. I've pulled it out and have it ready for use. I've prepared some gifts for her as well, to help make her visit even more exciting for her. I turned down the lights to make it more enticing.

"Knock, knock!"

"Come in, Alyssa!"

Alyssa

I thought this week would never end! At our last meeting, Mr. Wright promised me that at our next meeting, he would take my virginity. There is no one I would rather let be my first lover than he. I know I shouldn't have the hots for a teacher, especially the Headmaster, but I adore him.

Finally, it was Monday morning. I got up early and took a long shower. In the shower, I carefully shaved every vestige of hair from my virgin pussy. I didn't have much hair there to begin with, and I usually keep it closely trimmed because of the bikinis I wear, but I wanted to be totally smooth for Mr. Wright. I dried myself and put on my school uniform. I didn't do anything naughty with it, unlike last week. I wanted to show him I was on my best behavior.

When I got to his office, I felt an instant rush between my legs after I knocked and he told me to come in. I opened the door and stepped inside. I couldn't believe he had turned his sofa into a fully made and inviting double bed!

He came to me, hugged me, and kissed me on the lips.

"Are you ready for your big day, Alyssa?" he asked.

"Oh, yes, Sir! I've been longing for today to arrive all week!"

"Well, I have some gifts for you first. Sit down on the bed and open this first one."

I unwrapped it and pulled the lid off the box. I gasped when I saw what was inside! It was the sexiest little pink nightie I had ever seen. It looked absolutely perfect for me!

He handed me the next box. This one contained matching pink, strappy sandals with the highest heels I've ever seen!

"How high are these, Sir?" I asked him.

"5 inches!" he told me. "I hope you like them!"

"Oh, I LOVE them, Sir! They are so sexy! Thank you!"

The last box he handed me contained makeup. Rouge, eyeliner, mascara, pink lipstick, and pink nail polish.

"I want you to make yourself feel as sexy as possible. All the girls are getting similar gifts. Your first fuck should be memorable! I'm going to leave you now for about a half hour to give you time to get ready. I'll knock when I return. You can let me know then if you will need a little more time, ok, Alyssa?"

I threw my arms around him and kissed him. "Oh, thank you, Mr. Wright. This is all so perfect!"

As soon as he shut the door behind him, I divested myself of my uniform and underwear. I picked up my gifts and took them into Mr. Wright's private bathroom. I looked at myself naked in his full-length mirror. "I look pretty damn good!" I thought to myself. A summer of bikini wearing left my body with an almost all-over tan. There was just a little white around my nipples, and a little triangle of white around my pussy. I felt up my boobs and squeezed my nipples, thinking about what was about to happen!

I slipped into the nightie. The pink of it contrasted wonderfully with my brown skin. My nipples and pussy both showed through the transparent material. There was nothing on this nightie to get in the way of Mr. Wright's cock from penetrating my virgin pussy. I applied the makeup, and capped it off with the pink lipstick. "Damn, I look hot!" I whispered to myself.

I sat down and applied the nail polish to each of my ten toes. Then I painted my fingernails. I sat waiting for it to dry before I dared try on the shoes. I realized that Mr. Wright would be back pretty soon. My toenails were dry enough. I went back into his office, or bedroom as it was now, to try on the shoes.

I never wore anything so high, and my first steps in them were pretty wobbly, but I soon got the hang of them. I just hoped that Mr. Wright would think I looked as sexy as I felt!

He knocked on the door. "Are you ready, Alyssa?"

I leaned against his bookcase, one arm raised above my head, one knee bent, in what I hoped was a sexy pose.

"Come in, Mr. Wright!"

He opened the door and stopped dead in his tracks. He let out a low whistle.

"My God, Alyssa, you are one of the most beautiful sights I have ever seen."

I didn't move, and he walked over to me. He ran his hands over my body and said to me, "I am going to enjoy this at least as much as you do today, darling Alyssa!"

I couldn't believe he called me darling! I began unbuttoning his shirt. I was thrilled to see he was not wearing an undershirt. I removed his shirt and ran my hands over his bare chest. I planted little kisses on his nipples, which left a little lipstick on each of them.

I got down on my knees, undid his belt, and unzipped his pants. I yanked them and his boxers down in one motion, which caused his already hard cock to bounce in front of my face. I sucked on it for a minute, leaving lipstick on his shaft. He pulled me to my feet and lay me down on the bed, before kicking off his shoes and socks, leaving him totally naked. I couldn't take my eyes off his bare body.

"I'm going to have my dessert first," he whispered to me.

Mr. Wright got on the bed and lifted one of my legs. He brought my foot to his mouth and gently licked my toes through my sandals. Just looking at my foot in these impossibly high and sexy shoes sent wetness to my pussy. I've heard shoes like these called CFM, or "Come fuck me"-shoes. I just never thought I would own a pair of them, especially when they were a gift from my Headmaster!

He let my leg down, and spread my legs wide apart. He lowered his head between my thighs and began running his tongue up and down my dripping, pink slit. I shivered in pleasure from his tongue, and his breath on my sex. He pushed his tongue deep inside my hole, curling it to suck out my juices. Then his tongue found my clitoris, and he flicked it rapidly over my nub. Oh my God, it felt good!

"Oh, Mr. Wright, you are going to make me cum!"

"Then, CUM, little girl! Bathe my face in your cream. Make yourself so wet, my cock will easily slip inside you!"

My fingers grabbed hold of the sheets, and I howled my pleasure as my hips bucked against his face. My face must have been contorted; I was in such heavenly pleasure. He didn't let up, and my orgasm just went on and on! I was squirming and thrashing on the bed. I couldn't think straight; I was in such bliss! And then, oh my God, he pushed his finger into my asshole and began finger fucking me there. That only added to the intensity, and I was afraid I would pass out.

Finally, his tongue slowed down. He was gently licking me now. He looked up from between my legs and grinned at me. His face was covered in my secretions!

"Are you ready for my cock now, Alyssa?"

"Fuck me, Mr. Wright! Please fuck me! I need you inside me. I need you to own me. Make me yours, Sir, please!"

He got on top of me and kissed me. I could taste myself all over his mouth and face. He reached down and guided his beautiful cockhead into my slick pussy. He slid right in, but then he met resistance. He pushed, and I felt a sharp pain. I cried out and knew I was no longer a virgin.

Mr. Wright was so sweet then. He stopped and let me adjust to what just happened.

"Are you ok, Alyssa?"

"Oh, yes, Sir! Please fuck me. I need it!"

He began thrusting then, and the momentary pain vanished, replaced by an ever-increasing pleasure between my thighs. His hands squeezed my breasts through the thin material of the nightie, and his kisses warmed my heart. I wrapped my legs around his ass and pounded his butt with my slutty shoes.

Soon I was cumming again, my first orgasm as a real woman! I hugged him tightly and squeezed his ass with my legs. I was moaning out of control.

"Fuck me, Mr. Wright! Please keep fucking me. I need you. I fucking need you. Oh my God, oh my God! Fill me. Fill my cunt with your sperm!" I had never used the word 'cunt' before, but it seemed so perfect and right.

"Oh, Alyssa, I'm going to cum. I'm going to cum in your sweet cunt! OHHH!"

He stiffened and felt him spurt into my vagina, filling me with his cream. I felt spurt after spurt after spurt until he finally subsided.

He slipped his cock out of me and immediately straddled my face. He rubbed his gooey shaft over my face, and pushed his cock into my mouth.

"Do your job, little slut! Clean me!"

I loved hearing him call me names and give me orders like that. It made me feel like I was really his whore. I greedily lapped up our combined cum and swallowed it. He pulled his softening cock from my mouth and got up. He retrieved his phone and took some pictures of his cum oozing from my puffy, pink snatch. He showed them to me. I was so proud I made him cum so much!

I've never cum for so long or so hard in my life, but I wasn't ready for this to end. I wanted more. I NEEDED more!

I pushed Mr. Wright down on the bed on his back. His cock was limp now. It looked so different soft. I think this was the first time I had seen it like this, and I wanted to feel him swell in my mouth. I held it in my hand and smiled mischievously at him.

I began licking the underside of his shaft at the spot he told me it was most sensitive. I engulfed him in my mouth and let my tongue and lips work their magic. Soon I felt him start to swell inside my mouth. I was so proud I could do this to such a sexy man. It didn't take long for him to be back at full length and hardness.

I straddled his crotch and lowered my pussy onto his hard, thick shaft. Ohhh, it felt so good as I impaled myself on him. I went all the way down on his crotch, so the entire length of his cock was buried up inside me. I began riding him, lifting myself up and down on his dick.

Mr. Wright reached up and slipped the straps of my nightie off my shoulders, and then he pulled it down so my breasts popped free.

"Go faster, Alyssa. Ride me. Make those titties bounce!"

I really picked up the pace now. My 35B breasts bounced and jiggled. Mr. Wright grabbed my nipples between his fingers, and he pinched and twisted them both HARD! I cried out, as the pain of that, coupled with the pleasure his cock was giving me, was an indescribable combination that made me start to cum yet again.

"Hurt me, Mr. Wright! Do whatever you want to me. I don't care. Just use me. Make me your whore!"

My words caused him to start slapping my tits. He smacked them hard like he smacked my ass last week. He alternated between slapping them and pinching them. I was like a madwoman bouncing on him. My body was coated in a sheen of sweat. My hair was matted to my face. I must have looked a sight, but I didn't care about anything except the pleasure coursing through my body.

I discovered from all this that men can't cum as often or as quickly as women can. He was thrusting his hips as well, in time with my bouncing on his shaft. Finally, he said he was going to cum again, and he shot his load straight up into my eager cunt.

I collapsed on top of him, totally spent now. I think he was too.

We lay together, cuddling and kissing. I wanted to worship him and his magnificent body. I wanted to be his pet, his slut, his whore, his property!

Finally, he whispered to me that this had gone on much longer than it should have. It was time to get up and shower together before I got dressed and headed back to the dorm.

We got up, and I peeled the nightie from my body. I was nude except for my CFM shoes. The height of those heels put me on eye level with Mr. Wright. We hugged and kissed some more, and then he took my hand and led me into the bathroom.

"Excuse me, Mr. Wright. I have to pee first."

"Go ahead, Alyssa. I want to watch!"

I blushed deeply. "You want to watch me pee? Really?"

"Yes, Alyssa. You must learn submission. If that is what I want, you will do it!"

I sat down on the toilet. It was so embarrassing, but it was exciting too. He didn't take his eyes off me. I decided if this is what he wanted, I'll give him a show. I placed my legs on either side of the bowl, so he had a good view of my pussy as I tinkled into the bowl. He looked right at my crotch as I pissed. I wiped myself clean. He took my hand and stood me up.

"That wasn't so bad, was it, Alyssa?" he asked with a smile.

"No, Sir," I admitted. "It was fun, really."

He helped me remove my shoes and led me to the shower.

Mr. Wright

My mind was a whirl of confusion. This day went off in directions I had not foreseen. I'm the Headmaster of the school. The man in charge. I was supposed to train a young woman sexually and to take her virginity in a way she would find enjoyable and memorable. Well, I did all that, I suppose, but Alyssa is an amazingly intriguing and almost contradictory young woman. She was innocent, certainly, in that just two weeks ago, she had had no sexual experience at all.

She learned fast; that is for sure. After our first meeting, in which she masturbated for me as I watched, she went back to her room and essentially seduced her roommate. They both experienced their first girl-girl sex. The next week she showed up at my office dressed as much like a hooker as she could, and still be wearing her school uniform.

Now today, despite her desire to submit to me and be used, she also demonstrated power and control over ME! In all my years training girls here at The Progressive School, I have never encountered one quite like Alyssa. She has come so far, so fast in her training; I'm not even sure where to go next with her.

We just finished two absolutely amazing fuck sessions for us both that have left us both sweaty and disheveled. I made her piss in front of me, and then I led her to the shower in my office bathroom, and we got in together. The frenzied passion we exhibited in bed was replaced by gentle washing and cleaning. Alyssa was supposed to be my student, not my lover, but our emotions were getting away from us. We finished our shower and dried each other off.

I got back into my suit, and she put her school uniform back on. Suddenly, it felt more like a teacher-student relationship again. I hoped I could keep our relationship that way going forward. I put the gifts of her nightie, shoes, and makeup into a bag and handed them to her to keep. I kissed Alyssa on the forehead and sent her on her way, telling her I'd see her again next week.