File 194533

Student Name: Upfield-Smythe, Tiffany

Age: 19

Instructors notes:

This case was the usual breaking in procedure. The student (Tiffany) had been brought in by her mother. Tiffany’s parents were both Academy graduates and they wanted their daughter’s virginity to be taken in the traditional manner.

It began Friday morning when Tiffany and her mother visited the academy. Being in charge of new enrollments they were shown to my office.

“Tiffany’s quite shy, and has never been out with a boy.” Mrs. Upfield-Smythe informed me as she sat in one of my large velvet chairs. “Naturally being from a family with such a high position in society we can’t have her consorting with just anyone. Gerald had some crazy notion of pairing her with the Winston’s boy, but naturally I insisted she be broken here.”

“Rest assured Mrs. Upfield-Smythe,” I said smiling. “Our stud are of the finest stock and you can count on our discretion. We’ll have Tiffany trained in no time, and your family’s reputation will remain unsullied.” I stood and walked round to the front of my desk, and looked at Tiffany while I spoke with her mother; “Would you like to watch the training? A lot of parents like to view at least the first day.”

Mrs. Upfield-Smythe shook her head and picked up her handbag. “No, that shan’t be necessary.” She said and kissed her daughter, “I’ve a meeting to attend to in the city.” Then she was gone.

“Tiffany, stand up.” I said, wanting to get a good look at her. She was short and blonde, and had her hair tied back in a simple ponytail. She wore a tight summer dress that her small, pert, strained against as if seeking release. Her legs were long and smooth, and her skin was alabaster white. “Tiffany, do you understand why you’re here?” I asked her.

“No miss.” She replied softly.

“Don’t call me miss.” I snapped, “You will address me a Mistress, or Mistress Jade and nothing else. Do you understand?” Tiffany nodded, satisfied I continued: “Tiffany you have been brought here to be taught how to fuck. Here you will learn how to fuck a man; how to please him with your cunt, your lips, your hands, and the rest of your body. You will learn to obey, and you will learn to enjoy it...” I had been pacing the room while I made this little speech, but now I looked over at Tiffany, she was blushing bright red. “Does this excite you?” I said smiling. Tiffany shook her head in an embarrassed kind of way. “It’s OK Tiffany, you’re allowed to like it. It’s good if these thoughts excite you, but I will punish you for lying. I’ll ask again; “are you excited.”

There was a long pause. Tiffany shook her head.

In one deft movement I whipped my hand under her dress and down into her panties. Her pussy was dripping. “Ah ha!” I exclaimed, then started to rub my fingers back and forth over her juicing quim. “Your cunt is very wet Tiffany, this is a sure sign of sexual excitement. Your pussy is getting ready to fuck, it wants... it needs an orgasm from a big hot cock... or a tongue... or some fingers!” With that I pushed two of my fingers into her snatch and began to stimulate her from within as well. “You lied to me Tiffany. You should apologize.”

Tiffany was pressing against my hand. She was flushed and breathing heavily. She gulped and said; “I’m... I’m uh... sorry... very, ah, very sorry... Miss Jade...”

“You will call me Mistress!” I said, and pulled my hand from her panties. Then I forced her to put her hands on my desk and I spanked repeatedly. When I thought she had learnt her lesson I said; “Now Tiffany, follow me.”

I took Tiffany to the white room, and got her to undress. The room was completely empty and white except for a large pure white bed in the middle of the room. “Here’s where the real training begins.“ I told her. “Please sit down on the bed, and get yourself aroused.” Tiffany shyly sat on the bed and gingerly touched the edges of her pussy lips. It was clear she was too embarrassed. “No no!” I scolded. “Here I’ll help you this time.” I stripped naked myself and sat on the foot of the bed. I ran my fingers along her tight little slit, and Tiffinay gasped. Her pussy had only the tiniest amount of hair and was bright pink. Tiffany was breathing heavily and her pussy juices were beginning to ooze forth. I rubbed the juices along the length of her cunt. I dipped to fingers into her dripping snatch and began to work them in and out. “As I do this you will feel a powerful sexual feeling.” I told her; “you will feel hot and flushed, your heartbeat will increase, you will breath faster, and your nipples will harden.”

Tiffany was responding quickly to my ministrations; “Ohhhhh, ah, ah, yes.... ohhh... uh oh Mistress...” she panted like a bitch in heat.

“The most important part of your cunt is the clit.” I told her, and with that I bent over and licked it. This sent Tiffany over the edge. She cried out and arched her back.

“AWWWW GAWD!” She cried, then lay breathless on the mattress and mouthed the words; “thank you.”

I smiled, knowing that Tiffany had just had a relatively minor orgasm, and that much was still to come. “Keep playing with yourself.” I instructed as I walked out of the room.

Seconds later I reentered with a tall naked man. I had my hand around his cock and led him over to the bed by his prick. Tiffany had her eyes shut and was licking her lips and was still touching herself. She opened her eyes and looked up. She flushed red, embarrassed to have a man catch her in this position. I laughed. “Tiffany, this is Eric. He will be your mating partner for basic training. You should never feel embarrassed with him. Sit up. I want you to touch his cock.” Tiffany demurely sat up and gently touched his dick. “Caress it, explore his body.” I instructed her. At first she was shy, but then with increasing confidence she ran her hands up and down his shaft, and felt his balls. Eric took her hand and warped it round his cock, then showed her how to pump up and down. Tiffany watched her hand pump his prick in wonder. The huge dick was quite a handful and she soon changed to two hands.

All this time his cock had been at eye level. “Is there something you want to do?” I asked Tiffany. There was a pause. Then she nodded. “What do you want to do? Say it.”

Tiffany shook he head; “I... I can’t.” She said quietly.

I leant over her, put my head on her shoulder and pressed my tits into her back. I began to stroke her pussy; “Say it Tiffany. You can say it. I give you permission.” I whispered into her ear.

“I want... I want to suck it...” She said faintly.

“Excellent. That is every woman’s natural response when she sees a big juicy cock.” I reassured tiffany. “I want you to suck it, and suck it hard.” Tiffany put her lips around Eric’s cock and he sighed in ecstasy. She sucked hard, pushing her lips up and down his shaft. “Good. Very good” I said, “Try to get it deeper... deeper...” I put my hand on the back of her head and pushed her forward. She gagged a little and I let her back off. “You’ll get used to it soon.” I told her, “now, use your tounge on his balls... yes... excellent... suck some more..."

I could see Tiffany had worked Erc into quite a state, and she was already quite worked up. I knew they both needed some release soon. “Tiffany I want you to get on all fours on the bed. Eric is going to fuck you “Doggy Style.”” Tiffany did as she was told. I walked Eric around and positioned him so he was kneeling behind her. I could sense her nervousness. “Don’t worry, it’ll only hurt a little, then you’ll love it.” I told her. I gripped Eric’s cock in my hand and ran the head of his prick along her slit. Then I positioned him at her entrance; “Now!” I commanded.

All at once Eric rammed his full length into Tiffany’s virgin quim. Tiffany squealed; “OH he’s too big! I can’t take it... please Mistress...” She tried to squirm off his cock.

“No you don’t!” I said, holding her still; “Tiffany you WILL like this!” I told her firmly. “Do as I say and enjoy being fucked.”

Tiffany nodded submissively. I waited a few minutes for her to get accustomed to Eric’s gigantic prick, then I grabbed Eric by the hips, pulled him out and guided him back in again.

“Ungh” Tiffany grunted.

I moved Eric back and forth several times more. Then when he’d got the rhythm I wanted, I left him to carry on. Slowly but surely he rammed into her tight cunt. Again and again. Tiffany was crying out and the slapping sound as their bodies came together beat out a steady rhythm. “Tell me how you feel.” I ordered Tiffany.

“Ungh...ungh...ungh.. I feel...good...oh it’s good.. it’s so GOOD! Oh, oh... ah! Yes! Yes! Oh, I love that big... fucking... ungh cock... I want it in me!” Tiffany grunted, pushing back against Eric, rutting like an animal. “Oh god! Oh... oh! I’mmmm.... Im... gonna oh... I’m gonna cummm...” Tiffany screamed.

I ran around behind Eric and gripped his balls. “Don’t come before her!” I instructed, but he didn’t have to wait long as Tiffany soon yelled out her orgasm:

“OHHHHHHH YEEEEEESSSSSSSSS!” Cried Tiffany and fell forward coming off Eric’s dick with a slick popping sound.

Tiffany lay smiling on the bed. She was exhausted and covered in sweat. “Tiffany, Eric hasn’t come yet. “ I reminded her; “you should help him with that.” Tiffany sat up and quickly wrapped her mouth around Eric’s cock. In no time at all Eric was groaning and spurting his seed all over her face and chest. I watched her, proud of a job well done; “Yes, good. Rub it into your tits...”

Eric left quickly and Tiffany lay on the bed. She was all slick from cum and was stroking her pussy. “Thank you Mistress Jade.” She said to me “I can’t wait for the next lesson.

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