The Lessons

As he descended totally naked into the basement behind his beautiful new Mistress, John’s eyes became accustomed to the dim lighting. His bulgingly erect cock swung heavily from side to side as he stepped lower. If his hands hadn’t been secured behind him he would have grazed hold of his shake, at least to stop it slapping his stomach. There, in the middle of the room was a man, at least, it had to be a man. It appeared to have a cock, but there were all sorts of apparatus attached. The human was stood, legs spread shoulder-width apart due to a pole and shackles attached to its ankles. Although Pet, formerly known as John couldn’t see it, a pole with a 10″ dildo buried in it’s ass was anchoring this being to the spot. The head was covered in a gimp mask and it had a virtual reality headset attached. A ball gag was Secured in its mouth. Earphones were covering the ears, and much like John, its arms were secured behind, elbows also tied tightly. Where it probably had nipples were twoclamps, wires sprouting from them. The cock was half encased in a glove like device that seemed to pulsate and quiver. The wretched creativity was writing in what looked like ecstasy, moaning through the ball gag as though begging for something. The sound of mechanical titillation filled the air. It was both horrifying and intotoxicating to Pet who felt his cock swell even more, if that was even possible.

“This is my Gimp, Pet. Worthless piece of shit that he is. Only on Saturdays though. Rest of the week this is Patrick, my loving husband. But once a week he comes down here so I can take him to the edge of sanity by edge him until he is a dribbling fool. I always bring him back before he loses his mind. That’s why he loves and worships me. Like you will do in 28 days. He’s watching porn right now. Filthy porn. Obscene, disgusting acts. He loves it. He can’t hear me, and obviously he can’t see me, but he can feel me. And the various appliances are taking him to the edge of ejaculation again and again. We’ve lost count of how many times he begs us to come which is why we gag him. It get’s irritating listening to his pleading over and over.”

And with that, Jenny pulled the sleepe from Gimp’s cock and started stroking it really fast. Immediately he started to thrash about, whining, mewing, pleading through inhuman noises. Pet knew he was begging for relief.

“Come over here Pet. Kneel here.” She indicated to a spot directly in front of her gimp husband. He compiled, dropping to his knees. Jenny pointed the cock at her trainee.

“Suck this you whore.”

John looked horrified. He was straight. He wasn’t a cock-sucker.

“Listen you worthless piece of shit, if you don’t try and suck this cock as far down your throat as you can I will throw you out naked. We’ll keep your money and you’ll be on your own. Remember the contract. You will comply with all our instructions.”

And with that, Jenny grabbed the back of John’s neck and impaled his mouth on Gimp’s impressive 9″ rock solid cock. He felt the penis penetrate his throat and started to gag. She pulled him back, giving him some relief, but carried on wanking the cock. Then she brought it back into his mouth hole and started again. Wank, thrust, gag, withdraw. Again. And again. Tears formed in John’s eyes, but Jenny was shouting at him.

“Come on you worthless whore! Swallow his cock. Get ready to eat the cum. You know you’ve wanted this for so long!”

It seemed like this went on for ever, but the truth was five minutes later Jenny felt Gimp start to ejaculate, so she forced her Pet’s head and her husband’s cock together. After six hours of edging, the copious amount of semen was impossible for Pet to swallow. It poured from his mouth, dribbling down onto his chest. Gimp grunted and bucked, feeling the ecstasy surge through his body. Rutting wildly, he tried desperately to force his manhood deep into Pet’s face hole, like a dog trying to find a bitch’s hole. Finally, spent, she let the two separate. John was sobbing.

“Oh for fucks sake, why are you crying Pet?”

“I’m so happy. I don’t know what’s happened to me.” He was shaking with emotions. It was too much. Jenny let go of the scruff of his neck and he crumpled to the ground.

“Millie, help Pet to his lodging. Reset Gimp for edging. He needs another four hours tonight. Don’t forget to hydrate him through the IV and drain his bladder.”

And with that she retired for the night.

Six Months Earlier……..

John’s wife left him because she was fed up with his observation with sex. He wasn’t sad. She never even tried to satisfy him. Even so, it was all he could ever talk about and want. He drove her away, and after 20 years of marriage Sharon left him for the peace and quiet of living alone. And that is where our story would end except…

John was now able to go to the gym as much as he wanted, to watch what he wanted, to do what he wanted. And he wanted sex. All the time. So he did. Albeit on his own. But he no longer feared being discovered by a wife who wanted to catch him masturbating, so she could throw it in his face, call him a pervert, and leave. And so he spent happy evenings experimenting on himself, exploring his real sexuality, and he finally came to realize that he wanted to be someone’s sub. To follow explicit instructions, to have his sex drive harnessed and used for another’s pleasure. Vanilla dating for the sake of a traditional evening of groping and hoping followed by plain old fucking wasn’t what he wanted.

It was during one of his forays into the fringes of the World Wide Web that he stumbled upon a website for the more liberally sexual deviants of society. He joined the forum and enjoyed conversations asking others like him what they enjoyed, how they satisfied themselves and what he could do to become what he yearned for: A plaything, a slave and a follower of rules.

One day, out of the blue, he received notification that a fellow forum member had sent him a pm. Jenny explained that she was a dominatrix who was in the process of training an aptice and as such she needed a willing participant to help her guide her student in the art of domination. It would require one month of his time, and the training would be conducted in her home. If he would send nude photos of himself, fully erect, and videos of himself ejaculating she would let him know Whether he was suitable. If he was accepted she would provide him with a list of instructions with which he must comply.

Grasping both the opportunity and his cock, he made some artistic videos and photos and sent them to Jenny that night. John was so excited he pulled himself off three times that night before finally managing to sleep.

He awoke the next morning and checked his phone for messages. Sure enough, she had responded. He was delighted to find out that his exercise regime and beautiful, uncut 8″ cock had passed muster and that he was invited to join her at her place in Phoenix in two weeks. He had time to arrange his vacation from work, and it gave him an opportunity to prepare himself and a bag with all the things he would need. Jenny had also provided one photo. She was naked, sat bolt upright in a large wooden chair that was on a raised plinth in the center of what looked like a quintessential sex dungeon. Her legs were spread, and she Hold a leather crop over her pussy lips. Her face was stunningly beautiful and yet her hair was short cropped. Reminiscent of Sinead O’Connor. Kneeling at her feet on all fours was a woman, her legs also spread wide. She had an ornamental ball protruding from her ass, and she had both hands on Jenny’s large, perky tits. She was staring intently at Jenny’s bald cunt. It was the singularly most erotic thing he had ever seen. He was instantly hard. The instructions for his preparations were detailed.

1. Purchase hair removal cream (enough for one month) and remove all body hair.

2. Purchase a 10″ butt plug from the vendor of his choice and wear it every day.

3. Weight training twice a day to ensure maximum fitness. In addition run 5k every day.

4. Purchase Viagra from the internet vendors (as supplied). 28 pills.

5. Start eating your own cum every day, working up to twice a day by Friday.

6. Masturbate at least four times a day.

7. Bring $5000 cash training deposit, returned upon successful completion.

8. Start using an enema kit every day. Reduce food intake to ensure only one bowel movement per day. Cleanse after each bowel movement.

Finally there was a contract that required signing and returning by overnight mail.

I, John Crawford accept the following conditions during my stay with Jennifer Milford, 3rd December to 31 December 2024.

Should I decide to leave her home and training facility early I will forfeit my cash training deposit of $5000. During my stay I will receive enough food and water to sustain my life. I will sleep wherever I am told. I will comply with ALL instructions issued by Ms Milford and her student, Millie Haversham AT ALL TIMES. Should they wish to terminate my visit I will still forfeit my deposit.

John read it again. His cock was throbbing and painful. He stared at the photo whilst stroking his shaft. After reading the instructions again his imagination started to run riot and his orgasm came quickly. He shot the load into his left hand, then for the first time ever he tentatively took a sniff. He had never liked the smell. Determined to at least see if he could manage item 5 in the list, he licked a big glob of cum out of his palm and swallowed it quickly. It was not great. But boy, was he excited. If he didn’t think about it, just got on with it, he could get the load down. After all, he watched women doing similar on line. He managed to consume it, then printed and signed the contract before preparing an envelope for mailing the followinging day.

The two weeks passed excitingly slowly for John. He was pedantic in his following of Jenny’s instructions. His fitness levels were off the scale. He was eating all of his cum from all four wanks. His asshole had never been so clean. Finally, bag packed, he made his way to the airport. He had been told a driver would pick him up at arrivals, and sure enough a well dressed man in a dark suit was stood holding an iPad with his name highlighted. The driver took his bag and commented that it couldn’t be a long trip since the baggage was so light.

An hour later, after some heavy traffic, the car parked outside of a nice looking cul-de-sac home in the suburbs. John got out, his cock snaking down his left trousers leg in anticipation. The driver retrieved the bag and John tipped him $5 before turning and walking up the driveway to the front door. As he reached the doormat the door was opened to reveal who was rarely Jenny, but so much sexier than he expected for midafternoon. Standing in black 4″ heels, skin tight black jeggings, bare midriff decorated by a gold belly ring, black halter top, muscle arms, large enhanced breasts, long dangly gold earrings, bright red lipstick and smoke eye makeup, she took his breath away.

“Hello John. So glad you could make it. Come in come in.”

As he entered the house she hugged him and kissed him on the chef. Turning to her left, she extended her arm and pointed out Millie, who was stood to one side. Millie was similarly dressed and equally as beautiful. His cock got harder.

Millie hugged him too, then reached for his bag, also commenting how light it was. Jenny closed the door and invited him into a large office space off the main hallway. Jenny walked behind the big oak desk and sat down. There was only one other seat, and Millie put his bag on the ground then sat down too. John stood rather awkwardly in front of the desk, hands trying to cover his obviously erect member.

“We thoughht it would be best to get you accustomed to your place here as soon as possible, so first things first, please provide your $5,000 deposit, and the. We can start with the rules and exactly what we expect of you during your stay.” Jenny was firm but polite.

He reached down and produced an envelope from the side pocket of his bag before handing it to Millie who was closest. She began counting the notes whilst Jenny continued.

“Remove your clothes and place them on the desk. You won’t be needing them for the next month. Unless there is an emergency and you need to exit the house in a hurry, in which case you can grab a nice pink house coat from the front door closet. Excepting that situation, we expect you naked all the time. Do you understand?”

John nodded yes, then removed his Shirt, followed by his shoes and sock, and finally his pants and underwear. His penis was fully erect, his body too was rock hard from his exercise regime. Jenny stood up and came around from behind the desk, slowly walking around him.

“Oh we did very well Millie, didn’t we? Look at his physique!” She touched his body lightly, tracing her long fingernails over his chest, scraping his nipples. He shuddered in excitement. Reaching down, she grabbed his manhood and squeezed hard.

“That is a quality erection. Have you started the viagra yet?”

“Not yet. I Only got 28 tablets, I wasn’t sure when to start. You didn’t specify.”

Jenny looked disdainfully at him. “You are here for 28 days, and you have 28 tablets, therefore wouldn’t it be logical to have taken one already? This is day one isn’t it?”

“Yes Jenny. I can take one now. They’re in my bag.”

Millie left the room, then came back with a glass of water. She pointed at his bag, so he reached down to open it and retrieved the medicine.

“Good. One a day. Don’t forget. Other things not to forget, from now on I am Mistress and Millie is Miss. From this point on you will not look us in the eyes. You will focus your eyes on our breasts, cunt, ass, whatever body parts turn you on. But you look us in the eyes and you will be punished. Whether we flog you, use the stim machine on you, edge you to the point of madness, ticket you, pierce you or generally cause you disappoint, you will assuredly become accustomed to various methods to ensure you are trained to be a most respectful servant. All you will know is that keeping us happy is your sole purpose. Am I clear?”

“Yes Mistress!” John was giddy with excitement, and he lowered his eyes to star at Jenny’s substantial tits.

“Ok.Millie, handcuffs please. Now lets start in the place you will get to know intimately. Follow me.” And with that she led him to the basement door…