A COVID Journey Pt. 26

Howard said, "Perfect. Masturbate until you cum, but keep your eyes on me."

Jessica rubbed her clit harder. She was soon breathing harder as the warmth grew between her legs."

She began to moan, but their eyes remained locked on each other.

"Cum for me." He said.

Jessica forced her eyes to stay open as she began to quiver. She pressed hard against her clit, squirming on the bed as her climax engulfed her.

"Howard!" She cried, "Oh god, Howard."

Howard smiled. "Let me taste it." As he knelt beside her.

He grabbed her hand and put her fingers into his mouth, greedily sucking them.

As Jessica's breathing calmed, Howard said, "Go. You have seventeen minutes before your class."

"Thank you, Howard. I will always be available for you."

Howard smiled, "Go. I won't forget that."

Jessica left his room, and Howard went to take a shower.

As Jessica entered her room, she thought about how Howard was the only man she'd ever let dominate her. His controlling her masturbation was the hottest thing she had ever experienced. There was something about him that made her want to be his submissive.

STEVE BECOMES A PONYBOY.

When they got to the pony equipment room, Alice asked, "Adam, will Subbie's headphones and our microphone work in here and out in the yard?"

Adam replied, "Yup. They're connected to the WiFi system, and that signal is everywhere. These earbuds will work like the headphones and blend into the horse's head hood. However, they don't cancel noise as well as the headphones."

"Adam, you think of everything."

"That's what Howard pays me to do. By the way, I have a class this afternoon."

"That shouldn't be a problem. Jessica's class ends at 10:30 a.m."

Alice found the perfect hood for Subbie's transformation into a ponyboy. It was shaped like a horse's head. The mouth was wide open so that a bit could go into his mouth. The eye hole was just a narrow vertical slit that could be covered completely. It also had a bright red plume on its top. She found a matching butt plug horse tail and put them all in a bag.

Adam had finished setting up both stalls and was putting Michelle on the dildo pole as Alice left to get Subbie ready.

Alice went to the kitchen and got a tray to bring Subbie his breakfast. When she got to his cell, he was naked, on his spread knees with his hands behind his head, and looking at the floor.

Alice said, "Steve, you can get out of that position. You're not my Subbie until I prepare you for today's games. I do like how you were waiting for me. I still find it hard to believe that you have never had a mistress."

Steve replied, "I'm too shy around women to even look for a mistress. I have watched a lot of female domination porn to learn how to be a good male submissive."

Alice responded, "Well, you exceed Mistress J's and my expectations."

"I'm glad I pleased you. I've been wanting to serve a Dominatrix for a long time. I'm grateful this opportunity came along."

"You don't mind the pain we have inflicted?"

"As long as you and Mistress J are enjoying yourselves, then so am I." Steve said as he took the last bite of his breakfast."

Alice instructed, "Go brush your teeth, use the toilet, and then use the enema wand in the shower to clean yourself."

Steve went to the bathroom, and in ten minutes, he gave out freshly cleaned in and out.

Alice announced, "This morning, I am going to transform you into a ponyboy. Put your cuffs back on.

When Steve had finished putting on his wrist and ankle cuffs, Alice picked up the earbuds. "Subbie, these earbuds will work similarly to the headphones. All you will hear are the synthesized voices. You will hear some other sounds as they don't cancel the noise as well as the headphones. Put them in."

Steve put the earbuds in his ear.

Alice pulled the horse hood from her bag and had Steve place it over his head. She tightened the straps on it, put the bit in his mouth, and tightened that. She put his other hood in her bag.

Steve was grateful that the hood was not too tight around his neck.

She clipped his wrist cuffs behind his back and put a hobble chain between his ankles. She clipped a leash to the O ring on his horse hood's neck.

The final touch was to put the headphones back on him. She turned on her microphone, and Steve heard the computer-synthesized soprano voice say, "Subbie, you should be able to see enough so you don't trip.

It was challenging for Steve only to be able to see out a narrow vertical slit, but he made it up the stairs and outside with no problem.

Alice put the leash in his hands and grabbed his penis, and tugged on it. Steve heard the computer-synthesized voice say, "I like this leash better."

She moved quickly, and Steve had to hustle to keep her tug on his penis from becoming too intense. Alice sensed his concern and giggled.

They made it to the pony equipment room without any problems.

Steve noticed there were four stalls, each with a bed and en-suite bathroom. In one of the stalls was a woman already decked out as a pony. It appeared she was impaled on a pole. Around her neck was a wide, dark red collar. Ropes went from the sides of the collar to each side wall.

Alice synthesized voice, "Subbie, Michelle has asked to join you as a pony girl. Isn't she beautiful?"

Steve shook his head yes and tried to say yes through his bit.

On her head was a harness with a bright red plume on the top. One strap crossed her forehead and around to the back of her head like a sweatband. The strap on the back of her head had a large ring that her hair had been pulled through to form a mane.

On her forehead, the strap was shaped like a diamond. A strap went from the diamond over her head to the ring in the back. Another strap went from the sides and had horse ears on them. Where they crossed was where the bright red plume stuck straight up.

There was a strap from her ponytail ring to the collar. On the sides of her face were two more straps that were a continuation of the strap over her head that went down to the collar. Each strap had a ring that was aligned with her mouth.

In her mouth was a bit similar to the one in Steve's mouth. It had bars on both sides that went beyond the mouth and ended in a ring to attach the reins.

A dark red under-breast corset was connected to the collar with straps. She had one thick strap between her breasts and straps on either side attached to the middle strap at her collar. Over her breasts were rings that fit over her nipples and were held in place by thin strips that formed an X connected to the other strap. The corset ended in a thick, wide belt. On her nipples were little bells attached to her nipple clamps. She was jiggling her breasts so that the bells made a pleasant sound.

Her hands were in gloves resembling hoofs connected at the wrist to the wide belt. Above her elbow were cuffs that were connected so that her arms were pulled back, pushing her breasts forward.

On her legs were black thigh-high boots with no heel, as the toe was shaped like a hoof.

The final touch was a horse's tail butt plug which matched the color of her hair.

Her vagina was impaled on a dildo on a pole, so she could not move. It was clear from the expression on her face that she was enjoying it.

Alice's computer-synthesized voice said, "Adam, Michelle looks great!"

Adam replied in a tenor computer-synthesized voice, "I like Subbie's horse's head hood. Do you need help transforming the rest?"

Alice replied, "Sure."

Alice and Adam attached ropes from Steve's collar to each side, just like the woman had. Next, they instructed him to stand on some 4" blocks.

Alice measured the distance from the ground to his ass hole. She selected a pole and attached a dildo to its end. Alice squeezed a tube of lube into his ass. The dildo mounted in a pole was inserted into his ass, and the end of the pole went into a hole beneath him.

Soon, Steve was transformed like Michelle was, even with the corset. His accent color was blue. The only other difference was that his butt plug tail was attached to the belt at the bottom of his corset, as he already had a dildo in his butt.

Alice examined their work and said, "We need to decorate his cock."

She installed a ball stretcher and pushed a cock ring to the base of his penis. She hung a bell from the end of his cock. She tapped on her phone, and the dildo in his ass started vibrating.

He yelped in surprise, and Alice laughed.

PONY PLAY

Alice said, "Well, Adam, we have a nice pony girl and boy."

Adam replied, "And we won't have to teach my pony girl how to do high steps."

Adam and Alice attached long leads to Steve's and Michelle's collars.

Alice unhooked the ropes on Steve's collar attached to the side walls.

Steve heard Alice's synthesized voice say, "Subbie, We are now going to teach you to do high steps. That means you lift your knees high before you take each step forward."

Steve saw Adam hand Alice a buggy whip. He recognized it from the FemDom porn he enjoyed. It had a handle about six feet long with a six-foot-long thin whip at the end.

They led them outdoors. The bells on his nipples and cock tingled softly as he walked. Steve noticed there was a wide track around the back lawn.

Steve heard Adam's computer-synthesized voice say, "Mistress Alice, I will have Michelle demonstrate the step. You work with Subbie to get him to prance correctly. Now, let's lead them out to the lawn."

Alice and Adam stood about forty feet apart on the lawn in the middle of the track. Steve could see through the eye slits that Adam gave Michelle about ten feet of the lead and stepped back until the lead was taut. Adam flicked the buggy whip at Michelle's butt and made a clicking sound. She started moving around him in a big circle, picking her knees up high before moving her foot forward."

Alice told Steve, "Subbie, you are to do prancing steps like Michelle."

She flicked her buggy whip, and he felt its sting on his butt. He started forward. He moved his knee up, but not high enough for her. She cracked the whip on his thigh and said, "Subbie, You need to go higher with your knee. Try again."

It took a couple more revolutions and many flicks of the whip on his butt, but eventually, Steve consistently brought his knee up to almost his waist before kicking his foot out. The prancing steps caused the bells on his nipples and cock to ring.

Alice said, "Now, let's speed it up."

Adam and Alice both cracked the whip behind them. They started to do a prancing jog.

Adam said, "I think they have it. Let's get the carts attached."

Steve and Michele were brought over to the carts. The carts were similar to those used in horse racing. Each lightweight cart had two wheels, with a seat between them. A single pole stuck out the front under the seat's frame. The poles curved up at their end. He noticed that each pole had a dildo in it. He was not surprised when the pole was lifted between his legs, and the dildo went up his ass. Straps from the belt at the bottom of his corset attached the pole to keep the dildo in him. He noticed that the dildo on Michelle's cart was at a different angle, but that made sense as it was going into her vagina.

Alice said, "We're going to let you get used to pulling the carts before we get on them." She grabbed his lead and pulled on it.

He felt the weight of the cart pulling on the dildo in his ass. It was a strange sensation as they walked around the track.

After they had completed an entire circuit, Alice said, "Subbie, now you get the privilege of pulling me in the cart." She climbed onto the seat and flicked the buggy whip against his ass. He took off at a walk.

It was a little more challenging pulling the cart by the dildo up his ass with her on it, but the track was smooth, and the cart's wheels turned easily.

When he finished a lap, he noticed ahead of him that Adam was riding the cart that Michelle was pulling. Alice cracked her whip and said, "Okay, Subbie, catch and pass them."

He took off at a trot. Adam didn't notice them until Steve had caught up with them, and Adam could hear the bells on Steve ringing loudly. Adam urged Michelle to a faster speed.

Then Steve heard a male bass voice he hadn't heard before. "Okay, you two, if you're going to race, let's make it fair. Walk over to the starting line. Michelle gets the inside track."

Alice replied, "Okay, Howard. We'll do as you say."

So this was Howard—the ultimate Master of them all. Steve couldn't see much through his eye slits, so the person behind the voice remained a mystery.

When Steve was lined up next to Michelle, Alice asked, "So what does the winning pony get?"

Howard laughed and said, "Breeding rights... Greek breeding rights."

Adam and Alice agreed.

Howard got a starter cap gun, and when he pulled the trigger, they were off.

Michelle started with a slight lead, but Steve passed her on the first straightaway. The bells on their nipples and the one on Steve's cock rang crazily. Steve easily won the race.

Alice and Adam unhooked Steve and Michelle from the carts. Michelle's butt plug tail was removed, and it was attached to the belt of her corset. She was bent over a picnic table and secured. Adam squeezed a large amount of lube into her ass. Alice took Steve's tail, which was attached to the belt of his corset, and after squeezing lube into his ass, worked the butt plug end of the horse's tail into his ass.

Alice whispered in Steve's ear, "She wanted to lose because she wanted your cock up her ass. You know you want to please women, and this is how you will please Michelle." Then she said so that all could hear, "Subbie, you are to thrust into her ass until you cum. Don't you dare disappoint me!"

Steve's cock was hard as Alice's hands guided it into Michelle's rosebud. With the copious amounts of lube, it went in smoothly despite the tight fit.

Steve had never done anal, but it was clear Michelle had, as she enthusiastically thrust back on his cock as he thrust into her.

This was not something that Steve had ever wanted to do. His desire, as a submissive, was to be pegged, not to thrust his cock into a woman's ass, but this was something Alice wanted him to do, so he was all in.

Michelle was thrusting her ass back and forth. Steve matched his thrusts to hers. At first, he felt conflicted, but as Michelle started to utter sensuous moans, he realized that even in this, he was serving a woman. He thrust with more energy.

Alice said, "Cum into her ass, Subbie." And rubbed her gloved hands on Steve's naked butt.

That was all the stimulation Steve needed. His body jerked as he shot his wad into her ass. He soon collapsed onto her back.

Alice whispered into his ear, "If you weren't wearing the bit, I'd have you clean up your mess. We'll save that for the future."

Steve felt a hand on his hood, and he was plunged into darkness as his blindfold was reinstalled.

Steve heard Alice say, "Michelle, you need to return the favor to Subbie. Use this feeldoe in his ass."

Michelle replied, "With pleasure."

Steve felt multiple sets of hands on him and soon found himself in the position that Michelle had been in, strapped to the table.

He felt lube being squeezed into his ass and then the end of the feeldoe against his ass. The feeldoe was slowly worked into his ass.

As Michelle worked the feeldoe in and out of him, he felt the rest of his ponyboy outfit being removed. Alice instructed him to lift his right foot, and she removed his hoof boot. She repeated the instruction for his left foot.

Soon, all that remained of his ponyboy outfit was his hood. Michelle hammered the feeldoe into him faster and faster until he heard her orgasm. If he hadn't just cum into her ass, he would have cum also.

Alice instructed him, "Keep your eyes closed."

He nodded yes and felt the straps on his horse's head hood being loosened. When it was removed, the earbuds he had been wearing were removed. He could hear the sound of nature and not much else. Howard, Alice, and Adam were quiet. Michelle's deep breathing as she recovered from her orgasm was the only human sound his uncovered ears heard.

He kept his eyes closed as another hood was put over his head. It felt the same as the one he'd been wearing most of the time since he had entered the van. Once the hood was secured, his noise-canceling headphones were put back on.

He heard Alice's synthesized voice say, "Subbie, You may open your eyes."

He was disappointed but not surprised that he could not see, as the blindfold had been put back in. He felt his wrist and ankle cuffs being put back on.

Alice asked, "Subbie, What color?."

He replied, "Green, Mistress Alice."

Then someone shoved a penis gag into his mouth, silencing him.

A GAME OF POOL

Steve felt two sets of hands as they cuffed his hands behind his back. He still could only hear their computer-generated voices.

He heard the synthesized voice that he recognized as Mistress J say, "That was hot! I enjoyed watching the tail end of that. Can we play pool now?"

The synthesized voice that Steve knew as Adam said, "The modified pool table is ready."

Alice said, "Master Howard, may Mistress J and I take Subbie and play pool?"

A new synthesized voice, which Steve knew must be Howard, said, "Yes."

Mistress J responded. "Thank you, Master."

Howard said, "Adam, Michelle, let's go make ourselves an early lunch, and then I have a bunch of paperwork to get through in my office."

Michelle said, "Adam, maybe after lunch, you can tie me up and fuck me.:

Adam laughed, "For you, honey, I'd do almost anything."

Howard, Adam and Michelle departed the group.

Steve felt himself being led back into the house. He heard sliding doors open and then felt the rise of an elevator.

He was led down a hall until a door opened, and he was instructed to lie facedown on a board. Once his hands were strapped to the board's legs, he felt his legs being lifted and separated a little more than 90 degrees. His legs were strapped to the supports in multiple places.

His legs and torso were now on the same level. There was no support holding his balls up.

He felt the contraption he was on being moved until it bumped against something. He felt a hand lift his balls, and when they were released, he sensed his balls were surrounded on one side but exposed on the other.

He heard the synthesized voices giggle, and then Mistress J said, "Subbie, your balls are now the corner pocket of a pool table. Your legs are the side bumpers of part of the table. Mistress Alice and I are going to play a game of pool, where every pocket except your balls will be a scratch, and the ball will be returned to play. For the ball to go in your pocket there will need to be enough force to push your balls back a little. We'll switch on every ball, so we play until every ball goes in your pocket—the woman with the most balls wins. The cue ball will only be used for the break. I will do the break."

Steve heard the balls being racked.

He heard the cue ball being hit and then the racket as the balls separated. A couple of balls softly hit his legs, but not his balls.

Alice's synthesized voice said, "My turn."

Steve heard the crack of the pool cue hitting a ball and then felt the billiard ball hit his balls hard. He let out a "ugh."

He heard the two women laugh.

Steve heard a louder crack of a pool cue hitting a billiard ball, and his balls were hit with more impact than from the first ball. Steve screamed through the penis gag.

He heard Mistress J's synthesized voice say, "Damn, It bounced back."

The next ball hit his thigh hard and missed. "Ugh." was all the women heard from Steve.

The next ball hit his balls straight on, and he jerked in pain and let out an "Arrg."