Mistress Elaine Ch. 01-07

"Stop. I am Jennifer, one of Mistress Elaine's submissives and she wrote this for you. I am being punished for my mistakes, so she is making me supervise you today. She gave me a list of instructions and she will be checking on us by video at times. Do not talk to me, just do as I say. She knows how much I dislike being here at all."

Jennifer held up a long printed list of her instructions for him to see, then turned away to put her coat on a chair. Her face was angry as she unbuttoned her plaid cotton shirt and took it off, then unfastened her plain bra and put the clothing on the chair. She turned to face him, with her full breasts exposed and her nipples puckering in the chill.

"Mistress instructed me to be topless in skirt and heels, so this is punishment for us both. You are not going to have a good day."

He had to look, even as he hardened painfully, seeing the thin gold chain necklace she wore being carried in the valley between her creamy white tits, and the sway of her pendulous breasts as she came over. She leaned over him to use a key on the chain to unlock his leash, then gave it a sharp tug and snapped the crop on his thigh. Boxwood ignored the pain of the crop and instead focused on Jennifer's tits as they hung down begging to be kissed and fondled as she was leaning forward.

Jennifer did not share that moment with him. She was focused on her business at hand and nothing else. "Bathroom first, Boxwood. Go. "

He got awkwardly to his feet, with his knees stiff, and followed her with his eyes drawn to her skirt and bare back. In the bathroom she hooked his leash to the door and then her hands were on him, tugging his panties down and off. She watched, with her arms crossed below her bare breasts, as he awkwardly sat on the toilet. It was hard to get started sitting down, and the hot pee dribbled out of the cock cage. Jennifer watched, even angrier now, the shooed him into the tub. She sprayed him with ice cold water, squirted liquid soap on him as if he was a stack of dirty dishes, scrubbed him vigorously with a stiff bristled long-handled brush, sprayed him again with ice cold water, then tossed him a roll of paper towels to dry off with.

She stepped away, then came back with a small bundle Mistress Elaine had left - - blue frilly panties labeled "Friday" in script, and a lacy halter bra with the nipples cut out. His hands were still cuffed, so she had to dress him, roughly tucking the plastic cock container into the panties, lingering with the touch of her hand as she felt him try to harden inside his cage. He glanced in the mirror and saw two unhappy people- the topless woman and the cuffed male in training. The computer chimed with an incoming video call, Mistress Elaine's first inspection.

Chapter Seven

Jennifer adjusted the computer screen towards the floor. He and Jennifer assumed the inspection position, but on their knees. Of course he had no trouble clasping his hands behind his back because he was still cuffed.

"Boxwood, Jennifer, so good to see you. Boxwood. Tell me one thing of a sexual nature that you like about Jennifer and what you would like to do about it."

He was torn between pleasing Jennifer and pleasing Mistress Elaine. He knew that if he said what was really on his mind that Jennifer might be greatly offended. He also didn't want to displease his Mistress by telling a lie. Mistress Elaine could see the distress on his face.

"Boxwood. I know what you're thinking. You're thinking that if you tell me the truth that it will get you in trouble. That's wrongheaded thinking. You are always to tell the truth to Mistress Elaine. Boxwood, you're easy to read. I know when you are lying, and if you lie to me I'll not only be highly displeased, but I may accidentally lose the key to your cock cage. So tell me . . . .now."

Boxwood flinched like he was stunned by a cattle prod. Mistress Elaine's command reverberated in his head like a rifle shot. He leapt to action.

"Mistress Elaine, you know that there is nothing in the world I'd rather do than worship your body. But I've been in a state of constant sexual excitement and when I saw Jennifer's bare breasts I wanted to lick and nibble on her delectable tits. I also had an image in my mind of Jennifer bending over and gripping her ankles so I could see and lick her pussy and her asshole, then offering both to me for my pleasure. Forgive me Mistress for being weak and allowing my mind to wander away from thinking only about you." His cock painfully pulsed in his cage as he verbalized his fantasy of debasing Jennifer.

"Very good Boxwood. I know you are weak and would be seduced by Jennifer's obvious charms. Jennifer?"

"Mistress Elaine, I must confess that I did not have any impure thoughts whatsoever when I saw Boxwood. He is filthy, overweight, looks ridiculous in panties and that silly cock cage, and his collar smells to high heaven."

There was a pause. He and Jennifer both rose on their haunches.

"Boxwood has the best story. I think he is telling the truth. Jennifer, you should be flattered. And Jennifer, your story makes me very displeased. I want all of my subs to be in a continual state of suppressed sexual excitement. Jennifer, do you still have sex with men?"

"Yes Mistress Elaine. If you consider my husband a man."

"Manners now Jennifer. So do you still enjoy an occasional cock when you are not dreaming about your Mistress's pussy?"

"Yes Mistress."

"Good. Then it's settled. I want the two of you to act out Boxwood's fantasy. Jennifer. You have the key to the cage. Unlock it. You will go out and purchase a video camera and tripod using Boxwood's credit card and then create a video of you and Boxwood. You will bring the video to me tomorrow. You will lick my pussy while I watch it. If you do not make me cum by the time the video is over then I'll punish you severely and then let Boxwood use you as his sex slave for a week. Is that understood Jennifer?"

"Yes Mistress."

The screen went blank. Boxwood's penis was pressing so hard against the cage that he was wincing in pain. Jennifer looked at Boxwood and forced a smile.

Jennifer tied the leash to the wall. "Boxwood, you are going to wait here while I get the video camera and the tripod. Now be a good boy and tell me where you keep your wallet."

He pointed to this master bedroom. "It's on my dresser." Mistress Elaine had already taken over his house. Now he was resigned to relinquishing control of his bank account.

Jennifer hurriedly scribbled a note authorizing her to use Boxwood's credit card. She uncuffed him so that he could sign his name on the piece of paper. Jennifer decided to be generous and leave the cuffs off.

"Now Boxwood, I expect you to be in the exactly the same position when I return. If you're not I have permission to use the crop until you are in the fetal position crying, or have cum on yourself. And I have no intention of making you cum."

Jennifer left in a huff, slamming the door behind her. He had no idea what to expect. He had never had sex with someone who wasn't interested in having sex with him. His cock however had voted. It was gently throbbing in its cage in anticipation of Jennifer's return.

About two hours later Jennifer returned. She set her items down on the dining room table and then stripped off her top and her bra. The breasts that Boxwood had been lusting over jumped out and bounced against Jennifer's chest. Jennifer was oblivious to the sexuality of her gesture and went about setting up the video camera. Boxwood's cock was straining against its cage.

After setting up the camera Jennifer turned to Boxwood and said, almost as an afterthought, "Are you hungry?"

He nodded vigorously.

Jennifer dug through the many bags on the table and found a food carton with the leftovers from her lunch. She retrieved the worn dog dish and scraped the leavings of her lunch into the dish.

She placed the dish on the floor but did not give Boxwood permission to eat. "Boxwood, I just want to make sure you understand where you stand in the pecking order of Mistress Elaine's stable. I've been with Mistress Elaine for two years and have had to work my way up to my present position. You are on probationary status. Mistress Elaine hasn't even decided if you are worthy to be in her stable. That means that you are to be submissive to me at all times, even when I let you have sex with me. This is to make sure you remember your place."

Jennifer pulled her panties off, squatted over the dog dish, hiked up her skirt over her knees and proceeded to let loose with a stream of urine that went into the bowl and splashed on the sides of the bowl and on the floor. She then took hold of his leash and pulled his head into her urine soaked pussy. Boxwood inhaled the aroma of Jennifer's musky scent mixed with the smell of her urine. He couldn't decide if the odor was pleasant but readily accepted his task of licking her pussy.

"That's a good boy. Now make sure you lick all the way to my asshole."

Boxwood was now relishing his task and Jennifer could sense his enthusiasm.

"Enough," as she tugged the leash away from her. She took her heel and dug it into his back so he was pressed down with his face inches from the urine soaked dog dish.

"Eat all of your lunch and make sure you lick the outside of the dog dish and the surrounding floor. We have to keep your house spotless for Mistress Elaine."

He could not envision a greater humiliation than eating urine soaked food on the floor of his house that was served by a woman he had met under the most dire of circumstances not more than four hours before. His eyes gazed upwards at Jennifer's bare breasts as he willingly lapped up his nauseating meal. His cock continued to relentlessly throb.

When Boxwood had cleaned up the dog bowl and the floor to her satisfaction Jennifer had him stand in front of her. She knelt down and unlocked the cage. The plastic prison clattered on the floor and his cock immediately sprang to full attention. Jennifer eyed his six inch cock with true disinterest. "You men are all the same." She knew that despite all the humiliation she could dish out that he would be able to slough off that embarrassment for the chance to sink his cock into her pussy.

Without fanfare Jennifer took Boxwood's cock all the way into her mouth. She swirled her tongue around his cock. It had only been several seconds but she knew he was already close. She softly cradled his balls in her hand and stroked the area between his scrotum and anus. He drifted off into a dreamy state and within moments was unable to suppress his orgasm. His milky discharge flooded into Jennifer's mouth. She clamped her lips around his cock, almost to the point of pain, and drew back so all of his cum was trapped in her mouth. Jennifer walked over to the dog dish and spit the contents of her mouth into the dish. She then got a glass of water, swished the water in her mouth, and spit again into the dog dish.

"Here's a beverage to go with your lunch. Lick it up and we'll go about making Mistress Elaine's video. I wanted you to cum first so that you can fuck me for a long time without cumming. I don't want to disappoint Mistress Elaine and you don't want to disappoint me, do you Boxwood?"

He nodded no.

"And I'll remember that your infantile fantasy about my tits persuaded Mistress Elaine to let you fuck me. I'll get even."

He shuddered, now knowing that he had made an enemy of someone who was closer to his Mistress than he was. He also knew how clever Mistress Elaine was to pit him against Jennifer. They would both fight for Mistress Elaine's affections. And in the process she could weed out the weak.

He got on his knees and lapped up the contents of his dog dish. His cum didn't taste too bad and he knew he'd better get used to the taste as there were bound to be many more opportunities (he hoped) to do so.

Jennifer removed the collar. He instinctively reached for his neck, massaging the areas where the wide collar had started to cut into the skin. "Boxwood, go to your room and clean yourself up. Put on a nice suit and tie and meet me back here in 15 minutes."

He returned to his room. Everything (except for his wallet) was exactly where he had left it. It was if the whole chain of wonderful and horrifying events over the past twenty-four hours had not happened. He went into his shower and stood under the hot spray as long as he could, allowing for time to dry off and get dressed. When he sensed his time was up he reluctantly turned the flow of water off. He prepared as if he were going into the office, selecting one of his better fitting suits and a recently purchased shirt and silk tie. Presentable.

He went into the kitchen to wait. Moments later Jennifer arrived. She was wearing a crème colored jacket and matching pencil skirt. Underneath was a pale blue silk blouse that was unbuttoned half way down her chest exposing a hint of her powder blue bra. She completed her wardrobe with a pair of matching crème colored pumps with 4 inch heels. She looked absolutely stunning.

"Boxwood, you clean up nicely." He blushed at the compliment. "I took the liberty of buying a new outfit and shoes on your credit card. I knew you wouldn't mind. We have to be dressed appropriately for the video. I know when I've watched porn with Mistress Elaine that she enjoys the interview seduction. You are going to be interviewing me in your office and then you are going to persuade me to open up my blouse so you can suck on my tits. Then you can bend me over your desk so you can lick my ass and pussy. I'll then climb on the desk so you can fuck me. If you do a good job of it I'll let you fuck and cum in my ass."

"Now you'll be Ron Hightower, my real life boss who I wouldn't mind fucking. I'll play myself, Jennifer Hanson. We'll pause between scenes to move the camera. Are you ready?"

He nodded enthusiastically.

Jennifer set up the video camera in his office with an angle that would capture the people on both sides of the desk. The video started with Boxwood sitting at his desk flipping through papers.

There was a knock on the door.

"Come in."

He rose to shake Jennifer's hand. "Jennifer Hanson I presume?"

"Mr. Hightower, thank you so much for affording me to interview for your executive assistant position."

"Not at all, have a seat."

Boxwood held up a piece of paper. "I see here that you have a number of years of experience as an executive assistant."

"I do, I've worked at a half dozen major corporations. My husband recently transferred here so I'm looking for a new job."

"Well, right now I've already interviewed a number of candidates and I already have a half dozen candidates I'd rank ahead of you based upon your experience and strength of recommendations."

Jennifer showed disappointment on her face. "I'm so sorry to hear that. Did you receive my recommendation from my last employer, a Mr. Hotchkiss?"

"I did."

"Well, he wasn't able to put this on my recommendation." Jennifer carefully unbuttoned the remainder of the buttons on her blouse and removed her jacket and blouse and casually tossed them on the floor. She then reached behind her and unhooked her bra. She bent forward slightly to slide the bra off her shoulders. Her tits fell free. Boxwood's penis, already erect, was now rock hard. She tossed the lacy powder blue bra so it fell on top of Boxwood's head. One of the cups of the bra covered his face. He was able to smell a trace of Jennifer's perfume on the bra.

"Look at the label on the bra. You see here that Mr. Hotchkiss would have given me a 'D,' as in 36D, on my tit quality."

Boxwood examined the label and fingered the slightly damp cup of the bra. He was tongue tied. "I . . . well . . ahem . . . well Ms. Hanson, I'll have to make a handwritten note on Mr. Hotchkiss's recommendation. That may weigh heavily in your favor." Boxwood's hesitation was genuine and it came out as quite endearing in the video.

"Well Mr. Hightower, if you were to come around to my side of the desk I you'll be able to more fully appreciate what Mr. Hotchkiss was talking about."

Boxwood turned the camera off and then repositioned it to capture the action on Jennifer's side of the desk.

Jennifer faced Boxwood. He cupped the undersides of both of her breasts and leaned forward to draw one of her erect nipples into his mouth. He showed great surprise when he discovered that Jennifer had dipped her nipples in cayenne pepper. The burning sensation in his mouth took away any pleasure he might have experienced. He knew that Jennifer now had to be feeling the same burn so she must have been quite determined to deprive Boxwood of his reward. He pushed on, licking the nipple until the cayenne had dispersed in his mouth. As the numbing sensation in his tongue abated he began to enjoy the feel of the nubby skin of her nipple. He raised up her breast and ran his tongue the length of the underside of her breast. Jennifer was unable to suppress a sigh.

She unzipped her pencil skirt and let it puddle at her ankles. She kicked it off but kept on her heels. She bent forward so the top half of her body was prone on the desk. She then used her hands to part the cheeks of her ass. "Oh Mr. Hightower, I apologize but in my haste to get to this interview I forgot to put on my panties. Now about those two holes in my resume, if you come closer you'll see those two holes."

Boxwood had completely forgotten about the video or Mistress Elaine. Jennifer's exposed bottom as she balanced on her heels and bent over his desk was without a doubt the most sensual image he had witnessed in his entire life. He plunged his tongue with vigor into Jennifer's inviting asshole. He licked in broad strokes between her anus and her clit, savoring the taste of each. Jennifer, despite her proclaimed distaste for Boxwood, was impressed with his oral skills and was approaching an unexpected orgasm. Mistress Elaine had instructed them to produce an erotic video so Jennifer took that as a license to cum.

"Lick my cunt Mr. Hightower. Make me cum."

Boxwood was pleased that he had gotten through to Jennifer. He was worshiping her body and she approved. He redoubled his efforts to suck on her clit and for good measure started teasing her bottom with his finger.

"OhGoddddddddd!" Jennifer's feet wobbled back and forth like a ship pitching in a storm. A flood of juices covered Boxwood's face. Jennifer was gasping for breath.

Not to be denied his fantasy Boxwood took his long suffering cock and sunk it deep into Jennifer's sopping wet pussy.

"It's too sensitive . . . . . oh shitohshitohshit" Jennifer couldn't control the waves of pleasure that were crashing within her. The contractions in her pussy were pushing Boxwood to a premature climax. He had other plans that were at Jennifer's invitation. He pulled out his cock. Jennifer could sense the void.

"No, no, Mr. Hightower. Please put it back in!"

Boxwood fully intended to. Just not in the same hole. He approached Jennifer and put the head of his penis into her vagina to lubricate it and then against her rosebud.

"No, no, Mr. Hightower. Not there!"

Boxwood pressed forward. Jennifer was pinned against the desk so her anus gave way. He slid in quickly the rest of the way. The sudden penetration took Jennifer's breath away. She was taking short quick breaths and was unable to talk as Boxwood pounded away. The initial pain was giving way to an intense rush of pleasure. Jennifer moved her hand underneath her to rub her clit. Boxwood felt the surge in his penis as he did a full stop deep inside Jennifer's ass. His long period of denial gave way to the most satisfying orgasm of his life. It felt as if he was spurting cum for minutes.

"MR. HIGHTOWERRRRRRRRRRRRRR." Jennifer also forgot about the video or that she despised Boxwood. She had just been rewarded with one of the most tumultuous orgasms of her life.