Andrea: Mistress Susan's Proxy

"Lick me there Steven! It feels so good and it lets me know you really love me and know your place!"

Driven by love and longing he never felt before he went to his duty with passion, licking everywhere, rewarded by her sighs of pleasure.

"Now I want to feel your tongue inside me Steven! Deep as you can go!"

He felt her orifice relax a bit and slithered his tongue into it, feeling it pass her sphincter, until he felt the softness of her rectum. She moaned her approval, keeping him at it until his tongue tired. Then she had him worship her left cheek and hip before guiding him to where her pussy awaited, now oozing wet.

He nuzzled in her dense aromatic bush, his erection pressing all the more painfully against the spikes, the throbbing ache in his balls worsening beyond belief. She made him lick her slit, then rubbed her cunt full over his face to smear him with her juice, before pushing him back and away, resuming her seat. Steven took his place on his knees before her.

Their eyes met, and she was delighted to see his vacant gaze of utter enthrallment. But would she ever be able to break down any boundaries or limits he might have? At the session's end she meant to give him his first small test.

"Well and good Steven. I can feel your love for me and it makes me happy, though you have yet to fully prove yourself. Do your balls ache?"

"Yes Mistress!"

"Does the cage hurt your cock?"

"Yes Mistress!"

"Unfortunately, Steven I cannot grant you release yet. You have much suffering ahead of you to atone for your long history of wanton and heedless masturbation. That unearned pleasure carries severe punishment. I will not cane you this evening because I want you to heal first. Your welts will be allowed to scar and toughen before I add new ones. A fully scarred ass is one of the prices you must pay if you want to become my live-in slave. Now, I want to know every detail of your sexual experience. Anything you reveal that indicates selfish lust, mistreatment or disrespect of women will add to the length of your punitive ejaculatory deprivation. I will know if you are holding back and if I must pry things out of you that too will add to your punishment."

Steven had never been a big lady's man, but he'd had his share of women over the years. And he was indeed guilty of multiple transgressions, especially when young. He had never committed any violence against a woman but had pinched and slapped some asses and groped some women in bars when drunk. He had never raped but had more than once seduced a naïve young woman with blandishments just to use her for sex. There had been the typical promises to call them. He spilled his guts freely, fearing the consequences of holding back more than of confessing.

Had had married at age 26 and had found some measure of fulfillment of his latent longings with his wife, who had some dominant inclinations. She was very much the boss in the bedroom and every evening they made love she would dictate how she expected to be satisfied. But nothing she demanded approached the extremes his secret fantasies involved. He adored her and became quite adept at pleasuring her, even doing on line research to find ways to enhance her orgasms. But then she had been cruelly torn from his life, leaving him grieving in solitude.

Andrea's heart went out to him when he described his marriage and bereavement. She wondered if his wife might have become a full-blown Mistress if subjected to the proper influences, their marriage becoming female led. And, she was eager to test his skills at oral pleasuring.

Steven finished his confessions and knelt silent with head bowed. Andrea pressed him.

"Look at me Steven!"

He looked up, meeting her eyes.

"Is that everything? Don't bother lying. I will know, and you will regret it."

He looked into her eyes, unwavering. "It's everything Mistress."

"I believe you Steven. Your past transgressions are not of the most egregious sort, but still they cannot go unpunished. You will get another caning this evening and you will suffer denial of orgasm for another month. Any whining or begging will only add more weeks to your sentence."

She rose from her chair, picked up the cane that lay beside it and pointed to the chair. He knew to bend over it and offer his ass for punishment. Fifty harsh strokes fell on him. He cried out in pain with each, bringing wet warmth between Andrea's thighs. With the last stroke she grabbed his hair, pulled him back from the chair and slipped into it with legs parted, his face inches from her cunt.

"You may give me pleasure now Steven. You have all but boasted of your skills. Let us see if you can live up to that!"

She pulled his face into her crotch and shuddered in delight when she felt his tongue work begin. Indeed, his late wife had trained him well. He seemed to sense her readiness to come and after some initial lapping and tasting he focused on her clit and worked it hard, sucking it in between his lips and wriggling his tongue's tip against it. Her orgasm took her by surprise, its suddenness and intensity. She bucked and convulsed in the chair with a wail of ecstasy and then felt him continue with just the softest fluttering of his tongue on her clit. Half a dozen more waves of delight coursed through her body until she all but turned to jelly and lay draped in the chair, muscles too slack for her to move.

She lay in afterglow, softly petting his head, steeling herself against revealing the growing affection she felt. And there was no need she should deny herself the pleasures she had been deprived of for so long. He would spend the weekend with her, would share her bed and receive in depth and rigorous training. But she would let fall no hint how delighted she had been with his cunnilingus, lest he slack off in his efforts to please. She recovered herself and rose to sit upright.

"That was sufficient Steven, but barely. You are in urgent need of further training, so you will spend the weekend here with me. Now remove my boots and fetch the ottoman over here. Then you will lick my feet. There is much I have to say."

Steven obeyed, first helping her slip from her boots, then carrying the ottoman over so she could rest her feet upon it. He was mad with longing and feelings of passionate adoration and he poured them out in his worship of her feet, delirious amid the scent of her pussy and the salty leather taste of her toes. The ache from his balls was torment but he was overjoyed that he would not be made to leave after just a brief session. He ran his tongue between her toes and she sighed in pleasure and enlightened him about what lay ahead in their relationship.

"Mistress Susan has given you an idea what will be expected of you as a full-fledged slave. You will be expected to perform the more extreme acts she described as we go along but, but you will be introduced to them gradually. You must understand that when I do order you to perform one of them you must obey immediately and without hesitation. Failure to do so the first time will be punished by the whip and two more weeks will be added to your sentence of orgasm denial. If you fail a second time I am afraid I will have to terminate our relationship. I can settle for nothing less than absolute and unquestioning obedience and submission. Now I would like to come again so move the ottoman aside, come here and lick my anus to warm me up."

He obeyed instantly, pushing the stool out of the way and leaning in. She parted her legs and raised her knees. He saw her brown vortex there below her cunt, puckering in her anticipation. Leading with his tongue's tip he pressed his face into her wet crotch and went to work with adoring hunger, running his tongue in as far as it would go, thrilling to her moan of delight.

Andrea basked in the rapture of it. A tongue in her anus always brought slow but steadily building arousal to a point where her body cried out for sweet release. She kept him at it long, until the warm wet itch in her pussy was too much to bear, then gasped one last command.

"My pussy now Steven! Lick it and put your finger where your tongue was!"

It was a trick that never failed to produce a soul rending climax. She shuddered, spasmed, let out a shriek, then another and Steven could feel her orifice clenching rhythmically on his finger as the waves of orgasm coursed through her body. Then she seemed to melt in the chair and he had to press forward with his shoulders to keep her from sliding senseless to the floor.

When she recovered she sent him to the kitchen to fetch a bottle of red wine and a glass. He poured, and she put him back to work on her feet as she relaxed, picking up her phone, checking and returning emails and texts for an hour or so, sipping down two glasses. Then she laid herself belly down on the adjacent sofa and had him massage her back and legs with lotion, then flipped over so he could do the rest of her body. Her skin was silk beneath his hands. When finished she allowed him to kiss her everywhere. The intimacies with her luscious body inflamed his ache and longing and he poured out his worship. He wondered how he could ever endure an entire month without release. But the thought of failing her and losing her strengthened his resolve.

Andrea sensed the depth of his adoration and could barely contain herself. It seemed her time of loneliness might well be over. But he had yet to go much beyond the acts he had performed before in his life and remained untested. She would give him one such test that very evening, but his worship of her body had inflamed her, and she wanted to come one last time. She pushed his head down between her legs and guided him through a slow and tender cunnilingus. Her orgasm was soft yet all consuming and it sated her for the evening. Then it was time for him to be tested. She shoved him back gently and he knelt.

"Now lie on your back Steven!" She was pleased and encouraged by the immediacy of his obedience. She stood with his head between her feet and looked down at him briefly, then squatted so her pussy hovered above his mouth.

"That wine has gotten the best of me Steven. I see no reason to go all the way to the bathroom since I have you here. You will drink from me now. This will be the first major test of your submission and obedience. Spilling will earn you harsh punishment. Now open your mouth!"

She saw his eyes go wide in surprise and fear, but he still opened wide immediately. She let go.

Steven stared up at her pussy and saw a golden torrent cascade from her ragged labia. It filled his mouth and he nearly panicked, thinking he might spill but he gulped it down somehow, without closing his mouth and was filled again with her pungent, salty-bitter nectar. He had, at first, inwardly cringed in revulsion but, to his surprise, he looked forward to each filling of his mouth with growing thirst. It came from her and was suffused with her essence. He gulped again, and the flow continued through two more fillings and swallowings. Then she lowered her dripping cunt and he knew to lick and suck the leavings from it. Not a drop had fallen to the floor.

Andrea felt growing hope. He had passed his first test to perfection. She would delay the final and most profound one for the duration of his sentence of deprivation. His longing and desire had to be at their zenith and his release would be his reward for that ultimate act of submission. But now it was bedtime.

"Up on your hands and knees and follow me to the bedroom Steven. I'm exhausted, and very relaxed. This has been a delightful evening, but much hard work lies ahead of you."

He groveled behind her down a long hallway to a door at the far end. Her canopy bed was huge, larger in width and length than king size. She made him draw back the covers, laid herself down on the far side of the bed, had him lie crosswise to her with his head pillowed on her thighs then pulled the covers over them both. He lay with her bush tickling his nose and lips, drinking in her scent with each breath. His ache grew almost beyond enduring and his cock pressed ever harder against the cruel spikes. He felt her relax and slip into deep, sweet sleep of a satisfied woman. The warmth and comfort beneath the covers overcame him and, somehow sleep came to him.

Andrea awoke to see it was already 9:00. She woke Steven with a soft tug on his ear and made him lie between her parted legs and place his mouth over her pussy. With a sigh of relief, she filled his mouth with her strong morning piss and was delighted by the way he guzzled it down with a thirst. Then he served her orally from top to bottom through three fine orgasms.

When satisfied she sent him to the bathroom to shower, shave and relieve himself. When he returned she dispatched him to the kitchen with instructions on how to prepare her breakfast. Then she went to the bathroom herself to use the toilet. Donning her black silk robe, she we to the kitchen where Steven was busy making the very large omelet and toast she had ordered. He served her coffee first, the finished preparation of the eggs and brought her breakfast to the table. She made him kneel nearby while she ate. She finished a little more than half of her and put her plate on the floor, so he could stoop to hands and knees to eat it.

Breakfast finished, she ordered him to clean up and wash the dishes, then crawl to the living room to join her. She knelt on the seat of her chair, presenting her somewhat soiled anus and had him lick it spotless. He needed to get used to the taste. She made him linger at it well after she was cleaned, just to enjoy a fine rimming.

Properly cleaned and pleasantly rimmed she made him kneel before her and she released him from the chastity cage. His cock rose to near vertical, stiff as wood. She found this most pleasing and fondled and stroked it, nearly making him come.

"I've never seen a cock so hard Steven. Does this show how much you love me and want me?

"Yes Mistress!"

"Wonderful Steven! That makes me happy. I will let you be free of the cage for the weekend because I can keep an eye on you and I'm sure there won't be any hanky-panky. It also pleases me to see you so erect out of love for me. But your balls are another matter."

She opened a box that sat on the end table next to her. It contained multiple devices and she chose a soft black leather one with laces. It proved to be a stretcher that forced his balls far out from his body and parted them. With a sharp tug she tightened the laces, making his stretched scrotum tight and shiny. His balls soon turned a lurid deep purple. She squeezed each one between thumb and forefinger, making him moan from his ache.

"They must ache terribly Steven, not that it matters to me. Much suffering lies ahead for you to atone for your misdeeds and this is only just. Today I have multiple household chores for you to perform but first you will go and draw me a bath."

He went to the bathroom and started filling the big whirlpool tub. She came into the bathroom and shed her robe, then slipped into the steaming water and invited him to join her. He bathed her with loving hands, then dried her with a large soft towel as she stood splendidly nude. He made bold to kneel and cover her lovely behind with kisses and she permitted it, loving the feeling of once again having an adoring slave.

Then he helped her into her robe again and she ordered him to hands and knees, mounted him sidesaddle and rode him back to her chair. The list of chores was long, vacuuming, dusting, scrubbing floors on hands and knees, cleaning the bathrooms. He was also to prepare her lunch at mid-day.

She felt a sweet contentment as she watched her naked slave going about his duties, his jutting cock and purple balls attesting to his longing and desire for her. She had so much missed being waited on hand and foot and it was especially delightful to once again be able to enjoy orgasm whenever she pleased. A mere snap of her fingers sufficed to have him on his knees serving her and she availed herself several times during the day. He performed the cunnilingus with the adoring passion that only a long-deprived slave could show.

Supper time came, and she made him broil a large steak, bake a potato and make her a salad. As at breakfast and lunch, she ate her fill and gave him the scraps and half eaten leavings. The evening was spent stark naked in relaxation and playful, sometimes cruel pleasures, lubricated by ample quantities of wine.

She mounted his back and rode him room to room around the house, loving the absolute obedience of her steed to her every command. It aroused her, and she made him kneel and serve her. Then she had him stand at attention with his cock jutting and gave it a sound whack with her crop, just to see it wilt, then rise again, ready for another whack. She repeated until she was again aroused and enjoyed another exquisite orgasm under his worshipful tongue. Then it was back to attention while she flicked each of his tender, swollen balls with her finger until the pain put him on the floor in fetal position and groaning. And he drank from her at need.

All of it served to teach him that as her slave it was his lot to serve and suffer, submit and obey, and above all, give pleasure and satisfaction without expecting reciprocation.

Then it was bedtime again and another night of sweet longing beneath the sheets, nuzzling her pussy until sleep overcame them both.

Sunday morning was a reprise of Saturday. After her bath she enthroned herself and had him fetch a finely crafted wooden box from a nearby bookcase shelf. It was perhaps a foot long and six by six. She opened it and took out an object that made a thrill of mingled fear and desire run through him. It was a large strapon phallus, amazingly real looking with big balls at its base and a vaginal bulb at right angles to it for her pleasure. He stared, openmouthed, as he knelt before her. She laughed, but kindly.

"Yes Stephen; you are not the only one with a cock. The difference is that your cock will never enter my body but mine will one day enter yours. You remain a virgin in the truest sense of the word and, at the proper time, I will take that virginity from you. That time has yet to be determined. It may never come because you yet have some tests ahead of you and you might not pass them. But I think you most likely will and on a very special occasion I will use my cock to make you mine once and for all. And then you will come in a way that will give you such pleasure you will long for my cock every waking moment of your life and dream of it every night."

She laid the cock on the coffee table in plain sight, then found more menial chores for him to do for the rest of the day. It pleased and amused her to see his furtive and fearful glances at the big member as he went about his tasks. At eight o'clock in the evening she enjoyed one last cunnilingus, reinstalled his chastity cage and sent him home with instructions to return at the same time Friday evening.

Andrea contacted Mistress Susan with a progress report on Steven in case she was interested: "Steven is delightfully sweet and submissive and gives most satisfactory oral pleasure. He has drunk from me, a milestone, but the least of the tests of submission that lie before him. I have shown him my cock and told him what I mean to do with it. I wish you could see the way he looks at it, the fear in his eyes. But I sense he also wants it. He will be confronted with a sterner test this coming weekend."

Steven had thought the work week before had been an eternity of longing and torment, but it was nothing compared to the week that followed. He stuck to his cubicle, bent over his computer, either forcing himself to work or pretending as the throbbing ache in his balls and the stabbing pain of the spikes pushed him near the brink of madness. At home he had to drink himself to sleep.