The Pleasure Boy 28

Literotic asexstories – The Pleasure Boy 28 by Denker42,Denker42
The Pleasure Boy 28 (Short List)

Exactly one week after the interview with Myrna Stiles, I got an email from Judith Arruda herself inviting me to dinner at one of the best restaurants in the city, at a specified date and time, just four days later. Not by coincidence, I suspected, it was the same restaurant to which my father had taken me years ago when he apologized for opposing my intention to study history. The email also instructed me to expect a small package that would be delivered that same day by courier, and to follow the instructions it contained. When the package arrived, I found that it contained a top quality cock cage, a small lock without its key, and a letter ordering me to confine my genitals on receipt and to come to dinner dressed ‘appropriately.’

Nothing was said about removing the cage. Appropriate dress for the occasion was left for me to decide. Clearly, both my skills as a geisho escort and my pliability as a submissive were being tested. Having lived as an academic for the last several years, and done no escort work at all for months, I had to scramble to get myself properly groomed and dressed for this crucial first meeting. As for the cage, I could guess that refusal to wear it – refusal to take on faith that it would shortly be removed – would automatically disqualify me. I was not yet committed to Arruda in any way. I was not committed to accept the position as Arruda’s prospective lifemate if it was offered. In fact, this cock cage test struck me as presumptuous and arrogant. Notwithstanding, I put it on and locked it as instructed. I had no doubt that it would be removed in few days, when Ms. Arruda’s invitation to dinner was followed by an invitation to her bed as the second part of her interview. From Stiles’ written discussion of me as a candidate, she already had an idea what kind of assistant I would make. What she was testing with the cage was my intelligent obedience. Removing it in a few days, she would be testing my performance as a bed pet.

Four days later, I arrived at the restaurant exactly on time and found her waiting for me. She waved away my apology. “This isn’t a date,” she said. “It’s a hiring interview. I came early to wait for you for the same reason that I will pay our cheque here. I want it clear who will be boss if I take you on.”

“Before we start this interview,” I answered, “let’s get one thing straight. If I accept the position as your lifemate, I will call you ‘Mistress’ (or even ‘Goddess,’ if you prefer), and will obey you to the best of my ability. If I think you’re wrong about something, and there is time for discussion, I will speak up and try to give you the benefit of any relevant knowledge or experience I have. If your mind remains unchanged, I will obey you without further discussion. That is what it means to be someone’s submissive, as I understand the role.”

“But I am not yet your submissive. Until we sign a contract, we are equals. I am considering you as a Domme and lifemate, just as you are considering me. And if I understand the job, part of my role will be to coach you and other senior people at Woodruffe Electronics in being Dominant with intelligent and valuable submissives. Coming on so strong with such people – people like me – is exactly the wrong approach. As the Domme, you want an iron hand. But you want to keep it sheathed, whenever possible, and as long as possible, in a velvet glove. There are times to take the glove off and show your steel. But on these occasions, usually you will also want to show that you are removing the glove reluctantly because the twit you’re dealing with is too dumb to know that there is steel underneath.”

“Do you always talk this way to your employers?” she asked me.

“Ma’am, when you’re my employer, I promise to speak more gently and with due deference,” I answered her. But please consider what I’m saying as a first sample of the kind of instruction that you are hiring someone to give. If the job is as its been explained to me, you’re not looking for blindly obedient slaves who follow orders without questioning them. You’re looking for intelligent, autonomous but reliable subordinates, already highly trained in electronics or some other demanding field, who are worth what you’ll have to pay them, as assistants, or as subordinates to whom you can delegate responsibilities. They don’t need to work for you; they could work anywhere, for about the same money.”

“In addition, you’re looking for authentic submissives who hope, not just to earn their pay cheques, but to give support and love to someone who deserves it. And just like everyone else, they want love and respect themselves. Such people are rare and worth the respect they ask for. If they don’t feel loved or at least respected, they may stay with you anyway to honour their contracts, but you will not receive full value from them. You will not get all that they can give.”

She looked at me very hard, and was silent for a moment. Then, she said, “You’re right; I’m not your Mistress yet. You can call me ‘Ma’am’ to show respect. And I will call you ‘James.’ I like the way you stood up to me. You were right to do so. For now, let’s agree to be friends and see where it goes.”

While we were talking, the waiter had brought us a bottle of wine, opened it before us, and poured a little into Judith’s glass. Clearly, he knew that she was boss here. When she tasted it and nodded to him, he poured for both of us. Saying nothing, I picked up my wine glass and toasted her. She returned the gesture and we clinked glasses. Then to the waiter she said, “You can bring the menus, but leave us for awhile. We’re not in a hurry.”

He bowed and scurried away.

“Friends,” I said. “That’s a good place to start. But I can see right away that you have the makings of a Mistress, and I think serving you might be a pleasure.”

She grinned at me. “Please tell me,” she asked how can you sound like you just did and be a submissive?”

“There’s no contradiction,” I answered. “I enjoy giving pleasure to others, and I’ve been trained to do it. Much like the waiter who just served our wine, I take pride in serving well. But I’ve also been trained to the work that you want done. You’re not interviewing people now to see if they can pour your wine gracefully. You’re looking to hire someone who can learn to be your assistant in human resource management, but also teach you and other senior people at Woodruffe Electronics to function well as lifestyle dominants. That’s the person I’m trying to be. I stood up to you, because I didn’t want to let you walk all over me; and I think our waiter would probably do the same if you tested him. Just like him, I serve, but I also have self-respect.”

“I’m trying to get hired for a job, and trying to show you that I can do it. As an executive, I’m sure you know that giving orders is much harder than taking them. In a D/s relationship that’s still more true. A sub accepts to obey and serve. A Dom, then, takes responsibility for two lives, not just for one if he wants that service to continue. For that reason, training good Dominants is much harder than training submissives.”

“But why do you want this job? And, for that matter, why do you want to serve? As Todd Woodruffe’s son you could be working in the executive suite, learning to run the company. I know I’m asking you a very personal question. You don’t have to answer it, if you don’t want to.”

“I don’t mind trying to answer it, but I’m not sure I can. Mostly, it’s just who and what I am. Years ago, when I was a boy graduating from high school, my father wanted me study engineering in college and prepare myself to inherit the company. I wanted to study history, and went off to train as a geisho to have the means to do it. Push came to shove, I was my mother’s son more than my Dad’s.”

“Yes, I’ve met your Mom a few times at Company social events. I don’t know her well, but she struck me as a formidable lady, I understand that she was a geisha at one time, so you’ve chosen to follow in her footsteps.”

“How did your father feel about that?” How does he feel about you applying for this job and coming to work for me?”

“It was Dad who told me about the Mars project, his need to expand the company, and the plan to attract good senior people partly by offering them the company’s support in teaming up with lifestyle submissives. He told me that you’d be needing help, and encouraged me to send in my resume and apply for the job. But he warned me that the hiring would be up to you – that he would not intervene, and would not hold it against you if you chose someone else. He said – almost his exact words – ‘I think the job is right up your alley, but Judy Arruda knows her job, and it’s her decision. If she hires you, it will be on your merits, not because I told her to.”

Judith nodded and thought for a moment. Then she said, “OK. Let’s order now.” We were silent, looking at our menus. Then she caught our waiter’s eye and he came over.

After he’d taken our orders and gone away, she returned to our conversation. “Apart from the question (still to be tested) about our compatibility as lifemates, I do have one serious doubt about taking you on as my confidential assistant, though you seem qualified for the job in every way. While we’re talking about your father, let’s get it out of the way. He and I have an excellent working relationship, and we agree most of the time. Still, there have been times when my opinions, desires or interests are in some competition with your father’s. There will be such times between us if take you on.” I started to say that “there couldn’t be,” but she cut me off. “Of course, there will be,” she went on. “There always are, between any two people. It’s just that as a submissive you are promising that my desires will always prevail.”

“I have one big doubt about you,” she continued. As my assistant, I will be counting on your loyalty. But as your father’s son, you have his love, and will have his ear. So my question is, “Can I really trust you? When we come to a crunch (and, predictably, we will eventually), whose side will you be on?

“Dad saw this coming,” I answered her. “He knew you would see my possible conflict of loyalties, and he knew it would concern you. He said that if you chose me, my loyalties should always be to you in any such conflict, and he promised that he would not feel betrayed when I obeyed and supported you against his wishes. All I can do is trust him to keep that promise, and not resent it when I keep my professional commitment to you as a geisho and submissive.”

“Likewise, all I can do is promise that what I learn about you will stay between us, and that I will never allow my relationship with him – close as it has become – to infringe on my commitments and loyalty to you. I will never be his spy or secret agent. I will never tell him anything about your thoughts or plans or activities without your explicit permission. And even then, I will use my judgment and discretion to your benefit not his.”

“He knows that fidelity to you will be my professional obligation as a geisho. He will not mind my making this promise and keeping it.”

“So in the end,” Judith replied, “it all comes down to promises and expectations, and to whether the promises made will be kept. Very well, we’ll see if I can trust yours.”

“If you don’t trust that I’ll be on your side in any conflict with my father, and that he expects this and won’t hold it against either of us, you’d be wiser to choose someone else.”

“And that’s your professional advice?”

“Yes, Ma’am.”

The waiter brought our plates and we fell silent, concentrating on the food which was excellent, but something less than exquisite. Since the last time I had eaten here, with my father, when I was still a boy, I had learned the difference. On my escort gigs and with Natasha, I had eaten some wonderful food; and before that, at the Guild school, they had taught me what to look for, at restaurants and elsewhere, to distinguish the superb from the merely good.

When we finished, Judith told me to call for a taxi which I did, using my cell phone. While I was doing this, she called for and signed the cheque, putting its sum, with a tip, on her account. Then she gestured to me. I stood, walked around behind her and helped her stand. She smiled at me. “That was your interview,” she said. “Next comes your audition.” I knew exactly what she meant.

As we stood outside the restaurant waiting for our cab, Judith said, “There’s one more issue that I think we should face squarely, before I take you home and try you out as a playmate: As I remember from your resume, you’re 26 years old now. I’m 43, almost old enough to be your mother. How do you feel about servicing old women?”

I grinned at her, “Truth is I love to make it with older women or be used as a sex toy by them, especially when they treat me as a no-nonsense mother would treat her much loved but sometimes naughty son. Will you do that.”

“Take you over my knee and spank you?” she grinned back. “I can do that just for fun, even when you haven’t been naughty! As a cougar, I love to play with the pups and have them serve me. I make sure that they are properly respectful while they’re doing it.”

In a few moments our cab came, and we climbed into the back seat. She gave the driver her address, then sat back took a deep breath and looked me as the taxi started to roll. In a few moments, she reached over, got a good grip on the bulge in my pants and said quietly, “You’re wearing the penis cage. Good. Honour system now: Did you put it on the day it was delivered?”

“Yes, Ma’am,” right after I opened the box and read your letter.”

“You’re sure?”

“As a professional submissive, another promise I’ll make is that I’ll never lie to you. I may not tell you everything I do, but I will tell you everything I think you need to know, and will answer truthfully any question that you ask. A sub has no right of privacy. Rather than lie, I’ll take your punishment when displease you.”

“In return, I ask that you never to lie to me, although you do have a right of privacy and can always refuse to answer my questions.”

“We can work on those terms. Just one more thing: If I decline to answer, you will not snoop around to penetrate my privacy. You will not snoop around me, period. If you want to know something, you will ask; and if I decline to answer, you will live with it.”

Just as I agreed to this, the cab pulled up at Judith’s door. She paid the fare, then waited, ladylike, while I climbed out and helped her do the same. We walked to her door and she opened it, then gestured me do enter first. “Now strip and display,” she commanded as she closed the door behind us. “I want to see what I’m getting if we hire you.”

I gave a small bow to express obedience and then began the masculine striptease that I’d been taught at Guild school. This begins with a display of graceful bending to remove the shoes and socks, shows off the male body’s musculature with a routine of tensing and flexing in its middle phase as the outer clothing is shed, and ends with a shameless exhibition of masculine sexuality – caressing and tweaking the nipples as the undershirt comes up and over the face, briefly hiding it, and then, as the underpants or jock strap come slowly down, performing a lewd performance to show off shapely buttocks from the rear, and phallic power from the front. Stark naked now, except for the cage around my package, all I could was thrust my hips at Judith, fucking the air between us while stroking my bum and torso as I did this.

When I sensed she had had enough I bowed again as she applauded soundlessly, then knelt before her and kissed the top of each shoe. “How can I serve you, Ma’am,” I asked her. “What is your pleasure?”

“Hmmm,” Judith purred. “Let’s see. I’m wearing much too many clothes for what I have in mind, so you can begin by helping me undress.” I rose to my feet and began to do so, unzipping her dress, folding it neatly when she shrugged it off, and putting it aside on a table. I did the same with each remaining item of clothing until she was as nude as I was – more so, actually, since she was not wearing a chastity cage.

She smiled at me. “I don’t want your cock in me yet,” she said, “not unless or until we hire you. But I think a demonstration of your oral skills would be nice. Your mouth works very well for speech. Why don’t you start with my breasts, and show me what else it can do!”

I took her hand, led her to the sofa and started in – kissing, licking, suckling on her nipples and biting these gently as she moaned with pleasure. Still fondling her breasts, I kissed her lips and her neck. When I felt she was ready, I dropped to the floor and buried my face in her sex – first licking and kissing her inner thighs till they opened wider for me, then entering her vulva with my tongue and setting to work on her clit. It was not long before she came – not wildly, with screams of ecstasy, but sweetly, with a shudder of joy and a deep smile of contentment. As the climax ended, I watched her body relax all over. “Thank you,” she said.

“Do you want another?” Ma’am,” I asked her.

“Not just yet,” she answered. “Now I want to give you a spanking – not that you’ve been naughty, or done anything wrong. Just consider it part of this interview: I want to let you know that I can do it. And I want to see how you respond to pain. Any objections?”

“None at all, Ma’am. My bum cheeks, like the rest of me, are yours tonight.”

“Very well then, Do you see my purse on the table over there? I want you to bring it to me.”

I did so, showing her the elegant knee-walking (called suwari-waza in the Japanese martial arts) that I’d learned at Guild school. When I came back to her with the purse – passing it in the proper fashion, with both hands – she rummaged in it and took out a key ring and a hairbrush. Gesturing me to kneel in front of her, she used a small key to unlock the penis cage and take it off me. Thus liberated, it sprang at once to a full erection which she stroked with one hand while cupping my balls with the other. “Of course you know,” she said, “that you are not to cum without permission.”

After four days of abstinence, this self-control wasn’t easy; but as she stroked me, I remained immobile, even as my erection grew and became painful. Judith continued, watching me closely. Soon I was dripping pre-cum but suppressed the climax, my face a stoic mask, After some time, she decided she could not break my training and gave up.

Still without words, she signalled me, first to stand and then to come across her lap. She took her time arranging me to her satisfaction: palms flat on the floor, penis gripped firmly between her thighs, legs spread and bottom high in the air, so that my feet could not touch the floor. When I was mounted just the way she wanted, she did not start spanking right away, but stroked my bum cheeks gently, sensually, going up the back sometimes and also down my thighs. Spreading my legs a little wider, she caressed my scrotum and perineum, then gently probed my anus with a finger, bidding me squeeze it with the sphincter muscle. So far, this was all delightful, except that my woody, clamped between her thighs, remained hard and painful. But I did not climax and at length, she began to spank – at first softly, only with her hand, but soon with the hairbrush, setting my butt on fire. Still I did not squirm or struggle, merely accepted the sensation and took what she was dishing out.

At length she grew frustrated. “I see you’re pretty tough.” she said, “but I don’t want stoicism now. I want to see I’m getting through to you.”

“But don’t fake it either,” she continued. “If you can, just give in to it. Be spontaneous, and let me show me what you are feeling.”

Abandoning control, I came almost at once, spurting hot semen down her legs. She gave a little shriek and stopped the spanking. For a short time, we were still – both of us catching our breath and cooling down. “That took me by surprise.” Judith said. “You weren’t supposed to come without permission.”

“That was a double-bind, Ma’am” I answered. “When you said to be spontaneous, my body took that as permission to cum. I didn’t get to think about it. There wasn’t time. It happened all by itself. If you are angry and wish to punish me, I will understand.”

“Maybe tomorrow,” Judith told me. For now, kneel between my thighs and lick me clean. If that stuff dries, my legs might be glued together, and that would be a disaster for both of us.

“Indeed it would, Ma’am,” I answered, and hastened to obey.

When I was finished, she grabbed me by the hair, pulled my head up, spread her thighs even wider and proceeded to look herself over. “You missed a spot right here,” she said, pointing at her clit. No trace of semen could be seen there, but I knew what she wanted and continued licking earnestly until she came.

“Very good, James,” she told me then, leaning over and kissing me. “You’ll sleep here, tonight, at the foot of my bed. We’ll do a post-mortem in the morning. I’ll leave the cock cage off, but you are not to touch yourself.”

“Very good, Ma’am,” I said. I followed her up a flight stairs and into her bedroom. She took a pillow and large blanket from her closet, and I helped her arrange them on the floor, where she wanted them.

“Good night,” she bade me. “Sleep well.”

“You too, Ma’am” I said to her. “Thank you for a lovely evening.”

“Thank you, James.”she said. “Good night.”

She got into bed, settled down and was silent, making it clear that I was to do the same. This second interview had gone well, but it was clearly not over. I fell asleep wondering how it would continue in the morning.