Amber's New Job Ch. 03

It was December 20 of my senior year and I was headed for the Carribean in Willie Partman's private jet. You remember her, the red-head I met at my first yoga session, the one who settled her strawberry flavored pussy on my mouth. When she had introduced herself she said she worked at Greenvale Hospital, our community's best medical facility and biggest employer. Michelle, on the way home, told me Willie was being modest. Willie owned a majority interest in the hospital and was chairperson of its Board of Directors. As we prepared for landing I put aside the second volume of a large briefing book I had been provided. But I find I'm getting ahead of myself.

After Thanksgiving dinner with my family I had joined the Richards' at Willie's house for drinks. Willie was telling us how she'd been negotiating with the owner of the largest chain of hospitals in the Carribean to form what promised to be a very profitable partnership. The deal was ready to close when the owner's son began objecting. Willie would be flying down to meet with the family over the Christmas holidays to put Humpty-Dumpty back together again. She asked me to accompany her; my job would be part amanuensis, part lover, and part something else.

"The owner, Fernando Sanchez, has three children, a son in his early twenties and two older daughters. He is in poor health and leans heavily on his children for help. The sisters are much smarter than the brother. His name is Juan. Juan has little mind for business or, for that matter, much of anything else. He's always followed his sisters' lead and they support the deal. However, I've been concerned about the boy from the beginning. The girls kept telling me they could manage him, but the father is strictly old school; he gives Juan more deference than he does his daughters.

"When some of the hospital's executive officers and vendors realized the partnership would end some lucrative side deals, they befriended Juan, praised him, swelled his head, and turned him against the deal. His father has started to listen to him. Amber, I need your help in harnessing the poor lad."

I put down my brandy. "Sounds fascinating." I turned to Ron and Michelle, "I assume you two don't mind me missing a few days of work?"

Michelle smiled. "Of course not, I've told Willie you're perfect for the job."

Looking back at Willie I said, "Sign me up. What do I need to know?"

"A lot. Have you ever milked a man?"

"I don't even know what that is; I guess not."

"Well, that's where we'll start."

She turned to one of her servants, a well-built young blonde man. He, like all her servants, was obedient, invisible until summoned, and gorgeous.

"Sven, get ready in the entertainment room."

"Yes ma'am."

* * * *

We were met at the airport by a limousine which brought us to a local hospital to meet the family. That night we would attend a costume ball. Serious negotiations were set for the following day. I was wearing a business suit, slacks, a white blouse with a tie, and stylish black framed glasses. The briefing book, which indicated Juan had a thing for woman so dressed, was right, he immediately focused on me. After the meeting ended Juan offered to show me the hospital.

I told Juan what I wanted to see. He was more than willing to take directions from the pretty American lady. After visiting the operating room I asked to tour the gynecological/obstetrics wing and found the room Willie had ordered, equipped with an examination table and stirrups.

As we entered the room I dropped my voice tone. While still commanding, it hinted at the husky, sexual. Juan noticed immediately; his eyes softened; was he perhaps intriguing the pretty American?

"Willie says this is the service, taking care of women's sexual life, where the steady money is. I'd need to check out the equipment. Before we start Juan, empty your bladder."

"What?"

"Empty your bladder, before we check out the equipment the woman always empties her bladder."

"I am not a woman."

He was showing the expected resistance, but there was also confusion and a bit of embarrassment. I put my hand on his chest.

"That, dear boy, is obvious. I can ask one of your sisters to help if you'd prefer."

That idea he did not like at all.

"No, no, I will do as you say."

I donned a white doctor's smock. Upon his return I said, "Juan, call me doctor or ma'am."

He nodded, accepting the role I offered him. I took down his weight and height (he subtracted a few pounds from the former and added inches to the latter) and had him sit on the examination table while I took his blood pressure.

"All are good. We'll get your temperature in a minute." I handed him a hospital gown. "Remove your clothes and put this on. I'll return when your done"

His face reflected both surprise and joy. I had asked him to take off his clothes; apparently the pretty American was interested! I stepped into an adjoining room. A minute later there was a knock. He was done. His clothes were strewn around the room. I looked around disapprovingly, my voice stern.

"Juan, you've been a bad boy and made a mess. Please straighten your clothes."

"Yes, ma'am."

He dutifully obeyed, picked up his clothes, placed them on hangers, and hung them on a coat rack. As he did I examined his body. There was little muscular development, he was soft. My devotion to my health over the pasty eighteen months had left me strong and nicely muscled. Willie was right, I could impose my physical presence on this boy. At my direction he climbed onto the examination table.

"I'll examine your breasts first. Lean back."

I ran my hands through the opening of his gown, rubbing my hands over his chest. He closed his eyes and sharply inhaled, loving the sensation. His penis hardened. I increased the pressure on his chest, pushing him down onto the table.

"Your chest is fine. Roll over."

He obeyed.

I pulled the gown aside, exposing his bottom. I ran my hands over it. It might be his best feature, shapely, nice, border-line firm.

"Juan, you have a lovely little behind." I tapped it hard, bordering on a slap. "I'm going to take your temperature."

He looked over his shoulder. Had he heard me right? "Back there?"

"Of course, it's the most accurate way. Now be a good boy; there's no need to be shy. I've seen plenty of boy's bottoms. Spread your legs, open up for me."

He did so, hesitatingly. His face flashed red. Good, he was embarrassed and offering a bit of resistance. I tapped him lightly on his butt. "Come on, you can do better than that, be a good boy and spread wide."

Juan opened his legs and blushed again. His penis remained hard. I ran my hand softly over his butt, "Thank you, you're such a sweet boy."

Confused, aroused, embarrassed, he didn't respond.

"Now, now, don't be pouty. This must be done."

Grudgingly, "I'm sorry doctor, thank you."

"I am going to use some lubricant on your cute little tushie so it doesn't hurt." I put on rubber gloves and picked up a jar sitting on a stainless steel table, put a dollop of cream on my finger tip, and smeared it across the opening of his behind. Juan gasped as I spread the cold gel over his anus, rubbing circles around its rim, warming the lubricant and massaging his asshole. Juan, who had stiffened, relaxed. He enjoyed the sensation and his body sank back into the table. I studied his butthole; it had a nice sweet pink color and responded nicely. It opened and shut. It was time.

"Good, your ready."

It was not a question and I didn't wait for an answer. I placed a finger on each side of his anus and opened him as I slid the thermometer inside. I then ran a finger down his spine.

"Juan, since this is a room for examining women, you don't mind if I call your anus your pussy, do you?"

In an uncertain voice he answered, "I guess not."

"That's a good boy. You do have a very pretty pussy."

"Thank you ma'am."

I removed the thermometer and checked the temperature. "Normal." While taking off my rubber gloves, I added, "Now we'll examine your chest. Roll over."

He hesitated. His erect penis would be fully exposed. He wanted me to see it, and play with it, but the situation was strange. He was not sure what to expect, not sure what he should do.

My voice sharp and curt, "Juan."

His face flushed, he said, "Sorry ma'am," and rolled over. His hand drifted down and made a half-hearted effort to cover his penis. Ignoring his manhood, I moved to the side of the table and conducted an abdominal exam, palpitating his chest with enough force for him to understand who was in control. He reported neither pain nor tenderness.

"Put you feet in the stirrups."

"Isn't that for girls?"

"Juan, the words we use are ladies or women, not girls, but you're right, its mostly for them, but boys can play too. Do you want me to call your sisters?"

"No, no, I'll do it."

"That's a good boy."

He put his feet in the stirrups, angled inward. I pushed his legs aside. He was laying in front of me, completely exposed. He stared at me. When I caught his eye, he looked away. He was confused, unsure of how he should feel - part aroused, part embarrassed, part bewildered - but far too irresolute to stop me. I pushed his knees further outward with my elbows. He blushed. He knew something was wrong, that the game was spinning out of control, but lacked the gumption to say no.

For the first time I looked directly at his penis. It was throughly average. While he had lost his erection, it was still thick with blood. When I took it in my hand it instantly hardened. I rolled the foreskin back. He was clean and the skin rosy.

"Do you scrub it everyday like you should?"

"Yes, yes Ma'am."

"That's a good boy."

I applied rubbing alcohol to a cloth and cleaned its end, brushing my fingertips over the sensitive head. He gasped and arched his hips. I ran a fingertip down the shaft and cupped his scrotum, taking his testicles between my thumb and index finger, rolling them, massaging them, evaluating them. After finishing, I dragged a nail across his sac, over his perineum, to his anus.

"Seems normal. Juan, how often do you masturbate?

He stared at me.

"Juan, how often do you masturbate, how often do you play with your pee-pee?"

Stupefied, he said, "Once a week."

"Juan, you're lying to me. It's more often than that. You should never lie to a woman."

Although he was not sure why, he apologized, "I'm sorry, ma'am. I was lying. It's more than that."

"How often?"

"His face flushed red. "Every day."

"You are a horny little buy, aren't you?"

"I have lots of friends who..."

I raised an eyebrow.

"Yes ma'am."

"And when you do, do you have emissions? Does your seed drip out or spurt out?"

"Drip, mostly, ma'am."

"What was the last time you did it?"

He took a second. I stared at him, waiting. "This morning, in the shower."

I frowned and my voice took on a border-line harsh tone. "That's not good Juan, we'll need to take our sample later, when we're sure there is enough."

"I'm sorry ma'am. I didn't know."

I ignored his apology and made some notes on a chart. I picked up a speculum. His eyes focused on the shiny metal device.

"Juan, this is a speculum. It will hold your pussy open so I can see inside. Then we'll check your prostrate to make sure it's firm and healthy. That's a very important thing to do."

I didn't wait for a response. I sat on a stool at the foot of the bed and put on rubber gloves. "Spread your pussy cheeks, sweet boy." Grudgingly he pulled them aside and I re-lubricated his anus, rubbing the cream around the rim; the crinkled skin glistened with oil. I slipped a finger inside, leaving a dab of the heavy stuff within him. I lubed the instrument and its curved metal blades easily slid inside, opening him up. His gasp reflected pain and shock and, I thought, a bit of pleasure. I covertly glanced at his face; yes, it displayed both embarrassment and desire. His penis had re-filled with blood.

I looked inside him using a small medical flashlight, jogging the speculum a bit. He moaned. I removed the tool.

"You're such a good boy. I'm happy to report all is normal. In fact, you have a lovely pussy. Now I will massage your prostate to make sure it's okay."

I slipped two fingers into his well-lubricated anus, found his prostrate, and pressed on it. His rectum clenched tight on my fingers. I ran a hand across his chest.

"Don't be nervous, you can relax your pussy. I won't hurt your little tushie."

"Yes ma'am." He relaxed, his anus opening again.

"That's a good little boy."

He smiled.

I pressed his prostate with the pad of my fingertip. He closed his eyes and murmured; when I applied more pressure his moan deepened. I kept massaging him, drawing the examination out far beyond any medical necessity. His anus adjusted to my fingers, all apprehension left him. His penis was rock hard.

I kept working his prostate. He started to rock his butt, moving with me.

"Juan, you like my finger in your pussy, don't you. I can see your pee-pee is all hard."

His eyes closed, his voice dreamy, he said, "Yes ma'am, I didn't know, my butt, I'm sorry, I mean my pussy, could feel so good, you make it feel good."

I ran a fingernail up the length of his penis. His eyes popped open. "Good Juan, I'm glad to see your pee-pee is responding normally." I wrapped my hand around it head and worked it nice and slow. All resistence had left his asshole; I could make it open and shut at will. I took my finger out of his butt and stopped masturbating him. He groaned in disappointment.

"I have wonderful news. Your prostate is fine and your pussy is very sensitive. I have a special treat for you."

I removed a thin flexible dildo from a drawer. Hanging from one end was a battery pack. Juan was confused, apprehensive, curious.

"We're going to take advantage of your wonderfully responsive pussy to help build up your supply of boy-juice. We're going to put this inside you."

His face turned red and he said, "But I'm not a..." I frowned. His voice broke off.

"Not a homosexual. Of course you're not. This is play between a woman and a boy, not two men. You noticed I'm a woman, didn't you Juan."

He hurried to reassure me, "Yes, yes."

"We'll use this to increase your supply of boy-juice. Now be a good boy and pull your pussy lips apart."

He hesitated. I glanced at his penis. He hurried to comply. I worked another dab of cream in his asshole, watching it quiver. It was learning to obey. I lubed the dildo, aligned its head to his asshole, and while stroking his chest pushed the artificial cock past his sphincter, watching his body stretch as he accepted the intrusion gliding past his small, tight rectum. The toy was not large enough to cause him pain, but he was frightened and released his ass cheeks, grabbing the edge of the table. I ran my hand down his chest, cooing what an obedient little boy he was, calming him. I wanted him scared, but needed to keep him from panicking.

He lifted his head from the table, trying to see what was happening. The process might be strange and he certainly felt full in a way he had never experienced, but the pain was mostly in his head and, I knew, would soon be replaced by pleasure. When the dildo was all the way inside him I turned it on, the gentle vibrations resounded through his backside. In a matter of seconds his head fell back to the table and he started rocking his hips, emitting a happy coo. His penis, which had deflated, once again grew stiff; pre-cum dripped from its tip. He arched his back and let out a deep moan, "Unnnnnnhhhhhhhhnnnnnn."

"Juan, you have a very sensitive pee-pee and such a tight sweet pussy. The dildo is making you feel good, isn't it?"

His arousal was evident; I felt his heart rate increase. He hesitated. He was still a guy and reluctant to say what I wanted to hear.

"I'm sorry Juan, Mommy thought you liked it." I reached down to withdraw the artificial dick.

He blushed. He didn't want to admit it, but he did. "No, no, I do."

I adjusted my glasses. The look on my face was one of disappointment. He saw that I wanted to hear more.

His voice was hurried. "Yes Mommy, I like it."

"What do you like?"

"The dildo in my butt."

"Juan..."

"The dildo in my pussy."

"You like it when I fuck your pussy."

"Yes."

"Juan."

"Yes, I like getting my pussy fucked."

"With what, Juan?"

There was no hesitation this time. "The dildo Mommy. Juan likes getting his pussy fucked with the dildo."

"Good Juan, now Mommy is going to try something else." I pulled the dildo out about an inch, and pushed it back inside. He murmured his approval and I began, slowly and gently, to fuck him with the tool while encouraging and praising him. He found the sensation increasingly pleasurable.

"Ohh, Mommy, yes. I like it when Mommy fucks my sweet tight pussy. My pussy feels so good, it really really does Mommy. Oh Mommy, it feels so good"

"Now Juan, touch your pee-pee, but nice and slow, take your time."

He started jerking himself off. I pushed the dildo hard into him, securing his attention.

"Juan, I said slow."

He obeyed, barely moving his hand over his member. After a few minutes, when he began to pick up the pace, I said, "Juan," in a gentle tone. Fearful of my disapproval, he slowed down, took his time, fighting the desire to bring himself off.

As he did so I picked up the pace, twisting the dildo around inside him. Juan groaned. The muscles of his ass instinctively worked over the invader, massaging it, grabbing at it. I ran my free hand over his scrotum. Juan was breathing hard, fully absorbed in his body. Still, whenever the pace of his masturbation increased, I scolded him, reminding him to go slow.

"Isn't it wonderful Juan, to have such a responsive pussy?"

"Yes Mommy, thank you Mommy, my cunt, my pee-pee, they both feel so good."

"Mommy knows what's she doing, you should always obey Mommy."

"Yes Mommy, I'll be a good boy."

I started fucking him with the dildo's full length, watching it be repeatedly enveloped in his sweet puckered asshole. Juan squealed in delight. His hand was quivering, desperate to stroke himself to orgasm. Drops of pre-cum flowed from his cock like a fountain.

"What a good boy you are, making your own juice. Now go a little faster, but don't come."

His hand rocketed up and down his penis. His anus quivered, opened and closed, clamping down on the artificial intruder. I picked up the pace, fucking him hard with the plastic cock. His scrotum tightened.

"I'm, I'm getting close," he said.

I took hold of his hand. "Stop!"

Disoriented and confused, he obeyed. His stopped masturbating. His twitching erection glowed a bright red. I pulled the dildo from his asshole.

"Did I do something wrong?"

"No dear boy, you did exactly what you were supposed to. Remember what I told you earlier, that we needed a sample of your boy juice, but had to build up a big supply. That's what we've been doing. Now we'll milk you."

The faltering tone of his voice confirmed his confusion, but he was desperate to come. "I remember now. Do you want me to, y'know, in a cup?"

"No dear boy, that's the old fashioned way. I said I was going to milk you. You need to improve your listening skills Juan."

"I'm sorry ma'am, it's just that I don't understand."

"You will dear boy. Roll over."

His face flashed red, but he obeyed without hesitation. The combination of his infatuation with me, my calm self-assurance and air of command, the perplexing circumstances, and his weakness had ceded me complete control.

"All the things we've done, my playing with your pussy and your rubbing your pee-pee, they helped build up a big supply of boy juice. Now I'm going to extract it."

I put on a rubber glove, letting it snap it into place. The thwack of the glove against my skin reverberated around the room. Although his anus was already stretched and lubed, I unscrewed the jar of lubricant and used my gloved hand to smear it over his anus, coating the length of anal crevice and pushing several globs inside him. I praised him, told him what a sweet obedient boy he was, what a lovely soft pussy he had. His apprehension faded.