The doctor looked at Milo over the top of his half-moon reading glasses. The slim boy looked around the room distractedly.
“You say your mother thought you should come in? What seems to be the problem?”
“She thought something was wrong with my, uh, me.” Milo shifted restlessly in his seat.
“With your what?”
“With my thing. You know. Down there.”
“With your penis?”
Milo nodded.
“What’s wrong.”
“Nothing.”
“But you mother thinks there is? Is that it? Your mother thinks something is wrong with your penis?”
“Yes,” Milo said in a choked voice.
“Well, let’s have a quick look,” he said in a reassuring tone.
Milo quickly rose from the examining table and briskly dropped his trousers. Turning back to Milo and pulling on his examining gloves, the doctor gasped.
“My God, what happened? It looks like you’ve been burned!”
“No.”
“It’s swollen. It’s flaming red. It’s huge.”
“True.”
“How long has it been this way?”
“Always. As long as I can remember.”
With difficulty the doctor regained his composure. He kept mopping his forehead and adjusting his glasses. He gingerly grasped Milo’s member and turned it this way and that, looked at the top and bottom, and carefully examined his testicles.
“Well, Mr. Puzzlewick, that is astonishing. It’s surprising you can fit it into your pants.”
“I used to wear jockey shorts, but it kept stretching out the elastic,” Milo said brightly. “With boxer shorts there’s only a problem with it poking out the waistband of my pants.”
“I can see the problem. How do you deal with that?”
“I wear my shirt tail outside my pants so it’s covered. ‘Course, bending over is still uncomfortable.”
“Do you mean you never lose your erection?”
“My what?”
“Your erection. When does your penis go soft?”
“I didn’t know it was supposed to,” Milo blushed.
The doctor finished his examination and, for good measure, he took photographs. Reassuring Milo that he didn’t see anything to worry about, he saw the boy to the door and closed it thoughtfully behind him. Without a pause he went to his desk and picked up the telephone.
“Murray? Chester. I have something I think you should see,” he said, absentmindedly toying with the polaroid photos in his hand.
* * * * * * * * * * * * * * * * * *
Murray was a man who had had many different careers in his life, but the latest was the most lucrative. His latest job was providing gifted lovers to lonely, demanding or privacy-loving women. Often, the women were all three at the same time.
Murray liked this work. It was clean, it was safe from the police and he got to spend his time with interesting and attractive people. Much better than loan-sharking or fencing stolen goods. He got to wear nice clothes and work from a nice office.
The only fly in this lovely ointment was the Talent: there was too little of it. Oh, there were plenty of volunteers, but few of the men had the qualities of health, discretion and sensitivity that the work demanded. Women, after all, were women. Even if they were rich enough or kinky enough to obtain the services of a boy from time to time, they still wanted a little tender loving care and sensitivity. They would pay extra for it. And if these qualities were found in a person with a buff body and a large dick, they would pay even more.
That’s why a find like Milo was such a treasure. He was worth his weight in gold if, as seemed likely, he would be a good lover.
Milo sat opposite Murray waiting patiently. He wore a new designer suit and hand made shirt. His hair was done in a well-known shop which had also provided a manicure and pedicure. He looked good; he felt good.
“Milo,” Murray said in a soft voice, “it’s time for you to go out and try your wings. Your client’s name is Ariana and she’s a very nice lady who only comes to L.A. once in a blue moon, usually for the specific purpose of getting laid, er, getting male companionship. A very nice woman, an aristocrat, a Duchess, in fact.”
“That’s nice,” Milo said with a touch of excitement in his voice.
“You’ll like her. She’ll like you. You’ll see.” Murray hoped that Milo wouldn’t fuck up. Lady Sans-Regrette was one of his best — and most demanding — customers.
* * * * * * * * * * * * * * * * * *
Ariana Sans-Regrette smoked her third cigarette of the day as she looked out over the sea of lights which was L.A. at night. She needed a man and she hoped Murray’s new boy would be good.
Ariana was discontent.
She chafed under the limitations on her choice of men. They were either hardened, soulless porn stars with dicks like overripe cucumbers or shy, callow youths who withered at her first sign of aggression. And above all Ariana needed to be an aggressor. In her mind she saw herself as the Alpha lioness in a pride of lions. “I don’t kill,” she thought with a smile, “but I leave them licking their wounds.” With that thought, she passed her hand lightly over her pubis, as if reassuring her pussy that help was on the way.
Ariana had not always been a duchess. She had outlived three husbands, inheriting fortunes from all three and a title from the last. Actually, all of them had died at home between her legs. She had a gift to pushing men beyond their limits. In the case of husbands, she was willing to push them beyond reason.
She wasn’t a nymphomaniac but she was relentlessly sexual. She had a large appetite but she could control it, save it for the right time and right partners.
She had kept her looks, saved her money and knew how to spend it. Spending it on randy young men was one very good way. Ariana looked at herself in the hall mirror of her suite. She had nothing to be ashamed of. She still had a couple of husbands in her if she needed the money. She smiled.
Milo walked straight past the hotel desk as he had been instructed. The staff knew that Ariana was in town and expected a queue of men to go up to her room at intervals of four or five hours for the next several days. The women on the desk watched these men furtively, speculating on their charms. The men on the desk watched them pass with a mixture of envy and awe, wondering what happened upstairs that made them go up proud and come down shambling like old men.
The man at the door of Ariana’s suite did not show very much promise. He was very young and looked shy and nervous. Not that she minded a boy like that, it’s just that they didn’t last. They were more of a snack than a main course. With a secret sigh she led him straight through the suite to her bedroom.
“Well, come in,” she said a little impatiently when he lagged. She noticed that despite his nerves, Milo moved well, lightly on his feet like an athlete. She guessed that Murray had bought Milo’s clothes because they fit perfectly and were very expensive. “Gift wrapping,” she thought, “waiting to be torn off the present.”
“You know my name, Milo? Good. Do you know what I want from you?”
“Murray said you liked to fuck,” Milo said uncertainly, as if he had not prepared for an exam.
“Not the way I would have put it, but accurate.” She liked his fresh quality and his crooked smile. His face was mature with a suggestion of youth lightly overlaying a strong jaw and full lips. His eyes were blue, his hair nearly black with auburn highlights.
“What I need is a man, Milo. A good man. I only need one for a little while, but I need him very strongly for that little while. Do you understand?”
Milo nodded.
“Good. Let me see you.”
Milo hesitated.
“Take off your clothes, Milo, so I can look at you.” This sent a little thrill of power coursing through Ariana’s body. She liked to be in control.
While Milo undressed, she slowly rubbed her hand over her belly where the heat was beginning to rise.
Milo’s nerves made him clumsy and he found himself trying to take off his pants before he’d removed his shoes.
“Here,” she said impatiently. “Sit down on the bed.” She knelt at his feet and removed his shoes and socks. She sensed Milo watching her and could hear his breathing grow shallower.
“Stand,” she commanded, and she pulled his pants down and helped him step out of them.
When she reached for the waistband of his baggy boxer shorts (they were not her favorite) she noticed it for the first time. ‘It’ put a silly thought into her mind: “My God, he’s hiding a salami in his underwear!” Suddenly interested, she yanked down the shorts and was nearly struck in the face by his tool.
“Sorry, ma’am,” Milo said. “It’s real hard to control.”
Ariana gave a sharp intake of breath and impulsively put her hand around it, or at least partway around it. It was certainly the largest penis she had ever seen on a human being, at least twelve inches in length with a diameter in excess of three inches. It was also one of the hardest she had ever had the pleasure to know, standing rigidly at a steady ninety degree angle from his pelvis, twitching slightly in sympathy to the beating of his heart.
“Milo, that’s very nice, but do you have a license to carry a concealed weapon?”
“No ma’am.”
“It is loaded, isn’t it?” she asked, slowly stroking the length of it.
“I think so, ma’am.”
“You have been with a woman before, haven’t you?”
“No, ma’am.”
“Or with a boy?”
“Oh, no.”
Ariana was crestfallen. She had never had a taste for virgins. Young, yes, but not virgins. They were hair-triggered and wasted their potential with wild thrashing and clumsy thrusting. She made a note to ream Murray. She was also pleased that she’d had the foresight to schedule another gentleman caller in the morning. She resigned herself to making the best of it for the rest of the night.
She leaned forward and gave Milo’s dick a friendly lick and kiss. Immediately she felt his onrushing ejaculation and she got out of the way just in time to see the dense liquid cross the room in a stream making a heavy squiggle on the mirror opposite. She continued to stroke Milo as the awareness dawned on her that if her past experience was any indication the party was now pretty much over. The boy had emptied himself like a firehose and she doubted there was much more in the hydrant.
“Sorry, ma’am. You caught me by surprise,” he said shamefacedly. “But that felt real good.”
“I’m glad,” she said evenly. “And don’t worry, you’ll be hard again in a few minutes and then we’ll have a real nice time.”
“‘Again’, ma’am?”
“Yes. You’ll go soft for a little while then I’ll arouse the interest of this monster again.”
“Oh, ma’am, it never goes soft.”
“What?”
“I’m sorry. It’s real embarrassing. The guys in the locker room used to rag on me without mercy. But it just stays like this. All the time.”
“Not after sex,” she said confidently. “But you’ve never had sex….”
“Ma’am, I said I’d never had sex with a woman… or a man. I didn’t say I’d never come. I come all the time. Whenever I want. Without even touching it.”
Ariana had maneuvered Milo back to the bed and she was sitting next to him, still holding his cock.
“You never go soft? You can come anytime you want without being touched?” She was mildly skeptical. “Show me.” She took her hand away. “Come now without touching yourself.” She could not bear a braggart or a liar and she wanted to know which he was.
“OK,” Milo said. Closing his eyes, he gave forth with a throaty moan and his dick erupted wildly, spraying the ceiling and leaving a wet line across Ariana, the bed and the floor.”
“Oops. I should of caught that so I didn’t mess up your room. Sorry.”
Ariana was speechless, then she was hungry. “OK, Milo, let’s see how long you can, uh, keep this up, OK?”
“OK by me, ma’am. I’m game,” he grinned.
“Good. I’m the hunter.” Standing quickly, she pulled the long silk slip over her head with a single swift motion. “And this is my hunting license,” she said, moving toward Milo like a beggar at a buffet.
Ariana’s ‘hunting license’ was valid anywhere on the planet that heterosexual men gathered. Her hair was so black it had blue highlights and hung about her head in a dense cloud. She only weighed a shade over a hundred pounds and had just enough weight to smooth out the bumps and rough edges. Her breasts were as small as a girls and her nipples were the size of hazelnuts and just as hard. As she threw her leg astride him, Milo noticed that her crotch was slick and shiny with lubrication.
Ariana made no demand of Milo other than that he should lay on his back and take his medicine. It took her a minute to fit him into herself, to the accompaniment of her heartfelt moans and grunts. After a bit she had him in her up to the hilt and she rested there looking down at him, moving her hips slightly to help stretch her pussy. Actually, she was a little awestruck. She hadn’t experienced anything like this since she’d given up the stallion-sized dildo she’d used at girl’s school. She could feel his penis the full length of her vagina and pressing against the roof of her womb. She would have to be careful or she could bruise her ovaries, an excruciating experience she avoided like the plague.
Slowly she began to move in a regular motion, up and down and round and round. All the sensitive parts of her body were stretched taut and in play except for her breasts. She took Milo’s head in her hand and lifted it up until he had her breast in his mouth. Without prompting, Milo began to suck and lick her. After a while he switched to the other breast. Milo liked the taste and texture of her breasts, as well as the way it made Ariana moan.
She came more quickly than she had in years. Ariana had feared she was becoming jaded, that old-fashioned vaginal sex was losing its charm, but this was proof that old tastes were never dead, only dormant.
She wanted more pressure on her clitoris so she moved her knees back and lay full length on Milo, trading the pleasure of his soft mouth on her nipples for the electric sensation generated by her clit. She rotated her hips in a slow humping motion. Milo felt her pubis grinding against his and before long Ariana arched her back, caught her breath and screamed long but low.
After a minute, never stopping her motion, she looked down at him with eyes clouded by pleasure.
“Are you going to come?” she asked.
“Not yet. I don’t want you to get messy.”
“Nice. Wait as long as you can.”
She settled herself in to her work and her aggressive self came to the fore. She went back to her knees and worked herself around his cock, varying the stroke and the speed. When she felt her orgasm building again, she reached down and pinched his nipples hard between her fingers, as if she were holding on to keep from falling off. Milo made no complaint. Instead he reached up and locked her nipples in a similar grip.
The mix of pain and pleasure brought her to orgasm again, this one much bigger than the last. She lurched against him nearly out of control. Her smooth controlled movements became spasmodic and abrupt. She continued moving long after her shrieks ended, then slumped like a tired cowboy in the saddle. She released his nipples and he let hers go, giving them a gentle rub by way of apologizing for his roughness. His simple gesture caused the heat in Ariana to begin rising again.
He was as hard as ever, if anything he was more so. He looked up at her with a small smile that suggested both satisfaction and curiosity. He ran his hands along her flanks, up her sides to her breasts and back again. He had smart hands: there wasn’t an ounce of roughness in them. They were hands that knew a woman’s body intuitively. Experience would only make them better, Ariana knew, and the thought made her want to be the one to give him the experience.
“Are you ready to come?” she asked.
“Whenever. Do you want me to come?”
“Yes. Get on top and come in me. But don’t use your little mind-control trick. Come the proper way. Make me come if you can.”
“Yes, ma’am,” he said obediently. He rolled her over without pulling out. He arranged her body beneath him and she could feel the strength in his hands and arms. She noticed for the first time that his chest was sculpted like a gymnast and tanned like a lifeguard.
Her vagina had become more accustomed to his cock, but she was beginning to feel that her lubrication was failing. Fortunately, she was certain he would not last much longer and then she could go to the bathroom and use some vitamin E oil to reduce the friction.
He put almost no weight on her at all, taking his full weight on his arms. He rested for a moment, looking down into her flushed face, noting the dreamy look of satisfaction in her eyes.
“Do you want it hard or slow?”
“Hard. As hard as you can. I want to feel you come in me.” Ariana thought that approach would guarantee he would come quickly and give her a chance to go to the bathroom.
“Hard it is, then,” he said cheerfully. But he started off gently instead. She started with her knees drawn almost up to her chest to encourage his coming, but his motion affected her more than her position incited him. Soon she lowered her legs until they were flat on the bed. Milo’s instincts were good. He began a rotary motion interspersed with a few gentle thrusts, then a combination of the two. Soon he found a pattern that Ariana found irresistible. He heard her gasp and felt her move her pelvis into more direct contact with his and he settled into that motion. He was fascinated by her rising gasps and sighs.
“Gee,” he thought. “This is fun and I get paid for it, too!”
Milo sensed that there was a very narrow range of motion that worked for her. Too much and she moved to protect her clit, less and she grew bored. Once he knew what to look for, he started to show her a very good time.
She came with a throaty scream and scratched his back until she drew blood. When she collapsed he kept up his movements. She came back to herself slowly.
“Come in me! Come in me!” she demanded. It wasn’t so much her need for lubrication – her body seemed to have found previously unknown reserves. No, it was a clean, sudden need to feel him jerk and spurt inside her. She wanted this man to do the man thing in her.
“No,” he said flatly.
Ariana was speechless and just a little irked. She was mad at herself as much as at him. She had placed herself in a submissive position under him, waiting on his pleasure, when she had always kept the whip hand in bedroom games.
While Ariana tried to make up her mind what to do, Milo found a new motion that caught her interest. Her rational mind was suddenly unplugged by the little mind that lived under the hood between her legs.
The more he fucked her, the quicker and more violently she came. After a while her orgasms came like ocean waves, cresting every few seconds, never completely receding.
“Oh, please come. Please.” She was begging but she didn’t care. She was having trouble catching her breath and she felt like her skin was on fire. “Please?”
“All right.” He pulled her knees over his shoulders. He settled himself like a driver in a racing car. “Here it comes,” he said.
She wrapped her legs tight around his neck and held his head with both hands. His motion was powerful but not brutal. Her entire body moved to the force of his stroke. She felt she was holding on for dear life, afraid to let him go. Then her warmth began to rise against her will and she started the cycle of orgasms again. They weren’t explosive or violent. They were gentle ripples that washed over her all the time.
There was a point where her body began to rebel. Her cunt was sore and dry, her clitoris was overstimulated, her arms and legs were tired. Just then, as if by magic, Milo came in her. She felt it very clearly. The sperm splashed deep inside her and she could feel it covering his dick stroke by stroke. It lubricated him and made the last moments not only bearable, but pleasant.
He did not pull out of her, she pulled him out of her. She felt a little regret to part, however briefly, with her new friend and its owner. She went to the bathroom, cleaned herself up, and brought the bottle of oil back to the bedside table.
Milo lay on his back smiling at her, his dick standing vertically like a NASA launch vehicle. It showed no sign of use other than the liquid residue of sex coating its surface. Ariana stopped briefly and savored the sight. He was too good to be true.
“God,” she thought, “I’ve got to humble this arrogant boy.” That was Ariana: she needed to dominate. She wanted this proud boy to find his limits and for him to know that it was she who brought him to admit them. Then she would have the exquisite pleasure of sending him away the knowledge that he was inadequate to her need.
The problem was that by now most men would be drowsing off, trying to recoup their energy. Milo just looked at her fixedly with a smile that she found slightly challenging. Her work, it seemed, was cut out for her.
She lay on her back next to Milo. She reached over and grasped his cock with a proprietary air.
“Tired?” she asked.
“No. Are you?”
“I’ll let you know when I am,” she said.
“Do you want to go again?”
“Whenever you’re ready,” she said, suppressing a sigh. Then she had an idea.
“Here,” she said, “stand up.”
She positioned him facing the same mirror he’d spattered earlier in the evening. She grasped his tool and said, “Come when I say so.” If she couldn’t drain him one way, she’d drain him another.
“OK, now!”
In a couple of seconds his dick started to twitch and then to spurt spasmodically. Immediately she began to move his cock purposefully.
Milo saw that she was writing something on the mirror with his come. It was her name – ‘ARI’.
Milo laughed delightedly. “Your handwriting is awful!”
“I was using my left hand,” she said defensively. “I’ll show you.” She moved around to his other side and used her right hand.
“OK, ready.”
In a second he started twitching and spurting. Ariana’s handwriting was much improved, although the ‘ANA’ did not quite start where her ‘ARI’ left off.
“See?” she asked.
“Very nice. It’s what they used to call copperplate. An elegant hand.”
“Yes it is, considering that my writing implement is a little too large for my hand,” she smiled, “and runs out of ink quickly.”
“Sorry, ma’am. You’ll just have to dip it in the inkwell more often.” He surprised himself at his own boldness, but she didn’t seem to mind.
Actually, Ariana felt that Milo was challenging her and she committed herself doubly to wearing him out.
“Let’s write the rest of my name. OK?” She looked to see if he betrayed any sign of anxiety. There wasn’t any.
“OK,” he said. “Ready? Don’t forget to dip the nip occasionally!”
She finished writing her name, ‘ARIANA MARIE SANS-REGRETTE.’ Her handwriting was very good by the time she finished, but the ‘ink’ was running down the mirror, blurring the text.
“Say, don’t you ever run dry?”
“I don’t know,” he shrugged. He looked down at his cock in bewilderment. His most intimate part was also a deep mystery. Tonight it was revealing some of its secrets. It had been a very good night so far.
“Tired?” she asked.
“I want to do you again, ma’am. It felt real good.” His boyish grin was disarming.
Unfortunately, Ariana thought she wanted to give her cunt a little more rest.
“You’ve never been sucked off, have you? No, of course not. Well, I think you’re going to like this.” She had an educated mouth, strong lips and a cunning tongue. If she couldn’t fuck him into incapacity, she’d blow him there.
She dropped to her knees and looked the monster straight in its unblinking eye. “It’s you or me,” she thought, “and I never lose.”
Milo was electrified by the sight of this beautiful woman kneeling in front of him, servicing him. It was a powerful stimulant. Even though she could only take a few inches of him into her mouth, she was adept as giving him pleasure. Sometimes she licked him, sometimes she sucked him like a popsicle, and sometime she made her mouth a taught ‘O’ and simulated her cunt.
He caught her by surprise by coming in her mouth forcefully after only a minute. Instinctively he held her head so she couldn’t release him. She nearly drowned on his come and thought some come came out her nose when she coughed. When he came to his senses he let her go.
“Sorry, ma’am. I don’t know what came over me.”
“Came over you? Came in my mouth, you mean.”
“I’d sure like another one of those if you don’t mind,” he said shyly.
“Not now. I forgot my water-wings. Maybe later.” She was a little sour. Not only was he as ready as ever, she had sucked him off in the most submissive of postures. It was unlike her.
“Time for you to learn to be selfless,” she said.
“What do you mean?”
“Don’t you know it’s more blessed to give than to receive? Like I just gave pleasure to you, now you’re going to give it to me. Understand?”
“Just tell me what to do.”
Ariana had never given a man instruction on how to give head before. She had seldom found a man who knew how to do it half-way well, either. She wanted to come and was reluctant to go for a ride on his rocket. The solution was to teach him to give her pleasure the way she needed it.
“First, a little geography lesson…”
Slowly, patiently, step-by-step she taught him the ins and outs of cunnilingus. She taught him the wide, slow approach, the near miss, the ‘accidental’ encounter, the tentative general focus, and finally the culminating laser-like focus. She taught him to avoid fatigue by putting his face close and alternating the lips and tongue. She taught him to gently suck her clit – which was large and an ‘outie’ – when it was ready.
Milo loved it. He was a willing and gifted student. There came a time when Ariana lost interest in teaching. Even more, she lost the ability to think straight. Milo learned his lesson well and quickly began to embroider inventively on the themes he had been taught. He felt a certain comfort having his head lodged between her thighs, his mouth and nose brushing her cunt, her aromatic, earthy smell filling his nostrils, her salty taste filling his mouth.
By and by, Ariana began a long climb from ecstasy to ecstasy, orgasm following closely on mounting orgasm.
Ariana lost control, something she had seldom done since reaching adulthood. She gripped his head with both hands and locked her ankles in the small of his back. Milo wasn’t going to go anywhere until she was finished. She was in no hurry to finish.
Milo understood pacing. He matched his timing to her subtle signals, switched between his tongue or lips to avoid tiring himself. He discovered for himself that inserting his finger a few inches into her cunny with a niggling motion seemed to redouble her pleasure.
If he could have seen her face, he would have known that Ariana was lost in orgasm, something that had seldom happened to her with women and never with a man. Milo as a person disappeared; only a tongue and lips remained. The fire in her belly that had brought her to LA was being quenched by a deluge of sex.
Milo stayed on his knees serving Ariana until the night sky turned pale. Finally, Ariana let him go and collapsed. Milo poured Vitamin-E oil the length of his cock and spread it evenly. She raised no objection when Milo put his hands under her buttocks and lifted her off the bed, embedding his penis in her until they were pubic hair merged. She put her arms around his neck and wrapped her legs around his waist, locking her ankles behind his back.
Milo took Ariana by the waist and, standing in the middle of the bedroom, he slid her up and down his dick like some sexual appliance. He was slow and rhythmic, careful not to overtax her already heavily used clit. By and by he felt her lubrication come down again and he increased his stroke.
“The sun is coming up,” he said.
“Umm,” she replied vaguely.
Effortlessly he carried her over to the window overlooking LA and the ocean, never losing his stroke.
“Look,” he said. She didn’t respond, so he said again, “Look.” She turned her head and narrowly opened her eyes to the dawn and the hills and the sea. The moment seized her and him at the same time. They both came loudly as Milo slammed into her like a pile driver. When he came, Ariana thought she would faint. When she came, she did.
She recovered consciousness just as he pulled out and set her carefully on the bed. She was limp. She felt like her bones had been removed.
Milo saw her state and gently repositioned her on the bed. When he returned from the bathroom she was asleep. He lay down next to her. In her sleep she reached over and took his cock in her hand and gripped it.
He must have catnapped for a little while. When he awoke it was because his cock was uncomfortable from her constricting hand. He tried to gently remove it but she only increased her grip. She only freed him when she swam upward to full wakefulness.
“To make sure you don’t get away while I’m asleep,” she said with a dreamy smile. She was instantly shocked at this silly statement. What had come over her, the hard-boiled man-eater? Milo. Milo had come all over her!
Milo reflected on how long he had complained about his penis and how his feelings had turned 180 degrees overnight.
“Feel like doing a little writing?” she asked.
“‘Writing’ or ‘riding’?”
“Yes,” she said and slipped her mouth over his dick.