Milo’s Complaint · Part 1 (1/2)
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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!"
"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 finger
Milo’s Complaint · Part 1 (1/2)
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