Waking Tony for his morning milking reminded Alice of weekends at the beach. She'd milked him there once, standing out far enough that they were in up to their necks. She'd pull his stiffy out of his swim trunks and masturbate him until he shot off big juicy ropes of his boyish semen to swirl and twirl in the nutrient-rich waters of Reservoir Three, just off the brilliantly artificial white sands of Chlorine Beach.
Instead of sand for a castle, the little plastic pail she brought with her to his room was half-full -- all the way full and it might spill if Tony got overstimulated during milking -- of very warm, cardamom-scented water and a pristine white washcloth.
He was awake and eager, as he always was, and naked. His half-erection perked up to full attention the moment he saw her breasts, supported, but not covered by his favourite pushup. She sat beside him, flannel pyjama bottoms brushing his shoulder. Squirting a little oil over her palm, she took hold of his penis and began to stroke it.
"No wet dreams during the night?" she asked, reaching between her breasts with her free hand to unclasp her bra, sending her breasts tumbling, the left one in easy reach of his lips.
"I dreamed of you," he said softly, licking the big brown gumdrop of her nipple.
"Oooh!" she shivered, "Did you dream of sharing a bed again?"
"Oh, yes!" he moaned, his hips moving, "I thought of the coitus-training holos and then I was with you and -- Oh I'm sorry, I know we're not supposed to -- "
"That's all right," she increased her pace and pushed her nipple between his lips, "You know all thoughts are healthy, just so long as -- "
He released her nipple just long enough to mumble, "But in the dream I didn't reach my... uh... climax." He was close to a climax now, but still a bit embarrassed talking about it.
"That's why we have our regular milking, Tony dear!" She felt him begin to thrust up into her fist, "Now, give me a nice big -- Oh!" He was squirting now, big, healthy boyish streaks of glistening semen splashing his stomach and chest. These young men could go from soft to ejaculation so quickly! she thought.
"And that's why," she released his penis and reached for the washcloth, "Why boys have to be milked," she began to mop off his chest, "So you don't squirt your sticky on the sheets in the middle of the night!" She rinsed the washcloth in the pail and started to clean his pubic hair and penis, pushing the foreskin back to get off the last drops of semen and oil. "Besides, wouldn't you say the orgasms you have when you're awake are better than when you're sleeping?"
"Oh, yes!"
"And having someone else do it for you is better than doing it yourself?"
"Oh, yes!" Of course, he'd been taught to masturbate, given holos to watch if he needed the stimulation, and he did really enjoy doing it, (especially when Alice watched) but...
"You remember when I was in hospital for a couple of days and Mrs Henderson came to look after you?"
He remembered her. A very nice old woman who'd handled him with the skill of long practice. She'd always cup him first, massaging gently, saying she could tell how full a boy's balls were just from how they felt in her palm. Those thin, bony hands had masturbated him over and over that weekend. The ninth time, she barely managed to coax out a last few drops, just a few tiny pearls of balljuice splashed across his heaving abdomen, but even that felt so nice.... and when she thought he wasn't looking, he'd caught her furtively licking her fingers afterwards.
She taught him a little bit of an anatomy lesson too, doing her mok'bara routines nude and letting him watch while she showered, saying he shouldn't be just learning the idealized body forms they showed in the health education holograms or worked on in the practicums.
In Tony's memories of weekends, the two nights she'd spent with him were almost as memorable as trips to the beach with Alice. Since then, she'd had a starring role "looking after" him in quite a few of his wet dreams! "Old Annie" Henderson? Was she still --
"She's still working, but this time our friend Zora is coming to visit. She might stay here overnight and she might not, but she'll have charge of your penis for the days I have to spend at Regolith Research." Alice started wringing out the washcloth. "You've met her. You saw her a few times when she came over to help set up for the HourlyFun parties and you got extra credits to go to Sapphire's Game Room because we needed the entire apartment?"
"Oh, yes!" Zora was much younger than Mrs. Henderson. If she let him watch her exercise...
"She won't be getting here until the day before. I'm hoping we can have dinner together, but you may not see her until the day I leave. Anyway, we'll definitely talk on video before that, OK?" She kissed him on the forehead and got up to rinse the bucket and put the washcloth in the hamper. He pulled on his robe and went in the kitchen to start breakfast.
It was a few days before Zora got a chance to call. She was as he'd remembered, a loud woman, a bit coarse, perhaps, but with heavy, sensual lips that Alice had always described to Tony as "kissable."
The next morning that loud voice was waking him, "It is so easy to be hopeful in the daytime when you can see the things you wish on, don't you think?" Half forgotten dreams of poetry...
He yawned, smelling the same cardamom scent Alice had always brought, but the woman sitting next to him on the bed was a few years older, dark-skinned and wearing only skimpy white cotton briefs. Her breasts, heavier than Alice's, with even more prominent nipples, were definitely things to wish on!
He stretched, lifting his hips as she helped him pull down his pyjama bottoms. "Do you prefer baby oil or regular lube?" she asked, "Alice had to leave in such a hurry she didn't get a chance to tell me."
"Alice always liked the oil," he said, which wasn't really an answer.
"I like it too," she smiled, "So boyish and young!" Squirting a little of it on her cupped hand, she prompted, "All set? Got a nice hard-on ready for a lonely woman?"
He was more than ready, except he had to pull off his pyjama top, but when she wrapped her palm around his erection, she found it rigid, the head already engorged and purpling.
"You can suck on it nice and hard," she leaned forward, dangling a nipple in front of his face. "Ooooh!" she gasped as he latched on, "I can tell you're ready to give me a nice big load!" He could feel her hips moving now, as her thigh muscles tensed and released in time with her strokes. He wanted to reach out, to touch her, even though he knew touching was --
Anyway, seconds later she brought him expertly to his first climax of the day, squirting streak after streak of hot boymilk over his chest and abdomen.
"Aah!" she murmured, her hips still squirming, "Such a hot mess! Almost up to your chin, boy!" Chuckling with pleasure, she carefully massaged the last few drops out of his relaxing penis and then mopped up every trace of semen from his skin and pubic hair. Her touch felt so nice and warm, and she didn't even joke about how quickly he ejaculated, the way Alice sometimes did.
At breakfast she wore a robe, but left it open so he could see as much as he wanted of her. What he saw was her left nipple, still distended from his vigorous suction, but maybe it was just imagination.
When the conversation turned to plans for the day, she hesitated, then said a bit guiltily, "I may not be back in time for your lunchtime milking," she paused as she slipped the last piece of cruller between her lips, "I hate to leave a boy to masturbate by his lonely self, so the least I can do is give you some fantasizing material. What do you say?"
"That would be very kind of you," he said politely. That was the second time she'd said "lonely." Why?
"It's just a just-in-case," she smiled, "I'll hurry and be back here if it's humanly possible!" Then her smile faded, "I know stroking yourself isn't the same as being with someone." She paused, and he wanted to ask if something was wrong (lonely?), but she perked up, "So let's take a shower together." She put down her fork, "That'll give you some good fantasizing material." She blew him a kiss, "Think of me as dirty as you can!"
He couldn't think of anything to say, just smiled and nodded goofily. Alice had, of course, sometimes showered with him when they were in a hurry in the morning, sometimes even given him a super-quick morning milking with a soapy, slippery palm. But all the same he was very excited at the thought of Zora lathering him up.
This was, you remember, back when the public gyms were not so crowded and usually had room for separate showers for men and women, so for Tony it was a special treat.
He felt a tiny bit uncomfortable, though, as they hung up their robes, thinking that if he wasn't supposed to handle her breasts (or, indeed, any other part of her anatomy) when she milked him in his bed, was it really OK in the shower?
Then her briefs came down, and he saw her tightly curled black pubic hair was already shiny and wet, so wet the crotch of her underwear was damp. Would she let him --?