It was the day Carl had been half looking forward to, half dreading. The summer he turned nineteen, his parents had gone to South Africa and left him to be looked after by their middle-aged neighbour, Doreen. She had let him know on Friday that the following Monday a few of the ladies she used to work with were coming round and that Carl was to serve them coffee. He blushed, thinking about standing in a room in the tiny underwear Doreen had bought him, especially with five or six women looking at his body as he politely served them coffee and biscuits.
Doreen had told him about it on Friday because she knew that it would be on his mind all weekend. All she had to do was say the word 'Monday', even if it wasn't related to the ladies' coffee morning, and she could see his beautiful cock stiffen in the special underwear, which she made him wear at all times. It was almost like a Pavlovian response. 'Oh look, The Godfather is on TV on Monday,' she said, pretending to look at the TV guide but actually looking at Carl's penis just to see it twitch involuntarily at the mere mention of the M word.
When Monday came, Doreen didn't give Carl his usual early morning milking -- she had got into the habit of masturbating him every day. This departure from habit made his penis even more prone to getting hard than if she had emptied his balls of sperm. The fact that they had gone off schedule made Carl even more nervous about the coming encounter, so much so that he could actually see his heart beating between the two beautiful pectorals that were developing on his 19-year-old chest.
He was asked to shower thoroughly and stay in his room. Doreen took some breakfast up to him just to make sure he had some strength and to make sure he was ready in his underwear for when her friends arrived.
As he sat on the bed, his heart pounding, Carl heard the doorbell ring, then some ladies' cheerful voices, then the doorbell again and again. It sounded like quite a party down there.
Then he heard Doreen's voice call out, 'Carl sweetie? Can you come down?' He opened the door of his room and stepped towards the stairs taking him down to the group of expectant older ladies. 'I just want to introduce to my friends, dear,' she said.
He started down the stairs, his penis already growing at the thought of the audience waiting for him. Before he could see them, they could see his penis in the thin white briefs as he came down the stairs. There was an audible gasp among the ladies still waiting in the hallway.
'Here he is,' said Doreen, proudly as Carl reached the bottom stair. 'Stay there, dear,' she said to Carl, 'let us all appreciate you from up there. Your lovely genitals are nearer eye level that way.'
Carl looked around the group of six ladies, all in their 50s and 60s, grey haired and all dressed smartly as if they were going to church or to a wedding.
'Ooh, what a beautiful penis,' said one to another.
'It's his balls that I really like,' said her friend. 'And he's so smooth...'
Then one reached forward and slipped a finger into the underwear... 'This fabric is lovely. I would like some underwear in this... Wherever did you find it, Doreen?'
Carl didn't hear the answer. The brush of the woman's finger against his scrotum was enough to make his penis so hard that it actually stood out from his body, stretching against the fabric of the briefs.
'Well, I think Carl is getting very excited with all this attention,' said Doreen, 'so why don't we move through to the lounge while he gets us our coffee or we may never get any.'
With that she led the ladies through to the sitting room where they formed a circle sitting variously on her sofa, her armchairs and on a dining room chair that had been brought in from the adjoining room. 'Carl dear, you know where the coffee is. Don't keep us waiting, will you?'
Carl went into the kitchen where six cups had been laid out on a tray and a little cork mat had been placed so that he could take the coffee jug from the machine and put it on there. His penis was still hard and he could feel droplets of precum leaking out into his briefs, realizing they were very visible when he looked down. He blushed at the idea that these ladies would notice his excitement as he took the tray of coffee to them in the lounge.
And he was right about them noticing. 'Oh, look Doreen,' said a woman he heard referred to as Sophie, 'I think Carl has made a bit of a mess of himself.' Carl blushed so hard his whole face felt like it was burning.
Doreen just giggled and said, 'Well, that's teenage boys for you, isn't it, Sophie? I'm sure your neighbour would be just the same if he was getting all this attention. What was his name again? Kevin? Oh, he's very cute. You should have us over one morning, and we can see how Kevin serves us coffee...'
'I'll have to shave him first,' said Sophie. 'Get his balls as smooth as Carl's'.
As he walked towards the table to put the tray down, Carl burned with embarrassment, not only at the stain he'd made in his underwear, but at the idea that when he got to the table, he would have to bend forward exposing his hairless ass to the ladies. But before he could get to the table, Sophie, the smartest of the ladies, wearing what looked like a Chanel suit and some pearls, reached forward and put her finger on the precum mark, touching the end of Carl's stiff penis as she did. 'Look!' she said. 'He's soaking.'
He tried to ignore the contact and put the tray on the table, looking to Doreen for reassurance that he was being a good boy. She pursed her lips and gave him a little nod as if to say, 'Well done.' Still leaning forward, he began to pour the coffee from the jug into the six cups.
'Ooh, doesn't Carl have a delicious little bottom!' said another of the ladies.
'He certainly does, Elizabeth, but you wait until we milk him in a few moments and you'll see just how lovely it is.' Carl burned even redder at the exciting prospect of this. He had assumed there would be a milking but this was the first time anyone had mentioned it.
He picked up two of the cups and walked to the ladies who had taken seats on the sofa to hand them the coffee. As he reached out to pass the cups, one of the ladies put her hand forward and cupped his balls through the underwear. 'Oh, Doreen, I think there's a lot of sperm in these balls. Don't tell me you've been neglecting this boy's milking schedule...'
'Of course, I haven't. Have I, Carl dear?'
'No Miss,' said Carl, his voice breaking. This was the first time he'd spoken that morning, and it was like it needed warming up. His hands holding both coffee cups, Carl could do nothing to avoid being groped, not that he would have been allowed to be so rude as to deny a friend of Doreen's a feel of his genitals anyway. And not that he wanted to.
As he passed out the rest of the coffees, the other ladies all gave his hard penis and his balls and his ass gentle appreciative touches, cooing to each other and muttering, 'Ooh, lovely!' 'Isn't his penis just gorgeous!' 'I really can't wait to see his little hole. I bet it's as pink as a rose.'
As the women drank their coffee and ran their eyes over Carl, Doreen got up from the dining room chair. 'Stand up here so we can see you better, Carl dear,' she said, indicating the recently vacated chair with her eyes. Carl, whose blush was now down his neck and across his chest, did as he was told. He stepped up onto the dining room chair while the women looked and muttered and giggled excitedly. They all marveled at the boy with the hard penis bursting out of his almost see-through underwear standing on the chair.
'Just look how beautiful Carl looks,' said Doreen standing next to him, her face more or less level with his stiff and dripping cock. He felt the eyes of these older women all over him, making his penis leak even more precum.
As the ladies finished their coffees, Carl was allowed down from the dining room chair and asked to collect the cups. Circulating the room, he received more appreciative strokes on his penis, balls and bottom. With all the cups on the tray, he took it out to the kitchen and returned. The coffee table that the tray had been on was now cleared of the magazines and the flowers that were on there. Carl now realized where the morning's milking was going to take place.
Doreen came over to him with a look of ownership on her face. She proceeded to pull down the briefs as she looked from one woman to the next with a satisfied smile on her lips. 'Now I'm going to show you how we milk this boy and collect his sperm. Carl knows it's for his own benefit, don't you dear?'
'Yes, Miss,' said Carl, as the underwear fell to the floor and his unconstrained penis leapt up against his belly.
'Now, up you hop dear and get into position,' said Doreen, still looking at the ladies as if to say, 'Look what I can make this beautiful young man do for me.'
Carl got onto the coffee table, on hands and knees his head held down embarrassed. 'Look up, dear,' said Doreen. 'We need to see the reaction on your face as we milk you, don't we?'
'Yes, Miss. Sorry, Miss,' said Carl, looking up and trying not to focus on any of the faces staring at his naked body on hands and knees on the coffee table.
'Now, spread your knees wider, Carl,' said Doreen. 'Some of the ladies can barely see if you keep your legs together like that.' Carl did as he was told and could feel all those eyes looking at him. He could feel their gaze tracing from his hairless little ass, along his perineum, to his balls and then to his hard penis. The latter was stiff against his belly even in his hunched position and already dripping precum onto the surface of the coffee table.
'Oh, I think he's ready for you Doreen,' said Sophie, leaning forward and dabbing a finger in the precum. Carl could see she then licked it off her finger as if it were honey. 'Mmm, delicious,' she smiled at the woman next to her.
'Now, we don't start straight away,' said Doreen, as if she were giving an educational lecture to these ladies, as indeed she was. 'We let Carl get ready mentally for the process, don't we, dear?'
Carl nodded. She gave him a little swat on his bottom to remind him of his manners. 'Sorry. Yes, Miss,' said Carl.

'And when you can see the penis actually twitch... See that! It's happening now. That's when you start your milking. Carl knows that however excited he is to be milked, he's not allowed to come until permission has been granted. This is a way of building up his control over his orgasm. Not that he has much control over his orgasms,' she laughed. 'That's more my job.' The ladies giggled.
'And when he's quite ready, you start at the base of the penis... that's why I keep Carl nice and shaved so we can see exactly what we're doing... and you start to stroke upwards towards the head...'
Carl could see the ladies in his eyeline staring, not at his face but beyond it to where Doreen was starting the slow strokes that would eventually bring him to an orgasm in front of the gawking crowd.
'You go slow so as to prolong the experience,' said Doreen. 'Sophie, why don't you have a go, to see if you've understood what I mean.'
Carl could feel Doreen's hand pass his stiff penis to the other older lady, whose grip was tighter than Doreen's. 'That's right, grip it but not too tight and start slowly. Pull the foreskin forward and then back... Oh look, you're getting some lovely precum from Carl already.'
'Oh, Elizabeth, you must try this,' said Sophie over her shoulder to her friend in the armchair. 'His penis is so smooth and so hard... Come.' Elizabeth, even older than Sophie and with a short grey haircut and badly applied make up took Carl's penis from Sophie.
'Oh, you're right,' she giggled. 'It's so hard. That's why I love teenage boys, don't you? They get rock hard. My next-door neighbour, if he sees me watching him out of the window while he's out there sunbathing in his briefs, he gets hard just seeing me looking at him. It's quite funny, really.'
While this conversation was going on, and Elizabeth's hand rather expertly squeezed Carl's rock-hard penis, there was a little tap on the French windows and then the sound of the window opening and a voice saying, 'Doreen, are you in? Oh...!'
The 'Oh' was the moment the woman outside caught sight of what was happening on the coffee table in the centre of Doreen's lounge. 'Oh, Mrs. Martin, how are you? Sorry, we're right in the middle of something right now, but feel free to come and join us.'
Carl knew Mrs. Martin. She was a neighbour, a married woman of about sixty-five, always smartly dressed even on the weekends. 'We're just milking my nephew Carl. You know Carl.'
'Yes, of course. Hello Carl,' said Mrs. Martin as if a teenage boy on his hands and knees on a coffee table being milked by a group of older women was the most natural thing in the world. 'Hello, Mrs. Martin,' said Carl, polite even in the middle of having his penis massaged by Elizabeth.
'How's your husband?' asked Doreen. 'It's a shame you didn't bring him. Next time perhaps.'
'Oh, nice work,' said Mrs. Martin to Elizabeth. 'You're getting him quite excited. Look at that strand of precum! It stretches from the end of his penis to the table! And that's a very nice penis, Carl.'
'Thank you, Mrs. Martin,' said Carl.
'But you are missing a trick,' she went on, still addressing Elizabeth. 'If we can get Carl arch his back and to widen his knees a little...'
'Carl dear, do what Mrs. Martin tells you,' said Doreen, who was watching Elizabeth's strokes, to make sure they were being done correctly.
Carl widened his knees until they were on the edge of the coffee table and the cheeks of his ass had parted. 'You see,' said Mrs. Martin, 'if you get the cheeks parted like that, you can see the hole, which I'm glad to see you're keeping nice and smooth, Doreen.'
'Of course!' said Doreen. 'I like to shave Carl every day or every other day, so there's no stubble and just a nice smooth surface for me to work on.'
'But ladies, if you look carefully at the hole, you'll see that it tightens and relaxes as this lady does those nice long strokes. You see?' The ladies peered in and nodded.
'Oh, yes!', they exclaimed as they could indeed see how Carl's little hole was clenching with Elizabeth's strokes.
'I used to work in a men's sixth-form college with groups of 18- and 19-year-old lads, and a lot of them would need regular milkings just to keep a lid on their bad behaviour,' said Mrs. Martin. 'We found that if we could keep their balls free of sperm, they could concentrate on their studies much better.'
'Oh,' said Doreen. 'I suppose that makes sense.'
Mrs. Martin spotted the discarded underpants on the rug and picked them up, putting them to her nose. 'Mmm, musky,' she smiled. 'That's the smell of teenage boys.' And she passed the pouch panties to Sophie who smelled them and passed them on until all the ladies were cooing over the smell of Carl's underwear.
'Now, when you see the hole clenching like that, it means it wants to be touched,' said Mrs. Martin, sounding very much like the schoolteacher she used to be. 'So, what you do... If I may?' she asked as Elizabeth handed Carl's penis to her. The feel of Mrs. Martin's hand was so different to the other ladies' hands. It was stronger, it gripped tighter.
'So, while you maintain the stroke you take your other hand...' She held up her other hand then leaned forward to dip a finger in the pool of precum that was now on the coffee table, 'moisten it, either with spit or lotion or... seeing as Carl seems to be producing a lot of his own lotion...' The ladies giggled.
While still stroking Carl's stiff penis with an authority Carl hadn't really felt before then, Mrs. Martin put her finger, loaded with precum, on Carl's twitching hole. A shock of electricity ran through Carl causing him to shudder. 'You see!' said Mrs.Martin. 'That should bring a whole new dimension to this boy's milking. But don't let him have it, he has to ask for it...'
It was true. Carl was moving his hole towards Mrs. Martin's finger, burning to feel the touch of that woman's finger on him again. Mrs. Martin obliged, now circling the pink little hole with the sticky precum.
'And when you think he's got used to that...' Carl could feel the woman's finger prising his hole open, entering it. Nothing had ever gone in Carl's hole before. He was embarrassed about his ass but this woman wasn't asking permission, she was just worming her finger into it... and it felt amazing, but humiliating at the same time.
'If you put your finger in this way,' she was pointing down, though Carl obviously couldn't see, 'then you'll be touching his prostate and that's what will give you a really deep milking. So, keep your stroke but massage this spongy bit inside his anus at the same time. Doreen, why don't you have a try?'
Doreen stepped forward. To be honest she'd been feeling a bit annoyed at this woman's ownership of Carl's penis and hole, which were by rights hers to do what she wanted with. 'Now carry on with the strokes. Oh, you are good at that. You must have had quite a bit of practice...' The ladies in the room giggled. 'And, that's right, dab your finger in some of Carl's natural juices... Just touch the hole to start with and, yes, in you go. Maybe it would be a good idea to cut those nails down a bit for next time.' It was true, Carl could feel the sharpness of Doreen's nails as her finger went in and started to massage that secret bit inside of him.
After Doreen, Sophie had a go, and then Elizabeth and then the other ladies until everyone had had their fingers in Carl and were jokingly smelling his boy musk on those same fingers as they watched the next woman.
'But if I may, would you allow me to do the final milking and show you how the finger works?' asked Mrs. Martin.
'Of course,' said Doreen, who was now happy to have had this extra bit of instruction and actually quite excited at the sight of Mrs. Martin with her finger in her neighbour's private hole.
Mrs. Martin came back to Carl, resuming her stroke on the boy's penis. She alternated putting her hand to her mouth and to Carl's mouth so they could each taste his precum, which was actually quite delicious. Then, with some of that precum on her finger, Carl felt the most expert hand of all enter his hole again, massaging and pressing and teasing as she stroked Carl's rock hard penis.
Within a few strokes Carl was feeling that he wouldn't be able to hold out much longer. 'Miss...' he said. 'Would it be OK if I released soon?'
'Are you ready, Carl?' Doreen asked as if surprised, even though this session had now been going on for quite some time. 'Yes, as long as Mrs. Martin is agreeable.'
'Mrs. Martin, would it be OK if I released now?'
'Yes,' said Mrs. Martin. 'You've been a very good boy. I think it would be OK if you wanted to...' But before she could finish the sentence Mrs. Martin felt a tightening of Carl's hole around her finger, could feel the pulse inside of him and then the rush of sperm as it shot through the underneath of Carl, up his stiff penis and out onto the coffee table. As he came, he shuddered, the shudder going right through him, a shudder Mrs. Martin could feel in her finger...
As Carl's shudders became less strong and his head hung in sheer exhaustion, Mrs. Martin slipped her finger out from Carl's hole, and she too sniffed it. 'Oh, that is rather nice, isn't it?' he said to the assembled ladies. 'They should bottle it.' At which the ladies giggled.
'Stand up straight for us now, Carl dear,' said Doreen. 'We want to watch your penis go back to normal.' Carl stood, feeling all the eyes in the room on him as his penis slowly deflated, dripping the last drops of cum onto Doreen's Persian rug.
'May I?' said Mrs. Martin as Carl's penis finally went soft and before Doreen could work out what he was asking permission for, Mrs. Martin scooped up the sperm that was on the coffee table and put it in her mouth with relish. 'You really are delicious in every way, Carl,' she laughed as the boy blushed. 'I should bring my other neighbour's son next time to see how you compare.'
'And you can bring Kevin, Sophie,' said Irene. 'I'm sure he could do with a good milking.'
