Carl's first milking by Doreen

MarianneFromThePool

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Carl had never heard the term ‘milking’ before but he could guess what it was and felt dread and excitement at the prospect of his first session in equal measures.



‘Now, Carl, I think probably the easiest way for me to milk you would be if you hopped up on the dining room table, that way I won’t have to bend,’ said Doreen, indicating with her hand a table through an archway from her lounge. The table had been cleared of flowers and fruit, which were now on the sideboard, and a towel had been layed down, almost as if someone were about to sunbathe on the table.



‘Now, up you get, on your hands and knees and I’ll be in presently,’ she said, leaving the room. Carl did as he’d been told, climbed carefully onto the table, hoping it wouldn’t crack or wobble, and waited for Doreen to return on his hands and knees, feeling conscious that his arse and his balls were clearly visible to anyone who walked into the room right now.



As she came back in, the sight of Carl on her table on all fours as instructed took her breath away. He was so big, so beautiful, so powerful and yet he either didn’t realise that or he was happy to give his power to her, maybe because it turned him on. Whatever the reason, Doreen was determined to use her power over him.



She had been to the kitchen to collect a glass, which she put down on the towel under Carl’s belly. Then she started to stroke him all over. She stroked his feet – beautiful feet – then his calves, which she noticed had a little hair that she would have to deal with. His thighs were muscular and strong. Then she walked along the table and ran her fingers through his golden hair, caressed that beautiful, honey-coloured face now tinged with the pink of embarrassment. She gripped his neck, then ran her hands over his shoulders, his muscular back. Coming back down the table she stood between his feet.



‘Put your legs further apart, Carl,’ she said. He complied. ‘And arch your back.’



Carl didn’t quite know what she meant by that so she put a hand on the small of his back and pressed it down so his buttocks opened up. She was now looking at the little pink rosebud of his anus. What fun she was going to have with that little hole, she thought. And the balls, hanging heavy between his legs. She reached out and touched them, giving Carl a little shock at the contact of her hand. She weighed them in her palm, let the balls roll in the scrotum as she looked.



Carl’s cock, which she couldn’t see from this angle, was so hard it was parallel to his body, twitching and drooling precum onto the towel beneath him. He was desperate for Doreen to touch it, to grip it, to wank it, but she was taking her time. She brought her face close to his spread arse so he could feel her breath on him and inhaled the musky smell of her new toy. It was all she could do to stop herself licking him, putting her tongue on his hole but she was saving that for another time.



Then, coming to his right, she reached under him and took his penis in her hand. Carl groaned involuntarily. She gripped it then ran her hand up it until it was on the head, which was slick with precum. She took some of the precum on her fingers and started to work the head of Carl’s cock as he moaned and started to twitch.



‘Keep still, Carl,’ said Doreen, knowing full well how difficult it was for him to stop his body from reacting to her touch but wanting him to struggle. As she tortured his penis, her other hand was fondling his balls, massaging the hard ridge underneath his balls and occasionally brushing past his anus.



‘Don’t cum until I give you permission,’ said Doreen, almost sternly.



‘No, Miss. But I’m close Miss.’ She took her hand off his penis so that he didn’t spill that sperm before she was ready for it and watched it twitch as Carl bit his lip, trying hard not to disobey but desperate for relief. When Doreen noticed his penis had stopped twitching so violently, she gripped it again and Carl moaned again. She continued to rub, running her fingers over the head every third or fourth stroke.



‘Miss…’ Doreen took her hand away again and watched Carl as he struggled not to disappoint her, only returning her hand when the crisis seemed to be over. She continued like this for what seemed to Carl ages until at one of his ‘Miss…’ pleas, she said, ‘You can give me your sperm now, Carl.’



The words were barely out of her mouth when she felt his penis thicken, felt the area under his balls begin to pump and a powerful spurt of sperm shot from his cock and into the glass she had placed beneath him, a glass she’d repositioned until it was in the perfect spot to collect this precious liquid. Then another spurt. Then another. It felt like the spunk would never stop… and then it did and she gripped him at the base of his penis and ran that grip along his shaft to squeeze the last drops from him.



His head hung, she could see the beating of his heart through his whole body as she said, ‘You can relax now, Carl. Turn over and relax.’ She took the glass, half full of creamy white sperm from beneath him and he laid first on his stomach then turned over onto his back, his eyes closed, his face and chest red, his penis visibly shrinking and still dripping. It was a beautiful sight of a young man sated.



She let him stay there, watched him as he recovered, ran her eyes over him as she smelled then sipped the contents of the glass, spreading the stickiness over her lips, tasting the sweetness of it in her throat.



Eventually she told him to get up, took him by the hand upstairs to the shower where she used the hand-held hose to wet him before soaping him all over, rinsing him off and then drying him with a towel. She then took some lotion and rubbed it into his shoulders, his back, his buttocks, his legs, his feet and, finally, his cock, which, even though he had emptied himself just minutes before, reacted to her touch until it was half hard again.



She then handed him the pouch-panties, which he put on. She looked down at his cock, hammocked in the sheer fabric and smiled. And they spent the rest of the day like that. Carl helped her make lunch wearing the little pouch-panties so she could see his cock at all times, see it get hard pretty much every ten minutes. In the afternoon, they watched a little TV from the armchairs, which faced each other, Doreen’s gaze switching between the TV and Carl’s penis, which seemed to stiffen every time she looked at it.



In the evening, when it had got dark and Carl’s penis seemed to be permanently hard, Doreen milked him again, up on the table like the first time. When he had given her more of his sperm – again in a glass – she wiped his penis and led him up the stairs to his room by the hand.



‘As it’s your first night, I’m going to get in with you,’ she said to Carl. ‘So, take off your pouch-panties and climb in and I’ll be in in a minute.’ Carl did as he was told, got in under the pink duvet and waited. Doreen came back wearing an ugly nightdress. She pulled back the duvet, looked at this beautiful young man, whose hairlessness made him look even more naked, and climbed in and turned off the light.



Carl slept fitfully. Doreen’s hands were on him throughout the night. On his buttocks, on his balls, on his penis, which now seemed to be permanently hard, even on his anus. Every way he turned, her hands would find a way to explore him, even as he slept until the light started to appear around the edges of the curtain and he opened his eyes. She was looking at him, his cock in her hand… ‘Good morning, Carl,’ she said.



‘Good morning, Miss.’



‘Now, let’s get you up and showered and in your pouch-panties. It’s going to be a big day. We have your headmistress coming for a visit…’
 
Love this story! When I was younger I used to fantasize about being made the sexual slave of a much older woman. When I was in my late twenties I used to take my mother in laws panties to wear when I could, she was 62 at the time...loved the worn ones too... :)
 
Nice! How long before he ends up totally and completely naked in front of the headmistress before she gets to watch him getting another good milking.
Lucky Carl, the wanton, naked plaything of his next door neighbor and his head mistress!