tagMatureCraig & Irene Ch. 05

Craig & Irene Ch. 05

byjeffrey214©

This story contains Femdom themes – including dominant older women and submissive younger men, and perhaps some occasional F/m spanking. If this sort of theme does not appeal to you, please check out some other author's stories on Literotica that will better suit your tastes.

All the best to you!!!

This story is dedicated to all the Ladies in their 50's and 60's out there who are still hot women - your sure hands and knowing, comforting smiles are so good for us younger boys, who need your nurturing attention to keep our youthful genitals healthy...






Mrs. Douglas was delighted that she had drawn the duty of waking young Craig from his nap, and quietly entered his little room, seating herself on a small chair next to his bed. She had pushed the covers down to reveal Craig's nakedness as he slept, and she had just looked at him for a while before she began to massage his testicles in her warm experienced hand.

She simply adored well endowed young men. They were so beautiful to look at, so pleasurable to touch and explore, and wickedly delightful to dominate and control. And most especially delightful to see them writhe and whimper when an experienced woman makes them spurt out all their semen - and young men could be made to produce a lot of semen!

Particularly, she thought, the boys at the Larraine Institute, who were specially chosen for their large genitals and submissive tendencies. And the special pill that the boys took each day worked wonders to increase their semen production, causing a boy to have a physiological requirement of at least six to ten ejaculations each day.

She also had become quite impressed with the special 'genital development' cream that was massaged into the penis and scrotum of the boys at the institute after each ejaculation. It was clear to her that the skin of a boy's genitals grew increasingly sensitive to stimulation over time, and though it was difficult to believe, she knew that these well-endowed boys were continuing to somehow grow and become even larger.

She felt herself thrice-blessed to have worked her way up from a novice Booster of the boys' swim team to the exalted position as a Matron, and now was able to care for a boy, alongside her team members. The stated goal of the Matron team was to take care of 4 or 5 milkings a day, and to see to it that each milking served to feed the boy's submissive tendencies. She felt her team was doing a wonderful job, working together to control Craig's sexual pleasure so that every ejaculation the boy experienced reinforced his submissive feelings.

Mrs. Douglas just adored the feeling of making a penis go from soft to hard in her hand, and caressing it properly so as to cause ejaculation. The exhilaration of forcing a male, especially a younger one, to spurt whether he wanted to or not (and they always wanted to, she giggled to herself) was priceless.

As she caressed the soft hairless scrotum of her young 19-year-old charge Craig, she looked down at his cherubic face lovingly, whispering, "I'll take good care of you, dear, and you'll be a good boy for me...", her mind went back to earlier years and the thrill of taking her first young man in hand...

20 years earlier...

When Mrs. Douglas was just turned forty, she was feeling sort of down. Her rich husband was off in Europe somewhere on an extended business trip, leaving her home and alone to face the benchmark birthday.

Sitting in Mrs. Douglas' kitchen and having tea with her neighbor Ellen, a fifty-something elegant woman who had become a very close friend, they were discussing birthdays that end in zeros. Ellen was compassionate about Mrs. Douglas' feelings about her fortieth, but suggested a solution.

"Darla," said Ellen, "there's nothing magic about turning forty, or fifty, or sixty. You're still a woman, and a beautiful one at that. The only question is, are you enjoying life? At any age, that's what matters."

Mrs. Douglas took in this sage wisdom and answered, "Well, I'm bored and lonely."

Ellen understood, and with a wise grin she leaned close and whispered. "So, Darla, have you ever had the pleasure of enjoying a young man? A much younger man?"

"I'm married," said Darla Douglas, "Of course not."

"Pity," said Ellen, "they are quite delightful. And honestly dear, they are far more available than you might think. Why, just a few years ago, I invited my pool boy in for tea, and one thing led to another... Eventually every Saturday for several years, after he finished with the pool, he would sit with me for tea and I became intimately acquainted with his charms. I enjoyed him very much."

"What do you mean?" Darla responded in shock, "You didn't have sex with him, did you?"

Ellen giggled, "No, dear, I didn't do anything of the sort. But, I did ask him to sit for tea with me, in... ah... shall we say, a state of undress."

Darla sat back, "You don't mean he was...naked..."

"I most certainly do, dear. I'd have Billy come into my parlor every Saturday, once he'd finished with his work, and I'd have him take off his clothes for me, and have his tea with me in the nude. I of course remained fully clothed at all times." Ellen smiled at Darla's incredulous expression. "I assure you it is true, and it was very easy to get him to do it the first time. He was such a precious boy. I also had him pose for my paintings. You should come over and see them some time."

Darla was silent for a moment, and then with resolve she said, "I'm not sure I understand, so perhaps you should tell me exactly what goes on, in detail." A small grin played at the edges of Darla's mouth.

Ellen, the handsome 50-something woman, explained how her special relationship with Billy the Pool Boy started and progressed.

One day, many years ago, Ellen had looked out the window and saw that there was a new young man cleaning her pool. She had not changed the maintenance company, but they had changed the personnel. He was wearing a small pair of tight gym shorts, displaying the tanned and muscular physique of his legs, arms, and torso very nicely in the midday sun.

She watched him work and saw that, in addition to nicely developed muscles and a handsome face, they boy had a very cute bottom and a pronounced bulge in the front of his clingy shorts. She felt her heart beating and realized that she was interested to see the boy without the unneeded shorts on.

Ellen was an aggressive woman, a woman before her time those twenty years ago, and Darla knew she subscribed to Playgirl Magazine since she had seen them on her coffee table. Ellen also painted very well, and her specialty was to paint portraits. Her favorite subjects were men, and she usually painted them nude. She had a few of them on her walls and many in her studio...

Ellen decided she would invite the young 18-year-old gentleman in for some tea and see how things progressed. If they got on well, she might invite him to pose for her as she painted him. She asked him in and sat him down in the parlor, where there were several recent editions of Playgirl on the coffee table, and her best male nude painting on the wall.

She sat across from the boy so that he would see the painting over her shoulder, which was of a young man about his age, lying on silk sheets with his thighs apart so that his large hairless genitals were fully and magnificently displayed. The trap was set and she would see how the boy reacted.

They chatted amicably for quite a while, and she had time to notice his furtive glances as the painting and at the Playgirl magazines displayed on a nearby table. She could see that they made him a little uncomfortable, but perhaps not in a bad way. He sat casually as boys do, never able to keep his thighs from parting, and this gave Ellen an enjoyable view of his genital bulges, which sometimes betrayed a little swelling - much to her delight.

Ellen guided the conversation to the painting when she caught the boy obviously looking at it, and asked if he liked her work. Of course he was very complimentary, so she led him into her studio where she had set up many of her paintings on easels for easy viewing. They were all male nudes.

She took the boy by the hand around the room, pausing in front of each painting. They were of different young men, in different poses, but all of the paintings depicted the boys' genitals in full and explicit detail. Several of the paintings were of boys Billy's age, between 18 and 20 years old, with erections - making them even more inflammatory.

She adored asking the boy to tell her his thoughts on each painting, and she reveled in his obvious blushing embarrassment. But he did not, she noted, run screaming from the room, and his little shorts could not hide the fact that he was experiencing some embarrassing firmness and swelling in his groin area. Therefore at the end of the tour she took him back for more tea in the parlor to ask the question.

"How would you feel about sitting for me, Billy, and letting me paint you? Provided of course, that you prove to be a exceptional model. I do pay an hourly fee of $25 to my models..."

Ellen watched his eyes fill with surprise, fear, embarrassment, and just a hint of excitement. Perfectly natural. Without waiting for an answer, she simply moved forward. "Billy," she said firmly, "Please stand up and lower your shorts for me so I can have a look at you."

The boy was frozen, his eyes wide.

She stood and stepped to him, offering him her hand. He automatically took it and she lifted so that he would follow her hand and stand. "There, that's better," she said smiling, "Now let's have the shorts down to your knees, Billy, that's a good boy..."

She let go of his hand and just stood expectantly, waiting for him to obey.

Finally after a pause, he did it. It was amazing for Ellen to see how pliable young males are, as always.

The boy pushed his shorts down and they fell to his ankles, and he stood up straight with his hands at his sides. It was so cute that he was blushing and squeezing his eyes shut, afraid to look at Ellen as her eyes slowly roamed up and down his body several times, finally coming to rest on what was hanging between the boy's thighs.

She smiled as she focused her attention on his plump circumcised penis, throbbing just slightly as the boy couldn't help but become aroused. His testes were nice and big, hanging low in his soft scrotum.

He was delightfully endowed.

"Very nice, Billy," she said, "now I'd like you to step out of your shorts, leave them on the ground, and take your seat again in the chair.

He opened his eyes and moved to sit down, this time with his hands in his lap and his thighs close together, trying to hide his genitals and the embarrassing fact of his growing erection.

"Now Billy," she said, "It's not good for a boy to be so modest. You need to get used to being undressed in a Lady's presence, so I want you to take your hands out of your lap and stop squeezing your legs together. Now be a good boy for me and open your thighs and put your hands on the arms of the chair."

He sheepishly obeyed, blushing profusely and breathing shallowly. "That's a good boy," she said, "just relax and get used to freely exposing your body. Don't worry if you have an erection, that's perfectly normal for a boy and nothing for you to be ashamed of. That's it, good boy." She eyed the beautiful shapes between his spread thighs and said, "You look very nice without any clothes, Billy. I think I'd like you to be undressed whenever we are together. It's good for you to relax and let a lady look at your body."

She smiled as she could see his muscles slowly become less tense as he let her look at him, but he still felt quite embarrassed to let her watch as his penis slowly filled out and stiffened. They sat in silence together as he watched her watch him come to full erection, with his youthful penis standing up from his groin all thick and long and crowned with a swollen pink head.

"Very nice," said Ellen again, "you have a beautiful body, Billy, and you should be proud to let me look at you. Here, have some more tea, dear."

They again drank tea and chatted for a while, deciding what days and at what times Billy might be free to come and pose for Ellen's painting. They decided on Tuesday and Thursday evenings.

Once it was all decided, Ellen said, "Billy, I wonder if you'd feel comfortable if sometimes, when you come to pose, we could just spend time together? Occasionally, I won't have the right creative feeling to paint, but I would like you to arrive for your appointment and undress for me, and then just stay the two hours like we planned. I enjoy having a handsome young man around, and a boy is at his best when he is naked, in my opinion."

"I guess so..." he answered.

"Now Billy, I know you have to go and do other people's pools, and I've already made you late. But, in gratitude for your cooperation today, and in view of your present condition, I feel obligated to relieve the pressures a young man can feel..."

It was clear that Billy had no idea what she meant, so Ellen smiled and explained it better.

"Billy," she said in a very maternal voice, "You obviously have an erection, which will make it difficult for you to put on your shorts properly. I am offering to help to relieve your erection. Would you like that dear? Would you like me to caress your penis and draw out a nice ejaculation? I'm sure you must be feeling lots of pressure, with your youthful buildup of semen, so I think it would be best if I helped your penis to relax..."

His eyes went wide, but he certainly looked interested, and his penis throbbed in his lap to betray that this idea was exciting for him. He carefully nodded his assent.

"Yes, I thought you'd like that. Good boy."

Ellen stood and took Billy by the hand, leading him from the parlor to the kitchen. She had him stand with his back to the wall, and his penis jutting right out toward her, as she set a towel down across the kitchen table. "I want you to lie back on the table for me, Billy, so that I can help relieve your stiffness."

Billy laid down on his back across the table, next to the edge where Ellen had laid the towel, and once he was in position, Ellen stood next to his right hip and took hold of his penis in her soft, warm hand. As she gently stroked the shaft of his penis, she marveled how it's girth filled her hand so that her fingers couldn't touch, and she had to stroke long to cover the length of his beautiful shaft.

"My, you have a very nice penis, Billy," she said softly. "Whenever I have a young man spend time undressed in my presence, I always feel it is my duty to take care of his needs ejaculatory. Whenever a naked boy gets an erection, I always lay him down and take good care of his penis."

She smiled down at the boy, "So, from now on, whenever you're with me and you have an erection, don't ever be shy, Billy. I know that a young 19 year old is full of genital energy, and I'm always happy to help a boy to relax his genitals in this perfectly natural way. So you must always let me know whenever your pretty penis is beginning to feel stiff, so that I can rub it and make it all better. Can you do that for me, Billy?"

He nodded yes.

With her other hand, she began to feel the firm roundness of his testicles, each big enough to fill her palm. They felt warm and heavy as she rolled them between her fingers, relishing the soft texture of his scrotum, lightly dusted with hairs.

"Next Tuesday," she said, "when you come to pose for me, I'd like you to have shaved off all of your pubic hair. As you can see from my paintings, I feel that even a light dusting of pubic hair is unnecessary on males as it hides their beauty. I think boys look best when they are completely bare. If you are afraid to do it yourself, I can do it for you before you begin to pose. Ok, Billy?"

He nodded, moaning slightly as Ellen's ministrations to his stiff organ began to do their magic.

"Good boy," she said.

She stroked his penis for a while, slowly increasing tempo and pressure, and soon she had the boy writhing on the table and gasping and moaning.

"Shhhh," said Ellen, "take deep breaths and try to hold still for me, dear. I know it's difficult, but you need to learn to lie back and trust me to take good care of you. That's a good boy. You're approaching ejaculation, Billy, so I want you to do your best to relax. You'll soon learn that it's good for you to let go and surrender yourself to me completely. That's better, good boy, just let it happen..."

Suddenly with a gasp, Billy's body tensed and Ellen was rewarded with an enormous spurt of youthful semen that flew several feet into the air before landing on the boy's chest. There followed many more distinct spurts, each a little smaller and weaker, and then finally the last few pulses of semen simply flowed out of his penis as Ellen continued to milk his shaft with gentleness and affection.

"Oh, Billy, you did very well dear, I'm very proud of you," said Ellen warmly. "You gave me such fine spurts and you produced so much semen. You're a very good boy, Billy. Now just relax and let me milk out the last few drops, and then I'll get you cleaned up."

He nodded imperceptibly as Ellen continued to stroke his softening shaft in a root-to-tip motion, to express any remaining semen from the boy's penis. She obtained several last pearlescent drops, which pleased her greatly, and she enjoyed feeling the boy's penis as it became slowly softer and smaller in her hand.

Finally, she laid his penis down on his belly and warmed a washcloth at the sink. Returning, she gently and lovingly wiped up all of Billy's semen from his genitals, thighs, belly, and chest.

Once he was clean, she cooed at him to lie still a little longer, as she casually caressed his soft penis and emptied testicles with her soft, knowing hand. She comforted the post-orgasmic boy, massaging his genitals and caressing his face as she cooed soft encouraging words.

Ellen whispered, "There, there, dear, just rest now and let me take care of you. You're a very good boy and I am proud of you for giving me such a nice ejaculation. Just rest and let yourself surrender, knowing that I understand that a good boy needs to have his penis cared for. I know how to take proper care of your genitals to keep them healthy. You can trust me..."

When finally he'd rested enough, she helped him off of the table and held his little shorts for him to step into.

She gently cupped his genitals in her hand, gave him a peck on the cheek, and lovingly patted his bottom as she sent him out the door. "See you next Tuesday, Billy," she said happily, "and remember to be a good boy for me and shave off all your naughty hair so that your pretty genitals will look fresh and clean for me..."

In the ensuing years, Billy continued to pose twice a week for Ellen, and also continued to clean her pool on Saturdays.

He posed nude for her in whatever position she desired, and she painted many portraits of his beautiful body, always featuring his naked genitals prominently. She especially enjoyed having him pose with an erection, because that required that he stroke his penis from time to time to maintain the proper stiffness.

After each posing session, Ellen would lead her naked young man by the hand into her parlor, where she would take her time to play with and pleasure his penis with her hands. She adored bringing the boy to a writhing, gasping ejaculation, and would always coo sweet encouragements in his ear as he spurted for her.

On 'pool days' he was always quick to come inside when he'd finished his work, and take off his shorts to have tea with Ellen. She marveled that her young man was always so eager to undress, eager to have her eyes on his nakedness, and ever so eager to lie down and offer his genitals for her to touch and pleasure. Ellen was always gracious and happy to massage his penis and bring him to a much needed and relaxing ejaculation.

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byjeffrey214© 19 comments/ 111573 views/ 12 favorites

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