Blessed are those warm, friendly older women who generously use their bodies to comfort young men. Who have outgrown modesty and bashfulness and use their ample endowments for the betterment of young manhood. Selfless, they are.
B fell under the graces of such a woman once. She helped him through a hard time, her gentle hands holding him, her billowing warm bosom resting on his chest. She watched him satisfy himself the way a young man sometimes must, and she did not protest when he reached a resolution to his problems all over her clean linens.
It was late fall and B was in the middle of his third semester of college. The weather was gray and damp and B found himself getting depressed. His good friend and classmate Josh lived with his family in a town nearby, and B asked if he could stay there for a weekend. Josh’s mother was always very kind to B, and her warmth made him feel good inside.
When B showed up at their door with his duffel filled with clothes, Josh’s mother, Evelyn, answered and hugged him tight. She was a good looking woman, her body toned from religiously performed pilates, her breasts large and pendulous. She pressed her breasts against B’s chest and squeezed him. “Josh told me you were having a rough week,” she said. “Don’t worry, we’ll get you feeling better.
After a hot dinner and a conversation around the fireplace, B tucked himself into the big, pillow top guest bed. He slept better than he had in weeks. He awoke in the golden autumn morning light to the creaking of his door. Evelyn peeked around the door, and seeing that he was awake , shut is softly behind her and padded across the wood floor and sat on the edge of the bed. She was wearing her pilates outfit — thin brown sweatpants and a long sleeved white t-shirt — and to B she looked beautiful and inviting.
“How did you sleep?” She asked, smiling down at him in the sun. He told her he slept better than he had in weeks. “That’s wonderful,” she said softly, stroking his cheek. “Do you want me to rub your back before you get up?” B said that would be nice and rolled over onto his stomach as Evelyn pulled down the warm blankets and clean white sheets. He slept only in a pair of boxers, but something about Evelyn’s warmth made him not worry about it.
She rubbed his back and talked to him about school. Evelyn had studied massage way back when, and her confident hands felt great on his muscles. B told her how he’d been feeling. He told her more than he’d told anyone. “Roll over, I’ll do your front,” she said. Lost in a long winded explanation of this or that aspect of his emotional world, he turned over without considering that he had just woken up, and young men who have just woken up are sometimes very hard. They both stopped and stared at what was impressively poking up through his boxers.
Evelyn was kind and waved it off. “Oh, don’t you worry about that. I know what happens when boys wake up. Besides, it’ll go away.” With that she resumed the massage. She rubbed up and down B’s legs, giving his thighs a good working over. Her strong fingers in such close proximity to his hardon started B’s imagination running. He closed his eyes and felt her fingers knead his thighs, indirectly pulling the skin around his balls. So in short, it did not go away.
“Did you enjoy that?” She said, placing her hand on his bare chest. She glanced conspicuously down at B’s persistent erection. “Is there anything else you need to take care of before you get out of bed? I understand that a young man like you sometimes needs to let out some steam.” She leaned over him and let her large breasts rest on his chest. “I don’t mind if you want to relieve yourself before I go make us breakfast. I would understand completely.”
B was dumbfounded. His erection strained against his boxers, Evelyn’s generous breasts were falling against him, and she wanted him to jerk off in front of her. After a moment of silent deliberation, B agreed. “I guess it might help a little if I could get that out of my system. It’ll be real quick.”
“Go ahead honey,” she said. “I’ll just let you touch my bosom if you want, and you can take care of yourself.” She sat up and pulled the tight t-shirt and the yet tighter sports bra up over her breasts. They tumbled out of their captivity and eventually came to rest, hovering above B’s chest. Evelyn lowered herself back down so her naked breasts touched B’s chest. He reached down with one hand and popped his penis out of his boxers. With the other, he touched the top of her breasts, feeling their softness and warmth. “There you go honey,” she cooed. “How does that feel? Just get it out of your system.”
Such large breasts had never found their way into B’s hands before, and he was infatuated with them. He continued to rub his arching morning hardon with one hand and fondle Evelyn’s generously offered breasts with the other. She smiled at him tenderly and hummed along with his quiet groans. He began to beat off more vigorously and his hand brushed against her hip at the top of every pump. His motions were making her breasts jiggle against his chest. She stroked his cheek once again.
“Here you go honey,” she said, raising herself up over him. “I’ll let you kiss my chest while you pleasure yourself.” She hung her heavy swaying breasts on either side of his face and slapped him lightly with each by rocking her shoulders. He licked and sucked whatever part of her breasts got close enough to his face while he continued to jack off hard. In their new position, he was jerking off against her thigh, his precum leaving little wet spots on her sweatpants. “Oh honey, you just do what you need to do,” she said softly, pressing her nipple into his hungry mouth. “Just rub yourself against my thigh until you feel like you’re going to release, and then just let me know.”
Hearing her soft, accepting voice coaxing him pushed B close to the edge of orgasm. He wanted to lay her on her back and cover her big soft breasts with cum while she whispered her approval. But he was going to do as she said this morning. He pumped his swollen rod hard with his hand up against her thigh and groaned into her breasts. “Oh there you go B. There you go honey. I bet that feels awfully good.”
This pushed him right over the edge and he told her that he was about to cum. As B furiously rubbed his arched, rock hard cock, Evelyn sat up on her knees, grabbed some of the sheet and wrapped it around his penis. The sudden pressure of her grip on him sent him into a seismic orgasm. Just as he was plunging into it, she grabbed his hands and placed them on her breasts. “Just squeeze my bosom and let it all go. I’ll clean it up, don’t worry,” she cooed.
He shot his hot cum into the clean white sheet and into Evelyn’s hand. She pumped his throbbing cock gently in time with his orgasm. The cum soaked through the sheet and was making wet sounds as she moved her hand. “Oh there you go, honey. There you go. Let it all out. I’ll clean it all up for you. That’s perfect.”
Once his orgasm was finished, Evelyn bunched up the sheet and wiped the cum off her hands. “You sure needed that, didn’t you?” She said gently. She leaned down and hugged B. She stretched her long body out and pressed it up against his. His softening penis touched her belly, and her breasts rested on his arm. He felt at peace with his life.
Brad Michaels felt great when he got out of bed that morning, because he knew that day would be one of the best of his life, maybe better than any up until that time. He was going over to see Janet Green, the hot divorced woman who lived down the block from his parents’ house in a nice suburban neighborhood, something he had been looking forward to ever since his eighteenth birthday a week earlier. That day, when he became legal, had made him eligible to fuck the woman all his buddies except those younger than he had talked about so enthusiastically.
Janet immensely enjoyed sex with studly young men such as Brad and, when she found out he had reached that magic age, she had personally invited him to come and join her in her bed. Most of the mothers in the neighborhood were aware of what she liked to do and objected to it, which was why she made sure all her sex partners were past the age of consent. Most of the men knew about her too, but none of them cared, except to be envious of their sons, unless they were lucky enough to have known an older woman like her during their youth. She was divorced, and all her children were grown up and had left town, so she had no family to criticize her lustiness or what she did about it.
Those buddies who had experienced the charms of Janet Green welcomed Brad to “the club” and told him what to do and advised him to take a condom with him. His partner that day would insist on it, and she believed it to be the duty of the man to provide the protection. The guys who were younger than he expressed their envy and said how eager they were to reach that same, magical age. Local girls who even mentioned it just sniffed to show their disdain for the neighborhood bad woman and for those who would have anything sexual to do with her. Brad’s mother suspected what he would be doing, but she decided against saying anything. Telling him to stay away would have been pointless, so she just pretended to know nothing about what might be happening.
Brad didn’t care about any of that. He told his parents he was going to take the bus to the mall and hang out there for a while, and strolled down the block in the direction of the main street. That was where the bus stop was, and he went toward it strictly as a subterfuge. Once out of sight of anybody who might be watching from his home, he circled around the block and hastened to the small home of his paramour. She was waiting for him and, after he rang the doorbell, she checked out her caller through the peephole in the front door. Recognizing him as the man she was hot for, she let him in, making sure the door was securely locked after he had entered.
Janet already knew what the young man looked like, but she surveyed him again as he stood in front of her, and smiled at what she saw. He was tall and white and athletic, with a clear complexion and short dark hair, and he looked exactly like the kind of young man who could and would bring her to repeated orgasms, which was what she loved doing. He looked her over too, and saw a rather chubby barefoot woman in her late forties, with dusky skin and dark red hair, probably dyed, or touched up at least. He also saw her big tits, obviously not supported by a bra, and fought back the urge to reach out and grab them. That would have to wait until their hot sex session was underway.
She didn’t want any delay in getting things started either. “Hi, Brad. I’m glad you could come here, because I want to cum too. How does that sound to you?”
He caught the double entendre and grinned. “That sounds great. I want us both to cum. A lot.”
That was the extant of the seduction; they both knew what they were there for and made no pretense of anything else. After he removed his shoes, Janet took Brad’s arm and led him to the Promised Land — her bedroom — which he had been fantasizing about for the last week. When they stood next to her double bed, he saw the coverings had been removed except for the bottom sheet and a few pillows. She turned and started to loosen his shirt.
“I like to get comfortable,” she said, as she finished and stripped it off him when he turned around. “Don’t you?”
He turned back to her and started on her men’s flannel shirt. It was a bit awkward, because of the placement of the buttons, and he could feel his cock growing harder as the older woman’s big breasts came into view. As he had surmised, she was not wearing a bra. She remained facing him with her shirt open, so he started on her loose-fitting jeans. These were much easier, and he had the waist open in seconds and pulled them down to the floor so Janet could step out of them. While she did, she shucked out of her shirt, letting her big, succulent breasts sway provocatively. When her horny young visitor looked eagerly up at her, Janet leaned over and rubbed the delightful globes in his face for a few seconds, the way she liked to do, before straightening up so he could finish stripping her naked.
Brad’s limited sexual experience with girls included a few hand jobs in back seats of cars and one semblance of a blow job, and he had never smelled a pussy as close as Janet’s was to him. His buddies had mentioned it, but they couldn’t have come close to describing how heavenly the aroma was. He eagerly pulled down her panties and gazed at the source of the delectable fragrance, the first pussy he had ever seen, except on some online porn sites. He thought it was the most beautiful sight he had ever beheld, especially when she stepped out of her panties too and stood with her legs slightly spread and completely naked before him.
“Sit on the bed,” Janet told him, “and I’ll take your pants off.”
Brad avidly climbed onto the bed and sat with his legs apart, while his hostess knelt between them and reached out for his belt buckle. She took less time in unfastening his pants than he had taken with hers, and he raised himself from the bed while she pulled them down and off around his feet. After removing his socks, she grinned at the sight of Brad’s cock, standing hard and straight and protruding through the fly on his jockey shorts.
“That’s what I like,” she said, as she fondled it briefly before pulling his shorts down and off, leaving them both equally naked.
Janet moved in slightly closer, rested her forearms on Brad’s thighs and raised her face above the tip of his cock so she could start licking there. Moving slowly and relishing the velvety texture, she licked in concentric circles, lowering her face and engulfing more of his cock until her tongue was caressing under the hard ridge. She increased the pace then, engulfing his shaft until the end was pressed against the back of her throat. For about a minute, Janet stayed in that position, laving his whole cock with her tongue. She truly loved the way the girth of Brad’s cock spread her mouth open and how the smooth skin felt to her tongue.
Slowly, she began bobbing her head, stroking the thick shaft between her lips. Janet enjoyed sucking off a young man and swallowing his cum, but she had other reasons for making that their first sex act. She loved having her pussy eaten, and could reasonably expect him to go down on her after his climax. More important, she knew he was horny, and cumming into her mouth would take the edge off that condition so the fucking they would do later would last a longer time than otherwise.
Brad had never felt such incredible pleasure as he was feeling that day. The teeth of the girl who gave him head had scraped along the top of his cock, and it had been almost as much pain as pleasure. Besides that, it had only been in her mouth for a few seconds before she took it out and finished him off with her hand. Janet Green was obviously having fun too, and she was looking up at him with her big, green eyes as her lips stroked him. She was not at all pretty, but the sight of his cock sliding in and out of her mouth was the most erotic and enticing thing he had ever seen, except for her pussy. The blow job had been going on for only two minutes, and he could already feel his climax mounting.
“Oh! Oh! Oh!” he groaned as his body writhed on the bed in front of the woman who knelt before him.
Janet heard and saw him and felt his cock throbbing inside her mouth and knew her young lover was on the verge of cumming. She started sucking faster and tightened her lips, because she didn’t want any of Brad’s semen dripping out of her mouth and being wasted. The flavor of fresh cum was another of the things she loved about sucking a cock, and she wanted to get it all, including licking it off his shaft after he gushed into her mouth.
“Oh god!” the young man cried out joyfully as his cock jerked and he climaxed.
A big gob of semen exploded out of the end and, although he didn’t know it, landed right on Janet’s tongue where she wanted it. While savoring the taste, she kept sucking and was rewarded when Brad ejaculated twice more. She kept sucking until she was sure no more of that delicious treat would be forthcoming, and took his cock out of her mouth with her fingers, making sure to hold the shaft upright so none of the juices would run out and be wasted.
Janet swirled his cum around in her mouth, relishing the flavor and texture before letting Brad’s semen slip down her throat and going after the rest. Like a child with a lollipop, she licked everything off the shaft and under the ridge and, when she had cleaned that off, placed a thumb on the base right in front of his scrotum with her fingers on the opposite side. Slowly, she drew her hand toward her mouth, letting her tongue catch all the semen oozing out, until her fingers were against her upper lip and she had gotten it all. This mouthful was relished as the other had been, until it also slid down her throat, and Janet’s tongue licked her lips to get anything she might have missed.
“Did you like that?” she asked the young man who had just given her the two mouthfuls of semen.
“Yes. God, yes; I’ve never had anything like it.”
“Good. I hope you’ll do the same thing for me now.”
Brad’s more experienced friends had told him about that part of the tryst too, and all of them said he would enjoy it as much as he would the other things he and the older woman would be doing together. He had some doubts, but her pussy had been so beautiful and had smelled so delightful he was going to do what she wanted. He was also aware if he refused, she was liable to kick him out of the house and out of her life and, after the fabulous blowjob he had just gotten and all the great things he had been anticipating, that would have been a terrible disappointment. He nodded his head in response, and the naked MILF climbed onto the bed, lay on her back with her head resting on one of the pillows and spread her legs.
Janet was aware Brad was probably not very experienced and she would have to direct him in what she wanted him to do. “Start on my boobies,” she told him. “Give me a good licking up there.” With her hands, she held the luscious orbs in place for his lingual caresses.
He had fondled a few breasts, even under his girl friend’s clothing a few times, but no girl had ever let him lick her there. He knew what to do, though, and knelt beside the reclining woman to take a gentle hold on the breasts he had been wanting to play with. They were big and firmer than he had expected and, when Brad leaned over and started licking her big, dark pink nipples, he was surprised at how hard and erect they were. He had expected them to be soft and pink. This was certainly not something he would complain about, because he was delighted by the texture against his tongue. As he continued licking, switching before the twin beauties, the sensation was even better, because they became so hard he could feel the individual ridges in the nipples and the pebbly areolas.
He believed Janet was enjoying it too, because Brad could hear her cooing and feel her upper body squirming under him. When he glanced toward her pussy, he smelled the delectable aroma he had smelled before and, although he was having a great time licking her nipples, he started licking and nuzzling and kissing his way down her plump belly. She was elated at what he was doing, because she wouldn’t need to tell him, and she encouraged his actions.
“That was great, Brad. I love the way you licked my boobies, but it’s my pussy that needs your attentions now.”
She watched as his face reached her Mount of Venus, but he stopped there. “Get off the bed and get back on between my legs,” she instructed him.
Brad had no problem following the directions of the older and more experienced woman, and he did as she wanted. Once he was in the right place, she raised her legs and he ducked under them so they could rest on his shoulders. It was a natural thing to wrap his arms around Janet’s chubby thighs so his hands were in her pubic hair and his face was inches away from her pussy. From that close, the view was even more delightful, although he didn’t really have much in the way of experience to compare it too.
Her skin was as dusky as her face, and her pubic hair was a much lighter shade of red than the hair on her head. The most striking parts were her inner lips, which were thick and dark red and had expanded through the pink slit between them. He gently pulled apart the edges of that lovely aperture to gaze into its pink wetness. A cloud of her fragrance arose, and he leaned forward and started licking the juices from her lips.
“That feels good, but take it easy and make it last,” Janet advised him. Her belief that her partner that day was inexperienced was confirmed, buy she expected to teach him how to pleasure a woman, herself in particular.
The nectar from her lips had been so delicious Brad went in search of more, found some shiny streaks on the insides of her thighs, and licked them off too. His tongue continued to Janet’s crotch, and he started licking up drops of her juices as they trickled from the pink hole that was their source.
“Start here and lick me all over down there.” Janet placed her fingers on one of her outer lips.
Brad started licking the indicated place and found he liked it even more than her thighs and crotch. Her pubic hair was soft and clean and felt good to his tongue, and he liked the way Janet’s body started to squirm under his face. He felt good that he was giving pleasure to such an experienced woman, and his tongue meandered slowly until he reached her mons. When he looked up, he was even more elated to see how her whole body was responding to what he was doing, and her lips were parted in a smile of obvious bliss.
“Now the other side,” she directed him.
He started on the other outer lip, but not before he helped himself to all the fresh juices she had produced. The second lip was treated as the first had been, to a period of slow lingual caresses until Brad’s face reached her mons. Her movements had become more pronounced, and she was starting to slowly fuck up against the mouth which was giving her so much joy. After bringing his tongue back down to where he had started and feasting on all the fresh nectar, Brad raised his head again to see what she wanted him to do next. No instructions were given, but he saw how the outer and inner lips of her pussy were close together and started to lick between them.
“Right there! Right there!” Janet urged the young man to continue, and gave herself completely over to the pleasure of the moment.
As she felt the wet giver of joy probing between those two highly sensitive places, her movements became more frenetic. She rocked from side to side on her large ass and her legs started thrusting out and back besides Brad’s head. Once again, the young man was encouraged and highly gratified that he was giving the older woman so much pleasure, so he continued licking until he reached the end of her inner lip. He didn’t know it, but that lip and the other inner one meet there to form her clit hood. All he knew is that, when he raised his head to see what Janet’s responses were, he could see what looked like a lovely pink pearl where there had been none when he started.
He also saw her body thrashing on the bed under him, while her hips swiveled, thrusting out her legs. The aroused woman’s body was rocking from side to side and she was moaning while her head rolled from side to side on her pillow. Both her eyes were closed and her lips were parted in a grimace of extreme pleasure, so he knew she was not expressing pain, even though the two sounds were much alike.
When the licking stopped briefly, Janet opened her eyes and looked at the man who was doing such great things for her. “I really love that, Brad,” she said. “Don’t stop. Keep doing that until I cum!”
That was exactly what he wanted to do, so he brought his mouth back to below her pussy and licked up all the fresh nectar that had just been produced. After his delicious snack, Brad started licking between her other pair of inner and outer lips. He treated these as he had the first pair, taking a long time to reach the end. By the time he did, Janet’s moans had started ending in whimpers, and her thighs had turned out, fully presenting her pussy to his face.
“Suck my clit,” she gasped. “Suck my clit and make me cum.”
Tentatively, Brad moved his face and started licking the lovely pearl he had seen before. He was unsure, but he believed that had to be what she meant. When nothing more was said, he drew the succulent morsel into his mouth and started to suck, while his tongue caressed the swollen sides and top. It felt good to him, and Janet quickly let him know how it felt to her.
“Yes! Yes! Right there! That’s the place!”
The movements of Janet’s body became even wilder, and her whimpers were in the same tempo as the thrusts of her pussy into Brad’s face, until she suddenly cried out in ecstasy.
“Oh god! Oh god! I’m cumming! Keep sucking!”
Everything about what he was doing was so much fun, Brad wanted to keep doing it and, even if he had wanted, his head was held tightly by Janet’s heavy, strong thighs. She yanked him all over the bed as she sobbed in joy and her legs swung from side to side and back and forth. When she climaxed, all her muscles clenched, she uttered an even louder cry of joy, and rammed her pussy against the young man’s face for the final time. After her orgasm, she sagged back onto the bed, with her arms sprawled at her sides and her legs draped loosely over Brad’s shoulders.
He backed out, letting her legs drop to the mattress, but moved forward again to feast on the fresh nectar that had been produced while Janet was cumming. He licked it from everywhere it had spattered, even sucking it out of the pink hole that had been its source. When he was through with his repast, he stayed between her legs, wondering what she would want to do, and hoping she would want to fuck because, from the erotic joy of eating Janet’s pussy, his cock had become so big and hard it felt like a baseball bat sticking out from his crotch.
When she had caught her breath and opened her eyes, the MILF saw the young man’s prodigiously hard shaft aimed at her and smiled. “I hope you brought rubbers with you. I believe in always practicing safe sex.”
“Yes, Ma’am; they’re in my pants pocket. Brad hurried over to his pants where they lay on the floor, took the plastic packet from the pocket and returned, rolling the condom onto his cock as he approached the bed where Janet had sat partially upright.
She smiled lasciviously at the sight of the stretched latex and reached down to spread her pussy lips. “Right in here, Brad. Stick that nice, big cock right here.
He got back on the bed and walked on his knees until he was between her legs and leaning forward to support his weight on one hand while he steered his cock with the other. When he felt her fingers against the head, he stopped. Janet continued holding her lips apart with one hand and used the other to rub the tip in her wetness to spread the lubrication. He had greedily devoured most of her juices instead of thinking ahead and leaving them to aid in his penetration, but there were enough fresh ones for them to perform their natural function. When his cock was ready, she guided the head so it was centered on the hole that had produced those juices.