The Milf Pops The Question (Patreon Commission) WIP (Patreon)

A smile came to Lisa’s face as she looked at herself in her smartphone’s selfie camera, checking her looks one last time before her dear boyfriend was supposed to show up. As a woman in her mid-thirties with a boyfriend that’s barely starting college, she knows he must see a lot of younger and more attractive women during the day. Especially when he’s at work. So, she always tries to look her best for him. Lisa always makes sure that her blonde hair is looking almost perfect while her green eyes almost shimmer in the camera’s preview. Her soft lips curl into a gentle smile as a bit of lust washed over her, just in time for her lover to knock on her door and let her know he’s here.

“Just on time. Like the good little boy he is.~” Lisa giggled to herself as she got up from her couch and left her phone in her seat, making her way to the door with a bright smile on her face and opening it to let him in. “Darling! There you are. I was just starting to feel a bit… Needy.~” Without waiting for him to respond to her, she carefully wrapped her arms around his neck and pulled him in for a deep and affectionate kiss. A kiss that she didn’t bother trying to hide as she didn’t pull him away from the door, simply keeping him there as one kiss slowly led to a second and then a third.

After a few moments of stealing kiss after kiss from her younger boyfriend, Lisa smirked and giggled as she pulled herself away from his lips. She quickly turned her head to look into her hallway, just to make sure no one was looking, teasingly licking her lips before turning her attention back to her beloved and pulling him into her home. There was no hesitation as she closed the door behind her and wrapped her arms around him once again.

And yet again, Lisa pulled him for more loving affection. As one kiss led to another and then another, her hands started to drift around his body. She reached down and playfully grabbed his rear end, moved her hands from his ass to his crotch and gently rubbed his cock through his clothing, and even brought both of her hands underneath his top and massaged his chest. All while kissing him and leading him toward her couch.

When they finally got to her couch, Lisa felt her lover’s hands pressing against her shoulders to carefully push her away from him. And she couldn’t stop herself from pouting under her breath when she heard him speak up, something that didn’t even come to mind leaving his lips.

“What about your daughter? Aren’t you supposed to go and get her from preschool soon?”

Lisa’s heart skipped a beat in her chest when her boyfriend brought up her little girl. They hadn’t been dating for more than a few months and he was already thinking of her daughter’s needs like a father. It warmed her heart to hear the sincerity from him. But that didn’t stop her from bringing a finger to his lips and shaking her head no. “Not today. The daycare is taking her to her grandparents for the night. And her grandparents will bring her home tomorrow afternoon. So, we’ve got all the time in the world to spend together, dear.”

With a smile still on her face, she placed another kiss against his lips while climbing over him. She was careful to not seem too demanding as one of her hands slowly dragged down his body from his neck to his crotch, slipping into the pants and boxers that he was wearing before grabbing a firm hold of his cock. A quiet giggle left Lisa as she looked her boyfriend in the eyes, loving the fact that someone as young as him was able to get aroused and excited so easily and for so long. It made for wonderful nights of passion between the two of them, and she was all for it. Especially when he submitted to her and let her have her way with him.

However, now that she had his cock in her hand, she needed to get it out so that she could stroke it. And get it out she did. Without missing a beat, Lisa adjusted herself to be sitting beside her younger boyfriend, the only thing stopping her breasts from slapping down against his face being the low-cut top she was wearing. She happily unzipped his pants and looked him in the eyes, relishing in the quiet gasp that left him when his cock was freed from his pants and immediately in her hand.

Though, Lisa didn’t stop there. She quickly brought her free hand to her chest, pulling the top that she was wearing down under her breasts to let them spill free and into his face. She immediately brought that free hand to the back of his head and forced his mouth to her breast while keeping her eyes locked on him. “Drink up. I want you to drink every drop that you can.~” And much to her excitement, her boyfriend did exactly as she said. He wrapped his lips around her breast and started to suckle on her soft mounds, drifting back and forth between the two while drinking her breast milk.

Lisa’s heart raced in her chest at the feeling of his tongue traveling along her nipples. It felt so good to have him sucking on her breasts like he was. Especially when she could feel his cock only growing harder and harder in her hand. It was like he had wanted this just as much as she did, but couldn’t bring himself to say anything. Which she found utterly adorable as she started to stroke his shaft. All the while she had her hand on the back of his head, threading her fingers through his hand and gently caressing his scalp. “You’re so cute, my dear. Just how long have you wanted to suck on my breasts and drink my milk but haven’t said anything?~”

A quiet giggle left her as his cock throbbed in her hand, the question clearly getting to him in one way or another. Lisa felt her heart starting to race as she picked up the pace that she stroked his shaft. The feeling of him resting against her body and drinking her breast milk, the feeling of his member twitching and throbbing in her hand, and the lust that coursed through them both as they enjoyed this moment together. It was almost magical in her mind that they were able to truly sink themselves into this moment and not care about anything else in the world. Especially when she felt his tip starting to leak precum into her hand.

Of course, once she felt a bit of his precum on her hand, she picked up the pace of her stroking. Lisa didn’t only want her dear boyfriend to cum in her hand, she also wanted to see if he could cum on her chest from the position he was currently in, lying on his back in her lap. He was still young and virile and some part of her knew that he could do it, even if she had to coax the extra pleasure out of him. Which was why she leaned herself down a little more, squashing one of her breasts on his face while reaching down to his balls. The moan that left him and rumbled against her breast was unlike anything she had heard from him while they’ve been together. It was almost primal and instinctive in the way it sounded.

Of course, with the way his balls throbbed and pulsed in her hand from the sudden contact, she expected nothing less. But it made Lisa happy all the same to feel and hear his pleasure like this. Though, she wasn’t done just yet. She quickly brought the hand that was behind his head to his shaft, making sure to keep stroking him as her hand went a little bit lower toward the floor. And in a matter of moments, she was stroking his cock while teasing her finger against his asshole. But he couldn’t talk his way out of it this time since he was stuck in this position until she was satisfied.

Luckily, when she finally reached her hand down and pushed one of her fingers into his asshole, the sound that left him was pure and utter pleasure. Her heart raced in her chest as his asshole clenched around her finger and his cock throbbed in her hand, cum now leaking out of his tip for a moment. “It’s okay, baby. Cum for me. I want you to cum for me. Do you think you can be a good boy and do that?~” And almost as if on queue, just waiting for her to ask, he gave her exactly what she wanted from him.

Rope after rope of this thick and heated seed splattered into her hand and against her stomach and breasts. Lisa felt and relished in each and every drop that coated her body as she continued to stroke his shaft with his cum covering her hand. And the way he moaned and groaned against her breast while continuing to drink her milk was an incredible feeling. Especially when he bit down on her nipple to try and spark a bit of pain in her and make her move away. Unfortunately for him, it only caused Lisa to moan louder as she was covered in even more cum.

Though, after a moment or two, when his cum finally stopped flowing, Lisa did carefully pull herself away from her younger boyfriend and look him in the eyes. She didn’t say a word as she brought her cum-covered hand to her mouth and slowly, sensually, licked her fingers clean. Taking her time with each and every lick, she made sure to put on as attractive of a show as she was able to, loving the way it caused her dear boyfriend to blush and shudder on her lap. It especially made her happy to feel him cock twitch and throb against the hand that she was pulling away from his asshole.

“The way you react is just too cute, dear. I hope you understand just how much I love seeing you squirm like this.~” Lisa playfully licked her cum-covered lips clean before lowering her hand to her breasts and cupping one of them in her hand. “We’re not done yet, though, my love.~”

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Doing what she loved, it was no surprise to Lisa that she ended up in her bedroom with her head between her boyfriend’s legs as he sat on the edge of the bed. It brought a smile to her face to be able to feel his cock sliding down into her throat over and over again. She didn't know just how long she had been at it, having made him cum twice already just with her mouth, but she didn’t care how long she had been at it. The feeling of his member throbbing and pulsing as she bobbed her head up and down this length was something that she savored, something that she cherished and enjoyed. It was something she loved. And it was something that she wasn’t going to stop doing just because he had already cum twice for her while doing it.

Lisa enjoyed the feeling of her younger lover’s cock reaching deep into her throat and almost into her stomach. So much so that she didn’t hesitate to push herself all the way down to his base and simply sit there, swallowing around his member to bring him as much pleasure as she could. It made her heart race with joy to feel his hands tightening in her blonde hair as she sucked him off and brought him to the peak of his pleasure.

It was always easy for Lisa to know when her dear boyfriend was at his limit and about to cum. And she could always time things perfectly to either stop just before he came or drag things out by slowing her pace and purposefully taking her time. Just like she was right now. Lisa giggled under her breath as she pulled herself back and playfully popped her lips off from around his dick, her heavy breath being the only thing to touch it for a moment. If he came right now, her beloved boyfriend would cover her face in his cum and she would be more than happy to take it. But he wanted to see just how long he could last.

Which was exactly why she lowered her head and peppered a few gentle and affectionate kisses down his length. Her lips were curled into a smile the entire time while she moved her way lower and lower down his shaft, eventually reaching a point where her lips were resting against his balls and his throbbing length rested against her forehead. For half a moment, she thought about just making things end right there and making him cum in her hair, but Lisa had something better in mind for the two of them.

She didn’t hesitate to place gentle and affectionate kisses against his balls, making sure to press her lips as firmly as she could against his heavy and full sack. The scent that wafted into her nostrils was just as addicting now as when she started sucking him off a bit ago, allowing Lisa to groan and moan in bliss with each and every deep breath that she took. It was a wonderful thing for her, especially when his grip on her head continued to tighten, showing just how close to the edge he was.

And for as much as Lisa knew better than to keep him waiting to be able to blow his load, she knew that she couldn’t let him cum just yet. She had something else planned for him and wanted to make sure he enjoyed it the moment it started. Her lips parted for a moment before she took one of his balls into her mouth, lightly pulling it back and away from his crotch. And she couldn’t have been happier when she felt his cock throbbing against her face like he was going to erupt and actually cum in her hair and likely on her ass behind her.

However, Lisa stopped and pulled herself back enough to look him in the eyes, bringing both of her hands to her breasts as she heard him groan in slight annoyance. “You’re not allowed to cum just yet, dear. I have something very special planned for you. Very very special.~” Dragging her tongue along her lips, Lisa pulled her top up and over her head, exposing her leaking breasts to her younger boyfriend before wrapping them around his shaft. “Be a good boy and hold out for as long as you can, okay?~”

Without wasting a moment, Lisa playfully flicked her tongue against the tip of his shaft, looking her dear boyfriend in the eyes while she did so. But instead of immediately starting to move her breasts up and down the length of his member, she sat there and looked him in the eyes. She wanted to make sure her message of him not being able to cum yet fully sank in for him. And when Lisa noticed him nod his head, hot and heavy breaths leaving him, she felt satisfied. But she didn’t move just yet.

To test if her beloved could continue holding out for as long as she wanted him to, Lisa leaned her head down and wrapped her lips around the first few inches of his member. She didn’t start bobbing her head but instead simply swirled her tongue around his member, circling his throbbing shaft and teasing him without bringing him too much pleasure. She wanted to push him, but she didn’t want him to cum just yet. Especially if it would ruin the fun that she had in mind for both of them.

However, the sound of him groaning in bliss, that all too familiar sound of his moans filling her ears caused her to stop and look him in the eyes. And, for a moment, she could see a fire of lust that made it clear just how badly he wanted to cum in her mouth or on her face. Lisa giggled under her breath before popping her lips off from around his member, playfully licking them while she cupped both of her breasts in her hands. “I’m sorry, dear. You’re just so cute when you’re close to cumming. I can’t help but want to tease you.~”

Lisa sat in silence for a moment as she continued to look him in the eyes, simply appreciated and relishing in the feeling of his cock throbbing and pulsing between her breasts, his excitement and lust very clear to her. To the point that she could feel the pace of his throbbing slow down and she knew she had to start pleasing him again if she wanted to keep him on the edge. So, that’s exactly what she did. Lisa started to move her breasts up and down the length of his member, massaging his shaft with her lactating breasts.

Of course, she purposefully squeezed and kneaded her soft mounds as she moved them along his cock, using her breast milk as lube in order to bring him even more pleasure. Even if it wasn’t exactly what he wanted, Lisa knew that her beloved boyfriend enjoyed the feeling of his dick disappearing into her breasts and being engulfed by her soft mounds over and over again. Especially when she leaned her head down and flicked her tongue against the tip of his member, teasing him just a little bit while she did this.