The Forty Year Old Virgin

by Shakespearicles

Rating: mature
Tags: Sex, My Little Pony: Friendship is Magic, Romance, Original Character, Button Mash
Length: 6897

A forty-year-old virgin finally loses their virginity.

Mother's Day 2024

A forty-year-old virgin finally loses their virginity.

Published 2024-05-12 17:10:04 UTC
Last updated 2024-05-12 17:10:04 UTC

First Time at Last

Cream Heart's bedroom echoed with the sounds of raucous sex. The rhythmic thumping of a bed's headboard against the wall punctuating the moans and grunts of passionate, primal, ball-slapping fucking.

"Oh fuck! That feels so good! You're amazing at this! I'm gonna cum again!"

Button Mash panted heavily, feeling himself getting closer to cumming.

"I'm cumming!"

"Ngh! Me too!"

The rhythmic thumping of the headboard against the wall came to a shuddering stop. Everything went quiet in Cream Heart's bedroom except for her heavy breathing in the aftermath of her orgasm.

"That was incredible!"

"Yeah!"

"You were wearing a condom, right?"

"Of course."

The bed creaked as the stallion dismounted. Cream Heart rolled onto her side to look at her doorway. Out in the hallway the bathroom light turned on, casting the shadow of a stallion on the far wall, his fifth leg hanging under him, dangling the bloated condom to be discarded. He returned to the bed.

"You were amazing!"

"You weren't too bad, yourself."

"I really made a mess of the bed didn't I?"

"Don't feel bad. I take that as a compliment."

"Do... do you think we can do that again?"

"No. I'm sorry. You said you wanted to lose your virginity, and now you have."

"So that's it!?"

"I told you before we even started that this was all it was. I'd help you lose your virginity, but we can't be catching romantic feelings for each other like that. The purpose was for you to lose your awkward, first-time jitters. Now you need to go out and get yourself a proper long-term partner."

"I know."

"... Do you regret it?"

"No! Not at all! But... you're going to be a tough act to follow."

"That's fine. It just means that you'll have high standards."

"But I..."

"..."

"I mean... Thank you."

"You're welcome."

~

Most ponies would agree that an adult pony still living at home with their mother had its challenges. Button Mash and his mother, Cream Heart, were no exception. The harsh reality of the living arrangement meant that while one of them was having incredible sex on a regular basis, the other kept awake from the noise, more or less forced to hear it through their shared bedroom wall. While one of them filled with pleasured satisfaction, the other filled with envious jealousy.

Cream Heart watched the shadow of her son's latest conquest stagger down the hallway. She had never dared to think that would have raised a fuck-boy of a stallion. But it was a rare event when she was spared the noise of listening to him bed his "flavor of the week". Some naïve, inexperience young mare seeking the help of the "Virginity Guru", as he called himself on his podcast channel.

The monetizing success of Button's channel made her day job's paltry income pale in comparison. He kept the lights on and the fridge full. That was the real golden rule after all; whoever has the gold makes the rules. Not that she was relegated to housework, either. The few hours he 'worked' gave him ample time to step up and keep the house practically spotless. As much as Cream Heart wanted to impose the "her house, her rules" card, it was her house in name only. Even if what her son did made him seem like a whorse to her, it wasn't really prostitution. None of the mares directly paid him for his services. Who was she to tell a couple of consenting adults what they could or couldn't do in the privacy of his bedroom?

"Just his mother," she grumbled.

At the breakfast table, Button Mash poured himself a tall glass of orange juice. "Happy Birthday Mom! So, what do you want for your big four-oh?"

"I want you to grow out of this... phase!" Cream Heart said.

"What?"

"This... thing with you being a whorse!"

Button rolled his eyes. "Really? This again?" he asked.

"I don't like having to listen to it every other night!"

"I could buy you some ear plugs. Or some really high quality noise-cancelling headphone. With the money that I earn. That pays the bills."

Cream Heart sighed.

"I could buy you some sound-proofing wards for your room."

"It's not just the noise... I'm concerned about you."

"Mom, I'm not an idiot. I always wear a condom."

"But doesn't this lifestyle make you feel... dirty?" she asked.

"No." Button drank his orange juice. "In fact, I think I'm providing a valuable service to society. Helping these beta mares get over being nervous about their first time."

"Please don't call them that."

"I didn't coin the term."

"But why only virgins?" she asked. "Do you have a blood fetish or something?"

"What!?"

"I mean, because of the hymen."

"Oh! No. I've actually never broken a hymen. Every mare I've been with might never have gotten all the way with a stallion, but they have toys you know."

"So why do they need to... with you?" she asked.

"Because I know how to get a mare off. I help ensure that their first time is a positive experience, rather than... a disappointing one."

"You think a one-night-stand is a positive first time experience?" she asked.

He poured himself another glass. "I've never gotten any complaints."

"I'm complaining!"

"Well, I'm the stallion of the house!"

And there is was. It used to be her having finality in an argument by saying, 'Because I said so.' But without a father ever being in the picture, he was the stallion of the house and she couldn't argue against it. As distasteful as the situation was, she was in a position unsuitable to make demands.

Cream Heart frowned.

Button's expression softened. "Mom, I'm sorry. I didn't mean to... I don't want to fight on your birthday. Look, I know you're not into, that stuff, being an ace."

Cream Heart looked away. "Button, just because I don't have a revolving door on my bedroom doesn't mean I'm asexual."

Button raised an eyebrow. "I've never even seen you go out on a date with anypony."

"Button, I've spent your entire life selflessly raising you alone, being a single mother! I am still your mother after all."

"Oh. Duh. I guess it would be impossible for you to be ace. Otherwise I would never have been born... Unless I'm adopted. Mom!? Am I adopted!?"

"No. You're not adopted. I was pregnant with you for eleven long months."

"Right. So you've had to have sex at least once at some point."

"Well..."

"Well, what?"

"Well... not exactly."

"How did you get pregnant without having sex? Wait, is this that immaculate conception thing? Am I the fucking messiah?"

"Button, language!"

"Am I the son of Faust, praise be unto She!?"

"Praise be unto She!" Cream Heart echoed. "Also, no! Don't be ridiculous! I just went to a sperm bank."

"... wait, really?"

"Yes Button. I was twenty one, and I wanted a foal, but I remembered what stallions were like when I was in school, and I didn't want to have to deal with a dick. Or the penis attached to him." Cream Heart smirked at her own joke even as it sailed over her son's head.

"So you just..."

"Oh, I made a nice evening of it. Some candles, chocolates and roses. But it was just me and... uh, a turkey baster."

"But you were still a virgin?" Button asked.

Cream Heart shrugged. "Yeah. I had never even bought any toys either."

"So you still had you hymen?" Button asked. Cream nodded. "Wait, so does that mean the only hymen I've ever broken was my own mother's on my way out!?"

"Well, actually..." Cream Heart leaned back in her seat and ran her hoof over the old scar running in an arc across her lower belly. "Things got a little dicey when your due date was getting close. So you ended up being a C-section."

"So you've never had sex before, or since? Not even toys?" he asked. She nodded. "You're a forty year old virgin that still has her hymen!?"

Cream Heart blushed. "Well, you don't need to rub it in like that."

"No, Mom, that's... that's kind of amazing!" Button Mash was in awe. "Look, I don't relish the idea of you getting fucked by anyone. But you really should take the time to find somepony, somepony nice who actually cares about you. Because you've been missing out!"

"Yes, well, it certainly sounds like it," she said. Button actually looked genuinely embarrassed. "It's not that I was never interested in it. I just didn't want the hassle of a relationship at first, and then I was too busy being a mother. And... I was always worried that it would hurt."

"Why? Just because of your hymen?" he asked. She nodded sheepishly. "I mean, yeah, so I've been told. It can. A little. That first time. But having an orgasm is just... it's the best!"

"Oh, Button, I've had plenty of orgasms!" she said. He looked confused. "I have a hoof and a clitoris. But I just never felt any desire to be penetrated before."

"Before?"

Cream Heart shifted in her seat. "Well... I have been listening to a certain podcast for virgins who want to lose their virginity but are too nervous. And I heard about a certain... Virginity Guru who is supposed to be the best."

"Mom... you really want me to be the one to..."

She shrugged. "It's like you said; It should be someone who I know genuinely cares about me."

"..."

"Unless you don't."

"No! I do! But you're my Mom!"

"Oh, I get it. I'm too old. Some old ugly grey-mane destined to die untouched."

"No, Mom, it's not that! You are-" His eyes drifted over her body, seeing her perhaps for the first time as a mare. "You are objectively sexy! And if I were any other stallion-"

"Then I wouldn't be interested," she said quickly. "But you're not just any other stallion. You're the one I love the most in the whole world. And I should hope that I'm the mare you love the most."

"I mean..." Button quickly zipped through his mental directory to try to think of anything else to counter with, but he knew she was right. "Yeah."

"Then what else does it matter?" she asked. "Isn't breaking a hymen what you've been wanting all along?" He stared at her. She waited for him to make some kind of argument. But none came. The idea made its appeal visibly known. Button quickly crossed his legs. "Oh, please! It's not like I've never seen it before. To say nothing of the fact that I used to change your diapers, you strut around here with that thing swinging around every other day."

"I didn't think you were looking at it!"

"How could I not!?" Cream Heart blushed harder, biting her tongue. Shifting harder in her seat, it was her turn to cross her legs. "I mean, it wasn't like I meant to. But come on! You don't think I never caught you looking under my tail?"

"What? Nu uh!"

"You're either terrible at lying or remembering."

"I- I wasn't doing it on purpose. If I was. Which I wasn't!"

"Uh huh. So..?"

"So what?"

"You asked me what I wanted for my birthday."

"I did?"

"And I told you."

"Uh..."

"So..?"

"So..."

"So would you? Do that? For me?"

"..."

Button's mouth went dry. Normally he was the smooth talker doling out tips to boost confidence. Whether it was with a microphone, or directly with a beta mare. A stranger. A pony he never really cared about despite caring for. For one night. It was easy to act brave when there was nothing at stake. He had never set out to give anypony a bad experience, but even if he did, it wasn't his problem the next day. He wouldn't see them again.

But this was different. It was different in every possible way. Because she was different. Not because he would be stuck with her, but because he cared about her. It would change their entire relationship. And it would almost certainly change him. It was much to risk. But the thing about high risk... despite his jitters of fear, there was a glittering reward right before him that he had been blind to this entire time.

"Mom?"

"Yes?"

"I... don't want to fuck you."

"Oh." She looked like she was going to cry. "It's okay. I understand. I should never have-"

Button interrupted her. "But I think I would like to make love to you."

"Really!?"

Button looked at her and swallowed the lump in his throat. "Yeah... I do."

"Okay but if we do this, you need to stop all that whorsing crap."

"The wh- but that's how I pay the bills! You want to go back to the old times? The bad times? The no-air-conditioning-all-summer, letting-the-yellow-mellow, macaroni-and-cheese times?"

"You can still do your podcast. But I mean more of those one night stands! I can't listen to that after this. It'll break my heart! Okay?"

"... Okay."

"Yeah?"

"Uh, yeah."

He looked at her nervously.

"..."

"What, like... right now?" he asked.

She stood up and grabbed his hoof to pull him along upstairs to her bedroom. She pulled the blanket from her bed and draped it over herself like a hooded cloak. She turned in place, pointing her rump at him, using her tail to lift the hem of blanket just off the floor before turning off the lights.

"There. You barely even have to see that it's me," she said. "You can just... poke it up under there and get it over with quick."

"What? Mom, no. What kind of stallion do you take me for?"

"Um... I don't want to keep saying whorse, but..."

"No. Stop it. You're not just some anonymous mare." He turned the light back on. "You're my Mom. And I don't need to pretend otherwise." He pulled the blanket off of her. "And we are not going to just 'do this quick to get it over with'. This is special. And we're going to treat it as such."

"What do you mean?"

He turned to leave. "Wait right here. I need to do a few things. I'll be back soon." Cream Heart waited patiently on her bed. Several minutes later Button returned. "Okay. I'm ready."

"Well, come on then," Cream said, patting the spot next to her on the bed.

Button shook his head. "No. You come here." He waved for her to follow him.

"Ordering me around now?" she asked. "Is this that dom/sub stuff that fillies are into these days?"

"No, Mom, it's not like that. Come on."

She slid off her bed and followed him down the hallway to the adjacent bedroom where he stopped outside.

"What, on your bed?" she asked.

"Yeah."

"Button, I don't think I can bring myself to, after all the other-"

"I changed the linen for that, obviously," he said. "And I also..." He pushed the door open, revealing the room bathed in soft candlelight. The bed indeed sported fresh, clean sheets, covered with flower petals.

Cream gasped. "Button, I never took you for the romantic type."

"It's a special occasion," Button said. "And I was going to give you those roses for your birthday lunch."

"Romantic and practical," she mused, leaning over the bed. "Something for me to snack on while you mount me?"

Button turned her around to face him again. "Actually, I was think more of making you my snack."

She brushed him away with her hoof. "Don't be fresh."

"I wasn't trying to be," he said, shifting her backwards to sit on the edge of his bed. He leaned forward, bringing his face closer to hers.

She leaned back a little. "What are you doing?"

He paused and chuckled. "I was attempting to kiss you."

"Oh. Right." She sat forward and quickly kissed him on his cheek.

"That's not... quite what I was planning on."

"Oh. Did you want to kiss on the lips?" she asked. "Should we?"

"I mean, all other things considered..."

"No, you're right." She leaned forward and kissed him on the lips just as quickly before sitting back again. He grinned and tried to stifle his laugh. "What's so funny?"

"Nothing. I'm sorry," he apologized. "I'm not laughing at you. Really. I'm just laughing at the situation. The first time is always awkward."

"I'm being awkward?" she asked.

"You're just inexperienced," he said. "And that's okay. Here, just follow my lead."

He gently held her shoulder with his hoof, running it through her mane to her neck as he closed the distance and kissed her on the lips again. She was stiff at first, but he held himself there until she started to relax. He parted his lips and touched hers with his tongue. He felt a quick puff of her warm breath from her nose against his cheek as she she tensed for a moment, but only for a moment before she tried to copy his actions. Her lips parted and her tongue met his. he moved his tongue across hers, across her teeth and back again. He could feel her breathing quicken. He slowly withdrew his tongue and pursed his lips once more before gently breaking the kiss.

"There. How was that?" he asked. Cream Heart could barely hear his words over the thunder of her heartbeat in her ears. "Mom?"

Cream's eyes fluttered for a moment as she came back to her senses. "Yeah?"

"How was that?" he asked again.

"That was really good."

"Yeah?" he asked.

"Yeah. I mean, I know we've kissed before. And I know it's still you, but it just felt so different," she said. "Like you were a different pony. Or I was."

"It's a kiss for a different kind of relationship. For lovers," he said.

She looked nervous for a moment. "Is that what we are now?" she asked. "I mean, what we would be... if we do this? Instead of mother and son?"

"No," Button answered quickly. "You're still my mom, and I'm still your son. Nothing will ever change that. It's not an either/or thing. After we... if we do this, it would be both. If you want it to be."

"Do you?" she asked. "Would you be okay with that?"

Button smiled. "Yeah. I love you."

"I love you too."

Button moved forward to kiss her again. She met his kiss with her own participation. As they kissed he leaned closer against her to hug her in his embrace, slowly laying her back onto the bed. Her contented moan stopped suddenly when she was startled by the firm contact poking her midsection. She broke the kiss and pushed him away just enough to look between them. For all the times before that she had seen his penis, this time seemed so much different.

"Your... it's..."

Button lifted her chin with his hoof to bring her eyes back to his. "Don't worry about that," he said, trying to shift himself to minimize the contact. He kissed her on the lips again briefly before kissing her cheek, and then her neck before he lightly nibbled on the corner of her ear.

"Button..." She shivered from the chills he was sending through her body.

He kissed his way back down along her neck, down her chest and abdomen. All the other virgins he had been with never had foals. Their nipples were little more than tiny nubs amid the fur of their lower belly. But even though Cream Heart's swollen teats had been years long gone, her nipples were still as big as pencil erasers. She gasped as he gave one a gentle kiss and lick before moving to the other to suck on it.

"You always loved doing that," she breathed.

"Hmm?"

"Nursing," she said. "Don't you remember? You took forever to wean."

"I wish I never stopped," he said sucking her other nipple.

"You nearly didn't. Even after you got teeth, you didn't want to give it up. But you had to be weaned before you could start school."

"I wish I could remember."

"You were quite heartbroken over it as I recall."

"Well, we can make up for lost time." Button shifted himself a bit lower.

"Wait, where are you going?" she asked.

He grinned. "I want to kiss you somewhere else."

She snapped her legs together. "Oh, no. You don't want to do that. It's gross. I haven't showered since yesterday and listening to you last night got me all hot and bothered."

"That's okay. I like the way you smell," he said. She raised an eyebrow at him. "I mean, I assume I will. Not that I have before."

She snorted. "You really are a bad liar." Button blushed. "I suppose we are a bit past any pretense anyway..."

"Fine. But I meant what I said." He put his hoof between her knees, coaxing her to spread her legs for him. She slowly relaxed and he leaned forward to see her now that his eyes had adjusted to the low candle light. Before it was like looking at the sun; he would only steal a glance and then look away. But now his greedy eyes drank in the sight of her marehood. Just beneath the tuft of her brunette pubic fur, the exclamation point shape of her teardrop pussy, above the pucker of her ponut, and the dock of her draped tail. He pressed his nose against her pussy and breathed in her scent.

Cream Heart squirmed. "Button, please! I know you want to spare my feelings, but you don't have to pretend to like how it smells!"

Button smiled. "You're right about that. I don't have to pretend." He opened his mouth and cupped her vulva with his lips, pressing his tongue between her labia, eliciting another gasp from her. He ran his tongue up along her slit to her her clitoris, giving it a little flick before kissing it and lightly sucking.

"Oh! OH! Oh my goodness!" Cream Heart cried out. She reached down with her hoof and grabbed his mane. Not to push him away, like he expected, or to pull him in harder like others had. She just held him for a moment before her grip relaxed, just keeping her hoof touching his head. As though to convince herself that he was really there. It was really him.

Cream Heart could barely breathe. She had no idea that she was even capable of feeling this way. Her hoof had rubbed her clitoris to climax plenty of times before. But it paled in comparison to the expert dexterity of his tongue on her now. When he told her that she was missing out, she had only a cursory impression of what he meant. But now she had quite a vivid understanding.

"Those fillies definitely weren't faking..." she panted.

His tongue slid down and dipped just a bit inside the entrance of her vagina. He stopped for a moment to catch his breath, smacking his lips as he savored her taste on them.

"I have to see," he said. He turned on his streaming light.

"Button! No! You're not going to live-stream us having sex are you!?"

"Of course not!" He paused. "Although I would probably make a killing right before I got banned."

"I'm serious!"

"So am I. I don't want to get banned," he said. "But now that you mention it, we should probably film it."

"Button!"

"I just mean for posterity! This is a big event. Don't you want to remember it?"

"I don't need you to film it for me to remember!"

"Okay! Fine!" He knelt between her legs again.

"Are you going to turn off that bright light!?"

"Just a second. I want to see it."

"See what?"

"Your hymen." His hooves on either side spread her pussy, making her tight vagina gape ever so slightly. Just a short distance inside, he saw it. It didn't look like he had imagined, like some kind of freshness seal. It was a thin, ring-shaped membrane of skin that narrowed a point in her vagina. "Wow..."

"Are you done down there?" she asked. "You're making this really awkward."

"Yeah..." Button breathed. "Yeah, sorry." He 'accidently' clicked the camera before turning it off with the light. He turned around and stood between her knees at the edge of the bed. "Okay, are you ready?"

"I think so. Are you?" she asked.

He lifted his erection and laid it on her belly. "I'd say so."

Cream Heart's eyes went wide. "Oh my goodness!" For all the times she had seen it before, she never really had a sense of the scale of it until then. She put her hoof on her belly where the tip reached, imagining the length of it up inside her. "Button, I don't think I can..."

"I know. Don't worry," he assured her. "None of the other mares can take the whole thing. I won't go too deep. I know how to be gentle. Now let me just..." He fished his hoof around on the floor to find the condom. He picked it up to show her. "I wrap it every time. Just like I promised."

"I appreciate that," Cream said. "But... I don't think you need to worry about that with me."

He looked puzzled. "What are you talking about?"

"Button, I'm forty! I'm pretty sure my foaling days are behind me. So you don't need that."

"Wait- really!? We can raw-dog it!?"

Cream winced. "As long as you never call it that again. And you promise- promise that your whorsing around days are behind you!"

"Yeah! That's an easy promise!" he said, excitedly tossing the packet away. He shifted his stance and took a breath to try to curb his enthusiasm. It was still her first time after all. Bringing his hips back, he slid the length of his dick across her pubic fluff until his tip grazed down across her clit. He carefully rubbed it against her marehood, getting it plenty lubricated from her wetness. He lined it up with her entrance and looked at her eyes to check with her one more time. "Are you ready?"

Cream Heart chewed her lip nervously but nodded. He applied a bit of pressure, waiting patiently for her tight muscles to relax. She shifted her hips a little help get herself started as well, but it was slow going. It seemed like they would be stopped before they even got started. He gradually pushed with a little more pressure and little by little, her virgin vagina slowly stretched around the girth of his penis until he just barely had the tip pop inside. With barely a little more depth, she winced when he bumped into the point of firm resistance inside. "Mom, this might..."

"I know, Button" she said. "But I made it though a C-section for you. So I think I can handle a trivial little thing like this."

"Okay. I'm gonna..." he warned. She nodded one more time. He shifted back just slightly before making a quick thrust forward. He felt the resistance of the thin membrane give with a sudden snap. Cream Heart cried out at the sudden pinch of pain in her abdomen. "I'm sorry Mom!" Button said in instant remorse. He leaned over to wrap his hooves around her and hug her, holding her tightly. Her thighs reflexively squeezed his sides, holding his hips still as she hugged him back. "I'm sorry!" he whimpered.

Cream sucked in a breath through her teeth. "It's okay," she cooed. "It's okay. It didn't hurt that much. Really. Just be still for a moment." At her words, Button was still as a statue. One could have played a game of Jenga on his back. "Okay," Cream said a moment later. "Okay it... it doesn't even hurt anymore." Button still didn't move. "It's okay Button, you can-" Button let out a breath he hadn't realized he was holding. He stood up and pulled himself out. Seeing her in pain had made his erection wilt. Even in the low light, he could see the dark crimson stains on his bedding. "Where are you going?" she asked.

"What do you mean?" he asked.

"You're not done are you?" she asked.

"What? No! But I... did you still want to keep going?" he asked.

Cream smiled. "Well, it seems silly for us to have come all this way and not get to enjoy finishing it."

Button got so hard again so fast it almost hurt. His erection sprang up and slapped himself in the belly. He guided himself to her entrance once more. This time it was a little easier getting it inside. He slowly pushed in a few inches more. She took a deep breath as he moved past the point of the former barrier, finding the resistance now absent. They both sighed with relief.

"Okay," Button said. "Let's uh... have sex." Cream could help herself from giggling. "That sounded better in my head."

"It's okay," Cream said. "I hear the first time is always awkward." Button smiled along with her. She waved for him to be closer and they hugged again. "Don't be scared."

"I'm not scared."

"Are you nervous?" she asked. "You're trembling."

"I..." His voice wavered and he realized she was right. "I'm just excited."

"Okay..." She put one of her legs around behind him. "Come on then."

They hugged each other tighter, each pulling the other closer as more of his penis slid inside his mother. It was a brand new sensation to her, feeling filled with his soft, but firm texture. And it was new for him as well, without the barrier of latex dulling his enjoyment.

"So much..." she moaned. The speedbump of his medial ring reached the tight lips of her stretched pussy.

"This might be a little much for a second," he warned.

Cream felt the increased pressure at marehood entrance but she just nodded. "I trust you."

Button pushed a little harder and he felt himself pop though her snug O-ring. If she felt any discomfort, she didn't let it show. But he knew that would change soon enough. He could only ever get his medial ring inside before he'd end up bottoming out against a mare's cervix and have to stop. Knowing how close he was he proceeded even slower. Her leg squeezed behind him almost impatiently. He kept waiting to bump into her final barrier but it never came. At last he felt the warmth of her hips against his, with his balls resting against the pucker of her ponut. He looked down at their union in surprise.

"Mom! I've never been able to get it all the way in with anypony before!"

"Oh?" Cream propped herself up slightly to look between them.

Her movement made her inside shift slightly and Button felt the bottom of her womb graze the tip of his dick deep inside her. "Oh, there is it." He held her waist and pushed himself into her just a bit harder, feeling his tip just barely kiss her cervix. "Wow! It's like a perfect fit!"

"Button, I am your mother," she said plainly between breaths. "I should think that we would share more than just our fur tones."

"Well, at least now I don't have to worry about going too deep!" He pulled out and pushed back in again. "Wow!"

"Wow indeed!" she panted.

"This feels so much better without a condom!" he said as he pulled out and pushed in again a little faster, and again, getting into a steady rhythm. With his entire shaft well lubricated, they moved like a smooth machine. All of her discomfort had evaporated and was now replaced with only pleasure.

"You're right," she moaned. "I have been missing out!" Each time he hilted, his balls would lightly tap her pucker. The medial ring of his shaft moved back and forth inside a very particular spot inside her vagina. Cream felt an odd sensation rising, a pressure building inside her abdomen. "Uh, Button..."

"What? Does something hurt?" he asked, worried.

"No it's not that, but..." she panted. "I... I think somethings going to happen."

"Yeah, it's called an orgasm," he said.

"I know what an orgasm feels like, Button! But I don't think..."

"It's okay," he said.

Cream Heart trusted him, but she felt nervous just the same as the pressure began to feel more and more intense. It felt like an orgasm approaching, but it also felt like the older mare was about to have an accident. "Button, I... I... Ahh!" Her body tensed and her back arched, forcing Button to lean back to balance himself as she came. Her pussy quivered and squeezed around his dick and her clitoris winked as jets of her marecum spurted out in streams up along his torso, hitting him in the bottom of his chin. He looked down at her marehood, catching the next splash in his face. He opened his mouth in shock and excitement, but the next and the rest only made it to his chest.

"Oh my goodness!" Cream Heart cried out, covering her face with her hooves even as her body continued to shivered amid the most intense orgasm she had ever felt in her life. "I'm so sorry! I knew that coffee from breakfast was going to go right through me! I didn't mean to wet your bed!"

"Mom! I didn't know you were a squirter!"

"Button, I already feel terrible! You don't need to call me names!"

"No, Mom, don't you realize how special you are?"

"What are you talking about!? Button, I peed all over your bed." She looked at the droplets falling off his chin. "All over you!" she cried.

"Mom, please don't cry! It's not pee! Honest! It's mare cum."

"Button, you don't have to make things up to try to spare my feeling. I know I'm getting older and these bad things are just going to happen."

"Mom, it's not a bad thing! It's a wonderful, wonderful thing! Look, it doesn't even smell like pee, right?"

Cream scrunched her noes. "I... no, I guess not. But still..."

"Didn't that feel good?" he asked. "I heard that a squirting orgasm is the best a mare can feel."

She dried her eyes. "Well, I won't deny that."

"Do you think you can do it again?" he asked excitedly.

"I didn't know I could do it at all. I was just as surprised as you were."

"Can we try?"

"You actually want me to?" she asked. Button nodded like an excited puppy. "But your bed-"

"Mom, if that's the only time you ever do that, then I'm never changing my sheets again. I want to sleep in this."

"Don't be gross, Button."

"I mean it! This is..." He rubbed the damp linen. "This is just the best!"

"I still think you're being gross."

"Fine, but can we try to do that again?"

"If you really want to..." she said. "But I think it's more up to you than me. I don't think I really have any control over it."

"Okay! But... just don't feel bad about it, okay?"

"Okay."

Button started thrusting again. He tried to do it exactly like he was before. But his excited expression looking back and forth between her face and her marehood didn't help to put her any more at ease about it. "Are you getting closer?" he asked.

"Uh, I kinda feel on the spot now," she said.

"Oh. Sorry. Usually it's the stallion that has performance anxiety. Don't feel like you need to perform."

"Just telling me that doesn't really help," she said. "I'm just trying to manage your expectations here. Can we just... enjoy this for what it is?"

"Right. Sorry." He calmed himself and leaned over her to hug her again. This was her special first time, he reminded himself, and he wanted it to be a positive experience for her. He kissed her cheek again and she turned to meet his kiss with her own as they made intimate love.

"This is nice," she whispered between kisses. "I love you."

"I love you too, Mom."

Her legs wrapped around behind him, trying to embrace him as much as possible, holding him as close as she could. It didn't give him much range to thrust, but that wasn't the point in that moment. Aside from moving back and forth a few inches, his shaft stayed buried completely inside her. They both enjoyed the feeling of the ultimate closeness as the consummated her faithful love for him, forsaking all others. Having him for herself in this intimate way at last was all the reward she could have wanted.

"Mom, I... I'm getting close," he whispered.

Cream shifted her hips, trying to get just a little more contact from his against her clit. "Me too," she said. "Just a little more!"

Button grit his teeth and tried to hold out a little longer. But he could feel the pressure in his scrotum rising. The muscles in his abdomen tightened and his tip started to flare. He was about to go past the point of no return. It killed him to break her heart but he had to pull out.

Cream locker her legs behind him. "Don't go!" she cried out, hugging him tighter. "Don't leave me!"

He didn't have time to warn her. The words were a jumbled, guttural mess babbling from his mouth as he felt himself go over the edge. Her legs squeezed him hard into her, keeping his pelvis pressed against her winking clit as she cried out in her second orgasm. Her moans of pleasure became a duet as his joined in. Her powerful vaginal muscled squeezed and milked his dick as he also started to cum.

His tip flared just a bit bigger, pressing flat against her cervix, perfectly fit together like lock and key, lined up with the small opening to her womb. His dick twitched and throbbed as he came. The first thick rope of his virile seed rocketed out, filling what little space was left inside her vagina.

The tight seal of his flare kept none from escaping. The only thing to squirt out of her pussy was her own orgasm, the warm wetness gushing out from between their pressed hips. With each pulse of his dick, it pumped load after load. The pressure forcing the rest of her son's sperm to flood her womb.

Cream Heart moaned and cried, awash with so many emotions. She hugged him tighter. There was so much that she wanted to say in that moment. Despite him having never moved out, she said, "Welcome home."

He hugger her back. "No place like it." He kissed her again. "Happy birthday."

Cream Heart blinked awake at the sunlight peeking in through the curtains. She looked with dismay over at the pillow next to her, finding it vacant. She tried to move but her legs felt heavy. She looked down at where her son's body was draped across them with his face in her crotch. She tried to give him a little kick to shoo him away. "Button, it's time to wake up."

"Mmff... Mom..." he whined still half-asleep, "Five more minutes..." He hugged her thighs like a pillow and pressed his face harder into her pussy until his snoring sounded more like queefs.

Cream shifted uncomfortably. "Come on. You promised you'd make us breakfast after your podcast."

Button wanted to lick her pussy and make a joke about eating breakfast in bed. He wasn't really a breakfast pony, himself, and she knew that. But she didn't mince words. He sat up and rubbed the sleep out of his eyes. He looked over at the bedside clock. It was going to be a brunch before long. "Alright, alright."

He climbed out of bed and staggered down the hallway to his bedroom studio. He sat down at his desk and put on his headset. He turned on his light and checked his levels before turning on the camera. Draped behind his chair was a bedsheet with a faded red stain.

"Good morning Equestria! It's ya boy the Mare Masher back from a long hiatus! Formerly the Virginity Guru, I'm here today to start a new podcast series to guide you in maintaining a long-term relationship..."

Down the hall, Cream Heart stepped into the bathroom to wash up and enjoy a long warm shower.

"... I'm the Mare Masher, signing off, and reminding you all to wish you mother a Happy Mother's Day!"

Cream Heart was startled when the shower curtain opened.

"Hey. Room for one more?" he asked,

"I thought you were making breakfast."

"It's in the slow-cooker," he said, rearing up behind her.

"Button..." she complained, but didn't object as she felt his erection slide inside her marehood. "I just got cleaned." Any further objection she might have had faded from her mind and she just moaned in pleasure. "I am hungry, you know. Breakfast better be amazing."

"Don't worry," Button assured her as he wrapped his hooves around her, rubbing her gravid belly. "I cooked enough for three."

Author's Note

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