"Come now, you were so excited until just a moment ago…!" Melanie rushed after the man pacing his way down the stairs. "You were so open-minded when it came to having sex with an older woman, and now you'll play the prude?"
"Look…!" Steve turned around with an expression of distraught. "…You're very hot and all, but-"
"Hot?" Melanie brought herself close to him, pressing her large, motherly bust against his chest. "I preferred when you called me stunning." She whispered in his ear in a sweet voice.
Melanie Monroe was a tall, mature white woman with long, blonde hair, aged 45. Now divorced for 5 years, it took her a long time to consider dating again, something that she thought would be easy.
After all, she was gorgeous in every sense of the word. Melanie had a thick, curvy body, with the type of ass and breasts that made any man look her way when walking on the street. As an experienced woman, she knew just how to dress to increase the impact of her assets on the men around her. Despite no longer being young and having an 18-year-old son, her face and body competed easily with young women thanks to her efforts in the gym.
Naturally, after a failed marriage, she had little interest in finding a new man to be with – at least for now. Her mind was solely focused on casual sex.
…Of which she had attained a grand success of zero thus far.
Melanie was absolutely confident that she would be a hit with men of any age, which is why she started trying out dating apps to find sexy young men to sleep with. In a sense, her assessment was perfectly accurate: She had gotten hundreds of matches. However, because of her role as a mother, it was difficult to find the time to meet up with said men and assess whether they were good enough for her.
…And then, of the few she found the time to bring back home, none had slept with her.
…Was it all just because of her 'unorthodox tastes'…?
"Look, you're *stunning*, but I'm not okay with using any of those toys, got it?"
Yes. It was definitely because of her 'unorthodox tastes'.
"Come on…" She moved a hand down and firmly grabbed the hard bulge present in his pants. "…Don't you want to fuck and cum with a sexy MILF…? I can show you a whole new world…"
For a brief moment, she thought the man would be persuaded; Sadly, despite his reluctance, the man turned around and walked out of the house.
"Bye, Melanie. Sorry." He told her while entering his car.
"There's no need to apologize for being a coward." She wore a conceited smile on her face until the very end. The moment the man was no longer within her view, she let a bit of frustration show on her face. "Hah… Another night alone… There's only so much masturbating can do… Are there really no more interesting men in this world…? I already lowered my standards with this loser too…"
"Hey, mom!"
"Hm?" Melanie looked to the side. 'Oh. I guess it makes no difference whether I got ditched or not.' Her son, Barry, and his friend, Dylan, were entering her driveway on their bikes. "Hi, honey. How was it?"
"It's pretty cool! Karaoke bars are kind of awesome!" Barry was in high spirits. He was an average-looking, average-built young white man with brown hair and brown eyes, much like his father.
"Yeah, that was pretty fun." Dylan also seemed to be in high spirits. He was a short, young white man with an athletic physique, sporting long black hair and brown eyes. "You usually only hear about those in big cities. We got lucky."
"Yeah. Did you see the way Finn sang that song? It was the most…-" Barry and Dylan talked about the fun experiences they shared in the karaoke.
Usually, Melanie would pay attention, like a good mother. However, right now, her mind was focused elsewhere.
On her son's friend.
'Dylan is quite handsome, isn't he…? And he's short and young…' She inadvertently licked her lips while eyeing him up and down. 'And has long hair… Just how I like it… It's rare in men…' Without realizing it, she subtly gestured with her right hand beside her body, imagining herself wrapping his hair around her fingers like a leash.
While her thoughts ran wild, she caught a glimpse of Dylan eyeing her up as well. 'Oh, my…' Melanie looked down at her body. 'I AM wearing very tight leather pants and an unbuttoned, tight-fitting blouse, aren't I…? Does he like older women…?'
"Alright, bro, I'm calling it in for the night!" Barry ran into the house.
"Alright, see you around! Good night to you, Mrs. Monroe!"
"Hang on a moment, Dylan." Melanie walked over to him, standing in front of his bike.
"What's up?"
Melanie remained silent for a few seconds, observing his face and body. 'The way he's innocently looking at me…' She could feel her heart pounding. This mere interaction had been enough to get her vagina wet, which instigated her to probe further. "You've grown into quite the handsome young man, haven't you, Dylan…?"
"Thanks, Mrs. Monroe!" He scratched the back of his head, unused to compliments from beautiful women.
"Hm…" Melanie touched his shoulder. "These shoulders of yours are no joke… You might not look like it with this shirt, but you're actually quite lean, aren't you…? I bet you've got some nice veins around your body…" She maintained eye contact with him while running her finger down his arm. "Just how I like it…" She sweetly whispered.
"Th-thank you…" The small change in her look and touches were enough to make Dylan nervous, which was exactly her intention.
"How old are you now, Dylan…?"
"I-I turned 18 two weeks ago…"
"Really…? That's exactly what I wanted to hear."
"H-heh…?"
She walked around his bike and started running her fingers across his back. "A strong, sexy boy like you must be showering in women, right…?"
"W-well, I don't know…"
"Hm…" She subtly moved her hand to his hair, playing with the tip of his strands. "…Come on, you can just say it straight to my face."
"Say what…?"
Melanie brought her lips to his ear and whispered. "You're drowning in pussy, aren't you ♡?"
Her vulgar language caught him so off-guard that Dylan's body jerked to the side, making him fall down along with the bike. "Khh…! Ouch…!"
"Oh, my! Are you okay?" She helped him get up. "My bad. I just wanted to play with you a little bit. You look like such a kind, nice boy, I couldn't help but be a little mischievous. Can you forgive me…?"
"O-of course! I-I'm the one who overreacted…!" Dylan's eyes unwittingly wandered to her exposed cleavage. The moment he realized Melanie had noticed him, he looked away in a panic. "A-anyway, I gotta go! See you around, Mrs. Monroe!"
Dylan pedaled away- "Khh!"
Melanie stopped him by gently tugging on the end of his hair. After he groaned in pain, she let go. "Sorry. I didn't realize you were already going. I was just trying to get a feel for your hair. It's so beautiful."
"O-ok, haha…! Bye-bye!" Dylan pedaled away.
She watched him leave while sinking her teeth into her lips.
Her heart was racing.
It was true that she meant to verify the texture of his hair.
However, more importantly, she wanted to verify something else…
'His moan is so cute… ♡!'
***
A week had passed since the last time Dylan visited Barry's house. They preferred to do outdoor activities, like skating, but Barry had bought a new fighting game and invited him to play.
"That's bullshit! How are you doing that?! Teach me the combo!" Barry cried.
"You need skilled fingers to do that, I'm afraid. A moron like you would never learn!"
Barry looked at Dylan's controllers with a look of cynicism. "You're fucking kidding me, right?"
"What's wrong?"
Dylan was, quite literally, pressing every single button at the same time as fast as he could. There was not a single ounce of brainpower behind his finger movements.
"You have no idea what you're doing with your hands! You suck at this game!" Barry boldly claimed while getting his ass whooped.
"Oh, yeah?! Why don't you ask your mom?"
"Ask her what?"
"How good my fingers are!"
"…Would you like to show me…?"
…
…
…
Dylan froze.
The first question had not been asked by a male voice…
…Much less the second one.
He looked to the side with the widest eyes of panic and stiffest neck of his existence on this Earth.
Barry's mother, Mrs. Monroe, was standing by the doorway, wearing an outfit similar to that day when they spoke in the front yard. On her face, she sported a smile that he could not promptly decipher.
…Was it naughty…? Dylan was far too innocent and unused to interacting with sexy women to know for sure. 'S-sexy…? Well, I guess she is… Her legs are big…'
"Come on, mom, we're playing. Watch out, Dylan, I'm not going to pause!" Barry focused on the game.
He ignored Barry. "M-Mrs. Monroe, I-I…"
"Why don't you come with me, Dylan…?" Mrs. Monroe tilted her head, gesturing for him to follow her.
"N-no, it was just a j-joke…! T-trash talk…!"
"I'm not mad. I just need a pair of strong hands to help me out." She walked over to him and rubbed his arms. "These are more than enough. Maybe you can even show me what you mean with good fingers…? How about it?"
Feeling her fingers on his arm was enough to make Dylan turn into a statue. 'I-I haven't thought about it since that day in the front yard, b-but… Mrs. Monroe is s-super beautiful, isn't she…?' Being in such close proximity to such a gorgeous woman – one praising him, no less – was enough to make Dylan blush hard.
"M-mom…! You're making it weird!"
"What, can't I be playful anymore? Is it because I'm old?" Mrs. Monroe chuckled and looked straight into Dylan's eyes. "Don't you want to come with me to the kitchen while my son plays by himself for a bit…? Are you scared of being alone with me?"
"Come on, Dylan, ignore my mom. Let's go another round."
"N-no, I'll go. I-it's my way of apologizing for making such a crude joke…" Dylan got up, though he could hardly tell why. Despite what he just said, his reason felt like a lie.
The true reason was much more basic and primal: He felt compelled by the way she looked at him.
How was he supposed to say no to a stunning woman looking at him with so much pressure?
She wanted him to say yes, and so he would.
"We'll be right back, honey." Mrs. Monroe grabbed his shoulders from behind and gently guided him toward the kitchen.
It was a completely needless act since he clearly knew where the kitchen was.
Yet, Dylan said nothing.
Her soft breasts were pressing against the back of his head.
Though he felt bad for remaining quiet, they just felt too nice.
Dylan never knew Mrs. Monroe was so touchy.
***
"This way…" Mrs. Monroe whispered in his ear. "Just stir the pot like this and I'll have some delicious muffins for you two soon enough." She guided his hand by the wrist…
…While touching the side of his abs with her other hand.
"O-okay… Like this, right?"
"Perfect, dear… You are such a good boy. I only had to show you once and you already got it right." She backed away from guiding his wrist and started feeling both sides of his body at the same time. "…I think it's great when a young man can follow instructions." She pressed the front of her body to his back; Her cleavage directly touched the back of his head.
Dylan could not understand what was happening. He was unable to say no to Mrs. Monroe earlier – not that he wanted to say no – but did not expect the act of helping her to be so 'intimate'. All he wanted was to make up for the joke he told. 'Sh-she's way touchier than I realized…!'
In line with his initial goal, he decided to apologize while stirring the pot. "L-listen, Mrs. Monroe… S-sorry for saying that joke…"
"Why is that?"
"W-well, it was inappropriate."
"Inappropriate…? But you've yet to tell me what you meant by it." She let go of his waist and reached around to grab his chin, making him look up at her face; The height difference almost scared him. Dylan stood at 5'7 while Melanie stood at 6'1. "Inappropriate in what sense?"
"I-uh-D-In-Uuuuh…" The pressure of her gaze mixed with the warmth of her cleavage on the back of his head sent Dylan into a pathetic spiral of gags and stutters.
"Could it be that you were making a sexual joke about me…?"
"N-no…! I would never...!" The direct accusation was enough to bring him to his senses.
"Oh…? You don't think I'm attractive enough to warrant that sort of joke, then…?"
"No! Y-you're stunning, Mrs. Monroe…! Really…!"
Her eyes opened wide at his choice of compliment. "You know…" Her voice became soft and seductive. "…I don't mind it if you were thinking of me in a sexual way, okay…?" She caressed his cheek.
"B-but…"
"It's fine, Dylan… It makes me happy to know that a healthy, young boy like you finds me attractive. I almost think I could fall in love with a handsome boy like you."
"F-fall in love…?!"
"That's right. If I were your age and in your class, I'd be all over you… And then…" She let go of his chin, aware that Dylan was so mesmerized by her amber eyes and domineering smile that he would not look away. Mrs. Monroe slid her hands down from his chest all the way to his lower body, resting them on his hips, distressingly close to his crotch. "…I'd show you just what I can do with MY fingers…"
After that, she said nothing, staring at him in complete silence. Dylan felt fully wrapped under her control. As long as she did nothing, he could not move. His heart hammered against his chest, and there was intense burning between his legs.
"Good job. You can go now ♡." She stopped touching his legs and let go.
"H-huh?" Dylan looked at his hands. This entire time, he was still stirring the pot, like she ordered in the beginning. With everything that was going on, Dylan was certain that his body had been stiff like a statue; Apparently, he was wrong. 'Is it because she didn't tell me to stop…? I felt hypnotized…'
"Thank you for being a good boy and helping me out, okay? Go back and play with my son now. I'll finish up and bring the muffins to you two."
"'K-kay!" Dylan moved to leave the kitchen.
"Oops. Careful there, dear."
"H-hm…?" He looked back. Mrs. Monroe devilishly smiled at him.
"Your legs; They're trembling. Try not to fall, okay?"
"O-oh… I didn't even notice… Hahaha…"
"All the blood must have gone somewhere else…" She stared directly at his groin and then kept her eyes glued to it.
…Almost as if she wanted Dylan to take note of the fact that she saw his hard-on.
Dylan said nothing, fleeing the scene like a coward.
His boner remained until he got home and jerked off multiple times later that day.
While pumping his dick, the hand motion reminded him a lot of his moment with Mrs. Monroe earlier that day.
And, consequently, the lovely sound of her voice.
Dylan found himself obsessed with an older woman; His friend's mother, no less.
He was not the sort of man who masturbated frequently. Dylan barely spoke to girls, shy as he was. Yet, for the next several days, his desire to masturbate expanded tenfold, and every single ejaculation was a guilty homage to her.
His main fantasy was her whispering 'good boy' in his ear.
***
Dylan was on his bed, messing around on his phone. There were a couple of girls from his class that he considered texting but quickly lost interest.
If it were a few days ago, he would be trying his best, though with awful social skills. Dylan had lost the interest of many girls throughout his teen years and things did not seem to change. Consequently, he had yet to kiss a girl or go on a date.
Usually, he would be nervous about the subject; However, ever since the mysterious interaction with Mrs. Monroe several days ago, all he could think about was her, thus not caring about texting girls.
As if summoned by his mind, a new number suddenly texted him.
The profile picture left little room for interpretation: It was Mrs. Monroe smiling at the camera.
'Hello, Dylan.' She texted, accompanied by a series of emojis that made no sense. 'What are you up to?'
Though they were far apart, a mere text from her was enough to flood him with anxiety and a racing heart. Unlike with other girls, Dylan felt induced to text her back right away.
'Not doing much. How about you?' He tried to play it cool for some inexplicable reason.
Her response just made his heart beat faster.
'Trying to find a good man on these awful dating apps.'
Dylan had no clue what to respond to that; He had no idea what Mrs. Monroe could even be expecting as an answer.
Taking too long to text back, Mrs. Monroe took the lead.
'I wish I could find one just like you.'
'J-just like me?!' Dylan thought. 'Mrs. Monroe says the weirdest things…! I-I almost feel like she's hitting on me or s-something…! But there's no way… She's just Barry's mom. I mean… I-I wouldn't mind it if she were, but… I shouldn't even be thinking of her this way…' He was too loyal of a person to even fantasize about his friend's mother without feeling bad.
'What about you?' Mrs. Monroe texted again because of Dylan's lack of response.
'What about me?'
'How would you feel with a woman like me?'
Her text was so upfront that Dylan literally gasped, caught completely off-guard – something that seemed all too common around Mrs. Monroe after that night in the front yard.
Why was she even asking such a thing to him?
In a moment of ingenuity, he remembered the moment when Mrs. Monroe messed with him by uttering a vulgar sentence in his ear. She was likely just being playful in her own weird way. 'Of course…! She's not actually flirting with me… Hahaha… I'm losing my mind here… She's way too beautiful anyway… And Barry's mom… Uhm… So… What do I text…?'
This time, no matter how many minutes passed, Mrs. Monroe did not text again, waiting for his answer.
It should be blatantly obvious: Of course Dylan would be over-the-moon with a woman as gorgeous as her. 'But what if she takes it as shallow…? All I'd be complimenting is her appearance… What should I say…? Even if it's just playful banter, I should still be mindful…'
In an attempt to not come off as superficial, Dylan texted back with the best choice of words that came to his mind.
'I'd love to be with a woman that has such a great aura.'
…
…
…
'WHAT THE HELL DID I JUST TEEEEEEEEEEEEEEEEEEXT?!' He bit the sheets to keep himself from screaming in shame. 'THAT'S THE CRINGIEST THING IN THE WORLD! PLEASE, KILL MEEEEEEEEEEEEEEEEEEEEEE!'
Dylan was the type of guy who enjoyed being 'alternative'. In terms of music, art, spirituality, hobbies… Even the horoscope or ghosts. Inspired by many rock musicians of old, he even let his hair grow long. It was only natural that he would sometimes say awkward things.
That still did not let him forgive himself. If given the option to cease existing right then, he would take it out of pure embarrassment.
His internal ramblings of shame were silenced once his phone vibrated.
Mrs. Monroe was calling him.
A normal voice call.
With an empty head, he took the phone and accepted the call, too stunned to understand why his friend's mother was calling him at such a late hour.
"Good to know ♡." Was all she whispered in an incredibly provocative way before hanging up.
No more texts were exchanged after that.
Dylan was left slack-jawed for a long time.
Once he snapped out of it, he jerked off into the night.
'Good to know ♡.'
'Good to know ♡.'
'Good to know ♡.'
Those words echoed in his dreams.
***
Dylan biked his way to Barry's house. Earlier that day, he was invited to play videogames.
Upon arriving, his heart sped aggressively. 'His mom is probably home too, right…? I-I haven't spoken to her since that day last week…'
He almost considered leaving and making up an excuse, but ultimately powered through. 'I'm looking too much into it… I mean, there isn't anything to look into anyway! It's not like my parents haven't spoken to Barry before either…! Th-that's all…!' His mind sheepishly glossed over the salacious nature of his interactions with Mrs. Monroe. 'Let's just not say anything embarrassing today…! I henceforth ban the word "aura" from my vocabulary!'
The door opened a few seconds after he knocked.
To his bad luck, the worst-case scenario occurred: Mrs. Monroe opened the door…
"How's my aura today?" …And instantly teased him, giggling innocently.
Even worse: Her outfit immediately summoned the focus of his gaze. Mrs. Monroe sported tight-fitting blue jeans that showcased the thickness of her legs and hips; On her upper body, she wore an orange satin button-up shirt. However, unlike the intended nature of the shirt, she did not have it buttoned up at all. Only the bottommost one was buttoned, leaving a substantial portion of her toned midriff exposed; More interestingly, a record amount of her cleavage was made public, at least as far as Dylan's experiences.
Still, there was something else that made him incredibly flustered. Something he noticed unconsciously, but took his mind a second to catch up.
'H-holy…!' Mrs. Monroe was not wearing a bra.
If the shirt were slightly looser, her motherly bosoms would definitely slip out fully. 'Sh-she tucked the shirt into the jeans really tight…! I can make out the shape of everything…! Even a bit of her nipples…! Wh-whoah…!' The sight overpowered his common sense, leading him to unintentionally ogle her body slack-jawed.
"What a vigorous boy you are, Dylan." She cut him off from his daze with a playful look and smile. "Why don't you come on in?"
Dylan walked in while opening and closing his mouth like a mindless idiot, trying to speak.
"You didn't answer my question."
"Wh-what question?"
Mrs. Monroe bent over, bringing her face level with his. "How's my aura today…?"
Her bent body provided Dylan with a privileged view of her cleavage. Her boobs looked even bigger with gravity bringing them straight down. Without taking his eyes off them, Dylan did his best to answer. "I-it's awesome…!"
"I'm so happy to know. It's such a unique compliment to receive! Hm…? Oh, how cute!" She traced her thumb along his lips, scooping some sort of liquid. "Why were you drooling, dear? And why are you looking so intently at my chest? Is something there…?"
Dylan was far too agitated to offer anything resembling a coherent or smart answer. Having been caught drooling over her breasts, he favored dying of a heart attack as an excellent outcome.
Unfortunately, he lacked the power to die on demand, so he took the next best course of action. "NoIwasn't!" …Bursting an outright denial out of his mouth.
"No…? What's this I just scooped up, then…?" Mrs. Monroe brought the thumb into her mouth and swiftly sucked it clean.
Dylan stiffened up like a statue, witnessing his first kiss – albeit indirectly and filled with mind-numbing embarrassment; Also, the woman kissing him likely had no idea that they were kissing.
"Hm… I THINK it was drool… Oh, well, whatever it was…" She pulled the thumb out with a loud pop and twisted her lips in a mysterious smile. "…It had a great aura."
Far too agitated to realize she was giggling at her own joke, all Dylan could do was focus on the smile on Mrs. Monroe's face.
What was that supposed to mean?
He was an inexperienced virgin who had never even kissed a girl – directly – before. However, even he was forced to consider an astonishing possibility.
…Was it a naughty smile?
***
"So Barry is out of town with his dad…?" Dylan was on the living room sofa, chatting with Mrs. Monroe. "But he invited me to come over."
"I don't understand either. I guess it must be some sort of misunderstanding… But I'm pretty happy about it."
"Huh? Why…?"
"Because I get to be alone in this big house with such a handsome young man."
"A-ah…! Hahaha…! I-I guess I'm lucky too, then…!"
"Why?" She did not wait even a millisecond before following up on his statement.
Cornered too abruptly, Dylan could say nothing other than the truth. "B-because… Y-you're… A g-gorgeous woman too…!"
Mrs. Monroe said nothing. She simply smiled in clear approval of his answer and silently observed.
For multiple minutes.
Dylan did not understand what she was doing, but every second that passed made his frantic heartbeat more present. It lasted forever in his mind.
Initially, he moved his gaze all over the room, too nervous to maintain eye contact. Once he noticed his eyes were wandering toward her cleavage, Dylan decided it was time to flee, like a coward. "Alright, Mrs. Monroe…! I guess I'll just get going then…!" He stood up.
"…Why?"
"Heh? Because… Because Barry isn't here."
"Would hanging out with just me be so bad…? Because, for me, hanging out with such a nice boy like you sounds really fun… And you did say I'm gorgeous…"
"O-of course not…! And you ARE gorgeous!"
"Would you stay and have some fun with this gorgeous woman then…?"
"O-of course! Sure!" Dylan sat back down as fast as he stood up.
"Hm… You're a really good boy, aren't you? Sitting down right away just because I asked… I love men like that, you know…? And you're very cute to boot…" Mrs. Monroe tilted her head and looked at him… Seductively…? Her voice was like music to his ears. Dylan could not tell if she was speaking in a specific way to catch his attention or if it was just her normal voice. Right now, he was too allured by her. "Why don't we watch a movie together? Sound good?"
"S-sure…!"
"Excellent. I'll just make us some popcorn. Wait here, alright?"
"Okay. Oh, can I have some water?"
"Sure thing. Be right back."
While waiting, Dylan figured he would use his phone to ask Barry about-
"No phones allowed." Mrs. Monroe swiftly took the phone from his hand and put it in her pocket. "You have to give me aaall your attention, okay…?" She whispered in his ear, leaving before he could respond.
It was enough to leave him paralyzed and flustered. 'Wh-why do I feel this way around her…? There's just something about the way she speaks and looks at me…! I feel so… Small…' Dylan focused his efforts on calming his fast-thumping heart.
Such a thing was a mostly futile effort. The moment Mrs. Monroe returned, strutting her thick hips, his heart accelerated again; Her stature was too womanly and curvy to walk any other way.
"Thank you for waiting." She handed him a cup of water, sat on the other end of the sofa, and took the remote. "Feel free to eat whenever, okay?" Mrs. Monroe kept the bowl of popcorn on her lap, far away from his reach.
"O-okay."
"Also… I have to make a confession."
"Hm…?"
"I was already watching a movie before you got here… But it got to a tough part, so I didn't want to watch it alone."
"Oh!"
"So, thank you for keeping this old woman company, okay?"
"S-sure thing, Mrs. Monroe!" Dylan felt relieved, believing to have gotten a better understanding of the situation. 'She's probably scared of some horror movie or something… That's why she wanted me to stay! I really was looking too deep into it!'
"Can I start?"
"Yeah, go ahead." Dylan liked horror movies, so he was relative-
"Nghhhhhhhh ♡! Ooooooooh ♡! Yes, John… ♡! Fuck me good… ♡! Oh, yeeeees… ♡!"
'What the-!'
It was porn. Or so it appeared, at least. Perhaps it was just the sex scene in a normal movie.
But at the moment, it looked comically pornographic. Dylan's eyes shot wide and his jaw dropped – yet again – upon being caught off-guard.
It took his brain a few seconds to realize he was watching a sex scene alone with Mrs. Monroe.
Though he was by no means sheltered or religious, Dylan still had little experience with adult content. His daily masturbations consisted mostly of fantasizing about his crushes in entirely vanilla settings.
Yet, here he was, watching some actress getting proneboned hard while his friend's mother was eating popcorn close to him; The same woman to whom he had masturbated to several times in the last several days.
'…W-wait… Why did she need ME to watch THIS?!' Despite the pertinent question, his main worry soon changed. 'I-I'm embarrassing myself again…! I can't act this shocked because of some g-gratuitous Hollywood sex…!' To distract himself from his daze, Dylan reached out to grab some popcorn.
It was a colossal mistake.
Dylan did not look away from the screen before reaching out, leading him to miss his target.
Instead of grabbing popcorn, Dylan grabbed Mrs. Monroe's thighs, unintentionally sinking his fingers into them in the process.
Once more, in what seemed to be an uncontrollable habit by now, Dylan froze up, horrified by the unforgivable atrocity committed.
Mrs. Monroe's gaze implied something far different.
"We're too far apart, aren't we? How unfair of me, hogging the popcorn all to myself…" She grabbed his hand and pulled him toward her.
…All the way onto her lap. Dylan found himself sitting on her. It was a miracle that he did not drop any water on either of them.
'H-how… Did I end up here…?' The sex scene playing on the screen barely mattered to Dylan anymore. The fact that he was literally sitting on Mrs. Monroe's thick, warm lap while his back touched her soft boobs over her shirt was a far more pressing matter. Though he was a man and she was a woman, he looked tiny on her legs. If someone were to look from behind Mrs. Monroe, his silhouette would be non-existent, fully engulfed by her tall, curvy body.
"Here you go." She rested the bowl of popcorn on his lap, right above his crotch.
Right above his HARD crotch.
Dylan only realized it then: He had a hard-on. The bowl of popcorn applied pressure to his bulge, giving it light stimulation.
"Oh, my, why is it so hard to balance this bowl on your lap…?" She asked in a seemingly sarcastic way.
Utterly bewildered, Dylan opted to let his mind go blank as he slowly grabbed popcorn and moved it to his mouth. Chewing on something was the only way for him to distract his mind.
It worked for a minute… And then the next insane thing occurred.
Mrs. Monroe started touching his body all over, just like in the kitchen several days ago. She firmly pressed her fingers against his clothes, traveling the length of his body from his calves to his chest. "You really are quite strong, aren't you…? What a pretty boy… I am so lucky to have the chance to even feel you this up-close."
"Th-thank you…"
"What did you think of it…?"
"O-of what…?"
"Of my leg… You got a feel, didn't you…? Tell me what it felt like."
Though Mrs. Monroe held no actual authority over Dylan, he felt ordered to respond. "I-it felt nice."
"Was it the first time you touched a woman's leg?"
"Y-yeah…"
"Hm…" She went silent for a couple of minutes but kept touching his body. "…You know, isn't that just disgusting…? The movie scene, I mean."
"Why…?"
"That man is having so much hardcore sex with that MILF, even though she is married. To take someone else's semen so eagerly when a man awaits you at home… I just find it deplorable… Don't you think so?"
"W-well… Yeah, cheating is wrong…"
"That's right. Hardcore, fun sex should only be had if both parties are available. By the way…"
"Y-yeah…?"
She brought her mouth so close to his ear that he could feel her perfume suffocating his nose. "Just a reminder that I'm single ♡."
It was a harsh blow. With mere words and a bit of sweet breath against his ear, Dylan's body flinched to the point of spilling his drink all over himself. "Crap!" Thankfully, he shot up from her lap so fast that none of it got on her.
"Oh, no…" Mrs. Monroe brought a hand to her lips. "…I guess I'll have to dry those clothes of yours now."
"H-heh…?"
"You're such a good boy ♡."
***
Dylan was impressed by how much the day had changed from his initial expectations.
At first, he expected to visit his friend, play some videogames, and maybe be a little embarrassed around his bombshell mom who behaved in peculiar ways around him.
Now, he was alone with her in the house, wearing nothing but his boxers and socks.
Two things ran through his mind at the moment.
The first one: He thanked God for having come in boxers instead of briefs.
The second one: How the hell did she convince him to take his clothes off?
What would he do now?
'M-my clothes will take at least half an hour to dry up…! W-what do I do when she comes back?! This is so awkward…! She must think I'm such an idiot now…!'
By this point, Dylan was convinced he had a massive crush on his friend's mother. It was the only way to explain his quirky behavior whenever she was present. 'Good thing I'm so ashamed that my boner died down…' He breathed a sigh of relief. Wearing only boxers, there was no way it could be hidden. 'This is so wrong… Barry would be so mad if he saw me like this… What do I do…?'
"It's drying up." Mrs. Monroe entered the room with little warning and headed straight for the sofa, sitting down close to his side.
…Very, very close.
'Shoulders touching' sort of close.
The sort of close that made his face burn red and his head ache due to raw anxiety.
All while he was on nothing but boxers.
"You've really grown into a great boy, haven't you, Dylan…?" She reached around his lower back, grabbing his waist. "I can really see your muscles now… This sort of lean physique is definitely my favorite. I don't like it when guys are buff… And your long hair is really nice too… You don't mind if I call you a pretty boy, do you…?"
"N-not at all… Thank you…" His heart rammed against his chest so violently that her words got slightly muffled by its sound ringing in his ears.
"And you're so polite too." Mrs. Monroe giggled. "Oh, my, I wonder what your mother did when raising you. Barry is a kind young boy, but I wish he were as respectful as you are. But, even if your mother did a great job raising you…" She pressed the side of her covered boobs against his shoulder and brought her face closer while piercing his eyes with her gaze. "…There are some things only a different mother can do for you, right…?"
"L-l-l-like what…?" Dylan could not formulate sentences any more complex than that. It took everything in his body to avoid stuttering into a fully failed sentence.
"Well, what is the first thing that comes to your mind? What is something that only your friend's sexy, busty, mature… And *horny* mother can do for you… ♡?"
The special emphasis on 'horny' sent his mind full haywire. If it were at all possible, Dylan would have overheated into breaking; Sadly, he was no machine, and thus had to deal with the hurricane of anxiety and lust building up within him.
'…Lust…?' He looked down at his legs. 'C-crap…!' His boner was back. 'I can't let her see it! I need to cover it with my-'
"How adult of you…" Mrs. Monroe followed the path of his gaze all the way. In other words, she caught him staring at his own bulge and then caught him again when staring at her face.
Now, his eyes were entrapped under the pressure and dominance exuded by her attitude and body language. "You've barely turned 18, haven't you? To be so bold as to sport full-blown erections around your friend's mother like that… Did you think it was okay because you're on your underwear…? Or is it because you like my boobs so much…? I wonder what Barry would think if he knew you want to bone his mother…"
"N-no, I-I… Uhm…!"
"Either way, I take it as a compliment, so don't be upset."
"Compliment…?"
"Uhum…" She nodded. "…It means you got so turned on that you want to fuck me silly. Since you're such a kind, admirable boy, I'm sure you feel guilty because you're Barry's friend, but your attraction for me is stronger than even that. It makes my heart skip a beat… It's not a problem, okay…?"
"I-it isn't…?"
"No…" She put her other hand on his leg, very slightly fondling his thighs. "…Because I want to fuck you too ♡."
Her words echoed in his mind a thousand times during the span of a few seconds.
They were the killing blow.
Dylan's mind entered fight-or-flight mode.
Of course, he chose…
"I need to go! Thank you for everything!" The words burst out of his mouth without any conscious input. Dylan turned into a mess of nervousness. Just as he intended to shoot up and get out of there, yet another killing blow struck him.
A kiss directly on the lips.
Mrs. Monroe grabbed his chin and glued her mouth to his, not waiting even a little bit before shoving her tongue down his mouth. Because of how passively Dylan accepted her lips, she easily embraced his tongue with hers, imposing several more French kisses onto him.
…Not that he wanted to push her away. His mind easily turned to pudding.
After making out for half a minute, Mrs. Monroe concluded that she had successfully calmed him down and pulled her lips away. Then, she made him look straight into her eyes and whispered. "I'm going to take care of your boner, okay…?"
A third killing blow within the span of five minutes.
Dylan was so out of his zone that she could probably tap him on the shoulder to make him fall flat on the floor. His body turned to jelly under her words and soft touches. He could not believe what was happening.
Before he could recover from his fluster, Mrs. Monroe kneeled between his legs and pulled his underwear off. It occurred far faster than he realized.
His cock shot out, standing at a full mast. The moment it came into view, Mrs. Monroe's eyes changed from smug to lecherous amazement. "I could tell from the outline in your boxers, but it's even better when I look at it directly… You've got quite the dick for such a timid boy, don't you, Dylan…? This is the sort of powerful cock I expect from tall jocks… Not a good boy like you. You could probably break juicy pussies on the regular, but I can tell you're a virgin… That's so lucky…! I can't believe I've found a boy who isn't corrupted and ruined…"
He had no idea if it was a compliment, but it mattered little. His penis thought it was one, prompting it to twitch so aggressively that it nearly touched her face.
"Oh, I like it… Little Dylan is very enamored with me…" She moved her hands up his inner legs, teasing the moment when she would finally touch it. "…It should be, of course. I think I'm enamored with it too."
"Thank you…!" It was the best response that came to his mind. In truth, Dylan had not yet registered the true nature of what was taking place in front of him: Mrs. Monroe was aggressively coming onto him and they were likely about to have sex. To him, the present scenario was so outlandish that there had to be some other explanation.
Meanwhile, Mrs. Monroe continuously teased his throbbing cock with her lips and fingers, repeatedly pretending that she was about to touch it only to stop right before. Each time, it was more than enough to make it twitch intensely and produce new veins of arousal, flooding his member with blood.
"Little Dylan is so eager for me…" She stood up and kissed him again.
This time, Dylan managed to kiss her back, going so far as moving his own tongue around hers voluntarily; A couple of times, he even felt in control of the kiss. Each time that occurred, Mrs. Monroe touched his chest or caressed his legs, sending him into a daze that easily gave her back control.
Still, it was a mark of progress. Dylan was starting to grasp reality as it was. 'It's going to happen…! M-my friend's mom is into me…! And we're going to have sex…! I'm losing my virginity to her…!' At the moment, he was too agitated to feel guilty; His only focus was trying to calm himself and understand the situation.
"I'm going to teach you pleasure that most men don't know about, okay… ♡?"
"O-okay…!"
"It might look a little unorthodox at first, but I promise it's waaaay better than anything you could get from a boring, bitchy young girl. Just let Melanie coach you into the right way of having sex with an attractive woman."
"I-it's fine…! I'll follow your lead…!" He nodded frantically.
"Really…? Do you promise…? Will you trust me all the way…?"
"Yes! I promise!"
"Oh, my… Since you're such a nice boy, I'm sure you know that promises have a heavy weight to them. I'll hold you up to it, then… Let me teach you the right way to cum, then. Just trust Melanie…" She got between his legs again and covered her middle finger in spit.
Dylan followed every one of her movements with obsessed eyes, fully mesmerized by the assertive woman. He watched with great excitement as she locked eyes with him and slowly moved a hand toward his balls. Both of their smiles widened with each inch moved toward his sack…
…But only Mrs. Monroe maintained that smile when her hand ultimately went right past his balls and straight into his…
"Khhh!" A sharp pain made his body jerk up.
Mrs. Monroe inserted her middle finger into his ass.
His smile faded away, flabbergasted; Hers became wider, complemented by a blushing face.
"H-hey…!"
"Yes…? Is there a problem…?" She asked him with a playful tone.
It was a stupid question. The problem was evident. There was a literal finger up his ass, even if superficially. However, once he tried to voice his complaint, her question no longer sounded as stupid. It was Dylan's frustration that felt stupid.
After all, her face was drowned in euphoria. Mrs. Monroe's chest heaved up and down wildly, and her breathing accelerated. Clearly, she was having a grand time with Dylan.
…How could he possibly say anything to ruin the moment? Especially a virgin like him who hopelessly crushed on his mother's friend. "N-nothing…" Right then, Dylan discovered he was far more sexually open-minded than he ever imagined. "G-go ahead…"
"Haaaaaaah ♡…" His answer made her moan in approval. "That's exactly what I needed to hear ♡… I knew you were perfect from the moment we talked that night ♡…" Her eyes turned unfocused for a moment but quickly recovered. "Let me show you the right way to be a man…!"
Perceiving no further resistance from Dylan, Mrs. Monroe reached into her jeans and pulled out a small tube of lube. She removed her finger from his anus, covered it in said lube, and then slowly inserted it again. "It'll be easier like this. I just wanted to test your mettle ♡." She started slowly thrusting her finger up and down in his ass.
"Khhh…! Nghhh…! Uhm…!" Even if it was just Mrs. Monroe's small, feminine middle finger, it still felt incredibly thick inside his anal walls – and it had barely made room into him. Dylan wanted to ask her to take it even easier.
Ultimately, he suppressed his desire, not wanting to frustrate her. Mrs. Monroe's face was bathed in ecstasy. The act of fingering his ass was apparently of immense pleasure to her. As bizarre as Dylan found it, he felt masculine from making her feel good this way.
That feeling gradually changed as Mrs. Monroe slowly probed further into his anal cavity. "Nghhh… Uuuungh…" His groans of pain were steadily replaced by moans of pleasure. Keeping Mrs. Monroe happy by just powering through became secondary: Dylan started actually enjoying the act.
It became even better when she stood up and began making out with him while fingering his butthole. "Mnhhhm… Nghhhh…"
A problem soon surged: Kissing him made it difficult to maintain a proper angle of penetration into his hole. Dylan could feel her finger slowing down, but not out of a desire to be gentle; Rather, out of a lack of proper leverage.
In a moment of brilliance, he acted without any instruction from Mrs. Monroe: Dylan raised his knees into the air, angling his butt out for easier access.
"Wha-?" His voluntary, submissive act caught her by surprise. "Oh, no… I got way too good of a boy for me, didn't I… ♡?" Her look of shock was quickly replaced by one of pure joy. "I knew you were the sort of stud who could make a woman like me fall in love…!" Mrs. Monroe buried her mouth against his, aggressively intertwining their tongues together outside their lips to the point of strings of spit dripping down onto his erect cock.
At the same time, instigated and emboldened by the way he presented his ass for her, she started fingering him faster.
Too fast, in fact, making his moans of pleasure become once more mixed with groans and grunts of pain. "Khhh…! Nghh…!"
Nevertheless, Mrs. Monroe no longer cared, far too engrossed in the act of fucking his ass with her finger. Instead of slowing down, she inserted one more finger into his hole; Without waiting to build up the room and elasticity needed, she started burying them all the way to the knuckle each time, effectively turning her gentle fingering into light punches against his asscheeks.
"Khhh…!"
"Ah, that's it, that's it… ♡! I love the way your ass is coiling around my fingers…! You like it, don't you, Dylan… ♡? Come on, say it to me… ♡!"
"I-it feels good…!" He struggled to speak past his tensed-up midriff. Every muscle in his body contracted harder and harder to deal with the fingers tearing his insides apart.
"This is not that much… It's just two small fingers…! You can't be getting all agitated just yet, okay…? I want to have so much more fun with you… ♡!"
Her words scared him slightly.
Mrs. Monroe easily perceived that. "I love it when you look at me that way… ♡! Is it scary to let me take charge of your butt…? But it feels good, doesn't it…? I can tell from your face… But even better, I can tell from your dick…!"
"Nghh…?" Dylan finally built the gall to look away from her eyes and toward his penis. "Ghhh…!" Unbeknownst to him, the pleasure was so strong that his dick flailed about wildly for a while now, rubbing against her shirt – and even a bit against her revealed midriff - due to how little distance there was between their bodies. Because of the overwhelming feeling of burning pain and pleasure coming from his ass, Dylan had failed to notice such a thing; Now that he was aware, new waves of pleasure struck him.
Yet, as if to taunt him further, Mrs. Monroe moved her body slightly away, no longer allowing his dick to accidentally rub off on her. "None of that with me, okay… ♡? I'm going to ingrain far better pleasure in your body… A boy like you needs to cum from HERE…!" She curved her fingers into his anal walls and pushed against his stomach, making his entire being tremble in painful ecstasy.
It was enough to send him to the edge. "Nghoooooooooooh… ♡!" The longest, most feminine moan of his existence escaped his mouth. Dylan's eyes started twitching along with his swinging cock. With just a little more, he would-
"Let's stop for now." Mrs. Monroe pulled her fingers out without restraint, painfully scraping his insides. "I don't want you getting too carried away just yet ♡…"
"W-wait…!" Frustrated from stopping right on the verge of climax, Dylan rushed to grab his dick and pump himself to orgasm.
"Don't get too eager just yet…!" She grabbed his hand mid-air. "I still want to have a lot of fun with you… You wouldn't hurt me by betraying me like this, right?"
"B-but… Khh…"
"I promise it'll be worth it. Didn't you like it just now?" She brought his face to her cleavage and buried it in it while speaking. "My son only comes back tomorrow. Let's have lots of fun, Dylan ♡…" Realizing he had calmed down, she pulled him away. "Alright…?"
"F-fine… Okay…" The frustration on his face was quickly replaced with acceptance, and soon followed by renewed excitement.
"Hm… By the way…" Mrs. Monroe brought her two wet fingers to her nose and gave them a good sniff. "Ah… What a great scent… Just how I like it…" She inserted the two fingers into her mouth and licked them thoroughly while giving him a sideways glance.
Dylan was marveled at the woman's depravity. Innocent as he was, he had no idea that women could be so lewd. 'Even me… I didn't know I could like something as wrong as having my ass poked…! I-isn't this a bit too much…? What am I doing…? If anyone finds out… No, if Barry finds out… Or even my parents… This could be a big problem… This is super wrong… What will they think of me?! I betrayed my friend to have his mom stick her fingers up my ass?!' The more he thought about it, the more caveats he had about going forward with any of it.
While obsessively watching Mrs. Monroe devour her fingers, Dylan came to a decision: Things could not go any further. He was determined to stop everything here. 'I'll just open my mouth and say it…!'
"Puah…! This was great…! I forgot this wonderful taste, but I expect to get lots of it today…" She extended her hand toward Dylan. "Let's go to my bedroom." She ordered him.
"Okay!"
No amount of determination in his mind mattered when confronted with Mrs. Monroe's command.
Dylan was hopelessly magnetized to her.
***
The instant they went up the stairs and entered her bedroom, Mrs. Monroe closed the door behind them and inserted two fingers into his butthole without warning. "Nghh!"
"That's such a cute moan… ♡!" Mrs. Monroe curved her fingers into a hook and pulled up on his hole, forcing him on his tiptoes. "Come on, let's go to the place where the magic happens…" She pushed him along all the way to the bed, ultimately bending him over against it. "… Stay on your tiptoes for me, okay… ♡?"
"Y-yes…!"
"Good boy." This simple praise had already turned into magical words that made his heart race with happiness. Mrs. Monroe left him and walked over to a cabinet.
Dylan was beyond nervous. His main focus was on keeping his ass high while staying on his tiptoes, as ordered. 'Wh-why am I like this…? Isn't it the other way around…? I don't get it…' In his mind, Dylan tried to figure out what was about to happen.
Of course, such a question was no more than self-deception.
Dylan had enough brainpower to deduce what was about to take place, despite his inexperience and overall innocence.
However, if he let his mind think about it, he might chicken out. If he did that, Mrs. Monroe would be hurt and disappointed.
To ensure her satisfaction, Dylan lied to himself for as long as he could, internally playing dumb.
Well, it was not JUST for Mrs. Monroe's satisfaction…
…He was starting to get pretty curious himself.
"What do you think…?" Mrs. Monroe's suggestive tone captured his attention.
She was crouched before an open cabinet.
In it, there were dozens of strap-ons of different sizes and colors. Some even had different textures.
She traced her fingers around multiple ones while keeping her eyes locked with his. "They're pretty great, aren't they…?"
While observing her nimble fingers encircling the girth of several fake cocks, teasing him, Dylan could no longer lie to himself: Mrs. Monroe would buttfuck him with a strap-on.
"Th-they're great…"
She bit her lips, flooded with arousal over Dylan's easy approval. "Oh, you're just the best… I've found myself a hidden gem…! You won't run away now, will you…?"
"No…"
"Will you let me break your little ass open with my rubber cocks…?"
"Yeah… Go ahead…"
Confronted with what was about to take place if he did nothing to stop it, Dylan learned just how much of a good liar he was, but not because he accepted. Rather, because he had no idea how much he WANTED to accept it until faced with the direct invitation. He had deceived himself until the last moment.
His acceptance was ultimately completely voluntary. He could not lie to himself.
Dylan was obscenely curious about what it would feel like to have his rear dominated by the tall, powerful woman. While watching her fingers move around the fake selection of fake dicks, his eyes were wide open and bloodshot, hypnotized.
It was just a matter of formalizing which one she would use to obliterate him. "Which one do I take…?"
Breathing heavily, Dylan looked over each of the dildos. "Th-that one…" He pointed to the smallest white-skin-colored one.
"This one, then?" With a wide, sadistic smile, Mrs. Monroe grabbed one that was two sizes larger.
"H-huh? No, that one…!"
"Shhh…" She closed the cabinet and started strapping the fake cock to her hips. "…Men can always take two sizes bigger than they imagine. Probably much more. Don't you agree…?" She walked over and let the enormous fake penis dangle right in front of his face.
'NO, I DON'T!' Is what he wanted to scream, but her voice, body language, smell, and expression exerted far too much pressure over him, leading him to simply nod nervously. "C-can you… A-at least…"
"Hm…?"
"Y-you know… Take your clothes off…?"
"Oh…?" Mrs. Monroe giggled. To this point, she had yet to remove a single piece of clothing. The strap-on was strapped over her jeans. "…You want to perv on my juicy, mommy body, is that it, Dylan…?" She teased while blowing sweet air against his ear. "Young boys like you are just a lost cause, aren't they…? I've seen so many of you staring at me, crazy to get a good look at my ass…"
"I-it's because you're very gorgeous…!"
"Hm… I'm afraid it won't be happening either way." She suddenly slapped his ass hard while smiling straight at his face. Witnessing his yelp of pain made her chuckle. "I only fuck good boys, and you wouldn't be a good boy if you were a perv. You're my good boy, aren't you, Dylan?"
"Y-yes…!"
"Then no perving for you. But don't worry. I'll give you something much better." She brought her fake dick back, slapping his face with it. Mrs. Monroe once more chuckled at his groan of pain due to the strap-on's heavy weight. Then, she circled around the bed and positioned herself behind him. "You don't need to see my body either way. You're going to be spending most of the time looking either at the wall or bed…" She grabbed his long hair and harshly wrapped it around her wrist like a leash, and then pulled on it until his back arched to the point where he was looking up at her face. "…Or at my pretty green eyes."
"Hah… Hah…" Dylan felt something poking his ass. "I-isn't it too big…? A-are you sure…? Hah…" He lost control of his breathing and his entire body trembled; Whether due to excitement or nervousness, even he could not tell. Being bent over and arched under her grip made him feel tiny and submissive.
"Why don't we find out together…?" She tugged harder on his long hair, surprising Dylan with his newfound flexibility; His upper body was so arched that it was essentially perpendicular to the bed. Because of their height difference, it enabled him to easily maintain eye contact with her. "When it gets rough, just look into my eyes."
"D-do you mean 'if it gets rough'…?"
"No."
He shuddered. "I-is it so… I can relax by l-looking into your eyes…?"
"No." She used her other hand to reach around his face and insert two fingers into his mouth, hooking his cheek to the side until his tongue was forced out of his mouth. "…I just want to see what sort of face you'll make." Mrs. Monroe also breathed heavily, blushing in uncontrollable excitement.
"P-please… Take it easy…"
She did not verbally answer, but the way her expression contorted into a wide smirk was more than enough.
It was a trifecta.
Mrs. Monroe started moving her hips without saying anything. Her fake cock was so heavy and well-angled that it did not bend even slightly. Instead, his hole forced itself wide open to accept it.
The insertion took an eternity.
She did not slam forward. Instead, her hips gradually moved against his, pushing inch after inch into his butt. The millisecond that the tip of the tip entered his anal walls, Dylan's body spasmed frantically and his teeth clenched aggressively. These were not voluntary actions; They were mere defense mechanisms by his body.
"Khhhhh…! Nghhhh…!" In the process of clenching his teeth, he accidentally hurt the two fingers Mrs. Monroe had in his mouth. Similarly, his rectum would likely have crushed the glans inside his ass if they were not a literal lifeless object.
Fortunately, Mrs. Monroe was a forgiving woman. Though her face contorted in pain from having her fingers bitten, she did not punish or scold him; In actuality, she seemed to love it, looking at him with an intense lust-filled gaze.
His insides squeezed hard on the strap-on, slowing it down with every inch gained. Though Dylan was the one crushing the toy, he was the one feeling crushed, a mere consequence of how its sizable girth stretched his walls out. 'This thing is way too big…! It doesn't fit…! Oh, God…! And my ass is covered in lube from earlier…! Khhhh…!'
"I love the way you're struggling… Keep doing that…! Make it fun for me…!"
"E-easier…! Take it easier…!"
"Absolutely not! You're a big boy, aren't you? Just take it!" She removed her fingers from his mouth and slapped his ass violently, sinking her small hand against his flesh, leaving it branded. The sharp pain from the slap was so significant that it masked the excruciating feeling of being hollowed out by the strap-on.
Consequently, his cavity loosened up and allowed Mrs. Monroe to gain an extra inch.
…And she took note of that fact. "Ah, so that's the trick with you, is it? Your cute ass becomes more agreeable if I give that masochistic brain of yours something else to focus on…?"
"N-no…! Khh…! It's tearing me apart...! I'm going to split open, Mrs. Monroe…!"
Instead of addressing his worry, she tugged on his hair as punishment and then pinched his nipples with her free hand, drawing multiple soft gasps of pain. "Ghhhhh…! Khhh…!"
Once more, his hole loosened up and another inch pushed in.
"Too much…! It hurts…! It hurts…! Khhh…!"
"It's only because it's your first time. Come on, you'll power through for me, right…? You can take it, right…?" She brought her mouth to his ear and stopped abusing his nipples, instead sliding her free hand all the way down to his lower body; Her other hand simply refused to let go of his hair-leash. "You were so happy earlier… Remember how this big cock of yours nearly pumped out a biiiig load on my face…? Size matters, you know…? If you felt so good with just two fingers, imagine it with a fat cock like now. You'll be going nuts with pleasure soon enough…"
"But it doesn't fit…! Seriously…! I can't move…!"
"Come on, be a strong boy for me…" She repeatedly teased his throbbing member by running her fingers around his inner thighs and crotch but never directly touching it. "Isn't it fun that you're suffering a little…? Challenge makes a man grow, you know? I'm teaching you to be a tough, strong man in a way that your real mother never could…" While teasing him, she forcefully got another inch into his ass. Over half the dildo had made its way in already.
…And yet, Dylan could not cope with the idea of a single inch more. "I can't… I can't take it…! Ghh… It's breaking me… God…!" His voice turned guttural due to his abs' inability to stop squeezing. Soon, he also started running out of breath due to the tension accumulated in his body. "Out… Just for a bit… I need a pause… Ghh…"
"Do you…? But your dick is twitching so much… Look…" She loosened her hold on his hair, allowing his head to fall forward and look down.
Indeed, his cock was harder than he had ever seen; Or felt, for that matter. It burned an awful deal, covered in far more veins than he knew was possible. Dylan did not understand why, but it most certainly did not feel good. His mind was fully immersed in the pain of having his rectum brutally stretched out.
Soon, the pain took second place as his mind immersed itself in a more urgent matter.
Dylan needed to breathe, but it was impossible without at least a bit of physical relief. No amount of effort could get his muscles to relax, leaving him clad in veins while struggling for air despite no direct pressure on his neck.
"Oh, your face is turning red…? Let me see from a bit closer…" She pulled on his hair, forcing his back to arch again. "Ah… I've never seen a man running out of air without grabbing his neck. This is amazing…" Mrs. Monroe superficially pushed her nails against his skin and traced the entire distance from his inner thigh to his neck, gently grabbing it. "You're so tense, dear… Why don't you just take a breath, hm…? But I do like feeling these neck muscles popping out…"
"I can't… Nghhh…" His head turned dizzy. Though he did his best to keep his eyes focused on her face – purely out of a desire to please the dominant, sadistic woman – they inevitably became unfocused as his consciousness slowly phased out.
Just as his mind was going blank, the tension in his body miraculously let up. Instinctively, he gasped for air immediately. "Hah…! Hah…! Aaah…!" It took him several deep breaths until his face turned back to its normal color. "Huh…? What happened…?"
"I did what you asked ♡."
Dylan could not properly look behind him, but could feel a massive difference in his body; Namely, the lack of a massive object as deep into his anus as before. Mrs. Monroe still had a small chunk of it in, but most had been pulled out.
"Aren't you going to thank me…?"
"Thank you… For letting me breathe…"
She forced his head back once more and connected her lips with his. "You're gonna have to brace yourself and behave like a strong boy for me now. I don't want to hold back anymore."
"H-huh…?"
"This ass is just too perky for me. I wanted to bottom out before I really started giving it to you, but it's fine this way. Halfway in gentle and halfway in rough isn't too bad, is it?"
"W-wait… S-seriously…! I can't-"
"Do you want me to stop?" She cut him off with a dangerous question.
Despite the horrible pain, the answer was evident. "No."
"Then just take it like a big boy ♡." Mrs. Monroe began making out with him.
…And, while he was distracted by her tongue embracing his, she thrust her hips forward.
This time, it was not gentle or steady.
Mrs. Monroe slammed forward with every bit of strength available in her body's sturdy posterior chain.
It was then that Dylan realized how naïve he was acting before. It made sense that Mrs. Monroe cared little about his complaints of pain or limitations; She understood him better than he understood himself.
After all, it turned out that his butt and body could absolutely handle the massive rubber cock… For better or worse.
"NGHH! KHHH! UNGH!" He grunted with wide-open eyes while sharing tongue kisses with Mrs. Monroe. Neither of them blinked. Her eyes communicated sadistic delight at seeing his face contorting itself. Meanwhile, his eyes communicated masochistic pleasure at being dominated and getting his ass mercilessly fucked.
'P-pleasure…?! W-wait…! Nghhh…! Oh, fuck… Is this…! Ghhh…! Actually…! Mnghhh… Feeling good…?! Oooooooh…!' His eyes twitched irregularly as his brain acknowledged the crude truth.
It started feeling good. In truth, Dylan's mind and body had been bathing in pleasure all this time due to the direct, vicious stimulation. However, the pain of having his hole stretched out so badly completely overwhelmed any capability he had to feel it.
Now that he had grown mildly accustomed to the sensation of a hard, foreign object deep into his ass, the pleasure started to seep through the pain.
With it, came increasingly animalistic grunts. "Nghhhhhh…! Ghhhhhh…!" It took everything he had to maintain a steady pace of breathing while dealing with Mrs. Monroe's ruthless thrusts. Though only half her fake cock had penetrated him, it felt like it was so far in that his lower stomach was being directly battered. Naturally, such a thing was fictitious, but it was his mind's way of interpreting things.
"Hah ♡… Look… ♡! It's flailing again… ♡! Seeing a big, fat cock swinging without a single touch is so fun… ♡!"
To let him see what she meant, Mrs. Monroe once again loosened her grip on his hair. Dylan's cock swung around far more than during the finger-fucking on the sofa earlier. New veins had appeared on it, showcasing how much pleasure he was drawing from being buttfucked and dominated by the tall, mature woman.
Turned on by the increasing pleasure, Dylan moved a hand to grab his dick and pump himself to orgasm. Just as he was about to grab the flopping target, his hand was caught mid-air. "H-huh?!"
Mrs. Monroe caught it and restrained it behind his lower back. "No touching yourself… ♡!"
"H-hang on…! Nghhhhh!" She punished him by descending several slaps against his ass, branding his rear globes with the shape of her feminine hand. "I need to…!" In a show of urge-driven defiance, he tried to grab his dick with his other hand, only to be stopped again.
Mrs. Monroe easily restrained both his wrists behind his lower back. "If you're going to behave like a bad boy, I'll have to treat you like one, dear!"
"Khhh…! W-wait…!" With no hands to support himself on the bed, Dylan could not balance himself while solely on his tiptoes. The only thing keeping him in place with Mrs. Monroe's firm hold on his hair and arms. With each thrust, his body inched closer to toppling forward. "Nghhh! Khhh! Mnghhh!" In an attempt to regain some form of balance, Dylan tried resting his full feet on the floor, but it was an impossible feat because of the repeated hammering against his ass. Each time he tried to let his weight fall down, she rammed forward, denying his efforts.
Without planning for it, Dylan's entire body turned into a pendulum, bouncing back and forth because of his poorly-executed try at balancing himself. 'Th-this is even worse…! I-I thought having my ass fucked was shameful…! But…! Having my entire body at her mercy…! Is so much worse…!' Dylan felt tiny and submissive under Mrs. Monroe's oppressive hold and fucking.
She, on the other hand, felt young and energetic. "Ah, this is such a tight ass…! I am so lucky to have met you, dear…! Breaking a hole like this open… It fills me with life…! And you're loving it too, aren't you…?"
He absolutely was. Even if Dylan felt embarrassed about being used like a cockhole for Mrs. Monroe, the burning on his cock and the dopamine-induced dizziness in his head irrefutably proved that he was deriving great pleasure from the situation.
Still, with his hands removed from the equation, Dylan felt an unexplainable need to maintain some modicum of pride, and his words were all he had left, leading him to provide a half-assed answer. "A-a little… Nghhh ♡!"
"Just a little?" Mrs. Monroe stopped with the strap-on packed into his rectum. By this point, three-fourths were regularly making it in with each vicious slam, though not without fierce resistance from his anal walls. "Come on, dear ♡… It's just us here. Nobody else is watching, and nobody else will know…" She looked deep into his eyes with a dominating smirk. "…Tell me that you're loving it."
"I'd love it more if you let me touch myself…!"
The words shot out of his mouth without any thought on his end. They were both equally surprised upon hearing it. Mrs. Monroe's wide-open eyes and mouth made him nervous. 'D-did I hurt her feelings?! I don't know why I said that…! I-I just wanted to be a little defiant! She won't even let me touch myself…' Dylan was quickly left exasperated as he saw her face gradually shift from shocked to arrogant.
"Oh, I see… We're an even better match than I thought. You're mostly a passive boy, but if I'm not rough enough, you try to ask for it, is it…? Trying to be a powerbottom…"
"H-heh…?"
"I don't mind…" She let go of his hair and quickly engulfed her now-free arm around his neck, squeezing it with a tight hold while still keeping his arms restrained behind his back using a single hand "…I love having an excuse to give it to you harder ♡. But if you want rougher, you can just ask…"
"Khhh…!" Dylan could not protest due to the tremendous pressure on his windpipe. Unwittingly, he had taunted Mrs. Monroe into becoming even more aggressive.
There was no better way to represent this consequence than the pathetic, feminine groans that recurringly spewed out of his mouth from then on. "Nghhh! Ghhhh! Uuuuungh!"
Mrs. Monroe started pounding him with a violence he did not know was possible. Using the hold on his neck and wrists as leverage, she slammed her hips forward with brutality, not caring about the limitations of his body. The room echoed with the excruciating sounds of their hips crashing together. His perky bottom flattened each time, unable to sustain itself against the strength devoted to each motion.
Within the span of a few seconds, she managed to bottom out in his ass through sheer force, or so he assumed by the gut-wrenching pain that soon overcame his senses. "Ghhhh! Mnghhhh!" The painful anal brutality vastly overshadowed the pleasure he felt before.
Just a few minutes ago, Dylan had learned that breathing was difficult when there was enormous pressure forcing his hole open.
That was a distant memory by now.
Trying to breathe with Mrs. Monroe's cruel pressure against his neck and her hips savagely clashing against his was INFINITELY more difficult. His eyes quickly rolled into the back of his head while drool leaked out from the gaps of his clenching teeth at a mad pace. Dylan's face turned a dangerous shade of red, but she did not slow down for even a second.
In fact, with every few thrusts, Mrs. Monroe gained speed and became more heartless. "It's all the way in, dear…! I love it…! I wish I had a real dick to feel this, but just looking at your face is enough…! I wish I could see your eyes…! Come on, don't you want to roll them back for me…? Let me see the struggle in your eyes! What if I do this…?"
She pulled out slightly, leaving only half her cock inside his ass.
It was still a painful, brutal length, but Dylan had grown somewhat accustomed to it. Without the frenzy of her thrusts and with a slightly looser chokehold on his neck, he managed to recover a semblance of sanity, bringing his eyes back to normal.
"So cute… ♡!" The millisecond their gazes connected, Mrs. Monroe grinned and started thrusting again; At the same time, she restricted his neck harshly, constricting his airways.
"Nghhh…! Khhh…!" Without access to air and strained from the bestial fucking, Dylan soon lost all strength in his body. Unable to collapse backward because of Mrs. Monroe's violent onslaught, he soon tipped forward. His body turned into so much dead weight that she lost her own hold over him, prompting his face to sink into the sheets, staining it with drool.
Initially, the prospect of having his sight turned dark due to his face being buried into the bedsheets did not particularly please Dylan – not that he had much leeway, considering Mrs. Monroe immediately climbed onto the bed with one leg and continued to hammer at will.
Soon, though, he realized there was one big advantage: By merit of collapsing onto the bed, his hips also got very close to the sheets. In other words, each time Mrs. Monroe crashed her thick hips against his, his lower body jerked forward enough that his desperate cock rubbed against the dry fabric.
It was not a soothing feeling, but it was the direct stimulation he yearned for. The double-ended stimulations transformed his grunts of pleasure into guttural groans of euphoria. "Nghooooooh…! Uuuuuuuungh…!" It was such an intense feeling that he was able to groan even with her arm squeezing his neck and the sheets choking his mouth.
"You look so cute all smashed up…! I love submissive boys like you…! Nghhh… ♡!" Mrs. Monroe's own voice grew more and more strained, but not just out of physical stress; The strap-on intimately rubbed against her pussy lips as she fucked Dylan's ass. In other words, she derived immense mental pleasure from dominating him and intense physical pleasure from having her lower hole stimulated by the strap-on itself.
Dylan's body relaxed whatever little it could because of the direct stimulation that the bedsheets provided to his glans. This allowed Mrs. Monroe to more easily – and violently – stir his anal walls.
For a few minutes, their sexual encounter proceeded without surprises. Mrs. Monroe was pleased with his full submission, and Dylan distracted his mind from the pain by focusing on the friction against his cockhead.
…And then Mrs. Monroe realized what was going on. "Hmmm…? Dylan, are you being a naughty boy…?" She stopped thrusting after hilting her full fake cock into his anal walls. "I got so distracted by your cute booty that I didn't notice it, but…" She grabbed his hair like a leash once more and pulled on it until his upper body was far away from the bed, exposing his precum-drenched cock. "…You got crafty even while being choked… Did you want a bit of tugging that badly…?" Mrs. Monroe painfully scratched him all the way from his chest to his legs. "Would you like a bit of direct stimulation…? Is that it…? Is your dick so horny that you would behave like a bad boy just to get a bit of a rub in…? Even if it makes me upset and disappointed…?"
"Khh… S-sorry…" Despite Mrs. Monroe's taunting, she did not pull out of his ass. The deep internal pressure was killing his mind's capability to respond properly.
"If you beg me, I'll give you what you want ♡."
"Huh?"
"If you beg me, I'll give your dick all the direct stimulation it needs ♡." Mrs. Monroe bit his ear while teasing him. In similar teasing fashion, she circularly moved her fingers around his inner legs, aggressively suggesting she would touch his cock and balls at any moment.
Dylan immediately imagined her jerking him off… While destroying his ass and verbally degrading him.
…
Why did his imagination include Mrs. Monroe abusing his ass…? Moreover, why include her verbally humiliating him?
He tried to envision the scene again but with only the handjob.
It did not entice him even remotely as much.
The ass destruction and verbal were part of the deal, at least in his mind.
"So… ♡?"
"Y-yes…! Please, I beg you…! I-I really need you to touch my dick…! Please!"
"Do you feel really close to the finish line, but can't get off…? Is that it…?"
"Yes!"
"You're wrong ♡." She whispered in his ear with a sadistic tone.
For a moment, Dylan thought she lied to him and did not intend to keep her word. Yet, she soon forced his body to turn around while keeping the strap-on stuffed deep into his rectum. "Khhhh…! Nghhh…!" The feeling of his body's axis gyrating while the hard silicon cock remained stiff in place made him quiver multiple times. "Hah… Hah… Y-you're really going to do it…!" A wide smile formed on his face as he realized Mrs. Monroe and he were now facing each other in a missionary position.
"No, no, no. All I said was that I'd get your dick some direct stimulation… I said nothing about touching it, dear."
"H-huh…?"
Mrs. Monroe climbed onto the bed with both legs and raised Dylan's lower body into the air to the point of them hanging almost beside his head due to gravity forcing them down. As it turned out, he was far more flexible than even he knew; Dylan was easily taken to a piledriver position.
He felt tiny and dominated before the imposing sight of the mature, tall woman and her fat fake dick packed deep into his ass. As embarrassing as it was, he felt a fervent urge to hide his face and body from her somehow. It was humiliating to be seen in such a compromising position.
Yet, of course, he did nothing of the sort.
Mrs. Monroe's huge cock was shoved into his body. Right now, it was his job to make her happy by taking her at all costs. "Wh-what are you going to do…?"
"What I was already doing ♡." Mrs. Monroe pulled her hips back slowly, intimately gouging his bumpy anal walls.
"Nghhhhh…! Hah…! B-but you said you'd touch my dick…!"
"No. I said I'd give it direct stimulation. That's exactly it. Try not to go too crazy, okay…?" She giggled and thrust her hips as strongly as she could.
"Uuuuuuungh…!" Dylan understood her intentions right away.
With her violent lunge, his ass flattened itself against her hips, making his lower body shake and bounce as a mere result of physics.
Consequently, his hard, throbbing, desperate cock swung up.
And everything that goes up…
"Ooooooh! Nghh! Khhh! Ghhh!" Dylan turned into a machine of frantic groaning because of Mrs. Monroe's animalistic, heartless thrusts. She pounded his ass without an ounce of consideration for his inexperienced status. Each time, his cock swung up and then descended at full speed against his lower abs, producing loud wet slapping sounds due to the abundant precum. With his glans wet and sensitive as they were, this resulted in a tiny bit of stimulation.
That said, this stimulation brought zero pleasure; Just pain. It was akin to having his cock repeatedly harshly slapped hard, but with no hand involved. "Khhh…! Ghh…!"
"Do you see what happens when you're a bad boy… ♡? Nghhhh…! Now your penis is getting punished by your own body! How does it feel?"
"It hurts…! Hooooh…! Fuuuuuuuuck…!" Dylan gritted his teeth to suppress his squeals. "My ass is going to break…! Guuuuuuh…! My dick too…!" His eyes rolled into the back of his head from the pain. The sound of his cock smacking loudly against his abs gradually hypnotized his mind.
"Focus on me, dear…!" Mrs. Monroe reached down and slapped his face, regaining his attention. "And don't go shutting your mouth down…! Half the fun is hearing boys like you screeching while finding out how much you'd rather have your asses broken than fucking a tight pussy…! Nghhh… ♡!" She forced his mouth open by inserting her fingers into it, pulling on his jaw. "Ah, that's it…! That contorted face…! I love it…! Now that I'm bottoming out each time, it's hurting, isn't it…? But it'll feel good soon, don't worry…!"
"Khhhhh…! Hooooh…! Ooooooh…!" Without recourse, Dylan maintained eye contact with Mrs. Monroe while she brutally squashed his ass in frenzied, ruthless hammering. "P-please…! A different position…! This one is too much…!"
"It reaches deep, doesn't it?! It's fine! Just focus on the pleasure…! This is the best position…! You're about to find out why…!"
"I can't…! It hurts…! My dick's burning…!" Dylan panted due to the physical exhaustion imposed by having his ass and dick abused so viciously.
"Ah, what a crybaby…! Just a few minutes ago, you were totally getting off. I bet you were about to cum too… Let me help bring you back to that state. Try not to go too crazy afterward…" With a chuckle, Mrs. Monroe stopped thrusting and, to his surprise, pulled out.
Without an enormous cock stretching his ass out, Dylan felt like a new person. Though his ass felt hollow and he could vividly feel his asshole blinking, it was still a heavenly sensation of relief. "Hah… Hah… Hah…!" He had forgotten what it felt like to breathe at ease.
"Don't celebrate just yet, would you? This thing is going right back in." She raised the cock high for Dylan to look. It was soggy in lube and bodily fluids. However, that mattered little. His mind focused on something else.
Its girth.
"Th-that entire thing was inside me…?! All of it…?!"
"That's right." She let it freefall on his ass, making his body shudder in pain due to its heavy weight. "But don't get too distracted now. Let's see here…" Mrs. Monroe grabbed her dick and stroked it a few times, getting her hand lubed up. Then, she inserted four fingers into his ass.
"Khhh!"
"No crying!" She quickly gave his ass a cruel smack, marking it with her hand. "Four fingers are nothing compared to how gaped-open your little cockhole is now. Be a strong boy for me, okay? Now, focus on this…" She moved her fingers inside his anal walls.
At first, Dylan did not understand. All he did was flex his abs to keep himself from letting out any more embarrassing whimpers; He did not want another punishing slap from Mrs. Monroe.
Then, a sharp jolt climbed his body and made him quiver for several seconds before stopping. "Wh-what was that…?! Nhghh…!" It happened again… And again… And again.
They were not sharp jolts of pain.
Rather, they were of immense, mind-numbing pleasure. "Wh-wha…? Nghhhhhh ♡… Oooooooooh ♡…" Dylan's body immediately relaxed, letting out long, loud guttural groans of pleasure. 'It's like the sofa again…! Oh, God, it feels gooooood…!'
"Does it feel good…?"
"Yeah… Guuuuuh…" His head muddied up from the overflow of ecstasy.
"Do you know what this is…?"
"No… Uuuuuh…" No amount of focus could keep his lips from expelling repeated, low-pitched groans.
"It's your prostate. When a pretty boy like you gets poked here, it feels good. Most men have no idea about how good this feels. Thankfully, you have me to teach you, right…?"
"Ghhh… Y-yeah…"
"You're a healthy young boy, aren't you? How often do you masturbate…?"
"Khhh… A few times a week… I think… Uuuuuuh…" His eyes twitched as his legs constantly shook under Mrs. Monroe's skilled rubbing of his sensitive spot.
"And what feels better…? Tugging your own dick like you're some sort of stupid cow, or getting your little hole here massaged by my fingers?"
"Ghhh… Nghhhh…" Dylan did not want to respond out of leftover pride but it lasted little. Once Mrs. Monroe recognized his reluctance and smacked his face and ass, he crumbled easily. "Y-your fingers…!"
"How much better are they?"
"W-way better…! Khhhh…!"
"Good boy…" She caressed his face to reward his submission. "And, just out of curiosity, to what type of porn do you masturbate, hm…?"
"I-I don't watch porn… Ghhh… I just used to think of… Cute girls in my class…"
Mrs. Monroe raised her eyebrows after hearing him. "Used to…?"
"W-well… U-uhm… Nghhh…"
She pressed harder against his prostate, making him shake in unsustainable pleasure. "What have you been masturbating to recently…? I want to know."
Dylan mentally stalled for several seconds, embarrassed of the truth. With each second that he hesitated, Mrs. Monroe intensified the stimulation of his prostate, to the point where he started hyperventilating due to excessive ecstasy. "Y-you…! I masturbated thinking of you…!"
Mrs. Monroe promptly blushed with a sadistic smile on her face; She already expected his answer, but hearing it was another thing. It would have been cute if not for the fact that she stood up on the bed and aligned her fake dick with his asshole once more. "Focus on this."
"Huh…? Nghhhh… What…?"
"This feeling!" She crushed her fingers against his prostate. "Focus on this feeling. Got it?"
"G-got it…!" He had no idea what she meant, but did his best to keep her mind and body focused on the pleasureful sensation.
One second later, when Mrs. Monroe once more plugged his ass to the brim with her strap-on, he understood.
The pain was still very much present, but it was nothing more than background noise when compared to the main sensation provided by the attrition of the enormous cock shoved down his ass: The stimulation against his prostate.
By having it devotedly fingered for a long time, Dylan learned to focus on it; Now that she was pegging him again, he was able to immerse himself in the hard object crushing it far more violently than her fingers ever could.
…And far faster too.
Dylan's confession about masturbating to her spurred something deep in Mrs. Monroe's heart.
She started pounding him with an entirely renewed degree of brutality, annihilating his asscheeks in savage slams. Their voices were nearly entirely muffled by the loud sounds of their fleshes crashing together; If not for that, they would be hearing each other grunt like mindless animals.
The next several minutes were a blur. Dylan lost all sense of time, fully hypnotized by the mature woman passionately staring at him with a domineering gaze while fiercely churning out his rear hole like a toy for abuse. His brain became flooded with dopamine and endorphins, dropping any tinge of pride that existed before.
The intensity was so great that he entered a hyperventilating and quivering spree that seemingly lasted forever. Dylan could no longer remember what it felt like to breathe normally; Gathering air to endure the immense physical strain was necessary to keep functioning effectively as Mrs. Monroe's sex toy. His hard, heavy cock swung up and down like before, lightly bruising his lower abs due to repetition and strength; Yet, the pain no longer existed in his mind, completely drowned by the overwhelming pleasure.
This blur only ended when Dylan felt a massive rush of electricity climbing his body.
Of course, that was just a hazy, confused interpretation. There was no electricity present to shock Dylan.
It was an orgasm.
Having never felt an anally-stimulated orgasm before in his life, Dylan had no idea what to expect; He did not even know such a thing existed until the exact instant it hit him. "Nghhhoooooooooooh ♡♡♡!!!!"
The sensation was so powerful that he did not even think to close his mouth when cum started shooting into it. 'Huh…? What…? What's happening? I'm ejaculating…?!' His cock pulsated frenziedly, pumping the most explosive shots of semen that he had ever seen and felt in his life. As a consequence of his open mouth, several shots landed straight into the back of his throat, leading him to cough; The rest covered his face.
Nevertheless, he felt no shame over it for one simple reason: Mrs. Monroe did not stop spearing his ass for even a second. "Cumming in your own mouth on your first time… ♡! This is the best… ♡!" Her voice was unstable and her legs shivered wildly; Mrs. Monroe was having an orgasm of her own, turning her hip movements into sloppy thrusts, but never slow. "I've ensured a bright sexual future for you… ♡! You'll never feel good with anything other than this… ♡! But it's not over, is it… ♡?! When it's from the ass, it can go on for so much longer… ♡!"
"Huuuuh?! Nghhhhhh… ♡! What do you mean? Ooooooooh… ♡! W-wait, how is this… ♡?! Nghhhhhhh… ♡!" Dylan quickly understood Mrs. Monroe's point.
Over a minute had passed and he was still cumming.
Dylan had never orgasmed for more than a few seconds; He most certainly had never shot enough cum to fill his entire mouth up and gag, even if he had tried.
Yet, right now, he continued to release semen, and each jet was as strong, dense, and voluminous as the ones before it.
His penis refused to enter a refractory period. It was an endless cumshot.
The reality of an extended orgasm was both heavenly and hellish at the same time. Dylan felt his muscles contracting hard enough that they might tear off at any moment; His lower body burned in a way that suggested he might have been literally on fire; His cock and prostate pulsated mercilessly, sending his mind into a euphoric craze; Especially his prostate, which throbbed with sensitivity, swelling with an overflow of blood due to the aggressive stimulation.
It took an eternal amount of time for the orgasm to finally subside. By the end of it, Dylan's neck and facial muscles were horribly sore from relentless moaning, making it difficult to breathe or emulate expression. Similarly, his lungs and abs were exhausted from hyperventilating so intensely for so long. It was as if Dylan had sprinted for far longer than his body could handle.
"Ah, how cute… My dear boy is down for the count, is it…?" Mrs. Monroe teased him with a smirk. She was as sweaty as Dylan, but her body could clearly handle fucking for much longer, despite the veins and tensed-up muscles popping out on her skin. "You were such a good sport… I'm impressed that you could take on so much on your first time."
Dylan tried to say something, but all he accomplished was his face falling to the side.
"Oops! None of that!" Mrs. Monroe grabbed his head and quickly made him face her. "I don't want all that juicy spunk in your mouth dripping on the bed. It'd be such a waste…" She gently rested his body on the bed and lied down on top of him, turning their piledriver position into an intimate, romantic mating press. "Let me enjoy a bit of that, okay… ♡?"
"Nghhhh… Huh…?" Dylan barely grasped reality. Between his burning cock and overly-abused prostate and asshole, his mind had entered into a cum-drunk daze. Exactly because of that, he was very surprised when feeling his erect, throbbing cock being smashed under Mrs. Monroe's body as she brought her lips toward his for a long, passionate session of making out. She inserted her tongue into his mouth without an ounce of hesitation, swirling it around the pool of cum within.
For long minutes, they intimately kissed, embracing each other's tongues within the miasma of cum. Mrs. Monroe's technique was skillful; Dylan's was pure instinct due to his mind still scrambling from excessive euphoria.
At some point, without even realizing it, Dylan started grinding his hips against Mrs. Monroe.
"Oh, so you noticed it, didn't you…?"
"Mnhhm…? Huh…? What do you mean…?"
"You're still hard and horny. So much so that you're trying to hump me like a dumb animal… Or an excited pet."
'Wait, what…?' Mrs. Monroe's words brought him back to reality. 'She's right…! H-how can I still be hard?! Shouldn't I go soft after cumming?!'
As if she could read his mind, Mrs. Monroe smeared his ear with her cum-coated tongue and whispered in a seductive voice. "That's because you had a butt orgasm. You can have a tooooon of those before you stop cumming and go soft… And even then, you can still keep cumming if I force it enough."
"R-really…?" His heart, which had just started winding down, accelerated wildly, crashing against his chest. 'I-is she suggesting…?'
"That's why we're going to keep going, okay… ♡?"
"I-I can't…!" Dylan was so exhausted that he grew the boldness to say no to his mistress. "My body is dead…!"
"What about the promise you made me earlier…? Weren't you going to trust me all the way to show you heaven…?"
"Khhh…!" Her words made his heart ache with guilt. "B-but… I-I really can't…!"
"Shhh… It's okay…" She brought both her arms beside his face, isolating his entire worldview away except for her smile. "…I'll take it easy, okay… ♡? Just trust Melanie… I'll make you cum your brains out…" She paused and kissed him again, vacuum-sucking all the cum out of his mouth and into hers. Then, she loudly and explicitly gulped it all down, letting her tongue out to show him her dedication. "See…? Look what I just did for you. You can go a little bit longer for me, right… ♡?" Drool, sweat, and bits of cum dripped down her cleavage.
"I… Uhm…"
"You're loving getting pegged by me, right… ♡?" She started slowly moving her hips, once more scraping his anal walls with her fat, long strap-on.
"I-I… Nghhh…"
"You'll have tons of fun sex with me tonight, right… ♡?" She sped up a little more, now lightly slamming her hips against his perky ass.
"Mnghhh… I…!"
"You'll let me turn your ass into my cockhole, right… ♡?" She began pounding his rear with aggressiveness, leading to loud noises of wet squishing and flesh clapping together.
"Mnghhhh… ♡! Nghhhhh… ♡!"
"You'll be my good boy for as long as I want, right… ♡?" Mrs. Monroe crushed his head between her arms, using it as leverage to ruthlessly pound him. The bed creaked with her relentless, violent pummeling, making their bodies bounce lightly on the sheets.
At some point, Dylan must have submitted and said yes.
He knew that much because once Mrs. Monroe began her savage assault, it never stopped.
And if he never said 'yes' per se…
"Nghhhhh… ♡! Mnghhhhhhh… ♡!"
…His groans of pleasure most certainly did.
Not that they could be properly heard.
The room turned into an echo chamber of his asscheeks getting mauled by her vicious, lustful onslaught.