French Maid

Even though it’d been days since Jennifer agreed to join the party in an outfit of your choice you felt as if it was just moments before. And as you entered through the front door it struck you just how lucky you were to be in this situation. You just hoped that the costume you chose wouldn’t be too much for Jennifer.

“Elliot, you’re finally here!” - Jennifer suddenly appeared in front of you, still dressed in casual clothes.

“By the way, you look great!” - The woman said about the outfit you were dressed in.

You decided to put on a simple unbuttoned white blouse with a superman T-shirt underneath. Combined with a pair of nerdy glasses and slick black hair, you looked like Clark Kent, the iconic superhero character.

“Thanks.” - You said and looked around the inside of the house. - “Wow, the decoration looks incredible!”

The rooms were adorned with various Halloween themed ornaments like carved pumpkins or bat stickers and were lit by candles, giving them a gloomy look. It seemed like everything was ready for the party, except for Jennifer, who wasn’t dressed in her costume yet.

“Oh, is this for me?” - She asked, reaching out for the bag in your hand. - “You really should’ve given me more time to dress up.”

“Sorry…” - You apologized. - “It was hard to get something nice at the last minute.”

But Jennifer’s cheerful demeanor put you at ease quickly. - “Don’t worry, I was just joking. I’ll try to get ready as fast as I can, but until then why don’t you get comfortable and have some punch?”

And before you could say anything, she disappeared to her bedroom with the costume you had bought her.

Walking into the kitchen, you found Jake sitting at the dinner table and sipping on a glass of punch. He was dressed in a skeleton bodysuit, and had his face painted like a skull.

“What’s up, dude?” - He asked in a somewhat disappointed voice. - “I’ll have you know that my mom’s been nagging for the last four hours, telling me to hurry up and get ready instead of playing.”

You listened to him in slight confusion, but then he continued, looking at the clock. - “I’ve been waiting here for two hours now, when I could spend that time on getting my account to Plat…”

“Let’s be real, you’d get a bunch of inters on your team. And best-case scenario, you’d stay at the same rank you were before… Only bitches play SoloQ on Halloween.” - You said, and the two of you chuckled.

You sat down next to Jake at the table and poured yourself a glass of punch to sip on as well.

“So… what are you making my mom dress up as?”, Jake asked after a few minutes of silence.

“Uhh, just a maid outfit. Nothing special.” - You said half-lyingly.

However, it seemed like Jake noticed the nervousness in your voice. He raised an eyebrow as he looked at you suspiciously, having caught onto your obvious omission of truth. And the truth was that you had wasted so much time deciding on what you’d have Jennifer wear, that the only place that had any decent outfits left was a local sex shop. But, as inappropriate as that sounds, you did try and get the least erotic outfit there was, hoping that neither Jake nor his mother would realize.

Luckily, you didn’t have to wait long before you heard heels clacking against the wooden panels of the floor. And your heart ended up in your throat awaiting the moment Jennifer walked into the kitchen.

Any worries that she wouldn’t even show up in the costume were completely dispelled when you saw the woman stand before you in exactly what you had bought and nothing more.

It was a black low-cut dress that left more cleavage open than you had ever seen on her before, and it didn’t even reach halfway to her knees. Her legs were wrapped in matching stockings that hugged the skin tightly and disappeared under a pair of elegant black high heels that Jennifer must’ve found in her wardrobe.

Looking back up, you noticed a pair of long and smooth white material gloves stretched from her hands up to the middle of her forearms. And finally, a French braid, resting on top of her head, making it absolutely obvious that her costume was that of a French maid, a very sexy one.

“Good evening, young gentlemen.” - Jennifer said in the utmost respectful manner, bowing lightly to the two of you.

“What the hell is this?!” - Jake shouted, as if he had just seen the scariest sight in his life.

A look of concern filled Jennifer’s face, when she heard her son’s words. However, she didn’t say anything, looking like she wasn’t sure what he was getting at.

“You can’t wear an outfit like th-“ - Jake cried out, but then he saw you looking at him.

You weren’t sure why Jennifer didn’t seem at all bothered by the rather skimpy costume she was dressed in, but you weren’t going to make her question it either. Actually, you were very happy with how she looked in it, and while Jake was protesting, you helped him remember that he couldn’t object. - “You didn’t forget the terms of our bet, did you?”

“I… No, I didn’t…” - He mumbled out at a lack of words.

“I think you look incredible, Mrs. Hartnett!” - You exclaimed, having dismissed your friend’s awkwardness around his skimpily clad mother.

“Oh, thank you, Mr. Anderson. But you can just call me Jennifer.” - Jennifer said, and her cheeks turned a little red.

Mr. Anderson? You can call her by her first name? This was certainly new, but maybe she decided to roleplay a little bit in accordance with her current outfit.

“Of course, Jennifer.” - You said in a nice, yet slightly joking manner.

“Oh, come on. Let’s go and watch some movies already…” - Jake suddenly commanded, putting a stop to the situation that was visibly making him more and more uncomfortable. However, while you followed Jake into the living room you couldn’t take your eyes off Jennifer who had stayed behind in the kitchen. Her voluptuous body barely fit in the set of clothes you got her, and you realized that her butt was mere inches away from sticking out from under her short dress.

Sitting on the couch, you and Jake started going through the DVDs you had previously prepared for the night.

“Okay, we’ve got Zombie Prom Night, Attack of the Killer Garden Gnomes 2 aaaand Terror at the Toy Store.” - Jake announced. - “Which one are we watching first?”

But truth be told, you didn’t even hear what he was saying. Instead, having focused all your attention on Jennifer who joined you in the living room with a bowl full of popcorn.

You couldn’t help but notice how her tits jiggled with each of her steps, and how they almost spilled out of her dress when she leaned down to place the bowl on the coffee table in front of you.

“Here’s a snack for you boys.” - She said in a cheerful but slightly quiet voice, as if she didn’t want to interrupt the on-going conversation.

Having waited for an appropriate moment of silence, she continued. - “I know it won’t fill your stomachs, though. So, I was thinking that I could order a pizza or cook something for you.”

Looking slightly annoyed at his mother, Jake answered first. - “Pizza’s fine, mom.”

But before she walked away to make the call, she turned to you. - “And you, sir? Would you like pizza too?”

“Yes, I’d love a pepperoni pizza. Thank you!” - You said, and Jennifer gave you a warm smile, before turning away and walking back to the kitchen.

Keeping your eyes glued to Jennifer’s wide hips, you thought about the bizarre roleplay the woman was engaging in with you and Jake. You couldn’t help but feel like there was more going on than just a simple play. But, with the mother’s bubbly personality, it was safe to assume that she was just teasing you about the choice of clothes.

“Hey!” - Jake’s voice put you out of the trance.

“Wuh…” - You mumbled out, unaware of what he wanted from you.

“I asked if we could watch Terror at the Toy Store first.” - Jake looked at you with an annoyed expression.

“Uhh, sure…” - You answered, still taken aback by the view of his mother’s backside.

With the movie about to start, you got comfortable on the couch, pondering over Jennifer’s hot body.

You’d been ogling her for the last ten minutes, and she hadn’t done anything about it. You would even go as far as to say that her smile got a little wider when you did. Of course, this was out of character for the modest and proper woman that Jake’s mother always had been. But perhaps, since you were the one to choose her costume, she was happy to give you a good look at it. Or perhaps she wasn’t aware of what it was doing to the mind of a horny teenager like yourself.

“Mooom, the movie’s about to start!” - Jake shouted to his mother, who you assumed to still be in the kitchen.

And moments later, the woman showed back up in the living room, though she stopped at the entrance with her hands resting on the white apron that covered the lower front of her black dress.

“The pizza should be here in a while. Can I do anything else for you?” - She asked, looking between you and Jake.

“Just get on the couch and watch the movie, will ya?” - Jake was losing his patience with the unusually behaving mother.

You were surprised at how seriously she took the role of a maid, doing her best to serve the two of you. It’s not like she hadn’t prepared food or tended to her house before, but now she was taking it to a whole new level.

“Of course, sir.” - Jennifer said to her son and took a sit in the middle of the couch.

Your gaze kept alternating between the movie playing on the TV screen and the woman sitting next to you. Jennifer’s hitherto behavior didn’t let you focus on the horror, and you kept thinking about her eagerness to be of service.

You wondered if she would keep the act if you started asking her to help you with stuff. It would be fascinating to find the limit to her hospitality. And you couldn’t help but think of how to approach this best.

But finally, you decided on a slow way to begin the test.

Holding up a glass, empty of punch, you said out loud. - “Shoot, looks like I finished my punch already.”

“Well, go and ref-“ - Jake started saying, before getting cut off by his mother’s movement.

“Let me take care of that for you, sir.” - Jennifer took the glass from your hand and walked to the kitchen, paying no attention to the movie she had just been watching.

Not a minute later, she came back in a quick step, and handed a refilled glass right back to you. - “Here you go, sir.”

Well, it looked like she had no problem missing parts of the movie just to relieve you of something as simple as getting a drink from the kitchen. What’s weird though, was how casual she was being about it, not teasing you or making fun of the situation at all. Maybe it was time to ask for something more unusual.

Leaning over to the MILF on your side, you said in a quiet voice so that Jake wouldn’t hear. - “Hey, Jennifer…” - She instantly turned towards you, happily waiting to hear what you had to say. - “My feet are a little sore. Would you mind giving them a massage?”

Having expected her to refuse or straight up laugh at your question, you were totally surprised when she gave you a knowing smile and agreed. - “Of course not. Please, sir, take your socks off, and lay your feet on my lap.”

Stunlocked for a few seconds, you reacted to her words with a delay. But as soon as you realized that she was serious, you ripped the socks off and nearly kicked the woman’s legs with your soles. And just like that, Jennifer began massaging the area between your toes and the sides of your feet with her gloved fingers.

The material felt very nice in touch with your skin, and even though you lied about your feet being sore, you felt the massage bring them even bigger comfort than you could’ve imagined.

However, the massage was soon put on halt when Jake noticed what was going on and protested. - “Mom, are you seriously rubbing Elliot’s feet?!”

Getting caught by Jake caused you to instinctively take your legs off and put them back on the floor. And a mild feeling of guilt washed over you. Though, Jennifer looked confused and remained completely composed while her son accused her of doing something inappropriate.

“I’m not sure I see the problem, sir. If you wanted me to give you a foot massage too, you could’ve just asked.” - Jennifer proclaimed, not losing any of her cheerfulness.

“What? I don’t want a fricking foot massage!” - Jake shouted in annoyance and confusion of his own. - “And what’s up with the ‘sir’ stuff? You’re creeping me out, mom!”

Jennifer seemed to need a moment to process what Jake was asking of her, but soon she spoke with understanding. - “I’m sorry if I made you uncomfortable. If you’d like me to, I can call you by your name.”

His mother’s words hadn’t put Jake at ease at all, but he looked like he was tired of the absurdity and answered. - “Yes, I’d like that. Thanks…”

And just like that, you all got back to watching the horror movie in silence. At least until the doorbell rang, signaling that the pizza was here.

Jake paused the video as Jennifer went for the front door, but she assured him that the two of you could continue watching without her. And Jake did so without any objection.

Five minutes had passed since the doorbell rang, and Jennifer appeared in the living room with two plates. - “Who’s hungry for some pizza?” - She asked, proudly walking over to the couch to hand you the food.

“Margherita for… Jake.” - She announced in a careful voice, putting a plate full of slices in her son’s lap.

And then she walked up to you, slowly leaning forward with the second plate right below her sizable chest. Her tits wobbled erratically, only constrained by the smooth material of her dress that barely kept them from falling out. - “And a pepperoni with lots of salami for Mr. Anderson.” - She said, emphasizing the word salami when she noticed you staring down her cleavage.

Having been caught red handed, you couldn’t find the right thing to say. However, it looked like no words were needed. Because Jennifer started moving away from your view, though in a very slow manner. It was as if she wanted to prolong the action of showing off her tits as much as she could. And with a wink, she returned to her spot in the middle of the couch.

Was Jennifer flirting with you? She had always been nice, and at times made flirtatious remarks towards you, but you shook it off as her being playful every time. Now, she practically swung her breasts right in front of your teenage face and even acknowledged it.

The night had certainly been more than you could’ve expected so far. But it was far from being over. And you realized it when Jennifer moved away from the couch again.

It was like she couldn’t sit in place for longer than a few minutes. There seemed to always be something that she had to do around the house, was it bringing you popcorn, getting the pizza delivery or, like this time, lighting up candles that had gone out.

Jennifer positioned herself in a way that her ass stuck out straight towards you. And with her knees unbent, she leaned forward over a bunch of candles that laid on a cupboard.

Your eyes almost popped out of their sockets when the woman’s short dress ran up her backside and revealed her thick butt-cheeks to your unsuspecting eyes. The view was at least a thousand times better than any horror movie ever could be, so your gaze followed the alluring movement of Jennifer’s buttocks without drifting away anywhere.

This was the first time you got to see what the MILF kept under the dress, and you weren’t disappointed to find that she had chosen a thin black thong that got so lost between the mounds that it had taken you a few moments to even notice it. The small garment hid away the hole that your best friend, who was sitting at Cross C’s main character’s dick length, slipped out of around eighteen years ago.

Speaking of whom, Jake was luckily very absorbed in the slasher playing on the TV screen, and so he didn’t notice his own mother basically giving you a lap dance. But what you hadn’t taken into account was the garlic sauce drooping off your pizza slice until it ultimately fell right onto your pants.

“Shit!” - You groaned as the sauce splattered in a spectacular fashion. And now a huge white blob decorated your black elegant trousers. Your cry got the attention of both Hartnett’s, and everyone was staring at the dirty crotch of your pants.

Jake face palmed his face briefly after he noticed what you’d done. But Jennifer did something much more unexpected.

She rushed towards you, and immediately tried to take your pants off. - “Come on, let me wash them for you!” - She basically begged when you instinctively kept yourself from getting stripped in the middle of your best friend’s living room.

“Woah, woah, wait.” - You said, trying to keep the over-enthusiastic Jennifer away from yourself. - “I can handle it by myself.”

Making your way towards the bathroom, you noticed the woman follow right behind you, clearly having not taken a ‘no’ for an answer. - “Please, sir. I’ll do it for you. You just go and enjoy the movie.”

“I told you, I can handle it, Jennifer.” - You assured her. - “Also… You don’t need to pretend to be a maid. I got your point.”

Your words caused Jennifer to go quiet for a moment.

“Pretend?” - She asked in confusion. - “But I am your maid, sir.”

What the hell was she on about? Did she hit her head while changing into the costume or something? She couldn’t possibly believe that she was a French maid to a dude her own son’s age. But then, she did do everything you asked of her and hadn’t really been her usual self ever since she had showed up dressed up as a maid.

“What… What do you mean?” - You asked carefully, unsure if she was playing a joke on you or not.

“Sir, you and Mr. Hartnett hired me to serve you at your Halloween party. I’m just trying to do my job and help you out in any way I can.” - She said, without giving a single hint of insincerity.

“We… hired you as a maid?” - You inquired, in disbelief at what you were hearing.

“A sexy French maid, sir!” - She instantly responded, correcting you about her true role.

This revelation made you fall back and rest your ass against the bathroom sink. You needed a moment to process what you had just heard. And you scratched your head as you looked at the skimpily dressed French maid who sat on her knees in front of you, ready to wash your pants.

“So, can I take these off?” - She asked, pointing at the stained trousers, buckled around your waist.

Curious where this would lead you, you nodded and watched her unbuckle the belt and lower your pants, all the while staying in a submissive position at your feet.

“Thank you, sir, for letting me help you.” - She said, visibly relieved that you allowed her to strip you.

However, when the pants were off, a big bulge in your boxers became the center of attention for you and Jennifer. - “It’s not what you thi-“ - You tried to defend yourself, but she cut you off.

“Oh my… Did my little show cause this?” - She asked, biting on her finger.

This was wrong in all the ways possible. You thought, unable to break your gaze away from the infinite abyss that created itself between Jennifer’s boobs squeezed together by her arms. Your best friend’s mother was casually commenting your hard-on while he watched a movie in the room across the hall.

“Would you like me to take care of it as well?” - Jennifer’s words made you **** on your own spit.

“What?!” - You blurted out, getting continuously surprised by the MILF.

A worried look filled her beautiful face.

“Sorry, did I say something wrong?” - She asked nervously.

This was absolutely insane! Jennifer Hartnett, the mother of Jake, who you’d been friends with for years, fully believed that she was some kind of maid, obliged to serve you, and apparently not just with household chores, but also by relieving your sexual urges?!

One part of you wanted to pull the stained pants back on and run away.

But it was just a small part, well, at least in comparison to the part of you that was responsible for buying her a costume in a sex shop, and the one that fantasized about fucking your best friend’s mother since you had first met her. And so, shoving aside the voices telling you to stop her, you let your horniness corrupt you.

“Of course, you didn’t say anything wrong, Jennifer. I was just…” - You paused, having had to compose yourself. - “I was just a little surprised, that’s all.”

Instantly, her expression turned back to the cheerful and eager one. The one you’d seen the entire evening, but only now realized how much it was hiding.

“Please…” - You said mischievously. - “Help me out with my problem.”

“Right away, sir!” - Jennifer exclaimed, and her gloved hands shot right for your erection.

The maid had been stroking your dick through the smooth material of her long gloves for a while now. With one hand rubbing along your shaft, she moved the other down to your taut balls. And with gentle yet energetic movements, she massaged all the right parts, effectively bringing you closer and closer to orgasm. But, as amazing as the handjob was, you decided to push your luck for like the tenth time this day.

“Jennifer?” - You asked, lightly grunting from the pleasure.

The woman, who had so far been very concentrated on your manhood, turned her gaze up to your eyes.

“Would it be too much for you to take my penis in your mouth?” - You carefully asked, not wanting this steamy situation to end early.

“Mr. Anderson, I’ll gladly suck on your penis. All you have to do is ask!” - Jennifer answered, completely oblivious to the absurdity of her words.

And just like that, the sexy mother of one opened her mouth in the lewdest of ways and gave the length of your dick a long wet lick. Finishing at the tip, she suddenly wrapped her red lips around it. And with the girth of your dick slowly filling her mouth, she pushed her face down until all of it was enveloped in her throat, and your pubes tickled her on the nose.

“Fuck.” - You let out. - “This feels amazing!”

But, by the time you finished speaking Jennifer started slowly bobbing her head up and down. Her lips travelled from one end of your dick to the other, easily sliding on the skin and not leaving a single spot without her saliva. But, perhaps the most stimulation you felt was caused by her tongue twirling and dancing around your shaft inside in a way that only a real slut could replicate.

Your dick wasn’t short by any means; however, Jennifer required no help getting all of it down her throat. And, as much as you wanted to watch her do her magic, you shot your head back in pleasure as the tip of your dick kept hitting the very back of her throat.

Gagging and slurping sounds filled the bathroom as the woman expertly blew you. However, through those lewd sounds, you suddenly heard knocking on the door.

“Elliot, are you there?” - Jake’s voice could be heard from the hall.

A chill ran down your spine as you realized that only a piece of wood separated him from witnessing his own mother give you a sloppy toppy. And it became even scarier when you didn’t even feel her stop.

But as the doorknob started to turn, you screamed out. - “Wait! I don’t have my pants on!”

The door that had just begun to open quickly shut itself back, to your relief.

“Sorry! You didn’t answer when I called you.” - Jake explained himself, clearly thankful that he saved himself the view of your bare dick. If only he knew whose mouth it was penetrating…

“Do you know where my mom is?” - He asked.

Yeah bro, she’s over here giving me head. You imagined yourself reply, having your mind clouded by the pleasure coming from Jennifer’s warm mouth over your dick. She was looking you straight in the eyes while your balls bounced off her chin, and you felt the orgasm get irresistibly closer with each bob. Until finally…

“I’m coming!” - You cried out, feeling your hot seed shoot straight down Jennifer’s throat.

However, the rush of pleasure abruptly crashing into your brain was too much for you to handle. And you felt the world rapidly rotate until all you heard was a loud thud, and everything went black.