Go with the Flow

Author's Note:

Hi All, I've been an avid reader at Lit for the past many years until very recently I decided to write one myself. So here is my first attempt at writing, hope you all like it. I'm open to suggestions and criticisms as I believe it will help me develop as a writer. Happy Reading!!

A big thank you to MaximusTheMad for editing.

All characters are over 18, the persons and events described are entirely fictional. The author reserves all rights to the story and its reproduction with the exception of Literotica.

*****

There were just two weeks left to my brother's wedding, when the responsibility of planning his bachelor party fell upon me. So, here's a little background into our lives - We were a family of three, Melissa (my mom), James (my elder bro) & me (David). Mom was a single mother as our father cheated on her when she was pregnant with me. Things got pretty nasty between them and they got divorced within a few months. When dad left us, mom was a single pregnant woman and with no job to support us. She started out as a waitress at a local restaurant to support our family.

Today, we're financially stable. Mom works as a receptionist at a fancy restaurant. My brother works for a big tech company and I'm in my first year of college. Our lives were pretty normal until James proposed to his long-term girlfriend Megan. This news brought a whole sense of joy and excitement in all our lives. We have known Megan for a long time; she's a pretty nice girl who's on good terms with both mom and me.

My brother and I have always been notorious pranksters and gave mother a lot of grey hairs. By now, both Mom and Megan were used to our mischievous behavior. The last prank was played by James on my 18th birthday party when he forced me to walk naked in front of all my friends with him chanting "Shame, shame, shame..." (I lost a stupid bet). So far, I hadn't been able to get revenge.

With the responsibility of planning his Bachelor party, a monstrous and wild idea had taken shape in my head. Until that day, our behavior had resulted into broken bones, burnt eyebrows and plenty of other weird stuff. But, this plan of mine was going to be the MOTHER OF ALL PRANKS.

MOTHER OF ALL PRANKS - was the craziest idea I've ever had and, more importantly, for it to be implemented it required a person's consent, that person being our very own 43-year-old mother; this was insane. Her agreeing to being a part of the prank was as crazy as the idea itself. Nevertheless, I wanted to give this crazy idea of mine a shot, but if Mom wouldn't pull it off then I had to come up with something else.

Melissa was a pretty cool mother. She was very open minded and understood us both very well. Also, she's had to deal with our troubles so she deserved a Nobel Prize for that at the very least. Since the divorce, she hasn't really been in a serious relationship. She's dated a little but never really found someone whom she could love and trust completely. Mom used to say that she was happy with the two men in her life and she didn't want anyone else.

Mom defined the word MILF perfectly. Our friends would never miss a chance to admire her as they considered her too hot for her age. She's a brunette and has emerald green eyes which really brings out her face. Mom's body wasn't perfect, but she had curves in all the right places. She was pretty voluptuous and wore a 34D sized bra. Over the years her hips and ass had grown a bit wider but they really suited her body. Her ass was her best asset and she knew it. Mom resembled one of the porn stars, Rachel Steele, although I've never thought of her in that manner. Her dressing sense was really professional and classy, yet people would still stare at her when she passed by. Her office attire would mostly be knee length skirted suits or pants. Her hair was kept up to her shoulder. She would usually wear pantyhose along with high heels which she carried off with style.

*****

By the time I returned from college, Mom was already home after her afternoon shift. James was at work, so I thought this was the right time to speak to Mom and try convincing her. I mustered up the courage and went to the kitchen.

"Hey Mom what's for dinner today?"

"I've cooked your favorite -steak with mashed potatoes. How was your day baby?"

"Wow Mom you're the best. There's nothing interesting going on at college these days. Just the usual stuff. Anyways, I've set an appointment with the caterer for the day after."

"Great. You're such a sweetheart, son. God knows what I'd do without the two of you. But, your brother is getting married now and soon he'll move out with his own family," she sobbed a little.

"Don't worry mom, I'll always be there with you, no matter what."

"Oh David. I'm so lucky to have you as my son," she kissed me on the cheeks and hugged me.

After she broke apart from the hug, Mom asked, "Anyways, what is it that's bothering you?"

"What? How do you do that? I never said anything."

"I'm your Mother for heaven's sake. Mothers always know when their sons have something on their minds. So, what is it, tell me."

"Actually, Mom there's something I haven't told you. On my 18th birthday, I lost some stupid bet and as my punishment James made me walk naked all around the house in front of our friends."

"Hahahahaha. David, I do know about it. It was lame but very funny."

"Huh? But, how do you know. Did James tell you?"

"No stupid. It was altogether my idea."

"Mom why the hell would you even think of something like that. I was so embarrassed that day."

"I'm so sorry dear. Your brother called me and asked for my help. You might not know this but back in my day I was myself somewhat notorious like the two of you. This was before I met your father."

"Mom, how many times have I told not to mention him?" I scowled.

"David, I know you hate him because he left us all. But the truth is I did love your father once. As a matter of fact, I've never been able to love anyone besides him despite all these years."

"C'mon Mom, I think you can do better. You're still young enough and I believe there would be someone out there for you."

"I don't think so David. I'm no longer interested in dating anymore. Besides I still have you here with me, so I guess I'm happy with just the only man in my life now."

"As you say Mom. I just want you to be happy."

"Yeah, I'm very happy David. So, what is it that you wanted to talk about?"

"Well Mom, now considering that you helped James with his prank, I've come up with an idea for his bachelor party. It's, uhhh, you know actually, I would um, sort of need your help..."

I told mom every detail of my plan and waited for her to respond. Her silence was killing me as I tried to pitch as convincingly as possible so that she'd agree to it. I was worried that Mom would think of me as some creep. But I knew that if somehow, she agreed to it, then this would have been the best possible way to get revenge on my brother.

"Mom you ought to help me. I need to get revenge on James for embarrassing me in front of everyone and also remember you owe me one now. PLEASEEEEEEE MOMMMMMMM!"

She sat quiet for a while and after some careful thinking said, "Honey, your plan's brilliant but are you sure it would work because at parties like these sometimes things do get out of hand. It's pretty risky if we are to go forward with this."

"Come on Mom, I've thought about it. There will be nothing to worry about. It's just James, me and a few of our close friends whom you already know. I doubt things will get out of hand. Please Mom?"

"Ummm, okay, I guess I owe you one, so yes, I'll do it. But things can't get out of control, do you get it mister?"

"I promise Mom it won't. James is going to have the worst Bachelor's Party ever. He'll remember it for the rest of his life."

*****

The Bachelor party was at one of the hotel's in our town. We checked in by seven in the evening and our room was decorated exactly the way I had instructed the hotel manager.

James was excited for the party, "David, I can't tell you how excited I am for today."

"Indeed bro. Although, I'm more excited than you. Just wait and watch- what all I've planned for you. This is going to be one hell of a bachelor's party."

"Thanks bro. But, nothing too extreme or else Megan would kill me even before we get married."

"Don't worry. Everything is under control."

"Yeah but, you know Tyler right. It's just that I hope he acts a bit sober today."

"Don't worry about him. I'll make sure he doesn't go off the rails. You should stop worrying about everything and just enjoy tonight. I've got this."

A little background about our friends who were at the party. There was Ryan, Shane and Tyler who were our best buddies. Since our childhood, we were a tight knit group and almost inseparable. Most of the times, we used to hang out at our place since, amongst all the parents, Mom was the coolest of all. Ryan and Shane were pretty decent enough but Tyler was a maniac.

The evening began with us playing games on the PlayStation. We also had loads of booze as I had asked the manager beforehand to stock up liquor in abundance. As we gulped down a few beers, I played some of our favorite rock songs to get us all started. Then came more booze as we had everything right from wine to whisky. I made sure I drank just a little as I could not get wasted like the rest. As the evening grew on us, it was edging closer to eleven when my plan was to be executed. By then we had consumed considerable amounts of liquor and everyone was a little tipsy.

I checked up on Mom by texting her, "Hey mom, is everything cool with you?"

She replied back saying, "Yeah baby. Everything's totally fine. I'm still getting ready for the party. By when am I supposed to be coming over?"

"Mom, I shall text you somewhere around 11. Please do get ready by then."

"Okay mister. Don't you worry about that. I shall be ready to roll when called upon."

The boys were all getting excited as I had promised them a stripper. But little did they know, that the stripper that I had hired was our very own mother. I had planned to ruin the best part of James's bachelor party by asking Mom to be the stripper. When James would realise that, then his whole party would come crashing down and that would have served as my revenge for the birthday party. I think mom agreed because she only had to make an appearance as a stripper but not actually strip in front of her sons and their friends. Maybe she thought there wouldn't be anything inappropriate with that and also, I had promised that nothing would get out of hand.

It was five minutes to eleven when I texted Mom, "Mom, it's time. You ready to roll?"

She replied back instantly with a YES.

I had booked the neighboring room so that Mom could get ready, turn up really quick at our door and avoid bumping into anyone at the hotel. I wasn't aware how she would dress for the party. Yes, Mom was supposed to be the stripper but I wasn't sure whether she would dress like one. I expected her to dress like a clown or maybe something else and then ruin the party by revealing herself.

There was knock on the door and I exclaimed, "Boys, like I promised, it's time to get ready for the main event! James, you are so going to love this."

As the door opened, there standing right in front of us in skimpy clothes was Mom. For a second, I doubted myself whether it was really Mom or whether she had ditched me at the very last moment and sent someone else. But that wasn't the case as she stood there striking a sexy pose. Judging by the silence in the room, I realised that nobody except me had recognised that the woman standing at our door was Mom. The reason behind was that she had very smartly disguised her face with a Volto mask. As soon as Mom entered, the temperature inside the room soared.

Mom was wearing a schoolgirl outfit - a tight white blouse along with a classic red plaid mini skirt. Her skirt hardly covered her bottom and thus displayed her butt cheeks. Mom had put on black fishnet stockings which covered from her toes all the way up to her mid-thigh and was supported by a garter belt. To complete her stripper attire, she had worn a pair of 6-inch high heel shoes. Her candy perfume had filled the entire hotel room with a sweet aroma.

"Hello boys. I'm tonight's entertainment. Now will everyone stop staring at me and tell me who amongst you is David?" said Mom in a very slutty but assertive voice.

Now someone pointed towards me as I was still standing in awe. Mom walked towards me and took my hands as we walked over to the little kitchen bar away from the boys.

"David, I need to talk you in private," she whispered right in my ears. Now this had created a tingling sensation in my body as I followed her away from the group.

"Listen I know you definitely didn't expect me dressed like this but I thought of improvising on your plan and playing it a little dirty. See, I felt guilty over what happened with you on your birthday, so I thought that maybe we could push a few boundaries but stay well within our limits. I'll act like a stripper for real but spoil the fun right on the edge so that we can screw your brother's bachelor party. Sounds good, doesn't it?"

After hearing out Mom's plan, I realised that it was really risky. But, if mom were fine with it, then there could be nothing as big as this that would spoil the party.

"Yeah, Mom, as long as you're comfortable with it, I'm all game." I nodded along but was still left mesmerised by how she looked tonight. I had never ever seen mom in such a sexy outfit before. It wasn't that she always dressed conservatively. She did wear revealing outfits where she displayed a little cleavage or where she wore short skirts that exposed her legs and thighs. But it was only on occasions like a date or a party. But tonight's outfit was as slutty as it could be. I thought that my brain was going all sorts of crazy and thought to myself SHE'S YOUR MOTHER, STOP GETTING WEIRD THOUGHTS IN YOUR STUPID MIND.

"Come on you two. Are you going to spend the whole night chatting away?" shouted Tyler towards us. "The groom expects to see some action now, isn't that right, James?"

"Yeah, David and Miss...?" blurted out James who like me was mesmerised by Mom but the only difference was that he like the rest didn't recognize her because of the mask.

"Miss? Hahaha. Dude she's a stripper, not your Miss. What's your name bitch?" asked Tyler.

"My name keeps on changing every night but tonight you can call me Victoria," said Mom.

I was surprised to hear Mom playing out the role of a stripper to such perfection.

"Okay Victoria, so please come over here and get the night started, will you?" asked James.

"Let's get the party started, boys." Mom gulped down a few vodka shots as she whispered in my ear "Just GO WITH THE FLOW. I'll take care of the rest."

I nodded and thought that Mom had it all under control. Although, I must admit that some part of me was really excited to watch Mom dance in that outfit of hers.

She handed me a USB drive asking me to play it on the music system and headed out towards the group. I followed right behind her like a little puppy would follow his mother, trying not to see her ass moving up and down in that short skirt of hers. But to no avail, I could not help but admire Mom's bottom. I connected the drive to the music system and hit the play button (on a long night which would eventually change our lives forever).

Everyone had settled themselves, forming a circle of chairs as Mom stood right at the center. Some hot dance music started playing as Mom started moving her body very slowly but seductively, making some naughty movements and giving kinky expressions. I would have never, even in my wildest of dreams, thought of seeing Mom like this, dancing seductively in tight skimpy clothes in front of me, my brother and our friends.

As she moved around across the circle of chairs seducing like a stripper, shaking her ass and juggling her boobs, I was so aroused at the sight of my very own mother that a sense of anger and disgust filled inside me. I had never planned for anything like this but knew that here was a woman who had been sexually not so active for the best part of over a decade or two. Maybe Mom felt like tonight she could finally let out this sexy woman within her. I knew Mom was a sane woman and she'd know when to bust the party by revealing herself. However, the only thing I wasn't sure about was how I would control my thoughts as I saw her dancing around like a woman and not as my mother.

After a while, she said she'd need a booze break and broke out of the circle and headed to the kitchen bar where the booze was stocked up.

"Dude you're the best. You have hired the best stripper in town for this party. I've never seen a woman like her," exclaimed Tyler as he just couldn't control himself.

"She's a total MILF guys. I bet she's our mother's age but she's damn hot for a woman in her 40's," said Ryan.

"Totally man, like I would fuck her even if she were my mom," barked Tyler.

"Ewwww", "Creeeepy", "What's wrong with you", "Are you sick?" were the reactions he got from the rest of us.

"Tyler, please stop being weird for today at least. Anyway, guys she's neither Tyler's mom nor any of ours, so let's just ignore what he said. And David, you're the best brother/best-man ever. Thanks bro, for planning out tonight," James hugged me as it couldn't have gotten more awkward with what he just said.

"David could you come over here," shouted Mom from the kitchen bar and I immediately went to check up on her.

"Mom is everything fine? And, how long does this have to go for? Don't you think we've got him? I think it's best to reveal yourself and crash it right away," I tried explaining to her as swiftly as possible.

"David calm down or else they might hear you. Listen I've got it all under control. Let's just stretch out a little more and have a bit more fun and then I'll take my mask off. I'm really enjoying all the attention I'm getting tonight. Anyways, I wanted to know whether you had tequila in here? I think I'm going to need a few good shots of those"

"Yeah we do." I replied.

I was very surprised since Mom never had tequila. Wine or vodka were her choice of liquors and here she was asking me for tequila on a night where everything was going beyond expectations.

I cut open a few lemon slices and placed some salt on a plate. Then, I popped the bottle of Patron which I had ordered for tonight and prepared a few shots for mom and myself.

"But why tequila Mom?" I asked curiously. "I've never seen you having it."

"Well let's just say I'll need a few of these when I go back there. I just can't keep on dancing, maybe a little bit of stripping, but nothing excessive"

"Mom don't you think it would be a bit too much. I'm not sure about this."

"David, are you worried you're going to be embarrassed watching your old mother dancing and stripping?"

"Nah. You're not old at all Mom. In fact, you're the most beautiful woman in the world. And, I'm not saying this because I'm your son. All my friends think you're hot and they think you are a MILF."

Mom blushed when she heard that my friends thought of her as a MILF. Her face turned bright red and her nostrils flared. She knew that she was beautiful woman, but to be called a MILF by young boys was something else for any woman in her 40's.

"Thanks a lot baby and don't tell your brother that I told you this, but you are indeed the best son in the world."

She wrapped me in a tight embrace. There was nothing mother-like in that hug though and the fact that she was dressed so lightly didn't help matters as I felt a little twitch inside my pants. Then she did something I would never have thought of. She gave me a little peck on the lips, no tongue involved. Just a flirtatious kiss on the lips and gulped down the shots.