My Mom Chaperoned My Prom


My Story

It all started at the last Parent/Teacher meeting before the prom. I'm secretary on the student council (don't laugh). The meeting was about the prom and how it was going to be organized.

My mom was there and she made a big deal about having herself be nominated as one of the chaperones. She always has to make a scene wherever she goes. She made a big speech about it, even embarrassing me by mentioning that her son was on the student council and how that somehow gave her more of a eason to be a chaperone. I could tell most of the other parents and teachers there - especially our Principal, Mr. Turner - were totally not liking the fuss my mom made during the meeting, but my mom was still able to get herself nominated.

The week before the prom was just torture for me. I didn't even tell my friends about my mom being a chaperone because I knew they would just goof on me about it.

Because she works in real estate, my mom used one of her connections and was able to move the whole prom celebration to a ballroom at this big hotel. She made such a big deal about it saying how the school gym was "no place for a wonderful event" even though it meant everyone was going to have to drive like a half hour to this stupid hotel. And she was always on the phone bragging to her friends about it and about how much money she spent on her dress and shoes for the prom.

By then I didn't even want to go to the prom but I had to since I'm also the president of the audio/video club at school and it was my responsibility to run the sound and lights for the prom king and queen ceremony. The way my mom was acting it was like she thought she was running for queen of the prom!


My Mom

My friends, Brad, Randy, and Pete, goof on me about my mom because even though they all agree that she acts like a complete snob and always acts so stuck-up like she's so much better than everyone, they also all say she's a "MILF" and a "Cougar". Brad once even went so far as to say my mom looked like "a porn star on her day off." That got the other guys laughing even more.

After my mom and dad got divorced last year, she went and got herself a "makeover". I call it her "fakeover". She made her hair blonder and I'm pretty sure got botox in her face and something that made her lips puffy and even got a boob job. (I saw one of her bras in the laundry room and the tag inside said "36C"). That's when my mom started dressing all trendy and pretty much like the same way girls at my school do: kind of short skirts or low-rise jeans and pants with tight t-shirts and tops that were either tight or low-cut or both. Its like she wishes she was on her own reality show or something.


Prom Night

The night of the prom I was a nervous wreck. My friends had found out that after the prom had been moved from the school gym and to the hotel ballroom, it was because of the "new chaperone". They fast found out that the "new chaperone" was my mom! That's when they really started goofing on me.

Well you should have seen her when she showed up at the prom. It was like she thought she was like going to the academy awards or something. She was wearing this really long tight kind of purple and pink dress that was sort of low cut and pushed her fake boobs up at the same time and had a slit up one side that showed off her legs in the light pink sparkly nylons she had on and these pink strappy high heels that thock-thock-thocked everywhere she walked. Her blonde hair was all done up on the top of her head and she had on a lot of make-up. As soon as she got there, my mom was like the whole time acting totally snobby to everyone, even sometimes telling him or her to watch where he or she were stepping around her dress.

I knew right then prom was going to be a disaster for me.

The moment my mom showed up at the prom I spent the whole time trying to avoid her. She had already made such a scene when she first walked in I wanted to stay far away from her.

Already though I could see how everyone else was reacting to her. The other chaperones were giving her dirty looks. Mrs. Cross and Mrs. Dayle were giving my mom disapproving looks behind my mom's back, but would smile and act friendly to her whenever they had to speak to her. Our principal Mr. Turner was looking my mom up and down with a scowl on his face he usually gave to the students he saw smoking in the parking lot at lunch.

Just about every other student at the prom was pretty much looking at my mom and asking who she was and what was she doing there. I could overhear some of them making comments about her snobby attitude and how lame they thought she was. Some of the students who knew she was my mom would look at her and then over at give and me dirty looks. I just wanted to hide under the table.

Just when I thought it couldn't get any worse, some of my friends came over to my table and started goofing on me about my mom. Brad started in by saying how "hot" my mom looked. He even said she looked hotter than his own date. One of the guys even was saying that whenever my mom stood by the stage lights that he thought he could almost see through her dress and that when he stood behind her he could kind of see the outline of a thong showing through her dress. That got them all calling her "Thong Mom". They all laughed at that one.

Prom was becoming more miserable than I could have even imagined. To make things worse, my date - a girl in my math class that I sort of liked and asked out - had to leave when her parents came to pick her up at ten. I was sitting by myself since my date had to go home early, but I still had do stay at the prom because of the light cues I had to do backstage for the King and Queen ceremony.

I was totally bored and started to wander around the prom. I saw my mom. She kind of stood out from the crowd in her long pink-purple dress. She was saying something to Principal Turner. From the look on his face, he didn't seem to like what my mom was telling him. When I got closer to where my mom and Mr. Turner were, I could hear what they were talking about:

"After all, I was the one who arranged for the prom to be here in this ballroom," my mom was saying in a haughty tone. "It's obviously quite a success. Even you can admit that, can't you, Roger?"

Roger was Principal Turner first name and it seemed like he didn't like how my mom was talking to him. "It's Principal Turner, Mrs. McFarlane," he said to my mom.

"It's Ms. McFarlane," my mom corrected Principal Turner, which I could see made him even more angry, but before he could say anything, my mom kept talking. "And as a member of the Parent/Teacher committee, I would like to be recognized for my part here at this prom. The very least you can do is mention my name before the King and Queen announcements."

My mom was just being so snotty that I decided that maybe I could help Principal Turner out by pretending to have something to say. I took a step closer to them and cleared my throat. "Uh...excuse me, mom?"

Before I could say another word, my mom was looking at me with her typical snooty stare. "Tommy, do you mind? Can't you see your mother is having a discussion? Run along."

I glanced at Mr. Turner and was surprised to see he was looking right at my mom's cleavage that was pretty hard to miss the way her dress was pushing it up. He didn't notice me looking and my mom was too busy staring at me to see him. She pointed her finger off in the direction she wanted me to leave like she always does at home which means that she's done talking.


The Center of Attention

I was sitting by myself at my table and playing Warcraft on my cell phone when Mrs. Cross – a teacher and one of the other chaperones that night – came up to me. She told me the King and Queen Ceremony was getting ready to start and that it was time for me to take my place backstage to work the light cues.

Glad to be doing something instead of just sitting there while everyone else was enjoying the prom, I got up and went around to the side of the stage and up the steps and behind the curtain to the backstage area. There was a control board with switches and knobs to control the lights. That's where I stood and waited for the ceremony to start.

Sure enough, when the ceremony started, when I looked out from the side of the stage, I saw that my mom had gotten onstage to stand next to Principal Turner. She was looking out at everyone and smiling like she was so pleased with herself. Meanwhile, Principal Turner looked less than thrilled to have her up there with him. He stood by the podium microphone and said a few words to the students, and then with my mom staring at him as if to hurry him up, Principal Turner made a very brief statement about how having the prom here at the hotel's ballroom was thanks to one of the chaperones.It looked as if Principal Turner was about to continue, but my mom moved next to him so she could be in front of the podium microphone. She smiled and waved at all of the students standing in front of the stage and clapping. It was obvious my mom was enjoying being the center of attention.

"Thank you, everyone," my mom said. "I just want you all to know how special this evening is and I so proud to be part of it. I hope with my help, I'll have made this a memory for all of you that you'll never forget."

I could tell my mom wanted to say more, but then Principal Turner stepped close to her. He put one hand on her arm and the other on her back, guiding her away from the podium and to stand back by the curtain. My mom didn't look pleased with having her moment cut short. A snooty expression returned to her face as she said something to Principal Turner. She pulled her arm away from him and took her spot standing upstage by the curtain where she smoothes her dress along her figure.

As Principal Turner went back to the podium, I returned to the lighting panel backstage. From the bright lights onstage, I could see my mom standing in front of the curtain. Looking down, I also noticed the trail of my mom's dress sticking out backstage from under the curtain.

I don't even know what made me think of it or even do it...but I went over to stand behind the curtain where my mom was. I leaned down and grabbed the end of her dress and carefully snagged it around the hooks that were lined along the bottom of the curtain. Any second I thought my mom was going to notice and turn around, so I hurried back to the lighting panel.

But the thing was, my mom didn't notice. From her silhouette through the curtain, I could see she was still standing onstage and facing out to the student audience. I had enough of my mom being at my prom and I thought for sure she would have felt me snagging her dress on the curtain, be upset, and unsnag her dress and walk off. It just made me think she was probably standing there loving that everyone was looking in her direction.

I didn't even think it would work but I went over to the curtain levers and pulled them all until the curtain behind her started going up. I really thought by then she would just notice right away because of all the fuss she was making about her dress and that she would've turned around and unpulled her dress from the curtain but she didn't notice at all until the curtain was already going halfway up and lifting her dress up her legs.

Everyone started laughing. My mom tried to take a step away from the curtain, but that caused her dress to pull tighter against her. The slit that was on one side of her dress just began to tear all the way up the dress, exposing the lace tops of her pink thigh-high stockings. My mom only had a few moments to desperately pull at her dress before the curtain went all the way up and ripped her dress off from around her.

Everyone there was able to see my mom's big fake boobs. All she had left on was this tiny pink thong and pink glittery thigh-high stockings and her big pink strappy high heels. Everyone was just totally laughing and she was just standing there with her arms at her sides and looking up at what happened to her dress like "duhhhh" with this totally stupid look on her face.

I know it's weird to say but it was so great seeing like my mom like that. For once, I was finally seeing my mom looking stupid and not knowing what to do. Like a deer in the headlights. Or better yet, like a stripper who went onstage and didn't know what to do. And with everyone laughing at her, it just made it so much better.

After a few seconds like that, I saw some flashed going off and saw that students – the guys mostly – were taking pictures of my mom. That's when my mom kind of seemed to snap out of it a bit and started trying to reach up to grab her dress down, her boobs jiggling every time she tried. Even teetering on her high heels, she couldn't do it. If everyone had been laughing at her before, now they started howling and whistling and clapping. No one was even trying to help. I even saw Mrs. Cross and Mrs. Dayle standing by the stage and laughing too.

I have to admit I was laughing too. It was pretty funny to see. After like a few seconds of her trying to grab her dress and everyone laughing at her, my mom was like almost crying. She looked out at all of us laughing at her and then she put her hands over her boobs and ran off backstage.

As I was standing there with everyone else laughing...I started feeling a little bad about what I had just did. You have to believe me when I say I didn't think the curtain was going to tear her dress off like that. By now someone had gotten the curtain to start to go back down. That's when I saw Principal Turner step away from the podium and just under the curtain as it lowered to the stage.


Backstage Porn Star

After seeing Principal Turner duck backstage, I thought maybe I should go see if my mom was okay. I went around to the side and went backstage. I knew my mom wouldn't be hiding by the front of the stage and since I didn't see her at the side exit when I was there, I started to walk to the backstage area but it was dark and I had to walk careful so I didn't fall on anything. Pretty soon I started hearing some whispering and noises that sounded like Principal Turner saying stuff like whispering it but like he was angry like he always is so I snuck my way over there.

I saw Principal Turner was standing near this huge prop board. He was looking down at something and as I got closer, I could see it was my mom. She was on her knees, sitting on the back of her heels, still only in her pink thong and thigh-highs. She had her hands over her naked boobs, barely able to cover them. She was staring up at Principal Turner much the same way she had been looking up at her ruined dress: an expression of daffy confusion as if she still couldn't understand what had just happened.

"Well, it looks like you got just what you deserved, you stupid little bitch," Principal Turner growled at my mom. "You wanted to be the center of attention at the prom? You got it. The entire graduating class saw you half naked on that stage looking like a complete tramp. Now, if you want to walk out of here in my jacket, you're going to put on a little show for me. I want you to start playing with those big tits of yours."

Everyone in school knows Principal Turner is a pretty strict guy, but I couldn't believe what I was hearing him say to my mom. She was still just staring up at Principal Turner with that dazed look on her face. I saw him lean closer to her and say, "Start playing with your tits or I will march you back on that stage in front of everyone and e****t you right out of the prom in just that sexy little thong and heels you have on, sweetheart."

To my total surprise, I began to see my mom's hands start to slowly move her boobs around. She was keeping them covered, but sort of move them up and down. The whole time, she kept staring up at Principal Turner.

"That's right," he hissed. "Play with those tits. Squeeze them."

My mom did as he said. She was now squeezing and rubbing her own bare boobs. Principal Turner grinned and I saw his hand on the front of his tuxedo slacks. While my mom continued to massage her boobs, he unzipped his fly and I saw him free his hard erection from his slacks. My mom's mouth dropped open in surprise and she stopped rubbing her boobs.

"I didn't tell you to stop," Principal Turner scolded my mom. My mom started to play with her boobs and Principal Turner stepped even closer, bending slightly at his knees, and slipped his erection right between my mom's cleavage.

"I've been looking at these tits all night," Principal Turner began breathing heavy. "You in that dress just showing off. Wanting us to look at your tits. Well we all got a look at these porn star tits!" He stepped back from my mom. As she continued looking up at him massaging and squeezing her boobs, he stroked himself in front of her.

Principal Turner had just titty-fucked my mom! I couldn't believe what I was seeing. There was my mom, on her knees in just a tiny pink thong and thigh-highs, playing with her perfect tits while staring up at my principal, who was standing before her and stroking his cock! I had never seen my mom like this...her body, that she so prided herself on, exposed...and her, for once, not knowing how to handle some daffy daze over what was happening.

I know I shouldn't say this...but I felt excited to see my mom so helpless like that. I realized Principal Turner was saying the very same things I had been thinking the moment my mom arrived at the prom. Finally, I was seeing my mom look stupid for once!

Principal Turner was breathing faster and stroking his cock with fever. Sneaking a little closer from the shadows, I saw that my mom was starting to breathe a little faster too. She was sort of swaying a little, still in that daze, almost as if she were about to feint.

And then suddenly, Principal Turner stepped closer to my mom. He put one hand in her hair, her highlights spilling over his fingers. My mom gasped again and he used the other hand to rub the tip of his cock across my mom's face. He brushed it against her cheeks and over lips, smearing her glossy pink lipstick.

"You've done nothing but run this mouth of yours all night," Principal Turner said. "Time to do something useful with it!" He slid the tip of his cock past her lips and with his hand still in her hair, Principal Turner began making my mom suck him!

I didn't know what to do. I felt dizzy and my legs wobbly, but I couldn't move or look away. I could see Principal Turner's cock sliding in and out of my mom's mouth...her pouty pink glossy lips making his cock wet and slippery.... the tip of his cock would sometimes slip out of her mouth and he'd use his hand to rub it across my mom's face before pumping it past her lips...his other hand in her hair and guiding my mom mouth on his cock...I could hear her making wet, slurping sounds.

I couldn't stop watching my mom. Only a short while ago she had seemed so confident and snobby, but now she looked completely helpless, half naked, on her knees in just her tiny pink thong, thigh-highs, and heels, her hands on her heaving bare boobs and Principal Turner's hard cock in her mouth, his hand in her hair, guiding her lips along his glistening shaft. I thought I should maybe say or do something, but I didn't know what.

And then, just under the sound of Principal Turner's heavy breathing, I heard something else. It was my mom. She was making these moaning sounds around Principal Turner's hard cock in her mouth. It was as if he was somehow making her love sucking his cock. "That's it," he whispered harshly at my mom on her knees. "Yes. Suck that cock, you little slut!"

I was even more surprised when I saw my mom remove one of her hands covering her boobs and use it to start stroking Principal Turner's cock while still sucking him. He used his free hand to begin squeezing the boob my mom uncovered. His breathing was becoming faster. "I've been waiting to feel your fake fucking stripper tits all night, you snobby little bitch!"

Suddenly, Principal Turner let go of my mom's hair and her boob. He pulled his cock from her mouth and then grabbed her wrist and yanked my mom to her feet. She gasped and wobbled on her high heels, looking dizzy and confused. Principal Turner still had my mom by the wrist and her other arm was dangling by her side. He was giving her a dirty smile, looking her up and down. I could see my mom blushing under his leering gaze, but she couldn't seem to look away from Principal Turner. He laughed at her. "Can't even stand straight in your Come Fuck Me heels, can you? Maybe it's time someone fucked you in those heels!"

Principal Turner spun my mom around by her wrist. She stumbled in her heels and he was able to get behind her and bend my mom over what looked like a sawhorse that was backstage. With her firm ass up in the air, I could see the thin material of her skimpy pink thong between her legs. Principal Turner whipped off his jacket and dropped it on the backstage floor. He then stepped behind my mom and slapped her ass.

"Ohhh..!" I heard my mom gasp with surprise. Principal Turner spanked my mom again, getting the same response from her. He laughed. "Damn, you've got a sexy ass! You are one hot little whore aren't you?" Before my mom could respond, Principal Turner hooked his fingers in the flimsy pink material of her thong and pulled if from between her legs, yanking it to the side. He used his other hand to grab his still hard cock and smoothly guided it right between my mom's legs and began fucking her right there.

I was shocked to see Principal Turner manhandle my mom so easily. She seemed to have been in such a daze after her dress was ripped off and now it was as if she was for the taking. I'd never seen her so helpless and being told what to do by someone and especially like this! Principal Turner had both his hands on my mom's hips and was thrusting into her hard and fast, panting and breathing heavy. I could hear my mom breathing faster, too. And moaning...I couldn't believe it, but mom was moaning.

This only made Principal Turner laugh. He began fucking my mom even harder. He used one hand to grab her hair, pulling and forcing my mom to look back at him as he used her. My mom's eyes were wide with surprise. Even in the dark of the backstage area, I could see her body was shining with sweat, her perfect tits bouncing, I swear I could see her hips swaying to meet Principal Turner's thrusts.

I'd never seen my mom like this before. She was always so prim and snobby and stuck up to everyone like she was so much better than them. But now, she was like transformed into such a helpless slut! It was as if I was suddenly in a live porno movie starring my mom. I couldn't believe how things had so quickly turned this way and I was feeling sort of weird for maybe being the one who caused this to happen to my mom...but another side of me was excited to see my mom being used like a total slut. Her haughty, snotty attitude was completely gone. The way she was looking back at Principal Turner as he fucked was like she couldn't believe it was happening to her but at the same time, she was moaning and making these sexy little surprised gasps.

That's when I realized I had the biggest hard-on that I ever had in my life...and it was happening while I was watching my mom getting just what she deserved! Even more incredible was that it looked as somehow Principal Turner had was making my mom enjoy what was happening to her!

Principal Turner suddenly stepped back from my mom. I saw his hard cock slip out from between her legs, the length of it slick from being inside her. My mom was still bent over the sawhorse and moaning. Principal Turner grabbed her arm and pulled her up, turning her around to face him, then putting his hands on her shoulders and pushing my mom down on her knees before him. He grabbed his cock and stroked it, aiming it right at my mom.

I think my mom realized what suddenly was happening; because she lost the dazed look in her eyes and looked up at Principal Turner as if surprised he was in front of her stroking his cock. I saw her mouth drop open and her gasp with shock. She started to put her hands over her breasts but Principal Turner grunted and I saw a long white milky stream spurt from his cock and land across the side of my mom's lips and cheek and into her hair. More cum squirted from his cock and on went across her face, dripping down her chin. Heavy drops of it splattering on her neck and tits.

I saw my mom, her hands half on her cum splattered tits, arch back on her knees, her eyes closed, but nowhere to go as more of Principal Turner's load spurted into her hair, leaving her blonde highlights in pearls of jizz; more of it on her neck and chest...I could actually hear the wet splash of it on her skin. By the time he finished shooting his last load, my mom was covered in the thick milky splatter of Principal Turner's cum.

At that very same moment, I felt the front of my slacks stain with the warm wetness of my own load going off.

I always felt weird when I heard my friend Brad say my mom looked like "a porn star on her day off." But as I looked at her, now I knew what he meant. She had looked so glamorous when she first showed up in her long, tight pink and purple dress, with her hair up in a perfect styled twist and her make-up dramatically done. But now, her hair hung half undone, matted and sticky white gobs. Her heavy dark mascara around her eyes was smudged. Her glossy pink lipstick smeared, replaced by a glossy glaze of cum. Her neck and boobs – where she still had her hands half placed - looked sticky with runny strands of thick semen that dripped down between her cleavage, some of it even staining the silky material of her pink thigh-highs. Right then, my mom looked every bit like a porn star.

Principal Turner put his cock away and zipped up his slacks. His jacket was still on the floor. I saw him kick it toward my mom, who was looking up at him with that dazed look on her face. "Take the jacket and clean yourself up," he told her. "And then get the fuck out of my prom, you stupid bitch." Without another word, Principal Turner walked away from my mom.

I heard a sharp intake of breath and someone utter the word, "Slut..!" I turned to see Mrs. Cross had just stepped around the curtain from the front of the stage. She had what looked like the remains of my mom's dress in her hands, but now stopped at the sight of my mom.

My mom seemed to snap out of her daze at sound of Mrs. Cross' insult. Suddenly she was looking down at herself with what seemed like surprise and total embarrassment. My mom's hands fluttered around her cum soaked boobs and neck, as if trying to wipe it away without really touching it.

Mrs. Cross gave my mom a very angry and upset look, then just dropped what remained of my mom's dress on the backstage floor. She turned and walked back around to the front stage curtain. I saw my mom reaching for Principal Turner's jacket in front of her. Not wanting risk being seen by her or anyone else, I quickly hurried out to the stage's side exit.


Last Look

I had snuck out to the hotel's big lobby. There were plenty of students from the prom standing around and a bunch of the hotel's actual guests who were having drinks and such sitting around the lobby's big expensive sofas and chairs.

I headed for the men's bathroom so I could dry the front of my slacks. My tuxedo was a light grey and the stain I'd made while watching my mom with Principal Turner was pretty obvious.

They had no paper towels in the bathroom, just those hot air blowers. So I turned one on and tried to stand under it, but it just wasn't working. Not to mention the scalding hot air on my groin wasn't too good either!

The stain was still sort of noticeable, but had faded as good as it was going to get. I walked out of the bathroom and into the lobby just in time to hear the familiar sound of thock-thock-thock! My mom's heels hurrying across the lobby's marble floor. Everyone in the lobby was turning to look toward the ballroom at the other end, so I did too.

My mom was trying to walk through the lobby as fast as she could in her high pink heels. She had on Principal Turner's tuxedo jacket. She was trying unsuccessfully the keep the front of the jacket closed with one hand, but her jiggling boobs were pressing the jacket open, putting her sticky and cum glistened cleavage in constant view. The end of the tux jacket barely covered the pink lace tops of her thigh-highs. My mom was using her other hand to try and keep the bottom of the jacket from flapping open around her thighs and ass, but wasn't having much luck while walking so fast. She had made an attempt to put her hair back up, but her blonde tresses – tangled and matted with jizz - were coming undone. She hadn't bothered to fix her make-up and one side of her neck was still shiny with streaks of cum.

The lobby became abuzz with chatter, a few laughs, and even some wolf whistles. Someone asked aloud, "Is this a prom or a porn convention?" That brought bigger laughs from everyone in the lobby.

I found myself laughing a little bit, but then more just like everyone else. And as luck would have it, my mom walked right past me. She must have recognized me out of the corner of her eye, because she suddenly stopped. She tried to hold the jacket closed and just stared at me with a look of embarrassment. I couldn't help but to stand right there and look my mom over from her heels to the top of her cum sticky hair.

I saw my mom glance down at my groin. Her eyes went wide with shock and her mouth dropped open in surprise. And that's when I looked down and realized I had another hard-on and shot another load in my slacks! The spreading stain was more than obvious! I saw my mom blush and without another word she turned and continued her awkward walk of shame out of the hotel lobby with everyone laughing at her.

Thanks to my mom's appearance at the prom, she made it a night I'm sure no one will forget!

88% (50/7)
Categories: MatureTaboo
Posted by tommymcf
2 years ago    Views: 6,062
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1 month ago
Very nice!!
1 year ago
very good
1 year ago
Pretty good story, Maybe this will have an positive effect on your moms pompus attitude
2 years ago
Very sexy story, hope you have more to tell.
2 years ago
Very hot hot hot mmmmm thanks