*****All characters in the story are 18 years of age or older*****
As I slide up the Double Windsor knot of my tie, my stomach knots itself in a similar way. The dread of the upcoming evening percolates in my gut. I wish I could say I believed my mother when she told me this year would be different from the previous three, but I know deep down that it's another lie.
I go to a private high school in the Western Suburbs of Chicago. Every year around Mother's Day, the school hosts a mother/son dance for the boys and their moms. We've always jokingly called it the Mom Prom because the mothers usually make a big deal out of it resulting in a Prom-like atmosphere.
It's usually a great time for everyone despite the Oedipal overtones of the colloquial name; for everyone except me, that is. For some reason, my mom thinks this day is a perfect excuse to get all dolled up in some fancy, expensive outfit. Don't get me wrong, most of the moms do, but most of the moms aren't Instagram fitness models.
For the last three years, my mom has accompanied me in some outrageously sexy, ultra revealing mini-dress or something equally inappropriate that looks as though it has been painted on. As you might expect, this had led to years of abuse from my classmates telling me about how hot of a MILF my mom is, like I didn't already know. The worst part is hearing the constant berating from the upperclassmen about how they're going to fuck my mom.
The only reprieve this year is that I'm a senior and the underclassmen won't try to fuck with me, but that won't stop the rest of my classmates. Despite the awkwardness of the conversation, I finally gathered the courage to tell my mom what every one of my friends and classmates say about her. I pleaded for her to be like a normal mom and tone it down for my sake. She promised that she would, but with a caveat that she still had a reputation to uphold and needed to be fashionable for her followers. I can only imagine what that means.
Last year she wore a silver evening gown that practically looked like liquid metal dripping down her curves. Her ample bosom and cleavage were on full display, and the dress had a slit that showed so much thigh that if any of the girls wore a dress like that, they'd be sent home for a dress code violation. I'll give her credit though, she keeps it tight and she definitely knows how to get the attention of every man in the room.
The other moms are fully covered, most of them in frumpy, decades old gowns and dresses that do nothing to compliment their aged and overweight bodies. The few other moms that could be considered attractive wear modest dresses that are fashionable but not showy. Unfortunately my mom gets an unfathomable amount of clothing sent to her from designers and clothiers for her to wear as an influencer. I don't know who she thinks she's influencing at a High School mother/son dance, but it isn't the audience she's hoping for.
I must admit though, the freebies are a neat perk. It's great for her and provides the family with a lot of cool clothes, trips, food, etc., but it is exhausting always having to worry about her getting the perfect picture showing off whatever paid for our day. I won't tell you her name here, but she's associated with other fitness models/mothers on Instagram like Emma Glover or Jala Sue. Go ahead and take a look at their profiles and imagine being a high school student with that as your mom. That is what I have to deal with.
Pretty much every one of my classmates has my mom's Instagram page and OnlyFans page on bookmark. Thankfully she doesn't do nudes, but my horror multiplied exponentially after the first Mom Prom when the seniors learned they had a model in the school. One particular asshole introduced me to her OnlyFans page the next day. What a lovely way to learn that your mom is practically a soft core porn star.
I was embarrassed and angry and confused and oddly turned on. I had never seen my mother in that way before. In the picture I was shown, she wore nothing but black stockings and a pair of black pumps and was posing on her bed. Again, she didn't show anything X-rated. It was what is called an implied nude, but I had only ever previously seen her fitness related content. She was attractive, but I didn't see her as sexy. That picture blew my mind. I developed an obsession with black stockings. Instant boner alert if I even saw a woman wearing nylons, imagining if they were lace top thigh highs like the ones I saw my mom in that day.
It almost became a debilitating sickness. I would often find models online that looked like my mother, especially if they modeled in stockings. Finally, I broke down and searched for the picture of my mother that had caused me such anguish. I'm ashamed to admit that I came twice that day looking at that picture. Unfortunately, it wasn't the last. No matter how hard I tried and how much I tried to stay away, that picture was burned into my brain to stay.
My mom didn't wear stockings often, but when she did, I couldn't help but stare at her legs. They were like a vice and my eyes were trapped in their grip. I'm sure she noticed, but she had never mentioned anything about it to me. She usually had the attention of most men, so it wasn't anything she wasn't used to.
This year, a few of my friends and I were all traveling together. The moms rented a stretched Navigator for the night and planned on going out in style. We lived about 30 minutes from the school in the Southwest Suburbs, but the rest of my friends lived closer to the school in the Western Suburbs. The limo would pick us up first and then grab everyone else. Usually we'd all just meet up at one of their houses, but the moms decided that they wanted to drink in the limo beforehand.
I swallowed my fear and made my way to the living room to wait on the limo and my mother. I sat patiently on the sofa while my mother put on the finishing touches in her room upstairs. My dad came in from the kitchen with a beer looking like he was settling in for an evening watching baseball.
"All ready for your last Mother-Son dance huh?" He said as he sat in his chair and flipped on the TV.
"Yeah, I guess, as soon as Mom comes down."
"Ha," he laughed. "You know her. She won't be ready until she absolutely has to be."
I bet you're wondering why I don't say anything to my dad. Well, he's worse than my mom. He encourages her to dress and act the way she does. If I said anything about how my friends want to fuck his wife, he would be more proud than upset. But, I guess I can't blame him. At 44, he has a smoking hot wife who pulls in money and loads of free swag just for being hot. According to him, he hit the jackpot, and to be honest, he's probably right.
I relegated myself to sitting on the couch, wringing my sweaty hands in silence, as I waited for my date. I continued to hold out a sliver of hope that she would come down the stairs in something decent. I just stared out the window as I ran scenarios through my head, preparing comebacks for the punchlines that were surely to come my way. At last, I glimpsed the white Navigator as it pulled up to the house.
My dad yells up to his wife, " Hey Babe, you may want to wrap things up. Your chariot awaits and its best not to keep your chauffeur from his duties."
I rolled my eyes and shook my head. "Come on mom, let's go!" I hollered. "Everyone else will be waiting on us."
It still took another few minutes and I had to peek out the front door to motion to the driver that we needed a minute or two. Finally, my mother graced us with her presence as she seductively sauntered down the stairs, taking each step with her feet turned to the side, so as not to misstep with her heels.
My heart leaped up into my throat when I saw her. My eyes traced her body like in one of those old time movies where the camera pans up from the bottom. She wore black Louboutin stilettos with the red sole and an impossibly thin and high heel. Her long legs were on display in the shortest of black micro-dresses. The bodice clung to her curves, her breasts fighting to break free from the camisole. Spaghetti straps strained to hold the dress up around her neck. The dress was backless, save for the crisscrossing of 4 additional spaghetti straps in the back, with the skirt beginning just below her back dimples.
It was clear that she wore no undergarments. It would be impossible for her to hide them in such a revealing dress. Her auburn hair held a slight curl as it draped over her shoulders. Despite her 40 years, she wore little makeup, but still looked as youthful as ever. Bold eyeliner and false lashes highlighted her face with her lips and nails sporting a matching splash of red to go along with her Louboutins.
Despite all this, it was the black stockings on her legs that caught my attention. They were impossibly sheer and made her legs glisten as she made her way down the steps. My eyes were transfixed. I couldn't believe what I was seeing. My cock twitched in my pants as it awakened to the sight of the fantasy I had held for the past three years. I was furious with my mom, but at the same time, I was frustratingly aroused.
"Wow, I guess all that extra time was worth it!" My dad exclaimed from the chair, finally diverting his attention from the game.
"I wanted to go out with a bang for the last Mother-Son Dance," my mother cooed. "Do you think this will make all the other moms jealous?"
Her and my dad continued with their stupid game.
"I'd be more worried about what they call you behind your back," I muttered under my breath.
"What was that, Marty?" Mom asked.
"I said we better be going. We're already late." I retorted as I held open the door.
Mom gracefully joined me at the door as we finally headed out.
"You two have fun," Dad called out from the couch. "Make sure you take good care of your mother tonight, Marty. Show her a good time."
I closed the door and tried to hurry my mom to the limo before any of the neighbors saw us. The driver held the door open and not so discreetly eyed my mother as she climbed into the car, her dress rising ever so slightly to show the lace top of her stockings. The driver caught me staring and gave me a knowing look before he smiled and winked as he shut the door and made his way back to the front.
After a few minutes of exploring the perks of the limo, my mother poured herself a glass of champagne and I turned on some music. We sat in silence for the first fifteen minutes or so as we headed to pick up my friends and their moms. I did my best to avoid looking at my mom, but it was incredibly difficult to keep my eyes from wandering to her legs. I sighed out loud as I realized this dance was going to prove even more difficult than the last three.
"What's wrong baby?" My mom asked as she put a hand on my leg.
I looked at her and rolled my eyes.
"You're kidding, right?"
"This again? I thought that you would like this outfit. I picked it out especially for you."
"It's lovely Mom, you look amazing." I said sarcastically. "I can't wait to hear how amazing you look from all my friends."
"Well your friends aren't the ones who will be taking me home tonight!" She giggled.
I couldn't believe her cavalier attitude. Clearly she didn't care about how her outfits affected my life. This was all a joke to her. I turned up the music for the rest of the ride and stewed in my misery.
It only took about 10 minutes until we started picking up my friends and their moms, but it felt like an eternity sitting in silence. Mike and his mom, Denise were first, followed by Chris and his mom Claire. They were both overweight and middle aged women who felt like they could relive their youth through my mom, so of course they were thrilled with my Mom's outfit.
"Oh, you look so amazing."
"Who made your dress?"
"Are those REAL Louboutins?"
"Which company sent you all this jewelry?"
