Chapter 1

Caution: This Romantic Sex Story contains strong sexual content, including Ma/Fa, Teenagers, Romantic, School, .

Desc: Romantic Sex Story: Chapter 1 - There have been show moms ever since there have been shows. Maybe they should just have their own show.

Grooming always seemed to be the most time-consuming portion of these shows, from the local ones all the way up to nationals. Maybe it just seemed the most time-consuming because I hated it. I didn't even like grooming me. But it was an important part of the show. She sat in front of me, on the carpeted pedestal that each of the contestants were provided for final grooming, while I worked my way around her, making sure that everything sat just where I wanted it. The look wouldn't last long, of course, once the showing began, but by then it should have done its job of attracting the judges' attention.

The loudspeaker roared to life.

"Attention in the Grooming Area — the two minutes until the first division. Contestants should begin to assemble at the entrance to the show floor."

I gave her one final inspection.

"All right, Robin," I said, "let's hit the floor."

She slid off the pedestal and fell in behind me as we walked toward the entrance where the nine other finalists in her division were gathered. I was very pleased. After five months of training and competition, Robin didn't need to be led anywhere. We were seventh in line, and after the initial parade, we took our places -- Robin on her show pedestal, me standing beside her -- as they began to introduce the contestants. I gave her a wink, and heard her whisper back, "I am so hot right now." I smiled. Becca had said exactly the same thing.

It had begun, as so many things did in my life at that point, with my mother. One June morning, a week after my junior year in high school had ended (thank God), she sat down uncomfortably across from me at the kitchen table.

"You've heard about the National MILF Show, haven't you?" she finally asked after a good bit of fidgeting.

In response, I spat my coffee all over the table. So much for denying it. Of course, my mom, a junior high school English teacher, probably already knew as much about it as I did. Teachers always seemed to have this little network of information going.

"Well, yeah," I agreed reluctantly, mopping the table with my napkin. "It's the biggest thing on the internet. You going to enter?"

She blushed. My mom was a real good looking lady, particularly for forty-five, but I didn't see her as real MILF material. On the other hand, maybe it would do her some good. Ever since her divorce from Dad, she'd been in a bit of a funk. I raised my eyebrows. She turned her mouth down and threw a napkin at me.

"Asshole," she said. "I'm forty-five years old."

"I'm not saying you'd win," I protested. "But you'd give 'em a run for their money."

"I'm flattered you think I would even consider entering," she said, "but no, it's Mrs. Roberts."

"Becca Roberts next door?" I asked. "Shit, I'm gonna subscribe right now."

"Kenneth," she sighed before going on. She was always bothered by my swearing, although she'd gotten better. Or I had. Maybe both of us. "How much do you know about the show?"

"Everyone has to be a mom," I said. "They have a bunch of contests and the finalists end up at the big show. I think it's held over Thanksgiving. We were at Aunt Beth's last year, so of course, I didn't get to watch it."

Didn't get to watch it live, I thought to myself.

"Well, do me a favor, will you?" she twirled her hair as she sat across from me. "Here's a couple of websites. Read up on it and then we'll talk."

It was an odd request, but hey, it was Mom. I took the piece of paper she gave me and spent an hour or so on the computer.

The National MILF Show was three years old. It had actually begun a few years earlier when a bunch of Long Island high school kids managed to convince the older ladies that they were, uh, seeing, to meet together in a hotel ballroom. Two years later, the meeting had become the stuff of legends, and the kids, then in their second year of college, organized a national show. It started with a series of local and regional competitions where moms performed stripteases for their "handlers." Then, at the state level, things got serious. And sexual. By the time women reached the national show, they were expected to engage in a ten-minute blowjob and a five-minute "compulsory" program with their handler in order to win their division, and then a ten-minute freestyle program to claim the national title.

The final day of competition was broadcast live, over the internet of course, and was making damn good money. The prize money, in fact, was based on internet subscriptions; this year it would be a total of 2.5 million dollars, of which first prize was $750,000.

"Okay," I tried to say calmly when I returned. "What's up?"

"Well, Becca watched it last year," she began, "and she's convinced that she can win it."

"No sh — " I interrupted. "I mean, really?"

She smiled.

"Yeah, no shit. You've seen the pictures on those sites, what do you think?"

"All right, yeah, Mrs. Roberts is a serious MILF," I agreed. Rebecca Roberts was in her mid-twenties with a playmate face and a body to die for.

Mom visibly swallowed and took a deep breath.

"She wants you to be her handler," she blurted out.

"Her handler?" I barely refrained from screaming. "You mean those guys who lead the women around and show 'em off, and —"

I paused.

"And fuck them right there in the arena?!"

Was she kidding? I would have given my left and right testicles for a chance at Rebecca Roberts. And since her husband was a former professional football player, that's how I figured it would have ended up, too.

"Yes," Mom said. "Although you only do that if you reach the finals in Hawaii. Anyway, she wants you to do that for her."

"Why me?" I asked.

"Well, she likes you for one," she started. "She thinks you're good looking, which is a plus. And..."


"And she needs a well-endowed man to make her climax," Mom exhaled.

"And what makes her think I have a, um, a big one?" I asked. I did, but I couldn't imagine how Rebecca Roberts had known that. I certainly knew better than to get an erection anywhere near her, particularly when her husband was around.

"Well, she's seen you mowing the lawn in your shorts, and stuff."

That wasn't it. I waited and raised my eyebrows.

"Oh, all right, I told her."

"How the hell do you know?" I shouted.

"Look, do you want the job or not?" she shot back.

"Uh, sure, I guess," I said.

"If she goes as far as she thinks she can, you'll have to spend one weekend a month at shows, starting in early September," Mom explained. "Why don't I have her come over?"

I watched in stunned disbelief as she picked up the phone, explained that I'd accepted, and invited Mrs. Roberts over. Five minutes later, she answered the doorbell and ushered the entire Roberts family into the kitchen. I pressed myself back into the seat. It was a trap; I knew it!

But Bob Roberts came over and simply extended one of his meaty paws to me while Rebecca held onto five-year-old Bree.

"Appreciate this, Kenny," he said, as bashfully as a former offensive tackle could. "I'm gonna take Bree and go to the zoo for the day so you can talk this over."

And then he left, leaving me with his wife, Rebecca, in a short, orange paisley dress held up by the thinnest of straps. Mom came back into the room before I had had a chance to even say hello, and she and Rebecca both sat down at the table.

Rebecca took a deep breath of her own before she started.

"First off, why me?" she said. "Frankly, I watched it two years ago, and I thought, what a hoot. But I wasn't eligible until this year, because you have to have a child who's at least six as of September 1, and Bree won't turn six until this August. I wanted to do some beauty contest work when I was younger, but my family could never afford all the time and the travel. Now I can."

"Wow," I nodded.

"Second, why you? For one thing, of course, handlers have to be eighteen by the date of the state finals, which are in mid-October. Your mom says you turn eighteen on the fifth. And you can't be older than twenty-one on the day of the national finals. I think you're a good looking kid, I think you're nice, and you're taller than I am, which rules out a number of guys since I'm five-ten. Neither Bob nor I is excited about the idea of my trolling the internet to find somebody else, and the only other young man I know is my nephew Jimmy. He'd do me in a — I mean, he'd do it in a heartbeat — stop laughing, both of you — but I'd have to live with him smirking at me for the rest of my life. And finally, according to your mom, you've got what it takes to succeed on the final day."

"Yeah, before we go on, how do you know that, Mom?"

"So you're not going to tell her yes?" my mom countered incredulously.

Now it was my turn to blush.

"Of course I am," I said. "I'd do her in a heartbeat, too."

Now everybody laughed.

"But seriously?" I said.

She smiled.


"Marcy Rooney?" I asked. My first girlfriend? Well, to be fair, my only girlfriend until she'd moved East with her family around Christmas.

"She wanted some advice on handling your size, and she figured I would have had the same problem with your dad. Which, unfortunately, was one of the only problems I didn't have. But I asked her how big was your, uh —."

"Package?" Becca prompted after a small pause.

"Yes," Mom waved a flustered hand. "So that's the story."

"There is one thing," Becca interrupted. "Bob and I agreed that you and I won't do any fucking until we get to Hawaii. "

"What else would we do?" I asked.

"Lots of contestants like to practice before they get there," Becca said, "in order to find out if they're compatible with their handlers. If you're as big as Marcy said, that won't be a problem. But I will need to take a look before we commit to each other."

I stood and pushed my shorts down my thighs.

"Shit!" my mother said.

I raised my eyebrows at her, and missed Becca's reaction. Apparently, it was favorable, though, because she slid a piece of paper across the table as I pulled up my shorts and sat down again.

"Um, okay," Becca said, "why don't you read this contract, and then if you agree with it, your mother can sign it on your behalf because you're not yet eighteen. It's a standard handler contract, and I have to have one on file with the group running the show before I'm allowed to compete."

"So it says here I get ten percent of what you get?" I asked after a while.

"That's right," Becca was beaming at me now. "Just like a caddy."

"And what's this part about another handler?" I asked, pointing to another clause.

She smiled.

"Well, this is the third year, so there are already some guys known as so-called good handlers. What this does is say that if I drop you to pick up one of them in later rounds, you still get your full ten percent. His ten percent comes off what's left after that."

"Cool," I nodded. "Sign away, mom."

"Do you have a girlfriend you need to explain this to?" Becca asked.

"Not at the moment," I smiled back. "Maybe Marcy scared 'em all off."

Mom finished signing and Becca affixed her signature as well. Kissing me on the forehead, she told me she'd be back after lunch to go over the contest, and left to go register the contract on the website.

"You could have asked her for a peek, too, you know," Mom pointed out.

"I imagine I'll see enough of her pretty soon," I grinned.

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Story tagged with:
Ma/Fa / Teenagers / Romantic / School /