I call this a “true story of my imagination”.
“True” in that the main characters in the story are based on real characters – myself and a cute, young-adult woman that works the concession stand at my son’s Little League complex. “True” in that many of the non-sexual situations and non-sexual banter in this story actually took place EXACTLY as written.
“Of my imagination” because I have fantasized these situations evolving into hot, unbridled sex with this hot, young woman. To be clear: We never had sex. But there’s always next season.
I had to put this fantasy on paper (so to speak) so I have it to return to when I masturbate to it. And boy have I jerked off to it. I hope you enjoy this story. It’s long but I’ve tried to break it up into manageable pieces. Names and places have been changed to protect the innocent. lol All characters are over 18 years of age. Let me know what you think in the comments.
Key characters:
Leo Rotelli – Forty-five year old divorced father of two. Very fit, handsome and considered a DILF by his twenty-five year old daughter’s friends. Sexy, Mediterranean looks with a full head of long, black hair down to shoulder and dark smoldering eyes. Tanned and manscaped fully.
Tina – A tiny, cute but sexy and sultry 20-year-old, young woman who works the concession stand at the Little League complex where Leo brings his son to play. Standing five feet, one inch tall and weighing 120 lbs, has tits that draw your immediate attention. They are full and luscious D cups. She has shoulder-length, curly brown hair and brown eyes. IMHO, she is a spitting image of a [young Leah Remini](https://i.imgur.com/qx86Z8b.jpg) but with bigger tits.
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“Can I have two bottled waters, Tina?” Leo asked from the other side of the glass partition, directing his request to the only person in the concession room – a young, cute woman that he had seen working the stand for at least the last few years of the ten he had been coming to the little league complex.
“Sure,” Tina said, turning toward the cooler. Leo took the opportunity to admire her plump, apple-bottomed butt as she retrieved the water. She turned suddenly to catch his stare on her, and he quickly gazed back to her face, noticing a smirk across it as she returned.
“You surprised me that you knew my name,” she said sweetly, ringing Leo up.
“Oh, they mentioned it over the loudspeaker,” Leo responded, kicking himself in not coming up with a more impressive response.
“They did? I didn’t hear it. What did they say?” She said, as he handed her cash and waited for change.
“Bob encouraged spectators to patronize the concession stand since the proceeds support the league, and he said to say hi to the ‘beautiful Tina’,” Leo answered her honestly, referring to Bob the league announcer every week. He noticed Tina smirking and bashfully looking away.
“He did not,” she said, sweetly, as Leo took his change, feeling her finger-tips on his palm.
“He did, I swear!” Leo said. “I actually never knew your name so I thought it was someone else. But you’re Tina and you’ve been here, now, for a few years, right? You’re our concession girl.” Leo tried to tease, maybe flirt. She smiled sweetly, as Leo looked around to make sure no one was waiting in line behind him. No one was around.
“Yeah, I’ve been here for the last few years,” Tina answered.
“How old are you, Tina?” Leo asked genuinely, but suddenly realizing the creepiness of the question, as Tina’s expression had a look of concern.
“Twenty, why?” She said looking him in the eyes. Leo’s cock flexed under his cargo shorts. The young woman was stunning with smoldering eyes that burned through you and right to a man’s cock.
“Oh, I ust wondered because most people quit jobs like this when they turn eighteen,” Leo answered. Tina smiled again.
“My mom makes me work here,” she responded. “She’s involved with the league and convinced me to start working here years ago. I still do it cuz they have trouble staffing it, especially after Covid. I don’t mind it. I get to meet a lot of interesting people, like you.” She added. “How old are you?” She asked back.
Leo was a bit taken aback at her boldness. He wasn’t used to a twenty year old, you woman being so bold with him. Usually they were polite and referred to him as Mr. whatever. He was surprised at her comment about getting to meet him and her forthrightness at asking his age. He wondered if she was hinting, slightly, to being interested? Still, his cock twitched again, as they held each other’s stares.
“I’m forty-five. I’m old.” Leo Answered, smirking. Tina smiled sexily, holding his stare.
“Wow, you’re my dad’s age,” she quickly shot back. Then adding, “you look in much, much better shape than him.” She said emphatically, stressing the word ‘much’ as her eyes roamed over Leo’s body. Leo was suddenly glad he had worn a snug t-shirt that showed off the results of years at the gym. He decided to turn the conversation back to her.
“Are you in school, Tina?” He asked. Tina nodded affirmatively.
“Yeah, I’m a sophomore at state,” she answered. Leo nodded in understanding.
“Good. Get that education!” Leo said, grabbing his bottles. “Well, as much as I’m enjoying this, I better get back,” Leo said, again trying to lightly signal a flirt. He sighed deeply.
“Okay, bye,” Tina responded, flashing her pearly whites as her gaze burned into Leo’s eyes.
That night, under the covers of bed and in total darkness, Tina had shed her panties and was digging two fingers into her pussy imagining the mature man, Leo, fucking her. She had always been attracted to older men, and now, she was flirting with one. Not just any mature man but a hot, sexy one! She imagined his mature but hard and strong body filling her vision as he fucked her on the very bed on which she was lying. She imagined a throbbing, veined cock sliding into her tender, tight pussy as her moans filled his head until he emptied inside her. Under the covers, Tina arched her back and bit her bottom lip to stifle a moan as her body rocked an orgasm at the thought of Leo cumming inside her.
Across town, Leo sat in his study, listening to Nine Inch Nails. His kids were with their mom, and so he was alone. An empty glass of bourbon leaked condensation onto his coffee table next to him. Cum lay splattered across his bared stomach as he tried to catch his breath. Again, he had stroked his cock to Tina, the young woman from the concession stand. He had recalled their conversation and imagined it lead to her leading him into the back room where he fucked her standing up, against a pantry shelf. He imagined kissing her deeply to keep her quiet, as her body rocked through several orgasm; her young, tight pussy massaging his cock during orgasms and sending his cum flying inside her. He had cum masturbating at this final vision.
Source: reddit.com/r/eroticliterature/comments/vm6utd/part_1_the_concession_worker_the_dilf_m45_f20