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The Outing

Maddie falls in love with her babysitter, Matt.
It all started five years ago, when Maddie was thirteen. Being an only child, she needed a babysitter still when her parents were out of town or at an event together that Maddie couldn’t attend.

Usually, Maddie’s grandparents would come by to watch her, or she would go to their house. However, during the winter, her grandparents would go to their home in Florida.

Maddie could not remember where her parents went that night five years ago, but she remembered everything else. Her parents had asked Matt, a seventeen year old that was friends with the family, to watch Maddie for the evening.

Matt and Maddie had met before, so he wasn’t a stranger. However, it had been a while since they had seen each other.

Maddie had never had a crush before, but when Matt walked in the door that night her heart felt like it was going to burst through her chest.

Matt was on the basketball team at high school, so he was relatively well known by students throughout the school system. It made sense that Maddie had a crush on him since he was popular, good looking and nice.

Maddie spent most of the evening watching TV with Matt, but occasionally they would have some short conversations. One of which would stick with Maddie throughout the next five years.

“Matt, what do you look for in a girl?” Maddie asked, wondering what she would have to become in order to one day get her crush.

Matt laughed, which made Maddie pout for a moment. His response surprised her.

“I just want a girl that doesn’t date me for what I do, but who I am. It is annoying when girls just want to date me because I play basketball.”

Maddie paused for a moment, before she responded, “Well I think you’re really nice and funny! I don’t care you play basketball…”

Matt laughed once again.

“Thanks Maddie,” he responded, “But you are too young for me right now. In a few years I’d be honored to be able to date a girl like you.”

That response would be stuck in Maddie’s head for the next five years.

From that moment on, Maddie decided to never date another boy until she could date Matt. Even though they rarely saw each other, Maddie would always cling to his arm and cherished every moment with him. Unfortunately for her, Matt seemed to be oblivious of Maddie’s feelings, and two years later, he left for college.

Maddie was fifteen when Matt left for college, and spent most nights after school hoping for a response when she would either text him or send him a message through social media.

One day, shortly after her sixteenth birthday, Maddie found her mother’s dildo and discovered how to masturbate. She purchased her own dildo and pretended it was Matt’s cock almost every night. By doing this, Maddie felt less alone and almost felt like she was really Matt’s girlfriend.

Through most of this time Matt was busy having crazy college experiences with girls his age. Even though he was with many girls, he was never in a committed relationship.

During the summers, Matt would come home and see Maddie at a golf outing that their family friends had annually. For three years, Maddie would jump into his cart and play a round of golf, just the two of them. Each year, Maddie would put on something more and more revealing, attempting to make Matt see her in a different view.

It was a day of the year that Maddie thought was better than Christmas. An entire night alone with the boy she had the biggest crush on for what felt like an eternity.

At sixteen, Maddie had begun to start looking more attractive. By age eighteen, her senior year of high school and Matt’s senior year of college, she had a full chest and curvy body for her size.

At high school, Maddie had developed the title of a tease because almost every boy there wanted to date her, but she declined every offer. She claimed she had already made a commitment to someone else, never elaborating on who exactly.

The time came for the golf outing, and it was a cloudy day out. There was a chance of rain, but the outing went on anyway. Hoping that it would rain, Maddie wore a tight, white collared shirt to golf in which she noticed caught Matt’s eye when he showed up.

The two spent the first few holes catching up and having a great time. Maddie noticed Matt staring at her body a few times, specifically when she was bending over to place her tee.

During the middle of the fifth hole, it started to downpour. Each of the holes had a storm shelter on it, and since the course was so spread out, the two ended up having one to themselves, secluded by the downpour of the rain.

By the time the Matt and Maddie had made it to the shelter, they were each soaking wet. Maddie looked down and blushed as she noticed her fully erect nipples poking against her tight shirt. She looked up to see Matt had noticed too. He quickly looked away.

“So,” Maddie started with a seductive tone, “Do you think I’m old enough to date yet?”

Matt could only nod as Maddie moved in closer.

She had prepared for this moment for almost five years, but she was still incredibly nervous.

Her breasts were now pressed up against Matt’s chest as she felt warmth coming off of his body. She nuzzled into his chest and then moved her finger down from his sides to his pants.

Matt jumped back. “What are you doing? Where is this coming from?”

Maddie only responded with grabbing him and moving him closer.

“I’ve wanted to be yours for five years. Ever since you babysat me that one day I knew you were special. All I’ve dreamt about is you being able to call me your own, and you haven’t dated anyone else. I figured you were waiting for me too.”

Matt had no idea what to say. It was true that he had not been in a relationship for the past five years, but was he waiting for a girl like Maddie?

He looked down and saw the girl buried in his chest, squeezing his waist waiting for an answer. Even if it didn’t work out, at least it would make Maddie happy until he figured out what he felt.

“You haven’t chosen a college yet have you?” Matt finally asked.

Maddie looked up and shook her head no, tears filling her eyes.

“You should go to the college in town. That way we can be together.”

He leaned down and kissed her.

The rain continued to pour as they kissed, and Maddie eventually pulled up her shirt, revealing to the first man her large, now developed breasts.

Matt kissed down her neck and began to lick them while Maddie began to unbuckle Matt’s pants. Maddie reached her hand inside to feel the warmth emanating from Matt’s cock. It was a little thicker than her dildo too. She stroked it gently, feeling the blood rush to the tip.

Maddie then laid on her back against the picnic table and moaned in ecstasy as her dream was coming true. Matt continued to lick and suck on Maddie’s breasts and nipples while also moving her skirt up, revealing no panties underneath.

Maddie then used her feet to pull down Matt’s boxers, as his cock began to grind against Maddie’s virgin pussy. After a few moments of grinding, Matt lifted Maddie’s feet into the air and prepared his cock for entry.

“Gently please, I’ve been saving myself for you,” Maddie whimpered.

Matt moved his cock in and out slowly as Maddie’s pussy adjusted to the size.

Thunder boomed as Matt suddenly thrusthis cock fully into Maddie forcefully. The pleasure was unlike Maddie had ever experienced before. Slowly moving faster, Matt also enjoyed how tight she was, but also realized that he had never encountered a connection like this with anyone he had sex with before.

They stayed in the same position for about a minute, getting faster and faster until Maddie’s body straightened out and began to convulse with pleasure. Matt noticed her cumming and stopped, leaned in, and began to passionately kiss Maddie on the lips.

Maddie eventually pushed him back and then bent over the table, spreading her ass to reveal her holes for Matt to see. Matt then entered her pussy again, causing her even more pleasure as it hit whole new areas that made her moan loudly, drowned out by the thunder and pouring rain.

She could feel another orgasm coming and said between breaths, “Matt… come inside me. It’s okay... I’m on the pill…”

Almost as she finished the sentence she felt warmth fill her insides. She turned her head around to see Matt’s face wincing in pleasure as he came into her, not letting a drop escape from inside her.

They kissed again as they began to put on clothes. Maddie quickly grabbed panties out of her purse, and put them on, attempting to prevent as much cum from escaping.

Matt laughed playfully as he watched Maddie struggle to retain the fluids. They both began putting all their clothes back on as the rain died down.

This was just the beginning of their lifelong adventure together.
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