Too Old for a Babysitter? Ch. 01

"Oh, come on! A babysitter?"

Jeremy looked at his parents in disbelief.

"That's right." His mother replied, sternly. "We'd like to find the house where we left it."

"But I'm eighteen!"

"You turned eighteen three days ago." Jeremy's dad interjected. "You're still in your last year of high school. And you're still very much the same kid who set the couch on fire with a cigarette."

"That was an accid-"

"Come on, Jeremy." His dad said, with a smile. "Give it up, buddy."

The boy sighed, defeated.

"So, who's coming to b- To watch me?"

"June." Replied his mother. "You like her, don't you?"

Jeremy nodded, glumly. Yes, June was nice. She had a sweet face and a good sense of humor.

"So, when are you guys leaving?"

"In about an hour."

"Alright."

"You be good with June, Jeremy." Said his father. "Prove to us that you've really matured and we'll trust you enough to leave you here alone. Deal?"

"OK."

"And if your grades pick up a bit, we'll trust you even more." His mother added.

Jeremy groaned, then left the room.

A babysitter. How humiliating!

Fifty minutes later, the doorbell rang. Jeremy went to open the door.

"Hey there, birthday boy."

"Hi, June."

The woman walked inside, beaming at him. She was 36 years old and stood a few inches taller than the boy. She had bright blue eyes and a pretty pale face. Her skin was flawless, with a tiny hint of freckles. Her hair was brown and tied in a neat ponytail, leaving just a small lock of hair dangling on her forehead. Whenever she came over to watch Jeremy, she wore large, shapeless sweaters and plain jeans.

"My birthday was three days ago." The boy said.

"I know that!" June said. "But I didn't get a chance to wish you happy birthday in person!"

She gave him a sudden hug, catching him by surprise. She had never hugged him before. For the first time ever Jeremy realized that, hidden under those shapeless sweaters, June seemed to have quite the body. He felt two large, firm breasts pressing on his chest and enjoyed the comforting warmth of the embrace.

The hug lasted more than he had expected and, with a jolt of panic, the boy realized that his dick was getting hard. Really hard.

"Lovely." June said, squeezing him a little more.

Was she talking about-?

"Hi, June!" Jeremy's mother said, from the other room.

June gently let go of Jeremy, giving him a strange little smile that he didn't quite understand. The boy cleared his throat, hoping his massive erection would go away before June or his parents would see it.

"Hello!" June replied. "Here I am."

"You're a life saver." Jeremy's father said, walking in the living room to join them. "Sorry for the short notice."

"Not a problem."

"Honey, are you ready?" The man said, calling for his wife. "I don't want to be late."

"Coming!"

Jeremy's mother soon arrived, putting her earrings on.

"Ready."

"So, where are you guys going?" June asked politely.

"Business dinner. My boss organized it out of the blue. Only told us last night."

The man sighed.

"Well, we better be off."

"Thank you for watching him, June." Said Jeremy's mother. "I hope he'll be a good boy."

"Mom!" Jeremy said, embarrassed.

"Oh, I'm sure he'll be wonderful." June replied, with a bright smile. "You guys have fun."

"Thanks, bye!"

"Bye, June! Bye, sweetheart!"

The two parents rushed out, leaving the boy alone with his babysitter. A few moments later, they heard the car start and head out of the driveway.

"Alright." June said. "What would you like for dinner?"

Jeremy shrugged. He couldn't help but feel annoyed by his parents' behavior.

"I know this must be frustrating for you." June said, with a gentle smile. "Me being here, even if you're eighteen."

He nodded.

"It's nothing against you, June. I just wish they'd treat me like an adult. Or, at least, not like a child."

"I know." She said, stroking his shoulder. "But let's try to have fun anyway, OK?"

The boy nodded again, thinking that she was far more physical than usual. Usually, she never really touched him. He didn't mind, though.

"Think of it as a dinner among friends."

"Alright." He said, smiling. "How about we order some pizza, then? It's on me."

"You charmer." She said, with a giggle. "You're on."

"Great. Two pepperoni? "

"Perfect. I love sausages."

He got out his phone and called the pizza place. As he placed the order, he realized that June's words had sounded like a double entendre. Had it been intentional? And was it his imagination, or was she kind of staring at him?

"OK. Should be here in about fifteen minutes."

"Great." She said. "How about we find a movie to watch, in the meantime?"

"Sure."

They headed towards the couch. He sat down at his usual place, at the center, and picked up the remote. Usually, June sat at the edge of the couch, a foot away from Jeremy, but this time she sat right next to him. So close their legs were rubbing each other.

"Do you mind if I sit here?" She asked. "I'm kind of cold."

"Er- Sure."

He went through Netflix, looking a for a movie.

"What genre would you like? Action? Comedy? Horror?"

"Horror sounds like fun." She said, leaning her head on his shoulder.

OK, that was definitely a first.

"Er... right. Horror."

She looked up at him with those big, blue eyes. He had never quite realized how beautiful they were.

"So... How did you spend your birthday?"

"Oh! Well, I hanged out with a few friends, you know. Drank a few beers, had a few laughs. Regular Saturday night, really. It was fun."

"Guy friends?"

"Er- Yes, just us guys."

"And what about your girlfriend?"

He blushed, looking at the screen and trying to ignore her concentrated gaze.

"I... I actually don't have a girlfriend."

"I find that very hard to believe." She said, placing a hand on his knee.

"What do you mean?" He said, still looking at the screen. Her touch was starting to give him another erection. No girl had ever touched his knee like that. He felt very awkward and didn't know what to do.

"You're a sweet, funny, handsome boy. I would have thought girls would be lining up to date you, honestly."

He chuckled, a little shakily.

"Oh, yeah. All around the block."

June placed her other hand on his cheek and turned his head around. They stared at each other and the intensity of her eyes sent violent, pleasurable shivers down his spine.

"I mean it, Jeremy. You're quite the catch. Don't ever doubt it. If those little cockteases at school don't see it, it's their problem."

The hand that had been resting on his knee suddenly moved up his thigh.

"You are a very, very special boy." She said, as her face got closer to his.

"June, what-"

The doorbell rang. The two of them jumped a little.

"Oh, that must be the pizzas." Jeremy said. "I'll- Er, I'll go get it."

"Sure, honey." She said with a smile. It was as if nothing had happened.

Confused, Jeremy got up and walked to the door. His erection was now massive. He tried to act normal, but he noticed June's satisfied gaze resting on his visibly erect penis. The jeans didn't hide it very well. He also realized that he rather enjoyed her gaze.

The doorbell rang again. Clearing his throat, the boy walked to the door.

"Yes, sorry! I'm coming!"

"Not yet, you're not." June whispered under her breath, as she watched him open the door.

Her smile was wide and naughty.

They ate their pizza on the couch, while watching some stupid horror movie with ghosts in it. It was not scary in the slightest, but they had fun ripping it apart and laughing at the terrible acting.

"That was good pizza." Jeremy said, placing his empty plate on the coffee table.

"It was." June agreed, putting her plate on top of his.

The movie was about half way through. It was still quite early.

"Mind if I use this?" June asked, picking up a blanket. "I'm still cold."

"Oh, sure."

Smiling, she unfolded the blanket and covered both of them with it.

"What are you doing?"

"Come on, snuggle with me! Warm me up!"

"I- Yeah, sure."

June rested her head on his shoulder. Uncertainly, he placed his arm around her. The blanket covered both their bodies, leaving only their heads out.

"Man, that actress just cannot act!" Jeremy said, with a grin. "She's so bad!"

"Yeah, her fake boobs are also pretty bad." June said, with a smirk.

"Yeah..." He agreed, a little uncomfortably.

"Do you like boobs, Jeremy?" June asked, with nonchalance.

The boy felt a huge rush of blood to his cheeks.

"I... Er- What?"

June giggled.

"Oh, come on. It's an easy question! Do you like boobs?"

She was staring at his face now, the movie completely forgotten.

He kept looking at the screen, but he wasn't paying attention to it. He felt his heart thunder in his ears.

"I... Yes, of course I do."

June smiled.

"And do you like them small or big?"

He blushed even harder, which he didn't think was possible.

"June!"

"Oh, come on. It's just an honest question." She said, with a naughty smile. "Please answer me. I'll make it..."

Her hand crawled up his thigh. He let out a little gasp.

"Worth your while." She concluded.

Jeremy could feel his cock swelling. He didn't have much experience with girls, and the combination of her touch and the topic being discussed was... challenging.

"OK, OK... If you must know-"

"Oh, I must."

"If you must know, I prefer big boobs."

She grinned. Under the blanket her hand was now very close to his twitching manhood.

"Oh, do you now?"

He cleared his throat.

"Yeah..."

June moved the blanket, so that her chest was now exposed to the air. With her free hand, she pulled on her sweater, making it adhere to her body. Jeremy's eyes widened, as he stared and realized just how huge her breasts were. Also, judging by the hard nipples poking through, she wasn't even wearing a bra. They really were huge and, it seemed, incredibly firm.

"Like mine?" The woman asked, with a mischievous smile.

"I... Yes, like yours."

Jeremy felt her hand resting on his hard cock.

"Yeah, I can tell you do..." She said, deep satisfaction in her voice. Very gently, she started rubbing his erection.

Jeremey groaned, even that soft touch felt amazing.

"Did you know I had such big boobs?" June asked, as she kept stroking him.

"No..." He answered truthfully, trying not to moan.

He felt a violent urge to thrust his cock in her hand, but he managed to resist.

"I believe you." She said gently. "I've always been very careful about hiding my forms, when I work. It seems inappropriate, you know."

He nodded, still trying not to moan.

"Would you like to see them?" She asked, staring him with those beautiful blue eyes.

"June, I... I don't know if we s-"

She gently covered his mouth with her finger.

"Don't think about your parents or anything else. Just think about what you want. Do you want to see my boobs?"

He nodded.

"Wonderful."

The woman pulled up her sweater, exposing her amazing breasts to the light. The boy stared, in awe. Quite simply, they were magnificent. Each was the size of his head, if not larger. Despite their size, they didn't sag at all and actually stood proudly, defying gravity. Her nipples covered about a third of the surface and were a delicate shade of pink. They shined in the light, like glistening treasures.

"Holy fucking shit." Jeremy murmured, unable to help himself.

June chuckled fondly, clearly pleased.

"Why, thank you!"

She fondled her breasts proudly.

"Yes, these puppies definitely have their charm."

She pinched her nipples and gave him a lusty look.

"Would you like to touch them?"

"I... Really?"

"Yes, really. Surely you must have realized I'm coming on to you, Jeremy. I'm not being subtle about it, you know."

He smiled a little. With more confidence, he placed a hand on each breast and started fondling.

"Oh, yeah..." She moaned. "That's it..."

It felt glorious. They were soft, yet firm. Warm and smooth. He sat there, touching and admiring those amazing breasts, for what felt like an eternity. All the while, June moaned and smiled encouragingly at him.

"Good boy, good boy..."

Her hand found his cock under the blanket again. He was rock hard.

"Oooh, how about we take this out? I've shown you mine, you show me yours. It's only fair."

"I..."

Jeremy felt a little nervous. He had never taken his cock out in front of a girl. He didn't know if he had a good one or not. Would she like it? Would she-

June stuck booth her hands under the blanket and started unbuckling his belt.

"Don't you worry, honey. I can see you overthinking everything."

She unbuckled the belt and opened his pants, then started to stroke him through his briefs. They were wet with precum and she smiled appreciatively.

"You have no need to be nervous. Believe me."

She looked at him and smiled. He was still fondling her.

"I now want you to suck on my big tits. Do you want to do that?"

Jeremy nodded enthusiastically. What a night was this turning out to be.

"Good boy. Put your head right here."

He did as he was told, burying his face between her two monumental mounds. He rubbed his face against them, he licked them, he kissed them. Then, he started sucking on the nipples.

June whimpered with pleasure. They were clearly quite sensitive.

"Oh, yes... Just like that... Good boy..."

Meanwhile, she kept on stroking him through his briefs, under the blanket.

"I want to see that big cock. may I?"

Jeremy nodded, as he kept on sucking, fondling and resisting the urge to come in his briefs right then and there.

June pulled down his underpants and his cock sprang loose.

"What a magnificent thing."

Jeremy's cock twitched visibly, exposed to the warm air of the apartment. June looked at it lovingly, as if she had finally met with an old friend after a very, very long time.

Jeremy kissed June passionately, moaning in her mouth and squeezing her breasts.

Momentarily surprised, but definitely pleased, June returned the kiss with enthusiasm. Then, she finally put her fingers around his cock. A blissful moment for the both of them.

"Oh, God..." Moaned Jeremy.

"Oh, yes. Fucking finally!" June said. "Come here, baby. Lie on the couch."

She placed a cushion on her lap and placed his head there. He lied down, sucking her tits and stretching his legs. She caressed his hair with one hand, while stroking his cock with the other.

They stayed like this for a while, just enjoying each other's body. The room was full of excited, wet sounds and the moaning of the two lovers.

After a while, June stopped.

"Where are you-"

"Don't worry, honey." June said, gently lifting his head and standing up. "You stay right where you are. I just want a... closer look."

Jeremy could not believe his luck. June took off her sweater, then she climbed on the couch and placed her head right next to his cock. He could feel her breasts pressing on his thighs. Her warm breath on his shaft. She just stayed there for a while, resting on his lap and admiring his cock up close with a big smile on her face.

"Do- Do you like it?" He asked her, hating the slightly shaky quality of his voice.

She looked at him, a little annoyed.

"Seriously, Jeremy? You're asking that?"

"Well, I-"

"How's this for an answer?" She said.

And suddenly, she swallowed half his cock in one smooth motion, apparently without any effort.

"Oh, shit!" Jeremy moaned.

She bobbed her head hard, going deeper and deeper.

"Oh, Jesus, June! Where did you learn that?"

June kept on bobbing her head, but winked at him. She was incredibly hot. Her beautiful blue eyes, her hair, her jiggling tits. And the sounds! Those alone could have turned any man on.

She sucked and sucked for what seemed like an eternity. After about ten minutes, she freed his cock. There was a loud pop. June giggled and licked her lips.

"Delicious. Absolutely delicious."

Jeremy was in heaven. He had just lied there, enjoying the feelings and the sight. He could only grin a dumb grin.

"And I have to say, I'm very impressed by your stamina, babe. I've been with men twice your age who would have come after two seconds."

He blushed.

"It's your first time, isn't it?"

He nodded. No point pretending otherwise, right?

She smiled.

"Wonderful. It will be an honor. Now where's my pur-"

Jeremy's phone rang. He looked at the display.

"Ah, shit. It's mom. Just a second."

She nodded.

"Hey mom. Yes, everything is fine. Yes, we've had dinner. Yes, the usual piz- Gasp!"

June had started licking the head of his cock.

"No, everything is fine. I was- I almost dropped something. So, how's the dinner?"

Jeremy tried to concentrate, as June kept on licking his cock. He stroked her hair with his free hand and she gave him a loving look.

"Oh, you are?" Jeremy tensed up and June looked at him. "Sure, see you soon, then. Bye."

He hanged up.

"Fuck. They're on their way."

June looked crestfallen.

"How long do you think we have?"

"I don't know... Ten minutes, fifteen tops. Can... Can we make it?"

June shook her head.

"Nah, honey. Rushing your first time would be terrible. I want it to be good."

"But I don't-"

"Trust me, baby. Let's make it worth our while. You won't regret it, promise."

He nodded, glumly.

"Guess we should put our clothes back on, then."

"Why on earth would we do that?" June asked, genuine disbelief on her face.

"Well, you said-"

June laughed lovingly and stroked his upper thigh.

"Oh, bless your heart. Yes, we have to postpone having full on sex. But no way are you going to bed with blue balls, honey. I want your cum. Stand up."

He did as he was told, puzzled.

"I think it's time for your birthday present, honey." June said, with a naughty grin

She sat up on the couch, right in front of him. His cock was perfectly aligned with her boobs.

"Fuck these tits, Jeremy. Fuck the shit out of them. Now."

He almost came from her words alone. Still disbelieving, he placed his cock between her tits. June squashed them with her forearms, trapping his member in her soft, pillowy flesh.

"There you go..." She said, sheer joy on her beautiful face. "Fuck them, babe. You have ten minutes. Make them count."

Jeremy lost all control. He placed his hands around her face, gave her a kiss and started thrusting.

It was amazing. It was pure bliss. It was the most exciting, world-shattering experience of his young life.

He moved and moved, fucking those divine tits. All the while, June giggled and moaned and whispered encouragements.

"Yeah, fuck them, baby. Fuck my big tits. Fuck my big tits with you big, hard cock. Your delicious cock. Your beautiful, teen cock. Fuck your babysitter's tits. Fuck them. Fuck them!"

After five minutes of this, he started to feel very close to coming. June sensed it and had an idea. She leaned her head down and tried to see whether she could suck on the head, as it popped out of her cleavage. She could, easily.

"Oh, God!" Moaned Jeremy. He was so close, now. "You're amazing, June..."

She smiled at him.

"I know I am. And so are you, baby. But now, it's time to come, Come for me, baby. Fuck my tits and my mouth and drench me with your cum. Now."

Jeremy didn't need to hear it twice.

He started trusting frantically, moving his cock between her amazing breasts and inside her warm, wet mouth. He realized that his cock was so big, and his thrusts so hard, that, despite being between her huge tits, his cock still managed to choke her a little. She moaned and slurped and gagged a little, pure joy etched on every inch of her face.

He was fucking her tits and her face and she fucking loved every moment of it.

She looked up at him and winked. That was it. His muscles tensed. His mind started to cloud. His balls were tight and ready.