Babysitter Flashback
One Foot Tall Fiancé
chapter 17
by
copier
· original author:
rpcity
A smile crossed your face as you remembered a very specific woman from your past life, Irina squealed as she recognized the expression.
"Ooooh! There is someone isn't there!? I knew it! Tell us tell us!" she practically shouted.
Even Kimberly was curious. Partially because she hoped she could turn this little nostalgic romp into a trap to keep you away from her daughter permanently. She was all ears.
--FLASHBACK BEGINS---
"But mom! How many times do I need to tell you, I don't need a babysitter! I'm old enough to just stay at the house by myself!" you whine.
As you entered your teenage years, your Aunt Tara had convinced your mother that she needed to separate herself from her needy son and give herself some time to let loose. For the past few years, the sisters had been going out at least once a week. Unfortunately for you, your over protective mother refused to leave you in the house by yourself. Despite your constant protests, you saw a seemingly endless line of babysitters tromp through your house to "protect" you, even though you were mostly in danger with others around and safer alone.
These babysitters came and went, they were all a few years older than you - usually college students at the nearby community college that your mother or aunt had met at the gym or daughters of their friends. Because of their usual affiliation with Tara, the one thing you could count on was that they rarely had your best interests at heart. You were always thankful to see them leave, although they usually left you flattened and tucked away in bed. You saw more action than was likely healthy for a hormonal teen, yet your mother continued to bring them to your house.
Even now at 18 years old and preparing to graduate high school, your mother was preparing to introduce yet another new babysitter.
"Jake, this is June. Be sure you mind her and don't give her any trouble," your mom made quick introductions as she scrambled out the door to meet up with Tara.
For the first time, you were stunned to silence at the site of your sitter. June was statuesque. The tall blonde likely had an athletic background, but looked as though she gave up on regular exercise midway through high school. She carried her eye catching curves like a professional. Her round ass bounced and shook with every step she took and her tits jiggled with every breath she took.
June knelt down to pick you up in a gentle fist.
"Hey Jake. You don't look like you'll be too much trouble. Your aunt told me you're not too fond of traditional babysitters, so I'll make sure we both have some fun tonight. Ready for some sitting?" she asked with a giggle.
You wordlessly and dumbly nodded as June laughed and simply moved you to her waist where she let you tumble into her skin tight leggings. She moaned quietly as she felt you impact her bare flesh.
"Mmm, well it feels like you're all ready. I should get comfortable too," she said with a giggle as she not so gently plopped her ass onto your sofa and squirmed to get comfortable.
Normally this is where you started inwardly cursing your mom's desire to keep you under constant supervision, but something was different with June. Being squished beneath her perfumed ass felt like heaven.
--END FLASHBACK--
Kimberly and Irina giggled.
"So that was June. I complained a lot less about having a babysitter most of that year. That first visit she was content to just sit quietly, but she got a lot more aggressive after that. She'd have me wrestle her, or play cat and mouse...sometimes she'd even bring props or toys to use...." you drift off and quickly cut yourself off, remembering that you're talking to your future mother in law and her best friend.
"Oh I see," Irina said with a giggle. "And what's your missed opportunity?" she asks, prodding you further.
"Well, after a few months she transferred to a different school, I got a much more typical babysitter, and never saw her again. I never did work up the courage to tell her how much I enjoyed our time together. I just wish I would have spoken up at some point. Who knows what could have happened. We were just a couple of years apart after all...." you say wistfully.
Kimberly smiles and bounces you between her cheeks.
"Ok then Jake. I'll play the role of June, you be yourself, and let's see how this plays out shall we?" she giggles in anticipation.
...."Ok Jake, looks like your mom is gone. Ready to get comfortable?" Kimberly said getting into character immediately.
You shake yourself awake, surprised by how quickly Kimberly adapted to the role.
"....a....actually June, before we get started..."
"Ooooh! There is someone isn't there!? I knew it! Tell us tell us!" she practically shouted.
Even Kimberly was curious. Partially because she hoped she could turn this little nostalgic romp into a trap to keep you away from her daughter permanently. She was all ears.
--FLASHBACK BEGINS---
"But mom! How many times do I need to tell you, I don't need a babysitter! I'm old enough to just stay at the house by myself!" you whine.
As you entered your teenage years, your Aunt Tara had convinced your mother that she needed to separate herself from her needy son and give herself some time to let loose. For the past few years, the sisters had been going out at least once a week. Unfortunately for you, your over protective mother refused to leave you in the house by yourself. Despite your constant protests, you saw a seemingly endless line of babysitters tromp through your house to "protect" you, even though you were mostly in danger with others around and safer alone.
These babysitters came and went, they were all a few years older than you - usually college students at the nearby community college that your mother or aunt had met at the gym or daughters of their friends. Because of their usual affiliation with Tara, the one thing you could count on was that they rarely had your best interests at heart. You were always thankful to see them leave, although they usually left you flattened and tucked away in bed. You saw more action than was likely healthy for a hormonal teen, yet your mother continued to bring them to your house.
Even now at 18 years old and preparing to graduate high school, your mother was preparing to introduce yet another new babysitter.
"Jake, this is June. Be sure you mind her and don't give her any trouble," your mom made quick introductions as she scrambled out the door to meet up with Tara.
For the first time, you were stunned to silence at the site of your sitter. June was statuesque. The tall blonde likely had an athletic background, but looked as though she gave up on regular exercise midway through high school. She carried her eye catching curves like a professional. Her round ass bounced and shook with every step she took and her tits jiggled with every breath she took.
June knelt down to pick you up in a gentle fist.
"Hey Jake. You don't look like you'll be too much trouble. Your aunt told me you're not too fond of traditional babysitters, so I'll make sure we both have some fun tonight. Ready for some sitting?" she asked with a giggle.
You wordlessly and dumbly nodded as June laughed and simply moved you to her waist where she let you tumble into her skin tight leggings. She moaned quietly as she felt you impact her bare flesh.
"Mmm, well it feels like you're all ready. I should get comfortable too," she said with a giggle as she not so gently plopped her ass onto your sofa and squirmed to get comfortable.
Normally this is where you started inwardly cursing your mom's desire to keep you under constant supervision, but something was different with June. Being squished beneath her perfumed ass felt like heaven.
--END FLASHBACK--
Kimberly and Irina giggled.
"So that was June. I complained a lot less about having a babysitter most of that year. That first visit she was content to just sit quietly, but she got a lot more aggressive after that. She'd have me wrestle her, or play cat and mouse...sometimes she'd even bring props or toys to use...." you drift off and quickly cut yourself off, remembering that you're talking to your future mother in law and her best friend.
"Oh I see," Irina said with a giggle. "And what's your missed opportunity?" she asks, prodding you further.
"Well, after a few months she transferred to a different school, I got a much more typical babysitter, and never saw her again. I never did work up the courage to tell her how much I enjoyed our time together. I just wish I would have spoken up at some point. Who knows what could have happened. We were just a couple of years apart after all...." you say wistfully.
Kimberly smiles and bounces you between her cheeks.
"Ok then Jake. I'll play the role of June, you be yourself, and let's see how this plays out shall we?" she giggles in anticipation.
...."Ok Jake, looks like your mom is gone. Ready to get comfortable?" Kimberly said getting into character immediately.
You shake yourself awake, surprised by how quickly Kimberly adapted to the role.
"....a....actually June, before we get started..."
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March 28, 2025
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