Graduation Day
Tiny Brother VS Big Sister
chapter 29
by
copier
· original author:
rpcity
You smiled at Kate as she looked extraordinarily happy as you ate your egg whites and toast.
"All done Kate!" you sang as you swallowed your last bite with a bit of water. "Ready to get back to it?" you asked, finally at peace with the obvious conclusion that you desired to be near her soft, smooth backside.
"Actually Allen, today is going to be a little different," she said as she gently lifted you up. "Your first month is all done! Now, you still have your final exam of course, but from what I've seen from you I expect that you'll pass with flying colors and then it's off to the next set of drills," she said happily as she carried you into the next room.
"Oh..." you responded dejectedly. You had grown accustomed to your routine and would miss your time with Kate's ass, but if your trainer had taught you anything this month it was that you could expect your next month to be just as intense as the first. Your eyes widen as you see several women you recognize in Kate's living room - your aunt Susan, cousin Jennifer, sister Christine, and the woman from the gym Sophia who was "kind" enough to help you with your training.
"Wha...what's going on?" you ask nervously.
"Oh, they're all here to help with your final exam Allen. To make sure this last month was worth it. And once you pass, to celebrate your graduation!" Kate said happily before gently placing you on a cushion and gesturing for Sophia to step forward.
"Give him your best shot girl!" she sang. Sophia didn't have to be told twice. She had been waiting to get you back beneath her ever since that all too short session two weeks ago. She sprinted forward and jumped as high as she could before spinning in the air. To you, the Hispanic woman moved in slow motion, but in real time her ass cascaded down on you like an avalanche of flesh. You were instantly crushed flat, but sighed happily as you felt the familiar sensation of warm booty surrounding you. Sophia knew she couldn't enjoy this long, so she made the most of it - hopping in place and slowly grinding her ass across your body to ensure she cemented the memory of the feeling of your flattened form against her cheek.
"Susan, what would Allen's normal reaction be to something like this?" Kate asked her friend.
Your aunt laughed before answering. "Well, once he finally reformed, lots of moaning and groaning, probably a few choice swear words directed at your buddy. He hates being squished - says it hurts like hell. He whines a lot for such a little guy," she said with a smile.
When Sophia finally stood, the women surrounded you waiting for your reaction. As you finally popped back into shape, you sighed deeply with a contented look and a smile on your face.
"How did that feel Allen? Any pain?" Kate asked.
You shrug. "A little I guess. But it's worth it," you said with a smile in Sophia's direction. "Nothing I can't handle," you finish confidently.
Your family stand there in silent shock before Christine jumps in.
"That...that cushion must have made it too easy on him. Watch this!" she says as she knocks you to the floor before slamming her bare foot over your body repeatedly. "How do you feel now little bro?" she asks snidely once she finally removes her foot.
You pause for a moment. "Like I could use a shower?" you respond with a laugh. "Do you ever wash those things?" you say, pulling a laugh out of your aunt and Kate. Christine is furious. Squishing you just isn't as fun if you don't whine about it afterwards.
The women all congratulate you and Kate on the successful month and gather around to take pictures of the proud graduate. Most of them with you plastered against a massive ass or squished between a pair of tits. Even Jennifer gets involved now that she knows you can shrug it off. They all enjoy a healthy slice of cake, which you miss out on as you are sandwiched between Sophia's cheeks in darkness. She never enjoyed a cheat meal more.
Kate smiles and basks in the success of her program. She'll let you enjoy today, but tomorrow it's time to get started on month two, when the focus is....
"All done Kate!" you sang as you swallowed your last bite with a bit of water. "Ready to get back to it?" you asked, finally at peace with the obvious conclusion that you desired to be near her soft, smooth backside.
"Actually Allen, today is going to be a little different," she said as she gently lifted you up. "Your first month is all done! Now, you still have your final exam of course, but from what I've seen from you I expect that you'll pass with flying colors and then it's off to the next set of drills," she said happily as she carried you into the next room.
"Oh..." you responded dejectedly. You had grown accustomed to your routine and would miss your time with Kate's ass, but if your trainer had taught you anything this month it was that you could expect your next month to be just as intense as the first. Your eyes widen as you see several women you recognize in Kate's living room - your aunt Susan, cousin Jennifer, sister Christine, and the woman from the gym Sophia who was "kind" enough to help you with your training.
"Wha...what's going on?" you ask nervously.
"Oh, they're all here to help with your final exam Allen. To make sure this last month was worth it. And once you pass, to celebrate your graduation!" Kate said happily before gently placing you on a cushion and gesturing for Sophia to step forward.
"Give him your best shot girl!" she sang. Sophia didn't have to be told twice. She had been waiting to get you back beneath her ever since that all too short session two weeks ago. She sprinted forward and jumped as high as she could before spinning in the air. To you, the Hispanic woman moved in slow motion, but in real time her ass cascaded down on you like an avalanche of flesh. You were instantly crushed flat, but sighed happily as you felt the familiar sensation of warm booty surrounding you. Sophia knew she couldn't enjoy this long, so she made the most of it - hopping in place and slowly grinding her ass across your body to ensure she cemented the memory of the feeling of your flattened form against her cheek.
"Susan, what would Allen's normal reaction be to something like this?" Kate asked her friend.
Your aunt laughed before answering. "Well, once he finally reformed, lots of moaning and groaning, probably a few choice swear words directed at your buddy. He hates being squished - says it hurts like hell. He whines a lot for such a little guy," she said with a smile.
When Sophia finally stood, the women surrounded you waiting for your reaction. As you finally popped back into shape, you sighed deeply with a contented look and a smile on your face.
"How did that feel Allen? Any pain?" Kate asked.
You shrug. "A little I guess. But it's worth it," you said with a smile in Sophia's direction. "Nothing I can't handle," you finish confidently.
Your family stand there in silent shock before Christine jumps in.
"That...that cushion must have made it too easy on him. Watch this!" she says as she knocks you to the floor before slamming her bare foot over your body repeatedly. "How do you feel now little bro?" she asks snidely once she finally removes her foot.
You pause for a moment. "Like I could use a shower?" you respond with a laugh. "Do you ever wash those things?" you say, pulling a laugh out of your aunt and Kate. Christine is furious. Squishing you just isn't as fun if you don't whine about it afterwards.
The women all congratulate you and Kate on the successful month and gather around to take pictures of the proud graduate. Most of them with you plastered against a massive ass or squished between a pair of tits. Even Jennifer gets involved now that she knows you can shrug it off. They all enjoy a healthy slice of cake, which you miss out on as you are sandwiched between Sophia's cheeks in darkness. She never enjoyed a cheat meal more.
Kate smiles and basks in the success of her program. She'll let you enjoy today, but tomorrow it's time to get started on month two, when the focus is....
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May 30, 2025
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