Here's the third place caption idea from the poll I ran a few days ago!

Art by: ふとん

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“Ah fuck me! The damn thing doesn’t even fit!” Alex complained as he tugged at the clasps of his custom fitted bra, each tug digging the cups deeper into his ridiculous breasts. With the help of his older sister, who was oddly being very helpful and understanding of his changes, he had managed to get some clothes that fit his new body but because of his ludicrous tits he had to get a custom bra fitted. Unfortunately for Alex, after waiting for over a week for an expensive custom fitted bra, the bra was very obviously multiple sizes too small for him.

“Fuck Hailey!” Alex was frustrated as he struggled to get his bra fully on, “It’s not my fault she has cow tits!” All of Alex’s troubles had begun one day in school when he decided to pick on his peer, Hailey, who had macromastia which gave her rather large breasts for her size. Alex thought nothing of it at the time but his teasing of Hailey’s ‘Cow Tits’, as he put it, had eventually gotten to her as she had run out of the classroom in tears.

The following day Alex had awoken to a pile of flesh pinning him to his bed, his panicking alerted his older sister who found him and helped unpin him. She worked through with him what had happened and had offered to help him through this, which she first let him borrow some of her clothes to fit his new feminine body. The more awkward thing was finding a way to cover his new tits as no store would hold a bra that even came close to fitting him. They eventually found a custom bra fitting company who would send someone down to their house to measure him.

This day eventually came which was deeply embarrassing for him as some strange man was wrapping a cold measuring tape around his lewd tits. He could tell that the man measuring him hadn’t expected to see a girl of this size as he kept ‘accidentally’ tying the measuring tape too tightly around his bust. Alex managed through it anyways and then waited for days in his house, feeling the full weight of his breasts slowly torturing his back.

“Come on!” Alex felt his small arms straining as he barely got the clasp of his bra done. “Oh my god! I did it!” Alex began celebrating which sent his breasts bouncing and swaying. “Man the weight of these was starting to kill my back!” His celebration was cut short as he heard a slow tearing noise coming from behind him. “Oh fuck…” The tearing noise quickened to a loud and sudden rip as the back bands of his bra tore away, the sudden release of his massive tits weight pulling him forward as he fell onto the ground.

“Alex, are you okay? I heard a loud noise and I-” His sister ran into his room and laid her eyes on her brother, now sister, laying atop her breast that dwarfed his body as he struggled to get up.

“I’m fine I…I just can’t get up!”