Senpai is My Dress Up Doll

“Heehee…It looks sooo good on you♡”

“Ugh…!”

A lone girl stood blushing and shaking in humiliation before me. The overly childish clothes she was forced to wear was only the start of her embarrassment.

You could ask a hundred people they’d all think this lovely creature in front of me was either a middle school girl dressed like a little kid or a well developed elementary schooler. Who in their right mind would have guessed that she was really a college boy even older than me?

Back when he first enrolled, all the seniors in the club he joined doubted he was even a fully grown man because of his androgynous looks. His cute, round eyes and baby face matched his slender limbs. With a height under 160cm, he looked like a middle school kid that had accidentally wandered onto campus and gotten lost. Although he didn’t seem like much at first, I took a liking to his quiet, gentle demeanour and ended up reaching out to him.

“With how androgynous you look, I bet you’d be one hell of a beauty if you ever tried dressing like a girl.”

Once that thought struck my mind I almost forced him – my unwilling senpai, into wearing my old clothes from elementary school, which ended up looking better on him than I expected. Ever since elementary school I’ve always been tall (right now I’m just shy of 170cm) and the clothes I wore back then were quite a bit bigger than the other girls my age. Even still, I was amazed that a grown man could squeeze into them. The cheap, girly colours that adorned him from head to toe matched his ever young features excellently. There wasn’t much in the way of room down south as you’d expect since the skirt was short to begin with, but it basically turned into a super-mini skirt on him which somehow gave off a strangely erotic vibe. His soft, silky hair was already on the long side so I tied it into two tails up top, and after applying some light makeup he was nothing short of a real cutie.

It was hard to tell with the denim skirt, but he seemed to be worried about his crotch with how he was fidgeting and rubbing his legs together, and I dared to say he was getting all hard and turned on from his first time crossdressing. When I casually pointed it out, his face turned a deeper red than I even thought possible and he hung his head with a flood of tears welling up in his eyes. I just can’t believe what an adorable creature he is.

I had only just realised it, but I guess I must have some sadistic tendencies by nature. Seeing senpai all cute and embarrassed like this just makes me want to bully him even more.

“Oh～? Is your dick getting hard from wearing my old panties?”

I moved my head in close to ears and whispered as he shivered like a small animal.

“You pervert♡”

In that moment senpai’s body sprang up and his eyes squeezed shut as if to say he couldn’t take any more of this. Tears slid down his long eyelashes and heavy pants streamed from his little mouth. It seems like senpai is quite the masochist himself, I take it.

“I-I’m sorry. I’m sorry…!”

?

I’m the one teasing him here after unloading this selfish request of mine, so why’s this guy apologising to me? Seeing him saying sorry dressed like a little girl was so comically cute in such a weird way that I couldn’t help but feel sorry for the poor thing.


“Heehee. Don’t worry. It’s not like I’m going to tell anyone. ♪”

A sigh of relief flashed across his face as I said that, but in exchange I told him he’d have to let me take a photo of him posing for me. He managed to force a smile on his face as he waved peace signs in both hands like I asked, and seeing him make such a laudably strained, twitching smile while dressed as a girl only fanned the fires of the sadist inside me all the more.

I’d wager that the very concept of disobeying my word didn’t even cross his meek, timid little mind. He probably doesn’t realise I could use this photo to get him to do whatever absurd demand I could want from him down the line.

Well as far as I’m concerned it just makes things easier for me, and besides, that ditziness is just another part of him that makes him so cute.

“Thank you kindly. ♪”

I beamed a smile full of gratitude towards him and I saw the faint traces of happiness peeking out from the shame of his bashful face. He can be a bit simple and absentminded sometimes, but he really is such a nice guy deep down.

It’s not like I didn’t feel a twinge of guilt from humiliating such a kind and pure-hearted boy. It’s just that it was outweighed by my arousal and high hopes of how I’m going to toy with this plaything I’ve just got my hands on. I mean, this little senpai of mine is just so much more than I ever imagined. I’d be crazy to try and hold back this overflowing lust inside of me.

Now I wonder what kind of clothes I should make him wear next. ♪

He looked at me with upturned eyes like a child checking if his mother is angry. I looked back with a sidelong glance at him restlessly pulling down the hem of his short skirt and I started pondering to myself what I’d try on him next.