Will burst out laughing.

“Hahaha! I never expected you to like this sort of stuff! Bet you’ll look hot in it though.”

Helen was confused for a few moments, before correcting Will’s misunderstanding.

“No, darling. I’m not the one who’s gonna wear this.”

Will was still laughing, but it started tapering off a bit.

“What do you mean El? If you’re not gonna wear it, who is?”

Helen didn’t respond. She closed her eyes and lifted the clothes hanger to the ceiling.

“Bídeog.”

Her hand flashed white for a second, and the outfit shrank to Will’s size. He had ceased laughing completely.

“Wait, wait, wait.”

Helen giggled.

“You can’t be serious.”

“Oh, I’m serious. Dead serious.”

Helen gave Will a very menacing grin, which shook the young man.

“I don’t want to have to punish you darling! I’ve done a lot for you since getting together, so now it’s your turn.”

“I can’t! This is so humiliating.”

“Oh, you will do it. That much is certain.”

Will grumbled, but he knew she was right. Helen loved him very much, but he understood better than anyone that it’s not wise to defy her.

Helen dropped the shrunken clothes on the dresser in front of Will. He picked them up and took them inside of his dollhouse silently.

“Great! Don’t come out until you’ve got it all on!”

Inside his living room, Will took a good hard look at what he was about to have to wear. He held in his hands a crude, fetishistic, and tasteless mockery of a typical Japanese schoolgirl uniform. It was small and white with a pink ribbon, collar, and cuffs. The top was short sleeved and very tiny. The accompanying pink skirt was also quite short. It came with a pair of thin white knee socks and black dress shoes. Perhaps the most embarrassing item of the whole cosplay was the pink wig, with black ribbons placed on each side.

Will bit the bullet and began undressing from his usual outfit, until he was completely naked. He considered keeping his boxers on, but was afraid that Helen wouldn’t appreciate seeing them if she peeked under his skirt, which was very likely. He began by putting on the top. It was a bit small for him, clearly made for a female. He managed to get it on after struggling some, and looked himself in the mirror. His mind was overtaken with humiliation, even though no one was watching him. The small top only went down to his ribs. His entire stomach would be visible.

Will continued to swallow his pride and put on the skirt. It took him a minute to figure it out, but he eventually managed. He took another look in the mirror. The skirt and top combo looked a bit better than just the shirt by itself, but it was still very embarrassing. Will slid on the thin knee socks and black shoes. Even though they were made for girls, they fit well on Will’s small feet.

While Will wasn’t enjoying the embarrassment of this at all, he couldn’t deny that it was shockingly comfortable. In particular, going commando with a skirt on felt great. So much so that he considered keeping this one for future use. He finally put on the wig and took a good hard look in the mirror, one last time before facing his girlfriend.

Seeing himself cross dress made Will realize how androgynous he actually was. He rocked the outfit, almost looking like a professional cosplayer. His small, skinny, and short body perfectly complemented the look, and his light brown skin made a satisfying contrast with the white and pink of his cosplay. The complete lack of body hair also helped.

Will was shocked at how he look strangely… cute? It was an embarrassing thought, but he couldn’t deny that he kind of enjoyed seeing himself wear this. He had never been confident in his looks, but right now he felt pretty. He took a deep breath, and walked towards his front door.

* * *

Will hesitantly stepped out out of his dollhouse and stood in front of the entrance. Helen slowly lifted her gaze up from the magic book she was reading and looked over at Will. Her face froze for several seconds, eyes wide.

Will stared up a her with his hands behind his back and a flustered look on his face.

“Oh my god.” 

Helen said to herself.

“You. Look. So. Cute!!!”

Her eyes lit up. She looked like a ten year old who just got a PS5 for Christmas. Helen slammed her book shut and ran over to the dresser, lowering her face just a few inches from Will. She was breathing heavily, and Will could smell her sweet, mint scented breath.

“Oh, I could just eat you up, I could just eat you up!”

Will chuckled nervously. He really didn’t like the mental image of being “eaten up” by his giant girlfriend, even though she didn’t mean it that way.

Helen grasped Will tightly in her fist and began planting dozens of kisses across his face and body.  She was manic. Will was weirdly enjoying himself. The outfit had grown on him, and he was amused seeing his girlfriend so elated. 

Helen held Will in her hand left hand, while touching and prodding his body with the fingers of her other one. She ran fingers across his cheeks, flat stomach, legs. She held Will over her head to get a peek under the skirt.

“Ah, letting it all hang out I see!”

Will chuckled.

“I didn’t really know what you wanted in that region, so I opted for nothing.”

“Haha, good choice. You’ve got quite a package, I must say! You’re really pretty down here.”

It felt strange to have his cock and balls called “pretty,” but he couldn’t refuse a compliment.

“Haha, thanks El.”

“Alright, now you’re gonna pose for some photos!”

“Sweet!”

Will couldn’t believe that mere minutes ago he was dreading this. He and his girl were having a blast.

* * *

“Alright, give me a big smile and hold up double peace signs!”

Will made the corresponding pose, and Helen snapped the pic with her smartphone.

“Ahhhh!!! You are so cute, I just can’t take it!’

Will loved watching Helen’s heart melt at his silly poses. All insecurity and shame was gone; he was here to please his lover, nothing else mattered.

“Oh, I just got a great idea! Wait here one second.”

Helen stepped out of the room for a few seconds before returning with a small battery powered desk fan. She placed it on the floor in front of the dresser, pointed it up at Will, and turned it on full blast. Will’s skirt was blown upwards over his torso, exposing his junk.

“Eh?”

This all came as quite a shock to little Willie.

“Do the Marilyn Monroe pose! The one where she’s stopping the wind from blowing up her dress.”

He was vaguely familiar with what she was talking about. He placed his hands over his crotch, stopping the skirt from showing his package in all it’s glory.

“Perfect!”

Helen snapped the picture.

“Take your hands off now. I wanna get a naughty one, heheheh!”

Will gave Helen a wry smile and held his hands behind his back. He stared off into the corner and made a cutesy facial expression as his skirt blew up over his abdomen.

Helen snapped several pictures, all from different angles, with the biggest, stupidest grin on her face.

“I wanna get one where it’s erect!”

Will began to reach down to touch himself, but Helen stopped him.

“Wait, wait, wait, I know a better way.”

Helen put down her smartphone and took her shirt off, throwing it on her bed. Will stood stunned. She was wearing an expensive looking, black lace-trim bra. It was very big and had an intricate design. Helen smiled at the speechless Will.

“Hehe, I thought you would like it.”

“Like” didn’t begin to describe it. She was so sexy it hurt. Will’s penis immediately sprang to full mast.

“I’m not done yet, though.”

Helen reached behind her back and undid her bra. She flung it away onto her bed, letting her tits hang out unobstructed. They were just plain beautiful. So beautiful, it was hard to believe they even existed. They were very large, milky white in color. The nipples were a perfect size and shade of pink. They had an aesthetically pleasing round shape, and were naturally perky.

“There it is!”

Helen snapped the picture of Will with an erection, but he was too transfixed on her udders to even really notice. Helen giggled at his reaction, or lack thereof.

“All right, time for the last part of our photography session. I’m going to being filming, and you’re gonna jack off to my tits. I’ll turn it off when you cum. Sound good?”

Will nodded his head rapidly.

“Okay then, three, two, one…”

Helen tapped the record button on her phone.

“Go!”

Will grabbed his cock and immediately began beating it hard. He was circumcised, but cut in such a way that he could jack off without needing lube. Behind the camera, Helen was running her hand across her chest, groping her own breasts, and making sexy faces at Will. After a short interval of time, he came. Ropes of semen shot out from his cock as he fell to his knees with a loud moan. The wind from the fan blowing his skirt up kept him from getting his cosplay dirty.

The nut was so good, he nearly passed out. He laid on the dresser with his eyes closed for a few minutes. The airflow from the fan went out, meaning Helen must have cut it off. He slowly pulled himself up and opened his eyes to look at his girlfriend. While he was laying there, she had put on a grey t-shirt.

“See?  That wasn’t so bad after all, was it? Don’t lie to me; you had fun wearing that outfit!”

“You bet your ass I did!”

The couple exchanged mutual laughs.

“I’ve got a lot more that I want to see you wear in the future. I’m so excited, oh man!”

“Hey, wait…”

Will said suddenly.

“Where did my load go? I shot a lot out. It should be all over the dresser, but I’m not seeing anything.”

Helen grinned and licked her lips.

“That’s a good question Willie. I guess we’ll never know!”