The Sugar Baby

Shopping

Danny felt incredibly guilty. It had been a week since he had worn Ruby's pyjamas, and things had only gotten worse. How had it all snowballed like this?

The requests kept on coming from Sugar Daddy, and Danny was having to rely more and more on Ruby's wardrobe, which he hated. It felt like a betrayal. Like an invasion of her privacy. It had started with the pyjamas, but had extended into a couple of dresses too.

Before long, it all got too much.

"Hey Danielle, let me see your underwear xx"

This was too much for Danny. He felt guilty enough stealing Ruby's clothes, underwear was too far. He decided to reply bluntly to nip this in the bud.

"Sorry I don't have any nice underwear to show you."

Hopefully that would be that, but Sugar Daddy was persistent.

"That's not a problem my darling. Please go and buy some. I'll send you the money now".

Danny looked shocked, but then a notification pinged up on his phone.

"£100 transferred into bank account".

Fuck, he thought to himself. 

"I'd like some pictures ASAP. Get shopping baby" said Sugar Daddy.

Danny was nervous, but thought that this opened up a new opportunity. Surely underwear wouldn't cost anywhere near £100. He could pocket the rest and make a nice little profit, even if it did mean buying, and god forbid wearing, women's underwear.

He knew there was a women's underwear shop on the high street, so he headed out to go there and get it over with. 

Upon entering the shop, the nerves suddenly hit him. He didn't know what he was doing. What he needed. It was overwhelming, all the different styles and fabrics. 

Just as he was about to give up, he heard a voice behind him say "Hello miss, can I help you?"

He turned and saw a shop assistant, who stared at Danny's face and realised her mistake.

"Oh I do apologise sir, it's just from behind... you have lovely long hair you see... so I thought..."

"It's ok" Danny replied, eager to get this conversation over. "I'm looking for some, for some sexy underwear. Not for me of course!" he exclaimed a little too eagerly. "It's for my girlfriend." he lied.

"Of course, no problem at all. And do you have anything in mind?"

He shook his head, happy to go with what the woman recommended. After several more questions about colours and sizes, he found himself at the checkout with 1 bra and 1 pair of panties.

"That will be £85 please".

Danny's eyes widened in shock. He thought £100 would leave him about £60 or £70 left after buying underwear. This was madness! He begrudgingly paid the price and left the shop and hurried home, trying to hide the logo on his shopping bag from embarrassment.

Once back home, he checked his phone and saw that Sugar Daddy had left him quite a few messages, eager to see him in his new underwear.

Danny thought it was best to just get it over with, resentful of the fact he'd only made £15 on this deal.

He stripped naked and pulled the underwear out of the bag.

Firstly, he pulled the thong up his legs. It was a deep red colour and the feel of the soft lacy fabric as it grazed his smooth hairless legs gave him a tingling feeling. He shivered from the pleasure and grabbed the bra. This proved more difficult, as he struggled for several minutes with the clasp. Eventually he had them both on, and stopped to look in the mirror. An involuntary gasp left his body. 

He looked so different. His slim body suited the female underwear perfectly. He looked... good? No. He couldn't think that. That was so weird. But he did though. He couldn't help but acknowledge that the bra and panties kind of suited him.

Danny grabbed his phone to take the picture, before quickly realising the bulge in his panties. He hastily tucked his penis and balls between his thighs and squeezed them in place, before snapping a picture and sending it to sugar daddy, careful to make sure his neck and head weren't visible. Only his long hair that fell down beneath his shoulders could be seen.

He fell backwards on the bed still wearing the underwear, staring at the photo of himself.

As the messages came in from sugar daddy complimenting him, he continued to stare at the photo, mesmerised by his lovely feminine looking body.