The Sugar Baby

The Request

It had been a few days since Danny's first sale and business was... well it wasn't quite booming, but it was getting there.

He was now £150 richer and had been selling pictures of his feet with his red nail polish on to at least half a dozen men.

That still made him uncomfortable, but he tried not to think about where the pictures were going. Until one day he checked his phone, and it became very apparent the reality of what he was doing.

"Inbox: 1 message" read the notification from the app.

That was strange, he hadn't even realised he could get messages on there.

He opened it up, and saw a message from a man calling himself "SugarDaddy69". Danny didn't know what a sugar daddy was, but he recoiled at the sexual implications of the 69. Despite being grossed out, he opened the message:

"Hey baby. Gorgeous feet. Would love to see you in some strappy heels. Willing to pay more xx".

Danny didn't like being called baby. That didn't do his fragile sense of masculinity any good. But the promise of more money was appealing. He was still a long way from being able to buy his ticket, and if this would help him along the way, what harm was there. He was already in quite deep anyway. He had to just keep thinking of Ruby in a bikini. Remember why he was doing this.

There was only one problem though, he didn't have any heels. It seemed counter productive to buy some, since he was trying to make money not spend it. He thought for a minute, before an idea occurred to him.

"Ruby?" he called out. "Ruby? Are you in?". He walked down the hallway and knocked on her door. "Ruby?" he called again. She was out. He wasn't sure how long she'd be out, so he acted quickly. 

He opened her door and made a beeline for he wardrobe, where he saw a pile of shoes at the bottom. They were a mixture of trainers, boots, sandals, and the item he was looking for. Heels. He quickly rummaged through the pile before emerging with a pair of strappy silver heels that, annoyingly but conveniently, were exactly his size. He quickly shut the wardrobe and returned to his room, worried that Ruby might suddenly return.

Once in the safety of his room, he calmed down a little. He sat on the bed and took his socks off, then slowly examined the heels. They had a thin heel that was maybe 4 inches high, and had a silver strap that went across the foot just before his toes. There was another strap higher up that fastened around his ankle.

He felt quite nervous. This was another step further for him. First the nail varnish, now the heels. But he had to remember, it was all for a good reason. All for Ruby. All for his future. For him to be the man he needed to be to get his dream girl.

As he slipped on the heels, the irony wasn't lost on him that in his quest to be a worthy man for Ruby he was wearing her shoes, but he laughed that off. It was only a temporary thing and no one would ever know.

Danny fastened the straps and stood up to get his phone, but he stumbled as he did so.

"Fuck", he thought to himself, "how to girls do this".

He gingerly manoeuvred his way across the room and grabbed his phone, quickly taking several pictures of his feet, with his bright red toe nails and silver heels. He winced at how feminine he looked, but reminded himself that it was the only thing keeping the dream of Australia alive.

Once the pictures were taken, he was unsure how to proceed, so he messaged SugarDaddy69 back.

"Picture is taken. £50 before I send".

Danny was unsure if this was how it worked, but the man had said he would pay more so he thought he'd try his luck.

He threw his phone down and unstrapped his heels. He quickly threw on some socks to cover up his nail polish, before racing back to Ruby's room to return her heels. In an instant he was back in his room, panting slightly from his sprint down the hallway.

He was just thinking about how to spend the rest of his afternoon, before he heard a buzz on his phone. 

"Congratulations! £50 has been transferred to your account." read the notification from the app.

Danny was gobsmacked. It had worked. And it had been so easy. A few minutes work and he was £50 richer. He sent the picture over to SugarDaddy69 and started to think that Australia may be within his reach after all. He had a little over 2 weeks to go and things were looking up.

*Buzz*

"Inbox: 1 message".

Danny opened his phone and read the message.

"Sexy feet, even better in heels. Can't wait to see more. Next time purple nail polish. Will pay more xx"

Danny couldn't help but smirk. Without knowing it, this man could be buying Danny a ticket to Australia. All for some pictures of his feet.