The Sugar Baby

In Too Deep

Danny had been performing his new role as a sugar baby for a week now, and it had been as easy as anything. He spent a couple of hours a day chatting to the guy, and sent a few pictures a day too, all of his feet. Sometimes in heels, sometimes not. Always with his toe nails painted.

But it was at this point that things started to get a little more serious. One weekend, Danny was chatting to Ruby in the kitchen when he felt his phone buzz in his pocket.

He pulled it out to read the message, and started to blush. Ruby noticed and started to tease him

"Ooooh what's got you all embarrassed, somebody sexting you?" she laughed.

Danny gulped, but replied back "No no, just something to do with work, need to go and call them quickly" he said as he raced to his bedroom.

Once in there with the door closed, he reread the message.

"Good morning gorgeous girl. What are you wearing ;) xx"

Danny was shocked. Up until now things had been relatively unflirty. It was mostly just small talk. This was a step up and he wasn't sure how to respond.

"Just some pyjamas" he replied, hoping this was enough to keep sugar daddy happy.

"Are they sexy pyjamas? xx" he replied.

"Sure" replied Danny, wishing this conversion would fizzle out.

"Let me see xx" replied Sugar Daddy.

Danny panicked. What could he do? He didn't own any sexy pyjamas. He thought for a few minutes, before his phone buzzed again.

"?? I'm waiting xx" came the reply.

He panicked even more, thinking what to do.

To make matters worse, he heard Ruby's voice through his door.

"I'm heading out now Dan, will be back around 6 if you want to make dinner together".

"Sure", he replied hastily, "sounds good".

He listened and heard Ruby shut the front door, while his phone buzzed again.

"Don't keep me waiting Danielle".

Danny knew what he had to do, but he wasn't proud about it. He quickly checked to see that Ruby had indeed left, before quickly racing down the hallway to her room. He headed over to her drawers and opened the top drawer, and was met with piles of panties and bras. He felt embarrassed and quickly shut the drawer, before opening the next one down. Bingo. It contained several pairs of pyjamas, one of which caught his eye. It was a short and top set, pale pink with black lace trim. The top had straps and showed off the wearers cleavage, not that he had any to show off, but it would have to do.

He raced back to his room and saw that there was another message on his phone.

"This relationship works two ways Danielle. I expect you to answer my requests."

Danny was nervous, but saw this as his only choice. He threw off his own pyjamas and pulled on Ruby's pair, staring at himself in the mirror. He was annoyed that they were slightly too big for him. Ruby had a much bigger, firmer bum than him, so the shorts sagged a little around his bum. The top was slightly loose, and of course he had no cleavage to fill the top half. But what struck him was how feminine he looked, regardless of his lack of curves and breasts. From the neck down, he really wouldn't have been able to tell if this was a man or a woman, particularly with the painted pink toe nails.

He quickly snapped a pick of himself in the mirror, keen to make sure his neck and head wasn't visible, and at an angle that made his body look slightly more feminine. The result was good. Good enough that it wasn't glaringly obvious that he was a man.

Danny sent the picture over to Sugar Daddy and quickly stripped out of the pyjamas, racing to Ruby's room to return them.

When he returned, he saw a new message on his phone.

"Gorgeous <3"

Phew, he'd managed to get away with that one. But if Sugar Daddy had any more requests, things could quickly get out of hand.