Rob had always been fascinated by ladies underwear after he picked up a pair of his mum's and sniffed them. He also loved the feel of the material against his body. When he found his older sister's panties he was soon wearing them and pleasuring himself at the same time.
As he got older he would look at underwear as he walked round shops and was soon buying some for himself. He would put it on and stand in front of a full length mirror and admire himself while he wanked.
In the town that he lived there was a shop that was owned by his mum's best friend. Her name was Sally and as he was growing up he would call her auntie Sally.
The shop that he walked or drove past most days sold second hand clothing. Most of it was women's but also some men's. The window display was always women's which fascinated Rob.
He would sometimes see her outside the shop having a cigarette. He was always fascinated by the bright red lipstick she wore. Even though she was about the same age as him mum he fantasised about kissing her.
Eventually he braved up to go inside. As he browsed around Sally said, 'hi Rob, how are you, is there anything that you're particularly looking for?'
Rob felt very embarrassed as he said, 'I'm looking for some ladies clothing.'
'May I ask the age and size of the lucky lady. I may be able to help,' she replied.
Rob was suddenly unable to talk. Eventually he said, 'it's for me.'
'OK, that's fine, what have you got in mind,' she replied.
Before Rob could answer another customer came in and Rob said, 'I'll wait outside.'
After a few minutes Sally went outside and as they chatted she lit a cigarette. Rob was mesmerised as she put the cigarette between her scarlet red and sucked on it. Rob's mind was elsewhere.
She asked, 'do you just want a dress or a full sissy make over including make up and underwear?'
He replied, 'well to tell you the truth, I'd love a full makeover but please don't mention it to mum.'
'Of course not, your secrets safe with me,' she replied.
'Well I close at 1 o'clock why not wait until then, you don't really want people walking in and seeing you,' she said.
Rob waited patiently and as he went in on time she locked the door and pulled the blind down.
She said, 'I think you'll like these undies.'
She showed him a pink pair of panties which was fairly small and would barely cover his naughty bits but he like that idea. Next was a bra.
She said, 'I've got some padding that will look like you've got big tits.'
He embarrassingly stripped off in front of this woman he had known since he was a young lad. Even more embarrassing was that he was semi hard.
Sally said, 'the thought of this is clearly arousing you, don't worry about it.'
She asked, 'do you want to be dressed as a normal lady or as a sexy slut?'
'Oh, a slut definitely,' Rob replied.
Sally went into a back room and came out with various items of clothing. She said, 'as you'll be wearing stockings you need a suspender belt first.'
She slipped it around Rob's waist and fastened it then took a pair of fishnet stockings and said, 'sit down and I'll put them on for you.'
Sally knelt down in front of Rob and slowly pulled the stockings up his legs. She couldn't take her eyes off his fully erect cock which was now poking out the top of his pink panties.
She said, 'you know how when you were younger you called me auntie. Well I'd like you to call me auntie now.'
