Nanny had deliberately chosen this set of pretty lingerie, an old pair of purple French knickers with her new lacy white bra and her black stockings hoping that naughty Justin would catch a glimpse of her in her delectable silky lingerie. 

Justin at 18, was too old to have a Nanny, but he did have a much younger sibling, George.  His Mum had remarried after Justin’s father had passed away and after having a baby went back to her job in advertising in Soho.  Mum was hardly ever at home; she was often away working on an important product launch.  His stepfather mostly worked abroad in IT. They were well off and lived in a large 4-bedroom house in north London with more money than time. So, they went to an agency and hired Nanny to take care of the baby.  Maybe it was also to keep an eye on Justin? Nanny came with excellent childcare qualifications from Norland College and impeccable references from the agency.

Nanny picked up her white half-slip but straightened her seams first before putting on her slip. She heard a rustling just outside her bedroom door.

Justin peered through the crack in the Nanny's bedroom door.  He was hoping to catch her getting dressed in her pretty lingerie.  Oh joy, the naughty boy had timed it just right as Nanny stepped into her pretty white half-slip and pulled it up over her purple French knickers. Justin had an instant hard-on and slipped his hand inside his PJ’s to massage his stiff cock. This was not the first time Justin had masturbated seeing Nanny in her pretty lingerie.

There was an occasion about two months previously when Nanny had been bottle-feeding George in the nursery.  As she held the baby his feet had pulled Nanny’s skirt up slightly.  Justin was walking past the nursery to his room and could not help but notice a peeping slip and lacy stocking tops appear below the hem of Nanny’s black pleated skirt.  Justin knew from his intense study of porn on the internet what he was looking at, and he rather liked it.  His parents thought they had put a parental block on the home Wi-Fi to protect Justin. He laughed at this because he could connect his laptop to his phone’s hotspot and ignore the Wi-Fi. 

As Nanny came to the end of feeding George had fallen asleep so Nanny put him back down in his cot.  As she stood up, she lifted her skirt and slip to adjust her stockings knowing full well that there was a strapping young lad standing in the shadows just outside the nursery watching her in the mirror on the landing. 

Nanny was wearing a lovely pink blouse which was slightly sheer and showed off her pink bra nicely.  Her pink slip, suspenders and panties matched the blouse perfectly.  There were even flecks of pink in her lacy stocking tops.  She finished fiddling with her garters and dropped the skirt back down.

Justin had to retreat to his bedroom and pay attention to the huge boner in his pants.

From then on Justin paid careful attention to what Nanny was wearing.  She was really old, probably in her 30’s, thought Justin, but she became the centre of his teenage masturbatory fantasies. He couldn’t actually remember what her first name was, she was called Nanny by the family.  He didn’t really talk to her, just observed, he was actually scared that she would think he was a peeping tom.

 A few days after the first pink upskirt incident Justin noticed that Nanny was wearing a long pleated blue skirt so there was not going to be a flash of slip or stockings, or so Justin thought.  Just then Nanny leant over to pick up one of George’s toys off the nursery floor and Justin became hard again as he could see her legs in sheer black hosiery, blue heels and a very lacy blue slip under the blue skirt.

Justin went to his bedroom and shut the door quietly, dropped his trousers and pants and took hold of his throbbing member.  He lay on his bed and imagined Nanny taking off the pleated skirt to reveal a semi-sheer blue slip.  He wanked his stiffie hard as he imagined the thin slip would reveal her stocking tops held tight by her suspender strap and some matching blue lacy panties.  It was enough to make him cum thick ropes of hot white seed up into the air. 

There were other sightings that excited young Justin.  There was one day when he spotted that Nanny was wearing what looked like a two-tone slip under a grey dress, a bit of white and a bit of blue. Well, the slip had two rows of very pretty lace on the hem.  Bit weird but it didn’t really matter, he still had an amazing wank in his bedroom thinking about what he had just seen.

Nanny had in fact been wearing two slips, a lovely full slip in white and a separate blue half-slip underneath the full slip.  Nanny loved wearing two slips so she could feel one silky nylon slip sliding over the other one. Not weird at all.

What Justin did not know is that Nanny quite often wore two slips together, a full slip and half-slip.  Sometimes it was a nice colour contrast, such as the white and blue slips, but sometimes she wore a matching brown coloured full slip with a short brown half-slip with creamy lacy.

 Justin’s mind began to wonder what sort of bra and tits Nanny had.  If she liked lacy slips and panties, did she like lacy bras?  He thought about what it would look like as Nanny raised her full slip to reveal a pretty black bra.  Sometimes he didn’t need much imagination as he could actually see her lacy bra through a sheer blouse. OMG, another shot of spunk in the air. 

One day Nanny was wearing a tan coloured corduroy skirt and a brown jumper.  Justin noticed that she was wearing seamed tights and there was a little tell-tale sign of a lacy slip. Was it tights though? Perhaps it was actually classic seamed stockings?  Another spunk session as he imagined Nanny taking off her skirt to reveal her silky slip, stocking tops and maybe even a glimpse of silky panties. Spunk!

Justin began to realise two things.  Firstly, Nanny had a huge collection of different coloured slips.  When he glimpsed the hem of a grey slip worn with grey stockings did that mean Nanny was wearing matching grey lacy panties, a grey suspender belt and lacy grey bra. Probably. He would love to have explored her lingerie draws in her room to see if she had matching sets of lingerie, but she usually kept her bedroom door locked when she wasn’t there.

Then Justin noticed one morning that Nanny’s bedroom door was slightly open and he could see her getting dressed.  She was stepping into a grey checked skirt, but underneath was wearing a white slip with a huge lacy black hem.  The thin white slip also revealed white panties with black lacy hem and black stocking tops.  She was also wearing black leather boots.  Instant hard-on. 

As Justin was replaying the image of the white slip and black stockings, he had just seen, the second thing he wondered was if she was teasing him with the number of times he had “accidentally” glimpsed Nanny in her slip and stockings?  Well just maybe, he was right, it wasn’t an accident. Spunk, again.

Justin’s fantasies moved on.  He began to wonder what it would be like if he lay on the floor and could see right up inside Nanny’s skirt to see her pretty slip, stocking tops, suspender belt and even her silky panties.  Instant spunk!

Then he wondered what it would be like if Nanny was not wearing her dress or skirt but just dressed in a full slip and stockings kneeling on the floor in front of him so that he could masturbate right behind her and shower his hot white spunk all over her silky slip  But what would it feel like to actually rub his stiff cock over the nylon slip and her silky arse? Oh. Oh, oh… Double spunk! Justin’s imagination ran riot.

Back to the present.  Nanny pulled a purple blouse down over her head and down over her lacy white bra. Oh, she loved wearing pretty, silky lingerie.

Then she picked up her black skirt from the bed and stepped into it, making sure her slip was not caught up. 

Nanny bobbed down to adjust her black heels and noticed her black stockings had a slight ladder near the toes on both feet. Sheer seamed stockings were so expensive, but she thought she might have found a way to get someone else to pay for a new pair or two.

“Come in here at once, Justin”

Justin stopped wanking, his erection disappeared, he held his breath.

“Do you want me to tell your Mum that you spy on Nanny and masturbate whilst leering at me as I am getting dressed? Get in here now before your baby brother wakes up and wants a feed.”

Justin shuffled into Nanny’s bedroom.  Although he was terrified of Nanny, he was even more terrified of Nanny telling his mum what he had been doing. 

“Sit down, no not on the bed, on the floor.”

Nanny scowled down at Justin.  He looked up and could see her peeping slip as she loomed over the teenager.

Nanny lifted up her black skirt.

“Is this what you want to see, my purple knickers, my stocking tops and my slip?”

“Urggggg…” said Justin.  His erection was back and even bigger and harder than before.

“Lie down you miserable wretched boy and start wanking.”

Nanny stood right over the top of Justin, who was now lying flat on his back with his hand inside his PJ’s wanking the biggest erection he had ever had.  He looked straight up Nanny’s skirt to see her purple panties, white half-slip, black stocking tops. Although it was even better than he had imagined there was something Justin couldn’t quite make out in the way the purple panties bulged at the front.

“Do you want to see more of Nanny’s pretty lingerie, you naughty boy?”

Justin could barely speak with excitement.

Nanny stepped away from Justin and quickly removed her skirt and blouse.

“Do you like my pretty white slip and lacy white bra, Justin?”

Justin’s cum shot up into the air and some it landed on Nanny’s foot. 

“Oh, you naughty boy, you have just ruined my best nylon stockings. You are going to pay for that. “

Justin looked shocked and tried to dab the ropes of cum off Nanny’s black stockings. 

“No, not like that.”

“What shall I do, wailed Justin.

“Well, you can pay for some new stockings for a start.”

“Yes, yes, I can pay. I have an allowance from Mummy.”

“And you can wipe up the mess you have made.”

Justin looked around wildly for some tissues. 

“No not with a tissue, with these,” said Nanny reaching under her white slip and pulling down her large purple French knickers. 

“Use my knickers,” said Nanny.

Justin reluctantly took the purple panties.  He was starting to get hard again.  He knelt down on front of Nanny and started to dab at the wet patches that had by now soaked into her black stockings. 

“No, you twit not with your hand.  Put the knickers on and then use your stiffie in my stockings. 

“Oh, said Justin, “but I can’t wear….”

Nanny glared at him. “You know you want to.  You have been dreaming about this moment.  I did too when I was boy,” said Nanny. 

Nanny lifted her white slip to reveal a small cock nicely framed by a lacy purple suspender belt.  She dropped the slip back down again making a tent in the slip.

“Now put on those purple knickers and start rubbing your cock over my stockings.”

Justin was too shocked to say no.  He slid the knickers up his legs.  There was plenty of room for his stiff cock.  It felt wonderful.  It felt even more wonderful when he started to rub his nylon clad cock all over Nanny’s black stockinged legs and feet.  Soon he was cumming again all over the knickers and Nanny’s stockings. 

“Now stand up and take off the knickers,” commanded Nanny.

Jason took off the knickers and handed them to Nanny, ashamed of what he had just done.

Nanny snatched the knickers from Justin, lifted her slip and put the knickers back on.  She could feel Justin’s cum dripping out of the knickers.

She lifted her slip and turned her back to Justin and pushed out her bum. 

“Now young stud, you can fuck my silky arse with your large stiff cock. I know you are hard again looking at my lingerie, just like you have for the last two months.”

Justin thought it would be impossible to be hard again for the third time in thirty minutes but looking at Nanny’s beautiful purple panties was doing the trick.  

He took hold of her hips and slowly started frotting her knickers and bum from behind with his stiffie. Rubbing her stockings whilst wearing the panties was amazing but this was even better.   

Nanny reached into the front of the knickers and rubbed her own cockette. 

“Eat your heart out Mrs Doubtfire, you don’t know what you were missing.” Said Nanny as her cockette flood the purple panties in the front and Justin flooded them from the rear. 

Nanny let Justin keep the French knickers to wear in his own room at night after he had washed them.

Author’s note:

Nanny has indeed been to Norland College 10 years ago to train as a Nanny. He was the first male graduate.  One of the girls kept teasing him about trying on the girls traditional brown uniform and hat.   In the end, he gave in and tried it on, with tights, panties, bra and of course the traditional white slip.  The very slip in the story, that he was allowed to keep after his first dress up by his friend.  When he could not find work as a male nanny he gave in and presented himself as the typical Norland Nanny. From then on, she never looked back.