Tim found a seat on the train and made himself comfortable. As he sat down he was very aware of the silkiness of the panties he was wearing brushing against his cock. He slowly stroked his hand down the leg of his jeans feeling the little bump of the suspender as his hand passed over it. He felt himself becoming aroused, as he always did when he wore the lingerie.
It had taken him some time to pluck up the courage to go into Ann Summers to buy it, in fact, he had passed the open door at least ten times, until eventually an assistant had come to the door to ask if she could help him. It was just the push he needed, and she couldn’t have been more helpful. It had opened a whole new world to him and now he wore the lingerie every opportunity he could.
Since the episode at Diane’s house he hadn’t been able to get it out of his head. Not just his first sexual experience, but wearing Diane’s french knickers. Every time he had thought about it he had felt the urge to masurbate. In fact he had made up for last time, spending more time this term jerking off than in the last five years.
He found it particularly erotic shooting his cum into his panties which were not dissimilar to the ones he worn for Diane. Diane popped into his head, he hadn’t seen her again since the incident in her bedroom and he was determined to pluck up the courage to knock on her door. If nothing else he wanted to show her his lingerie. He longed to have her tell him how ridiculous he looked, but for the life of him he couldn’t work out why.
He put his key in the door, shouting as he entered “Mum i’m home !”
His mother came down the stairs.
“Tim why didn’t you ring i would have picked you up from the station ?”
“It’s fine i had to pop into town”
Tim took his case upstairs and unpacked, careful to put his lingerie where his mother wouldn’t think to look. Then he went downstairs.
“Just in time for dinner darling, how was your term ?”
“Ok, you know, always busy, how have things been here ?”
“Same as, been very busy in the office”
“Have you seen much of Diane ?”
“That’s a strange question, no more than usual, don’t tell me you have a crush on her ?” she laughed, but was oblivious to Tim’s blushes
“Don’t be silly mum, i just wondered if the wardrobe door was ok ?”
“Well she hasn’t mentioned it so i guess it’s fine. I’m out tonight Tim, sorry to leave you to yourself on your first night back”
“Don’t worry mum, it’s fine”
Tim was secretly pleased. He wanted to go next door, and now he wouldn’t have to wait. As soon as Tim saw his mother drive off he left the house and went next door.
He rang the bell feeling his mouth go dry, but, determined to stand his ground. The door opened. Diane didn’t seem surprised to see Tim. She smiled.
“Hello Tim, come in, i was expecting you, but didn’t think it would be quite so soon.”
He thought she looked amazing. She wore a white dress. She had been abroad and it showed off her tan. She had bare legs with little white strappy sandals with four inch heels. Her nails were painted deep coral, which matched her lips. Her hair was loose and dishevelled which added to the allure of her.
“Mum’s gone out so i thought i’d come and see how you are ?”
“Did you now ?”
Diane had a glint in her eye and smiled, which made Tim blush.
“I wanted to show you something Mistress”
Diane looked at him
“So i didn’t mishear when you called me Mistress, well i rather liked it, what i want to know is why you’re still on your feet ?”
Tim fell to his knees and kissed her beautiful feet.
“I’m sorry Mistress, forgive me”
“Ok stand up, now what did you want to show me ?”
Tim unzipped his jeans and pulled them down to expose beautiful lilac panties, matching suspenders and black stockings.
“Excellent Tim, but i think we can take it further than that”
She took his hand and led him into a room at the back of the house. There was a rail with beautiful satin dresses hanging on it, pink, yellow, black. Diane took down a pink one.
“Take off your clothes”
Tim did as he was told excitement filling his whole body. Diane handed Tim the dress.
“Put it on”
He stepped into it, and his whole body felt electric.
“Turn around Tim, have a look at yourself in the mirror”
“Oh Mistress i love it”
Diane smiled, she knew he would. Tim watched as she got onto her knees in front of him. She pulled up his dress and pulled down his panties. He was expecting to feel her mouth around him as last time, but was in for a shock. He felt some pulling and tugging and then heard a click. Then Diane was back on her feet.
“There we are slut, have a look”
Tim looked down to see his cock neatly encased in a pink chastity device. He was speechless. He looked at Diane waiting for some sort of explanation. She smiled at him.
“This is the beginning of your training Tim. You will spend the duration of your holiday locked up for your Mistress. I expect you here every day doing house work for me. Is that clear ?”
Tim lowered his head.
“Yes Mistress, perfectly clear, thank you”
“Good, off you go sissy, i will expect you here in the morning at nine. Close the door as you leave.”
Tim walked out quietly closing the door, wondering how he got into this situation, and what was in store for him.