My Sister, My Mistress

Story Info
Crossdresser gets caught.
1.8k words
4.11
149.1k
29
0

Part 1 of the 3 part series

Updated 10/23/2022
Created 09/18/2003
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
fido43
fido43
29 Followers

Alan was twenty years old, and lived at home with his parents and younger sister Carol, who was eighteen. He and his sister never really got on, they were always arguing about something, and lately things were worse than usual. Alan was trying to save up so that he could get a place for himself, and nearly had enough for a deposit on a nice little flat. Alan liked his privacy. He had friends and liked to go out weekends, but he also liked being alone so that he could indulge himself in his fantasies. Alan liked to cross dress, and nobody, but nobody knew. He was always hoping that he could find a nice young lady that he could pour his heart out to, but he wasn’t ready to tell anyone yet. Although he couldn’t dress fully at home, he did own a few things, and liked to wear his femme underwear under his jeans.

One particular weekend his parents had gone away, and his sister was spending the weekend with a friend, and so Alan was going to be alone, and looking forward to relaxing in his girls clothes. He was very slim and only about 5ft 6ins, so he could get into lots of nice things quite easily. He would never go out in public though, as he didn’t think he could carry it off.

His parents had been gone a little while, and Carol was getting ready to go herself.

‘Hurry up.’ Said Alan impatiently.

‘Piss off.’ Carol said through gritted teeth. ‘I’m going as fast as I can. I’m looking forward to getting away from you for the weekend.’

Alan leant in her bedroom doorway watching her pack. He noticed the sexy things she had, but not liking his sister, wouldn’t fancy wearing them.

‘Why do you want to get rid of me so quickly creep?’ She asked ‘What are you upto?’

‘Nothing’

‘I bet.’ Carol said, and looked at him suspiciously.

It wasn’t long before Carol was ready and was leaving.

‘Bye then.’ Alan called sarcastically.

‘Bollocks’

He was alone, and his stomach was turning somersaults. The whole weekend dressed up was going to be fantastic. He watched his sister leave, and when she was out of sight he ran upstairs and took the suitcase from under his bed, unlocked it, and emptied out the contents. There were numerous pairs of lacy panties, some sexy flared mini skirts and an assortment of bras, tights, shoes and a few wigs. He waited for ten minutes, just to make sure Carol had gone, then stripped off and stood totally naked with his erection standing out before him. Alan was also hairless, he kept his legs clean shaven, and loved the feel a pair of tights being pulled up his smooth legs.

He picked out a pair of white lacy tanga style panties, that had a pattern of small blue forget- me- nots on them, a matching bra, a pleated, white mini skirt and a white blouse. He also chose a pair of red stiletto shoes, and thought he would look nice and tarty ,especially with a blonde bob style wig.

He got dressed slowly, as he liked to watch himself in his mirror, and feel the sexy smooth clothes against his skin. Unfortunately, being aroused made wearing skimpy panties a little uncomfortable at times, but after a while his erection would subside, and fit nicely into its sexy covering.

This particular day, his whole world was going to be turned upside down. Alan had been upstairs getting ready for quite a while, and went downstairs to make himself a coffee, and relax in front of the TV. He drew the curtains, even though it was day time, just in case somebody could see in and got on with being his femme self. He put his feet up and settled himself down for the rest of the day.

Alan sat up with a jolt. He’d fallen asleep. He stood up and went into the kitchen to make another drink. That’s when he saw Carol’s suitcase in the hall. His heart missed a beat, and then raced. She must have seen him, or maybe she didn’t go into the living room. Alan started panicking and stood very still and tried to hear any sound. None. He went back into the living room to get his shoes and thought it best to go and get changed, just in case. That was when he saw the note, and the photo from the instamatic camera. The note said‘well well well. A nancy boy for a brother, I'm going to have some fun now, ha ha ha.’ The photo was of him asleep on the sofa, fully dressed, and showing his panties, where his skirt had ridden up. He ran upstairs to get changed, although the damage had been done. He burst into his bedroom, and there was Carol sat on his bed, looking through his things.

‘What are you doing? He shouted at her.

‘What amI doing? She laughed.

‘Get out of my room, and don’t you dare tell anyone about this, I’ll kill you if you do’

‘Who are you to threaten me?’ Carol was angry. ‘I think you had better watch your tongue. If I show anyone the photos, your life will be a living hell. As I said, I’m going to have some fun. So if you don’t want this to get out, you had better start showing me some respect. From now on you will do exactly as I say! Do I make myself clear?’

Alan stood and stared at Carol. He was speechless, and trying to think of some way to get out of this embarrassing situation.

‘I said. Do I make myself clear?’

‘Yes.’ Alan said looking down. His face was burning red, he felt angry with himself and Carol, for being so stupid and letting her of all people see him.

‘Yes what?’ She said standing up.

‘Yes Carol?’

‘Try, yes Mistress!’

Alan fought to find the words.

‘Yes Mistress’ he finally said.

‘Now get on your knees, crawl over here and kiss my feet.’ She hissed at him.

He fell to his knees and crawled to his sister and pressed his lips to her bare feet.

‘Stand up.’ She ordered. ‘And take that ridiculous blouse off, and that skirt.’

He did so, and stood there in his matching bra and panties.

‘You look pathetic.’ She chided. ‘My big brother likes to wear girls clothes.’

Alan just stood looking down, full of embarrassment and guilt. Carol made him follow her back downstairs.

‘From now on, and not just for this weekend.’ She started. ‘You are going to be my slave. You will obey everything I tell you, even when mum and dad are back, or we have friends around. Don’t worry, I wont have you grovelling in front of them, just do as I say, and things will be fine.’

‘Yes Mistress.’ Alan said without prompting.

‘Good. Unfortunately, I didn’t give you permission to speak, so I’m going to beat you.’ She smiled. ‘Bend over and touch your toes.’

Alan did so. Carol picked up a riding crop from the hall cupboard and went and stood behind Alan. He looked most awkward with his pretty panties riding up his bottom.

‘I’m going to beat you six times, and when I’m finished, you are going to thank me and kneel at my feet again, do you understand?’

‘Yes Mistress.’

The searing pain of the riding crop tore through Alan’s bottom, and tears began to well in his eyes. After his Mistress sister had finished he turned around, knelt before her and put his face at her feet again.

‘Thankyou Mistress.’ He said timidly.

Carol sat down and crossed her legs.

‘First you will get me a glass of wine, then you will massage my feet, and kiss and lick my toes.’

‘Yes Mistress.’

The next hour Alan was kept very busy, getting his Mistress glass after glass of wine and paying her feet attention. She was getting quite drunk, but not too drunk, and her hatred for him didn’t diminish any.

‘I need a piss.’ She said, and stood up a little unsteadily. ‘Now, come with me.’ She ordered.

The two of them went upstairs to the bathroom. Alan was getting a little nervous, what did she want him to follow her to the toilet for? She ordered Alan to kneel in the doorway, and watch her as she slid out of her jeans, and kicked them off at him. She sat on the toilet without taking down her knickers, and looked Alan in the eyes as she pissed through them into the toilet.

‘Come here.’ She said, and beckoned him with her finger.

He crawled to her, and she stood up in front of him.

‘Lick it.’

Alan looked up at his Mistress.

‘Fucking lick my crotch you fucking wimp!’

Alan pressed his face into the piss soaked crotch of his sisters knickers and gingerly poked out his tongue, and tasted the sweet, tangy taste of wet cotton.

‘Do it properly.’ She ordered.

So Alan started to lick her wet knickers, he licked and licked until he was ordered to stop. Carol took off her wet things and stood in front of her kneeling brother totally naked from the waist down. She had had enough wine not to worry about it, and Alan was too scared to say anything. She stroked his head, and told him to take off his panties and put on her wet ones. He did so and resumed his kneeling position. Again she stroked his head.

‘If you are a good slave, I will make your life a little more bearable.’ She finally said. ‘Are you going to be a good slave for your sister?’

‘Yes Mistress.’

She moved a little closer, so that her cunt was millimetres away from his face. He could smell her warm fishy smell, and the sweet smell of her piss. She held his head and gently pulled it into her moist sex. Without prompting, Alan began to lick her and suck at her moist hole, forcing his tongue in as far as it would go and trying to eat her, to please her, his Mistress, his sister. She turned around and bending over pulled his head up to her arse. She parted her bottom cheeks exposing her anus. Alan hesitated.

‘Well slave.’ She said. ‘Lick my arse!’

Again Alan used his tongue to please her. His fear of being exposed was more powerful that the feeling of committing incest. There wasn’t anything she could make him do that was worse that what he had just done. To use his tongue, not only on his sisters cunt, but to clean her anus with it, was the limit, surely.

‘Tomorrow.’, She informed him. ‘I will teach you how to serve properly. You will curtsey, sit properly, walk properly and pamper me for the rest of the weekend. Oh and by the way, Julie will be coming around first thing, so you’d better be on your best behaviour. I’ve told her about you, so you had better show her the same respect that you have shown me. Do you understand?’

‘Yes Mistress.’ Was all he could say.

fido43
fido43
29 Followers
Please rate this story
The author would appreciate your feedback.
Share this Story

READ MORE OF THIS SERIES

Similar Stories

Accidents Happen! A brother and sister make a discovery.in Incest/Taboo
The Sleepover Brother interrupts sister's sleepover, lingerie party.in Incest/Taboo
Sister's Panties Brother with a panty fetish gets caught by sister.in Incest/Taboo
Kim Gets Off to College His sister helps disguise him to attend all-girls' school.in Incest/Taboo
Family Affair: Backseat Sister Brother takes sister's virginity during family road trip.in Incest/Taboo
More Stories