Crystal's StorySite

Warning This is a work of fiction.


Mother's Sexy Clothes

by Sissy Son


It was a typical Saturday night in our household. I was preparing for another night in front of the television, while my Mother was getting ready for a night on the town. There was only the two of us in the house since my Father left us when I was about four years old.

I was eighteen years old, but due to being skinny and boyish looking people took me for being about fifteen. I was also very shy, especially around girls. I longed to have a girlfriend, but I just did not have the confidence to ask anyone out.

Mother, on the other hand, had no shortage of admirers. She was 42 years old, slim, with long blonde hair and she was very pretty for her age. She was a very feminine woman. Her make-up was always immaculate and her fingernails were constantly long, sharp and painted. She tended to dress quite provocatively, especially on her nights out. She always had men chasing her and sometimes had two or three boyfriends on the go at once.

I was flicking through the TV guide when Mum came into the room.

"How do I look, Scott?" she asked. I peered up from my magazine and immediately blushed in embarrassment at my Mother's sexy appearance. She was wearing a tight, short black mini-dress, underneath which were black stockings and garter belt and shiny black stiletto shoes with four inch spiked heels.

"Uh, you l-look great Mum" I stuttered, and she giggled at my obvious discomfort as I squirmed in my chair. She teetered over towards me, bent down in front of me so that her cleavage was right in my line of vision and planted a kiss on my forehead, leaving an imprint of her bright red lipstick. Then she turned and left with her usual wiggle of her bottom as she walked. My Mother's slutty dress sense and behaviour were a constant source of embarrassment to me and I had tried to tell her this in the past but she never listened. Mother was far more assertive than me so she would always win any arguments. I would dread the nights when she bought her lovers back to the house as I was often kept awake by her gasps of pleasure which she made no effort to stifle.

I sat on the couch after Mum's departure and wondered whether she was the cause of my recently developed urges. The urges to wear her underwear and clothes. Was it her sexy attire, or the way she flaunted her femininity which made me like this. It didn't help that when I was a boy, she would sometimes punish me for being naughty by making me wear girl's clothes. Anyway, whatever the cause, all I knew is that I just could not resist the urge, however hard I tried.

I climbed the stairs and headed towards Mum's bedroom. I was already full of shame over what I was about to do, but also full of excitement. I knew I was not gay, on the contrary I adored women, but I also knew that I just could not help myself from dressing in my mother's things. Firstly I stripped naked of my male clothes and opened one of Mum's drawers. I was confronted by a wonderful site of many types and colours of female underwear. Tentatively, I picked up a pair of black stockings which had obviously been worn and a black garter belt. Pulling the stockings up my legs sent a shiver of pleasure through my whole body. With trembling hands, I attached the stockings to the garter belt around my waist.

Next, I approached Mum's dirty laundry basket and retrieved a pair of black silky knickers which she had probably worn the previous day. The feelings of shame and excitement heightened as I pulled the panties up my legs and around my waist and now stiffening cock.

Reaching into the laundry basket I recovered a black lacy bra and proceeded to fix it around my boyish chest. I filled the bra with my own socks to give the impression of female breasts. Now my underwear was sorted it was time for Mum's sexy clothes!

After opening the door to Mum's huge wardrobe, I reached for her shiny red satin blouse and a short black mini-skirt. When I put the garments on I noticed that the skirt was so tight that my erection was clearly visible sticking out at the front. For my footwear I grabbed a pair of red spiked-heel stilettos from the bottom of Mum's wardrobe and put them on my feet. I felt like a sexy and tarty woman as I walked around in the heels. I was really turned on by now and began to rub my erection through Mum's skirt and panties.

Suddenly my feminine escapism was bought to abrupt halt and my worst nightmare came true. There I was parading around the room in Mum's high heels when a familiar voice stopped me in my tracks.

"What are you doing darling?" It was Mother. I was not expecting her back for another two hours and I was overcome with shock.

"Er, I-I'm sorry Mum.." I struggled for words as my shame and humiliation reached fever pitch. I really did want the earth to swallow me up. What would I say?

Mother stood there with her hands on hips and I noticed that she did not appear to be very shocked and she even had a wry smile on her heavily made-up face.

"Well well, I thought someone had been wearing my things." She said. "I came home early tonight to see if it was true and look what I find." I could not look my Mother in the eye as my face was crimson with shame. I just stood there, looking at the floor as she continued,

"My, my, you do look pretty." She giggled. "Is this why you don't have a girlfriend? Perhaps you would rather have a boyfriend? What would your mates say about this?

"No, No." I protested. "I am not gay. Please don't tell anyone about this Mum. I'm sorry for wearing your clothes. I just can't help it." A wicked grin appeared on my Mother's face as she stated,

"Suddenly so apologetic and humble aren't we son? It's a change from the usual sullen little man giving me attitude and criticizing me." I wondered where all this was going as she walked over and sat down on the edge of her bed. I just wanted to leave the room and get out of those clothes, to escape the shame of being dressed in women's clothes in front of my own Mother, but it was not to be.

"Get me my cigarettes and lighter from my dressing table while I figure out what I am to do with you." She ordered. Puzzled, but in no position to argue I did as she asked without a moment's hesitation. As I approached her with the items, she snapped,

"Get on your knees and offer me one properly." This startled me somewhat and my Mother's sudden assertiveness was beginning to unsettle me but in a strange way, excite me. I suddenly felt really submissive and weak and just wanted to please my Mother so I dropped to my knees and tentatively held out the opened packet towards her. She took a cigarette and I noticed her long sharp fingernails which were painted red. Mum put the cigarette to her lips and I meekly offered her a light with my shaking hands. She took a drag from her lit cigarette in the most feminine manner and teasingly blew smoke in my frightened face. The fear and humiliation I was feeling were suddenly joined by erotic sensations. To my horror, the sight of my Mother smoking in her sexy mini-dress and heels caused my cock to stiffen and it could clearly be seen bulging through the tight mini-skirt I had on. Mum noticed this and smiled triumphantly.

"You're enjoying this, aren't you sissy boy." She cooed as she raked one of her long red nails down the side of my cheek. All of the mixed emotions I was going through prevented me from speaking and I felt totally at her mercy. She continued, "well Mummy's enjoying it too. And seeing as you like wearing my clothes so much I have decided I'm going to make you dress in them more often, as you are far more obedient like this."

I could not believe what I was hearing. I thought that Mum would just tell me to get out of her clothes and the whole thing would be forgotten, but it seemed like she had other plans entirely. She then stepped up the humiliation one more level as she looked down at me and stated,

"Although I think you look so cute in my clothes I am going to have to punish you for borrowing them without my permission." My mind raced. What does she mean by punish? I thought. My questions were soon answered as Mum went to her wardrobe and fetched a thick leather belt. She commanded me to raise my skirt up and place myself over the edge of her bed with my bottom exposed.. Of course I did exactly as she said and she proceeded to smack my arse with her belt while at the same time verbally demeaning me.

"How dare you wear my clothes without asking" she shouted, and the belt hit my behind with a loud THWACK. "You are going to wear my clothes only when I say so, aren't you sissy boy?"

"Yes Mummy, yes." I replied with tears welling up in my eyes from the sharp stinging of the belt. "I will do whatever you say." THWACK went the belt again. Mother continued,

"And you are going to do all the housework and show me more respect." THWACK again. "You will never criticize my appearance and lifestyle again.You are going to tell me when I look pretty AND sexy without me having to ask you." Another THWACK from the belt. "Seeing as you are a sissy little faggot, that is how I will treat you from now on. You are going to be Mummy's sissy boy slave aren't you" she hissed, followed by another THWACK.

"Yes Mummy. I just want to be your sissy boy. I will never disobey you again. I will do my best to please you and do as you say." I could not believe I was actually saying these things, but I was only doing it to stop the pain of the belt. At least the whipping had got rid of my erection. When I realised my punishment was over I turned round to face Mother while I rubbed the tears from my eyes. I could tell she was really enjoying this and I could not understand where this cruelty in her had come from.

"Crying like a true sissy." She mocked. " I really do have a wimp for a son. Now, get out out of those clothes and get ready for bed." Relief overcame me on hearing those words. Finally I could escape this bizarre scenario and get to my own room and my own bed and out of Mum's garments. As I started to make my exit from her room she blocked me and said,

"You can get undressed in front of me. I have seen it all before you know." Dejected I slowly removed the shoes, skirt, blouse and bra as Mum stood in front of me staring at me mockingly. I was just about to remove the bra and stockings when she stopped me again.

" Leave those on." She snapped. "You can sleep in those tonight and a nightgown of mine." She marched me over to her drawers and selected a pink frilly nightgown made of silk. She helped me into it then caught my eye and seductively whispered, "Now, help me out of my things."

I thought I had been taken to the depths of humiliation but I realised there was more to come. The colour drained from my face and I hoped I had misheard her.

" Come on" she cooed, " Shoes first.". I sank to my knees once again and carefully removed her shiny spiked heel shoes. "Unzip the dress now, sissy." She added. I stood up and moved behind her and unzipped the tight dress and moved it slowly down her legs so she could step out of it. My Mother's black stocking tops, garter belt and perfect bottom were now on full display to me. I was shaking more now than ever before as I unclipped her Bra. I was too scared to move from behind her, so she turned round to face me and I immediately looked down at the floor so as not to be confronted by my Mother's tits.

"Now who's a shy little boy?" she purred as she put a finger under my chin and raised my head to meet her glance and naked bosoms. Her expression and hard nipples told me she was taking great delight in teasing me. She looked alluringly into my eyes and asked, "What about my stockings and panties Son?" My heart sank as I returned to my knees. I unclipped the stockings from the garter belt and slowly slid them down my Mother's Legs. This was certainly the most humiliating yet also the most erotic task of the night. I was trying so hard not to get excited by it all, but I had no chance against my Mother's feminine beauty and sexual dominance.

Finally I was kneeling before my Mother with my face inches from her black lacy panties. Her pungent female odour was overpowering and I could see the panties were damp from her obvious excitement over tonight's events. I gently took hold of the panties and glided them down her long legs. As soon as I caught sight of her pussy, any restraint was impossible and my cock was harder than it had ever been in my life and I was aching to cum. I was really looking forward to getting into my room and relieving myself. Mother looked down condescendingly at the bulge in my panties and spoke,

"You really are a dirty little pervert aren't you. What kind of a man gets his kicks by wearing his Mother's clothes and jerking off into them? From now on there will be no more jerking off from you without MY permission. I don't want your disgusting cum all over my panties and nightgown. You will sleep with me in my bed tonight where I can keep an eye on you."

Once again I was mortified. But there was no way I was going to stand up to her. I was totally defeated. My masculinity had been crushed. I moved obediently to her double bed and climbed in, with the bulge in my panties still begging for relief. Of course there was no way I dare do anything about it, so I just lay there all night in state of trepidation and sexual tension, dreading my new life as my Mother's sissy slave.




2003 by Sissy Son. All Rights Reserved. These documents (including, without limitation, all articles, text, images, logos, and compilation design) may be printed for personal use only. No portion of these documents may be stored electronically, distributed electronically, or otherwise made available without the express written consent of StorySite and the copyright holder.