I feel my suspenders stretch as I reach up to dust the top shelf in the library. The stool wobbles slightly and I am afraid I may fall. I can feel “Sir’s” eyes on me as I work. I am so self-conscious that he may see my knickers as I work.
The thought of that triggers mixed feelings in me. My mind drifts to feel the softness of my knickers. My cock starts to stir as the silky nylon prison brushes my cock as I move. When I step off the stool, I feel the frilly lace ride up my backside. I almost reach around to tug them out, but manage to stop myself. That would probably trigger Sir. He would probably want me to “service” him in one way or another.
“All done Sir, may I carry on with my other duties?”
“Yes of course my dear. Oh and Sarah.”
I pause on my way out.
“Yes Sir?”
“When you serve dinner tonight, you should wear your other uniform.”
I can feel my face redden.
“As you wish sir. “
“Good girl. Off you pop then.”
As I make my way down to the kitchen to prepare Sir’s dinner, I hear the now-familiar click of my heels on the wooden floor. I can feel the swish of my skirt about my legs. I can’t deny it is turning me on. The thought of what I must wear tonight adds to my excitement.
My current uniform is a practical hotel maid's uniform. Black dress, black stockings, and a plain white apron. Tonight, though, I will be wearing what I think of as a French maid’s uniform. Frills and lace everywhere.
This is all my own fault. If only I could have controlled my gambling. My wife left me due to that habit. She worked hard, and I had to keep house. I tried to get a job, but I was bad at most jobs and couldn’t even hold down a menial one. My wife once said, if you’d have been born a girl and been pretty, you would have been OK. You could have found a well-off bloke to take care of you.
Maybe her saying that had tempted me. I was bored and had hovered the house, done the washing, and was putting away her underwear. It felt so soft, and I wondered how it would feel to wear it. It felt amazing. I got hard instantly. How did it happen so fast? My wife often complained about my lack of sex drive, but just wearing her knickers had me raring to go.
I gradually increased what I wore, and in a few weeks, I was doing the housework fully dressed. That was how she found me. She came home early because she had found out I had emptied out our joint account. I had a sure tip, 20 to one, it couldn’t lose. Except it did.
She threw me out. I had to beg to be allowed to change clothes. She said if I came back, she would tell everyone I knew about my “filthy habits”.
I slept rough that night. Not an experience I would care to repeat. I slept in an old factory with only rats for company. Luckily, I ran into an old friend Dave, the next day, and he let me come to his place. It was a small, rundown flat. Dave was a carpet fitter, but had a drinking problem. His flat was a mess. He told me I could stay if I did all the housework. I agreed, and life went on for a week or so, then the urge to gamble came surging back. I needed money. Dave refused to give me any. He told me to get a job.
I asked around the housing estate for anyone who could lend me £100 for a nailed-on cert in the 3.30 at Haydock. I was told about a guy called Pete. He was known as Hawkeye by his customers for some reason. He loaned money on a short-term basis. He was a loan shark, and I knew I shouldn’t borrow from him, but I couldn’t help myself. The horse won. I had a grand. That’s when I should have quit. I didn’t.
Over the next two months, I won a few small bets but lost the larger ones. I soon owed Hawkeye eight grand. He was coming round the flat to collect what I owed. I decided not to be there. I wandered the streets until midnight and came home. The flat was a mess, and Dave had a black eye and a cut lip.
“You stupid bastard.” He said.
“You utter moron. You’re as good as dead now. Why the fuck did you borrow from him?”
“I’m so sorry Dave. I had no idea he’d do anything to you. What am I going to do now?”
“Well you can’t stay here. He’ll be back looking for you tomorrow.”
“I’ve got nowhere else to stay. I’ll have to sleep rough.”
“That’s no good. They call him Hawkeye because he tracks people down, you know like that guy in the old movie. A tracker or something. One bloke moved to Stoke with his brother. Two weeks later, they found him floating in a river.”
“Oh shit. I have to hide somewhere.”
Dave looked thoughtful.
“Well, there is one place you could try, but the guy is a bit odd.”
“Anywhere, Please!”
"The guy lives in a mansion in the sticks. I did a carpet for him last week. He is looking for a housekeeper. I don’t think they would track you down there. It's off the beaten track. But as I said, He’s a little odd.”
“I don’t care, Dave. Just point me in the right direction.”
Sir Malcolm Gutteridge picked me up at 10AM from Chingford station the next morning. As we drove further into Epping Forest he explained what he expected from me. I was to call him Sir at all times and do everything I was told. I was to work seven days a week, with no time off. I would be paid, but I was expected to stay on the grounds at all times.
They were terrible terms, but it beat floating dead in a river. So I accepted and started work the same day. I would be paid £100 per week directly into my bank. This was under minimum wage, but I had no bills to pay, so I figured I could use it all for betting.
He was odd. The second day I was there, he told me I needed to wear a housekeeper's uniform. I didn’t mind as I had very few of my own clothes. That was until I saw it. The shoes were feminine-looking moccasins. The trousers were women’s slacks with a zip on the side. There was also a white blouse. He even presented me with a few pairs of socks. These were made of flesh coloured see through nylon.
“But Sir. These are.... are ...”
“ARE WHAT!”
He was a large man. Around 6ft 3 inches. He towered above my 5ft 6 inches. I don’t know why I agreed to wear them. Perhaps it was the fear of being thrown out to the mercy of the men who sought to find me. Maybe I was used to doing what bullies told me to do all my life. It could even be that I wanted to wear those women’s clothes.
Sir seemed to treat me a little better after I wore the new uniform. He would stand and watch me work as I dusted. What I found strange was how he would touch my bottom to get my attention as I cleaned. Who does that? I thought about complaining, but I was honestly a little scared of him.
He didn’t leave the mansion often, and we had deliveries for food and other supplies. One driver said “Thanks miss” when I signed for a delivery. I was stunned and went to look in the mirror. My face did look a little feminine. Sir insisted I shave three times a day. He said stubble was a sign of laziness. He had a full beard, so it was only lazy if I wasn’t smooth.
He told me to take the package up to the attic room. I had not been in there before, and the room surprised me. There was a four-poster bed with a pink silk canopy. The carpet was soft and expensive. When I opened the large closet, I was stunned to see a huge array of women’s clothing. I couldn’t help myself. There were dresses and skirts in bright colours, skirts, blouses, shoes, and boots. I felt myself grow hard.
My wife had a typical modern woman’s wardrobe. A few basic dresses, but mainly jeans and leggings. This closet was full of silk, satin lace, and frills. My breath caught when I saw what must be a maid's dress. The skirt had layers of net lace sewn in. It would flare out when worn and bounce when you walked.
I ached to try it on. What if he caught me? No, I couldn’t. I closed the door and stole a quick look in the drawers of the dresser. An explosion of soft fabric and lace greeted me. I let out a sigh. I longed to try on each and every item. Bustiers, bras, knickers, so many pairs and styles of knickers. Stockings, suspenders and even garters. I shuddered at the thought. The dresser was covered with makeup and hair brushes. It fascinated me.
“Francis!”
Sir was calling. I ran downstairs and stood before him.
“What were you doing upstairs? You took your time.”
“Sorry Sir. I wasn’t sure where to put the package.”
“You weren’t snooping then.”
“err, no Sir”
“That was my maid’s room. I had a maid a few years back. I provide all her clothing. She had to leave it here when she left. Did you see anything you liked?”
I turned bright red. Did he suspect? After all I was wearing what was essentially a woman's uniform now. Even though he called it unisex.
“No Sir, of course not”
He laughed and said.
“Well any time you want to, just let me know. I would like a maid swishing about the place again. I used to love seeing her petticoats flounce as she dusted the shelves. I would call you Sarah. That was the name of my last maid.“
He stared at me. Did he know? I felt my cock grow at the thought of wandering the mansion dressed as a maid with a feather duster. Did he really want to see me like that, or was he winding me up?
Everything changed two weeks later.
“Francis come here quickly.” He sounded panicked. I had never heard him sound anything but confident.
“What is it Sir”
“ There was a large man who called himself Pete at the gates. He was looking for you. I told him I had never heard of you. They demanded I let them in, and I refused. “
“Thank you, Sir. I owe him some money. He's not a nice person. He may kill me if he catches me. “
“Don’t thank me yet. You know the walls keep everyone out of the grounds, well, they keep everyone in too. I just saw on the camera, one of the men has a crowbar and he’s trying ot open the gate.”
“Call the police please.”
“Oh Francis, you naive little fool. You don’t realise how I make my money. I can’t have police snooping around.”
I panicked.
“What am I going to do! He’ll kill me!”
“Me too probably. There are four big guys with him. I might stand a chance against two, but four? Let me think.”
I could see on the gate camera, they were bringing more tools.
“What if Francis wasn’t here? What if he found just me and Sarah my maid.”
“What?”
“Go up and change. Be Sarah, my maid. There is a wig at the back of the closet, I think. Be quick and come when I call you.”
I was terrified. I had this slim chance, but it might work. Who would suspect the maid? The butler, maybe. What an odd thought. I ran up the stairs and stripped off. I threw my clothes under the bed. I dressed so quickly that I never got any pleasure out of it. When I dressed in my wife’s clothes I would slowly pull on my knickers. I would feel the lace tickle my legs as they slowly ascended toward waiting cock. Not this time. It was a mad rush. I pulled on a pair of frilly white knickers with rows of lace, black hold-up stockings, a white bra that I stuffed with handfuls of lacy underwear.
I grabbed the maid’s dress I had seen earlier and forced my feet into a pair of low-heeled court shoes. How long did I have left? I searched the closet and found the blonde bob wig. I put it on and sat at the dresser to apply a little makeup. I stopped as I saw myself in a wig. The hair framed my face perfectly. My hair is brown and cropped short. I looked quite feminine.
I had almost no idea how to use makeup. I dusted myself with face powder, then a little red powder on my cheeks. I picked up some lipstick and as I started to apply it, I heard.
“SARAH! Come down, please. We have guests. “
My time had run out.
To be continued..
This part has sex scenes
On the way down to Sir’s office, I slipped into my room and quickly took out the bottom drawer of the dresser and threw the few possessions I had in the space. I put the drawer back and carefully made my way downstairs. The shoes felt strange. The heels were only two inches, but I wasn’t used to them.
My heart nearly stopped as I went into the office. I tried hard not to show any feelings as I saw Pete and two of his goons standing there. Even in heels, I was the shortest in the room. They stared at me as I walked around the desk to stand next to Sir.
At first, I thought they must know who I am. Then I realized that they were looking at my legs. I looked down and saw that one of the lacy stocking tops was just visible beneath the petticoats. Sir smiled at me and said.
“Wardrobe malfunction, Sarah dear.”
My face turned red as I carefully slid the stocking into place. As I looked up, I saw Pete’s goons almost slobbering. This was new to me. No one had looked at me before with desire. I felt so conflicted. I was scared, but felt powerful. They wanted me. Not that I wanted them, but it was obvious that they didn’t recognize me.
Sir broke the silence.
“So, er Pete. You can see my housekeeper is the lovely Sarah, not that Francis fellow you are looking for. “
Pete’s eyes narrowed.
“Sir Malcolm, I am well known for tracking down anyone who doesn’t repay a loan. My problem is, I know Francis came here to see you. His friend told me you were looking for a housekeeper, after we persuaded him that is.”
Oh God, I hoped Dave was OK.
“As I explained Pete, he did come here. I offered him the job, but then Sarah returned. She worked for me last year. She is a lot easier on the eye than Francis.”
As he said that, I felt his hand go up my dress and stroke the bare flesh above my stocking top. I wanted to jump back, but knew I would draw attention to myself.
“Sir Malcolm, I can track anyone. I have methods and contacts better than most police forces. I tracked his phone to this address. So you don’t mind if my boys have a look around, do you?”
“Be my guest. I can see how important this is to you. But I can assure you, he came and I turned him away. “
“His phone was active from the Thursday he ran, until Friday.”
He could track my phone! No wonder he had a reputation. My phone ran out of charge during my first day on the job. My credit had expired, and I had forgotten my charger, so I never did anything about it.
I felt Sir’s hand progress to the back of my knickers. I felt him gently rubbing his hands over the frilly lace. I wanted to slap him, but knew I couldn’t. I found it strangely erotic. It sent an electric shock through me as the soft nylon rubbed against my bottom.
“When Francis turned up and I told him Sarah had returned to her old job, I felt sorry for him and let him stay the night.”
Pete gazed at me. He smiled when he saw where Sir’s hand was.
“I suppose that would explain it. I know he came here. His debit card was used to buy a one-way train ticket to the local station. He only has £20 left in his account. Have you any idea where he has gone? I can’t trace his phone. I may have to go to the next level and trace him.”
What did he mean next level? Did he have access to security cameras? He had access to my mobile and my bank account. This was like something from the TV program called Hunted.
“If you don’t mind me asking Pete, why go to all this trouble for a few thousand pounds?"
Sir said.
“ I loan money all over London. I have a reputation. The amount doesn’t matter. If he gets away with it, everyone else will try.”
“But all these resources on a petty thief?”
“You know how people like us work. Reputation. If just one little scum bag gets one over on me, my reputation is ruined.”
“Aren’t you worried about him going to the police?”
“You should know better. You are almost as well-connected as I am. The last one that tried that ended badly. You remember the headless body they found last year in the Thames? That was him. Even if he introduced a copper to me, all they would find is a spotless record. I don’t even have a speeding ticket. As I said. I’m connected. It’s not like Pete is my real name anyway.”
“As you can see Pete. Only myself and Sarah live here. “
It was hopeless. As soon as I left and used my bank card or phone, he would have me. How could I survive without money? I just stood there as Sir started to squeeze my ass cheeks. Then Pete’s goons returned.
“We found nothing. One bedroom with men’s clothes and another with some very sexy women’s clothes. You should see the underwear, it is.......”
“That’s enough Terry!. It seems you are telling the truth Sir Malcolm. You have my number. I may pop back from time to time. If you hear anything, call me. Oh, and I know what business you are in, so I know you won’t be calling the police now, will you?”
“Heaven forbid no. If I hear anything, I will be in contact.”
“Just make sure you do,” said Pete as he left with his men.
“Sir thank you so much. I thought he would recognize me.” I said.
“Well my dear, you’re quite convincing as Sarah.”
“What am I going to do Sir?”
“The way I see it, you have no choice. You have to stay as Sarah. If you want, I can give you a few hundred pounds in cash, and you can go. But I think you won’t last very long.”
I stood next to him, considering. I barely noticed his hand move around to the front of my knickers until he gently rubbed my cock though the nylon. I was too terrified of my situation to notice much. If I took his money, I could buy a tent and some food and live in a forest. I’d never been camping in my life. I knew I wouldn’t last long.
“What do you mean, stay as Sarah, Sir?”
“You would become Sarah 24/7. You would live, dress, and work as a woman. Francis will be gone forever.”
I had no choice, at least at the moment, but I knew there was a price attached to this offer.
“What else would you want of me for hiding me Sir Malcolm? You aren’t doing this out of the goodness of your heart.”
“There’s my girl. I thought you were bright enough to notice. I have certain tastes. Odd tastes to some. I like ladies like you, Sarah. Especially fresh virgins like you.”
This was a nightmare. Death or a pervert's sex toy. I weighed up my choices, but in the end, I didn’t want to die. I had to take his offer. I didn’t dislike dressing as a woman. I enjoyed it. The idea of being forced to dress constantly was quite frankly one of my fantasies, but sex with a man?
“I will do as you say Sir. I will be your Sarah.”
He grinned at me. He looked like a cat that had caught a mouse.
“Splendid. I will order you some more clothes tomorrow. Before I do, though, we need to seal the deal. “
“Do you want me to sign something?”
“No, dear. I need to be sure of your commitment. Be sure you will comply. Get on your knees.”
Oh God. I knew this would happen. I was hoping it might be a few days off, though. In a daze, I got onto my knees between his legs. I felt my knickers riding up my crack. I felt the petticoats tickle my knees. I must have looked so feminine to him. He had taken his belt off and pulled down the front of his boxers.
“There you are, You know what to do. Think of it as payment for keeping you safe. You keep that happy, and I will keep you safe.”
I stared at it. His cock was much larger than my 4 inches. It was nearly twice the size and thicker. No wonder my wife was never satisfied with me. He was circumcised. I suppose that would mean it was clean. I knew I had to do it. When I had worn my wife’s clothes and jerked off, I had sometimes thought about being a woman having sex with a man. To do it for real is something else.
“Come on, girl. Start by licking my balls.”
I tried not to think about what I was doing. For the first time in my life I held another man’s cock. I lifted the semi-rigged organ up so I could lick his balls. I slowly licked his hairy balls. He smelled fresh, but tasted a little salty. I couldn’t believe I was doing this.
“Oh, you dirty girl. Yes lick my big balls you whore.”
I suppose he thought that was encouraging. I kept it up for a few minutes, then he pulled my face up to look at him.
“Good girl. That was the starters. Now the main course. “
I looked back down and saw he was now fully erect. The head was full and bulbous. If I did this, I would cross a line. I would be a cocksucker. I would be gay, wouldn’t I? Then I thought, women do this for their men all the time. I didn’t think less of my wife when she did it. I had to think like a woman. I was dressed like one, so I would play the part.
I licked the tip, and he shuddered. I traced the whole length with my tongue. His cock was twitching and he was breathing hard. I put my mouth into a “O” shape and slowly swallowed as much as I could.
“Oh, yes, Suck that cock woman, get it in you.”
A little over half way down, it hit the back of my throat and I almost gagged. I slowly bobbed my head up and down, carefully making sure to cover my teeth. I could hear him groaning as I concentrated on my task. I could feel the veins with my lips and almost threw up. No, I had to do this. I used my right hand to wank the part I couldn’t fit in my mouth, I used my left to tickle his balls with my nails.
“Oh you little cock gobbling slut. You are a pro at this.” He said.
For a moment, I felt a surge of pride. I was doing a good job. He loved what I was doing. I felt his organ swell and tried to pull away. He held my head down and came hard in my mouth. It was salty and slimy and it kept coming. I was coughing, and he let me go. I fell back onto my backside. He reached into a drawer and gave me some tissues.
“Clean yourself up girl, then redo your makeup. I’ll have dinner a six.”
That was that. I was now Sarah. Sarah, a cock sucker, Sarah a maid, Sarah a woman. I suspected I would have to do that every day. How do women put up with it? I had a feeling I was going to find out.
The rest of the day I was in mild shock. I robotically carried out my duties in my maid's uniform. Sir told me to have an early night. He told me that I should remove all of my hair before going to bed. He reminded me that, as I was now Sarah, I should sleep in her room and use her clothes. I just said "Yes Sir".
I found several tubes of Veet and a pack of pink lady razors and got to work. I had always wondered what it would feel like to be hairless when I wore my wife's clothes. The material was so soft, but you don't feel it with a coating of hair.
I found some hair dye in the bathroom. Platinum blond? I thought in for a penny. It took hours to do all the work. After much shaving, I showered for the last time and looked at myself in the full-length mirror in my new room.
My light brown hair was shining blond. My body was smooth all over. I removed everything from my eyebrows down. I felt so sensitive. It was if I could feel tiny movements of air on my skin. What would the clothes feel like now?
I must get some sleep, I thought. I looked through the drawers, my drawers? I found a pink silk baby doll. It was made of smooth silk with one inch of black lace around all the edges. I had to wear it. I slipped the top over my head, and my nipples hardened as the silk made contact. I let out a little moan. I felt the lace on the hem tickle the backs of my legs as I bent to put the knickers on.
Oh, but the knickers. I shivered as I pulled them up my legs. I did it slowly. The lace felt slightly scratchy, but so thrilling. I got hard instantly. I couldn't believe how good it felt. Women must feel this every day. I felt so cheated.
I slipped into bed and gently stroked myself from outside my silky nightwear. Then it all hit me. What was I doing? It had happened so quickly. I had to spend the foreseeable future as a woman. I had just sucked a man's cock. The thrill of having some of my fantasies come true was wearing off. This was very real.
Was I gay now? I didn't feel any different. I was so confused. I had to lie low until Pete, or whatever his name was, forgot about me. Would Sir be happy with just oral? I suspected not. There is one thing in having fantasies, but having no escape from them is something else. Could I just pretend to be someone else? How could you do that without needing I.D. to drive or to get a bank account? I had seen off-grid videos on Youtube, but I had never even been camping.
My thoughts were interrupted when Sir came into my room.
"I'm glad you have settled in, Sarah. All this is yours now. I expect you to wear most of it."
He sat next to my bed and inspected me. He pulled the covers back and whistled in appreciation.
"You look wonderful, my dear. I like the hair. It's a little short, but it will grow."
His hand reached down to the front of my knickers and gently stroked the outline of my cock through the silk. I couldn't help it. My hips thrust forward to get more of this wonderful sensation.
"Oh, but Sir, I'm not.."
"Gay Sarah? No, nor am I."
He gripped my cock throuugh the knickers and I felt the lace tickle my balls. This really did feel gay to me.
"Let me explain, my dear. I can see you are confused. I love femininity, but I don't love women. I went to public school and often the boys experimented. The people I deal with would not take me seriously if they thought that I was gay. I don't think of myself that way. I like women who are a little different. Women like you.
"But Sir, I'm not a woman."
He chuckled.
"You are more woman than man. Just look at yourself. I bet you couldn't wait to wear these clothes. I think the moment you saw this room, you were thinking of how you could try everything on."
How did he know? My breathing got harder as he sped up his rubbing. His left hand pinched my nipple through the silk and started rubbing in slow circles. Oh, god, it felt so good.
"You love the feel of this silk, don't you, my dear?"
I really did. I mumbled, "Yes Sir."
"Imagine Sarah. You can wear silky knickers every day. You will feel the lace as you move. The petticoats will brush against your stockings. You will feel your bra tightly hugging you, reminding you that you are a woman."
Stockings! How good will they feel on my smooth, sensitive legs? My hips were bucking, trying to get more sensation from his hands.
He moved slightly and took his hand from my chest. I closed my eyes. I needed to cum. It had been so long since anyone had touched me.
"I will take care of you, Sarah. Your life will be soft, sexy clothes. Makeup, perfume, cleaning, washing, and cooking. You need not have to worry about money or anyone being out to get you. Be my Sarah, be the woman you know you want to be. "
With that, he suddenly slipped a greased finger into my backside. I screamed. "YES, YES! Oh please, yes"
I shot a huge load into my knickers. I had never felt this turned on. I kept pumping and almost passed out. It was so intense.
"I'm so glad you agree, Sarah. I suggest you change your nightwear wear my dear."
I was still dazed as he got up to leave.
"Tomorrow I would like you in the traditional maid's dress when you serve me. Breakfast at 8.30. Goodnight."
As I calmed down and lost my "horn" I was getting the feeling of buyers regrett. What had I got myself into?