The Live-in Maid Ch. 01

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Married man loses everything due to crossdressing.
5.5k words
4.21
53.5k
36

Part 1 of the 3 part series

Updated 06/08/2023
Created 01/07/2018
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Quietoldie
Quietoldie
1,014 Followers

The back story

I found my wife Carol through a dating website. She'd been in an abusive relationship before we met and realised I was not going to be any kind of threat in that way. I'd been single for a year or two and didn't want to jeopardise our relationship by explaining to her that I had a cross dressing and foot/shoe fetish. She's a few years older than me. Her previous experience of men has made her cautious and tough. It took over a year of pestering before she agreed to move in with me. We married a year later.

Carol can be a bit controlling where I am concerned. I don't mind, in fact it's a bit of a turn on when she orders me around particularly in the bedroom. I think it's an over reaction to her previous relationship. She insists on me licking her cunt before intercourse, pushing my head down under the duvet. I found this unpleasant at first but have grown to enjoy it over time. We are happily married although with my job taking me away from home a lot I think Carol would like to see more of me. I'm involved with a project at the moment which is taking up a lot of my time so that even when I'm living at home Carol complains that she hardly ever sees me.

Tim, our next door neighbour, is the commanding officer of the local Air Cadet group in the town where we live. We often see him on Monday evenings getting into his car in full uniform on his way to attend their regular meetings. I notice Carol looking wistfully at Tim on Monday nights and realise that she has a thing for a man in uniform.

Tim is also a member of Rotary. They are holding a special Charity dinner, a proper black tie occasion. Tim is divorced from his wife and has no one to take with him. He asks Carol if she will go.

"What do you think David darling? We never seem to go out together these days."

"You're right dear, but don't you think it's inappropriate to go on a date as a married woman with another man. I'll try to get a night off soon and we'll go out dancing."

Just putting what she is asking for into words causes a stiffening in my trousers. I know my Carol, always wanting to please others. I imagine them dancing together, their bodies touching, my penis jerks a little.

"A date? It's not really like a date. He just needs a 'plus one' otherwise he says he won't go. Of course if you say I can't I'll accept it and that would be the end of it, but I know you'll be working on the project on Friday night and I could do with a night out."

"Okay darling, you can go. I'm sorry I've been neglecting you lately."

I can't tell Carol, but the truth is I've suddenly discovered that I want her to have a date with another man. Anything could happen. It excites me. My reaction surprises me. Until now I had never suspected that I might enjoy the humiliation of allowing my wife to spend an evening with someone else, someone she apparently finds attractive.

On the Wednesday morning a large package arrives addressed to Carol. Carol takes it up into our bedroom to try it on. It's her dress to wear for Friday evening.

"I don't have anything suitable to wear for such a posh do." Carol tells me on her return to the living room, trying to make light of it. She doesn't add that he's sent her a low cut bra, a garter belt, dark stockings and a flimsy pair of see through panties. Carol finds his choice of underwear much more daring than her usual lingerie. It excites her but she's not sure she has the courage to wear the items.

I am of course out at work when Tim arrives to pick her up for their 'date'. He's arranged for a taxi to take them to the venue. Tim, dressed immaculately in his dinner suit, adopts a commanding pose as they sit in the rear seats.

"I want to see your panties. Pull up your skirt for me. I want to be sure you've worn what I requested."

Carol hates to make a scene. She's generally compliant but feels this request is going too far.

"Of course I'm wearing what you asked" she says blushing. "You'll have to take my word for it. Besides the taxi driver will see."

"Stand up and turn your back to him. Quickly now. You're my date tonight. You should do as I say."

Carol hesitates but still stands firm.

"No, I can't." she says defiantly although she has to admit that the idea of displaying her body to him does make her feel aroused.

Tim quickly grabs the top part of the back of her dress and before she has time to struggle she finds herself laying across his knees, her rump suddenly higher than her head. His rough behaviour takes her completely by surprise. He draws her skirt back revealing what she had refused to reveal. She's worn her panties outside the straps from her suspender belt so he easily pulls them down to her knees. Then, in full view of the surprised driver, he delivers two hearty slaps to her bare bottom.

He releases her and within seconds she's respectable again sitting on her smarting backside. She hangs her head and a tear runs down her cheek. This is a man who likes to get his own way. She realises her panties are damp. She's decides to be more compliant for the rest of the evening wondering what's in store for her.

As he pays the taxi driver the man says;

"I wish my wife would wear a suspender belt and stockings when I take her out."

"Ah, but she's not my wife." Tim says. Carol notices the man raising his eyebrows. He's looking towards her wedding ring. She colours up again. She's thinking that taxi man has concluded that she is Tim's mistress. This thought only tends to increase her arousal.

The restaurant within the hotel is packed. They are seated on a long table. Her chair is very close to Tim's and she has just about enough elbow room to eat her meal. Another man is seated on her other side and he seems to be there without a partner. Tim is surrounded by other men from his own club and preoccupies himself with discussing club business which she knows nothing about. His hand is on her knee for most of the meal. He eats with his fork in his right hand. Carol doesn't want to cause a scene, removing it firmly the first time but leaving it there when it returns almost immediately. He's stroking up the outside of her leg, slowly getting higher. She's trying to have a conversation with the man on her other side but finds Tim's behaviour distracting. He reaches the part above her stockings and pinches her bare leg. It makes her jump. The tablecloth conceals his activities. She glances towards Tim realising that her sudden movement has ended Tim's conversation with his friends.

"Are you alright Carol dear?" He says.

"I'm fine, it was just a shiver. I think someone's just walked over my grave." Carol says. What a stupid thing to say? It was the best she could come up with.

"Carol's not used to wearing a backless dress are you dear? I expect you're feeling a bit cold."

"No, it's not that. I'm fine." She takes another gulp of wine and Tim tops her glass up. She makes no comment although aware she's already had more than enough.

The hand is still there. He doesn't pinch her again but begins stroking the bare leg above her stockings. Her dress is bunched up around her waist. She knows no one can see and she's thrilled by Tim's audacity. So far it's been the outside of her leg receiving attention but after reaching her panties and giving them a light tug he moves back to her knee again and moves his fingers to the inside. Her legs are close together.

"Open." He hisses so close to her ear that no one can hear him. She relaxes, letting her legs swing wide. This experience is totally outside her normal behaviour but she decides to passively allow him access. Tim reminds her of her last boyfriend but unlike him Tim possesses all the social graces. He's from a different strata of society. The hand slowly, almost imperceptively moves higher. Once above her stockings he strokes her bare leg but goes no higher. Carol is soaking. It's tantalising to feel his hand almost as far as her wet panties and as the meal continues she wants more.

"Finger me, please." She has her mouth to his ear and the comment is barely audible even to him.

He gives his answer with a brief shake of the head.

"Sorry dear, what did you say?" Other guests stop talking and look towards her.

"I need to powder my nose." Carol says thinking quickly. How could he embarrass me like that? She moves her chair back and stands up. The men on the table all stand up respectfully embarrassing her even more. She walks briskly in the direction of the loo.

After the meal and a few boring speeches she begins to relax as the DJ plays a selection of dance tunes. Tim is a good dancer and most of the dances are in hold. Tim takes the opportunity to put his hand on her butt and she finds his knee pushing into her crotch at times. This helps to keep her aroused. She has accepted that he can do what he likes with her. He must know that by now but instead of whisking her away to a quiet place they are on view all evening.

They kiss in the taxi on the way home liberally sharing tongues. Carol feels disappointed that Tim chooses to go no further.

It's 1o'clock in the morning when they arrive at her house. Carol is surprised to find a light on downstairs. Tim walks boldly to the door behind her and follows her in.

"Get me a whiskey. Carol will have a glass of wine." Tim says. I've waited up and am surprised to find Tim inside my house. I find myself rushing to the kitchen to get the drinks he's ordered so rudely. Why am I obeying this arrogant man? He has mastered an ability to get people to do what he wants. Have his tactics worked on Carol too? My penis stiffens.

He is sitting next to Carol on the sofa. They are holding hands like young lovers.

They are looking into each others eyes.

"Have you put ice in my drink?"

"Yes sir." 'Sir'? Where the hell did that come from? I've just abdicated all my authority in my own house.

Tim addresses me whilst still looking towards my wife.

"Carol whispered something to me during the meal that made me think she's not getting the attention she deserves. She's just given me a long goodnight kiss. You wouldn't take her out dancing so you let me do it for you. There's something else she needs and I will do that for you as well." He turns to me with a wicked grin on his face.

"I'm taking her upstairs to fuck her and I can tell by the shape of your trousers that you won't lift a finger to stop me. Come on Carol, he can listen at the door if wants to."

I look Carol in the face. She looks happy. As he strides towards the stairs she meekly gets up and follows him taking her glass of wine with her. I would have heard her moans if I had stayed downstairs. Instead I stand behind the half open door unable to show my shame to them, watching him impregnate her through the hinge crack. My trousers and panties are round my ankles as I'm masturbating furiously. It seemed afterwards to be one of the most exciting moments in my life. They both undress and she gasps when she sees the size of his cock but seems more than willing to get it inside her. It fits her like the proverbial glove and he drives it in and out as if he's trying to go for some kind of speed record. I can see and hear that she is enjoying herself.

"Faster darling, faster, that's what I like. I'm cumming but don't stop. Don't spurt just yet. I want this all night long. Oh, oh, oh, oh, oh." She screams at the top of her voice. This is a side of Carol I didn't know existed.

Tim continues his fucking moving her around into different positions. I know she likes it when I take her from behind and soon his hands are kneading her nipples and breasts whilst his large member penetrates her cunt from the back. Will she want me after this? My cock's gone flaccid after spurting and the excitement and euphoria have given way to fear and doubt. A real man would have prevented this. Carol doesn't know it but she's married to a panty wearing sissy. I'm not a real man. I fantasise about living as a woman but that could never happen. I'm not transgender. I get a sexual thrill from dressing up in women's clothes that's all.

I feel a stirring in my penis as Tim reaches his climax. What if she gets pregnant? Our form of contraception is by condom and Tim has ridden her bareback. Why would that excite me? I begin stroking again as Tim pushes her head down towards his crotch and I see her engulf the cock she loves so much with her mouth. It must be about six inches when flaccid. It's as if she is on her knees worshipping the phallus. Did her last boyfriend make her do this? She's never given me a blow job. It seems like it's a means to an end because as soon as its hard she pushes him on his back and climbs aboard. This time the fucking is slower and takes much longer. I lose count of her orgasms but it seems like forty minutes to an hour have elapsed before they stop, both exhausted.

I scuttle off to the spare room. I can't get to my supply of pyjamas as they are in a drawer in our bedroom so I climb into bed in the panties I was wearing under my jogging trousers earlier. It seemed fitting for me to spend the later part of the evening up in my den in the loft whilst Carol was out. Carol has never been up there, she's too scared of heights to go up the 12 foot ladder. It's my refuge from the world where I keep all my clothes. I've collected shoes over the years, some to fit me and other smaller ones I use for wanking. There's not a stitch of male clothing up there. She probably thinks it's a small area without flooring in the way some lofts are.

It's hard to sleep but I finally drift off wakening to more of Carol's screams. Trust Tim to have brought a supply of Viagra with him. She probably thinks he's a superman. I'm tossing and turning after that so I creep back to my position by the crack in the door. They are lying on top of the duvet naked in each others arms. I see him blow in her ear, then lick it. How can he know she likes that? She stretches luxuriously very relaxed, like the cat with the cream.

"Thank you for such a wonderful night Tim darling. I know what men are like, particularly your type of man. Once you've had your oats you drop the woman and move right on to the next one don't you? If that's the case okay. I've got my memories." She sighs. "I WAS hoping for more."

"You should know me better than that living next door. Have you seen a continuous stream of women coming and going?"

"No".

"Well then. I've had my eye on you for some time. You're a very attractive woman. I've also been observing that hubby of yours. There's something he's not telling you. And he's hardly ever at home. I got to thinking you might be missing out. I was right. Did you know there's a velox window in the back roof?

"No, that's strange, I just thought he used it for storing Christmas decorations, that sort of thing."

"Last winter I'd be down the garden in my greenhouse of an evening and often as you left the house the light would go on up there. There's something going on that you don't know about. I'm sure of it. Have you ever been up there?"

"No, I don't do heights. I get vertigo standing on the back step. Has he got a cannabis farm up there do you think?"

"Dunno, maybe, but you'd know all about it if he smoked the stuff. It's doubtful, you'd have smelled a rat when the first electric bill arrived. I know what, first thing tomorrow send him out to the shops and I'll take a quick peak whilst he's out. Maybe he's a serial killer with pictures of the victims on the walls." He bursts out laughing at this knowing how preposterous it sounds. Carol smiles but I can see she's worrying.

"Okay love. You're a star. Now I need to get my beauty sleep." She snogs him briefly then they get back under the duvet turning their backs to each other.

There's been times over the years when I've wanted to tell her about my cross dressing and love of women's shoes. I'd make the decision to talk about it but bottle it at the last minute. I've always been scared I might lose her. It's out of my hands now but the timing is all wrong. What can I do? There's no time to change the room to hide all my women's gear. I'll just have to go with it and see what happens. I lay there going over all my options. There are none. I can't sleep so I tiptoe downstairs and sit on the sofa thinking that my life is probably in ruins. I've allowed my penis to override my common sense. Why had I let her go out on that date?

I started wearing women's clothes in private when I left home to go to college at the age of eighteen. I'd always liked reading the stories in Literotica and other free erotic story sites and became drawn to the ones about cross dressing. I was always rather shy and quiet when I was younger and it took a lot of courage to walk into a shop and buy items to try on. Time and again I would enter a shop intending to buy panties and walk out again with nothing. I could understand why some men steal clothes from washing lines but would never steal from other people. My mother brought me up properly.

"Do as you would be done by." She'd tell me and it's a maxim I have always followed throughout my life. She taught me to respect others and treat them in the way I would want to be treated myself. "Honesty is the best policy." was another saying that she drummed into me as I grew up. She was quite strict my mum, not afraid to spank me if she found I'd not done something she asked me to do or particularly if she found I'd done something she'd told me not to do.

I was quite well behaved as a child but I had a butterfly mind, jumping from one idea to another, my head in the clouds. Teachers at school constantly complained I was not paying attention in class and although I am reasonably intelligent, my grades were well below average. Mum despaired about me ever getting a decent job.

"You'll end up sweeping the streets if you don't book your ideas up young man" she said one day as I was laying across her knee with my trousers around my ankles whilst she spanked my bare bottom. She probably noticed my willy stiffen as the slaps rained down but never made a comment about it.

So I would never have dared to put on panties whilst I was living at home. There were a lot of rough youths attending the school I went to and I realised I had little in common with them. The girls were much kinder and more thoughtful so I mostly hung around with them during the break. They recognised that I had a sensitive nature and I think, if I'm honest, they sometimes protected me from the bullies. I would often daydream about being a girl and I think that may be a reason for my fascination with the clothes they wear.

Anyway I eventually succeeded in buying my first pairs of panties in a large department store. It may have been my imagination but the female shop assistant just seemed to know I was buying them to wear myself. She smiled at me in a knowing way and I immediately felt my penis rise. From the stories I was reading at that time I knew I was turned on by humiliation connected to anything sexual. She seemed to have an understanding nature so I made sure she served me for other similar purchases. If she hadn't suspected anything that first time it must have been obvious after two or three further occasions.

"Are you wearing anything special today?" She whispered one day as I approached her counter.

I hadn't expected her to come out with a comment and didn't know what to say.

"Er, yes." I managed with difficulty, my penis erecting as it had before.

She put her finger to her lips. "Don't worry love, it's our little secret. I've not told the other staff. Always ask for Doreen when you come in."

The dressing up was always kept private, something I did behind closed curtains. I was okay with the fact that one other person knew my secret and trusted Doreen to keep it to herself. As we got to know each other better she'd arrange for me to come in at closing time if there was something I wanted to try on. I'd let her see me en femme and found her advice helpful.

Quietoldie
Quietoldie
1,014 Followers
12