This story contains sex scenes
I knew one day I would be seen or caught. I couldn't help it. The urge was just too strong. All crossdressers suffer the same feelings. Guilt and shame. I was a man. Why was I lessening myself wanting to dress and appear as a woman? I had tried to stop before. I had gathered up all my clothes, shoes, wigs, and makeup. I filled three bin bags and threw them in the a skip.
Within a month I was craving the feel and the calm the clothes gave me. I started to buy clothes again. The money I wasted throwing my previous collection out, was sheer madness. I grew to accept I was going to be a sick pervert for life. I was disgusted with myself. Why couldn't I be a "real" man like my father. Mind you, he used to come home drunk and hit my mother then use his belt on me once she was unconscious. If that was a real man, then I was glad I wasn't it.
I had never had much luck with women. I could chat with then fine, but they never liked me on a sexual level. Women seemed attracted to money, power and confidence. I had none of that. I worked in telesales for a pig of a boss and lived in small bedsit above a fried chicken shop. Yeah, women were queuing up for guys like me.
I had learned from chat rooms that I was not unique. I had done, what was known as "purging". They also advised me not to throw anything away if I wanted to stop. Just pack it all away. One "gurl" told me I like many of the broad spectrum that is CD/TV/Trans, had an itch that you could almost never stop scratching. I was told that the lucky ones just like wearing women's underwear sometimes. Some of the unlucky ones were truly trans women. She told me that most trans women could never hide what they were for long, and when they "came out" they were subject to hate, ridicule, and prejudice.
I had graduated from being happy just dressing fully, to wearing a wig and makeup. I looked in the mirror and saw the smiling happy woman I should be. Not the failure of a man I was. I needed to share her with the world and had started to venture out when it got dark. My heart nearly exploded the first time I did it. The thrill of walking pass people in the street was amazing. The fact that they only glanced at me I passed by with my one inch heels clicking as I walked by, gave me a rush.
I had on my ginger bob wig, a knee-length dress, black stockings, low-heeled ankle boots, and a coat. The indifference meant that everyone assumed I was just an average looking woman on her way somewhere. It was a wonderful feeling, being accepted.
I was feeling good as I went into the small alleyway that led to my bedsit. I heard a loud click and turned.
"Well, well, well. Look at you. Don't you just make a lovely looking ladyboy?"
My heart felt like it had jumped into my throat. I saw it was Jim from my office.
"Excuse me. I need to get to my flat. Can you please move?" I stuttered in my best high-pitched voice. I had not practiced talking like a woman. I had never expected to talk to anyone.
"Don't try that on me Ken, I know it's you. So you're a sissy, a ladyboy. They are going to wet themselves when I show these pictures at work tomorrow."
My heart sank. I couldn't bluff my way out of this. I was caught. he was going to expose me to the world. I could feel the panic rising in me.
"No, my name is Kara." I said.
Then I realised, I was not going to get away with it.
"Please Rob, don't please." I almost sobbed the last please out.
"Yeah, old Jegs is gonna love these. You know how he feels about poofs."
Mr Jegs was our boss. He had a gay brother and hated gays. He would find a reason to sack me for sure. I saw my whole future getting even shittier than it already was.
"Please Rob don't tell anyone. I'll do anything."
"Anything eh? I know you've got no money, you're crap at selling. No, I'll have to think of something else. Invite me in for a coffee."
I hated the thought of him coming into my home, but what could I do?
He sat down and looked about my bedsit.
"My God, this is grim, isn't it? Milk and two sugars."
It struck me as odd. Here I was flitting about the kitchen in a dress and heels making coffee for a man I had invited into my home. I had a weirdly erotic feeling. This was like graduating to the next level. Well, it would have been if Rob wasn't such a misogynistic prick.
I gave him his coffee and sat next to him on my small worn sofa. He slurped his coffee and burped loudly. He was drunk, judging by the smell of him.
"So, Rob, will you delete the pictures now please?"
He put down his coffee and put his hand on my knee. He stroked the top and the underside with his fingers. Instinct told me to slap his hand away, but the feel of his fingers through the soft nylon sent shivers down my spine.
"If you think I'm letting go of this golden opportunity, you must be soft in the head. It is gonna cost you a lot to get out of this."
He took my right hand and placed it on his groin. I felt his stiffening cock grow at the presence of my hand.
"Be a good girl and rub me now. If you don't you know what happens."
Possibilities flashed through my mind. Punch him in the face? He was 6ft 2. I was 5ft 7. He would beat me to a pulp. Tell him to fuck off? He would show the picture of me at work. I would lose my job and have to move. I had £20 in the bank to last a week until payday. How could I move and start again?
I was stuck. I had to do what he wanted. After all, I wanted to feel like a woman right?
He unzipped his fly.
"Reach in bitch. Pull it out."
It was like watching someone else do it. I saw my delicate-looking hand with pink nail varnish disappear under the waistband of his pants and fish around for his cock. Slowly I pulled out his stiff, cut cock. It twitched in my hand.
"There you go, girl. Just what you sissies love. Get busy."
"But.. Rob, I have never, I mean..."
"Don't tell me you are a virgin? Bloody hell. This will be more fun than I thought."
His right arm came up and forced my head down to his groin. My face was next to his cock. I could smell it. He hadn't showered before he left home tonight. His rod twitched again and the head seemed to be throbbing.
"Get on with it bitch." he said.
Then he directed his cock towards my lips. I closed my eyes and opened my mouth. His right hand pushed my head down until I engulfed half his shaft. It really didn't taste of much. My tongue explored the shape of the glans. In my head, I thought of myself as a girlfriend giving her first blowjob. I would get through this. This is how I would cope.
Rob threw back his head and groaned.
"Oh, my God. Do you know how long it has been since my wife gave me a blowjob?"
Years, I thought if you act like this with her you pig. I thought.
I started stroking the shaft with my finger as I bobbed up and down. I felt it swelling in my mouth. He was about to cum. he pushed my head away.
I was surprised but grateful.
"Do you have any condoms?"
I was not ready for this. Surely he wouldn't? No, I couldn't."
"No sorry. I don't."
"OK. Lay on your bed on your back."
I didn't know what was going on, but I obeyed him. As I lay down he pulled me until my head was overhanging the edge of the bed. He shrugged off his trousers and lifted up my dress.
"Stockings and suspenders. Beautiful."
He leaned over me and slid his cock into my mouth. I gagged as it slid down my throat. I just wanted this to be over and concentrated on stopping my gag reflex. As he pumped his cock in and out of my mouth his balls slapped into my eyes. I was totally at his mercy. My world was reduced to his balls banging into my face and his cock sliding down my throat. This had all happened so fast. I just wanted it to be over.
He withdrew suddenly and squirted cum all over my face. I shut my eyes and coughed. It was over. When I could talk I sat up and said.
"You will delete the pictures now won't you Rob?"
"Not just yet."
"What? You said..."
"I will. I just have one more thing I need."
"If you fucking show those pictures I will tell everyone you asked me for a blowjob."
"I'll just deny it. You enjoyed it anyway. Look at your knickers."
I looked down. There was full-on tenting going on down there. What the hell was happening to me?
"I promise, just do this and I will give you my phone to delete the pictures ok?"
"Ok, Ok. I just want this over with. What do I have to do?"
"My wife is away at her mother's this weekend. I want you to be my stand-in wife. She has lots of sexy clothes she never wears. You can wear anything you like. I expect you to carry out all the duties of a wife. Saturday morning until Sunday evening. Deal?"
"What was I going to do?"
What do you think Kara should do?
This story contains crossdressing and sex. If you don't like sex stories, please don't read it.
I had a few sleepless nights after my encounter with Rob. I woke up from a dream where I was in an old TV ad. The Shake and vac woman was dancing in her heels and skirt, hovering up Shake and vac. She had my face. I remember seeing the ad on Youtube. She looked like a typical 1980's housewife. I found her a turn-on. The thing is, I didn't want to have her, I think I wanted to be her.
Friday lunchtime I was sent my sales figures. I was always worried about this. I knew I was close to getting fired. When I got the email, there was an extra £50k on my figures. That made £62k! That was more than I did in a month normally. That would give me over £600 in commission, and save my job.
"Did you see your figures?" Rob said quietly in my ear.
I turned and said.
"Yes. A little better than I thought."
"I have to look after my little stand-in wife don't I?"
"It was you then?"
"Yes. The old man was talking about getting rid of you, so, I thought I'd help."
"Wow, thanks Rob. I'm really grateful."
"You can show me how grateful you are this Friday night. Do you have a black wig?"
"Err, yes, several different colours, why?"
"Bring them all with you. I want to choose what you wear. See you Friday. I'll call when I want you to come over. Come as Ken. I don't want the neighbors to see another woman."
I felt a lot better about Rob. He had saved my job and effectively gave me £600. As I thought about it later during my lunch break, it was almost like being a prostitute. I was being paid for sex. He saved my job so he could use me. The blackmail would not be so effective if I lost my job.
I was just not used to anyone helping or being nice to me. In an odd way, even this abusive situation made me feel valued. Someone wanted me. God, I was fucked up.
I got the call from Rob at 9 pm. I had packed a bag with some of my clothes shoes and makeup and driven over to his house. I parked one street away as instructed and knocked on his door.
Rob had a shit-eating grin on his face when I arrived at his detached house. The house must be worth almost a million. I never realised he was this wealthy. Sales management had been good to him.
"Upstairs, turn left 3rd door. There are clothes on the bed. Wear your black wig and black eyeshadow."
What the hell was this about? I thought as I climbed the stairs.
On the bed was what looked like a wet look fake leather one-piece woman's swimming costume, fishnet tights, a black lace mask, and a pair pvc, thigh-high boots. The heels must be 6 inches high. This was a dominatrix outfit. This was confirmed when I lifted the boots and found a small leather whip.
I stripped off and started to dress. The fishnets were the large hole variety. The clothes were making me excited. My little cock kept poking through the tights. My mind told me I was being used by this man, my cock said good, enjoy it.
The body had a snap crotch. I'm sure it would be used later. I managed to secure my cock between my legs and did my makeup. Black eyeshadow and dark red lipstick. My eyes looked amazing. It was a shame to cover them with the mask. I picked up the whip and looked at myself in the full-length mirror.
Oh, my god. I looked stunning. I felt my cock strain at the sight of myself. My legs looked like they went on forever in the shiny PVC boots. I was a little unsteady. I had never worn anything this high before.
The door opened and I heard Rob whistle.
"Fuck me. If you're not my wet dream. Kara, you look out of this world."
I felt a surge of pride. I am not used to compliments. No one ever says nice things to Ken.
"In case you are wondering, I got that for Valentine's Day for my wife. Fridged bitch has never worn it."
While I was not a woman. I knew enough to know this wasn't for her. It was for him to live out a fantasy. A fantasy he would be living out with her stand-in. Me.
Rob stripped off. His cock was at full mast. Just the sight of me did that. I felt a weird sense of power. I could make a man lust after me. This was a new sensation.
"Punish me, mistress Kara, tell me I have been a bad boy."
I had watched enough porn to know what he wanted. So I pushed him toward the bed and got him to lie face down.
"You disgusting man perverts like you need to have some sense whipped into them."
I took a gentle swing with the whip onto his buttocks.
"Harder please mistress." He said.
This was all new to me, but I did still feel some anger toward him. The whip was fairly light but I started to really lay into him. Soon faint red stripes appeared on his buttocks.
"Thank you, mistress, I've been a bad boy."
I didn't wonder that his wife didn't want to do this. It was exhausting. Not something I was into. Suddenly he turned and grabbed the whip and threw it across the room.
"I think I have paid enough for my sins. Now it's time to sin some more."
Rob held both my wrists and pushed me onto my back. My boots flew up and the heel of my left foot scraped his chest.
"Oh, you naughty girl. On the bed with you're legs in the air. You're just asking for it aren't you?"
I think he had satisfied his kink, now he was getting down to what he really wanted. His hand went to my crotch and popped it open. I thought he would pull down the tights, but he just used both hands to rip them and expose me.
Here it comes, I thought. I had been practicing with my dildos at home. I had a couple but rarely used them. I knew this was in the cards before I came here. I was lubed up, and prepared as I could be. Then he did something totally unexpected. he bent over me and took my little member into his mouth.
This felt incredible. No one had done this to me for years. I had forgotten how good it felt. I closed my eyes and lay there enjoying his attention. His right hand played gently with my balls. I was getting close. Suddenly I felt a finger enter me. It pushed past my lubricated entrance and plunged inside. I screamed a girlish high pitched scream and came like I never came in my life.
It felt like I fainted for a few seconds. I had just had gay sex and it was the best of my life. What was happening to me?
Rob looked down at my relaxed form and said.
"My turn now."
I tried to get up, thinking he meant that I use my mouth, but he pushed me back onto my back. He took my ankles in both hands and dragged me to the edge of the bed, towards his rampant hardness. I felt a little pain as he entered me. He was not too well endowed. I was grateful for that. I yelped a little, which drew a smile from him. He was watching my eyes intently as he slid all the way in. I screw my face up and moaned. He seemed to like that too.
When I opened them I looked up and saw his face framed with my feet in those glistening boots. My heels were over his shoulders. It looked so damm sexy I clenched up.
"You love this, don't you? You sexy bitch. I knew you were up for it."
Soon he built up a rhythm. I felt his balls slapping against my exposed buttocks. This felt good too. When I used my dildos they were cold and unyielding. His cock was warm, hard, yet flexible. It felt nice to be "wanted", to be lusted after. I had never experienced that before. I won't say he was making love, but this felt so different from anything I had felt before. I felt a warm glow spreading through my body. I felt another orgasm approaching.
Just then, Rob let out a satisfying sigh and fell on top of me. I felt him grow soft inside me, then he slipped out with a plopping sound. I wanted to get up to clean myself up, but his arm snaked around my waist and pulled me into him. We were spooning now. He kissed my shoulder.
"That was wonderful. Thank you, Kara. Get some rest. You have a busy day tomorrow. I got her a maid's outfit for Christmas last year."
I started to drift off. Instead of dreading tomorrow, I was rather looking forward to it.