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?