Geoff was bored. He had a good job as a product manager for a high-tech electronics manufacturer and the work was interesting, but he’d been doing it for too long. It was too easy. His wife had left him four years ago, when she discovered that he was having an affair with a girl ten years her junior. The girl had ditched him soon after. He’d fallen for her badly and therefore couldn’t focus his attention on pulling anyone else. After Susie, he just didn’t fancy anyone nearer his own age. As result, he was lonely as well as bored.
If our terms are acceptable, perhaps you would telephone me and arrange an appointment to discuss the amendments.
Yours sincerely
A. Prentice (Mrs)
Managing Editor
Geoff telephoned the number given in the letter and asked for Mrs Prentice. She was in a meeting, so he explained his purpose and was put through to her secretary, who gave him appointment for Tuesday at 3:00pm. He could leave work early.
He found the address in Covent Garden easily enough and went through the glass door. A receptionist, whose bosom he couldn’t help but notice because of her low cut top, announced his presence by telephone and asked him to take a seat. After browsing the FT for a few minutes, Geoff watched a gorgeous, leggy blond come down the stairs behind the reception desk and walk over to him. As he looked up, she asked ‘Mr Carswell?’
‘That’s me,’ he said, getting up.
‘Mrs Prentice will see you now. This way please.’
He followed the girl up the stairs to the first floor and through an open plan office. The office was quiet, with everyone seemingly intent on their computer screens. The girl showed him into a glass-partitioned office at the far end of the floor.
The woman behind the desk did not rise, but said: ‘Take a seat Mr Carswell. Would you like coffee?’
‘That would be nice. Um – white without, please,’ he answered.
‘Be a dear, Zoë, and bring me one too,’ Mrs Prentice said to the blonde secretary.
Geoff sat opposite the woman who was regarding him intently over her glasses. She was slim with short brown hair and looked to be approaching 40. She was wearing a navy trouser suit and a man’s tie. She sat a little back from her desk with her legs crossed. After a moment Mrs Prentice spoke. ‘I enjoyed reading your novel, Geoff. May I call you that? It was very dirty, which is exactly what we want, I suppose. I got quite excited at times.’
Geoff smiled at the apparent compliment, imagining her with one hand down the front of her trousers and his book in the other.
She went on ‘I wanted us to have this preliminary meeting to discuss some cuts that our house style requires, but I also want to get some insight into the way you think. Would you describe yourself as a normal man?’
‘Yes, I suppose so.’
‘How old are you, Geoff?’
‘I’m 34.’
‘In the book you describe very convincingly how a man feels while he’s being buggered. Have you ever tried it yourself?’
Geoff was shocked. ‘No, I haven’t,’ he said. He had bought and tried a vibrator to get some authenticity though.
‘I suppose you use a vibrator up your arse then,’ said Mrs Prentice, to Geoff’s utter consternation, ‘and you can’t possibly have described the way it feels to be dressed in sexy underwear so well, unless you tried it out yourself. Come on, be honest with me Geoff.’
He paused, confused. ‘Well yes, I did find that I had to research those things a bit.’
Zoë brought the coffees in and left.
‘I bet you dressed up as a girl while you typed the female-viewpoint narrative. I bet you really saw yourself as Tania during those sessions. But never mind that, how about the punishment scenes, have you ever been caned or whipped by anyone – or caned a woman’s bottom?’
Now he’d started, Geoff felt obliged to be honest again: ‘A girlfriend of mine used to ask me to tie her up before we made love sometimes and she let me spank her once too. But I haven’t been spanked since childhood.’
Mrs Prentice paused at this, and then said, as though coming to a decision: ‘I want to find out more about you Geoff. If you were dressed as Tania, I think I could ask her my questions more easily. Are you brave enough to take my dare and come to this office dressed as Transvestite Tania? I really feel we can’t proceed with publishing your book until I meet the true author.’
Geoff was dumbstruck. He had indeed bought women’s underwear. It had been sexy to put it on. This had led to him wanting to try dresses and high heels. Next, he needed to learn how to apply make up. He looked so ridiculous in the mirror the first time he did so, that he bought a wig. He had felt like Tania. How did this woman see through him so easily? But he wasn’t a transvestite. From what he had read about it, TVs seemed to want really to be women and to conceal their male parts. Geoff had tried this but he always got such a hard on when he put on a dress, that concealing his sex between his legs was agony. He had fantasised about going to a TV club but never had the courage even to walk to the shops dressed as a woman. But the idea did intrigue him. Did he have the nerve? Mrs Prentice was silent, waiting for him.
‘What do you mean exactly?’ Geoff said eventually.
Mrs Prentice suddenly leaned forward and placed her hands on the desk: ‘If you want us to be your publisher, you will come back to this office on Friday dressed as Tania. I want you to make her as realistic as possible.’
She picked up the phone and dialled.
‘Zoë, Mr Carswell will be leaving in a moment. Would you show him out?’
She replaced the receiver and sipped her coffee. Geoff hadn’t touched his. Now he was afraid his hand would shake if he picked the cup up.
‘Here is our contract for you to sign, and this document details the cuts we will need,’ she said pushing some papers towards him. ‘Tania can bring them back for my signature on Friday. Be here at 4:30 sharp’.
Geoff put the papers in his briefcase as Zoë came in to collect him and show him out. On the tube home, he kept getting an embarrassing erection.
On Wednesday, he called in and said he’d being working from home for the rest of the week. He practised dressing as Tania and perfecting her make up. It made him horny and he had to relieve himself twice. He practised walking in high heels.
Geoff realized that he couldn’t bring himself to walk down the road like this; he had no woman’s overcoat and, worst still, no handbag. He would need one, to put money in. Without a coat, his maleness might give him away. Next morning he went to a nearby luggage shop in Acton and chose a small leather shoulder bag – saying it was a gift for his wife. He found a woman’s car coat that looked as if it would be big enough in a charity shop in the High Street. He tried the coat on when he got home and looked in the mirror in his bedroom. His legs would give him away. The hairs showed through even black stockings.
Geoff found an old shaving brush and a stick of shaving soap. He took these with a razor into the shower. After washing, he turned the water off and lathered his legs. Carefully, he started shaving the hair off his calves. He was amazed at how smooth his skin felt when he rinsed them under the showerhead. Then he thought he’d better go well above the knees – in case anyone looked up his skirt while seated on the Central Line. Somehow, he ended up shaving right up to the crack between his buttocks and, taking extra care, he shaved himself between the legs. The hair on his chest was visible over the neckline of his favourite dress when he dressed up. Remembering this, he decided to go the whole hog. After drying himself and trying some stockings on his newly smooth legs, he found a pair of scissors and trimmed as much hair as he could off his chest and arms. Then he went back to the shower and lathered these areas for shaving too.
That evening he went to the pub after cooking dinner. He was sure that none of his mates saw anything amiss – but he had made sure to wear a polo necked sweater.
Friday dragged until lunchtime. He tried to work but couldn’t concentrate. He made a sandwich at lunchtime and thought he’d better start getting ready. Knowing from his previous experiments that this would be the trickiest task, Geoff applied himself to making his face up first. He washed and shaved his face with extra care. Then he found the wash bag where he kept his make-up things and took it, with the shaving mirror from the bathroom, into the dining room. He applied a tiny amount of cream foundation to the whole of his face with a sponge then some green eye shadow to his upper eyelids. He found a pencil and very carefully drew a black line around each eye, adding a smile line at the outer corners; he would have to practise that. Mascara wasn’t too hard and he applied some to his eyebrows as well as lashes. Rose blusher and some bright red lipstick completed the job. He put his wig on and looked at himself. To his surprise, a woman’s face stared back at him. Not a beautiful woman but definitely female. She looked a little older than Geoff did. He went to the bedroom and put on a black bra and a pair of black cotton knickers with a tiny bow at the front and a pretty lace trim. He found the breast enhancers that he had bought and put them in the cups of the bra. Then he pulled and rolled sheer black tights up his smooth legs. He looked in the mirror on the wardrobe door and slipped on his high heels. Most women wouldn’t be ashamed of those legs, he thought. He squeezed his artificial breasts. They felt surprisingly realistic. Dressing up like this made him feel incredibly sexy and horny. He wiped the fluid from the end of his penis with a tissue and decided to tape it to his stomach with surgical tape as soon as he could make it flaccid enough, by sheer willpower. This done, he pulled up the briefs and tights again and stepped into his favourite dress: a short-sleeved navy one-piece in stretch fabric. With difficulty, he managed to zip it up the back. It was a tight fit and hugged him around the waist and chest. He put his wig on again and looked in the mirror. There was Tania: tall and slim, if a bit stocky for a woman, with small but visible breasts, slender, shapely legs and straight, dark brown hair that curled in at her neckline. Geoff was glad the wig covered his ears; he wouldn’t need earrings.
At 3:45, Geoff put on his secondhand coat, picked up his new bag and stepped out of his house and into the street in high heels for the first time. As he had expected, he had to take very small steps and swing his hips to walk in heels. His calf muscles had started to hurt by the time he got the station. As he waited on the platform, and throughout the rest of the journey, he glanced around to see if anyone had found him out. He got on a train and sat with his knees pressed self-consciously together and his new bag resting on them. He pretended to read the publishing contract that he had brought with him.
When he teetered into the Crewel Knit reception the familiar face of the receptionist looked up. He was about say his name when he stopped himself and, affecting a soft rather than high voice, said ‘Miss Hyde. I’ve an appointment with Mrs Prentice.’
He stood until Mrs Prentice’s lovely secretary – Zoë wasn’t it – collected him and led him upstairs. She was wearing a charcoal jersey dress that hugged her body. He tried not to look at her swaying hips as he followed her up the stairs.
Mrs Prentice invited him in with a ‘Tania, how lovely you look. Please take a seat.’
He handed her the contracts and she signed both copies.
‘Congratulations on becoming an author, Tania. I hope this will not be your last novel with us. Do you intend to write more in this vein?’
Geoff said he had a sequel sketched out already.
‘In that case, you should try to inject more realism into it. I am particularly concerned that you’ve never experienced spanking. Would you like to try – just to see what it feels like?’
Geoff didn’t think he wanted to cross that line; fantasy was one thing, but . . . But the cross-dressing had helped his muse though. ‘I’m not sure. I don’t think I’d like to at all but, well I’m slightly tempted: just to know, just once,’ he stammered, conscious of his man’s voice again.
‘I’m glad you agree, because you deserve a good spanking for being late.’ Her tone was that of an angry headmistress. Giles hadn’t worn his watch because it was a man’s model. He looked at the wall clock. It was ten to five already.
‘Across my desk, you naughty girl. Now!’ she shouted.
Geoff thought she must be joking. He looked round. The open plan office was deserted.
‘My staff leave early on Fridays,’ said Mrs Prentice. ‘Now over my desk! Grip the edge.’
Geoff thought that he might as well. He stood and bent across the desk resting on his palms as his fingers gripped the edge. This was a bit exciting.
Mrs Prentice opened a drawer in the desk and said ‘I’m going to handcuff you for your spanking, to make it more like what happens in a book. You can experience the feeling of helplessness that bondage brings about.’
She produced a pair of handcuffs and clipped them onto his wrists. Next, she bent and picked up something. She clicked a padlock to the short chain joining his wrists. Geoff tested it. The chain must be fixed at its other end somehow. Climbing over the desk was his only escape route, but he’d still be chained to the spot, he thought. Mrs Prentice came round the desk and carefully pulled up Geoff’s dress to above his waist. Then she pulled down his tights to his knees. He certainly felt helpless now.
‘What pretty knickers the naughty little baggage has on. Let’s take them down and see her naughty bottom that deserves to be punished.’ She took his panties down and then squeezed his scrotum hard enough to be uncomfortable but not hard enough to really hurt. Keeping hold, she said ‘Ask nicely for your punishment Tania, you worthless slut.’
Geoff thought of scenes in his book and said ‘Please spank my naughty bottom, Mistress’.
She started spanking him slowly. It hurt, but not as much as he expected. She spanked harder until he started pleading with her to stop.
‘Ouch! Ouch! No more please! Please, Mistress, stop; please.’
Eventually she stopped. His bum felt like it was on fire.
‘Get your tart’s legs apart,’ the woman commanded, pulling one of his ankles and then the other until his stomach was on the desk. With her hand resting on his waist, she picked up the telephone. ‘Zoë, be so kind as to bring the cane to me.’
Geoff tried to protest and get up but she stopped him easily with a few hard smacks. He didn’t want that girl to see him this way: feminized and vulnerable. He felt himself blush as he heard the door open. Zoë handed a rattan cane to Mrs Prentice. And he hadn’t agreed to a caning. Had he? He was too embarrassed to say anything.
Mrs Prentice felt underneath him and found his prick. It was hard. As she stroked it, he heard her whisper. ‘Now I’m going to give you six hard strokes across your pathetic arse with my cane for being late for your appointment, slut. Zoë will watch. It will remind her of what will happen to her when she’s late for work.’
The first stroke fell across Geoff’s right buttock. The pain didn’t come until a second or two later, but when it did, it stung like mad. Mrs Prentice waited, applied the next stroke to the left cheek and waited again. When all six strokes were over Geoff had tears in his eyes.
‘Very well, girl. I’m pleased and surprised that you took your punishment so well, Tania. Look what a lovely colour her bum is, Zoë. Now I’m going to untie you if you promise to be a good girl and do what you’re told in future.’
She waited until Geoff said, in his most servile and girly voice, ‘I’m sorry I was late, Miss, and I promise to be ever so good and do what I’m told always.’
She unchained him but left the cuffs on. He stood up painfully. His arse was ablaze still and now ached as well.
‘What’s that ridiculous little thing stuck to your tummy, Tania? Turn round and show Zoë. What do you think, Zoë?’
He turned reluctantly, still feeling helpless in the cuffs. Zoë approached and pulled the tape off. It pulled away some of his pubes with it and he winced. ‘It looks like a man’s penis, Mistress,’ said Zoë.
He felt utterly ridiculous, standing there in high heels with his skirt round his waist and his knickers and tights round his knees.
Pull your clothes up properly, you shameless tart,’ barked the older woman.
Geoff did this as best he could with his cuffed hands. Mrs Prentice came round the desk again and grabbed him by the scrotum as she handed Zoë some keys. ‘Cuff her hands behind her.’
Zoë unlocked the cuffs, and Geoff put his hands obligingly behind him when Mrs Prentice squeezed his balls harder. Zoë clicked the cuffs onto his wrists. Mrs Prentice pulled the dress down and Geoff – or was it Tania – felt a little more respectable. If only that girl hadn’t seen his humiliation. She was drop dead gorgeous and he would have loved to have had the chance to chat her up as a normal man might. She’d think of him like this now. She probably thought he was just a sad pervert.
‘Stand there,’ barked Mrs Prentice, pointing to the corner of the desk to Geoff’s right.
As he obeyed, she walked over to the younger woman and, to Geoff’s surprise put her hand up the girl’s dress. The girl didn’t move.
‘Zoë likes watching naughty girls spanked and caned, don’t you Zoë?’ asked the older woman. ‘Your cunt’s wet, you dirty lesbian slut. You’ve been think your filthy queer thoughts again haven’t you?’
‘I’m sorry, Mistress,’ said the girl. ‘I’ve been naughty and deserve to be punished’.
Giles could feel the fluid leaking from his prick and making his knickers wet at the front. He hoped the wetness wouldn’t show through his dress.
‘Over the desk!’ shouted Mrs Prentice.
The girl did as she had been instructed and then slowly pulled her dress up to her waist, revealing a taut bottom. She spread her legs wide apart and lay waiting. She was gripping the edge of the desk tightly and Geoff saw her knuckles whiten.
Mrs Prentice stood facing Geoff as she gave the girl six hard stokes of the cane. Zoë counted each stroke out loud, ending with ‘Six. Thank you, Mistress’.
‘Stand in the corner. Face the wall.’
Zoë got up stiffly and held her dress up so that her bottom and her neatly trimmed pubes were visible. Geoff saw that she was crying. She went to the filing cabinet in the opposite corner and stood facing it, still holding up the dress. Geoff could see the livid red stripes that the cane had left on her bottom.
Turning to Geoff, Mrs Prentice said ‘so now you begin to understand how it feels to be a slave, to be punished and dominated by your cruel Mistress, Tania. You feel helpless and humiliated. You love your Mistress though. You want her to spank you across her knees next time you’re a naughty girl, don’t you, you shameless hussy? You want to thank her and kiss her shoes.’
Geoff stared at his feet.
‘On your knees and thank your Mistress. Now, slut!’ she shouted at him.
Geoff did feel helpless in the cuffs and the tight dress and high heels. He knelt and started kissing the domineering woman’s shoes, over and over again. She bent forward as he did this and unlocked his handcuffs.
‘Get up slave,’ she said, ‘and get out of my sight. I want to think up your next punishment.’
Geoff got to his feet. Mrs Prentice was holding out his coat and bag. He took them silently and left the room. Tania’s scanty knickers felt sopping wet as s/he walked to the Underground.
When Geoff got home, he stripped and examined his bum before dressing. It was badly marked and very sore. He cooked dinner and went to the pub, where he stood at the bar – not wanted to sit down if he could help it. Mentally, he vowed never to do anything like that again. The cruel bitch had tricked him. He’d avoid going to that office again if he could help it. He’d write no more porn.
That night he dreamed of Zoë. Mistress was caning her. Now he was fucking her from behind as she lay across a massive desk that seemed to extend to the horizon. But it wasn’t Zoë. He was pumping frantically in and out of Mrs Prentice, who was moaning with pleasure. Zoë was caning him from behind.
He woke to feel the wetness of his ejaculation underneath him. He moved to another part of the bed and went back to sleep. The dreams continued all week and he also found himself daydreaming at work about both the dreams and the things that had actually been done to him. In one dream, he was Tania. She was working as Mrs Prentice’s secretary. Mistress was telling her off sternly and threatening to send her away if she wasn’t a good girl. Tania was crying – as was Geoff when he awoke.
On Wednesday, it just got too much. In the evening, Geoff called the mobile number that was on Mrs Prentice’s business card. Her voice answered. ‘Yes!’
There was traffic noise in the background.
Geoff spoke in a high voice. ‘It’s Tania, Mistress. I’ve been a very naughty girl, Mistress. I’m sorry, Mistress, I just wanted to tell you – just wanted to hear your voice. I–’
Mistress interrupted. ‘Very well, Tania. Be at my office at five on Friday. That’s an order’. She rang off.
If our terms are acceptable, perhaps you would telephone me and arrange an appointment to discuss the amendments.
Yours sincerely
A. Prentice (Mrs)
Managing Editor
Geoff telephoned the number given in the letter and asked for Mrs Prentice. She was in a meeting, so he explained his purpose and was put through to her secretary, who gave him appointment for Tuesday at 3:00pm. He could leave work early.
He found the address in Covent Garden easily enough and went through the glass door. A receptionist, whose bosom he couldn’t help but notice because of her low cut top, announced his presence by telephone and asked him to take a seat. After browsing the FT for a few minutes, Geoff watched a gorgeous, leggy blond come down the stairs behind the reception desk and walk over to him. As he looked up, she asked ‘Mr Carswell?’
‘That’s me,’ he said, getting up.
‘Mrs Prentice will see you now. This way please.’
He followed the girl up the stairs to the first floor and through an open plan office. The office was quiet, with everyone seemingly intent on their computer screens. The girl showed him into a glass-partitioned office at the far end of the floor.
The woman behind the desk did not rise, but said: ‘Take a seat Mr Carswell. Would you like coffee?’
‘That would be nice. Um – white without, please,’ he answered.
‘Be a dear, Zoë, and bring me one too,’ Mrs Prentice said to the blonde secretary.
Geoff sat opposite the woman who was regarding him intently over her glasses. She was slim with short brown hair and looked to be approaching 40. She was wearing a navy trouser suit and a man’s tie. She sat a little back from her desk with her legs crossed. After a moment Mrs Prentice spoke. ‘I enjoyed reading your novel, Geoff. May I call you that? It was very dirty, which is exactly what we want, I suppose. I got quite excited at times.’
Geoff smiled at the apparent compliment, imagining her with one hand down the front of her trousers and his book in the other.
She went on ‘I wanted us to have this preliminary meeting to discuss some cuts that our house style requires, but I also want to get some insight into the way you think. Would you describe yourself as a normal man?’
‘Yes, I suppose so.’
‘How old are you, Geoff?’
‘I’m 34.’
‘In the book you describe very convincingly how a man feels while he’s being buggered. Have you ever tried it yourself?’
Geoff was shocked. ‘No, I haven’t,’ he said. He had bought and tried a vibrator to get some authenticity though.
‘I suppose you use a vibrator up your arse then,’ said Mrs Prentice, to Geoff’s utter consternation, ‘and you can’t possibly have described the way it feels to be dressed in sexy underwear so well, unless you tried it out yourself. Come on, be honest with me Geoff.’
He paused, confused. ‘Well yes, I did find that I had to research those things a bit.’
Zoë brought the coffees in and left.
‘I bet you dressed up as a girl while you typed the female-viewpoint narrative. I bet you really saw yourself as Tania during those sessions. But never mind that, how about the punishment scenes, have you ever been caned or whipped by anyone – or caned a woman’s bottom?’
Now he’d started, Geoff felt obliged to be honest again: ‘A girlfriend of mine used to ask me to tie her up before we made love sometimes and she let me spank her once too. But I haven’t been spanked since childhood.’
Mrs Prentice paused at this, and then said, as though coming to a decision: ‘I want to find out more about you Geoff. If you were dressed as Tania, I think I could ask her my questions more easily. Are you brave enough to take my dare and come to this office dressed as Transvestite Tania? I really feel we can’t proceed with publishing your book until I meet the true author.’
Geoff was dumbstruck. He had indeed bought women’s underwear. It had been sexy to put it on. This had led to him wanting to try dresses and high heels. Next, he needed to learn how to apply make up. He looked so ridiculous in the mirror the first time he did so, that he bought a wig. He had felt like Tania. How did this woman see through him so easily? But he wasn’t a transvestite. From what he had read about it, TVs seemed to want really to be women and to conceal their male parts. Geoff had tried this but he always got such a hard on when he put on a dress, that concealing his sex between his legs was agony. He had fantasised about going to a TV club but never had the courage even to walk to the shops dressed as a woman. But the idea did intrigue him. Did he have the nerve? Mrs Prentice was silent, waiting for him.
‘What do you mean exactly?’ Geoff said eventually.
Mrs Prentice suddenly leaned forward and placed her hands on the desk: ‘If you want us to be your publisher, you will come back to this office on Friday dressed as Tania. I want you to make her as realistic as possible.’
She picked up the phone and dialled.
‘Zoë, Mr Carswell will be leaving in a moment. Would you show him out?’
She replaced the receiver and sipped her coffee. Geoff hadn’t touched his. Now he was afraid his hand would shake if he picked the cup up.
‘Here is our contract for you to sign, and this document details the cuts we will need,’ she said pushing some papers towards him. ‘Tania can bring them back for my signature on Friday. Be here at 4:30 sharp’.
Geoff put the papers in his briefcase as Zoë came in to collect him and show him out. On the tube home, he kept getting an embarrassing erection.
On Wednesday, he called in and said he’d being working from home for the rest of the week. He practised dressing as Tania and perfecting her make up. It made him horny and he had to relieve himself twice. He practised walking in high heels.
Geoff realized that he couldn’t bring himself to walk down the road like this; he had no woman’s overcoat and, worst still, no handbag. He would need one, to put money in. Without a coat, his maleness might give him away. Next morning he went to a nearby luggage shop in Acton and chose a small leather shoulder bag – saying it was a gift for his wife. He found a woman’s car coat that looked as if it would be big enough in a charity shop in the High Street. He tried the coat on when he got home and looked in the mirror in his bedroom. His legs would give him away. The hairs showed through even black stockings.
Geoff found an old shaving brush and a stick of shaving soap. He took these with a razor into the shower. After washing, he turned the water off and lathered his legs. Carefully, he started shaving the hair off his calves. He was amazed at how smooth his skin felt when he rinsed them under the showerhead. Then he thought he’d better go well above the knees – in case anyone looked up his skirt while seated on the Central Line. Somehow, he ended up shaving right up to the crack between his buttocks and, taking extra care, he shaved himself between the legs. The hair on his chest was visible over the neckline of his favourite dress when he dressed up. Remembering this, he decided to go the whole hog. After drying himself and trying some stockings on his newly smooth legs, he found a pair of scissors and trimmed as much hair as he could off his chest and arms. Then he went back to the shower and lathered these areas for shaving too.
That evening he went to the pub after cooking dinner. He was sure that none of his mates saw anything amiss – but he had made sure to wear a polo necked sweater.
Friday dragged until lunchtime. He tried to work but couldn’t concentrate. He made a sandwich at lunchtime and thought he’d better start getting ready. Knowing from his previous experiments that this would be the trickiest task, Geoff applied himself to making his face up first. He washed and shaved his face with extra care. Then he found the wash bag where he kept his make-up things and took it, with the shaving mirror from the bathroom, into the dining room. He applied a tiny amount of cream foundation to the whole of his face with a sponge then some green eye shadow to his upper eyelids. He found a pencil and very carefully drew a black line around each eye, adding a smile line at the outer corners; he would have to practise that. Mascara wasn’t too hard and he applied some to his eyebrows as well as lashes. Rose blusher and some bright red lipstick completed the job. He put his wig on and looked at himself. To his surprise, a woman’s face stared back at him. Not a beautiful woman but definitely female. She looked a little older than Geoff did. He went to the bedroom and put on a black bra and a pair of black cotton knickers with a tiny bow at the front and a pretty lace trim. He found the breast enhancers that he had bought and put them in the cups of the bra. Then he pulled and rolled sheer black tights up his smooth legs. He looked in the mirror on the wardrobe door and slipped on his high heels. Most women wouldn’t be ashamed of those legs, he thought. He squeezed his artificial breasts. They felt surprisingly realistic. Dressing up like this made him feel incredibly sexy and horny. He wiped the fluid from the end of his penis with a tissue and decided to tape it to his stomach with surgical tape as soon as he could make it flaccid enough, by sheer willpower. This done, he pulled up the briefs and tights again and stepped into his favourite dress: a short-sleeved navy one-piece in stretch fabric. With difficulty, he managed to zip it up the back. It was a tight fit and hugged him around the waist and chest. He put his wig on again and looked in the mirror. There was Tania: tall and slim, if a bit stocky for a woman, with small but visible breasts, slender, shapely legs and straight, dark brown hair that curled in at her neckline. Geoff was glad the wig covered his ears; he wouldn’t need earrings.
At 3:45, Geoff put on his secondhand coat, picked up his new bag and stepped out of his house and into the street in high heels for the first time. As he had expected, he had to take very small steps and swing his hips to walk in heels. His calf muscles had started to hurt by the time he got the station. As he waited on the platform, and throughout the rest of the journey, he glanced around to see if anyone had found him out. He got on a train and sat with his knees pressed self-consciously together and his new bag resting on them. He pretended to read the publishing contract that he had brought with him.
When he teetered into the Crewel Knit reception the familiar face of the receptionist looked up. He was about say his name when he stopped himself and, affecting a soft rather than high voice, said ‘Miss Hyde. I’ve an appointment with Mrs Prentice.’
He stood until Mrs Prentice’s lovely secretary – Zoë wasn’t it – collected him and led him upstairs. She was wearing a charcoal jersey dress that hugged her body. He tried not to look at her swaying hips as he followed her up the stairs.
Mrs Prentice invited him in with a ‘Tania, how lovely you look. Please take a seat.’
He handed her the contracts and she signed both copies.
‘Congratulations on becoming an author, Tania. I hope this will not be your last novel with us. Do you intend to write more in this vein?’
Geoff said he had a sequel sketched out already.
‘In that case, you should try to inject more realism into it. I am particularly concerned that you’ve never experienced spanking. Would you like to try – just to see what it feels like?’
Geoff didn’t think he wanted to cross that line; fantasy was one thing, but . . . But the cross-dressing had helped his muse though. ‘I’m not sure. I don’t think I’d like to at all but, well I’m slightly tempted: just to know, just once,’ he stammered, conscious of his man’s voice again.
‘I’m glad you agree, because you deserve a good spanking for being late.’ Her tone was that of an angry headmistress. Giles hadn’t worn his watch because it was a man’s model. He looked at the wall clock. It was ten to five already.
‘Across my desk, you naughty girl. Now!’ she shouted.
Geoff thought she must be joking. He looked round. The open plan office was deserted.
‘My staff leave early on Fridays,’ said Mrs Prentice. ‘Now over my desk! Grip the edge.’
Geoff thought that he might as well. He stood and bent across the desk resting on his palms as his fingers gripped the edge. This was a bit exciting.
Mrs Prentice opened a drawer in the desk and said ‘I’m going to handcuff you for your spanking, to make it more like what happens in a book. You can experience the feeling of helplessness that bondage brings about.’
She produced a pair of handcuffs and clipped them onto his wrists. Next, she bent and picked up something. She clicked a padlock to the short chain joining his wrists. Geoff tested it. The chain must be fixed at its other end somehow. Climbing over the desk was his only escape route, but he’d still be chained to the spot, he thought. Mrs Prentice came round the desk and carefully pulled up Geoff’s dress to above his waist. Then she pulled down his tights to his knees. He certainly felt helpless now.
‘What pretty knickers the naughty little baggage has on. Let’s take them down and see her naughty bottom that deserves to be punished.’ She took his panties down and then squeezed his scrotum hard enough to be uncomfortable but not hard enough to really hurt. Keeping hold, she said ‘Ask nicely for your punishment Tania, you worthless slut.’
Geoff thought of scenes in his book and said ‘Please spank my naughty bottom, Mistress’.
She started spanking him slowly. It hurt, but not as much as he expected. She spanked harder until he started pleading with her to stop.
‘Ouch! Ouch! No more please! Please, Mistress, stop; please.’
Eventually she stopped. His bum felt like it was on fire.
‘Get your tart’s legs apart,’ the woman commanded, pulling one of his ankles and then the other until his stomach was on the desk. With her hand resting on his waist, she picked up the telephone. ‘Zoë, be so kind as to bring the cane to me.’
Geoff tried to protest and get up but she stopped him easily with a few hard smacks. He didn’t want that girl to see him this way: feminized and vulnerable. He felt himself blush as he heard the door open. Zoë handed a rattan cane to Mrs Prentice. And he hadn’t agreed to a caning. Had he? He was too embarrassed to say anything.
Mrs Prentice felt underneath him and found his prick. It was hard. As she stroked it, he heard her whisper. ‘Now I’m going to give you six hard strokes across your pathetic arse with my cane for being late for your appointment, slut. Zoë will watch. It will remind her of what will happen to her when she’s late for work.’
The first stroke fell across Geoff’s right buttock. The pain didn’t come until a second or two later, but when it did, it stung like mad. Mrs Prentice waited, applied the next stroke to the left cheek and waited again. When all six strokes were over Geoff had tears in his eyes.
‘Very well, girl. I’m pleased and surprised that you took your punishment so well, Tania. Look what a lovely colour her bum is, Zoë. Now I’m going to untie you if you promise to be a good girl and do what you’re told in future.’
She waited until Geoff said, in his most servile and girly voice, ‘I’m sorry I was late, Miss, and I promise to be ever so good and do what I’m told always.’
She unchained him but left the cuffs on. He stood up painfully. His arse was ablaze still and now ached as well.
‘What’s that ridiculous little thing stuck to your tummy, Tania? Turn round and show Zoë. What do you think, Zoë?’
He turned reluctantly, still feeling helpless in the cuffs. Zoë approached and pulled the tape off. It pulled away some of his pubes with it and he winced. ‘It looks like a man’s penis, Mistress,’ said Zoë.
He felt utterly ridiculous, standing there in high heels with his skirt round his waist and his knickers and tights round his knees.
Pull your clothes up properly, you shameless tart,’ barked the older woman.
Geoff did this as best he could with his cuffed hands. Mrs Prentice came round the desk again and grabbed him by the scrotum as she handed Zoë some keys. ‘Cuff her hands behind her.’
Zoë unlocked the cuffs, and Geoff put his hands obligingly behind him when Mrs Prentice squeezed his balls harder. Zoë clicked the cuffs onto his wrists. Mrs Prentice pulled the dress down and Geoff – or was it Tania – felt a little more respectable. If only that girl hadn’t seen his humiliation. She was drop dead gorgeous and he would have loved to have had the chance to chat her up as a normal man might. She’d think of him like this now. She probably thought he was just a sad pervert.
‘Stand there,’ barked Mrs Prentice, pointing to the corner of the desk to Geoff’s right.
As he obeyed, she walked over to the younger woman and, to Geoff’s surprise put her hand up the girl’s dress. The girl didn’t move.
‘Zoë likes watching naughty girls spanked and caned, don’t you Zoë?’ asked the older woman. ‘Your cunt’s wet, you dirty lesbian slut. You’ve been think your filthy queer thoughts again haven’t you?’
‘I’m sorry, Mistress,’ said the girl. ‘I’ve been naughty and deserve to be punished’.
Giles could feel the fluid leaking from his prick and making his knickers wet at the front. He hoped the wetness wouldn’t show through his dress.
‘Over the desk!’ shouted Mrs Prentice.
The girl did as she had been instructed and then slowly pulled her dress up to her waist, revealing a taut bottom. She spread her legs wide apart and lay waiting. She was gripping the edge of the desk tightly and Geoff saw her knuckles whiten.
Mrs Prentice stood facing Geoff as she gave the girl six hard stokes of the cane. Zoë counted each stroke out loud, ending with ‘Six. Thank you, Mistress’.
‘Stand in the corner. Face the wall.’
Zoë got up stiffly and held her dress up so that her bottom and her neatly trimmed pubes were visible. Geoff saw that she was crying. She went to the filing cabinet in the opposite corner and stood facing it, still holding up the dress. Geoff could see the livid red stripes that the cane had left on her bottom.
Turning to Geoff, Mrs Prentice said ‘so now you begin to understand how it feels to be a slave, to be punished and dominated by your cruel Mistress, Tania. You feel helpless and humiliated. You love your Mistress though. You want her to spank you across her knees next time you’re a naughty girl, don’t you, you shameless hussy? You want to thank her and kiss her shoes.’
Geoff stared at his feet.
‘On your knees and thank your Mistress. Now, slut!’ she shouted at him.
Geoff did feel helpless in the cuffs and the tight dress and high heels. He knelt and started kissing the domineering woman’s shoes, over and over again. She bent forward as he did this and unlocked his handcuffs.
‘Get up slave,’ she said, ‘and get out of my sight. I want to think up your next punishment.’
Geoff got to his feet. Mrs Prentice was holding out his coat and bag. He took them silently and left the room. Tania’s scanty knickers felt sopping wet as s/he walked to the Underground.
When Geoff got home, he stripped and examined his bum before dressing. It was badly marked and very sore. He cooked dinner and went to the pub, where he stood at the bar – not wanted to sit down if he could help it. Mentally, he vowed never to do anything like that again. The cruel bitch had tricked him. He’d avoid going to that office again if he could help it. He’d write no more porn.
That night he dreamed of Zoë. Mistress was caning her. Now he was fucking her from behind as she lay across a massive desk that seemed to extend to the horizon. But it wasn’t Zoë. He was pumping frantically in and out of Mrs Prentice, who was moaning with pleasure. Zoë was caning him from behind.
He woke to feel the wetness of his ejaculation underneath him. He moved to another part of the bed and went back to sleep. The dreams continued all week and he also found himself daydreaming at work about both the dreams and the things that had actually been done to him. In one dream, he was Tania. She was working as Mrs Prentice’s secretary. Mistress was telling her off sternly and threatening to send her away if she wasn’t a good girl. Tania was crying – as was Geoff when he awoke.
On Wednesday, it just got too much. In the evening, Geoff called the mobile number that was on Mrs Prentice’s business card. Her voice answered. ‘Yes!’
There was traffic noise in the background.
Geoff spoke in a high voice. ‘It’s Tania, Mistress. I’ve been a very naughty girl, Mistress. I’m sorry, Mistress, I just wanted to tell you – just wanted to hear your voice. I–’
Mistress interrupted. ‘Very well, Tania. Be at my office at five on Friday. That’s an order’. She rang off.
