Sissy Denial Pt. 01

Here's the problem... Men who do not fancy men sexually, crave cock when they dress up as women. They know they aren't passable, which drives them crazy with frustration... it is usually their face: too masculine, too angular. It is just not real enough. And yet they continue to fantasise and dress up and yearn.

Tom was such a man. He was a sissy in his head. He drove his car and saw women walking along the street and stared at them, They probably thought he was being creepy and crude but he was fantasising being them, not wanting them. He wondered how many men did this really, every day in every town in every country.

Tom would wear a thong all day under his male clothes and wish he could wear a bra but that would show through his clothes and he couldn't have that. He sometimes used a butt plug and sometimes a cock cage but that was uncomfortable so he probably needed a better one but didn't know enough to do that. He muddled on, wearing his wives clothes when he was alone in the house.

He trained with a 7" dildo. He could suck it and he could get it into his throat but not very often. It turned him on and he invariably wanked afterwards, always adamant that he would clean up his own cum afterwards but as soon as he came, he couldn't be bothered: the desire evaporated with the first squirt of cum into his palm.

At work, he worked diligently. He kept himself to himself, worked hard and went home. There were only a few other employees plus the boss. It suited Tom. He got paid, he went home, he fantasised, he fought the thoughts and then went back to them and wanked and the feeling faded. This cycled around for years and Tom got used to it.

His wife knew something was wrong. Tom was not very attentive to her needs and eventually they split up and Tom was alone again, rueing the day he messed up with his wife but happy that he was free to dress up whenever he could at home: he bought females clothes online. He bought some shoes from specialised shops and he loved his corset.

Tom was living the crossdressing dream of wasting his life in pursuit of a dream and he didn't really know it.

One day, things changed for Tom. It all started at work, of course, when a co-worker saw what he thought was the top of lacey knickers sticking out of the top of Tom's trousers as he bent over, lost in the mundane work.

The worker complained to the boss and the boss acted.

The boss called Tom in to his office and closed the door. Tom sat down and the boss sat down behind his desk. His boss stared at Tom and Tom got nervous.

"Tom." He stopped. "I don't know how to start this." He paused. "There has been a complaint about you."

"A complaint? About what?" Tom was genuinely shocked. He wracked his brain. What had he done? Not done? "Who... who has complained about me?" he asked.

"That doesn't matter Tom. What matters is how we proceed after this." The boss was staring at Tom intently. Tom was nervous but his boss's focus was freaking him out.

"I am not going to act on the complaint Tom. This time. I do want to talk to you about it though. But not here. How about I come round to yours tonight and we can have a drink and talk errr man to man about it. What do you say?"

Tom was nonplussed. "What is the complaint, boss? I don't know what i have done."

His boss waved his hand around vaguely. "It doesn't matter now. Let's leave it. Take the rest of the afternoon off and go home. I will pop over after work, say 6pm? WE can chat then OK?"

"Hmmmm, OK boss." Tom was shocked. He stood and left the office, leaving the works and drove home to his one bedroom apartment. He sat there and fretted. What had he done?

Some time just after 6pm that evening, a knock on his door and his boss was there with beer. His boss smiled and stepped in, taking in the apartment quickly.

They sat down in the chairs in the main room and drank some beer, mainly in silence. His boss coughed and began to talk but quickly stopped and seemed lost for words.

"Look boss, just tell me what it is, will you. I can't stand this not knowing"

"OK OK. Someone - it doesn't matter who - errrr. They errr saw your ermmm." he faded to a stop.

Tom was at a loss. Saw what? His boss was pointing to the waistband of his own trousers, indicating inside.

The penny dropped then for Tom and he flushed red, unable to hide the reaction. "Ahh. Right." Tom looked at his boss in horror. "Shit" he mumbled.

His boss looked at him as all this was playing out on his face, like an open book.

"Show me".

Tom ignored the phrase, still in his personal shock.

"Show me, Tom"

Tom came to and looked at his boss. "I beg your pardon?"

"you heard me Tom. Show me. Here. Now"

Tom just sat and stared at his boss. "I... I... I dodn't know what you mean" he stumbled.

"Yes you do Tom. Show me that what the other person saw is correct. I want to see them."

Tom had frozen. "I can't," he said, lamely.

His boss coughed nervously. "I have never done this sort of thing before Tom but it interests me. I am now interested in you. So show me what you are wearing. I assume you are still wearing them?"

Tom stared and then simply nodded, whilst remaining silent. He was like a stunned rabbit in headlights.

"Go you your bedroom then Tom and get ready in anyway you want to and come back in here. How about that?"

Tom agian was just staring at his boss, at a complete loss. His can was held fixed halfway to his mouth, unused.

"I assume you have more clothing in your bedroom?" his boss pointedly asked Tom. Tom nodded, surprised with himself. He had admitted it. "Good, go in there and change then. For me." Tom remained sitting. "Now Tom." his boss said, in a tone that made Tom stand up.

He put his beer down and walked unsteadily to his bedroom, before opening the door, going through and closing the door behind him.

"shit, shit, shi, shit" thought Tom as he leant his back against the door. "what the fuck do i do?" he asked himself. "What the actual fuck do I do now?" He paced his bedroom and tried t to hyperventilate. He took deep breathes and clutched at his chest.

Back in the main room, his boss waited and drank his beer. He had told the truth - he had never done anything like this. Tom was the perfect patsy though. Tom had been found out and his boss held all the cards. He felt safe now. He knew Tom would do what he was told. He just had to wait for him to come out.

He waited. Five minutes. Ten minutes. half an hour. He was getting irritated with the wait now. "Hurry up Tom. I can't wait for ever. Get out here"

The door opened slightly. It paused and then opened fully. Tom appeared and stood there. He was wearing lingerie. He had a bra and knickers and hold up stockings with high heels. He even had am anklet chain on his left leg.

Tom looked at his boss as his boss stared up at him from his chair. His boss had his mouth open slightly, in shock, no doubt.

Tom fidgeted in the doorway. "Well, there you go. Now you have seen me. I am changing back now." and he began to walk back into the bedroom.

As he was closing the bedroom door, it banged open on the foot of his boss who had gotten up and walked over in that time. Tom recoiled as his boss stepped into the bedroom. His bedroom. "Now look, boss. I think you had better leave. Right now." and his voice was pitching higher as he said this.

Tom almost screamed out as his boss placed an arm around his waist and tried to pull him close.

"Look Tom, I am your boss. A complaint has been made against you. A quite serious one. I don't want to have to let you go." His boss laughed quickly then at the souble meaning of his words.

"What are you saying?" asked Tom, still held by his boss and standing so very close to him now.

His boss took a deep breathe. Here it was. Here it comes...

"I want you to please me here and now. Will you do that?"

"How do you mean?" squeaked Tom, knowing full well what was being negotiated here and now.

"I want you to perform... tasks... for me, dressed like that."

"I... I can't. I have never....." stuttered Tom.

His boss was stroking Tom's back with a finger and holding him tightly with his palm. Tom inched closer by act of this force. "there is always a first time, Tom, for anything. Tonight, it is your first time to please me. Isn't it?" his boss pressed the advantage with his tone of voice.

Tom gulped and offered a quick nod.

His boss visibly relaxed then and he smiled at Tom and said "Good. You are going to be a very good sissy for me."