Crossdressing Tales I: Master to Missy

By Kelly Burke

A new teacher in a California college, Jack Gillis is bullied and abused by the jocks who make his life miserable. Only the girls come to his aid to befriend him. By chance, he is forced to dress as a girl to escape a potentially disastrous situation. Yet in his new female guise, it does not go unnoticed that he is an identical twin of a well-known celebrity, Meredith Blake. The real Meredith has problems that force her to temporarily disappear from public life, and Jack is blackmailed into taking her place for several days. When Meredith’s absence becomes permanent, it is the beginning of a new life for Jack. As Meredith. The beginning of a program to forcibly feminize him. The beginning of the long, hard road to femininity. And at the end of the road, there is no going back for the pretty new female celebrity.

• Language: English
• Publisher: Hades Publishing
• Release date: Aug 23, 2012
• ISBN: 9781476369419

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CROSSDRESSING TALES I - MASTER TO MISSY

By Kelly Burke

SMASHWORDS EDITION

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Chapter One

He gazed across his class, thinking for the umpteenth time how lucky he was. His English Lit course was attended by almost entirely coeds – gorgeous, long-limbed, California girls. Jack Gillis was in his first year at Mount Raymond, and enjoying every moment of his first lecturing post. He was still young, at twenty-three, and looked a lot younger, little more than a kid. At only five feet six inches tall, he was often mistaken for a teenager who was still growing. And sometimes worse. He was a blonde guy, nice looking, with the long, curling hair and blue eyes of some of those California beauties he taught. For a girl, it would have been heaven-sent. For a guy, especially a teacher, trying to assert his shaky authority in his first post, it was a source of constant irritation. He was just too good looking. Not quite manly enough. He worked out at the gym, went jogging for several miles every morning, anything in an attempt to put on some muscle tone. He’d always been fit, fitter than most men his age. At one time he’d even played quarterback for his high school team. But still, somehow he never achieved the respect he felt he deserved as just one of the guys. He stared at his class.

We’re looking at the Merchant of Venice this morning, Act Two, Scene One. Have you all read the play?

Julie Southby smiled at him. I tried to watch it on DVD at the weekend, Jack, but I couldn’t make it out. I was totally confused by the second act.

He encouraged all the students to call him Jack. University was a relaxed, adult environment. He didn’t want to be thought off as a pompous ass. Even so, some of the boys took advantage, and he’d often heard them, behind his back, calling him Jackie. He did his best to ignore it.

What did you have problems with, Julie?

She was probably out chasing guys instead of watching the play, with a bottle of Jack Daniels inside her, a low voice muttered. Jack sighed inwardly, Annie McGregor again, causing trouble. The problem was simple. Annie was very pretty. She was also the Head Cheerleader, and one of the popular kids. She could pretty much say and do what she wanted. And she usually did.

Ok, pipe down, Annie. Julie, if you’ve got trouble understanding the text, remain here after class and I’ll do my best to explain it to you.

There was a loud murmur of jeers and catcalls. Again, he ignored them and got on with the lesson. When it finished, he breathed a sigh of relief and sat down to wait for Julie, so they could go over the play.

She sat down close to him, too close, and he noticed her tiny skirt stretched over her ass and thighs. It was so short it almost rode up over her fanny. Almost. How the hell did girls wear skirts like that? It looked as if it defeated the laws of physics. Her firm young breasts were squeezed into a too-tight blouse, and her dark brown hair was teased up into a back combed, sixties bouffant style, like the late British singer Amy Winehouse. Her face was painted with enough cosmetics to empty a pharmacy, and her feet were encased in elegant, high-heeled shoes. He felt a twinge of arousal and forced himself to calm down. She was a student and he was her teacher. He went through the part of the play she’d had problems with, line-by-line.

Do you get it now, Julie?

She fluttered her huge eyelashes. He noted with surprise they were false. He hadn’t realized that before. God, it must take her an age to get dressed and made up every morning. He wondered what it would be like to wear those complicated female clothes. Difficult? Probably. But pretty, very pretty.

I really do, Jack, thanks for explaining it to me. It’s much better now.

Good. If you have any more problems, let me know.

Yeah, I will. Jack, could I ask you a personal question?

He felt a twinge of concern. It was not the way a teacher student relationship should work. But he didn’t want to sound stuffy either.

Of course, go ahead.

Do you fancy me?

Oh shit! This was going in entirely the wrong direction.

Er, you’re very nice, Julie. But I can’t think about those things, you’re my student, and I’m your teacher.

And if I wasn’t your student?

He smiled. I guess I may think along those lines, yes.

She nodded gravely. That’s a shame, then.

A shame? Why’s that?

Because you’re a nice guy, and I’m a lesbian, so I’d hate to disappoint you.

He felt a tremor of shock run through him. He was quite relaxed about sexuality, lesbians, gays, bisexuals; he was fine with any and all of them. But this was a bit ‘in your face’. Maybe she did it deliberately, so kind of girlie power play. And it was a severe dent to his masculine pride. He forced another smile on his face.

Well in that case there’s no problem, is there?

She smiled. No, there isn’t. Listen, Jack, the reason I told you is this. Could I call around to your place later, run a couple of things past you? You know now you’d be safe.

He shook his head. That wouldn’t be a good idea, Julie. You know why.

She nodded, her face a picture of disappointment. Then she brightened. Look, why don’t you call around to my dorm, then you could show me some more of that difficult Shakespeare I’m trying to bone up on.

He shook his head. Same answer, you know the deal.

When classes ended, he hefted his shoulder bag filled with documents and his laptop and went out into the car park. His car, a neat little Mitsubishi MX-5 Miata was parked on the far side. The nearer spaces were reserved for the older, tenured staff. In between the main building and his car a group of boys stood laughing and chatting amongst themselves. He looked for another way to reach his car, but he had to go past them. The boys of the psychology class, which was run by Professor Ethan Bradshaw. A sneering bully if ever there was one, and his students seemed to take their lead from him. Jack walked calmly towards them, and almost made it past.

Hey, Jackie, you going to meet your boyfriend? one of them shouted.

Jackie, you heard of that new play? Romeo and Jackie?

The boys laughed uproariously. Oh Romeo, Romeo, wherefore art thou Romeo? Its okay, Jackie’s here, she’s called to see you, Romeo.

Words he could live with, although they were like daggers cutting into him. But they blocked his path, so he couldn’t reach his car.

Where are you going, Jackie?

He felt a flush of anger. Get out of the way, you’re out of line, all of you. You should know to behave better than this.

Ooh. Listen to her! Is Jackie upset with the bad boys? What are you going to do about it?

It was Dexter Merano, their leader, and a bully. He was also one of the popular kids, and the colleges quarterback. He sported a heavily muscled, but slim body, handsome looks and a buzz cut hairstyle. He was as macho as they came, and he reveled in it.

Dexter, you’ll be in trouble if you try to mess with me or any of the staff. Now move out of my way.

He laughed. Make me, Jackie.

He wondered if he should push through them, risking a physical confrontation, or go back and wait for them to disperse. But the decision was taken out of his hands.

What the fuck are you guys doing? Why don’t you get out of the poor guy’s way, he hasn’t done anything to you!

Jack recognized Julie’s voice. He turned around, and saw her with three other girls, all literature students from his class. Dexter sneered at them.

Come to rescue your girlfriend, have you, dyke?

Julie turned to her friend, Abbey Brent. "Abbey, would you go and call security? Last time I heard, sexual harassment like that was an automatic suspension from college. This stupid ass will get