Madam of Maple Court (34 page)

Marcy looked at Pam. "Would you do this for him?"

Could she? Why not? She'd do some research and do her best to make him look the way he wanted. After all, she'd done it with two little girls.

Two weeks later, James arrived at the club at a little after seven. Marcy and Pam had rearranged the all-purpose room on the third floor with several full-length mirrors, a dressing table, and a clothes rack with a selection of dresses in what they estimated to be James's size. Several pair of low-heeled sandals with enough buckles to adjust to most sizes sat in boxes in one corner. Undergarment sizes were a little more difficult to judge, but they had enough of an assortment that it should work.

James was shown upstairs and his eyes widened when he entered the "dressing room."

"This is wonderful," he said.

Pam had never seen him standing up but now she guessed that their estimations of sizes were pretty good. "James, come in. I think we're pretty well organized. There's no one else on this floor this evening, so you can come and go to the bathroom as you wish without anyone seeing you. Why don't you strip down to your shorts so we can get started?"

An hour of body and leg shaving, facial depilatories, and moisturizers satisfied him that he was ready for the next step. His hair was long enough that styling gel and a curling iron created a pretty nice-looking head full of curls. Pam thought he looked a bit like Little Orphan Annie, but he seemed delighted by their progress.

Fitting him for a bra and panties almost made Pam laugh, but he seemed so delighted that she was pleased for him. "You even got breast forms for me," he said, putting the pads into his bra.

When he was organized, she said, "Okay, now let's pick out a dress," and the fashion show began.

Using a digital camera she took photos of him in several dresses, letting him use the pictures to make his final selection. "This one," he said, selecting a spring floral print dress with an off-white background, soft rose flowers, and moss green leaves and vines. They arranged the straps on a pair of off-white sandals and added a strand of green beads with matching screw-back earrings.

Wearing his feminine clothing, Pam thought he didn't look half bad. They'd talked throughout the process and Pam found herself liking the man very much. He was, as he'd said, heterosexual and was planning to be married within the following year. "I wanted to do this before I give up even thinking about it for good."

"You can't necessarily control your thoughts, only your actions."

"I know that, but I can try, for Nancy's sake."

"Now for your make-up." Pam had spent several hours searching the Net, learning tricks for making wide faces look narrower, long noses look longer or shorter, cheekbones look more prominent, eyes look wider, and generally camouflaging facial flaws. She snapped photos as she worked.

She wouldn't let him look at himself as she worked, so she steeled herself for his reaction when she finally she turned him to face the mirror. As she looked over his shoulder at his new look she was amazed at what a good job she'd done and what a fairly decent-looking woman he made. "Wow," he breathed. "Wow. Is that really me?" His face was wreathed in smiles and he almost giggled.

"It certainly is. Do you have a name for this persona?"

"Denise. I've always wanted to be Denise."

They took dozens of posed pictures, then Pam said, "Okay, girlfriend, let's get out of here. Oh, and walk slowly. The shoes will take a little getting used to."

Together they went to a small club Marcy had suggested. No one seemed to notice James/Denise, and at one point a man made flirtatious eye contact with him/her. "He's looking at me like he wants to come over. I don't think I'm ready for that."

"Shall we leave, then?"

"I think so."

Back at Club Fantasy, James disappeared into the bathroom to shower and change back into his street clothes while Pam printed several of the pictures, then wrapped his new clothing, shoes, undergarments, and an assortment of make-up in a large box for him. When he returned from the bathroom Pam handed him the camera and a stack of photos. "The camera's yours, so there's no worry about us having any of the pictures. If you notice, too," she said, pointing to a group of snapshots, "I took step-by-step pictures of your make-up so you can duplicate it if you want to."

At first she'd been skeptical about the whole thing, but now, seeing his delight with the photos and the package of goodies, she was more pleased than she might have imagined. "Pam, thank you," he said, then he kissed her on the cheek. "You're wonderful and a lifesaver. Not only did you do this for me, but you made me feel so comfortable about it."

"I'm glad you're happy."

"Oh, I am. You can't imagine what a thrill it is to become someone so new."

Pam considered the previous year. "Actually, I think I can."

In the middle of June, a man entered the all-purpose room on the third floor of the club, dressed in a sweatsuit and sneakers. He was in his mid fifties, short, with a belly that had started its trip outward. His thinning salt-and-pepper hair was cut short and his face was creased with laugh lines. His most striking features were his deep blue eyes. "Yes, Ms. McAllister, you wanted to see me?" His voice had a hint of an English accent.

"I did, Gordy," Pam said in her guise as the teacher. "You've been tardy to my class three times in the last two weeks." She wore a prim white blouse, straight black skirt, and thick-soled shoes. She had slicked her hair back and twisted the strands into a bun.

"I'm sorry, ma'am. I've been trying to train for the track team. Sometimes I don't get showered in time."

She raised an eyebrow from her seat behind the large oak desk that had been positioned in the middle of the room after the rest of the furniture had been removed. Maps hung on the walls, a flag drooped in the corner, and several smaller desks were scattered around the room. They'd rubbed chalk on two erasers and then banged them together just before he arrived so the room had a schoolroom pall and even smelled like she remembered her school smelling. "That's not really my problem, is it?"

"No, ma'am. I'm sorry for being late to class."

"Good. I'm glad you recognize your difficulty."

"Difficulty, ma'am?"

"The rules state that three tardy reports can get you expelled."

"Expelled?"

His seemingly genuine fear always surprised her. They'd played this scene several times, and each time he behaved as if it were all new. That was one of the wonderful things about fantasy, she'd discovered. For some men it didn't matter how often they played out the same one, it was as exciting the last time as it had been the first. Some men changed their desires over time, but others, like Gordon, or Gordy, as he preferred to be called in this "classroom," honed it, making it closer to perfect for him each time they played. "Yes, Gordy, expelled."

"But, ma'am…"

"No buts, young man. I'll have to call your father."

He looked as if he were going to cry. "You mustn't do that!"

"I mustn't?"

"I'm sorry, ma'am. You can and should do whatever you need to, but he'll kill me if I'm expelled."

"Hmm," she said, picking up a long, slender paddle from the desk. "I haven't reported any of your tardies yet. I guess I could overlook one if you're truly repentant."

Words came spilling forth. "I am. Oh, I really am. I'm sorry about it all and I'll be on time for the rest of the semester. I promise I really will."

"Oh, I'm sure I can impress upon you the importance of being on time." She slapped the paddle against her palm. "I know I can." She stared at him. "Drop them!"

"Do you have to do that?" he wailed.

"Excuse me? You're the one who doesn't want me to call his father."

"I know, ma'am, but it will hurt."

"It certainly will. Do you remember the word?" They'd agreed on a safe word before they played this scenario the first time. If he said the word "Red" at any time, everything would stop. That way he could cry, beg her to stop, without worrying that everything would indeed stop.

When Marcy first asked her about playing this scene with a new client, Pam hadn't quite understood some people's desire for a little pain. She'd read about it, of course, but this would be the first time she'd actually done it.

"Pain heightens a sexual experience for some people," Marcy had explained. "I don't mind a little swat on the ass from Zack occasionally, but some seem to need more than a little slap."

"It's not my thing," Pam said.

"Mine either," Marcy said, "but a few of my ladies really enjoy being on the receiving end of a power/pain session."

"Why me, then? Why not one of them?"

"Receivers, masochists, bottoms, they don't usually enjoy being on the other side, and the two ladies who do enjoy being tops are otherwise engaged. Do you think this would bother you?"

"I don't know, but I don't think so."

"Would you help me out, then?"

"Sure."

So she'd had her first session with Gordy and had found that although it didn't excite her much, it didn't repulse her, either. Seeing a man get so much pleasure pleased her tremendously, however it happened.

" 'Red' is the word, ma'am," Gordy said now as Pam continued to slap her palm with the paddle.

"Good boy. Now drop 'em!"

Slowly Gordy began to pull down his sweatpants. Through his white shorts, she could easily tell how aroused he already was. "Everything. Quickly!"

He stripped. "Now fold your clothing neatly." Anything that dragged the scene out increased his excitement. With shaking hands he put all his garments in a stack on the corner of the desk. "Good. You're doing well. Now assume the position."

He leaned over the front of the desk, cradling his head on his folded arms, stark white, white behind easily accessible. His cock was long and swollen.

"Now," she said, now slapping the paddle lightly against her thigh, "how many today?"

"Five, ma'am?"

"Oh, come on, Gordy, three tardies?"

"Ten, ma'am."

"Okay. We can start there. Now count. You know how to do that, don't you?"

"Yes, ma'am."

She swatted his naked ass once lightly with the paddle.

"One, ma'am, and thank you for helping me learn."

Again. "Two, ma'am, and thank you for helping me learn."

The next few were relatively soft, gradually increasing in force, but at about eight, she began to spank him really hard. "Eight, ma'am," he said, his voice cracking, "and thank you for helping me learn."

Nine and ten were as hard as she could make them and she found that, by the end, her arms were getting tired and her hand stung from the force of the paddle. Originally she'd used her palm to administer Gordy's punishment, but with his approval she'd switched to the paddle when her hand began to hurt as much as his ass. "Ten, ma'am, and thank you for helping me learn." He stood up almost in tears, his erection looking almost painfully hard.

"Now you'll have to show me how sorry you really are." She sat down behind her desk and crossed her legs. "Touch your dick."

"But, ma'am…" He shuddered.

She merely raised an eyebrow and smiled.

"Of course, ma'am." He wrapped his fingers around his erection.

"Now don't make a mess," she said, "while you stroke it."

He took a breath as if to protest, then began to slowly rub his hand over his hardness.

"Oh, Gordy, you can do a better job than that."

"Yes, ma'am." He began to stroke his cock in earnest, a look of pure bliss on his face.

"Use your other hand to play with your balls."

As he did, Pam tapped and rubbed the paddle on the desk in an imitation of Gordy's motions on his cock. As he stroked, his eyes never left the movements of the paddle. Faster and faster she moved the wooden slat, and his hand moved in time with its rhythm. Finally, when he couldn't hold back any longer, he spurted semen onto the desk, his entire body jerking as he came.

Silently they cleaned up. She checked the hallway, then he crossed to the bathroom and showered. Later, back in the "classroom," he was dressed in a golf shirt and slacks. He picked up his sweatsuit and stuffed it into a small black duffel. "Pam, as always you were wonderful."

"Thanks, Gordon," she said. He was only Gordy to his teacher. "I always enjoy our times together."

"See you next month?"

"Of course."

He closed the door behind him and Pam quickly changed into a pair of jeans and a T-shirt. She knew that Marcy would take care of scheduling and charging his credit card.