One day Debbie came to see Dennis and announced that she had bought a "present" for him - three pairs of thong jockey shorts! Black, red, and white to match his growing pile of bras and stockings. They were cut high on his legs with a pouch in the front for his dick and balls. Debbie liked how they bared his ass and eliminated "panty lines". He had to admit that he felt hot as hell with them on; they made him feel like some sort of male stripper.

The next day Debbie brought in large shopping bag. "Now don't freak out, okay?"

"Have I freaked out yet?" Dennis said petulantly. He sat on the bed, wearing only his bra and thong shorts. His hair was pulled back in the familiar pony tail but a careful observer could see that his bangs were ever so slightly teased.

"Okay, but this is different," she said as she pulled out of the bag a little pile of white fabric.

"What's that?"

"A nightie."

"Oh, God," he said, falling back on the bed.

"Dennis, you promised."

"I can't wear that."

"Why not?"

"It's too ... too much."

Debbie put the white satin and lace nightie up against her body and danced around the room. Then she turned to Dennis, "Aren't you curious to see what it feels like? It will be great against your sensitive skin."

"No... I don't know." Debbie rolled her eyes.

"Come on little baby, get up. I want to see how it fits you." Dennis reluctantly obliged and she held the nightie up to his body. "Take off your bra and put this on." Dennis gave her a withering look and slid off his bra.

Dennis's now dainty foot trembled as he stepped into the tiny heap of white. As he pulled it up, the stretch material clung to every curve. Finally he eased the spaghetti straps over his shoulders and a moment later he was taking tentative steps around the room, staring down at his body moving under the tight thin material. The thin straps and plunging neckline exposed his soft shoulders and abundant boobs. The top of the nightie strained to contain its heavy load. It hugged his twenty-two inch waist tightly. The hem extended only barely lower than his thong shorts. His legs looked sleek and lightly muscled. "Don't you want to see yourself?" Debbie said, rushing him toward the door.

"Yes, but ..." His father had still not seen him wearing a bra, let alone satin and lace. The last thing Dennis wanted was to surprise him in this hot little number that displayed his gorgeous knockers unashamedly. And yet, he was terribly curious about how he looked. Debbie's face waited expectantly for his nod and even the faint whisper of the satin against his ass seemed to urge him on. He relented. "Okay, let's go." Debbie opened the door, looked both ways, and they ran to the bathroom.

The reflection literally took his breath away. He was hotter than a blow-torch. A new emotion was stirring down deep inside, an emotion that confused and frightened him. He was almost proud as he turned this way and that to view his profile. Debbie also noticed the first signs of a feminine vanity creeping into his demeanor. She was dying to undo his ponytail and brush his hair out and Dennis must have been thinking along similar lines because after observing himself for a long moment he discarded the rubber band and shook his head. The long auburn waves, free at last, framed his face with a kittenish dishevelment that literally forced his face into a pouty sultriness. He turned to Debbie. "I look really good, don't I?" He blushed deeply. "I mean, do I look okay?" he said, painfully aware she had caught him basking in the ecstasy of feminine conceit.

"Yes, you're gorgeous. Now let me brush your hair out."

Dennis smiled and sat down on the edge of the tub like a princess awaiting her chambermaid. The brush moved through his tangled curls reluctantly at first but soon Debbie's hand pushed down easily and the snarls resolved into a smooth cascade of mahogany, the strands aligned like exquisite wood grain. It felt so wonderful he wanted to purr. "I've been wanting to do this for days," Debbie said. "It's a sin to have hair this beautiful and not brush it. In fact, it's a sin not to have it styled."

Dennis turned to look at her. "But I can't do that. I'd have to leave my room."

"So, you're going to stay in your room forever?"

"I'd like to. I'd like to have you come brush my hair every day and talk to me and bring me ..."

"Girl clothes?"

"Yes. And we could be together like we used to be."

"It'll never be exactly like it used to be."

Dennis folded his hands in his lap. "I know."

Debbie glanced in the mirror and caught Dennis's eyes. "You know, there's one thing I can't teach you here that's absolutely essential."

"What?"

"Shopping at the mall," Debbie laughed. "Why don't we go out together to the mall tomorrow. You need to get some things that fit. You'll love it."

Dennis was skeptical. "What would I wear, I mean this isn't exactly right for the mall."

Debbie smiled. She knew he was ready. "There are a couple of skirts in the bottom of the bag the nightie came in, Princess."

SHOPPING SPREE

The next day was Saturday. Dennis got up at dawn to prepare to leave the house as a girl for the first time. Around nine o'clock his mother knocked on the door and delivered his breakfast. Clothes were strewn all over his room and he wore only a see-through white blouse. "You okay, honey?" she asked.

He turned to her and smiled. "Yes, I guess. I'm supposed to go to the mall today with Debbie."

"That's great!" she said. "Have you figured out what to wear?"

"Yes. No. I don't know."

"What's wrong?"

"Mom," he said with exasperation, "It's not what to wear that's the problem. It's wearing a bra and stuff out there," Dennis said. He turned his head to the window, creating a curvy cameo against the blue sky.

His mother put her arm around his waist. "It'll be fine. No one will ever suspect."

He spun out of her grasp. "No will ever suspect what?" he demanded.

She stepped back in alarm for a brief moment. Then regaining her composure she said deliberately, "That you're not a girl."

"Even though I look like one?"

"Yes, a very lovely girl," she added. Tears welled up in his eyes and he said, "I'm scared, Mommy."

She hugged him. "I know, honey. I know. It'll be fine. Everything will be fine."

An hour later the door opened and Dennis emerged like a shy butterfly. He wore his old jeans jacket over a tight black turtleneck sweater and denim skirt that Debbie had brought him. The denim material was thick enough to keep the bulge in his crotch from showing. His sweater accentuated his bust in a way that both embarrassed and excited him. They drove to the mall in silence. Dennis looked out the window and played with the end of a pig-tail. When they arrived his mother said, "You'll be fine. Try to have fun with it." Dennis made an effort to smile. She watched him walk across the parking lot, losing track of him as he blended into a crowd of teenage girls headed for the mall.

Dennis arrived at the appointed meeting place early and sat down on a bench to wait. His breasts felt bigger and more conspicuous than ever and he unconsciously began to hunch over to hide his curvy new figure. When he saw Debbie walking across the mall he straightened up a little.

"Hi!" Debbie said excitedly.

"Hi."

"You look great."

"Thanks." He blushed. "Everything feels so ... tight."

"That's because you're such a big girl. Are you ready?"

"Not really."

She pulled him up off the bench and they headed off to Dillards. Debbie took Dennis back to the dressing rooms, and said, "Wait here. I'll be back." He sat down and fidgeted, trying not to listen to the sounds of dresses dropping and bras hooking.

Soon Debbie returned with clothes, quite happy with her selections. She had picked out clothes that she knew would turn Dennis on. She had a strechy little top, black leather micro-skirt, and stiletto heals. Dennis was going to have a coronary. Until he admitted he loved it. She walked into the dressing room and found Dennis shyly huddled in his stall.

Debbie dropped the clothes on the seat. Dennis picked them up. "I can't do this," Dennis said holding up the top.

"Dennis, don't be silly," Debbie said in a deadpan voice, "put it on."

"But it's so thin and the skirt is too short," protested Dennis.

"I'm not getting you anything else until you try that on," replied Debbie.

"I'm not going to forget this," Dennis said as he slowly began to dress.

"No, I doubt you ever will," she replied.

He pulled on the top, his breasts stretching the thin blue garment to the breaking point. It was so low cut that it exposed the top of the dark areas around his nipples. And it was cropped so his flat belly was left bare. The tight material lifted his breasts and pushed them together, giving him fantastic cleavage.

Dennis pulled the tiny black leather skirt up his long legs and over his ass. It melded to his ass like a second skin, but was substantial enough to suppress the buldge of his cock in the front. "They're both too small," Dennis complained. His nipples were clearly visible and the skirt was compressing his lower stomach and butt.

"Don't be such a whiner," Debbie said unapologetically, "You should show off a great bod like yours."

Debbie admired how the short skirt looked over his thong briefs. She would swear that Dennis had nothing on beneath it. When he leaned forward to put on the high heels, the dress rode up and Debbie got a good look at his bare asscheeks. "How am I supposed to walk in these stupid things?" Dennis complained as he staggered in the little dressing cubicle. The stilettos finished off the look, accentuating his calves and long flowing legs.

"Oh, shut up," she said, "they make your legs look like a Rockette's and you know it."

"I want to look in the mirror," he said as he quickly opened the cubicle door. He paused in the doorway, bent forward a little leaning against the doorjamb. Dennis looked back over his shoulder at Debbie, made a little kissing motion with his lips then winked at her and headed for the full length mirror in the dressing room hallway. Debbie laughed and followed him out.

The girl in the mirror looked like a whore out to pick up tricks. A very gorgeous whore. Dennis posed and primped until another woman wanted to use the mirror. Dennis and Debbie darted back into their dressing room, giggling and blushing.

He spent the rest of the afternoon taking off clothes and trying on others. Debbie had a great time selecting things and then having him model them for her. There wasn't much of a leather selection at the mall, but they found lots of other sexy stuff. Soon he forgot who he was and where he was and began to look forward to trying on the tops, skirts, dresses, bras, stockings, garter belts, nightgowns, shoes and slippers that Debbie chose for him. His own reflection turned him on immensely.

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