Evelyn McDonald, his sister's future mother-in-law, caught him dressing in a nightgown; she forced Gary to confess he was a cross-dresser and demanded his obedience.

Gary now sat on a lounge chair poolside, Mrs. McDonald had selected, and his eyes darted from his phone to watch Mrs. McDonald. The adults had returned to their conversation poolside. She didn't glance his way and seemed to ignore him, but he couldn't focus on the game on his phone, just the older woman sitting across the patio.

Mrs. McDonald was tall, lean, and attractive. Her shoulder-length brown mane framed her tanned face with long layers of feathered hair, and she wore minimal makeup. She was dressed in a white, off-the-shoulder knit blouse and body-hugging Capri pants with matching promenade flats.

Mr. McDonald made reservations for the six adults to dine at the town's premier restaurant. Monica and Tom told their parents they would meet them at the restaurant and left to do errands. At the last moment, Mrs. McDonald had to excuse herself due to a migraine and went to her bedroom. With a quick kiss and a hug from his mom, his parents and Mr. McDonald drove away in the McDonalds' large Cadillac.

Gary walked downstairs to the large family room in the basement. It looked very much like a pub with a long wooden bar lined with stools, a couple of square tables with chairs underneath, all flanked by a pool table. On the opposite side of the bar, two leather wingback chairs surrounded a matching couch, which faced a large TV hanging on the wall.

He found the remote, flicked on the TV, and then sat on the couch. Gary scanned the channels and paused at an old movie that looked interesting. He took out his phone and began to play 'Star-land'. He did not hear Mrs. McDonald come down the stairs.

"Gary, dear," she said, "Didn't you hear I had a migraine? And here you are with that TV blaring?"

Gary jumped at her voice and looked backward. Mrs. McDonald had gotten dressed for dinner before becoming ill. She now wore a long, pink bathrobe that fell to the floor, but she hadn't removed her evening makeup, although her hair was now pulled back in a ponytail. She stood there, arms crossed, staring at him over her glasses with an exasperated expression.

"I'm sorry. I didn't think you would be able to hear the television."

"Just like a man, thinking of yourself."

The tall woman sighed and marched forward. She reached out and clutched one ear and drew Gary off the couch. She dragged the small teen up the basement steps and deeper into the large house. The older woman led him into a large, opulent bedroom and stood him facing a vanity. He rubbed his pained ear.

The teen watched Mrs. McDonald in the mirror as she unbelted her robe and tossed it to the side. She wore a short, black leather halter that exposed her breasts, while her bare midriff was cut by a tight black leather mini skirt. Her wonderfully long legs were encased in black thigh-high hose, and she wore four-inch patent stiletto pumps. Gary’s mouth dropped open as he openly stared at the sexily dressed older woman.

“Get dressed, dear.” She commanded, pointing toward the clothes setting on the vanity.

Gary looked down at his clothes and questioned, "Uh?"

"That's twice," she held up two fingers and warned. "Get into the nightie on the vanity. "

Gary looked at the clothes on the vanity; he didn't understand what was happening. Gary removed his oversized hoodie and kicked off his deck shoes, then pushed down his pants and underwear as one. He reached out and took the clothes from the dressing table. There was a pink, polyester nightie trimmed with white lace and matching thong panties. He slipped the nightie over his head, and it fell to his just above his hips, then slipped on the thong. He turned to look at Mrs. McDonald, who stood there, arms crossed, lips pressed angrily.

"I hoped you would be bright," she said. "Come here, dear."

She pulled out the chair from the vanity. He sat down in the chair while Mrs. McDonald retrieved several items from the vanity’s drawer. She turned him away from the mirror and opened a small bottle. The woman pulled back his hair and wrapped a hair tie around it. Afterward, she dabbed a bit of makeup on a sponge and applied it to his face.

"You have a very nice complexion. Have you started to shave yet?"

"Ah, no... Ma'am, I don't shave."

"How old are you? "

"Ah... I'm eighteen. "

"Your mother said you were eighteen. I found that hard to believe," she commented.

"I guess I'm small for my age, Ma'am," he looked down, embarrassed.

"You take after your mother. She is petite and slender, too," she said, playing with his long hair. "Do you shave your body hair?"

"Just my underarms and around... my... You know, Ma'am."

She had noticed the lack of body hair on the teen when he was swimming. He was hairless and smooth all over. She applied short strokes with a pencil to his eyebrows, then eye shadow to his lids, and mascara. Mrs. McDonald tilted his head back and smoothly applied a dark lipstick and gloss. She brushed out his dark hair quickly, tied a yellow ribbon in his hair, and turned him to look at his reflection.

Gary gasped at the image in the mirror. A pretty girl stared back at him. It was him, but never had he imagined he could look this way. He openly admired himself in the vanity mirror.

"Please stand up, Gary," she said, then placed a hand on his shoulder. "We can't continue to call you 'Gary'. What do you call yourself?"

"I sometimes call myself 'Gina'," he admitted.

"That is too common. Your name is 'Regina'," she stated. "Please stand up, Regina."

Regina stood up, and Mrs. McDonald stepped back to examine her. She moved behind her and tugged at her rear hemline. She fixed a few errant locks of her hair, and she seemed satisfied with the results. Mrs. McDonald took her phone from her skirt's pocket and aimed it at her.

"What are you doing?" Regina asked fearfully.

"You turned out very pretty," she said.

"You can't."

Evelyn McDonald raised an eyebrow at the defiance. She marched forward, spun the cross-dresser about, and spanked her hard on the bottom. Regina cried out in surprise, one hand on her wounded ass cheek. The older woman towered over her menacingly.

"If you think I am going to allow some effeminate boy-whore to tell me what I will or won't do, you are mistaken. I am in charge here. Do you understand me?" She challenged. "You will do as I say."

Regina nodded and did not debate the woman, but did as she was told. She made Regina pose for her. First, at the vanity, then leaning against one of the posts of the giant bed, and finally, with Regina posed sexily on the bed. Regina began to have fun and tried to pose quickly. After the shots, Mrs. McDonald stopped and appeared to send the photos.

"Ma'am? What are you doing?" Regina asked.

"You turned out so pretty, I had to share your photos with my husband," she explained.

"Ma'am... Mr. McDonald will not show anyone those pictures, will he?"

"Do not worry, Regina. I did not permit him to," she casually assured the cross-dresser and started to snap photos again.

Regina thought about her photos being sent while she continued to pose. Mrs. McDonald was extremely forceful and stern, but Mr. McDonald seemed to be a very dominant man. Regina began to worry that the photos might leak onto the internet.

Regina broke her pose and asked, "Ma'am, please, I don't want the photos to..."

"That will be enough!" The woman interrupted angrily.

Mrs. McDonald gripped Regina's arms and drew her close. Regina had not been close to a powerful and sexually exciting woman before. Before this, the teen's only sexual experience was when she pulled up nude photos on her phone to masturbate. To be held this close by this attractive woman was beyond excitement. She became excited; her dick grew in her thong.

"Slut, you will do as I say, when I say it. If you do not, you will be punished!"

"I'm sorry!" Regina cried out to the powerful and exciting woman.

"Stop that mewling!" Evelyn McDonald shouted at Regina. "Come here," she demanded, leading Regina across the room.

The older woman sat down on a long, padded bench and forced Regina to lie across her legs. With surprising strength, she gripped Regina's thin wrist and held it behind her back, painfully. Regina ineffectively struggled and tried to escape.

"Ma'am, you're hurting me!" Regina whined.

"Be quiet!"

Mrs McDonald expertly slipped on a leather cuff around Regina's wrist and repeated the process with her other wrist. Regina wrestled against the bonds, but the tall, sexy brunette had successfully fettered her. Still, Regina squirmed on the woman's lap and fought against the Amazon. Regina's writhing made her cock pop out and caused her to rub against Mrs. McDonald's nylons.

"Ahhmm," Regina whimpered in excitement.

"You filthy whore!" Evelyn McDonald angrily exclaimed.

The older woman reached behind the bench's cushions and brought out a small, black paddle. Rapid strikes fell on the teen's exposed cheeks. Regina cried out! With each blow, she tried to escape, pushing against the woman's nylons, effectively stroking her small, hairless cock. Regina became confused. Although her cheeks were inflamed from the blows, the nylons' silkiness stroking her member caused her ecstasy.

When she moaned softly, the blows stopped, but Regina continued to writhe on the woman's lap. Regina felt Mrs. McDonald's hand drift over her tender buttocks softly. Her fingers found the thong and traced the strap down the middle of her cheeks. They slipped around the material and snapped it against her hole.

"Oh!" Regina squeaked.

Mrs. McDonald pushed Regina off her lap onto the floor. The woman stood up and glared down at her.

"Kiss my feet," she commanded.

Regina blinked at the command and submissively knelt, then pressed her lips to the toe of one of the woman's shiny pumps. She felt no shame; it seemed natural to her. She kissed it and the other foot, softly, almost reverently.

"Good. Now, sit on the bench. and spread your legs."

Regina did what she was told, and the woman examined the cross-dresser. Her small cock, outside of her thong, stood erect. The leather-clad Amazon placed the toe of her high-heeled shoe onto his hard dick and began to massage it. Regina closed her eyes to feel the sensation coursing through her loins. Evelyn began to grind her patent pump into the cross-dresser's groin enough to have her new thrall instinctively close her legs. A soft groan escaped the budding slave's lips.

At the sound, Evelyn reached out and pinched one polyester-covered nipple, and was rewarded by seeing the bound victim's body leap in lustful excitement. The cross-dresser's bound arms twisted in sexual agony, while her hips bucked into the toe of the black pump. Regina's eyes were closed tightly, trying to block the sensations she now felt.

Evelyn McDonald lifted her shoe from the secured teen and gripped Regina's chin with her fingers. She shook the slave's head viciously, then forced a thumb between the red-stained lips. Instinctively, Regina began to eagerly suck the woman's digit.

"Oh dear! You are greedy," she chucked evilly.

She reached under his nightie to twist the other nipple on his chest and smiled when a cry escaped Regina's mouth. She continued to abuse the tiny breasts, watching her subject writhe in her restraints. Evelyn glanced down to notice that Regina's dick's head was wet with pre-cum.

"Regina, you bad girl!" Evelyn shouted.

"Yes, Ma'am. I am," Regina said huskily.

Evelyn McDonald straightened herself and smiled wickedly at the cross-dresser. She slowly unzipped her leather halter to display her firm, tanned breasts. The teen was enraptured and sat with her mouth open. The woman guided Regina's mouth onto one of her brown nipples, and the cross-dresser began to suckle.

As Regina sucked on her breast, the older woman with a free hand pushed the cross-dresser's head hard against her body. Mrs. McDonald bit her lower lip and fought back the urge to reach between her legs. Instead, she reached down and began to fondle the tiny, hairless dick between Regina's legs. Within seconds, she was rewarded.

Thick streams of cum shot into her hand. Evelyn tried but could not catch it all. Regina shrieked in pleasure, releasing Mrs. McDonald's tit, falling back against the bench; her body jerked and twitched. The older woman did not let go but continued to pump her dick. She pushed Regina back against the couch and pulled her hand off his dick.

"Eat this, whore!" Mrs. McDonald said and pushed Regina's cum into her mouth.

Regina tasted her thick, salty seed as it forced over her lips. She had tasted her cum often, but the amount surprised her, and she gagged. She heard Mrs. McDonald laugh.

"Like most men," she sneered, "Don't worry, dear. You'll get used to it."