Hal(ey)

Act I: The Secret Hobby

"Have a good day at work, honey," Emma told her husband, kissing him on the cheek.

"You too, dear," David replied, before departing for the day.

Emma looked across the breakfast table at their eighteen year old son. "I'm going to stop by the market on the way home from work today. Is there anything you need?"

"Not that I can think of," Hal answered.

"Alright then. Call me if you need anything," Emma responded before she too left for work.

Hal leaned back in his chair, waiting and listening for the sound of his mother's car driving away, thinking.

From a very young age, he'd discovered he'd liked dressing up in women's clothes. He'd often snuck into his parent's bedroom when they were gone, trying on his mother's dresses, skirts, blouses, and even panties and bras. This usually ended with him masturbating and then quickly trying to fold and replace the items before his parents returned home.

Emma and David were both fairly young parents, each only 37 years old. As such, Emma was still in great shape, the best of her life, and her clothing was no exception. She had a wardrobe full of sexy miniskirts, all styles and colors of panties and bras, and several styles of dresses. She also had a collection of lingerie stashed away that Hal had easily found, consisting of garter belts, corsets, bustiers, and stockings. These were some of his favorite things to dress in.

For a long time, he hadn't really ever thought about his mother, even whilst wearing her clothing. But then one day, he'd decided to pluck a pair of her panties from the laundry bin, and after inhaling the aroma that still lingered on them, he began to fantasize quite frequently about her. She was gorgeous after all, a tall blonde bombshell with long legs, crystal blue eyes, and a toned body.

Hal himself was rather lithe. He had never really gotten into sports and only exercised enough to keep himself thin, not muscular. His hair was blonde like his mother's, albeit a few shades darker. He kept it long, finding that it gave him a more feminine appearance when he dressed in his mother's clothes.

He knew this would probably be one of the last opportunities he'd have to do this. It was the Summer break between his last year of high school and his first semester of college. Once he heard the familiar sound of his mother's car fading into the distance, he hurriedly cleaned the table and rushed into his parent's room.

Hal knew exactly what he wanted today. He dug into his mother's lingerie stash, removing a pair of black lace panties and a set of matching stockings. Before returning to his room, he also stopped by the laundry bin, grabbing a sexy little blue thong.

Upon reaching his room, he excitedly tore off his clothes, slipping the black lace panties up his legs. He sighed happily as he felt the silky smooth material slide over his ass and encase his cock, which was already getting hard. He sat on the edge of the bed, slipping the stockings up his legs one by one, smoothing them out and taking the time to admire his shapely legs in them. He kept his body shaved for the same reason he kept his hair long, to maintain a feminine appearance for his dress-up playtime, and so his legs looked smooth in the stockings, just as a woman's would.

With the panties and stockings in place, he slid back to lay on his bed, his head coming to rest on the pillow. He took the blue thong, placing it over his face and inhaling deeply. He shuddered in delight at the scent of his mother's pussy. With his free hand he reached down, pulling just the front of the lacy panties down so his cock sprang free. Wrapping his fingers around it, he began to jerk off, steadily sniffing the thong he held to his face.

Hal closed his eyes, continuing to pump his cock. He imagined that it was his mother, smiling down at him dressed in a sexy corset, heels, and stockings, giving him a handjob. The thoughts swam in his head as his hand became a blur. Precum began leaking out, dripping over his fingers.

He opened his eyes and put the crotch of the thong in his mouth. He began to suckle at the material, and was rewarded with a very faint hint of his mother's pussy. He could just barely taste a bittersweetness, and this combined with the smell and the thoughts of incest running through his mind brought him to orgasm. His hand clenched tighter around his cock as he pumped a few final times, shooting jets of warm, sticky cum all over his stomach.

Hal lay there for a few minutes to catch his breath, his mother's blue thong still on his face. Thoroughly satisfied, at least for the moment, he cleaned himself off before replacing his mother's clothing. He always felt a twinge of guilt afterwards, wondering what if meant for his sexual orientation that he liked wearing women's clothing, and what anyone would think if they knew the dark, primal thoughts he had about his own mother. In the end though these thoughts always faded, and he found himself coming back for more.

--

Act II - In the Dark

The rest of the day went by normally. His parents had both come home from work, they'd all had dinner, watched some TV, and eventually retired to bed. Hal had fallen asleep rather quickly at first, but found himself awake just a few hours later. He stared at his alarm clock, reading 12:07 in bright red letters. He sighed and got up, unable to fall back asleep. Dressed only in a pair of blue and green plaid boxers, he decided to go downstairs for a midnight snack. On his way down the hall though, he stopped dead in his tracks.

From his parent's room, he could hear his mother moaning. Even though he'd been fantasizing about her for a long while now, he'd never once tried to peep on her. But hearing her moan, his cock gave a twitch and he couldn't help himself.

Hal turned the knob very slowly, cracking the door open just enough to peek in. Through the darkness, he could make out his mother bent over the bed in nothing but a pair of fishnet stockings and three inch black stiletto heels. David stood behind her, thrusting his cock hard and fast into her pussy, holding onto her hips tightly.

Hal's cock was immediately hard. He couldn't make out much because of the darkness and the angle, but he could see his mother's breasts sway as David continued to pound into her. It was more than he'd ever seen of her before, and he couldn't help himself. He pulled his boxers down around his thighs and began to jerk off, eyes glued to his parents fucking just a few feet away.

Though he was extremely horny now and jerking his shaft at a steady pace, he couldn't decide what to look at. He could make out the stockings and heels on his mother's shapely legs and feet, and absolutely loved the look of them on her. And then there was his father's dick, pumping in and out of her pussy, which he'd only ever gotten to smell and taste, and even then only by proxy. Then there were her breasts, nipples as hard as his cock, swaying with each of David's thrust. He knew from his wardrobe raiding that they were 36Ds.

Just when he thought it could get no hotter, he heard his mother speak in the most sultry voice he'd ever heard. "I'm ready for it now," She whispered to her husband.

Without missing a beat, David slipped his cock out of her pussy, the entire thing slick with her juices, before pressing it against her asshole. Hal's eyes went wide and his hand stopped temporarily, as he couldn't believe what he was seeing. David slowly pushed his rock hard, pussy-slicked cock into Emma's ass, inch by inch, until he'd buried the whole thing deep within. Hal heard his mother moan again.

As David began to pump in and out of Emma's tight ass, Hal again began to jerk off, faster than ever before. He couldn't believe his mother loved anal. He'd never even considered the thought, but here she was, asking for it and by the sound of things, enjoying it too.

He couldn't hold it back any longer. He felt his balls tighten and raised his free hand to catch the hot spurts of cum that short forth from his dick as he continued to pump it. He leaned against the door frame to catch his breath, still watching his parents. David's thrusting became quicker and more erratic, and he too felt his orgasm approaching. With a guttural groan, he began pumping his thick seed deep into Emma's ass, savoring the feeling of her anal walls clenching his cock and milking it dry.

As his parents collapsed on their bed, he snuck back to his own, cleaning off his hands and this time having no trouble falling back asleep.

--

Act III - Caught Up and Out

The next morning, Hal awoke extremely horny, still thinking about the previous night. Glancing at his clock, he saw the familiar red numbers read 9:17 and knew his parents were both long gone for work. He practically ran from his room to his parents', again accessing his mother's stash. He took the thigh high fishnet stockings that he recognized from the night before, as well as the black stilettos, and a neon pink thong. As he passed the laundry bin, he noticed a pair of black French-cut panties on the top of the pile, and knew they were the most recently worn pair.

He quickly trotted back to his room, stripping out of his boxers and pulling the thong up his legs. As usual, his cock was already hardening. He loved the feeling of the fabric between his ass cheeks, and the silky material stretched taut in the front to contain his growing member. He then slid on the fishnet stockings, smoothing the tips out over his thighs before slipping into the heels. He'd worn his mother's heels on occasion, and had gotten very good in walking in them. He had no trouble getting to the full-length mirror in the bathroom.

Hal stared up and down at his reflection. The heels emphasized his calves, and looked spectacular in combination with the fishnets. The neon pink thong perfectly fit over his bulge as well, and he began to rub his cock through the material. At the same time, he lifted the used panties he'd taken from the laundry bin to his nose, inhaling deeply. He closed his eyes, taking in the scent as he pulled aside the front of the thong. With his cock now free, he wrapped his fingers around it and began to pump, opening his eyes to admire the sight.

With the stockings, heels, panties, and his long blonde hair, he looked so feminine, and seeing his dressed up reflection just made the entire scenario hotter for him. He moaned and closed his eyes again, bringing the crotch of the French-cut panties to his mouth so he could suckle on it, tasting the memory of his mother's pussy.

"What the fuck are you doing?" Came a familiar voice behind him.

His eyes shot wide open and he froze. He could see his mother in the mirror's reflection, standing behind him, her arms crossed. She was clearly dressed for work, in a white button up blouse, black knee-length pencil skirt, black thigh high stockings, and sensible black heels. Her hair was up in a neat ponytail, with a few strands loose in the front for style.

"I-I-I-I..." Hal stammered. Finally able to move, he quickly tucked his cock back inside the pink thong and turned around, covering his erection with his hands, still clutching the pair of French-cut panties.

"I only had a morning meeting to attend at work today, but I sure as hell didn't expect to come home and find this, even after catching you watching your father and I last night," Emma said sternly.

Hal's cheeks burned bright red in embarrassment, "y-you saw?"

"You were standing in the doorway jacking off. It was pretty obvious."

Emma entered the bathroom, closing the door behind her.

"M-Mom?" Hal asked sheepishly, confused.

"Why are you wearing my things?" She asked matter-of-factly.

"Well you see...I...it um...the thing is...well see..." Hal stuttered, trying to come up with an excuse but failing spectacularly.

"Just tell me the truth, Hal," Emma said, stepping closer to her crossdressing son. She looked him up and down, from her heels on his feet to her panties wrapped around his cock and in his hands.

"It just...feels sexy, mom," Hal admitted, staring down. He felt his mother's finger on his chin, lifting his gaze to meet hers. It was much softer now than when she'd first spotted him.

"What does? Wearing my things? Because they're women's clothes or because they're mine?" She asked, a sudden gentleness in her voice. It helped Hal become more honest.

"Both, I guess," He said quietly.

"And watching your father and I?"

"It was just...your clothes...and you mom...look really good," His voice was almost a whisper now, his cheeks still burning red.

"So you like my clothes...and me, huh?" She asked. "Oh honey, there's nothing to be ashamed of. Don't feel bad. C'mon, cheer up," she said, leaning forward and hugging him close. He was so confused, at first he just stood there. He was ashamed of being busted, and still felt more than a little awkward standing there in a thong, fishnets, and heels in front of his mother. Eventually he returned the hug though, wrapping his arms around her.

Emma kissed her son's cheek, spinning him around to look at the mirror again. As she did, she began to play with his hair, smoothing it out and brushing it with her fingers.

"My clothes look good on you too, you know," she said with a devious little smile. At this point Hal didn't think he'd ever stop blushing.

"Th-Thanks mom..." he said, hands still covering his crotch, although his erection had gone down from the shame of being caught.

Emma reached down, taking the black French-cut panties he still had in his hands. She lifted them, noticing the wet spot on the crotch.

"I was just in these yesterday. You really do like me, huh?" She brought them to her nose, inhaling her own scent.

"I can't help it mom. You're just so pretty," Hal squeaked out, staring at her reflection.

"I'm flattered. And you like the way I smell, huh? And taste too, apparently."

Hal nodded silently.

Suddenly Emma took him by the hand and led him to her bedroom. Hal followed behind, still confused and embarrassed by the entire situation. She stood him next to the bed and knelt down on her knees in front of him. She tossed the pair of black panties back into the laundry bin and then groped his cock through the neon pink thong. Hal gasped.

"I never would've thought you liked me that much, Hal," Emma mused. She could feel her son's cock getting hard through the material of the thong. "I haven't felt as attractive since I became a mother. That's why I have such sexy things lying around. Your father always says I'm gorgeous but...I don't know."

"Mom...you're the best looking woman I know," Hal finally opened up. "I've fantasized about you for years. You ARE gorgeous."

Emma smiled and looked up at her son.

"Well, a good boy like you deserves a reward then, doesn't he?"

She pulled the thong aside so that Hal's cock sprang free, now fully erect again. His jaw dropped as he watched his mother lean forward, opening her mouth and swallowing his cock down to the hilt in one motion. He was a virgin, and he'd never experienced such pleasure before. A warm, wet mouth enveloping his hardness. He couldn't help but moan. Seeing his mother on her knees in front of him was the sexiest thing he could've ever dreamed of.

Emma began to slide her mouth up and down the length of her son's cock. Her soft lips caressed the smooth skin, and her tongue wriggled along the underside, coating it with saliva. Even in his wildest dreams, Hal never imagined it feeling quite this good.

Emma lifted one hand and began to jerk off the bottom half of his cock, while continuing to blow the top half. With her free hand, she unbuttoned her blouse, wriggling out of it to reveal her breasts held back by a lacey white bra with tiny pink bows. This sight drove Hal over the edge and he felt his balls begin to churn.

"M-Mom..." he squeaked out meekly. She didn't even slow down though. In fact, she bobbed her head a little faster, her warm mouth sliding over the head and first few inches while her hand pumped the rest. It was all too much, and Hal felt his dick spasm and spurt after spurt of hot cum shot into his mother's mouth. To his surprise, she swallowed it, before finally releasing his cock from between her lips.

"Mmm. You taste good, sweetie," Emma cooed.

She got back up to her feet, and pushed Hal back onto the bed. He watched in awe as she unzipped her skirt and let it fall to the floor. Her panties matched the bra, tiny little pink bows emphasizing the white lace. He also caught sight of the tips of her black stockings, hugging her thighs so perfectly.

"You've only ever smelled and tasted me on my panties. How would you like the real thing?" Emma asked, smiling sweetly.

Hal gulped. Even though he'd had the most intense orgasm of his life to date, he was still plenty horny, and unable to refuse the offer.

"Y-Yes please," He responded.

Emma's smile widened as she reached behind her back. She unclasped her bra and let the straps slide down her shoulders, before she let the entire thing fall off. For the first time Hal got a good look at his mother's breasts. They were supple and perky, even for their size, with pink nipples that stood out, already hard. His gaze only lingered here a moment, as next she hooked her thumbs in the sides of her panties and turned around, bending over and sliding them down her legs. He watched as her completely shaven pussy came into view. His cock gave a twitch at the sight. The pink lips were already glistening.

Remaining in her black thigh high stockings and heels, she crawled up onto the bed and mounted her son's face, hovering her pussy just inches away.

"Go on, honey. Smell it. Taste it. Fulfill your fantasy," she cooed, running her fingers through his hair.

Hal needed no further invitation. He inhaled deeply and immediately his cock gave another twitch. If the smell lingering on her panties was one thing, it was nothing compared to the real deal. It was so much stronger now, and even better than he'd imagined. After another moment of enjoying the aroma, he lifted his head and stuck out his tongue, nimbly flicking it across her clit. He felt her fingers tighten in his hair as he did, and heard her moan.

"That's it baby, just like that," Emma purred.

Hal opened his mouth wider, letting his tongue run the length of her slit. The flavor was so much more potent than what he'd ever gotten off her panties, and he loved it even more than the smell. His eyes nearly rolled back in his head as he pushed his tongue into her hole as far as it would go, lapping up every last ounce of fluid he could.

Emma began to gyrate her hips instinctively now. Hal moved right along with her, alternating between delving his tongue deep within her pussy, and suckling her clit. As he feasted on his mother, his cock slowly became hard once more.

"Keep going, keep going, keep going..." Emma began to repeat, moaning and gyrating her hips down against her son's face.

He latched his lips around her clit and flicked his tongue across it repeatedly. He thought she might suffocate him as she pressed her pussy against his face, and he felt his face moisten as he brought his mother to orgasm. She slid down his body, kissing her son deeply for the first time. Their tongues intertwined and she could taste herself on him.

"You're good at that," Emma said, kissing all over his face, trying to clean it of her juices. "Have you ever been with a woman before?"

"N-No.." Hal admitted sheepishly.

As she continued to kiss his face and neck, Emma began to rub her pussy up and down her son's dick, slicking it with her thoroughly moist slit. Hal moaned. The heat emanating from it was almost unbearable. After a few moments of this, she reached down, positioning her son's cock at her entrance, and with another deep kiss, she slid down. Hal moaned into the kiss as he felt his mother's pussy envelop his cock; tight, wet, heated walls clinging to every inch of it.