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.
