Down the Rabbit Hole

"In another moment, down went Alice after it, never once considering how in the world she was to get out again." -Lewis Carroll

Chapter I: Opportunity

Zack considered himself an average guy. At 23 years old, he worked a steady job in IT, had his own place, and was fairly fit and healthy. The only thing that stood out was his love of stockings.

He'd gravitated towards adult films featuring women wearing them, realizing that he enjoyed seeing them in them rather than being totally naked. But after a few years of this, it awakened a sudden desire in him.

He realized he wanted to wear them himself.

Being too nervous to go out and buy them in person, he had decided to order several pairs online. On the day he knew the package would arrive, he hurriedly rushed home from work to find the box on his doorstep. He snatched it up and headed inside his apartment, locking the door behind him.

He quickly stripped out of his work clothes, getting completely naked. Ripping open the box, he peered inside. There were several pairs of stockings; one white, one black, one fishnet, and one rainbow-striped, all thigh highs.

He selected the pair of black stockings, sitting down in his computer chair and setting the box down next to the monitor. He leaned over, slipping one of them up his right leg until the lace at the top snugly fit around his thigh. He took a moment to appreciate the feel and run his fingers over the fabric, and his cock began to grow.

Zack then took the other, sliding it on until both legs were encased in the sheer, black fabric of the nylons. He ran his hands up and down his legs, his cock now fully erect, just from the feeling and the kinkiness of it.

He stood up and walked into the bathroom, looking at himself in the full-length mirror. Being a fit, modern man, he trimmed regularly and so his figure was rather feminine. He had jet black, neatly trimmed hair and emerald green eyes. He admired the look of the stockings on his legs, and the feeling of the fabric clinging to his skin.

"I can't believe I'm doing this," he whispered to himself.

Taking another moment to admire the look of the stockings on his legs, he wrapped his fingers around his cock and began to pump. He moaned, his eyes fixated on the nylons. He'd never once considered crossdressing before in any capacity, so this made him hornier than he'd ever been up to this point. He thought he'd need to watch a lewd video to get off, but just the sight and the feel of the stockings on his legs was enough.

His hand became a blur over his cock as Zack felt himself approaching orgasm. He lurched forward slightly and let out a low, long moan as spurts of cum shot forth, landing on the mirror. He stood there, breathing heavily and staring at his reflection, the lower portion now stained with his seed.

"Best orgasm ever." He muttered to himself, before cleaning up the mirror and stripping back out of the stockings.

-

The next day, Zack was still so thoroughly turned on by the thought of wearing stockings that he decided to wear a pair to work. He settled on the pair of fishnet thigh highs, slipping them up his legs and admiring them before pulling his pants on over them.

Most of the day turned out to be uneventful, until lunch when a coworker decided to sit with him.

Her name was Brandi. She was a secretary to one of the higher-ups in the company, and the two had only ever spoken in passing before now. She was a gorgeous young woman, only 21 years old. She had straight, blonde hair that she kept up in a neat ponytail, and her blue eyes were bright and sparkly. She wore a white, button up blouse and black pencil skirt, along with black stockings and heels. Zack had always taken notice of her stockings, but of course said nothing of it.

"How's it goin' today, Zack?" She asked, taking a seat at the table across from him.

"Nothing out of the ordinary. Another boring day in the office," he replied, trying desperately to think of something more interesting to say.

"So um, I know this is a personal question but...do you have a girlfriend?" Brandi asked hesitantly.

"What? Er, no. No I don't. Do you?" He asked mindlessly.

'Do you?' he thought to himself. 'Why would you say that?!' To his surprise, Brandi giggled.

"Not since college." She said.

"O-Oh. Well then," Zack said, clearing his throat. Just the thought of this vivacious young lady with another woman made his cock twitch.

"I was wondering if maybe you wanted to go out after work for a drink."

"I'd love that!" He replied, perhaps a little too fast, though Brandi still didn't seem deterred.

"Great! Meet in the lobby at 5?" She asked, standing up so that Zack got another great glimpse at her black thigh highs.

"Definitely," he replied, trying his best not to stare.

Chapter II: Syntax

Zack couldn't wait for 5 to roll around, and as soon as it did, he clocked out and rushed to the lobby. Brandi was already there, little black purse slung over her shoulder. She smiled as he approached.

"I was thinking maybe we could try Vizzini's, that new bar just a few blocks away."

"That sounds great, it's only a block away from my apartment." Zack said, trying to contain his excitement. He'd had several girlfriends in the past but the last year or so had been quite a dry spell, so this was his first actual date in a long time.

The pair traversed the few blocks to the bar and took a seat at a booth inside. Within moments a waitress approached. She was tall and slender, her work uniform consisting of a black skirt and green blouse. She had fiery red hair that hung down well past her shoulders, and her already impressive height was boosted by the three-inch heels she wore. Brandi gasped.

"Hannah?!"

"Brandi!" The waitress squealed.

The two hugged before Brandi sat back down next to Zack, who was beginning to feel a little out of his element.

"Zack, this is my friend from college, Hannah. Hannah, this is my coworker, Zack."

"Oooh, he's cute," Hannah said with a sly grin.

"Hannah!" Brandi chastised her friend with a laugh.

"Alright alright. I'll leave ya alone. What would you like to drink? They're on me."

"Mojito for me," Brandi answered, eyeing her college friend as she in turn was looking over Zack.

"Crown and Coke for me, please," Zack requested.

"I'll bring 'em right over," Hannah replied before disappearing to fill the drink order.

Brandi leaned close to Zack and whispered.

"That's my girlfriend from college."

"Her? W-Wow," Zack whispered back, amazed. He tried his best not to immediately fantasize about the two together but failed spectacularly, and felt himself getting hard. He was suddenly very grateful to have a table to help hide his erection.

"You sound so impressed," Brandi laughed.

"Oh er...sorry. That just...I mean the two of you...together..." Zack stammered, desperately trying to keep his cool. Brandi laughed again.

"Stop worrying so much. It's totally fine. I haven't been with a woman since college. I kind of miss it, honestly."

Zack felt his heart sink and nodded his head, but luckily didn't have to reply as Hannah reappeared with their drinks. She set each down on the table with a napkin, and both Zack and Brandi's had her phone number scrawled across it.

"Don't be a stranger, you two," Hannah winked and moved away to handle other customers.

Brandi snickered at the napkin, but nevertheless folded it up and placed it in her purse. Zack absentmindedly picked at the edge of his, thinking maybe she'd rather have her than him. Brandi seemed to notice this though, and edged closer to him in the booth. He felt her hand on his thigh and his eyes widened.

"Don't worry, Zack. I'm bisexual. And I wouldn't have asked you out with me if I didn't think you were hot, too."

Zack felt his cheeks grow warm at the compliment, and the hand on his thigh. He fidgeted in the booth a bit.

"Th-thanks," Was all he could think to say.

The two continued to talk for a long while, sipping their drinks and discussing everything from work to home life. It turned out that Brandi also lived alone, and like Zack, hadn't been in a serious relationship in a long time.

As they finished their drinks, Zack suddenly felt Brandi's hand on his thigh again. This time it was only inches away from his crotch, and he gulped. He felt hot, from her touch and the drink he'd consumed. She edged closer to him, leaning over and whispering in his ear.

"How about we..." she paused, groping his crotch through his slacks. He nearly jumped out of the booth but tried his best to remain calm and appear normal. "...go to your place? You said it's real close, yeah?"

Zack gulped. He could feel himself getting hard as she caressed his bulge. He nodded excitedly. "Check please," he called out, his voice breaking as if he were going through puberty. This gave Brandi another laugh.

Brandi took him by the hand and led him from the booth. She blew a kiss towards her college friend and said, "I'll call you later, Hannah."

Zack and Brandi were both so excited they jogged the distance from the bar to his apartment. He fumbled with his keys and threw open the door, and the minute he did, Brandi was all over him, kissing him deeply and slithering her tongue into his mouth. Her arms wrapped around his neck and he in turn wrapped his around her waist. Their bodies ground together in a primal lust as he kicked the door shut and the two moved awkwardly in tandem further into the apartment.

As they stumbled into the bedroom, Brandi shifted her arms between them and began unbuttoning her blouse. Zack helped push it off her shoulders and she threw it to the floor. Between their impassioned kisses, he managed to get a glimpse of her bra, a sexy white lace number with a floral pattern that was mostly see-thru. He began to grope the soft flesh of her breasts through the bra as they continued to make out, lips locking and tongues slithering across one another.

Brandi then unbuttoned his shirt, and he let it slide off and fall to the floor with hers. He then felt her fingers on the clasp of his pants and a sudden realization hit him.

He was still wearing the stockings.

He panicked and reached down, grabbing her hands and holding them within his own.

"H-Hey, wait a sec."

Brandi seemed insatiable though and managed to slip free from his grasp. Before he knew it his pants were undone and she yanked them down quickly, exposing the thigh high fishnets.

An awkward silence fell upon the room. Brandi took a few steps back, looking Zack up and down, whose cheeks were now flushed. His erection began to wane from the embarrassment of being caught.

"I-I can explain," he began.

"Please do," Brandi responded, far too calmly, which made Zack more nervous.

"I uh...I uh...um..." Zack coughed. He desperately tried to think of an excuse, any excuse that would make sense.

Brandi crossed her arms over her chest, still only covered by the bra. She wasn't making any move to put her blouse back on or try to leave, and Zack was having a hard time gauging her as a result.

Zack sighed and gave up trying to think of an excuse. He looked down and spoke quietly. "I just really like stockings."

A grin crept across Brandi's lips. She unzipped her skirt and let it fall to the floor, stepping out of it, revealing a set of panties matching her white lace bra, and the tops of her thigh high black stockings.

"I bet you love the look of these then," she said, placing a hand on her hip.

Zack slowly looked up, and right away he began to harden again. Seeing her stockings in their entirety now, not to mention the heels that emphasized their look, gave him a second wind.

"You're...not weirded out or anything?" He asked quietly, unable to stop staring at her sexy figure.

"I'll admit, I've never been with a guy in women's clothing before but, it is pretty damn sexy. I like stockings myself."

He felt like a weight had been lifted, hearing that. He was suddenly very horny again, realizing that he was about to fulfill his fantasy of having sex in stockings, while his partner wore them as well.

Brandi took a few steps forward and pushed him so that he fell back onto the bed. He lifted his head and watched as she reached behind her, unclasping her bra and letting it fall to the floor with the rest of her clothes. Her breasts were just the perfect size, not too big, not too small, a perky, well-rounded 36C. At the center were pink nipples, already hard.

She then hooked her thumbs in the sides of her panties and pulled them down, letting them fall so she could step out of them. Now she stood before him, dressed in nothing but a pair of black thigh high stockings andheels. He too was completely naked, save for the fishnets on his legs.

Brandi sauntered over to the bed, crawling up on top of it and slithering up his body until he felt the heat of her pussy on his dick, which was now achingly hard. It twitched in response. She kissed him passionately, thrusting her tongue into his mouth once more. As she did, she began to grind her hips downward, and Zack felt his dick slip in between her pussy lips. They were already moist, and the feeling made him moan into the kiss.

She continued like this for a time, rubbing her pussy up and down the length of his cock as they kissed, their stockinged legs rubbing together and sending tingles down Zack's spine.

Finally, Brandi sat up so that she was sitting on his cock, her wet folds clenching the sides of it. She slid along the length of it a bit more, smiling down at Zack as he looked up at her in awe.

She lifted herself up, reaching down and pulling his cock up so that the head rested against her heated opening. Zack ran his fingers along the tips of her stockings as she slowly slid down his length, her hot, wet pussy engulfing the entire thing.

Brandi came to rest against his pelvis and remained there for several moments, just enjoying the feeling of his cock filling her up. She wanted more though, and eagerly began bouncing up and down. Zack watched as his dick, now shining with her juices, disappeared into the pink tightness every time she brought her hips down.

He couldn't believe this was happening. Just the night before he'd settled in for a lonely night of wearing women's stockings and masturbating, and now here he was in a pair of fishnets while this gorgeous blonde woman bounced on his cock, wearing black thigh highs and heels.

He couldn't stop running his fingers over the fabric of her nylons as she continued to thrust her hips downward, her tight cunt engulfing his throbbing shaft with each pass. Although she was very tight, the wetness made it easy for his dick to sluice in and out, and he groaned as he felt her walls clenching him, bringing him closer to orgasm.

Brandi began to buck her hips faster. She leaned back slightly, giving him an even better view of his rock hard cock disappearing into her wet pussy. She balanced herself on his legs as she continued to bounce, her fingers gripping the fishnets.

The sensations were just too much for him. Her stockings rubbing against his own, their hands caressing the nylon fabric that encased each others legs, and most of all the tight tunnel that was clenching him. Zack began to thrust his hips up in time with her movements, and moaned as he felt his cum pulse deep into Brandi's dripping wet hole. At the same time he could feel her muscles contracting as she had her own orgasm, her pussy clenching him tightly and milking him dry.

She collapsed on top of him and the two shared another intimate kiss. Finally she slid off of Zack, laying beside him, and placed her arm over his chest. He lay there, catching his breath, still in disbelief at what had just happened. Brandi too took a moment to catch her breath, but she was the first to speak.

"Fuuuuuuck that was hot. I never thought about a guy in stockings before but you definitely have the legs for them."

"Thanks," Zack replied breathlessly. "You do too."

Brandi rolled on her side so that she was looking at him as they spoke. Zack turned his head to meet her gaze.

"Have you ever thought about going further?" She asked curiously.

"What do you mean?"

"Like dressing up like a woman. Wearing panties, a bra, skirts, dresses. That kind of thing."

Zack shook his head.

"Not really. I just really love stockings, they're so sexy and they feel so great. To be honest, I only put a pair on for the first time yesterday. Today is only my second day in them."

Brandi considered this for a moment before replying.

"Well you can wear them anytime we're together." She smiled coyly. "We should do this again tomorrow."

Zack excitedly agreed.

"Definitely."

Chapter III: Old Habits

The next morning, Zack decided to again wear a pair of stockings to work, this time in anticipation for his second date with Brandi. He decided on the rainbow-striped pair, and was excited to hear what she'd think of them.

The day at work seemed to drag by until lunchtime had arrived. He got up from his desk and began making his way towards the cafeteria, but as he passed by the boss' office, he was suddenly yanked inside.

Brandi closed the door behind him and locked it, smiling. She was in her usual secretarial outfit of a white blouse, black skirt, and the trademark black stockings and heels.

"Where's Ms. Granger?" He asked, looking around the office.

"She took a half day, so I figured we could borrow her office. Fucking you in those stockings last night STILL has me worked up. I want more."

"Well I'd hate to disappoint," Zack said with a smile.

Their hands suddenly became a blur as they worked to undress each other again. First tops, then bottoms, until they were left in just their undergarments. Today Brandi had on a sexy white strapless bra and a black satin thong. Of course, Zack's favorite part of the ensemble were the thigh high stockings and heels. He stood in just his blue boxers and rainbow thigh highs.

"Oh those are just too adorable," Brandi giggled. She dropped to her knees, rubbing her fingertips along the fabric, which made Zack moan.

She slipped off his boxers, setting his hard cock free, before taking it in her mouth. He moaned again as her soft lips enveloped his meat, slipping all the way down, trapping the length of it in her warm, wet mouth, before slowly sliding back up so that barely more than the head remained. She repeated this, her hands still caressing his legs, clad in the rainbow stockings.

Zack placed a hand gently on her head, running his fingers through Brandi's silky blonde hair as she gave him the best blowjob of his life. Her mouth felt so good, with her soft lips wrapped so snugly around him as they worked their magic. All the while he could see her hands running along the length of his stockings, which enhanced the image and brought him even closer to orgasm.

"I'm about to cum," he warned Brandi with a strained whisper.

She continued to bob her head however, sucking his dick even faster, slurping it deep into her mouth and slobbering all over it as it suddenly throbbed and shot several jets of thick spunk into her mouth. She swallowed his salty load and released his cock with a pop, licking her lips.

Though he'd gotten off, he still wanted Brandi to as well, and so he leaned down, taking her hand and helping her stand on those sexy black heels. He led her over to their boss' desk and slid her panties off while she unclasped her bra. He then helped her sit on the edge of the desk as it was his turn to sink to his knees.

Her pussy was completely shaven, and this was the first time he'd gotten an up-close look at it. The aroma reminded him of fresh-cut roses, and he licked his lips in anticipation, before pushing his head between her legs and latching onto her soft folds. He ran his tongue through them, savoring the sweet flavor that washed over it.