Down the Rabbit Hole

He could feel Brandi's hands on his head, her fingers running through his hair as he ate her out with abandon. His tongue traversed the soft folds, deep into her pussy, and up to her sensitive clit. He was enjoying the sensation almost as much as she was.

While he worked, he ran his fingers over her black stockings, occasionally glancing sideways so he could admire them wrapped around her thighs. Before long she began to buck her hips, pressing her pussy against his face as she came, her entire body shaking from the intense feeling of the orgasm.

Zack stood up and Brandi leaned in to kiss him, tasting herself on his lips and tongue. After a moment of this, she lay back on the desk and spread her legs.

"Fuck me, baby," she said in a sultry voice.

Zack needed no further invitation. He'd gotten hard again while going down on Brandi, and was more than ready to keep going. He stepped close to the desk, grabbing her ankles and placing them on his shoulders. He loved the feelings of her stockings against his skin as he placed his member at the edge of her opening and pushed in. He sighed in pleasure as the lips stretched around his cock, until her dripping wet pussy had swallowed the entire thing.

He began to pump in and out of her quickly. Both were having trouble keeping their moans down to an acceptable level. Zack stared down, watching his dick disappear into her tight cunt, while her shapely legs wrapped in black nylons rested upon his shoulders. Below that he could see the rainbow nylons still on his legs, and the sight of both pairs made him pump even faster.

He was thrusting harder into her now and Brandi was clutching the desk, groaning in pleasure. She arched her back as her body shook from an intense orgasm. Zack could feel her tight muscles contracting and squeezing his cock as this happened, driving him to his own orgasm, his cock releasing its payload of hot, white cum for the second time today.

With a long, low moan, he slowly slid out and helped Brandi up. She immediately fell to her knees again, hands finding his rainbow stockings as she slurped his cock back into her mouth, cleaning it of her juices. Afterwards, she stood up and they kissed again.

"I have no idea why I waited so long to ask you out," Brandi said breathlessly.

Zack smiled at this.

"I feel like I should be thanking you. I mean, you're totally cool with the stockings and everything."

"Well of course I am. They're sexy and feel great," Brandi giggled, spanking his ass before gathering up her clothes.

"I've got a girls night planned with Hannah tonight, but how about we get together again this weekend? Say Saturday afternoon?" Brandi asked with a coy smile.

Zack nodded excitedly. "That'd be great."

-

That night, Brandi and Hannah went out for dancing and drinks. After a few hours of this they retired to Brandi's apartment. Brandi was clad in a little black dress, with a black thong and strapless bra on underneath, and a pair of two inch heels. Hannah was dressed in a cropped t-shirt that was cut off halfway down her midsection, exposing her toned tummy. She also had on a red, plaid miniskirt and strappy red heels.

The two sat on Brandi's sofa to relax and catch up. They had both had several drinks and were feeling no pain.

"I'm so glad I ran into you again," Brandi said with a smile.

"Me too. I haven't had this much fun since...well, since we were in college."

Brandi noticed that Hannah was staring at her body, her green eyes examining every inch and curve as they spoke. An idea suddenly crept into her mind.

"We did have a lot of fun in college...it was my first time with a girl, y'know," Brandi said, grinning.

"Mine too." Hannah replied, licking her lips.

Brandi edged closer to her friend, placing a hand on her bare thigh.

"We could relive that time," she whispered.

Hannah shuddered excitedly at the thought. She was already turned on from the dancing and the drinks, but was unsure if Brandi would still be up for this.

"But how about, if we do, we let Zack join us? We always used to talk about trying a threesome."

"Zack is pretty hot, too," Hannah said, considering it for a moment. "I'm in."

"Great!" Brandi exclaimed happily.

"But I've gotta have you now," Hannah said hungrily. She climbed onto and straddled Brandi's lap, leaning in to kiss her passionately. Brandi returned the kiss, running her hands along Hannah's exposed sides.

Brandi took the initiative now, lifting Hannah's shirt and quickly unclasping her bra, tossing them both away. She took her college friend's right nipple into her mouth, gently grazing it with her teeth. She then did the same with the left, while Hannah ran her fingers through Brandi's shiny blonde hair.

Hannah moaned, both of her copper colored nipples achingly hard at her friend's moist lips and tongue. Suddenly, Brandi groped her ass and stood up, holding her. Hannah wrapped her legs around her waist for balance as Brandi carried her into the bedroom. She dropped Hannah onto the bed and slid on top of her, pressing their lips together once more and parting them so that their tongues met.

Again Brandi worked her way down Hannah's body, kissing her breasts and suckling on her nipples, before moving down further. Hannah lifted her hips off the bed so that Brandi could slip off her skirt and panties in one swift motion, leaving her in nothing but the red heels.

Hannah's pubic hair was neatly trimmed, with only a small amount above her slit, and it was fiery red just like the hair on her head.

"God I've missed this," Brandi said. She lowered her head in between Hannah's thighs and stuck out her tongue, running it along the length of her slit. Hannah moaned, her fingers again finding their way into Brandi's hair.

Brandi began to lap at her friend's pussy. It tasted as good as she remembered, and she wanted more. She began to push her tongue deep into the hole, getting a stronger flavor as she wriggled it within.

Hannah however tugged on Brandi's hair, pulling her head up. Brandi pouted, her face shiny with nectar.

"I want some too," Hannah demanded. Brandi slid down the straps of her dress and began to take it off as Hannah sat up to unclasp her bra. She then stood to slip out of her thong, so that now she too was only left in her heels.

Crawling back up on the bed, she positioned herself above Hannah in a 69 position. Almost immediately she felt her friend's tongue pressing against her pussy, already wet and hot. She thrust her head back down between Hannah's legs and resumed eating her out as well, suckling the sensitive little clit into her mouth.

Both girls feasted on each other's wet pussies, savoring the flavors and warmth on their tongues. It wasn't long before each came, their body shaking from the orgasm. Hannah still hadn't had enough however.

As Brandi slid off of her, Hannah turned around and slid closer so that her left leg was beneath Brandi's, and her right was above. She pulled Brandi in closer by the hips so that their pussies, still heated and wet, were rubbing against one another. Brandi moaned.

"Oh god, I'd forgotten how good this felt," she moaned, holding onto Hannah's knee for support.

Hannah gyrated her hips so that they rubbed together, the wetness making them glide easily against one another. Their clits connected and Brandi felt as if sparks were flying. The two found a rhythm together like this. The heat and wetness felt amazing to both of them, and each felt another orgasm fast approaching.

Their hips began to move faster as they ground against one another, and finally, Brandi felt herself orgasm for the fourth time today.

"Fuuuuuuuuuck," she moaned.

Hannah continued to work herself against Brandi for a few more seconds until she too came. Her body shook until it was over, at which point she pulled Brandi in for another kiss. Then the two collapsed on the bed, laying in each others arms.

"We are gonna blow Zack away Saturday," Brandi whispered with a giggle.

"Can't wait," replied Hannah.

Chapter IV: Duty

Zack and Brandi both arrived for work excited that Friday. Zack merely thought he was going to get lucky again, while he and his insatiable blonde girlfriend both wore stockings. Brandi however, was excited for the surprise she knew was in store; not only was Zack going to get lucky in stockings, but he was going to get lucky with not one but two lusty ladies.

Midway through the morning, Brandi approached Zack's desk with a concerned look on her face.

"What's up?" He asked curiously.

"Ms. Granger wants to see you. She didn't say what about. She sounded weird, though."

Zack gulped.

"You don't...think she knows?" He whispered.

"How could she? We were the only two in that office. I'm sure it's nothing."

Zack stood and took a deep breath, before proceeding to his boss' door and knocking.

"It's open," came the reply from within.

Zack creaked open the door and slowly stepped inside. Sitting behind her desk was he and Brandi's boss, Harley Granger. At only 30 years old, she seemed almost too young to be the boss, but she'd always done her job well. She had straight, light blonde hair that went several inches past her shoulder, though at the moment she had it pulled up in a neat pony tail, so that only her bangs remained framing her face. Her brown eyes seemed timid, but everyone knew she was anything but. She was dressed in a knee-length black pencil skirt, red button-up blouse, and a black ladies suit jacket. Beneath the desk, she had on a pair of black thigh high stockings and sensible two-inch heels.

"Close the door and sit, please," she said plainly.

Zack gulped again, trying to hide his nervousness as he shut the door. He slowly walked forward, moving around the chair in front of her desk before sitting in it, folding his hands in his lap.

Harley stared at him for a long time, and neither of them said a word. Zack was having trouble keeping his eyes on hers, feeling more nervous by the second. Finally, she broke the silence.

"This is a very nice desk, wouldn't you say?"

Zack slowly looked down to her desk, remembering Brandi being firmly planted on it the day before.

"I think so, yes," he responded quietly.

"Is there anything you'd like to tell me?" Harley asked calmly.

"N-No," Zack replied, trying to sound confident.

"Hm," Harley said simply.

She turned her computer monitor around so that Zack could see it, and his eyes went wide. On the screen was Brandi laying on the desk, with him pistoning in and out of her. His jaw dropped. He then realized the angle was from above the desk and his eyes traveled upwards, until he saw it. On the bookshelf behind the desk, mostly obscured by books and knick-knacks, was a camera.

"How long have you been a cross-dresser?" Harley asked. Her voice still sounded strangely calm.

"C-Crossdresser?" Zack gulped again, and shook his head. "N-No. I'm not. I just like stockings, that's all."

"Stockings are for women, so I'd still call that crossdressing, sweetie."

Zack remained silent, unsure of what to say. Harley's eyes returned to the screen for a moment before she turned the recording off. She then stood up and walked around her desk, leaning against the front of it, just feet away from Zack.

"I suppose you like these then?" She asked, before raising the hem of her pencil skirt up just far enough so that he could see the lace pattern at the tops of her black thigh highs. His cock gave a little twitch.

"I uh...I uh..." he stammered.

Harley laughed.

"Don't worry. Your little fetish is safe with me, as is your job, if you do what I say."

"Ma'am?" He squeaked out.

"You see Zack, I have a secret of my own," she paused and lifted her skirt up higher so that it was bunched up around her waist, and through her black lace panties he could see a bulge. His eyes suddenly widened.

"I think your little fetish is sexy. It's a shame you don't wear more women's clothes, I think it'd look good on you," Harley spoke as she slid the fabric of her panties aside, letting a natural, half-erect cock bounce free.

Zack had never been attracted to men before, and had never considering any kind of sex acts with them. But he had to admit Harley was sexy, and something about this turned on him, though he still felt uncomfortable.

"I uh..." he stammered again.

Harley stepped forward and moved close to Zack, so that her cock was now only inches away from his face.

"Just give it a little kiss, and you and that little blonde slut get to keep your jobs, and I won't tell anyone about your little secret. C'mon darling, I know you want it," she purred.

Zack still felt uncomfortable, but he also knew that some part of him did want this somehow. He had never once entertained the thought of sucking a cock, or even a shemale for that matter, but here one stood before him now, with her semi-erect member just inches from his face. After a moment of hesitation, he leaned his head forward, and place a soft kiss on the head. Harley shuddered.

"Mmmm. That feels nice. You have really soft lips."

Zack repeated the kiss again, this time parting his lips just enough so that his tongue could flick across the slit. Harley moaned again and he felt her fingers in his hair.

He shyly raised his hands and placed his fingertips on the lace tops of her stockings. Harley couldn't help but smile.

"You really do love stockings, don't you?"

Zack nodded his head silently before giving her head another little kiss. He parted his lips a little further this time, taking just the tip between them. It felt spongey and soft, despite the fact she was getting fully erect and hard from his attention. He grew bolder, and opened his mouth, taking the entire head within now.

A tiny droplet of precum leaked out and a salty taste washed over his tongue. Zack found that he enjoyed the flavor, however. He slid his lips further down her shaft, managing to take about half of it into his warm, wet mouth until his gag reflex triggered.

He coughed and slid his head back up for breath, realizing he wouldn't be able to take the entire thing. Harley didn't seem to mind though, as she simply stood there, happily watching him work. He raised his right hand, wrapping his fingers around the bottom portion of her cock as he placed his lips back around the top half. He moved his mouth and hand in tandem, simultaneously jerking her off and blowing her at the same time.

Harley moaned again. The feeling of his nimble fingers and warm mouth wrapped around her cock gave her tremendous pleasure, and she knew it wouldn't be long before she came.

Zack's head and hand became a blur as he now expertly worked his boss' cock. He'd grown used to the feeling and the size, and was actually enjoying it. He'd grown hard in the process, his own member straining against his boxers. Regardless, he continued sliding his lips up and down Harley's cock, his hand pumping what he couldn't take between them. All the while with his free hand he continued to caress her stocking-clad legs.

"Oooooh god. Don't stop, don't stop...oh Zack don't stop!" Harley repeated, clutching his head tightly as spurt after spurt of thick white spunk shot into his mouth. It took Zack by surprise at first, but he found that he enjoyed the taste, and managed to swallow most of it, though a tiny amount dribbled out of the corner of his mouth and down his chin.

As he released Harley's cock, she leaned down and licked off the little bit of seed that had escaped his mouth, before kissing him, shoving her tongue past his lips. He kissed her back, his head swimming with disbelief over what he'd just done.

Harley slid her cock back into her panties and smoothed out her skirt before moving to sit behind her desk again.

"Very good work, Zack. You're a natural cocksucker."

His cheeks flushed at this. Though he had just done it, and quite happily, he still felt a twinge of shame at being called that.

"I know you have plans for Saturday already, but this Sunday I want you to come to to my suite. How does 2pm sound?"

"I'll be there," he replied, as if he had much of a choice.

"Excellent. You may return to work now."

Zack stood up and slinked out of the office, quickly returning to his desk.

-

The rest of the day dragged by without incident, but Zack had trouble concentrating on his work. He'd gone from having a simple stocking fetish to fucking his new girlfriend while they both wore stockings, and then sucking his shemale boss' cock. When the time to leave had finally arrived, he stopped by Brandi's desk.

"Want me to walk you out?" He asked politely, wondering if he should tell her about Harley.

"No, Ms. Granger said she wanted to see me before I left today. Speaking of which, how did it go?"

Zack gulped. She wanted to see Brandi too? He again wondered if he should warn her, but thought better of it and shook his head. "Oh it was fine. Um, nothing really. I've got to go, I'm sure it'll be alright. See you Saturday, yeah?" He said, before departing in a hurry.

Brandi watched him leave suspiciously, raising a brow. After she'd finished straightening up her desk, she entered Harley's office, who was once again sitting behind her desk.

"Come in and close the door." She said calmly.

Brandi obeyed and moved closer to the desk; the same desk she'd gotten fucked on just a day earlier.

"So I understand you and Zack are an item now," Harley began.

"I suppose you could say that," Brandi replied, clearing her throat nervously.

"You suppose, do you?" Harley chuckled.

Again she turned her monitor around, and Brandi stared at the screen. She saw the same image Zack had earlier; her laying on that very desk, getting fucked hard and fast.

"You and your stocking obsessed boyfriend seem to be a very active couple. Couldn't wait til you got home?"

"Ms. Granger, I'm so sorry," Brandi began, as the monitor was turned back around. "It'll never happen again, I swear."

"Now now, let's not be hasty here," Harley said calmly, standing up from behind her desk. She moved around in front of it to face Brandi, smiling. "I'm willing to let it happen again...if, we could work out a little deal."

"A deal?" Brandi asked, fear fading into curiosity.

"I'd like to have you in that same position."

"I er..." Brandi thought about it for a moment. Harley was rather attractive, and after her romp with Hannah, she was definitely ready for more girl-girl action. "Do you...have a strap-on here at work or something?"

Harley laughed.

"Oh no, Brandi. Something much, much better."

For the second time today she hiked her skirt up around her hips and pulled her panties aside, letting her cock spring free. Brandi gasped, staring at it.

"You have a...so that means...you're?"

"I'm the best of both worlds, sweetie," Harley responded with a wink.

"It's...I mean...I've never been with...that's kind of hot though," Brandi mumbled.

"I'm glad you think so. Are we on, then?"

"If I get to keep my job, sure."

Harley laughed again. "Of course you get to keep your job. Might even get a raise."

Harley picked Brandi up, setting her on the desk. She slid her skirt up like she'd done to her own, and pulled Brandi's little black thong aside to reveal her shaven pussy. Harley took hold of Brandi's stocking-clad knees and knelt down just as Zack had done the previous day. She inhaled deeply, and then leaned forward, sucking Brandi's clit between her lips.

Brandi began to moan immediately. Like Zack, she'd never considered being with a shemale and yet she was extremely turned on by the possibility. She felt herself growing wet with ease as her boss' tongue explored her nethers, delving deep within her and flicking over her sensitive clit.

Once she'd gotten nice and wet, Harley stood up and easily slid her cock into Brandi's tight pussy. She groaned at the tight, warm feeling, the pink walls clenching her member as she thrust deeper.