Down the Rabbit Hole

He looked up at Harley, who was simply watching him expectantly. He brought his gaze back down to her panties, looking at the curves her member created in the fabric. He finally reached up and pulled the panties aside, so that Harley's cock was freed of it's confines. He leaned it and kissed the underside of it softly with his pink-painted lips, and Harley moaned.

"Oh that's nice, Jill," she said sweetly. "I knew you couldn't wait to have more of this."

Zack was too turned on at this point to be embarrassed any further. He'd dressed up in sexy white lingerie and was now being called Jill, and he didn't even care. All he cared about was this vivacious shemale sitting in front of him, and her growing member in his face.

He opened his mouth and wrapped his lips around just the head, running his tongue all along the surface. Once it was nice and wet, he brought his head down further, enveloping more of her cock in his warm, wet mouth.

"Oooh Jill," Harley purred. She brought one hand down from the back of the sofa, caressing his cheek.

Zack began having the same issue as the first time, only managing to take half of Harley's thick meat before his gag reflex kicked in. As a result, he wrapped one hand around the bottom portion of her dick, pumping it as he continued to slide his lips over the top half. All the while his free hand was still on her leg, rubbing the black stocking.

"Oh baby, I think you can do better. You're just not trying hard enough. Come on Jill, you're a better cocksucker than that," Harley said with a devious smile.

She grabbed a fistful of the wig hair, and managed to get some of his actual hair in the process, and proceeded to push his head down further. Zack's body convulsed as he gagged and tried to get used to having a cock in his throat. His mouth felt so full and he began to struggle to breathe, but finally Harley pulled him back up so that only the head remained between his lips.

He took a deep breath and found his head immediately thrust back down. This time it felt like his gag reflex was completely broken as he suddenly felt Harley's cock in his throat, and his lips pressed against her pelvis. Again she held his head here, until he began to have trouble drawing breath, at which point she again let him come back up for air.

"See Jill, I knew you could do it," Harley giggled.

She released her grip on his hair and Zack took an extra moment to catch his breath. He was now more confident in his ability though, and once he felt ready, he again slid his lips down the soft skin, taking a full third of it within before he had trouble. He found a rhythm, taking the majority of Harley's rock hard cock into his mouth. Saliva began to drip down his chin.

Harley suddenly stopped him however, and he pouted, his mouth feeling so empty now that there was nothing to fill it.

"Don't worry you little cockslut, we're not done. Not by a long shot," Harley said, devious smile still adorning her features.

She finally stood up, and brought Zack to a standing position with her. She turned so that her back was facing him.

"Be a dear and take this off, would you?" She asked, her voice sickeningly sweet.

Zack fumbled for a moment with the clasp of the bra before he managed to unhook it. Harley turned back around, slowly slipping the straps off her shoulders. She teasingly held the cups over her breasts for a moment before finally pulling the garment away, casting it off.

Zack stared hungrily at her breasts. They were just slightly bigger than Brandi's, with hard, copper-colored nipples. He licked his lips and Harley snickered.

"Go on. Have at them, Jill," she invited.

Zack lowered his head and wrapped his lips around her left nipple, biting it gently while he cupped the other globe of soft flesh with his hand. She caressed his cheek while he went to work on her breasts and rock hard nipples, ravishing them both in equal measure and kissing all over the tender flesh.

Harley took his head in both hands and lifted it up. He stared into her brown eyes as she leaned forward and pressed her lips to his. The two shared a passionate, intimate kiss, as their tongues found each other and entwined. Zack could smell her perfume, and the sweet scent perfectly complicated the smell of the incense.

Harley broke the kiss and wrapped her arms around Zack's neck now, staring into his eyes.

"Are you ready for more, Jill?" She asked in a tone barely more than a whisper.

"Yes ma'am," Zack whispered back. His head was swimming.

"Mmm, that's a good little slut," Harley purred. She took Zack's hand and led him into the bedroom, where Zack finally realized the scent of the incense was coming from. The room was immaculate. In the center was a king-size bed, covered in red silk sheets. Off to the side was what almost looked like an altar, with several sticks of lit incense in ornate, decorated holders perched on the top. Several candles surrounded these, their flames flickering. On the opposite wall was a closed door, which Zack figured either had to be a closet or master bathroom.

She led Zack and gently pushed him so that he sat on the edge of the bed.

"Get me nice and wet again, Jill," she commanded.

Zack leaned forward without hesitation, taking her cock back between his lips and sliding them over the soft skin. Once he'd thoroughly moistened it, she again withdrew from his mouth, this time pushing him back so that he lay on the bed with his stockinged legs hanging over the edge.

"Take off your panties," she said in a commanding, yet sultry tone. Zack obeyed, slipping the thong down his legs and catching it on one of the sexy white heels, before kicking them off completely. His cock was so hard it pressed against his belly.

Harley moved to the little shrine and unscrewed the lid off of a small jar. Zack could just barely make out the silhouette of a naked woman on the jar but nothing else. The shemale took some of the material from within and slathered it all over her shaft. As she returned to the bed, he could see it now shone with his saliva and the lube she'd applied.

"Time to make you feel like a woman, Jill," Harley said as her devious smile returned.

Suddenly, Zack felt a twinge of fear. He knew what was about to happen, but he realized he wanted it. It was a very conflicting feeling, even after all the events that led up this point. He had never considered going this far, and it never crossed his mind that it would progress to this, even after he'd donned the white lingerie and heels.

Still, deep down, he knew he wanted to feel the sensation. The fear however made him tense up, as he realized it was going to hurt at first, and this made him nervous. Harley however seemed to notice this, and the expression on her face turned softer as she began to run her fingertips along his white stockings.

"It's alright Jill. It'll only hurt at first. Then you'll love it."

Zack nodded and took a deep breath, trying to prepare himself for what was to come. The gentle touches on his stocking-clad legs helped him to relax as Harley stepped forward, pressing the slicked head of her shaft against his virgin hole. She was being extraordinarily gentle now, which he was definitely thankful for, as he felt the head slowly slip inside him. Right away he felt like he was being split in two, as his asshole stretched to accommodate it's new visitor.

Harley gave him time to become accustomed to having her head within before she slowly pushed another half inch inside. She could see him wince and knew that he had to get used to the feeling. "You're so sexy Jill, so tight," she encouraged him.

Zack could feel his ass opening up as she slid another full inch in, and a searing pain shot up through his spine. "It hurts," He whimpered.

"Sssh, it'll be alright, baby," Harley whispered.

She slowly slid another inch inside, and while she knew Zack was having trouble growing accustomed to having her thick member inside him, she felt nothing but pleasure as his super tight anus clenched her.

The pain was finally beginning to wane for Zack. As she slid more and more of her hard cock inside him, he began to enjoy the feeling of it filling him up. The pain slowly subsided and gave way to pleasure as Harley finally reached the brim, her entire length buried in his tight ass.

"See, that wasn't so bad, was it?" She cooed, staring down at Zack, dressed up as sexy virginal Jill, still in her white camisole, stockings, and heels.

Zack shook his head but remained silent. Even though it was beginning to feel good, he was still having trouble wrapping his head around the fact that his shemale boss' dick was now buried balls deep in his asshole.

Harley slowly, teasingly slid her length out until only the first inch still remained within the tight confines, before pushing back inside, the combination of saliva and lubrication making the tight tunnel feel moist and wet, delivering even more pleasure.

"Oh god," Zack finally let out a moan, unable to hold it in any longer as Harley fucked him. She began to thrust a little faster, pumping in and out of his tight ass. She grabbed his ankles and placed them on her shoulders so that she had a prime view of her cock disappearing into him. The white nylons felt heavenly on her shoulders, and she enjoyed seeing the heels strapped to his feet, right at eye level.

Zack was going into sensory overload. He could feel every last inch of the thick cock sliding in and out of his ass, as well as the soft nylons on his legs and the material of the camisole on his chest. He was rock hand himself at all the sensations, and more turned on than he'd ever been in his life.

"Fuck me, Harley," he whispered.

Harley giggled as she continued pumping deep into him.

"I knew you'd like this Jill, you little slut."

Just when he thought it could get no better, he felt her nimble fingers wrap around his cock. She began to jack him off in time with her thrusts, and he groaned, already close to the edge. Precum dripped out over her fingers.

"Oh Jill, you're so tight, I'm about to cum. Oooooh here it comes!" Jill shouted, pumping harder into his ass. After a few more rough thrusts, she felt her cock spasm and unload thick jets of cum deep inside him, his tight anal walls clenching her, milking her dry. As Zack felt his ass fill with the hot cum, it became too much, and he arched his back, shooting his own load across Harley's hand and his own stomach.

Harley leaned down, scooping up his cum with her tongue, then she lay on top of him, her cock still lodged deep within, and kissed him deeply, pushing his own cum into his mouth. He was so lightheaded he easily accepted and swallowed, kissing her back.

Finally, she slowly withdrew from Zack's thoroughly fucked ass and lay beside him on the bed, caressing his stockings.

"I think someone deserves a raise," she mused. "And perhaps a promotion to my personal concierge, as long as you're willing to dress the part."

Zack turned his head to look at her. He felt so fulfilled after everything that had just happened. He'd gone from a kinky threesome one day, to crossdressing and getting fucked in the ass the next. But now he was being asked to dress up like this in public.

"I don't know if I'm ready for that," he replied hesitantly.

"Take some time to think it over, Jill. Either way you know your job is safe, and you're welcome to come over any time you want." She kissed his cheek and snuggled up next to him. The gentleness of the situation was a definite change from before, when she acted more like a mistress than a lover. Zack enjoyed it nevertheless.

"I'll think about it," he finally answered.

Chapter VII - Revelations

Zack had trouble falling asleep that night. After he'd stripped out of the lingerie and put his own clothes back on, he felt a strange feeling, almost like he was leaving something behind. Now that he'd made it home and settled into bed, his thoughts kept him awake.

Did he feel guilty about letting his boss dress him up and fuck him? Did he push the boundaries too far, by letting it all happen? He'd always considered himself to be a straight, mostly normal person, aside from his love of stockings. But now, he'd fully dressed as a woman, gone by Jill, and gotten fucked in the ass, and he'd loved it.

Still, something felt off. A nagging feeling gnawed at the back of his brain as he tried to sleep. Had he cheated on Brandi? They were a new couple but with the threesome that had happened, they seemed to be in an open relationship.

He just couldn't put his finger on what was bothering him. After a lot of tossing and turning, he managed to finally fall asleep, though his alarm woke him just a few hours later. Now Monday morning, he knew he had to return to work, and face both Harley and Brandi.

-

Things seemed to be normal enough however. He barely saw Harley, as she typically remained in her office for most of the day, and Brandi seemed unchanged as well. As the end of the day rolled around, he came around to Brandi's desk.

"Hey, wanna go out for a drink after work?"

"Ms. Granger requested another meeting with me babe, I'm gonna have to take a rain check for now," Brandi replied, straightening up her desk.

"Oh...alright then," Zack replied. He gulped, thoughts racing through his mind. Was she going to tell Brandi what had happened? He thought about coming clean right then and there, but couldn't bring himself to do it. "Have a good meeting." He offered before quickly departing.

After Brandi had cleaned up her work space, she entered Harley's office. As usual, she sat behind her desk, staring at her computer monitor. Seeing her secretary enter, she paused the video she'd been watching and stood up.

"Ah Brandi. Thank you for meeting with me again."

Harley wasted no time for any further pleasantries. She began unbuttoning her shirt as soon as she'd finished speaking. Brandi was excited to be with her sexy shemale boss again and followed suit, stripping down to nothing but her heels and black thigh highs.

As Brandi approached, Harley bent her over the desk and began to rub the head of her cock along the slit, which was already moist and warm.

"You're so wet already," Harley remarked.

"I've been thinking about this since you told me about the meeting this morning," Brandi admitted.

Harley easily slipped her throbbing member into Brandi's hot snatch. Even though she was dripping wet, it was still super tight, and Harley moaned as she felt the vaginal muscles contract around her cock as it slid in deeper.

"Oh fuck yes," Brandi moaned.

She couldn't believe how insatiable she'd become lately. Between her new boyfriend Zack, her college girlfriend Hannah, and her shemale boss Harley, who was currently thrusting in and out of her from behind, she just couldn't get enough. She moaned, fingernails digging into the desk as she gripped it tight, an orgasm rocking her body already.

Harley slowed her thrusts, but continued to pump in and out at a steady pace. Her trademark devious smile crept over her lips as she began to speak. "Brandi, turn my monitor around and press play."

"Right now?" Brandi asked, unbelieving.

"You're going to want to see it," Harley replied, giving a particularly hard thrust deep into Brandi to drive her point home.

Brandi lifted her hand to turn the monitor so that she and Harley could both see it. She then pressed play and watched as Harley fucked a raven-haired beauty in white stockings and heels on a large bed covered in red silk sheets. All the while Harley continued pumping into her pussy, digging her nails into her hips as she held on tight.

Then it hit Brandi like a truck. That wasn't a woman. It was Zack! There he was with his stocking-clad legs over their boss' shoulders, in a wig, camisole, makeup, and heels, while she thrust hard into his ass.

"What the fuck?" Brandi asked, bewildered.

Harley stopped pumping temporarily, but kept her thick cock firmly lodged deep inside Brandi's clenching pink tunnel.

"It would seem Zack enjoys a little more than simply wearing stockings," Harley thought aloud, slowly pulling her soaked shaft out and then slipping it right back in.

"That's actually...kind of hot," Brandi admitted. "He looks really sexy dressed up."

Harley laughed and began thrusting with earnest again, making Brandi moan.

"I was hoping, nnngh, you'd say that," Harley moaned as she felt her cock spasm. In a few more thrusts, she deposited a sticky load deep inside Brandi's pussy, before slowly letting her cock slide out, a little bit of cum still on the head.

Brandi turned and dropped to her knees, taking it into her mouth and cleaning it off as she'd done the first time they'd done this. She found that she loved the taste of herself on a cock, mixed with the remnants of Harley's own cum.

Once she'd finished, Harley helped her up and the two began to get dressed. As Harley slid her skirt back on, she spoke.

"I'm thinking I have him dress up again, while you lie in wait ready to catch him. Then the three of us can have fun together."

Brandi thought about this as she slid her shirt back on and began to button it up.

"I'm on board with this all the way. I bet my friend Hannah would be too."

"Oh, another kinky slut to join us? The more the merrier," Harley grinned. "You and Zack both have the day off work tomorrow. I'll make sure he comes over. You just bring your friend along and be ready for action."

Brandi couldn't wait.

-

That night, Zack sat on his sofa, mindlessly watching tv when his phone rang. He saw that it was Harley calling, and answered nervously, "Hello?"

"Jill, darling," Harley began, using a seductive sultry tone, "You have the day off work tomorrow. I expect you at my suite at noon. Understand?"

"Yes ma'am, I'll be there," Zack agreed without hesitation.

As he hung up though, he still felt the familiar nagging feeling picking away at him, as though something were wrong.

Little did he know that things were actually about to be very right. He had no idea what lay just around the corner for him.

Chapter VIII - Down the Rabbit Hole

It was hard to pinpoint just who was the most excited for the day. Harley of course, as the architect of the orgy, was worked up from the moment she woke up. As the time quickly approached for Brandi and Hannah to arrive, she showered and got herself ready. She slid on a teal, satin thong, tucking her cock neatly into the front. Instead of a bra, she opted for a see-thru, sheer black camisole. She then took the time to slowly slide black thigh high stockings up her legs, and finished with a pair of stiletto heels that matched her thong.

After she'd styled her hair and applied makeup, she patiently sat on the couch, waiting for the first arrivals. She'd told the clerk to follow the same protocol as before, and so she simply had to wait for her door to swing open.

Her timing was almost impeccable. Just as soon as she'd gotten comfortable on the sofa in the same pose she'd waited in for Zack, the door opened and there stood Brandi and a sexy redhead, whom Harley had to assume was Hannah.

The two entered, wearing the same trenchcoats they'd donned the night of the threesome with Zack. After closing the door, they both looked Harley up and down hungrily. Hannah licked her lips.

"She IS hot," she remarked. "Do you really have a dick?" She then asked bluntly.

Harley simply smiled and uncrossed her legs, revealing the familiar budge in her thong. Hannah licked her lips again.

"That is so fucking hot."

Without waiting another moment, Hannah slid off her coat. She stood before Brandi and Harley now in nothing but a pair of black heels, and a black fishnet bodystocking, with holes at the breasts and crotch.

"Very, very nice," Harley said approvingly.