Catherine II
written by:
mcerotic

Lots of people wanted a sequel. So here it is.

Catherine liked her assistants young. Young and straight. Straight as in into boys, and straight as in straight out of high school. She liked them petite and boyish too, she wasn't into big breasts. Fiona, her latest, was perfect. Once they started working for her she would train them, not just how to do their job in the office but how to satisfy her in bed. She always made her assistants become her girlfriends, bending them to her desires. So straight as in straight into her panties as well.

But she made one concession to her assistants being straight. She let them have cocks occasionally. It seemed to keep them more emotionally levelheaded than a diet consisting solely of pussy.

She was interviewing a boy. Tim, he was called. Also straight, as in into girls and straight out of high school. She liked her boys barely ripe too. But they needed to have a little experience. Although she was hiring them as interns she was mostly hiring them to fuck her assistant occasionally. So straight as in straight into Fiona's cunt as well.

While Catherine watched. She liked to watch.

In fact she had a rule. Her assistants could only have sex with boys in her office. It was fine for them to have a cock in them from time to time but she didn't want her girlfriends having a true relationship with a boy too. Only with her. And the best way to ensure that was only to let them fuck in front of her.

"So," Catherine said to the boy. "I've got a couple of questions. Personal ones."

"Fire away," Tim said.

"I don't just want you as an intern. I want you to service my assistant."

"Service?"

"Fuck her. You have had sex before?"

Tim looked very surprised at the question but answered promptly anyway. "A few times."

"Do you feel you're experienced?"

"Not very. But I've had a few different girls."

"Do you know how to lick a girl?"

He blushed. "Well, I've tried it a couple of times but I never...you know...made her get all the way."

"Have an orgasm, you mean?"

"Yes. It's...well, harder than it looks from porn on the net."

"Or maybe the girls just weren't relaxed enough. It is pretty stressful the first couple of times having someone inches away from your pussy. Teenage girls are very self-conscious about their pussies."

"I'll train you to lick anyway. Or Fiona will, she's no longer self-conscious about hers. Along with all the office stuff you also need to learn."

"Gosh. This is so weird. Not what I expected."

"It will be even better than you expected. Did you see Fiona on your way in?"

"Yes."

"Would you like to fuck her?"

"Of course. She's cute."

"So let's get a look at you. Stand up and take off your shirt."

Tim stood, unbuttoned his shirt and slipped it off. His upper body was nicely muscular although not ripped. Catherine got up and ran her hand across his chest. She rubbed one of his nipples with a fingertip, feeling it go hard.

"Nice," she said. "Now slip off your pants for me. I hope you have a big cock. I like big cocks."

Tim undid his belt, undid the zipper on his pants and pushed them off. Without being asked he also pushed down his underwear. He kicked off his shoes and stepped out of the pool of clothes at his feet, completely naked. His cock was semi-hard from the sexual tension in the air. She felt her pussy quiver with anticipation of having it inside her.

"Mmm," Catherine said as she wrapped her hand around him. She gently stroked him feeling him start to grow even more between her fingers. "Stroke yourself while I get out of my clothes."

Tim stood their stroking his cock to full hardness as Catherine took off her jacket and blouse and slipped off her own pants. She reached behind and unclasped her bra and released her breasts. Then she pushed her panties over her hips. The two of them were both naked.

"I want you to fuck me," she said. "I want to see if you are good enough."

She walked across the office to where she had a large sofa, lay back on it and spread her legs. Tim moved across the room and positioned himself between her legs. She reached out and grabbed his cock. She was pleased he was big, thick rather than long, just how she liked them. She guided him between her lips so his cockhead was nestled in her entrance.

"Start gently," she said, "until you are worked inside. Then go hard. When you are about to finish, pull out and cum in my mouth. Teenagers taste so sweet."

Tim pushed his hips forward until Catherine's body resisted a little. Then he pulled back before pushing forward again, a little harder, working his thick cock inside. Catherine felt her body flood with excitement and her vagina relaxed. Tim slipped completely in.

"Now fuck me hard," Catherine commanded.

Tim started to thrust hard. He would pull his cock almost completely out of Catherine's cunt before ramming his hips forward and driving it back into her. Catherine couldn't stop herself grunting each time he slammed into her. She had already decided to hire him, she couldn't wait to watch little petite Fiona taking his lovely big cock.

"I'm going to cum," Tim said. He pulled out and moved up onto the sofa. She wrapped her mouth around his cock as time stroked himself. His cock jerked and she felt the familiar taste of cum pumping into her mouth. She used her tongue on his pink knob as he continued to stroke his own shaft. He produced jet after jet of cum and it was all she could do to keep it in her mouth. She swallowed his cum, the best snack a woman could wish for.

"Get dressed," Catherine said. "You can start on Monday."

"Wow, great. Thanks."

Tim pulled his clothes back on and left. Catherine sat down naked at her desk. She considered having a little touch of herself but then had a better idea. She pressed the intercom button on her desk and Fiona came into her office. She was no longer surprised to find her boss naked.

Without being asked, Fiona opened Catherine's desk drawer and took out a strap-on cock. She stepped into the harness and buckled it. Since she was fully-clothed and her boss was completely naked it all looked a bit incongruous. She moved between Catherine's legs and guided the plastic into her.

"How was that candidate?" Fiona asked as her hips started to move between her boss's outspread thighs.

"He is a pretty good fuck. You will enjoy him?"

"I get to fuck him? I thought I was only allowed to fuck you."

"You can fuck him occasionally. But only in this office while I watch. Or in our hotel room if we take him away on a business trip."

Fiona laughed. "That sounds a bit kinky."

"You've never had a threesome?"

"No. You know I only had two guys before I started here. Before you had me. You know you were my first girl. When you pushed your hand between my legs and your finger into me."

"You can have him on Monday. But I warn you he is big. Make me cum now."

Fiona reached into the desk drawer again and got out a little bullet shaped vibrator. As she fucked her boss she pressed the vibrator onto her clit. It only took a moment and then Catherine was squirming around on the sofa as her orgasm inflamed her body.

"Oh Fiona, you know just what I like. I'm so glad I picked you."

Fiona slowed down, gently sliding the plastic dildo in and out of her boss as her orgasm peaked and then died. Fiona bent forward and kissed Catherine.

"Thank you, that was nice," Catherine said.

Fiona pulled out of her boss. She took off the harness and put the toys back in the desk drawer. Then she picked up her bosses clothes off the floor. She squatted in front of Catherine as she stepped into her panties and pulled them up. Then she let her step into her pants and pulled them up, pulled up the zipper and did up the little clip. Next she picked up her bra and did it up for her. Finally she moved behind Catherine, held out her blouse as she slipped her arms into them, then her jacked. Finally she moved around to the front and did up the buttons on the blouse. Catherine was dressed again. Her pussy was still quivering with the excitement of Tim's earlier fuck. She didn't fuck boys very often, mostly just girls, so it was always a special feeling when she did.

On Monday the three of them were in Catherine's office. Since they all knew that Tim was going to fuck Fiona there was a definite feeling of anticipation. Catherine's pussy had been rippling all weekend and she was sure that Fiona's would have been even more active, reminding her that on Monday she would once again experience a cock, a real live cock attached to a boy, not a plastic one attached to her boss.

"Why not strip to your waist for him?" Catherine said to Fiona.

Fiona now knew just how to do a strip in a way that she took her time and teased. She slipped off her suit jacket. Slowly she unbuttoned her blouse, but kept it together so Tim just got a glimpse of her bra. Only when she had it completely unbuttoned did she open it up revealing her little bra covering her tiny tits. She reached behind and undid the clasp but held the cups of her bra against her breasts. She could see Tim's eyes glued to her bra as she slowly lowered it and he got to see her surprisingly big nipples.

"You need to get your shirt off too," Catherine said to Tim.

He was wearing a polo shirt so he just pulled it off over his head. Catherine could tell from the bulge in his pants he was already getting excited.

"Show her your lovely big cock," Catherine said.

Tim undid his pants and pushed them down along with his underwear. His cock sprung free, already almost completely erect. Fiona gasped when she saw it. Catherine knew it must be the biggest of the three Fiona had ever seen. Although Catherine's strap-on was not small and she had already been stretched.

Fiona didn't need to be told. She undid her own pants and took them off, standing in just her panties. Then she turned away from Tim and lowered her pants, giving him a good view of her ass and, perhaps, a peek at her pussy between her thighs as she bent over. She walked over to the sofa, covered her pussy with her hand, and sat down. She spread her legs, still keeping her hand over her pussy so Tim couldn't see it.

Tim was rock hard now. Catherine could see that Fiona was staring at it as if it was scarily thick. Catherine couldn't wait for the moment that her petite assistant was penetrated by the monster cock. She loved to watch and her favorite moments were watching it go in, especially the first time, and watching him cum all over her. Or sometimes cum inside so she could have the pleasure of licking it out.

Finally Fiona moved her hand letting Tim see her shaved pussy for the first time. She reached down and spread her lips open, revealing all the little pink folds inside and offering herself to him. Catherine could see that her cunt was glistening with arousal. Tim moved between her legs. Catherine, still fully dressed, moved over so that she had a better view. As she watched, Tim's throbbing pink knob vanished into her assistant. She reached between his legs and stroked his balls as he worked his way in deeper. Fiona was already moaning and letting out little squeals each time his cock thrust into her tiny cunt a little bit deeper.

Catherine let her thumb fall between Tim's ass cheeks. As Tim fucked Fiona, Catherine stroked his balls and pressed her thumb into his asshole.

"You are so fucking tight," Tim said as finally he got his whole cock into her.

"Oh that feels so good," Fiona encouraged.

"Fuck her hard," Catherine said, roughly pressing him forward with her hand.

Tim's hips started to thrust harder, Fiona started to moan louder, and Catherine worked her thumb deeper into his ass. Tim had not lasted all that long with her and she was sure Fiona would be tighter. Plus she was hotter.

"Cum all over her," Catherine said as she sensed his balls tightening on her fingers, felt his asshole clenching lightly. She knew he was close.

He pulled out. Catherine continued to stroke his balls as he stroked his cock and sprayed cum all over Fiona's body. She could feel his whole body pulsing as he spurted and spurted. He produced an amazing amount of cum and by the time the final dribbles emerged, Fiona was covered in a lattice of thick white cum.

Catherine moved alongside, bent down and started to lick up all the cum. She'd clean a little of Fiona's body and then swallow it. Gradually Fiona's skin was cleaned up and Catherine had swallowed it all. She moved between Fiona's legs and started to lick her clit. In seconds Fiona was groaning and moaning and a moment later she came herself.

"Oh yes, oh fuck that is good, don't stop," she squealed as her body burned with passion and trembled with the thrill of her orgasm.

"OK guys," Catherine said. "Get dressed. Be discreet and don't flirt with each other. Unless you are in my office when you can do whatever the fuck you want. Including fuck. But I need to get some work done."

The two younger people got back into their clothes, unlocked the office door and went back into the main office.

The next day Catherine summoned them both again. Fiona was in a suit with a skirt.

"Bend over my desk, pull up your skirt," Catherine said. Fiona did as ordered.

Catherine grabbed the waistband of her panties and pulled them down and off. She spread Fiona's legs and then her cheeks.

"Gosh your asshole looks so tight and sexy. You have never been done in there, right?"

"No," said Fiona. "The very idea is bizarre."

"Today is bizarre day then. You are going to be done anally for the first time in your life."

"Oh my god. Really."

"Yes, you can take Tim."

"But he is huge."

Catherine turned to Tim. "Get your clothes off. You are going to have her anal virginity in a few minutes."

She turned back to Fiona. "I'll get you ready."

"I guess. I'm scared though."

Catherine opened a desk drawer and got out a bottle of lube. She dribbled a little in the crack of Fiona's ass. Then she used a finger to rub a little on the tight pucker of Fiona's asshole. Her virgin asshole. If her vagina had been tight, her asshole had to be still tighter. Catherine was already anticipating watching Tim go in there, her pussy was fluttering at the thought of what a thrill it would be to see.

She circled a finger on her assistant's asshole and then centered it and pushed just the tip inside.

"Fuck that feels odd," Fiona said.

Gradually she worked a single finger inside. But she needed to open Fiona wider than that for Tim's cock. She squirted some more lube in the area and then forced a second finger into her assistant.

"Fuck that's extreme," Fiona grunted as her boss dilated her.

Once two fingers moved easily she slipped in a third. Well, slipped in is a euphemism. She forced in a third. She twisted her fingers back and forth enlarging Fiona's asshole ready for the intern.

"Oh my god," Fiona grunted. "I don't know that I can take it."

Catherine directed Tim to come over. She picked up the bottle of lube, squirted a generous amount onto her hand and then stroked Tim's rock-hard cock so it gleamed. She grabbed it and positioned it on the tiny starburst of Fiona's asshole.

"Push hard. It won't go in easily," she said.

Tim pushed his hips forward as Catherine held Fiona's cheeks spread wide.

"Fuck that's painful," she complained as Catherine watched the head of his cock start to force its way into her assistant.

"You can take it," she said. "Be brave."

Catherine watched as Fiona's asshole distended and Tim's cockhead started to enter her ass. Catherine's pussy was quivering as she watched and she could sense her assistant's discomfort at the intrusion.

"Work it in there," Catherine said.

Tim pulled back a little and pushed forward even harder.

"Shit," Fiona groaned as Tim's knob slipped into her. "That's intense."

Tim pulled out a little, just the rim of his cockhead emerged from her ass, then he roughly thrust his hips forward. Fiona wailed but an inch or two of Tim's shaft was finally inside her. Gradually he fucked his way in. Catherine was amazed at how exciting it was to watch. She reached around Fiona's body and started to finger her clit. Fiona was groaning and moaning, it was hard to tell whether it was because she was so excited or so uncomfortable. Probably both. Eventually Tim's cock was completely inside Fiona's ass. Her asshole gradually relaxed so he could move easily.

"Hard," Catherine said. She slapped Tim's ass and instinctively he thrust himself forward into Fiona's rectum. She started to spank him with one hand while she continued to finger Fiona's clit with a finger of the other.

"Oh my god I'm going to cum," Fiona wailed.

Catherine rubbed her clit harder and faster. She spanked Tim's ass harder as if she was a jockey encouraging a racehorse.

"Ngh," Fiona grunted as her orgasm burst. Then she was cumming loudly. Catherine hoped nobody was just outside her office, Fiona was not being quiet at all and there was no doubt what was happening if someone heard.

"Wow that's powerful," Tim said as he felt Fiona's asshole contracting around his shaft, grabbing him tight.

Catherine felt her pussy flood, it was so exciting to watch. Somehow watching a virgin take it in the ass was the ultimate, like really good porn. But it was real, a personal show just for her.

"I'm nearly there," Tim said.

Catherine turned around and squatted beside Fiona's ass.

"Fuck my mouth," she said.

It felt so dirty when Tim pulled his cock from Fiona's tiny tight rear entrance and immediately pushed it into her mouth. Well, it was dirty. But Catherine's pussy was loving it. Tim started to thrust back and forth roughly into the back of her throat. It took all her willpower not to gag on it.

"Ngh," Tim groaned, almost exactly the same sound as Fiona had made a short time earlier. His cock jerked. And jerked again. Catherine could taste his cum. Her pussy was spasming with the thrill of feeling Tim's cock twitching in her mouth knowing that he was blasting his thick cum onto her tongue. She knew her panties must be soaked, she was so excited. Finally Tim was emptied.

Fiona stood up. She pulled her skirt down.

"No panties for the rest of the day," Catherine said. She knew how on edge Fiona would be. Not just because her pussy was uncovered but her asshole was still all lubed up. Maybe she should have made Tim cum in her ass so she would also have to contend with his cum seeping out of her. But no, having him cum in her mouth was a not-to-be-missed delight.

Tim slowly got dressed and the two teenagers left. Catherine wondered whether to masturbate but decided it would be more fun to leave her pussy dying for attention for a few hours. She would call Fiona in later, have her get naked, and relieve the stress with her tongue. And orgasm delayed was often so much more intense.

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