Chapter 1

Catherine looked across her desk at the interview candidate. Fiona had just graduated high school. Catherine liked to hire smart high school graduates who had not been to college as her administrative assistants. They didn’t have bad habits and she could train them herself. Plus they got very loyal, she had given them their first opportunity.

But she had another reason. She always made her assistants become her lovers, and she liked them young and only just ripe.

She also preferred them boyish. The girl across the desk was just the sort Catherine liked. Not too tall. Very small breasts. Short black hair. She’d interviewed another girl earlier but she was not so ideal, more curvy. The earlier girl didn’t do anything much for Catherine’s pussy but this girl had it quivering gently in anticipation of future fun.

“So I have just a few more questions,” Catherine said.

Her strategy was to gradually get more and more personal with them, so they hardly noticed that they were being seduced. The skill of seducing a young girl was that it was over before they realized it had begun, even though it wasn’t something overnight. It would take time.

“OK,” said Fiona.

“Do you have a boyfriend?”

“No.”

“But you’ve had boyfriends?”

“Yes. It’s hard to get through high-school without…you know…doing it.”

“Fucking.”

Fiona blushed. “I thought it was best not to use that word.”

“How many boys?”

“What does this have to do with my job?”

“I don’t want any slutty behavior in the office.”

“Two.”

“Two boys or two times.”

“Two boys. Maybe ten times in total. Once with one. The rest with the second.”

Catherine thought that was the perfect number. Not a skittish virgin who had never spread her legs for anyone before. But not so many that sex wasn’t still novel and thrilling and a little bit dirty. Her pussy quivered a little more as she mentally undressed the girl in front of her. She idly wondered if she was shaved and presumed she would be.

“OK,” she said. “I’ll hire you.”

“Really?” said Fiona as if she couldn’t believe it.

“But I expect total loyalty. I’ll train you. But I’ll strip you down and build you back up. Work is not high school.”

She liked to slip in ambiguous words like ‘strip’ with a sexual connotation.

“Gosh, I can’t believe I’ve got a job.”

“You can start on Monday, okay?”

“More than okay.”

“You are cute,” Catherine said.

Fiona blushed. “Well, thanks, I guess.”

“We’ll have fun. Not just work.”

“I feel so inadequate. Like I haven’t a clue how to do my job.”

“Don’t worry, I’m going to be a good teacher. If you do everything I say you’ll do fine.”

“What should I wear?”

“Wear whatever you want.” She laughed. “Well, not shorts and a sports-bra or anything. This is an office. Then we’ll go and buy you some appropriate clothes since I very much doubt you own any. The company will pay, of course.”

“Wow. I guess I’ll dress like I did for high school. Pants and a top. Or something like that.”

“That’s perfect. I’ll see you on Monday then.”

Fiona got up and left Catherine’s office. Once she had gone, Catherine locked the door. She sat back down, lifted up her skirt and slipped her hand into her panties. She slipped a finger inside her cunt. She was not surprised to find how wet she was. She let out a little sigh as she let her finger, coated with her juice, drift up to her clit, already hard with desire.

She started to stroke herself as she imagined what Fiona would look like naked. Something she planned on finding out early the following week. Those cute little tiny tits. Her shaved pussy. Even the tight little virgin pucker of her asshole. She felt her orgasm begin as she imagined the first touch of Fiona’s tongue on her pussy. Her pussy quivered with joy as she imagined it was not her own finger on her clit but her new administrative assistant’s tongue. She let out a little moan of pleasure as her pussy throbbed with arousal and her finger coaxed the final moments of pleasure from her body. She pulled out her hand and licked her fingers, tasting the afterglow of her pleasure. She pushed her skirt back down and got back to work.

On Monday Fiona showed up. She was dressed conservatively in black pants, a white blouse and, although her breasts were small enough she didn’t need the support, the hint of a white bra underneath. Catherine felt a little quiver of excitement. This was the week that the seduction would begin.

Catherine spent all day with Fiona. She taught her about spreadsheets and stuff. Fiona had learned something about it all in school but not enough to function in a modern business. The basics but not the database stuff, pivot tables, setting up a complete business model. Soon it was 4pm.

“Do you have to leave immediately?” Catherine asked.

“No, I guess.”

“Then let’s go buy you some professional clothes.”

“Really?”

“Yes. I like to dress my assistants.”

Fiona laughed nervously. “Not literally I hope.”

Catherine almost blurted out that actually she preferred to undress her assistants before she realized it was too soon.

They went to Nordstrom. Catherine made Fiona tell her size and then picked out several outfits.

“Let’s go try them on,” she said.

The two of them walked to the fitting rooms. Catherine knew Fiona would expect her to stay outside but she had no intention of doing that. She followed closely behind her and they ended up together in the fitting room. She could sense Fiona’s embarrassment but also knew she was too shy to ask her to leave.

“So let’s see them on,” Catherine said.

Fiona blushed. “But…”

“Don’t worry. We’re all girls. It’s a hell of a lot faster this way.”

“Okay,” Fiona said doubtfully.

“Put this on.”

Catherine held out one of the suits they had picked. She knew that to do that would require Fiona to take off her clothes down to her underwear. She couldn’t wait to see her body, not naked, but the next best thing.

Fiona clearly didn’t want to make a fuss on her first day so she meekly took off her blouse and pants. As quickly as possible she put on the suit that Catherine had selected. Of course not before Catherine had seen her in her underwear. Catherine felt a flutter of arousal. She realized that she had picked well during the interview process.

Catherine made Fiona try on all the outfits that they had brought into the dressing room. Each time she got a sight of Fiona’s body. Her little white panties, nothing special. Her bra that was more for convention since her breasts were too small to require a bra. And, she knew, each time Fiona let Catherine see her in her underwear she was getting more relaxed about her body.

They picked a couple of the outfits and Catherine paid for them.

“Gosh, thanks,” Fiona said.

“It’s not me personally paying for them. It is the company.”

“Even so. It feels like you are treating me to outfits I could not afford.”

“Let’s go and have a drink.”

“I’m not 21.”

“Good point. We can go to my hotel room.”

“You have a hotel room?”

“I work out in the hotel across the road. Unless they are totally booked out they let me use a room for an hour or two for free. We give them a lot of business. They know I’m the decision-maker as to where our people stay when in-town and they have competition. It is Monday. They won’t be booked out.”

Up in the room, Catherine got two vodkas out of the minibar. The price was ridiculous, of course, but vodka was a lubricant to a girl’s panties coming off. Plus, often, the hotel comped her on anything she drank. They didn’t want to risk losing hundreds of room-nights over a few dollars of alcohol.

She added tonic and ice and the two girls drank from the unsatisfactory plastic cups. It would be so much better in a bar, of course. But that was one of the prices to pay for liking them so young. Old enough to fuck but not old enough to buy a beer for, which Catherine thought was ridiculous.

“Okay,” Catherine said. “Let’s get you some wonderful underwear.”

“What?” Fiona said.

“I know nobody can see it. But it is important for me that my assistants wear really good underwear. It will give you confidence.”

“Really?”

“It will. Trust me. That crap you are wearing is not going to make you feel good. We are going to get you some better stuff.”

“Victoria’s Secret?”

“No. That is only semi-good. We will buy you some really good stuff.”

“Wow. Like where?”

“Back in the mall across the road. I know a place.”

They left the hotel and crossed the road to the mall again. Catherine guided Fiona to a specialized underwear shop. Where she knew the assistant. Who would help with the next stage.

The assistant measured her and picked a few bras and some panties. Then the three of them went into the changing room.

“Slip those things off,” the assistant said casually, as if it was totally normal for a woman’s boss to be in there too watching. Fiona was clearly embarrassed but also too timid to do more than slowly slip off her pants and top, then take off her bra.

Catherine got to see Fiona’s breasts for the first time. They were tiny but her nipples were not. Her areolas were like copper pennies, brown and small, but her nipples stuck out half an inch like those dowels you get in Ikea furniture. Light brown and hard. Well, not quite that long. Catherine realized she had involuntarily licked her lips.

“And the panties,” the assistant said insistently.

Fiona slowly slipped her panties down.

Catherine was pleased that she had been right. Fiona was shaved, a nice smooth fleshy mound. She liked them shaved. It made them look even younger. Her pussy was hardly even visible. She wasn’t one of those girls with a deep slit at the base of her belly, more like a hint of a furrow where her body curved back underneath her. Catherine couldn’t wait to touch it. She felt a flutter of pleasure at the anticipation of the moment she would get to play with it.

Fiona tried on all the underwear and they picked some of the things that fitted well. A woman’s bra-size and a bra’s bra-size don’t always match up that closely. They put all that they had selected into a bag and Catherine paid for everything.

“Let’s go back to the hotel,” Catherine said, knowing full-well that Fiona might hesitate and go home.

“Okay,” she said without really thinking about it.

It was not that much later they were both lying on the bed with another vodka in their hands.

“How was it?” Catherine asked.

“I can’t believe all the stuff the company bought me.”

“You need to look good if you are going to be my assistant.”

“Well, those clothes will do the trick I guess. They were so expensive.”

“Not just the clothes. You look good without any.”

Fiona blushed again. “I don’t…well I know I’m not that bad looking but…nobody has told me about my body before.”

“Your boyfriends didn’t”

“I’ve only had one boyfriend. The first time was more of a hook-up. With one of my older brother’s friends. I was only fifteen.”

“So your boyfriend didn’t tell you that you had a great body?”

“No. I don’t think he ever got over the fact that I let him see it in the first place. Plus he’d never seen another body for comparison.”

“He was a virgin the first time you fucked him?”

“Yes.”

“You have a great body. Let me be the first person to tell you then.”

Fiona blushed again. “Well, I’m surprised. I mean I don’t have anything much in the breast department.”

“Not everyone likes massive breasts.”

“Gosh,” Fiona said. “Boys all seem to go for the girls with the big boobs.”

“Girls don’t.”

Catherine reached over and gently ran a hand over Fiona’s breast. Of course she was still in a blouse and bra so it wasn’t like touching her skin. Even so Fiona shivered slightly. But she did nothing to brush off her hand. Catherine left it there.

Catherine broke the embarrassing silence. “You have a lovely body even though you don’t have D-cup breasts.”

Fiona laughed. “I’d be happy to be big enough for a true A-cup. I’m so flat-chested it’s embarrassing. It seems such a waste of money when I have to buy bras.”

“Don’t worry. There are plenty of people who love tiny tits. Me for one.”

Catherine undid the buttons on Fiona’s blouse. Fiona just lay there frozen, totally unsure of how to behave. Catherine opened up the blouse and pushed Fiona’s bra up exposing her breasts. Catherine so wanted to kiss Fiona’s nipples but decided that would be going too fast. She knew Fiona had never been touched by a woman before. Instead she took one nipple between finger and thumb and gently rubbed it. Fiona let out a little moan. Her nipple went rock-hard instantly. Catherine couldn’t resist. She bent over and took Fiona’s erect nipple between her teeth. She flicked it with her tongue as she gently nibbled it. Fiona was shivering, her eyes shut. Catherine’s pussy was shivering too. She knew her panties would be damp. Fiona’s too, she hoped.

Catherine knew that probably she could undo Fiona’s pants and she wouldn’t get stopped. But only probably. So she didn’t want to risk it so soon. She would have to content herself with Fiona’s breasts for now. She moved her mouth to the other nipple and felt Fiona’s body twitch as she bit down on it. She stroked one of Fiona’s thighs as she licked and nibbled. Her fingers were almost touching Fiona’s pussy and it took real willpower for Catherine not to just move her fingers there and rub her through her pants. But that would be a treat for another day.

Reluctantly Catherine took her mouth from Fiona’s breasts and lay back on the bed again. She took a sip of her vodka. Fiona opened her eyes as if she was unsure if she had been dreaming or not. Her boss was lying there casually sipping her drink, not the slightest sign that she had been tormenting her nipples a moment before. But her blouse was open and her bra was pushed up, so something must have happened. Fiona pulled her bra back down, clearly a bit embarrassed now, and buttoned up her blouse.

“I need to get home,” she said.

“Did you have fun today?”

“I learned so much. Thank you. Plus the clothes. I can’t thank you enough.”

“You will learn much more. About work. And life.”

In the office the next day Fiona was in one of the suits that they had bought the previous evening. Fiona came into Catherine’s office.

“You look great in that,” said Catherine. “Which underwear did you pick?”

“The cream silk ones.”

“Show me.”

“What do you mean?”

“Pull up your skirt and let me see how they look on you.”

“Really?”

“Yes. You need to learn to do as I say. You can shut the door first though.”

As if in a daze Fiona shut the office door, then stood in front of Catherine’s desk and slowly pulled up her skirt. Gradually the cream panties came into view. And gradually Catherine’s pussy started to flutter. Fiona pulled her skirt up around her waist so her panties were completely on view. Catherine could see the little bulge in the silk that she knew concealed Fiona’s hairless fleshy mound.

“Nice,” she said. “I hope you are wearing the matching bra.”

“Of course,” said Fiona. Without being asked she undid the buttons on her blouse and opened it up to reveal the cream bra. She stood there oozing sexuality, her blouse open, her skirt around her waist, her underwear on view. Catherine couldn’t wait for the next phase of the seduction to begin.

“I am going on a business trip next Monday and Tuesday. You will come too.”

She taught Fiona more about how to do her job during the week. But Sunday couldn’t come fast enough. On Sunday evening they sat side by side on a plane to the town where their subsidiary was based. They got a taxi to the hotel.

“We have to share a room,” Catherine said to Fiona as they walked into the lobby. “To keep expenses down.”

Fiona gasped as they walked into their room.

“But there is only one bed.”

“That’s fine. We’ll manage.”

Of course Catherine had explicitly booked a room with a single king bed. A bed she was looking forward to sharing with Fiona.

“You can have the first shower,” Catherine said. “What do you wear in bed?”

“Usually just a T-shirt.”

“Panties?”

“Not normally.”

“You like to be able to touch yourself, don’t you?”

Fiona blushed a deep red.

Catherine laughed. “I can tell from the color of your face that I’m right. Do you do it every night?”

Fiona looked down as if it was something to feel guilty about. “Usually,” she said quietly.

“Well I don’t want tonight to be an exception.”

“What do you mean?”

“I want you to touch yourself. Just because I’m in bed with you is no reason to forgo your nightly pleasure.”

“But…gosh…I’ve never even talked to another person about it before. Let alone actually do it alongside them.”

“I can pretend to be asleep if you like. But I want you to finish.”

“Finish?”

“Have an orgasm. You do have orgasms when you masturbate, don’t you?”

“Yes. Although I might not be able to get there with you here too. I’ll be so self-conscious.”

“Would it help if I masturbated too?”

“Gosh…I have no idea. It might make it worse.”

“I like to touch myself at night too. Every night. And I won’t want tonight to be an exception either. That’s not going to upset you is it?”

“No,” said Fiona unconvincingly, as if she was used to having another woman masturbate alongside her.

“Go and have a shower and put your T-shirt on then.”

Fiona went off to the bathroom. Catherine heard the shower go on and ten minutes later Fiona emerged in a T-shirt that came about halfway down her thighs. Her nipples poked through the thin material. Her face was pink. She was clearly somewhat aroused.

Catherine went and had a shower. She walked out of the bathroom naked. It was the first time Fiona had seen her body. She had medium sized breasts, much larger than Fiona’s of course. A nice figure from yoga and working out. Her pussy was shaved but she kept a patch of hair above her slit. She liked her assistants to be shaved and girl-like but liked to keep a slightly more womanly look herself.

“I usually sleep in the nude,” she said casually. It wasn’t even true but tonight she didn’t want to bother with anything.

Fiona was already in bed, lying there looking half-terrified as her naked boss slipped under the covers beside her.

“Did you do it yet?” Catherine asked.

“No,” Fiona whispered.

“We’ll do it together.”

Both women spread their legs and started to stroke themselves. Catherine watched Fiona but Fiona had her eyes closed. Catherine stroked her clit but carefully avoided getting too close to orgasm. When her orgasm finally happened she wanted Fiona to be the one to deliver it.

“I’ve got a better idea,” she said suddenly. “We do each other.”

Without waiting for a response, she slid her hand between Fiona’s legs, pushed her hand away and started to caress Fiona’s pussy.

“You can’t touch me there, you’re a woman,” Fiona said pushing Catherine’s hand away.

Catherine just put her hand back again.

“No,” Fiona said, pushing her hand away again.

Catherine put it back. She found Fiona’s entrance and pushed her finger into her.

“Oh my god,” Fiona moaned.

“Are you okay?” Catherine said quietly.

“Yes and no. My brain is not okay but…between my legs is loving it.”

“Just go with your pussy’s feelings.”

“Oh wow,” Fiona moaned as Catherine’s finger slid back and forth in her pussy. Catherine noticed how wet and tight she was. Wet and tight and exciting. After finger-fucking her for a bit, she pulled her finger out and then slipped it up between Fiona’s labia until she felt the unmistakable little point of her clit. She started to rub it gently, experimenting to see what seemed to elicit the most intense sounds of arousal before she finally settled in on a rhythm.

“Oh my god, it’s going to happen already,” Fiona moaned. Then it did. Her body jerked and then her hips started to thrust and her pussy throbbed with pleasure.

“Oh I’m cumming,” she moaned unnecessarily.

Catherine flipped the bedcovers back and dived between Fiona’s legs while she climaxed. She plunged her tongue into Fiona’s throbbing pussy. Fiona barely noticed since she was lost in the excitement of her orgasm. Catherine swirled her tongue around inside Fiona as her orgasm slowly died away.

“Fuck, what are you doing?” Fiona said once she felt Catherine’s tongue.

Catherine lifted up her head for a moment. “Licking you.” Then she pressed her tongue back onto her pussy.

“Oh my god. I’m not a lesbian.”

Catherine lifted her head again.

“You want me to stop?”

“No. It feels wonderful.”

“Did you boyfriend lick you?”

“Never. I wanted him to. I wanted to experience it.”

“And how is it?”

“Ethereal. Intimate. Arousing. Do it again.”

Catherine lowered her head. Now she explored Fiona’s pussy in a more leisurely way. She pushed her tongue inside and then let it slip up to her clit. She pushed it back inside again and then went the other way, until the tip of her tongue felt the rough pucker of her asshole. Fiona started to sigh and moan with pleasure again.

Catherine circled her tongue on Fiona’s clit. She pressed a finger against her opening and slipped it inside her cunt. As her tongue danced on Fiona’s clit she stroked her insides. Fiona was moaning continuously. It would not be long before her second orgasm of the evening.

Fiona’s hips were making little tiny thrusts under Catherine’s mouth as she got close. Catherine licked her clit a little harder and faster and finger-fucked her more vigorously.

“Nnnnggh,” Fiona suddenly grunted. Her body jerked and shook and she was moaning. “Oh that’s so good, don’t stop, yes, yes.” Her hips thrust a little harder as she fucked Catherine’s tongue.

Fiona lay there limp for a moment. Then she opened her eyes.

“Fuck that was something,” she said.

“How do you mean?”

“I’m embarrassed,” Fiona said. “I’m still not used to talking about sex as if I’m grown up.”

“Don’t feel embarrassed.”

“I’ve never cum with someone before. Only with…you know…my finger.”

“You never came with your boyfriend?”

“No. He never worked out my anatomy enough to…keep going for long enough in the right spot.”

“Boys can be a bit clueless about what we have between our legs.”

Fiona laughed. “That’s an understatement.”

“Do you want to try it?”

“What?”

“Licking. I want you to lick me.”

“This is so weird. I’m not a lesbian but I loved it when you fingered me and licked me. At least my body did. But licking you seems…I don’t know…a challenge.”

Catherine spread her legs.

“You like challenges,” she said.

Fiona moved between Catherine’s thighs. She lowered her head close to her pussy.

“Oh gosh I’ve never seen one before. Up close.”

“Just push your tongue against it. Anything will feel good. Then try and imagine your tongue is your finger and you are doing yourself like you do each night.”

Fiona pushed her tongue onto Catherine’s pussy. Catherine’s pussy fluttered with excitement, partially from the tongue and partially because she had managed to get her little young assistant to finally do her. It would be easy to get her to go further now.

“That’s right, like that,” Catherine sighed as Fiona experimented with how to move her tongue amongst her folds.

“Put a finger in me. Like I did with you.”

“You did? I guess I was so far gone I didn’t even notice.”

Fiona’s finger tentatively probed between Catherine’s lips seeking the entrance.

“Yes, there,” Catherine said as Fiona’s finger nestled in her opening. Slowly Fiona pushed inside as if she was afraid of hurting Catherine.

“Now lick my clit and finger me. I’ll cum in no time.”

Fiona’s tongue rubbed on Catherine’s clit. She was a bit rough and inexperienced but nothing would stop Catherine cumming that night.

“Keep going,” Catherine sighed. Her orgasm was welling up inside her. And then it burst. “Oh fuck you clever girl you did it. Oh, oh, oh, wow it is strong.” Her body throbbed with ecstasy as her assistant’s tongue and finger drove pleasure into her.

Catherine reached down and put her hand on Fiona’s head. “Enough,” she said.

Catherine pulled Fiona up alongside her, wrapped her arms around her and kissed her for the first time.

“Are you a lesbian?” Fiona said.

“No. I like cocks too.”

“So do I. Not that I have had that many.”

The two women kissed again. This time Catherine drove her tongue into Fiona’s mouth. After a short crisis of confidence, Fiona responded and the two women’s tongues jostled together.

“We’d better get some sleep,” Catherine finally said. “We have a long day in the office tomorrow.”

During the day they reviewed the business performance of the subsidiary they were visiting. Catherine couldn’t wait for the moment when they were back in their hotel room alone again and her assistant would be out of her business clothes. Out of her clothes completely.

Up in the room Fiona looked embarrassed, unsure of what she should be doing. Catherine lay on the bed watching her.

“Strip for me,” she said.

“I don’t really know how.”

“Start by taking off your jacket. Then undo your blouse. Take off your pants. Then tease me a bit, undo your bra but hold it against your breasts so I have to wait a little before I get to see them. Finally, turn so your back is to me and slip off your panties. Give me a good look at your ass before you slowly turn around and I get the full naked girl effect. Wait, I’ve got a better idea. Come and lie on the bed and I’ll do it for you first.”

Fiona slid onto the bed as Catherine got to her feet. She stood there swaying as if dancing to the non-existent music. She let her suit jacket slip off her shoulders and put it on the chair. Slowly she unbuttoned her blouse, opened it up and it joined her jacket. She undid the clip on her pants, undid the zipper, turned her back to Fiona and slowly lowered them. Since she was wearing a thong, her ass was nicely on view.

She turned back to face Fiona, just in bra and panties. She reached behind and undid the clasp. Then, holding her bra against her breasts, she pulled the straps off her shoulders. She slowly lowered the bra so that her breasts gradually came into view. She tossed the bra onto the pile of clothes on the chair. Once again she turned her back to Fiona and slipped the waistband of her thong over her hips and let it fall to her ankles. She could sense Fiona’s eyes on her ass. Slowly she turned around completely naked and showed Fiona her pussy.

“Your turn,” she said as she got onto the bed.

Fiona stood and took off her jacket. In a moment she was down to her bra and panties. Just as Catherine had done, she unclasped her bra but held it onto her breasts. Then she turned away from Catherine and tossed the bra onto the chair. Slowly she slipped her panties down. She put her hand over her pussy and an arm across her breasts and turned back to face Catherine.

“You aren’t allowed to see,” she said.

“You tease.”

“OK, just my breasts,” Fiona said as she moved her arm, still keeping a hand covering her pussy.

“You want to see it don’t you? My pussy.”

“I do. Show it to me.”

“And what does it get if I show it to you?”

“I’ll fuck it.”

“That sounds fun. OK. Three, two, one.”

Fiona held her arms out wide, hiding nothing of her naked body. Catherine was pleased with her choice of assistant. She was just the perfect mixture of boyishness and girliness. Little tiny tits. A young girl hairless pussy. Not really a curvy feminine figure. Short hair. She was the perfect androgynous teenager. Catherine felt her pussy flutter with desire. A desire that she knew she could satisfy, that now Fiona would do whatever she wanted.

“You really do have a lovely body,” Catherine said as she inspected her assistant.

Catherine got up off the bed and went to her suitcase.

“You know you said you like cocks. Well, I brought one with me.”

She pulled a large plastic cock out of the case. It was realistically shaped, a realistic flesh color, and very large. She reached into the case again and pulled out a harness.

“Wow, it’s big,” said Fiona.”

Catherine laughed. “Bigger than your ex-boyfriend I guess.”

“For sure. Scary big. Are…I’m not sure how to phrase it…are there men that size?”

“Not many. But a few.”

Catherine strapped the harness on with the cock. She stood there, a naked woman with an incongruous big pink cock. She reached into her case again and took out a small plastic bottle of lube. She dribbled some on the cock. Then, as if she was a man masturbating, she stroked the cock to spread the lube all over it.

“Lie on the bed and spread your legs,” she said.

Fiona got onto the bed, lay on her back, and pulled her knees up towards her chest so that her little shaven pussy was completely exposed. Catherine moved onto the bed and positioned the cock so that it was just nuzzling between Fiona’s lips. She pushed her hips forward and a little of the knob of the cock vanished into her assistant.

“Fuck it is enormous,” Fiona said.

“It’ll stretch you.”

“It’s like my first time all over again. Go slowly. It is hurting.”

Catherine pulled back a little and then pressed forward, pushing the huge dildo a little further into Fiona. She gradually worked it in, doing her best not to really hurt Fiona but also enjoying the fact that she was causing a little discomfort. A little discomfort was sexy, like a light spanking. Finally she got it buried totally inside. Fiona was moaning and sighing with pleasure, her eyes shut, lost in her own world of arousal.

Catherine started to fuck Fiona hard, ramming the plastic cock into her cunt, her now wet and welcoming cunt. Fiona was moaning and groaning, her mind overwhelmed by her pussy. The cock slid easily inside Fiona’s slick hole.

“Oh god that’s so good,” Fiona moaned as the plastic invaded her cunt. “Better than my boyfriend.”

“Bigger for sure,” Catherine said.

Fiona laughed. “Yeah. But fuck me hard. It feels so good.”

“Will you cum?”

“I never have before. But maybe. It feels close.”

Catherine fucked Fiona vigorously, roughly, enthusiastically. Fiona was moaning and thrusting her hips back up against the plastic cock each time it slid into her.

“Oh my god I think I’m going to cum,” she squealed.

Her body froze and then she was shaking and moaning and quivering.

“Fuck me, yes, oh my god I’ve never cum like this. Fuck me harder. Don’t stop.”

Fiona’s body shook with pleasure as Catherine remorselessly rammed the dildo into her cunt. Catherine bent down and kissed Fiona as she orgasmed, still thrusting the cock into her pussy as her tongue thrust into her mouth,

“Oh yes,” Fiona moaned, “That is so good.”

Catherine pulled the plastic cock out of Fiona as her orgasm faded. She bent down and gently used the very tip of her tongue to caress Fiona’s clit as she gradually came down from her orgasmic high.

“Oh wow, you know how to pleasure a girl,” Fiona sighed. She looked down at her boss between her legs gently touching her clit, knowing just how hard to touch given how sensitive it was after an orgasm.

Catherine finally stopped licking and the two women cuddled on the bed.

“We’d better go for dinner, I suppose,” she said. “And afterwards…”

“Yes?”

“You wear the harness and fuck me.”

“Wow. OK. You know I’ve never done anything like this before?”

“I know. But I also know you are a fast study. You’ll learn in no time.”

Back in the office a day later Fiona brought Catherine a cup of coffee from the break-room.

“I’m so horny,” said Catherine. She was on the point of ordering Fiona to lick her but she really wanted her to volunteer on her own. The last stage of her training. When she anticipated Catherine’s desires before she even expressed them.

“Let me do you,” said Fiona. She reached up under Catherine’s skirt and pulled off her panties. Catherine spread her legs. Fiona plunged her tongue deep into her boss. Her boss lay back, pleased at her choice of assistant. For the next couple of years she would have a daily orgasm to go with her coffee. Life was good.

Chapter 2

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. An orgasm delayed was often so much more intense.

Chapter 3

Since I left high school I have had quite an adventure. I decided not to go to college, at least immediately, and to get a job for a bit while I decided what I wanted to do with my life. I thought it might be difficult to find a job but in fact I was offered one at the first place I interviewed. It turned out to be an experience rather different from what I expected. My boss, Catherine, didn’t just teach me all the office stuff, she also taught me what to wear and bought me clothes I could never afford. Then, one evening, when we were away on a business trip together she took me. I came out of the shower all innocent and by morning she could get me to do anything she wanted sexually. She really knew just what my body desired even if I didn’t myself. After a few weeks I’d do anything for her. Not that I felt like her slave, I was totally smitten. I was her girlfriend.

But she had a rule. Now that I was her girlfriend I wasn’t allowed to have other lovers. Not that I had anyone in mind but I did miss the masculinity of being fucked by a guy. Not just his cock—Catherine had a big plastic cock and really knew how to use it to get my body shaking—but the different feel of a male body. I needn’t have worried. Catherine knew I’d be like that and she hired an intern. To be honest, I think she hired him just to fuck me. But I was only allowed to fuck him when she was there. I don’t know if it was just that she liked to watch me being fucked or if it was to make sure that we didn’t develop too much emotional attachment. Sometimes she would join in and touch us but usually she would just watch as we fucked, usually with her skirt up or her pants down, and her hand in her panties.

I didn’t tell my friends, never mind my parents, about what was going on. Firstly, I didn’t want to break the spell and secondly nobody would believe me. My boss, an older woman, seduced me and I’m OK with it. She hired a random guy to fuck me and I’m OK with it. Sometimes, when she is on edge, she makes me get her off with my tongue in the office and I’m OK. Of course if you’d asked me the day I walked into the office I’d have said I’d never do those things. Shows how well I know myself. Well, I’m still just a teenager so I know I’m still clay to be shaped but even I am surprised at what I have done when I think back.

Catherine had closed a big deal of some sort. The guy from the other company was coming to sign the contract in her office. Quarter of an hour later she summoned me into her office.

“This is Pieter,” she said.

He was a tall, very tall. Dutchman. Blonde hair. Thin without being a beanpole.

“Isn’t she perfect?” she said, turning to him.

I felt my pussy quivering. She had something in mind even if I didn’t know what. I expected her to ask me to strip, maybe bend me over her desk and let him take me while she watched. I was ready to do it, of course. I would never dare to disobey Catherine.

“Why don’t you take her to dinner,” she continued. “She’d like that.”

She turned to me. “Have you ever been on a going-out-to-dinner date?”

“Only with you on business trips. Unless you count pizza.”

“I certainly do not count pizza. I made you both a reservation at the Mandolin.”

The Mandolin was one of the most expensive restaurants in town. Totally out of my league. The one boyfriend I’d had was a high-school student so that wasn’t the sort of place he was going to take me either.

“Very convenient,” Pieter said. “That is where I’m staying.”

The Mandolin was on the ground floor of the best hotel in town.

“I know,” she said. “Seven-o-clock. That’s just over an hour away.”

I felt a pang of disappointment that I wasn’t going to be ordered to get naked for him. But she had set me up for dinner with Pieter. In a great restaurant. In the same building as his hotel. As his room. As his bed. I was pretty sure what I had to do.

“Can I take her now?” Pieter asked. I thought for a moment he meant between-my-legs take me, but he just meant whether Catherine needed me for the rest of the afternoon.

“Sure,” she replied. “Buy her a couple of drinks before dinner.”

She picked something up off her desk. It was her credit-card. She passed it to me. “Make sure he doesn’t pay for dinner though. And you’d better call your parents.”

I knew Catherine, and I knew from the way she said it just what she meant. She didn’t mean to tell my parents I would not be home for dinner. She meant to tell them I had to go away overnight on a business trip. She was giving me to her client. If he wanted it, I should fuck him. In fact, if he didn’t want it then it was my job to make him want it. And then fuck him. Then stay the night. And fuck him again before breakfast. Instead of feeling insulted, or like she was my pimp, I felt thrilled. My pussy was even more thrilled and was already enthusiastic and wet.

Half-an-hour later I was sitting in the bar at the Mandolin with Pieter.

“What would you like to drink?” he asked.

“A coke, I guess,” I said.

“You aren’t twenty-one?”

“No.”

“Then I’ve got a better idea. Let’s go up to my room and you can have a drink there. A real drink.”

My pussy fluttered. Go to his room. His bed. Get a little drunk. My panties were probably coming off even before dinner. The two of us went to the elevator and went into his room. A typical up-market hotel room. Big king bed. A desk where his computer was open but its screen blank. A huge flat-screen TV.

I expected Pieter to get one of those tiny bottles of scotch or vodka out of the minibar but he picked up the phone instead and dialed.

“Room service?”

“What champagne do you have?”

“Dom Perignon sounds perfect. And a bottle of Absolut. And lots of tonic.”

He put the phone down. Apparently we were going to drink champagne. I don’t think I’d ever drunk real champagne before. Like from France. And I thought Absolut was vodka but I wasn’t sure. I’d not had that either, as far as I knew. When Catherine regularly made me a vodka and tonic out of the minibar when we were on business trips, I never bothered to see what brand. It was just a nice relaxing aperitif before what came next. And I don’t mean dinner.

A few minutes later there was knock on the door. A man in a white jacket came in with a trolley. There was an ice-bucket containing the champagne. Another bucket of ice. A bottle of vodka with condensation dripping off it. Lots of glasses since the hotel had no idea how many people Pieter was serving. Pieter tipped him with a $20 bill and he left.

Pieter picked up the champagne bottle out of the ice.

“Do you know how to open champagne?”

“No.”

“Let me show you. First you remove the capsule, this foil that covers the cork. Often there is a little tab you can pull that makes it easier. See, the cork is held in by a wire cage. Put your thumb over the cork like this just in case the cork wants to come out early, which it shouldn’t. Undo the wire here and then remove the cage. Now hold the cork with one hand and hold the base of the bottle with the other, like this. Now turn the bottle. The bottle not the cork. It should slowly come out. Not with a pop, with a little hiss. Like a nun’s fart someone once told me.”

Pieter turned the bottle and the cork came out almost silently. He poured some of the champagne into each of two glasses, waited for the foam to subside, and then topped up each glass. He passed one to me.

“Cheers,” he said and we clinked glasses.

We made small-talk as we drank our first glass of champagne. There was definitely a tension in the air. A middle-aged man alone in a hotel room with a teenager and a bottle of champagne was likely to lead to something. He was born in the Netherlands and came to the US when he was about my age, to go to university. His plan was to go back after graduation but like so many people he stayed.

He poured us both a second glass of champagne. I could already feel the first going to my head.

“How is Catherine as a boss?” he said.

“How do you mean?” I genuinely wasn’t sure quite what he might have meant.

“I’ve heard rumors about her and her assistants.”

“What sort of rumors?”

“Oh come on. You are her assistant. Even if they are just rumors you must have heard them.”

I had no idea what to say, how much to reveal, how much he knew.

“Are you her girlfriend?” he continued.

“I’m straight,” I said, a little evasively.

“I know,” he said. “But I think the rumors are probably true.”

I blushed. I didn’t know precisely what he had heard but probably it was accurate.

“You are so cute when you blush,” he said. “I won’t ask any more. Your face answered for you.”

“It’s all true,” I suddenly blurted out. I don’t know why, maybe I was already a little drunk.

Pieter got up, put some ice into a tumbler, poured a huge amount of vodka into it and topped it up with tonic water. He passed it to me.

“Tell me,” he said.

I took a gulp of the vodka. The drink was so strong it burned my throat.

“I only know about me, of course,” I said. “But I know I’m not the first.”

“Did she make you strip when she interviewed you?”

“No, she just asked me if I was a virgin.”

“And were you?”

I blushed again. “No. I’d had a boyfriend.”

“When did she first get you naked?”

“She took me away on a business trip. We shared a room. With only one bed.”

“Was it fun?”

“To be honest, my mind was all confused. I’d only had boys before. But my body loved it.”

“I bet your body looks great naked.”

I had no idea how to reply to that. But the vodka had an idea of its own and I stood up. I watched him watching me as I pulled my top off over my head. Then I reached behind and undid the zipper on my pants and slipped them off. I stood there in just bra and panties. I turned away from him and I could feel his eyes on my back as I undid my bra-strap and took it off. Finally I slipped my panties down. I could feel him staring, inspecting my ass, trying to get a little peek at what I had between my thighs. Slowly I turned around. His eyes went from my breasts to my shaved pussy and back.

“Very nice,” he said. “You are lovely.”

I moved up onto the bed and undid his belt, opened up his pants and took out his rock-hard cock. I wrapped my mouth over it as Catherine had taught me to do with Tim’s cock. He groaned when I caressed his knob with my tongue.

“Oh babe you do that well,” he sighed as I started to move him in and out of my mouth.

I slid my hand inside his underwear so that I could stroke his balls as my mouth fucked his cock. As I felt his arousal building I took him deeper into my mouth. Into the back of my throat.

“Oh babe, make me cum,” he moaned.

I let my hand slip deeper between his legs until my finger felt the rough pucker of his asshole. I knew he was close. I took him as deep as I could into my mouth, fucking him harder and faster, at the same time I forced my fingertip into his ass.

“Oh gosh, yes, babe, go on, suck me dry.”

His cock twitched and I felt the first warm jet of cum shoot into my mouth. His cock was twitching and his asshole was clenching as he pumped my mouth full of his delicious cum. Finally, when his cock was still, I sat up. I opened my mouth so he could see the amuse bouche he had given me and then I swallowed it.

“Time for dinner,” I said.

Dinner was amazing. I’d no idea what half the stuff on the menu was. I’d never eaten in that kind of place before. I ordered a steak and Pieter told me that was boring and ordered a fish dish instead. I knew from Catherine that my pussy loves it when someone takes charge and it was just the same with him. I couldn’t wait to finish dinner and get back upstairs. My pussy wanted his cock like I’d never desired before.

Back in the room he poured me another glass of champagne. He’d drunk wine with dinner but I couldn’t. I was too young. I felt the alcohol almost with the first sip. My pussy was desperate to be filled. Not just because he was a man but he seemed to be so in control. In control of me.

Without even discussing it I undressed. Down to my panties. Although since I was wearing a tiny thong, not much was hidden. Just the lips. I could feel his desire, his longing for me to slip off my panties. To see my slit. My mound. To lay me back and spread my legs.

I lay on the bed. He reached down, ripped my thong and tore it off me. He forced my legs apart, not that I was resisting. A moment later I felt the wonderful feeling of his tongue everywhere, in my pussy, on my clit, even in my ass. I was moaning uncontrollably, my body was shaking. I don’t think I’d ever been so aroused. His tongue squirmed around in all those folds down there. I knew I would cum for him almost immediately, I was just a bundle of excitement. My pussy was flooded with arousal and his tongue was lapping it all up.

“Oh my god,” I heard myself moan. “I’m going to cum.”

My body froze for a split second and then I was shaking again as my orgasm exploded. His tongue swirled around inside my pussy as it pulsed with pleasure. It seemed to go on forever.

“Oh god, don’t stop,” I moaned as my body throbbed and my toes curled and my scalp tingled. I don’t remember what happened next but when I recovered from my climax I realized he was inside me already. His cock was sliding back and forth inside my wet cunt, and wonderful feelings radiated out from between my legs throughout my whole body. I was moaning again, I just couldn’t keep quiet if I’d tried.

He pulled out of me and rolled me onto my front. I got my knees underneath me so my pussy was on offer to him between my thighs. I felt like a mare presenting to a stallion. His cock slipped back into my body easily, he felt so big and long and deep inside. He grabbed my hips and started to fuck me hard. Vigorously. Almost violently. My clit was dying for a touch. I put my hand between my legs and started to masturbate.

“Oh babe you are so tight,” he said as his wonderful cock pumped my body full of arousal.

I squeezed my pussy around his cock, tightening myself even more.

“Oh fuck babe, you are going to make me cum.”

He pulled out of me. I rolled onto my back just in time to see his cock detonate and a thick string of white cum shot up between my little breasts. His cock jerked again and again as my body was latticed with his sperm. I rubbed my fingertips in it and then stroked my nipples using it as a sort of lubricant. They were hard as little pebbles and incredibly sensitive. It was if there was a direct connection between my nipples and my clit. As I rubbed them I could feel my pussy rippling with delight. I’d read somewhere that some women can cum from playing with their nipples. That evening was the only time I’d felt I could even get close. I pinched my nipples hard. He slipped his cock back inside me. Somehow it felt even bigger than before. He let his arms relax and laid his body on top of mine. We lay there like that, our bodies almost glued together with his cum, his cock softening inside my pussy. I wrapped my arms around him and held him against me. He kissed me, twirling his tongue against my own. I could feel my pussy getting interested again already.

“Oh babe,” he said. “You have a fabulous body.”

I felt so proud. I know I don’t have a supermodel sort of body, no boobs for a start, so I don’t get told I’m attractive very often. It makes me glow all over with a special sort of warmth on the rare occasions that it happens.

Pieter finally peeled himself off me. I went into the bathroom and had a quick shower. When I came out again, he had made me a new drink, lots of ice, vodka and tonic. The perfect after-sex drink. My brain was softly buzzing from the earlier alcohol, my pussy was softly buzzing from the earlier sex. It felt perfect. I’d already told my parents I was going away on an overnight business trip with Catherine so I could stay until morning.

I had never woken up in bed with a man before. I had spent nights with Catherine but the only cock I’d had recently was Tim’s in her office. I knew it would be special to wake up with a man beside me for the first time in my life. Plus I knew that however late it was when I finally got to the office that Catherine would not tell me off. She would want me to make sure Pieter was as happy as I could make him. And my pussy was in the mood to make him very happy indeed.

He still seemed to be asleep when I awoke. I put my hand on his cock. Despite being asleep he was rock hard. I slid my body over him and moved so that his cockhead was nestled in the entrance to my cunt. I slowly pushed back. I was surprisingly wet and he slipped in easily. He opened his eyes.

“Oh babe you know how a man likes to be woken up.”

I sat up on his cock and started to rock my hips.

“Touch yourself,” he said. “I like to watch a girl pleasure herself.”

I reached down and started to stroke my clit as I fucked him. It felt wonderful, his lovely cock inside my body and my finger caressing the most sensitive little spot on my body. His eyes watching me as I put on a show for him. After a few minutes I was getting close to orgasm. I stroked my clit a little less intensely letting him catch up. When I felt that he was getting close to cumming too, I rubbed my clit hard.

“Nnggh,” I grunted as my orgasm hit. I felt my cunt spasming around his cock.

“Oh babe, you made me cum too.”

I rocked my hips and pumped his cock empty inside me while I continued to coax the last little ripples of pleasure from my clit.

“Did you fuck him?” Catherine asked me when I finally got to the office.

“Yes,” I said. “Wasn’t that what you wanted?”

“Of course. Was it fun?”

“The best I’ve ever had. It was incredible. I’ve never felt so grown-up. It’s the first time I’ve woken up in bed with a man.”

“Sounds like he is a good lover.”

I laughed. “You should have him yourself next time.”

“Maybe,” she said. “Or perhaps we should both have him together. That would be fun.”

The next time was a couple of weeks later. Not with Pieter but with Sam. Catherine told me the room number in the hotel. Going up in the elevator I was terrified, almost shaking with fear. Or maybe with arousal, they all mix together sometimes. I’d never done anything quite so blatantly sexual as going to a hotel room to fuck someone I’d never even met before. I knocked lightly on the door, as if perhaps I could escape if nobody heard it.

“Hi,” Sam said. I stood there unable to say a word. Catherine had provided a surprise for me. Sam was a woman. Maybe fifty. Attractive and dressed in what looked like they must be very expensive clothes. Elegant. She looked at me with uncontrolled lust.

“I’m Samantha,” she said, looking me up and down. “You must be Fiona. Catherine said you were cute and you are.”

She bent forward and kissed me. I was completely taken by surprise, still standing in public in the hotel corridor outside her room. She drove her tongue into my mouth and put a hand on one of my breasts. I couldn’t stop myself letting out a little moan. She pulled me into her room and locked the door. Her fingers were on the buttons to my blouse, then my bra strap, my belt buckle, my zipper. In a few seconds she stripped me down to my panties and a moment later they were around my ankles and her fingers were between my legs exploring. I was purring with delight as her finger found my opening and penetrated my body.

“I bet you taste nice,” she said quietly as she pushed me onto the bed. I spread my legs for her without being asked and then there was the wonderful feeling as the tip of her tongue found my clit. My pussy was soaked with passion as she pressed her finger back inside me. I was moaning and quivering with excitement. Somehow she had a finger in my asshole as well as one in my pussy, and her tongue knew just how to work its magic on my clit.

Suddenly she went away. I opened my eyes and watched as she slowly undressed herself. She had a tight body although I could tell immediately that she had had children. She must have been stunning naked when she was my age, I thought. She had large breasts, much larger than mine of course, larger even that Catherine’s. Her pussy was a deep furrow at the base of her belly, shaved but with a patch of hair left for decoration. I could see the pink of her inner lips nestled between the smooth hairless swellings of her outer lips.

She moved onto the bed. I thought she would start to lick me again but she moved further up the bed, pushed me down on my back, straddled me and pressed her pussy against my mouth. My tongue pushed forward and slipped inside her. She tasted sweet, like a fine wine that was perfectly aged. She sighed with pleasure as I started to lick her, running my tongue up and down between her labia, pressing it inside her entrance, feeling for the tiny hard button of her clit.

“Oh yes,” she sighed. “Catherine has trained you well, you little slut.”

She started to rock her hips a little, fucking my mouth with her pussy, pushing herself even harder onto me as if to get my tongue deeper inside her cunt. Then she moved her hips further forward.

“Lick my asshole you dirty slut.”

I pushed my tongue against her asshole and circled it there. As I felt her body relax a little I pushed the tip into the center.

“Yes, that’s right. Get it right in there,” she said, pushing her ass hard against my tongue.

I felt her asshole start to open up, felt my tongue start to go inside her. She was squirming around on my tongue clearly loving it. Finally she moved her hips back so her pussy was over my mouth again.

“Now lick my clit and stick a finger in my ass.”

I reached up and found the rough skin around her asshole, slick with my saliva. I circled for a few seconds and then pushed hard. She groaned as I felt my finger slip inside the tight ring of muscle.

“Make me cum, slut.”

I fingered her asshole as I attacked her clit with the tip of my tongue. She was sighing and moaning encouragement. Suddenly she let out a long wail and I could feel her orgasm in her ass. She pressed her cunt down hard on my mouth, almost painfully, as her climax burned through her body. Her pussy flooded my mouth with juice as I struggled to keep my tongue on her clit until she was completely finished.

She lay down beside me and casually caressed one of my tiny breasts, rubbing the hard nipple, sending little flashes of pleasure across my chest. She looked over my naked body. I felt very self-conscious, her gaze was so intense.

“You are like a boy with a pussy,” she said.

“Sorry, I don’t have much of a figure. Or much in the way of breasts.”

“It’s fine. You have lovely big nipples. And an adorable little pussy that I can’t wait to lick again. Let me see it.”

I pulled my knees up towards my chest and spread my legs as wide as I could hiding nothing. I felt really exposed like that, I don’t remember ever deliberately showing someone my pussy like that before. Only myself in front of a mirror. She reached down and spread my outer lips apart with one hand, so she could have a good look at all the little pink folds hidden within. I could feel how wet I was, there was a little dribble running out of my pussy down to my asshole. She moved her hand and rubbed my juice onto the tight pucker.

“Have you been fucked in here?” she asked.

“Yes.”

“Did you like it?”

“Not really. It’s uncomfortable. But I love the feeling of surrender when I am forced to do it.”

“You really are slutty, aren’t you? I think I’ll force you to take me there with my dildo.”

She got up off the bed and went to her suitcase. She came back with an L-shaped toy, like two cocks joined together. She slipped one of the cocks inside herself leaving the other sticking out as if she was a boy. She rubbed the head of the cock against my lips, coating it with the slippery juices that were seeping from my cunt.

“Spread your ass cheeks,” she ordered.

I reached down with both hands and pulled my cheeks apart, exposing the tiny tight entrance that Tim had been the only person to make use of.

She moved between my legs. She grasped the fake cock and pressed it against me and pushed forward hard. I squealed at the sudden burst of pain but she didn’t relent. She roughly forced the unyielding plastic inside. I felt tears well up in my eyes. At least the plastic cock was quite a bit smaller than Tim had been when he took me there. She started to fuck me hard, gradually forcing more and more of her cock into my ass. I think she enjoyed the fact that I was in pain, she liked to be totally dominant. I could feel tears running down the sides of my face as I lay there, pulling my knees against my chest and spreading my ass open, with a huge dildo reaming my asshole mercilessly. As with Tim, I hated the pain in my ass but I loved the feeling of total submission, letting Samantha do whatever she desired with my body.

Of course the end of the L-shaped dildo that was inside her was turning her on as she fucked me. She clearly was having trouble concentrating, she kept stopping her thrusting before she realized she was the one in control, I couldn’t do much more than lie on my back holding my cheeks apart for her pleasure. At least my asshole was finally relaxed enough that the dildo could move more easily and I was no longer in pain. In fact I was starting to really enjoy it. She was fucking me hard, almost pulling the plastic rod out of my ass before slamming it deep into my rectum. I was whimpering, and also letting out a little grunt each time she roughly re-entered me.

Suddenly she pulled the cock out of me completely. Before I even realized what was happening she violently thrust it between my lips into my pussy. I came almost instantly, my pussy throbbing around the cock, my asshole still throbbing from its earlier mistreatment.

“Oh my god,” I moaned as she pumped my arousal to new heights. My body was glowing all over, warm and excited and consumed with the ecstasy of my climax.

“Yes, cum for me you little tomboy slut,” she said as she roughly thrust her hips back and forth as my body felt like it was on fire. She reached down and pinched my nipples hard. Very hard. I screamed with pain. But somehow the pain in my nipples just made my orgasm even more intense. I reached up and put my hand on her breasts, so large and soft compared to my tiny firm ones. I looked down as my orgasm finally started to die away. It was erotic to see her between my legs, pumping the plastic cock in and out of my throbbing cunt. Finally, when my body was still, she stopped her thrusting and pulled out of me.

“Have you ever been spanked, slut?” she said.

“No, never.”

“Sluts need to be spanked regularly. To keep them obedient.”

She walked over to her case and pulled out a paddle. It looked a bit like a ping-pong bat except it was longer and narrower. It looked terrifying.

“Actually I prefer a cane. It makes such a pretty pattern on the girl’s defenseless ass. But a cane won’t fit in my suitcase. So you will get spanked in the morning. Then I will kiss you. I promise you it will be the tenderest kiss that you have ever experienced. Spanking does that, the brightest dawns follow the darkest nights.”

I could tell that I was going to have a hard time during dinner and in bed later, trying not to imagine how painful the spanking would be. Thank goodness she didn’t have a cane. I’m not sure I’d be able to stand that.

We went for dinner together in the hotel, and then to bed naked. We wrapped our arms around each other and kissed gently and softly. The soft pillows of her breasts pressed against my nipples. For a time I managed to forget about the spanking and we fell asleep together. Next thing I knew it was morning and Samantha was shaking me awake.

She got out of bed and took the clothes-iron out of the closet. She put it in the middle of the bed.

“Stand on the floor at the end of the bed and hold the iron with both hands,” she ordered.

In that position my body was stretched out, my ass completely exposed.

“Keep your legs straight,” she said. “If you bend your knees or let go of the iron then that stroke doesn’t count.”

Without warning she swung the paddle. It really stung and it was all I could do not to cry out. I had a feeling she was starting gently and it would only get more painful. I gripped the iron tightly, my fists tightly clenched around the handle. After a few more strokes my ass was on fire. I couldn’t stop myself crying out, almost screaming. But to my surprise I was having little spasms in my pussy. I could feel my wetness, feel juice seeping between my lips.

Suddenly her finger pushed into my pussy. “I knew you’d be soaked,” she said. “You are so slutty.”

The next stroke was much harder. The slap of the paddle on my ass echoed around the room and then my ass-cheeks erupted with pain. I felt tears well up. The next stroke was harder still. I let go the iron and put my hands over my ass for protection. It was completely automatic, I just couldn’t help myself. She didn’t even need to say anything. I meekly moved my hands back to the iron and grasped the handle.

“Sorry,” I said. “I broke the rules.”

She picked up her iPhone from beside the bed and I heard the sound of her taking a photograph.

“Look how red your ass is,” she said, showing me the picture. My cheeks were bright pink, glowing. My pussy was exposed between my thighs, but my legs protected it from actually being touched by the paddle, thank goodness.

She raised the paddle again. I could just see it out of the corner of my eye through my tears. Then it vanished and I heard it, felt the sting, felt my ass burning, my pussy quivering, having little spasms. I was in pain but I was also totally turned-on. The pain was now in the background. I was no longer crying out, tears were running down my face and juices were running down my thighs. I lost count of how many more strokes she gave me. They got harder but now it seemed that the more it hurt the more I was aroused. I wondered if I could cum from being spanked.

“Stand up,” she said finally.

I stood. She spun me around and kissed me. As she had promised it was the tenderest kiss I’d ever experienced. I felt like I was going to cum just from kissing. It was as if she was making love to me with her mouth and her tongue. My eyes were closed but I sensed her finger between my legs, rubbing my juice all over my clit, touching me. But barely touching me, her finger was like a feather on my clit. But it was enough. It only took a few seconds and I came. I felt my knees buckling underneath me but she had an arm around me and sort of held me up until I managed to regain my balance. She continued to touch me lightly as my clit erased the pain in my ass by flooding my entire body with pleasure. Finally she slipped her finger inside me and persuaded my cunt to do its share. She fucked me with her finger as my pussy spasmed around it. I was moaning and crying. I was definitely not quiet. Being spanked and then kissed had been quite an experience.

“Thank you,” I whispered.

“You may be a slut. But you are a really pretty slut. I want to have you again next time I’m in town.”

Later that morning I was in Catherine’s office. It was a lot better being there than at my desk, it was so painful to sit down.

“She told me she spanked you,” she said.

“Yes.”

“It’s an experience, isn’t it?”

“It is. I thought it would be just painful, I’d no idea how excited I would get.”

“Let me see.”

“What?”

“Your ass. I bet it’s red.”

I pulled up my skirt, pushed my panties down to my knees and turned so she had a good view. I bent over. She got up from her desk and came over for a closer inspection. She licked my ass as if her saliva was some sort of pain-killer. It felt so delicate and affectionate. I could still feel the heat from my early morning spanking.

“You have such a sweet pussy,” she said and then I felt her sink her tongue into it. This was a day that I would remember for the rest of my life. Who knew what future treats my job had in store in the future?