It’s a story as old as time, or at least as old as sex: powerful corporate executive uses status to have sex with impressionable young girls. Yup, I do that. I’ve done that too many times to count, in fact. Thankfully, however, there are a few things that set me apart from the Weinsteins, the Aileses and the Cosbys of this world.
First of all, I never use coercion to get those young, sweet, impressionable girls to sleep with me. When I seduce them, I make it clear that I am interested in fucking them, but I generally go to the point of killing the mood in asking for clear consent. This is partially to do with the horrible, perverse things I want to do to these girls, but I’ll get back to that later…
Second, if the girl is working at or for my company, I make it very clear that sleeping with me, or refusing to do so, will not affect their position in the company in any way. She gets no favours if she does it, and there are no hard feelings and no repercussions if she doesn’t.
And third, I am a woman.
Yes, that’s right, a woman. My name is Cathleen, I’m 45 years old and I’m what your average financial weekly would call a business tycoon. A tycoon in pretty panties, to be precise. I brought out my first lingerie line when I was 23, straight out of fashion school. This was followed by my own shop, then another shop, then another, and finally a substantial company worth many, many millions. The business is focused on high-end women’s knickers, bras, suspenders, bustiers and stockings-anything to make a woman feel the power of her sex. In fact, our mission is to make women feel sexy, to make them look good to themselves rather than to their boyfriends or husbands.
And yes, I’m a dyke. My interest in girls was provoked in college, at the tender and innocent age 18, when I was seduced by my 50-something English professor. She wined me, she dined me, and she made me feel things no man had ever even come close to making me feel. I still considered myself to be hetero at that time, but after a brief failure of a marriage I started developing my bi side more and more. At some point, I realised I was almost exclusively dating women, and I just went with it. And, as I entered my late 30s, I also discovered my intense lady-boner for fresh, young, nubile girls. Girls who smell like summer, with fresh faces, soft skin and supple bodies. Girls full of life and dreams, full of energy and hope. Girls who are just discovering their sexuality, who can be persuaded to allow a thirsty lesbian cougar to help them on their journey-regardless of whether that journey leads to a long and fruitful new path or to a dead end.
Generally, I pick these girls up in bars. Sometimes, I hire escorts. And sometimes, they’re my employees. The first of the latter was a gorgeous teen girl of Indian descent, who wanted a modelling contract and had somehow discovered my love of ladies (which I generally keep fairly quiet). She emailed me pictures of herself posing seductively in our lingerie, saying she would do anything for a modelling gig. A few back and forths later, she knocked on my door wearing (as instructed) high heels, a gold necklace and earrings, a beige raincoat – and nothing else. When she dropped the coat to reveal her firm bosom and pert little pussy, I sat back in my vintage leather chair and thought to myself ‘I can get used to this’. When, about half an hour later, she was down on all fours, licking my clit with her hands tied behind her back and a big black plug in her virgin ass, I thought to myself ‘I can definitely get used to this’.
Oh yes, I should probably add that I have a pretty kinky streak. I have a basement that could reasonably be called a sex dungeon, considering the contents. But we’ll get to that later.
The main story I want to tell you over these chapters is about Claire. Claire came into my office one day looking for a job, and I was instantly smitten. Claire had angelic golden hair, full pouty lips and the most gorgeous green-blue eyes you have ever seen. She was slim yet rounded in all the right places, with C-cups and a perfect apple butt. Her legs were like a ballerina’s, long and perfectly shaped. Most of this I discovered later, as she came into my office wearing a shapeless pantsuit that didn’t flatter her figure at all.
It was a Friday. I had been working like a dog all week, trying to put together a distribution deal in the Middle East (you wouldn’t believe how many women over there wear delectable, expensive panties and bras under their burqas). I was interviewing a bunch of prospective hires for a range of positions, including modelling work. We run a program where girls and women of all shapes and sizes can apply to model our lingerie, and if they have the right energy and look, we give them a sort of apprenticeship where we teach them how to look great before the camera and maybe put them in our catalogue. For some reason, Claire’s resume had landed on my model pile.
“Please, have a seat,” I said, putting on my reading glasses.
“Thank you.” She sat down and crossed her legs, smiling slightly uncomfortably. She had a certain poise, a straightness of posture that led me to suspect she came from an upper class background, and a fancy school. She was every inch a lady.
“Are you nervous?” I asked, my standard first interview question. Those who deny it are liars and have no place at this company.
“A little.” she said, shifting her weight and brushing a streak of golden hair out of her face. Good, I thought.
I flicked through her papers, noticing something was missing. “You should include headshots.” I said.
“H…Headshots?” She screwed her face, confused.
“Yes, headshots. I mean, you’re very pretty but we need to know what you look like in the hands of a photographer. Have you not applied for modelling jobs before?”
“Modelling?” She seemed even more confused. I looked down at her resume, which listed two PA jobs and two years of college. Uh oh.
“I’m sorry,” I said, suddenly the one under the spotlight. “Long day. You’re here for the personal assistant role. I just assumed that you, looking like that…” I stopped myself before finishing the sentence. She giggled, flustered.
She didn’t stand out as a perfect candidate, being only 20 and fairly inexperienced, but I hired her on the spot. I could not let this one walk out. The beaming smile on her angelic face alone was worth a few months salary. We shook hands and she walked out, smiling from eye to eye.
Just as she passed through the door, she turned back.
“Thanks for mistaking me for a model!” she said.
“Easy mistake to make.” I said, with a wink. “I will see you monday, Claire.”
Claire started out well, working hard and keeping on top of my crazy agenda. I was impressed. We got more acquainted over the following weeks. I found out she was living with her high school boyfriend, who was in law school. She grew up in the suburbs of our large city, where her parents still lived. I also noticed that the pantsuit was not a one off; most of her outfits were ill fitting and unflattering. I got the idea that she shopped for high fashion brands but at outlet stores (hence the bad fits), and/or that she didn’t want to draw attention to her sublime figure.
I didn’t really have a plan for getting in those oversized pantsuits at the time. Business was crazy, and other things kept drawing my attention away. Then, after about three months, Claire’s performance started to change dramatically for the worse. She came in late two or three times a week, always looking flustered. She misrecorded an important appointment with a supplier, which caused me more than a little embarrassment. And she looked tired most of the time, with bags under her eyes and messy hair. I had to find out what was going on. So, on a Friday afternoon, I called her into my office.
“Yes, Cathleen?”
“There’s something we need to discuss. Would you like to get a glass of wine?”
“Uhm, OK…” She didn’t say much in the taxi ride over to my favourite wine bar. She seemed a little apprehensive. We finally settled down in a quiet corner of the bar, sitting next to each other on a big chesterfield with a glass of Merlot.
“So, Claire-how are things?”
She looked at me with her big teal eyes. Her lips began to tremble. Then, without warning, she broke down.
“Please… Please don’t fire me.” She pleaded, her voice shaky. A big tear rolled over her cheek. Then, the floodgates broke. The poor girl started sobbing uncontrollably into her jacket sleeve. “I’m so… So sorry.” she said softly, as I put my hand on her shoulder. “This is so unprofessional… I know I’ve been bad… Please, please give me another chance. I’ll do anything…”
With any other girl, this would be an opportunity to take advantage of the situation. But somehow, doing so didn’t feel right with Claire. This wasn’t how I wanted to get her, even if I did want her. Badly.
“Claire,” I said, “Look at me.” Her deep sea eyes climbed slowly to meet mine.
“In this company, we care about more than work performance. If there’s something wrong with someone in our family, we want to help.” Trite, but accurate. I put my hand on her knee.
She smiled through the tears. “Thanks… That really means a lot to me, Cath… But I don’t think you can help me with this.”
“You’d be surprised.” I said “Try me.”
She told me her boyfriend had cheated, that she had broken up with him. (Attagirl). But, because she had been living in his apartment, she was forced to move back in with her parents. As it was an hour long commute, she was tired all the time, and often late. She said she was looking for a new place, but affordable one-bedrooms and studios were almost impossible to find in our city.
A plan began to form in my head. A few years previous, I had bought an apartment in the middle of the city, as an investment. It was a clean, minimally furnished but still luxurious and spacey one bedroom on the 9th floor of a new tower block. Sometimes, I rented it out to tourists. Sometimes, I let friends and business relations stay there if they were in town. And sometimes, it was a convenient place to take my young and pretty prey after a hunt in the bars below.
“What if I told you I have a place here in the city you can stay until you get back on your feet?”
“Wh… What?”
“I have an apartment. Only a few blocks from here, in fact. I usually rent it out, but I’m between tenants. You can stay there until you find a place, it’s like 10 minutes walk to work. No more excuses for being late.” I smiled.
Her face beamed up, carrying an expression you would expect from a person who had just won the lottery. “Oh Cathleen, thank you! Thank you so much!” She hugged me, tightly. For the first time, I felt her gorgeous body against mine. It felt good.
I promised Claire she could move in on Sunday, and I took the Saturday to set things up. My goal, over the coming weeks, was to give her some clear hints about both my sexuality and my desire for her, without being too obvious. I put a big book of fine art photography on the coffee table, which contained lots of naked ladies, some of them kissing and touching each other. I hung up one or two pictures of a similar bent. And the giant box of lingerie, dildos, vibrators, butt plugs, lube and porn that I kept around for my dates; I hid that badly on the bottom of the closet, hoping she would snoop.
My original plan was to show up one evening unannounced, to ‘check if everything was OK’ and take it from there. But then, luck dealt me a much better card. I was invited to a fashion conference on a beautiful, warm island, about two hours flight away. We received two tickets.
Claire had improved immensely since I put her up in my place. It was like night and day. She was confident again, more confident than before even. She making jokes and forging good relationships with the other girls in the office, joining them on nights out. She had a certain nonchalance about her now, like she could handle anything. So, I thought, let’s see if she can handle a cougar attack.
On a balmy June afternoon, we arrived at our rather nondescript concrete box of a luxury hotel near the beach. The rooms were nice and big, with king-size beds, huge flatscreen TVs and walk-in showers in the bedroom. Our rooms were next to each other, with a dividing door which I made sure was kept unlocked. Our evening of arrival was given as free time, so that everybody had time to recover from their journey. After about an hour of settling in, I knocked on the dividing door.
“Come in!”
Claire was still unpacking, wearing a blouse and baggy navy suit pants. On her bed, she had laid out her underwear. Very, very boring and plain stuff, all. The kind of undies you might buy in ten-packs at a supermarket. I saw an opportunity, and jumped on it immediately.
“Claire, Claire, Claire… You work at a lingerie company… How can you be wearing this… this generic, off-brand stuff?” I asked, tutting for extra effect.
She shrugged. “Oh, that’s never really been for me… I like underwear that’s comfortable, not the fancy stuff. Plus, I don’t have anyone to show it to anymore.”
“See, that’s what most women get wrong about lingerie. You don’t wear it to attract some stupid guy. You wear it to attract yourself.”
She looked at me, nonplussed. I had to explain myself better.
“Let me give you an analogy. You know those guys with a hard-on for the army, who aren’t actually in the army? The guys who go out in public wearing combat fatigues and dog tags?”
“Yeah, so? They’re fantasists. What do they have to do with lingerie?”
I sniggered. I loved pontificating about this stuff, given the right occasion. “Those guys wear their camos because it makes them feel empowered. It makes them feel like they’re macho men, super soldiers. Even if they’re accountants. Even if they would shit themselves in anything resembling a combat situation. It doesn’t matter. As long as they’re wearing their fatigues, they’re indestructible in their minds.”
Claire was still skeptical. “And the lingerie is like those fatigues?”
I nodded. “Sort of. Even if a woman doesn’t fit traditional beauty standards – and don’t get me wrong Claire, you fit all those standards and more – but even a woman who doesn’t fit those feels sexy and empowered when she wears a bra and panties that compliment her figure. That’s what it’s all about.”
Claire said nothing, but she looked so pretty being skeptical that I almost wanted to leave it at that. Instead, I made my move.
“You know what?” I said. “Just wait.” I walked back into my room and grabbed the pile of underwear I had prepared so carefully.
“Here,” I said. “These are some samples I took along for the conference. Luckily, I think everything should just about be your size. Why don’t you try these on?” Luck, my fragrant ass. I had agonised over the right sizes since the second she agreed to join the trip.
Claire sat on the bed, looking unsure.
“Claire,” I said, “I made a fortune designing and fitting lingerie for women. This is my talent, my great skill in life. Let me show you.”
She hesitated for a few seconds. “Okay… If you say so, Cath. Where do I start?”
“Here.” I handed her the first set I had picked out so carefully: a fairly conservative dark green number with medium butt coverage and no push-up effect in the bra, and a pair of standard hold-up stockings.
Claire shrugged. “Wouldn’t hurt to try, I guess.” She went into the bathroom with her new clothes. I sat back on the bed, crazy with anticipation. Then, finally, the bathroom door opened and my perfect princess came out, still adjusting her bra strap. My god. She looked better than I could have imagined, even in my wildest fantasies (and they had been pretty wild). Those long legs, that perfectly round butt, her perky and firm breasts…
“Claire,” I said, clasping her arms gently, “Tell me, how do you feel?”
She looked down at herself and smiled. “I feel… Good! Really good! You weren’t lying.”
I grinned. “It’s my job. But I think we can do better. How about this?” The next set was far racier, dark blue and lacy, with a push-up bra, a suspender belt to hold up a pair of beautiful net stockings, and a tiny little thong. “Have you ever worn a suspender belt?”
She shrugged. “I’ll figure it out.”
And figure it out she did. As good as she looked in outfit no. 1, outfit no. 2 made it pale completely in comparison. The thong, especially, was a perfect addition. Seeing those unbelievably shapely pink cheeks in full glory… I had to contain myself not to throw her on the bed and feast on them.
“And?” She said, twirling around and nearly giving me a heart attack. “What do you think?”
“Claire,” I said, “Let me put it this way. If I were to put you in our catalogue wearing this, Victoria’s Secret would steal you away the next morning.”
She giggled, blushing. “Stop!” She made a flirty ‘oh, you’ gesture. This was almost too good to be true.
“Can I… Can I have a pair of these?”
I smiled. “They’re all yours. If you admit I was right?”
“You were completely right.”
I hadn’t been sure beforehand whether I could give her the third pair I had picked out at all, as they were very risqué. Both the bra and panties were almost completely made out of see-through mesh. Only a few tiny, strategically placed decorations covered up the nipples and vulva. But Claire was unleashed.
“Go on, give me one more.”
I hesitated. “Okay, this last set is pretty revealing… I can leave you alone with them if you like.”
“Nonsense,” she said, eagerly grabbing the set from my hands. “I need your opinion!” And she was gone again. Waiting for her, I was more aroused than I had been in a long time, and I was aroused very, very often.
“Wow, I see what you mean.” Claire said, checking herself out in the bedroom mirror. “Good thing I have little nipples.” I could only nod in stunned agreement, fairly sure that my panties were soaking. I could see almost every inch of her flawless body, including a well-groomed bikini line.
“So,” I said, composing myself. “You’ve just learned an important lesson, my dear. Why don’t you keep that on during dinner?”
We had a pleasant dinner in the hotel restaurant. I had a hard time focusing on our conversation, however. I kept picturing that goddess-like body in almost wholly transparent lingerie under the frumpy pantsuit, and the things I wanted to do to it.
After dinner, we retired to our rooms. I got out of my dress and turned on the shower. Once under the hot water jet, I squirted a generous helping of scented soap on my hand. Working the soap into a lather over my breasts and tummy, my mind again turned to Claire. I thought about her hair, her smell, her 1,000 watt smile. I thought about her firm breasts, jiggling under one of my prettiest bras. I thought about kissing her neck, running my hands over her tight abdomen and clasping her butt cheeks. And, before I knew it, my middle finger had slid down to my pussy, and began to slowly circle my clit. I leaned back against the shower wall and closed my eyes. Oh Claire… To hold her, to kiss her, to touch her…
“Are you thinking of me?”
I opened my eyes, startled. There she was, standing in the bathroom door opening, looking at me without any apparent emotion. A bath towel covered her torso, her long legs sprouting underneath. I was caught en flagrante by my employee while pleasuring myself in the shower, and I panicked. Instinctively, I tried to cover myself with my hands.
“Claire, I…” I began, still trying to form coherent thoughts in my panic. Claire stared straight at me. Then, in a sleek and deft movement, she pinched the towel and pulled it loose. It dropped to the floor, and I finally got to see the work of art that was her body in its entirety. She took another step towards me, opened the shower door and stood right in front of me, still not breaking eye contact.
“Do you want to fuck me?” She asked, almost matter of factly,
“Because you can fuck me if you want.”
I was taken aback completely, but I was very willing to go with the situation. Without thinking, I put my hands on her hips and moved my mouth in for the kiss. Claire, however, put her index finger on my lip.
“If we’re going to do this, I need you to tell me one thing”
“Anything.”
“If this goes wrong, for whatever reason, you won’t fire me. We’ll go back to being boss and employee, no hard feelings.”
“Yes.” I said. “Naturally.”
“Good.” Claire was a good two inches shorter than me, but in this moment it felt like she towered over me. She pulled my face to hers and kissed me. Her lips were even softer than I could have imagined, and she tasted like strawberry and mint. Slowly, tentatively, her tongue came out to explore my mouth and meet my own tongue in the middle. God, this girl could kiss.
Her hands were on my hips, gently feeling her way around the contours of my body. I felt like a little girl who had the toy store all to herself, not even knowing which toy to play with first. Being more of an ass woman than a tit woman, I decided to start by rubbing my hands over her lovely round cheeks. Her mouth curved into a smile, encouraging me on. I ran my fingers lightly through her crack, teasingly brushing past both her rosebud and the bottom of her labia before circling back up to the top of her butt. Her heavy breathing informed me how much she liked that.
Meanwhile, Claire had gotten hold of my breasts. I’ve always been proud of my round D-cups, though the ageing process had been taking hold in recent years and they’d started to sag a little. Looking at Claire’s face, however, you would think they were no different from when I was 21. Her eyes were fixated on them as she cupped me with her soft hands, like she was holding a priceless jewell. Then, she pushed her face in, attacking my breasts vigorously with her lips and tongue. I threw my head back in ecstasy.
Suddenly, Claire withdrew. She turned the shower off and got out.
“Come.” she said, throwing me a towel. Once we were dried off, we got back to making out in the bedroom, sitting on the edge of the bed, our nipples hard from the change in temperature and our pussies soaking wet from horny anticipation. Claire put her towel down on the bed, then pushed me on. We kissed, lying next to each other, hands everywhere. Then, suddenly, she unlocked our embrace again. She held my face in her hands and looked me straight in the eye.
“I want you to eat my pussy, Cath.”
It was almost a command. Now, this was indeed a part of my usual routine. I liked to eat girls out early in our lovemaking, to make them feel at ease and to ensure their first sexual contact with a lady was something they would not forget. Then, after I made them cum like never before, I could escalate the situation into my perverted fantasies. But, in this case, Claire was the one taking charge. This was a very unusual experience for me, and it made me more than a little uncertain.
On the other hand, I really wanted to taste that sweet, sweet young cunt and so I slid down the bed kissing her tight tummy before landing between her legs. I spent a few seconds admiring her clean-shaven little snatch. Then, I began to playfully run my index finger in little ovals along her labia. Eating pussy is one of my most prized skills, and I’ve learned over my twenty-something years of playing with girls that the key is to build up slowly. So, this is what I did. I ovaled up and down, only occasionally brushing by her little clit. Then, slowly, I entered her with my fingertip, letting my tongue taking over from the finger. She tasted so, so sweet. I kissed her clit hood, applying pressure with the tip of my tongue. Claire, meanwhile, groaned with pleasure and put her hands on my ears. I entered her further and started to finger-fuck, while simultaneously lick-sucking her clit. Her hips started swaying up and down, she was breathing hard.
“Oooooh… Cath…”
I was headed the right way.
While pleasuring my young conquest, my naughty, dirty mind started playing up again. I pulled back for a second and opened my eyes, glancing down. I have to admit, I have a little bit of an anal fetish, and I couldn’t help but wonder how Claire would respond to some contact with her cute little rosebud.
“Keep going!” Claire moaned, and I went back to my previous lick-suck-fingerfuck combo. But, at the same time, my left hand moved under the right, and my left index moved in on her asshole. I started with a light tickle. No noticeable response. So, I slid my tongue down and gently started to lick her other hole.
“No no no,” Claire said, clasping my head. “Not yet. Keep doing what you were doing. I’m close.”
Slightly disappointed (spoilt brat that I was), I got back to pussy eating. It wasn’t long before I felt her perfect thighs close in on my ears. Her breathing became deeper, her hip thrusts more frequent. Then, just as I was entering her with a second finger, she came. Hard. Her pussy cramped together in waves and she pushed me off.
A little later, we were lying down under the covers, spooning.
“How did you know?” I asked, gently running my hand over her breasts.
Claire scoffed. “Please. Do you think I’m stupid?”
This was a reaction I had not expected.
“I asked around. Some girls in the company had some interesting stories to tell.” I laughed, knowing I still had some higher ground. I was counting on the girls telling the stories I allowed them to tell.
“And then the apartment. The high-art lesbo porn book was a pretty big hint. And then there was the big box of toys you had ‘hidden’.”
I giggled. “You find it, then? Did you…?”
“Did I watch your porn while wearing a pretty silk negligee, with a plug in my ass and a massage wand on my slit?”
Wow. Did she? I said nothing, hoping for an answer. Also, hearing her talk dirty, with that perfectly high-class accent of hers, was a major turn on.
“I thought you’d have the place rigged with secret cameras. You didn’t?”
I giggled. “That would be creepy. Well, creepier. No, even I have my limits. But… did you?”
“That,” Claire said, “Is a question I will answer in due time. For now, let’s just say I’m more of a freak than you thought. Now, I should go to bed. We’ve got an early start in the morning.”
Alone in bed, my thoughts went back to my crazy, passionate night. Although my trip with Claire had already exceeded all my expectations, I still had a slight yet nagging doubt. Never had I expected her to take charge the way she did. It felt like she held all the power, barging into my shower and making me eat her out like that. It was time for me to take it back…
Source: reddit.com/r/eroticliterature/comments/79je7s/beauty_and_the_cougar_pt_1_ff
more please! :)