The Mentee

Introduction:

"Mid-life crisis" are real...Some men will get a new car and others a mistress. I have done neither but my mind is on overdrive and there are no topics that seem to be off limits. My fantasies combine real life factoids and my imagination on steroids. Hope you enjoy my initial Literotica effort. Comments are welcome.

Chapter 1 involves a woman that worked for me and my damn ongoing mid-life crisis...

A mentor to her and in all the right ways; along with my vivid imagination of what could evolve.

After she left the company where we worked together, I did engage her ...Below is a combination of reality and fantasy...

Laura:

Involved in the hiring of Laura about 6+ years ago, just out of college, when she had just turned 23. .

Nice young woman and very good from a technology point of view like much of her generation.

Laura is attractive and laughs easily She lacked confidence when we hired her but it was enjoyable to see her grow into a young professional.

Always encouraged her to speak up and take chances, in short to go outside of her comfort zone.

We had some fun conversations, mostly kidding back and forth during her tenure.

Remember one such time when she was heading to New Orleans for a bachelorette weekend.

Told her to behave reasonably decently to which she just laughed.

So tempted to challenge her upon returning to work to share one thing that she did outside her comfort level while in New Orleans but bit my tongue...

Mind Starts to Wander:

Friendly with most of the people in the department and on occasion would join them for a beer or two after work on Friday, pick up the bill and leave. They would continue on with their younger colleagues, male and female.

Mentioned to one fellow, Chuck, who worked with Laura that she was on her way to New Orleans for a bachelorette party.

Chuck responded, "knowing Laura it will be a weekend of what happens in New Orleans stays in New Orleans"

I was both surprised and intrigued...

"Really, Laura?", I was incredulous.

Chuck raised his eyebrows and said,

"Laura has been known to enjoy herself.

Find a guy for some fun over a couple of months and move on...

In fact, I think Laura can be a very dirty girl and possibly a bit kinky"

Chuck was clear that these were his impressions and he had no personal knowledge but based on what he heard thought there was a fair amount of truth in what he said...

" outwardly in public, rather shy but can be very slutty in the bedroom"

"Well Chuck, this has been a very interesting conversation" and reminded him that "what is said in the bar remains in the bar ".

With that I picked up the couple rounds of drinks for the members of the team said good night and was off.

The Fantasies

Mind is in overdrive, thinking of Laura as "a bit kinky". Have always loved the ones that tended to have different public and private personas. In addition, there is something so hot about helping a good girl - go bad.

That said, I'm twice her age and really have no interest in anything long term with such a young woman. But damn this mid-life crisis and where my mind goes. Always hot, frequently kinky, and "what happens in your mind stays in your mind" or at least that is what I thought.

The Condo:

Laura returned from her New Orleans weekend. Made sure to stop by and ask her, how it went and assumed she had behaved reasonably well.

She smiled and replied,

"you know me, always the good girl but had fun"

There was a slight twinkle in her eye as she replied, but was it my imagination based on Friday's bar conversation with Chuck or was she flirting?

Damn this mid-life crisis!

She then proceeded to tell me after living at home for 3 years while she saved money and paid off student loans was now ready to purchase a small Condo.

I was truly very happy for her, told her thought it was great and sure she felt it was time to be on her own and not have to worry about checking in on Saturday night with the parents.

Also reminded her that her parents provided her a roof after college and be thankful they did so.

She both acknowledged the parent's generosity and the desire to be on her own.

"Not having to check-in - priceless!", she said

Damn, there was that twinkle in her eye again...

The Invitation:

Over the next 3 months Laura bought her condo, did renovations and finally moved in.

She shared the pictures of the renovations and she had very good decorating instincts.

Laura was proud of her work and pointed out how she tried decorating things she had never tried before.

Ever the encourager said, "I bet your good at lots of things"

She immediately replied, "What?"

I had not realized how my statement could be interpreted and there was no intention to have a double meaning to my comment or did my mid-life mind take over again.

Quickly went on telling her again that she is a talented woman and will be good at just about anything she chooses to do.

"Regardless, the reason I stopped by is to give you a nice bottle of Champagne. A "house warming" gift.

Now, don't share this with just anyone as it is a very nice bottle of champagne"

She thought for a moment, hesitated and said,

"Would you like to join me for dinner and champagne and see my condo?"

Talk about double meanings!

"Well Laura, I would be honored, But don't want your colleagues to think your sucking up (that one was intentional) to your boss, so let's keep this between us. If you can do that then I would enjoy sharing a dinner and champagne and seeing your Condo"

We set a "date" the following Thursday. Over the next week I was all business, stopping by her work area less than usual.

The day before the dinner she provided me her address.

Told her was looking forward to it and would see her the following evening.

Laura Shows Me Her Condo

I wore a nice tan sports jacket, a blue shirt and slacks. Nice but not overdone and had no idea what Laura would wear.

With her generation, dungarees, sweat pants were possibilities

Arrived 4 minutes after the appointed time and even bought a bottle of red wine to accompany the Champagne.

"Wow" was all I could say as Laura answered the door.

Wearing a dark grey blouse, short black skirt, black stockings and nice heels.

Her eye make up matched the blouse and her lipstick was red, a color she never wore at work.

Kissing her cheek and handing her the bottle of wine commented how fantastic she looked.

"Yes, I can clean up nicely", commented Lauren.

"You look beautiful, very sophisticated. A June Cleaver look". I commented.

"Who?", replied Laura.

Laughing and a bit embarrassed and feeling old, which I am.

" Growing up. Leave it to Beaver was a TV show. June Cleaver, the very domesticated wife, would prepare dinner always dressed up and looking fabulous"

"Sometimes, I like being domesticated", said Laura, as she walked into the kitchen and handed me the corkscrew to open up the wine.

"Normally, I would open the wine myself. But since I'm feeling very June Cleaver like and you're in charge tonight, you do it", said Laura

There goes my mind again and I think I'm starting to stare - damn this mid-life crisis.

We sip the champagne and chit chat,

"Would you like to see the Condo?" asked Laura

"If it's okay with you, let's wait . Have cocktails, dinner, chat and then show me around", was my reply.

Light appetizers, a toast to the Condo, a clink of the glasses, dinner and a bottle of wine followed.

Lot's of laughs, despite agreeing not to talk shop, she tells me how everyone at work respects me and most even like me.

Laura blushed and says, "some of the women even think that I have a thing for you and they tease me"

"Well, I'm flattered that they would even think such a young, attractive woman as yourself would find me appealing", I reply.

There was a moment of awkward silence, which I break by laughing and saying,

"Come on, let's clear the dishes and you can show me how you decorated and put your own touch on the condo"

Laura jumped up and together the dishes are cleared and the final glasses of wine are poured.

"Okay Laura the unveiling time is here and particularly interested in what creative things you did.

As I said before, you have many talents and you should continue to develop them."

Laura shows me the walls she painted, the new floors she had put in, the accents and it all goes together very well.

"You created a nice home for yourself. Young, fresh, a bit eclectic and enough sophistication without being stuffy". I commented.

"There is one more room that I haven't showed you which is my favorite" says Laura.

Since the bedroom is the only one that I haven't seen it doesn't take a genius to figure this out and now I am getting a bit uncomfortable.

Every part of me is saying, thank her for a lovely evening and leave but damn this mid-life crisis.

"Ok Laura, show me your boudoir but I'm looking at it only from a decorating perspective"

She opens the door and turns on the lights low which illuminates the bedroom without overpowering it.

I look around and it is truly nicely done. All the typical feminine touches with a healthy dose of spice thrown in.

"Very nice, very nice and if I may add very sexy too Laura"

My eyes take in the room, I see Laura again looking spectacular with the silk blouse and short skirt.

My defenses are weakening but I can't do this, it could mean my job.

I look around the room and see a book shelf in the corner of the room and walk towards the shelf vs. pouncing on Laura.

"Let's see what your taste is in literature and then I really do need to go"

Walking over to the bookshelf there in prominent display is the 50 Shades Trilogy.

I look at Laura and she clearly understands what I am seeing.

"What can I say", says, Laura "I'm Kinky"

BINGO Chuck's words confirmed.

"Laura, I suspect you will have more than enough suitors lining up for miles, volunteering to help you with your needs, particularly if you wear outfits like the one you have on", was my lame attempt to extricate myself from a situation that could only have one outcome - me loosing my job.

To which Laura replied, "I'm looking for one man, one that is much more mature than the guys I normally hang out with. They don't have the experience, the authority to meet my needs. I want a more mature man. In short, I want you to be my mentor and meet my desire to explore my submissive side"

There it was, a very direct request. "Laura, you have no idea how much I would enjoy assisting you in your journey but can't loose my job"

"I recognize that which is why I'm resigning tomorrow and have taken a job at the local University. Just so you know I decided it was time and they will let me get my MBA for free after working there a year". Laura looked at me with wanton eyes.

"Make the resignation, effective immediately" was my reply and she did. Going over to her iPhone Laura sent me an email to my work address; "Per our discussion, I have resigned my position effective close of business today. I'm sorry for no notice but want to take my unused vacation prior to starting my new role in a week. Your mentorship has meant so much to me and I hope you will be willing to continue doing so, even though I'm no longer part of your team".

And So It Begins:

I walked over and asked for Laura to reapply her very red lipstick and put on even more eye shadow and blush.

She excused herself and went into the bathroom.

When she came back into the room, she looked sooo hot.

A bar stool/chair with a back had been moved from her kitchen counter and placed in front of her bed. When Laura reentered the room. I patted the seat and Laura climbed up onto the stool/chair.

The lights were low but not totally off. The room was sexy, sultry but could see her ruby red lips, her smoky eye shadow, her short skirt, her black stocking and her pumps. She sat on the stool and the skirt was 3/4 of the way up her legs...Laura made no attempt to pull it down...

I moved behind Laura, smelling her hair, nuzzling her neck.

"Don't move. I want to take you in, smell you, kiss you, touch you. But you may not reciprocate unless I tell you to.

Tonight I want to learn more about the other Laura"

"Laura, have always believed you can learn about a woman by looking through her lingerie draw. So while you sit and watch I'm going to do just that and see what I can learn about you"

Laura shifted a bit uncomfortably in her chair, which did not go unnoticed but said nothing..

I opened her top draw and saw the typical cotton panties, padded bras, which I hate, socks, stockings both sheer to waist and control top. which I also hate. If Laura wanted to explore she would have to do better than this.

"Laura for a woman that says, she is kinky, I would expect to see more exotic lingerie"

Laura instructed me to check the draw #3...I moved over and started rubbing her leg.

"Laura, when together I want you to be thinking sexy lingerie, panties and bras. All Sheer or lacy bras, no padding. I like au natural and enjoy seeing a women's nipples through her bra or mound underneath her sheer panties. If you wear stockings then no control top. Some nights you will wear hosiery and other nights you will not"

Laura responded. she would do as I directed her.

Now let's see what is in draw number 3"

Slowly I opened her draw and started to take out her lingerie piece by piece, holding them up, inspecting them and then placing them on her bed. Indeed Laura had some nice lingerie, teddy's, thongs, the aforementioned sheer bras and panties, thigh highs and more revealing negligees"

"Very nice Laura, very hot, I so look forward to having you put on a fashion show for me at a future date and possibly a photo shoot along with the show. In fact, once a week, Thursday evenings like tonight, you and I will get together here and see what mischief we can get into and how I can help you explore your submissive side.

"There are a few more things in the bottom draw", said Laura.

Opening the bottom draw there were sweaters and underneath them I felt the outline of what could only be sex toys. Not one, not two but three.

The first was the largest, the Magic Wand, which I was familiar with. The second slimmer but also a vibrator and the third even more slim but had two heads. Laura explained, the second was a combo vibrator/dildo that she used for internal and external pleasure and the last provided for insertion into her pussy and ass at the same time.

Laura reiterated, "like I said. I'm kinky"

Instructed Laura to stand up and stand still. Laura complied. Button by button I opened her blouse,. Working down from the top. Finally the last button was opened. revealing a black lace bra that thank goodness was only very slightly padded. My hand rubbed her shoulder and slowly worked my fingers down to her cleavage, using one finger running it along the outline of her bra. Laura's breathing was increasing and her neck becoming a nice red hue but not close the her luscious red lips.

Standing by her slide, my hand begins to rub her stocking covered legs, her inner thighs, moving up underneath her skirt.

"Do not move Laura", I repeat.

Truth be told I'm enjoying playing with Laura, moving my hand to just below where her leg ended and her womanhood began.

"Don't move" I reiterated, as I rubbed her ass and back to her thighs and back to her ass again. Telling Laura how nice her legs and ass feel.

Laura tries to push herself against my hand and I quickly told her to stop. She was beautiful and quite honestly feeling as though I had won the lottery feeling up this beautiful young women; however, was playing the role of being completely in charge and letting her believe this is how I treat all my mentees.

Moving behind her I removed my shirt and pants and socks and now just my shorts are separating me and Laura. My hard and erect cock is pushing up into Laura's ass cheeks while I hold her arms to her side...Kissing her neck, she is responding, moaning and pushing herself back into me...Letting go of her arms, I wrap my hands around her and cup her tits through her bra.

Laura instinctively reaches behind herself and begins to rub my cock. Quickly her hand is pushed away and this time I lightly grab her hair, whispering in her ear that she is not to touch me until she is given permission. Once again, Laura acknowledges she understands and her arms return to her sides.

"Since you want to use your hands, kindly lift your skirt up to your hips. I plan on taking you all in"

Laura is standing in front of me, blouse open, skirt around her hips, looking absolutely beautiful.

Moving in front of her the blouse is pulled off her shoulders and now rests near her elbows, making it difficult for Laura to move.

Now my hands become more aggressive and I kneel down on one knee and rub her legs, her ass, and then between her legs.

"Stand still" Laura is reminded.

"Are you getting wet Laura"

"Yes very. And when I orgasm sometimes I squirt"

Jeez I hit the lottery.

"We'll have plenty of time to explore what you can do" and I smack her ass.

Laura replies "oh fuck".

The good girl is starting to go bad.

Standing up, Explain to Laura that its time to see her more of her body and how she can follow instructions.

Circling Laura my mind is deciding how best to unveil Laura for my pleasure.

Nuzzling and licking and smelling her neck while Laura stands in front of me with her skirt pulled to her hips is well, priceless.

What can I do next to help her explore that submissive side and then I see the answer.

On her dresser there is a small sewing scissor and I pick it up.

Moving towards Laura, she is instructed to bend over and put her elbows on the seat of the bar stool that had been bought into the room. Laura is reminded to keep the skirt pulled up to her hips.

It's almost too much to take, looking at this beautiful woman, half my age, bent over in front of me.

Part of me wants simply to undress her and make love to her but I know that is not the role she wants me to play.

One more time she is reminded not to move. Very slowly and carefully the scissor cuts her stocking on the back seam covering her ass. Not all the way to her hips but rather about a third of the way up. The next cut is the most difficult, cutting around the cotton panel on both sides. The last cut is a repeat of the first but up the front seam.

With one quick rip with my hands Laura's panty covered womanhood is there for the taking, while her ripped stocking legs make her look vulnerable and ready to be taken.

Once more thought enters my mind for my mentee.

Instructing her to stand up again, moving in front of her, the scissor is placed between her bra cups and with one snip the cups separate and her tits and nipples are revealed...

Laura's tits are not particularly large, a 34-36 B bra but perky and very kissable.

Moving in front of Laura, I start touching her breasts and around her areolas with my fingers. Her nipples respond growing hard and extending.

"Laura, I want to kiss you but that red lipstick is just so hot and enjoy looking at you standing in front of me, so vulnerable. It makes my cock hard"

Laura is instructed to use just the tip of her tongue to kiss my tongue and to keep her eyes open as we do.

Our tongues meet between our mouths, Slowly first and then with increasing urgency.

It looked so dirty to see Laura kissing me like that, eyes open and my hand continues to feel her up.

Moving from her tits to her nips to her ass and then start more aggressively between her legs.

Laura is indeed very wet and know if I continue she will cum but I have one more idea for my mentee.