Her name is Mary, and she's been my part-time assistant for over fifteen years now. Did I mention, she's twenty years my senior?

Her husband had passed about six years ago, and she'd been quite active socially since then. She'd married Ron when they were both twenty and adored him every day.  Unfortunately, time does march on, and Ron's unending smoking sent him home.  Mary leaned on me a lot for the first year.  It was more just for someone to talk too back then.  She was quite capable of taking care of her own affairs. Mary had always handled the money, which there had been plenty of for the two of them.  

Since Ron's passing, Mary spent more time filling up her life.  She joined a gym, began a weekly night out with her girlfriends, and generally was more social.  She also had many gentleman friends that tried desperately to attach themselves.  But Mary wasn't about to settle down and told me so numerous times during our twice-weekly office lunch out.  You see, she'd been working with a personal trainer for the last six months. Mary was quite toned and looked twenty years younger.  She was always in good shape for her age, but now she was closing in on being hot.

It was during the latest lunch that Mary was uncharacteristically brazen.  She'd always been open and honest and even a bit forward. But there'd never been a sexual component to our relationship.  

"May I ask you a personal question, Sam?" Mary inquired with an eager look in her eye.

"Of course, Mary, you know that you can ask me anything," I responded.

She moved her chair closer and proceeded to whisper into my ear.  "I need your help with something rather personal."

"You know that there is nothing that I would refuse you.  You have been a dear friend and loyal employee for a very long time.  What can I help you with?"

"I'm thinking of getting back on the horse and could use some personalized instruction."

"And you mean what, by that?"

"I've only ever been with one man in my whole life, and it's been over ten years since I was with him."

"So, we're talking about sex here?  Wait, you want to have sex with me?"

"Yes.  I need it to be with someone that is already close to me.  I'm afraid that I'll be too nervous with someone I don't know that well."

"But Mary, we're friends.  Very good friends as far as I'm concerned.  I don't know that I could even do that with you.  I've only ever thought of you as a dear friend."

"Okay, I understand your hesitation.  And I agree, we are excellent friends.  But how about you stop by the house tonight after dinner for a nightcap, and we continue our talk.  I really need your help with this, even if it's just through conversing."

"That sounds like a good idea.  Now let's get back to enjoying our lunch."

We went back to the office after lunch, and Mary finished up her duties.  Before leaving, she said, "How about eight o'clock tonight? Does that work for you?"

"Sure, Mary, eight o'clock is good for me.  I'll see you then," I answered before she disappeared through the door.  It was almost five when she left, so I put in another hour before leaving.  With our talk still turning in my head, I opted for dinner at the local pub.  I knew that I could get a decent meal and a beer or two.  I figured a little alcohol would strengthen my resolve in our upcoming debate. However, I did limit myself to two beers and enjoyed a nice steak for dinner.  I definitely didn't want to go there drunk.

I was finished at about seven-thirty, so I called Mary to see if it was okay for me to come a little early.  "Seven-thirty is fine," she said as she seemed to rush me off of the phone.  I took her dispatch to mean that she was not quite ready for me.  With that in mind, I took my time on the five-minute drive over.

I pulled into the driveway and sat for a moment.  I was trying to think of all the possible rebuttals that she might come up with.  Mary was a smart lady and usually got what she wanted because she knew how to ask.  She never whined or begged.  So I sat a little longer to mentally prepare. In hindsight, I should have known that I was no match for her diligence.

When I thought I was ready, I headed toward the door.  I didn't even get to knock before Mary opened the door.  She was wearing a wraparound red dress that passed her knees.  I was pleased with this choice as she didn't seem to be playing the 'great legs' card. She was wearing black stockings, which are a particular weakness of mine.  Did I ever tell her that?  Did I mention that I saw her once leaving the gym in her spandex?  That vision had appeared repeatedly in my brain since lunch.  Needless to say, she has great legs. Not only for someone of her age but also for someone half her age.  And it was there again.

Mary asked, "Would you please come in kind, sir?  I believe that we have lots to discuss."

I moved inside the door and said, "Thank you, young lady," as she walked me toward the living room.  

"Chair or couch," Mary inquired.

"Chair, I said quickly, thinking that I'd outsmarted her already.

With a little smirk on my face, I watched Mary head for the kitchen while asking, "Drink?"

"Just water for me, thank you!"  Another one in the win column tonight.

Mary quietly got my water and made herself a vodka on the rocks.  I sat there watching her make the drinks and caught myself staring at her hour-glass figure.  She started my way, drinks in hand, and I snapped out of my ogling.  Damnit, that was one for her!  Women are just so much better at subtlety, that it's not even fair.  She placed my water in front of me and then went to sit on the couch.  Once she was settled in, Mary slipped off her shoes and curled her legs up beside her.

All comfy looking, she started, "So let me say right up front that I appreciate your taking the time to talk more.  You brought up some very valid reasons for not wanting to do this.  I, too, truly appreciate your friendship and wouldn't want to do anything to jeopardize that.  So, in conclusion, is there anything that I can say to get you to change your mind?"

"Mary, I think that you are a beautiful woman, and most men would be lucky to have the chance you're offering me."

"But," Mary interjected.

"But we are great friends and co-workers.  I've seen too many people cross that line and have it blow up on them."

"So, it's not only the friendship but being co-workers that throws a wrench in this?  Even if I quit, we'd still have that very trusting friendship to contend with.  The friendship that saw me through the loss of my husband and you through a divorce.  That's a friendship that could stand almost anything, don't you think?"

Damnit, she is good!  As I carefully built my response, Mary sipped her drink across from me and stared with bedroom eyes.  My resolve was weakening, and she knew that.  I took a sip from my water and just winged it, I had nothing else.

"What if we do this, and I fall hard for you.  Do you really want me chasing you around like a lost puppy?  Calling the cops to get a restraining order.  Hiding from me at every corner as I stalk you throughout our town?"  Her eyes looked at me with even more desire.  I added, "Or, what if you fall hard for me and I don't want you.  Wouldn't that break your heart?"

"It would," she admitted.  "I see your point.  Clearly, you've thought this through much more than I have.  And why is that?"

Fucking hell!  She got me again.

"Are you trying to talk me out of it or yourself into it?" Mary whispered with a wry smile on her face.

With nothing left, I simply stated, "I'm sorry, Mary, I just can't do this," as I rose to leave.

Mary stood quickly as I turned for the door and so sensually breathed, "Don't you want to see what you'll be missing?"

With my hand on the front doorknob, I knew that I shouldn't turn around, but couldn't resist.  There she stood, with her dress untied and pulled completely back.  My eyes started at the bottom and ran along her long, firm legs covered in black thigh-high stockings.  They were held up by a see-through black mesh corset with a quarter-cup bra.  Mary's large brown nipples were prominently displayed above the lace cups.  Her panties were also black mesh, and it was clear that her mound was neatly trimmed.  Se had the well-toned body of a forty-year-old, and I was beginning to harden as I gawked.

"Why don't you lock the door and follow me into the bedroom," she uttered.  Mary dropped her dress and turned away from me, exposing her plump ass covered only by a g-string.  I was frozen in place as she slowly strutted toward the hallway.  When she realized that I wasn't moving, she did a little head turn.  Mary raised her hand and gave me the curled finger come hither signal as she continued to stride.  I think it was the pain of my restricted cock trying to break free of my briefs that brought me about. I adjusted myself, locked the door, and followed cautiously behind her shimmying buttocks.

Once we were inside her bedroom, I closed the door and turned back to find her right in front of me.  We looked into each other's eyes for a moment.  In a brief moment of clarity, I offered, "I didn't think you'd play your trump card.  I'm a foolish man led by his base desires, and I will give you whatever you want or need. But, you already knew that, didn't you?"

Mary pecked me lightly on the lips as she unbuttoned my dress-shirt.  I stood perfectly still like a child that was scolded.  Mary kept up the light pecks while suggesting, "Feel free to touch anything you like, Sam."  My hands moved as if controlled by her invitation and touched her thighs just above her hose.  The contact caused her to shudder ever so slightly, like when a chill runs through your body.  I would have missed it if I hadn't been so unmoving. Mary's eyes also changed focus as she gently exhaled.  To anyone else, this would have been a sign to have their way with her.  But, to me, it meant I needed to take my time and let her enjoy every second.

Just as Mary regained her composure, I began a tortoiselike climb along her bare hips.  Goose-bumps rose on her tender skin as I reached the full width of her tempting loins.  She again paused as I stopped and pressed into her for a sensual kiss.  Our lips pressed and pulled until finally, I pushed my tongue between hers.  It was like breaking a dam as she slipped her tongue into my mouth, and we explored.  Mary's hands left my shirt and clasped my head firmly as hunger took her over.  I moved one hand to the back of her head and kept the other securely wrapped around her waist.  We smooched and sucked face for a very long time.  I let her decide the pace, and she seemed enthralled with kissing.

At some point, Mary paused and asked, "Can we lie down, please?  I'm getting tired of standing."

"Whatever you want," I answered.

Mary stood steady as I slipped an arm behind her thighs and scooped her up into my arms.  She pressed hard into my mouth and smashed her lips into mine as I carried her to the bed.  Reaching the bed, I gently lay her down before climbing in next to her.  Mary climbed on top of me and held my face as our tongue-tango continued.  We got going pretty heavily once again as she began grinding her steaming box on my stiffened penis.  I could also feel her unyielding nipples as they dug into my chest.  Mary was clearly working herself into a frenzy.  So I thought I'd add a little to it by letting my hands roam.  I started at her shoulders and softly caressed my way down. Once I reached the bottom of her corset, I paused for effect.

Mary's mouth broke free from mine, and she begged, "Please don't stop!  I need this so badly, please!"

As I let my fingers dance across her exposed cheeks, Mary went back to sucking my face.  I lightly traced her buttocks with just my fingertips as her grinding began anew.  She was almost back in her frenzied state when I started massaging her cheeks with purpose.  It was then that I accidentally brushed across the g-string.  As a devilish thought crossed my mind, I pulled easily on the string. She jumped a little before grinding even harder.  I waited for a few seconds before doing it again, but a little stronger and held it there.  Mary grabbed the hair on my head as she slammed her honeypot down and screamed, "Oh my Goddd!"

To be continued...