Pillow talk

We untangled ourselves from each other, climbed under the covers, and tangled up again.  She slid under my arm, I hugged her tight, and we cuddled naked, spent, and warm.  There was a ticking clock, I allowed myself about 4 hours from the time I walked in her door, and I’d only spent between 30-40 minutes to this point.

For a while we held each other. She placed one hand on my heart, and I placed my hand over hers.  She felt my heart beat, as I listened to her sigh and purr.  I turned my head to look out her window, seeing a tree and blue sky. I know that tree well now, having been in her bed many times since then, in this exact position, holding her post coitus.

After a few moments she took my chin in her hand and turned my head to face her. “Hey, what are you thinking?” She asked.

I smiled and replied quite honestly, “Not a damn thing.”

“If there is something on your mind, I want to hear it” she implored, “Please, share with me.”

“I mean it. There isn’t a thing in my mind. All thought is gone.” I said, speaking only the truth. “Some where outside of this bed, I think there is this world. If I remember correctly, in that world, I have some family function to attend, and you have a class to be at in a few hours. I don’t know. Nothing outside of this bed… Matters.”

“Really?” She asked. I looked down at her big doe eyes.

“Really.” I said with a smile.

She shifted, and lifted her head above mine, and rested her breasts on my chest. She seemed to be examining my features. She traced my nose and lips with her fingers. She straighted my hair, and scanned my face up and down with her eyes.  I didn’t interrupt her, I submitted to her scrutiny, for I was examining her too.

Finally she spoke. “Why me?”

“What do you mean, ‘why you’?” I asked.

“I mean, why me?” She repeated. She paused a moment, thinking. “Why me, of all the women around? Why not some one prettier?”

I was stunned a moment, I’m sure my face  squinted up with confusion. “Um… Have you SEEN you? I figure you must have walked past a mirror in the last few days, really. You are gorgeous!”

She blushed a deep red, and buried her face in my chest. “Stop!” She said, all muffled. She looked up again. “You could have any woman you wanted. Why me?”

I cleared my throat, only to give me a moment to really compose my thoughts. Obviously me responding with something like ‘you are an incredibly intelligent super model with huge boobs, whose also a genius with a giant rack and talks to me like a best friend with enormous tits’ wasn’t going to cut it.  And this nonsense about me being able to ‘have an woman I wanted’ wasn’t something I was ready to accept either.

I took my time, and went back in my mind…

“My first impression of you was that you were incredibly charming and well spoken.  That is an opinion held by just about everyone I know that has met you.  As time went on, and we started speaking more and more, and I got to know you… well, I’ve always enjoyed our chats.  Good conversation is hard to come by, in my experience.” I thought a moment, then continued, “That really is the core of it. Being physically attracted to someone is easy.  I can find myself attracted to a stranger on the street for a fleeting moment, but that is a matter of aesthetics and preference.  With you, well, yes, I love your body, you are beautiful, but it wouldn’t have mattered if I hadn’t been able to connect with you on an emotional or intellectual level.”

She blushed deeply, then quickly kissed me…



Let’s back up

Karen is what you might call A Giver.  While a very sexual being, her focus in the act is on her partner, with her pleasure being secondary.

I’ve always shot for a balance, I guess.  I take my pleasure as a given. I will have an orgasm 99.99% of the time during an intimate encounter.  I can think of only a very few occasions where I did not climax during sex.  But knowing that I am for the most part easy, I really focus on my partner, whose pleasure I take very seriously.  For me sex is… a game.  A challenge.  It is something to do well.  I have a highly competitive nature, which oddly extends to sex.  I know that in a given session I will orgasm at least once, but I need my partner to orgasm minimum twice.  That doesn’t always work out, and sometimes I get a big 0, but it makes me try harder.

Karen puts her partner’s pleasure first too.  She is fine not climaxing, so long as her partner is pleased.  This speaks to a larger part of her character where she is just a people-pleaser in general.  Overall she is an extremely kind and generous person, which is something we have in common.  We often compete with each other to better please the other, which is working out just fine really.

She isn’t the first Giver I’ve been with.  I had a girlfriend once who had a complete oral fixation, and would perform oral sex on me at any time, often times as a surprise for me.  I would often wake up receiving oral sex from her in the mornings.  Honestly, this was a pretty good deal for me.

Karen is similar.  All I have to do is ask, or order, or even just point at my genitals, and oral sex will commence immediately.

Also, Karen is almost a stranger to masturbation.  Self stimulation is something I take for granted that everyone does, whether they will admit it or not.  Coincidentally, Karen and my a fore mentioned Ex both had an aversion to masturbation, for I believe the exact same reason: Shame.  A few other girls I had been with also didn’t masturbate, but it seemed to me that the reason was unfamiliarity with their own bodies.

We had long conversations on oral sex an masturbation prior to engaging physically.  Masturbate? Maybe once or twice, but she did use the word Shame as a reason for abstaining.  I don’t understand the shame, but she had a very religious upbringing.  Giving oral sex? Yes.  She aims to please.  Receiving oral sex?  A few times, which she did enjoy, but it not on her agenda as a people-pleaser.  So, why did she stop me from performing oral sex on her…?

She thought she was being polite.  She thinks of a man performing oral sex as some kind of sacrifice.  She never expects it, certainly never requests it, and thinks its something most men don’t do, and don’t want to do.  After our first time in my office, once we had finished I kissed her, and she pushed me away and covered her mouth, thinking it was impolite to kiss me because she had just swallowed my semen.  She has some barriers that I just don’t have, yet I feel compelled to break them down.

After we connected, and the doors opened, we would begin to sext.  One night, I was able to get her to try to please herself while I sent her messages.  This went over very well, although there was some lingering reluctance for a while.  Gradually she has become more comfortable with the idea, and we have experimented a bit more, her on her own, and us together, which I will detail later on I’m sure.

As to receiving oral sex, that is something else we have worked on, and I think I’ve gotten some positive results there as well.

And I would like to note that it feels strange to speak of things like this, in these terms.  I suppose that is why I created this space, so I could get somethings off my mind.  I do feel often in this relationship that I am teaching her things, expanding her mind.  She is an incredibly smart person.  Her studies are over my head, and way outside my area of expertise.  I feel like I’m guiding her, however.  I guess that would be a natural thing given the big age difference.


Okay, dear reader, moving on, we return to our story, which again is explicit sexual content and thus password protected. The password is: forward4

Click here to read it only if you really want to, or wait for another post on down the line.

PS:  I’m doing this password thing because I know sexual content isn’t something that everyone accepts or enjoys.  Not that I care who is reading or why.  I’m writing for my own purposes.  I will say that I think this has been a net positive however, as the locked posts have about half the readers of the unlocked ones, so people are making conscious choices here.  I like that.

Life on the other side of the line

Over the course of months we came closer, and closer to the line. We set foot over a little… Then ran right over it.  We came to an understanding that we would continue seeing each other.

After our last encounter we each went home, cooled off for a bit, and had a moment of “is this real? Did that just happened?”. Yes it was, and yes it did.  She was a mistress now, of a married man, and cheating on her own significant other.  I’m not a stranger to this, she is, so I would layout modes of behavior.  The one thing I was a stranger to was sleeping with a friend’s girlfriend.  That was quite new.

On Thursday of that week we had our first little test.  I arranged a party, and it would be the first time we were in the presence of our others since we crossed the line. It was a big party, so everyone’s attention was divided. Our first concern was appearing normal. Quick hug hello, light banter, separate, quick hug goodbye. She did make the request that I ‘check her out’ occasionally, which I said was silly on the grounds that I was going to anyways.

The party was large, but not raucous.  It went on for a few hours. A few of my oldest friends were there, one of whom took enough of an interest in her as to comment to me about her later on. A glowing and impressed review, which meant a lot.

Our hugs, exactly 2 mind you, were quick but strange. She remarked on it too.  Like they were now too little… Too light.  But the evening went off without a hitch. It would be some time before we knew when we would see each other alone again.

On the following Tuesday, I had a family function to attend, so time was tight. However I was able to arrange a false emergency at work, giving myself several hours to play with.  I gave myself the time to go off course, and visit her apartment for the first time.

I was nervous the morning of. Timing was critical.  I did have someplace to be, but just a few hours to go off the grid.  Our encounters are still like this, for the most part. We meet in her apartment, or one of our cars, or my office, and occasionally, later on, a hotel room. All of this requires a lot of planning.  Our relationship so far hasn’t allowed for too much spontaneity.

The morning before I saw her, I was dead set on wanting to talk. I was worried, nervous. I wanted to clear the air, and make doubly sure that we had an understanding.  She was accepting. “Just come over. We’ll talk” she said. I made that drive, radio on lightly so I could hear the GPS instructions. I was dressed in my Sunday best suit and tie.

I pulled up to her apartment, and took a moment to breathe. I don’t know why I was so nervous, as we’d already had sex, but I was. I got out of the car, straightened myself out, and sent her a one word text: “Here.”

I walked from the parking lot to her apartment building’s door, and as I was looking for a doorbell, the door opened.

She was wearing, as they say, the ‘little black dress’.

She led me upstairs to her apartment, and walked me inside.  She took my coat, hung it neatly in her closet.  Her apartment is well ordered and kept, befitting her mind, and as a student apartment goes it is quite large. Karen has a job on top of her studies, but I surmise that she also comes from money.  She gave me the tour; kitchen, living room, office, coming to a stop at her bedroom door.

“So, we should talk?” she asked with a smile, standing in front of the bedroom door, yet motioning towards the living room.

“Yes… talk.  Yes.”  I said, looking back towards the living room.  I turned and nodded towards the bedroom. “There is as good a place to talk as any, I suppose.” She started walking backwards through the door as I started walking towards her.  We went different directions at the corner of her bed, she went left, I went right, until we were facing each other on opposing sides.  I put a hand on the bed to steady myself as I kicked off my shoes.  She placed a hand on the bed as well.

Our eyes were locked together, we talked in soft tones about how we were ‘going to talk’. She placed a knee on the bed, I mirrored her.  She climbed up on all fours, I did the same, and we met in the middle, face to face.  Talking ceased, and we just stared and smiled at each other.


Now, dear reader, again I give you a choice. The next part of the story is explicit sexual content. You don’t have to read it. You can if you want, but it is password protected.  If you really want to read it, the password is: squared64

Click here to read the next part, or you can read the safer part later on when I’ve finished writing it.

Well over the line, Part 3

We raised our heads, and smiled at each other, both of us covered in sweat. “Um… Have you seen my shirt?” She asked.

“Uh, oh… One second,” I replied, looking around the room. I stood up, pulled up my pants, then reached for the switch to the bright overhead light. I spied her blouse, grabbed it, and tossed it to her.  She fiddled with it a moment, still breathing hard. “You might want this first,” I said with a smile, twirling her bra around.

She giggled.  I was staring at her, grinning from ear to ear. “Do you like what you see?” She asked, dropping her shirt, reclining naked on the couch.

“I really do,” I replied. I tossed her the bra.    “I think I need a drink of water. Would you like one?”

“Good lord, yes please!” She replied.

I quickly put my shirt back on, and left my office to get two cups of water from the water cooler.  When I returned, she had just finished pulling up her pants. I handed her the water, which she drank deeply, as I drank mine. I walked back to my desk, and sat in the big chair. I leaned back and breathed, closing my eyes a moment. I opened them to see her start buttoning up her shirt.

We made eye contact again, and smiled like fools.  After a moment I motioned a chair beside my desk. “I, uh… Suppose we should talk, huh?”

“Yeah,” she whispered.  She came and sat before me, straighting her clothes.

“I love G, you know?” She stated.

“I know. I love D. With all my heart.” I said.

“Uh… Am I the youngest of your… Affairs?” She asked.

“Yes. By far.” I replied. “Am I the, uh, oldest person you’ve ever been with?”

“Yeah. By far.” She answered. “I mean I don’t think of you as old really, but yes, 18 years is a big age difference.”

I elaborated on my affairs. I’ve been very open with her, and on this matter I’ll be more open with her than you, dear reader.

“If… Um… Well, you can clearly lie. You have done all of those things…” She broached, “Should I trust you? I mean, like, can I?”

“Good question.” I paused. “I will say I will always be open and honest with you, but that means you have to take the word of a known liar and cheat.”

She sat silently for a few moments. “I want this to go on. To continue. With you.” She said.

“This is going to be complicated. This isn’t an easy thing to do. There are a lot of things you have to keep in mind.” I explained. “This is secret. Secrets are hard. Lying is work. Is this something you think you want to do, really?”

She thought only a moment more before replying “Yes. Yes I do.” She smiled, stood, walked towards me, and bent down to put her face inches from mine. “You will have to teach me. I just want…”

I stood to meet her. We looked at each other smiling. “I want to be with you.” She finished.

“Congratulations.” I said with a big grin. “You are now my new mistress.”

“Oh my god!” She exclaimed slapping her hand over her mouth. Her eyes wide as can be, she took her hand away and said, “I really do not like that word! You’ll have to call me something else!”

We hugged each other close, and laughed.

Think you missed something? You might have, depending on how you came in.  This is Part 3 of a story.  Part 1 is here.  Part 2 is here, BUT, I warn you, part 2 contains strong sexual content, and isn’t for everyone.  If you want to, really really want to read it, you need this password: OverTheLine2.  It is entirely up to you. — The Management.

Well over the line, Part 1

Its Monday now, and the previous days encounter of course is on a loop in my head.  But Karen and I need more. Much more.

I had an idea.  I had moved some personal items to my office’s storage back when we bought the house.  They’d been there a while, and could probably stand to be moved back.  So I created that excuse as to why I would be staying late in the office that night.  I told Karen I needed some help sorting some things, and loading them into my car, and asked if she might give me a hand.  She said sure.  For some reason we continued double-speak for a while.  It actually complicated things at times, never being really sure what we really meant.  Fortunately we dropped that.

She showed up around 5:30.  We have some people who habitually work late, but I had reason to suspect, given the company’s schedule, that this wouldn’t be a problem.  By the time she arrived only one person remained in the office.  I gave her the tour of the building, we found a quiet corner for a kiss.

Not knowing how long this person would be remaining in the office, we set to the task of sorting through my things, and moving boxes to the car, like I said we’d be doing.  The person stopped and said good night to us on their way out.  We set our things down and moved to a window to watch them walk to their car… get in… and drive away.  We took one quick walk around the building, verifying for a fact that we were indeed alone, before proceeding back to my office, holding hands along the way.

My office is pretty nice, I must say.  Big desk, big leather chair… couch…  As we walked in, I pointed out some of the art I keep around, and with some small slight of hand, I produce a small gift wrapped box.  I spied an item while we were out shopping on our first pseudo-date, and grabbed it for her a few days later.  It was a small thing really, something cute she’d commented on.  I handed it to her, and sat in one of the chairs, while she sat behind my desk.

She was thrilled to open it.  She looked up, smiled, and said, “And now it’s time for your present…”  She stood, and opened her blouse revealing that same bra she was wearing in The Picture that set us firmly on this course.


Now, here is where you get a choice, dear reader.  You can choose how you will finish the chapter.

Part 3 is going to skip right to the end, and finish this chapter.  Part 2 is the “Director’s Cut”, added material if you will, and contains graphic descriptions of sexual intercourse.  2 is password protected (password: OverTheLine2), so you have to be real sure you want to read such things.  I leave it to you.  Choose your own adventure.

Well over the line, part 2 (password: OverTheLine2)
Well over the line, part 3

On Alex

Throughout our story so far I have mentioned a woman I call Alex.  She is my secret friend that no one knows about, that I share things with.

I met Alex shortly after I set foot out the door of my marriage, on equal terms, but under very unusual circumstances.   We live a world apart, so most of our interactions have, have been online.  When we met we knew we were both cheaters.  I was just stepping out, she had just stepped back in.  I was looking for an affair, she’d just ended one and was trying to live more honestly.

Alex is a beautiful woman, an intelligent professional, and insightful person. She solved her infidelity issues by seeking an open marriage, which in the years I’ve known her has worked out well.

We connected intellectually and emotionally.  For a time we carried on an online affair, sexting, pics, the whole 9 yards.  We shared a lot. I told her all my secrets, she shared all of hers. We met one weekend for a few kisses, indeed she was the first real meaningful kiss I had just starting out, but… Well, she digi-dumped me after a while. It hurt a lot. Eventually she came back as just a friend, albeit one who knew me so very well.

In the time since, we are still in each other’s pocket, we still talk, and share. We listen to each other’s problems in relationships, matters of work, children. Things that matter.

Alex has listened and watched throughout this story, and offered an ear and advice.  Even though I decided to ignore the latter, it’s always been sound.  She cares for me, and is guiding me through this mistake, as she has guided me through a few others, without (much) judgement, and only support for my well being.

Alex is having a hard time at the moment, and I’m trying to be there for her. It’s just life, granted that hers is far more complex than most. While I will speak frankly, and offer support, I don’t offer her too much advice, because I know, like she knows, people aren’t always looking for advice when talking about their issues.

Often, people just need to know they are being heard.


It was gentle, that first kiss.  It went on for a long time, her lips on mine, my hand on the back of her neck while we sat in my car, during what was becoming a bad storm.  After a moment we pulled back to look at each other.  She and I both smiled wide.  We leaned in again and kissed once more, then rest our foreheads together.  Now we spoke in whispers.  She and I began to speak about the things that you, dear reader, have read up to this point.  How we noticed each other, the uncertainty that accompanied what we now knew to be a mutual attraction, all the little events and tipping point moments that led us here, to this place, for that first kiss.

We stopped speaking… and kissed again.  And again, harder and harder.  My hands grabbed at her, her’s grabbed at me.  She unbuckled her seat belt and climbed into my lap.  I held her and we kissed with increasing ferocity…. until I happened to look up to see a car driving towards us.  She climbed back into her seat, removed her coat, and put her seat belt back on. We were breathing heavy, watching that car come towards us with great anxiety and no small amount of annoyance.

There was a storm, the weather had been bad, no one should be here right now, yet here this individual came.  At least it wasn’t a cop, which in a situation like this would have been far worse.  The car drove up next to us slowly, very slowly, creeping along.  We avoided the drivers gaze and talked… about that car, and what the hell it was doing there, and will they be going away?!  The car parked behind mine, its bumper facing mine.  We looked at it in the rear view mirror, wondering what to do next.  A few moments later, the car started to move again, and slowly drove back into the park.

We looked away from the car, and back to each other.  We smiled.  She quickly took her seat belt off, and once again climbed into my lap. I cradled her in my arms, looking down at her beautiful face.  She is truly a beauty to behold.  We kissed once more, long and slow… then more, then faster, then harder, then my hands-

What the fuck…  That car…  I looked up quickly and saw it coming back towards us, slowly, creeping along in the storm. I drew her attention to this.  We were both exasperated.  I have this point between annoyed and angry where, I’m told, I become funny.  She withdrew from lap to the passenger seat, and I started a rant that had her in stitches.  I started the car while she laughed, and we drove back to my office.

I’d hoped that perhaps the cleaning crew was done.  I left her in the car to go look inside.  No sign of the crew, but their equipment was left out in the hallways, so they must be coming back, I figured.  I returned to the car, and told her we had to move on.  She began to kiss me again.  I was getting very excited, so was she.  I started driving again.  Another park?  Closed.  Oh! Cemetery! Cemeteries are good for things like this! … Chained off… Okay, big empty parking lot for a closed business.  It would have to do.

Belts off.  Coats off.  Back in my lap. Start slow, tender… more, harder, faster.  I moved my hands between her legs.  I could feel heat radiating from her sex.  I was erect, straining my jeans and pressing into her.  There was an energy that was building between us, and had been for some time, but now we were approaching critical mass.  Then… headlights. Of course.  People were pulling into the parking lot.

Like teenagers we steamed the windows.  She receded into her seat, we both let out gasping breaths.  It was time for me to go, and she needed to return to her studies.  It was finals week in her doctoral program, so this was a big allowance of her time.  I returned us to the original parking lot where we had left her car.  It took a while for us to mentally prepare to separate.  We wanted so much more, but the circumstances wouldn’t allow for it right at that moment.  She gave me one more kiss… which of course would lead to another and another.  It took a herculean act of will to separate at that point, but finally she was in her car and driving away.   I returned to my office for one thing, to discover the cleaning equipment left in the exact same place, untouched….

We chatted later on in the day, into the night.  We had developed an urgency, an immediate need, to be alone together for an extended period of time.  I had an idea however, one which we could work on when I got to my office the following morning.

Post Script:

When I returned to the office in the morning, the cleaning equipment was still exactly where it was the previous day, untouched.  Cleaning crew comes on Saturdays… but they didn’t pick up after themselves when they were finished.  I had their hours reviewed by accounting, and suggested another cleaning company… because, that was just not cool.