What Was and What Should Have Been - Cover

What Was and What Should Have Been

Copyright© 2015 by DEMONMASTER62

Chapter 1: The Set-Up

Erotic Sex Story: Chapter 1: The Set-Up - Not a "Do Over". More of a "Re-Imagining". Most of us have memories of moments in time that we wish we could go back and re do as the person we are now. Most of mine revolve around sexual situations. Where the "Now ME" can do what the "THEN ME" wouldn't do for whatever reason. Except for actual names and specific locations, the "WHAT WAS" is/are 100% true. The "WHAT SHOULD HAVE BEEN" is how, I as The Demon/Dom I am today would handle it. Codes will be added as needed.

Caution: This Erotic Sex Story contains strong sexual content, including Ma/Fa   Heterosexual   True Story   High Fantasy   DoOver   InLaws   MaleDom   First   Oral Sex  

I had left a wife and 2 kids to come back home to Orlando. Things between my wife and I were ok when I was in the Navy. When I got out, and we tried the Domestic life together, we just clashed, badly.

Partly, it was because we lived with her parents, our entire married life. Which was fine, when I was gone 6 months out of the year. Afterward, when I had a regular job and we saw each other every day, it wasn't so fine.

I mean, I loved her Mom, still do. She was and is a wonderful person. Her father on the other hand, well let's just say, "Not so much." He and I just could not connect on anything. Of course, I could be accused of placing the anger and rage at the sins of my own father, on him.

Anyway, Any time, I and his daughter/my wife got into a shouting match, I was always the bad guy. I should have known better. We had went steady in both Junior and Senior year. We fought every day then, so why would it be any different now?

When you hear that line, "Never marry your High school sweetheart" you think "bullshit". All I can tell you is Don't, just Don't.

DON'T!!!!!!

Oh, I'm not blameless here. I have said on here somewhere that I was cursed/blessed with the Libido from hell. I fucked every friend she had in High school. 3 virgins including her, 2 that weren't. Only one of her friends never showed any interest. I was to find out later she was a Lesbian. Cliche' I know, but true.

Remember, every part of the "What Was" section is 100% true, except for naming names or specific places. I want nothing to come back on me.

My "Not keeping it in my pants" got worse in the Navy (OK, it's never stopped). If it was female, had a heartbeat, and stayed still long enough, I tagged and bagged it. Size didn't matter, nor did looks (as long as she didn't break mirrors). I've done Beauty Queens, and I've done the Doggiest of the Dogs. And all points in between.

I would hang my head in shame, except I just don't care. I am what I Am.

Why did I marry this woman, who I fucked around on and fought with from day 1?

Because to THIS day, She gave, and probably still gives her second husband, the best, most mind blowing Blow Jobs I have ever had. It has been 28 years since the last time I got one from her, and it is still Number 1!

If you tell her, I'll deny it.

But, other than that, she was as frigid as frigid could be. I can only prove that I got to make love to her at least twice, because I have two children. Who now have children of their own.

OK, so We finally decided we were no good together, and I came home to Florida.

Fast forward a couple of years. I had continued my ways. Until I met the next person that was going to take up 5 1/2 years of my life.

We met at age 25, just a month apart in age. And, wonder of wonders, she was still a virgin. I Am NOT kidding.

We dated for 3 months before we had sex that was anything more than a blow job (Well, I wasn't going to go with out nothing, you know.) And trust me, She bled like a stuck pig when the time came.

After she had sex for the first time, she couldn't get enough. We did it anywhere at anytime.

This was right around the time that I started to be more aggressive in sex. I always was, but it kicked up a notch or two in this period.

I even managed to stay faithfull to her for a whole year and a couple months, before I couldn't ignore the "hunting" instinct anymore.

During this period was when she started calling her self My "Little Girl".

She was so into it, that she would stick her tongue out at me, and I made her stand in the corner for it. This would usually lead to a rough Head job, or an even rougher fuck, right there in the corner.

Sometimes I would just tell her she could get out of the corner, and we would sit and watch TV, and I'd never touch her except for kissing her goodnight. Frustrated girlfriends can be a lot of fun, as long as you don't push it too long.

She never lived with me, but stayed at least two weekends a month with me.

There are a lot of these "WHAT WAS and WHAT SHOULD HAVE BEEN's" that could feature her. Let's call her Debbie. That's far enough from her real name, that I shouldn't get any grief.

Just as we were reaching the end of our third year together, Her best friend from her childhood in New York, came down to visit her and her family.

And of course, the first thing Debbie had to do was bring her to her boyfriend's place.

It was in the middle of one of the coldest winters that Florida had in the late '80's. My cheap little Apartment had AC but no heat. So, when they arrived, the friend who was a little heavier, and had that New York "On all the time" personality, said right off the bat, "Oh hey Baby, we come bearing gifts, you lucky boy." And hands me a bag that has a brand new but small space heater in it. I still to this day, have that thing stashed away in one of my junk piles somewhere.

That heater got me through more than one winter, trust me. Anyone that tells you it never gets cold in Central Florida, just smack 'em. We may not get the months of sub zero weather like up North, but when it dips into the 30's with that wet wind blowing it right through you;

IT IS FUCKING COLD!!

ANYWAY, So I forgot the friend's name 5 seconds after I heard it. I am terrible at remembering names. I mostly stick to, Baby, Honey, Lover, Sweety ... etc. It has saved my ass more than once.

I did however admire her skin tight jeans, hugging a not so much fat, but ample ass.

A very nice set of DD's up top setting very pretty. The tight jeans also gave her a very alluring "Camel-Toe", Which I'm sure she knew. and made sure I was usually in a good position to see it.

As with most girls built like this, she was cute as hell. And just as bubbly. My "Hit" or "No Hit" mental meter was definitely on the "Hit" side. Too bad she was my Girl friend's BFF from childhood.

From the first time I met Debbie, I always loved that she wore very very short skirts and dresses, so that all she had to do was breathe hard, and you got a panty shot. I think she was compensating for her lack of boobs. I loved her, she was gorgeous, she was all I could want in a sex partner at that time. But, her tits were non-existent.

They were more like mashed marshmallows (regular size) with a candy nipple planted in the middle of each one. They were fun, because they were very sensitive. Any attention to them at all would have her bouncing off of the ceiling, cumming like crazy.

WHAT WAS;

After eating the fast food they had brought, we settled down on my couch, which was actually a pull out bed, if you remember those.

Debbie was giving me my quota of panty shots. No way could the friend not have noticed.

The friend also noticed that on the lower shelf of my junky coffee table, I had a couple of "Adult" VHS tapes. (long before DVDs)

She kind of conversationally related to us that she had always wanted to see one, but was too chicken to try. She still lived at home at 28, and still feared her parents.

Debbie and I exchanged looks. She knew what I was going to do, and just nodded. So, I made the friend pick the title. She chose the one that sounded the nastiest, and it indeed WAS really very nasty. I got it all running, and we sat there and started watching it.

The friend was on the far left, Debbie in the middle, and I on the far right.

I say "far" but truth be told, while we weren't crushing each other, we were definitely in contact with the person next to us.

As I said, this movie was really nasty. The sound of all of our heavy breathing was audible to everyone else.

I got an Idea. Something that I had wanted to do with Debbie for awhile, but you never really know how far to push things with someone you are in a relationship with. I didn't know anything about safe words or anything like that yet. I just had the aggressive urges.

I looked at Debbie, she looked at me. I think she thought I was going to kiss her and feel her up, and looked more than ready for it.

What I did however, was make a motion with my head, which she caught on to right away. Of course I was motioning for her to blow me.

At first she looked like she was going to refuse. I just gave her my "I mean business" look and she slowly slid down to the floor to comply.

I scooted more into the center for more room. I did not help her in any way. She had to open my pants, unzip, and get it out herself.

To her credit, once I was "Free", she went right to it. I actually had to put a hand on her head to slow the pace. I wanted to enjoy this. She then mentally shrugged I guess, and began giving me one of her best.

I was slowly coming to learn that she liked to be shamed by having to do things in front of others.

The only light was from the TV, we had turned off all others so we could see better.

Well, the TV was now at Debbie's back. So while I and her friend could be seen pretty well, except for a few shadow areas, Debbie and my cock were pretty much in those shadows, though it was easy to tell what was happening.

I, being the pig I am, instantly think "Hey, My first Threesome!"

As soon as the thought struck, I put my hand on the friend's leg. I just knew she would push me off, but alas, she didn't!

We started carrying on a running commentary on the movie for Debbie's sake, as my hand inched ever so slowly, higher and higher.

One more inch would have put me right on her camel-toe, and she wasn't stopping shit!

What I had not noticed in my fever to get to this girl's crotch, was that Debbie was looking for my hands. I can only guess she had some kind of idea what I had in mind, as we had discussed it before. Usually as a fantasy to get one of our fucks even more heated.

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