What Was and What Should Have Been
Chapter 1: The Set-Up

Copyright© 2015 by DEMONMASTER62

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.

She found my hand so far up her friend's leg, that it took her by surprise. She pulled herself off of my cock so hard, that even the hand I had on the top of her head wasn't able to stop it.

If looks could kill, I would have burned to ashes right there. I had never seen her look this mad before. Then it turned into a look of hurt.

Oh God, no man can take that look from someone he loves, it just hurts too much. I'd a rathered she had kept the mad look.

We held eyes for what seemed like hours, but in reality was just 20 or so seconds.

Eventually, I used the hand she was holding to push her head back down on me.

From there she sucked until I came, and she swallowed. She moved back so that I could move out of her seat. She sat down. I turned off the TV. The lights were turned on. and they sat there just telling light stories of them growing up together.

Even then, I somehow knew I could still get what I wanted. But, as I said, there was a relationship at stake, and I wasn't ready to risk it.

So after a few nice goodbyes, Debbie rushed the friend out as I had to work early in the morning and the job I had then was a Bitch.

The next weekend that Debbie came over, I asked her what her friend had said. She just said she was cool about it. She told Debbie that she wouldn't have let me go any further.

Debbie did tell me in a later love making session, out of the blue, that she would have done whatever I wanted that night, she was just surprised.

I believe she would have too. But, that look of hurt that was so vivid in her eyes that night, was enough to make me never try that again.

We still had plenty of wild times, some that could have been wilder, But, I was never to try the threesome thing on her again.

WHAT SHOULD HAVE BEEN;

If I could pick the exact moment that the "Now Me" would take over for the "Then Me", it would be right at the moment that Debbie's hand found my hand, so close to her friend's crotch.

"Well, Of course!" you say.

I just wanted to make sure we are on the same page, so to speak.

I have had years to think about this moment and how it could have went, if I had had the balls to carry it through.

One way, that I like, and is the simplest; I would have pushed Debbie's head back down as I did. I then would have taken the friend's hand and put it on Debbie's bobbing head, and made her control the up/down movement, and vary the speed as I gave her orders to do so. This could have had the potential to turn into a lot of things.

That one, I am pretty sure I could have gotten away with regardless. Debbie would have gotten the kind of shame she needed to get off. The friend, in all probability would have confessed to Debbie later that she wished they had experimented when they were kids. Of course, that would have been a secret between them only.

Another more recent fantasy on the matter, would have been to push the friend down there with her and get the old double BJ, and who knows where it could have gone from there. The friend had already shown submissive tendencies by letting my hand get so high up to begin with.

THE one that has stuck with me through the years, even now as I am typing this, it is the one I would most want to make happen.

It is as Follows;

Once Debbie had grabbed my hand, the Demon would have taken over, and the look of hurt would not have affected me much at all.

I would have told the friend to turn on the light switch that was right above her head. As I pushed Debbie roughly back down to her mission. Once the lights came on, she would have been seen in all her shame and glory with a cock that she was fucking with her mouth.

Now that she had been seen, I would take her hair and pull upward until she climbed up my body for herself. I would then flip her dress up, if it wasn't already and quickly spank her on the pussy at least 10 times. She would be crying, but she would be wetter than hell as well. I know my girl.

"What are you?"

"I'm your little girl"

"My WHAT!"

"Your little girl, Daddy."

"Tell her what you are, Debbie"

"I am my Daddy's little girl"

"And what were you doing?"

"I was sucking my Daddy's cock real good like I'm supposed to"

I tell the friend to feel the little girl's pussy. She does so instantly ... Bingo!

"You've wanted to touch that for a long time, haven't you?

She shakes her head, but says "Yes"

"Yes What?"

"Yes Daddy?"

"Good, now you are going to be my little bitch. I have My little girl, and My little bitch."

"What are you?" I ask the friend.

"Your little bitch, Daddy."

"Both of you strip, you have 20 seconds starting now!"

Debbie was used to this, she was done in 10 seconds.

The bitch, first had trouble getting her tight jeans off, and then didn't want to take off her panties.

I very quickly took the bitch's hair and pushed her face down, ass up, onto the couch. I told Debbie to start smacking her ass until the panties vanished.

Debbie didn't take it easy on her. That ass is a nice shade of red before the panties are completely gone.

I tell the bitch, "I can fuck your asshole, or you can join your friend on your knees and suck my cock, your choice."

Debbie surprises me. She holds her friend down by taking her hair out of my hand and using her own.

"Daddy, I want you to teach her just like you taught me, remember?"

What a wicked grin she is wearing.

I reach out my hand and feel that the friend's pussy is sopping wet. I nod.

I then mouth to Debbie "Ask her."

"Do you still have your cherry, bitch?"

"Yes." she is sobbing, but you can hear desire in there if you listen close.

"Pussy or ass, bitch."

"Both"

I slap her ass hard. "Say Mistress"

"Yes Mistress, I have both, Mistress!"

We can both see the juice just running freely from her as yet unused cunt.

"I think you are really turning her on, little girl."

"Am I turning you on, bitch?"

"Yes Mistress!"

"Lick her Daddy, please? I want her to be jealous of me."

I spread the bitch's lips and french kiss her tight little slit.

"She is burning up, little girl. Make her choose!"

"Daddy is going to take one of your cherries bitch! He'll take it hard too. Which one, tell me now?"

Now, "THIS ME", Knows about safe words. "If you want to stop and have my little girl take it for you, say "Omni" bitch!"

Debbie looks at me questioningly. This is new to her, too.

"Take my pussy! take my pussy!, I've wanted to be fucked for so long, but I was scared, I am scared. I want to feel you in me. Nobody wants me. Tell me you want me."

"I want you, bitch."

Debbie slaps her ass, "I was hoping he'd take your asshole. Well, it could happen yet, I guess. Take her Daddy, make her a woman!"

If a 28 year old isn't a woman, virgin or not, I don't know what is.

I do know I was done waiting. "Debbie reach down and play with her nipples. Give her mind something else to think about. Do Not let go of her hair."

"Yes Daddy"

I spread her lips and lube her with her own juices as best as I can.

When I take a virgin, I only have one way to do it. I've had 7 in my real life, and did every one of them the same way.

Doesn't matter the position, it is all the same. I line up my cock and place it just at her entrance so there will be no off target thrust. I then start talking to her, asking her how long she has wanted to lose her cherry. I make her tell me how close she's been to losing it ... There is a moment there when they are thinking more about the talking than the impending event, and they relax ever so much.

That is when I "pull the trigger". One thrust hard and deep, no return.

It takes just a moment before the pain hits. I am already rubbing the clit by this time. Again, there is that moment of relaxation.

Now I am fucking. And without quite knowing it, they are fucking back.

Instinct, it is all instinct.

I stroke long and hard. She is meeting each stroke. I tell Debbie to turn loose of her hair and kneel beside me.

"Are you on birth control, Bitch?"

"No Daddy"

I sigh. I knew somehow that she wasn't. Well, I had the "pull out" method down to a science, by the time I got out of High School

I looked at Debbie. She knew what was coming. She did it every time she and I had sex.

I feel the bitch's walls contract. She moans loud and long. I would find out later that this was her first real orgasm. I ride her until she has given her all.

I am there. I grab Debbie's hair and hold her as I invade her mouth, and cum very hard down her throat, fucking her face as she has become to know so well.

It is there that the fantasy ends. Partly because I don't want to hear Debbie upset because there was blood with the cum she swallowed. Virgin blood.

It does lead to a lot of cool stuff for Debbie and I down the road in what would be a new Timeline. But, eventually we still break up at the time we break up, and for the reason we break up; my Dick not staying in my pants.

I sometimes think of making her friend eat Debbie's pussy, because she took the load for her.

Other times, I see things happening a whole different way from the beginning.

I guess that's why we have imaginations, instead of real do overs.

You can always restart the imagination at any time if it isn't going the way you want.

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