What I Wish Could've Been

This story is mostly based on true events. Say eighty percent truth, the rest is fantasy. Although in real life it didn't lead to anything, albeit I wanted it too.

In real life my mom passed away before I could really show her how much I loved her. Saying is one thing, showing is another.

But this is Literotica, where the stories only go as far as the imagination of the writer.

-

Names, dates, and some other details have been doctored to keep privacy and to comply with literotica rules and stipulations.

If you or anyone you know has been through any situations portrayed in this story I apologize, I am just portraying some fears I've had/have and don't mean to offend anyone that might have gone through such events. If you have I'm sorry for your lose and wish you the best.

You'll understand that last bit later on.

* this was very emotional for me writing this story. Most is nonfiction but some is fiction.

Without further ado...

••••••

Almost everyone can remember a time in their childhood, where they look up at a parent(s) and thought, "I love you so much Mom or Dad!"

But few think or feel more than the usual, I'd say normal "parental" love that you would give to your mom and or your dad. Or even a normal "sibling" love but that is a story for another time.

At one point or another I've had fantasies for both my parents, together and separate. Some might me considered vanilla, others kinky.

Like for instance. Who's into this kind of thing hasn't thought, what if...

"You we're having some (more than motherly fun in her room) your dad walked in, seeing everything and instead of Flipping a Lid he joined in." Either as a straight player or a bisexual one.

There's always that excitement that comes from the "taboo" nature of doing something that "as a society as a whole" frowns upon and or looks down to.

When I was growing up I didn't really see it that way. I just saw it as I loved my family that much more than what most other families go through.

I'll get into this a bit in my story, but this generation doesn't realize the pain of "Dial up Internet"! I will always remember the frustration and annoyance of waiting for the bar and percentage to hit 100% and the sound.

Thinking about it now, I could've gone out for a smoke waiting for the family Compact computer to boot up.

Also in middle school went from 6" to 3" floppy disks also to "OMG" a max of 512mb flash drives.

*******

I guess it all started to make more sense to me back when my mom brought me with her and my sister Jane, to get her first car. Why she decide on a Jetta of all things I just don't know. Maybe it's a chick thing?

While they were with the sales rep. Doing their own thing. The sales rep laying it on thick the deals that they could have. As well not very enthusiastically that there was a hail storm that hit the lot recently and that there would probably be more savings with that in mind. I remember the hail damage wasn't that bad to me, think 50+ pea sized indents on the roof, hood and trunk, but they got $4000 of msrp.

While this was going on I was in the waiting room at the dealership. It was kinda small for a Volkswagen dealership, maybe 60ish cars on lot. Me doing my homework minding my own business.

"Man I hate homework!" Why oh why does there need to be such a thing. Many a time, I've wished it away, heck wish all the answers would magically appear on the paper.

I was good at math and science even though I didn't like them. But was ok in English and language arts but didn't like them either.

Even a few times wished my dog Sara(miniature black poodle) would eat my homework. But sadly this was not the case this time, I had to do it.

There never was a time that she "ate" my homework but there was a time she chewed up my math homework. You can guess what my teachers reaction to me telling him what happened to my homework... Among thinks "You must think I was born yesterday!" And "That's one of the oldest in the book, couldn't you have thought something original?"

Me "but it seriously happened teach, I'd show you the evidence but my dad threw it in the trash!" Him "Uh-huh! Right! And my names Clint Eastwood! Regardless if I believe you or not, you still have to redo it." At least he didn't outright call me a lier.

Later at a parent teacher conference, my dad did clear up the "dog eating my homework" event relating its truth. Him not happy vacuuming up the confetti of my homework from the living room to the sitting room.

***

Sorry about that rant, lost my train of thought. Oh right! Ok, was almost done with my homework when my mom came in the waiting room for a min to relay to me that they were finishing up with the final paperwork and would be done in ten or so minutes.

I was like "ok mom! I have to go to the restroom, So I'll meet you back here when I'm done."

She smiled and said "that's fine Jonah, I'll see you in a bit.

I smiled back and said "ok mom!"

After she turned around and headed back to the office, to my sister and the financial representative to finish up. I went over to the receptionist and asked her "excuse me miss? Where might the restroom be?"

She looked up from some papers and after a small smile pointed and said, "it's down the hall there second door on your left."

I returned the smile, thanked her and went to do my business. After I was done and probably because I'm a bit of a snoop. Although at times it was because the toilet paper ran out. I went and looked through the drawers and cabinet under the sink.

And guess what I found under the sink. A porn magazine. Although I didn't know it at the time, you might consider it like a Maxim magazine but for auto enthusiasts. Naked and near naked women around, against and on exotic foreign and domestic cars and trucks.

I was fascinated by it all. All the beautiful women and vehicles together and by themselves. I wanted to take it with me, but thought it would be suspicious if after I went in to the restroom that the magazine would go missing. Plus I thought what my parents would say if they found it. God forbid if my sister caught me looking at it too.

So I thought of the next best thing. Since I brought my school binder/case. I had a small pair of scissors in the binder.

So I could cut out a single picture from the magazine. One that would either go unnoticed or one that wouldn't be missed.

After going through the magazine a time or two to decide on the picture and also what size would go unnoticed, hopefully.

I ended up finding a small, maybe 2x2" picture of a blond woman that was using two wrenches to cover her nipples near the back of the magazine.

I put the picture behind my pencils and other school utensils in the pouch in my binder and headed out the restroom.

As I'm waiting back in the waiting room for the women of family to finish the paper work. I had a thought. "If there are naked women in magazines, why shouldn't there be on the Internet?" After that my whole world changed, hopefully for the better.

Before this, I didn't really think much about sex or masturbation. Boy did that change after this realization.

To do the deed I needed to be carful not to get caught either by my sister or by my parents. I had to either wait for everyone to be out of the house or asleep. If asleep I turned off the external speakers connected to the computer so the noise might not wake up my sister.

*

To put this in perspective, let's see if I can help you picture my house.

It's about 4100 square feet, backyard on a hill but has Plato's. Two story, 5 bedrooms, 4.5 baths, a fairly large deck with a grill, a 5 ft pool shaped like a bean, a half basket ball court, and a three car garage, with a driveway in the shape of a lower case "n" with a tree and some grass on the middle.

The garage has two doors, a single car on the outside to the left facing the house from the street and a two car door to the right of the single door. Facing the house the garage is on the left side of the house.

Outside the front door there is a overhang that protects a partial low fenced 4 foot wide front porch with a bench on either side of the front door.

Once your go through the front door, if you turn to the right there is a doorway to the guest room, it has a small connected bathroom with sink, toilet and shower.

If your looking in through the front door, on the right are the twenty-ish steps to the second floor which is carpeted, as is every room but the bathrooms and kitchen as they're white tiled.

If you go up the stairs and turn right, you will first be facing a double door linen closet. To the right of said closet is my sisters room. To the left of the closet is the computer room. There is a connecting bathroom (shower/tub combo) with two sinks and a large mirror between the two rooms.

If you turn left out of my sisters room, across a railed six foot wide bridge you would be facing a door that would be to a room that we use as a game room.

It has a couch that folds out to be a bed against the wall to the right once you go through the door, a 35" box tv with my ps2 and a DVD player hooked up, a foosball table to the right of the couch and ping-pong table to the left of the couch.

Once through the main door into the game room if you turned to the right, against the far wall is a door leading outside to a small wooden deck, maybe four foot wide by seven foot long with two chairs.

On the left wall if looking through the main doorway again, about in the middle is a door that leads to a smallish bathroom. Just a single person glass walled shower, toilet, and sink with a oval mirror that connects to my room.

If you step back out the game room, turn back around to face it but turn left would be my room.

Not counting bathrooms, both me and my sister's room are mirrored copies of each other, just on different sides.

But something we both share is a big four foot wide by five foot tall window in the middle of the wall facing the front of the house, with a lounging area under the window with two drawers for storage.

Back downstairs to the first floor, straight ahead through the front door is a tiled walkway, six feet wide for fifteen feet or so and then it tee's.

Straight ahead is a carpeted twenty by twenty foot sitting area with a couch and four chairs and a cabinet on the left wall. The two bottom spaces filled with the family photos, since my dad was a boy.

Also with the wall straight ahead practically all windows looking out at the deck. Think massive fort foot wide by ten foot tall windows.

If your turn right at the tee, straight ahead is a small restroom(sink and toilet only).

If you turn right out the restroom theirs a four foot wide tiled walkway that leads to my parents room. If you take a single step in my parents room, to the left is a glass door that leads to the deck.

If you turn right, go ten feet and turn right again. You will be looking into the master bathroom. On the left first is a clear glass walled five by five foot shower. Past that on the same side is a three maybe four person jacuzzi. The room kind of looks like a square letter "P." The wall you would see slightly to the right and straight ahead looking in had the door with just the toilet. The wall to the right once you walked five feet in had a sink with a few drawers and a large rectangular mirror. The other wall to the right of that one had the same things.

Back to the tiled tee section. If you turn left there is a tiled walkway that goes towards the living room (which is carpeted). With the entire wall facing forward is integrated shelves and a boxed indention to house a tv with the proper cable connections and power plugs.

Half way down the walkway to the left is a door that leads to the garage, to the right is a opening in the wall that leads to the kitchen.

The kitchen is kind of like a upper case "D" but with 5 sides. Picture The curved parts a "D" are three straight sides. The middle one has a glass door leading to the deck. The walls on either side of the door has large nearly floor to ceiling windows.

The space between the kitchen door and the door in my parents bedroom is about twenty-four feet. Heading away from the house about fifteen feet, in that space is a table that can seat eight. One at each head and three on either side. On the right side of the deck facing out is where the grill is. On the left is a bench integrated in the wooded railing.

Slightly to the left of the grill are ten or so steps that lead down to the bean shaped pool. At the bottom of the steps are two lounge chairs with a small round table for drinks. On the opposite side of the pool from the stairs are two sitting chairs spaced apart. On either side of the pool in the middle is a three inch wide, two foot deep hole to stick the poles for a Volleyball net.

To get to the half basketball court you turn left from the stairs, walk straight till you hit grass. Take a right. Walk down a grassy hill for about forty-forty five feet. Turn right and there is the half basketball court. That also also has a integrated bench in the two wooden walls that are up against the court.

*

So now you know, if you think about it. My sister could possibly hear me on the computer looking at porn. Sometimes watching videos if I was too loud. It was possible if she heard me, she could investigate and catch me in the act. The fact I could get caught both scared and exited me. What would I do if I was ever caught...hmmmn...maybe that could be another tale?

It was during one of many porn searches that I came upon the incest category which branches off into many sub categories. Which include mother/son, mother/daughter, father/son, aunt/nephew uncle/niece, cousins female/male

male/male, and so on. But what I more so focused on was mother/son and with sister/brother as a close second.

Let me tell you a little bit about the women of the family and about me.

My mom Rebecca, has short Maybe four inch black hair. green/brown eyes. average nose. without lipstick red lips. Is five foot-five. one-forty-five-ish lbs. Caucasian. Curvy in the right places with a small belly, but with a large 42D breasts with a bit of sag. Heck she is 48 at this time and still looks good.

My older Sister Jane, 21 years old. has shoulder length brown hair. green eyes. smallish nose. slightly red lips. five foot-six. one-fifteen lbs. Caucasian with usually lightly tanned skin. mostly like toothpick. except for some small maybe 32B cup breasts.

Me Jonah, 18 years old. I have short maybe two inch dark brown hair-looks almost black when wet. Hazel eyes with some gold around the iris. slightly left crooked nose. idk I guess a fleshy light brown with a bit of pink lips. five foot-eight. one-thirty-five lbs. Caucasian. swimmers build. very little body hair pits and groin mostly.

******

My sister Jane had a on again-off again girlfriend at the time. In One word "lithe" came to mind thinking of Jane's girlfriend. Cecelia is Five foot-nine. blonde hair. sea-green eyes. my best guess 36b/26/30. possibly one-twenty-ish lbs. Caucasian and usually didn't have to wear makeup to look good.

My dad is a medical director and because of his work schedule would be away on business 3-5 days out of every week. Most of the time 3 days and with my sister out of the house doing her own thing most of the time with her semi-spontaneous escapades. It would just be just me and my mom at the house most of the time. At times we'd play together in the pool, fool around. Play ping-pong or foosball or watch a movie. We also danced slow or fast and just making fools of ourselves having a good time teasing each other.

*******

This all escalated one night. When my dad was out of state for work and my sister was out to dinner with her girlfriend and would be staying the night.

It was just me and mom at the house.

We had a enjoyable day at the house with a game or two of ping pong, some swimming and lounging around the pool. Before we went inside and had a cooked shrimp on salad early dinner, maybe five-thirty or so.

Afterwards she went around to her room and I went upstairs to my room.

While mom was cooking I took a quick shower, so I was already clean and had the Chlorine out of my hair, eyes and off my skin.

I was thinking of playing NFS: most Wanted on my ps2 for a bit.

But to be courteous to my parents and to follow the rules while I lived under their roof. I had to ask permission first before I use it. Even though the game room is next to mine, if I misbehaved with the ps2, it could still be taken away for a unknown duration of time.

So I get off the couch in the game room, and head downstairs to my parents room.

Because of the doors and walls, I can't tell if the shower is running until I open the door. I thought my mom was reading, so after knocking on the door with no response I opened the door.

It was at this time I heard the shower running. Also noting that the door to the bathroom was cracked open by about a foot or so.

Not think much of it at the time. I walked over to the door and was about to call out my question to use my ps2.

I got as far as "hey M..." when I just gawked at her. Granted there was some steam but with the fan running and the door how it was I could still almost perfectly see her through the glass. Also because of the fan plus the shower she didn't hear me. So she just kept up with her shower.

While I on the other hand was starting to get hard. It just so happened when I arrived that she was almost finished washing her hair. So she had her back to me and I was taking in the full view of her ass and just simply the complete view from behind.

Then as she starts to rinse out her hair she turns to face me. At this point my dick's too hard not to do something about it but I freeze when she turns to me. Hard dick in hand starring first at her breasts. Then Noticing her nipples are slightly peaked and that her mons Venus is slightly aroused.

Then she turns around and lowers the spray down and starts to soap up her whole body. Watching her do this has made me feel like my dick could hammer nails and was pumping fast. Leaking some pre-cum. I was feeling so blissful and in my own zone that I didn't notice the shower cut off.

Next thing I know, I hear a gasp. Also "Jonah!" I froze completely, like a deer caught in headlights. For what felt like an eternity but was probably only really a few seconds. Until just like a deer my next big thought was "flee!" So that's what I did, or at least try at first.

In my hast to flee, I forgot my shorts and boxers were around my ankles. I immediately started to fall down. Luckily I caught myself like doing a push-up with my nose a few inches from the carpet.

In my next hast to make a quick retreat. I kicked off my shorts and boxers and high-tailed it up the stairs to my room.

For a spit second I thought it invigorating to streak through the house in my birthday suit. At least until I remembered my current predicament.

I was just caught by my "MOM" masturbating to her while she was naked in her shower and now I'm naked running to my room.

"Shit! Shit! Shit! Fuck! Why couldn't I have just asked mom to play on my Ps2. WHY did I have to keep watching her in the shower?! And WHY did I have to get CAUGHT in the ACT about to BLOW my SHIT!? FUCK!"

I was so not looking forward to the conversation I knew was bound to happen and soon. Fortunately or unfortunately, not sure which. I didn't have to wait long.

A few tense minutes laying on my bed with just a single sheet on me staring at my fan spinning around. I heard a double knock on my door and a "Jonah? Can I come in?"

With my dirty mind, my first thought was "I know somewhere I'd like to cum!" But immediately berated myself for thinking that and said "Yea Mom. Come on in. Doors unlocked."