This story takes place in the future universe after "What I Wished Became My Reality".
***
It was quite a few months ago that I first had a sexual experience with my mother. Both my dad and sister were out of the house. My dad was off on a business trip. My sister was off on a date with her girlfriend and spending the night. I caught my mom in the shower and watched her for awhile. She caught me peeping at her, and the following event that night led to my mom and me starting a sexual relationship. On top of the normal mother son relationship we had.
Things with my mother have been different ever since then. We have been helping each other with our sexual needs and having fun while doing so.
One time when we were doing the nasty by the pool. Unbeknownst to us, we had a audience. That audience was my sister Jane.
After that event. She didn't act as usual around either me or mom. At first we both didn't know why. But later we found out that she knew about us.
At some point me and my sister also started a sexual relationship. That would be normal for a average couple. But thats not what happened here. In this tale we did have some fun together. But it was different from previous experiences. I'm not sure if this will happen again this way or if we would continue as we had before this. Only time will tell.
This is my story how I was caught by my sister and what happened next.
*******
It all started on what would be assumed to be a normal saturday night. My dad was off on a business trip for his work in New Mexico and would be back in a few days. Mom had some plans later on with some of her friends. The plan was to go to a movie around seven or so. I would be on my own for dinner, but didn't have a problem with that. I could just heat up some leftovers or cook a frozen pizza or something.
***
My dad is out on business trips for at least half of every week. While me and mom do have {Our Special Time} Coupled with Jane, my sister. Is usually out and about with her girlfriend or off doing something for herself. With all that I find some time for myself.
Ever since I Found about it on the internet. I've been a bit hooked. (Lately When I'm Alone, I've been obsessed with this secret "playing...")
In my porn searches on the internet of course had come across things such as straight, gay, lesbian, shemale and many others. But then I found the trap or passable crossdressing category.
Frankly I was interested and masturbated to that and many other categories. At the time I thought of myself as bi-curious. (Later would come to find I more so identified as pansexual)
When my dad was out, my mom busy or asleep and with my sister out. I would try on her clothes. Since I already had fun with her and mom, I wasn't interested in used panties and such for the most part.
I wasn't interested in sniffing her panties or anything like that. I've partaken from the nectar at the source. But sometimes I would steal a pair or two to masturbate in and or prance around both the game room and my room.
But I didn't stop at just my sisters underwear. I also tried her skirts, her blouses, her dress pants, skirts and also her dresses.
I even tried on her heels. I can tell you that wasn't easy. But her tiled bathroom was four feet wide by fifteen feet long. There, after quite a few first stumbles but with something close to grab onto just in case. I got better, and more confident in myself. But both her room and the connected by the bathroom, computer room was carpeted. As well as the second story bridge, (separating my sisters room and mine) my room and the game room were also carpeted.
With more practice, I got good even walking around on carpet. I was ecstatic when I would be able to walk around the top floor with hardly a single mistake. One time I took a chance to walk around downstairs in just heels. Boy was I nervous but there was something satisfying hearing the click of the heels as I walked through the kitchen and tiled hallways.
But jumped in fright and fear as i heard the garage door opening. Dad was still on business. So it must be mom back from grocery shopping. I quickly run as fast as I can in the heels. Out the kitchen, through the halls and up the stairs to my sister room. Where I quickly take off the heels. Then put them back where I'd found them and ran to the game room.
Where i quickly booted up my PS2 and loaded "Need For Speed: Most Wanted!" But kept the door slightly ajar and the volume low. So I could still hear my mom if she needed me.
As if on Q, she called up to me to help her stow away the groceries in the fridge and pantry. As I'm heading downstairs to help, actually doing the deed and heading back upstairs, I'm thinking. I'm thinking of many things but mostly how glad I was that it was mom and not Jane!
Sometimes but not always. Jame doesn't park her jetta in the garage in her spot. But at times she will park in the turn around near the front door, of the driveway. And simply come through the front door. If that happened instead. "I WOULD HAVE BEEN SCREWED! AND MOST LIKELY HAVE BEEN CAUGHT RED HANDED!!"
(That revelation really scarred me. It pushed me to keep going but with a fair bit of caution for future endeavors.)
***
It was a few weeks later. That I found out that dad was going to be away on business again for two days and a night.
Mom was going out to a movie with some friends of hers. (Some of them were my friends mothers.) As well, my sister was going out on a dinner date with her blonde girlfriend Cecilia.
I recently had also began to experiment with a little makeup. First starting with just, I believe it was peach lip gloss. Quickly graduating to lipstick. While also experimenting with my sisters blush, mascara and eye shadow.
At this time I wouldn't say I was fem looking in my normal clothes. Or even terribly masculine. I was a comfortable middle ground of both.
I have green/brown hazel eyes with a golden circle surrounding my pupils. Some black eye shadow with a carefully applied line with a black pencil really brought them out. A average nose but a slight crook to the left. Slightly small lips, more so brown with some red in there. For a man I guess slightly larger than normal eye lashes, they really popped with some mascara on.
(Think that bartender from the movie "BURLESQUE" with his black bowler hat and black leather vest.)
I am just under five foot eight without shoes or socks on and weigh around a buck thirty. I guess I have a lithe swimmers body with a nice tan. After almost a whole summer biking a few miles to Barton Creek from my house. Then hiking and swimming the day away and biking back home. I was reasonably fit. I wasn't noticeably muscular but I didn't have a lot of body fat on my either. My chin was round and my ass a bit bubbly.
My waist size was twenty-eight inches and my hips were thirty inches. So I could fit comfortably into most of my sisters clothes. Sadly, not most of her bras by themselves... Only training bras at first. Till i had the bright idea to use two water balloons nit completely filled. And put them in the cups. Making me look close to my sisters b-cup breasts. But maybe a high a-cup. (shrug)
That night would change me and my sisters relationship a bit more than it already was. She already was cheating on her with me. But hadn't cheated before on her till me and her started fooling around. She still loves her something fierce and didn't plan on leaving her. But me and her would look at each other a bit different after this.
That day as mom said good bye to me and took off to meet her friends at the movie theater. Then twenty or so minutes later I heard the front door close and the bolt shift over. I ran upstairs from the living room to my sisters room to doll myself up and have a little fun.
The precious day I had used a disposable razor and carefully shaved all of my pubes off. As well as my underarms. With those two area's void of hair, I didn't have to deal with much. I was practically hairless except for my head. I did have arm, chest and leg hair but it was fine like peach fuzz and sun bleached.
But today I was going to go all out! I stripped to my birthday suit and started the hit water in her bathtub. I then borrowed/used a pink disposable razor of hers and proceeded to shave my legs, ass, arms and a but of my chest. Making fairly quick work of it. This wasn't my first rodeo. Then threw in a a strawberry bath bomb as the water finished filling up to where I liked it. Maybe around four inches or so from the top.
I used her coconut shampoo in her unused
second sink on the right side of her bathroom and washed my now six inch dark brown hair. Using a spare towel from the linen closet between her room door and the door to the computer room. Then I got in the bath and let the hot water and bath bomb do it's thing. For twenty minutes or so I soaked in the pleasantly warm water. (Thinking back on the first time I used a bath bomb.)
After that, I quickly dried off my body. Then with a briefest amount of hesitation (Should I? Fuck It!) I desired to throw a bit of caution out the window and paint my fingers and toes this apple-ish red color.
While it was drying, I was thinking of what I wanted to wear. (A blouse and skirt? No! But Tempting... A blouse with jeans and sandals?... No!...) Then I thought of that black dress of hers that she was wearing, that time a while back when she accidentally kissed me. Before she and I started the sexual aspect of our now current relationship.
"That Will Be Perfect!" I say out loud. Before I het up from my seated position on the edge of the tub and head to her closet. I rummage around a bit and find what I'm looking for. I hold it up and am beaming in happiness that she didn't use it in her current date!
I go and set the dress on her bed and go looking for a bra and some panties. But I fortunately find a stocking, panty and set
in all black! I yip and jump in glee at my discovery and also set them on the bed for a minute.
Then I think of what to do next.. Then I realize I realize I'm forgetting something... My home made bra inserts. I quickly run downstairs and to my work bench in the garage and open a drawer. I take out two water balloons and quickly run back upstairs to my sisters room. Then proceed to fill them up with hot water and set them to the side for now.
I do decide to first put on the stockings and panties. Followed by the bra, with my inserts. (Even without makeup on. In this and from behind! I would probably get a whistle from either sex!) I then decided for this dress, I would first put it on. Then the makeup. Followed by some black three inch heels.
Most of Janes dresses are the pull up and zip up variety. But she does have a few that go over the head and hang on the shoulders. This dress is in the latter category. Also so I don't get makeup on the inside of the dress! ("IF Jane found out, She'd probably ring my neck! Or tear me a new one!")
I looked at myself in just the stockings and dress visible in my sisters full length mirror. One of those that ones with a stand that adjusts the angle in the middle. Like that one from that scene from the Kevin Bacon movie "Invisible Man" where she is brushing her hair and kevin keeps moving the mirror toward the ceiling. (I don't look half bad! But I'm not done yet!) "Now For The Makeup!"
