My Sister Catches Me Crossdressing

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Bdsm

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 şişli grup yapan escort 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 şişli masöz escort 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!”

I was pleasantly surprised to see that Jane had gotten semi recently, some of that waterproof/sweat proof makeup. She did have makeup remover and scrub pads. So I wasn’t worried. I tweezed my eye brows a bit to get a few hairs I missed. Then started with that black pencil with a line just above my eye lashes.

At first was a bit difficult for me. Especially to stay still while doing it to ones self. But with practice, I got good at it. Once that was finished, I went with the black eye shadow. Covering my eye lids and a bit bellow my eyes as well. I continued down my face, next with a bit of blush on my cheeks. Finishing with a bit of foundation to blend it all together.

Thus satisfied with my work so far and almost done. I looked through my sisters lipstick collection. I had maybe fifteen different colors to choose from and at least a few shades in every color.

I ended up choosing a cum fuck me ruby red lipstick. Think what Jessica Rabbit would wear. I slightly dreamily thought to myself that.. (if a manly man..or a woman tried to mess up my makeup! with their lips. That it would stay until i personally removed it with some remover and scrubbers!)

I was immensely happy with my work.

I could totally pass for a hot dolled up teenage girl waiting for her man or girl to pick her up and take her to a nice dinner. Or a dinner and a movie. I yipped in glee and pranced around her room for a bit.

Then I started to get thirsty and thought it would be a thrill to get a soda from the fridge as I am right now. Boy was it ever! Walking down the stairs dressed up (imagining a partner waiting on the ground floor for me. set my heart a racing and blood pumping) but continued over the tiled entry floor to the kitchen. Smiling to myself hearing the click click of the heels on all the tiled floors except for the carpeted living room and front sitting room.

I sipped my soda in the kitchen. Looking around and seeing my reflection in the microwave glass and the metal toaster and smiled. Posing here and there looking as my body’s image changed.

I took another sip and steeled myself for what I was to do next… I walked over to the kitchen door that leads to the back deck, opened it and walked through. I left the lights out (made me feel safer) but because of the fence. The backyard and deck isn’t viewable to the next door neighbors. Still, I was a bit frightened. Although no one can see me, this was the first time that I’m stepping outside in full get up. There was a thrilling excitement from walking around on the deck and hearing the clunk clunk of the heels on the wooden deck!

After a bit, I decided I’d had enough and went back inside to the kitchen. Once there, I threw out the finished soda can in the recycling. But first checking to make absolutely sure that there was no lipstick on it before it was tossed in the bin.

Then i walked out of the kitchen. Through the hallway and towards the stairs. I walked up and then back into my sisters room. Where I proceeded to check myself out in her full length mirror. Twisting her and then there, posing in one way or another. blowing a kiss to the mirror.

(I was so into what I was doing that I didn’t notice till it was too late.

Creak! a floorboard goes off behind me. the only one i could think of was to the right of my sisters şişli otele gelen escort Bedroom door. (FUCK!)

Then I see a outline of a person in the reflection of the mirror before I hear..

“WHO THE FUCK ARE YOU! HOW DID YOU GET IN MY FAMILIES HOME!?”

I could see her glaring at me in the mirrors reflection. I slowly turned around to face her. And saw the changes in her facial features. First a fury looking face and eyes. To glowering but a bit of confusion. To utter confusion. To finally realization and one of her sexy smirks. (shit! she knows!)

(I’M FUCKED!) (DAMN! IF I’D JUST GONE STRAIGHT TO MY ROOM, SHE MIGHT’VE NEVER KNOWN!…)

[Jane] (IS THAT MY DRESS SHE’S WEARING!!?) (WHO IS THIS GIRL IN OUR HOUSE!?) (WAI- IS THIS JONAH?! HMMNN!..)

[me] (FUCK! FUCK! FUCK! FUCK! FUUUUUCK!!)

“WELL, WELL… I HAD NO IDEA YOU WERE INTO SUCH THINGS,…JONAH!” She tells me with a sly smile on her face.

“YOU LOOK BEAUTIFUL IN MY DRESS. WITH HEELS AND MAKEUP ON.” As she licks her upper lip before returning it into her mouth in a smile.

I gulp quietly. “S-SIS…!?” “I-I THOUGHT YOU SAID, YOU WERE GOING TO BE HOME LATER…”

“THE PLAN CHANGED…INSTEAD OF A MOVIE AND FUN AT HER PLACE. SHE WANTED TO ORDER PIZZA INSTEAD! THEN WE ATE EACH OTHER OUT WAITING FOR THE PIZZA TO ARRIVE. THEN LICKED EACH OTHERS FACES CLEAN WHEN FINISHED.”

“BIT THANKS TO THAT, I GOT TO SEE SOMETHING AMUSING!! ALSO AROUSING!!”

“IS THIS WHAT YOU NORMALLY DO WHEN YOUR HERE ALONE AT THE HOUSE?!” With clear amusement in her eyes…

… At first I simply just turned away from her. Feeling my face heat up as blood rushes to below my cheeks, nose and a bit of my forehead. Blushing hard in my embarrassment and shame…

She walked over to me and put her lips close to my left ear as I heard her whisper into it. “PERVERT.”

“AAH…” (Fuck!) “WHA-” I don’t get a chance to finish.

“I WONDER WHAT MOM, AND DAD..WOULD SAY…IF THEY SAW YOU LIKE THIS..AS YOU ARE NOW…” “IT COULD GO EITHER WAY!.. As she simply shrugs.

It barely takes me a second to consider what I will do next. I quickly hike up a bit of the dress. Then do the best bow I can while in this dress and in three inch heels on carpet while about to speak. (The kind of standing bow that my legs are straight up and I am bent at the waist at a ninety degree angle.)

“I-I’M SORRY!, PLEASE DON’T TELL THEM!? PLEASE FORGIVE ME!!?”

“HA! HA! HA! I DON’T KNOW…, WHAT SHOULD I DO…?” “OH WELL…, I GUESS IF YOU’LL DO ANYTHING I SAY FROM NOW ON…” “I’LL FORGIVE YOU, OK…”

I don’t even think for more than a few seconds before I straighten back up and glare at my sister! (I wonder if I still look sexy when mad right now?… never mind!)

“FUCK THAT JANE! I WON’T BE YOUR TOOL FOREVER!…” (But I do pause. Partially to think of a counter. The other to give dramatic effect!) “BUT I WILL DO ANYTHING YOU SAY…, UNTIL MOM GETS BACK!” “IF I HAVE TO…” “I’LL WAIT AS I AM, AND BOTH SHOW AND TELL HER HOW I AM!” “I BELI- NO!” “I KNOW! SHE WOULD STILL LOVE ME REGARDLESS!”

“If I Like To Dress Up, Occasionally…”

She stares at me for a good bit. Maybe twenty or thirty seconds before she replies. “FINE. BUT YOU WILL REFER TO ME AS MISTRESS UNTIL THAT TIME CUMS!” “If mom comes home early and want to talk to you for any reason. I’ll divert her attention enough, so you can get cleaned up and go into the computer room. “DEAL?!”

“DEAL!” I say. But she gives me a pointed look. “MISTRESS!… I AGREE MISTRESS!” With a nod.

She smiles triumphantly, and quickly says. “GO AND TAKE OFF MY DRESS! WHILE YOUR AT IT, TAKE IT AND SOME OTHER OF MY DIRTY BLACK UNDERWEAR AND THROW IT IN THE WASH. SET IT TO DELICATE AND COLD WATER! UNDERSTOOD!…?”

I quickly take off the dress and look through her dirty clothes before I find some of what she asked. “I’LL BE RIGHT BACK MISTRESS!” I said with a slight bow of my head. As I turned and left to do what she asked.

After a few minutes, I returned to her room with her waiting for me, patiently sitting on the edge of the bed. “GO OVER TO THE MIRROR! LOOK STRAIGHT AHEAD AND PUT YOUR HANDS BEHIND YOUR BACK!”

I walk over to her mirror but stop half way. “B-But?…”

“WHAT WAS THAT!? DIDN’T YOU PROMISE ME TO DO ANYTHING I SAID!! … GRANTED NOT FOREVER. JUST FOR ANOTHER HOUR OR TWO, YOU..ARE..MINE!”

I sigh, but walk over to the mirror and look straight ahead. In the mirror I see her get up and walk over and behind me. But her right hand is behind her back. I hear her say “HMM.. YOU LOOK BEAUTIFUL JONAH…!” I relaxed a bit. I couldn’t help a

small smile. Seeing it in the mirror, it looked a bit sexy.

“ACK!!” All of a sudden I hear a lot of small fast clicks behind me. It quickly dawns on me that I’m now handcuffed but they feel they feel a but fuzzy. Then am forced on my knees hunched over. “W-WHAT ARE YOU DOING!!?”

“THIS WAY I CAN MAKE SURE THAT YOU CAN’T GET INTO ANY DIRTY MISCHIEF!!” She says with a sexy smirk on her face.

She takes a knee behind me before saying. “HOW DOES IT FEEL TO WEAR MY UNDERWEAR?” As she first glides her right hand over the right side of my rib cage and belly.

Then she pushes the right cup of the bra

over and pokes that side nipple. “AH!?” “COME ON SIS, THAT TICKLES…!” “AHH!”

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