My Sister, My Mistress

I’ve always been a little snoop. When I was a little kid, I was always getting in trouble for digging through my older brother Jack’s room. Now that I was 18, I had refined my snooping to an art form. I was much more careful in how I left things when I snooped and hadn’t been caught for years.

I particularly enjoyed sifting through Jack’s computer ever since I figured out his password about a year ago. He had hidden it in a maze of letters and numbers under the plotter on his desk. It wasn’t so hard really, 00unjt1800 turned out to be “username: JThomas18” and xoxpwtjt777xox was “password: Tobie(our dog)jthom777.”

It frustrated me that he usually deleted the search history, I wondered what had made him so paranoid (lol), but occasionally he forgot to delete it.

I discovered my brother was a frequent visitor to the Dominatrix Veronica web site. So, Jack was into that kind of stuff huh? I was surprised. Jack is 6’ 1”, 185 pounds of muscle, beautiful brown eyes, and sandy brown hair. He was the starting running back/linebacker for our high school team. He didn’t strike me as the type that wanted a woman to dominate him – but I guess you never can tell about things like that.

I also found a file full of naughty pictures hidden in a file labeled “Homework Back-up.” There were over 300 pictures of women, usually in leather, with their big boobs poking through open leather bras. Those pictures convinced me my brother was really into that sort of thing.

I imagined watching my brother being humiliated by a dominatrix when I masturbated late at night in my room. I never imagined myself in the role of of dominatrix because at 5’ 7”, 133 pounds, and 34A breasts, I didn’t come close to the pictures of Jack’s dominatrixes.

Occasionally, I would click on one of the thumbnails in Jack’s collection to get a better look at the action. After a month or so of doing this I got the shock of my life when I opened a photo to discover it wasn’t a photo at all. It was a disguised file folder full of more pictures – pictures of me!

Most of the pictures I recognized. Vacation photos of me in my bikini, backyard shots of me sunbathing, and one of me reading on the sofa I didn’t recognize. Jack must have taken it with his iPad when I was unaware. My skirt had ridden up making a bit of my panties visible and he had blown it up into a crotch shot!

Jack, obviously, had thoughts about me too!

I found another file folder well beyond the scroll line. I clicked it open and discovered a dozen photos of me nude. Wait, it was me, but not my body – close to my body type, but not me. Jack had photo shopped my face onto nudes. He even had one of me with big boobs in a dominatrix’s outfit (I actually looked pretty hot, lol.)

You have no idea of the time I spent thinking about all of this and how many times those thoughts ended in a great masturbation session.

I was frustrated by a lot of things these days , but by a couple of things more than all. First, could I and would he, ever let this mutual attraction go somewhere? Second, there was a code I couldn’t break under his desk blotter – xxxlssm287xxx and xoxpwjt782xox. Obviously the later was a password, a variation of his name and the number 782, but to what site? This was all about to change.

Three weeks ago I went on his computer and the history was intact. He had been to a site called LushStories.

I went back to my computer and checked it out. Now this was a cool web site. Dirty stories, some naughty pictures, and chat rooms. I joined right away. Was lssm287 Jack’s “LS” name? After a few tries, I discovered a member named submale287. His profile said he was a 21 year old male from Ohio. But Jack was almost 19 and from Minnesota, but who told the truth here, right? After all, I had joined as “a 26 year old nurse from Florida, named MistressLeta.”

On his profile page, Submale287 said he was 6’ 1”, 185 pounds, brown eyes, and sandy brown hair. This was Jack, it had to be. I logged in using the “pw” jthom782 and was in! I discovered a photo album with pictures of his cock – in various states of arousal. Was this really his cock? I was dying to know.

I logged out and started developing a plan. All during dinner and for the rest of that evening I looked at Jack and pictured that cock between his legs. By bed time, I was so wet and horny I thought I would explode.

I got naked and climbed into bed and logged on to LushStories. I sent a friend request to submale287 and waited. In the dark, lit only by the soft glow from my iPad, I started to rub my little breasts and teasing my already erect nipples. I was running my hands over my body, enjoying the sensation from my touch and the cool sheets. I raised my knees up and my legs fell wide open, fully exposing my wet pussy. I slowly massaged my inner thighs as I teased myself getting closer, but not quite touching my labia.

My fingers now started their slow and steady assault on my opening, running along the outer lips that were already swollen and begging for separation. I was about to enter myself when my iPad announced a response; Submale287 said, “Hi.”

I was ready for my role. “Do you wish to be my boyworm?” I typed.

“Yes, Mistress,” he replied.

“Good, you seem to understand your place worm,” I replied, “I may allow you to be my worm if you behave properly with me this evening. Tell me about your self, your real name, where you are, and what you are wearing. If you lie to me once or fail to do what I tell you to do, I will never let you speak to me again. Is that clear worm?”

“Yes Mistress,” he replied, “My name is Jack, I live in Minnesota, I am almost 19. I am in my bedroom and I am wearing boxers.”

There was no doubt now, submale287 was my brother.

“Very good Jackworm, I believe you,” I typed, “Are you alone in your house and is that your pitiful little cock in picture album?”

“I am alone in my room, my parents are downstairs in their room. My little sister is across the hall in her room. That is my cock, I hope it pleases you Mistress,” Jack typed.

“How old is your sister Jackworm?” I asked, “and is your little cock hard now as you talk to your Mistress?”

“My sister is 18. Mistress. Yes, my cock is very hard. May I please rub it while we talk?” Jack wrote.

“Do not touch that little cock, worm. But take off your boxers and lay there in your bed exposed for me.” I then added, “tell me about your sister. Have you ever played with her?”

“I am naked Mistress and I am so hard it hurts,” typed Jack.

“Good, I want it to hurt worm. But I asked you to tell me about your sister, describe her.” I wrote, “Do not neglect my orders again!”

“Her name is Jenny. She is small but very, very hot. I’ve looked at her bras and she is size 34A. She has long black hair with streaks of red and brilliant light blue eyes. I have never done anything with her, Mistress,” Jack typed.

“So the big perv has been digging in my underwear drawer?” I thought. “I will remember that.”

“Why haven’t you played with her, worm?” I wrote, “Are you afraid she would laugh at your little weenie?”

“I am sure she would tell my parents and I would be thrown out of the house if I tried anything Mistress,” Jack explained.

“Is your sister asleep now worm?” I asked.

“I don’t know mistress,” Jack replied.

I have an order for you worm. If you fail to follow it, I will not talk with you.” I went on, “when you are sure she is asleep, go across the hall to her room naked as you are now. Stand there for one minute and watch her sleep. Do not touch yourself while you are there. When you leave, you may go back to your room and masturbate. I want a full report from you at this same time tomorrow night. Do you understand?”

I kicked off my covers, put on my soft night light, and put my iPad away. I laid there spread eagle, naked, and “asleep.”

****************

Across the hall, Jack meanwhile had typed, “I understand, Mistress. Could I please wear a robe?”

After a few moments, Jack read on the screen, “MistressLeta seems to have left the conversation.”

Jack laid in his bed stroking his throbbing member, thinking. After a few minutes he got up and walked across the room with his cock pointing the way. He stood still and listened, slowly he silently opened the door and walked out into the dark hall. There was no light visible from under Jenny’s door. He was glad for the carpeting as he softly shuffled to his sister’s door. He listened.

Nothing, just the slow and steady breathing of his beautiful baby sister sound asleep. He quietly opened the door and entered.

The soft glow of Jenny’s night light illuminated her naked body and his. Thank you God, he thought, she is nude! Her little breasts were just as he pictured them and she did shave. He wanted to move closer and examine her beautiful little pussy, but he was afraid she would wake. Her head was turned toward him, he had to be careful.

He reached down and started to stroke his throbbing penis, never feeling it this hard before in his young life. He wanted to do so many things to this magnificent little angel. But he knew better, he had completed his mission. His mistress would be proud – she didn’t have to know anything about the rubbing.

He slowly, silently, existed the room and returned to his own.

***************

At last my hand could rush to my throbbing clit, I could breath now, I was amazed I could carry out the slow breathing with my heart racing as it did while Jack stood naked in my room watching me.

I had had my eyes slightly open the whole time, enough to see everything. It certainly was my brother’s beautiful manhood in his pictures – I was sure of that now.

My fingers probed my opening, seeking relief. I smelled my sex filling the room. I had smelled it as I lay naked in front of my brother and I wondered if he had smelled it too.

With one hand still massaging myself, I rose and walked to the door. I listened and slowly opened it and walked to his door and listened again.

I heard soft moans. He was masturbating, just like I was. As I leaned against the wall, my fingers fucking myself, I listened to him building to an orgasm just as I was. I knew we both were imagining the same thing.

I wanted to go into his room right now, but I was sticking to my plan.

****************

Jack had barely made it back to his room as he ejaculated in his hand while remembering the erotic vision of his naked sister in her bed moments before.

Exhausted, he lay on his bed reliving the evening. His erection was still as hard as it had been earlier. He had never masturbated his cock slippery with his cum before. God, it felt so good. He pictured Jenny sneaking across to his room and opening the door. She stood there naked, masturbating herself as she watched him doing it. He wondered if he had imagined the smell from her room, was she masturbating earlier? He could swear he smelled her again as he came for the second time that night.

****************

At breakfast the next morning, Jack and I exchanged the usual banter, however, I couldn’t shake the feeling that he thought I was up to something the night before. Quickly, I dismissed the thought as preposterous.

My mind raced through so many things that day and I couldn’t wait for evening to fall. At bedtime, I rushed upstairs, stripped off my clothes, and jumped into bed with my iPad signing in to LushStories. MistressLeta was on the air!

For the next twenty minutes, I hung out in the Lush Basement learning more about BDSM fantasies. I slowly massaged my naked body as dirty thoughts cascaded through my mind.

Finally, Submale287 logged on requesting a chat with his mistress. Jack gave Mistress Leta a full report of his activities as his mistress had ordered – minus the part about stroking himself while he watched Jenny sleep.

“Well done worm,” Mistress Leta typed, “As a reward, you may masturbate while we talk tonight.”

At his new Mistress’ request, Jack shared some of his BDSM fantasies. He told her how he wanted to be tied to a wooden “X” naked, exposed, and vulnerable. Mistress Leta told him if he was a good boy, she may allow him to serve her this way. If he obeyed her orders.

“Do you have cable TV with all the pay stations?” asked Mistress Leta.

“Yes,” typed Jack.

“When your parents are out and you are alone with your sister, your are to ask you sister to watch the soft core Starz series, Femme Fatale with you,” Mistress Leta ordered. “You are to wear nothing but a bathrobe.”

“What if she refuses to watch it?” Jack asked.

“That is for you to handle. During the show, let her catch a glimpse of your cock ‘accidentally’,” do you understand?

“Yes Mistress,” Jack typed, “I will try.”

“You will not try worm,” the heartless Leta replied, “you will do as I tell you worm! After she says something, offer to show her more. Do what she tells you. I expect a full report this time tomorrow, worm.”

“Yes Mistress,” Jack replied as received the message from Lush: “MistressLeta seems to have left the conversation.”

****************

Over the breakfast table, Jack and I were told that our parents were going out on their “date night” that evening. We were told that we should order a pizza and not wait up as them as they would be out late.

I detected a slight crimson blush on Jack’s face. I wondered if he would follow Mistress Leta’s instructions tonight.

****************

“I’ll order the Pizza Jen, if you go to the door. Okay?” Jack offered after their parents had left, “I want to take a quick shower before it gets here.”

“Whatever,” I sighed in my most natural teenage drawl.

The Pizza arrived in thirty minutes and I called up to Jack to come and get it while it was still hot. Jack came down his hair wet, in his bathrobe.

“That was a quick shower?” I sarcastically pointed out.

“Whatever,” Jack spoke, returning my volley from earlier.

“Wanna watch TV while we eat?” I suggested.

“Sure, if I get to pick the first show tonight.” Jack negotiated.

“As long as nothing gets blown up,” I countered.

As we settled in, eating our pizza, watching some show called Femme Fatale, I said, “Jack, this is porn! I am not watching this with you!”

“No, no Jenny,” Jack protested, “this is the new adult drama from Starz that I wanted to try. You said I got the first pick…”

“Whatever,” I said as I settled in with a can of Mountain Dew to my lips.

Whether it was anticipation of his Mistress’ orders, or the beautiful naked woman on the screen, Jack had a raging hard on that he let become very obvious to me.

Jack was aware that my eyes were glued to his groin. He watched as I bit my lower lip and shifted my seating several times.

“You want to see it Jen?” asked Jack, fulfilling his mistress mission.

“Take off your robe.” I ordered.

Jack was shocked. I am sure he expected me to scream out, “eeeeew, gross.” He seemed very pleasantly surprised by my response.

He stood up and walked over to to me. As I watched, he undid his robe and let it fall to the floor.

“There it was,” I thought, as I stared a foot away, from the erect, pulsing male organ of my brother right at eye level.

After a few moments I stood up, picked up Jack’s robe and removed the belt. I took Jack’s hands and tied them behind his back saying I was afraid he would “lose control.”

Jack did not protest.

I led my naked brother back to his chair and sat him down. I picked up the bathrobe and leaned into Jack making sure I pressed my small breasts against his face. I wanted him to feel my hard nipples through my shirt, against his cheek.

I whispered softly in his ear, “I don’t like you looking at me”, as I slipped the robe over his head like a large blindfold.

“What are you… what are you going to do to me?” Jack stammered.

“Shut up slave!” I ordered. I slowly looked over my brother’s naked form. Moving in for close looks occasionally.

Convinced he couldn’t see me, I quickly stripped off my clothes and pulled a chair close to him as I slowly began to masturbate staring staring at my brother’s nudity.

With the robe over his head, Jack’s senses were dramatically inhibited. He couldn’t be sure what I was doing. His imagination, however, caused his cock to twitch every minute or so.

I came with a powerful orgasm staring at his cock. After cuming, I went over to my brother and knelt between his legs. I was sure he could feel my naked body on his legs. I repeatedly brushed my little tits over his thighs. I then wrapped my hand, wet and slippery from my own juices, over his cock and began to slowly masturbate him.

“Oh God Jenny,” that feels sooo good!” he moaned.

Occasionally, I reached down and replenished the moisture on my hands from my pussy, still very wet and slick from my earlier masturbation.

Jack’s moans increased and I sensed he was about to cum. I watched the white cream shoot from my brother’s cock in rapturous fascination for the first time. I was amazed by the strength of the spurts and the amount of cum my brother generated as I milked every drop from his familial cock.

I spent a few moments slowly rubbing some of Jack’s cum from my hands onto my flushed chest. I quietly rose and went into the kitchen and washed my hands. I dressed and went back out to Jack who was still where I left him.

I helped him up, untied him, and told him this never happened Jack and it will never be discussed. Is that clear?” I added, “you got that slave? Now clean this mess up before our parents get home.”

“Yes,” was her slave’s reply.

I was thrilled with the new power structure that was now in play in our sibling relationship.

As I went to bed, I softly mumbled to myself, “this is only the beginning …worm.”