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.
