It All Started with Just One Click

In the Beginning

It has been a busy time as of late. I had just started a new job and finished a restoration of the house. My little sister Sarah needed a place to live and I decided to convert the basement into a place for her with a large bedroom, office, and her own bathroom. Nothing too fancy but she was very happy with it. I was happy to have her back close; she was my best friend. No one understands me like my baby sister.

Sarah was very appreciative of my letting her stay with me. She was always asking if there was anything, she could do to repay me. I would always tell her that I love my little sister and there wasn't anything I wouldn't do for her.

One time she asked "Steve, what can I do to repay you? You have done so much for me and I feel bad I can't pay you back."

I looked her right in the eyes and said: "If you weren't my sister there would be plenty you could do to repay me." I laughed and she blushed and smacked me on the shoulder and scurried off down to her room.

To help out around the house Sarah would help clean and cook. This is something I did not mind at all because if there was something I hated more than anything it was cooking and cleaning. The longer we went on this way, the more it felt like a marriage. She would cook dinner and we would sit down together and talk about our days. We would clean up after dinner, then retire to the couch and watch TV. She would head off to bed first then so would I. Just there was no sex; like I said like a marriage.

This one time over dinner we got to talking about relationships and why neither of us was attached to anyone. Me, I could understand. I am a quiet person until I get to know you. I'm 40 years old about 6 foot 3 and about 225 lbs, with brown hair cut short and hazel eyes. Sarah, on the other hand, is 32 years old stands about 5 foot 8 inches and has a perfect figure with curves in all the appropriate places, she has long brunette hair and beautiful green eyes. I asked Sarah why was it she did not my at least a boyfriend.

My little sister told me "I can't find someone who makes me feel as special as you make me."

I then looked at her and told her "If you're waiting for someone as awesome as me then you are going to be alone forever because I'm awesome." She laughed and rolled her eyes.

This is how things went for a while. Sarah and I would spend most of our free time together. We enjoyed being together so much that we went everywhere together. More than once we were mistaken for husband and wife. One day I asked Sarah how the job hunt was going.

She said, "great I just got a job where I can work from home, for some decent money."

This was such a relief. I know she was stressed out about the fact that she did not have a job. We were both happy as could be.

When Worlds Collide

One day when I came home from a long and stressful day at work, I came home to a note on the stove that read, 'working late tonight bro, you're on your own for dinner. Sorry, Sarah. This was ok I was pretty tired and I grabbed a bottle of water and headed upstairs to change. When I got down to my underwear the idea came into my head that I had not cum in some time. I figured since I was on my own for a little while I mine as well enjoy myself.

I plopped myself down in my chair at my desk and went to some of my favorite porn sites. I clicked on a few videos got my cock nice and hard and began stroking my cock to the images dancing on my screen. But the more I watched the more I realized that nothing I could find could scratch whatever itch or prevision I had at this time. It was as I was watching a brunette girl jerking a large cock and its cum into her mouth that I noticed an ad for a cam site. I figured maybe some live-action was exactly what I needed.

I click and was greeted with a slew of options for me to shake my stick at. I click around for a while, an emo girl here, pierced girl there. Most of the girls were just sitting there and they looked bored. Then I saw one that piqued my interest. It was an icon with a nice ass in a thong with white stockings on. I clicked on the room and was immediately treated to one hell of a sight to behold. This beautiful woman was riding a dildo in the middle of her shower while fingering her asshole. At first, I thought to myself 'nice tile, it's the same one I put into Sarah's shower. HA, what a nerd I thought. I could not see her face but could tell she was a brunette from the wet hair sticking to her back. This was exactly what I needed. I began to pick up the pace of my hand, stroking my hard cock up and down. Coating the head and shaft of my dick with the pre-cum that was leaking out of the tip. I wanted to time my cum blast with hers. I had to slow down a couple of times to keep from cumming too soon. I knew once I let myself cum that it would be one hell of an explosion. Just when I thought I could not take it any longer this goddess on my screen took the entire dildo into her perfect pussy and yelled that she was cumming. That's all I had to hear and in mid-stroke, my cock twitched and stream after stream of milky white cum came flying out of the tip of my glistening cock. I sat back in my chair to come down from my orgasm. I could feel my cum running all over my pubic region, but I did not have a care in the world at this moment. I felt like I was the only one left in the world. This I needed. I reached for the tissues and began to clean up the mess I just made. The angel on the screen was still coming down from her orgasm. She came off the dildo with a sexy slurping noise that indicated how wet her pussy had gotten during her fuck session. My cock started to stir again, how could it not. The beauty on my screen sat down in the middle of the shower and started to play with her pussy. Her tits now came into view and they were perfection. I could spend all day playing sucking and nibbling on those nipples. Then the angel said the words that I will remember for the rest of my life.

"Look how puffy and wet my pussy is. That was one of the best fuckings I have given myself in my whole life. Thanks for letting me share it with you all."

Just as my heart sank my cock sprang back to life. I had just pleasured myself to my baby sister and I was about to do it again and again and again.

Down the Rabbit Hole

Ever since that night, all I could think of was getting home and watching Sarah do her thing on cam. On the days when she did not have a cam show planned, we were back to our usual ways, dinner then TV then off to bed. I would always look forward to our alone time. But I also loved my alone time. I had become a regular in my baby sisters' cam room. She knew me by the name of SteveO. I bought all of her videos. I had even started to get custom videos made by my dear Sarah. I was addicted to seeing my little sister fuck her sweet little pussy.

There were times when work would get in the way of my voyeuristic ways. I have to travel from time to time because of the work that I do. Thank God for my little video collection. I would always make sure to take my laptop with me on the road. This way after a long day at work, when I get to my hotel, I would pick a video and go to town. But I would always miss being around my little sis. Even when she was downstairs doing her shows it turned me on knowing that we were both masturbating at the same time not too far away.

One night was almost more than I could bear. I mean this was one cam show for the ages. Sarah came onto my screen wearing black yoga pants with a green stripe at the top. She also had on a matching green sports bra. Her hair was also braided. She looked like an angel. I was instantly hard as granite. After a little while, I gave my sister the tokens needed to get the show started. The losers on that site have no idea what she is capable of. If they did it would take her no time to get started.

My little sis thanked "her Steveo" for the tip and proceeded to get naked.

Once naked my baby sister got out her favorite realistic dildo and stuck it to the wall so she could blow it like she had not had any cock for years. You could tell by the way she sucked that fake cock that she loves to give head. I was in heaven and stroking my cock feverishly. I could feel my first orgasm building in my balls. My sister then stated, "I think it's time my little pussy gets some attention, what do you guys think?" With that, Sarah sat back on the floor and spread her perfect sexy legs revealing her bald wet pussy. You could hear how wet my sister's pussy was when she ran her fingers over it. Sarah put one leg in the air as she began to finger her sopping wet cunt with her fingers. Just then with the other hand, she was caressing her ass and rubbing her asshole. All I could do was whimper "please finger your tight all sis." It's almost like Sarah could hear me because just as I said that she put her middle finger into her ass. I came instantly. I took a second to catch my breath but kept watching the incredible seen Infront of me. I was soon hard again. This time my little sister took her dildo and mounted it to a table that I built in her office. The next thing I knew Sarah was riding that cock for all it was worth. I started to stroke my now fully erect cock hard up and down, matching the thrust of the dildo in and out of my sisters' fuck hole. Sarah was screaming like I had not heard her do in some time. She said she was about to cum and with that, I came with her for my second cum of the night. Little did I know it would not be my last.

After all the excitement of the cam session with my sweet Sarah, I needed something to drink, I did after all just lose a lot of liquids. I headed downstairs for a drink and headed to the couch to watch tv for the rest of the night. After a few minutes, I heard my baby sister coming up the stairs. She was not running up the stairs like she normally does. I could tell she must be exhausted after her fuck session with herself only minutes ago. I did not give away that I was in the living room; I figured the TV noise did that. I heard her grab a bottle of water from the fridge. Then my sister came into the living room. She asked if I wanted any company, and I said sure without looking away from the TV. When I did look at my dear Sarah I am sure that my eyes came out of my head like something out of an old cartoon. Sarah had put back on the yoga outfit she was wearing before the cam show. She looked even better in person.

She said, "sorry I'm all sweaty, I was working out. I hope you don't mind me being all gross".

"Not at all" I stammered.

My baby sister lay down on the couch next to me and put her head on my thigh. I was starting to get hard again. Then to my surprise, Sarah placed her hand right next to her head and up my leg a little bit next to my crotch. I was shocked. I by no means wanted her to move it but I also did not want her to feel the growing hard-on I was sporting in my pants. My cock kept growing closer and closer to my sister's hand. I was in agony. All I could think of was 'what would happen when she feels my rock-hard dick?' This whole time I had my hand on my baby sisters' hip. I did not know where to put it when she lay down as she did. I noticed that Sarah was fast asleep. Suddenly Sarah grabbed my hand off of her hip and held it to her chest. All I could think of at this point was at least she won't feel my erection, though when I cum in my pants she might notice'. My right hand was between her right hand and her right breast. The feeling of her skin under my fingertips was almost more than I could take. Her skin was perfect. I did not dare move my hand no matter how badly I wanted to squeeze her tit. Just then I could hear a familiar sound coming from my little sister. She was moaning, not only moaning but I could have sworn my name came out of her mouth. I was so hot and paralyzed in fear. After only a minute of this, Sarah started to stir from her slumber, and I froze. It seemed to be my go-to move. Sarah awoke and looked at me and smiled. I returned the gesture. She asked how long she had been out and I said not long. She let go of my hand and told me she was going to head off to bed. I said yeah, I was going to do the same. She kissed me on the cheek and we headed off in our separate ways, her to sleep and me to jerk off one final time.

Even though I looked forward to our meetings online I knew the time would come when I wanted more. And the more and more time I spent with my sister online the more I wanted to take our relationship to another level. There were so many times when I wanted to tell her over dinner that I was SteveO. But the thought that she would hate me kept me from telling her the truth. I could not stand to lose my sister. She was all I had. I was in hell.

Party On

I decided to take a break from watching Sarah and see if I could kick my addiction. It was not easy at first but I was able after a while to keep myself from visiting her room or watching her videos. I still had mixed feelings about what I had done and I knew one day I was going to have to come clean. I don't like keeping secrets from my baby sister. It was towards the end of the year and things with Sarah were back to normal. We would do our old married couple night when it didn't interfere with her working late. One day a co-worker told me that there was going to be a holiday party for all the workers in my department. It was going to be a swanky country club and if I didn't want to be the butt of everyone's jokes, I would need a date. There was only one person I could dream of bringing to this type of thing. Sarah had not had a date since she moved in and I'm sure she could use a night out on the town. When I got home to ask my little sister if she would like to accompany me to my work event, I noticed the standard working late note. I thought nothing of it and warmed up some leftover dinner from the other night. I ate my dinner and promptly fell asleep on the couch. I was awoken by someone stirring in the kitchen. I got up to see Sarah looking for something to eat in the fridge. What she was wearing blew me away. Sarah wore a blue button-down dress shirt half unbuttoned; one of mine, white cotton panties, and nothing else. Needless to say, I was rendered speechless by this angel that stood in my kitchen. My little sister made no effort to hide herself when I walked into the kitchen.

"Hey big bro I did not know you were still up", Sarah said.

"I fell asleep on the couch, so technically I wasn't up", I told her with a little laugh.

I was hoping she would not notice the bulge growing in my pants.

"So, listen Sarah, I was wondering if I could ask you something." I nervously asked.

"Sure, you can ask me anything," she told me.

"So, my work is having this fancy holiday party in a month and I was wondering if you would like to join me?"

"You want your little sister to be your date? I would love to. I have to go dress shopping and get my hair done, oh man this is going to be so much fun. Thank you, Steve, our date night is going to be awesome."

Then she gave me the biggest hug. I could feel her breasts pressing against me. She had to be able to feel my hard-on now. I kissed her on the top of her head and she ran downstairs to shop. Date night with Sarah, I could not wait.

For the next month, all Sarah could talk about was our coming date. Her words, not mine. She loved calling it a date. She would beam with excitement when she said the word. She did eventually find a dress that she said was perfect. That's all she would tell me. She said she wanted it to be a surprise. As the day came closer and closer the bubblier and more excited became. She was like a kid again. I loved seeing my sister like this.

Anticipation

The day of the party was finally here. My little sister was a ball of energy earlier in the day. When she came upstairs for breakfast she was wearing a pair of sweatpants and a tank top with no bra, I could see her nipples poking through her shirt.

She was prancing throughout the house singing "I can't wait for tonight; I can't wait for our big date".

She kept calling it a date, which I thought was cute. Since Sarah was so excited about going on this "date" with her big brother I decided to pull out all the stops and treat it as if it was a real date. I got myself all groomed up nice and neat, I even rented a nice limo for the evening. Nothing is too good for my baby sister.

Shortly after lunch, Sarah retired to the basement to take a nap and get ready for the party. I reminded her that she needed to be ready at 5 pm. She rolled her eyes and shot me an "as I could forget." I decided that I would try and rest up before the party as well. I knew this could be a long but fun night and I wanted to be at my best for my date night with my little sister.

I was amazed at how much sleep I was able to get when I was so nervous about our date. I was worried that one of us would let it slip that we were brother and sister. I don't think I would ever live it down that I brought my little sister to the company holiday party. But the more I thought about it the more I did not give a shit. This was all about Sarah tonight and she deserved the night of her life. With that, I calmed down a bit and proceeded to get dressed. I put on the best pair of boxer briefs I had and put on my three-piece suit. It was a dark gray with light pinstriping. I took one final look in the mirror and thought I looked pretty good and headed downstairs to wait for my little sister.

When I got downstairs, I headed to the kitchen to pour myself a drink and help calm my nerves. Why the hell was I so nervous about a night out with my baby sister? This night should be a lot less stressful with the fact that sex is off the table. I returned to the living room and had a seat. As I settled in and enjoyed my drink, I heard Sarah coming up the stairs. I could hear the click and clack of her heels coming up the stairs. "I'm ready big bro; let me show off my dress before we go." As I looked up Sarah came around the corner and my jaw must have hit the floor. My baby sister was standing in front of me in a black dress that must have been sent from the heavens. She had on black strappy high heels and what I could hope were nude thigh highs. The dress came to about halfway down her thighs; it was sleeveless and showed off more than enough of her breasts. I was awestruck and could not move. I wanted to drink in her beauty until the day I died. I knew I was in for a night I would not soon forget.

We both climbed into the limo and headed off. Sarah sat right next to me and cuddled up next to me and placed her head on my shoulder.

"Thank you," she said.

I told her "You welcome, for what?"

She went on to tell me that she had felt a little lonely since she started her new job. That we did not get to spend all that much together and she missed me.

"Oh, well, my pleasure. I've missed you too little sis" I told her.

It's time to Party

As we entered the hall I could feel all eyes on me and my little sister Sarah. Well, all eyes were on her I was just in the way. We winded our way through the sea of people holding hands so I did not lose my date. I introduced Sarah to some of my co-workers; I think they were shocked I had such a beautiful date.

We walked across the dance floor and I could tell my sister had something on her mind.

"What's up? I asked her.

She asked me "Are we going to do some dancing tonight?" with some excitement in her voice.

Normally I would say no but how could I resist this angel? I told her we will and she gave a little squeal of excitement. We walked by a table with prizes on it and she asked what they were for. I told her they did a prize draw after dinner and before the dancing.