My sister, the hooker!

Note : This story is completely fictional!

I didn't know if I should write this, but I couldn't hold it in any longer. Something happened to me a few weeks ago and it's been killing me to tell someone.

I work as a security guard and often work long night time hours. I sleep most of the day and therefore have little to no social life. This doesn't bother me to much, but sometimes I get very lonely. I have no roommates at home because of my weird hours and I live far away from most of my close family, except for my sister.

My sister’s name is Claire; she is 25 years old and 2 years older than me. She moved out of the house when she was 18 to go to college, but found herself not enjoying it and quit. mom and dad were furious and they had a huge fight and she moved out here (2000 miles from our parents). When she was 16, I was really close to my sister. She wasn't the typical older sister who wanted nothing to do with her younger, hormone crazed brother, quite the opposite actually. Claire actually hooked me up with some of her single friends. Now, I'm no super model, but I not that bad either. I'm 6'3, 205lbs, dark brown hair, pretty muscular in a thin way. I'm also not a porn star (like most of the male writers in here think they are). If 6 and a half inches hard is average, I'm a bit more than average at 7 and a half with what I would call normal thickness. 

Anyway, my sister was always hooking me up, telling me that she had the perfect girl for me and then getting me a date. At first I was nervous about her doing this for me, but as the girls she kept picking out for me were her friends and they were all attractive, I soon became used to the attention. I had a lot of fun in those years and the experience really boosted my confidence and my appeal towards the opposite sex. Listen, everybody knows girls talk about guys.

Let me tell you a little about Claire. Unlike plain old' me, Claire is strikingly beautiful. She takes after my mother, who is very attractive still to this day. Claire stands at about 5'8, strawberry red, curly, below the shoulders hair, medium sized breasts, about 115lbs, and long, long legs.

Now I've never really fantasized about my sister, but when I was younger, I saw her with one of her boyfriends. She was giving him a blowjob in the game room of our house. The game room was where the kids (Claire and I) entertained our friends. Boy, was she entertaining! His pants and underwear were down around his ankles, and his arms were clasped around the back of the chair. My sister was bobbing her mouth up and down on his dick. She was making a lot of noise, sucking and slobbering, but it seemed to be just the thing cause the guy, whose face I couldn't see, was sure enjoying the treatment.

I stood there quietly in total shocked amazement, and even though it was my sister, I found my self harder than ever before. By this time in my life I knew about masturbation and was a frequent flyer. Absentmindedly, my hand went to the bulge in my shorts and as I watched the action I started to stroke my cock in time with my sisters bobbing head.

I had no sense of time, no sense of being, nothing. It was like I'd entered another universe. All I could see was my sister sucking this guy’s cock, and all I could feel was my hand on mine. Suddenly I was brought back to reality be a sound. "Oh god, Claire, I'm gonna cum!!" My sister picked up her pace and started massaging his balls. I to, felt the oncoming release. Mystery guy lifted his ass off the seat and grunted loudly, "Here it comes baby, drink it all for up for me." I heard my Claire groan and I saw her throat contract as his load emptied in her stomach. That’s when I came. Cum went six feet straight out from me and on the carpet. Whether I knew it or not, I grunted. My sister, mouth still glued to the cock she was sucking, just looked up and to the side, noticed me and winked!! I ran as fast as I could outta there and into my room under the bed.

I was so embarrassed. I didn't know what to do. I had just been caught jerking off to my sister giving a blowjob to some dude. After about 20 minutes, I heard the front door close and a car drive away. Then I heard a knock at my door. "Alex, can I come in please?" I gulped and went to my door ready for the beating I knew was gonna take place. Claire came in and sat down on my bed. She was wearing night time stuff, tee shirt and boxers, and then she patted her hand on my bed telling me to come and sit. 

"Alex, I'd like to talk about what you saw tonight. I'm not mad that you saw me and Tom, but I want to be sure you are ok with what you saw." I was beside myself. I thought she was gonna kill me for spying but here she was worried about me! "I'm sorry that I walked in on you and watched, but I was frozen in place and couldn't take my eyes off of you and what you were doing. I mean some of the guys from school told me about that stuff but I never thought I’d see it for real." My sister smiled at this, "Alex, there will be a ton of chances for you to see that again in the future if you play your cards right and treat women with respect and honesty." She paused for a second then continued. "I guess what I want to really know is why were you jerking off? Did you know that you were doing that? Was it because of me or just the blowjob I was giving?" I had to be honest with her and with myself. "I knew that I was touching myself, and it was a combination of all those things. What you were doing was so sexy and it looked like he was really enjoying himself." Claire smiled and giggled a bit, "I sure hope so." I continued, "I just never knew you did that and when I saw you, I couldn't believe how beautiful it and you looked." 

Claire stood up and walked to my door. "I hope we can keep this to ourselves little brother? Oh and by the way, I cleaned up the mess you made down there. It's very impressive Alex. You are gonna make some girl real happy some day." 

From that day on, Claire and I got along better than ever. She started hooking me up with friends and her friends were very accommodating when it came to sex and women. Sometimes I would sneak into the game room and watch as Claire would have sex or give blowjobs. She often had guys over and I started to notice that they were different all the time, some repeats but mostly different. Every time I did that I came harder than ever, even when I was myself having sex. I couldn't really explain it. Was it my sister that was causing me to orgasm hard? Sometimes she would see me and get more worked up and start getting real wild. I started to think that she was doing this for me and that it made her hornier to know that I was getting off because of her. We would never talk about it but we knew deep down that we had something special between us.

When Claire went to college I thought my social life would plummet, but it didn't. Like I said earlier, girls talk about this stuff. With my sister’s help, I had made a name for myself as a nice, considerate lover who took his time to ensure that the girl had a great time. I missed my sister but knew that the time apart would be short as I was planning to move to the same college as she did.

Then she quit. The fight between her and our parents was explosive and ugly. Claire had just not found what she was looking for as a person. My parents couldn't and wouldn't understand it. They fought for weeks until finally with a hug and a quick kiss for me, she was gone and out the door.

A couple of years went by and we heard from Claire every so often. I graduated and I got a long letter from her saying now I could finally come live with her. I could go to school and she would help me pay for it so Mom and Dad could have no say in what I did. This was good news from me because ever since Claire left things had gotten pretty bad around there. They were always fighting about Claire and that one or the other should have done things differently. I couldn't wait to leave and be 2000 miles away.

When I got there, Claire had changed only a little. She looked fantastic. A little more makeup than I was used to seeing, but still breathtaking. She ran up and gave me a big hug and to my surprise, a kiss. Not the kind of sisterly peck one would think, but a deep, tongue kiss that made my dick stain to get out of my pants. I broke the kiss, took a deep breathe and just stood there with a shocked look on my face. My sister just smiled and said, "Man o Man have I missed you little brother." I followed her and I couldn't help but admire the sway of her hips and the shake of her ass. 

During the ride home, I noticed a few things. Her car was really nice. Brand new, expensive and full of sex stuff, condoms, dildos, panties, bras, lube, and all kinds of things. I looked at Claire and said, "Um sis, what’s with all the goodies?" 

"I can't tell you right now, but we will have this conversation soon ok?" She had a smile on her face so I knew the news couldn't be bad. "Ok Claire, when you are ready to tell me, I'll be here for you."

I got settled in and the apartment was nice and roomy. I had my own room and my own bathroom. There was a door with a lock connected to my sister’s room and my own door was also a lockable one. We ate very well and school was fun as well as educational. I met some friends and some girls, even had a couple of elicit encounters. Then the day came. This is what I've been trying to say now for this entire letter.