Blackmailing my sister for sex

1912 words | 8 |4.46

I was lucky enough to catch my sister giving her boss a blowjob.

It was the summer after my high school graduation and I had nothing to do till I started college in the fall. I had not been able to find a summer job so I was just going to hang out and relax for the next couple months. We lived in an upper middle class neighborhood in a nice house on a two acre lot and we had a pool at home so I expected to spend a lot of time in it and to invite friends to come over and join me. I was planning to invite a lot of girls and hopefully convince them that swim suits were not required.

My name is Rex and I had just turned 18. I lived with my mom and dad in a suburb of Dallas. I also have a sister named Sandra. We all called her Sandy. She was 22 and had her own little apartment a mile or so from home. She worked downtown at a company that has something to do with financial investments. She was the company president’s personal assistant.

One day I got the urge to go down and have lunch with Sandy so I arrived at the building that the company was in at a few minutes before noon. Her lunch started at noon. I went up to their offices on the 12th floor. Everyone there knew me so no-body questioned it when I walked in, walked past them and went back to the president’s offices. Sandy had a desk in his outer office but she was not at it.

The door to his office was closed but not completely. I thought about asking him if he knew where Sandy was. Maybe she had started lunch a few minutes early and had already gone out with some of the others from the office. If so, it would not do me any good just to wait around for her to get back to her desk. I started to knock when I saw something thru the small opening in the doorway that made me stop.

Mr. Donniger who was about 50, chubby and going bald was leaning against the front of his desk with his pants on the floor. Sandy was on her knees in front of him, giving him a blowjob. You could see enough of both of their faces to easily tell who they were. She had her top off and he was fondling her breasts. She was doing a great job. Sandy has big tits and I have always wanted to get my hands on them but never figured out a way to do it. I guess that being her boss was a good way. She is attractive and about 5’5″ and not more than 120 pounds with tits that I am sure are D-cups. They did sag a little but I guess that it is hard to hold up all that weight.

I pushed the door just a little way further open and took out my cell phone. Using the video camera function, I took almost a minute of movie footage as she brought him to a climax and he shot his cum on her face and in her mouth. Before I could get caught, I quickly left, telling the others that I would see Sandy later.

As soon as I got home, I downloaded my pictures on to my computer and with a big smile on my face and an erect cock I watched them about six times while I jacked off. Finally I blew my load in my hand, turned off the video and went to the bathroom to wash my hands and prick. When I got back I closed the file and shut down my computer. I sat on my bed thinking about how I could use this for more than just something fun to masturbate to.

The next evening I had my plan figured out. I e-mailed what I had shot to Sandy. The subject line said, “Looks like you were having fun.” The next morning about eight thirty, after Mom and Dad had gone to work, I was still in bed just thinking about getting up for the day, when my bedroom door flew open and Sandy stormed in. I smiled, “Hi Sis.” She crossed the floor and gave me a hard slap across the face. I just smiled at her. “What the fuck do you think you are doing taking pictures like that? I want you to get rid of them right now.” I told her that I had it saved in several places and had made copies of it on DVD and flash memory sticks and that I had no intention of deleting any of what I had.

She sat on the edge of my bed and started to cry. I sat up and put my a arm around her shoulder. She shook me off and pushed me away. I only had a sheet covering the lower half of my naked body. “What do you want me to do?”, she sobbed. I pulled the sheet away and she got a good look at my thick seven inch erection. “The same thing you did to your boss and more.” “No fucking way. That’s blackmail and you’re my brother. Put that thing away, you pervert.”

“Maybe I should send it to the general mailbox at your company so they can all watch it. How would you like that?” “Well Mr. Smartypants, it just so happens that everyone there knows just why I was hired and just what my duties are. They call me his sexretary. I can’t type worth shit. So there.” “Then what if I sent it to Mom and Dad and your boyfriend?” More quietly, Sandy said, “you wouldn’t do that, would you?” She sat there for a minute and then asked, “If I give you a blowjob, will you destroy all that footage?” “Nope, but I won’t send it to anybody as long as you are keeping me satisfied.” All she said was, “Asshole.”

After another pause, Sandy reached out and took my rock hard manhood in her hand. “You do have a really nice cock. The last time I saw it, you were four.” She stood it up with her hand and then leaned over, licked off the pre-cum that was starting to run down and slipped her lips over the end. My cock jumped with excitement at the touch of her lips. This was even easier than I had dreamed it would be. Maybe she also had been wanting me but did not know how to let me know.

Sandy held my cockhead between her lips and jacked my shaft with her hand while licking around the tip. After a minute of that, I wasn’t getting what I wanted so I put my hand behind her head and pushed her further down onto my skin flute. She took the hint and removed her hand and started bobbing up and down on my pole. She didn’t take me into her throat but did get about five inches of my meat in her mouth. That was enough to satisfy me. After a couple minutes, I actually heard a little moan of pleasure come from her and she picked up speed and sucked harder.

She took my cock out of her mouth and said, “Warn me when you are going to come.” I told her, “No way. I’m going to surprise you.” Sandy gave me a dirty look but went back to blowing me. As she kept sliding her tight lips up and down on me, I started matching her with little up thrusts, trying to get even deeper in my sister’s mouth. A couple times I made her gag slightly and she punched me on the thigh. I think she could feel my ball sack tighten and my prick swell but I didn’t tell her I was ready to come and she did not stop. I moaned and held her head and let go with what I am sure was the biggest load I had ever produced. I jerked four times. Each time , I shot a powerful blast of baby sauce into her mouth. She never spilled a drop or asked to go spit it out. After she had swallowed, she looked at me and said, “Fuck you.” I thought I might have seen just a little smile on her face.

To my delight, I remained hard. “That’s exactly what I had in mind. You’re going to fuck me. Now strip.” Without any hesitation my sister started removing her clothes. Again I thought I saw that tiny smile as she cussed me out, “You’re a fuckin’ blackmailing asshole. I should cut your balls off.” I took just a minute to admire the beauty of my sister. Her smooth skin, her perfect proportions, her firm breasts, they were what I had dreamed of for years and now they were mine.

I lay on my back. “OK, get on and ride.” Sandy got up and put a knee on either side of me, lined my cock up to her fuck hole and dropped down onto it. She rode me hard and fast and deep. She had her hands on my shoulders and I was playing with her tits as she fucked me like a cowgirl riding a galloping horse. It wasn’t long before she had a hard orgasm. She screamed out in pleasure and I felt her cunt juices flow out around my cock and onto my balls and in my pubic hair. She stopped with her eyes closed for just a couple of seconds and then started riding me again but this time with a slower pace. “I hope you are on the pill because I’m not going to stop till I’m completely empty.” She replied, “I am.”

I bet I lasted another five minutes and I could see her starting to sweat heavily. She had two more small orgasms as she rode my manhood. I could tell that I was not far from my own ending. I started fucking rapidly up into her cunt and then I filled her womb with as much spunk as I had filled her mouth with earlier. She held still with me fully in her as she felt it pulse and felt the streams of fuck fluid fill her. When I had finished, she rolled off me, exhausted. “You’re not done yet. Get back down there and suck me clean.” she did it without complaint.

We lay side by side on my bed. “I saw you giving your boss a blowjob. Does he fuck you too?” Sandy quietly said yes. “Does he fuck your ass too?” She hesitated for a minute and then said yes. “I’m happy to hear that,” I told her. “I’ve gotta go. Did you get everything you wanted?” I told her that it was a good start but I was far from finished with her.

Sandy got up and stared getting dressed. Before she left she told me that Ted, her boyfriend, was going to be out of town for a couple of days and suggested that I might come over to her apartment for a visit. Just before she walked out the door, she surprised me with a big deep French kiss. Then she was gone but I knew that we had only started something that would last for years.

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