Bree had begun babysitting for us when she was 15 years old. Her real name was Briana, but she didn't like that, so she always called herself Bree. Now she was 18 and in the last year of high school.
I often used to kid her about what she wanted to be when she “grew up” because even at the age of 18 she was only about five foot four, about 100 pounds and cute as a button. With shoulder-length blond hair and the face of an angel, she looked like a very young Britney Spears. Only unlike Britney, she radiated a delightful innocence.
That was until she became a senior. A lot of people—me included—believe you can tell if a girl is a virgin or not merely by looking in her face. As a senior, Bree still radiated innocent beauty, but she also radiated a knowledge of her sexual attraction that she did not have before. I knew that she had a boyfriend, Chris, who was a high school football hero, so I suspected he was the culprit who had robbed her of her virginity. Lucky man.
Also, as a senior, she began asking us if she could invite someone over on babysitting night “to help me study.” Usually, the person she invited over was gone by the time we got back, but I began to suspect the study mate was Chris.
My belief was confirmed when after returning one evening from seeing a movie, I went to the bathroom and happened to notice something unusual in the basket by the sink. I bent down. It was a foil wrapper for a ribbed Trojan. Since I had had a vasectomy ten years before, I knew it was not from me. I pocketed the wrapper.
The following Saturday was our 10th anniversary, so I invited my wife Ally out for dinner. But while she was in the bathroom getting ready, I did the setup. I took our video camera and laid it down behind a couple of stacks of books on the top of the entertainment center, directly across from the couch. Looking under the stack of books, the camera had a clear shot of the couch, which was the most likely place Bree would sit. I had loaded the camera with a slow-running four-hour tape. Just before my wife came down, I pressed the On button. The camera is very silent, and you can barely hear it, but just to be sure, I turned on the TV. Knowing how most teenagers are, I figured Bree would just leave it on, and it was very unlikely that anyone would spot the camera or know it was on.
Bree arrived right on time. Lately, she had taken to wearing a skirt instead of jeans when she came to babysit, and I wondered about that as well. She was wearing a blue and green pleated skirt that fell to her knees and a man's style white shirt. Generally her dress tended to be conservative since her father was the local Methodist minister and disapproved of nearly everything, especially things that teenagers might do. She also was carrying two school books.
“The kids are both asleep,” I said to her as my wife and I got ready to leave.
“Okay. Is it all right if I ask someone over to help me study?”
So we left.
We returned about four hours later, I paid Bree and drove her home.
“I'm going to stay up for a couple more hours,” I said to my wife after I returned. She was just going upstairs. “I want to finish this book I'm reading.”
“Okay. Try not to wake me when you come to bed.”
After I knew that she was safely upstairs, I pulled the camera out from behind the books, rewound the tape, turned the sound down on the VCR, and inserted the tape. As with any movie, I had to fast forward to the good parts, but I got to them soon enough.
As I had suspected , Bree's “study mate” was boyfriend Chris, and he also was carrying two books. But he discarded them on the coffeetable as soon as he entered and drew Bree into a passionate kiss.
They sat down together on the couch, and he began caressing her breast through the white shirt. Since I had the sound turned down, I could not hear what he said to her, but it must have been something suggestive. She got up, walked over toward the entertainment center, turned around, and began unbuttoning her shirt. Unfortunately for me, her back of course was turned to the camera.
She took off her shirt and tossed it to Chris. Then she pulled down the zipper at the back of her skirt, stepped out of it, and tossed that to him. She also stepped out of her shoes. Then she unfastened her bra and tossed that. Finally, she hooked her thumbs into the waistband of her panties and pushed them down. She kicked them over to him.
He of course had the best view in the house, and the camera had the poorest since all it saw was her bare back and her pretty little butt.
Apparently knowing what was expected of him, Chris unfastened his belt and pushed his pants and shorts down to his knees. His cock was already hard and standing. Bree walked over to him and sat sideways on his lap. Now the view was a little better but not a whole lot.
He kissed her again and caressed her breast. Finally, he separated her thighs and slipped his middle finger inside her. It looked like she was starting to moan. She grasped his cock and jerked it up and down. He stopped her after awhile and took a wrapped condom out of his pocket. He pulled it out of the wrapper and rolled it on his cock.
Then, at what must have been his suggestion, she swung one leg over to straddle him, and he inserted his cock into her. Even from the back I could see that. I turned the video off. I had seen enough. It was all very nice and told me what I wanted to know, but it did not satisfy me. There must be some better way I could use this tape.
And then I thought of one. The idea was despicable of course, but when a man sees a never-again opportunity, sometimes “despicable” is the strategy to use.
My wife Ally and the two kids were going away the next weekend for their annual visit to grandma's house. Grandma and I did not get along, so I always stayed home. This was the perfect opportunity.
I called Bree on Saturday morning and told her I had something very important to talk to her about and could she stop in some time today?
“Sure,” she said.
She arrived about 1 p.m.
“This is not about a babysitting job,” I said, “Ally and the kids are away for the weekend. This is about something I want you to look at.” I led her into the living room and indicated she should sit on the couch.
As she did, I turned on the TV and the VCR with the remote and then clicked the tape to start. I had already advanced it to the part where she was removing her clothes. I could see her grow pale as she watched it.
“I was doing some videotaping that day, and I apparently did not realize that I had left it on when I put it on top of the entertainment center next to some books,” I said. “Or else, maybe the cat stepped on the On button.” I did not know if she would believe either one of those unlikely stories, but it did not matter. “I realized it was still running when I came home since it's a long-running tape, so I put it in the VCR after my wife went to bed to make sure the tape was not damaged—and this is what I saw.” Now, on the tape, with her back to the camera, she was completely naked. She looked up at me from the couch.
“I don't know what I should do with this,” I said. “As a responsible parent, I know I should turn the tape over to your parents. But I also know how strict you father is, and I can see this getting Chris into real trouble as well as you.”
“I'm…sorry,” she stammered.
“Well, I know how young people are, and I guess it's a fairly normal thing to have happen, but I don't like the idea of my home being used as a motel.”
“I'm really sorry. I'll never do it again.”
“What do you think I should do with it?”
“Well, I don't want to do that, but I'll tell you what. I'll make a deal with you. I'll sell the tape to you.”
“But I don't have any money,” she said.
“I'm not interested in money. But you could buy it in another way. Even though I'm old enough to be your father, I'm still a man, and I can certainly appreciate the fact that you're an exceptionally beautiful young lady—especially when you're naked. If you would provide me with the same things that you provided Chris with—for just one time—I think I would be willing to give the tape to you.”
She stared at me incredulously. “You want to have sex with me?”
“You got it.”
She looked down.
“I'll tell you what. You don't have to decide now. Why don't you go home and think about it. Then tomorrow, if you decide that's what you want to do, come over here around the same time in your cute little cheerleader outfit. I'll take that as the sign. Okay?”
She didn't respond but got up. “Is that the only copy?” she asked.
“Of course. Do you think I'm going to risk taking it to the photo shop and having it copied? Once you buy it, it's yours—to do with as you see fit….And by the way, I don't think I would mention anything about this to Chris. This is between us.”
She turned and left.
She came back at about the same time the next day. And guess what? She was wearing the high school cheerleader uniform of a pleated blue and white skirt, a blue and white sweater, white shoes, and knee socks. She looked quite fetching as I let her in.
“So you've agreed to the terms?” I asked.
She nodded and walked into the living room.
“What do I have to do?” she asked, turning in front of the couch.
I walked in and sat on the couch opposite her. “Well, I guess the first thing you should do is to take your clothes off, slowly if you don't mind.”
She drew in a deep breath, then pulled her sweater over her head and dropped it on the floor. Then she unzipped her skirt from the back and let it drop. She was clad only in a white bra and white panties, having left off the black cheerleader pants.
“You can leave your shoes and socks on,” I said. “The floor is cold.”
She reached behind her back and unfastened her bra. Then she pushed it from her shoulders, letting it fall on the rug. Her breasts were small but quite beautiful. Finally, with a sigh, she hooked her thumbs into the waistband of her panties, pushed them down to her ankles and stepped out of them. She had a very cute little blond bush, and she made no attempts to cover it but held her hands at her sides.
“You're very pretty,” I said.
“What should I do now?” she asked.
“Well, you could smile for one thing. This isn't the end of the world, you know. I'm not asking you to kill your dog or something. The only reason I'm asking this is because you're so very pretty, and I envy the treats that Chris has been able to enjoy.”
“Isn't this illegal?” she asked.
“Well, it may be immoral, but it's not illegal. You are of legal age, and you're consenting. Any by the way, since I had a vasectomy ten years ago, I don't have to use a condom with you as Chris did. I found his wrapper in the bathroom basket.”
“Now, if I'm not mistaken, you've also provided Chris with a blowjob from time to time, so I would like that as well.” I was just guessing at that, but I could see from her face that I was right. I unzipped my fly and took it out.
She got on her knees before me and took it in her hand. “You're bigger than he is,” she said.
“Why, what a nice thing to say.”
Then she took it into her mouth. At first she gagged a little, but then I guess she decided she was going to do what it took to get that tape back, and she began to suck and lick in earnest. She actually looked like she was enjoying it, and it was all I could do to keep from coming in her mouth.
“That will be enough,” I said. “Now stand up and straddle my lap.”
She did so, with her knees on either side of me. Her pussy was very small, and I could see this was not going to be easy. I wet my finger and tried to stick it inside of her, but she was really tight. “Stand up on the couch in front of me,” I said, “I'm going to have to lubricate you.”
She did so, and I enjoyed thoroughly the act of performing oral sex on her, sticking my tongue in her and lavishing my saliva on her until she was quite wet—and I hoped some of it from her. I thought how interesting it would be if my wife came home early and walked in on this. I could turn and say: “It's not what it looks like, dear”—but I'm not sure she would believe me.
“Now I think it will fit,” I said.
She slowly lowered herself and taking the initiative took it in both hands and gradually impaled herself. She grimaced a little when she got to the bottom of it.
“Does it hurt?” I asked.
“Sorry about that. But it would be really nice if you could go up and down on it slowly.”
Closing her eyes, she did so. I don't know what she was fantasizing, but I could see from her face that she actually was enjoying it. I grasped her by the side of her naked hips. She was as tight on my wet cock as the tightest glove.
“I can't stand any more of this. I'm going to have to come inside you,” I said. “Is that all right?”
Still with her eyes closed, she nodded. And I came inside of her so hard that I was surprised it did not squirt out her nose. She collapsed against my chest, and I held her naked body. I was tempted to try and kiss her, but I thought I ought not to try and go that far. A kiss, after all, is personal. But tight or not, I know she would be leaking down her thigh for the rest of the day.
She looked at me.
“Yes, you can get off now,” I said.
She found that even that was not easy. Even with a soaked pussy, she was still tight.
I knew as I zipped them up that I would have to wash these pants myself.
As she was dressing, I stood, walked over to the bookcase, and pulled out the tape from behind some books. After she finished dressing, I handed it to her.
“This is the right one?” she asked.
“Yes. I wouldn't try and cheat you.”
She took the tape but hesitated.
“What is it?”
“Maybe I shouldn't tell you this, but towards the end, I was actually beginning to enjoy it.” She looked up. “Does that make me a slut?”
“No, it makes you a healthy, normal girl, and I'm so glad you told me that. It makes me feel better about blackmailing you.”
“You're a very bad man,” she said with a smile.
“I know, but I just couldn't resist when I saw you naked.”
She hesitated. “When are your wife and kids going away for the weekend again?”
“I don't know. Maybe around Christmas, I guess. Why?”
She gave me a very wicked smile. “Maybe I could come over.”
And she did. Come over. With a present…that needed unwrapping.