Catching Debbie Red-Handed Ch. 1byJRob©
I never had a brother, but if I had, I would have hoped for someone like Danny.
Danny O'Keefe was my best friend since sixth grade. For some reason, while other kids were getting caught up in a myriad of new friends and adventures, we bonded. We played inline hockey together, travel ice hockey on the same team, joked and shared our young life's pleasures.
There was one major reason why I was happy we weren't related....Danny's sister Debbie.
Debbie O'Keefe was two years older than us. We knew her first as a tomboy, but later she became the featured player in many of my masturbatory experiences. When she was a sophomore in high school she would tease us relentlessly, parading around in her bikini or short skirts and tight tops, a girl of 17 going on 25. She'd flirt, joke and cause us much embarrassment when she caught us trying to look up her dress.
Yes, Debbie was a hottie, a first class hottie. But as she progressed into her junior and senior years Danny and I became more an afterthought and finally ignorable as she went around with her older crowd and we with our younger one.
Danny hated it when I teased him about having a hot sister, but over time he began to ignore my barbs and comments. Usually our talk would get around to other girls, but in the back of my mind I would fixate on pretty blonde Debbie. My bubble burst one sweltering summer afternoon when, after joking with her, she told me to cut out the wiseass comments I was making. Throughout the day I felt it was merely innocent flirting, but she took it personally. Her put down, in front of a dozen of my friends, gave them reason to relentlessly tease me.
Oh well, as time went by I realized there were other fish to fry. I began lusting after Jill, a young cheerleader, Carrie, a brunette who sat across from me in several classes, and Mrs. Vance, the young science teacher who had a spectacular set of legs. Danny and I would trade stories about what we would like to do and with whom, secretly wanting to be the first to lose their virginity.
One Sunday afternoon Danny came by the house, looking bummed out and mentally beaten. "She told me I was a little twerp, and then called me a jerk off," Danny said sadly after an unexpected tongue lashing from his now 19-year-old sister. "Debbie has turned out to be such a bitch, and she has my parents wrapped around her fingers."
"What do you mean?" I asked, thinking of Debbie as not only beautiful but perfect in every way.
Danny looked at me, as if deciding whether to go further, then started spilling his guts.
"She gets her way, no matter what," said the dejected boy. "She wants a new outfit, she gets it. She wants to borrow the car, it's hers. But what really drives me nuts is that I end up holding the bag on things. I mean, she doesn't do a bit of work around the house, but when I get home from school I have to first do household chores before I can head out to play. And the other day when Debbie had the car I had to bike all the way over to the drug store to pick up mom's Tylenol. I mean, why couldn't Debbie get it, she had wheels."
I laughed and told him he needed the exercise, but he wasn't laughing.
"Hey, she might be a pain in the ass, but she really has a nice looking ass!" I said, laughing as I described watching her stroll out of the house in a pair of painted on white shorts and a tee top recently. "Any time your parents want her to get out of the house you can have them send her over to mine! Besides, she will be off to college soon and out of your hair."
Danny just shook his head.
"Laugh all you want," he said. "But she is a serious pain at times. She is always mocking me in front of people, she's driving me nuts. I thought as she got older she's be nicer to me, but now that she has turned 18 she's gotten even worse."
We had similar conversations over the next several weeks, and he continued to bitch about her actions while I agreed to some extent but still thought fondly of her building beauty. She was turning into a teenage bombshell, something all but a blind man could see.
Then came the phone call.
"Rob, can you get over here?" asked a subdued Danny.
"Sure Danny, want to shoot some hoops?"
There was silence, then Danny said, "No, I'm grounded, but if you come around the back of the house you can get into my room from the window."
He wouldn't tell me any more, only that he was to stay in his room during his free time for the next two weeks. So after wrapping up a couple chores I headed over to my friend's house. Good thing Danny's room was on the ground floor!
"So what's the big secret?" I quietly asked, once inside his unkept room. Even my room, with clothes thrown all over, didn't have a, well, putrid smell like Danny's.
"This time she has gone too far," said my best friend, pointing toward his sister's room. "This time I got grounded for something she said I did, and I am pissed off about it."
For the next half hour I heard Danny's tale of woe, of how his sister, after being told "no" for the 18th time about the purchase of a slutty red gown for her prom, stole money from her mom's purse and from the milk money in the kitchen to buy the coveted dress. She did it over several weeks, pocketing some away here and there.
"Did you see her take the money?" I quizzed.
"No, but I know she did it. It had to be her."
"So what has that got to do with you?"
"Plenty," he replied. " I needed a couple bucks for a watch, and she told me to go take some of the money out of the milk money bottle. I did, and that night I was confronted by my mother, who demanded I tell her where I got the watch, the money for the watch, and what did I think I was doing? I said I got it out of the bottle, but I didn't mention Debbie, because I didn't want her to get into any trouble. Then my mom blamed me for missing money from her purse, and before you could wink an eye I was grounded, and when dad got home I got the belt. It was 20 smacks and my ass still hurts."
"Why didn't you tell them about Debbie, I mean, she told you to do it," I asked.
"I really didn't want to get her into trouble, but then I realized she was just using me as a foil for her stealing, I mean, I heard her talking to Julie about the dress, how she was going to stop somewhere after leaving here prom night and change into it, and how she fooled my parents into blaming me for the stealing. Right away I knew I had to get her back."
"But how," I asked.
Danny lowered his voice before asking me a question. "That's where you come in. Do you still have your video camera?"
"Yes, my dad's but he lets me use it."
"OK, here's the deal, I know she is still short money for shoes and accessories for the prom. She can't go to mom and dad for money, because they think she's wearing a more conservative outfit. Mom is lending her some jewelry and shoes, so she has no need for money. I'm thinking when things cool down a bit she's gonna be looking to swipe some more cash. We have the video hidden, catch her in the act, and the rest, well, leave that up to me."
It didn't take much thinking for me to agree. "I'm game!"
It took months of trial and error as we sought the best and safest location. We finally realized the palmcorder would be easy to disguise amid his mom's plants on a high kitchen shelf. Timing was still a problem, since even on extended play we could only tape about three hours at a time. After reviewing tape after tape we found nothing incriminating. After a week of nothing, we decided to tape in the afternoons after school, when Debbie was first home and was alone for a while.
Two days later we hit the jackpot when the camera caught Debbie sneaking her boyfriend into the house. The twosome disappeared from view, but not before we watched the boy sneak a delightful handful of Debbie's pear shaped ass. The boy made a quick exit through the kitchen door about 30 minutes later. Debbie followed into the kitchen soon after, clothes askew.
"You don't think they..." I said, leaving the end of the sentence off.
"Nah, no way, I can't imagine she's having sex with anyone, much less that Jerkoid," said Danny, who turned 18 the week before. We continued to watch after the boy left. Low and behold there was Debbie reaching into the milk money container and slipping a couple bills out.
"We've caught her!" we said in unison. "Yea, baby," I added, slipping into a little Austin Powers.
"Say," Danny quizzed. "How about we tape her room to see if she and Jerkoid are up to something."
We spent the next several days formulating and carrying out our Bond-like plan. We drilled a small hole from Danny's closest into Debbie's next door room, set up the camera, and slipped out of school early to hit the record button. Again, the first couple days were total zeros, although we did catch a good view of Debbie in her underwear heading into the bathroom.
It wasn't until day three that our patience paid off. On that day, midway through the tape, we saw Debbie enter the room along with Jerkoid, and the two begin making out. The two locked lips for several minutes before Jerkoid got up from the bed and appeared to leave the room. Actually, he only left the camera's field of vision as he soon re-entered the view in only his underwear.
We saw the two lovers kissing, talking and kissing some more for a few minutes, when, unexpectedly to us, Debbie's hand crept into the boy's bulging underwear.
"Oh my god," my 18-year-old mouth exclaimed as I turned to Danny. My buddy's eye's were riveted to the television screen, and they nearly popped out when Debbie pulled out the boy's cock and began to lovingly stroke it up and down. She continued to kiss him while she jerked him off, and within minutes the boy scrunched up his face just as his cock exploded all over Debbie's hand and bed comforter.
"That's incredible," said Danny, "And we have it all on tape!!!"
It took me a minute to regain my breath. "That was really hot," I added.
That was the only time we caught the twosome doing anything out of line, but it gave us all kinds of ideas. I copied the tape, capturing the sex act and the pilfering of the milk money, and safely placed the copy beneath the floor boards of my room. Then Danny and I met to discuss what to do with the original.
I started the ball rolling. "I think we should give her the tape and get something back in return, like maybe what Jerkoid got."
"Ew, gross," said Danny. "She's my sister."
"But she isn't mine," I laughed.
We talked about the tape and the money and the pain she had caused Danny, and ultimately he came up with what turned out to be our proposal. Two days later when Debbie arrived home from school we put our plan into action.
"Hi Debbie," I cooed as she walked into the house.
The girl ignored me, and walked right past us as Danny said hello. Just as she started to her room I mentioned this great movie we had. She continued to ignore us until I let out a loud "whoa". That caught her attention, and she turned. Then, as she focused on the television screen, her eyes widened and mouth opened as if gasping for air.
The video of her reaching into the milk money jar was decent, but the following tape I spliced together of her jerking off her boyfriend made her run to the television set and hit the eject button on the tape machine.
"Where did you get this," she demanded, waving the tape in the air.
"Oh we got that and more," I replied, neglecting to mention that there was no more incriminating video on any of our tapes.
"I'm going to destroy this and then deal with you two," she added, heading for the basement.
"Ok, sis," replied Danny, "but there are copies of that tape."
Debbie stopped in her tracks. "Copies?" she said, incredulously. "What copies?"
"Well, we wanted to make sure we had an extra copy to give your folks," I deadpanned. "It's only right, since it will get Danny off the hook with your parents about the money, and all."
Debbie gasp for air. She looked at the tape, us, and started shaking her head. "I can't believe this. Please, give me the copies. I will make things up to you Danny. And you, Rob, I can't believe you did this."
I looked her in the eyes. "No, you did this Debbie, and it's time for your charade to come to an end. Unless..."
"Unless you are nice to us, really nice to us."
Debbie fell into a chair, not believing what she had heard. "What do you want?" she meekly asked.
"Nothing much," I said, taking on the role of negotiator. "Just a couple things. We will give you the tape and copies if you never again steal any money from mom and dad. Second, you do to us what you did with your boyfriend. Third, we get to give you what your dad gave Danny. And four, you treat us nice from now on, no more little boy jokes and lots of respect."
Debbie's goose was cooked, but she shook her head. "There is no way I'm gonna touch Danny, no way. He's my brother."
That was great news! She was willing to negotiate. We talked for a few minutes, but nothing broke the impasse. She argued long and hard about leaving her brother out of things, while I wouldn't give an inch on my side.
Finally it was Danny who came up with a workable solution and we all agreed that we'd hand over the tape over the weekend after Debbie completed her new instructions.
That Saturday afternoon, when Danny's dad was playing golf and his mom was out shopping, we handed Debbie a note and said we'd be waiting for her in Danny's bedroom. She simply nodded and read the note.
"Dear Debbie. Here are the instructions. You are to go to your room and put on the shortest skirt you can find, with a tank top, high heels and no underwear. We would prefer you wear red lipstick, but that's your call. Come into Danny's room and get on the bed. Lift the skirt, and show us how a good girl like you takes care of herself when her boyfriend isn't around. It had better be good, because it has to get Danny off. Once he has cum, you will call for Rob. Danny may leave the room or he may not. You are to take out Rob's cock and get him off with your hands. After Rob has cum, we will give you the tapes and you will agree to be pleasant to us in the future. You will never tattle on Danny again.
"At some time over the next week you will invite us into your room and let me, and Danny if he wishes, give you a bare bottom spanking. You will have the tapes at this point, so you can back out of the bargain, but we want to see how honorable you are. This is our last and final offer."
Words were not exchanged as Danny and I left the room and went to his bedroom. About 10 minutes later Debbie entered, wearing her cheerleader's miniskirt and tight top. She sat on the bed, looked at us, and then lay back. She lifted her skirt, and our eyes strained at the sight of her closely trimmed pussy.
Debbie closed her eyes, leaned back, and began caressing her thighs, gradually moving toward her hot, wet pussy. Once there, she began fingering her pussy, slowly, but with a purpose in mind. Her head tilted back as she slid first one, then two fingers along and then into her hole. It was the most erotic thing I had ever seen, even more sexy that watching her jerk off her boyfriend.
My dick nearly broke the zipper on my Dockers, but I kept it in my pants. She could have asked me to leave the room, but she didn't and I stayed in my chair as if stuck there with Crazy Glue. Danny was a little self-conscious with me there, but after a few minutes he slowly pulled out his cock and began stroking it while gazing intently at his sister.
Debbie pleasured herself in front of us, slowly and tantalizingly playing with her pussy while we intensely watched, just a yard or so away from her. She worked her hand on her pussy, using one finger to rub her clit. She was an erotic picture of multiple forms, acting as if she were alone rather than performing in front of two horny teenagers. She alternated long, luxurious strokes of the pussy lips with an index finger sliding inside her wetness. The strokes were insistent on ensuring pleasure, as she knew how and where to caress her honey box.
It didn't take much, but when she slipped three fingers inside her wet pussy Danny groaned and fired off numerous shots of his long-denied slimy load.
All became quiet, except for the sounds of heavy breathing, as Danny began cleaning up his mess and Debbie smoothed down her brief skirt to regain some semblance of modesty.
A few minutes Danny stood, nodded at me, thanked his sister, and left the room. After Debbie caught her breath, I maneuvered my way to the bed, sitting right next to her prone body.
"Lift your top for me," I asked, embarrassed with my words but anxious with my voice. Debbie slowly lifted her top and displayed her perky breasts for me. "No touching," she shyly demanded.
I wanted to grab them, fondle them, kiss them, of course, but that wasn't part of the bargain. I inspected her breasts and lusted at her as she smiled and held them in her hands, tweaking her nipples to hardness. She nearly floored me when she told me they "must like me because they are growing."
After a few minutes of watching her fondle herself, she reached over and unzipped my pants, reached into my underwear, and brought my cock out into the open. "You must like me a lot," she smiled, mimicking her prior saying, "cause you are giving me a standing ovation."
Like a zombie, she began fondling my hardening cock, getting to know its girth and feel with her eyes closed. She began stroking my cock, slowly at first, then faster and faster, as I began to rock in tandem with her effort.
Her skirt slid up her leg, offering me a perfect up close and personal view of her pussy, and I nearly shot. Somehow, though, I held it in, wanting to extend the pleasure of her hand. She jerked me off as I continued to enjoy. One hand was on my cock, the other played with her pussy, and I imagined how hot and wet it would be deep inside her womanhood.
I was in ecstasy, I was on cloud nine, I was floating above the earth.
"Danny, are you going to cum soon?" she nicely asked, startling me back to reality. "My hand hurts."
I merely grunted a basic I'm not ready response. I closed my eyes, thinking of disasters to keep from cumming. Then I felt something wet on the tip of my cock.
I opened my eyes, and nearly fell off the bed. Debbie was licking my cock. Unbelievable!!! Like lightening, I shot a load of stored up cum. The sticky sauce cascaded all over her face and hands as I had the first orgasm not sparked by my own hand. She continued stroking my dick until I was totally spent.
Staring at her youthful body I nearly collapsed. My first time is one that will be etched in my memory forever.
I lay down on the bed next to the girl, who caressed my head in a way I never thought possible. She used my tee shirt to wipe my cum off her face, and said she hoped that since she completed her end of the bargain, and more, she could trust me to give her the telling tapes. As I recovered, I told her that of course she could have them, then puppy lovingly professed how wonderful I felt. She sort of smiled, as if to confirm she knew.
Danny re-entered the room, his eyes averting our mass on the bed, and sat down on the chair across from us. There was a sense of embarrassment as each of us averted our eyes from each other.
"Sis, the tapes are on the shelf there."
Debbie nodded, rose, collected the evidence and started to walk out of the room. Before she exited, however, she turned and quietly said she remembered there was the matter of the spanking in the agreement between us. She said she would indeed uphold her end of the bargain.
"That was unbelievable," I said to Danny after she had left the room with the evidence. "She blew me."