Catching Debbie Red-Handed Ch. 2byJRob©
In an earlier story, "Catching Debbie Red-Handed", I told the tale of getting the goods on my best friend Danny's sister. Not only had we spied on her stealing from her parents, but we caught her in a nasty but sensual situation with her boyfriend. The incriminating evidence was all on videotape. Once we presented her with the data, the once aloof girl turned into a wet dream of a woman. We had convinced her to masturbate for us, and I was lucky enough to have an agreed upon hand job turn into a scrumptious blowjob. What follows is the remaining task Debbie had to accomplish before we'd completely let her off the hook: a bare bottom spanking.
On Thursday night, the week after we had unveiled our evidence to his sensuous sister, I arrived at Danny and Debbie's modest single family home with a hard-on sparked by anticipation over what might happen. The last few days had been hectic, as Danny and I had to use every bit of power we had not to blurt out to the world what we had done with his sister.
Their parents were at the theater, and wouldn't be home until after 11, so there was little chance our tryst would be interrupted. Good think, too, because we expected the girl to cry out in pain at least once or twice as we satisfied the terms of our "agreement".
Deep inside I wanted the world to know the beautiful cheerleader had jerked me off before giving me a mind-blowing session of oral sex just days before. How she had masturbated for both of us, and how she agreed to our demands to give her a spanking like the one her father had given Danny months before. Of course, letting anyone know would ruin everything.
That spanking was the result of Danny getting the blame for Debbie's larcenous behavior. He took the heat on his ass for her, and now that we had the video of her in action with her boyfriend and stealing from her parents, we had the upper hand.
Although we had given her the tape, presumably divesting ourselves of any and all evidence, Debbie had committed to completing her end of the bargain. She told us in no uncertain terms that she would receive the agreed upon spanking and that our deal would be complete.
What Debbie didn't know is that her darling brother had taped her blowing me, a hole card that he and I decided not to play. At least, we wouldn't play it at this time. That didn't mean we didn't watch the tape, as each of us had kept it for a night, memorizing each bob of her head on my dick that quickly exploded.
Danny greeted me at the front door of their suburban center hall colonial, saying his 20-year-old sister was in her bedroom, waiting for us, resigned to her fate. He mentioned that she was concerned we might go overboard, and that our smacks might be too hard and would show over the weekend when she was supposed to go with friends to the beach.
"I told her we'd be careful, that her ass would be warmed and she would be humiliated, but we wouldn't permanently mark her perfect ass," said Danny with a smile. "Geez, I just can't believe she's following through with the spanking, because she does have the tape. But I think this is to make sure we don't open our mouths!"
"Well, she sure knows how to open her mouth . . . and close it," I flippantly replied, adding that "maybe I should request a repeat of last week's oral workout."
Danny demanded I cut it out, that his sister had done what she had agreed to do, and that I needed to own up to our end of the bargain.
I knew he was correct, she had shown me the best night of my life and I had a tape of her doing it. Tonight I would get to pulverize her perfect white ass until red, and that would undoubtedly be an event etched into my mind for ages.
Danny called up to his sister, informing her we were on our way up to her bedroom. She had a beautiful room, complete with chiffon sheets, fluffy pillows, and bright, friendly color coordination. Dolphins rode atop the whitecaps in a poster on one wall, while a set of Barbies sat on one of the shelves above her bed. The room's accoutrements paled in contrast with the pretty young cheerleader.
Debbie lay against pillows adorned with white lace. She wore a tee top that covered her generous breasts. A short pleated white tennis skirt barely covered her midsection, displaying her creaming white thighs. She looked up as we entered the room, a smile crossing her lips.
"Well, you boys showed up, huh? Wasn't the other night enough for you?" she asked, attempting to make light of the situation. "Now you know, I have the tape, so I don't have to do this."
Secretly, I really think she wanted to be spanked. I mean, why else would she submit to this demand?
"Nope, sis, a deal is a deal. I've been waiting for this moment," chirped and enthusiastic Danny, slapping his hands together in anticipation. "Remember that whipping dad gave me after you stole from mom's purse? Now the proper person will be punished."
Debbie's smile was replaced by a frown. "Now, you promised not to go overboard. Remember? I said I would go along with your perverted desires, but you guys promised to be gentle…no marks. Agreed?"
We nodded our heads in unison. Of course, we would have agreed to jump out the window at this point if we got to whack her pretty ass. Heck, a broken neck would pale in relation to copping feels of her perfect little ass. Debbie was the subject of hundreds of boys' nocturnal fantasies, and while she normally wouldn't show a guy like me the time of day, since we had her under our thumb for at least a little more I knew I would be making the best of this lucky situation.
We shuffled on our feet in anticipation, a fact that wasn't lost on the tantalizing girl. In retrospect, I think she was enjoying our enthusiasm, enjoying the teasing. I, however, planned to wipe that smile off her face soon.
For a few seconds Debbie was in control. But once I sat on the bed, motioning her to drape herself over my knees, her power subsided. She slowly got off the bed, straightened her skirt for some strange reason and then moved closer. Debbie finally was standing next to me, directly across from her brother Danny, who sat on a chair. He appeared mesmerized by the scene being played before his eyes.
"Okay, Jon, what do I do," quietly asked the girl who had expertly sucked my dick the week before.
I nodded toward my lap. "Over my knees, girl, it's time for your punishment!" I commanded.
Debbie bent over at the knees then wrapped herself over my knees. Her skirt covered her butt, and I gazed at the beauty of her legs. Slowly I reached down and lifted the skirt away from her skin and up onto her back, baring her red satin tap pants. I reached up and began tugging them down, unwrapping her creamy ass. I left those satin panties midway down her thighs.
Glancing up at Danny, I noticed his eyes were riveted at the marvel of his sister's beautiful bottom. I began softly stroking her ass as a prelude to the spanking, and watched Danny's eyes nearly pop out of his head. He looked sort of strange, his mouth and eyes wide open.
I caressed Debbie's ass, slipping a finger up and down her tightening ass crack.
"Jon, watch where you are going. We didn't agree to anything funny back there," said the subdued girl.
My hand continued to stroke her behind. It was so beautiful. She was so unattainable. And her I was, with her at my mercy. It was almost unfair, but since she had agreed, I was going to take advantage of each and every minute. My dick pulsed against my zipper, which in turn was wedged against her midsection. If she felt my bulbous cock, she didn't say anything. She sort of just squirmed against me in anticipation of the spanking.
I lifted my hand away from her ass, and she pulled in a deep breath and clenched her buttocks. My hand moved about a foot above her ass then whisked down, firmly catching the tops of both butt cheeks. "Ouch," she said, a cry that became more frequent and louder in the next minute.
I began spanking her ass, using strokes slightly harder each time. I saw her pretty ass begin to turn from creamy white to red to a bright crimson before too long, and the tears began flowing from her baby blue eyes.
"Jon, you are hurting me," she blurted out at one point between swats. "Stop! Please stop."
Ignoring her pleas, I pressed on. Smack! Whack! On went the striking of the beautiful girl's creamy ass.
I looked at a smiling Danny and he mouth the word harder to me. Earlier we had discussed the session, and he asked me to give his sister a series of hard slaps for him. His plan was to have be give her the spanking, then, when she expected him to take over, he'd say she had been punished enough for her actions. He'd look like the good guy, and he hoped that his conniving sister would remember generosity in the future.
Danny's dick was out of his fly, and he was stroking his hard cock to the beat of my slaps to his sisters' hot ass.
I struck her ass hard, then softer, alternating strokes for a while so that she couldn't be sure what would come next. Along the way she begged for me to stop, that she would never cause Danny trouble again, and that she would be a good girl from now on. I didn't really listen to her pleas, simply basking in the glory of being the guy who was pulverizing the beautiful, unattainable, sexy girl's behind.
Slap, Slap, Slap whisked my tiring hand against her ass cheeks to the beat of a bass laden song on the radio. "Ouch! No! Stop!" came the groans from the supine girl. Boing, boing, boing pulsed my dick against my trousers.
Debbie's ass was a bright share of delicious apple red, warm to the touch. Every once in a while I would stop the slaps, caressing her ass, before starting over once again. Several swats were with her hairbrush. What seemed like hours, yet only minutes, later I asked the girl if she would be treating Danny with respect from this point on.
"Yeeessss," Debbie cried out. "Yeeesssss."
Danny, I noticed, had already shot his load on his sister's floor and was standing in front of his sister with his wilted dick hanging out of his pants.
"Do you want me to stop?" I asked the beaten girl.
"Please stop, Jon, I'll do anything. Please stop you are hurting me!"
I smiled at her response, and asked if she would masturbate once again for me in lieu of finishing her spanking. She quickly agreed. "Oh, and kiss Danny's dick!"
As she spouted the anticipated "NO" I pulverized her ass with a series of crisp hairbrush aided spanks, bringing a change of heart. "Ok, ok, I'll do it," she said, lifting her head to kiss her brothers' cock. She kissed the tip of his dick as Danny began stroking it back to hardness. He jerked himself against her cheeks, and soon shot a second load of cum against her face.
I stopped the spanking and caressed her ass, squirting on some hand cream that was on her dresser and rubbing it gently onto her ass while Danny rubbed his load against her face. Her ass was warm, and her breathing hard as I stroked her pretty buttocks. Danny zipped up his dick and exited the room. At that point I allowed her to get up from over my knees.
Debbie rubbed her ass as the tears stopped flowing from her eyes.
"That hurt, Jon, you were rough with me. And that bastard Danny took advantage of me."
"You said it was okay, Debbie. And besides, I wasn't as rough as I should have been, considering all the trouble you caused Danny," I replied. "But you were a trooper. You took it like a lady. If you want to end it here, that's okay."
"Nope, I agreed to play with myself, so I will. But I will have to sit on some pillows, my behind smarts!"
Debbie somehow was back in control of the situation. She told me to sit on the chair that Danny had sat, and I did, lowering my Dockers and underwear. Debbie sat on a fluffy pillow and lifted her skirt. She lowered her tap pants, displaying her closely trimmed pussy. She looked into my eyes as she stroked her slit, slowly at first. I could swear she was soaking wet, and I could smell her sex from across the room. Apparently the spanking had lit a fire in her panties.
"Ohh," she cooed, stroking her slippery slit. "You spanked me so hard, and my ass hurts. But I am so hot."
Debbie was lost in her trance, slipping her fingers up and down her pussy lips. Every once in a while she dipped one, then two, fingers deep inside her wet cunt. It was a sight to behold, and it wasn't long before the stroking of my cock was in concern with her stroking of her sex. I watched as she played with her pussy, and the view sent me over the edge. I shot a second load onto her flooring as I head Debbie cry out that she was cumming too.
We were both lost in our orgasms for a few minutes, before opening our eyes and realizing what we had done. Debbie quickly pulled down her skirt while I pulled up my boxers and Dockers. We were both a bit embarrassed, having shared intimate moments apart together.
After a bit of silence Debbie quietly said that we were all even. "I hope you enjoyed yourself today, Jon. Thanks for not going over the edge with the spanking, I appreciate it. But don't get any ideas. The deal was sealed, I did my part, and now we are all square. I know you will keep this all quiet, and I know you won't be trying any funny stuff down the road."
I smiled and told her that of course Danny and I would adhere to the terms of our agreement. I left the room and smiled once more, as I knew that tape locked in my bedroom might come in handy down the road, especially if she attempted to get back at Danny for cumming on her face.
Not to worry, though, as for the next month the sexy cheerleader treated me…and Danny…with a respect we had not anticipated. What a surprise. What a series of surprises. What surprise would be next?