6 comments/ 327981 views/ 29 favorites Catching Debbie Red-Handed Ch. 1 By: JRob 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 what?" "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." Danny nodded. Catching Debbie Red-Handed Ch. 1 "How did you know," I asked. "You were in the other room?" "Well I don't for sure know," he calmly said. "But you have no reason to lie. And besides," he said, pointing toward his bookshelf, I was recording everything." We watched the tape, cocks hardening, and wondered if we'd ever show Debbie her second starting role. To Be Continued... Catching Debbie Red-Handed Ch. 2 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?