9 comments/ 52868 views/ 20 favorites Amber's Vacation: Day 01 By: Strangebuddy Amber drove home from school with a mix of excitement and anxiety. Her school's winter break had just started and she was about to have two weeks of vacation with her dad and stepmom. The three of them were going to go up to her grandparents' house in Hawaii and have a great time at the resort they owned with the rest of her dad's side of the family. There would be almost a full week of sunbathing and sneaking drinks with her cousins. What made her nervous on the other hand was her stepmom, Jean. It wasn't that she hated her stepmom, she actually loved her just as much as her dad, she was just nervous about what plans for tasks and punishments Jean had for her. For the past six months, a little after she turned 19, Jean had been training her as a sub and she had recently become more creative with Amber's sessions. Jean had been gloating about how she'd already selected Amber's bathing suits and had to special order them from a site in Japan and she expected Amber to wear them unless she said otherwise. Jean had also hinted strongly that she had a couple friends in Hawaii who would love to have a show or even play with Amber if she misbehaved. Amber enjoyed being tested by Jean but her stepmom really liked pushing her comfort levels. Amber pulled into her garage, went upstairs and stripped out of her clothes so she could get into something more comfortable. She slipped off her jeans and took off her panties, revealing a carefully shaved mound. She then pulled off her shirt and took off her bra, releasing her B32 breasts which pushed up proudly from her skinny, 5'2 frame. Amber carefully inspected herself in her full body mirror for any body hair before she slid on some pink booty shorts and a black tank-top that held tightly against her flat stomach. Even when Jean had just been her stepmom, she had tried to slip in more casual clothing into her wardrobe but now that she was her mistress, she expected Amber to dress a lot skimpier than normal when she wasn't in school and had a strict no-underwear rule for her while she was home, even around her father. Amber shivered as she walked to the thermostat and turned the heat up a little before going into her mom's study. She wasn't done with her tasks for the day. In addition to keeping shaved, Amber had to keep a diary and clean her step-mother's strap on. She started with the dildo as she waited for Jean's desktop to boot-up. The thing was a practically a black obelisk at ten-inches long and a circumference that Amber could just get her hands around. Jean had never actually used it on Amber, preferring to use smaller toys and her own "hands-on treatment," but she had always shown her it during their sessions and told her that one day she would slide the whole thing into Amber's tight little pussy and slap its rubber balls against her. Amber feared it but a part of her was always curious if it could actually fit: She knew that Jean liked to play with her dad's ass and had shown her some of the toys she had used on him, which had included some surprisingly wide and long butt plugs. Amber licked the head of the detachable dildo and carefully worked her mouth over it, taking the facsimile into her mouth. The dildo was designed to have a circumcised look to it so aside from its size and plastic taste, it was like the two guys Jean had made her suck. As Amber slid inch after inch of the mighty tool towards the back of her throat, she thought back to the night she had given her first blowjobs. Jean had made sure that Ted was out for the evening (while he knew that Jean and Amber had been engaged in some kind of bdsm play, he had no idea how far they had gone) and blindfolded Amber while she knelt in a thong and a push-up bra in the living room. Two men she didn't know then entered and dropped their pants while they made small talk with Jean. They ignored Amber for the longest time, occasionally coming near enough that she could smell the sweat on their crotches. For a while, Amber had thought that Jean was just trying to embarrass her when all of a sudden Jean acted like she had just noticed her and told her that she should have said something. Jean then allowed the two men to spank Amber and slowly mouthfuck her one at a time while she laid across Jean's lap. The men weren't particularly big but the taste of their precum and the new experience of accepting cocks into her mouth made her nauseous and gag. Jean had been patient though. She kept encouraging Amber and even chastised one of the men when they grew angry at Amber's gagging. After they filled her mouth with cum several times and had been able to build a good speed and even hit the back of her throat with the head of their dicks without Amber gagging, Jean had placed Amber on the couch and escorted the spent men outside. She had then sat next to her step-daughter and let her play with her soaking pussy until Ted came home a few minutes later. Amber had desperately begged Jean to let her finish but Jean just playfully smacked her on the ass and told her she would have to be faster at finishing her tasks if she wanted to pleasure herself. Amber then had to sneak upstairs, her mouth still tasting of spunk and her body aching for release. She felt so slutty but extremely excited. Still, Jean kept to her word and refused to let her cum until two days later. That was how her stepmother worked; being gentle when she was pushing Amber's limits then keeping her horny so she couldn't think of how embarrassing the task was she had just done. Amber pulled the large dildo out of her mouth and finished by licking the parts of the phallus she hadn't been able to deepthroat. She inspected her work and, believing her stepmother would be satisfied, started to type. There hadn't been much going on at school today, she had just had three finals and left without talking to anyone. Amber had always been awkward around others, not helped by the fact that her mother had pulled her out of school for two years after she divorced her father and had failed to be much of a homeschool teacher. When Ted got custody of Amber back, she had to be put back two grade levels behind her former friends. While Ted, and later Jean, tried to get her to interact more, it was difficult for her to make friends and even now, in her senior year, she only had a couple classmates that she actually hung out with outside of school. It didn't help that she was still bullied somewhat by people that thought her poor social skills and age meant she was retarded. As Amber thought about that, she began to type out the sexual fantasies she had been having lately. Some were just thoughts about her sessions with Jean, while others were a bit more elaborate. Amber didn't mind typing these out for the most part; they let her relive the fantasies, making her nice and wet, and Jean couldn't possibly make some of the more embarrassing ones happen (at least, that's what Amber thought). However, there was one fantasy Amber had been having that she was reluctant to type out. The fantasy involved Chelsea, a girl from her class that had been one of her bullies. The girl was stunning, 5'8, tan skin, trim body, brown hair, green eyes, a luscious ass, and C-cups that drove the boys wild. While she did pick on Amber, Chelsea mostly ignored her as she was too busy with volleyball or her friends to take time for the awkward girl that ran track. The fantasy had started a couple weeks back when Chelsea and her had gotten done with their practices at roughly the same time. While seniors normally got the privilege of private showers, there were too many girls in the locker room at the same time, so Amber and Chelsea had found themselves under the same group shower head. It was then that Amber got to see Chelsea completely nude for the first time. Amber had barely been able to be discreet as her eyes wandered up and down Chelsea. Amber couldn't help but get aroused as she watched Chelsea cover her breasts in suds and wash the small triangular patch of pubic hair she had above her pussy. She was so lost that she was almost caught staring and had to quickly try to cover up while Chelsea cast a suspicious glare. Amber had tried to make small talk but Chelsea had just ignored her until suddenly the lights went out. The luscious volleyball player had let out a shriek and fell forward into Amber. Amber instinctively had wrapped her arms around Chelsea, pressing their bodies together. Neither one of them said anything, letting their stunned eyes look into each other and their panicked breaths blow on each others lips, until the lights came back on a minute later. When they did, Chelsea walked away without saying anything and Amber had stayed behind, washing herself. Amber had then waited till everyone had left and then went home and pleasured herself while thinking of the way Chelsea's breasts felt. Jean had discovered her and went to town on her with a riding crop but Amber had just become even more aroused. The fantasy she had been having was her and Chelsea making love while Jean stood nude next to them, directing their actions and even joining them after Chelsea and Amber had kissed her feet and licked the stiletto heels that Jean loved to wear. Amber typed out the fantasy, her breathing becoming deeper from a mix of arousal and nervousness. She knew it would raise a lot of questions from Jean. Her Stepmother would ask if she had been hiding this fantasy for long and likely punish her. Not to mention, while amber had known that she was bisexual since she was 14, she had never told anyone, even her own father. Jean might become uncomfortable and stop being her dominatrix. When they had started six months ago, Jean had been very hesitant and had tried to focus more on the control aspect of their relationship and rarely touched her. Now, Jean was more comfortable using toys and occasionally would rub her and even had Amber eat her out on occasion, though she would always leave before climaxing. Jean had always been reassuring Amber that they were "experimenting" and that they weren't really ever having sex with each other. Amber sighed as she saved the document and leaned back. "Well, at least it will be out in the open." Amber sighed as she leaned back. "What'll be out in the open, my little slut?" a sultry voice said from behind Amber. Amber yelped as she heard her stepmother speak and felt her hands clasp her slender shoulders. She looked back and saw Jean grinning slyly at her. At thirty years-old, Jean looked drop-dead gorgeous. Even though she was wearing a sweater and some jeans at the moment, Amber couldn't help but admire her stepmother's fit body and large D-cup breasts that she knew almost every man in their housing division had lusted after. Jean leaned down and lightly kissed her stepdaughter on the forehead, letting her long blonde hair fall over the two of them like a veil. She smiled, her azure eyes beaming as she looked over her stepdaughter. Without warning, Jean painfully squeezed Amber's nipples. Amber cried out with a pathetic yelp but didn't try to resist. She kept her arms down and tried to ignore Jean messing with her already-hard nipples. "You know, my little slut, you are supposed to help me whenever I have something to carry in." Jean said coldly as she slipped her hands under Amber's tanktop and started to pull on her light pink nipples. "Aaah!" Amber cried out, "I'm sorry mommy! I didn't hear you drive up." Amber blurted out. She was already transitioning to her submissive state; whenever one of their sessions started, Amber was only allowed to call Jean "mistress" or "mommy." Jean leaned in next to Amber and whispered, "Oh, that's okay my little candy drop, I didn't know you would get done early" she twisted Amber's already stretched nipples, drawing an agonized moan from her stepdaughter, "but that's not why I have to punish you. Now, can you tell me why I have to hurt your cute little nipples?" Amber tried to think what transgression she could have made to anger her stepmom but it was hard to concentrate while her nipples were being tortured. After what seemed like hours of having her precious little titties getting pinched and twisted, a revelation hit her: "Is it...is it cause I forgot to call you when I got home?" Jean kissed her on the neck but pulled as hard as she could on Amber's nipples. "That's right, my little slut. You're always supposed to call me when you get home. I want to know that my precious slave is safe and sound. Not to mention," Jean motioned towards a bag she had left in the doorway, "I don't want you seeing any of the fun little toys that Santa is bringing you for Christmas." "I'm sorry mommy, I was just really excited that finals were over and I forgot!" Amber cried out as tears started to form from the pain. Jean released Amber, letting the younger woman breathe a sigh of relief before she ordered her to take off her tank-top. Amber quickly complied and ripped the little thing off of her body without a moment's hesitation; she wasn't afraid of being nude around her stepmother and her abused tits were being irritated by the cloth. Jean then ordered her to stand up and take her shorts off so she could be inspected. Amber once again did so but grew nervous when Jean withdrew her riding crop, which consisted of a small rectangular patch of leather attached to a flexible, black metal wand. Amber knew what Jean could do with that little instrument and shuddered a bit as her stepmother slapped its tip against the desk to test its durability. As Jean took a seat in the chair that Amber had been using, Amber noticed that Jean hid a couple of objects behind her back. Still, Amber knew she wasn't supposed to ask questions while she was being inspected so she stood in front of her stepmother and held her arms behind her back while her stepmother looked her over. Jean carefully examined every inch of her stepdaughter's naked front, trailing the riding crop's leather tip across Amber's pale flesh. She started with her feet, making sure that Amber had kept her toenails clipped and painted a light pink. Satisfied, Jean guided the crop between Amber's legs and ran the length of each leg up to her shaved mound, searching for any hair; she smiled a wicked grin when Amber shivered from the crop being placed near her privates and delivered a light smack to the young girl's left inner thigh. "Don't move pet. It makes it harder to see if you've been my good little toy or not." Jean ordered as she saw Amber try to suppress a squeal of pain. Jean spent some time rubbing Amber's mound, even taking some time to part her swollen labia and patting her engorged clitoris with the riding crop. She observed the wetness of Amber's pussy and kept a curious gaze on her face as she once again looked up at her stepdaughter's face. "So I guess today's entry is particularly steamy?" Jean pulled Amber's right arm from behind her back and began sniffing and licking her fingertips, searching for Amber's scent, "Or have you been playing with yourself without permission again?" Amber tried to keep a straight face as she answered but Jean kept stimulating her nether regions with the cold riding crop and Amber was already so aroused. "No mistress Jean, I just wrote what you wanted me to and...oh, please don't make me answer while you're doing that." A hard slap on her right thigh made Amber shriek with surprise. Catching herself, she finished: "And I just got really aroused." Jean took the crop and used it to push up each of her step daughter's proud little breasts. Satisfied that Amber managed to keep a straight-face, Jean led the crop up the young-woman's chest and put the leather tip in front of her mouth. Amber sucked on the tip, tasting her own wetness until Jean pulled it out. Jean smiled, "If you're soaking from just writing, I can't wait for you to read it aloud to me and my friends." Amber gasped, horrified that she would not only have to reveal her sexual preferences to her stepmom but she would also have to do it while Jean's online friends watched. Jean's friends were a kink group that met online to share stories of their conquests and occasionally have meet-ups with each other. Jean had recently started a private channel for them where they could watch her carry out her sessions with Ted or Amber. They only responded through text but they loved watching Amber be embarrassed in front of the camera. Sometimes, when she was too busy, Jean would even let them direct the session and Amber would have to take all their requests. Seeing her stepdaughter's frightened face, Jean just rolled her office chair over to the door and retrieved a couple of objects, a candy cane and a set of nipple clamps. from the bag while she put on a sadistic smile. "Present yourself, slut." Jean said as she unwrapped the candy cane. The thing wasn't really a cane so much as it was a thick pole of sugar with a candy-cane stripe. Amber nodded and obeyed, albeit reluctantly. She turned to face the computer monitor and bent over so her face was only a few inches away from the screen and her butt was proudly pushed out towards Jean. She then spread her legs wide so Jean would have an easy time examining her ass. "That's really good, pet. Here's a treat for you, be sure to make it nice and wet." Jean said as she pushed the candy cane into Amber's mouth. Amber sucked on it hungrily, using her right hand to steady the piece of candy once Jean released it; she had a good idea what it would be used for and wanted to make sure she narrowed the thick thing down as best as she could. Jean then attached the clamps. Amber let out a soft cry; she wasn't used to nipple clamps, having only had them used on her a couple of times, but they felt better than the previous abuse Jean had given her poor little nipples a few minutes ago. As she tried to get used to the pain, Amber heard a slight jingle of bells. She took a quick look down and saw that, attached to the ends of the little strips of metals that hung from the silver clamps were small bells. Amber tried to focus on whittling the candy cane down with her mouth but started to blush as she felt Jean slip a red Santa hat over her forehead; Jean loved dressing Amber up when she wasn't in school and it was clear what type of cosplay she was going to make Amber wear. Jean confirmed her fears by buttoning an extremely small skirt around her waist. The little skirt was a felt Santa red miniskirt with a bit of white faux fur running around its bottom. Amber could feel her ass hanging out and figured that the miniskirt barely covered anything. Amber's embarrassment wasn't over though, as she hear Jean pull on some latex gloves with a chilling snap. Jean just chuckled as her slave shivered in fear: "Just keep enjoying your little treat, my little slut. Mommy is going to make sure you're nice and presentable for her friends." Jean said as she squeezed Amber's butt cheeks and pulled them apart, searching for any little hairs. Amber kept focusing on the long stick of candy in her mouth, which she had worn down to a narrow point on one end. Her mouth was almost dry from all the sugar and her tongue was almost worn out from all of the sucking and licking. She was about to stop and move down the pole when she heard Jean start to click her tongue. Knowing what was coming, Amber took the candy out of her mouth and bit down on her lip. "Oh my, little slut, you seemed to have missed a few hairs." Jean said, pulling open a drawer and retrieving a pair of long metal tweezers. Jean had to look hard for them but she had found a five small hairs right outside of her young submissive's asshole. "Don't you worry though, your mistress is going to fix this right up for you." Jean plucked one of the hairs, taking her time to uncurl it and stretch it out before ripping it from its dark little follicle. She grinned as the act drew a squeal of pain from Amber. Amber's Vacation: Day 01 "Poor baby." Jean said mockingly as she uncurled another hair and playfully tugged at it, "You know, you could just ask me to stop and we could sit on the couch, stepmom and stepdaughter, talk about our vacation and do girly things." Despite being on the verge of tears from the clamps and her very sensitive hairs being pulled, Amber shook her head. She knew Jean was trying to get her to say her safety-word so she would have to spend the next few days begging her step-mother to start up their sessions again. This had happened several times in the past and Jean had always made her go through hoops before she would even let Amber so much as lick her boots. "Good girl," Jean said, an earnest smile spreading across her face. She didn't give any mercy to Amber though; each hair was ripped out in rapid succession and Amber was left with her legs buckling and a couple of tears streaming down her innocent face. Jean took a moment to comfort and praise her faithful pet. Wrapping her arms around Amber's waist, Jean cooed, saying, "You're doing so well pet. You have no idea how proud of you I am. When we're done today, if your father's not home yet, I want you to think of a nice little reward for yourself." Seeing Amber brighten up, Jean returned the tweezers to the drawer and withdrew a small jar of lube. She pulled off the lid and dipped her right index and middle fingers into the mess, coating them in a thick goop. She stroked the small of Amber's back with her left hand and shushed her as she slid her index finger into her ass and encountered some resistance as she began to thrust in and out of her ass. Amber started to squirm; the lube was a warming jelly that that was mixed with a bit of ginger root to give an intense heat. The warmth was driving Amber mad but it was also making her even more aroused, as the stimulation from her stepmother's probing fingers, the warming lube, and the jingling nipple clamps made her start to moan from a mix of pain and pleasure. "You're such a beautiful girl, my little pet." Jean said softly as she pushed her middle finger into Amber's ass and started to pump it in and out along with her index finger. "Thank you...mistress." Amber panted out between her grunts and moans of pleasure. Amber thought of how ridiculous this would of seemed a year ago: if she had been told at eighteen that in less than two years she would be bent over and having her ass probed by her stepmother while she was dressed up as a slutty Santa's helper, she would have laughed. Now, as a small bit of drool escaped her lips and the heat intensified in her tight little rectum, Amber couldn't imagine life without these sessions. "Does that feel good, slut?" Jean inquired as she sped up the thrusts of her fingers which were now flying in and out of Amber's loosening butthole. She then took her other hand and reached under Amber, being sure to ring the nipple clamps, and took the candy cane from her. "Yes, mommy, it feels really good." "Then why don't you get the show started so our friends can join in?" Jean suggested as she added her ring finger and readied the candy cane. Amber nodded and logged in to the private channel; she was nervous about being dressed this way in front of the perverts on the stream but at least logging in would let Amber pull some of her attention away from the number Jean was pulling on her ass. As the stream loaded and synched up with Jean's webcam, Amber kept hoping that no one would be on; she always felt awkward not seeing the people she was naked in front of. Even though Jean had made Amber service several men in the past, at least she had been able to see what they were doing or feel them. With the webcam, she had no idea who was on the other side other than the fact that they always wanted her to do naughty things and were always insinuating the even more extreme things they were planning to do to her. To Amber's chagrin, two of Jean's friends were on: Dirtydad69 and Jockoff. Amber knew the two of them really well; they never missed a chance to watch her. Jockoff loved making Amber masturbate and always kept complimenting her figure and giving advice how to get in better shape while making her exercise in the nude. Dirtydad69 always made Amber feel really uncomfortable, which was why Jean loved leaving Amber alone in the study with him. He wanted her to always call him 'daddy' and loved telling Amber how much he wanted to have her over and be his naughty daughter. He always requested that Jean take the paddle to Amber and beat her butt red, even if she had been good. Jean only occasionally complied but she loved threatening Amber by telling her that she would leave her at Dirtydad69's house for a weekend if she didn't keep her grades up or disobeyed her. Jean always hinted that Amber knew these two, in addition to several other members on the channel, which creeped Amber out even more. Dirtydad69: Hey Jean, glad to see you on. Jockoff: Sup Jean? I just got off work, glad to see I didn't miss you. What's on the menu today? Jean laughed, "Oh I figured Amber and I would wish you all a Merry Christmas before we went to Hawaii." With that, she spread Amber's cheeks and, removing her fingers, drove the candy cane in, which led to Amber shrieking in surprise. The lube made the part she had narrowed slide in easy but only for the first inch. The sudden entry had tensed her muscles and her rectum clamped on to it. Jean kept pushing, despite the resistance, until the thickest part of the candy cane was spreading Amber's tight little ring open. Amber groaned, she wasn't used to anything of this size in her ass and Jean was pumping it in and out just as fast as if she were working Amber's busy with a small dildo. Still, Amber had learned to appreciate the feeling of being stretched open and the lube was making the whole thing a lot better. The pleasure was almost equal to the pain. Dirtydad69: That's a bad girl Amber. You shouldn't make a sound until your mistress tells you to. Jean, might I suggest a good spanking? Jockoff: I agree. Amber, you're normally so well-behaved...I like the outfit by the way. Jean moved the camera first so they could see the nipple clamps and then so they could see Amber's butt and the stripped piece of candy that was being thrust in and out of it. "Thanks Jockoff. You know, you two are right but since this is the biggest thing she's ever taken, I think we should be lenient. How about twenty whacks?" Amber grit her teeth as she read the next responses; even with just her hands, Jean could deliver some serious damage. Dirtydad69: Okay, but if she makes another sound, I want the paddle to come out. "Of course. In fact, how about if this little slut makes a single shriek, she spends tomorrow with you?" Jean said with a wicked laugh as she delivered the first smack on Amber's ass, never interrupting the use of the candy cane. Amber bore it with a few tears building up but kept silent. Dirtydad69: Sounds great! Maybe she could teach my girl to take a little punishment. Jean just smiled and kept making small talk as she smacked Amber's ass with all the force she could muster. Each smack filled the room with a deafening crack and soon Amber's cheeks were as red as her face. Amber let her tears flow freely as the twentieth smack landed on her ass. The candy cane was now going in and out of her really fast and she knew she was going to cum soon. Though it was tempting to just let Jean finish her off, Amber knew she would get in trouble if she came without permission. She motioned to speak. "Yes Amber?" Jean asked as sweetly as she could, "Now that your ass is red for the holidays, do you have something to say?" Amber nodded. "Yes mommy. I'm sorry I made a noise before and also...uhm," Amber stammered, embarrassed that she had to say it in front of an audience, "I'm going to cum." Jean sighed and stopped driving the thick candy cane in and out of Amber's ass. "I'm sorry, mommy." Jean petted Amber's short hair. "No, that's a good thing you did, my pet. You need to learn to be less sensitive but we can work on that." Jockoff: What a good girl! Jean, why don't you give her a reward? Oh, and could you take a picture of her ass? I want to make that my new desktop." "Yes to the picture, dear but no to the reward; Amber will be having a playmate come by in a little bit so I think she can hold on till then." Jean answered as she withdrew a digital camera and snapped several photos of her stepdaughter's ass, the candy cane still lodged inside and its cheeks as red as the little skirt she was wearing. Jean put it away with a wicked smile: she had some plans for those pictures. "Now Amber, since we have an audience, why don't you sit on my lap and read what you wrote?" Jean asked as she finally slid the candy cane out of Amber's ass and looked at her open asshole; her stepdaughter had progressed quite a bit in the last six months, she'd soon be taking more in both holes. Amber practically collapsed on her stepmom's lap, her entire ass still sensitive from the spanking and the candy cane. She almost jumped up when she felt the rough denim of her stepmom's jeans rub against her tingling ass but settled down, not wanting to get punished further. She quickly scrolled up, hoping Jean hadn't seen the last part yet, and began to read slowly through her entry. Dirtydad69 and Jockoff remained silent for the most part, occasionally making her repeat a sentence or ask Jean to squeeze and shake Amber's tits so they could hear the nipple clamps ring. When they got to the section that concerned Amber's fantasies, they started making tons of comments. This was because Amber's first two fantasies were a bit more kinky than usual. The first one involved three men breaking into the house, ripping her clothes off and gang-banging her until she passed out from exhaustion, cum leaking from her holes. While Amber wasn't too much into the pain part of her training, she loved when Jean blindfolded her and took charge, sometimes inviting men over. Dirtydad69: Last I checked, hasn't Amber not even taken a dick in her ass? I think you might be biting off a bit more than you can chew little girl. Jockoff: That's right. Besides, there's no way Jean would let anything happen to her precious baby girl, right Jean? Jean's eyes beamed. "You're right Jockoff, I'd never let anything happen to her and we live in a safe little house with security cameras everywhere." Jean took a moment to kiss Amber's neck. "Though if my sweet little Amber were to get violated in this house by three men who just happened to have a spare key, I'd be sure to ask your help in watching the footage for hours so we could bring them to justice...or another round with her." She laughed as she felt Amber stiffen in her lap as the two people online typed out agreements and 'lols.' Without offering any reassurance that she would protect Amber from such an event, Jean ordered her to continue and began rubbing her pussy, whispering that Amber had better hope she didn't cum if she didn't want to be thoroughly punished until her father got home. Amber continued, the second fantasy involving sex with Santa Claus. Amber had seen some porn online of a beautiful girl being ravaged by a mall Santa Claus. Amber thought the idea was kinky, like her sessions with Jean, it was a taboo act that combined rough treatment with someone caring. It wasn't a really fleshed out fantasy, she would just catch Santa Claus in the act and he would ask her for a present in return. Dirtydad69 ate it up, suggesting that Santa Claus should punish her for being a naughty girl and tie her up after smacking her ass. He could even pull out some adult toys from his bag as her presents and make sure she liked them by satisfying her with them. Jockoff and Jean just laughed and said that at least Amber was already dressed for the part. Jean felt Amber get close again so she stopped rubbing her slit, "Go on honey, why don't you read the last bit so I can get you ready for our guest?" "Mommy, before I read it, can I say something?" Amber said, desperate. Jean squeezed her nipples and pulled on the clamps but she nodded. "Okay, but make it fast." "I really love having you as a mistress and a stepmom. I don't want this to stop, punish me if you want but please don't hate me for what I wrote." Amber stammered out as she shivered in Jean's lap. Jean looked puzzled but she released her stepdaughter's nipples. She wondered what could be worrying her so much considering the fantasies that had come before it. Still, she prodded Amber and ordered her to read. Amber sighed and started. The two people online paid attention, loving the details of the two girls' bodies intertwining and the orders the fantasy's Jean gave to them. Including things like sharing a double-sided dildo and taking turns with a strap-on. To Amber's surprise, both Dirtydad69 and Jockoff knew Chelsea and both had fantasies about her, Dirtydad69 was especially interested in Amber's desire for her classmate. Jean remained silent throughout the reading, not even commenting when Amber got to the part where Jean joined them and began pleasuring Chelsea and Amber before fucking Amber who would be eating out Chelsea. "And then, when I make Chelsea cum, mommy turns me over and French kisses me until she makes me cum with the strap-on. When I do, she pulls a blanket over all of us and keeps whispering how much she loves me while I tell her the same and the two of us rub our pussies together until we cum together and fall asleep in each other's arms." Amber finished, waiting for a reaction from her audience. Dirtydad69: Damn! Now that was a hot little story. I'll have to go show it to my pet right away. Jockoff: So glad to see you have some fantasies outside of men! Remind me to stop by some time and join in. Jean, I had no idea the two of you were that close, I thought you were keeping things "nice and professional." Knew you couldn't keep away from tasting the forbidden fruit. Jean just gave a half-hearted smile, "Well, it looks like that's all the time we have today. Jockoff, I'll send you those photos later." She then logged off and looked at Amber. "So my pet, how long have you hid that you were bisexual from me?" Jean asked, her voice not betraying how she felt about this revelation. "I've known since I was fourteen. I would have told you but I was worried you wouldn't want me as your pet anymore." Amber admitted. "And how long have you wanted me to sleep with you and not just be your mistress? Amber gulped. "After you started living here, when I was fifteen. It was that day we only had one working shower so you and me had to share it. I saw you naked and couldn't get the thought out of my head. You're just so sexy." Amber started to cry. "When you took me on as your slave, I was so happy. You made me feel so good and when you let me touch you, I was in heaven. I knew I should have told you when you started letting me lick your pussy but it was just so good that I didn't want you to stop. I'm sorry. You're a great mom and a great master and I'm such a horrible person; I should have told you." Amber was now in hysterics. "Amber, there's nothing to be sorry about." Jean said, hugging her and taking off the nipple clamps; she only called Amber by her name when their sessions were over or if she wanted to talk to her as her stepmom during their playtime, "You're my beautiful, smart, kinky, little stepdaughter...you are a great person and I won't have you think of yourself any other way. True, you should have told me but I wouldn't have turned you away." Jean turned Amber around and held her half-naked body to her, ignoring the snot and tears that still streamed down her stepdaughter's face and fell on her sweater. "I love you Amber. I love being your master and getting to control you but I never want you to have to hide a part of yourself because you think I'll hate you for it." Jean said, kissing Amber's cheek, "Besides, it wasn't like I didn't suspect you were a little attracted to me. Now, I thought you were just trying to find an outlet for your sexuality, and seeing me and your father go at it just got your motor running, but this does make more sense. If I had known though, I would have been more careful to bring some women over so you could explore that part of your sexuality." Amber dried her tears. "Mommy...Jean, I really do find you attractive and I do love you. You've been so kind to me and I know dad is crazy about you. I'd be more than happy if we just kept things like they are but I would like to get to make love to you as a woman, not just your submissive." "I'll have to think about it Amber. You have to understand, your father isn't crazy about the two of us doing what we already do, and that's just what we let him see, but he tolerates it since he sees it as drawing you out of your shell; if we had sex, we couldn't really look him in the face and tell him it was just innocent; and I'm not going to lie to my husband." Amber looked glum but put on a quick smile. "So it isn't a matter of you not being attracted to me, huh?" Jean chuckled. "When did my little candy drop get such a smart mouth? Look, how about you get washed up, we'll have dinner with your father, and we can bring it up while we're in Hawaii; he's a lot more suggestible when he has a few drinks in him." "That still doesn't tell me what you think about me Jean. Besides, don't I have a guest I need to see to?" Amber asked, rising out of Jean's lap. A mischievous smile came over Jean's face, "You're absolutely right my little slut. As a punishment for not telling me about that fantasy earlier, you have to meet him alone. Still, it's a pretty simple task: just serve Walter a piece of pie without using a plate or a spoon. Be careful though, he doesn't want that pie frozen and you can't use the microwave. If you can't figure it out, I've given him free reign to do whatever he wants. When you're done, or Walter's done with you, wash up and come to my bedroom for inspection. Oh, and if Walter makes you cum, you go home with him and I'll be by to pick you up in the morning." Jean playfully pinched Amber's still engorged clit. Amber nodded and ran to the kitchen where she ripped a frozen key lime pie out of the freezer and broke off a slice. Walter was another of Jean's friends that creeped Amber out; he was the sixty-five year old mailman that delivered mail to their street. While he was a perfectly nice man most of the time, the idea that someone she knew from before she even wore a training bra wanted to fuck her was disturbing. Possibly because of this, Jean loved getting the two of them in the same room or finding ways to involve him. For a while, Jean had even stolen Amber's panties and let Walter jerk off into them; making Amber wear them and feel his cum on her private parts as she walked around during the day. He also had been bringing bukkake porn for the past three months for Amber to watch and was more than happy to tell her about how much he'd love to see her in a film. Amber tried to think of a way to warm the pie up and serve it to Walter, when a horrific realization came over her. Knowing what her stepmom meant, Amber sighed and got up on to the dining room table, laid down, and placed the piece of pie between her legs, placing what she could of her miniskirt over it. The pie was freezing on her private parts and it wasn't making her any less aroused, so Amber tried to think of anything else. She tried squeezing the key lime pie with her legs, hoping it would start to thaw. She kept at it for ten minutes, until the front door opened and she heard the sound of boots stomping snow off in the doorway. Amber looked up at the ceiling when she felt Walter's gloved hands on her legs. She heard a nasally grunt as his rough snow gloves rubbed her inner thighs. She figured he would just flip up her skirt and start eating the pie but instead he skipped over it and let his hands travel up to her breasts where he started to squeeze and fondle them. Amber squirmed from the touch and moaned; her already abused b-cups were still very tender. Amber's Vacation: Day 01 "Oh, Amber, I didn't see you down there." Walter said with his gravelly voice as his head moved into Amber's view, "Your mom left a slice of pie for me, have you seen it?" Amber took a moment to look at Walter's face before she answered. He was wearing his blue trapper hat over his gray hair and his chin was covered by the collar of his thick warm coat but Amber could still see his leering smile and hungry black eyes. Walter had a heavily wrinkled face, even for his age, and it always seemed to be contorted into a wicked little grin. He was also a heavy smoker and Amber could smell it on his breath and clothes. Still, while there were a lot of things she found disgusting about Walter, she couldn't help but get a little aroused by the absolute desire in his eyes. "It's under my skirt, Walter. I wanted to try and warm it up so it wouldn't be too hard for you to eat." Amber said, trying to look away. Walter looked down at the tiny little skirt but just grinned and leaned in till his crooked nose was just a few inches away from Amber's. His warm breath filled her nostrils and she had to suppress a cough as she tasted the tobacco smell on her tongue. "Not that I don't trust you Amber but I was told it was some pretty special pie. I better make sure you didn't sneak any of it." Walter said before he plunged his tongue into the young teen's mouth. Amber knew it was coming but she still almost gagged. Walter was extremely aggressive with his tongue, practically assaulting her little tongue and scraping the sides of her mouth with his rough tongue. Amber took a couple seconds to adjust to the older man's kiss and met it; while she wasn't that into it, she knew that not doing anything would just make Walter keep going. She started trying to tangle her tongue with his and let her right hand slide up behind Walter's hat and pulled his head in close. She then let a soft moan, half-faked, issue forth from her mouth when Walter stopped to take a breath. Wanting to see if she could speed things up, Amber let her left hand slide out and rub against Walter's crotch; he'd clearly been thinking about this moment for some time based on the size of his bulge. Despite how nervous she was, Amber kept trying to pleasure Walter so he would hurry up; Walter wasn't quite like Jean's other friends, he didn't need to be in charge and really just wanted to get a little action. "Well, Walter," Amber said, gasping as their lips unlocked. "Are you convinced that I didn't eat any pie?" "I guess so, baby girl." Walter said with one of his big belly laughs. He moved back to the other end of the table and lifted her miniskirt up, revealing the now thawed piece of key-lime pie. "Mmm, this pie sure looks good!" Walter said, licking his lips, "The key-lime looks good too, by the way." Amber nervously laughed at his bad joke, hoping he would quickly eat the pie and leave. However, Walter took his time, spreading her legs and licking the bits of pastry that were stuck to her thighs. Amber tried to exaggerate her moans but soon found herself loudly moaning for real as the elderly mailman started teasing her slit by running his tongue between her labia and taking small bites of the pie that was precariously balanced on top of her mound. "Shhh...girl, I'm trying to enjoy this pie." Walter said as he licked all the way up her slit and flicked her little bean-shaped clitoris, letting the pie almost flip over. "Here, how about you share some of this with me?" Walter took a large bite out of the key-lime pie and carried it in his mouth back to Amber. This time, Amber gave in much easier to Walter's advance and let her tongue dart around his as he pushed the piece of pie into her mouth, slowly tearing the confection apart as the sweet tangy taste of the key-lime mixed with the whipped cream on their taste buds. For a moment, Amber forgot who she was kissing and just enjoyed the feeling of Walter's tongue and hers cleaning each other's mouth of every delectable particle of pie. Walter pulled away, grinning, and repeated the process with another bit of pie. Amber surrendered to Walter and even made authentic moans of pleasure as they broke each kiss; the experience of having her senses of taste and touch stimulated at the same time as she was aroused was driving her insane. Walter let his gloved hand rub the young woman's sensitive mound, keeping her nice and wet. Amber started involuntarily thrusting against his hand, her body aching for release. The last bit of key-lime almost fell off before Walter quickly lunged at it with his mouth and caught it like a dog going after a biscuit. He smiled as he quickly gulped it down and flashed a toothy grin. "Glad you liked the pie Walter," Amber panted, trying to hide how close she was to cumming from just his touches. "Maybe we can do this again some time." Walter just rested his mouth back down on her slit, saying, "Who said I'm done yet? We've still got all these crumbs to clean off you." With that, Walter started greedily sucking and licking all of Amber's sensitive tissue, making the teen start humping against his face and cry out in an animalistic moan of pleasure. This continued on for a few minutes, with Amber trying to desperately think of anything that would keep her from getting any hotter and climaxing. Luckily, she was able to hold on until he stopped. Unfortunately, Walter was just changing tactics. "Well, you look pretty good down there," the lustful senior citizen said as he unzipped his fly and fished out a very thick six and a half inch dick, "but I think a couple bits of pie went up your snatch. I better go fish them out with my rod here." Without even waiting for Amber to protest, Walter lifted up the teens legs and started to thrust wildly into her tight cunt. Amber knew Walter's cock well, he was one of the first of Jean's friends to go to the clinic in town and get tested for any type of VD; Jean's only rule for getting to be brought in on her sessions with Amber. While it was only around average length, Walter's cock was so thick that Amber could barely touch her thumb and middle finger together when she was stoking it. It also bent upwards, so it was directly touching her g-spot as it was thrust into her. Even though Walter wasn't very attractive to Amber, she had to admit that his cock felt amazingly good and the energy he had as he thrusted straight through her resistances and planted his dick all the way into the hilt and slapping his nuts against her bottom was so primal that Amber couldn't help but scream out in ecstacy. "Walter, please, you're going to make me cum." Amber pleaded in between moans. Walter just smiled and kept penetrating her little hole. "Well, I can't help if that's what happens." Walter said, chuckling, "I'm just trying to make sure you don't have any pie crumbs in your snatch." Amber realized, as her climax came ever closer to being inevitable, that Walter probably knew what would happen if he made her cum and wanted to take her home with him so he could really cut loose. If she was going to be spared, she'd have to find a way to make him stop stretching her pussy open. "Oh, Walter, it feels really good, you have no idea how good," Amber said, trying to act seductive as Walter sped up his thrusts and made her pant like a dog, "But if you made me cum, I'd have to go home with you and I wouldn't be able to try on the swimsuits my mommy got for me...Japanese swimsuits, by the way" Walter slowed his thrusts. Amber knew she had his attention, whenever she had watched the porn he had given her, she noticed that he really loved Asian bukkake films where the girls were dressed in sukumizus or other types of swimsuits. He loved when the girls' swimsuits were completely soaked in cum and often wished to see Amber go through the same experience. "Besides Walter, I just got done with school and I couldn't give you the attention you deserve," Amber said, hooking her index finger around her lower lip, "If you waited till after we got back from Hawaii, I could come over to your house and spend the whole day with you and some of your friends, and we could spend the whole day going at it until I was drenched." Amber tried to hurry, as she felt an orgasm approach, "If we went there now, it would just be you and me for a few hours before we got tired. Tell you what, if you let me finish you off in my mouth, I'll come over on the Sunday before I go back to school and let you have me till I have to go the next day, as long as my mommy agrees." Walter smiled and pulled out. The aged postman then clambered up on to the table and crawled over the teen's nude form until he was kneeling in front of Amber's face. He put his dick in front of Amber's gasping mouth. "I'm gonna hold you to that." Walter said as he pushed his hardened dick into her mouth. Amber just nodded and accepted his manhood, having to almost painfully stretch her mouth around it. Since she didn't have enough room to move around her tongue as Walter forced his member into the back of her throat, she just tried to shift it underneath his dick and lightly sucked on his length. Walter took his time but made sure each thrust went back as far as Amber's mouth would allow. He had clearly been close to shooting his load as only five minutes later he pulled out of her mouth. "You've gotten so good girl!" Walter moaned as he jerked off in front of her face, pulling her face up to it. "Here it comes Amber!" Walter shot four large loads over Amber's clean face. The first warm load landed right in her mouth, the second made her gag as a bit of it went up her nose and the final two loads landed on the sides of her mouth. Amber hesitantly licked up the cum; she really didn't like the taste, which was bitter and salty from all the coffee and cigarettes Walter had during the day, but she knew Walter expected it. Walter zipped up his fly and withdrew a manila envelope which had a decorative ribbon tied around it. Placing it on Amber's belly, he crawled off the table and walked towards the door saying: "Make sure that gets to Jean and I'll see you after you get back," Walter said, a croaking laugh issuing forth from his throat as he walked out the front door. Amber waited till she heard the aged postman walk down the block, away from her house. She was utterly humiliated, her face covered in the cum of a man she normally found disgusting and an extremely sensitive pussy that was begging for release from anything after it had been violated by the same man who she now had to spend a day with after she got back from her trip. Amber sighed and got off the table, walking to her step-mother's bedroom, which was closed. "Mommy, I know you wanted me to get cleaned up first but Walter gave me something to give to you." Amber said, knocking on the door. "Just slide it under the door, pet." Jean said from behind the wooden door. "I'll get to it in a moment. Now go clean up; I've left some underwear for you in the bathroom to wear when you come back, now hurry up and stash your Santa outfit under the sink." Amber did as Jean said and slid the envelope beneath the wooden door. She was confused as to why Jean wanted her to wear something when she inspected her but Amber just went to the bathroom at the end of the hall, sliding her skirt and hat off. Now nude, the teenager entered the bathroom, flipped on the lights, and quickly tossed the two bits of clothing in a drawer under the sink. She spied the underwear Jean had selected for her and was surprised at how conservative the panties and bra were; they were just cotton underwear, no special cut or style. Confused, Amber stepped into the shower and began to wash off with the movable shower head. Amber had to be careful to not give her legs and pussy too much attention; she was still only a couple of kisses or gentle touches away from having an earth-shattering orgasm. She just made sure that Walter's slobber was washed off and dried off her mound with a wash cloth and then focused on washing out whatever bit of the sticky mess she could from her ass. It was still very sensitive work but eventually Amber got out whatever remained of the jelly. The young woman then washed her hair and the rest of her body as quickly as she could before she stepped out and gently dried herself on one of the white towels that were stacked next to the sink. Amber let out a small whimper when she dried her breasts; her nipples were still extremely sensitive and the rough fibers on the towel were irritating them. Sliding on the black cotton underwear, Amber headed back to Jean's room and knocked on the door. The door slid open and Amber looked stunned when she saw Jean, who was beckoning to her from the king-sized bed that sat in the middle of the room. Amber just walked over silently and let her eyes wander over her stepmother. Jean had shed her jeans and sweater and had now wrapped her fit, tan body in a light blue robe that had a neckline that plunged all the way down to her perfect breasts. The luscious stepmom was drinking from a wine glass and reclining on her right arm as she lustfully gazed at her stepdaughter, who nervously crawled on top of the satin sheets over to her. The two of them stared at each other in silence for some time, both having an idea what was about to happen but neither one wanting to say it. Jean was the first to break the silence as she took a sip of wine before laying the glass down and started stroking Amber's wet hair. "So, did you and Walter have a good time, Amber?" Amber just nodded, becoming more nervous and curious as Jean rubbed her face. "I watched the two of you on the security camera; he really let you have it, didn't he?" Jean asked. She placed a finger on Amber's lips when the young girl tried to speak, "Do you want me to let you cum?" Amber nodded. Jean didn't speak but instead turned her over so her young stepdaughter's cute little back was facing her. Jean crawled over the top of the bed and spooned with Amber, giggling when one of her breaths on the teen's shoulders made her shudder. She started kissing Amber's cheek and went down to her neck and shoulder while her left hand slid under the elastic of Amber's black panties, tenderly touching her ass, and then let it travel to her crotch where Jean began to rub her shaved mound. It didn't take long for Amber to be brought to the edge of the orgasm that all of the stimulation she had received over the past couple of hours had been pushing her body towards. Jean didn't give Amber any mercy and let her thumb flick and rub the now moaning girl's clitoris. Jean nibbled on Amber's ear, saying: "Go ahead pet, let it all out, just you and me now." Amber started to squeeze her legs against Jean's hand pressing it nice and tight against her privates. Jean rubbed even faster before she finally plunged two of her fingers into Amber's sobbing wet pussy. From experience, Jean knew exactly how to reach Amber's g-spot, so it only took a second for her middle finger to begin massaging Amber's most sensitive place. Amber started to writhe under and thrust her hips against the invading digit, she then began to moan so loudly that Jean was worried the neighbors would hear. Between cries of 'fuck' and 'oh god,' Amber finally orgasmed, her juices flooding all over Jean's hand. The young woman shuddered on the bed, her legs still clamped down on her stepmother's hand as she slowly rocked with the waves of pleasure that poured throughout her entire body. As she let out a sigh of relief, Amber felt Jean's hand slip out from under her legs and travel up to her mouth. Amber dutifully licked her master's fingers clean of juices and swallowed the nectar with a smile. She just laid there, consumed with the afterglow of her own orgasm and the feeling of Jean's breathing on her neck, until she felt a tug on her arm. "Come on my little slut, your reward isn't over yet." Jean said as she sat up and pulled Amber up so they were on their knees. "Now face me." Still tired from the orgasm she had received, Amber turned to face her stepmom and looked in stunned silence as Jean dis-robed, leaving her magnificent body only hidden under a blue push-up bra and a little lacy g-string. Amber didn't get time to even question what was happening before Jean launched at her with a kiss. Even when she realized what was happening, Amber was unable to resist the much more skilled tongue's effect on her and limply tried to get her own tongue to match it, surrendering a moment later as she let Jean have free access to her mouth. When the kiss broke, Amber finally spoke, her heart pumping like mad: "What are you doing, mommy?" Amber asked as she felt her stepmother's hand move behind her back and unclasp her bra, "I thought you said you wanted dad's permission first?" Jean ignored her and pulled Amber's bra off, with a quick move of her hands before she finally answered her stepdaughter's question: "Oh we'll get that soon enough but this is just a reward," Jean said with a lustful smile. "Besides, now that I know you're bi and have the hots for a girl in your class, I have to start training you to pleasure women and I'd rather do that now, rather than later. Not to mention, I think four and half years is too long a time for my precious slave to go without a good scissor fucking." Jean kissed her quickly on the lips and then pointed to her own bra. "Now could you be a dear and get this off me?" Amber just nodded and let her hands go back to the clasp on Jean's bra. Partly due to her only experience unfastening bras being her own and partly due to her nervousness, the nineteen-year-old took some time clumsily pawing at the clasp. Jean kept quiet at Amber's inexperience but couldn't suppress a laugh when Amber finally managed to get the stubborn garment unfastened and went wide-eyed as Jean's breasts bounced free. "Well, don't just stare at them pet, you aren't going to learn how to please a woman by just drooling over her tits." Jean said as she grabbed Amber's hands and placed them on her round breasts. Amber looked into Jean's eyes as she slowly began to knead her stepmother's breasts. She felt how firm they were and was surprised how much the nipple's on Jean's dark areola stuck out. She brushed the little nubs and hesitantly started to pinch them between her fingers. "Come on slut, you aren't going to get a woman off just touching her breasts," Jean said, getting a little impatient. "We can stop if you're not ready, I'm sure some of my friends wouldn't mind giving you orders if you don't want to take my generous gift." Amber shook her head and tried to be more aggressive but all it amounted to was just lightly squeezing Jean's tits as she shook, almost petrified. Jean sighed and kissed Amber on the cheek. "Amber, is this really bothering you? Look, I'm not gonna force you or punish you if you don't want to go further but I need to know what's wrong." "I'm sorry Jean, I...I've just thought of this for so long that I guess I can't believe it's happening. I really want this, I'm just not sure what to do." Amber stammered. "I think I understand," Jean said, pushing Amber back down on the bed so she was staring up at the ceiling. "Look, since this is your first time, why don't we drop the master/sub play for a bit and we'll just take our time," Jean then added with a wicked gleam in her eye, "I'm going to expect you to only need this soft treatment once though; it's all paddling and anal play if you don't properly please me in the future." Jean then positioned herself over Amber and kissed her, "Now I'm going to play with you a while and I want you to just lie back, stay quiet, and think of what feels good. Jean began to kiss and lick every inch of Amber, starting at her forehead, then going down to her nose, her lips, her chin, etc. until she reached her chest. Jean took one of Amber's breasts and began to lightly suck on her nipple while she squeezed and massaged the teen's free breast with her right hand, drawing some light moans from Amber as her sensitive nipples were pleasured. Jean switched off between the two wonderful lumps of flesh, occasionally tweaking Amber's taught nipples. Despite her stepdaughter's silent protests, Jean rose up on her hands and stopped teasing her nipples. Jean took a moment to admire the teen before she spoke: