Training Big Brother III free porn video

The next day was Saturday. Tom was up early hoping to avoid his little sister. He emptied the dishwasher. That job was now all his since it could be done when their mom wasn't around. Karen had only agreed to continue her jobs that were visible to their mother in order not to arouse her suspicions. Karen must have heard him clattering about. As he was finishing up the dishwasher she appeared, still in her nightgown. Their mom was still asleep. "You're up early," she said. "Uh huh," he muttered, putting the last of the silverware away. "It's Saturday. I've got things to do." "Well before you go running off, we're going to do a panty check. Unzip and show me what you're wearing." Oh Jeez! Was he supposed to be wearing panties? She hadn't said anything last night. "Uhhhh... I... I'm not wearing panties. You didn't say I had to." "You're not wearing panties?" She asked incredulously. "Saturday's no different than any other day. Did you forget about rule number one? Panties. Every day except gym days." Tom gulped. He'd thought the rule just applied to school days. Obviously Karen had a broader interpretation. "Now run upstairs and put on a pair of my panties." Thankfully he remembered rule number four. No arguing. Up the stairs he went. "What color did you choose?" Karen asked five minutes later when he was back downstairs. "White," he muttered, a little embarrassedly. "Oh... That's a boring color," she teased. "Does it at least have some frilly lace?" Tom shrugged. "I don't know." "Well let's check. Come over here and show me." It was humiliating to have to submit to a panty check by his thirteen- year-old sister. His penis, which had begun stiffening upstairs while he was changing into them, became fully erect as he unzipped so she could see the panties. "Uh uhh. Drop your pants. I can't see if you picked a pair with lace." Damn! But Tom acquiesced and, after undoing his belt, pushed his pants down to his knees so Karen could examine him. "Whoa! What's this?" She giggled and was stared at the stiff little tent pole in the panties. "And you didn't want to put on panties this morning. Ha!" Tom's face turned a bright red and he moved to cover himself with his hands. "Uh uhh." Karen blocked his hands. "I want to see." She grinned and pulled the front of the panties out and down, freeing Tom's erect penis. "Somebody's happy I sent you back upstairs for panties. I bet rule number one is his favorite." She giggled and lightly swatted his erection. "Don't... Don't do that," Tom gasped, backing away. Christ! His little sister shouldn't be touching him there! "Uh uhh. Rule number four. We do things my way. No arguing." She slapped his erect penis again. "Or I'll invoke rule number three and you'll be wearing a bra today?" "No! I can't do that! Mom's home today!" "Then I get to play with your little 'pee pee'." Oh Jeez! This was so wrong! But he didn't have a choice. Karen slapped his penis back and forth. He was aroused and getting more so with every slap of her hand. Before he could stop himself, he began spurting excitedly. "Oh my God!" Karen exclaimed. She hadn't expected this! Looking up she saw her brother's face contorted with embarrassment and excitement, caught in the throes of his orgasm. "Look at the mess you're making! It's all over the floor!" He couldn't stop. His penis continued to spurt, sending globs of wet, sticky cum to the floor in front of him. Finally he was spent, gasping as he's erect penis began to deflate. "Ewwww," Karen exclaimed, looking at the mess on the floor. "I think you'd better clean that up before mom comes down." Tom couldn't agree more. After pulling his pants up, he grabbed a paper towel. Karen stood over him while he fell to his knees to wipe it up. She hadn't known she could make him cum just by batting his penis. She'd only done it because he didn't want her touching him there. Making him give in to her served to emphasize his newly learned obedience. His unexpected orgasm was an added bonus and she decided that some more humiliation would help to cement her newfound authority. "Tom," she began when he'd finished cleaning up his mess. "I think we ought to go to the mall today. We both know my bras are a bit small for you. It's time you had your own that fit you. What do you say?" Oh Jeez! No! "C'mon Karen... I can't go shopping for... a bra." "Rule four. We do what I say. There's to be no arguing. And of course, you can go shopping for a bra. I'll ask mom to drop us at the mall." Christ! She was really serious! He groaned as Karen went on to explain that before they went she'd measure his chest so he could buy the right size. When they were in the lingerie department, she'd help him pick out something sexy. Two or three bras with matching panties. Maybe a camisole. It would be fun. What she didn't tell him she was going to ask Becky to join them. Three hours later they were at the mall. Their mom said she'd pick them up at three o'clock and to be outside waiting. Karen and Becky got out of the car, chatting away happily. Tom wasn't nearly as happy but he followed the girls, afraid of what was in store if he didn't. "Oh Tom," Becky exclaimed in a somewhat loud voice as they entered the mall behind another group of teenagers. "Aren't you glad you're finally going to buy your first bra?" She grinned at Karen as Tom's face turned a deep shade of red. "Not so loud," he whispered frantically. One of the girls in front of them turned to look at him. "You should be happy... Now you won't have to borrow your sister's bra anymore." "Becky! Stop!" Tom's face was beet red. The girl was giggling to her friend and pointing at him. Becky laughed, enjoying his embarrassment. Although Tom was bigger and three years older, Karen's new rules meant he had to put up with Becky's teasing. He didn't have a choice. Tom followed them into the department store and up the escalator, feeling quite self-conscious as they entered the women's lingerie department. Furtively glancing around he was relieved to see they were the only shoppers. That relief disappeared when a cute salesgirl approached them. "Can I help you girls?" she asked pleasantly. Tom gulped. The salesgirl looked to be maybe a year or two older than he. He felt himself blush when Karen said they were looking to buy some new bras and panties. "Well you came to the right place." She looked first at Karen's chest, then at Becky's. "I bet you're both thirty two's... A cups?" The girls nodded. Then Karen spoke up. "We're also looking for something a little bigger..." She grinned mischievously. "We decided you could fit into a thirty six, didn't we Tom?" Oh Christ! This couldn't be happening! He wanted to disappear into the floor! The pretty salesgirl looked at him, a smile forming on her lips. "Sure," she said, doing her best to act normally. "We can find a thirty-six that should fit. What size cup?" Tom couldn't answer. Mortified, he was silently cursing his sister while turning a bright red. "I think an A cup," Becky piped up, an impish smile on her face. "Unless you have anything smaller. It's really a training bra." The salesgirl paused with a thoughtful look on her face. "Yes... I think we have a few thirty-six inch bras that come in a AA cup. Let's take a look." She led them up the aisle to another counter. "Here's one," she exclaimed, holding up a pink bra with bits of lace. "I think this one even has matching panties." Looking down at the collection of underwear on the counter, she found what she was looking for. "Here it is." She held up a pair of frilly pink panties. "These are a medium. I think they should fit," she said, measuring Tom's waist with her eyes. "What do you think, Tom?" Karen's impish smile said she was totally enjoying her brother's embarrassment. Tom's face turned a deeper shade of red, if that were possible. Christ! The salesgirl had the bra in one hand and the panties in the other, holding them out for his approval. "Fine," he muttered angrily. He just wanted to get away. "He wanted a couple of bras. And some more panties," Becky chimed in, winking at Karen while Tom glared angrily at her. "Well," the salesgirl began, rummaging through the bras on the counter. "Here's another one. More of an everyday bra." She held up a white bra. "And here's some panties to go with it." "He'll take it," Becky said. "And he wants some more panties... Maybe three more." She nodded her approval when the salesgirl selected a three pack of frilly, multicolored medium sized panties. "Now that he's taken care of, we also want some new underwear." With that the girls went about selecting new bras and panties for themselves. The salesgirl handed a very embarrassed Tom his new purchases while she helped Karen and Becky. When they were ready to checkout Tom placed his new underwear on the counter with his sister's. "Uh uhh," Karen said. "Mom only gave me enough money for mine. You pay for yours." She separated the underwear. The salesgirl rang up hers first. Tom's was next. "Two bras and five pairs of panties. That will be $46.75." Tom gulped. He'd been saving his money but not for this. He handed the fifty dollars he'd brought to the salesgirl. "Here's your change." Smiling, she handed him $3.25. "Now just a minute while I put your new undies in a bag." Then she proceeded to hold up each item and fold it before placing it in the bag. Tom glanced around, wondering how many people were watching. He noticed several store employees looking over at them. Christ! This was so embarrassing! When Becky had paid the three of them went back out into the mall. They still had an hour to kill before Karen's and Tom's mom came to pick them up. "How much money do you have left, Tom," Becky asked. "Just about three dollars. I didn't think I had to buy all that stuff." "That's too bad. Next time bring more. It's going to be summer soon. You'll definitely need a new bathing suit." She grinned at Karen and the two girls giggled. "Well why don't we at least go look at some bathing suits," Karen said. "That way you can think about what you want to get next time we're here." Next time! Christ! Weren't the bras and panties enough? They couldn't make him wear a girls bathing suit! Or could they? The girls took off for another store. Tom followed, carrying his bag and the two the girls had given him. Halfway through the mall Karen stopped to look at a scantily dressed mannequin in the store window. Tom looked up at the store name. Oh Christ! It was Victoria's Secret! "Oh. We should have started here. Tom would definitely look cute and adorable in these sexy bras and panties." "Oh well," Karen replied. "There's always next time." She paused for a moment. "But there's no reason not to go inside and look around. I'm sure they have bathing suits." "You go in. I'll stay out here," Tom said, hopeful he could avoid further embarrassment in the store. Karen smiled. "No Tom. You're coming in with us. We're going to look at bathing suits. And we're probably going to look at some bras too, although I doubt Victoria's Secret stocks many AA ones. Come on now." Damn. But he followed the girls into the store. Their first stop was a counter featuring a line of extremely sexy bras and panties in a multitude of colors. "What do you think, Tom?" Becky asked in a somewhat loud voice and an impish smile. He just shook his head and grimaced. A salesgirl noticed them and headed their way. "Can I help you?" she asked. "My brother was just wondering if you carried training bras or maybe something in a AA cup," Karen explained. "He's a little bit embarrassed to ask himself." The salesgirl, a bit taken aback, gave Tom an appraising glance before answering. This wasn't the first time she'd had a male interested in lingerie, but it was the first time one had been brought in by his younger sister and a friend. "I'm afraid not," she answered, smiling apologetically. "The department stores would most likely have them." "We were just there," Becky chimed in. "And they do. Tom bought his first bra today." She grinned impishly. Tom's face had turned a bright red. "But then we were passing by and he just had to come in." She turned to him. "Don't worry, Tom. Soon you'll outgrow your training bras and be able to shop here." Tom glared angrily at her but kept his mouth shut. He just wanted to disappear! He glanced at the salesgirl who was smiling, obviously enjoying his discomfort. Then, out of the corner of his eye, he caught sight of two girls he recognized from school. Oh Christ! Leslie was in his history class and Beth was a cheerleader. He couldn't let them find out he was shopping for girl underwear! His life would be over! He had to leave! He quickly muttered, "I've got to get out of here." Then he turned, doing his best to hide his face, and made a beeline for the door. Becky and Karen called after him but he ignored them until he was safely out of the store. "Just what do you think you're doing?" Karen exclaimed when she caught up with him. "You don't run away from me like that!" "Please Karen!" Tom was beside himself. "There were two girls from school in there. I couldn't let them see me shopping!" "So...," Becky said. "What's it worth to you? We could post one of our cute pictures of you. Or we could go back inside and finish looking around. We haven't even seen their bathing suits yet." Oh Jeez! He would be mortified with either alternative. "Please Karen," he tried again. "Please! Can't we just go?" He gulped, hating that he was begging his sister. "I'll do anything you want. Please!" "Anything?" Karen smiled. She enjoyed the power she had over her older brother. It was a turn on, watching him plead with her. "How about you put on a little show for Becky and me... Dress up in your new undies and let us take some more pictures. Would you do that?" "Uh huh," Tom replied, resignedly. He just couldn't go back into Victoria's Secret and have the girls see him shopping. "We can do it at my house," Becky chimed in. "My folks are away until tonight." With that decided they walked around the mall until Tom and Karen's mom arrived. So it wouldn't arouse her suspicions that something was going on between her children, they decided that the two girls would be dropped off at Becky's house while Tom went back to his house. He would then go out, ostensibly to play, and hightail it over to Becky's. The girls made it very clear what would happen if he didn't show up. o o o o o "Oh, hi Jill. I thought you were out." "I was but got back early." Becky's older sister was in the family room when the two younger girls came into the house. She was a senior in high school, a year ahead of Tom, and a cheerleader. Karen looked questioningly at Becky. "Tom's going to be here shortly," she whispered. "What about the little show he's going to put on?" Becky laughed. "He can still put on the show for us. Jill knows what he's been up to. I showed her some of the pictures." "You didn't!" Karen exclaimed, unable to keep the smile off her face. Her brother was in for it now! "Yup," Becky replied. "Jill... didn't I show you pictures of Becky's brother? You know... all dressed up." "You did. In fact, you even sent me a couple." Jill smiled. "I haven't shown them to anybody yet, though." "See," Becky said, turning back to her friend. "Jill knows. In fact, I bet she'd like to see the show Tom's going to put on." The girls proceeded to show Jill the girl underwear Tom bought and was going to model for them. Karen held up one of his AA bras and the girls all laughed. A boys first training bra. Karen then explained to Jill how she'd found one of her bras with the hooks pulled out. The only explanation was that someone with a larger chest had been wearing it. And that led to her brother, Tom. The rest was history. Now he had to do what she wanted. The girls decided that Tom might get a bit freaked if he saw Jill when he arrived. It would be better if she appeared after he'd changed into his new underwear. Becky suggested hiding his clothes outside so his options would be severely limited if he panicked at the sight of Jill. Meanwhile Tom, resigned, had left his house and was headed to Becky's. He wasn't happy about having to dress up for the two girls but it was better than having his secret exposed to the girls in his class. Just the thought made him shudder and, not surprisingly, gave him an erection. It wasn't a long walk and in a few minutes he was knocking at Becky's door. "Hi," Becky greeted him. "C'mon In. We've been waiting for you." Tom followed her into the family room. Karen was laying his new underwear out on the coffee table. "We thought you might like to try these on first," Karen said. She held up the pink bra in one hand and the matching panties in the other. "Then we'll get a few pictures of you modeling for us. Ok?" Oh Christ! Did he have to go through with this? Seeing his hesitation, Becky retrieved her phone and brought up one of the more embarrassing pictures of Tom. "Or we can send this out to our friends. Which would you prefer?" "Fine," he muttered. The damn girls had him over a barrel. He pulled his shirt over his head and dropped it onto the floor. His shoes were next followed by his pants. "Ooh! I forgot you were wearing my panties," Karen exclaimed, giggling. "Take them off and put on your new ones." She held out his new panties. Blushing, he took the panties and turned away from the girls so he could change with a modicum of decency. Becky quietly picked up his clothing and disappeared into the kitchen and out the back door while he was stepping into his new underwear. "Now the bra," Karen directed, handing it to him before he had chance to turn around. "Arms through the straps and then I'll hook it for you." As his sister pulled the bra tightly around his chest, she teased. "You'll have to learn to do this part yourself." Red faced, Tom turned around as Becky stepped back into the room. He caught the smile she gave his sister and then looked down to where he'd dropped his clothes. They weren't there! "Hey! Where are my clothes?" "Safe and sound," Becky replied. "You don't need them now so I put them away. Out of sight, out of mind as they say." "But... but...," Tom sputtered. He was stuck wearing girl's underwear until Becky gave back his clothes. He felt his penis twitch. "No buts," Karen said. "You're staying in a bra and panties. Behave and you'll get your clothes back later. When we're ready." Her brother gulped at the sound of her determined voice. "Now model your new undies for us so we can get some pictures." Reluctantly, Tom began posing while the two girls snapped pictures, adding to their collection of embarrassing photos. With his penis now fully erect, the pictures were even more humiliating. "Becky. What's going on down there?" Tom gulped at the sound of a third voice. Oh Christ! Was that Becky's sister? Oh God! He heard footsteps on the stairs. "Oh Jill... Are you home? I thought you were out," Becky said, grinning at Karen. "We're in here. In the family room." Tom was beside himself. God! Jill was a cheerleader and a year ahead of him in school. This couldn't be happening! Unfortunately, it was. His penis twitched as the realization Jill was going to see him all dressed up in girl underwear. Oh God! This was going to be so humiliating! "What the heck?" Jill stepped into the family room and took in the sight of Tom in a bra and panties. "My God!" she exclaimed in mock amazement. "Whose underwear is that?" Tom wanted to disappear; he was so embarrassed. Unfortunately, he couldn't. Instead he stood there with a raging hardon, humiliated beyond belief. Then his penis totally betrayed him. He couldn't stop himself and a moment later he began spurting into the panties. Oh God! Christ! His penis continued to erupt, filling the panties. He saw the looks of astonishment on the girl's faces and he wanted to cry! His embarrassment was total! "My God!" Jill exclaimed! "What are you doing?" Tom couldn't answer. He was still in the throes of his pent-up orgasm, emptying himself. His panties were a mess; the front was completely soaked with his sticky fluid. When it was over, he gasped breathlessly and stood staring at the floor, humiliated. "Look at him," Jill said, pointing at his crotch. "He just shot his load." Karen quickly got her phone out to capture her brother's humiliation. "Oh wow!" Becky exclaimed, her gaze immediately fixating on the large wet spot on the front of his panties. She quickly walked over and, before he could react, grabbed his waistband and pulled the panties out so she could look at his shriveling erection. "Ewwww!" Her fingers had touched the wet spot. It was sticky and yucky. She then yanked the panties down to mid-thigh. Tom's spent penis hung limply for the girls to see. "Well it looks like somebody needs to change out of his panties," Jill said. Then to Tom she said, "Step out of them. They're a mess." Feeling very humiliated, Tom had no fight in him. He pushed the panties down until they dropped to his ankles. Then he worked them over his heels and stepped out of them. He was naked from his chest down. "Becky," Jill said. "Go get a wet washcloth. Our little sissy needs to be cleaned up." Jill took the wet washcloth from her sister and cleaned Tom's sticky penis. "Somebody made quite a mess," she teased. "We'll get you into a clean pair of panties and then maybe I'll invite a couple of my cheerleader friends over." Oh God! No! Not that! "No! Don't do that! Please!" Seeing his frantic reaction, Jill continued her teasing. "I think Sally and Kim would love to see you in a bra and panties. Do you know them? They're in your grade." Oh God! Yes! He knew them! "Please! Please don't," he murmured beseechingly. His flaccid penis twitched and began to stiffen. Jill was still wiping him and noticed. "I could invite them over. I bet if we sent them a picture or two, they'd be over in a flash." "Oh Jeez! You can't do that! Please don't!" "Are you sure? This little fellow seems to like the idea." Jill removed her hand to allow Tom's now erect penis to spring upward. She smiled impishly and the other two girls giggled. "Suppose we get you into clean panties now. I don't think you want Sally and Kim to see your little pee pee sticking out like that." She playfully batted Tom's erection. Oh God! She couldn't be serious! "Please! Please don't let anybody else see me like this!" "Now, now. Don't be so bashful. Now step into these panties," she said, handing him a pink and blue flowered panty. Tom did as he was directed, quickly pulling the panties up to cover his erect penis. "Please!" he begged. "Please don't invite Sally and Kim over! I can't let them see me dressed like this!" "Well...," Jill said thoughtfully. "I suppose... if you do a good job trying to be as girlish as you can be... maybe we won't invite them over. Do you want to do girly things?" "Yes. Yes," Tom eagerly replied. Anything as long as nobody else saw him like this. "Ok," Jill said with a wink at her sister and Karen. "Girls don't like to have hair on their legs and underarms. I bet you don't want any hair there either. So are you going to let us get rid of that yucky hair?" Jeez... Shave his legs and underarms? That was a bit much. But did he want Sally and Kim over here? Nope! "Ok," he muttered, nodding his head. The girls led him upstairs to their bathroom where they proceeded to shave his legs and underarms. Luckily, he didn't have any chest hair yet. To his further humiliation they even trimmed his pubic hair so it wouldn't stick out of his panties. He'd thank them for that when it became time for a summer bathing suit. Next Tom learned how to put his bra on like a girl; reaching behind his back to hook it. He struggled at first, hooking the wrong hooks, but eventually he managed it. They had him practice for a bit. Karen wanted to make sure he could do it without her help. It was getting late, close to dinner time. Karen said they needed to go, but it might raise their mother's suspicions if both she and Tom arrived home together. She'd leave first while Becky retrieved Tom's clothes. "Bye Karen," Becky said shutting the front door after her friend left. She turned back to see Tom waiting in his bra and panties. "Can I have my clothes now, Becky?" She glanced at Jill who shook her head. "Not just yet, Tom," she replied. Her sister stepped forward. "We'd like to make a little video first," Jill said. She had her phone out. "Say your name and tell us how much you like dressing up in girl underwear." Oh Jeez! No! Christ! If that video ever got out he may as well be dead! "No Jill! I can't do that." "Do you want your clothes back?" "Yes! But... but," he sputtered. "Make the video or walk home dressed as you are." Oh Christ! He couldn't do that! The girls had him over a barrel. He had no idea where Becky had hidden his clothes. With a gulp he nodded his head. "Ok." They had him say his full name, the school he went to and what grade he was in. Close to tears he confessed that dressing up in girls' underwear got him aroused. The girls got a closeup of his erection, barely hidden by the panties. He went on to explain he had bought the bra and panties he was wearing in the video. Jill then directed him to prance around to end the video. It was an extremely damning video. Tom wanted to cry as Jill played it back for him while Becky went to get his clothes. "Please! Please don't share that with anyone," he pleaded as he got dressed. The girls laughed and explained it was simply insurance to make sure he would continue to dress up for them. It was important to practice. There was so much to learn. Makeup. Nails. Walking in heels. Poor Tom gulped as the list went on. They were fully intent on feminizing and training him to be a sissy. Oh Christ! He started to remove his bra when Jill stopped him. "Get used to wearing that under your shirt," she said. "But... but... I can't let my mom see me in this. She'll freak." "You mean she doesn't know her little boy wants to be a sissy?" Jill asked. Tom looked down at the floor, ashamed and shook his head. "Ok. You can take it off." Tom breathed a sigh of relief and, using his newly learned skills, reached behind and unhooked the bra. Karen had taken the department store bags so he stuffed it into his jeans pocket. He pulled his T-shirt over his head and slipped into his shoes. "Ok Tom. We'll be seeing you again," Jill said, opening the door for him. "Maybe next time Sally and Kim will join us." She smiled sweetly. "Bye." Tom stepped off the porch thankful to be free, at least for the time being. Christ! Karen, Becky and now Jill had made him dress up like a girl. And not only did they have humiliating pictures; they also had that damn video. He was definitely over a barrel and was going to be feminized whether he wanted to or not. He felt like crying at his situation. He got to his house and, after saying 'hi' to his mother, headed up to his room. He gulped when he stepped through the doorway and saw his department store bag on his bed, in plain sight. He quickly pulled the bra from his pocket and stuffed it into the bag with his other new underwear before hiding the bag in his closet. Christ! He hoped his mother hadn't seen it. "Hi big brother." Karen stepped into his room all smiles. "Becky sent me a cute little video." She laughed. "I was wondering what was taking you so long." Oh great! Now she had a copy of the video too. "Where's your new underwear?" "I put it in the closet." Then he gave her an accusatory look. "Why did you leave it out on my bed? Mom could see it." She ignored his question. "I can see you're not wearing a bra under that T-shirt but you better still have panties on. Do you?" "Yes," he replied, but he was still upset. "Mom could have seen the bag and looked inside." "Tom," Karen said firmly. "We're talking about whether you're wearing panties. We're not talking about whether mom saw the bag. Now undo your pants so I can see if you're telling the truth." Damn her! It was humiliating to have to drop his pants for a panty check. But not as humiliating as the alternative. Grudgingly he undid his belt and pushed his pants down so she could see the pink and blue flowered pattern. "Happy now?" he asked a bit snarkily. "Don't use that tone of voice with me, Tom." She glared at her older brother. "I'm not your little sister anymore. I want to be treated with respect. Understand?" "Yes," he muttered realizing she held all the cards. "Yes what?" "Huh? What do you mean?" "What I mean is for you to show me some respect. How about a 'Yes ma'am'?" "Ok," he replied. Then seeing the look on her face, he realized she meant now. "Yes ma'am." "Much better. I like that." At that point their mother called them for dinner and they went downstairs. The rest of the evening was uneventful. Tom disappeared to his room and thankfully, Karen left him alone; choosing instead to stay downstairs to watch TV. He found a better hiding place for his new underwear, in the back of his desk drawer. His mother never went through his desk. He kept out one panty and put it in his underwear drawer, beneath his boy underpants. Karen would expect him to be wearing them tomorrow and he knew better than to disobey her. He was learning.