Date: Thu, 22 Oct 2020 21:12:28 +0000 From: S Hardman Subject: THE MEAN GURLS Chapter 4 Teen Transgender **None of this happened. All the adventures of the characters were between completely consenting individuals. It's not real. If sex acts like this offend you or you are not 18 do not read it. **Consider a donation to Nifty.org THE MEAN GURLS Chapter 4 I'm back!! The leader of the slutty sissy teen schoolgirl sisterhood! This gaggle of cock gaggers is ready to regale you with stories of our escapades with different strong manly Daddies and their leaky dongs! The Sissy Squad abides. You've met all of our participants. There is me, Cherry, the head cheerleader and lead head giver. There's Alyson, She's a bona fide boner-inducing curly blonde haired bombshell with a mouth and boipussy of legendary renown. There's Jessica, the flute playing future sissy wife of the band director with a very sweet disposition and even sweeter lips. There's Violet, the seductive stepdad ex-lover, and lewd vixen who's growing more confident every day and making men's cocks grow stiffer every day as well! And last but not least there's Josie. She's the alumnus of the squad and the caretaker and jerker-offer of Mr. Hardman, the school assistant principal. She is a red headed firebrand. Now you know all the parties. Let's see how this all ends. It will of course end with cocks in our ends! Well as I've mentioned a few times Aly and I started a company. It's called Cocks Unlimited. It is only incorporated on a secret website on the internet that's password protected. It's really word of mouth that gets us our clientele and then they get our mouths and hands. Aly had the grand idea one day as she was down on her hosed knees while a man grunted dirty sounds at her as his cock was buried in her throat. Her mouth is a powerful weapon and he's a powerful businessman in the next town and wondered if she had a friend who might participate with him and a group of some of his most powerful clients. It would be sort of a retreat for wealthy men with trashy teen femboys as a prize. While her face was being pounded an idea lightbulb popped up over her head. She'd charge these horny dudes for services for doing what she already loved doing which was being a sissy slut. She ran the plan by us late one night as we had a little gossipy drinking session with the Squad. I was immediately a yes. Jess had to pass. She's decided to be faithful to her man. Josie was also a no. She loved the idea of getting her mouth fed cock by multiple men at a time but was afraid it would jeopardize her relationship with Hardman. She was in love. Blah blah blah. Violet was going to think about it. I knew that meant she'd do it, too. First a little refresher on where we are. Josie is handling Hardman's hard one nightly. Jess is holding out for the band director's baton while playing flute and his bone until graduation. Aly is playing the field, not like the softball girls playing with and munching the grass between each other's legs. She likes her bats firmer and more on the mature side. Violet is now running the school paper and yearbook. She's living with her dad who is a prominent attorney in town, Richard `Rich' Rodman. Yes, her name is Violet Rodman. As for me, I'm very busy cheering and updating the Cocks Unlimited secret website. I actually ended up spending quite a bit of time at Violet's house. You see I really do enjoy Rich's company. The thing about femboys is that we are ladies but we like guy stuff, too. I've already laid out our case as the perfect humans. I love football so I can be just like the best guy friend, too. Every Sunday I spend at the Rodman's house watching our beloved Dicktown Dolphins pro football team. You can probably see where that is heading, eventually in my tight end. So let's get started with the end of the story. Our first real gig was after a board meeting at a local bank. Dustin Stiffer, the CEO, surprised 6 board members with sissy blowjobs in addition to their yearly bonus. They wanted to bone us but Cocks Unlimited limits service to handies, foot jobs and oral unless otherwise agreed upon. Alyson and Violet and I sissied out and did a slutty dance to music in nothing but pantyhose with our little hard gurl cocks. Yes, Violet decided to join us because making a ton of money for doing what she already loved seemed agreeable to her. We rubbed our little sissy sticks over the soft sheer fabric seductively and then we each dropped to our knees in front of a suited board member, loosened his tie and released his very important cock. Some were bigger than others but no one paid attention as we each begged the Daddy in front of us to release his prestigious sperm on our faces and flat chests. We stroked and sucked each rod to release and each one squirted with a manly groan and then we performed the same act with the other 3 gentlemen. For our services we each made $5000. Not bad for 17 and half minutes of work. We put on our frocks and heels and sashayed out with cum still dripping down our faces. The elevator ride was interesting with 2 old ladies with looks of horror as ejaculate plopped onto our dresses. We can't help it that we're willing to the job that real girls won't and get paid for it! Besides those men had all seen us cheering the previous Friday night and wanted to see our little femme bodies up close and were willing to be very generous. Discretion was secondary then but we've learned to keep it more private since those early days. I spent the following Sunday at the Rodman's in a tiny skirt that hardly covered my gurly clit, a skin tight football t-shirt and heels teasing Rich. Violet is just fine with me chasing after her father. She thinks he needs some companionship and she knows that sissies can't help themselves once they get a cock they want in their sights. We're like dogs to bacon! I know that I told y'all about spending time with Randy Dickens in the first chapter. He is so sweet and he was my first real man. He punished my sweet back pussy. He and I still see each other sometimes secretly but it is not serious. Rich on the other hand gets me soaking wet in my pantyhose. He hadn't realized what my intentions were just yet but he came around. Besides Violet was preoccupied with another man. She loves married men or in this case separated men. She's is a natural home wrecker. Violet got a text and kind of breathlessly said "He's here!" The `He' is our principal. Yes, Dr. Driver was there to pick her up. She was entertaining the principal of our high school. She opened the door and he came in. I was a little shocked and so was he when he saw me. A little warning for both of us would have been nice. He stammered a hello and said something about being interviewed by her for a school newspaper article but he knew that I knew that was a bunch of baloney! He was here to pick up a slutty little feminine sissy boy and get under her skirt. She looked dreamy. She had on a flowy short pink dress and nude pantyhose and pink fuck me pumps. There was no interview going to take place unless it was Violet interviewing his dick one on one. If she twirled you could've see her cock plain as day under the sheer nylons and I'm surprised she didn't. Driver and Rich seemed to know each other and they didn't seem all that awkward around each other. Birds of a feather, I guess. This particular bird is one who lusts after tight femboy cunts. They then vacated pretty quickly as I winked at her. Come to find our Violet had been teasing Dr. Driver for months and the married but separated father of 3 had one day finally just asked her out on the pretense of school business naturally. Yeah right!! He had 2 kids in college that were costing him out the ass and his younger son had mysteriously disappeared after 2 months into his freshman year at our school. I bet we'll find out more about that. Violet had to go to his office often for expenditure approvals and Dr. Driver always made sure to oversee the matter personally. He was being driven mad being so close to this gorgeous sissy and she had fallen pretty hard, too. He was a real alpha male. He was the former quarterback and class president and had been knocked down a few pegs by life but obviously still held an appeal for a simpering sissy like Violet. She wanted to be man-handled by a real man. I'm touching myself just thinking about it. But where do you take someone when you don't want anyone to see you and it's a school night? Neither of them cared how far they had to go. They drove nearly 200 miles just to have dinner. Dinner was very fancy at a very exclusive private place where femboys and their Daddies weren't an unwelcome or unfamiliar sight. There was no pretense anymore once they arrived. This coupling was going to happen and Violet made sure he knew it could happen whenever he wanted. She dropped her shoes on the floor and put her hosed feet in his lap as dessert arrived and rubbed them over his prodigious cock. The Sex in a Pan was abandoned pretty quickly as he yanked her out of her seat. When they settled in the car she said, "Do you want me to suck you right here or are we getting a hotel room? If so, I think you better call in sick tomorrow because I know I am." He made beeline to the Marriot Dicktown and booked a room. She'd didn't have an overnight bag but had neatly folded some slinky nightwear into her oversized gurly bag. She told him to relax as she freshened up. When she came out his dick stood at attention. This little femme had on a sheer white baby doll nightie and virgin white hose and she began rubbing her sissy clit and then she slithered up his body on the bed and their lips met. She smelled amazing. Their tongues encircled each other and their dicks met for the first time through the diaphanous fabric and she sissygasmed big globs from her gurl stick making a mess while moaning in his mouth. He immediately pushed her off onto her stomach and pulled up her hips. He pulled down her hose and buried his tongue in her pink fuckhole. She started moaning and bucking. He used his spit to lube up her love tunnel and worked it with his fingers. This train was headed straight to Sissy Fuck Town and he was the engineer! After a lengthy tongue bath she started to beg for his manhood. "Please Daddy! Please! Make me your bitch! Fuck my sissy hole!" How could he say no? He parked at the tunnel entrance and she began to rock back a little and over the next minute he slowly sunk his man missile. He started pumping and then lost his mind and got pretty rough. He pounded her hole with abandon. She was screaming and he covered her mouth so the management didn't think a murder was taking place. She bit his fingers and he yelped. They both calmed a little and then he felt a shudder as she spunked again all over the sheets while he blew his load deep into her boi bowels. They collapsed and the seed started to leak out of her and drip down onto her pantyhose. They had made a sticky mess and he picked her up, stripped her and carried her to the shower. They soaped each other and fucked again. After cleaning themselves they called for fresh sheets but the new linens were filthy with cum by morning, too. Her hole had been pounded harder than ever before and she was in some discomfort but she always also in something else, LOVE! She now knew she liked it rough and she was hopelessly in love!! She was walking funny for 3 days. The squad loved it! From then on there were at least 3 newspaper/yearbook meetings a week that lasted at least an hour. The staff never bothered him during those meetings and very little actual school business was done. They did save the noisier stuff for his bedroom at home. They probably should have been more discreet but no one wanted to tear apart such a happy couple. She rarely went to class but still got straight A's. I wonder why?! One night as she lay across his chest she asked where his son Manny had been. He'd been gone for a long time. He sighed and said Manny had gone to a special school because Manny was now called Mandy. She screamed in both shock and excitement. She wanted to know everything. Manny had been stealing his mom's clothes and got caught mid tug. The mother didn't approve and it was partly the cause of the separation which was obviously going to be a divorce soon enough. She pouted and sweetly said, "You have to let Mandy come back to school. She is probably miserable and I know just how to help her. She will have the Squad now if you let her come back! Femboys are nothing without a man to take care of. She is going to need a man. She also needs our sissy support!" And just like that Mandy got to come back to school. Mandy was so sweet and happy and wore short bouncy dresses and white pantyhose every day. She had a shortish dark feathered femboy haircut and creamy mocha skin and braces. She seemed very innocent but very horny, too. Dr. Driver wasn't keen on letting her explore men yet. Vi would work on that. We put her on the cheer squad because a spot unexpectedly opened up. That was some serious juicy drama! Becky Muffin quit the cheer squad pretty suddenly and the reason why was some syrupy gossip for sure. She got caught getting finger banged by the center fielder of the softball team in the coach's office in her pantyhose. It would have been ignored but the coach thought she was only one mowing Becky's grass field. Coach Lana Kutch was pretty pissed and word got around and Becky decided a hiatus would be the right thing for her at the time. Come to find out the prettiest, most popular girl in school who was also captain of the swim team and president of the fashion club was a shrub scout and had been passed around through most of the outfield and coaching staff as well. She had also been with multiple members of lady soccer and basketball team and bumped fuzzies with 2 female gym teachers, too. Rumor has it that she rarely spent an afternoon where her skirt wasn't hiked up with a rug muncher burying their tongue in her gash. So Mandy joined the cheer team and our femboy squad grew one more. I had spent 7 Sundays in a row at Rich Rodman's watching football. I was getting plenty of dick with my side hustle activities but I wasn't getting the attention I wanted from him. I'd worn the shortest cheer uniform and dresses I had but wasn't getting anywhere. He was a hot rich middle-aged lawyer and that was just my type. I got there early and made a game day food spread that Sunday morning and he came in and was pretty surprised. He seemed impressed I could cook. I was really playing up my ability to be a good little submissive girl and possible sissy wife. We watched the game and celebrated the Dolphin win with a quick fun embrace but it wasn't going to suffice for my needs. Eventually I excused myself to the ladies room and when I returned was only in sky high heels and pantyhose. I decided to take charge and consequences be damned. My little cock was hard from stroking it in the bathroom and I dropped down in front of his chair and unzipped his pants. I pulled out his gigantic snake and started stroking it. He has in literal shock but it started to stand at attention and I slurped my mouth over it before he could stop me and there was no turning back. He started moaning and saying my name which drove me on even more. It didn't take long before he finished in my throat and I cleaned it and tucked it back in his pants. I got up and left the room. I dressed and literally ran out of there. I didn't want to talk about it because if he told me to leave him alone forever I would just die. I raced home and jumped into my bed and rubbed myself to sleep. I let it ride all week and Violet was her normal bubbly self so if she knew she never said anything. I would normally text and plan if I needed to bring anything for the next weekend's watch party but I didn't this week. I didn't hear from him either and I worried but also kind of smiled to myself because I had a feeling. I was actually toying with him a little. Sure enough on Saturday night after we had pleasured 4 Japanese businessmen on a yacht I checked my phone and had a message from Rich. He asked if I was coming to watch with him. He really wanted me to. It was a big game. Haha. Sure. We were playing a winless team at home and it literally meant nothing in the standings. I said I'd be there and I yelped out from excitement. Violet heard but I wouldn't spill the beans as to what was up. I did spill some semen in bed later though. I got up very early and worked extra hard on my makeup and outfit. I wore a tight short red dress, hose, red heels and put my hair in an updo like it was prom night. I showed up and it felt like he was a little extra cleaned up, too. I sat in my normal chair but he said he thought I'd get a better view of the game on the couch next to him. I couldn't get there fast enough. I didn't bother to sit next to him on the couch. I jumped straight into his lap and we smashed our lips into each other's. Our tongues met and I started moaning his name. "Oh my God Rich!" Men love that! He had my dress of in 10 seconds. I threw off my heels and he laid me back on the couch and started kissing my flat little titties. I was a little disappointed about how much time I'd spent on my made up face. It was a sloppy mess already. I was moaning and breathing really hard and I yelped when he grabbed my dick through my pantyhose. I said to him. "I know you're Violet's father but I want you to be my Daddy! Take me! Take what belongs to you!" He didn't need to be asked twice. He flipped me over and tore open my hose and sunk his tongue into my back pussy. It acted as lube and he pulled my hips up to him and rammed his cock into me. It was momentary agony and then pure fucking ecstasy. He was all business as he jackhammered me and I jammed back into him to take it all. He loved that and then pulled me up and kissed my back and down my delicate neck. After a while of pumping he pulled out and grunted and covered my back in his seed and I came, too. I was so happy. We made love all afternoon and evening and didn't even care when Violet came home from Dr. Driver's house. She giggled when she saw the trail of our rumpled clothes from the living room to the bedroom. "Hi guys, I was wondering when this was going to happen! I'm so happy for y'all! You're perfect together. I can't be mad anyway. I'm freshly fucked, too" Mandy was a virgin and was also constantly horny. Her teen hormones were running wild. We all understood. She would be watching a movie with Vi and her dad and suddenly she'd jump up and run out to her room. She spent an inordinate amount of time in her room pounding her little gurly stick and moaning loudly. Dr. Driver would come in and ask where she was and Violet would say, "You know where she is. She is jacking herself off in her room." Then she'd show up straightening her dress and hair. Lying in bed one night they heard her moaning and grunting and Violet said, "You have to let her find a man. A sissy needs a man. She can't help it. A sissy needs a man to please and fill all her little dirty holes! She needs more than just fantasies, honey. Pleasssse baby! She needs to lose that virginity and then she'll settle down." He, of course, said yes because he couldn't say no to Vi. It was suddenly known around town that a new sissy had her virginity to offer and horny men started sniffing around her sweet boipussy! Violet took charge. Mandy looked up to Violet like a mother even though Mandy was 11 months older than her. Violet had a lot more experience and she was going to figure out who got to be Mandy's first time. This meant teaching Mandy all there was to know about being a sissy. She took her shopping for dresses and makeup and pantyhose and shoes. She stressed that femboys don't get a day off. You have to look your best all the time. There are no jeans or sweatpants days unless your full-time Daddy says he wants you to have one. She reminded Mandy that a sissy has one job above any other and that is to be ready to please men all the time. Then when the time comes to please that man make sure they're pleased like never before. Make sure you make lots of eye contact and make them know you only care about them and no one makes you happier. Listen and learn what they like and do that! Treat a man right and he'll repay the favor in spades with both dick and riches! But be sure to leave them aching for more of your sweet bussy. She mulled over several candidates but one very rich man became the obvious choice. Aly said she had spent a few nights with William Wanx. He was a reclusive millionaire that lived on a big ranch outside of town. He'd invented some internet widget that everybody used and was now filthy rich, bored and alone. Aly made the connections and it was set. Mandy got dolled up with Vi's help and was picked up and driven out to his home. It was huge and a middle aged very in-shape hot man answered and let her in. Wanx was very sweet to her. She was very nervous and he calmed her immediately by telling her they didn't have to do anything she wasn't comfortable with. That was all the invitation she needed. Her fear melted away and her sissy instincts took over. She leapt into his arms and kissed him. She was in heat. Nothing is hotter than a teen femboy in heat! She dropped to her knees and unzipped his shorts and plucked out his cock. She slobbered like a starved dog all over it and it eventually made a mess all over her pretty dress. He tore her clothes off and was obviously very impressed with her oral skills. He loved how she looked and looked at him. So impressed that he carried her off to his quarters and ravaged her behind with his thick man meat. He laid out the sweet fem trap on her back and she spread her silky legs. He lubed up her unspoiled cunt and eased his veiny monster in. It took a while until it allowed the intruder access but nature took its course quickly. A boicunt's natural state is with a thick cock parked inside it. As he took her back side she looked into his eyes and cooed, "Oh Daddy pound my tight pink pussy! Make me your little sissy bitch! Own me! Drop your load in me but be careful. I don't want to get pregnant on my first time." Oh she was very cheeky. She had obviously been practicing what to say to a real man to make him hard as a diamond. He stiffened more if that was possible and sunk his pole in her hole and made it his own. When he climaxed and it popped out she had never felt so empty and so disappointed. Not to worry, it was filled many more times that night and most nights since then. She stayed all night and the next day. When she arrived home a few days later she was walking very funny. Vi laughed at her state. She was very familiar with it. She shared all the details while her father was out of the house. He didn't want to hear about his femboy daughter being savagely and beautifully fucked for the first time. Violet was a proud teacher and jumped for joy with her. Mandy was a natural cock pleaser! Other things that happened include Josie deciding to run for mayor. She won in a landslide. She had a real active street team that helped with fundraising and vote getting. They were real hands on. It helped that the squad had grown by a ton. Sissy femboys who were confused before suddenly felt comfortable being themselves. To say the girls bathroom became a fashion house is an understatement. There was forever a sissy fixing their makeup in the mirrors to impress the next hunky man that happened by. That doesn't mean it was all wine and roses. There were lots of catty fights over men being broken up all the time. The scratching and hair pulling was a daily occurrence. It's so silly. There are plenty of men for these little sissies to share. There was a revolving door to the janitor's closet with ladyboys getting their tight boicunts poked pretty constantly. There were lots of occurrences of sissies blowing a teacher or coach in a dark corner of the school or after class. The teacher's lounge was pretty off limits if you were not loving a sissy because it was often in use as a boudoir! Cali and Cami Cox were our first set of femboy twins. They became invaluable. Sissies are notoriously bad drivers. They're accustomed to the man being in charge and that includes doing all the driving. Cami was driving pretty poorly one night and got pulled over by the local Chief of Police who just happened to see her swerving. She was very embarrassed and he took pity on the poor crying little pouting sissy. She really played up the damsel in distress routine. Sissy are a natural at that. He let her sit in his squad car and calm down. She quickly pulled it together. She mostly calmed down by reaching over and extracting his cock from his pants and sinking her sweet mouth over it. He probably should have stopped her but she was just too talented and he blew his wad in the back of her throat. She licked her lips and said "Oooh Yum Officer Daddy!" He has been seen with her in his patrol car at least 10 times. At least it looks like her, it might be her sissy twin sister! There a rumors they both like to service his weapon sometimes at the same time! There was enough of a voting bloc in our group to easily hand the Homecoming Queen crown to our hand-picked representative. She represented the Math Club. We gave it to newly out femboy Elizabeth `Liz' Leak. She made a very lucky guy's dick leak after the ceremony, too. He's local car lot owner Seth Hardbody. She enjoyed putting her hands on a hardbody! We warned her not to get attached. There is plenty of dick for a hot little tranny to sample. I, of course, won the title of Prom Queen. Being leader or our band of the sissies has its advantages. I promised to pretend to be wholesome when I actually want a dick in my hole some or a lot really!! God I looked good that night. Rich welcomed his little femme queen into bed that night and I welcomed his thick rod into my sweet boi hole! He crowned me for sure! Becky Muffin eventually felt free enough to embrace her Sapphic lifestyle. She even reformed the defunct drill team with some other feminine girls who also leaned that way. 13 hot femme lesbos make up the Pink Roses. They were often seen at basketball and softball games along with their duties at the football games. There was a lot of late night intermingling at one of the pitcher's homes. Her 2 mommies invited the drill team in to help with massages for the team. All the Pink Roses usually attended. She made up with Coach Kutch and hoped to move in with her one day and be her wife. It did not last long though. Kutch is too much of a young lady coochie hound and she can't be faithful to Muffin's muff! Pretty stupid of her if you ask me. Becky found love eventually with one of her young lady friends on the golf team. That girl's mother was the Pink Rose sponsor. She also enjoyed the company of the hot young drill teamers. Ahhh, a happy ending! Aly found her forever man with City councilman Nick Von Deek. He was a football coach turned local politician. She loves the muscle-head type. He is kind of a moron but she seems happy. He'll eventually fuck up and she'll divorce him and take his money. She is a tease and sometime the mailman takes a long time to complete his route as stops to explore her sissy backside. After graduating from school there was a spate of sissy weddings. They are so damned fun to attend. Everyone gets laid. Jess married her band director and became a sissy stepmom. Her teenage son is always at her side. The squad will have a new member soon. He had real femboy potential. He'll be a really penis pleaser. I became Violet's stepmom. I am now Mrs. Cherry Rodman, respected but slutty sissy step mommy and housewife. My ex, Randy, attended the wedding and looked sad until Liz Leak sat in his lap. They disappeared soon after that. I owe her a big thank you! Violet became Mrs. Violet Driver and step mom to Mandy. Mandy became Mrs. Mandy Wanx a few years later. She is a very rich pampered house sissy! She sometimes had to invite the gardener in to help her with her plants. He's really just planting a penis in her sissy pussy hole. Aly became Alyson Von Deek and future very rich divorcee. Josie is the mayor. She and Hardman won't get married until she gets out of college and becomes at sissy psychologist. Cami and Cali have their very important cop boyfriend to keep happy. We control the school, the cops and city hall. This town is our own sissy oasis! We have enemies that think we wield too much power. We know that with great power comes great responsibility. Sissies are bullied from an early age and we've learned from that. Just because jealous losers call us the Mean Gurls doesn't really mean we are mean. We can have a very vindictive side though. We treat everyone with kindness and respect until we are crossed and then the femboy fingernails come out and start clawing! We are always very careful with those claws though, No sissy wants a snag in their silky pantyhose unless caused by a strong dominant man! As always, the Sissy Squad abides. Xoxo Cherry and the always growing Sissy Squad