sissyboy-dressup-2

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Subject: Sissyboy Dressup Two (gay adult-youth) Sissyboy Dressup Two (gay adult-youth) By Beautiful Creamer I don’t do this stuff and you shouldn’t either. What you should do is contribute to fty. One � Free at Last You probably think that the life of a former super model for “Sissy Boy” magazine’s spinoff smash hit, “Sissy Boy Lingerie” would be leading a glamorous life. A life of dawn-to-dawn lust. Of men circling his delicious body for an opportuty to breathe the same air as the beautiful, young lovely. A life of all the ball-detonating sex anyone could ever conjure up in the filthiest recesses of the mind. A life where all he must do is nod and any man with a palpitating testicle would do his bidding. And you would be almost 100 percent right. Let’s say 95 percent because not everyone is rational. My name is Kelly Sweetlove (not my birth name, but so what?) and I’m living that life. And loving it. Three months ago, when I was age 12 and two months, my boss, Biff Buggerall, the editor, publisher and supreme overlord of “Sissy Boy” magazine and Sissy Boy Enterprises, gave me the bad news. Despite my stunng career at the “Sissy Boy” family of publications, I was too old for further “pictorials.” I was crushed. I KNEW I was still young-looking and incredibly beautiful and sexy, and Mr. Buggerall agreed with all that. But… “It’s not me, it’s the readers, Honey,” Mr. Buggerall said. “They’ve been spilling sperm over you since you first posed four years ago with your panties down and your little pes up in `Sissy Boy Eight’ [a magazine for `connoisseurs’ of the beauty of younger models]. “Since then, you’ve been our go-to model, even when you drifted into wearing lingerie and female clothing in your real life. But looking at the big picture, readers are always looking for `up-and-cummers’ in our business. You’ve had your four-year run in `Sissy Boy.’ Now your real fun begins.” By that time I was crying desperate tears. Sobbing bitterly. I had thought my huge fame and stupefying fortune that the very generous Mr. Buggerall had amassed for me would never end. Yet, it ended. Wait. What did Mr. Buggerall mean about “Now your real fun begins?” Mr. Buggerall smiled. “We’re not just setting you adrift, my darling. Oh no. You’ve made me millions upon millions of dollars and I am very grateful. I have big plans for you if you accept them.” My tears had already begun to dry. “Like what, Mr. Buggerall?” I asked. “Kelly, you’re already richer than you know. I know you think you made one million dollars per year working for me. The sad part of that was that your greedy parents confiscated almost all of that. The truth is, I was holding back the bulk of your earngs until I could get you liberated. Liberated? What did he mean? “My legal guys went to work and fixed it so that you are a liberated minor. You are no longer the wage slave of your parents. Nor are you subject to their control in any way. Plus, you now have $44.7 million, your fair share of what you earned for me, in savings.” He let that sink in. It sank. No more working for nothing. No more servant to my greedy parents. I threw myself into Mr. Buggerall’s arms to thank him. Then I dropped my panties and let him fuck me. Twice. It was a very emotional moment. Actually, two very emotional moments what with the second fuck and all. When our balls were sufficiently drained, I asked for details. “We have a luxury condo complex here in town, Kelly. Complete security. Total maid and concierge service. You won’t have to do anything but go to school, look pretty, entertain men and boys of your choosing and, whenever you want, date some men that I suggest you date. Subject to your approval, of course.” Oh. A stabbin’ cabin of my own. Where I can be the girlish boy I want to be. I was fainting with happiness. Or maybe I was just sleepy from two slam-bang fucks. Anyway, I wasn’t worried in the least about the notion that Mr. Buggerall would be sending some men my way for a good fucking. I like fucking. And I like men. I was rich. And independent. Life couldn’t be better. Or could it? Two � Sissyboy Life It was so cool to have my own place. Far away from my parents, who loved me the way they would love an ATM in their living room. Well. That was over. Mr. Buggerall showed me around my new place with obvious pride. By obvious, I mean he was fiercely erect the whole time he gave me the guided tour. A lovely, modern kitchen filled with healthy, figure-friendly food. A living room the exact right size for entertaing a maximum of three guests. [I had no intention of having a bunch of my so-immature schoolmates partying in my home, touching my things, breaking my things.] A fabulous bedroom, of course, with a mammoth bed and vats of Slickyboy Masturbation Cream (a Spermbutt Industries Product) and Spermbutt Anal Lubricant. But the best part was the three massive, walk-in closets, already half-filled with girlish lingerie, dresses and shoes! And a carte blanche at Sissy Boy World to fill the other half. Not to mention a small dresser with boy clothes. I mean it. I’m sorry I mentioned it. But my all-boys school has a uform that I must wear. Oh well. I was so overcome with gratitude for Mr. Buggerall, again, that, well, you know what happened. Mr. Buggerall was such a dear. He didn’t want me to be all alone my first ght as a liberated minor, so he slept with me. We didn’t actually sleep very much, but it was a great ght anyway. Mr. Buggerall even made me breakfast, since it was my first schoolday as a liberated minor. I wanted to wear a miskirt with stockings and big heels, but he talked me off that ledge. “You’re a grown-up now, Kelly,” my wise bumfucker said. “Don’t call unnecessary attention to yourself.” He was right, of course. Grudgingly, I put on my Slickbutz Academy uform. It wasn’t exactly the standard outfit for Slickbutzers. We 15 declared sissyboys at the academy wore a modified version. Anyone who wondered if I was a cock-hungry, panty-wearing sissy need look no further than my almost skin-tight, tiny short shorts that went with my standard knee socks, clunky shoes, white shirt, school tie and school blazer. It’s good advertising. Lots of my 14 schoolmate, fellow sissyboys have gotten some amazing hookups while wearing that outfit. Not me so much. I’m known in school to be in a league of my own. And not just because of my 23 pictorials in the “Sissy Boy” family of fine periodicals. Each of which has produced a medium-sized lake of sperm from men around the world. Most men and boys think that international popularity makes me unapproachable by my schoolmates, teachers and fellow citizens of my town. Not true at all. I like sex. I like men. And, occasionally, some boys. And I like variety. So when the occasional classmate or teacher walks up to me and makes a lewd suggestion, I usually ask, “Your place or mine?” Now that I have a place. Mr. Shagwell, my school’s headmaster, is special. Mr. Shagwell was the man who introduced me to my fabulous new life four years ago. I had just turned eight years old and was beginng the third grade. Already men were sizing me up as fodder for their masturbatory fantasies, but I hadn’t noticed. Thank goodness Mr. Shagwell noticed me. Three � A Star is Recruited On the fourth day of third grade, I got home from school, had my milk and cookies from Mom and carried my book bag upstairs to my room. I was planng on changing from my school uform into my play clothes when I noticed the corner of something unusual sticking out of my bookbag. I pulled it out and recoiled in amazement. It was a magazine. Not just any magazine. A magazine with a naked boy around my age on the cover! The boy was smiling at the camera. He was a very pretty, young boy. But his face was all smeary with something creamy. There was a caption that said, “Thanks, Daddy! That was a big one. I think you needed that. I know I did.” The magazine was called “Sissy Boy Eight: for Connoisseurs of Lovely Younger Boys.” I didn’t know what a connoisseur was. But I knew what naked was. And that boy was starkers! With a little pes around my size at the time. It was skinned and the head was red. Like mine got sometimes when I looked at certain men on TV or around town. I was terrified. If my mother or father saw that filthy filth, I would be exiled to some filthy island with filthy people. And who dared to give me that magazine? Did they think I was some little sissy who liked being naked? I was so frightened that I almost didn’t open the book. But I did. And saw lots of naked or near naked boys saying all sorts of odd things. One naked, little angel was bent over playing Twister. His heie hole was pointed right at the camera so that all the men who paid $39.99 for the book could see his pinkness. Another young beauty had pointed his bum at the camera and was looking back over his shoulder. His bumhole was shiny, like it had been greased or something. The boy looked a little scared and the caption read, “Your finger felt so good in there, Mr. Hotness. But I’m scared about you putting THAT in me.” And another had the boy standing, facing the camera. He had skinned back his knob and was pointing his pes north saying, “Do you really think my pee pee is beautiful Mr. Bigrod?” Yet another, even filthier, had a beautiful boy pointing his bum at the camera, looking back over his shoulder and looking worried. Looking at his bumhole, it was clear why. His hole was WIDE open! And it was oozing that same creamy stuff that the cover boy had on his face. The boy’s caption said, “Are you SURE my bottom will close up again so I can poop, Daddy?” Daddy?!!?! That little doll was doing nasty naked stuff with his Daddy?!?!? Filth! Disgusting. So why was I convulsed with something I had never felt before? Was I dying? No. It was my very first dry orgasm. Though I didn’t know such things existed. I was AROUSED by what I saw. I was captivated at the notion of being naked with the unseen men in the magazine. And I knew one solid fact for sure. I was prettier than any of the boys in the entire, 100-page periodical. Someone wanted me to reach that conclusion. Was it Daddy? No. Daddy wasn’t smart enough for such things. And too pussy-whipped by Mom. There was one other strong possibility. I pursued that lead the next day in school. Fifteen minutes before classes started, I stopped by the headmaster’s office and escort asked to speak with Mr. Shagwell. The man practically flew out of his office when he heard my voice. He ushered me in, closed and locked the door and asked, “How may I help you, Kelly?” I reached into my bookbag, extracted the “Sissy Boy Eight” and said, “I believe this is yours.” I loved watching Mr. Shagwell sweat. Did he admit it and risk incarceration? Did he deny it and risk celibacy? An incarceration threat was worth it for a chance to be sexual with me. “Yes it is, Kelly. Thank you for returng it. Did you enjoy reading it?” The ball was back in my court. I volleyed. “I enjoyed it very much, sir,” I said as I dropped my regulation uform shorts, then my underpants. Mr. Shagwell smiled broadly. And joined me in below-the-waist nudity. Oh dear. I was eight years old and halfway nude with my halfway nude headmaster. Then I was eight years old and fully nude with my fully nude headmaster. And so it began. Mr. Shagwell was quivering as he drew me to his naked body. I felt his chest hair as he hugged me and picked me up by the bum cheeks. And then he kissed me. My first kiss. I love kissing. Mr. Shagwell was a great kisser. And an even better hugger. Especially with my teeny peeny rubbing on his chest hair. In that position, I had no access to his pes, which I had only glanced. But at eight years old, I figured there was no hurry. Soon enough I would see Mr. Shagwell’s prick and many others. OK. So maybe the man was a perv. Me being eight and all. But no one held a gun to my head. The only thing he held to my head was his pes when he stayed standing and had me get onto my knees. Giving me a really good, closeup view of the first man’s pes I had seen. It was and is a beauty. I’m just an airhead sissy, not good at math. So I don’t know how many inches it is. But it’s big. And even then, I knew he expected me to kiss it. So I did. It was leaking some really ce clear stuff, which I licked up greedily. Yum. Was that the stuff the magazine cover boy had on his face? I didn’t think so. Remember, I hadn’t even had sex education in school yet. So it was all a mystery to me. I did know that when Daddy gave me a bath, he would pull back my foreskin to wash my knob, the exposed part felt really good when he rubbed a soapy washcloth over it. So I skinned him back and started laying soft kisses on the tender parts. See. I was a natural. Even then. Mr. Shagwell sure thought so. I guess he felt rushed, what with me needing to be in class in seven minutes. So he didn’t hold his spunk back at all. Maybe I was just that exciting [giggle], but wow did he shoot early and often. Nine mammoth spurts! I wasn’t even familiar with what a man’s orgasm looked like, let alone know that I was supposed to swallow it. So he kind of deluged my face and hair with it. Good thing I was nude. And had short hair. Otherwise, getting cleaned up and to class on time would have been impossible. As it was, I barely made it. Actually, barely is the right word. Dressing hastily, I left my white cotton underpants in Mr. Shagwell’s office. When I saw him after school for a more thorough, less rushed anatomy lesson, he refused to return the undies. “An angel like you should be wearing panties, Sweetie. These look like your size.” He handed me seven pairs. Where did they come from? Oh well. I slid a pair of pink biki dazzlers on and I was hooked. Never wore boy’s undies again. Which meant I would have some splain’ to do to Mom, my laundress. Turns out, no explanations were necessary. By the time I got home after Mr. Shagwell and I had exchanged after-school fellatio delights, Mom was sitting in our living room pouring Mr. Buggerall a third cup of coffee. It turned out that Mr. Shagwell was one of Mr. Buggerall’s “talent scouts.” He had picked me out three weeks earlier and arranged for Mr. Buggerall to stalk me a little. Then it was time for Mr. Shagwell to do a field test to see if I liked men and was willing to help men satisfy their filthiest urges. No one was surprised that I was highly qualified. So, I discovered that Mr. Shagwell didn’t really love me. He just wanted to see if I was willing to be in Mr. Buggerall’s underage, incestuous, homosexual enterprises. Which was more than fine with me. It was also fine with Mom, who had already deposited my $500,000 “signg bonus” in her savings account. And so it began. I was pretty nervous at my first photo session. The photographer was very gentle with me, telling me not to be afraid of being nude for the photos. I would be doing the men of the world a great service by sharing my beauty. It was all very tasteful. Not filthy at all. I wasn’t really afraid of being nude in front of a man who was going to share my beauty with legions of connoisseurs. I guess I was nervous about the fact that I was only going to have one photo in the next “Sissy Boy Eight.” It was make or break and I wanted make. So that darned photographer had better be a good one. I began to relax when I lowered my panties and stood nude before the man. He gasped. I like when men gasp. So I knew he would do a good job for me. The picture Mr. Buggerall selected from that first photo session was one where I was standing next to a big bed with white, crispy sheets. I’m looking at the camera with my blue eyes. My expression is one of total innocence mixed with curiosity. My pes is stiff and standing straight up. I’ve pulled back the foreskin all the way, exposing my deep-pink knoblet. The caption Mr. Buggerall added in the magazine was “You’re right, Daddy. It feels really good to pull the skin back and forth.” The picture was on page 32 of the May issue. Within microseconds of it hitting the mail deliveries and the newsstands, Sissy Boy Enterprises’ email server blew up. “Who is that angel on page 32?” “The page 32 babydoll is the cutest you’ve ever shown us. More!!” “I want to marry the babe on page 32.” They liked me. They really liked me. So much so that Mr. Buggerall changed his policy regarding single shots only for “Sissy Boy Eight.” I was going to be the subject of the next issue’s first complete pictorial. A fact that was emailed to all of the 96,439 emailers who wanted more of me. The next issue had seven printings. And made Mr. Buggerall about $50 million in profit. My pictorial (a classic!) began with me taking a bath. Undressing. Bending over for various tasks � thereby “showing pink” for the first time. Washing all my parts, especially the good stuff. I dried off and padded into my bedroom, where I put on, for the first time, a pink, wispy, transparent, tiny ghtie that didn’t seem to have its matching panties available. I lay on my back, opened my legs, lifted and spread my knees, showing my heie hole, my stiffie and my pink purse. The caption said only, “I’m ready, Mister.” Just that. The nation’s economic numbers sagged that next month. Men were staying home to wank to my pictorial instead of going to work. OK. Maybe that’s an exaggeration. But I was a huge hit with the connoisseurs. And an even bigger hit with the man making all the money from me. Four � Back to Age 12 I was NOT washed up at age 12! I was NOT! I was rich. I was independent. And the great majority of men would still want to fuck me. The danger was that I would try to overcompensate and do dumb stuff to prove I wasn’t washed up. Hey. I’m an international fuck star. I don’t do dumb. Usually. I loved all the stares and wolf whistles I got at school that first day of my freedom. It felt so different knowing that I wouldn’t have to go “home” and be with people who robbed me of 95 percent of what I earned in four years. It was a good feeling. Mostly. Those robbers were my Mom and Daddy, after all. And I had never really lived alone. In a place by myself. Solo. Mr. Buggerall had been kind enough to stay with me the ght before, but I know that being an international billionaire philanthropist is a busy life. Especially when he’s scheduled to “interview” three boys for upcoming pictorials in “Sissy Boy Nine.” That’s a publication for, you know, connoisseurs of the male form at age ne. It’s different from “Sissy Boy Eight” in that it shows men plowing the ne-year-old boys’ bottoms and cumming in their faces and mouths. Tastefully. So I guessed I would be staying by myself that afternoon and ght after school. Hmm. Mr. Buggerall had been kind enough to provide me with a crew of four drivers/bodyguards, who were with me in shifts around the clock. “They’ll also fuck you if you want, Honey,” my billionaire benefactor told me. Fucking one’s chauffer on the first free ght seemed a bit low-class to me. As well as desperate. So after second-shift Harry drove me home and saw me to my door, I gave him a ce kiss and went into my new place alone. First order of business was to get out of those awful boy’s clothes that I rarely wore any more. No, wait. First order of business was to set up a date for that eveng. I addressed my phone and asked for a random contact. Hmmmm. Mr. Pleaselad. Thank you, Fate. I called. He answered on the first half ring. He was hyperventilating when I gave him the address and asked him to stay overght. “Please be here in exactly 90 minutes, Mr. Pleaselad,” I asked sweetly. He would be. No doubt. I alerted Harry about Mr. Pleaselad so the man wouldn’t be shot or something. Then I stripped nude and took a quick shower. Drying off, I sat at my large vaty in the nude and did my face. I love how cosmetics make me look. Prettier than any two-pussy girl. When I had reached uverse-class beauty, I sissied into my lingerie closet and selected a lovely, all-pink set: seamed, fully-fashioned, reinforced-heel-and-toe stockings; garter belt; see-through, floor-length peignoir; strappy sandals with a four-inch stiletto heel. No panties. No bra. Thank goodness Mr. Buggerall had made sure there was a defibrillator in the bedroom. Maybe I would even learn to use it. Oh well. My bodyguards probably did. It was a good thing I hurried getting ready because I barely had 17 minutes of self-admiration-in-a-mirror time. Anything less than 15 minutes is unacceptable. Take that, you fickle “Sissy Boy” readers. Let’s see if that fresh talent Mr. Buggerall says you want could top that. Oh! The bell rang. It was Mr. Pleaselad! Smiling like a crazy person and panting with lust. He and I had met at a basketball game izmit escort bayan at my school and we had fucked three ghts since then. Though not in the past 22 days. Had he been staring at his phone waiting for me to call all that time? Probably. [Giggle] “You’re spectacular, Kelly!” the man bellowed. I get that a lot. He stepped right into me, kicking the door closed with his foot as he kissed me and told me how much he missed me. Giving me just enough praise and joy without sounding needy. I don’t like needy. When we got past the greeting kisses, Mr. Pleaselad looked around a bit. “This is a lovely place you have here, Kelly. I was so happy to hear that you’re a liberated minor now. Do you like that?” I liked that Mr. Pleaselad seemed interested in me. Not just interested in fucking me. We chatted a little as I led him to the bedroom. The situation demanded action, not talk. I hadn’t cum in over ne hours! Mr. Pleaselad and I still chatted as he stripped nude, leaving his clothes in a neat pile. Then he sat on the right side of my two-seater loveseat. Aptly named for our intentions. I slid off my peignoir and sat on his hairy lap. His delighted prick stood tall against my right thigh as we kissed and cuddled. Mr. Pleaselad is a very good kisser. And an even better pple-worshipper. It was all coming back to me. That was why I liked Mr. Pleaselad so much. He does pples better than anyone. I’m not sure if my pples are so big and puffy because of genetics or because of the countless hours adoring man have suckled on them. No matter. They’re spectacular. And those pples, along with my makeup skills and insistence on wearing lingerie to make love are a big part of why a good hunk of the hunks love me. I keep their little heterosexual consciences clean. It’s not homo to sleep with me and do all the non-sleeping things one can do. I’m not really a gay boy giving it up for a pervy gay man. No. They look at my femmed-up beauty as they fuck me and say, “What I beautiful girl I’m fucking! I am a major hetero stud.” Or something like that. Am I offended? No way. It expands my possibilities greatly. Giving me access to the men who think they’re hetero. The kind I like best. And, it’s a role I can play until my 60s or 70s, as opposed to sissyboyhood. The prime of which I had just discovered ends at age twelve years, two months and two days. Plus, if my men are sleeping better with clear consciences, they’re better at fucking me. Anyway, Mr. Pleaselad had me in quite a dither from his excellent pple sucking, but I needed to cum. So I gasped out, “I need to cum.” My attentive lover had me stand in front of him in my stockings, garters and big heels. I fed him my cock. Whimpering with delight as I felt his tongue engage my glans. Oh! Had Mr. Pleaselad been practicing fellatio since we met last? I thought so. He was VERY good. And I was VERY needy. It occurred to me that, now that I had my own place, I could scream out my orgasmic appreciation much more loudly than I could when I was living with the embezzlers. So I did! And I wasn’t faking. Mr. Pleaselad had brought on a delicious cum. He’s such a dear. And so oral! I pelted him with kisses, then invited him to lie on the bed on his back. “I know you enjoyed that little appetizer, Mr. Pleaselad,” I said, “so how about your favorite meal?” The man smiled broadly. I love making men happy. So I straddled his shoulders, facing his feet, and lowered my bumhole onto his adoring lips. And tongue!!! Oh my! My manfriend had been PRACTICING! His tongue almost gutted me. It was so delightful that I almost omitted the unselfish part. As Mr. Pleaselad was feasting on my nether regions, I bent forward and took his hard, leaking cockhead into my mouth. I love sex. Don’t you? As I listened to our mixed grunts of sexual pleasure, I recalled more about my spectacular career as a sissyboy super model. That first pictorial I did for “Sissy Boy Eight” really shaped the rest of my career, let alone my life. I still don’t know where the photographer got the inspiration to have me put on that tiny, wispy, pink ghtie, but it was a life-changer. I felt…pretty. Really pretty. Not femine exactly. More like a femmy boy. I could see the effect it had on my photographer. His erection was ripping his pants. He used two rolls of film photographing me in the ghtie, on my back, legs spread. Then, unable to resist, he dove in to eat my little pucker until I screamed with erotic agony. Two times. Then he used three rolls of film photographing me in the same pose. Guess which session made it to the magazine. The one bummer with “Sissy Boy Eight” was that no men were allowed to be portrayed touching the boys in the photos in the book. And Mr. Buggerall didn’t allow any real-life fucking of the boys either. Including himself. Which was very difficult for him, I know. You see, Mr. Buggerall is a man with morals. He believes that an eight-year-old boy is too young to fuck. Which is admirable, right? Mr. Buggerall fucked me on my nth birthday. My first time. And second. And third. Needless to say, I liked it. I think he was only able to manage that third time because a) I was so pretty b) I was so sexy c) I was an anal virgin and d) because of the lingerie I was wearing when I seduced him. Or he seduced me. Does it matter? Anyway, I was all in white: stockings, garters, bra, big heels, and a tiny, flyaway ghtie. Like a bride almost. And perhaps the last hetero corpuscle in Mr. Buggerall’s blood was urging him to fuck my beautiful, femmy bum. So lingerie became my signature item. Readers of “Sissy Boy Nine” clamored for me in lingerie when I appeared in my first pictorial there: “Kelly and his schoolmate.” They matched me with last year’s ne-year-old up-and-cummer, a kid named William. The premise was that I brought William home from school with me, took him to my room and he watched me lingerie up as foreplay. When I was all dressed, we rolled around, kissing and sucking, but neither of us could cum. It was still a hit, but not up to my usual blockbusters. Mr. Buggerall made a course correction for the next pictorial. A high school seor named Marco took the fully-lingeried me to his bed and fucked me silly. Cum everywhere! It was delicious. Even though it was a tiny bit hokey. We actually filmed everything over four days so that Marco would have maximum cummage for the photos. I liked Marco. He and I were an item for like ten days after that. The last day of our torrid little affaire was the day our pictorial hit the newsstands. Suddenly, I was an international sex star. I was OK with that, but Marco couldn’t accept my success over his. Dumb ass. I would have stayed with him at least another week. For my third pictorial for “Sissy Boy Nine,” Mr. Buggerall set me up with a hairy, buff, cely-cocked beau named Beau. Beau was AMAZING! My heie was sore the entire time I knew him. A good sore. And we were swimming in sperm throughout the pictorial. That was when Mr. Buggerall gave me a full-time set of bodyguards. To protect me, but to protect his investment too. Men were giving blood to get money to buy the magazines I graced. Which made it more difficult for them to get erections, I guess. Oh well. My age-ne year went by in a spermy whirlwind and before I knew it, I was ten and eligible for the mainstream publications. I was soon quadrupling sales of “Sissy Boy Lingerie” every time my beauty graced its pages. Oh my! I learned how to use cosmetics to send my beauty to the stratosphere. I perfected my walk in five-inch, stiletto pumps. And this is the big one, I started to SPUNK! It happened when 32-year-old stud Patrick and I were posing for a pictorial where he takes me out on a dinner date then takes me to his apartment, strips me to my lingerie and fucks me. Trite, maybe. If anyone besides me had done it. As Patrick lay on his back, I gave him a long, slow, pes and testicle massage with LoveOil and Slickyboy Masturbation Cream. The look of agony on his face and the puckish look on mine drove the readers wild. Then, when he defied me by not cumming yet, I oiled up my body from belly button to thighs, straddled his hips, and rubbed my oily balls and “taint” along his tortured cockhead. That was the end of Stud Patrick’s first of that day. Messy messy. Thank goodness he had more. Being a ce man, Patrick decided to satisfy me the same way. He had me lie on my back as he oiled my cock and balls erotically. He rubbed. Stopped to bend over and kiss me. Yum! He rubbed some more. Then it began to happen. A rumbling “down there.” Not like the previous rumblings. Was I about to cum wet? Cum for real? Like a big sissyboy? Wait. Did the guys in the crew have their cameras ready? Was I being filmed? I didn’t want history to miss this. It was so different than the… Oh! I’d like to say it was a geyser. It was more like a trickle. But it was 100 percent, gen-u-ine, U.S.-inspected sperm and semen. My first. And a life-altering experience. This was why men wanted me. So they could feel this, I thought. Well, the men were pretty darned smart. Everyone would want THAT to happen. Like a proper sissyboy, I began to cry. Happy tears? Yes. Tears for lost innocence? Defitely not. I wanted to get rid of my innocence as fast as possible. Patrick made me spunk two more times that day. And I rewarded him by carrying on a mostly exclusive love affair with him for nearly a month. After all, there were lots of other men who needed my comfort. And I sure comforted them during my last previous years of spectacularly spunky Sissy Boy stardom. Five � Casual Day I asked Mr. Pleaselad to leave early the next morng � 7 a.m. He was a little disappointed, but the poor man was so exhausted I feared for his health. Anyway, it would take me longer to get ready for school that morng because Mr. Shagwell had instituted a new policy. One day a week would be no-uforms day. That didn’t mean jeans or any other sloppiness, he told the students. He needn’t worry about me. I was dressing up for sure. It took a little longer in the shower that morng because Mr. Pleaselad’s cum seemed to be on most surfaces of my body. Especially my hair. But I was resourceful and emerged clean and ready to soup up casual day to the best of my ability. First stop was my lingerie closet. Seamed, fully-fashioned stockings were hanging izmit sınırsız escort from a display, creating a forest of femity. Black today? No. Too grownup. Too “fuck-me now.” I decided to save the black stockings for my dates. Tan would do the trick. Perhaps a darker tan. Ah. There. There are few non-fucking sensual pleasures like putting on a pair of sheer stockings over shaved legs. I quivered as I put them on. Thinking of the effect I would be having on a herd of male humans that day. As I snapped on my garters, I considered a proper reward for Mr. Shagwell for his implementation of casual day. He knew I would love it. So he must have done it for me. Men seem to do things for me. Should I just give him an hour’s worth of me in his office at lunch time? Or should I invite him for an overghter that very day? Aren’t my set of choices awesome? I slid into a tiny, black miskirt, then a white blouse. I selected black, four-inch-stiletto, patent-leather pumps for that day. Then I set to work on my cosmetics. When I had transformed my face to match my lovely body, I made myself a pop tart, grabbed my bookbag and headed downstairs to meet Peter, my morng-shift bodyguard/driver. We arrived at school ten minutes later and my moment was at hand. Peter opened my car door, I looked out to see at least 30 of my male schoolmates staring at the car. I slid one long, sexy, stockinged-and-heeled leg out of the car. The gasp was audible in the downtown area five miles away. The second leg was met by whoops and whistles. I stepped out, looked left and right, gave Peter a long, tonguey, thank-you kiss goodbye. Then I wiggled my way into school. So. All the boys and men at my school no longer needed to feel “homo” when they looked at my hot ass in my tiny school shorts. Dressed as I was, they were free to think about sucking my cock and fucking my bum without gay guilt. I hoped that Mr. Shagwell was ready with riot police. I prickteased all the way to my locker, then turned to see two other girls. That was odd. The school was all boys. Except for me on casual day, of course. But there were two girls just leaving their lockers. One was dressed in a white blouse with a peter pan collar; a pink cardigan; a modest, knee-length, pink-plaid skirt; white knee socks; and penny loafers. With penes in them. The other almost out sluttied me. She was wearing a micro-mi-skirt and big heels. Who? What? When? Where? How? Oh! The “girls” were actually two of the 15 openly sissy sissyboys in our school. Like me, they saw casual day as an opportuty to dress up and drive home the point that we liked our own gender, thank you. Although, Miss Pink Cardigan seemed a bit timid about it. Who were they? I found out quickly, since they made a beeline for me. “Oh, Miss Kelly,” they said, “thank you for showing us how to be brave.” Holy Bruce Jenner! Was I a role model? Didn’t see that coming. Anyway, as the day went on, I spotted two more femmed up sissyboys -so five of 15 took the plunge. And none of us were devoured whole by our ravenous classmates or teachers. As far as I knew. At lunchtime, I went with my first instinct and made Mr. Shagwell happy that he had been born a man by sharing myself with him for a lovely hour. By the end of the day, I had asked my four dress-up “sisters” to come to my place for some afternoon fun. The schoolmate who had almost out sluttied me had to decline. An afternoon with Mr. Shagwell was scheduled for that lucky sissy. Franco, my bodyguard that afternoon, was surprised when I piled three femmed-up sissies in the back seat. I had told Franco once that I wasn’t expecting to bring schoolmates home. Franco seemed a bit disappointed. Not that I had changed my mind. But he was disappointed that four sissyboys would be conveng in my condo and he wouldn’t be invited. There was a lot of oohing and aahing when the sissyboys walked into my home. And even more oohing and aahing when I stripped to my garters, stockings, bra and heels. I invited them to do the same. They all did so, including “Pink Cardigan,” who was embarrassed to be in a girlish undershirt, white, cotton panties, and knee socks. His name was “Leslie.” After showing my other two schoolmates where my bed was and inviting them to have fun, I held Leslie’s his hand in mine and led him to my closet. Oh! The little dear was gasping for breath. Fearing self-asphyxiation, I gave him a pair of black stockings with garter belt, a black bra and a pair of black, patent-leather pumps. Miraculously, everything fit. Even more miraculously, shy little Leslie was transformed by his image in one of my condo’s eleven full-length mirrors. For the first time, he spoke to me without being asked: “Oh, Miss Kelly! Thank you so much for your kindnesses today. You’re my idol. I want to be a `Sissy Boy’ star like you. I want men to ADORE me the way men adore you!” “Well, Honey, you certainly are pretty. How old are you?” Leslie blushed. “I’m almost ten and a half!” Which for some reason the young beauty followed with a sob. “What’s the matter, Sweetie?” I asked empathetically. {Since I was liberated, I figured I should be more empathetic, you know.] He sobbed again. “Oh, Miss Kelly. I’m too old. Over the hill.” Well. He was right in some ways. Mr. Buggerall wanted to meet his superstars when they were almost eight. But Leslie had potential. “I you apunking yet, Honey?” I asked him. “I started two weeks ago, Miss Kelly. I can show you if like.” We were certainly moving in that direction that lovely afternoon. But I said, “In a bit, Baby. Tell me, why were you wearing that 1965-Catholic-schoolgirl-on-a-supervised-by-a-nun-in-full-habit-date outfit to school?” Now Leslie was showing real tears. “I told Mommy that I looked dumb in that, but she insisted. She wants me to be in “Sissy Boy” too, but she said it would draw the right kind of attention.” She was right about that. Leslie’s dowdiness made me want to slut him up a bit. A big bit. And the contrast between 1965 Leslie and 21st Century Leslie was an eyecatcher. “I can certainly put in a good word for you with Mr. Buggerall. But you’ll have to fuck him. Are you OK with that?” He looked stunned. “Biff Buggerall!??!? You know Biff Buggerall?!?!? And you would get me a fuck interview with him? Oh, Miss Kelly! How can I ever thank you?” The answer to that question appeared to us both simultaneously. I don’t have a lot of sex with other sissyboys. But Leslie was a peach. And it was time to take a big, juicy bite. Now remember. I was wearing the dark tan stockings and white garter belt. Leslie was all in black. I led Leslie to my bed and we found it occupied by the other two dressup sissyboys named Jamie and Tracey. Jamie, the sluttier of the two, was lying on his back as a kneeling Tracey did an awfully good slurpy job on Jamie’s cock. Ignoring them, since the huge bed made that possible, Leslie and I fell in together, tongue kissing and rubbing bodies together. Cocks were involved. I slid down to take Leslie’s pes into my wet mouth to verify claims of spurting and …wouldn’t you know it?…Leslie was telling the truth. Six juicy ropes of boy’s cream, fresh from the dangling dairy. Yum! What a lovely afternoon we were having already. And I hadn’t even cum yet. Leslie’s eyes were flooded with tears of gratitude. His idol had just sucked him off. How often does that happen? He looked so pretty and randy and grateful and vulnerable that a strange notion grabbed my testicles. I wanted to FUCK Leslie. For the first time, I wanted to be the TOP! He was just so darned submissive. I could feel his emotions begging me to stick my peener in his bum. This was all new to me. I had always been the one giving it up. That was who I was. Wasn’t it? But I was liberated. And older. Too old, my former fans said, to take me seriously as their wettest fuck dream any more. I knew I would NEVER try to top a man. But Leslie was a boy. A young boy. Old enough to spunk. But just barely. And oh! He wanted me to fuck him. Know how I knew? He grabbed me around the shoulders, pulled me toward himself and whispered in my ear, “Please fuck me, Miss Kelly. I want you to. And I know you want to.” He was taking a big chance. I could have said, “This concludes this afternoon’s tour. Please gather your things and move toward the exits. Thank you and drive carefully.” But I did say, “Unnnh!” And I kissed the little twinkie with all the lipsticked sexiness I could. The eager fuck-needer grabbed for the nearby bottle of Spermbutt Anal Lubricant, pumped it all over his right hand and fingers and lubed his own bum as I stared in awe. He then drenched my stiffie with Spermbutt Anal Lubricant, lay on his back and positioned his hips for maximum fuckage. Wow! Who turns down an offer like that? Not me. I lined up my shot and missed. Jitters. Unfamiliarity. Probably. Leslie grabbed my cock and aimed at the peehole properly. I pushed. Zowie! So that was what it felt like! No wonder men turned into rutting beasts when they were doing that. It felt fantastic. Even better when Leslie’s lubed fingers found my bumhole as I fucked him. Everyone needs new perspectives now and then, don’t you think? Like a liberal watching Hanty for a week or a conservative watching Maddow. This was better than either of those. The kid could fuck. And so, it seems, could I. He even screamed when he shot his creamies. Which, for the only time in my life thus far, made me feel just a smidgie bit macho. The macho dissipated when I gave out my own girlie squeal as I filled his bum with Kelly Cream. Just to make sure we did that right, we did it again. One of the many advantages of youth is that it is often possible to stay hard enough after an orgasm that one could stay immersed and get on with Round Two. I took advantage of that advantage. At 6 p.m., my bodyguard Kevin interrupted us to say that there was an APB out for the three boys in my bed. Not one of them had had the good sense to tell their mothers they were going to a liberated minor’s house to fuck and suck all afternoon. Kevin said he would take them home and deal with it all. I thanked him and said that when he returned, my body would need some close guarding all ght. He liked that. And so did I. [I’m ending this here because a) I don’t know where to go with it without being repetitive b) the space aliens who dictate these stories to my brain have ceased transmitting on this one c) I’m eager to move on to another story d) my fingers hurt from typing e) I’m lazy. At least two of these are true. B for sure. And at least one more.] Please tell me what you think at ail.

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