by Gingerfred Man
A Pantyboy Profile
"Call me Cheryl"
See, I'm not some dumb pantyboy. I know my literature. "Call me Ishmael" was the opening line in "Moby Dick." Which, by the way was a HUGE disappointment to me. I mean I only had to read like a page or two of that million-page novel before I figured out that it was NOT about what the title implied. I thought it was about big "man parts." You know, as in, "Wow, Baby, your dick is MOBY!" But it was about whales and stuff.
Anyway, I'm a pantyboy. And a pretty smart one. So smart that my three pouffy roommates gave me the responsibility of telling all of our life stories. Our lives so far, I mean. We're only in our twenties, so we've got a lot of living to do. I told you about Amy in "Service," Judy in "Test Driven" and Sandy in "Sissy Stepmother." Now, you lucky reader, you get to read about me.
Chapter One What's the Rush?
It's no wonder that the Baby Boomer generation has been so uptight. They're always in a rush to move the big events of their lives along. They graduated from college in four years! Can you believe that? Four years? Then, a lot of them actually left home!! At age 21!! Some even got married. In their twenties!!! And had children before they were in their late thirties or forties. Is that ridiculous or what?
When I graduated from high school, my name was Charlie LaFemme and I was a slacker. In fact, I'm still proud to call myself a slacker. My two older brothers, Scott and Joey set a standard I was eager to emulate. Especially Scott.
Scott graduated from high school at age 18 and immediately set the LaFemme family standard by declaring that he was taking a year to "find himself" before he went to college. I was only five at the time, but even then, I realized that I was observing something important.
After Scott's year of getting up at noon, eating heartily from Mom and Dad's bountiful table, hanging out with his friends, especially several babes, staying out all night and wearing clothes that his mother washed and pressed, Scott went away to college. Scott switched majors four times, skillfully avoiding courses that would move him toward the satisfaction of graduation requirements, and graduated six full years later at age 25. Of course, after the pressure of constant study, Scott needed a year to "get his head together." Mom and Dad appeared to be homicidal the night Scott announced that aspect of his life's creed, but since he was their first, they were unsure how to handle things. This all worked to Scott's advantage, allowing him an additional year of relaxing, late puberty. Mom and Dad strongly and frequently suggested that Scott get an actual, I hate saying the foul word, "job," but he resisted, saying that the way for him to truly succeed was to get his master's degree. Scott began grad school fulltime at age 26 and put his greatest efforts into getting thesis extensions, thus stretching an 18-month course into three years, but grudgingly graduating at age 29. What do you think he did then? That's right, he took a year off to get his head together.
At age 30, Scott joined the working world, gaining a "position" with a public TV station that paid him less in a year than Dad paid for his monthly tuition. And at age 31, he met a girl with a real job (one that paid) and moved in with her. Mom said something like, "She'll be sorry." What was that supposed to mean?
All I knew was that Scott was my idol!!!!
Scott was Joey's idol too. He's four years younger than Scott, but has followed Scott's perfect slacker pattern. He was 28 and entering his third, and perhaps final, year of grad school. He and his girlfriend live in California, so that eased my parents' financial pain a little. But they still wrote those tuition checks.
At 18 and just graduated from high school, I had high hopes for my next 12 or 13 leisurely years.
Mom had other plans for me.
Chapter Two Mom's Other Plans
I guess I should have been suspicious when Mom and Dad started asking me about college applications early in my senior year in high school.
I was baffled by their questions. Didn't they know that extended puberty was my birthright?
Mom would sort of insist that I apply for college somewhere and I would sort of say nothing. Then Mom would say weird stuff like, "I'm not making the same mistake three times." What could that mean? I came along ten years after Joey, so I guess Mom had a lot of time to stew about her boys.
Mom and Dad went so far as to send away for college applications and fill them out for me, then just tell me to sign them. I refused, of course. I needed that year to find myself. Then Dad talked to a guy he knew and got me a job doing road construction for the year of finding myself. What another horrible idea! I refused that too.
When I told my best friends, Mark and Brian, they were horrified too! We were all taking that needed year after the mental exhaustion of high school.
Things began to turn against me when my friends' parents became infected by the idea that their sons should "make something of themselves." Poor Mark and Brian faced the same form of "child abuse" that I did. Was my Mom spreading that horrible concept?
We resisted, of course, and at graduation had what our parents called "nothing going for us" and we were proud.
Things were OK for a day or two after graduation. Then the roof fell in.
That fateful morning, Mom woke me at the ungodly hour of 10 a.m. That's right a.m.! She even made me get out of bed and sit across the dining room table from her before she fed me my usual pancakes, sausages, eggs, juice. Things a young man who's finding himself needs to light his path.
Then she spoke.
"Charlie," the unreasonable-creature-who-had-taken-over-Mom's-body said. "The game is up. You have three choices college, a full-time job or something that I'm pretty sure will make you go to college or to work."
Listening to my alleged "Mom," I sort of expected that her head would spin 360 degrees or she would breathe fire or something. No sane, 21st Century mother could dare to expect industriousness from her 18-year-old son, could she?
Fear gripped my soul. But then I thought, wait. She said three options.
"What's the third option, Mom?" I asked.
Mom smiled sardonically and said, "You and your little slacker friends, Mark and Brian will dress as girls. Full time 24/7. Panties. Stockings. Heels. Garterbelts. Miniskirts. Babydoll nighties for sleeping. Make-up. Girlie hair. You can only be a boy again when you go to college with a full, academic load go to work, or leave home and support yourselves."
She couldn't be serious. Girls? Us? But worse, school, work or supporting ourselves?
After a lot of whining and pleading and questioning, I determined that Mom was indeed serious. She added that if any of us violated the rule, dressing as a boy or even going out without makeup, or standing to pee, the offender would be kicked out of his house to fend for himself.
Mom had me by the shorthairs! Why was she being so cruel? All I wanted from her was complete and total servitude to my every need while I did nothing. I just wanted to be 18 forever. Who doesn't?
Clearly, Mom was a woman who had thought this through and was enjoying herself very much.
I tried every angle. The other boys would call me a faggot and beat me up. I would be marked for life.
Mom's answer was almost too horrible to record "Then get a job or go to college and graduate in four years."
I didn't have to listen to that! "I won't!" I said, and stomped my little feet.
"It's your choice, Cheryl," Mom said.
Then Mom added, "I imagine Marie and Barbara are making the same choice you are right now. It should be interesting."
It was certainly that.
Chapter Three Dressed
Looking back on it, I had some odd ideas about things.
I mean, when I decided to start dressing as a girl, it was all about being a "freedom fighter." Slacker freedom. Freedom to avoid adulthood's responsibility while reveling in its benefits. Every young man's right!
A man's gotta do what a man's gotta do, right?
So I guess you could say that I was quite surprised at the path my decision took me down.
That day, Mom told me to go into my parents' bedroom and strip naked. Well, I wasn't about to do that until Mom said, "State university (with a full academic load) or road construction?"
Naked it was.
I was very embarrassed to be naked in front of my mom. But that was just the very tip of what was to come.
Mom handed me a ladies' razor and told me to go into her bathroom and shave my legs. Then I was to call her and she would shave my bottom, including <blush> between my cheeks.
Freedom fighters must endure discomfort, I thought, so I did as she asked. The worst part of it all was that, as Mom made me "all smooth" in my most intimate place, my <blush> anus, I produced half an erection.
Where did that come from?
I hadn't had much experience with anything sexual. My attitude about girls was the same as my attitude about life in general. I felt "entitled" to girls and, even though I hadn't met one who would recognize my entitlement to her, I was confident that, like my brothers, I would. So, frankly, I didn't think about sex much and hadn't even masturbated. Strange but true.
Anyway, shaving above the waist was pretty easy because I didn't have any hair to speak of there, even on my face. She checked me out very carefully as I stood there naked. It was humiliating, especially since I had a cock that seemed to want to stay the way it was when I was 11. Small and unused.
Thinking back, that was the first time Mom had seen my cock in a long time, so she was probably surprised how "poorly endowed" I was. Little did either of us know at the time that it was a genetic gift.
Mom had me lift my balls when she shaved between my legs and she had me spread my bottom cheeks and hold them apart as she shaved every hair from my most private place. It was the first of what would prove to be a series of frightful humiliations. Still, it was, I thought, the kind of pain a true revolutionary must suffer.
Even then, I had a very high opinion of myself for some very strange reasons. Being naked in front of your Mom when you're 18 doesn't do a lot for a guy's self-respect, so it was good that I had that high self-opinion the day Mom started my unwilling transformation to hot babe.
Mom ordered me to take a shower, then dry off. "And there had better be no rubbing with the towel," Mom said. "Girls pat themselves dry. And you're going to act like a complete girl or ELSE! After the shower, join me in your bedroom, Missy."
The demon within Mom snarled the threat with some glee. Things were getting out of hand.
I finished my shower, patted dry, wrapped a towel around my waist and padded into my room to see Momzilla.
She was enjoying it all, getting revenge on Scott and Joey through me. That was the worst part.
Mom was sitting in my easy chair, twirling a pair of skimpy panties around her right index finger as she smiled sardonically. Were those for me?
It appeared so. "Get 'em on, Tootsie," Mom said.
So I was FORCED to put on my first panties by an evil dominatrix. Pretty cool, huh? Though not entirely true. If I had surrendered right then and gotten one of those job things or taken a full course-load in college, Mom would have been completely happy and would have never given pantying her youngest son a second thought.
She started me down a path neither of us thought had pantyboy royalty as its terminus.
But back to the first panties.
They were lovely. Pale pink and sheer. Little, white hearts along the waistband.
Mom handed the little teasers to me and barked at me to put them on.
How embarrassing. How emasculating. How deliciously exciting.
I won't say that when I touched the panties, electricity surged through my body and girlishness possessed me. It wasn't like that at all.
But I was prepared to hate wearing panties and I didn't. Hate them, I mean. I didn't.
I slid my right leg into the panties. Then the left. I stood and sort of shimmied them up my legs. By the time they reached my mid-thighs, I had three-quarters of a stiffy. When I nestled my balls in the bikini treasures, my little tickler was red, rock-hard and throbbing.
Mom noticed. I knew it from her smile. But there was enough of the old Mom in her that she didn't mention my arousal.
My chubby had practical considerations. The panties were stretched and didn't fit right. The silky, girlish material was tormenting nerves in my knoblet that I didn't even know I had. I didn't have much time to think about it because Mom was behind me, adorning me with a matching bra. Was that necessary?
My nipples seemed to think so. When Mom laid the silky material over my little nubbers, I winced in erotic discomfort. Where were those feelings coming from? I had never given my nipples a second thought, but the friction of that lacy bra had me in the early stages of a dither.
The dither blossomed a bit when Mom sat me on her bed and sat next to me. "This is how a girl puts on her stockings, 'Princess.' You roll them into a little doughnut, then point your toes like this and roll slowly."
Mom then demonstrated by rolling a nice pair of black, sheer stockings over her very good legs. Did Mom usually wear stockings? I couldn't remember.
Maybe I was just a tad self-centered at that time of my life.
Mom then handed me a pair of tan, very sheer stockings and had me roll them into doughnuts. A little film of sweat formed on my upper lip. Like any male, I knew I was crossing a big river. A scary river. What if I liked the other riverside better?
Mom didn't allow much time for appropriate reflection. "Roll them up, Cupcake! That's it. Oh, nice legs! The men and boys will be whistling at you when I take you out this afternoon."
As humiliating and terrifying as Mom's threat to show the femmy me off in public was, my brain couldn't focus on it. The only meaningful input was coming from my cock. Not unusual for an 18-year-old boy. But what was so sexually thrilling to me about being in my first panties, bra and stockings?
I was half an impure thought away from a shuddering orgasm.
And that was a lot scarier to me than the thought of being paraded en femme in public.
But Mom had more. She produced a garter belt an object of clothing I didn't even know existed then showed me how to put it on and hook it to my stockings.
I looked at my legs encased in smooth, tan nylon. They looked wonderful! And the feelings were delicious. I saw the little webbies between my toes and felt my balls stir yet again. Mom slipped a tight pair of pumps on my feet. The heel was ridiculously low only two inches but I struggled to keep my balance.
Mom led me to her full-length mirror and said, "Look at yourself, Miss Sissypanties! Is this how you want people to remember you? This is how it's going to be. In fact, I'm going to give you a blouse and a miniskirt and I'm taking you to the beauty parlor for a makeover. In public. Today. Do you give up?"
Mom not only underestimated the depth of my sloth, she completely misread how I would react to being dressed as a girl.
I had never been so excited in my life. I had no make-up, hair styling or accessories. I could barely stand in two-inch heels. I had been in lingerie for about 15 minutes.
But I knew. Mom didn't know. And she didn't know I knew. She just thought I was obstinate.
Thinking quickly for one of the first times in my life, I told Mom I had to go to the bathroom before she put the "street clothes" on me. Mom sighed in exasperation, but thank goodness, she let me go.
I barely made it to my bathroom and got my panties down before I began spurting cum so hard that it drove me to my stockinged knees. Good golly! My guts were torn open and I sprayed cum all over. My eyes filled with tears, which Mom would take as my reaction to her plan to humiliate me into responsibility.
Somehow, I managed to clean up the sticky evidence and report back to Mom for my blouse and miniskirt.
Mom looked at me curiously. She clearly thought I would have caved already. I wondered if Mark or Brian had caved. But mostly I wondered what was happening to me.
It felt so weird to go out our front door, in girlish gear, carrying a purse, and stepping carefully in heels. I guess I still walked like a boy, but I tried to walk a bit girlie so I wouldn't be so "obvious."
No one saw me, I think, during that short, but important walk to the car. Mom was recalculating things a bit. My biggest fear at that moment was that Mom would cave telling me I could get out of my girlie clothes and live the slacker life enjoyed by my brothers.
No way. She may have seen her youngest son begin his evolution as a pantyboy, but in Mom's mind at that time, anything was better than a third slacker in the family.
We drove in silence. Mom reasonably mistook my discomfort as humiliation. It was really caused by a heady mix of confusion, anticipation and large dollops of sexual arousal.
Chapter Four Slack Like Me
On the ride to the beauty salon, I also wondered what Mark and Brian whom Mom and their mothers had renamed Marie and Barbara were doing? Had they caved in, leaving me alone in the fight for slacker rights? Had they stayed in character as the born slackers they were, refusing any efforts to coerce their entry to the adult world? Or were they <gulp>, like me, frantically excited and astonished at their first visit to Girlyland?
Brian and I were smaller boys. I had never seen Brian's "equipment" and didn't know if he was as dainty as I, but, like me, he was slim, with long legs. I tried to picture Brian as a girl and, amazingly, I was able to do so. He was cute, in my imagination. And girlish. Though as a boy, Brian had been hygienically-challenged, perhaps he would be a neat girl.
No such picture emerged of Mark. He was six-foot-two, 200 muscular pounds. Ripped abs. Muscular legs. A real "guy" face. I was afraid for him if he were to wander out dressed as a girl.
But there Mark was, with his Mom, walking into the beauty parlor as we pulled into the parking lot.
Mark was in full girlie gear, minus the make-up and hair styling. And he looked ridiculous.
Mom gave a little toot and Mrs. Cumwell stopped and waved at us, then waited until we got out of the car. Mark looked miserable. And he was something else. Interested about the way I looked. And walked.
Mom and Mrs. Cumwell were congratulating themselves about our torment, so I managed to pass on a "revolutionary's message" to him. "Stay strong, brother."
Mark gave me the oddest look and said, "Easy for you to say. You've never looked better in your life."
I did? Was that a compliment? Did he really think so?
I got the weirdest tingle and my stiffie returned.
"Come along Marie, Cheryl," Mrs. Cumwell said. "I'm sure your pretty little friend Barbara is inside having her face done."
Mark groaned. I quivered at the thought of having my face "done."
I tried not to look at Mark. He was huge. And manly. And ridiculous-looking. Maybe a day in a beauty salon would help. Maybe Al Gore and George W. Bush would be teammates in a Wednesday-night bowling league.
For the first time in my life I entered a feminine sanctuary a beauty salon. Women who cared about their appearance were having their nails, hair and faces done. I looked around for Brian, AKA Barbara. He was in a chair, receiving a make-up lesson. His Mom, Mrs. Harder, was standing smugly beside him, urging him to pay full attention to make-up technique.
Oddly enough, Brian seemed to be hanging on every word, watching every technique. And oddly enough, Brian was, as I had imagined, extraordinarily cute as a girl.
It was clearly the strangest day of my life. And probably the most important. I caught Brian's eye, giving him a little wave and a "thumbs-up" as I was led to my chair for make-up, manicure and pedicure.
Mark acted as if he were being led to his execution.
I was so excited, I was trying valiantly not to cum in my panties.
Oh my. A beauty technician named Phoebe was quite amused to have a boy in her chair, but even she was impressed with the make-up results. I was VERY pretty. Darned-near beautiful. And very feminine-looking. Mom was shocked. Phoebe was shocked. Mark and Brian were shocked. When I looked at myself, I came in my panties. No one even noticed, so great was their amazement at my beauty. Thank goodness I was wearing a black miniskirt.
I looked over at Mark. He was looking at me in the weirdest way. Almost lust. I wasn't sure and neither was he. Brian was looking at me with what may have been envy, though he was darned cute as a girl.
When they got done with me, hair, nails and all, I was feeling pretty good about myself. But then I looked at Mom. She was processing reevaluating. Was she changing her mind about making me dress as a girl?
I had to act.
"Mommmmmmmm," I whined in my best slacker voice. "This is horrible! Please don't make me do this. I'll be beat up. Everyone will call me names."
Mom's face hardened. Her strength renewed, she said, "Will you get a job or go to college full time."
I put on my best brat face and said, "I won't! I won't!"
So the "blackmail" continued.
Chapter Five Two Brave Revolutionaries
Mom and I rode home in silence too, though I caught her sneaking puzzled peeks at me.
When we got home, Mom escorted me to my room, where Dad was just finishing up some modifications. He had shoveled out the dirt, taken down the blacklight posters and removed all my boy clothes from the floor and my closet. A full array of girlie stuff was in there now, as well as a pink bedspread, stuffed animals and a vanity table with a stool and a full array of make-up items.
Mom had apparently enlisted Dad fully into her evil plans.
But I thought the whole situation was not half as bad as I had anticipated. I mean, so far I liked dressing like a girl. A lot.
Later that day, I got a call from Mark. Mom insisted that I answer the phone saying "Little Sissy Cheryl speaking." Mark laughed when he heard that, then he apologized.
Then he really apologized. "I believe in what you're doing, Charlie, I mean Cheryl, but I can't do it. I look ridiculous, but, I must say, you look great. Really great. I mean, good, you know?"
Something odd was happening with Mark, don't you think?
"Anyway," Mark went on, "My Dad got me a construction job. I start tomorrow. Then I'm going to college full time in the fall."
The HORROR!! I thought. Mark was no longer a slacker. He was practically an adult!!!
I should have been very angry at him. I was, sort of. Why then, when I got into my pink babydoll nightie and got into bed, between my silky, scented, pink sheets, did I think about Mark? At a construction site. With his shirt off. Muscles rippling.
Why, as I fell asleep, did I lightly touch my peeny with my fingertips while thinking of Mark? And why did my tummy clench and why did I start spurting that sweet cream that the boys would love so much later on?
The next morning my tummy was sticky with dried boy's cream. The girlie clothes had me in a stimulated mood, so it was clear to me that I would be doing some serious self-love, complete with its requisite guilt about being so stirred up by my feminine self.
The only alternative to being an apparent sissyboy was to give in to Mom. And that was not on my agenda.
I yawned and padded into the bathroom, sitting to pee. Would Mom be dommy today or could I just girlie up and see where things took me? And other than occasional heavy lifting, what was Daddy's role in all this?
I took a shower, brushed my teeth and even shaved. Phoebe had given me some foundation that would cover my light beard very nicely, so I used it as a base for my face that day. I spent some time with my eyes and, though I veered a bit toward trashy, had my baby blues looking pretty girlish. Lipstick, blush, powder and perfume and I was ready to put on my bra and panties. But first, I'm sorry, I just had to relieve my "tensions." Looking at my lovely face in the mirror as long as I did had me quite worked up. I stood in front of my three-way mirror naked, with a tissue in my left hand and my popsy in my right. I held my pretty knoblet between my thumb and forefinger and rubbed. It didn't take too many strokes or too much of a fantasy. My own beauty had me shooting my first creamy load of the day into my soaked Kleenex.
A narcissistic sissy is a happy sissy.
My panties were still "pointed" when I put them on. The rubbing of my silky bra against my swollen nipples was going to have me in a sexual "state" all day. Those sheer, black
stockings I rolled up my excellent legs had me "on the verge" as well. Mom insisted that I wear the three-inch stilettos that day just to torment me. She actually thought at that point that she would win.
Well, when I slipped my pretty blue dress with white polka dots over my head, then added a ribbon to what was clearly a boy's haircut, despite the salon's best efforts, I was ready for the worst Mom could dish out.
She was very surprised when I showed up in the kitchen, before noon, in full feminine splendor. Mom took it as defiance, not sissiness. If she had thought that I was enjoying myself, she probably would have done everything she could to make me butch. Especially after .
More about that later. Anyway, Mom went back on the offensive. "Don't you look wonderful, Cheryl, dear? Doesn't she, Roger?"
Dad had the funniest look on his face. A look I've seen from men thousands of times since that day. He grunted an affirmation, but didn't break "the look."
Mom went on, "Have a bowl of Special K and skim milk, dear. You're little sissy friend Barbara and her mother will be by any minute. We're going on a field trip."
Mom had nothing good in mind for that excursion, I was sure. But from my end, at least, her planned nastiness was like a trip to Disneyland.
Barbara (Brian) and Mrs. Harder arrived 15 minutes later. The moms were clearly enjoying themselves. But even Mrs. Harder was impressed by my beauty. Mom was too, but wouldn't admit it.
Barbara's panties were tented when she saw me, but whose wouldn't be? I'm fabulous! And, you know, Barbara was pretty good-looking too. We didn't get much opportunity to communicate early that day, but I was pretty sure that Barbara was enjoying herself as much as I was.
The moms hustled us out the door because we had to get to a big, downtown construction site at lunchtime. The men were all sitting out, wolf-whistling the girls, when we arrived. Barbara looked miserable when she assessed the situation. Was she acting? I knew my look of misery was fake. I was eager to be sexually harassed by throngs of horny men with calloused hands and hairy chests.
Mom and Mrs. Harder had dressed sort of hot for the occasion as well both were attractive, and when they chose to dress like women, very attractive. They had big heels, stockings and short skirts. Did they enjoy walking past construction workers too?
"All, right, girls. Let's walk down this path. If any of those men call out to you, the ladies will take you over and introduce you properly to the nice gentlemen. Let's go."
Barbara and I walked as if we were in our funeral procession. Barbara was either an excellent actress or she hated dressing girlie.
How could anyone hate dressing girlie?
Groups of hard-hatted men seemed to coalesce in front of us as the four feminine forms wiggled toward them. Mom drove the herd onward. Ten yards away, the first man made a sound a deep, loud, wolf-whistle. That broke the mood of awe, and several men whooped and called out clever things like, "Hey, Baby" and "Hey, Pretty Mama."
My cheeks were red hot. I guess it was one part humiliation and two parts sexual excitement. Not that the men would ever do anything other than catcall, but the situation was gorging my starving ego.
When the men had concluded their performance, Mom spoke loudly. "Thank you, gentlemen. That's so sweet. It's so sweet of you to salute two older ladies like us. Surely you weren't calling out to Cheryl and Barbara, our sissy sons. They like to dress as girls and tease men. I'm guessing they even have sex with men now and then, but we've never caught them doing that. Surely, men like you aren't interested in pansies with little penises, are you?"
Was Mom trying to have us torn apart by an angry mob? If so, she failed miserably. And proved once again that she didn't understand men.
A man in the back responded to Mom's question. "Girls like them deserve a man's full attention. They're pretty enough to be in Panty Boy magazine!"
That brought vigorous agreement from the crowd and inspired Mom to get the four of us moving again.
What an interesting response. Did men really lust for "girls" like Barbara and me? And what in the heck was "Panty Boy magazine?" I soon found out.
Chapter Six A Revolutionary Council
Mom and Mrs. Harder were prepared to lead us into several more life-threatening situations that day, but decided to take us home and cut their losses.
I was surprised when Mrs. Harder went home and left Barbara to spend the night. With me. In my room.
At around 8 p.m., Mom, still directing, but losing a bit of her edge, told Barbara and me to get into our nighties, then we could come downstairs and watch TV together on the couch.
Alone at last.
I took Barbara to my room and closed the door. "So, what do you think?" I asked. Then I turned and said, "Would you unzip my dress?"
Barbara unzipped as she answered. "Good question," she said. "What do you think?"
I shimmied my dress over my head, exposing my lovely, lingeried body to Barbara. "I asked you first," I pointed out correctly.
Barbara looked scared. To admit to someone that you like cross-dressing is not easy. "I think that you look amazing in girl's clothes," she said, cheating a bit, but gaining points with me.
"You look pretty good yourself," I said, unhooking my bra and exposing my puffy nipples. "Aren't you going to get undressed and put your nightie on?"
Barbara gulped. Then she began to undress. "Everything's different now, isn't it?" she said.
"Yes," I said, unsnapping my garter belt and starting to roll down my stockings. "But we could always go back to being boys. We just have to do what our Moms want."
Barbara got up her courage and said, "I don't think I want to go back. Not right away, anyway."
I said, "Me neither," then went over and kissed her lightly on her glossed lips.
We took that no farther, managing to get into our teeny nighties, panties and stiletto mules without sexual incident.
We rejoined Mom in the family room, where she and Dad had begun watching "Victor/Victoria."
Poor Dad. His eyes were bugging out when he saw two delicious, 18-year-old, scantily-yet-sexily-clad pantyboys in plain sight. The poor guy's trousers were extended as well.
Dad kept sneaking looks at us. So much that Mom dragged him up to bed halfway though the movie, leaving Barbara and me on the couch, next to each other, warm, silky thigh touching warm silky thigh.
I actually think Mom was trying to make us disgusted by the homo-ness of it all sitting next to each other, sleeping in the same bed.
As with every plan Mom had made, it backfired.
I had never seen "Victor/Victoria" before and I was kind of enjoying it. Especially how a man's man like James Garner could be attracted to Julie Andrews, who, he thought, was a crossdressing man. Sort of like those construction guys earlier in the day.
I was so into the movie that I almost didn't notice that a soft hand had insinuated itself under my pink nightie and was reaching for my left nipple. Then I noticed.
"Thank you for that kiss earlier, Cheryl," Barbara said. "I enjoyed it very much."
Apparently so. The bad little creampuff was twiddling my left nipple between the thumb and forefinger of her right hand. It felt incredibly wonderful. I moaned a little and parted my lips. Barbara covered my mouth with hers. Then she gave me her tongue.
Why we were doing "things" with each other was a mystery to me. A few days earlier, if "Brian" had kissed me and twiddled my nipple, I would have a) thought he had gone insane, then b) attempted to dismember him.
But sissied up and pretty in our girlie things, with girlie names and girlie looks, it seemed all right. Very all right.
I wiggled with pleasure. The kissing. The friction on my nipple. Then Barbara's hand dropped and slid inside my panties.
Still kissing me, Barbara tickled my sensitive knoblet with her gentle fingers. Skinning it sweetly. Exposing the pink, slick head and all its tender skin. After several glorious minutes, I squealed softly, sucked her tongue very hard, and filled my panties with warm, girlish cream.
Barbara was right. There was no going back for us.
Barbara took my hand and led me up the stairs to my bedroom.
What would Mom have thought if she saw us holding hands, faces flushed with sexual arousal? Pretty little "points" in our panties.
Mom would have probably been pissed that her plans had failed yet again. Then she would have started blaming herself for turning her son into a "little sissy faggot."
Well, I am not a "faggot," let me tell you. I adore men and make them very happy they were born with a Y chromosome. But I'm a completely different gender from men. And women. And they both know it.
And Mom surely didn't turn me into anything. All she did was wake me up. To life, as well as my true identity.
You never know what will happen when you put a young man in panties other than the fact that he'll probably make a big creamy mess in them. Most of them enjoy the experience, though they wouldn't admit it to anyone, especially themselves.
Barbara and I were letting instinct guide us, something we're all discouraged from doing most of our lives.
It was great.
We got on my double bed and grunted and panted as we kissed and groped each other. I had Barbara's nightie up over her nipples and her panties down below her little bag and popsy. I was VERY excited.
Her "Passion" perfume was entering my nose, then telegraphing my brain. Following instructions from my brain, blood was rushing to my penis, making it stiff and needy again. She was enjoying the attention tremendously, panting and gasping as I kissed and licked her left nipple and massaged her teeny peeny.
Barbara's nipple erected sharply as my glossed lips and moist tongue tormented its sensitive flesh. Her pretty eyes were closed and her back arched as she surrendered to the pleasures we were avidly exploring.
I was fairly certain that she was "on the verge," when an impulse of passion seized me. I stopped licking her pretty nipple. She whimpered softly and made a pouty face. What a surprise. I thought a pouty face would be well, pouty. But Barbara's pouty face was quite sexy. Seizing the initiative, I scooted my panties off, then reversed my body on her. She was on her back and I was on my right side my lips inches from her penis and her lips inches from mine.
We both contemplated the very big step we were about to take. We would be cocksuckers. Marked forever.
Barbara's cock was so tiny, it wasn't entirely like being a cocksucker to take it into my mouth. Is there such a thing as a semi-cocksucker? If I sucked it twice, would I be a full cocksucker
Too much musing. I kissed Barbara's pretty, pink pole. And didn't die. So I licked it. Mmm. That was nice! Barbara squeaked. Then I felt a warm, wet mouth around my cocklet for the first time in my life. And I was hooked. Sucking and being sucked make me very happy.
I slurped and licked and kissed and made lots of noises of genuine satisfaction. Barbara was a talented cocksucker. And references on my cocksucking skill are available on request.
Since Barbara hadn't cum yet that evening, she was the first to lose her girlish cargo. She made such a sissy squeal that I was afraid Mom and Dad would burst into the room with a SWAT team. They didn't.
If they had, Barbara and I would have sucked the SWAT team's cocks. We were very randy and very eager to try out our new skills.
Barbara gave me my very first mouthful of cum. And she must have been saving it up, just for me because it was plentiful and deliciously creamy. Who knew that I would love the taste of cum so much? To me, it's the nectar of sex.
Like a good sissy, I swallowed my lover's whole load. Barbara moaned and whimpered as I continued to lick and polish her knob well after her seizure. Then she resumed sucking me.
I liked that a lot. I sort of kissed Barbara's pink helmet as she tongued my treasures. It was all so naughty and exciting. And girlish! I was a girl being sucked by a girl. Frilly girls. Pleasuring each other with abandon.
Would I be able to please a man as I had pleased Barbara? Would I want to? Would a man want me?
Then I got a strange, but clear mental picture of being girlied and half-naked, in bed with a man. Specifically Mark. Mark was making love to me and making me cum and cum. Where did that come from?
Wherever, it led to a cum that was so intense, it almost exploded the head of my cock. Barbara was choking and cum was drooling from the sides of her mouth!
When we settled down a bit, we got under the covers, kissed and hugged, then fell asleep in each others' arms.
Chapter Seven Barbara's Betrayal
Barbara and I had similar enjoyments once at around three a.m., then a last when we awoke at seven.
I didn't know where this was all leading, but the journey sure was fun.
Mom looked at us funny when we went downstairs for breakfast. We had cleaned up, a bit, but Mom could probably still smell the cum. Or maybe Dad could. He was certainly acting disturbed at breakfast.
Anyway, the next week or so was very odd. Mom was less confident that she would "win," but she was nowhere near being ready to give up! She spent a lot of time at the library and on the Internet, looking for new tactics in dealing with me. Getting me to enroll in college and start moving ahead. As a boy.
It was late June and Mom always went to visit Grandma for two weeks. My "petticoat punishment" would apparently have to be put on hold for a while, unless Mom trusted Dad to push me. Dad had never been very good at being a disciplinarian, so I was assured of an easy fortnight.
Barbara and I had "gotten together" several times since our breakthrough night and I was looking forward to seeing her a lot with Mom gone.
Oddly, Mark had begun calling me around ten o'clock most nights. Every night, actually. Telling me about his day and asking me about mine. Telling me his feelings! Asking about mine! Before, we mostly grunted "Hey Dude" at each other. When we did talk, all we ever talked about was girls, video games, school, cars, sports and pizza.
Mom even asked me to drive her to the airport. She liked seeing Grandma, so she was in a good mood. Could she be softening toward me?
I liked going places as my girlie self. The airport was lots of fun for me. In fact, wherever I went, men would watch me. Undressing me with their eyes. I enjoyed it too, being a prickteaser. That's what I was. The prickpleaser part came later.
When we left home for the airport, Mom told Dad that her flight had been delayed, but when we got there, we found that it was back on schedule. So I arrived back home two hours before I was expected.
Why does that always seem to cause problems?
I pulled into the driveway, then sissied into the house in my big heels. Giving the male neighbors a great show. Maybe I would call Barbara, I thought, and we could exchange some creamy fluids. Mmmm.
Maybe I would wear that new black babydoll, and those black, seamed stockings I hadn't worn yet, I thought, as I went up the stairs to my room.
I was so lost in carnal plans that I didn't hear the grunts and squeals and moans of two people in a sexual clinch. Until I was outside my parents' door.
Mom was out of town! Did Dad have a lover?
Impossible. Mom had him so cowed.
But something involving cum and noises was happening in there.
I know, I know. You're thinking, "Why didn't that busybody, big-mouth Cheryl mind her own business? Why didn't she just stroll on by that bedroom door?"
I had to know. I slowly opened the door and confirmed part of what I thought to be true. It was a quite naked Dad on top of another person.
Seeing your Dad naked, fucking his brains out, was bad enough. But wait, there was more.
Dad was having the time of his life. He had a beautiful, feminine person in lovely lingerie under him. The two were involved in deep, mutually pleasurable coitus. The woman's face was obscured, but I could see that Dad had her calves on his shoulders and he was pushing his big bruiser in and out of her bottomhole, not her pussy.
I asked myself, was that possible?
Was I ever that young?
There was something familiar about the woman. I had to see who it was. Then I did.
It was no woman.
It was Barbara.
Daddy was fucking one of my two best friends.
In my house.
My best friend was letting my Daddy fuck her. Worse, she seemed to be enjoying it a lot more than when she and I made love.
My eyes filled with tears. I was short of breath.
I ran out of the room and they never even saw me. The fucking fuckers! The nerve!
I had to get out of the house, so I grabbed my purse and got into the car.
I had to drive. Get away. Find comfort. Where could I go?
My brain was brimming with questions. Horrible questions. Was Daddy gay? Didn't he love Mom anymore? Was Barbara gay? Didn't she love me anymore? Would Daddy leave Mom and marry Barbara? Would Barbara be my stepmother? Was I gay for sucking a gay person's cock?
Somehow, I ended up at Mark's house. Would he be home? It was a Saturday, so it was possible.
I touched up my makeup no sense looking frumpy. Then I tottered over on my new, four-inch stilettos, and knocked on Mark's door.
He was home! And alone! And very concerned about my distress! And VERY handsome and hunky from all that manual labor on his job.
Maybe the day was improving.
Mark invited me in and I began to cry. Tears were flying from my eyes, as it did in those old romance comic books, remember? Anyway, Mark hugged me to comfort me. He asked me to tell him what was wrong and I raised my head to tell him. But my eyes locked with his clear blue eyes. And he was hugging me so nicely.
Then. somehow, we were kissing.
Good golly, it was wonderful.
If my life depended on me telling Mark why I fled my house to come to him, I would be six feet under. All I could think of was how wonderful Mark's lips felt on mine. How his manly beard rubbed softly on my tender skin. How his big, calloused hands felt as they caressed my bare shoulders.
It was so wrong. We had been boys together since we were five years old. I shouldn't <gasp> be letting him <pant> kiss me like that. Overpowering me. Ruling me.
I learned a lot about myself at that moment. I wanted very much to submit to a man. A nice man who would cherish me as he dominated me. A man who would take my problems on as his own.
I sort of surrendered to Mark as he held me and kissed me. I felt something leave my body forever. I think it was what remained of my masculinity.
Mark felt it too. And he did exactly the right thing. He stopped kissing me and we sat on the couch. He put his arm around me and made everything all right. Then he asked, "What happened, Cheryl?"
He called me Cheryl!!
With little, girlish sobs, I said, "I caught that little tramp Barbara, I mean Brian, no, I mean Barbara and my father in bed together. Doing 'things' together."
Mark looked genuinely shocked. Then he looked very thoughtful. "What exactly were they doing? Tell me everything."
Obviously, Mark thought it would be therapeutic to do so. I sniffled and said, "That tramp was on her back. She was wearing a sheer, black teddy, unsnapped at the crotch and her trampy pricklet was sticking straight up. She had her legs, which were encased in fully-fashioned, black stockings, all the way back. She had her trampy calves over my Daddy's shoulders. Daddy was naked and on top of her. His big 'business' was stiff and he was pushing it in and out of that little tramp's tight bottom."
Mark's eyes lit up. With great interest he asked, "Are you sure he had his 'thing' in her bottom?"
Sniffling, I nodded.
"I'm sorry to ask this, Cheryl, but did it appear that Barbara was in any pain?"
An odd question, but I answered it honestly. "No pain. Lots of pleasure. For both of them. Isn't that disgusting?"
Mark nodded his agreement, but I think he was thinking bigger thoughts. And there were bigger things growing in his pants.
Mark gulped and made a very important declaration.
"Those moments when we were kissing were the best of my life, Cheryl. I'm not gay, so I never thought that I would fall in love with my best friend. I mean I read 'Panty Boy' magazine and everything, and I guess your Dad does too, but I never thought you would be I mean "
And then he stopped talking and started kissing me again.
It was deeply delicious. I had no idea what he meant by "Panty Boy" magazine. But I think he had big plans for us that day.
I was ready.
Mark broke the kiss and asked, "My Mom and Dad won't be home for about ten hours. Would you like to visit my room?"
Try and stop me, I thought.
Mark asked, "Do you want to call home and tell them you'll be late so your Dad doesn't call the police?"
Hmmmph. I thought. I knew those two were too busy to answer the phone. But I took Mark's advice and left a message.
Then we went upstairs, hand in hand. I was very nervous. Shaking, even. But Mark was so sweet and strong. I put myself in his hands.
Unlike my room when I was a boy, Mark's room looked as if a human being lived there. The bed was made and the sheets were clean. They wouldn't be for long.
I was so glad I had worn clean underwear. At least some of Mom's advice had been good.
That day, as I recall, I was wearing a cute, white sundress, white bra and panties, a white garter belt, seamed, tan stockings (with a dark weal on the thighs), and the prettiest, white, strappy sandals with four-inch stiletto heels. That get-up, along with my perfect make-up, natural beauty and submissive attitude, had my young man in quite a state.
I turned to let my man unzip my sundress, which he did as he was softly kissing my neck and creamy shoulders. I whimpered as he slowly inched the zipper down. He ran his rough hands gently along my shoulder blades as I wiggled out of my dress.
I stood before my first man in bra, panties, garters, heels and stockings. My panties were very pointed as I watched Mark strip naked. When he was without a stitch, he lay on the bed on his back. I hadn't seen his johnson since we were nine or ten. It had grown. From what I could see, it was bigger than Daddy's!
Mark beckoned to me to join him. Should I get into bed with my big sexy heels on? That seemed to be what he wanted? Apparently. Stilettos in bed are sexy, don't you think?
So is a naked, beautiful, muscled man with his arms open. I sissied to the bed and threw myself into his arms.
We kissed a little as Mark explored my body with his hands. I think he liked what he felt. I have great legs and a better bottom. He spent some time exploring both.
Then he decided that my bra was too confining for me. He reached behind me and unhooked it expertly. Oh, how I would have liked to have flopped out two C-cup, brown-nippled puppies for him. But Mark was thrilled to expose what I did have two sharply pointed, erect, nipples that ached for his kisses.
They stopped aching.
Mark applied his mouth and lips to one of my pouty little puffers. And I felt things I knew I wanted to feel for the rest of my life.
Desired. Loved. Sexy.
And sexually frantic.
I wiggled and whimpered. It was a fully armed assault on my body's erotic core. Then Mark brought in reinforcements.
The naughty lad reached into my pretty panties. I felt calluses brush the tender flesh of my testicles and penis. Was he going to No. <Rats!>
Mark wiggled my panties down far enough so that the heel of his hand was on my little peanuts. Still kissing my left nipple, tongue rubbing the tender flesh, he slid his thick, rough, middle finger between my bottom cheeks and <gasp> lightly touched my anus with the pad of his finger.
Sissies have limits. Your friend Cheryl reached hers at that moment.
I screamed. And began to pump large globs of creamy goo into my panties and tummy.
It was spectacular. Sensational. Crippling even.
The night was young.
And Mark had big plans.
He seemed delighted that he had made me cum all over myself. I don't know where his inspiration came from, but he did two things that were exactly right. First, he moved his mouth from my nipples to my glossed lips. I really needed some kissing right then. Second, he pulled my panties all the way off and began to scoop up my cum with his fingers and apply it to my <blush> bottom.
Mark's kissing muffled my squeals as his middle finger entered my virginal anus. He was lubricating me "down there" with my own cum and his thick, rough finger.
It was heaven.
Or at least a full preview of it. My limp popsy was flopping as the masterful man dug into my most intimate place. As if he owned me.
After a few moments, Mark added a second finger. Then both intruders found my prostate. And rubbed. As we kissed.
I was in an erotic trance. My pricklet was semi-soft, though I felt I would be cumming any second. The darned pressure on my prostate was driving me wild. But I wasn't hard, so I couldn't Aggghhhh!!!!
A sharp pang of erotic agony devoured me. My balls were volcanic. Searing heat flushed through them and suddenly, creamy, pantyboy juices were everywhere!
I was on a different, better plane of existence. A wet, messy plane. And Mark wanted to join me there.
He was going to fuck me. Just like Daddy was fucking Barbara. Except Mark and I had something pure and beautiful. Not like them.
Mark rolled me onto my side. He was going to fuck me from behind. But then he changed his mind and rolled me onto my back. I was going to be fucked like a woman!
I knew I could say no and he would stop. But why on earth would I want to do that?
I wanted IT!
And I was about to get it.
My panties were discarded, and all I had one were my stockings, garter belt and heels. I felt a little slutty with the heels still on. I liked that. So did Mark.
I hadn't really even touched his cock and it was about to be inside me. Rubbing my secret "trigger" in my special place. Pumping his cream into me.
Shyly, I took little peeks at his weapon of mass deflowering. Its eye was looking at me. And dripping. Did it wink at me?
I think I was blushing about being so exposed and submissive. If anyone had walked in on us, I would have been humiliated. But I would have insisted that Mark continue.
Mark gently rocked my legs back. My knees were against my ears and my pussy was exposed to my man. I saw him looking at it lovingly and his cock stiffened a notch. Mark told me later that he loved seeing my seamed stockings and sandals framing my pussy and my "privates." He said it was the prettiest sight in the world.
Then he fucked me.
I know that's what you've been waiting to read. I do meander a bit telling a story, don't I? Anyway, he fucked me.
Very nicely. My first time. And certainly one of my best.
Mark leaned over my body and kissed my lips. Then he sat straight up and concentrated on his welcome task. His big helmet was skinned and slick. I was making little sounds of encouragement. He introduced the invader to the gates of paradise. I felt a sharp pang of fear. Then a tiny, but sharp pain as he pushed the dark red mushroom into my cum-lubricated hole. I squealed with pleasure as he pushed the whole big thing in. I had been totally penetrated. Gorged with cock. I was on my back, like a girl, "getting it" from a man. And loving it.
Mark had an excellent rhythm going. He was obviously enjoying himself tremendously. So was I. I loved how his balls slapped into me each time he plunged into me. I loved how his cock rubbed my prostate with that big, round head of his. At that moment, I was three-quarters in love with Mark! And the lad seemed to be quite taken with me as well.
I think at that point, Mark entered the stage of the fuck where a man almost forgets he's with someone and concentrates on his own orgasm. I didn't begrudge him. He had already given me two major, seismic events. And a third one was brewing.
I was about three-quarters erect. The last, quarter erection seemed to be eluding me because of that blunt object in my bottom.
Mark was pushing and pulling. He looked so intense. I closed my eyes and felt what was happening to me. It was awfully good. Each push against my prostate sent an electric jolt into me, straight into my balls. I wrapped my stockinged legs around my man and pulled him into me harder.
That did it. For both of us.
Mark's huge nuts boiled over. He incinerated my insides with six thick spurts of his male lava. I felt the first two. The last four occurred during the largest pantyboy orgasm ever recorded in North America. If a nuclear device had exploded next door, I wouldn't have noticed.
My little peanuts almost separated from my body. And my "little person" pumped out so much hot sissy cream that it ran off both sides of my tummy and the sheets, mattress cover, mattress and box spring were totally permeated.
I don't think I was in a coma longer than two or three days. Or maybe it was a few seconds. Regardless, it was delicious.
When I had been resurrected, I felt Mark pull out and gently help me lower my legs. He lay next to me and began to kiss me softly.
I was a mess! My hair was disorderly. My make-up was smeared. My stomach and thighs were drenched in my own cum and my bottom was drooling Mark's manly juices.
Mark said I was beautiful. And because he did, that's how I felt.
I think we fell asleep for an hour or so. I awoke first. Mark was naked, on his back and breathing heavily. His cock was limp and flopped up and almost to his right hip.
There was no going back to being a boy now. I knew that. And I didn't regret it one bit. Maleness was for real men like Mark. Not little nancyboys like me.
My real man's cock was still largely unexplored territory for me. I decided to change that.
I took its considerable substance into my right hand and hefted it gently. It was heavy! It was slick with my anal juices, his cum and even <blush> little dribbles of my poopy. I got onto my knees by his hip for a closer inspection. Wow, what a set of nuts my man had. And the bag was so dark and hairy. I gave them a good feel-up. Mark stirred a bit. They looked scrumptious, so I leaned over and gave Mark's balls a nice lick-up. All over. With my tongue. A nice, warm, ball bath for a nice, warm man.
Mark groaned nicely, but didn't awaken.
I decided that I wanted his awakening to be a very pleasant experience.
So I skinned Mark's bulbous cockhead and kissed it lovingly. With a series of flutter kisses. Then I took the throbbing, slick head into my mouth and licked and sucked it with all my love and all my growing skill.
Mark's eyes fluttered and he awoke, then smiled when he saw my loving attentions. And he adored what I was doing.
So did I.
Oh, girls! Cocksucking is a wonderful experience for the donor and the recipient. Warmth. Fluids. Sounds. Smells. Intimacy. Love. Then the girl gets her big reward. In her tummy. All over her face. Maybe both.
Mark's eyes got really big right before he came down my willing, eager throat.
The ability to give someone pleasure like that was the most empowering feeling I had ever had.
Chapter Eight The Big Surprise
Over the next two weeks, Mark and I had a white-hot affair. I gave myself to Mark body and soul and he taught me how to fully appreciate a man's adoration.
Dad and that little tramp Barbara gave us a lot of room. Barbara figured out that I KNEW. She didn't care. Dad, who was getting the dream pooty of his life didn't care either. Mark spent a lot of time in my room, fucking my pretty bottom all night long, then going to his construction job. Somehow, he didn't fall 20 stories or saw off a hand or anything.
Life was beautiful.
Then Mom came home.
Mom was supposed to come home on a Sunday, so Mark and I were a little bummed that Saturday afternoon in my room. We had some Plan Bs, but us together was central to all our plans.
Despite our anxiety about the future, we were having a great afternoon. Mark and I had discovered how much we enjoyed him "eating me out." Mark would lie on his back and I would straddle his shoulders, facing his feet. I would lower my bottom onto his eager mouth and he would lick and dig his tongue into my bottom until I was cumming frantically and squealing out his name. Then, since I was so wet and open, Mark would flip me onto my back and fuck me hot and hard.
Mark and I had gotten immune to the sounds of sex coming from my parents' room. That little tramp Barbara seemed to be treating my father like an amusement park. And was enjoying every ride.
I guess we were a very noisy bunch that afternoon and were oblivious to our surroundings. I remember thinking vaguely that Dad must have used the Venus Butterfly or the Mexican Hat Dance or some other move on Barbara, because she was screaming enough for two femmes.
Mark was on top of me, pushing that big boy into me when a portion of my brain alerted me to the fact that there was, in fact, more than one girlish voice in the room next door. But before I could crystallize the thought, the door to my room was flung open and there stood there stood Mom!!!
She had come home a day early to surprise us. Yet, surprised herself. First by seeing her husband fucking my pantyboy friend, then her nightied and pantied son being thoroughly fucked by his other best friend.
Sometimes such a shock causes temporary blindness. Or life-threatening violence.
But Mom was made of different stuff.
She only screamed once more, then she ran down the stairs, got into Dad's car (it's newer) and drove off.
She never came into the house again.
Chapter Nine Life after Mom
Well, I certainly didn't want that to happen. Frankly, though, I think it made Dad very happy. They hadn't gotten along well for sometime and except for getting skinned alive by Mom's lawyer, Dad hardly had to deal with her again.
I loved Mom, but in a way, it was all kind of her fault. When you put a boy in panties, don't be surprised if he likes them.
Dad and Barbara became completely open about their "affair" and, skipping ahead a bit, when Dad's divorce was final, he married Barbara. In Vermont, but that counts, right?
For a month or so after the Afternoon of Big Surprises, Mark and I spent every free moment having sex.
It was wonderful. But I must admit, I was becoming totally aware of the power I had over men. I saw the way men looked at me when I was out and about when Mark was at work. Rich men. Powerful men. They wanted me.
And I began to want them. I was too young to be with just one man. Even a man as easy to love as Mark.
One night at Mark's house, things changed.
We had just made glorious love. I was wearing only black, fully fashioned stockings and a matching garter belt. My bottom was gaping and leaking Mark's cream. My privates were sticky with my own spendings.
For some reason, something popped into my mind. "Mark," I asked. "Didn't you say once that Daddy read some magazine about girls like me?"
Mark looked at me curiously. "Yeah," he said. "Are you saying you never heard of Panty Boy magazine?"
I hadn't and said so.
Mark was so eager to please. He got up, said, "I'll get you one." And he left the room.
Moments later, Mark returned, clutching a glossy magazine. He handed it to me.
I looked at the cover. Oh my.
Until that moment, I vaguely imagined that there were two pantyboys on earth. And I was the pretty one. That little, Daddy-stealing tramp Barbara was the other, not-so-pretty one.
That vague imagination ended when I held Panty Boy magazine issue number 83 in my trembling hands and beheld its cover.
I had some serious competition for the "prettiest pantyboy" title. That was the bad news. The good news was that I was not alone.
A stunningly gorgeous "boy" in full make-up was kneeling in front of a stern-looking, middle-aged man who looked like a teacher or a principal or something. The man's very large cock had just produced enough sperm and semen to float a small country's armada. And it was all over the lovely, perfectly cosmetized beauty's face, hair, neck, flat chest and fingers. Rather than appearing offended, the pantyboy seemed to be joyous, a broad smile exposing her perfect, white teeth. The little creampuff was wearing only pink panties, from which protruded a tiny, spewing penis.
There were people like that in our world?
The men at the construction site, Daddy and Mark, "read" this magazine and saw pictures like that? Pictures of beautiful pantyboys submitting to stern, powerful men?
I was wearing only a lavender babydoll that didn't cover my privates, stockings and a garterbelt. I didn't tear my eyes away from Panty Boy to look at Mark, but I knew that he could see my frantic stiffie and aching pellets, just from looking at the cover.
I opened the magazine. The first pictorial was called "The alumni let the cum fly" and it was all about this private boys' school. The first two pages showed several good-looking young men in school uniform. They were doing school things, learning and stuff, then studying after dinner. A caption at the bottom of the second page said, "But let's see what happens at Fillbottom Academy at 8 p.m. each evening."
I turned the page. And saw the boys taking on a whole different manner. They began stripping and then suddenly, they were all naked!
Turned the page. The "boys" were all putting on make-up, tiny nighties, stockings, garter belts, and big, stiletto heels. They were all pantyboys! And pretty ones.
Next page. They were pairing up. Like Barbara and I did before she got trampy. Then they were kissing and sucking and licking. Oh, it was incredible. I wanted to reach for my popsy and relieve the awful pressure building in my "pink purse," but just then, I felt Mark's warm, wet mouth consume my peener and begin to suck it sweetly.
Oh, girls. Imagine reading the best porn you've ever seen while your lover is polishing your knoblet! That was world-class sweet of him!
I turned the page again and there were men! Naked men! Hunky, naked men! They were the teachers. No wonder they wanted to work there. Each hunky, naked man carried off a delicious cupcake for a full night of fucking. Only Jennifer, the babe on the cover, remained. She was to be the Headmaster's "date" that evening.
Jennifer seemed shy, but excited as she entered the headmaster's office. Her blonde hair was in a boyish cut and one could see her 2.5-inch penis standing straight below the hem of her diaphanous, pink nightie. But those were the only boyish parts about her. I was envious. Must be camera angles, I thought. No pantyboy is prettier than I am. Which is true, by the way.
The headmaster looked to be about 60, with white hair and a real "attitude," you know? Like he's the king of everyone. Jennifer sure acted submissive around him.
Mark was sucking me to the edge of Cum Cliff when the headmaster exposed his huge cock and said, "Look how ferociously rampant you make me, Jennifer! You're the most exciting, most feminine person on this earth. I love you, more fully and more hotly than I could ever love anyone!"
All those pictures and what made me whimper, then explode into my lover's mouth were those words of love and devotion from an authority figure, a Daddy, for his pantyboy lover.
My back arched and I saw new constellations. And planets where truly alpha males ruled over beautiful, submissive pantyboys. Where the sissies lived to serve their men and the men treated the sissies as the world's royalty.
Poor Mark. He had only sucked me off a couple of times before that day. I don't think he was ready for the deluge of cum that my first reading of Panty Boy wrenched from my balls.
What kind of publication was that? Who read it? And where did they find the pantied princesses to fill its pages? Did they use the same cuties over and over? Or were they always finding new "material?"
I was about to ask Mark all those questions, but his mouth was still full of Cheryl cream, the tastiest treat on Planet Earth. <giggle> And I didn't want him speaking with his mouth full.
As Mark continued to pleasure my pricklet orally, I turned the page on my "guide to a better world." Sorting my feelings out at that moment was a bit difficult, other than the feeling that I really loved having my pricklet pleasured. But I did recognize the obvious fact that I, an apparent, natural-born sissy, was deeply and incredibly turned on by the prospect of submitting to an alpha male who was older (even the 60-something "headmaster"), handsome, and very "masterful."
Young men are fun. But oh, you "daddies."
I dared to turn the page.
Dr. Fillbottom, the headmaster had removed his trousers and the lovely Jennifer was sitting on his naked lap. They were kissing deeply with a passionate exchange of tongues. The headmaster was tickling the pretty angel's jewels with his massive right hand. Jennifer was skinning the hood of Fillbottom's massive weapon with her fairy-like fingers. In the next picture they were both cumming helplessly, consumed by their passion and deep, mutual love.
My balls stirred, sending me a reminder that they were still producing that stuff I love to shoot.
On the next page, Fillbottom was licking Jennifer's creamy spendings from his drenched hand and saying to the delicious, little creampuff, "That was wonderful, Darling. You're an angel from heaven. Aren't you glad I 'pantied' you and the other seniors at this formerly all-boys' school?"
"Oh, yes, sir," the little doll said. "Being a pantyboy your pantyboy is my whole life now."
My balls actually throbbed when I read that. The idea of being "possessed" by a powerful, older man stirred my little peanuts like no other notion I had ever had.
I turned the page.
Fillbottom kissed his lover, then laid her on her back on a bed in his office. Positioning himself in a chair at the foot of the bed, Fillbottom lifted Jennifer's left, porcelain foot to his loving lips and began to kiss each enameled toenail. Apparently, that was on Jennifer's "top ten things that make me cum hard" list because her recently used peeny was up and red again and her head was thrown back in anticipation of ecstasy. It was not long in arriving. Jennifer had her nightie pulled up over her nipples and she was teasing them (and Fillbottom) by rolling each sharp, erect point between thumb and forefinger as Fillbottom kissed, licked and sucked each gorgeous digit. Inevitably, the "reader" was treated to a picture of a sexually frantic Jennifer HEAVING cum from her tiny prick. Then ejaculating helplessly again when the naughty headmaster tongued every square millimeter of his sensitive, sensual lover's right foot.
I was pretty sure that Fillbottom was going to fuck Jennifer eventually, but I didn't need to wait to see that part of the "pictorial." The toe sucking did me in. Even Mark was surprised by the tsunami of sperm I jettisoned from my balls when Jennifer spurted, eyes wide and completely helpless before the power of her man.
I was whimpering and crying so much that Mark thought I was ill. The long, slurpy, grateful blowjob I gave him then must have rid him of that notion.
We were so exhausted from the intensity of our emissions that we slept after that for several hours. If, when I awoke, I had just made love to Mark and ignored the Panty Boy magazine at the foot of the bed, with its massive cumstains new and old, my life may have been very different.
So it's a good thing that I didn't.
Mark was still sleeping as I looked at the next 30 or so pictures of Dr. Fillbottom and Jennifer. The little sweetie had small "parts," but an amazing ability to produce and discharge large quantities of thick, creamy cum. Kind of like me <giggle>.
After Jennifer's sweet agony from the toe sucking, Fillbottom licked up every drop of her precious cum from her flat, soft tummy, paying particular attention to the angel's "innie" belly button. Jennifer squirmed, but managed to keep her fresh "cargo" on board. The look on Jennifer's face was one of pure adoration for Fillbottom. Either she was a great actress or they were an actual "item" in real life. I found the second idea to be phenomenally exciting.
When Jennifer was de-spermed and clean, Fillbottom accepted her earlier invitation to worship her puffy nipples. They weren't quite titties, but they seemed to be showing just the faintest hint of developing into them. How was that possible?
Anyway, Fillbottom was as skilled and adept at nipple adoration as he was at every other facet of lovemaking. Jennifer was soon, once again cumming helplessly and copiously in an agony of delight. Later, I discovered that Panty Boy magazine photographs their pictorials over several days, allowing the pantyboys and their lovers to be photographed cumming at least a dozen times each in what appears to be two hours or so. At that moment, I was wondering why Mark and I only seemed to be able to spew our goo seven or eight times each day.
Watching Fillbottom pleasure his Jennifer, comparisons with Mark, the only man who had ever "seized my assets," were inevitable. I was vaguely aware that Fillbottom was fictional (clearly a distinct advantage over the very real Mark). So perhaps what I concluded was unfair. But some was quite accurate.
Fillbottom was very oral. Which was very smart, since at 60 or so, Fillbottom couldn't get a "big boy" nearly as often as a man like Mark, one-third his age.
When Fillbottom did manage a "chubby," he employed it as one would impart a treasured asset. Fillbottom, and to my thinking, all older men, valued their lovers more. Young guys like Mark, I reasoned, had more woodies, but older guys applied every asset they had to ensure their lovers' complete satisfaction.
Plus, older guys had money.
A nice, little extra, don't you think?
I sighed and decided to see what else was in that lovely publication.
I sort of skipped past the rest of the Fillbottom-Jennifer story, noting that Fillbottom's second erection ended up in Jennifer's delicious bottom. And Jennifer's cum ended up breathing free air.
The middle part of Panty Boy magazine book was a lot of "candid" photos about some party a guy named Nick Nickerson had at his home. Nickerson was the editor, publisher and 100%-owner of Panty Boy. He called his home the "Panty Mansion" and it was in some place called Fromage, Wisconsin. Isn't fromage the French word for "cheese?"
Anyway, the party was incredible. Male, A-list celebrities all over the place. I don't mean some Congressman from a Rust Belt state or the guy who played Jason or Freddie. I mean the top guys! And they ALL had something in common.
Each A-list guy had a scrumptious, feminine pantyboy on his arm or in his arms. Each pantyboy was beautiful and perfectly made up. Each was wearing a lovely, evening gown and five- or six-inch-stiletto sandals over her perfect, stockinged feet. Most had boyish haircuts and flat chests, but some had longer, even long hair. And some appeared to have breasts!!! How was that possible?
Whatever. I learned a lot from that dumb pictorial. There are lots of pantyboys. The Panty Mansion appeared to be the epicenter of world pantyboydom. Nick Nickerson is the king of pantyboys.
That was good to know. Really good to know.
I flipped to the last pictorial. It was a good one.
The title was odd. "Whipping Cream."
I lay on my back next to the still-sleeping Mark and read on.
A pantyboy who, once again was almost as pretty as I, was on her back, in bed, in a huge, luxurious bedroom. She was wearing only black, fully-fashioned stockings and a ruffled garter belt and appeared to be barely 18. The naked man who covered her with his body as he shoved his cock vigorously in and out of her perfect pootie, was quite handsome and appeared to be in his early 20s.
They were kissing passionately and the man, identified as Ray, seemed relaxed and appeared to be enjoying himself immensely. The pantyboy, identified as Paula, was enjoying the fuck, but seemed very anxious for it to be over.
I soon found out the reason for her anxiety.
"Oh, Raymond, please hurry," the pretty cupcake said. "My husband will be home any minute and he's insanely jealous!"
That young thing had a husband? A husband rich enough to afford that luxury? Now that was interesting.
Ray was a bit of a cad. "You worry too much, Baby," he said. And he kept fucking her.
Despite her discomfort, the little doll was being well-fucked and she made a messy cum all over herself. Twice.
Still, her eyes were fixed on the clock as Ray moved toward his climax. "Oh, please cum, Raymond. You have to leave. Trevor will be home any minute. Why did I ever do this?"
But Ray just pushed on, taking his time until he began grunting and spurting his big load into the married lady's bowels. Just then, Paula heard the front door open.
Paula became panicked, pushing Ray off her and whispering frantically to "Get out! Out the window! Now."
In his post-cum lethargy, Ray was slow getting off his pantyboy lover. He kissed her, picked up his clothes and, finally, went out the bedroom window and down the drainpipe to the ground.
The door flung open. Trevor took one look at his pantyboy wife and assessed the situation quickly and accurately. Cum was oozing from her bottom. Her make-up was smeared. And she had the guiltiest look in the history of civilization.
Trevor, who was a delightfully handsome and fit man in his late 30s, also noted the open window. But instead of running to the window, he ran to the closet. And emerged 15 seconds later with a fully-loaded rifle. Paula screamed when Trevor took the rifle to the window, got into firing position, took aim and fired a single shot. Trevor smiled, stood and returned the rifle to the closet.
Paula screamed again. Had her husband just shot her lover? Was she next?
She seemed terrified.
They had good actors in Fromage, I thought.
Was Trevor going to strangle Paula with his bare hands?
He walked toward her. She began to sob and wail, begging his forgiveness. Telling him that she would never do anything bad again.
Trevor was angry. Very angry. But he also seemed to be enjoying himself just a little.
Paula expected the worst. And she wasn't far off. I remembered that the title of the pictorial was "Whipping Cream."
As Paula sobbed and begged and promised to repent and reform, Trevor silently removed all his clothing. He had a great body! Then he sat in a hard chair and beckoned Paula to him.
Paula's heart lifted just a notch. Was he going to accept her apology and engage her in makeup sex which can possibly be the world's best sex?
No such luck.
When Paula reluctantly obeyed her husband and stepped next to him, he grabbed her writs roughly and flung her body across his knees.
He was going to spank her!
My little nuts were quivering in their pink bag again.
I turned the page. Almost absentmindedly I noticed that Mark had awakened. He had unhooked my left stocking from its garter straps and was sensuously rolling the sheer treasure down my leg, over and off my foot.
That was nice, but I wanted to see what was happening in the "Whipping Cream" story in Panty Boy.
Paula began crying and begging again as she lay across her husband's knees, her pink bottom exposed to his raised hand. Her [late?] lover's cum was impudently oozing from her anus, infuriating Trevor even more. I could actually see the tears fly from Paula's pretty eyes when the first slap hit her tender butt.
Oh. It was so exciting and I didn't know why. The very bad little kitten was being punished for betraying and humiliating her loving husband. He was taking a "firm hand" with her. And she was in complete and total submission to her husband. I adored it all and my little doodle was fiery red and aching for relief yet again.
That was the exact moment that Mark, my dear Mark, showed me how much he understood me and took care of my needs.
Mark raised my left foot to his lips and began to lick and suck each of my toes. Just like Dr. Fillbottom did for Jennifer in the first story. Of course Mark knew that lovely scene was in the story. The pages on that part were already stuck together when Mark first gave me the magazine.
As Mark rolled his tongue around my little piggies, I tried to read the Panty Boy story. He was so darned good at toesucking. The heck with the story. I slammed the magazine down, arched my back, squealed and came. Thoroughly and delightedly.
Mark was the best! Actually, he was the "only" for me to that point in my life. His only real drawback.
My little dickie was sore from cumming so much and so hard. My prince was making it feel all better by kissing it and licking up my spendings. What a doll!
But that was making it stiff and achy again, <Sigh>
Anyway, I was calm enough to read the tale of reddened tail again.
Poor Paula was getting spanked really hard from her husband Trevor. The model who portraying Paula was either a great actress or she was really getting pounded. The Academy award moments were yet to arrive, however. The first one occurred when, having counted the 30th swat from Trevor's hand, Paula heard Trevor say, "Now for your real punishment. Stand up, you little tramp."
Paula's ass was fire-engine red and her face registered horror. What was her cuckolded, furious, perhaps murderous husband going to do?
She was crying and sniveling as her husband placed her hands on the seat of a chair, her sore bottom completely exposed for further abuse. Which appeared to be imminent, since Trevor was retrieving the belt from his trousers.
Paula was getting the strap! Oh! She deserved it, the trampy little tramp. She was trembling and panic-stricken, but didn't move. Most oddly, her tiny prick was red as her bottom, stiff and twitching.
Oh. So was mine. Did I want a firm hand from a man? If so, did I really want it to be THAT firm?
Mark was rolling down my right stocking as I turned the page. He took my toesies in his mouth as I saw THE picture of the whole issue of Panty Boy.
Tears were flying 360 from the fallen angel's eyes as Trevor's strap slammed into Paula's sinful bottom. She had obviously screamed, but the odd part the best part was that Paula was cumming as if she were possessed. Two-foot-long cum ropes exploded toward the camera. From the strap. The discipline. The submission.
Mark's mouth and lips were giving my toes the imperial treatment. Panty Boy was filling my head with a new vision of who I could be. It was a very good day for me.
He kept licking and sucking my piggies so nicely as I turned the page and saw Paula sent to the corner after ten wicked strokes. Welts were strewn across her soft, crimson globes. Trevor's big monster was thick, stiff and ready for the final humiliation. Moving up behind Paula in the corner, Trevor pushed his prick into her painfully sore anus with one smooth stroke. Completely taken by surprise, Paula yelped.
I yelped. And, once again, I jettisoned my sticky load. I was whimpering and squealing, then begging Mark for a kiss and then another. And another. Then Mark mounted me, entered me and fucked me hard. Oh, I wanted it so badly. From him. From Trevor. From Dr. Fillbottom.
Poor Mark. He was my first, which meant he wouldn't be my last. A part of Mark knew that. But at that moment, I was all his. Under him. Skewered by him. Then I was a receptacle for his sperm. A willing, loving receptacle.
I was filled with love for Mark, but with a greater love for the life I knew I would have.
Chapter Ten A Pantyboy for "Panty Boy"
"Whipping Cream" had a happy ending. Just thought you would like to know. Trevor took Paula into the shower and got under the warm water with her. Lecturing her on fidelity, he washed her all over. She eagerly agreed with everything he said, hoping that her punishment was over.
Trevor dried her off, then watched as Paula powdered and perfumed herself and fixed her face. Then slid into a little pink nightie, pink stockings and pink puffy mules. She was beautiful! And Trevor couldn't help himself. He loved her. And Paula knew it. In the final photos, the married couple made up. In the best way possible.
We never did find out whether Ray, the slimy homewrecker, survived the experience. Of course, we must remind ourselves that he was just a fictional character.
The next few weeks were divine for Mark and me. But I think even he knew what I had to do.
I bought a digital camera, girlied myself up and took lots of pictures of my magnificent self. Then I picked out the ten best photos (they were outstanding!). That day, a Thursday, around noon, I sent an email to Nick Nickerson, publisher of Panty Boy magazine. With 10 very nice attachments.
Figuring I wouldn't hear anything for several weeks, if at all, I enjoyed my usual lovely night with Mark, giving him the usual delicious sendoff when he left for his construction job at 6:30 a.m. Mark would be going off to college in three days. I was very sad to let him go, but sort of happy about the possibilities, you know?
I was at the curb waving as Mark got into his car and drove off to go to work that morning. As usual, several neighborhood men were sneaking peeks at me out their windows. I guess I was quite a sight in my see-through peignoir, stockings and big heels. And I guess I did have a faceful of Mark's cum.
I went inside and took my shower, then got dressed. Just as I was thinking about scaring up some breakfast, there was a knock on the door.
A neighborhood man desperate for some pantyboy pootie?
I opened the door. To a stranger. In a dark suit, white shirt and black tie. And a chauffeur's cap?
My mouth was open. But his zipper stayed up.
Then he spoke. "Miss LaFemme, my name is Maxwell. I'm Mr. Nickerson's personal assistant. Mr. Nickerson requests that you accompany me to Fromage, Wisconsin. He wants you to grace the cover of a future issue of Panty Boy."
Did I hear Maxwell correctly?
I asked to be sure. "You're going to drive me to Fromage, but that's "
"Oh, no, Madam," Maxwell said. "Mr. Nickerson's private 'Panty Jet' is at your local airport, awaiting your arrival."
Let's see. It's exactly what I want. And what I want apparently wants me.
"Give me a moment to pack, Maxwell."
"That won't be necessary, Madam. Mr. Nickerson will provide every thing you need."
Just like that, I left my old life and the people in it. Even Mark. Which may have been a mistake.
Time will tell.
Find out what happened to all of us, Amy, Judy, Sandy and me in "Sissies and the City," an upcoming story same panty time, same panty channel on this web site.
Please tell me what you think at firstname.lastname@example.org
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