A Song for Sissies

Chapter 4

Chapter 4

Society's Progress

Society's Progress

"After ten thousand years of women being oppressed, the pendulum has swung backwards. Modern society encourages girls to freely express themselves. To dress like sluts at school and post videos on social media dancing with their tits out. Girls courageous enough to post nudes on OnlyFans to pay for college (and shoes) only prove how far women have come. Society's progress.

The reason boys are drawn to become girls is that they're jealous of them. Everywhere they look, girls are having way more fun being the center of attention. Growing boys know one fact in modern society: females, not males, are the key holders to sexual pleasure. Which means girls get to play dress up and suck big cock whenever they want.

That jealousy and horniness boils inside until these boys ask, "If I become a girl will I get unlimited access to sexual pleasure?" Once that idea is planted in their head, they're screwed. They shave, moisturize, and dress to become the center of attention. Willing to degrade themselves in any way to hold the keys to sexual pleasure. The subject of this book is boys of this type. We call them 'sissy'.

They don't stop until one night dressed in white teddy lingerie, they look up at a real man that's twice their age. Outside of this room, he's known as 'boyfriend', 'husband', or 'daddy'. But here, in secret, he's a tense body filled with sexual energy. He's a cock that drools cum begging for release.

At this point, Mother Nature or Biology takes over, and it doesn't really matter what's between the sissy's legs. The sissy, now holding the keys to sexual pleasure, unlocks him."

Swaroski, A. (2023).Psychology of Sissy Training. Stowling Publishing.

Getting ready in my sister Valerie's bedroom felt more natural. Prancing around in front of her white dresser, I prepare myself like a horny teenage girl excited to go out with her boyfriend.

"Dick and balls shaved?" I run a finger across my skin, and it glides smoothly. "Check."

"Ass squeaky clean?" I point my bottom towards the mirror and spread myself revealing the pink hole that will take a man's cock tonight. It gapes and winks. Proud of how thorough I was, "Check!"

"Body moisturized?" I rub another handful of lotion into my face and body. My body is so moist it sparkles. "Check!"

"Outfit ready?" I snap the waistband of Valerie's baby blue thong. My invitation for a man twice my age to proceed despite what was between my legs. I look over my shoulder and see the narrow blue fabric decorate my ass. "Check."

Having passed the 'Prepared to Get Butt-fucked Checklist' I step back from the mirror and observe my reflection. A soft 19-year-old with long brown hair dressed in his sister's panties. Valerie's panties struggle to hold back my stiff penis. I was so proud of myself but there was no one I could tell. Except one.

I reach into Valerie's dresser and pull out a white cami top that fits perfectly on my small frame. It made me feel less vulnerable than just wearing panties. Also less cold. White top. Blue panties. I take a deep breath and whisper quietly to myself, "You're ready."

Walking back to my boy bedroom, I grab black sweatpants and a hoodie to cover my girly clothes beneath. My weathered journal rests on the desk. The place where it all started. Nearly a hundred pages of stories now turning into reality. Who could have guessed that a little innocent dreaming of getting fucked by strong men and playing dress up in my sister's panties would lead to this?

I wonder what my parents would think if they knew the whole truth.

My mom admires my love for writing... but she doesn't know my stories are about me being filled with the cum from strong men.

My supportive parents let me stay in the family home during college break... but they don't know I use the bathroom to shave and enema my asshole. No idea that I wear their daughter's panties.

My busy dad works two jobs and was so proud that he bought me a car... but he doesn't know that I use it to travel to another man's house to suck his cock.

Did they know that they gave me everything I needed to become a girl?

I write a final sentence in the notebook before heading to my car to see James.

Can the bottom that my parents once lovingly wiped, powdered, and diapered become mine to shave, moisturize, and decorate to make dominant men cum?

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As I drive into the neighborhood, I see the community swimming pool covered for winter and illuminated by a lone sedan's headlights that is parked nearby. I park three spots away and hear silence as I turn my car off. My racing heart is the only sound. Thump. Thumpity. Thump.

I'm so nervous and intentionally avoid eye contact with the car. I know based on the description that James is waiting for me. My car door opens, and I walk briskly to the sedan, and feel the winter air kiss my upper thighs. The thong underneath my sweatpants does nothing to keep me warm.

The gentle thud of the sedan doors unlocking greets me as I arrive at the passenger door. I take my place in the warm leather seat and buckle up as the smell of a man's cologne fills my nose. James and I make eye contact for a few silent seconds. In the dark, his smile starts as a smirk and slowly grows into a grin. On the short ride to his house, we have awkward conversation about how reliable his car manufacturer is.

We walk innocently into James' house. It feels like I'm just hanging out with one of my friend's dads. His house is large, and I can tell from the silence that we're the only ones here. In the living room light, I see James is handsome. He has a tight hair cut with gel keeping his hair in place and is clean shaven. As I look up at him, I can tell James is about 6'2" and 190 pounds with an athletic build. His chiseled chest visible even with a shirt on. The smell of cologne is overwhelming.

James reaches into a cupboard and pulls out two stemmed wine glasses and says, "I'd offer you some wine but at 19 I don't think you can drink." James laughs. He fills a glass with red wine and the other with ice water.

"You have a really nice house. I like the furniture a lot," I say as he hands me the glass.

"You should thank my other half," James replies and grabs a picture frame from the kitchen counter. He gently rests a hand around my waist as we look at the picture of his smiling family on a tropical vacation. Tall blonde wife. Two kids. One girl. One boy. Both look like they're in their early 20s.

I feel a sense of shock with how transparent he is with showing his family. Wasn't this the guy that had to be 'super discrete'? A part of me wonders if he is so used to being the grateful husband? Or maybe he just wants to see me squirm?

What does he think about a boy who was younger than his own biological son who liked to dress up in woman's clothes... but I guess the answer was obvious. I take a sip of ice water.

He asks me about school and what classes I take. James is really friendly and at ease with me in his home. I respond, "I have to go back to college in a few weeks to start the Spring semester. I'm at my parent's now but I'll go back to the dorms."

After a few minutes of talking his body grows tense. His attention shifts from my words to my body as he wonders what is under my boy clothes. I promised him that I would wear my sister's panties tonight.

"Why don't you go upstairs and get comfortable in the first bedroom on the left. I have a surprise for you up there. I hope you like it. I'll be up in a few minutes, okay sweetie?" he says while smiling and takes a sip of wine.

Turning the doorknob, I enter his daughter's bedroom. Not the first time I've prepared in a girl's room. It felt similar to my sister Valerie's room. Girly pink accents on the walls, trophies on the dresser sit next to cheerleader Pom Poms. Pictures of her with girlfriends and a few boys decorate the wall and dresser. The smell of woman's perfume hovers in the room, perhaps from a visit over the holidays.

James left the surprise on his daughter's bed. A silver metal buttplug with a blue gem on the end. A note next to it says, "Hope you enjoy the surprise baby girl <3." I hold the buttplug next to my face to appreciate its size.

I slowly disrobe the sweatpants and hoodie to reveal my girly outfit. With a finger, I lube the toy and warm its cold metal surface. I lay down on the bed and push aside the blue thong to reveal my innocent asshole. With my legs in the air, I begin pushing the toy against the entrance of my virgin asshole. Above the headboard of the bed, I read upside down a motivational quote written in cursive that says, "Who runs the world? GIRLS!"

The buttplug finally penetrates my defenseless asshole. I feel happy and full. Returning the thong to its place, the fabric of my sister's panties is so narrow it does nothing to hide the blue gem of the butt plug. It sparkles.

James' voice echoes from downstairs. It sounds like he's talking to someone. What the fuck? Is someone else home?

Instinctively, I hide in the en suite bathroom and listen. The talking fades and my racing heart slows. Here in the daughter's bathroom, bottles of perfume sit on the vanity. Her closet full of outfits and a laundry hamper with clothes. On top lays a beautiful lacy white thong slightly wrinkled from use.

Can I really steal clothes from two young women? I grab the pair and hold them against my hips. I think they would fit around my hips, and they will match my white cami top. The thought is interrupted as I hear James talking again.

I return to the bedroom and drop the panties next to my boy clothes. My ear is pressed to the door but hears nothing. Creeping down the staircase I see James on the phone. He notices me and is shocked for a minute as I present my girly self to him for the first time in person. He motions me to the kitchen table to sit.

"Yeah. Mmmhm. Yeah." James says to whoever is on the phone.

On the main level I see the master bedroom where James and his wife must sleep. James' eyes are fixed on me, and he motions me to come to him. He holds me close, and I can feel his cock bulging from his pants. It radiates heat into my body. I hear the voice of a woman on the phone.

He traces a finger down my cami top and to the front of the blue panties. His long arms reach behind me and a single finger is inserted between my sister's panties and my butt. The probing hand finds the surprise he gave me in its proper place. Stuffed in my virgin asshole. He smiles at me so big, and it melts my heart.

His head lowers and we kiss passionately. His tongue explores my 19-year-old mouth and makes slurping noises. My soft skin feels the roughness of James' stubble. I ignore what the woman is saying while James pushes the buttplug further into me and then back out. He fucks me gently with the big toy. Our kiss prevents my moans from being heard.

"You're absolutely right," James says distracted to the phone.

Dressed up in front of this grown man I feel feminine. His fingers curl around my thong's waistband and they slowly slide off my ass until the fabric pops loose. They don't fall to the floor but rest around my upper thighs. The kitchen lights' shine a spotlight on my semi-hard 5-inch penis that appears gentle, shaved bare, and surrounded by small milky-white thighs covered in goosebumps. There's a cuteness to my physique.

"...forget we have to go to my parent's house this weekend. My flight back is on Friday." the voice that must be his wife can be heard saying through the phone.

James' body is on fire and he's losing patience. He unbuttons his jeans and drops his black briefs to reveal his masculine physique. Standing next to James I notice how different his manhood is from mine. Okay, now I know why people call it a 'cock'.

8 inches long and girthy. The most unique feature of him was the giant head of his dick. A pink-red helmet the size of a baseball. The urethral slit of his cock had to be at 2 inches long. My small penis disappeared beneath the shadow created by his shaft. I don't think about being too small. In fact, I don't think about my size at all. I'm not the man in the room.

"I have to go soon sweetie the game is almost on," James says to his wife.

He drops me to my knees and I'm eye level with the head of his huge cock. The urethral opening of his cock glistens with pre-cum. As I grab his cock and appreciate its size, I feel fucking weak. I stroke his stiff cock and see his full balls bounce with each stroke. The source of James' seed. The source of his family in front of me. I continue to stroke his giant dick and tenderly kiss his balls with the affection he deserves. James moans into the phone.

I open my mouth wide to fit my lips around the head of his cock. The smell of an actual man penetrates my head, nose, and throat. In case you don't know it's the smell of sweat, cum, ass, balls, and cologne rolled together, and it will absolutely make you go lightheaded. It smells really fucking good.

The voice on the phone says clearly enough for me to hear among all the slurping, "Are you there?"

I slow down sucking his dick and look up to see his face wearing a serious expression. He still holds the phone near him, but his eyes are wild. Shifting between me and the ceiling. Occasionally he looks down at my 5-inch penis that drools pre-cum on his wife's kitchen floor. He's in total ecstasy. I pop the dick out of my mouth and hold it over my face and smile at him. His shaft is completely covered in saliva.

"James are you okay?" His wife asks with a worried tone in her voice.

He shakes his head and comes back to reality. He uses a hand to guide my head back on his swollen cock and responds to his wife, "Yes, I'm fine sweetheart."

Unable to hold the phone any longer he stabs the speakerphone button before letting the phone fall to the kitchen counter. The head of his cock swells up larger in my mouth and James' hips start bucking as he fucks my throat. My gagging echoes in the kitchen and saliva streams out of my mouth and nose onto the kitchen floor.

"What's that sound?" his wife asks, filling the house with her presence.

James uses both hands to secure my mouth onto his mature penis.

"Sorry I have to cum." He shouts towards the direction of the phone. "I mean go." James corrects himself and reaches for the phone to end the call.

But before he could end the call, his eyes caught my face impaled on his cock. The 19-year-old boy working so hard to please him. Slurping, gagging, and swallowing his cock in his wife's kitchen. The young boy who made James feel like a man again. James balls tense in front of my face and I feel the slit in the head of his cock open wide.

"Have a good night, James. I love you." I can barely hear his wife say.

The smell of cum from the father of two fills my head. Shot after shot hits my throat. My 19-year-old mouth open wide to receive his sexual stress. Hundreds of millions of sperm from a real man swim in my mouth.

James takes a second to catch his breath before he reaches towards me and helps me off my knees. He holds me close and ends the phone call with his wife as he says "I will have a good night. Love you sweetie."

It takes me three swallows to drink his cum. James ignores the cum still on my cheek that I left behind and kisses me deeply. It tastes like salty cum and sweet red wine. His arms reach behind me and tugs on the buttplug until it pops free from me. My asshole gapes from emptiness. It would much rather be filled right now.

The butt plug that penetrated my core now hovers in front of my face. My eyes look from James serious face to the buttplug. My face reflects on its metal surface as I open my mouth wide and wrap my lips around its head. Accepting it as mine to clean, the little contribution I can make. The blue gem is the only visible part of the butt plug in my mouth. It sparkles.

James' hands drop my sister's panties to the floor and rip the white cami top off. His hands are so large next to my tiny 5-inch penis that is oozing pre-cum. He cradles my pathetic looking 19-year-old balls for a moment before directing us upstairs.

He follows closely behind me as we walk up the stairs. My virgin ass dances in front of his face. As I walk upstairs, he pushes a thumb against my virgin asshole. My moist hole welcomes the attention, and his large thumb penetrates me with little resistance. When we round the corner to enter his daughter's bedroom, he knows that I'm ready to be fucked.

Big hands force my body to lay on the bed of his biological daughter. My naked body is surrounded by white pillows and warm furry blankets. The swollen cock of a man twice my age points threateningly at my virgin hole.

James appears angry as he reaches into my mouth to remove the butt plug. Dripping saliva and sperm, he places it on the night stand next to a picture frame of his daughter. She's wearing a graduation cap and gown, and the frame includes a quote:

"Take pride in how far you've come. Have faith in how far you can go. But don't forget to enjoy the journey! Congratulations!"

"OOOOOOOOHHHHHHHHHHH FFFFFFUCKKK," my scream fills her bedroom as the giant cock head of her father pushes against my entrance.

James doesn't hesitate as he drives his hips into my 19-year-old body. Never have I felt something so intense. Never have I taken anything like this up my ass. Right when I thought about giving up, my asshole's defenses fail, and it swallows James fat cock. Welcoming the invader.

His racing pulse echoes in my body. I'm connected with a real man at last.

I'm not sure what it is at this moment that makes me feel like a real girl.

Maybe it was my useless penis that rests flaccid.

Maybe it was the wet noises my ass made as it stretches around cock.

Maybe it was the girly bedroom or the animal pillow that I was squeezing to brace myself.

But there was no denying the moment I hear the words, "Brett you feel so fucking good," as cock touches the deepest part of my 19-year-old body. That in this moment, the last remaining shreds of my masculinity are erased.