A Song for Sissies

Chapter 2

Chapter 2

The last barrier between a real man

The last barrier between a real man

"There are two main reasons boys show interest in wearing female clothing. First, decorating themselves in the accessories of a woman allows them to explore the gender role in the flesh. Given male's reliance on visual stimuli, they will stare at their transformed identity reflected in mirrors or take pictures of themselves and realize how much their idea of a 'female' is attributed to clothing and stereotypical behaviors like compassion and obedience.

If the cross-dressing experience is positive, they will navigate their environment in creative new ways such as exploring their mother's closet, preparing, and cooking a meal, and folding laundry, all while wearing female clothing.

The second reason boys are interested in wearing thongs, pantyhose, and high heels is because it feels really good and is fucking fun. It's unknown how common cross-dressing is because of social stigmas that prevent many from sharing this behavior publicly.

Recently, we conducted research to understand the psychological changes that come from wearing female clothing. We sought 18-21-year-old boys and asked them to wear a full lingerie set including garter belt, stockings, and high heels and record how this singular event impacted their sense of identity. The interest was tremendous, and we turned some away.

Dressed fully in lingerie, the boys mindset shift was so obvious you could see it in their eyes. See it in their body language as we removed the barrier of stigma, and they grew comfortable in their new identity. Realizing switching sex roles from male to female is possible. Natural even.

One notable participant refused to remove the clothing as the experiment ended. Begging us to let him take the lingerie home. Stuffing the high heels in his backpack, he made his way back to the dorms hiding the lacy, white lingerie underneath the clothes he arrived with. Kept secret from the world."

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

The next morning sunlight filled my bedroom, and I stirred gently in a sunbeam until I woke. My mind raced again with thoughts... I'm hungry, time for breakfast. I walk downstairs to the main level of the family home where I am staying for the December school break. My folks are travelling for work leaving me by myself. I didn't mind the solitude and it was a comfortable place to stay. Days of being alone did cause my mind to wander as you can probably tell!

With the only sound in the house was me chewing, a thought came to me. Why in my stories does the protagonist wear female clothing? A man can still have sex with my extremely submissive and perverted protagonist without decorating his young body in woman's panties. Right?

After another bite of cereal, I came to believe that wearing women's clothing was a personal choice you have to make. To purposely ignore what was between your legs and dress in a way to become a target for real men. Tempting them to proceed with reckless abandon.

The goal was to dress so sexy that men boiling with sexual desire wouldn't stop themselves after they ripped off your clothes and saw that you weren't female. A boy dressed in lingerie was an external sign of consent, submission, and obedience. It says, in bubbly pink letters "Fuck me please!"

After another bite I think to myself how important this non-verbal communication is given the fact that there's two men and a hierarchy needs to be established. Wearing lingerie wouldn't cause you to be mistaken for a real girl, but maybe it helps to play the role? Maybe it makes you vulnerable to their cock?

I assumed in reality a boy wearing women's clothing looked a little ridiculous given the tight hug of panties on his manhood, and of course if you got hard then I guess it would push the whole thing off your body! Despite how ridiculous a boy wearing woman's clothes seemed, deep inside I knew that dominant men would love seeing a naïve boy who purposefully embarrasses himself for attention.

The thought of a hairy hand reaching into a thong filled with smooth balls and cock made me horny. My penis began to harden.

How can I get access to female clothes to see for myself what it feels like? Does my protagonist go to the store and pretend the undergarments are for his girlfriend? The thought terrified me. Or even worse, do people admit they're for themself and get some fashion advice from a worker? I dreamed of walking into a closet full of women's clothing that I could try on and pick my favorites in secret. I need to decorate myself for men and feel the anxious energy of their sexual tension boil over.

The first option I considered was a neighbor up the street who I occasionally helped dog-sit and had a daughter who was close to my age. I had a good feeling that she owned a couple pairs of cute panties. Maybe I should look at her mom's closet too just in case? A feeling of disgust fell over me to think about sleuthing through a perfectly happy nuclear household for women's undergarments to steal. Oh well that's my only option! I would spend time rationalizing this behavior until the opportunity presented itself. I did do them a favor after all by dog-sitting. What's the harm in compensating myself for my time?

I walked upstairs to my room and before I touched the doorknob I stopped and looked behind me. The house was still. What about Valerie's room? She's my older sister that has gone to college for a time and left the house but maybe she still has something in her dresser? I proceeded into my room to sit and fully consider the idea. It may be difficult to believe that I didn't once think about looking in my sister's dresser for clothes. But I'll have you know the thought did somewhat disgust me - this was my sister after all... After some time I convinced myself to just "look" but had no intention of actually removing clothing from her room.

Despite the house being empty I acted as if there was a camera watching me. I knocked gently on her door and then asked, "May I come in?" Of course no one responded, and I slowly walked into the room that was left in a similar state as when my sister lived there. A white dresser with pink flowers in bloom and a white bed frame with a white and pink lined bed set. I started pulling dresser drawers and saw her clothing. Socks, shorts, pants, more socks, t-shirts, panties, bras, and pajamas. After getting a full inventory of the dresser contents I slowly pulled again on the drawer handle that hid her panties.

My heart was thumping with anticipation that I may find something I like. Inside, rested a see-through black lacy G-string that was barely any fabric, a leopard print cheeky with black waistband, baby blue panties that said "Calvin Klein" on the waistband, and various colored Granny Panties that were of lesser interest to me. Not even I was that desperate.

I grabbed the first three and wadded them up and headed to my room. As I walked to my room I realized if I was caught that there's no excuse. Nothing I can say to explain my actions. This was a moment of 'no turning back' and I accepted that.

I placed her unmentionables in the bottom of my sock drawer for safe keeping. The feeling of disgust filled me as it wasn't lost on me that my sister, who I didn't even really like that much, was the original owner and wearer of these panties. An intrusive thought wondered if a real man filled with sexual desire had ever ripped off a denim skirt to reveal these panties before. Did the thin fabric provide the last barrier between an actual man and where he will cum? Did large fingers rub the fabric until they became damp? Was this underwear wadded up and shoved in the mouth of my biological sister to prevent her from making sounds in her bedroom? I pushed all these thoughts away except one.

Will my sister's panties make me sexy enough to attract a man?

As dusk approached and the room darkened the desire to wear my sister's panties grew too much. I undressed completely and stared at my soft white body in the dresser mirror creating a "Before" image in my mind.

I watched my slender hourglass figure as I was quite skinny. My long brown hair was of a skateboarding punky style. My dick and balls were noticeable but appeared gentle except for a small tuft of brown hair. I twirled and caught a glimpse of my white butt cheeks.

My heart was beating fast in anticipation. I took a deep breath and began. Reaching into the drawer I started with the sluttiest looking one which was the see-through black G-string. I slipped it on and looked at myself in the mirror. Unfortunately, the narrow fabric in the front of the panties could barely hold me in as the fabric wedged itself creating a camel toe effect with my scrotum. I liked the breezy feeling these gave me because there was so little fabric, but they just didn't look that good. I took them off feeling disappointed that I only had two more chances and grabbed the leopard spotted cheeky. This one had more fabric to hold me in and as I worked them up around my ass it felt secure. The leopard spots were really cute and would catch attention but were a bit bold for my taste.

I was nervous as I tried on the last pair of panties. These least impressed me when I first saw them. The baby blue underwear. I worked them up my legs and felt the fabric contact my butt and covered my balls and penis causing the fabric to bulge. The waistband said "Calvin Klein" in big letters that wrapped around the waist. To my surprise these fit PERFECTLY, even as I started to get hard the fabric stretched and created a bigger bulge that I looked at while watching myself from a sideways perspective in the mirror. I turned around to check how they made my butt looked and the blue fabric created a beautiful contrast with my white ass.

I loved them. Nothing ridiculous or showy. A boy wearing baby blue panties is suggestive enough, right?

I turned around and spread my ass cheeks in front of the mirror and looked back over my shoulder as I watched the narrow blue fabric struggle to cover my pink asshole. After a few moments filled with confidence I said to myself, "Damn I look sexy." It's amazing how different I felt after wearing my sister's panties. I hoped the baby blue girly underwear would be a clear sign of my submissiveness and consent. A sign that I was willing to humiliate myself to be targeted by men.

The slats in the blinds were open slightly and I adjusted them to make sure no one could see me from outside. Kept secret.

Girly, sexy, eager, and fuckable.I thought to myself and felt relieved.

I sat in my bedroom with my new underwear decorating my body as nighttime covered the room with darkness. From the corner of my bedroom a strong man stared at me quietly. His dark eyes fixed on my body as he approached. I feel small next to him. His big hands touch my exposed skin and work down my body to hold me by my hips. Large fingers suggestively play with the waistband of my new panties. He tugs up on them and I feel the thong wrap tightly and squeeze my ass and balls. I remain silent except for a small gasp.

The baby blue thong on my delicate 19-year-old body indicated which of us will be the woman in the bedroom this evening.

Our eyes met and I smiled up towards him. My heart didn't race but it felt full and went THUMP, THUMPTY, THUMP sending blood and hormones all through my body. My penis starts to harden but the thong keeps me secured.

His warmth radiates into me and warms my small body. I'm totally exposed except for the tiny blue fabric of my sister's panties. They are the last barrier between a real man. The last thing separating him from the hole he will cum in this evening.

These panties weren't a barrier. They were an invitation. An assurance that I will relieve him of his agitated sexual energy, despite what was between my legs. My purpose.

My gaze submissively moved to the occupants in the mirror's reflection, but to my disappointment, the reflection revealed I was the only one in the dark room. My dreamy eyes and bulging thong with visible dampness showed how badly I wished to be with this man. How badly I wished he were real.

My broken heart wrestled with one question. Is there someone out there who will accept me as I am? Someone who can appreciate a naive boy with a secret, uncontrollable urge to wear women's clothing and satisfy dominant men. I longed for the comfort of a strong man who would tell me that all of these crazy thoughts have a purpose. Someone to tell me that my fantasies of being a sexual object for men was normal. That, somehow, I too was normal.

I pulled the front of my panties away from my body to reveal my soft penis leaking pre-cum that darkened the baby blue fabric. I didn't even orgasm. Anticipation alone soiled the thong with creamy wetness like a woman at peak ovulation. My sperm swim on my sister's panties searching for a target they will never find. "Like a bitch in heat," I said frustrated. It echoed in the room and sounded like someone else was speaking.

My creaminess saturated the panties and the pool of pre-cum was so much that it wet my bottom. I removed my sister's thong and placed them gently on the bed to dry. I felt my bottom glazed with cum from the panties. How the hell did I leak so much?

My head fills with fantasies. I cream my sister's panties as they are removed without consent. I salivate as cock rests on my tongue. My wet asshole opens to attract a dominant man to deposit his seed. My eyes dilate as I stare up at him, hoping that I'm what he wants.

But fantasies aren't enough anymore.

My stories about attracting men twice my age isn't enough.

Wearing women's clothing in my bedroom alone isn't enough.

I realize for the first time that I passed the 'No turning back' sign long ago. It's impossible to say at which point I could have "turned back," but it certainly isn't tonight dressed in my sister's thong.

I used a finger and cleaned myself by gathering the cum from the head of my penis and between my butt. With a glob of pre-cum on my finger, I rub it suggestively on my asshole. A sticky-moist noise filled the room as I touch myself. I push against my entrance. My cum made my asshole defenseless, as my finger slowly enters with little resistance.

Turning back to the mirror I spread my butt cheeks revealing my pink asshole glazed white from the wetness I produced. The mess I made. Millions of sperm swim directionless searching for a female object.

Was this natural for a boy like me? Did Nature ever plan for a boy's cum to lubricate his own asshole and turn it into a pussy for real men? I spread my cheeks wider and watch my ass quickly gape open and close, decorated with my sticky white cum. My tight hole advertises that it is ready to be filled. For the first time in my life I realize my whole body betrays my secret desire for men.

How can I possibly keep this a secret when every cell in my body aches for a true man?

I sensed something bad would happen if I didn't satisfy this itch in me. In return I was ready to give him anything he wanted. If I can find a real man that gives me answers and make me feel the warmth of being protected and understood, then what did it matter if he tugged on the thin fabric of my sister's panties and removed the last barrier that separated us? What did it matter if he uses me to cum?

Maybe this is normal for boys like me? To dress our soft bodies in cute clothes and satisfy Alpha men. It wasn't embarrassing, it was my goal. Maybe Nature intended for me to ignore 19-years of loving parental guidance and social norms and reduce myself to a breeding hole for a real man.

But where is he?