Good Girl Ch. 01: Discovery

Good Girl, Part 1

The first couple summers after I graduated high school brought a lot of changes and I had not found my direction or motivation yet. Uncertain if I wanted to go across state to the university, I decided to take courses at the local college to get some credits and find work to save some money.

My mothers' friend, Miss Anne, had recently completed construction on her new home about an hour outside of town. She asked if I could help her look after the house while it sold. I was allowed to remain in their old house while she sought a buyer. There were several houses nearby that were listed so confidence was low the house would sell quickly.

I was tasked with keeping the lawn tidy and the house clean in event the real estate agent brought by potential buyers. It was a too-good-to-be-true situation for me, close to campus and free rent. But what I found to be the biggest benefit was the solitude.

About two years earlier, I had discovered the joy of dressing in women's clothes.

Miss Anne took a trip out of the country for business and I had the house to myself.

She was barely out of the driveway by the time I loaded porn on my laptop. I settled in for a gooning session that started with female domination, which lead to pegging, cuckolding, and feminization/crossdressing.

One particular video that caught my attention featured a smooth-skinned, femme male serving a dominant couple. The wife had dressed the star of the show in pink panties and a satin maid uniform. She instructed her subject to kneel before her husband. With one hand, she pulled her husband's engorged cock from his pants and directed it at her kneeling subject's face. The husband towered over his new submissive maid. With the other hand, the wife pulled the maid's head toward the swollen, glistening head and whispered in his ear, "Service him, slut. Your training begins now."

The maid followed every command. Having satisfied her new master, she was rewarded with thick jets of cum that filled her mouth and covered most of her face.

He finished by rubbing his giant cock across her face and commended her with "Good girl, now swallow it."

I nearly lost my edge and I strained desperately trying not to cum.

Motivated by my favorite new video, I spent nearly the entire week trying on Miss Anne's panties, stockings, bras, corsets, dresses, blouses, and skirts.

I went completely down the rabbit hole. I slept in a baby-doll nightgown I found in the back of her closet. During the day, I often wore sundresses without panties.

At a meager 5 foot 4 inches, I am only two inches shorter her. Some boys are "late bloomers", my mother once said I am a "never bloomer". I'm petite and I like it.

Most women are taller than me. Some will us terms of endearment and it feels like emasculation. I like the sweeties, honeys, and sugars.

Rarely an older man will do it. I just smile and lean into with my submissive nature. It never leads to anything. I could only be so lucky.

Some of her older clothes fit my slender frame quite well. She is buxomly and my flat chest could not fill out her tops. Her little panties fit me perfectly though.

I picked out her clothes that accentuated my slim build.

Feeling the soft and delicate fabrics clinging to my smooth skin was exhilarating.

I experimented with the make-up she left behind. I enjoyed wearing her glossy lipsticks, eyeliner and mascara.

I did not stop to give consideration to those feelings, but I was instantly addicted. I want to feel more. I needed to feel more.

With each passing moment, my desire to be increasingly feminine bloomed. By midweek, I was consumed.

When I did venture out of the house, I wore a lacey, pink thong with a ribbon in the front and thigh-high stockings under my pants.

I fantasized about how it would feel to go out into the world fully dressed. And, I fantasized about being trained as a "full-service" sissy maid as well.

As that week neared an end, I felt dread that I had to return to my previous life lest Miss Anne discovered my new hobby.

I spent the last day, returning her clothes from where I found them and did all I could to cover my activities for the week.

Never again did I have an opportunity to explore my feminine-self...until I had the house to myself for the whole summer.

---

As Miss Anne was packing the last of her personal belongings, she was bombarding me with last minute instructions.

She was bossy in a alluring way. Perhaps a skill honed from whatever corporate job she has.

"Don't forget to water the lawn.

Make certain the trash goes out weekly.

Keep the bathrooms clean.

Pick up your clothes.

No parties or overnight friends.

Keep your cellphone handy in case the realtor needs to show the house."

As Miss Anne was walking out the front door, she told me she left some written instructions for tasks she did not have time to complete. She asked me to take care of the things on that list and she would call to check on them. She flashed me a smile, kissed my cheek, and said, "Don't have too much fun. I'll be checking in on you from time to time".

Once she left, the house felt bare. Some furniture and décor was left to dress the house for perspective buyers. It didn't feel like the same home anymore.

I began to wander the rooms to survey all the changes when I found the list she had left. Most of the items on it were about keeping the house tidy. But the last item read, "Please take the clothing in the guest bedroom to the donation bin when you no longer need them... enjoy yourself ;)"

That was oddly worded and unusually playful for her. I could not recall her using an emoji in the notes she has left me in the past. My mind began racing as I hurried to the guest bedroom.

No longer need them?

Laid out neatly on the bed were the panties and stockings I wore during my magical week two years prior. Hanging from garment racks, there were an assortment of dresses, blouses, skirts... and my favorite white baby-doll nightgown.

My body went cold. My heart was racing. I fled the room into the adjacent guest bathroom fearing I was going to be sick. I hovered over the toilet bowl with trembling legs for a minute while I regained composure.

How could she know? I came to the conclusion that it was only a coincidence. My mind was creating a narrative out of paranoia.

Then I noticed a bag on the sink that I did not recognize. Did she leave this behind as she was packing her belongings? As I opened to investigate, a note fell out to the floor. On it, written in pink lipstick was Miss Anne's handwriting:

"Be a good girl and throw out Mommy's makeup when/if you are done with it ;)"

Mommy?

The box was full of lipsticks, mascara, eyeliner and cosmetics with which I was not familiar.

This wasn't left for me. What was this?

I backed out of the guest bedroom and closed the door in a desperate attempt to shut the situation out of my mind.

An hour must have passed as I nervously paced the house. Then my phone rang. It was her. But, her contact name in my phone was change from Miss Anne to "Mommy" flanked by a heart and lips emojis.

My anxiety was overwhelming and my hands were shaking, but I tried to remain calm and still the tremble in my voice.

She said that she had just arrived home. She talked about traffic and what she need to get for her new home.

Then she asked if I had gotten to the items on her list yet. I sensed she knew I looked, but I lied nonetheless. She replied, "There's no rush. Take your time with it...and have fun, sweetie~".

I could sense a smirk in her tone. She was enjoying this cat and mouse play.

That evening, I could not fall asleep. I was trying to solve my dilemma: How did she find out? How would I get out of this? How could I explain it away? Why is she doing this? Did she tell my parents?

In my mind, I saw the words form, written in pink lipstick, "Be a good girl" and heard the voice from the video "Good girl, now swallow it".

The urge overcame me and I needed to wear panties, to feel feminine and alive again. I chose a cherished pair she had laid out on the bed. The caress of silky lace against my skin recalled that long lost feeling from my magical awakening two years ago. I felt my arousal under the fabric as I ran my fingertips up my bare thighs to my ass and around to the small triangle of fabric in front. I did not even create a discernable bulge in the fabric. There was almost no trace of masculinity and I admired how neatly the front of my panties laid flatly against my pelvis. I went to the guest bathroom mirror to see how they fit.

The note remained on the floor where I had left it..."Be a good girl"

I sifted through the bag looking for a good shade of lipstick. I found a set of press-on finger nails, shades of nail polish, and at the very bottom of the bag something familiar... a pink micro chastity cage. I have seen these in a number of videos. The sissy maid in my favorite video was locked in a similar, albeit larger, device than this one. The one I held was designed like pussy in the front with an elongated opening down the middle. I didn't pause to question my discovery. I wanted to know what this feels like. There had to be a lock for it, so I dumped the remaining contents of the bag onto the guest bed.

The last item to fall out was another note. It read, "A good girl keeps her clitty locked".

Taped next to the words was a vial of superglue. I was a puppet on strings. I did not waste a moment. Once I had the cage glued tight, I admired my little pink cage in the mirror.

The cage laid flat, capturing its little prisoner and pushing it into me leaving only small testicles clinging tightly against the bottom ring. I pulled my panties back up and, taking one last glance in the mirror, thought to myself, "I am a good girl."

I must have stayed up to nearly dawn putting on nails, practicing with make-up, trying on dresses. When I awoke, it was nearly midday. I was wearing my white baby-doll, chastity cage, and panties.

I heard the unmistakable sound of the front door lock followed by the door opening. My stomach was in my throat.

I flew to the bedroom door and locked it.

An unfamiliar male voice called out, "Hello?"

There was more than one set of footsteps.

The real estate agent...

Just then my phone started to vibrate.

I called out to the voice, "One moment, I'll be right there!"

From Miss Anne, a text read "(Mommy) I told Mark he can show the house this morning, I hope it's not bad timing. Be a baby-doll and make your guest feel at home." She set this up! I was about to be discovered - I had to act quickly.

I dropped my phone, threw off my baby-doll and shoved everything off the bed into the closet and dresser drawers. Thankfully, my pants and t-shirt were in the room. I pulled them up over my panties, tucked my painted nails into my pockets, curled my painted toenails, and opened the door.

Mark was standing right outside. I didn't expect him to be right there. I almost planted my face into his chest as I started out of the room. Stopping in the doorway, I apologized and made up an excuse that I had been out late and I was just getting my day started. I explained that I was going to take a quick shower while he showed the rest of the house and then he could show the guest room. He smiled, winked and said, "take your time" as he walked back to his clients.

Instantly, I realized I fell asleep with my makeup on and I was still wearing the candy pink lip gloss, eyeshadow and mascara.

I closed the door, ran to the bathroom, turned on the shower and began washing my face. I would say that I was practicing for a part in a college play.

I could hear voices moving through the house as I undressed and climbed into the shower. I was nearly finished when I heard a knock at the bathroom door. Mark had let himself into the bedroom and was now standing outside the bathroom door. I turned off the water, picked my panties up from the floor, and tucked them into my pants pocket. Not yet dry, I wrapped my waist with a towel and opened the door.

Mark was in the doorway as it swung open. He towered over me - I had to look up to see his face. I estimated he was early 40s. He had tanned skin and black with salt and pepper hair and a neatly trimmed beard. He had removed the blazer he was wearing when I nearly ran headlong into him at the bedroom door. His forearms were thick. His sleeves, rolled almost to his elbows, strained against the circumference of his arms. They were nearly as thick as my thighs.

His dress slacks appeared fitted - tight through the butt and thighs giving testament to his powerful stance and hints of his significant manhood.

He broke the awkward silence, "The clients saw all they needed to see..as did I. Sorry if I surprised you. Ms. Anne said I could... cum. And, she promised you would be willing to accommodate me." As the words left his lips, he produced the note that, during my haste to hide along with all the evidence from the prior evening, had fallen to the floor. He smirked, "But I see you found the present I left for you. I trust it fit; she told me you were very small." He glance at the towel, "Tell me, princess - Is your little clitty locked? Are you a good girl?"

I was speechless, frozen.

Am I still asleep and dreaming? Is this really happening?

Before I could react, he reached forward and pulled the towel off my waist and let it fall to the floor. He didn't need to look, my reaction confirmed what he knew.

My hands darted forward to cover my vulnerability.

Without any reservation, he reached around and grabbed my waist just above my bare butt. His large, rough hand ushered me out of the bathroom and into the bedroom. He stopped beside the bed. He had opened the bedroom window and blinds to let more light in. The cool air against my wet skin made me feel somehow more naked. It didn't help that anyone walking down the sidewalk would be able to see me, in my current state, through the open window.

Trembling, I conceded to my predicament and let my hands fall to my side. Their clever trap was on display for his amusement as well as anyone in the neighborhood who chanced to pass by. Although he didn't need to see my cage to size me up. It's obvious in the stark contrast between us.

I was both terrified and excited by what has happening, and what might happen. I had never before been so vulnerable. I felt a sense of submission to the man before me.

What was he going to do to me?

My excitement began to grow and it was I an obvious nervous wreck. I could barely speak. My throat was dry and my voice was shaky. "What did she promise you exactly?" I squeaked.

He enjoyed the question as much as my nervousness. He produced the baby-doll gown I had stowed in the closet and handed it to me. I held his gaze as I carefully pulled it over my head and pushed my arms through the puffed sleeves. He straightened the pink ribbon bow on the front and then reach up to caress my face. With his thumb rubbing my lips, he whispered, "too bad you wiped the lipstick off, princess." Then he slid his thumb into my mouth. I offered no resistance. As if in a trance, I instinctively let it slide over my tongue, closed my lips around it and gently sucked on his invasive thumb.

Our eyes locked and only broke gaze when my phone vibrated again.

He lifted my phone from the bed and glanced at the message before handing it to me. A short message read, "(Mommy) service him, slut."

He unbuckled his belt then placed his hand on my shoulder guiding me to a kneeling position at his feet. I knew what he expected from me. He was part of Ms. Anne's game.

I felt him study me as I freed him from his briefs. His cock was everything my clitty isn't. He was thick and uncut with large, full balls. His hair was trimmed short around the base of his cock.

I was up close and personal with my first cock, and it was exactly what I hoped it would be. I was unsteady but I hoped he would make me do things about which I had only fantasized. I must have stopped breathing for a moment because I suddenly felt out of breath. The weight of him in my hand was impressive. I had only seconds to take in the view before I felt his hands urge my head toward him.

I let out an involuntary sound somewhere between a whimper and sigh as his cock and balls were resting on my face. My mouth opened and I took in one of his balls. I sucked on it and rolled my tongue around. His eyes rolled back and then closed.

"I'm a good girl"

I sucked and bathed his balls with my tongue, alternating from one to the other. I savored the texture and taste in my mouth. He smelled masculine which contrasted with the flowery body spray I found in Miss Anne's drawer.

His cock hardened in my one hand as I massaged his thigh and ass with the other. He continued to undress as I explored his stomach and chest with my massaging hand. I found a nipple. It was hard and elongated. If my mouth wasn't otherwise occupied, I would liked to have sucked on it too. I gave it a pinch and tug. By the sounds he made, he enjoyed the nipple play.

Returning my focus squarely on the duties "Mommy" promise of me, I kissed and then licked his head. Then I traced my tongue around his glans and flicked my tongue along his frenulum to his meatus.

I was putting into action all the techniques I had seen in videos along with the fantasies I had of being a cum-covered sissy maid myself. He was so hard. I knew I was pleasing him by his moans. He had released my head and was allowing me to have my way.

I started to take him into my mouth, but he pulled away. I watched, fixated on the cock I nearly had inside me, as he laid back on the guest bed. He beckoned me with a hand gesture. Patting the bed, he directed me, "Up here, slut."

I climbed up between his thighs, but he had another idea. He pulled on my arm to swing me perpendicular to him and lowered my head down toward his proud cock. I let out another audible whimper as he slid himself past my lips. His cock filled my mouth and I began to bob up and down making him as wet as I could. I was salivating... drooling on him. This was the feeling I had been chasing. I felt like I was where I belong.

Now, I want to make him cum. I want to taste him. Swallow him.

I increased my pace and took him deeper. On the edge of gagging with each thrust, I began making a throated noise similar to gargling along with my rhythm.

I felt his hand reach under the hem of my nightie and find my ass. His palm cupped an entire cheek. I felt small. He squeezed my bare ass, encouraging me. Then his fingers started searching. He took my breath away for a moment when he found his mark. His strong fingers applied pressure and he found his way inside me. I heard a muffled, high-pitch moan. Was that me? He breathed out heavily, "your pussy is so tight". His words coaxed another long moan from me.

Suddenly his body tensed and his cock swelled.

My mouth was instantly flooded. I felt jet after jet of cum spray my tongue as he grunted and thrusted deeper into my mouth. I swallowed all I could before the rest started to spill down my cheek and chin. I continued to suck on his cock to get all the remaining cum I could. I wasn't about to stop until I was told to stop. As his cock began to soften he slapped my ass and told me I was done.

My phone vibrated: "(Mommy) Good job, cum-slut. Don't forget to thank your new Daddy and smile for my cameras".