A Tale of Two Sissies Ch. 01

Then she crouches behind me. One mature arm sliding around my chest. The other into my crotch. Her fingers slip inside my silk panties gripping my hard little pud.

"Mom, w...what are you doing?" I ask.

"Do you really think this teeny wee could satisfy a woman?" She huskily breaths in my ear. My mother squeezes my nothing cock as an exciting shiver runs through me. "That it could satisfy anyone?"

She starts jacking me in my panties. Using only a couple fingers. It's all she needs.

"I feel sorry for any girl that takes a chance on you. She would just be wasting her time." Mom slides her free hand under my bra. Pinching my nipple hard.

"You're nothing but a pathetic wimp!" She says loudly. My little raisins throb as I drizzle my cum all over her fingers.

"Aww, look at that. Little sissy is done already." She says bringing her fingers up to my lips. I obediently suck my own jizz off them as my dicklette drizzles in my panties. Finally tasting my own cum.

Then she stands up with a sigh. "This is our life now Willard. I have always been too submissive, and it looks like you are too. You just should have been born a girl."

I look up at my chubby, beautiful mother. Sexy in her lingerie. I am humiliated, but also a very excited.

"Tonight I want you to sleep on that." She points at the pillow I was still straddling. The pillow now stained with cum. "Lay your pretty little face in it, like a good girl. In the morning throw it in the wash before school." Then she leaves to go to her own room.

I sit for a while longer, in a puddle of my own cum. Then I get up and wash. Change into a short silk negligee, and lay down in bed. My cheek resting on a cold, sticky, puddle of my own dick slime.

Monday morning I slip on a pair of blue silk panties. My pathetic nubbin twitching with excitement at the humiliating act. I match it with a training bra. Also blue, dotted with cute little sunflowers.

Then I button up a purple blouse, and a dark blue pleated skirt. It stops a couple inches above my knees, showing off my freshly shaved legs.

Then I pull on purple, knee high socks.

Checking myself in a mirror, I look ridiculous.

An effeminate boy in girl's clothes. But it's what Clayton wants. I don't look sexy. Just demeaned.

I get some shocked looks walking to school. It isn't till I get there that I get laughed at.

Red faced I quickly go to my locker then to my first class.

"Are you wearing a girl's shirt?" Someone asks as I sit down and shrug.

I can hear students chuckling as the bell rings.

It only takes old Mrs Harson a minute to zero in on what was disrupting her class.

"Willard! Come up here this minute!" She orders in her shrill voice.

I walk to the front of the class. Kids openly laughing at me.

'Oop!' I gasp when someone gooses my rear.

"What are the meaning of these shenanigans?" She looks around the room. As if daring the other kids to be in on it. Before landing her steely gaze on me.

"S ... sorry ma'am." I say. Nearly a whisper.

"What's that? Speak up!" She orders.

"I ... I'm a sissy, ma'am. I'm not allowed men's clothes." The whole class laughs.

"To the principals office young man!" She shouts over the din.

Soon I am sitting, waiting for the principal to see me.

When he orders me in I explain that I am expressing my individuality. Exploring my options.

Being a liberal arts major, he is very understanding.

He writes me a note for my teachers, and warns me that transitioning would be tough. But I had his support.

The rest of the day passes in a humiliating blur.

Vic had dressed similar to me. He has a short white skirt, with a lot of lace along the bottom. And a white tanktop with pink polkadots. I don't think he has a training bra on though.

"My bitches." Clayton says happily in the gym room after school. "You did good!"

He has us bend over a table side by side. Then I feel him lift up my skirt. Cool air brushing my silk clad ass. His big hand rubs my rear. I can feel my little pud get hard.

My ass clenches when he pulls away. Almost as if it wants to be fucked.

"Ha ha! Great. You sissies are coming along nicely. Now I have some special pills from my mama's homeland. I want you to take one each night before bed. Understand?"

We nod as he lets us stand back up.

The black boys leaves. Apparently not interested in us today.

I head back to Mrs. Harson's classroom. She had told me to stop by to make up the class I'd missed.

I can sense something wrong as I step in.

"Shut the door behind you." The old teacher orders as I walk in. I do as I'm told. "Come over here." She stands up next to her desk. I walk over next to her. She is taller than me, and skinny. She has an angular face that always looks stern.

"Bend over the desk. You will learn the lesson of shenanigans."

Docily I bend over her desk. Leaning on my elbows. I suspect I know what is coming. This has never been a fantasy of mine, at least not with a teacher so old. But my little nub is hard in my silk panties all the same.

"You whippersnappers are all the same." I hear a 'swish!' Somewhere behind me. The old teacher lifts up my skirts. "Well I'll give you a whip 'er snap!"

Whoosh, CRACK!

"Mmmmmm." Tears come to my eyes at the line of fire across my ass. My silk panties offering no comfort.

"Say your sorry for causing a commotion." She commands.

Swish, SNAP!

"Uuunh! S ... sorry ma'am." I sniffle.

"No. Not yet, but you will be." She states cruelly.

Over and over her ruler strikes my increasingly burning ass.

Finally she relents. She grabs my hair and forces me to my knees. I reach behind to rub my inflamed bum.

"You dirty students are all the same. Sex, sex, sex." She sits down in her chair and scoots it toward me. So that I am kneeling between her bony knees. "I'll show you your proper place." She lifts up her long dress, revealing her crotch.

I stare between her wrinkled, pale thighs. She isn't wearing underwear. Her old cunt is surrounded by grey pubic hair that glistens with moisture.

She grabs my hair again and pulls my face forward. "Start licking." She orders.

Timidly I stick my tongue in her old, salty twat.

I do my best to please her as my teacher moans above me. She gives me instructions on being a better pussy licker.

I am down there for a good twenty minutes. My tongue licking and tickling, my lips sucking and nibbling.

Finally her thighs tremble as she comes. She grips my hair painfully. Shoving my head deeper in her crotch. She rubs her cunt all over my face as her bitter juices flow.

Finally she shoves me back. "Dirty boy." She chides. Lowering her skirts. "Go. Get out. Now!"

I stand and quickly leave. Her fuck slime all over my face. I head to the nearest bathroom to clean it off.

When I get home I find two big bags of clothes by the front door.

"They are your old, boy's clothes. You don't need them anymore, so I'm donating them." Mom tells me when I ask about it.

From now on I am only to dress as a girl. But I'm not. I'm not a girl!

I take my first pill that night.

During the next week I am be ridiculed during the day. Sometimes I go down on my mom in the evening. And at night I'd take my pill.

Friday after school Mrs. Harson spanks me and makes me eat her out again.

I spend most of the weekend in my room.

I am miserable. Humiliated at school and emasculated at home. True to her word, mom had donated all my boy's clothes. Now even being home isn't a reprieve from being a sissy. Just a constant reminder if my new life.

Even when I'm at home I'm dressed in girly panties. I usually wear a skirt and a tank top. Though no bra, unless mom orders me to. Which she does a lot.

At night I wear a short nighty to bed. Either silk or satin. I have to admit, I like the way they feel against my skin.

"I think you're very brave." I am in science class. Partnered with a mousy redhead girl named Cynthia. She wears glasses and has slightly crooked teeth. She had no noticeable breasts, and is super geeky.

We get paired for labs most of the time because neither of us have friends in this class.

I don't have friends in a lot of my classes.

I don't have a lot of friends.

"I...um, thanks?" I answer.

"I'm sure it must have been hard. Coming out and all." She says, pouring chemicals.

"I...I'm not gay." I protest.

She looks at me. "No, no. Of course not. You're transgender. I get it."

"No, I..." I what? What an I? "I'm just a cross dresser I guess." Now I can't look her in the eyes. I'm so embarrassed.

She puts her delicate hand on mine. "It's ok. You should always be who you are. I support you."

I can't help but notice how green her eyes are as I turn to look at her.

She really is kind of cute.

Before I realize what I'm saying, "Do you want to go out tonight? Like on a date. Um ... with me?"

"Yes!" She says excited. "I'd love to."

So we exchange details, and make plans.

As I walk home after school I feel like I'm walking on clouds. Butterflies in my tummy. Happy for the first time in weeks.