I feel humiliated, but my little dicklet is still hard as a rock. I try on the negligees she picks out. silks, satins, and lace.
Finally we head home with my new wardrobe.
During a quiet lunch mom can’t stop looking at me strangely. Afterward we heads upstairs where she helps me shave my whole body. I can’t help that my tiny penis keeps getting hard.
Afterward, she heads to her bedroom.
I put on a pair of pink silk panties and a big T-shirt. I stare at the training bras laid out on my bed for a few minutes. Fascinated and shamed by the thought of wearing them.
With no pants I feel vulnerable walking around the house. Vulnerable and strangely feminine. The air caresses my shaved legs as I walk. My sissy bump keeps getting hard in my panties.
In the evening, when she comes downstairs mom has put on lingerie. A sheer white set, with little blue bows. Stockings, a short skirt that doesn’t quite cover her ample ass and matching bra that barely holds her big tits. I can see that she isn’t wearing panties.
“I need you to make mommy feel good, Willard.” She tells me as she sits on the couch and spreads her legs. “Strip to your underwear, but put on a bra.” I rush upstairs to do as told. Excited, even though I know this is wrong. So deliciously wrong.
I pull my T-shirt off. Shivering as I grab it by the bottom and pull it over my head. Like a sexy woman would do in an R rated movie. Feeling even more feminine.
I pick out a pink silk bra. One that matches my panties. I struggle to pull it on. Not used to the strange clothes. It still feels tight around my chest. Binding, like the whole world is dominant over me.
I stop and stare at my mother in the couch. Her in some slutty lingerie. Me in girly bra and panties. The whole thing feeling unreal.
“Good, now crawl to mommy.” She orders, giving me a stern look. Slowly caressing her inner thighs.
I get to my hands and knees and crawl. Stopping between her meaty thighs. The awkward bra feels tight around my torso, and over my shoulders. I feel warm, there are butterflies in my tummy.
“Lick mommy’s pussy. That’s a good girl.” She tells me.
I brush her small skirt out of the way and lean in. I kiss her bare pussy all over, fascinated by her soft, warm flesh. Excited at our incestuous play. Mother leans back and moans her pleasure above me.
She shivers as my tongue tickles it’s way between her labia. She gasps when I drive it as deep as I can, tasting my mother’s juices.
She whispers some advice on being a better pussy licker as she gets closer and closer to orgasm. Her hands squeezing her own big breasts. Pinching and pulling her nipples through her sheer bra.
Mom finally cries out her pleasure as I lap up her free flowing cum.
I lay my head in her lap after our…interaction. Still kneeling before her. I say, “You know I’m not a girl.”
“Oh, honey.” She says kindly. Petting my hair. “Of course you are. You are my little sissy girl, and I love you.” My body shivers at her words, and my little prick gets hard.
“Uh, what about my needs?” I can’t believe what I’m asking.
She nods, and I get excited when she leads me upstairs.
I had always thought my mom was hot, but was never sexually attracted to her. Not until I saw her get fucked like a whore. Not until she sucked on my little dick.
Now my tiny pecker was hard as a rock as I thought about what we were about to do.
When we reach my room I’m surprised when she pulls my pillow off the bed and makes me straddle it on the floor.
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.