Today I wore a pair of Jelly's black, hipster cut panties under my boxer shorts and I feel amazing.
I walk to Jelly's house in the morning just in time to watch her put her makeup on. I love when she wings her eye shadow. If I wore makeup I would do the same.
"Jenny, will you do me a favor before school?" I ask with puppy dog eyes.
"Is it Wednesday, sweetheart?" She asks as she puckers her lips while applying bright red, hooker lipstick.
"No... But I was thinking maybe we could do it more often. I don't know. I feel like it isn't enough once a week anymore."
"I can't just blow you whenever you ask." She says while admiring her makeup in the mirror.
"I know... But" I start to talk and she interrupts me.
"Shut up and take off your pants." She says sternly.
I get up and drop my jeans and boxers completely forgetting that I'm wearing her underwear.
"Wow!" She says, Taken back a step.
"Oh my god. I am so sorry. You probably think... " I start to explain, but she cuts me off again.
"That is sexy. You little cross-dressing, sissy." She says as she pulls the panties down to expose me, and she rests her mouth over my bulge.
I lay back and relax while she works her magic. This is the start to a beautiful Friday.
"You kids are going to be late for break..." Jenny's Mom opens the door with two plates of eggs, bacon, ham and toast, and she stops dead in her tracks. Jens head stops moving, and she's perfectly still but doesn't remove me from her mouth and I stare her mom directly in the eyes.
"I see you've already started breakfast. I'll leave you two alone, and we'll talk about this later." Her mom says and it seems like the three seconds she was in the room was an eternity.
"Do I finish?" Jelly asks with my dick in her hand.
"Yes." I answer and she does as she's told.
"Your mom saw me half naked with a pair of panties around my ankles." I say in disbelief after she finishes.
"My mom saw me with a cock in my mouth. I don't think the worst part of her morning was that you're a cross dresser." Jenny says as she looks into the mirror to make sure her makeup is still great for the day.
We eat our cold breakfast. I like my eggs sunny side up and Jenny's Mom always does it perfect for me. She treats me like a member of the family.
"I love how your family treats me like a member of the family." I say as Jen makes a few wardrobe adjustments before we walk to school.
"My family treats you like a human being. You're just not used to it because of how you're treated at home." She says.
"You seem bitter. Is everything okay?" I ask.
"Oh, everything is great. My mom knows I'm a cocksucker and my boyfriend is a cross dresser." She says with a wink.
"... Boyfriend?" I say with an inquisitive tone.
"You know what I mean! Sometimes I wish you were gay so you could get some guy to blow you and you could help me more with fashion sense." She says with a chuckle.
"You wish I was gay?"
We walk to school holding hands and the questions start to come.
"How long have you been wearing my panties, sissy boy?"
"A while but today is the first time I've ever worn them outside of my bedroom."
"Busted on the first day! So why do you wear them? Do you want to be a girl? Are you gay? Please tell me you're gay." She says with an extra skip in her step.
"It makes me feel good. Sometimes I wish I was born a girl. I'm not gay. I'm not attracted to men but sometimes I want to do some things gay men do. I might be bisexual? I don't know." I tell her and her extra skip is throwing me off because I want to walk slow.
"You want to do things they do? You want to fuck ass? You already fuck mine so you want to have your ass fucked? Of course, you do. If you were a top you wouldn't wear panties like a sissy girl." She says and she can't stop giggling.
"I have thought about that but mostly just oral..." I squirm as I speak and stare down at my shoes.
"Oh my god! You know what this means, right? Three-ways with two men. What about Kyle Williams? I heard he swings both ways! Can I be there for your first time? I'll be your sissy trainer, sissy." She asks.
"Woa, slow down. I didn't think you would think this is such a good thing. I'm not even one hundred percent sure I want a penis in my mouth." I'm taken aback by just how excited she's getting about this.
"Big, bad, punk rocker Jeremy. Punk and guitarist by day - cock sucking sissy by night. Imagine if people found out?" She asks and sticks her tongue out at me.
"That's why nobody is ever going to find out anything."
"You're going to agree to a three-way with two men or I'm going to tell someone on the football team that Mr. Big bad punk rocker is wearing my panties."
"That's blackmail." I laugh.
"I know what blackmail is. I'll give you until lunch hour to agree!" She says as she runs ahead of me and into the school.
She's not serious. She can't be serious.
YOU ARE READING
Tapioca PuddingGeneral Fiction
Is he alone or is he the most popular person in town? Jeremy struggles with borderline personality disorder and other mental illnesses as well as self and sexual identity issues in this dramatic tale about change and challenge. Watch his everyday li...