Briar Pt. 02

Amy and I meet up on Saturday. She's waiting downtown, wearing a big coat and huge sunglasses, and she looks down at me as I get off the bus. She's a lot taller than I remembered, though I don't think this weird transformation had anything to do with my height.

I'm wearing a tanktop that used to fit me when I was a boy but now barely covers my nipples, underneath my usual hoodie. It was super warm on the bus so the hoodie is a little less zipped up than I was intending on it being.

"Wow, flaunt your stuff girl," Amy smirks as she holds the door to the store open.

"I..." I start to make an excuse but I can't think of a good one. Truth be told, it kind of turned me on dressing like this. And the way that Amy is appraising at my body doesn't help with that.

"OK, so this store is great," Amy continues, ignoring my lack of reply, "Because it's run and owned by queer people. So you've got a good chance of finding something that's going to work for you."

She's of course referring to binders, because wearing masking tape to school definitely doesn't seem to be working for me.

"I've had a few friends who needed binders, and a couple of them had a lot to bind, so we should be fine, what about this?"

I turn away from the wall of dildos to look at the binder she's pointing at.

"That might work?" I say, though I have no idea. I glance back to the wall of dildos, wondering if there are actually cocks as big as the bigger ones.

"Oh, do you need a sex toy?" Amy asks, "If you want privacy I can go outside?"

"No, no, I'm ok."

A cute androgynous clerk comes by and leads me to the changing rooms. I try on the binder, and surprisingly it fits me pretty well. It's super weird crushing my tits against my chest, but if I want to pretend to be a boy, I probably need to do so.

I pull my hoodie back on over the binder and pop out.

Amy checks me out for the third or fourth time today.

"Like, if your goal is to be breast free I think that works!" she says, gesturing at my now flat chest. "You might want to do something about your hair though."

I think about cutting it and immediately feel anxious.

"I... I want to leave it as is," I mumble, pushing back into the change room.

"You can leave it! I just mean if you want to pass as a boy," Amy says from the other side of the door.

I pull the binder off and pull my tanktop back on, looking at myself in the mirror. My tits look fantastic under it and I bite my lip as I feel my pussy tighten.

I honestly look hot. Like too hot to talk to myself from before hot.

Amy's looking at dildos when I get back out, and she looks so casual about the whole situation. I blush as I roll my hoodie under my arm and stand next to her with my basket.

"Hey," Amy says, still looking at the dildos. "Got everything you need? I'm trying to decide if I want to pickup anything."

"Yeah," I say, swallowing, "I think so."

"Do you have a dildo? Never can go wrong with a good dildo."

"I..."

Amy grins at me, and then looks concerned. "Uh, Briar, you're..."

I look down and my nipples are basically visible through my now wet tanktop. I'm leaking again.

"Oh fuck," I moan, handing Amy the binder so I can pull my hoodie back on. "Let's buy this and get out of here."

--

"You're hanging out with that girl a lot." Apollo says, more passive aggressively than he probably intended, as we stand in line to checkout at lunch.

"Yeah, she's been helping me."

"Just like, you know that people are going to start thinking you're like her, right?"

I don't look at him, but I can hear the worry under his comment. He doesn't want to be seen as gay for hanging out with a trans woman.

"Don't worry, I won't mess with your straight cred." I say, glancing back at him.

His eyes register my hurt and he immediately stammers incoherently while I check out.

We find a quiet table, and eat in silence. Even though I'm not looking at him, I can feel his eyes on me.

"How'd you... how'd you hide your... tits?" he whispers the last word.

I look down at my chest, the binder crushing my breasts.

"I'm wearing a thing that Amy told me about, it's called a binder."

Apollo nods, as if that explains everything.

"I didn't mean what I said earlier," he says quietly. "I just... I'm worried about you. I don't know what's going on but I'll always be here to take care of you if you need me to."

"Oh, you know I'll always need you," I say, absentmindedly taking his hand with mine. He squeezes my fingers, while we eat in silence.

Then I feel the tightness in my pussy and I pull back. He looks shocked, and then embarrassed, his face turning red.

"I should... I'm going to go... gotta study." he says, grabbing his food tray and almost running away.

I sigh and finish my food, trying to ignore the pain in my stomach and my arousal.

--

It's my final class of the day and I'm still fucking turned on from a really brief moment with my best friend.

Possibly because I can't stop thinking about it. About how natural it felt. About how strong his hand felt when it wrapped mine.

I cross my legs, then uncross them, then cross them with the opposite legs.

This is too much.

I gingerly rub some hand sanitizer onto my hand and after a moment, slide a now sterilized finger into my panties, pushing into vaginal cavity. Probing for my g-spot. Nothing like having a pussy to realize how bad at sex you were before.

I brush my finger against the inside of my pussy and gasp audibly as I discover what I was looking for.

A bunch of students look at me, and the professor stares briefly before returning to his lecture. Fortunately, I'm at the back of the room and normally go pretty unnoticed.

I push my finger in deeper, trying to get the same sensation as before, while carefully keeping my mouth closed to prevent unnecessary noises.

The back of my hand presses against where my clitoris is, and the pressure sends a different sensation into my pussy. I change tactics, pulling my finger out, and start kneading my labia around my clitoris, carefully keeping my mouth shut while I'm doing so, pretending to pay attention to the professor as he's talking.

He's one of those young, fresh out of teacher's college professors, who's only ten years or so older than me. A neatly trimmed beard with shaggy brown hair implies a reasonable understanding of what makes him look good and a well built body that suggests time at the gym.

I imagine that he takes me in the bathroom, that he shoves me against the wall of the bathroom, breasts into the tiles.

In my mind I moan as he pushes my panties aside so that he can slide himself into me, covering my mouth as he does.

Then he grabs my ass and thrusts himself into me, fucking my wet pussy as my tits press against the wall.

I think in this fantasy I start leaking milk against the wall of the bathroom as he fucks me, and another teacher enters the bathroom while he's doing so. I watch, unable to do anything as the other teacher, an old, unattractive man, begins to jerk himself off at the sight of my professor fucking me.

He pulls out a camera and begins to record me.

"This is going on 4-chan," he says, "Tranny slut gets fucked by her professor."

"Do you want a turn at this pussy?" I imagine my professor asking, and he pulls out of me, pushing me against the old man, who bends me over the sink to enter my already sore cunt.

"Oh, this is what I wanted, as soon as I saw you changed genders," the old man moans as he fucked me.

"Briar?" my professor asks and it takes me a second to realize he's not the professor from my fantasy, but the real professor, standing over me, my hand in my panties. The classroom is now empty aside from the two of us.

"I..." I stammer, as I see his eyes follow my arm down to my pussy.

"Are you jerking off in class?" he grabs my arm and pulls it out of my pants. The friction is too much and I gasp as I cum all over my fingers. He curses loudly and jumps back, and I fall onto the floor.

"This is unacceptable behaviour." he says, looking furious. "I'm going to have to report you."

"Oh god, please don't report me," I say, trying to push myself off of the ground. "I'll literally do anything, I really need to stay in school."

"I have a duty to... What the fuck is that?" he asks, pointing to the milk soaking into my t-shirt from my fall, obviously starting below the binder.

"Uh..." I close my eyes. "It's milk?"

"Milk? Like... human milk?"

I nod.

When I open my eyes, he's no longer looking furious, and instead is just looking pensive.

"You weren't jerking off a cock were you?"

I slowly shake my head.

"Come with me."

--

"Strip," he says, arms crossed.

We're in his office and we're standing across from each other. He's between me and the door.

The windows facing the campus are uncovered, which means that anyone with binoculars that could see a seventh floor window could see everything that's happening.

"I..."

"I record all my lectures." he says, "If you tell anyone about this I'll release you fucking yourself to the internet."

I swallow.

"If you don't do what I say, I'll release you fucking yourself to the internet." He crosses his arms. "What's it going to be?"

Slowly I pull off my t-shirt, and pull off my binder, my bare breasts flopping down, wet with milk.

"And those." he nods at my leggings.

I pull them down, and the wet panties underneath, revealing my freshly waxed pussy to him.

"So this is what you were playing with." he says, curiously eyeing my genitalia. "I could have swore you were male. Or are you a transgender man? I'm not up on the lingo."

I'm standing naked in front of my professor, who has threatened to share a video of me masturbating, and he wants to worry about lingo?

"I'm... I'm not certain what I am."

"Why are you binding these? They're fantastic." he walks up to me and takes one of my breasts, squeezing it, letting my nipple push through his fingers.

"So that people don't know I'm... not a boy?" I say, gasping as he pulls on my nipple, spraying milk all over the floor. "What do you want from me?"

He leans back against his desk and smiles at me. "I haven't fucked someone who is lactating in years!"

"You want to... fuck me?" My fantasy is becoming a startling reality. One that I'm not certain I actually want.

"Oh, yes, if you want to continue to attend this school I think it's going to be necessary for you... to put out."

His cock is hard against his pants, desperate to escape, and he leans back against his desk, hands on either side of him.

He's opening his mouth to speak when we both hear a knock on the door.

"Excuse me, professor? I was told that my friend Briar was with you?"

It's Apollo's voice through the door.

"You're interrupting." My professor says, glaring at me.

"I realize, I just..." the knob jiggles, "Can you open the door?"

My professor gestures at my clothes and mouths "put those on".

He goes to the door, and opens it slightly so that he can talk to Apollo.

"We're having a very important discussion about Briar's future here," he says, "It's extremely inappropriate of you to-"

"I know, I know, it's just that Briar's mom is in the hospital, she had an accident,"

I take a deep breath, which distracts my professor long enough that Apollo is able to push the door open wide enough to get his head through. His eyes widen as he sees me half naked.

"Excuse me-" the professor says, as I push past him, into Apollo's chest.

"Sorry, sorry," Apollo says, pushing me behind him so that he's blocking the professor.

I don't look back to see how he reacts.