Journey to Girlhood Ch. 02

Story Info
Steve is blackmailed by his bully into coming over.
2.5k words
4.58
30.3k
37
14

Part 2 of the 4 part series

Updated 06/14/2023
Created 01/24/2023
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

After what had happened with Max, I spent the next week living in fear. I was so anxious about going back to class that my dad actually believed I was ill with something, and so I took a couple of days off. But eventually I had to go back.

Molly tackled me as soon as I walked through the front gate, and I pushed her away instinctively thinking it was Max.

"Jeez Steve, what's got into you?" she said, picking herself up off the floor. "First you don't reply to me all week, now you're pushing me over?"

"Sorry," I said. "I've not been feeling great."

"Clearly, ya big weirdo. Well, medium weirdo. I'm short as heck and you're barely taller than me."

As we walked into class, I saw Max. He smirked at me, and I blushed and looked away. How the hell was I going to get through the rest of the course with him around, a constant reminder of being emasculated. A constant threat that it might happen again?

As I thought about this, I felt my cock twitch, and my face went even redder. What the fuck was wrong with me?

*

The next few days of class went ok, and I got out of swimming because I was so nervous I puked. Instead I sat on the poolside, trying to finish some homework but being distracted by the swimmers. Max's cock, the cock that had abused my throat, the cock that I had licked clean - was clearly semi-hard in his speedos as he did backstroke.

I felt someone's gaze on me, and turned to see Darren standing on the poolside, water dripping down his muscular chest, smiling at me. I smiled back, but he didn't respond. I heard a giggle, and turned to follow Darren's gaze behind me. Katie, one of the cutest girls in our class, walked past me towards Darren, her curves bouncing as she walked.

"What are you looking at?" she said to Darren, letting out another giggle.

"Someone who's supposed to be swimming laps," he said with a smile. "Which stroke are you going to use?"

"I was thinking breast stroke," she said.

He laughed, "That's my favorite too."

"Stop it!" she said, hitting his arm playfully.

Darren, noticing I had been watching their conversation, gave me a wink. I smiled, and turned away, only to see Max looking at me from across the pool. He glanced down at his crotch and my eyes followed, and when I looked back up at him he winked at me too.

*

As I was leaving for the day, I felt a hand on my shoulder. It belonged to Max.

"Wait up a second Stacy."

My eyes widened in alarm, but Max just laughed.

"Relax slut, there's no one around to hear." He grabbed me by the wrist, and pulled me around the corner of the building where it would be even less likely we'd run into someone.

"I'm disappointed you missed so much class. I might need to discipline you."

I finally found my voice, and tried to pull away from his grip on my wrist as I whispered at him. "Let me go Max! I don't know why you think you can talk to me like this but you can't!"

"I treat you just like the other girls that like sucking my dick. You did like sucking my dick, didn't you Stacy?"

My face went bright red and I looked away. "Of course I didn't!"

"I saw how much you were leaking. How hard your clit got. How much effort you put into cleaning my cock, after I'd cum and stopped fucking your face." He leaned in closer.I felt his breath on my ear, and I shuddered. "Most girls don't smile while they're cleaning a cock, but you did."

"I only did what you made me do. Please Max stop this, I'm a guy it's not cool! I'll do whatever you want, just stop-"

"Yes, you will. Come over to my place tonight, I've got a gift for you. And make sure you're shaved smooth beforehand."

"Max I-"

Before I could get another word out, Max's free hand was around my throat.

"Shut the fuck up. You're going to do what I say, or I'm going to tell everyone you begged to suck my dick. And who are they going to believe? A virgin sissy? Or a guy that fucked half the girls in our high school?"

When he finally let go I gasped for air, and started to sob.

"See you tonight slut." And with that, Max let go of my wrist and walked away. I felt the tears stream down my cheeks as I massaged my neck where he had choked me. As I stood there, crying and trying to work out how I was going to get out of this, I realized I was also hard as a rock.

*

That evening, I knocked on Max's front door. I hadn't thought of a way to escape the situation, and had spent the afternoon in a daze, preparing myself as I'd been instructed in a numb but methodical state. I had shaved smooth all over, moisturized, and put on the girl's underwear under my own clothes. I'd put the rest of the outfit in my bag. My shoulder-length hair hung soft and silky, and I could faintly smell the floral scent from the conditioner I had used.

The door flung open, and Max stood there in gym shorts and a t-shirt. Judging from the sweat stains, he had been working out. I inhaled involuntarily, his manly scent invading my nostrils. He ushered me in.

"My parents are away for a few days so I've got the place to myself," he gestured to a large but modest living room, with a three-seater gray sofa and a gaming rig setup in front of the TV. Laid out on the sofa was a cute black skirt, pink crop top, and a matching bra and panty set in white. There was also what looked like lipstick, eyeshadow, and nail polish.

"I got you an outfit ready. Bathroom is through there if you want to get changed," he said. He dropped down in a lazyboy next to the sofa, and picked up a beer he was halfway through. When I didn't move, he frowned at me.

"What the fuck are you waiting for sissy? Aren't you grateful I got you these?"

He had that look in his eyes again, the same one he'd had before when he'd hurt me. I nodded and muttered a thanks under my breath, grabbed the clothes and ran to the bathroom. The new clothes were much cuter than the uniform, and the pink nail polish went well with the top. I did my best to put it on quickly but neatly, not wanting to keep Max waiting too long. And then did my best to go for a cute look with the eye-shadow and lipstick. When I had finished, I came out and sat on the sofa, putting my other clothes in a neat pile next to me.

Max ignored me for a minute or so as he finished up a racing game, and I sat there quietly. I was terrified, and freaking out about the whole situation. But I also couldn't help but admire my nail polish - it did look pretty cute. I could also feel my smooth legs rubbing against each other, and I felt a tent start to form in my panties as I thought about my smooth skin.

"Yes!" yelled Max, throwing the controller to the floor. "Fuck yeah. Been trying to beat that one for ages."

He finally turned to look at me, and laughed. "Holy shit, are those the clothes I gave you last week?" he said, indicating the panties on top of the pile of clothes next to me. "Did you take them home, and then fucking wear them today? Fucking hell, you're even more of a girl than I thought you were."

I blushed and looked away. He chuckled again, then picked up his beer. He drank the last of it while appraising me. "You do look cute in that outfit." He put down his empty bottle, and stepped over to the sofa. Pushing my clothes to the side, he dropped down next to me and put his muscled arm around me, his sweaty pit close to my nose.

His hand went lower, slowly tracing my arm and then moving to my hip. He looked me over, as if appraising a piece of art.

"You like being cuddled like this, don't you?"

When I didn't reply, I felt his hand grip my hips tightly. I exhaled sharply and nodded.

"I know you prefer to use your tongue for things other than talking, but I think you need to use your words more Stacy."

"Yes," I said.

"Good girl," he said.

I blushed. It felt weirdly good to be called a girl like that. He pulled his arm from around me and turned towards me. His hand moved to my face and turned it towards him, his thumb tracing my lipstick-covered lips and moving down my cheek.

"You did a good job Stacy. I'm impressed."

"Thank you," I said after a moments hesitation. His hand was soft and almost comforting on my neck, but I was still on edge about the entire situation. And most of all I didn't want to do anything wrong again - I remembered what his grip tightening around my throat earlier today had felt like.

"Thank you what, Stacy?"

I looked at him quizzically. "Thank you Max?"

"Call me sir."

I opened my mouth to respond, but before I could he surprised me by leaning in and kissing me. His strong hand moved to the back of my neck, holding me in place as his lips moved against mine. His stubble scratched against my smooth face as his other hand moved to stroke my knees. I felt so under his control, and before I had even comprehended what had happened I was leaning into the kiss, my tongue moving to meet his as it moved into my mouth.

After what felt like hours, but was probably less than a minute, he broke off the kiss. Breathing heavily I stared at the floor, trying to understand what had just happened. I'd enjoyed that. I couldn't have gotten away if I had tried, but not only did I not resist, I leant into the kiss. This was too weird. I needed to get out of here as quickly as possible, and find a way to stop this from happening.

Max broke my train of thought by turning my face to look up at him, where I had no choice but to meet his gaze.

"What do we say, Stacy?"

I swallowed, and closed my eyes before answering. "Thank you sir."

"Good girl. Do you want a drink?"

I was caught off guard by him asking me what I wanted, but I did want something to take the edge off. He smirked when I said "yes sir".

When he came back he handed me a beer, then dropped down on the sofa beside me and picked up his controller. I had expected he'd make me blow him again, but I wasn't going to question it. And against my better judgement, I felt cute dolled up, sitting on the sofa and drinking with him.

I sipped my drink, and he passed me another controller. For a while we played multi-player and drank, even cracking jokes like we were friends. I was starting to feel the buzz from the beer when Max got up from the sofa. He motioned for me to stay where I was, and came back a few minutes later with a small box.

"I told you I got you a gift, so close your eyes Stacy."

I swallowed nervously, and sat up on the sofa with my eyes closed. What the hell kind of gift would he have gotten me? More makeup? A necklace?

I felt him step closer to me, as he opened the box. For a moment nothing happened, as I heard him fiddling with something, then I felt him kneel in front of me. A moment later his strong hands were on me, my skirt being flipped up and my panties pulled to the side. I gasped in shock and opened my eyes to see Max sliding a pink ring over my soft penis, before he shoved my balls through the tight gap. I cried out as he did this but he react, holding the ring and myself in place with one strong hand as he used his over hand to pick up another pink object, this one a stubby cylinder which he popped over my penis as well. There was a click as it slid into a fitting on the ring.

"You're smaller than I thought," he chuckled. "I could have gone down a couple of sizes." As he said this, he pulled a key from his pocket, slid it into the pink object covering my penis, and turned it before placing the key back in his pocket and standing up.

I lay back on the sofa, my legs wide, my skirt and panties askew. My eyes were wide in shock as I stared up at Max.

"What the fuck?" I whimpered, my hand moving down to the object covering my penis. My balls stung from where Max had forced it on.

I instantly regretted saying it. Max looked down at me with the same cold look he'd had when he'd choked me, and for a moment I stopped breathing.

After a tense moment, he smirked, and I started breathing again. "You know how badly you just fucked up slut. I'm going to let it slide this time. But what should you have say when you're given a gift?"

"Thank you sir", I whispered.

"Good girl."

I pulled myself up, straightening my panties and investigating my gift.

"You know what your gift is, right?" said Max.

"No sir."

"It's a chastity cage. The back piece goes around your little balls to hold it in place, the front piece covers your little clit, and the lock holds it all together. And while I have the key, you can't take it off, and you can't cum."

I looked up at him with my mouth open, wanting to scream at him but too scared to form the words.

"Well, you might be able to cum. But not from playing with that little clit."

I shut my mouth and blinked back tears as I straightened up my skirt. This had gotten so out of hand. How had it gotten worse than it had been in the locker-room?

"If you're good I might let you out but... well, there's not much point, given how pointless that thing between your legs is compared to a real cock," he laughed. He grabbed his bulge through his pants, and I knew it wasn't going to be long before I'd have to do what we both knew I was really here for.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
14 Comments
et1sw1064et1sw106412 months ago

Love this story. keep going. ignore the ones that forget this is "FICTION"

SissysuziSissysuziabout 1 year ago

Great story,I love it! I don’t understand why people are so critical,it’s a story ffs! If you don’t like it jog on.

AnonymousAnonymousabout 1 year ago

Never heard of a gay bully..... Why don't these forced fem stories ever have the victim tell friends or parents or simply cut the cage off?

AnonymousAnonymousabout 1 year ago

wish i was the sissy

AnonymousAnonymousabout 1 year ago

This is so romantic I hope she marries Max he is such a sweetie giving her gifts

Show More
Share this Story

READ MORE OF THIS SERIES

Similar Stories

But I'm a Boy, Not a Cheerleader! Accidentally a cheerleader at the basketball party!in Transgender & Crossdressers
Sissy - For Rent Brian is forced to serve his landlord as a sissy for rent.in Interracial Love
Making of Tina Ch. 01: Caught A story about forced feminization.in Transgender & Crossdressers
Mommy's New Daughter Pt. 01 Mother and friend think of an unorthodox punishment for son.in Transgender & Crossdressers
Mother's Greed Ch. 01 Mother gives in to her desires.in Transgender & Crossdressers
More Stories