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[Chapter 4](

***ZACH***

I didn’t know what was keeping me in bed more: all the beer I drank last night, or all the cum I drank last night. It was a real toss-up. Double whammy, too. Apart from my head throbbing from the noonday sun peeking through the curtains, I also couldn’t face anybody ever again, particularly Keith. My drunkenness had unfortunately not erased the memory of his giant cock between my lips, and I pulled my blanket over my head with a groan.

There was a knock at the door, and my stomach lurched, cause ambiguous. After a moment, somebody stepped in, and I was relieved to hear mom’s voice.

“Zach, sweetie? It’s already lunchtime, are you getting up soon?”

“Soon,” I mumbled, my voice no doubt muffled to her. Still, she seemed to find out adequately.

“You weren’t home last night after dinner; your father and I couldn’t find you anywhere.” She paused before chuckling once. “I’m guessing Keith snuck you out to go drinking with his buddies last night?”

My stomach lurched again, so strongly that I almost puked. I wasn’t exactly conscious when we came home. Did mom or dad see us? I was also currently only in panties in bed. Keith must have undressed me when he… He carried me home to bed, and undressed me so I could sleep comfortably. It was so sweet, and I hated how giddy it made me feel.

“I’m not mad that you went out drinking, I just want to make sure you’re safe,” mom continued. “I’m glad Keith was there, but you shouldn’t get so drunk that you’re hungover ’til noon the next day. Try to be more moderate in the future, okay?”

Based on the fact that she wasn’t flipping out on me, Keith must have put my girl clothes somewhere out of sight. He’d even taken my wig off. I bit my lip at the wondered before remembering to answer mom.

“Okay. Sorry,” I stammered. “I’ll, uh… be right out.”

“It’s mac and cheese today,” she announced before leaving, and I let out a breath I was holding.

Getting out of bed, the first thing I did was change out of my panties. I spotted myself in the mirror and saw my makeup was smeared from sleeping in it. I was suddenly glad I had my blanket pulled over my head for that conversation just now. Couldn’t expect Keith to take that off too. I just hoped I didn’t have a break out.

After cleaning myself up, I made my way to the dining room for lunch, finding it was just me and mom. dad was at work, and Keith was apparently already out somewhere. After eating I returned to my room and checked my phone to discover it filled with messages and missed calls from Ellie. I wasn’t in the mood to talk to her about last night, but…

“What happened to you?” was the first thing out of her mouth when she answered the phone. “Are you okay?”

“I’m fine,” I replied. “Just a bit hungover, that’s all.”

“Well hurry up and come over so we can talk about it! And bring your girl bag!” She was telling me to pack everything I needed to crossdress, and I sighed.

“Ellie, I kinda don’t feel like–”

“You don’t come over to my place, then I’ll be going to yours,” she threatened.

“C’mon, Ellie,” I groaned. “Fine! Don’t come over, you’ll… My mom’s home, we just can’t. Just gimme a few, alright?”

“Hehe, sweet. I’ll see you later, then.”

Hanging up, I sighed and threw myself back onto my bed. I really didn’t want to talk to Ellie about this, because talking to her meant facing the truth. Truth was like a gas; it at all times wanted out and it’d seep free into the open given half a chance. And sometimes it fucking poisoned everybody to death.

—

“Wait, how much?” Ellie’s eye were about ready to pop out her damn head. A look of incredulous joy was plastered on her face, and I grumbled again before answering her.

“It was filling my throat, coming out my nose, almost overflowing from my mouth,” I muttered, my face burning from embarrassment. “I swear, it felt like a gallon being pumped… into me…”

She chuckled, shaking her head. “As much as you guys wish for the contrary, men can’t actually cum buckets. Average is, like, a teaspoon.”

“Well I didn’t bring my measuring cup, alright?” I groused. “It was like… three tablespoons or something, and I wasn’t ready for it. What, you want me to give you a reading in milliliters next time?”

“‘Next time?’” Her eyebrow shot up, her mouth beginning to curl into a grin. “Is taking a daily protein supplement going to become a habit of yours?” I gulped, and when I didn’t answer, her expression softened into something gentle and solemn. “Did you like it, Zach? You can tell me the truth.”

“I don’t even know what the truth is,” I lied. She remained unconvinced, staring at me as if simply waiting until I admitted how I felt. I chewed my lip, looking away. “I’m not gay, alright?”

“Is there something wrong with being gay?” she asked, almost defensively.

“No, no, I didn’t mean that. It’s just… I like girls. I’ve always liked girls, and I still like girls. Being gay just hasn’t ever been who I was my whole life.” As I wondered about my feelings, Ellie moved from her usual spot on her bed over to me, curling up on the beanbag with our bodies touching.

“Are you afraid of all this change?” she guessed quietly. I gave a small nod. “So you’re bi. So what? You think I was always like this, or understood my feelings as soon as I discovered them?”

“It’s different for guys,” I pointed out with a sigh. “Guys are binary when it comes to this stuff. Either you’re a ‘real man,’ or you’re not. You’re straight, or you’re not. You suck one dick and you’re the guy who sucks dicks forever now.”

“Then what is more important to you? Being a ‘real man,’ or doing things you enjoy and that make you happy? Because I know crossdressing makes you happy, and recently whenever you talk about Keith, it’s the happiest I’ve ever seen you talk about him.”

My eyes widened in surprise, feeling so exposed at this candid conversation with her. She, out of everybody in my life, was the only one who seemed to find out me, sometimes even better than myself. But she at all times managed to make me feel safe. She was off limits, but God damn it, I was falling in love with her.

“You never answered my question,” she noted. “Did you like sucking his cock?”

What a fucking question. But I couldn’t deny it. Feeling Keith dominate me, want me, cum for me, it felt amazing. I could still smell his thick cream in my nose, and it was intoxicating. Feeling his seed coursing down my throat was something I *needed* to feel again.

When I nodded, Ellie got to her feet. “Alright then. Well, since I’m such a great friend, I’m gonna do something nice for you. Go take a quick shower, and make sure you wash yourself clean.”

She pointed to her ensuite bathroom, and once my shock subsided, I quickly obeyed. Holy shit, was this it? Was I gonna get to have sex with her? To think, that all I had to do to get my chance with her was to become gay. I actually laughed to myself as I scrubbed myself from head to toe. I walked back out in a towel, and she walked over to me and tenderly pulled it off, like a lover. Needless to say, I was standing at attention.

“Go lie down on the bed. And close your eyes,” she murmured.

Trembling with excitement, I did as she asked, taking deep breaths to keep myself steady. She’d been showing more and more interest lately, and it still surprised me that things were moving so quickly. The mattress shifted as she got on the bed, and she spread my legs out, pushing them up a bit. I heard the sound of a cap opening, hoping it was a bottle of lube. And I was right, in a way.

A cool wet finger touched my anus, and I jolted away from it, eyes snapping open. When I tried to sit up, Ellie pushed me back down calmly, raising my knees up further so she could spread lube over my puckering hole. This was definitely not going how I imagined. Curious how I wasn’t resisting more.

“I’m gonna put it in now,” she whispered. Her voice was so seductive that I didn’t put up a fight when she started spreading me open with her finger. I gasped and twitched a few times as she very slowly sank the first knuckle into me. She gave me a moment to adjust before she started moving her finger in and out, letting me get used to the sensation. Between the lube and how slowly she was going, it didn’t even hurt at all. It just felt foreign… and exciting, I think? It wasn’t really feeling *pleasurable*, per se. That is, until she started pushing up to the second knuckle.

“Oh shit,” I gasped, moaning as more of her entered me. Whenever she withdrew her finger, it would curl and make her fingertip brush my insides, forcing pathetic whimpers out of me. Before we started, I would have been happy with fingering her, but now I had no complaints.

“Here we go, last third,” she warned, popping the second knuckle inside and proceeding to push the rest of her finger in my ass. I couldn’t even tell what sounds I was making anymore. It was just one finger, but because of how gentle and erotic she was doing it, I couldn’t control myself. I felt her bottom out in me, and I began panting like a bitch as she started fucking me with her finger. Every time she brushed her fingertip over a little spot in me, my tiny prick would twitch and my legs would spasm. She noticed and focused her efforts there, rubbing and pressing it relentlessly.

“Ellie, sto–” I whimpered, right before shooting three short spurts of jism onto my pelvis. I sighed with relief, letting out a drawn out moan as she eased her finger out of me. “God… Oh God, what are you doing to me?”

I heard the squelch of her squeezing out more lube, then the slick sound of her spreading it over something. Was she…?

“Do you trust me?” she asked softly.

“Yes…” I breathed.

She took a deep breath, and I felt something press against my hole again. It wasn’t her finger. “I’m turning you into a sissy,” she uttered, right before something round slipped through my sphincter.

I cried out, more out of astonishment than pain. Finally opening my eyes, I looked down to see Ellie knelt between my legs, still fully clothed, holding a string of anal beads on a T-grip. And they were studded. When she twisted the black latex toy, I could feel all the little bumps of the bead’s surface rubbing my insides. I couldn’t tell how it felt, but it was forcing moans out of me, if that was any indication.

“Ready for more?” she crooned, and I swallowed and nodded. In came the second bead, with Ellie twisting the toy to tease it in easier. My eyes rolled back as the studs slowly drilled my hole open before it swallowed the bead in one fell swoop. “That’s two now, sexy. Does it hurt?”

“No, it… it feels good,” I panted, and she bit her lip. She called me sexy. My dick throbbed, and she eyed it before taking it with her thumb and two fingers, stroking it delicately. Dear lord, she was touching my dick.

“You should be thanking me,” she murmured as she jacked me off. “I’m giving up my lesbian gold star for you by doing this.” I whimpered again in response, mewling as I felt her start to twist the third bead into me. “Thank me.”

“Thank you…” I groaned, feeling my ass spread open for the studded ball that was raking my entrance.

“Mistress,” she hissed, prolonging the entry of the bead and jacking me off harder with her three fingers.

“Thank you, mistress!” I screamed, and she shoved the rest of the third bead into me. Another shot of cum sputtered out of me, leaking down my short shaft and over her fingers.

“Good girl.” She let go for a moment and slathered the remainder of the toy with more lube before resuming her fingerjob, no longer warning me as she pushed the next bead in. I was bucking my hips now, both trying to escape the alien pleasure of the beads, while also lengthening the stroke of her fingers on my puny member. It was already softening, but I could still feel a third orgasm building up.

“I’m… not… a girl…” I moaned.

“With this useless thing? Coulda fooled me.” No sooner had the fourth bead cleared my tight ring than she was already cramming the fifth one in. “This is nothing but a useless limp clitty, and it’s about time a real man showed you what a *cock* looks like.”

As the fifth bead rammed into me, I clutched my chest and viciously pinched my nipples. Was Ellie really gonna make me into a girl? Why was it that words that were used to bully me sound so hot coming from her lips? She had a sadistic look on her face. I should be hating this. Yet when the sixth and final bead plunged into my ass, I climaxed again, balls tightening and my little clitty shooting absolutely nothing out as I came.

I collapsed onto her bed, drenched in sweat while Ellie pushed the rest of the handle into me. The T-grip was concave, and it fit snugly against my taint and crack, the toy acting almost like a buttplug. Dazed, I didn’t notice Ellie scraping up the cum on my pelvis until she was pushing her fingers into my mouth.

“Eat it all,” she ordered. “Get used to the taste. Your brother will be feeding you more soon enough.”

I dropped my head back on the mattress, obeying her and scooping up more of my cum to lick it off my fingers. Already I was idly fantasizing about swallowing more of Keith’s seed. While I was still dazed, I felt something hard cupping my balls, and then the same thing was slipped onto my dick.

*CLICK.*

I jerked upright, and I had pink plastic trapping my genitals. “Ellie, what the fuck! Is that a chastity cage?!”

“Don’t fuss,” she said, holding up a small silver key. “I’m giving you the key. But only Keith is allowed to use it, do you understand?”

“I–” Unable to even discover the words, I floundered wordlessly at this whole situation.

“I can’t hear you,” she snapped sternly. “Speak up, you sissy slut!”

With how the anal beads were tucked against my body, it didn’t seem like she had any intention of taking them out. Later, she would pull panties over both my cage and the toy, forcing me to remain like this until my master or mistress removed them. And as humiliating and fucked up as everything was…

“I understand, mistress.”

NSFW: yes

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