Jerk Bros to Sissy Sisters Ch. 04

The clothes Greg and I had ordered online arrived after a few days and we could hardly wait to try them on. We had taken our bodies' measurements and got some basic stuff for starters.

We had assembled 2 different outfits we thought were pretty casual. I went for a 'goth look', as Greg said, while Greg was a bit more on the 'bimbo' side.

Getting ready I looked in the mirror, and glanced at a different body. Simple dark blue converse shoes, and over the knee thigh-highs, leading to dark gray shorts. A gap of an exposed belly and a black crop top. The same feeling of pleasant tightness was all over me. Multiple pieces of fabric hugging and squeezing my body.

Greg looked stunning, he rocked the same thigh-highs in white, along with a short pink skirt and light pink tube top.

"God, you look gorgeous," I admired.

"You too hot stuff." He nodded towards another package, containing a make-up kit.

Well, now we'd have to complete the look. We sat down in front of each other, saw a few short tutorials and did our best painting each other's face. It didn't go as smoothly, obviously. His hands were definitely more skilled than mine.

"Goddamn," he shouted.

"Quit being such a baby."

"You stabbed my eye you bitch."

"I am holding a sharp instrument near your eyeball, I insist you keep calm." I smirked and kissed his nose.

"Now you're ruining my contours" he complained.

"I will literally shove this up your ass. "

"Ooh, how uncivilized." Greg mocked. "Speaking of shoving in ass, guess what else came in the mail." He picked up the large dildo we had bought, waving it like a flag.

It surprised me, it was bigger than I thought. Undoubtedly bigger than both of us. "Well, there's plenty of time for that later." I assured him, and kept applying make-up.

It wasn't great, but it was bearable, something we'd just have to practice more. He did some dark sharp eyelines on me, while I added some rouge mascara and red highlights on him.

Looking at the mirror side by side, we were transfixed. Nothing masculine in our reflection, we had stripped it and covered it all away. Only thing that remained was 2 cute and hot girls.

"We need to change our names," he said. We can't call ourselves Greg and Stan, it just doesn't quite fit anymore.

"Soo, what do you suggest?"

He thought a bit, "Hmm, how about, for as long as we are in sissy mode, I go by Ginny, and youuu...Stacy."

"Alright then," I straightened my back and extended my arm. "Hello there Ginny, I am Stacy," pulling him-no, her- close, "Very pleased to make your acquaintance." Calling myself a girl caused a flutter in my stomach. Like the seams of my masculinity were being stretched and ripped.

"Pleasure is aaaall mine Stacy." Her hand moving to my bulging crotch.

"And what do we have here? Oooh, you naughty, naughty girl. So pent up." Rubbing my shorts, till my penis peeked out. I moaned flustered, god that was hot.

We kissed passionately and landed on the couch, feeling our bodies and clothes intensely. We changed positions, as she rubbed her face on my shorts and I lifted her skirt, uncovering her tasty prick. I licked my lips, knowing I'd be occupied for the next minutes.

We happily moaned while sixtynining, appreciating each other's dick. I wanna fuck her face so bad, I thought. My legs wrapped around her head, locking it in place, thrusting lightly, while my mouth and tongue sucked hard. Mmm, give me that cock-juice, I wanna get to the center of this juicy lollipop. Gre-Ginny- squeezed my ass with abandon, and slapped hard. I let out a girly shocked moan. I heard her laughing with her mouth full of dick, must have felt it twitch harder.

Another slap, even harder, again, and again. I could only melt in her relentless embrace. How debauched I was, dressed so feminine, devouring my friend's dick, while she sucked mine and smacked my butt.

We came into each other's mouths, exchanging our essence, moaning in unison. After cuddling a bit to recover, Ginny asked, "Hey, want to take a closer look at the Big Johnson?" She pulled out the dildo and left it in my hand. I grabbed it firmer and inspected it. "Well, it's certainly...imposing." I noticed.

"I know right, can you imagine how it'd feel?"

"To be honest, I don't know...shouldn't we build up to it?" I asked.

"Build up?"

"Yeah, that thing is gonna tear us apart, personally, I'm not a big fan of that."

"Hey," she grinned sarcastically, "Don't be a sissy."

I pouted.

"Alright, alright you butthurt baby, how's that? We get some medium sized anal plugs, and then we'll see." Ginny suggested. Now that was more like it.

Soon our plugs arrived, along with some new clothing. We got a few more so we could toss together different mixed outfits. We also got gym sets, meaning sports bras and yoga pants. We did want healthier, leaner, tighter bodies, so we decided to exercise together. We started with aerobics, since we were new to this, and then took to heavier stuff. The only weights we did were for legs, glutes and ass, trying to make those butts pop out.

It was too early to see the difference, but we certainly felt it. So much more energetic and active. Hornier too. All this panting and heaving close to each other made us end our workouts with hard-ons, jerking together in the shower.

It was time to try the butt plugs. They were simple pink medium ones. We cleaned our asses with enema and Ginny applied some lube liberally all over my hole. She then inserted the appendage, drawing a gasp from my lips. It was supposed to be medium, but it was still pretty big for me. She must have sensed my tension, 'cause she went slower and caressed my ass.

"Shhh, good girl, almost there, relax for the last bit."

My cock twitched, I wanted to be a good girl. I wanted to be such a good girl for her. I laid down, ass up, relaxing every single muscle, like she told me. She took it out, applying more lube and trying deeper. Bit by bit it was prodding deeper, and I felt less and less resistance, and more and more pleasure. Once the plug pushed itself forward and lodged in my rectum, I moaned shocked. Another heavy blow on a neglected masculinity.

"How does it feel sweetie?" Ginny asked, patting my cheek.

"Mmm, feels great girlfriend, I am stuffed." I turned around slowly, trying to get used to this new sensation.

"Let me do you now," I said picking up her plug. She lowered her panties and bent over the table, resting her torso on it, legs spread, cock and ass looking so inviting. How could I resist?

I kneeled down between her feet, face buried under her ballsack, slowly jerking her off, while nibbling her balls. She moaned lewdly. My other hand lightly pressed the lubed plug on her asshole, as she now grinded her scrotum all over my face. Damn, why did I like this so much? I was turning out to be quite the cock-slut for her. Was it her soft skin? The tingling sensation that came with cum? The fact it was Ginny's dick? This is no time to wonder, it is time to suck slut.

I took the balls in my mouth, savoring them, feeling her cock in my hand, all the while pushing the plug inside. Her bouncing on my face made it go even deeper. Hungry whore, I thought smiling.

Her plug went all the way in, as she gasped loudly.

"Oooh, fuck, mmm, take off your hands and open your slut hole," she commanded.

My arms fell slack on my sides, while she backed up a bit, raising her ass, then slammed down into my mouth. I gagged as she suddenly filled me down to my throat, but fought the urge to take it out. This is where it belongs, this is my place, a cock-sheath. I want her to cum. I need it. I am a cum-bucket. The only bad thing is I wouldn't taste it, as it would go straight to my stomach. As she pistoned away, I didn't know how to time my breaths properly and felt my oxygen lessening.

"Gaawd, this pluuug feels ammmaaazing," Ginny moaned in debauched delirium. I knew what she meant, every time she thrusted downwards, my ass pressed on the floor, the plug nudging my prostate.

W-wait, how did I turn into this? When? A voice in my head screamed against this.

Another voice, sultry and feminine drowned it in sweet velvet. Stacy.

Why didn't I turn into this sooner?

"Mmmmnnnnghyessss babyyyy," Ginny pushed once more, exploding in my throat. I lay there taking it, watching her balls and ass tighten, shooting rope after rope down my stomach. My own penis leaked as my prostate pushed me over the edge in a hands-free orgasm.

She pulled her cock out, legs shaking, kneeled in front of me and kissed me lovingly, as I was coming down from my own trance.

"Now we put them on, we just keep them for a few hours, 'kay?" she suggested. A bit dizzy from the oxygen depletion, I answered.

"Mmm'kay."

"Mmm, such a good girl," she whispered, kissing me more.

I never wanted this to end.

We kept going, further and further. The plugs were used daily for a few hours, we got used to stretching our asses and keeping them full. More clothes arrived, this time sluttier. Chockers, tight dresses, thongs, stockings, garter belts... We were on that trail for good.

Our normalcy got even more extreme. We wore these clothes all the time, panties as underwear was the default, and we even started following a few tutorials on making our voices more feminine. Also, we switched to applying depilatory cream, instead of shaving, seemed more convenient and permanent. It felt better too. We took better care of our bodies now. Exercising, using creams, conditioners. Things were looking good.

Then there was work. My job was being a graphics designer, not much need to get out of home. I messaged any clients and then worked on my computer. A while ago, I would sketch and draw playing music in the background, now I enjoyed listening to hypnos and erotic audios. It kept me in a constant state of arousal and alert, Ginny loved to see. She worked as a developer at a company, it was a hybrid situation, where most of the work could be done remotely, but she had to attend a few meetings or speak with clients. That horny slut wore panties and plug a few times she was there. Told me it was the most interesting meetings she's ever been.

Lately I've been thinking. I had noticed I constantly thought of Greg as Ginny and spoke with...him, in such manner. Even more so, I thought of myself as switching personas, jumping from Stan to Stacy. Hearing her voice, her call, sensing her tender touch, her sexy clothes. She was so sweet, and horny and soft. A stark contrast to the hard cock she had started craving. Ginny was incredible, with her delicate skin, cute looks and delicious prick, but a new hunger was awakening. A deep desire for meaty cocks, plunging deep, stirring my insides. Wearing panties all the time had an effect on me. This soft fabric, caressing my skin, wedging between my cheeks, brushing over my hairless asshole, it made me...

Made me want cock.

One day I couldn't take it. I took out the large dildo we had bought. I placed it on the floor and stared. Damn, was it thick. Like a real man's dick should be. I bent and kissed it, while my dicklet twitched impatiently. I enveloped the member and slowly began deepthroating it. It was not a hot, real cock, like Ginny's, but it was filling. It stretched my jaw to its limits and I practiced breathing effectively. After a while my ass grew greedy. I wanted this beast inside me.

Nearly shaking, I got up and squatted over the rubber dick. It teased my anus with its triangular head, promising to tear me apart. This time I couldn't wait.

Slowly, my hips lowered, bringing more of the shaft inside me. I shivered. I stopped at the point of discomfort, allowing my body to get accustomed to the intruder. When sufficiently stretched, I lowered more. This went on until I passed the bottleneck of my sphincter, and my ass swallowed the entire toy. It shocked me, but I began lightly bouncing. It felt so bizarre, yet incredible. My insides were wrapping around the big phalus as it poked my prostate, sending waves to my entire being.

Fuck, the whole thing is inside me, I am taking it like a whore. My heart was beating like crazy and my ass was on fire. Head down, ass up, I moved my waist, bottoming out the dildo, then going all the way up to its head. So divine, this heat building up, this sweet pressure inside my very core. At one point, my frantic movements caused the toy to come out. Nnnooo, go back innn. My hand pulled it back in the warmth of my flesh. I was beginning to grow tired, I hadn't trained these muscles extensively before and my pace let up. If only, if only someone would pound me.

I heard the keys unlock the door. Greg entered the room, he came from outdoors so he wore male clothing. He saw me fucking myself on the floor, like an animal and grinned.

"Couldn't wait you little restless whore."

"P-please," I pleaded with shaky voice, my insides felt they were liquefied. "Please fuck me."

He undressed smiling, "How can I say no to that?"

"First, get me ready," he commanded undressing. I obeyed. I took his hardening cock in my mouth, and felt it growing rapidly. He only wore his boxers now. I saw him staring my ass, still stuffed by the thing, with need. He was a slut just like me. Underneath his clothes, the facade he showed outside, he was like me. A sissy slut. I was just more helpless, couldn't hide it.

She and that dildo spitroasted me, every thrust transferred to my ass, pushing harder on the toy. This silicone cock made me realize. It wasn't just Ginny's prick I wanted. It was dick. Every dick. I wanted to submit to every meaty pillar I could, please it, stroke it, suck it, bury it in my ass.

Ginny pushed deep, holding my head in place, while unloading inside me. I came leaking at the bliss of her seed, as my bottom buzzed happily on the dildo. It was my first proper sissygasm. This climax was different. I felt my need for more, undiminished. I still wanted it raw.

I swallowed her sperm in stupor. "Mmm, you still haven't fucked me..." I complained.

Greg panted, his cleaned cock twitched vigorously. I smiled and turned around, showing him my gaping hole. "Mmm, baby...I want you to do what your ex would only let you dream of doing. Plunge deep. Claim my virgin ass. Fuck me silly."

I twerked under his cock, making it spring up.

"Hah, hah," he panted, "lie down bitch. On your back, I want to see your slutty face when I fuck you." His voice cracked, he craved it.

I laid back and spread my legs for him, such an eager whore.

He wasted no time, guiding his member in my hungry hole. I moaned ecstatic as his warm cock entered me, a real dick, for the first time. With that, I gave up my virginity. Not to a woman, but a dick. He panted as he pulled away, making me whimper, only to thrust balls deep, making me yelp. I was blown away. Greg grabbed my legs and pushed me, fucking me relentlessly. Yesss, this is what I wanted. At long last, a cock showed me my place, as a desperate whore on the receiving end. But something was amiss. Greg, he...He wasn't being true. He wasn't a real man. That's what I needed. I either needed to be fucked by a hunk, or I needed Greg to be himself, to be Ginny.

He stopped for a few seconds, losing his pace, I found my chance and pushed him back, getting on top of him.

"Aah, mmm baby, you are not honest with yourself, are you sweetie?" I asked sultry. "You look a bit confused, little gay boy."

He seemed flustered and nervous, like I had hit a sensitive spot. I kept bouncing on his cock.

"Mmm ah, ah, don't worry baby, you are not a gay boy. You are a little sissy slut, and I love it. I love it so much. I know you love it too, don't deny it." I laid on top of him, sucking his earlobe. "Give me, give me my girlfriend. Give me that cute cock. Give me your girliest moans. Mmmm pleeease."

She had started breaking through, her feminine moans took over his panting. I could see that gorgeous beauty coming out, this time permanently. Just gotta give it a little push. I grabbed the dildo and teased his ass. His whimpers were adorable. I pushed deeper and harder, breaking apart the vestiges of masculinity, the last resistance of his, tearing down Greg the man. It was time for Ginny the woman to blossom. I rode her cock while thrusting the toy into her, she soon grabbed my penis and jerked with abandon.

"Aaah, yes, YES. Show me. Show me how much you want it. Show me how much you need cock," I screamed blissfully.

"I FUCKING LOVE YOU GINNY."

Our girly moans weaved like a choir, reaching a debauched crescendo of mutual penetration.

She was ecstatic and released, her tongue hanged out, catching my ropes of cum that landed on her face, as her jizz filled my insides. So good, so warm. I want it inside me forever. I fell on her and we stayed like this for a while.

"You are not a man, you are a sissy like me. Feel how better this is baby?"

She didn't answer until later, when her panting died out.

"Thank you," she said. "I love you too." We kissed and cuddled tenderly, until we fell asleep.

It was time we shed the facades of our false masculinities. We were girls.