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The Derrick Dilemma Pt 01

The Derrick Dilemma Pt 01

by sclew101
19 min read
4.49 (7800 views)
adultfiction

"It's almost here..." I stared gleefully at my phone. The tracker for my package inched closer and closer to its destination. After ordering the product a month ago, I was about to change my life forever.

My name is Thomas, and for most of my life, I've felt more like a woman on numerous occasions. I am biologically male, with a proud set of dangly parts. Yet from time to time I will be more feminine. The way I move, talk, express myself; it all feels so natural. Thus, I have always wondered what it'd be like to be a female. Thanks to a recent breakthrough in medicine, that wonder switched to a wish. Homollata Tortum, also known as gender pills, rocked the world.

Saving up my money over half a year, I was able to acquire the gender pills. Expensive little buggers, but worth it to realize a side of me I could only imagine expressing. I worked four days a week, giving me a long weekend to enjoy myself. Thus, I waited in anticipation. I've never had my nose glued to my phone screen for so long.

*Knock knock*

The GPS must not have been updated yet. My heart dropped and I bounded across my studio apartment to the door. I swung it open. Lo and behold, plopped haphazardly onto my welcome mat was a small, inconspicuous box. I hoisted it inside and locked the door shut.

I moved to the kitchen counter, fumbled with a boxcutter, and undid the hard work of those who carefully packaged my dream come true. I tossed aside the packing paper and saw it inside. Wrapped by a paper receipt was a small medicine bottle with a blue cap. A pink, glittering card sat beside it with nothing more printed on it than a big red heart. Cute, but unnecessary. I tossed the trash and dashed into my bathroom.

I twisted the bottle in place to read the label. From what my physician told me, by taking a gender pill, I would come down with a heavy fever. The flu-like symptoms were a sign that the pill was working. They said to go to the hospital if the symptoms never came. The bottle affirmed this, as well as other warnings and side effects. It mentioned drinking plenty of water to hydrate, as well as not mixing any substances while on the pill. Side effects if mixed with recreational drugs or alcohol included nausea, drowsiness, headaches, change of behavior, cognitive or memory problems, or insomnia. Severity varied, so that I would need to experiment with. The fever would eventually knock me out, and it advised me to not drive while going through the effects. Fine by me; it was 6 PM, and I had no plans for the night.

I didn't need to stand on ceremony. I unscrewed the top and shook out one of the pills. Pink - how appropriate. I poured myself a cup of water, downed half the cup, and tossed the pill down my throat.

Easy. As. That. I felt my nerves flare up, but it was a nice kind of tingle. Like seeing an attractive woman. It would take time to change me, so I went about my evening drinking water and pacing. What would I look like? How would I feel? Is it working? Will I turn back into a male? The final question made me check the container. '1 PILL/3 DAY DURATION' was printed across the bottom of the label. As it crossed my mind, the words blurred. I felt a sinking in my body, like being hit by a wave. My body heated up, my head began to pound, and I felt sick to my stomach. It was happening. I stumbled to my bed, groaning in agony. The nauseating pain became cacophonous. All I knew was this fever. Until I fainted, and all went dark and silent.

***

I brushed my hair aside as I rolled over my sheets. My body ached a bit, but perhaps it was due to an uncomfortable position. The stretch that followed surprised me out of my stupor. My chest shifted with weight, and my usual morning wood was obviously absent.

These realizations snapped me awake and I jolted up. With a new, feminine voice I exclaimed, "Boobs!"

I gazed across my new body: feminine curves beneath my now baggy clothes, locks of hair framing my view, and legs for days. My mouth hung open in shock at how flawless the gender pill worked. My beard was gone, replaced with a petite, smooth jawline. My legs had less hair, but I definitely needed to take a razor to them.

My breasts were a decent size, and their weight was noticeable. I instinctually fondled them -- sensitive. I lifted my shirt up and let them swing. Childishly, I wiggled them about and giggled. Pervertedly, I loved watching them bounce. I ran my hands along my sides and across my hips. All of it was so sensitive. I recall what the doctor said; the sudden shift in hormones will cause me to have a heightened sensibility. Aside from touch, I was vibrating with excitement and joy.

I danced about, "It worked! Heheh! It friggin' worked! I'm a girl!"

I plopped down on the edge of the bed. I shifted my attention between my legs. I was so used to having a package, that the absence of one was truly alien. The moment of truth; I untied my PJs and let the pants fall. I sat and admired the sight -- a pussy. Like my boobs, I glided my hand and fingertips along my new genitals. The feeling was extra electrifying. Sooo sensitive! It felt like the tip of my cock after being teased for hours on end.

"Well, it was bound to be..." I weakly said. I laid back, eyes closed, hands on the prowl. One hand ran from tit to tit, slowly glancing the nipples. My other hand pressed my wettening slit open. The sensation was wild, but I used my knowledge from past experiences to finger and tease myself. From rubbing the clit to pushing two fingers in and working them in and out.

The amount of time I spent on the bed masturbating is unclear. Groping, tickling, and shifting positions to find the best spots that my new body enjoyed. My gasps and moans only turned me more on. Everything compounded until I surprised myself by cumming. It erupted far differently than when I was a male, but it felt very similar. Less explosive in one spot and more like a deluge of internal water. I let out a long sigh, smiled like a doofus, and could hardly contain my laughter. I fucking loved every bit of it.

I revisited exploring my body in the shower. Each part of it excited me more and more. I was so sensitive. My nipples would perk up, my pussy remained wet, and my body tingled as I ran my loofa over its curves. The only annoyance was my longer hair. It came down to my shoulders, instead of the few inches of mess on top. Afterwards, I fetched myself some breakfast. I thought about the trip I needed to take to the mall to grab female clothes. My dude clothes wouldn't really do. I'd be a female for three days straight, but the bottle contained twelve pills. Bras, pants, and tops were vital for me to live the full experience.

One of my best friends, Megan, volunteered to help me on this adventure. As I texted her about my transformation, I decided to let my closest friends and family know. My heart sank a bit as I wrote to my parents. They weren't the biggest fans of any combination of 'sex' and 'change'. However, it wasn't my choice if they accepted it or not. I was happy.

Many showed the same feeling. Curiosity and encouragement flooded my phone. My sunken heart lifted. My friends planned a get-together two days from now, but I wanted somebody's immediate reaction. I needed a guinea pig. The nearest friend was Derrick. A bro if there ever was one, I met him as a coworker almost a decade ago, and we've been good friends ever since. I hadn't yet contacted him.

"Yo, you available this morning?" I texted.

Two minutes later, "for the most part what's up?"

"How about you come on over? I got something cool to show you."

"Ok give me 10."

Boom! My nerves were riled up, but I couldn't wait to see how somebody would take to my new body. I threw on one of my t-shirts and gym shorts and waited.

*Knock knock*

I stood up. My heart rammed my chest -- I mini-panicked. I steadied my movement and breathed in, then breathed out. I calmed myself -- no need to freak out. This is who you are. He'll be cool with it.

I swung the door open and piped, "Hello hello!"

Derrick stood there like a bump on a log. His hands were tucked in his hoodie pockets. His lax eyes sparked to life when he set his sight on me, and heard my welcome. It quickly changed to confusion and awkwardness.

"Hi..." he trailed, his eyes darting past me into my apartment. "Is Thomas here?"

"Yeah, dude! You're lookin' at him!" I took a step back and presented myself in a showman manner.

Derrick stepped inside and closed the door, still perplexed. He removed his flats after fumbling with them under his baggy jeans. He doubted my presentation, "Sorry to say, lady, but you're about a foot too short and far too pretty to be Thomas."

"Hey!" I furrowed my brow. Standing before Derrick, he wasn't wrong about my height. I hadn't even noticed until he pointed it out. I rolled my eyes, "I am Thomas. Wait here..."

I popped into the bathroom and popped back out with the gender pills. I handed him the bottle and watched as his confusion turned quizzical.

"Homollata Tortum?" he muttered.

"Gender pills," I translated.

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Derrick squinted his eyes from the bottle to me. I watched them trace my body with his eyes. A couple times on my breasts. He cracked a smile and snorted, "Yeah, right."

"Huh?"

"You're saying Thomas took these pills and became a woman?"

"Well, only one pill. It lasts three days, and then I change back. Any more than one would compound the effect. Three days, nine days, twenty seven days, etcetera, etcetera. With my work schedule, one lets me enjoy them all weekend long."

"You expect me to believe this? C'mon, Thomas, you're better at pranks than that!"

Derrick talked past me, and he dropped the bottle back into my hands. This frustrated me, "I am Thomas, and I took these pills! This isn't a joke, or a prank. Here...ask me a question only I, uh, Thomas would know."

Derrick spun in place to face me. Amusement coated his face, "Okay...what's my middle name?"

"Sanchez," I obviously knew.

"Okay, okay, that was an easy one. Something Thomas could have told you...uh, Tiffany."

"That's...Tiffany?!" I glared at him.

"Yeah, I don't know your actual name, so I'll just give you one. Sure as hell won't call you Thomas...unless you somehow prove it," Derrick shrugged.

"You bastard...fine! Ask me another question!" I demanded.

"Woah, calm down. No need to wrinkle that beauty of yours," Derrick mocked.

"Shut up, oh my god..." I grumbled. I felt my face redden in embarrassment.

Derrick contemplated, "Let's see...ah, I got one. Last year on our group vacation, who suggested we go to Tony's Bar?"

My brain froze: who did suggest it? I barely remember what I had for dinner last weekend. I scrunched my face and guessed, "Megan?"

"Nope, wrong -- it was Thomas," Derrick crossed his arms victoriously. I gasped and tugged on some of my hair. As my mind filled in the blanks of my memory, Derrick put it in words, "Thomas wanted to try out their new cocktail."

"I did! I remember that now!" I slapped my forehead.

"Damn, I hadn't even asked the hard question yet and you failed to answer medium difficulty. Shame, shame. The facade is up," Derrick smirked.

"Ask me the hard question! I'll knock it out of the park!" I pleaded. No way was I going to fail this stupid test of his.

"Alright...may I see your tits?" Derrick buried his hands in his hoodie again and coyly asked. The question shocked me. He saw this and snorted, "I know Thomas wouldn't take a prank that far. So I'd be willing to think you're him if you..."

I didn't even let him finish. I tugged my shirt up and let my girls free. They jiggled a bit. Derrick choked on his words; his eyes were transfixed onto my knockers. Dumbass thought I'd be too insecure? I was known for going shirtless all the time. So what if I had tits now? That wasn't gonna stop me -- not at home, at least.

"How's that, Derrick? Proof enough?" I strutted in a circle and occasionally wiggled my shoulders to let my breasts flop. Again, they weren't large, but they were fine and firm.

"I, um, have to admit...I wasn't expecting that," Derrick scratched the back of his head. The dude was probably starstruck. For the past few months, he'd not have any women in his life. He barely complained, but at that moment I saw a tit-starved man. Plus, it was fun having him squirm, instead of me.

Then, he just casually reached out. Before I could swat the hand away, it pressed into me. Sensitive! His thumb brushed my nipple and elated my entire chest. I gasped, stammered, and then slapped his wrist. He recoiled like a wounded puppy.

I tucked my shirt back over my breasts, "Dude! Don't just manhandle my boobs! What's wrong with you?!"

"Uh, sorry, it was kinda instinctual. I mean, they're a nice set of tits...and you were showing them..." Derrick's confidence waned.

"I showed them to prove a point. It'd be the same as if you grabbed my nuts while I was a guy. Not cool," I chastised. I wasn't entirely mad, just rattled.

Derrick composed himself, "Yeah, fair point. I'm sorry. I guess that means you're Thomas..."

Victory was mine, "Thaaank you! It's about time."

"But why the moan, dude?"

"Moan?"

"When I grabbed you, you moaned. That kind of moan," Derrick studied me.

"Oh, well, the pills make me sensitive. Everything is sensitive, even my face," I rubbed my cheek to emphasize. That simple act alone felt nice.

"Have you...y'know, played with yourself?" Derrick held back a grin.

What a pervert...but I understood. I'd be curious, too, "Yeah, of course. I did the whole shabang."

"Was it as good as jerking it?"

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"It was different, but the same. Hard to say since I've only done it once. The sensitivity might be doing something extra for me," I shrugged.

Derrick leapt at the chance to ask, "Need a hand?"

"Derrick, please, do I look stupid? I know what you're trying here," I glared.

"Now, hear me out," Derrick put up his hands defensively. "Aside from the guy you just flashed, who can you call on to help you explore that avenue?"

I thought for a moment. I'd been single for two years, with no woman looking my way or taking my advances. I hated to admit it, "Nobody."

"All I'm saying is if you want to really learn your likes and dislikes, I'd be glad to help. If at any point you become uncomfortable, because it's me or how it feels, we can stop. Otherwise, that'd be uncool," Derrick stated his case.

My mind raced; how much of my curiosity and imagination was because of the pills, and how much was it my own curiosity? I needed to make sure Derrick wasn't being sleazy and self-interested, "Under one condition: throughout the whole process, your pants stay on."

After a moment, he nodded, "Sure."

Shit, he's serious. I let out a sigh and gave in, "Alright, but we stop when I say stop."

"You're in control," Derrick confirmed.

Unlike a minute ago, I was nervous to raise my shirt. Why? It's just my friend, Derrick. I lifted my shirt up to my neck and gave Derrick access to my bare torso.

His enthusiasm was apparent. He stepped closer and started the rub down. Derrick's hands were warm. They squeezed my boobs and sent shockwaves throughout my body. They worked in tandem to stoke a fire inside me. His fingers circled along my nipples, and it felt just as good as when I did it. His thumbs worked from beneath, as his palms pressed firmly. He was being quite forceful.

"Hey, take it easy, man..." I barely could speak.

Derrick grinned, "Your nipples are getting hard. I can tell you like it, Tiffany."

"That isn't my name," I scowled.

"Calling you Thomas while pleasuring you is gonna be weird."

Before I could retort, Derrick leaned down and wrapped his lips around my nipple. A cried out in pleasure. However, the cry snapped me out of the sexual sensation and I pushed against his shoulders. I sounded so girly. I covered the wet nipple, "That's not fair!"

"You still liked it," Derrick returned to his lax stance and smug expression.

"Of course! You'd like it if your dick were being rubbed and licked. It's pretty much the same thing!"

"That does sound good..." Derrick cocked his head to the side.

I scoffed before lowering my head. As I did, my sight graced the bulge in Derrick's pants. He was rocking a hard on...for me. My body did that to him. The feeling was a strange mixture of pride and disgust. This was my friend, dammit! I told myself I wasn't interested in this shit. Yet here I was wet as water and hot as the sun.

Derrick positioned himself closer, and one of his legs past mine. Our thighs touched and I sharply inhaled. Little me blushed up as his hands slid across my hips. He stared into my eyes as his eagerness wandered onto my ass.

"Derrick!" I cried. "I don't like my ass being touched!"

"Well, I guess we're about to find out if this body is truly different, Tiffany."

"It's Thomas!" I sounded so bratty. My friend's hands massaged my ass. It was plump, refined by years of track and cross country. It carried over into my female body, but I never expected a man to ever put his hands on it.

My gym shorts made the touching far less personal than bare breasts. Not to mention, I was holding back a smack. I truly did not like my ass being messed with.

As Derrick surveyed my reaction, I rejected him, "See? Nothing. I'm tempted to hit you, but I'm trying to be kind here."

"Seriously? Hmm, I think I know why..." Derrick dared. His hands plunged under my waistband and groped my bare ass. I straightened up with an 'eep'. I reached for his forearm and held his arm at bay. His hand, so much larger than mine now, engulfed one of my cheeks. Again...so sensitive!

"What's the matter? I thought you didn't like your ass being played with," Derrick taunted.

I pouted, then steeled myself. I let go of Derrick's arm and surrendered. Would I actually like this? It wasn't as sensual as my tits, but it still did something to me. Derrick even brought my pants down past my hips. My privacy, never seen before by another man, was his to peruse. His eyes locked onto my pussy, but I was too enthralled by his sensual touch to care. His fixation was actually hot.

His hands enthusiastically groped my cheeks. He moved them, bounced them, and spread them. I bit my lower lip; I wanted to make noise. I hated that I wanted to make noise. But...it felt good having somebody touch me like this...

Derrick anchored one hand on my ass as he brought the other around. His fingers traced along my smooth stomach as it inched downwards. He watched for any denial from me. I had none.

My friend split my mound and rubbed into me. He answered my aching pussy's craved attention. The apprehension faded. All that was left was pleasure. I leaned into Derrick as he cradled my ass and fingered me. I was soaked, and his energetic fingers rocked my world. He eventually got them knuckle deep, and it forced the moans out of me. He decidedly pressed his groin into my thigh; he made it apparent how hard he was. I couldn't even register that another man's cock touched me for the first time.

Derrick pushed me. With his hands all over me, and my weakened senses, I couldn't resist. We met with my table and he sat me up on it. When did he get so strong? So manly? Derrick splayed my legs apart, completely exposing my slicked pussy.

"You are soaking wet," Derrick breathed a laugh. He was really into it now.

"I'm tellin' you, it's a wild feeling. It's almost dizzying..."

He dragged his fingers across it, made me hiss, and then held the slathered digits up to my mouth. I resisted instinctually, but the smell was intoxicating. My juices enticed me -- I probably tasted sweet. I wrapped my mouth onto his fingers and received my pussy juice. The taste was as great as the smell. Like some cock-hungry whore, he fingered my mouth as I suckled.

"How's it taste?" Derrick asked.

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