The Derrick Dilemma Pt 03

When I took showers, the water felt like a hundred fingers tickling my body. My physical senses were heightened and I couldn't put it to the back of my mind. Ever since I turned back into a male, my libido wouldn't die. If only I had a friggin' girlfriend! Curse my busy career!

Alas, my hands would do. I enjoyed letting them dance around my hardened member. I squeezed it and worked the shaft with wild strokes. My other hand cupped and massaged my balls. I watched intently as they bounced, as my head bulged, and as the cum shot out. It all felt so new compared to the years of half-minded masturbation.

I barely saw Friday arrive. I was so focused on work and dealing with my hormones that the weekend arrived sooner than expected. As Tiffany, I'd need to be firm and not allow Derrick to play any games.

I took the pill Thursday night. I drank plenty of water, became dizzy, and collapsed in bed. In the morning, I woke up as Tiffany. Seeing myself, Tiffany's body, gave me goosebumps. My breasts were firm in my grip and my body vibrated with excitement. A burst of energy jolted me from the bed and a giddy smile dominated my face.

I showered, enjoyed the rippling sensations, and dressed up for Derrick's arrival. I chose a brown blouse tucked into a thigh long black skirt. Wearing a skirt felt freeing -- I saw the appeal of kilts. I bent in front of my bathroom mirror to make sure nothing peeked. Check, but I did like the view. If Derrick weren't coming, I'd be all over myself. However...

*Knock knock*

Derrick arrived in an undone button up, tight undershirt, and his usual jean get-up. He cast an intrigued gaze up and down at me, before saying, "Good morning."

"Come on in," I invited him. He passed me by, and as I closed the door, I could feel his gaze. The blouse had some cleavage and back exposure, and most of my legs were exposed. Admittedly, there was plenty to see.

I turned and asked, "So what's this scheme of yours?"

Derrick turned around and sighed, "Okay, first thing's first...I need to apologize."

I remained quiet, but crossed my arms to show a little reaction. Derrick continued, "I've had all week to think. Talked to some friends, thought it over, and I realized the other day that I have been a complete douchebag. I let the alcohol get the better of me."

"Derrick being regretful? Color me surprised," I grinned.

Derrick coughed a laugh and shrugged, "Yeah, it's not fair to you either way. Whether you're actually Thomas or some hired chick, I shouldn't act that way. So, I'm sorry."

Things were finally relaxing. I joined Derrick in the living room, "Apology accepted, even if it took too damn long. However, I'm ready to settle this once and for all."

"That's the easiest part of all this. We can just spend the whole day together. Let me see who you really are," Derrick said.

"Oh, wow, that is easy. Um, okay, I don't have any plans today," I readily accepted.

"Yeah, nothing elaborate. I didn't graduate college for a reason," Derrick joked.

I laughed and walked into the kitchen, "Want something to eat? Beer?"

"I'll never say no to a beer, and having breakfast served by a pretty lady is always welcomed," Derrick flopped onto my two-man couch.

The compliment made me scoff, "Dude, shut up..."

I scoured through my cabinets and refrigerator. To my surprise, I didn't really have much. I needed to buy groceries. I asked, "Sooo, you wanna go out to eat? I've shit-all here."

"Sure, though it's a bit odd you'd suggest breakfast, but not have anything to cook," Derrick begrudgingly got up from the couch.

"We already established I have poor memory," I responded with an attitude.

Derrick and I went out. Being out and about in public with Derrick was different than with Megan. With Megan, my nerves were on fire, and I felt like everybody was watching me. With Derrick, I was more at ease. I was far more used to being a woman. That or maybe being a young babe next to a taller guy resembled a papa bear protecting its cub.

Derrick's mood was a lot lighter. We decided to grab breakfast at a diner. We cut loose about sports, movies, and anything funny. We were Derrick and Thomas again...though with some notable differences. Derrick held doors open, and followed behind me in narrow walkways. He welcomed my opinion more openly than when I was Thomas. He complimented me more. I actually liked it all. I was being appreciated.

By the end of the day, I wasn't angry anymore. Coming up the stairs to the apartment, Derrick allowed me to go up first. With him behind me, and me at a higher vantage, I knew my skirt would catch his wandering eye. I casually swayed my hips and tilted them back. I'm not sure if it worked, but I felt like I was rubbing my ass in his face. As Thomas, he'd probably hit me and tell me to stop. No such retort as Tiffany. My tease ended as we entered my apartment. As I unlocked the door, I stole a glance at Derrick's groin. A bulge; he was looking!

We entered my apartment and I snagged a beer from the fridge. Derrick opted for my half bottle of whiskey. He took a seat at my dining table with two glasses. How considerate.

"Whiskey for lunch?" I asked, bewildered.

He poured himself some of the whiskey and nursed it, "Oooah, yeah. Fuckin' crazy week. Work's been nothing but shit, and I've been burnt out. Things have been overall bad. I really need this."

I sat at the table with him, "You're telling me. My whole world is spinning and changing."

Derrick didn't acknowledge my comment as he sipped more whiskey, "Yeeeaaah, that hits the spot. Didn't care too much for the weak shit at the party."

"Can I ask you a question?" my curiosity, and lightened mood, encouraged me. Derrick simply raised an eyebrow as he finished his whiskey. Damn, he drank fast, "Why did you become so hostile during the party? I thought we were getting along perfectly, until I found you with Bob."

"You want me to be honest?"

"Please..."

Derrick snorted a laugh and grabbed the whiskey, "Alright, gonna need another one of these..."

He poured a glass and then shotgunned the whiskey. I cocked my head and leaned on my arm on the table. The dramatics were unnecessary, but whatever. Derrick shivered, made some horse noises, and then sighed, "Because you're fucking hot."

This floored me. My gut rolled, my face burned, and my words were lost. Derrick shrugged his eyebrows and then poured more whiskey, "And I'm not saying that because I finger blasted you at this table. You have pretty eyes, a fun personality, and one helluva ass."

I sank in my chair, "Come on, man. I've barely been a woman for long, and you have a crush on me?"

Derrick squinted, "What's wrong with me finding you attractive? Whether you're Thomas or not?"

Floored again. It was so simple for him, but so problematic for me. If I were Thomas right now, I doubt he'd say it. I liked the compliments, but from Derrick? I definitely had mixed feelings. I abandoned the beer and poured whiskey into the second glass. I only filled it with a shot's worth, and downed it. Derrick seemed surprised, but I understood why he opted for more liquid courage. This was some heavy shit...

"Wait, you got angry at me for being hot?" I needed clarity.

Derrick sank this time, "No, it's because of Miller..."

It finally clicked, "You got jealous?!"

"Shhh!" Derrick hissed. He looked around like the FBI were watching. He then grumbled, "Yeah, sure, what the fuck ever. I didn't like seeing you two kissing, and then getting busy in the bathroom. Sue me!"

I rolled my eyes as hard as I could, "We didn't get busy. I was curious about my attraction to guys. I found out I like being touched and kissed, just like when I'm male. So I asked to see his junk to see if there's anything sexual there."

Derrick leaned back, obviously pained by the explanation, "Oh yeah? What's the results, doc?"

I paused to reflect. Miller's long member lived rent free in my mind all week long. As Thomas, I simply envied it. Now, as Tiffany, my heart picked up its pace. Intrusive, lewd thoughts warped my opinion. I hid behind Thomas, "It didn't do anything. No feelings...aside from envy."

"Envy?"

I cracked a smile, "Miller's packing a python."

Derrick confidently challenged, "Oh yeah? Is it bigger than seven inches?"

I nodded in response, and Derrick barked a laugh. He finished his whiskey and then headed to the bathroom. He closed the door without a proper response. Did Derrick have a seven incher? Was I the smaller guy in our group?! What the fuck?! I ignored the heat in my stomach as I served myself more whiskey. It burned my throat, but numbed my mind. My anxiety was curbed.

Derrick's phone pinged. He'd left it on the table. As I looked at it, I saw he'd gotten a text from Bob. The short preview immediately caught my attention.

"NO WAY!! Tell me how the date goes with her and if..."

The words stabbed my heart. Her? Date? I quickly poked the notification and hoped it would open. It did! The full text was on screen, as well as its history. Derrick previously sent a text with a picture.

"Check it out I'm on a date she said yes," and the picture that followed Derrick's words was of a selfie of him, with me in the background at the diner. I sat peering out a window in the background as he paid at the register.

What the fuck?! How did I not see him take this? And he's telling Bob we're on a date?! I scrolled up. Previous texts from that morning showed a conversation between the two. Derrick promoted his plan to ask me out on a date. Bob showed doubt, since he believes I'm Thomas, but Derrick affirmed that if I said yes, it would prove I wasn't Thomas.

The fucker lied to me and my friends!

"What are you doing?" Derrick said, right behind me. It spooked me and I dropped his phone on the table. With a mixture of shock and hatred, I turned to face him. I was met with an apathetic glare.

"What the hell have you been telling Bob?" I demanded answers.

"Just having some fun. You need to calm down," Derrick picked up his phone and pocketed it.

"Fun? You're telling him we're on a date and that it proves I'm not Thomas!"

"It technically was a date," Derrick grinned.

"No! Fucking stop, dude! This isn't cool!" I was on the verge of tears.

"What is your problem?" Derrick became very somber. His icy cold eyes drilled into me. It was...intimidating. He pressed, "You let me finger you, you take the name I gave you, you pretend to be Thomas, you ask fuckin' Miller to pull his pants down, and now when we hang out, you wear a skirt and wiggle your ass in front of me. Why do you keep contradicting yourself?"

I panicked, and feebly said, "I was just...having fun..."

Saying it out loud didn't help. Derrick's frustration flared, "Oh! You can have fun being my 'friend', but I'm an asshole for taking the bait? Fucking please!"

I had to defend myself. I had to try, "I..."

"You're not Thomas! Not even close. All day today you've let me pamper you," Derrick interjected. "He hates when people do that. He wouldn't flirt with me, he wouldn't want to kiss dudes, and he definitely wouldn't ask a guy to pull their dick out!"

I wanted to run and cry. My choices, from getting back at Derrick to simply having fun as a female, thoroughly convinced Derrick I wasn't Thomas. To him, I was a girl who got naked for him on their first meeting. Regret rattled my brain.

"Fuck it! I bet you're lying about your bathroom quickie with Miller. You've lied about everything else!"

"It's not true..." I whimpered.

"Prove it, then."

I was about to ask how, but Derrick read my mind. He ran a hand across his groin, and began rubbing himself.

I looked him right in his smug face, "You're kidding me..."

"Thomas is straight as an arrow. If you saw Miller's dick and turned it down, it should be easy to turn me down. I'd be much more convinced if you did," Derrick said.

I went back to watching his hand. It stroked along the bulging length. My nerves took over and I recalled how tempted I was with Miller. I had the urge to kick Derrick out, but that'd solve nothing. The alcohol gave me the courage to glare and show my defiance, "Fine, do it."

Derrick unbuckled his belt, while staring lustful daggers into me. Before he continued, he said, "You'll need to be on your knees. Mine is smaller than Miller's, after all."

I wanted to deck the grin right off his face, but I was done fighting. I wanted to get this over with. I obliged, kneeled, and put my face inches from Derrick's crotch. Down here, the bulge seemed so much larger. It eclipsed my sight, and all I could do was stare and wait with bated breath as Derrick opened his jeans.

His bulge pushed past the zipper. His briefs were barely containing his member. He was not small; another fucking lie. I tried to mentally prepare myself, but Derrick went ahead and lowered his briefs. His cock head swung out and slapped my nose before resting on my cheek. Not small! My slow reaction emphasized my shock as I pulled my head back to take it into view. Where Miller had him beat in length, Derrick surpassed him in girth. It was thick halfway up the shaft and right under the bulbous head. His engorged cock resembled a club. My eyes took it all in with absolute wonder.

Then he flopped his balls out. I don't even recall Miller's balls, but Derrick's stood out. They were big compared to mine, and they hung ever-so-slightly. They looked so plump and healthy...

"Dude...what the hell? Why is it...so..." I didn't want to say it.

"So what?" Derrick asked.

"Thick..." I sighed. Derrick flexed it, and it lurched towards me. It didn't reach, but something about it 'reacting' to me set butterflies free inside me. I continued to survey the douchebag, "Like, seriously, this isn't anything like mine, or Miller's."

"Does it do anything for ya?"

My eyes pretty much devoured it. The guttural temptations returned. Derrick's cock was amazing, not ugly as I had hoped. I couldn't let him win. I cast my eyes away and stared out my window. I needed the distraction, "I don't like it. I don't like it at all."

I sounded so bratty, and I think Derrick picked up on it, "Nah, you and Miller were in the bathroom for a hot minute. You'll have to stare at it for a few minutes before I accept your denial. Here, let me give you a better angle..."

Derrick repositioned himself in front of me at an angle. Here, I witnessed its full length and girth, rather than straight on. Even the underside of the cock was thick, where his urethra looked more like a fire hose. Seeing his erection and balls swing as he moved was hypnotizing. He stroked it a couple times, and his grip detailed the veins. Dammit! Why did Derrick, a manipulating asshole, have such an amazing cock? I had to admire it for just a bit longer...

It flexed a few more times, and each time it bounced. I watched it intently. I'd steal a glance at Derrick's face, and he oversaw with lustful delight. His member remained erect and pulsing. The intrusive thoughts flourished, and the longer I stared, the more vivid they became. His cock started to look and smell delicious. I wanted a taste. At some point I had started breathing heavily through my nose. The sound of sharp air was practically deafening in the silence. The moistness between my legs became apparent to me, and my whole body burned. I could barely contain myself...

Then Derrick cupped my face with a hand, and he moved my view up. He spoke gently, "Say it, Tiffany. All I ask is for honesty. I'll know if you're lying."

He would; hell, I'd be stupid to try and continue denying it. Yet some part of me seized my mind, breath, and body. I struggled to say, "Derrick, I can't say it. I'm Tho..."

Derrick placed his thumb on my lips, "Shhh, not now. You are Tiffany. What does Tiffany think?"

So domineering -- I hated it. My nerves shook my body and formed tears in my eyes, "If I say it...then..."

Derrick interjected again, "Then my cock is all yours."

The line broke me. I released my held breath and whimpered. Derrick made me whimper. The last week flushed from my mind. Derrick closed the distance and laid his thick cock across my face. Another man's member filled my vision. The smell was nice. Cock smelled nice.

"Look at you, Tiffany. You're stressed out. I'm trying to help you. Hell, I'm not even the one fighting it anymore. You're doing this to yourself. It's so stupid."

It was my fault. I was repressing my feelings. The warmth of his shaft on my face felt like I laid against an arm. It comforted me in my deprecation.

"Say it, Tiffany."

I lost, Derrick won. I surrendered, "I like it."

"You like what?" Derrick grabbed the base of his cock and rubbed it up and down my face. It wiggled between my chin and eyes. I almost recoiled, but that's what Thomas wanted...

"I like your cock..." I forced out. It was liberating.

"Do you want my cock?" Derrick's voice was so apathetic, but with a guttural sexiness to it.

"Y-yes..." I forfeited.

"Go ahead. It's all yours," Derrick readjusted to a straight on view, his shining helm right at my lips. I stared down the barrel. It flared and precum leaked out. It dribbled on the tip's underside. How did it end up this way? I had one of my best friends' dick in my face. The same guy I'd have standing next to me at my wedding. The same guy who for the past week painted a false picture of Tiffany. I let myself get cornered.

It was too late. I wrapped my fingers around the shaft and hoisted it up. It had heft to it, and it pulsed in my grip. When he flexed, its hardness staggered my mind. So manly -- I admired it. Where was I supposed to begin? I decided to pretend it was mine, and did the things I would enjoy.

I kissed the shaft. Warm. I kissed it again, and I pecked up and down. A man's genitals were tougher than a pussy -- its stiffness made each touch seem impactful. I made out with a cock. Derrick watched with a shimmer of satisfaction. After another kiss, I actually felt his urethra pulse, and precum emerged from the head. It trickled down towards me, and be it curiosity or primal instinct, I licked up the staff and to the reward. His precum coated my tongue as I reached the top of the mountain. With my mouth wide open, I dove. I let another man inside my mouth. Thanks to his lube, it slid in with ease. His precum was sweet -- so delicious. As I sucked on my first cock, I was delighted each time more juice came out. I could feel the slight ridges and bumps all across the head. The tip ramped across my tongue and glanced my roof. His girth widened my mouth. It also kept me from taking any more in, as my gag reflex kicked in. I lurched, and pulled back. His thing slipped out and bobbed in front of me. Some precum painted my lower lip, and as I tried to lick it up, it just spread it across. Sucking dick wasn't as easy as some made it look.

"You good?" Derrick's dumbass grin was on his face again.

"Don't give me that," I scolded him. My entire mouth was caked in his sweet, slippery precum. Derrick's dick was waiting at attention for more affection. I grabbed its base and glared up at him, "You know you have a big cock. This thing won't fit in my mouth."

"Might fit somewhere else," Derrick winked.

"Shut up..." his words sliced into my consciousness. Would it fit? I buried the thought as I sucked along his mass. Would we try having sex? I buried the thought as my taste buds lit up. My saliva mixed with his cream. How long were we going to go? I buried the thought as I reached up and cupped his balls. Derrick's balls were so plump in my small, feminine hand. I massaged them, and he groaned. I peeked up at him, and saw his head rolled back. I pushed up and squeezed, but not too hard. This forced his club to flex, and I earned more cream. It was so tasty; and gaining some control in the situation emboldened me.