The Derrick Dilemma Pt 05

"Gender pills?" my boss raised an eyebrow. I stood in his office, with my coworkers outside glimpsing in at little ol' me.

"Yeah, it'll wear off in a couple days or early next week. Then I'll return to being Thomas," I explained. Since I took them a day later, it meant that I had to come into work as Tiffany. However, boss man wasn't buying it.

"Did Thomas's dog eat his homework, too? What kind of excuse is this? He already called out sick yesterday, and now he's no call, no show?" my boss grew agitated.

"Please, just let me work today and I'll..."

He cut me off, "Not happening. You are not an employee, and I can land in hot water for that."

"But..."

"Forget about it. And let's say you are Thomas, I don't know what that means for our company. It's weird already having some lady call herself Thomas."

"It's not weird, I'm just...more of myself."

"Right, it's weird," my boss narrowed his eyes. Weird to change myself? What an asshole. He topped off the conversation with, "Whenever you see Thomas again, let him know this; he's fired."

"Fired?!"

"His performance has been slacking, he doesn't jive with the others, and he didn't show up today. Might as well pull the plug, let him...or you...find somewhere else that deals with this...this bullshit," my boss waved me away and went back to his computer work.

I walked like a zombie out of the office. A few heads turned, but nothing more. I wasn't Thomas to them, just some random girl.

I returned home and cried into my pillow. Thomas lost the trust of his friends, and now he lost his job. What a fucking joke of a week.

I checked my bank account and saw two months of rent inside. That gave me one month, plus bills, groceries, and gas. Available jobs near me weren't prospective. I needed a hard solution to a tight problem.

I glanced at my counter and saw the container. I remembered my happiness when they arrived, my excitement when I first became Tiffany, and all the positive feelings being a woman. My mind then flipped to all the negatives of Thomas. A mild mannered, poor working, spiteful butthead. Derrick was right; I was a completely different person when I took the pills. I was...happier.

After considering my feelings, thoughts, and circumstances, I decided that I could tackle them better as Tiffany. I popped a pill, downed a bunch of water, and body slammed my bed. The effects of taking a second pill meant I'd be Tiffany for nine whole days. I started laughing uncontrollably.

I laughed and laughed -- no need for Thomas.

***

I spent the next day in a far better mood. I masturbated like crazy -- I had a lot of steam to blow off. Each time I finished, I framed my worked pussy in my sight. It was so sensitive, and my fingers barely got the job done. I hit up Derrick early on in the day to see when we'd be going on our date. I was so giddy!

However, bad news struck when he told me he'd need to pull a double. Damnable work, but at least he had a job. I played it cool and told him we could just go on our usual days off. The anticipation started to eat at me immediately. I spent that evening making myself cum twice, fantasizing and unashamed by my attraction. It was still not good enough. I needed more.

The next day was when Megan called me. She was surprised Tiffany answered. She asked if Thomas was okay, which confirmed her doubts of us being the same. I simply told her that he was okay and that he was working through some issues. The news relieved her. Then, she said something peculiar...

I started, "Derrick's been helping me out, but he's having a hard time, too. His grandmother just passed away."

"Oh? I thought she passed away last year from cancer," Megan pondered aloud.

An oddity if true...but, Derrick wouldn't lie about that sort of thing. I even had picture proof, "He sent a picture. She didn't look so well. Maybe...it was his other grandma?"

"Oh, maybe. That makes more sense," Megan laughed. I followed with my concerns of how harsh we sometimes treat the guy. Megan liked that so much that she said, "I'm actually glad you're not Thomas."

My heart sank a little, but I asked, "Why's that?"

"Because I think you're pretty awesome, Tiffany. You're fun, kind, and I think you work well in our group. I dunno, I want to get to know you without the whole body swapping thing with Thomas."

Her response mixed my emotions, but I took it in strides, "Thanks, Megan, that means a lot. I like you guys, too. I'll wait for Thomas to get through this rough patch to figure out what to do."

"Send him our love!" Megan ended it there.

I went to bed that night wondering if Thomas should care anymore. One thing was certain: Tiffany didn't.

Once the week passed, Derrick came knocking on my door late in the morning. I answered it, to see a well-groomed, cologne-dabbed, stud of a man. He wore his usual baggy get up.

"Good morning, Tiffany," Derrick stepped in.

"Morning, Derrick," I smiled. It felt so casual. I closed the door and faced my date. He took me in; I wore a long sleeve, v-neck black top that showed a little tummy. No bra; the shirt squeezed me enough. I had on my nice skirt again, and with my special black panties underneath. I wanted to feel sexy, and the way they hugged and framed my hips and ass were undeniable. I wore a red beanie with the motif of a Pokeball. It was gonna be cold today.

"I like it," Derrick said.

"Thanks," I tucked my hands behind my back and swayed. "So what do you have planned?"

"A festival is in town. I figured we can go there for the day, and then crash here for a movie," Derrick said.

I nodded, "Standard date -- sounds good!"

There was some apprehension for Derrick, and he asked, "You're oddly chipper about this whole thing. Is something going on?"

"After this week, I am ready to have fun," I avoided a direct answer.

"Wanna talk about it?"

"Thomas got fired. They didn't think I was him. I'm ready to go," I twirled on the spot and headed out the door. Derrick followed, but had no more questions. My abrasive dodges made it clear to him.

The festival was everything I needed. Games, rides, and distractions. Like the last time we hung out, Derrick was gentlemanly and considerate. I stayed closer to his side this time. He even wrapped his arm around my shoulders as the day went by. I didn't resist, and leaned into him.

A burning heat roared inside me. Each time Derrick touched me, it intensified. I always checked his pants in hopes of seeing an outline. My mind played against me, always fantasizing about him pulling me into a dark corner or over in a ride and going to town on me. I'd catch him admiring my curves and skirt. It wasn't too windy, but I bet he wished it were. If I were bold, I'd bend over from time to time. I wanted to get him turned on.

Afternoon soon turned into evening, and Derrick checked his wallet. He said, "Got enough for one more thing. Tunnel of Love or Ferris wheel?"

I pretended to think hard, and then, "Well, we're not boyfriend-girlfriend, so I gotta go with the Ferris wheel."

"Tch, if you say so," Derrick buried his hands in his pockets and led the way. With the sun teetering to the horizon, the lights of the festival were like dancing fairies. The Ferris wheel dominated the dusk sky. We sat across from one another in the carriage and rose to the sky.

Derrick was the first to ask, "Enjoying yourself?"

I didn't want to deny it, "I am. I really am."

"Wanna do it again some time?"

"Yeah, I think I do."

We stared at one another. It wasn't the same as before. It wasn't the same as Thomas. Something else was there. It made my heart race.

Derrick's eyes dropped to my skirt. I spread my legs, and allowed my skirt to slide up. The exposure had him lean back. I pulled the skirt up and let him enjoy the full view. It was moist, and desperate for his attention.

"What do you want?" he asked.

"Your cock," I said without hesitation.

Something supernatural was on my side as the Ferris wheel slowed to a stop. We weren't all the way up, but somewhere around the 11 PM point. Derrick stood up and cautiously moved closer to me. I reacted by sitting up and leaning forward. He undid his pants and yanked out his handsome cock. It hung and swung, halfway erected. It twitched bigger and bigger.

"For me?" I licked my lips and flashed him a sexy smile.

"Just for you," Derrick used a hand to tug on my shirt bottom up. Once he tugged enough up, to where it all scrunched up under my breasts, he widened his stance and worked his erect member under the shirt. His warmth wormed its way between my breasts, and I watched with bated breaths for the head to peek on through my cleavage. When it did, I giggled -- it was cute between my jugs. My shirt held it all together as Derrick began pumping his meat for a titjob.

It wasn't wet and slippery like the porn I used to watch. It was rough and raw. His hips slapping my tits overwhelmed me; I liked my knockers being knocked around. I lowered my head enough to where his cock head would rub my chin. I tucked my chin and stuck out my tongue...contact! His head kissed my tongue. Derrick's thrusts were more intent. We both were desperate for his dick to penetrate any of my holes. His prick was like a match striking a fire inside me.

Derrick grabbed my shirt and pulled up, until he yanked it all off. His cock flopped out along with my boobs. We were ready to go. However, the Ferris wheel started again. Derrick nearly fell over, but I grabbed him. He tumbled on top of me and we laid across my seat. We stared longingly in each other's eyes. So close to heaven...I could feel his bulging member twitching on my thigh.

Before the ride came to an end, Derrick tucked his weapon away and I corrected my outfit. We hopped out of the Ferris wheel and left the festival. I was buzzing. All I had on my mind was his big cock pounding my slutty pussy. I stared at him the entire way home, my hands slightly pressed into me under my skirt.

Derrick would notice, and a grin won over his face. He used that commanding tone, "Lift your shirt up."

I obeyed, and let my tits drop. It amused him, and he went on, "I dare you to keep them out until we get back in your apartment."

How exciting, but my nerves were present, "What if somebody sees me?"

"Then I guess they know you're gonna get fucked good tonight," his words buttered my perversion. He parked his car and we got out. It was a little late, but sunlight was still present. I listened to Derrick, and strutted out of the car with my tits on full display. Having them out and in the open was exhilarating. Anybody could see them. I hurried into the apartment stairwell, and dashed up the stairs with Derrick on my tail. Luckily, nobody was in the stairwell. We entered my apartment, and I quickly dropped my shirt down.

"Oh my god, I can't believe I did that!" I was laughing.

"Sexy as hell. You're a kinky lady, aren't you?" Derrick followed me around the apartment. I popped open the refrigerator and inspected the bounty. Beers, of course. I got one for me and Derrick, and we moved over to the couch. We found a mindless action movie to watch. Derrick leaned back and gestured for me to come over. I snuggled up into him, lying my head on his chest. I was completely sideways on the couch. He rubbed my arm and side as the movie began.

"Are you available next weekend?" Derrick asked as he moved his fingers from my arm into my hair.

I let out a small, insecure laugh, "I'm jobless now. I have all the free time in the world."

Derrick continued brushing my hair, "I can help if you need it."

"I don't know. That doesn't seem fair to you. I already feel bad that you paid for everything at the festival today."

"It's not a problem, actually. I don't mind spending money on you," Derrick's fingers traced my jaw and neck.

"But why? I'm useless, and all I do is cause trouble..."

"You're not useless. You make me happy."

"Pfft, you mean I make your dick happy."

"Same thing," Derrick adjusted. I saw why he did, as the bulge below my face pressed up against his pants. So close...my lips parted instinctually. He said, "I mean, does it make you happy?"

I sucked my lips in, "It does..."

"So we both make each other happy. We like each other's company. Even if it is just a bunch of sex, why not enjoy what we have? Why fight it? Doesn't that seem stupid to you?"

He was right. His mound flexed, as if summoning me. I answered the call and placed a hand on it. I stroked its length. So big, so powerful. The more I stared and touched, the more his words made sense. It was stupid.

"Say it," Derrick said the magic words.

It was my choice. Yet there was only one answer I ever wanted to give, "Your cock."

Derrick and I moved so he could stand up. He dropped his pants and let his log hang out again. His balls looked heavy; the taste of his cum lingered on my thoughts. I wouldn't mind it going down my throat. He sat back down, bottomless, with his prick at attention. He jerked it slowly with spread legs; I admired its beauty. I moved between his legs, on my knees, face-to-face with it.

"I've been thinking about it all week," I admitted. My hands rubbed his thighs as he jerked it.

"Why's that? Isn't Miller's bigger?" Derrick asked with a grin.

"He is, but yours makes me happy," I locked eyes with Derrick and opened my mouth. I stuck out my tongue and lowered it towards his crotch. He guided the head and slipped it in. It was a clean, tasty cock. It glided with ease on my salivated tongue; my moist, warm gape accepted his mass with an eager moan. It twitched inside my mouth, and my tongue explored its girth. I was more used to it, or perhaps less afraid. I fantasized about him plugging my throat.

I spun my tongue around the head and neck. His shaft bulged each time I tickled underneath the tip. I massaged the bulbous head with my lips while bobbing my head. I blew him fast, making some hectic slurping noises all the while. I proudly only used my mouth. I hugged my arms together to push out my tits.

"Goddamn, babe," Derrick lurched forward and held my face. I drew back slowly, sucking in, until his cock popped out.

"Too much?" I gasped for air.

"You're really into it, huh?"

I stroked him enthusiastically. I loved watching it pulse. This weapon could knock somebody out. I wiggled it around and watched the head like a hypnotized slut. Time to get serious. I tossed my beanie off and stared intently at him. I was really into it, "I want to take it all."

I shoved my mouth around it. I worked harder to force more in. I was able to handle the bulge, but the head hitting the back of my throat made me gag a little. I coughed, tears welled up in my eyes, and precum-fused saliva dribbled out. I was determined more than ever, slathering it with my mouth pussy. The fever of giving head enraptured me. His taste and my consumption erased everything from my mind. All I wanted was to deepthroat his cock.

I drenched Derrick's club. Strings of precum dripped from the shaft and my chin. I sucked on Derrick's dick over and over, each time inching closer to the base. I was so close, and his girth kept stretching out my throat. It was a mixture of pain and pleasure. I recoiled and rubbed my neck, gasping for air and moaning.

"Come on, babe, you can do it," Derrick encouraged. He believed in me; Thomas never received such pleasantry.

I relaxed my throat and slid his wet man meat back in. I deliberately took long strokes, and let it naturally shape my throat. First the head, then the bulge, and slowly the rest of the shaft. I coughed, and nearly gagged, but I clutched onto his thighs and braced. After another inch, my nose touched Derrick and his balls tapped my chin. I unsheathed his whole cock and gasped wildly. The deluge of liquids draped down onto my cleavage. We made a mess.

"You did it," Derrick congratulated me with small claps. I laughed and held my fists up like I just finished a marathon. His thing twitched like crazy -- it really liked the attention. Derrick leaned forward though and whispered, "Now for your reward."

Derrick helped me up, but remained sitting. He used his strength to spin me around, my ass now in his face. He crossed a hand along my rump before giving it a smack. I yelped, before saying, "Mmm, you like my ass?"

"Fuckin' love it," Derrick slapped it again. I fit my thumbs under my skirt's waistband and pulled down. As I did, I bent over. I bent as far forward and stuck my ass out as much as possible. My wet mound and thong-framed ass cheeks were his to plunder. I could only imagine the sight.

"Fuckin' A," Derrick carressed my cheeks. He pulled and bounced them, while I stayed bent. I could see part of him between my legs. I saw the sweet nectar pouring out from his cock.

He removed my panties. He stood up, and intentionally dragged his member along my leg and up to my rear end. He tugged on my shirt, all the while spinning us until we switched places. I faced the couch now, and I did a little sideways kick to fling my panties away. Completely nude, I was ready for him to conquer me again. He shoved me onto the couch. He was so aggressive -- I loved it. I loved being manhandled. I rested on my knees and elbows, propped on the back of the couch. I stuck my hips out and started to rub my pussy. Derrick laid his cock between my ass cheeks.

"Are you ready?" he asked, his hands hooking their fingers onto my hips.

"Yes," I spread my pussy open. Derrick's helm pressed into it, and I let out a small groan. When he shoved more in, and it split me open, I let out a satisfied cry. Thrusts soon followed, and I was back in heaven: his mighty cock rocked my world.

I immediately crumbled under his power. He pounded his meat into me, warping my aching snatch to his rod. The bulge in his shaft rubbed every inch of the canal. It overwhelmed me, made me hot, and sent my mind into a spiral. Wave after wave of pleasure shook my couch. My ass jiggled, my tits swung, and my pussy flared. I tried to control my breathing, but it was so hard. He was so hard.

"Sooo...goooood..." I cooed. My fingernails dug into the couch, and I braced myself as I pushed back. Our juices mixed enough to trickle down my thigh and envelope his member. As I pressed more and more back, with one strong euphoric plunge, Derrick shoved his whole cock into me. I let out a sharp cry. His head smooshed into my womb and my vagina hugged his girth. It was unbelievable.

"Oh yeah, there we go," Derrick's thrusts slowed. He grinded his cock all the way in and out. Each time he pulled, he stole my breath. Each time he pushed, he stole my gasp. He methodically pleased me, "You're so tight, babe."

"You're so big," I reached back and pulled on my ass. I felt like I needed to do something to spread myself more. I propped a leg up on the couch, and that helped. Derrick had more to strike, and he pounded away.

"OH! Derrick...it feels so good..." I gasped. The couch creaked under the pressure of our fucking.

Derrick said, "You deserve my cock. You deserve to be happy."

His words were hot honey drizzling across my mind. It was all so hazy. The overwhelming sensations made it practically impossible to think straight. Heat started to build up in my stomach, and my vision blurred. I was closer and closer with each delivery from Derrick. My moans quieted, as my body started to buzz. My insides vibrated and that same numbing warmth flushed my body in a near paralytic state. I barely got out, "I'm cu-u-um...I'm cumming..."

"Cum on my cock," Derrick commanded. His generosity and hard work made me squirm. I could only feel his cock plowing in and out of me, nothing else. I discharged on his mighty cock -- my body seized up. I remained still as Derrick churned my pussy. I became elated, smiling and giggling like a cheerful whore, as I kicked my legs and forced my hips against his pounds. My pussy sputtered with wet slaps. I felt alive. I was beyond happy.