The Derrick Dilemma Pt 04

Steam rolled across the water in my bathtub. I watched it curl across my cleavage. I was mesmerized by my breasts, and found it scintillating how the nipples peeked up out of the water. My fingers gently circled my clit. I didn't need a hectic rubbing session. I favored relaxation and massage.

Thoughts of yesterday overtook my mind each time I closed my eyes. A man's throbbing mass in my face; I salivated, and imagined its weight pressing into me. The smell, the feeling, the warmth; I liked it.

I liked cock. I'd even go so far as to say I preferred it after how it made me feel. I chalked it up to the euphoria of a new experience. It's a bit crazy to admit it after all the denial. Yet my ventures as a woman would have put me down that path eventually. Could Derrick have been less of an asshole? Sure, but we both got something good out of it.

The thing that bothered me are the texts I saw. If Derrick was lying about us on a date, what else would he lie about? He had the fuel to tell them we fucked...another of my mistakes. I decided to beat him to the punch. I called Megan and asked to come over and talk. She was relieved to have me, as my abrupt departure from the party worried everybody.

Megan and Joyce lived in a really nice townhouse. They had spotless floors and walls, organized furniture and kitchen, and the smell of cleaner and lemons.

Megan and I sat across from each other in their dining area. Joyce was working in her office, and said she'd join us later. I sported a tight-fitting tank top and short-shorts, no bra. Megan dressed to the nines, with an artsy long sleeve shirt, shorts, and pearl earrings. She wore makeup, I didn't; I'd yet gotten any. Seeing Megan in all her petite, pretty glory, maybe I should try a little harder in presenting myself.

"How ya been, girl?" Megan asked, a cup of tea in hand.

I sipped on water, "I'm doing okay. Sorry for worrying you guys last weekend."

Megan showed pity, "Yeah, Miller told us about how Derrick was eyeballing you. We heard yelling, both of you stormed out, and then you were gone. Derrick didn't say much and so we just figured there was a falling out."

"Kinda..." I felt shame for the anger that night. After how Derrick helped me yesterday, I could ignore it, "That's why I'm here. Derrick came over yesterday."

"Uh oh, big drama?" Megan braced herself.

"Well, he came over, apologized, and suggested we hang out for the day. He wanted to try and get used to me being Tiffany," I started.

"Oh, great! Good for him doing the right thing. So all is well, right?"

I sucked my lips in before sipping loudly on the water.

"Right?" Megan pressured.

"We had sex!" I blurted, before recoiling in the chair and holding my clenched hands to my face. Megan nearly mirrored me, but she slammed her hands on the table and recoiled.

"Aaah! What?!"

"We came home, some shit happened, we got drunk, and I fucked Derrick," I was like a writhing fountain.

"Thomas-ah! I mean, Tiffany-ah!" Megan gawked. "You and Derrick?! How? Why?"

I calmed myself down and explained. I mentioned how Derrick doubted who I was, how he lied about us being on a date, and the anger we both felt led up to the deed.

Megan nodded slowly, "Is that hate fucking? I've never done it, but it sounds fun."

I slapped my forehead and Megan laughed. That's when Joyce walked in with a confused expression. She wore a cream open-shoulder knit sweater and dark jeans. She asked, "Why the hell are you two screaming?"

"Tiffany fucked Derrick," Megan continued laughing.

Joyce curled her nose at me, "Ew."

We filled her in on the story and she sat next to Megan. Joyce took the news more seriously, "Was this with consent?"

I left out the coercion part. I simply skipped to him offering his dong and me reciprocating with an open mouth. I was coerced, but I didn't want to stick Derrick into any creepy category. He was just frustrated and horny, "Yes, no worries. Though the alcohol probably helped me kneel."

"Damn, was he any good, at least?" Megan sought details.

"I've...never had an orgasm like that before," I praised Derrick.

"Never woulda guessed," Joyce shrugged. Megan ate up the gossip, but Joyce didn't seem to care outside of my wellbeing.

I came out, "I apparently enjoy dudes in bed. I think still being Thomas made me apprehensive, but it is what it is. Plus, I wanted to say it before Derrick goes around claiming some kind of victory."

"Fair enough," Joyce shrugged. Did they even care about Derrick's lies? Was I overreacting?

"Question is: are you going to be interested in guys as Thomas?" Megan wriggled her eyebrows.

I hadn't considered that, "I don't know. Heh, maybe I should invite Derrick back over when I'm Thomas again."

"They're gonna bash butts," Megan sang. Joyce rolled her eyes. I did, too, but now my imagination saw Thomas face-to-face with Derrick. Little ol' me getting onto my knees and awaiting his hard, throbbing...

"What about ladies? Do you still find them attractive as a woman?" Joyce asked. As she did, Megan did a purposely horrible job at posing and winking.

I shrugged, "I mean, you both have always been pretty to me."

"Riiight, obviously we're pretty. That's not what I meant..." Joyce put an arm around Megan and grabbed both her sides. She then pulled Megan's shirt slowly up. Megan and I raised our eyebrows as Joyce lifted the shirt past Megan's breasts. Her frilly, designer's bra hugged her B-cups. Megan puckered her lips and sharpened her eyes. Joyce smirked, "I meant do you like this?"

Joyce proceeded to fondle Megan in front of me. She squeezed them above bra, at first. Megan moaned, and let out a cute gasp when Joyce tugged her bra up ever-so-slightly. Her perky breasts were soon fully exposed. Joyce massaged her wife's breasts. My eyes stayed fixed on the caressing hands.

"She's staring so intently," Megan hooked a hand around Joyce's head. We all watched each other with sexual tension.

"I...don't know what to say. It's fucking hot," I nervously laughed.

Megan used her hooked hand to pull Joyce to her. Their mouths collided in a passionate fury. They made out like long lost lovers. Joyce squeezed her wife close. Then Megan, eyes closed and tongue tied, gestured with her fingers for me to come over. It was time. I'd never been involved with another couple or any kind of threesome. Yet my ever insatiable lust worked me to my feet. I stepped around the table and stood on the opposite side of Megan.

Megan detached her lips from her wife's and said, "Her turn."

Joyce smiled and circled around my backside. Now I stood in the middle, face-to-face with my longtime friend. Megan's wet lips curved into a delicious smile. Joyce's hands started on my hips, slid up and around my stomach, until they graced my tits. Like with Megan, she lifted my shirt, but my tank top was snug. The lift pulled them up, and I saw Megan's eyes light up for the drop. When my tits dropped out, Megan leaned forward with a satisfied grin and she wrapped her mouth around a nipple. Oh...so sensitive! I winced in pleasure, placing a hand on her head. Joyce drew her fingers across my body. They tag teamed me.

"Maybe it's not just Derrick having a thing for you..." Joyce said. She walked around and bumped her butt against Megan's. She groped my free breast, and then latched onto it with her lips. Both wives had themselves suckling on me. I let out a cry. They were well-versed in the art of nipple teasing. Megan lapped at it like candy, while Joyce nibbled the tip. I loved each sensation. Joyce finished her thought, "Maybe you're just hot as hell, and we're all attracted to the new girl."

"R-Really?" I uttered. I laid my hands on their arms, afraid to touch them. Why was sexual stimulation so debilitating? I felt so submissive to their whims.

Megan agreed, "When we left the party, we both confessed that we'd bang you."

"Even though I'm...mmm...Thomas?" Megan and I always saw each other like siblings. It's why we never had a problem hanging out.

"You're not Thomas -- you're Tiffany," Joyce said, and an echo of Derrick sounded in my head. "And you're gorgeous."

Gorgeous? That was a new one, but it all started making sense in my head. Derrick's attraction, the shower of compliments at the party, and my interaction with Miller.

Simultaneously, Megan and Joyce reached up between my legs. Their hands pressed into me, and a familiar spark of eroticism swamped my mind: I needed them. However, this surprised both women, as they stopped making out on my tits and looked at each other with awkward laughs.

"Awe, babe, you wanna hold hands?" Megan teased.

"Great minds think alike, I guess," Joyce said. Her hand returned to my groin first, and Megan's hands circled around my thigh. Joyce's pressure and Megan's exploration, especially when she slipped her hand under my pants and enraptured my ass, forced heavy breaths out of me. Joyce pulled my pants down, followed by Megan dropping my panties. Their hands met again, petting and entering my wet pussy. My mouth hung open and I moaned as the two women ravaged me. When I looked down, Megan pulled her drenched fingers out and sucked on them. The lewd expression blew me away; I'd never seen my friend act like this before. My world began to spin.

Joyce stopped tickling my insides, but left her fingers in, "How about we pick this up another time? When I'm not working?"

"Yes, please," Megan laughed like a frat girl and gave my ass cheek a couple more squeezes. She was an excitable type of sexiness. I sighed and collapsed into a chair, and my good friend dashed off with my glass to fetch more water.

"A threesome with you two...sounds great..." I smiled stupidly. My lust was off the charts.

"Megan and I have been looking for a third person to spice some things up. We used to have somebody, but he turned out to be an asshole, and Megan wasn't really into him."

The idea of all three of us really turned me on. It was every guy's dream come true -- even if I was Tiffany.

"And maybe by then...I'll be able to turn into a dude..." Joyce held a mischievous tone. I was confused by this, but then I recalled what she said at the party.

"Oh, really?" I joined the mischief.

"Heheh, yeah, but don't tell Megan. I want it to be a surprise," Joyce leaned to see into the kitchen. The coast was clear, "I saw they have a mixed pill. I'm going to the doctor next week to iron out the details. If I can make it happen...maybe we can fuck my wife's brain out together."

What a raw thing to say. I knew what she meant by mixed pill, though. It was a lite version of what I had, where the only thing that changed was your genitals.

Megan returned with the iced water. I drank some, allowed my mind to settle, and left. We promised to find a weekend to spend more 'quality' time together. When I arrived home, my body buzzed with excitement. I dropped my pants and went to town on my pussy. I let the thoughts of the women wash over me. Thinking of them spreading my legs wide and both tonguing my pussy sent me over the edge.

***

The next day was the first day I wasn't horny. Tranquility and peace exuded from me...or some bullshit like that. Maybe I was finally satisfying a growing urge after my actions with Derrick, Megan, and Joyce. Maybe what I needed was an outlet or just somebody to talk to openly. Bottling up emotions and thoughts rarely was a good idea.

As I enjoyed my sixth day as a female, I decided to reach out to some of my friends. I wanted to know if my new self attracted them like the ladies said yesterday.

First in my contacts was Beth.

"Good day, Beth! Are you busy? I had a question for ya."

"??? what's up"

"So, I've noticed some people taking a liking to my new, feminine self. I wanted to get your opinion on it."

"she's pretty, I get it"

"Get it?"

"all the boys were eyeing you up at the party. they do the same when Laura or I wear dresses. you do it, too"

The male gaze. I sighed, and then responded, "Damn, so this is what it's like. I get it now, too."

"try not to think about it too much. you're just pretty to look at"

I proceeded to think about it. What I wore and how I moved meant much more as a female. Beth says to ignore it, but is it that simple?

Next was Bob...oh, boy...

"Yo, I have a question to ask. You free?"

"Hey! Oh, is this Tif or Tom?"

"Tiffany."

"Hahah, cool! How was the date with Derrick? Or, wait, oops! Am I not supposed to know that yet?"

"It wasn't a date, Bob. Derrick was just being a goof. We were hanging out because he isn't used to me being Tiffany yet."

"Oh, so you are Thomas?"

Damn you, Derrick, "Yes, Bob, I am Thomas. And I am Tiffany."

"Man, Derrick's weird about it all. Maybe that's why he hasn't responded to my texts? Oh well, how can I help you, m'lady?"

"It actually has to do with all this. Has Derrick ever mentioned how attractive I am?"

"Yeah, but he's usually agitated before or after. I think it's because he still thinks you're not Thomas."

I put an eye-rolling emoji, "Whatever. What do you think about me?"

"I dunno. I haven't really looked at you," Bob sent. Thanks to Beth, I highly doubted it, but he responded first, "Send a pic. I'll judge that."

I was in my bamboo pajamas: a tee top and shorts. My hair was fluffed up, but not brushed. It would be candid, at least. I leaned back on my bed and took a selfie. Hmm, bad angle. I tried again. Nope. I probably spent ten minutes taking thirty pictures until I got one that I agreed with; an upper body shot with a sweet smile, head slightly tilted.

"Wow! Yowzer! Hot mama!" Bob responded. It's all I needed.

"Thanks, Bob."

"Can I get one without a shirt?" followed by two fingers pointing at each other.

You've got to be kidding, "No, Bob."

"Pleeeaaase, Tif! You have really nice boobs! And you're Thomas. I'd let Thomas see my boobs. If I turned into a woman."

A twinge of excitement crossed my mind. I did enjoy sending nude pictures of myself to my partners years ago. Sexting was a normal thing for me back then. Posing nude as Tiffany might be sexier...I tested it out. I rolled up my shirt, but draped it over the nips. At the angle I took the picture, I was hiding my lower face with the shirt, while exposing my stomach and underboob. My nipples barely peeked out.

I sent the picture. Bob responded with multiple heart emojis and, "Woah! That's a ten outta ten if I ever saw it!" followed by howling wolf emojis.

"You think so?" followed by a blush emoji.

"Encore! Encore!"

I indulged Bob, and technically myself. Each picture made me hornier. I loved seeing my body peek from under its clothes, or posing in provocative ways. I teased more underboob, took some in my panties, and hugged my breasts together. Bob loved it, and complimented my sexiness. I loved the admiration. I ended it with a daring position; I set the timer on my phone and propped it on my dining table. I stripped naked and laid on my belly. I faced away from the camera, but kept my legs closed. I peeked over my shoulder with a sly smile. When I checked the picture, it came out perfectly. My position hid my front, but my legs, ass, and back were on full display.

Bob lost his shit when I sent it, "Friggin' hot! Damn, your ass looks so juicy. I wanna watch it jiggle."

A video, eh? The temptation was there, but I could feel my pussy warming up. All these pictures were getting me hot and bothered. I decided to end it there, "That's the grand finale, bud. But don't go sharing. Derrick's already making it a nightmare for me to have fun."

"Awww! OK! Thanks for the show! We pervs need to stick together."

Next was Laura.

"Good morning, Laura. Are you busy? I have a question."

"Currently loathing existence with my deceased, familial spirits...but go for it."

I paused. Laura was the embodiment of a big titty goth girlfriend. She loved goth and emo stuff, did the whole tarot cards and incense shtick, and blogged about death and murder mysteries almost all the time. Pegging down her tone in texts was always a challenge, "Well, maybe I can distract you? I noticed a bunch of our friends find me attractive. Do you find me attractive?"

"Why does my opinion even matter?"

"Because I'm your friend?"

"A question mark??? How tragic"

I prepared to call it quits, but Laura responded with an actual answer, "You're my friend, Tommie. It's a cringe question."

"I'm actually Tiffany right now," I corrected.

A long wait until Laura texted back, "What's the difference?"

I was ready to argue the differences, but echoes of Derrick rang true in my head. When I'm Tiffany, can I really claim to be Thomas? We were different...weren't we?

"Tif's cute, but we're friends. Crash in the friend zone. Sayonara" followed by a skull emoji.

"Wait, you'll call Tiffany cute but say nothing for Thomas?"

Laura eventually responded with an image of a chibi mushroom humanoid holding a large kitchen knife. Nothing else.

"Okay...thanks."

"May I return to my eternal struggle?"

"Have at it, girl," I sighed. Laura gave me a monkey wrench. At no point in our group's friendship did anybody find Thomas interesting. Tiffany on the other hand...

I skipped Jonathan since he rarely texted back. Knowing him, he'd pass along the same compliments as Beth and Bob did. If there was more to it, I feel like it'd only complicate my current state of mind. I spent the rest of the day lounging and watching television.

That night, as I laid in bed, my mind was stuck on everybody's reactions. I was more attractive as Tiffany, even to the point that I turned myself on. I stared at the selfies I sent Bob while petting my puss. My mind went to Megan's bra slipping down. Then to her sucking on my nipples. Then to Derrick eating me out. Then to Derrick pulling his pants down. Then to Miller's cock swinging like a pendulum.

I hadn't texted Miller today.

"Hey, are you up?"

"Yeah, working a late shift, though. No gaming tonight."

"I wasn't going to ask about that. I've been lying here as Tiffany, thinking about everything that's happened over the last couple of weeks."

"Oh yeah, how are you?"

"I'm okay. Just stressed."

"I figured. You had us worried after you left last weekend. So what's been on your mind?"

My body buzzed again, and my moist pussy convinced me to ask, "Your cock."

It took a little longer for Miller to respond, "Yeah?"

"May I see it again?"

"Damn, Tiffany, you sure?"

I sent one of my selfies, "Please..."

No response. I laid there waiting for twenty minutes, staring at my phone's screen. My head started to throb and I became hot. My mouth dried up and I tried to move, but painful aches riddled me. I rolled over, breathing heavily, as my vision blurred.

I blacked out.

***

When I awoke, I had no ailments. I sat up, and saw Thomas's -- my -- body. The bamboo pajamas squeezed my body more so than Tiffany's. As I grabbed my phone, I wobbled to the bathroom to relieve myself. I examined myself in the mirror. The pajamas hugged me just right. My hips and ass were phenomenal. At just the right angle, I could probably pass as a woman. My bulge was evident while front facing. It twitched underneath my pants. Seeing it while wearing female clothing kinda got to me. I lowered the pants enough to let my cock bounce out. Seeing my feminine erection was lovely. I jerked it in the mirror. It was smaller than Derrick's. Smaller than Miller's. Miller...

I gasped and checked my phone. One message from Miller, with an attachment. I swallowed nervously as I opened the text thread. He responded around midnight, "Sorry for replying late. Couldn't just take it out at work. Hope it helps."

The picture was a high angle of a fully erect monster of a cock. It was veiny, and the tip was lathered up. He'd masturbated before or during the picture. Seeing such a beast poking out of work pants did something to my brain. I instantly thought of giving Miller a blowjob under his desk. Wrapping my mouth around the serpent's head and gagging on it halfway down. Fuck, what was wrong with me?