The Derrick Dilemma Pt 02

I stood before the mannequin and admired the yellow dress. It wasn't too bright, and looked comfy. Compared to button ups and shorts, I was ecstatic to expand my wardrobe.

Today marked my second day as a female. The first was...a wild ride. However, my main focus today was clothes shopping and hanging out with my friend Megan. Brilliant mind, short and sweet, but with a humorous edge that matched my own sense of humor. Our energies were so synced that I considered her more as a sister than a friend. We've known each other since high school.

"How about this, Thomas?" Megan returned from her fetch quest. She brought a small selection of outfits for me to try on. I took them and glanced at the changing room.

"Only one way to find out. I'm completely depending on you for this one," I smiled nervously.

"Based on your measurements, this should be fine for now," Megan opened her phone to a digital notepad. "Whatever doesn't suit you we can toss aside, and for the next few pills you can hone in on what you like. Then we can take a real shopping spree. Oooh, I can't wait!"

"I appreciate all the help. I thought I was more prepared for this side of the experience, but I'm outta my league..."

"Give it some time. Once you're done acclimating, all will fall into place. When Joyce switched over from girly stuff, she had the same issue. Come Christmas and birthdays, I needed to learn the size conversions for men and women real fast, hahah!"

"I bet!"

"Well, no more dilly dallying! Let's see how good you look in a dress. Montage time!" Megan giggled.

I wish it would turn into a montage. It'd be a lot faster. I shuffled my way into the fitting room and locked the door. I promptly dropped my shorts and took off my top. I stared at myself in the mirror.

Megan and I picked up underwear before anything else. Wearing women's underwear was nice, and it made me look nice, too. I still had the male mindset, and seeing a nearly naked chick in the mirror was pretty hot.

An intrusive thought sprang up -- finger myself in a changing room. I'd seen it in porn before, and sexual fun outside the bedroom was always a rarely explored kink of mine. My hands traced my bra's lining and tickled my cleavage. Chills, and a pang of lust, flooded my senses. Even a day out from the transformation and I was still horny. Was it the pill, or just this new body?

"Megan..." I not-too-loudly called out.

"Wazzup?" I heard just outside the door.

"You're bisexual, right?" I asked. She gave a short, affirmative answer, and I followed with, "What makes you attracted to men and women? Is there a difference for you?"

"Hmm, I'd say it's mostly the same. I like assertiveness and confidence. That's mostly a guy thing, but there's plenty of ladies like that. I'd say it's more a type thing than the actual team a person plays on," Megan explained. As she did, the shallowness of my question became clear to me; of course it isn't about what's between your legs. But as a straight person...what recently went down between Derrick and I...

"Why do you ask? Are you interested in men now?" Megan asked.

I faded Derrick from my mind, "I don't know..."

The conversation ended there; maybe Megan could tell I was mentally struggling. I tried on the choices Megan brought me, found some likes, and bought what I wanted. It'd take some time and experimentation to figure out my fashion.

As Megan and I hopped into her car, we discussed the get-together the following evening. Everybody wanted to see the new Thomas. I liked the idea. We collaborated for the rest of the day to make a party of it. Snacks, drinks, friends, drinks, and some more drinks. After Megan dropped me off, my confidence in this new lifestyle revitalized.

I spent the evening trying on each of my new articles of clothing. Megan suggested picking up a pair of underwear that made me feel sexy. The ones I picked were black, slim, and emphasized my curves. More thong than panty. Seeing myself in them made me horny. Before I knew it, I was tweaking my nipples and going to town on my pussy. Is this how women always felt? Am I just a pervert?

Thanks to Megan's company, I had mentally blocked yesterday's 'fun'. However, as my fingers rubbed in and out of my pussy, I couldn't help but imagine Derrick. I did my best to not let it consume me, but when I came, his prominent bulge was all I saw.

After showering and playing more with my body, I went to bed half-horny. Masturbating, for some reason, didn't satisfy me...

***

For the party, I went with casual wear. A sleeveless crop top that exposed my cute belly button and jean shorts that ended halfway down my thighs. The tight fit snuggled me. My shoes were a rocking pair, as well. I looked like your everyday beauty.

I arrived early in the evening, but I was pretty much the last one. We had it at Miller's place; a two-story family home. He inherited it from his parents, who were retired. When I knocked on the door and it swung open, I was showered with cheers and whistles.

Bob, Miller, Jonathan, Megan, Joyce, Laura, and Beth were there. Aside from Megan and her wife Joyce, everybody's reactions were of surprise and wonder. They were amazed I was actually Thomas. Some complimented my looks, others were like Derrick and wanted me to answer a question to prove myself. Funny enough, it only took one answer to satisfy them. Fuck you, Derrick.

We weren't young and rambunctious anymore, and so the party dissolved to sitting around a room chatting, drinking, and playing miscellaneous card games. They asked how I liked the new body, how different it was, and which sex I preferred. Good, depends on specifics, and male were my respective answers. When I said male, I did note that this was just my third day. It might change in the future, but for now, I looked forward to being Thomas again.

"What should we call you?" Bob asked. They called me Thomas up to this point, but some were weirded out by that. I, too, didn't feel right being called Thomas while having a female body.

"...how about, Tiffany?" I smirked. Why the hell not?

People were cool with it, and from there on, Tiffany was my female name. Derrick will flip his lid, but he's usually juvenile. It'll be our little secret.

Soon thereafter, almost like thinking about it summoned him, Derrick showed up. He seemed a bit disheveled, but greeted Miller with a smile and fist bump. When he came into the main room, his eyes locked onto me.

"Oh..." Derrick showed a rainbow of emotions. He ended the spectrum on cool, "Lady of the hour, right?"

"What's up, Derrick?" I casually greeted as I held my cocktail in the air.

Miller moved into the picture, having just closed the front door. He gave an unnecessary, forced introduction, "Derrick, this is Tiffany. Tiffany, this is Dorkrick."

"Fuck you," Derrick responded, but his eyes remained on me. Everybody laughed, thinking he retaliated against Miller. Little did they know...

"Yep, I'm Tiffany. Figured a more feminine name was needed for my transformation. I think it'll stick," every word I spewed came with an edge. I finished with a dainty sip of my cocktail.

"I need a drink," Derrick declared. The laughter carried on, and Miller guided Derrick to the kitchen with an arm around his shoulders.

Derrick joined us in the living room and added in little snips and jives here and there. Things seemed normal between us, though I could see some anger behind those eyes. Each time he used my female name, I smiled like a doe-eyed, innocent angel. The tensions lessened as the night waned. Derrick relaxed with a few drinks, and soon enough, we were buddy-buddy. He even clanked my glass and congratulated me for my change. He no longer doubted who he was looking at -- Thomas.

The drinks flowed. I just finished my second cocktail. My body floated in place; a good indicator of my drunkenness. Jonathan just finished talking about a car he sold the other day. Beth turned to me and asked, "You good, Tif?"

"Fucking fantastic," I cheered with an empty glass.

"Is it okay to get drunk while changed? There won't be any side effects?" Beth was a nurse.

"None that really stick out. Nausea and becoming more tired. Stuff like that," I assured her. There were probably more, but I didn't really care to recall.

"Would you recommend them?" Joyce asked. Megan laid in her lap, running her hands through her wife's pixie haircut.

"Sure, why?"

Joyce became embarrassed as she licked the corner of her mouth. She couldn't make eye contact when she said, "Maybe somebody wants to give it a go as a man..."

The room lit up at the suggestion, with coos and oohs. Megan equipped a sly smile and added, "Be easier than wrestling a strap-on."

This tipped the room. Everybody bellowed with laughter, and Joyce hid her face in Megan's chest. When it calmed down, Bob was next with a question for me.

"Speaking of bedroom acts, have you...y'know, flicked the bean yet?" Bob gestured with his hand.

The ladies in the room booed him, but it was all in good fun. Bob needed to defend himself, "Oh yeah, Joyce can ask about growing a dick but I can't find out a man's perspective to jilling off? No respect, no respect at all!"

They relaxed on Bob, and when I saw an opening, I said, "Yes, I have."

A bunch of oohs, and then Bob's follow-up question, "So which feels better?"

I paused to reflect. This drew everybody in. They were hung on my pause. I answered, "If I had to be honest, having a dick feels better."

My answer divided the room. The women waved it away while the men nodded along and liked my answer. When I looked at Derrick, he's the only one to not react. Instead, he was in his own little world, staring out one of the windows.

Bob snorted, "That settles that. Men rule."

"It wasn't a competition, you idiot. I'm hungry," Megan hopped up from Joyce's lap and broke up the chat session. Everybody dispersed to hit the bathroom or check their phones. After I placed my glass in the sink, I decided two cocktails was my limit tonight. Each step I took got me closer to the clouds. I did not want to black out. Especially with my body changing back tonight.

I headed to the bathroom. Before reaching it, another exitted out. It was Miller. We greeted one another with a smile.

"How are you holding up?" Miller asked.

"A little wobbly, but it'll clear up with some snacks and water. I gotta be back home by eight. Any later and the fever will kick in, and I don't want to be driving when that happens," I giggled.

"Hmm, okay. Yeah, my trans friend in Florida told me about gender pills. How they work and all," something was off about Miller. He was uneasy. Was it me?

Miller went on, "How did your parents take it? I know you were worried about that."

I chuckled and drunkenly rambled, "Step dad doesn't care, as long as I'm happy. And mom thinks I'm going through some things right now. Says 'I need to stop dealing in silly things' and 'I'm fine the way I am'. Not a shred of encouragement."

Miller winced, "Yeeeaaah, I've heard that before. Don't let it get to you. Hopefully she comes around."

"Maybe..."

Miller's unease opened up more, "Did you notice anything about Derrick earlier?"

I squinted, "Nooo..."

"I'm pretty aware of the guy's behavior. He was extra quiet, and he could barely take his eyes off of you," Miller said.

"Pfft, please, the dude is high half the time. He probably hit it up before coming over," I needed to redirect.

"Marion, my friend in Florida, struggled with a roommate when they transitioned. They ended up catching feelings. First things got weird, then it got worse," Miller explained. His concern and unease were fully revealed, "I think you should have a talk with Derrick. Set some boundaries. Trust me, it'll go a long way for you while you're Tiffany."

Boundaries. Those would have been useful on the first day. What if Derrick did catch feelings? I let him fondle me, but that's not much room for connection. He certainly acted more repressed.

"That's a good idea. I'll talk to him tomorrow, when my head is cleared up. These spiked hormones are hard to handle. My nipples are constantly begging for attention," I complained.

"You lucked out on looks, and with a male mind, it probably doesn't help each time you look down," Miller gestured to my breasts.

I did a full body shrug, "Exactly! I can't think straight!"

Miller laughed, "I believe we men have used that line a few times."

He could say that again. It only ever seemed like sex was on my mind. The situation with Derrick weighed on me, too. Miller must have noticed, because he asked, "Something wrong?"

I said, "I'm trying to figure this all out."

Miller pondered, "Hmm, well, why are you doing it?"

"What do you mean?"

"Why be Tiffany at all?"

That was simple, "Because I want to be happy."

"Are you?"

"I think so..."

"Then what's tripping you up?" Miller sought the core issue. I knew it, and so I opened up.

"I'm a female now, and I've always been attracted to women. Never guys. Yet, a part of me is wondering if I do now. It's...vexing."

"Hmm, well, what about me?" Miller spun in a circle. I checked him out to see if anything sparked. He wore a graphic tee and slim black jeans. He still had a quarterback's body, with broad shoulders and defined arm muscles. His black, wavy hair framed a squared jaw. When he gave me his back, I stared at his ass. Less flat than Derrick's. Why was I thinking of Derrick?

I shrugged, "Nothing really. No offense."

"None taken, but it's a start. I mean, there's merit in asking yourself those questions. Do it now as Tiffany, and again when you're Thomas. It may even change with your form. You shouldn't be afraid of how you feel," Miller was always cool like that. He and Beth were on and off, but their careers always pulled them in opposite directions.

I felt safe asking, "Could you do something for me then?"

"What's up?"

"Can we kiss?" asking felt wrong, but necessary.

"Oh, well, I'm sorry to say Tiffany, but I'm married to my job. I'm flattered, though," Miller played around.

"This isn't a confession. I trust you, and you're the one who suggested I try this," I said.

"Ah, my big mouth lands me in trouble again," Miller laughed.

What a bro. We moved closer, and unceremoniously kissed. Right before our lips touched, I was hit by the same sensation one gets right before a roller coaster's drop. His lips were warm, and he pressed on my firmly. Our lips were locked for only a few seconds, but it lasted long enough for an opinion to form. When it ended, Miller asked, "And?"

I winced, and spilled my honesty, "I...liked it."

Miller busted out laughter, "You sound so pained!"

"I don't get it. I've never been interested in guys. It's such a weird feeling!" I panic-dumped my thoughts.

Miller moved in again. My panic melted as our lips danced across each other. His hands cupped my jaw like guardrails. We made out. I made out with another man.

He brought me into an embrace with his arms, and I latched my hands onto his side and shoulder. I slipped a tongue into his mouth, and invited him into mine. He tasted nice, and the heat raised. His body nearly engulfed mine. We stumbled sideways into the bathroom and closed the door. I braced against the sink, and we continued our venture. I was so into it.

Miller let me breathe and released me from his embrace. We both breathed like track runners, "There you go. Did that help any?"

I sighed, "I liked it. I guess I should just accept that being touched, regardless of by who, is nice."

"Great, glad we could clear that up, but we have to stop here. Or things might get out of hand," Miller nodded down. My eyes naturally lowered to the new bulge in his jeans.

"Oh man, I'm sorry!"

Miller laughed it off, "I did it to myself. Macking on such a pretty face will do that to ya. You should know what I mean."

It was true; almost everything popped a boner for a guy when getting physical with a hot lady. A small warmth lingered inside me; that was twice somebody called me attractive. Their bulges were evidence. This was Miller, though. Far more respectable than Derrick. I continued to be adventurous, "Can I ask one more favor, Miller?"

"Sure."

"May I...see it?"

Miller squinted his eyes and tilted his head. One of his hands crested the bulge and squeezed. Was that defensive, or was it a lure? He asked, "Are you sure about that?"

I explained, "I'm not attracted to guys, but I like the touch. So the last thing I need to figure out is how I do with male nudity. Is what I'm feeling just sexual?"

Miller nodded and unbuttoned his pants. After the zipper was lowered, he dug his hand under his underwear and grasped his member. He wiggled it, and watched intently. With just a couple feet between us in the bathroom, he whipped out his cock. It wasn't fully erect, but it was getting there. To my shock, the dude packed a schlong that reached halfway down his thigh. Miller's half chub was bigger than mine when fully erect!

"Good god, man! It's h..." I was able to stop myself from saying what every man always wanted to hear.

"How is it?" Miller asked with a grin. He used a hand to gently stroke the shaft. It curved downwards. The head pointed straight at my crotch, demanding attention.

My heart raced and my face flushed, and it wasn't the alcohol's fault. I devoured his monster with my eyes. Thomas and Tiffany wanted to say polarizing responses, but Thomas won out, "I gotta say, I'm not feeling anything. It's...it's a nice cock, though. I see why Beth sticks around."

"Hey, come on, it's not the only reason," Miller asked for more credit. He pinched the head as he spoke, and a little liquid came out.

I finally pried my eyes from his log and glanced to the side, "Yeah, I don't like it..."

"Then away it goes," Miller respected my choice and I heard the zipper zip and buttons...buttoned. When I looked at him, I immediately checked his groin. It continued to bulge, and was slightly hotter with just the outline. He snapped his fingers, "Hey, don't go staring if you don't like it."

I shook my head, "Sorry, it's just I've never seen another in person. Plus, yours is on the bigger side..."

"Ten inches -- yours?"

"Dude, you're twice my size," I admitted. It wasn't anything to be ashamed of. I'd satisfied plenty of partners. Admittedly, a big cock was easy to be in awe of...especially this close.

Miller nodded, "Well, best have a substantial one to see if you like them or not. Any other requests? If you want me to go shirtless, I'll send you to Jonathan. His six pack could be used as a grill."

I laughed and rolled my eyes, "I'm good, thanks. I think I need to just focus on comfort and boundaries. One step at a time."

"Keep at it, Tiffany. You're battling a new body, new emotions, hormones, and judgment. If you like it, you like it."

He had a point, "True. Thanks, Miller."

"No problem," Miller exited the bathroom. "I'm gonna go check on everybody."

I nodded and began closing the door, "And I need to piss. Then I'm going to stuff my mouth with crackers."

I took care of my delicates -- much different than having a hose -- and washed my hands. Miller's cock was seared into my mind. As I stared at myself in the mirror, my imagination went wild. Damn, seeing me drunk in the mirror kinda got me going, too. My nipples were slightly hardened. Not in a guest's house, I told myself. I'll wait to go home.

I left the bathroom and made my way down the hallway. The noise from the living room was far more subdued. Gentle music, and little to no talking. Was everybody winding down, or leaving? That's when I heard voices coming from a closed room in the hallway. I slowed down next to it and eavesdropped.

"...weird, is all I'm saying. It doesn't add up," Derrick's voice came through.