All characters are at least 18 years old.
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Zach
If my dad knew he was bringing a gay crossdresser to Catholic church, I'm pretty sure he'd have an aneurism.
Well, not gay per se, just perhaps bicurious. I wasn't gay yet. Not that it was a definitive eventuality. Confused! Yes, that was the term. I hauled my confused ass into the car with the rest of my family, ready to head home from the late morning service. Keith had been avoiding me as much as he could all morning, which suited me just fine. Mom always had us in dress shirts for church, and the contrast to what I was wearing last night was probably giving him whiplash. I couldn't blame him, but I'd be lying if I said I didn't find his discomfort entertaining.
I looked over at him, taking note of his attire. He was in a navy button-down and black jeans, and I had to admit he looked good. It was probably the first time I really gave thought to how attractive a guy was, and I squirmed a little in my seat at that revelation. This was all Ellie's fault.
Maybe dad's friends were right and "the gay" really was contagious, I chuckled to myself. Dad worked in construction, so he was always around a bunch of macho men. Thankfully, he didn't go as hard on the traditional male values as some of his buddies, but he was still a man of his time; some opinions weren't yet fully up to date with what was politically correct. Not that it really mattered, since it never came into play. The only reason it would ever be an issue is if, for example, one of his sons came out as a crossdresser. That... That might raise some questions.
"You two are awfully quiet today," mom remarked as we arrived at home. She gave us both a good-natured but questioning look as we got off the car and headed inside. I was mom's favorite and Keith was dad's. Unfortunately, mom showed it by babying me like crazy, which didn't help my image. Dad sometimes voiced concerns that her behavior would make me soft, and, well... There were so many factors at play that I had no idea to what exactly I should attribute how I was. At some point my brothers and I suspected that mom always wanted a daughter, and if she were married to a less traditional man, she might've dressed me up as one once or twice.
"Just thinking about college in the fall," I replied faintly.
"Attaboy," dad grunted as we guys seated ourselves at the dining table while mom went about cooking lunch. He turned to Keith and continued, "Hey, Champ. You make sure to take care of your brother, you hear? He's a man now, and you gotta show him how to act like one on campus. Can't have everybody thinking he's a pansy, can we?"
Keith coughed and cleared his throat, glancing over at me awkwardly before nodding. I maintained a wooden expression, sure that we both were rolling that statement over in our heads, contemplating it in a different light.
"He's not a pansy, honey," mom chastised.
"I know that, darling, but we just gotta make sure everybody at that little university of theirs knows that too." He stood up to pour himself a mug of coffee, propping himself up by the sink before turning back to me. "You give your major some thought yet, boy? You could always go into business like Keith here."
"I... haven't decided yet," I mumbled.
As lunch progressed, dad went on about my options for school. I was already set to go to the same school as Keith; a legacy of a mom and two brothers basically rules out going anywhere else. However awkward the conversation was, it certainly beat talking about my masculinity. Afterwards I just had to get out of the house. Lucky for me, everybody else was doing the same. Dad was going to a friend's to watch the game, while mom was doing the same for book club. And Keith was off... doing Keith things, I guess. So funnily enough, I had the house to myself and didn't have to leave after all. I texted Ellie if she wanted to hang out, and her swift reply said she was on her way.
Before I knew it, I was opening the door to her mischievously smug face. She was in a tight white sleeveless hoodie and cargo pants, her favorite outfit. It was my favorite of her outfits too, particularly when she added a red sports jacket on top during the winter. Did I mention I had a crush on her?
"How's my favorite trap doin'?" she teased.
"I'm not a trap," I groused, walking her to my room.
"It's literally what you're doing to Keith right now," she reasoned.
"Except he
knows
I'm a guy. Ergo, not a trap."
"If you see a bear trap and step in it anyway, does it stop being a trap?" I groaned in exasperation and she chuckled. "So, what's the plan for today?" Her eyes widened, and I could practically see the lightbulb over her head. "Wanna go out as a girl?"
"What are you, fucking insane?" I scoffed. "I can't just walk out, full fem, just like that. I don't have breast forms, I don't have my girl voice down pat... I'm just not ready."
"You are," Ellie insisted, expression suddenly full of conviction. "You don't need the breast forms, and I can just tell people your voice is out for the moment. You might not think it, but you're more ready than you realize." She took my hands in hers, looking at me intently. "You're ready, Zach."
I was still skeptical, but Ellie just seemed to have this gift for making me feel brave. She was just so confident and tough that I suppose it was only a matter of time before it started rubbing off on me.
I stripped down while she laid out one of my outfits on the bed for me. What I wasn't ready for was the panties she'd chosen. As in, she wanted me wearing panties on this outing. I lifted it up a bit with a finger, then turned to her expecting her to leave so I could get changed. She regarded me steadily, making no move to step out of the room.
"Uh..."
"Is there a problem?" she asked, her voice low and slightly raspy.
I gulped. She'd never seen my junk before. I guess today was the day then. Hooking my thumbs into my briefs, I took a deep breath before yanking them down quickly. She didn't sneer at my inadequate size, just continued staring at my body as if it was what she expected. My erect three inches throbbed under her gaze, and I bit my lip before tucking it between my legs so I could slip the panties over it.
She pulled the tight white tank top over my head, then held the short shorts out for me to step into. She was just dressing me, but it had me panting all the same. Standing behind me, she tugged the shorts up, yanking me back until my ass was against her hips while she buttoned them. Her body pressed against mine... I was worried my dick would spring out from my panties in excitement.
