In the Closet Ch. 03

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.

I managed to put on the thin pink cardigan myself, but Ellie even did my makeup for me, seeming more tender than what would be considered professional. It was so intimate. Sensual, even. Finally came my pink wig, the only one I owned. Definitely needed to get more colors for some variety, and to attract less attention. Then she took me by the shoulders and stood me in front of the mirror, letting us admire my getup together. Her face was close to mine as she stood behind me, wearing a gentle encouraging smile. Like a big sister dressing up her little brother, though we were the same age.

"See?" she purred into my ear. She was being kind of dominant, and it made me feel extra girly. "Wouldn't you like to fuck that girl?" I swallowed and nodded, getting aroused at my own reflection. She was going to turn me into Narcissus or something. "You're beautiful, Zach. Never doubt that."

The urge to cum shot through me, and I clenched my teeth to hold back my orgasm. The eroticism of this whole exercise was already too much, and now those words of affirmation almost pushed me over the edge. Oblivious, Ellie stepped back and grinned.

"Alright, I'll go make sure the coast is clear, then we can head out, okay?" Without waiting for an answer, she headed outside, and I had a quick moment to pull my pants down and shoot a load into a tissue. Fucking Christ, she was gonna drive me nuts.

--

"What if we run into Keith and Cody again?" I whispered.

Despite my shy nature, I didn't think I had social anxiety. However, being out in public dressed up like this, I was starting to get a pretty good idea. I was getting a few looks as we walked along the street downtown and, contrary to my fears, none of them were in disgust or bewilderment. Didn't mean I wasn't freaking out though.

"You think Cody would even recognize you?" Ellie laughed. "And Keith's already seen you, right? So what's the big deal?" She didn't know about the thumb incident last night, and because I didn't want her getting too zealous about it, I left it unmentioned.

Why did I agree to do this on a weekend? There were tons of people on the street this afternoon, and I really was getting my share of appreciative looks. Ellie looked pretty stereotypically lesbian, so we probably looked like a couple. And despite the minor stigma toward gay relationships, who didn't want to stick their dick between a pair of hot girls?

"You're kidding me." Somebody had just walked out of a store in front of us, and I couldn't believe it. Of all the rotten luck in the world, why did I seem to have so much of it? Keith stood there on the sidewalk, looking sharp and dapper in a navy three-piece suit with a garment bag slung over his shoulder.

"Hey Keith," Ellie greeted. "Why you so dressed up?"

"My internship needs me to own the proper attire for stuff, and I usually like to wear clothes I buy as soon as I buy 'em. How do I look?"

"Like a million bucks," she admitted, looking impressed.

He nodded appreciatively, then turned his attention to me, taking me in. By now he could apparently recognize me on sight. Noticeably leering at my legs, he inhaled before speaking. "So what are you two doing?"

"Limit testing," Ellie replied.

He swept his gaze over the throngs of people around us and nodded. His eyes flickered back down to my legs again before addressing Ellie. "Y'know what? I can help with that."

She eyebrow arched cynically. "Yeah? How? Why?"

Keith stared off into the middle distance in contemplation before answering. "I've been... kind of a bitch to Zach for, like... ever. Thing is, I've always wanted to help him with his confidence. Honest. I just didn't think..." He took a deep breath, looking my way now. "Anyway, I'm going out to a bar with my friends tomorrow night. I could introduce them to... Zoey here, and see if they show any interest. If everything goes well, they can flirt with her, hit on her, buy her a couple drinks. Should be a good boost to the ego."

Ellie looked to me on how to proceed, but I was kind of in the middle of losing my shit. Keith was taking me out to test me out on his friends? That was quite the vote of confidence; not only did he think I could fool them into believing I was a girl, he thought they'd actually find me attractive. He was being... sweet?

Seeing that I was catatonic, Ellie turned back to Keith. "And what if things don't go well? How are you even gonna get her into a bar?"

"Just let me worry about all that," he replied.

The confidence he exuded with that statement was insane, like he was telling me I was safe with him. I was so not used to this side of him. Something else I wasn't used to? My heart fluttering at his words. Like a fucking girl. Before I could stop myself, I was nodding my assent. Ellie looked at me in surprise, while Keith returned the nod.

"Then it's a date," he concluded. A date? Like I was his free use girlfriend? More heart-fluttering riddled with shame. "Get dressed up after dinner. I'll distract mom and dad so you can sneak out the back. Meet me 'round front, maybe at the corner, and we'll catch an Uber near the main road."

With that, he walked off toward a parking lot, his garment bag still over his shoulder. I watched him go breathlessly, just marveling at how fucking cool he was. Damn, he was good. It was no wonder he didn't have a problem with girls. I could see it. I could feel it.

"Alright, wasn't expecting that," Ellie remarked, interrupting my thoughts. "Like, at all. Forget limit testing, tomorrow's gonna be a trial by fire. You sure about this?"

Unable to speak, half because I was crossdressing in public and half because I was still tongue-tied, I found myself nodding. Her brows bounced in surprised acceptance before chuckling and breaking into a smile.

"Well, you're obviously obligated to tell me everything afterwards. Can't help but feel like he's pimping you out, but... it should be fine. Just try not to catch any dicks anywhere like last time, hm?"