Left to Their Own Devices

I was cleaning up the last of the dishes from my dinner when my apartment door swung open and my roommate, Eric, entered with a woman following close behind him.

Eric and I couldn't have been more different. We were both seniors in college, but that was where the similarities ended. He was tall, athletic, ruggedly handsome, and outgoing; an archetypal gym bro. I was short, slight of build, with softer features, a quiet personality, and a nerdier set of interests. Nonetheless, we had always gotten along well.

"So yeah," Eric explained, looking over his shoulder at the woman, "this is my apartment. And this is my roommate, Caleb. Caleb," he said, looking at me now, "this is my little sister, Claire."

There was an obvious family resemblance between Claire and Eric. She had a strong jawline like his, the same brown eyes and dark brown hair color. She was smaller than him and just a little bit shorter than me, but still a few inches taller than the average woman, and though she was a hoodie and baggy sweatpants, I could tell she had a bulkier frame than most women too.

"Nice to meet you," said Claire, stepping forward to shake my hand without a moment's hesitation. I took her hand and shook it, amazed by how firm her grip was, feeling her weightlifting callouses against my softer skin.

"Nice to meet you too." I replied, managing to look into her brown eyes for a moment before my usual shyness kicked in and I looked away.

"Claire's going to be crashing on our couch this weekend," Eric explained. He stepped over to the kitchen counter and immediately grabbed a couple of glasses out of the cabinet to make protein shakes.

My eyes lingered on Claire as she turned away from me and picked up one of the protein shakes. There was something captivating about her. She carried herself with confidence. Her clothing wasn't especially flattering and she wasn't wearing makeup and her hair was in a loose bun, but she was pretty in an unusual, rugged way. Maybe she didn't care as much about her appearance as other women (or maybe it was because she had just been at the gym), but it was still quite appealing to me.

Fortunately, I managed to tear my eyes away before either Claire or Eric turned around, the shakes finished. It was a little uncanny how similar their movements were. Eric opened his mouth to say something, but abruptly stopped himself and reached into his pocket, pulling out his phone. He looked at the screen and smiled.

"Caleb, I'm going to need you to show Claire around the place. Make her feel welcome, you know? Looks like Natalie wants to see me tonight."

There was a look of surprise and maybe a hint of disappointment on Claire's face as she looked at Eric, but she hid it quickly and replaced it with a smile.

"Nice, bro. Have fun." They fist bumped, and Eric set down his gym bag and made his way to the door.

"Thanks. If I'm lucky, I won't be back until the morning." He said, stepping out the door and closing it behind him, leaving me and Claire alone in the kitchen.

There was an awkward silence between us for a moment. I wasn't sure what to say, and it seemed like neither was Claire. She deflated a little when Eric left, the confidence she'd had when she'd shaken my hand no longer visible. Finally, realizing I was supposed to be the host, I decided to speak.

"I guess I should show you where you can set your bags down." I turned and led Claire to the living room, motioning toward the couch. She rolled her small black suitcase over to the end of the couch, leaving it there and setting her gym bag down on top of it.

"So, uh, can I get you anything to drink?"

"It's been a long day. I could use something with alcohol in it." Claire sat down on the couch, looking up at me.

"Are you old enough for that?"

"Ha! Eric said you were like that."

"Like what?" I asked, puzzled and a little embarrassed. What exactly had Eric told her about me? He'd told me she would be staying the weekend, but that was about it. I suddenly felt like I was at a disadvantage.

"A stickler for the rules. The good boy type." There was a hint of teasing in her voice.

"Guilty as charged."

"Come on," she wheedled, "if Eric's appointed you as my chaperone, I'm sure he trusts you to make sure I don't go too wild. Besides, I'm nineteen. That's old enough in most countries." She had a playful look on her face as she finished her appeal.

"I think we've got a bottle of vodka in the freezer." Maybe I wanted to prove Eric was wrong about me, but more importantly, I was finding it hard to say no to Claire. I've always been shy around girls, and it wasn't often I found myself alone with them. Especially not ones as attractive as Claire.

"Well then, how about you grab some shot glasses?"

I headed back to the kitchen and did just that. Returning with the bottle and two shot glasses, I sat down in the chair across the coffee table from Claire. I poured us each a shot and slid a glass across the coffee table to Claire. She picked it up and downed the shot without hesitation, then smiled at me. Somewhat hesitantly, I picked up my own glass. Suppressing my nerves, I threw it back in one gulp, the alcohol burning my throat. I coughed, feeling my face heat up.

"Not much of a drinker?" asked Claire with a little grin.

"No, not often. It's Eric's bottle."

"How did you two meet, anyway? You're not what I expected his friends to be like."

"The apartment complex assigned us together randomly." I paused a moment. "What did you expect his friends to be like?"

"I don't know, more... like him, I guess. You know, loud, outgoing, gym-bro type?"

"You kind of have the gym bro thing going yourself."

"Our whole family's like that." Claire said with a shrug before refilling her glass and taking another shot.

Not wanting to be outpaced by a 19-year-old girl, I took another shot of my own, once again coughing after feeling the burn in my throat. Claire covered her mouth, but her eyes showed her amusement. Still, it was nice of her to try not to laugh at me.

"I bet it was fun to grow up with Eric."

"He's a good brother, but there was a lot of pressure to follow in his footsteps growing up. I guess that's how I ended up kind of tomboyish."

"It suits you." I said, surprised with myself for being so forward. Maybe the vodka really was helping. Claire blushed just the tiniest bit.

"Thanks. Hey, can I ask you a question?"

"Sure."

"This girl Eric went out to see... Natalie? Do you know her?"

"I've met her once or twice. Why?"

"I was just curious what she's like. Eric never mentioned a girlfriend."

"Honestly?" I hesitated for a moment, not sure how much to say. I didn't want to make things weird between my roommate and his sister, but on the other hand, I was two drinks in and I wanted to keep Claire talking to me. "I don't think she's his girlfriend. He kind of just has this... roster of girls he rotates through."

The smile faded from Claire's face and she looked down at the coffee table. When she didn't say anything for a moment, I decided to speak up.

"Something wrong?"

"No, it's just..." She trailed off, staring at the wall behind me for a moment, looking like she was trying to figure out how to say what she wanted to say. "I guess I'm a little jealous. Whoa, wait, not like that. That came out wrong."

Claire blushed and hurriedly poured herself another shot, downing it immediately.

"Like, it's not some weird Freudian incest thing. I'm not jealous of her. I'm jealous of him. You know what I mean?" She was talking faster now, nervous and stumbling over her words, and not because of the alcohol.

"Uh, I'm not sure I do."

"It's just... It's different for him because he's a guy. He can go out and fuck around with all these girls and it's cool and something he can brag about to you and everyone thinks he's more of a man for it. I guess I'm just jealous I don't get to experience sex like a man does."

Suddenly, it clicked into place for me. Claire looked up to her older brother, and she had always wanted to follow in his footsteps. The weightlifting, the appearance of confidence, trying to fit in as one of the guys. But here was this very primal, fundamental thing where she couldn't be one of the guys, couldn't be like him. That's why she had given him that look when he announced he was leaving to hook up with Natalie, and why she had hidden it before he could see it.

Claire looked at me expectantly, waiting for me to say something.

"Well..." I said, not sure how to respond to something that heavy. "We don't all experience it like that. Men, I mean."

"What do you mean?" She had a look of puzzlement on her face, probably not too different than the one I had had earlier. Now it was my turn for deep personal revelations. I was starting to miss the small talk.

"It's... guys like Eric have a very different experience with sex and dating than guys like me. He's ripped, he's confident, he's the alpha male type. I'm... well, not like that, I'm sure you've noticed by now."

Claire was nice enough not to say anything to confirm that last part, but she reached for the bottle again. She poured and downed her fourth shot, and then started looking me up and down intently, sizing me up. Her stare became uncomfortable after a few seconds, and my heartbeat started to pick up. I looked away.

"Caleb, can I ask you another question?" Her voice had that same nervousness it had had earlier when she was explaining her jealousy of Eric, but now there was a slight smile on her lips.

"Uh... sure?" I asked, puzzled about where she was going and why she was looking at me that way.

"Sorry if this sounds weird, but..." Claire paused, glanced at the bottle, seemed to seriously consider taking another shot and then kept going. "Do you and Eric ever... you know... do anything sexual?"

My heartrate spiked and my cheeks and ears flushed burning hot. I couldn't believe she'd just asked that question, and I stared at her, my mouth slightly agape, totally flustered and unsure of what to say. She was the one to break the extremely awkward silence.

"It's just -- how do I say this? You just seem kind of..." She looked at the bottle again but soldiered on without another shot, blushing red (but probably not as red as me) and speaking nervously. "You've got this kind of feminine energy, and you're pretty for a guy."

Somehow, my face flushed even hotter, and I could hear my heart pounding in my ears. I was freaking out internally. I had never felt too secure in my masculinity, but I didn't realize I came across as that feminine, especially to someone like Claire who had only just met me. It felt like she had managed to uncover a secret of mine.

"Shit, I made this weird. I am so sorry." Claire said, now flustered herself. "I didn't mean to offend you. I guess I'm a little drunker than I thought. Look, I just got back from the gym with Eric, I should probably shower. Where's the shower?"

"Each bedroom has a bathroom. You can shower in Eric's. That's his room."

My heart continued to pound as I watched Claire grab a few things out of her suitcase and sheepishly hurry off to Eric's room to shower. It was the furthest thing from the confidence she'd had introducing herself to me just ten or fifteen minutes earlier.

I let out a breath as she closed the door to Eric's room behind her, only just now beginning to regain my wits. Her question hadn't so much made me offended as afraid. The truth was, she was closer to the target than she could have known.

No, I did not have any kind of sexual relationship with Eric. But I did have a secret: I had taken up crossdressing a few months earlier. I had never felt like an especially manly guy, had always felt alienated by and out of place with other guys. One day, I had found an abandoned bra and panties in our building's laundry room and tried it on, and found that it somehow felt right. And looked right, too: I had always had a slender build and a delicate face, and the features I had thought of as unmanly and unappealing actually looked pleasantly feminine in the right clothing.

This interest had snowballed in the last few months. I had taken my measurements and begun buying women's clothing online, trying it on in my room. I had begun shaving my body hair, started a skincare routine, and had even begun to experiment with makeup. All of this was in strict secrecy: I had never told anyone I knew in real life. But I had posted a few pictures (with my face cropped out, of course) online, and had received many gratifyingly thirsty replies.

Staring dumbfounded at the door to Eric's room, I listened to the sound of the shower and replayed the interaction with Claire in my head over and over. She had clearly seen me as effeminate from the start, but she had been friendly the whole time. She didn't seem to think it was off-putting or contemptible. She had spent a long time staring at me, sizing me up, but she had had a smile on her face when she did it. She seemed so nervous asking me that question, and so panicked when I didn't answer. And she had mentioned wishing she could experience sex like a man...

Wait, had she been hitting on me? I wasn't used to getting a lot of attention from women. I had been with girls before, but not many, and they weren't as good-looking as Claire. I had subconsciously decided she was out of my league and never considered the possibility she might be attracted to me while we were still talking, but now that I thought it over, it was starting to seem plausible. My heartrate picked back up as I thought about what to do.

I had to make a move, right? I had to see if she was really attracted to me. I'd always had a huge thing for athletic, tomboyish girls, but never had one reciprocate those feelings. This was the chance of a lifetime. I couldn't just let it slip by. My heart raced as I thought of the possible downside: what if she was just drunk and rambling, what if it was all in my head, what if I tell her my secret and she's repulsed and tells Eric and my whole life gets fucked up?

But, if I was right....

I looked at the bottle of vodka on the coffee table. Now I could really use the liquid courage. I poured myself another shot, downed it immediately, ignoring the burning in my throat, and headed into my bedroom.

I opened the bottom drawer of my dresser, where I kept my secrets. I dug through the women's clothing with desperate urgency, trying to figure out the best possible outfit. After considering a few options, I decided on a short black miniskirt with matching black thigh-highs, a set of white lace panties and a white, lacy lingerie bra. I wouldn't have time to do makeup, so the clothes themselves would have to be enough.

After hurriedly tearing off my jeans and t-shirt and changing into my new outfit, I examined myself in the full-length mirror on the bedroom wall. As I had hoped, I looked good. The miniskirt barely made it a quarter of the way down my thighs, and the thigh-highs stopped just above my knee and pinched the little fat in my thighs, leaving a few inches of smooth, slender, enticing skin visible between them and my skirt. My thin waist and flat stomach were visible between the waistband of the skirt and the bottom of the lacy bra, and the straps of the bra framed my narrow shoulders and dainty collarbones nicely. I had no makeup, but my face was naturally pretty, with delicate features, blue eyes, and straight light brown hair that stopped just above chin level.

I could hear the water stop running in Eric's bathroom, meaning Claire had just finished her shower. I stepped over to the closed door of my bedroom and listened for a few agonizing minutes, my heart racing. Finally, I could heard the sound of the other bedroom door opening and Claire's footsteps in the living room. Taking a deep breath, I cracked open the door to my room, but didn't step out.

"Claire?"

"Yes?"

"Can you keep a secret?" My heart was pounding so loud in my ears I was afraid I wouldn't be able to hear her answer.

"Uh... yes?" came her voice from the other room.

"I really mean it. You can't tell anyone. Especially not Eric."

There was a brief moment of silence before she answered.

"I promise I won't tell Eric. What is it?"

I took one more deep breath. It was the moment of truth. I pulled the door open and stepped into the living room. Claire was sitting on the couch, her suitcase open by her feet. She was dressed in loose but short shorts and a baggy white t-shirt, showing off bulging leg muscles and thick arms. Her dark brown hair was still wet from the shower (I hadn't heard a blow dryer, after all) and hanging down just past her shoulders as she looked up from the couch at me. I scrutinized her face carefully, hoping for a good reaction.

An expression of shock formed on Claire's face at first, but soon it gave way to a warm smile and a playful glint in her eye. Encouraged, I took a few steps forward. Her eyes were fixed on me, looking me up and down once again.

"I knew it," she said, a hint of vindication in her voice. "But wait... you said it was a secret and I couldn't tell Eric. So that means..."

"He doesn't know. No one does. Except you now."

Claire patted the seat next to her on the couch. I slowly made my way around the coffee table, heart racing, breathing heavily. I sat down, my leg practically brushing against hers. I couldn't meet her stare and looked down at our legs, noticing that her bulky, muscular thighs were twice as large around as each of my slender ones.

"That look suits you."

"Thank you." I blushed bright red, elated that she actually liked it but still trembling with nervousness. Maybe the vodka would help steady me. I reached for the bottle, but Claire's hand caught mine. Looking over at her, I noticed her leaning in.

Clarie's lips met mine in a kiss. Her breath smelled like alcohol from the shots she had taken earlier, but it still felt amazing to have her warm lips against mine. Besides, I'm sure my breath smelled of alcohol too, but she didn't seem to mind. Her other hand reached behind me and grabbed the back of my head, holding me in place as our lips locked. Finally, she slowly pulled back from the kiss.

"Your lips are so soft," she whispered.

"Thanks. I use a couple products for that." I admitted

"Ah, that makes sense. Never really bothered with that stuff, but maybe I should start." She caressed my face and then ran the back of her hand down my neck, shoulder, and arm.

"The rest of your skin is so soft too."

I giggled, and felt Claire's hand grasp my wrist and pull me in even closer. Turning, I swung my legs to the side and climbed onto her lap, straddling her massive thighs and looking down on her, placing my hands on her shoulders to keep me steady. Through the white t-shirt, I could feel that her shoulders were thick and muscular, which didn't surprise me considering the size of her thighs and her arms.

She grabbed my hips with both hands, pulling me even closer as she leaned in, passionately kissing my neck. I tilted my head back in pleasure, feeling her lips move up and down my throat, kissing it over and over. She worked her way down past my collarbones and slid the bra down, starting to suck my nipple. I let out a gasp, which made her pull away and giggle.

"So sensitive." She said with a smile.

"Sorry, it's just... I've never been like this with anyone before."

"Like how?"

"Girly? I feel so... vulnerable."

Claire smiled at that.

"But you like it, don't you?" She bucked her hips a little, rubbing her lower abdomen against mine, highlighting the unmistakable erection I now had.

"I love it." I admitted.

She grinned widely and kissed my neck again, running a hand down the small of my back and letting it rest on my ass. I gasped, and then paused for a moment, looking Claire in the eye. She stared back up at me.