Baiting the Hook

I sat in the campus dining hall, alone for a change. A chair scraped, and I looked up to see my friend Michelle taking a seat. We were in a few classes together, and we had found that we had similar personalities, including a love of gossip. Right now, she seemed to have a frantic energy about her, like she was about to burst.

"Oh my God, Ryan. I have to tell someone about this," she said, eyes wide.

"About what?" I asked. Michelle took a deep breath, but it didn't seem to calm her down much.

"Before I say anything, I need you to promise to keep the secret to yourself. It's about Rachel. You know Rachel, right?" She was talking fast, almost tripping over her words in excitement.

"Your roommate? Yeah, I know her. We're in the same precalc lecture, but we don't really talk much."

"I feel like I can't keep this to myself, but I don't want rumors going around about her. Promise to keep it secret?"

With a lead-up like that, I knew this was going to be good. I've always been a sucker for gossip.

"Yeah, I promise I won't tell anyone. What is it?"

Michelle leaned across the table to me, blonde hair falling over her face. She quickly parted it before speaking in a hushed tone.

"You would not believe what I walked in on Rachel watching last night."

"What?" I didn't feel like guessing.

"Okay, so like I wasn't trying to intrude or anything, I just poked my head into her bedroom to ask if she was fine with me cooking the last of the chicken in the fridge."

"What, you didn't knock or anything?"

"I did, but she didn't answer. Anyway, so I poke my head in and she's got her headphones on and she's staring at her laptop watching this crazy-ass porn."

"Like, what kind of crazy?"

"There was this guy dressed up in a schoolgirl costume getting fucked in the ass by some girl with a strapon. Like, just fucking railing him. Going to town on his ass while he was gasping and moaning at the camera. And Rachel looked like she was totally into it, had her hand down her sweatpants and was just staring."

"Uh... wow. That is crazy. It's always the shy ones who are into some weird shit, isn't it?" I replied, trying to sound casual and natural. The truth was, it actually did sound kind of hot to me.

"I know, right? It was called 'Bitchy Boss Fucks Sissy Secretary' or some shit like that. Rachel's so quiet, but damn, she's got a freaky side buried under that shy exterior."

"Ha, yeah, really freaky." Hopefully Michelle didn't pick up on my unease.

"I actually feel a little bad," continued Michelle, sShe noticed I was standing there and slammed the laptop shut. I've never seen anyone blush that red before. Poor girl was really embarrassed. Remember, don't tell anyone else about this. I just had to talk about it."

"Don't worry, your secret... well -- I guess her secret -- is safe with me."

Michelle changed the subject after that, talking first about the acting class we were both in, then a trip she had planned for the weekend, then a complaint about how dramatic some of her other friends could be. I had a hard time focusing on the conversation; as Michelle rolled through the things she wanted to talk about, my mind kept drifting back to Rachel and her unusual interests.

In fact, I shared some of those unusual interests with Rachel, not that I would tell anyone. It had begun with costumes. I was a theater major and an aspiring actor, and sometimes I had to play a female role for one of my classes as an exercise in stepping outside my comfort zone and learning to act like someone other than myself. I'd always been a pretty boy, with delicate facial features and a slender build, and I started to like the way I looked in the costumes even though they weren't meant to be sexy.

From there, I'd started experimenting with women's clothes on my own. Privacy wasn't a problem; I hadn't grown up with siblings, so I didn't like the idea of roommates, and my parents were well-off enough to rent a studio apartment for me instead of making me share an apartment with someone else. I had gotten myself a few dresses, then a few skimpier dresses, then got skimpier still with crop tops, short shorts, miniskirts, fishnets, and lingerie.

At first it had strictly been for my own curiosity, my own enjoyment of the taboo, my own thrill at seeing how well the clothes suited my body. But, as is usually the case with theater majors, I loved attention. So I had begun to post some of my better pics on Reddit and Instagram, delighting in the rush of the upvotes, the favorites, and of course, the replies and the direct messages. Despite my love of wearing women's clothing, I was much more interested in women than men, but I was still flattered and gratified by the dozens of men sliding into my inbox to tell me how pretty I was, to tell me how much I turned them on, to tell me the things they wanted to do with me, sometimes offering to buy me clothes or even to fly me out for a weekend.

Now, the idea of a girl being turned on by my crossdressing, a girl wanting to do the things those men told me they wanted to do with me... that wasn't just flattering, that was exciting. But I really didn't want Michelle to know I was thinking about that, so I smiled at her stories and nodded along and occasionally asked a question until the meal was done and we went our separate ways for the evening.

My thoughts were still about Rachel when I made it back to my apartment. I didn't know her that well, but from what I could remember she was a quiet, mousy brunette, not a head-turner but certainly not ugly. Unlike me, Rachel was shy. When a group of us would hang out at Michelle's apartment, Rachel wouldn't join us, instead making only brief small talk before retreating to her bedroom. Michelle didn't talk about Rachel often, but when she did, she painted a picture of a smart but timid girl who did well in class but didn't seem to have a lot of friends. But apparently, despite that outward shyness, she was turned on by the idea of dominating and pegging a guy.

Out of curiosity, I searched for the title of the video Michelle had caught Rachel watching. I was pleasantly surprised to find Michelle had remembered the name correctly, and soon had it open on my laptop.

As is usually the case with porn, it wasn't going to win any awards for the writing or acting. It was a pretty basic setup: the actress, a brunette woman with glasses, berated the actor, a thin younger blonde guy, her secretary, for messing up something on the job and threatened to fire him. He pleaded and said he'd do anything to keep his job, and then she made him strip and put on a schoolgirl costume, after which she put on a strapon and fucked him in various positions: bent over a couch, on his hands and knees on the floor, pressed against a wall, all while she called him a bitch and a slut.

As an actor, I wasn't impressed with it on an artistic level, but as a crossdresser, I still found it hot, especially since the Sissy Secretary looked kind of like me. Of course, I had a prettier face, a slimmer waist, and a nicer ass.

Now that I was comparing myself to the Sissy Secretary, I decided to take a look at the girl who might want to be my Bitchy Boss. I found Rachel's Instagram page without too much trouble. There weren't a lot of posts; the occasional group photo, some drawings she'd done (pretty good, actually), one gym pic, though I couldn't get a good impression of her body through the sweatpants and hoodie she was wearing. She did have some resemblance to the actress in the video; not as busty, but she was younger and had a cuter face, and was leaner too. Interestingly, she was also following me on Instagram, along with a lot of male models and influencers who looked like me; pretty faces, slim bodies, effeminate air about them. I smiled as I realized I was definitely her type.

Maybe I could send her some pics, ask if she was interested, invite her over. But where would be the fun in that? That video had been all about an aggressive woman taking the guy she wanted, feminizing and dominating him. I wanted something like that, not just a regular hookup.

A plan began to form in my mind. Rachel and I were in the same math lecture (even a theater major has general education requirements). Surely there had to be a way to leave myself at the mercy of her darker urges. As I drifted off to sleep, I fantasized about what it would be like to have her in the bed with me, groping me and pawing at me and nipping at me with her teeth before ramming a strapon into me.

----------------------------------------

I awoke the next morning and immediately thought of Rachel, my heart beating a little faster. Today was our weekly precalculus lecture. If I didn't do something today, I probably wouldn't get another chance until next week. It was time to make something happen.

Going through my closet, I scanned for something that might pique her interest without being too blatant or revealing me as a crossdresser to the entire university. I decided on a pair of tight jeans and a teal t-shirt that only just made it down to the waistband of my jeans, leaving a hint of my flat midriff exposed if I raised my arms. Turning and looking over my shoulder in the mirror, the jeans had their intended effect; they hugged my slender legs and showcased my ass, which was shapely and large enough to make some girls jealous. The t-shirt clung to my narrow shoulders, and my hair hung down just past my eyebrows. I had a vaguely feminine air about me, even though I wasn't wearing women's clothes.

I made my way across campus to the lecture hall. On the way over, I caught more than one guy surreptitiously checking me out. I smiled, less to encourage them and more because their attention validated me and confirmed I'd picked the right outfit for the job.

I entered the large, amphitheater-shaped lecture hall and scanned around. There were already at least fifty students there, but it didn't take long to spot Rachel sitting by herself about halfway between the door and the podium. Heart fluttering with anticipation, I made my way across her row. I turned to the side to slip past her, giving her a good look at my ass in the jeans before I sat down next to her.

"Hey, Rachel." I said.

"Oh, uh... hey Ryan." There was a hint of nervousness in her voice. She had her brown hair in a ponytail and glasses on her face, reminding me of a librarian. Looking down at the desk in front of her, I could see she already had her notebook open to a page half-filled with immaculately hand-written notes from the previous lecture.

"How's it going today?"

"Oh, it's... going." For some reason, she was trying not to look at me. Was she flustered just from talking to me?

"Yeah, I know how you feel. I hate math."

"Uh-huh." She paused, sounding like she was trying to think of something to say. Just then, our professor, a middle-aged man with the dullest monotone I'd ever heard, took the podium and began his lecture, saving her from having to continue the conversation.

The professor went on for an hour, walking us through various concepts and equations. He wasn't an engaging speaker, and I'd always found math dull, so it wasn't hard for me to look helpless and lost. Out of the corner of my eye, I caught Rachel stealing glances at me every few minutes throughout the lecture, her gaze lingering on me for seconds at a time, but her head always snapped back to look at her dense page of notes every time I turned to look at her.

Mercifully, the end of class finally came. I looked over at Rachel and then down at her notes as the rest of the students in the hall filed out.

"Can you follow any of this? I'm really struggling." I asked. It was true, but I really wanted her to know it.

"Yeah, I think I'm staying afloat." Perfect, there was my opportunity.

"Can I ask you for a favor?"

"Uh... yeah, what is it?" She was making eye contact with me, but I could tell it was taking effort for her to maintain it. Her cheeks were a little red.

"Are you doing anything later today? I could really use some help studying for this class. The online quizzes are kicking my ass."

Rachel looked surprised, and her cheeks got a little redder. She was quiet for a moment, and then when she spoke, she spoke fast. She really was nervous.

"Yeah! I'm free later. What time works for you?"

"How about 1:00? Can you come over to my apartment?" I passed her a note with my phone number and my unit number.

"Of course! See you at 1:00!"

I smiled and grabbed my backpack off the floor, bending over a little bit to do so. I couldn't tell if she was checking me out, but I thought I'd give her the chance. Walking out of the lecture hall, I made my way back to my room. I still had about an hour and a half before Rachel arrived to study with me. I straightened up the small studio apartment a bit, then grabbed one of my lacy black bras and left it hanging over the towel bar in the bathroom. For good measure, I pulled up the browser on my laptop and opened my Reddit account with my lewd, crossdressed pictures in a tab in the background.

There was a knock on the door at 12:55 PM. Rachel was either punctual as a habit or very excited. I chose to believe it was the latter. I opened the door for her and smiled broadly. Rachel stood in the doorway, dressed in jeans that weren't nearly as tight as mine and a dark blue blouse with a high neckline. She gave a nervous but excited little grin of her own as I welcomed her in.

"Hey, thank you so much for coming! I'm so lost in this precalc class!" I stepped up for a hug. Rachel hesitated for a moment before wrapping her arms around me. Maybe I was flattering myself, but she lingered in the hug a few seconds longer than normal, and her hands seemed to cling at my back.

"Yeah, of course, any time." She paused for a moment. "Glad to help," she added quickly.

"Your notes just seemed so thorough, and Michelle says you're really smart." Her smile grew a little wider, but her cheeks flushed at the compliment. This girl really did like me.

"Th-thanks."

I gestured to the table where I had my laptop and my class notes. Rachel shrugged off her backpack before sitting down and pulling out her notes.

"Do you want a glass of water or anything?"

"Yeah, sure, I'd like that."

I wasn't looking at her, but I could feel her eyes on me as I filled the glasses. When I turned around to bring them back to the table, though, she was gazing intently at her notes, almost like she was trying not to get caught staring at me.

When I sat down across from her, Rachel launched into explaining the material without any more small talk. Her nervousness faded as we dove into the material; she was clearly more at ease talking about exponents and logarithms and limits than she was trying to make casual conversation with me. I wasn't good at math, but I played even dumber than I actually was, asking lots of questions and waiting with wide eyes for her patient and thorough explanations.

After about twenty minutes of her walking me through concepts, equations, and explanations, she asked if she could use the bathroom. I pointed her toward it and waited as she got up, my pulsing speeding up as I thought about the bra I'd left there for her to find. The sound of the faucet came on, and the moment seemed to stretch with anticipation. Finally, the door opened and she returned to the table.

"I didn't realize you had a girlfriend," said Rachel as she sat down across from me.

"Uh... what?"

"Looks like someone left a bra in the bathroom."

"Oh! Right, that. Yeah, uh..." I paused for effect and broke eye contact, then looked away while I continued. "You wouldn't know her, she goes to a different school. What about you? Do you have a boyfriend?" Hopefully she'd pick up on the obvious lie and the hasty subject change.

Rachel arched an eyebrow in puzzlement. "Uh... no. Still single."

She blushed a little and returned to the work. But now she lacked the focus she had earlier; I caught her looking at me more frequently, her eyes lingering on me as if she were sizing me up. I made a little show of avoiding her gaze when I caught her staring at me, focusing on the page and trying to act nervously like she had earlier.

Even though neither one of us was really focused on math at that point, Rachel eventually got us through three or four more problems. Worried that Rachel would forget about the bra and get too focused on studying again, I decided to add a little more bait to the hook.

"Can you help me with the online quiz for this week?"

"Sure."

I pulled up the screen on my laptop again, the online quiz in one browser tab and the Reddit account with my suggestive crossdressing pictures in the other. Rachel moved her chair around to my side of the table and looked over my shoulder at the screen. I had the quiz pulled up, but there was no way she could miss the other tab.

"Hold on, let me use the bathroom before we start," I said as I got up without locking the screen. Hopefully she was curious enough to snoop around when I was away. I took my time in the bathroom, washing my hands for a good thirty seconds when I was done. When I opened the door and returned to the table, Rachel was sizing me up even more intensely than before, her brown eyes peering at me through her rectangular-framed glasses.

It was a quick quiz, but Rachel seemed even more distracted now than she had been after she'd returned from the bathroom herself. She must have taken a look while I was gone, must have figured out the secret by now. She was trembling slightly, her eyes constantly darting over to me while we went through the questions, a delay creeping into her answers about my math questions as if something else were on her mind. My heart began to beat faster as I realized my plan was working. Now to just get her to close the deal.

"Rachel, you're a lifesaver! I'm so screwed if I don't pass this class. I can't thank you enough."

"Oh - it's okay. I don't mind going over this stuff with you." She still needed a little more prompting, but I didn't mind giving it to her.

"Really, you've been so helpful. Is there anything I can do to repay you?"

Rachel took a deep breath and paused, looking like she was working up the courage for something as her brown eyes bored into me. She brushed an errant strand of her brunette hair behind her ear.

"Ryan, can I ask you something?" She was jittery again, but she didn't seem quite as reserved and nervous as she had when she first came over.

"Uh, sure... what is it?"

"You don't really have a girlfriend, do you?"

"Wh-what are you talking about?" I was really putting my acting classes to use, trying to seem as shocked and nervous as possible. But underneath the act, there was some real nervousness, mixed with excitement. She was actually going for it!

"You don't really have a girlfriend who goes to another school. That bra in the bathroom is yours, isn't it?"

"I-I" I stammered performatively, then paused. "Yes." I said quietly, deliberately avoiding eye contact. Glancing up a moment later, I saw a smile growing on Rachel's face.

"And that's not the only thing you have, is it? This is a habit of yours, isn't it?" There was an edge to her voice now.

I nodded. Rachel was actually shaking even more than I was. She took a moment to collect herself before continuing.

"Show me."

"What?" I tried to sound scared and taken aback.

"You asked how you could repay me. I want to see you in one of your outfits."

Breathing fast, I stood up. Holy shit, she was really going for it!

"Tell you what," said Rachel, standing up behind me. "I won't watch you change. I forgot something in my apartment. I'll be back in twenty minutes. Be wearing something cute when I come back." With that, she picked up her backpack and scurried to the door before I could answer, leaving me alone in my apartment.