The next morning I awaken to a surprising (if not a little more familiar than I would prefer it to be) sight. I open my eyes and about halfway across my small, shared room is Jake - naked, wet, and glistening. His cock is approximately eye-level while I lay on my bed, so I'm greeted with a view of his dangling, impressive manhood first thing in the morning as he rubs a towel through his hair.
"G'morning sunshine," he says with a grin, pulling the towel from his face. He lays it at the foot of his bed and begins to, with absolutely zero haste, rifle through his drawer to fetch some underwear. This man has absolutely no shame - and I can't blame him. If I had a cock that big I'd be swinging it around for everyone to see, too.
"Morning..." I say, doing my best to look anywhere but in his direction. "You got class today?"
"Nah. Gonna go see this new chick I met" he explains. Does this guy ever go to class? Seems like all he does is get laid. And where does he find the time to meet these women when all he does is have sex?
"Another one huh?"
"Yeah, man. This cute little brunette girl. We met on one of those anonymous dating apps, so I don't know her face but I've seen her body. She's a little flat, but a nice ass."
"Don't you get tired of...I dunno...constantly putting in the work with so many women?"
He pulls out a pair of boxers, then turns and walks toward me, boxers in hand. As he closes in I lose my war with myself, there's nothing I can do to look away any longer when he gets close enough to place his free hand on my shoulder, sort of half bent over looking down at me. Now, rather than look away, I'm doing everything I can to maintain eye contact for fear of making him think I'm looking at his dick.
"See there's your problem. What do you mean 'work?' It's not that hard my man" he explains. I stare him in the eye as he does, knowing that his dick is still out and dangling in my periphery. I feel my cock strain in its cage. Really? Even this is doing it? I really have changed.
I do nothing but nod in response - too intimidated to utter a response. It's not that I got the feeling that he was trying to scare me, but his raw energy was overwhelming me. Jake breaks eye contact and backs up, now fully standing upright - dick again at eye level. I glance at it but quickly look back up at his face. He's not even a little hard and easily 3 times my size.
"Just gotta have some confidence, my friend. The ladies love confidence. The rest comes easy."
He's right. I'm always stumbling and stammering over my words. I need to be more confident. "Thanks for the advice, Jake. I'm lucky to have you around."
Jake grins and pats me on the shoulder. "Don't mention it bro. But hey, it's not like you need my advice. You and Jenna do the deed yet?"
"Oh, uh" I begin to stammer but Jake's advice is firmly latched in my mind. "Totally man. Yeah, we fucked last night. She was tight" I say, trying to exude the same level of authority he does.
"Nice bro" he exclaims, holding his fist out for a bump.
I press my fist to his. Why lie? I guess on some level I want to impress him. He's got his shit together with women. I want him to think I'm cool. He's pretty much my only friend on campus so far.
He turns and finishes getting dressed before leaving for class. Fortunately, I have some time before my first class of the day. I check my phone and notice a new text. Must've happened while I was talking to Jake. I cross my fingers hoping to see Jenna's name, instead, I see Cameron's.
"My room. We have a deal to discuss."
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I knock at Cameron's room.
"It's open" I hear from the other side.
I enter to find Cameron in nothing but his boxer shorts, laying in bed smoking a joint. What's with the people at this school? Jake is always fucking, and Cameron is always smoking.
"Hello, Sir."
"Alright, I have a new rule for you bitch boy. I don't want to have to tell you to strip every time you come in. So from now on you come in and strip before saying a word. Got it?"
"Yes Sir," I say, realizing that I never changed into my panties - and I don't even have the bra! I begin to strip, getting fully naked.
"Do you see a problem with this sight, bitch boy?" Cameron asks, rising from his bed and pointing to a mirror. I turn and look at myself in the mirror as Cameron walks up behind me. His taller, hairy, more imposing frame loomed behind my hairless and, by comparison rather feminine body.
"Y-yes, Sir."
"What do you think the problem is?"
"I'm not wearing the" I begin to say before he cuts me off, finishing my sentence.
"The underwear I was nice enough to give you" he growls. "That's a little rude, don't you think?"
"Yes, Sir" I respond "I apologize but I...left my bra in Jenna's room."
Cameron cackles. "That sounds like a fun story. But I'm not in the mood right now. So unless you'd like me to call Jenna up and tell her exactly where that bra came from, you'll do 2 things for me. One - you'll go to your room and put your panties on. And two - you'll come back here with all of your boxers in hand. Now."
"All of th-" I begin to complain before he cuts me off again, this time with a slap to the face. I recoil from the slap, shocked at what has occurred.
"I didn't ask for a response. I told gave you a command" he says calmly before shifting to anger to say "Now go."
I don't even turn to look at him, I just grab my clothes and fumble to put them on as I walk out of the door, walking quickly down the hall to my room. I do as he says, and return with all of my boxers in hand. As I enter I remember the other command I was given. I drop my boxers and immediately strip - this time down to my panties.
Cameron pulls out a trash bag and begins shoving all of my boxers into them. "If you can't do something as simple as wearing your panties when you come here, I guess you'll just have to wear them all the time" he explains. "These are going in the trash."
"But-" I begin to protest but stop when he shoots me a glare. "Yes Sir."
He throws the bag of boxers into the corner of the room, then pulls out the same bag that my panties came out of and tosses me 2 more pairs. "Now you have no excuses."
I examine them. The original pair I was given is a sort of cheeky cut lace. The two I just received are far less modest - a purple thong and a pink g-string.
"Now. You owe me for some weed. How are you gonna make that happen?"
"I don't have much money, Sir..."
"I figured as much. So offer me something else."
I look up from my new panties, trying to read his body language for a hint as to what he might want.
"M-my mouth, Sir?"
"M-m-m-my m-m-m-mouth" he mocks. "I already have that whenever I want. Try harder."
I gulp, knowing where this is going. Remember, Erin. Confidence. "My ass" I state as confidently as I can.
Cameron grins and I feel like I've walked into a trap. This is what he wanted all along, isn't it? And I'm playing right into his hand. I've never taken anything up my ass before, but it seemed like the only logical next step to offer.
He reaches into a drawer, then tosses me a douche, some lube, and a butt plug. "The next time I call on you. You better be ready to pay up."
"Y-yes, Sir."
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After classes are done for the day I return to my room. I stare at the collection of tools given to me by Cameron and realize that, when he calls on me, I'll have to move pretty fast, and I have no idea what I'm doing with them. I pull my laptop out and start googling. "How to douche." A video shows up in the search results, and I hit play.
A man starts explaining how to insert the device, and about 2 minutes into the video there's a knock at my door. Who could that be? I hit pause, then shove the douche, lube, and plug under my bed sheet.
I open the door and see Allie. "Sorry, Jake isn't here..."
She doesn't respond, simply pushing past me into the room. First, she walks over to the cabinet where Jake and I keep snacks. She grabs a bag of fruit snacks, then sits on Jake's bed and lies back. "Let's talk," she says, popping a fruit snack into her mouth.
"Is this about...the bra?" I say in a hushed tone.
She eats another fruit snack and leans forward, resting her elbows on her knees. "Duh." At this angle her shirt is hanging low, and her cleavage is catching my eye. "So spill. How long have you been a sissy?"
"I'm!" I shout before lowering my voice "I'm not a sissy..." I say getting closer to her, sitting on the futon in the middle of the room. "You gotta promise not to tell anyone but...I'm being blackmailed."
"For wearing a bra?"
"No! For...well, public indecency. But he's making me wear a bra sometimes. Among other things."
Allie looks at me, perplexed, chewing on a fruit snack. This close up I can smell her perfume. The more I learn about Allie, the harder it is to not be attracted to her. Her shoulder-length black hair shifts as she lays back again, half reclined in a similar position to the other night when we talked, this time lifting her feet to lay them on my lap.
I force back the urge to question what is happening - remembering that confidence is key. I shouldn't let this bother me. Time to swing my big dick, like Jake.
"So another guy is forcing you to wear women's clothing because he has a picture of you with your dick out?"
"Pretty much."
"What does he get out of it, though? Do you send him pictures of yourself in the bra?"
"Not quite..." I say, my confidence wavering.
She stops chewing and sits back up, eyes wide. "You're sucking his dick!" she shouts.
"Shh! Keep your voice down" I plead.
"Man I knew you were a wimp but this takes it to a whole new level," she says, returning to her feet up recline, popping another fruit snack. "You're truly spineless."
