My Roommate Made Me a Sissy

CH 11

Aaron stared at me for a minute and I didn't know how to take it. I didn't waste time when I got home from Ashley's, I went right to him and told him that I wasn't getting paid next week like I thought, but it was the week after. He paused his game and told me to turn on the light. It was late and he always gamed in the dark when it was night out. I flicked the light on and he just stared at me.

"I'm gonna get it," I said after a few minutes of his eyes on me.

"Nah, man. That ain't even it. I'm just trying to figure you out. Like, is you serious or what because no matter what the fuck I do for you, there's always something with you. There's always some excuse. Some situation that came up. It's always somethin' and I'm just flat out done givin' any shit about your excuses."

I started to talk and he held his hand up.

"Naw, I don't even want to hear it. It's gonna be some bullshit about how you're gonna pay and it's this or that. I don't even want to hear it."

My face sank. I didn't know what to do or say. There wasn't anything I could do or say, I was at his mercy right now. He was right about all of it. It was in my best interest to just not talk.

The silence was unbearable as he stared at me. I wanted to plead my case or make it better. How could I make it better?

Should I get on my knees for him? Should I go over and suck him off?

The thought went back and forth in my head. It would show him that I was still willing to keep going on our deal, that he didn't need to ask and I was at his mercy. He always seems to like having the power in this relationship, should I just give it to him?

I gulped and thought a bit deeper, should I bend over for him and offer myself?

I didn't want to do that, I was too scared. What if he plunged in with no lube. I don't think I could take it, and then what? But I had to do something, so I walked over to him and got on my knees in front of him. It felt hard to breathe and I couldn't look him in the eye for more than a second. I wanted, well I don't know what I wanted but I just needed him to say something and tell me what was going to happen so I could agree to it and I could get rid of this fear.

Swallowing my pride, I started pulling at his pants, gripping the fabric at his thighs and tugging down on it. His eyes looked through me, then pulled his pants back up and said, "naw, it ain't gonna be that easy this time."

"What do you want then? Please, I'm sorry. I know, I'm full of shit but I'm trying."

I felt so vulnerable. My voice quaked as I talked. I was trying and I don't know that he realized it or not.

"Look man, I get that you're upset and none of this shit was in your plan or whatever, but you gotta look at this from my point of view. All I got is a cock suckin' bitch who keeps ridin' their lips for free. If you're gonna get all you need then you're going to have to give up some more. I know you ain't gonna like this but since you already broke our agreement I'm gonna have to do some of my own breakin."

I sat back and looked at him confusedly, "like what?"

"I'm gonna employ you for a night. You like how those lips are carrying you so much, you can show them off to a few friends of mine. Don't worry, they don't know you and ain't never gonna know you. I won't be sharing your name or nothing, but you're gonna be our waitress for the night. I got them coming over to discuss our weekend and you're gonna do all the shit we don't want and then some of the stuff we do."

My face must have looked horrified because Aaron started laughing.

"Oh T, man, that ain't even the half of it. I'mma take you shoppin' and you gonna pick out something nice and pretty for the night. I'mma spend a lot of money on you. You gonna go get your body waxed and your hair done and, you know what, I'm gonna take you out and get some nice make-up done too. You won't even be recognizable."

I could only blink.

"It's this or get the fuck out tomorrow. Either way, I'm finally gonna get what I want instead of constantly giving you chances."

My mouth fell open to say something but there were no words.

"Tomorrow we goin shoppin'. You can bring your girl along if you want tips on what to get," he laughed.

"They comin' over in a couple of days and we gonna drink and get food and watch some football. You can be our bitch and treat us like kings, got it?"

I continued staring, dumbfounded.

"Got it?" Aaron reached out and grabbed me by the hair and shook my head. His jaw was tight. I looked at his eyes and they were blazing. I could see his teeth clenched tight behind his lips. My eyes lingered there on his mouth before I nodded meekly.

"Yeah, I g-got it. I, unh huh."

"Good, now get your ass to bed," he shoved me away and went back to playing his games.

I make it to my bedroom, crawl into bed with my clothes still on and somehow fall right to sleep. My dreams are filled with me in awkward situations, usually naked, and unable to cover myself. Everyone is staring at me and no matter where I go I can't stop people from staring at me and talking about how they can't believe I'm out here with no clothes on. I start to cry in my dream and everything moves around me as if normal. People walking and carrying on their conversations while I sob and my hand is between my legs stroking my dick. Nobody acknowledges it but I keep doing it until I bring myself to orgasm in front of these stranges, which is when I wake up in the morning. When I roll over, still hazy from my dream, I find that I've had a wet dream and there's cum all over my bed, blanket and sheets.

I didn't bother cleaning it or changing the sheets, but I laid in it until Aaron knocked on my door and yelled, "get ready to go. We leavin in a minute."

I made sure I was ready quickly, throwing on some clothes and waiting for him by the door. Last night was such a strange experience, the way he told me it was going to go could have been a lot worse but the way he grabbed me so aggressively at the end really shook me. There was legitimate fear in me and I didn't want to bring it out in him again.

I followed Aaron into the elevator and out of the building to his car. It was nice inside, he kept it very clean and must have had it detailed regularly because it looked like it was just off of the dealership.

After a few minutes of driving he turned the radio down and said without looking at me, "you awfully quiet today T. Not looking forward to your shopping spree? Most chicks would kill for this kinda shit."

I let the fact that he called me a chick slide because I knew what he meant.

"Yeah I just, don't know."

"Don't know what, man?"

"What I'm supposed to do, or get or whatever. Anything."

"I'll tell you what to get, for the most part. The variety of it I'll let you settle on. Like first, we goin to Victoria Secret and you gonna pick out somethin sexy for the guys. A nice little corset top with some thong panties."

As he talked he had a big grin on his face like it was all so funny for him to humiliate me like this.

"Yeah, whatever. But what do I say? I can't say I'm buying this for me."

"Why not?" Aaron took a quick glance at me before turning his attention back to the road.

"Because its lingerie. Why would it be for me?"

"T, but it IS for you."

"Yeah, but," I didn't have an answer for that so I stopped talking and went silent again.

"Look, I don't give a fuck what you tell the sales girls as long as you get something that fits you. Tell'm you gay and pickin something out for your boyfriend who's the same size as you if you don't want to say its for you. But fucked if I care. Tell'm it is for you, say you're into crossdressing. Who gives a shit, you ain't gonna know these chicks."

Sighing long and hard and buried my face in my hand. Right, just go and tell them I'm gay or I'm trans or a cross dresser. Sure, easy conversation to have. I'd like to see him go in and say he's buying this for his personal male cock sucker and see how he feels about that.

Aaron walked me into the mall and to the store but he didn't go in with me.

"This part is up to you, T. I don't care about color or flair, but I gave you the instructions of what I want you to get, now go in and get it. I'mma be over here waitin so don't take long. We got a few stops to make."

The store wasn't that busy, which was probably worse because the girls that worked there would have more time to help me even though I didn't want them to. I figured I could pick something out myself. I didn't know what cup size I was or anything, but it wasn't much and I knew A was the smallest so I'd just go with an L size A or whatever. I just hoped that's how the sizes worked.

"Can I help you?" A short blonde girl sidled up next to me sounding overly chipper just as I had taken one of the corset tops off of the wall and held it up to me.

Well, there goes any chance of saying it's not for me.

"Um, no, I mean, yeah. I uh, don't know what I'm doing. I uh, need to get something and I don't know what to pick. Are the sizes the same for like, everything?"

She smiled her bright, store clerk smile with her exceptionally white teeth and sweet smelling perfume.

"Yeah, like, is it for someone else or," she trailed off to let me answer the awkward part.

Clearing my throat, I bit the bullet, "no, not someone else. It's, yeah no."

She nodded quickly and dropped her smile and turned on her helpful mode.

"Okay, yes. Well, if it's for someone who is of bigger stature then I recommend a bit bigger as the sizes do tend to run snug and just in case they aren't used to wearing this type of garment they might not feel as comfortable."

She handed me an XL of the same item I was holding.

"You're welcome to use our dressing rooms if that's something that may be needed," she pointed towards the back.

"No, no. No. No," I shook my head profusely.

Just as she began to walk away I remembered I needed another item and called out to her. It was better to only have to do the awkward introduction once than have her get busy helping someone else and have another girl ask me if I needed help picking out panties.

"Do you have, uh, panties?"

What a stupid fucking question. Of course they have panties. Jesus.

"We do. There's an entire table of them out front over there and the various sizes can be found in the drawers below."

"Do the sizes work the same?" My face must have looked pained because she took pity on me and walked me over and picked out the pair that best matched the corset top I had.

"Would you like me to ring you through?"

"That would be incredible, yes, please."

She was incredibly sweet and very attractive. I always thought it was funny how they found the most attractive women to work at this store, as if there was some endless supply of them always needing work. The entire experience was awkward but couldn't have gone better and I told her how much easier she made everything.

"I'm happy to help and I'm glad you felt comfortable enough to allow me to assist. Good luck and I hope whoever its for loves the way it looks."

I smiled and left the store. When I spotted Aaron sitting on a bench a few stores down I held up the bag and shook it a little, giving him a smile before realizing what I was doing and dropping my hands down and clearing the expression off of my face.

"See, not so bad huh? Even get to talk to a cute chick I'm sure," he nudged me with my elbow.

"Yeah, but I'm sure she thinks I'm fuckin gay so its not like I could ever do anything about it."

Aaron just laughed and we headed back towards the car, but on the way he stopped and pointed at Sephora.

"So, tomorrow afternoon before the guys are over you're going to come here and I want you to see one of them make-up chicks in there. You're gonna have them paint your face up real nice. Some eye liner. Mascara. I want you pretty, with some nice bright red lips."

I was surprised how casually he was saying this out in public with people around. He was pointing and talking as if we were home alone in the apartment. I wanted to groan and protest but it wasn't my place. I knew I had run out of chances and this was his call now. Anything he says goes, so I just stared and nodded and followed him out to the car.

We drove to a little place that did wax jobs but he came in with me this time. He took a look at the board on the wall of all of the options they have and then shook his head before turning to the lady behind the counter.

"Hi, Miss? I don't know what any of this stuff is but my friend here needs a full on wax job of his entire body. You see, he came in last in our fantasy football league this year and that's the penalty for coming in last. I know, men are so juvenile, right?"

Fuck. Why didn't I think of that for the lingerie? God damnit.

The woman behind the front desk laughed and nodded to Aaron.

"So you want a full body wax?" She smiled sympathetically in my direction.

"I want this boy hairless aside from the eyebrows up," Aaron smiled at her then looked in my direction.

"Okay then, we can do that. Will you be joining him for the pleasure of witnessing it or is that too much?"

Aaron laughed and shook his head, "naw. You take care of him and I'll wait here. And I'm payin', that'd be cruel to make him pay for it himself right?"

She laughed and nodded, "oh yes, that would be really awful."

She then turned her attention to me, "okay, you can come with me."

The entire experience was a blur. A painful, humiliating blur. I had to strip down naked and had every part of my body stripped to the roots of any semblance of hair on me. My entire privates felt like they were on fire along with my ass, my chest and my armpits. I caught a glimpse of myself in the mirror and I was red all over. Putting my clothes back on made everything worse and each move I made shifted my clothes this way and that flared up the irritation on my skin. The closest thing I could liken it to was if I had a horrible sunburn on my balls.

When we got home Aaron told me to strip in the doorway, that he wanted to get a look at me.

"Come on, I wanna see what your twink ass body looks all hairless and shit."

I had never considered myself small or anything so hearing him describe me as a twink made me feel a bit self conscious. I wasn't overly tall or broad shouldered and I was a bit on the skinny side but, I guess he had a point but it wasn't something I thought of often. I took my clothes off without hesitation and stood as he gawked at me.

"Fuck, T. Yo, you look fuckin amazing, man! Who thought you'd look like such a chick with no hair. I can't wait to see what you look like all done up. Fuck, man, the boys are gonna get a fuckin kick outta this. You'd make any tranny jealous as shit with that body. All you need is some HRT and some little tits and you'd basically be a chick."

He laughed and turned around and walked back to his bedroom. I was sure he was going to ask to fuck me then. He'd take me out and around town, doll me up and then bring me home and fuck me for the first time. But no, he didn't. I even stood in the living room for a few minutes expecting him to come back but he never did, so I grabbed my clothes and went into my room and stood in front of the mirror on my closet to get a better look at myself.

Aaron was right. With all of the hair gone my body did give off feminine vibes, especially with how shrunken my dick was after all the abuse the surrounding area took today. It was so small it looked like a nub. I ran my hand down between my legs and felt how smooth everything was. It reminded me of the way Ashley felt when I was between her legs and feeling her inner thighs. I was tempted to try on the lingerie to see how it looked but wasn't sure I was ready for that just yet. It was probably best to do all of that at once.

I spent most of the day in my room, avoiding Aaron and avoiding life mostly. There were so many things I needed to get my head around that I was having a hard time sorting them all out. I skipped dinner and thought it was for the best as well, if I was going to be serving these guys to do whatever it is they want I'd probably not want to have a full stomach. I had to anticipate everything.

Aaron sent me away an hour or so before the guys were supposed to show up. I had to run to Sephora and I planned on using the lie that Aaron did about losing the fantasy football league and this was my punishment. It worked pretty well as the girl said she would make me look amazing and in turn make them all look stupid for making me do this as I'd look so hot.

I texted Ashley and asked how she was as I hadn't heard from her much since I left her place. She responded but it was short and without much details so I could tell she was still upset. I left her too it then, I couldn't deal with trying to sort her shit out and mine at the same time. Not with whatever was going to happen tonight on my mind.

The makeup did look good on me. The eye liner really made my eyes jump out and I looked like a cabaret singer or something. The red on my lips was a little bright but it was what Aaron wanted so I had to oblige.

When I walked into the apartment the guys were all in the living room, Aaron grabbed me and shoved me down the hallway before they could turn around and get a good look at me. He pulled me into his bedroom and closed the door.

"Hey, T, I got you something for tonight," and he held out a small plastic thing that I couldn't tell what it was.

"Okay, what is it?"

"Strip, I'll show you."

I looked at him for a second then dropped my shoulders in annoyance and took off all of my clothes. He got down on his knees and disassembled the plastic device and began guiding my dick into it.

"What is that?" I said, looking down at him.

"It's a chastity cage. I got it because I know what kind of a little needy whore you can be and I don't want you tugging at your dick tonight and cumming before everybody is done playing with you."

"What's it do?"

"It prevents you from getting hard, and if you do, well, it's going to make you want to not be hard because there ain't no room to go nowhere."

With that he clicked the lock and put the key on his dresser.

"Now go on and get dressed and come introduce yourself to the guys. We got food and beer and shit and you need to start your night."

Aaron seemed like he was in a really good mood. I don't know if it was the night or having his friends over or what, but he was practically giddy. He practically ran out of the room and yelled to his friends, "she's almost ready!"

It was so annoying the way he kept referring to me as a girl. I'm not a fucking girl, I'm a guy. Then I sighed and mumbled, "yeah, a guy that fucking sucks dick."

The girl from Victoria's Secret was right, the corset top was very snug and I'm glad I got a size up as it was really tight on my midsection. The panties were a stupid idea as they barely covered anything, especially with the chastity cage, and the thong felt so unnatural between my cheeks I had to keep pulling it out.

As I walked into the room the three other guys turned around and Aaron put his hand around my shoulder, hugging me in.

"Hey, guys. This is our help for tonight. No names, just refer to her as waitress or Miss or whatever you'd like and she'll be right there to help you with WHATEVER need you may have."

With that Aaron slapped me on the ass and I didn't expect it. I stumbled forward a bit and fell into one of his friends.

"Hey," he said with a wide smile.

"Um, sorry. I'm sorry," I mumbled softly.

"Don't worry about it," he looked at me with his dark brown eyes and light brown skin. He had a slight accent as he talked, Hispanic, but it was just a hint on certain syllables I could pick out. He didn't stop smiling at me, then bit his lower lip and dragged it out from between his teeth.