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  • Being My Roommate's Sissy Pt. 01

Being My Roommate's Sissy Pt. 01

We approach the door to my dorm, walking slowly with our hands in our pockets. Glancing over at her she seems sort of detached from the conversation, maybe thinking of what she's going to say when we reach my door? I feel kind of nervous as we step our way through the dim-lit corridor, it must be at least 11 at night now; all the dorms are so quiet - making a surreal kind of atmosphere. I have never really been on a date before so I didn't really know what I was supposed to be saying right now, this whole thing was so new to me. I really liked this girl though, Kara. She was so mature and funny, and I wish I wasn't so nervous talking to her because then maybe she could grow to like me as well. Instead, I stumble most of my sentences and usually just answer her questions about me.

I mean, of course it didn't go as well as I thought it would. In the picture perfect date I imagined in my foolish excitement before this night she would be giggling right now, holding my hand, as we make our way, inseparable, through this corridor. I guess this is just how it works, it takes time to get intimate with a person. I didn't have experience with this anyways, so I shouldn't beat myself up about it. During high school, I preferred to spend time alone - instead of competing to lose my virginity first at parties. The little dates and relationships I had, more fueled by social pressure instead of interest, ended short and abruptly, leaving the girl unpleased and me anxious.

And now we were at the door, face to face. She smirked a bit and blew some air through her nose, now glancing up at me.

"So, that was fun, right? Haha."

"Oh yea, definitely." I say in reply, rather quickly.

I look in her eyes... wow she was pretty. Kara was definitely way out of my league, and even though I promised myself to ignore appearances when looking for girlfriends it was still really hard not to notice. She had the most beautiful complexion which made her face so cute. And from the vague clues her outfit told of her body she seemed to qualify for a model magazine. Really, she was wearing skinny jeans that just barely looped around her ass, and a slightly see through tank top that made her boob crevice even more visible. In her stature she seemed so petite but was still so tall, and her auburn hair, sort of a mess, was simply mesmerizing.

"So.. I guess, see you in Calculus tomorrow?"

Oh crap. What do I say? Do I invite her in? That obviously means sex, but I feel obligated to. Kara's twisting her cheeks in an awkward fashion. My eyesight trails off from hers a bit.

"Wait.. Uhmmm."

I'm overcome with feelings of doubt, I really do feel like I am at a crossroad here. I feel obligated to invite her.

"Do you want to, uh, maybe come in?"

And this is followed by silence. She's visibly uncomfortable from my request as she looks down at her toes and takes in a deep breath.

"Sorry... I'm just not really looking for that right now."

I feel so stupid asking her, I don't know what to reply with and I think she can sense it.

"Plus, it's pretty late, I should be going home right now."

"Oh yea... I understand."

I bite my lips and feel so awkward, Kara smirks again, and I look down at my toes.

"Sorry about that, haha... But yea, I'll see you in math. I hope we can do this again som-

"Yea, haha, so I guess I'll see you in math. Thanks for the dinner! I had a great time." She says, smiling, and with that note she turns away to walk further down the hallway. I feel so unassertive in that moment, why did she cut me off? I can't help but to look at her ass one more time, swaying so sexily from side to side as she walks away. I feel so stupid asking her that, why did I have to convince myself? I just hope it won't be awkward between us. I sigh and push through the door to my room.

The lights are on for some reason...

"Clap. Clap. Clap."

Startled I whip around to the source of the noise, Tanner's leaning on the wall by the door, oh my god, did he hear all of that?

"Great job Princess, amazing job." He said, assertively - like always - and in a mocking tone. He resumes to his 'arms crossed' position, accentuating his pecs and biceps even more.

"My favourite part is when you apologized, it took all of my power not to laugh. I could just imagined your cheeks getting flushed like they always do."

I can't believe he listened to that. I can't.. I could feel my cheeks getting red. I didn't want them to, I didn't want him to be right. God Tanner was such an asshole.

"Hahaha, there it is. You know sissy, it's nothing to be embarrassed of, that is, apologizing of course. Everything else that wasn't apologizing you should definitely be embarrassed of." He said, with a chuckle on the end. So much shame in one night, embarrassed, I look at my feet, not feeling the power to make eye contact anymore. I fumble around with my fingers awkwardly, I just want him to finish soon.

"If you were a good girl you would have apologized for the entire night, for wasting that pretty womans time. Tell me princess, if she knew you got little sissy boners from being humiliated do you think she would even bother with you?"

"I..."

"Speak up. I know you get scared when you're by real men but that's no excuse to not answer my questions."

I feel completely powerless, my mind is going through a rush of emotions that feels bad but so good at the same time. Self-consciously, with Tanners eyes on my now trembling body, I muster up the will to say what he wants to hear.

"No.. no sir. I don't think she would bother."

I feel my penis reluctantly getting semi-hard in my underwear, not wanting Tanner to see I try to cover it with my hands, bending my knees like a girl wanting to go to the washroom.

"I can't believe it. Are you actually turned on from this?"

I wanted it to stop, I wanted Tanner to stop, this was all so embarrassing and I just wanted to go to bed.

"Move your hands Princess. I want to see how pathetic this is. Put your hands behind your back like a good girl."

But I don't want to, and I simply look up at Tanner with pleading eyes and a pathetic half-smile, trying to connect with him on some other level where I could find some mercy. Tanner stopped leaning on the wall and started approaching me, each step he took made my heart sink with fear a little more.

"Tanner, th- this is getting kind of silly don't you think? Haha.. I.. I, -"

And with that I see Tanners arm come up, muscles flex, and palm hitting my left cheek hard. It stings really bad and already know his palm will be visible on my face until tomorrow. I look down at his boots, he's so close to me now. I feel so scared that all I can do is submissively wait, cheek stinging with pain. I expect him to say something but he just stands there, cold and solid. I think he's letting me soak in the position i'm in right now: in huge discomfort trembling underneath his power.

"Good girl. You speak when spoken to. Now take off your pants and then put your arms behind your back. I'm not going to ask again."

".. Yes sir." I mumble, and with fingers trembling I look down at my belt, I feel so self-conscious undoing it that it takes me twice as long, but Tanner doesn't care, he enjoys it. I try to hide my eyes, now with small pools of tears in them as I shimmy my pants and underwear down to my ankles. My penis, 2 inches, sticks out, semi erect. I quickly put my hands behind my back.

"Oh my god. I didn't expect it to be that small... Haha. Is that what you call your dick sissy? I know why you were so embarrassed of it now. I would be too if I had that cute little thing as well."

I tried to resist but my clit bobbed up and down from pressure, it was at it's max length after that sentence, which was still only a bit more than 3 inches.

"Don't enjoy yourself too much Princess. And tell me, did you honestly expect Kara to not laugh you out of the room when you imagined taking off your pants? Or did you not think that through?"

I can't believe he's doing this, I have to reply.

"No sir, I... I didn't think it through."

"Then Thank Me. Thank me for saving you that embarrassment and getting you in touch with your real self."

"Thank You -sniff- .. sir."

"That didn't sound too grateful Princess, I want my efforts appreciated."

At this point I notice the bulge in his jeans, even though the fabric was tight I could see the outline of his cock, with its head visible at his thigh! It must have been at least 8 inches, and thick too, I suddenly remember all the girls I have heard Tanner fuck through the wall, how jealous I always was, this is what they were sucking, obediently. My clit is invisible in jeans, yet his monst-

Slap.

Just when I forgot the pain of the first slap came this second one, leaving his palm on my right cheek.

"Is Princess getting distracted? Did you even hear what I said? Thank me."

"Yes. Thank You s- sir. Thank you for saving me that embarrassment I am so grateful to have you as a roommate. Thank you sir so much I don't know what stupid things I would be doing without you sir." I say, rather panicked from the pain.

"Ahaha.. Good girl... And I don't fuck faggots, so drool all you want but you need to earn a cock like mine... Now I want you on your knees in front of me, head resting between my shoes. Take off that shirt too."

I startle a bit, Tanner is pointing at the floor. I take off my shirt and drop to my knees, which comes naturally as they are weak by him anyways. I slowly start moving my head to the floor when Tanner pushes it all the way down with his foot. My cheek feels cool on the cold wooden floor, alleviating the sting from the slap. I feel his boot pressing against my hair now, I can't move my head whatsoever.

"Here's what's going to happen Princess, while I'm going over some things you're going to be jerking your little clit until you cum in a cute little pool underneath you. I know that won't take a long time, so I'll be quick, of course. Understood?"

"Yes, Sir."

"Good..." He says, pressing my hair a bit more with his shoes. I start to rub my 'clit' with two fingers.

"Kara didn't go home because she 'wasn't looking for that' right now, in fact, it was just an excuse to let you down easy. What really happened was she realized how much of a faggot you were and didn't want to bore herself to death with your attempt at sex with a girl tonight. I know this because Kara is easy, my friends always talk about her being slutty at parties... Haha... my friend Jake actually fucked her last Sunday... and he said she begged for it like a whore. Don't you think that makes your rejection even more embarrassing Princess?" He twisted his boot a bit more to add to the pain.

"Yes - ah- yes sir." I reply, rubbing my clitty still.

"Now I don't usually go for girls like Kara, I do have some standards when it comes to woman. In this case however, I think I will make an exception. Just to prove a point to you. And in a couple days you will be sitting at the bathroom door, listening intently to Kara being treated like a slut. You will listen to me make her beg to experience me, something she wouldn't think of doing with you in a million years. When Kara has had the best orgasm of her life and is proudly wearing my cum on her face I will quiz you Princess, things like how many times she gagged or how many times I slapped her ass. This is to make sure you were listening intently, because if you get something wrong I won't be easy with a punishment. And that would be rather embarrassing in front of your crush wouldn't it?"

I couldn't believe it! My clitty was saying yes but my brain was saying no, I don't want him having sex with Kara! And is that whole thing even true? I feel so angry and powerless at the same time - and he's making me jerk off to this as well! I know there's nothing I can do now... maybe I will talk to him when he isn't this horny?

"Yes.. that would be embarrassing sir." I reluctantly say.

"Ahah, I can sense the anger in your voice sissy. You really shouldn't be jealous you know. If you really do like this girl then you should be happy that you influenced me to have sex with her, in this case at least she will be satisfied in the end."

And with that sentence, feeling the the discomfort of my position, the pain in my hair, and the sting on my cheeks, I cum. It comes in 3 spurts that hit my stomach and settle in a small pool between my thighs, my entire body shakes with pleasure.

"Done already? Ok." Tanner gets off my hair. "I'll give you some time to register all this Princess. I'm going to bed now.. You can expect Kara to be here in the next two days...

And spread your legs for me, I want to see that cute little pool."

I can't believe all this has happened. Tanner has never been this mean to me... I'm too embarassed to make eye contact so I keep my eyes on his boots as I move my head up and spread my thighs. They are sticky and there's a small line of cum stringing between them.

"Aww, you got so excited didn't you? Now thank me. Show me your good sissy manners."

I feel my stomach turn, i'm not that horny anymore but i'm still scared of Tanner.

"Th- Thank you Tanner."

"Oh you can do better than that Princess. What are you thanking me for?"

I thought he was going to bed.. When will he leave me alone? I say what he wants to hear.

"Thank you for making me cum all over myself.. Sir. Thank you for reminding me of my place and... and thank you for considering Kara for sex. Thank you for everything tonight I am very grateful."

"Ahah. Good girl. Now kiss my boot goodnight."

Defeated, I move my lips to his shoe and gently kiss it. The same one that was pinning me to the floor just a minute ago.

"Now look up and wish me goodnight."

"Goodni-" My heart sinks, Tanner is filming me with his phone!

"Oh that face is perfect Princess, stay like that."

I am completely lost for words. How long was he filming me? I was so scared to look up. The camera can see everything! My watery eyes, my clitty, the string of cum between my thighs!

"Don't worry, if you're good I won't show anyone. Except for Kara of course."

"Tanner! Don't show Kara this, come o-"

Slap.

"Stop acting up. Now say goodnight like a good sissy."

I look back down at my thighs - covered in my cum -, why do his slaps have to hurt so much? In my weakest voice I say it.

"Goodnight."

"Good girl. Now clean yourself up, you're a mess." Tanner pats me on the head and leaves the room, going through our shared bathroom into his own room. This leaves me on my knees - naked - in a puddle of my own cum. How did I manage to get myself in this situation? Why did I ever agree to be Tanners sissy?

I knew that this whole thing could be over anytime I say the safe word but I can never get myself to say it. I love being a submissive sissy, being completely in someone's power just feels so good. I know it, Tanner knows it... and soon Kara will know it as well. I think of what's in store for me. Despite myself, my mind races in excitement.

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