Being My Roommate's Sissy Pt. 03

Kara bursts out laughing. "Oh my god, am I doing this right?" She, says, turning her gaze to Tanner.

"You're doing it more than right, you got me a bit hard as well." Tanner says. Kara giggles again.

"My ex used to enjoy this stuff... the humiliation, not really the dress up. So that may have been some instinct kicking in." I glance to my left, my eyesight is aligned with the bedsheets draped across Tanners thighs, allowing me to peer underneath them. It looks hard but not at it's full length, still - of course - it's a lot bigger than mine.

"So how many times have you two fucked?" Kara asks.

"Me and Carly? Never. She's a virgin, and I like keeping her that way." My cheeks turn a bit more red but I notice that the sting is starting to fade, thankfully.

"Really? You're a virgin?" Kara asks, and after a short silence I realize she is talking to me. I quickly make eye contact with Kara again.

"Yes."

"Aww..." She pauses and I try very hard to maintain the eye contact. "So you wanted me to be your first then, didn't you?" Kara asks.

"Y-Yes. I did." I say, but I start to feel sad with the thought. I did want her to be my first, and now I'm here.

"Well that's a shame..." Kara says, but then she notices the slight glaze in my eyes. Her eyes change, they lose some cruelty. I start to panic, I don't want her to actually feel bad for me. I hold back my tears.

"And if you weren't so awkward, maybe you would have even had a shot." Tanner says. He pats my cheek twice, making me squint. "You would, of course, disappoint a beautiful girl like Kara in the bedroom. She, no doubt, has higher standards than 3 inches and an awkward fifteen seconds..." I expect Kara to reply, to deny what he's saying, but she stays silent - and with it, Tanner continues. "But at least you could have claimed you lost your virginity, and I'm sure that would make you feel a bit better. Kara would probably try to talk less and less with you after it, but maybe the feeling of approval would balance that out... In my opinion, I think it turned out for the better - didn't it, Carly? Kara got to sleep with a real man, I had some fun, and you were even allowed to watch! It's really a no-brainer, don't you think?" Tanner's arm guides be back to face him again. I try to ignore the cock under the bedsheets right in front of my face - along with Kara's foot touching the outside of his thigh.

"Y-Yes, Sir." I say, superficially, but after my words I start thinking about it more, and I start to realize. It all starts piecing together in my head, the entire story - my failed date with Kara, Tanner's texts, last night, this moment. It all comes together, like an 'Aha!' moment at the end of a detective movie.

"Let's hear it from you, Princess. Do you think it turned out for the better?" Tanner asks. I feel my eyes water.

"I, yes, I think it's better this way."

"You see! That's what I thought." Tanner says, but with the thought, I sense the last bit of my denial giveaway, a swell of sadness starts rising from my stomach.

"Maybe you went too far, Tanner?" Kara says with some concern. My vision starts to blur with tears, all I want is to put my head down but Tanner still holds me there.

"It's natural, don't worry. This is progress for him if anything." Tanner brushes some of my wig hair behind my ear, he's looking at me. "It's ok, Princess, let it out." But then, Kara gets out of the bed, revealing her naked body. She kneels down beside me and takes my face into her hands and points me to look at her. I'm startled by how close she is.

"Shh, shh. Don't worry." She says. With her thumbs she brushes my tears off my face. "I went a bit too far. Don't cry." She lets a smile show and we stay like that for a moment - face to face. My whimpering slowly stops, and I start to feel better. "Shh"

Her hands feel so soft on my cheeks, all the pain of Tanners slap just flushes away. From this close, I start to notice every detail in her face - the details you don't see in day to day conversation. I notice the freckles under her eyes, the curvature of her lip, the bend in her eyelashes, and her eyes - which are just so focused on me. Her smile has faded, and we just stare at eachother like that.

"Feel better?" She asks. I sniffle.

"Yes..." Kara smiles again. The room is filled with silence.

"So what do you say?" She says, "Keep going? This is pretty hot." Kara's touch feathers away my doubts - it all seems fine now in some sense. I sniffle one last time.

"Ok." I say.

"Wow, you are a good subby, aren't you?" Kara says, lightheartedly. I smile back at her.

"Yes, ma'am. Haha.." She wipes away another tear on my cheek with her thumb, then let's go with her left hand. I notice it goes down to my panties. She slips her fingers into them, her fingers touch my clitty and she gently pulls it out of my panties so my balls rest in her hand. Some blood rushes to my head and to my clitty, but it only makes it lift a bit - from a soft 2 inches to a semi-soft 3. I look down at her hand, my clitty is completely shaved, making it look so cute in her palm.

"I know what will cheer you up, darling." Kara says, looking at me with a smile. "Because I think someone finally deserves to lose their virginity, don't you think?"

"Yes, please." I say to her, my mind rushes with excitement, but then I start to doubt what she meant... Her fingers massage the underside of my balls, then she looks back up at Tanner with a playful look. Silence fills the room once again, but their eye contact communicates so much.

"And I've always wanted to see two guys have sex.." She says.

"Alright."

"Oh how exciting!" She bounces my clitty up and down in her palm. "Your first cock!" I bite my lip, for a second, I thought Kara meant sex with her, but the thought quickly leaves my mind. This is me not pretending, like Tanner said. "How about we start with a nice, sensual blowjob?" Kara asks. I feel butterflies in my stomach. "That's ok with you, right Caleb? "

"Yes."

"And you're not doing this because Tanners blackmailing you or something right? You do want it right?"

"No, no! I do want it. I am enjoying this, I am.." I say, and it really is true... I've always wanted to suck Tanner's cock. It's been a fantasy since I first met him, and he's been holding it over me for months. Sometimes I'm less horny and more jealous and angry, but the lust for him always returns. I turn to look at him, I try my hardest to put on a cute, innocent face. He smiles.

"Well that's good to hear." Kara says.

"Let's put that clitty away first." He says. I nod and tuck my clitty back under my balls, and into my panties. Without much thinking, I adjust my position so I'm kneeling in front of Tanner - right between his legs. I move my hands to the side of the bedsheets to uncover his cock, they are trembling a bit. "Stop." My hands freeze. "Did you even ask? Did your sissy manners just fall out of your head?"

"N-No, Sir. Sorry. I'm just all excited, that's all - sorry."

"Try again." He says. I feel embarrassed, I think back to all the training videos Tanner made me watch throughout the year - how to be girly, how to seduce a man, how to look cute. I think back to the deepthroat trainers too, or the times I gagged myself on my bed whilst pretending it was him. I bite my lip and look him in the eyes, putting on a submissive face.

"Please Sir, may I suck your cock? Please let me put it in my mouth, Sir. Let me taste it, please."

"Go ahead." He says. I smile in return, then uncover the rest of the bed sheets. There it is, his perfect cock. I lean further into his legs, my side brushes against his calves. I take it into my hands... It's beautiful. Tanners cock is semi-erect and it still has a sense of 'weight' in my hands. It's skin is perfectly smooth apart from a couple veins along the shaft. Just holding it makes my clittty throb, but thankfully, it's well hugged by my panties and thighs.

"Put it in your mouth, darling." Kara says, kneeling beside me. So I do. I push the foreskin back to uncover the full head, then put my lips to the tip - the cock grows and pushes against them in reply. "Have you ever sucked a mans cock before?"

"No, never. I do practice a lot though."

"Well I guess it's time to show us what you learned." She says. In reply, I run my tongue over the top of the head, swirl it around it, and take it into my mouth, where I lick the tip a bit more. I try to recall all the porn videos too, ones in which the girl was really seductive - I don't want to let Tanner down now, I have to give him a good blowjob. His cock grows a bit more in my mouth.

"Mmm." I moan.

"That's good." He says. I look up to make eye contact, god he's so hot, and his comment makes me feel so good. I take it out my mouth, smile at Tanner, and spit on it, then I rub the spit down his shaft with my hand. His cock must almost be full length now. I duck under it and place my tongue near the end of the underside of the shaft, then slowly start to lick back up to the head - I can really feel the weight when it rests on my face. Once I reach the head, I start working on it again, swirling it around my mouth. I try to make my actions gentle and submissive, I know that Tanner likes them that way. It symbolizing a deep sort of submission, not the kind where a person acts - screaming 'I'll do anything Sir!' - but the kind where the submissive 'knows' their place, and demonstrates it subtly, not needing any words to validate it. The dominant wants, the submissive accepts and even tries to go over what is expected.

I notice Kara is holding my hair back. I take it into my mouth again, this time I think I'll go deeper - I remember to relax my throat and take a deep breath and then, prepared, I start moving down the shaft. It travels across my tongue and hits the end of my mouth, pressing against the entrance to the throat; I want to gag already but I push harder, relaxing my throat a bit more. It slides in after some pressure, but I panic from the unexpected size girth and I manage to get two inches down before I gag and reflexively take my mouth off his cock.

"Princess, that wasn't even halfway." Tanner says. I feel myself blush, I look up at him.

"I - I know, I'm sorry, I've been practicing Sir, I promise, It's just that I'm not used to this size."

"It's alright, you just need some help." Tanner says. Kara lets go of my hair as his arm comes out from behind him, reaching around my head then grabbing a fistful. With fear, I nod, and put my mouth back on his cock. I tell myself to relax, I can hear my heartbeat again and I can feel Tanner's hand behind my head, he's not pushing, but the thought of how much control he could have scares me. Tanners arm would no doubt be able to push me to any length, for any amount of time. He could even make me pass out if he felt like it, even if I did put up a sissy fight. I try to ignore the thought. I swallow and breathe.

I move down his cock, his head slides down my tongue, further into my mouth until it hits the entrance again. I wince and push, until it pops into my throat - there goes air. I push further and further, I get to the point where I quit last time but contain it, pushing an extra inch. My throat is filled with his cock, I can feel it stretching the sides. I look up at Tanner.

"More." He says. So I try, but I feel my eyes water, then I gag and try to push back but I only retreat an inch before Tanner reacts. His hand pushes me back down to where I was, plus an extra inch - it physically hurts my throat. I wince even more and tap his thigh with my hand, pleading for air.

"Use your tongue too."

"Mmm!" I moan, but realize the futility. I look at his abs again, I'm almost and inch away from the ending. I push my tongue between my lips and the underside of his cock at the entrance of my mouth, holding down another gag. I only manage to get a bit out, but once it's there, I move it back and forth and I feel his cock pulse in reply. The feeling of nausea is overwhelming and when I think I'm about to throw up, Tanner pulls me off of his cock. I gasp for air, but instead of letting me rest, he pushes my face under his cock and towards his balls, I catch all the strands of drool on the way there. With some sissy instinct, I quickly start licking them. I put them in my mouth too, but with caution so I don't hurt him.

"That's a good girl." He says. I push my nose into them and try to lick the skin behind the balls too. The smell and taste of his balls differ very much from mine; Tanner's ball sweat is pungent and almost overwhelming, whereas mine smell mostly like sweat.

"Surprising me even," Kara says, "You'll have to teach me some tricks later, Carly." I turn to look at her and unexpectedly smile out of excitement. She places her hand on my lower back, "Keep going." I nod in reply. My mouth goes back to Tanner's head. I know he will be more rough with me now and it makes me scared but I also don't want to disappoint him. I put the tip in my mouth once again, his hand is behind my head and I sustain a submissive eye contact.

"Hands behind your back." Tanner says, I put them behind my back. "I don't want a drop of pre-cum or drool that has touched my cock to hit the floor, do you understand?"

"Yes Sir." He stares at me for a while longer, holding my lips at the top of his cock. I feel Kara's hand reach under my clothing now, touching the skin above my butt.

"I am going to fuck your throat, Princess. I've been thinking about it for a couple weeks now." I gulp, suddenly becoming very aware of his hand on my head. "You won't enjoy it, but you don't really have a say in that. You understand that, don't you?"

"Y-yes Sir."

"If you cry, I won't stop. If you try to push away or resist, I'll acknowledge it, but know that you don't really have a say in how deep or for how long. Do you understand that as well?"

"Yes, Sir." I say, with a shaky voice.

"And you want that, don't you?" He asks. The question pushes me into conflict - do I want it? I feel scared, but my submissive side clashes with the fear. I want this. It's deep inside - I want Tanner to use me, I want to be a good girl and I want to be a good throat toy. I don't enjoy getting my throat fucked, I enjoy the thought that it's for him, and that is more powerful than any fear or uncomfort.

"Yes Sir." I say. "Please use my throat. I've been waiting so long. Please. I don't care if I'll cry, Sir, I just want it so much." He smiles.

"So be it then." He says, then tightens his grips. I relax my throat before he pushes my head down his cock - it hits the entrance to my throat and then he pulls me back to do it again. He hammers my the entrance like that, bucking his hips as well, for a good minute before I get a break. Then, after a breath that was way too short, he pushes me down to deepthroat his cock - pushing me even further than before. I feel it pass the entrance and expand my throat, it's horrible, I feel tears welling in my eyes and then he pushes me an extra inch so my nose is in his lower stomach. One of Kara's hands holds back my hair and the other moves down towards my hole, rubbing over it with her finger. I can't pay much attention to it, all I can think about is controlling my nausea and the uncomfortable feeling Tanner's cock lodged in my throat, I want to get off but I know there's no use. "Moan for me." He says.

"Mm-mmph!" I moan. Then he starts to massage his cock by moving me up and down the final inch of his cock, I want him to stop. I wince from another reflexive gag and just when I think I'll break down he finally takes me off.

I'm panting, but notice a strand of drool about to fall from his cock and quickly move under it to catch it with my tongue.

"Good girl." Tanner says. I smile in return and put my mouth back on his cock. Tanner starts again, this time facefucking me from my mouth to halfway down my throat. It continues like that for another 5 minutes. Afterwards, I'm exhausted and sick. I think he's done when he stands up, and I let myself feel relief, but then he lifts me up and puts my back on the bed so my face is hanging off the mattress - his hand pinning my chest. He starts facefucking me again. I gag and spit out drool and precum onto my face at some constant rate, in the short breaks he gives me before using me again. In and out, varying tempo too. One of his hands lean on my chest and the other gently holds my throat, with the thumb right below my adams apple - feeling my throat go up and down as his cock enters it and leaves. My vision is blurred with tears and spit but I can still see his balls hanging in front of my face, moving towards and away from me, or slapping against me, or occasionally pushing into my nose and eyes. Kara comes up on the bed too, she sits by my thighs and starts playing with my clitty and ass.

In the next 20 minutes, there were many times where I felt completely at his mercy - like when he held a deepthroat for too long, or when I would arch my back and tap him with my hands in a desperate plea... but he would keep going, pinning my wrists or leaning on my stomach to face fuck me without a distraction. It made me realize that Tanner knows my limits more than I do - physical and mental, and since I'm a scared sissy, my mental limits fall way short of the physical ones. This leaves a gray area between the two - between the bought of fear from the thought of losing air and actually losing air, between the gut feeling of nausea and actually throwing up... Tanner knows this gray area all too well, it's his play space and he keeps track of its boundaries with a meticulous caution. It what makes him so amazing. The first minutes, I realize, were for exploring. Now, knowing these limits better than I do, he oscillates me - with a negative peak below the mental boundary, and a positive peak nearing the physical one. From letting me lick the spit off his balls and thanking him, to patting the side of my cheek with his cock lodged down the length of my throat and a single tear of mascara running down my face.

Kara, all the while, entertaining herself with my clitty and sissy pussy. Not jacking me off... just teasingly flipping it back and forth, slowly moving her finger along the side, or gently flicking it. For a second, I thought that I could grow to enjoy the feeling - a point where the sissy dopamine released matches the discomfort. It ends abruptly, however. When his cock unexpectedly pulse whilst down my throat and it suddenly started to feel warm and liquidy. I gag reflexively and immediately. He massages his cock in that last inch - leaving me no choice but to try to swallow, as there is no other way for it to go.

"Uuuhh" Tanner moans, and his cock leaves my throat, it feels like I'm drowning, and a fountain of his cum overflows my top lip and moves downwards towards my nostrils, the side of my nose, and my eyes - which are already squinting from the strands of saliva and pre-cum over them. All I want is to put my head up, to stabilize - as one wants when they accidently go upside in a pool, but Tanner's weight holds me still, one hand on my throat and one on my stomach. He's not done cumming too. His cock, now out of my mouth, shoots three more strands of cum over my face, whilst I am still trying to figure out what happened. He finishes cumming before I swallow the remaining cum on the walls of my throat and finally gasp in air. I feel as though I draw a full breath when contrary to expectation, Tanner makes me deepthroat his cock again - all the way down, nose nestled into balls.

"Close your lips around it, Princess." He says, and it's difficult, but of course, I obey. He then starts sliding his cock out - letting my lips wipe off the mess of cum and gag spit around it. Similar to how one might use a tissue. Once it gets out, I swallow the thick, salty liquid that accumulated in my mouth. "That's a good girl." Kara's stopped playing with my ass as well.