The Roommate Pt. 01-06

Sitting on the train, my mind starts to linger. Oftentimes when I let my mind wander, I land on something that makes me horny. This time is no different, and soon I am trying to discretely browse porn on my phone. I can feel my clitty leaking into my thong as I pull up images of thick cocks. I keep my legs crossed, so hopefully nobody notices. I have found a subreddit of guys pulling their dicks out of their boxers, and I become so entranced. Moments like this make me love the internet. My eyes glued to the screen, I see numerous cocks of varying shape, and size, and color all flop out aiming right at my face. I get so distracted that I almost miss my stop! Only when I hear the familiar beeping that indicates the door to the carts are closing do I look up and see the familiar signs. Leaping out of my seat I manage to just catch the door with my backpack and it automatically reopens, allowing me to pass through. Once I get to the platform I look back to my seat to make sure I haven't left anything. I seem to have gotten all my belongings, but there is a veritable puddle of precum on the plastic seat. I quickly turn and walk away as if trying to run from the humiliation. Of course, that follows me and my rosy red cheeks are the evidence.

After a few minutes of catcalls and divulgent breezes I finally reach my apartment. Once I get inside, the whole place is eerily silent. I quietly enter my bedroom, assuming Ruby is taking a nap or something, and start to strip out of my embarrassing ensemble. My thong is completely soaked, so I remove it and toss it into the laundry hamper. It is soon followed by the skirt and top. Turning towards my wardrobe, I catch sight of myself in the mirror. It really is pretty amazing that I could look so different in a matter of days. I reflect on what Charles told me about being on the forefront of scientific exploration, and looking at myself I am forced to agree with him. I never believed something like this could be possible. I knew women transitioned and stuff, but for it to happen so fast and so... intensely. I don't know, it's just something I never expected to exist, and definitely not something I expected to happen to me!

I weigh up my breasts with my palms. They don't look much bigger than before, but they feel a bit heavier, a little more rounded. My clitty looks much the same as it did this morning too. It doesn't even dangle between my legs anymore, it's too small, it just pathetically sits there, taut yet soft. Feeling a bit naughty, I turn around and crane my neck to get a look at my butt. It really does look pretty damn good, I can't deny it. Spreading my cheeks a little, I take a look at my boipussy. It looks tight, but it's clearly been well used today. Still glistening from cum and lube, it pulses slightly, looking very inviting. As my eyes cast up again, I realize just how messy my makeup looks. I thought I had gotten most of it off with the towel, but I was mistaken. There are still remnants of mascara dripping down my face, my foundation is a bit splotchy, and my lipstick is spread around my mouth. Now that I think about it, I have been face fucked three times today, so I guess my makeup could look even worse given the circumstances. I also have the realization that this might have contributed to some of the gawking I received on my journey home.

Without re-dressing, I walk to the bathroom so I can wipe this makeup off. After I grab a makeup-wipe and run it over my eyes, cheeks, and lips I take a look in the mirror. My face is still undeniably feminine, but at least now I don't look like a discarded hooker. I hear the click of a doorknob nearby and realize it's coming from Ruby's room. Without time to get back to my room to cover myself, Ruby walks into the hallway and sees me standing over the sink in the nude.

"Did you just get home?" She asks, standing on her back foot and sizing me up with her eyes.

"Uh yeah, I just got in a few minutes ago." I say, tossing the wipe into the wastebasket at my side.

"A little later than usual isn't it? Doesn't your class end at like noon or something?" Ruby inquires, slightly closing her eyelids into a glare like she's interrogating me.

"Yeah, it does, but I had some stuff to do after class. Like, school stuff." I reply, trying to walk through the door of the bathroom into the hallway. Ruby lets me past her and I push the door open to my bedroom.

My back turned to her, she mockingly says, "Ohhh, you mean your appointment with Dr. Charles?" She bites her lip and giggles when I look back at her in surprise. I'm sure I have quite a 'deer in headlights' look on my face. "I mean obviously I knew about this appointment Nel, I am part of the lab group. Or did you forget? Your pretty little head must be to filled with thoughts of sex that it totally slipped your mind!" She teases, relenting and letting me stew a little as I stand in the doorway. We lock eyes for a moment, but I don't let her get a rise out of me. I turn around and start rifling through panties from my drawer. Ruby leans in the doorway to my room and watches me.

"Was he good?" She asks, raising her eyebrows.

I try to ignore her, but I can feel my blood pressure rising and my face getting hot. "Hey don't be embarrassed Nel! I mean, he is pretty hot, isn't he?"

I look up at her smirking, and although she is trying to tease me her sentiment does feel sort of jovial. "I mean... he's definitely not bad looking." I reply, my eyes wavering with a tinge of embarrassment at this admission.

Ruby immediately starts giggling, "Oh my god, you totally slept with him didn't you?" She claps her hands together laughing, "You are such a slut!"

"Hey wait, no! I did not sleep with him!" I protest meekly, trying in vain to defend my honor. Ruby, still giggling, looks at me and raises her eyebrows again waiting for the qualifier.

"Buuut?" She says, dragging the word out and coming closer to me.

"Well, I sucked his dick." I reply, my cheeks feeling fiery. I turn back to my underwear, trying to hide my face as Ruby bursts out laughing again.

"There it is!" She exclaims through her laughter. "Of course you did!" She says as she starts regaining her composure. "I mean I can't blame you, he's pretty cute!" My embarrassment dampens a little bit with this as it makes me feel a bit better about surrendering to him. Ruby doesn't let me off that easy though, rounding on me.

"Does he have a big cock?" She asks, coming around to look at my face. I let my eyes wander, trying to avoid her gaze. "Come on, dish! We're both girls here."

Ruby's casualness and insistence that we have girl talk makes me feel a strange mix of femininity, shame, and excitement. The idea of getting to gush a little about all this makes me feel excited, which makes me ashamed because I shouldn't feel excited about gossiping about guys. The excitement gets the best of me though, and I relent.

"He's pretty big." I admit with a slight grin.

"I knew it!" Ruby beams, giving my shoulder a nudge. "How did it feel? I mean that's the first cock you've ever sucked right?"

"No, I actually su--" I catch myself, having started speaking without thinking. I look at Ruby to read her reaction. She's squinting at me with a devilish grin.

"You actually what Nel?" She says, pushing her face closer to me, applying the pressure. I shrivel under her gaze.

"I actually... well I sucked off another guy this morning before I saw Dr. Charles." I admit, all the humiliation from earlier washing over me again.

"So you're telling me sucked two different guys off today?" She questions me, grinning from ear to ear. I'm in this far right? Might as well go with the whole truth.

"Three, actually..." I confess.

Ruby steps back from me, her eyes wide open and her taunting smile wider than ever. "Wow. You sucked off three guys, in one day? And to think this is coming from the girl who whined and complained about wearing a schoolgirl outfit!" Ruby says giggling. She pauses for a moment and looks back at me. "Wait so who are these mystery men you sucked off? Dr. Charles, and who else?"

"Well the first was some guy in my anatomy class. I sucked his cock in the bathroom so he wouldn't tell everyone who I am." I explain, trying to justify it to myself more than to Ruby.

"Who you are? Ohh, you mean who you were?" Ruby says, trying to emphasize, and remind me, that I'm no longer a man.

"Sure, whatever. And then the second guy was, well..." I pause, trying to find a way to explain this hook up without admitting that I initiated sex with a total stranger because I wanted to lose my anal virginity.

"Come on, spit it out!" Ruby demands, looking at me expectantly.

"Well I was really horny after I blew the guy from my class, so then I went off campus and saw a hot guy reading a book so then I asked him if he wanted to hook up because I wanted to lose my anal virginity and then we fucked in his apartment." Forgetting to pause and take a breath, the words flow rapidly from my mouth. "And then after that I met up with Dr. Charles and I ended up sucking his dick too." I finish, inhaling deeply.

"Wow, so you not only sucked your first cock today, but you lost your virginity too?" Ruby asks, looking stunned. I nod submissively. "Did you ever have sex with a girl before this?" She inquires. I shake my head no. "Oh wow, so this really was your virginity? Like the first person you have ever had sex with was a guy popping your cherry? That is so cute! Oh my god you are such an adorable little tramp!" Ruby says these words as though she is holding up a newborn puppy.

"This calls for a celebration!" Ruby exclaims before rushing out my door. I hear the sound of the refrigerator and some glasses before she returns moments later with two glasses of champagne. She hands one to me and holds out her glass. I obediently clink my glass against hers and take a sip. She lets out a satisfied "ahh" after she swallows. "Awh, they grow up so fast." I can tell she's making fun of me, which makes me blush. I put the champagne down on my bureau and start finally putting my clothes on, having felt awkwardly exposed during our whole conversation.

"I'm sure I already know the answer, but do you have any plans tonight?" She asks before taking another sip of her champagne.

"What do you mean?" I'm confused, why does she feel like she knows the answer?

"Well, let's be honest, since I started living here I've seen you spend every Friday night here on your computer."

She's right, but it's still a bit embarrassing to hear her say it. "As a matter of fact I do have plans tonight." I say, pulling the waistband of my skinny jeans over my ample butt.

"Oh really? Do I get to know what your big plans are?" Ruby asks with a voice that sounds like she thinks I'm lying.

"I've been invited to a house party!" I proclaim, feeling prideful that I am proving her wrong. She watches me as I pull a tank top over my head.

"A house party huh? And you're going to wear that?" She looks me up and down. "No, you're not." With this, she darts out of my room leaving me standing alone awkwardly. I sigh and take out my phone, remembering that I hadn't texted Jamal yet. I send him a message with my address and he responds almost immediately, "Thanks cutie, see you at 9."

Shortly after, Ruby comes bursting into my room with bundles of clothes draped over her arm. She steps past me and drops the clothes onto my bed. "Okay, strip down to your underwear and let's pick something out." Ruby says, turning back to the clothes on the bed. I dutifully obey her command and take off my clothes. Standing next to her in my underwear, I survey the clothing she's brought. With her hand under her chin she turns to observe my body. "Oh my god." She sighs. "Take off the underwear too, you can't wear those to a party." I look down at the hip-huggers I'm wearing over my clit.

"What's wrong with them"

Ruby sighs again, "Those aren't very sexy! They're comfort panties, you need sexy panties if you're going to a party, duh!" With that, she steps over to my wardrobe and pulls out a black g string. Tossing it at me she says, "This is what you'll wear." I hold it up and examine the nearly non-existent piece of fabric. I know not to argue with her though and do as she says, replacing the underwear.

"Okay, with that, let's see what our choices are." She holds up a seductive black dress with a deep neckline that shows a lot of cleavage and a large slit up the dress to show off some leg. "This is pretty, but maybe a bit too elegant for this kinda party. We'll save this for another time." She says, placing it back down on the bed. "Oh but this... this could be perfect!" She grabs a short red tank top that has straps for its back and is made of a velvety material. Looking around, she finds the short skirt with a matching fabric. It has a few sections of small silvery chains on the waist and one that goes down the back of the skirt. "Yes, this is hot!" She proclaims, holding the outfit up to help imagine me wearing it. "Put this on while I find some jewelry to go with it."

With Ruby returning to her room, I start trying to get this outfit on. I get the tank top over my head and the straps untangled. The skirt goes on much easier, and once it's on I notice that it also has small slits on the side to show off more of my thighs. I have to admit, this outfit feels pretty sexy, although I'm not sure what it looks like. Before I have a chance to look in the mirror Ruby is back holding an ensemble of silver jewelry.

Sitting me down on the bed, she takes out my earrings. My ears are still quite tender as she replaces my current earrings with some small silver hoops that match the chains on the skirt. She follows that up by adding a couple silvery bands to my fingers and a simple silver bracelet. Stepping back, she admires her work. "It's all coming together sweetie," she says, giggling. "There should be some red heels in your closet that will match this. Try to find them and I'll do your makeup." Once again, she goes to her room to pull more beauty products into my room. I'm not sure why she didn't just take me to her room, but I don't bother asking. I find the shoes like she asked and sit on my bed again, pushing the clothes to the side.

Ruby comes back with a box and two bags. Her makeup collection looks like what someone would bring on a 3 month vacation, so this is somewhat conservative for her. "Okay sit back and I'll make it look really good." She says while uncapping some concealer. As she applied it to some of my blemishes she starts to properly inquire about the party.

"So, do you need a ride to this party? Where is it?"

"I'm not sure, but I don't need a ride." I reply, trying to play the cards close to my chest so I don't get teased.

She uses a small sponge to spread the concealer and some foundation on my face. "Oh really? Who's going to be driving you?"

"Uhm, this guy Jamal. He's the one who invited me..."

"Oooo, why have you been hiding this information? Do you have a little crush on him?" She taunts, "That is so cute! Nel has a boyfriend already!" She says, sounding like a schoolgirl. I feel like she's about to start rhyming about us kissing in a tree.

"I don't have a boyfriend!" I protest, my cheeks getting red.

"Wow if I keep up like this you won't need any blush!" Ruby mocks. "But honestly, if you need me tonight just call me. I'll be at a party tonight too but I can not drink if you need me to pick you up."

I'm surprised by the earnestness of Ruby's comment. It makes me feel like her little sister, but it also makes me feel guarded since her kindness is usually followed by something devious. I try to brush it off while also returning the niceness, "No that's okay, you let loose! I can handle myself okay."

"Yeah, right." Ruby snickers. Finishing up with my foundation she applies some blush and moves to my eyes. With my eyes closed, she starts brushing on some eyeshadow from her sizeable palette. She pauses for a moment, "Did you say Jamal? He's not on the soccer team is he?"

I open my eyes, "I have no idea I only met him today. Why?"

She brings the brush to my eye again as I close them. "Oh no reason, just curious..." She says innocently. I get the sense she's hiding something, but I don't have any leverage to question her on it. Ruby silently applies eyeliner as I try to keep my eyelids from fluttering. I can sense her focus as she performs the delicate task. "Okay open your eyes." I obey, looking up at her. "Nice, this is looking really good. Okay, just let me do your lipstick and you should be good to go."

Once she has applied my lipstick she starts putting some of the makeup she used into a small red clutch she brought with her. "Bring this with you. It has concealer, mascara, more lipstick, some gum, and makeup wipes in case you want to take it all off. Oh, and some condoms." Handing it to me, I feel she's acting like my guardian. She looks at my dumbfounded face and rolls her eyes. "I know, I'm not your mom. But you're clueless about being a girl and about partying, so you need all the help you can get." Even when she's nice she finds a way to make me feel embarrassed. "Plus, if anything happened to you I would get in so much trouble with Dr. Charles."

She stands up and starts collecting her clothes and makeup as I take out my phone. It's 8:38, so I have a few minutes to kill before Jamal will arrive. I'm getting more nervous as 9 o'clock approaches. Ruby is right, guy or girl, I've never really been to a lot of college parties and I'm not sure what to expect. I consider cancelling, but I know that if I do I would probably regret it. I put the heels on and stand to take a look at myself in the mirror. I'm pretty shocked at how I look. Ruby actually didn't make me look trashy! She was light with the blush, gave me a kind of purply-brown smoky eye effect, and sexy but not overbearing wings with the eyeliner. To top it off, she put a glossy champagne colored lip plumper on my lips, making them look even bigger. The tanktop pushes up my breasts and gives me some nice cleavage and the skirt shows off my smooth and ever-thickening thighs. I feel sexy, I can't lie, but I also feel much more comfortable than I did in the humiliating school-girl outfit.

With the few minutes I have left I use the bathroom, brush my teeth, and spray on some of Ruby's vanilla perfume. I take the last few remnants of her clothes into her bedroom. She's sitting at her desk doing her own makeup now. "Is he here yet?" She asks, as I awkwardly stand around not wanting to sit on her bed. I still feel strange coming into her room, since invading her space partially started this whole mess.

"No, not yet." I reply, looking down at my phone. "Still a couple minutes before 9 thought."

"Well, if he bails on you, you can come with me to my party." She says, applying mascara to her eyelashes. "I can't let all that work go to waste tonight."

At that, I hear an alert tone from my phone. Looking down I can read, 'Jamal: Hey girl I'm outside. I'm in the silver Lexus.'

"Okay, he's outside!" I say, scampering to my room to grab the clutch. I pause as I walk past her room to get to the door outside.

Ruby turns in her chair, "Well I would say 'Don't do anything I wouldn't do,' but the last time I said that you sucked three cocks and lost your virginity!" She cackles, "So I'll just say have fun!"

I can't help giggling a little at that jab, "Okay, you too. Are you coming back here tonight?" I inquire.

"I'm not sure. We'll see! Now get out there you little minx!" She yells playfully as she turns back to her desk mirror.

Going down the stairs, my stomach is doing somersaults. I walk carefully, as I still don't feel terribly comfortable walking on stairs in heels. Once I get out of the building the cold air hits my legs and midriff. It's chillier than I expected, I would have brought a jacket had I known, because now I feel like my cold nipples must be visible through this top. I scan the street looking for Jamal's car until I finally spot it down the road. Walking towards his car, I can hear the sounds of people partying in a building nearby. The thumping bass and hollers are an affable reminder that it's Friday night. The sounds prepare me for what to expect tonight...