The Roommate Pt. 01-06

Chapter 1

Initiation

I lean forward, staring at a big cock going in and out of a girl's tight ass on my computer screen. I'm jacking myself off so hard, and I can feel the tight thong pressing against my asshole. I don't know why it's turning me on so much right now. I'm getting close, and stare intently at how the cock rhythmically thrusts into her ass. Suddenly, my dick erupts cum into my hand, filling it with a huge load. A feeling of shame washes over me. This isn't my thong, it belongs to the girl who lives in my apartment. I pull it off, feeling guilty about taking it, and ashamed that I wanted to wear it. I'm a man, men don't get turned on by wearing thongs. At least, that's not what a man is supposed to like. I stare at the cock...I mean, her ass, for a few more seconds before I close my computer.

I poke my head out the door to the hallway and make sure nobody else has come home. Then I sneak over to Ruby's room. We've lived in the same apartment together for 7 months. We were paired together to be roommates by a questionnaire from my college. I had written that I was looking for someone clean, organized, relatively quiet, and very respectful of privacy. I think she had written that she wanted someone who cooked, was willing to keep the place clean, and didn't mind her taking long showers. A natural fit as roommates. I delicately place her thong back into the top drawer of her dresser, sheepishly arranging it to look like it hasn't moved. I close the drawer and look around her room. It's pretty standard, and similar to mine. She has a nightstand with a lamp, some books, lotion, and deodorant. On her desk is her computer, pencils, a sketchbook, and what's this? Something I hadn't noticed when I came into her room earlier. Partially blocked by a tissue box I can see a tube of lubricant and a very realistic fleshy dildo. I take a step forward to get a better look, but simultaneously hear someone unlocking the door to the apartment. I quickly, but quietly, tiptoe to the door of her room and gently close the door. I scamper back to my bedroom and sit in front of my computer, trying to look casual.

"Heyah" I yell to hear as I hear the door open.

"Hi, say do you mind coming out here and helping me?" She replies, somewhat fretfully. I can hear the crackling of paper bags and realize she needs help with groceries.

"Oh yeah, no problem." I say, getting up from my desk. I walk into the living room and grab some of the bags from her.

"Thanks, just bring them to the kitchen and I'll put everything away." As she walks ahead of me to the kitchen I can't help but stare at her ass. It's being tightly hugged by her jeans, and it slightly sways as she walks. A nice ass is somewhat hypnotic.

She has dirty blonde hair that falls over her shoulders and halfway down her back, and it's razored at the edge to make it seem like that's how it is naturally. She's wearing a green jacket, sort of like an army jacket, but more stylish and fitted to her body. Her ass sways in her jeans because she's wearing 2.5 inch black high heels. She wears them religiously, probably because she knows the effect it has on her swagger.

I put the groceries down on the marble tabletop of the island in the kitchen. "Anything else you need help with?" I ask, trying to be polite. I try to be extra nice to her because even after 7 months we haven't gotten to know each other very well. "Umm" She says looking around the kitchen and biting her thumbnail. "Not that I can think of." She replies, looking back at me. She makes direct eye contact, which in the light of the kitchen allows me to see her gorgeous eyes. They're a piercing jade green, but the edges are accentuated by a bright orange. She has pale clear skin, topped off with a few adorable freckles. Her nose is slim, and her large lips add to her aura of femininity.

"Alright, well if you need anything I'm not busy." I say as I turn and start walking back to my bedroom. I look back at her as I go into my bedroom. She is putting her long hair up into a ponytail and taking off her jacket. I've always thought she was cute, but am too cautious to ever make a move.

In my bedroom I take a look at myself in my wall mirror. My face is slim, but rounded, which has always made me look younger than I am. I've been 19 years old for 2 months and I still sometimes get asked for my ID to buy lottery tickets. My eyes are almond shaped, and a bright blue, on which I often get complimented. I'm somewhat tan, which apparently adds to the effect of my eyes. My eyebrows are rather thin and shaped, unlike the bushy eyebrows my brothers have. My hair is light brown, and I keep it rather short and tamed. I grew it out when I was younger, but my brothers would tease me about it, so I've kept it short ever since. To match my face, my body is quite slender. My arms have always had much more tone than bulk, although I've been ignoring the gym so much that they don't have much tone left either. I have fairly nice legs though, since I walk almost everywhere and used to bike ride. I've been doing squats in the safety of my own home lately to keep my thighs strong, although unfortunately I think it's mainly just been making my butt more shaped. I'm a little short too, around 5'5", which makes me look even less intimidating. I'm comfortable in my body though, I guess I never tried to be really bulked up.

After looking in the mirror, I sit down at my computer again. I whisper to myself, "You don't like wearing panties. I know you've been doing it for a few weeks now, but tomorrow you won't, because you're a man. On top of that, only lesbian porn tomorrow, you love lesbian porn for fucks sake." As I'm talking to myself, the guilt fades away, and I'm able to do a little bit of my homework. I'm doing anatomy homework, mostly because I needed a biology credit and all the biochem classes were full by the time I registered. I wanted to be in a biochem class because that's what Ruby studies, and I wanted to share at least one class with her. In anatomy, we're studying the reproductive organs, which can sometimes be a bit embarrassing in class when we have to look at diagrams, but everyone remains pretty mature considering we are in college. Tonight I'm just studying the function of each part of the penis for an upcoming quiz.

However, because the guilt had washed away, the desire to wear panties has already started to come back, along with a few other nagging desires. I start thinking to myself, "Well, you should probably look at some pictures of cocks, since you need to study for the quiz." So I start to watch porn, with men and women. Soon, though, I begin looking at just pictures of dicks. I examine how each of them differ, how some are more veiny than others, or the head a little more pink and delicious...Oh god, I mean, a little more pink and, uhm, rounded. Ruby's call from the kitchen pulls me back into reality, and I quickly try to close the tab as she opens the door to my bedroom.

"Hey, do you think you could..." Ruby says to me, before she glances at my computer screen, "Hey hey, haha, what are you looking at there?" She says jokingly, as she leans over and grabs my laptop.

"Hey wait, give me that back!" I say, standing up and reaching for the computer. She pushes me back playfully, holding the laptop with one hand.

"Wow, lots of pictures of dicks here huh?" She says laughing.

"It's for an Anatomy quiz, Jesus." I say as I snatch my laptop back from her and close it on my desk.

"Hahaha, I'll take your word for it. But anyways, could you help me with the TV? I tried to get the Wii hooked up to watch Netflix and I've messed it all up." She asks me, still slightly giggling. She looks at me playfully, much like an older sister would.

"Oh yeah, no problem." I say, getting up and following her into the living room. "It really was for anatomy class though." I can tell I'm still blushing.

"I believe you, honestly." She says chuckling, I don't know why, but it infuriates me that I know she doesn't believe me. I go behind the TV and plug in the cables from the Wii, I'm a little unsure how she's so bad at this every time. I grab the remote and turn on the TV, the Wii menu is up on the screen.

"Alright, there you go. What're you gonna watch?" I say, giving the remote to her.

"I dunno, maybe some Breaking Bad or something, are you gonna watch with me?" She sits down onto the sofa and looks at me. I look at the clock and see that it's almost eleven, which makes me start to feel tired.

"Uhm, I don't think so, I have class early tomorrow morning and I don't want to be too tired." I say to her, half-yawning.

"Oh, alright well then maybe tomorrow night?" She says to me, turning on her show.

"Yeah, that sounds good. G'night." I give her a playful tap on the head and start back towards my bedroom.

"Night" she calls from the living room as I close my bedroom door.

After closing the door, I walk into my room and feel something under my foot. I look down and see that it's a pair of panties. "How the hell did these get here?" I whisper to myself, thinking back to make sure I did put the thong back into Ruby's room. "Did she drop them, or, maybe they were on the floor and she accidentally kicked them in here." As I'm trying to figure out how they got into my bedroom, I can feel myself start to consider wearing them to bed. It doesn't take more than a few seconds for my will to break, and I give in to my desire. I slip off my trousers and boxers, and slip on the comfy, soft, sexy, frilly black panties. I give my ass a look in the mirror, it looks so feminine in these. Actually, it would even be a nice ass if a girl had it. I put some pajamas on over the panties, turn my light off, and go to bed. The apartment is always kept really warm, so I don't bother putting a blanket on over me. I have a hard time falling asleep because my mind is wandering, and stressing about anatomy class. Plus, I keep getting distracted by the comfort of the silky panties against my body, against my ass. Eventually I fall asleep. Half awake and dozing, I open my eyes and see my alarm clock says 3:30. It feels cold, so I pull the blanket on top of my body and fall back asleep until the alarm wakes me up.

I hit the off button and take a look at my alarm clock. It reads 6:45. I snuggle with the pillow for a moment, and then force myself to get up. I pull of the covers, stand up, and then walk to take a look at myself in the mirror. I'm still wearing my panties, actually, I'm not wearing my pajamas! I turn around and see them on the floor, I guess I must have overheated and kicked them off in the night. I take the panties off, feeling a bit of guilt again after sleeping, and put on my pajamas again. I tuck the panties into a drawer in my desk to return to Ruby's dresser later. Then, I put on a t-shirt and go into the bathroom.

The only downside of this apartment is the horrible bathroom. I don't mean horrible like the sink doesn't work, I just mean that it is the ugliest bathroom in history. The floor is bright green tile that has been yellowed and tarnished by years of use, paired with a sink, toilet, and bath set that is a dark orange rust. I turn the shower handle to the hottest it goes, undress, and wait until the water is steaming before I step in. I love warm showers, they make my skin feel so smooth and soft afterwards. After letting the warmth wash over me I lather up my body with Ruby's lavender scrub, it smells amazing. Then I grab my Old Spice shampoo and conditioner, but when I turn it upside down, nothing comes out. Realizing it's empty, I grab Ruby's shampoo. I look at the label, "Strawberry and Cream", whatever, shampoo is shampoo. I wash my hair and can't stop sniffing the air as it fills up with a sweet strawberry smell.

After washing my hair, I hear Ruby knock on the door and yell, "Hey! I made some breakfast if you want any before you head out!"

I turn off the shower and reply through the door, "Really? Thanks! I'll be right out." I quickly dry myself off with a towel and wrap it around my waist. I grab my clothes and scamper from the bathroom to my bedroom. I don't really like women seeing my body, since it's not anything impressive in terms of masculinity. As I'm searching for some clothes to wear in the closet, the idea crosses my mind to put on the panties under my boxers today. I swiftly put it out of my mind, but the thought keeps coming back. I think, "If they're under my boxers, nobody will know. But, if I just jacked off right now then I'd be disgusted by the thought of it. No, it's okay for a guy to wear panties, it's just because they're comfy, it's not gay or anything." My dissent breaks and I open the drawer and take out the frilly panties. I slip them on, put on my boxers, and then put on some jeans. I grab a t-shirt that's just a bit too small, but I like Passion Pit too much to get rid of it. When I walk out into the kitchen I see that Ruby has made some eggs, toast, waffles, and already put some coffee on the table for me.

"Woah, thank you so much. Is this coffee for me?" I ask, pointing at it.

"Yup, I already had a cup myself. Sorta why I've had enough energy to make this much this morning." She says to be, turning around from pouring the syrup onto her waffles.

I chuckle, and grab the cup. I take a long sip, knowing I'll need a couple cups to be able to stay awake during the lecture I have this morning. The coffee tastes really good, but I can't really put my finger on exactly what the added flavor is. "Hey Ruby, what'd you put in this?" I ask, after finishing the last gulp. "It's really good."

"Oh yeah, I think it's this new cream." She says, reaching into the refrigerator and taking out a bottle of Almond Joy flavored half and half. "Do you want me to pour you another cup?" She asks with a smile, reaching out for me to give her the cup. She seems to be in a really good mood, which is rare for her so early in the morning.

"Yeah, thanks." I say, giving her the cup. I walk over to the table and start eating the plate she's prepared for me. I hear her pour the coffee, and then hear a small plurp as she pours in the cream.

"Here you go, if you want any more don't hesitate to ask." She says from behind me, putting the coffee on the table. "I think I'm going to start making breakfast more, I kinda like it." She says, smiling, as she sits down across from me and starts eating.

"Well, the food is damn good." I say between a mouthful, it is really good, and so I'm eating it fairly quickly. I chug the coffee, after which Ruby grabs me one more. I chug that one too after finishing up the rest of my food. I bring my plate over to the sink.

"Do you want any more?" Ruby asks, looking at me. I'm in a bit of a rush, since I realized I'm a few minutes late to be leaving since I got so distracted.

"No thanks, I've got to get going since the lecture starts in half an hour." I reply, putting on a jacket I grabbed from the back of the chair.

"Oh! Okay, well I'll see you later then, I'll probably be back here around 6, we can watch something then!" I turn to her, smile, and nod. She looks me right in the eyes, and then leans forward and gives me a small kiss on the cheek. I blush, and then go to my bedroom, quite flustered.

I think to myself, "Heh, wow does she like me? Or, was that like a friend thing? Or a brother-sister thing? Or does she actually like me? Hmph..." Then I notice, strangely, that I'm not hard. Normally if a girl did something like that, I'd be embarrassingly hard, but I don't feel anything except the comfort of the panties against my ass and cock. I put it out of my mind, grab my school bag, and then head out the door.

"See you later!" I yell to her as I go out the door to the street.

The lecture is incredibly boring, and despite the coffee I still doze off during it. The only thing that stands out during the entire lecture is a guy sitting behind me who jokingly tells me my hair smells good. After a few hours, the lecture finally ends. I'm lucky to have had so to do little today, because for some reason I'm really tired. Rather than study at the school or get coffee, I go straight home on the subway, on which I also doze off. When I get home, Ruby is gone, and I fly straight into my bed. It's warm, so I pull my pants off and throw them onto the ground. I get cold pretty soon after though, and pull the covers up onto me before I fall asleep.

As I sleep, I have a dream that I'm walking down a street in the city. For some reason it seems vaguely familiar. I look at the signs that hang from the buildings up the street until one catches my eye. It reads, "Frisky Business" and has a black and red sign with a picture of handcuffs. I walk into the store, and am immediately met with a visual onslaught of cuffs, panties, garters, dildos, lubricants, condoms, butt plugs, chastity belts, vibrators, and a million other things. I walk up to the clerk and buy an ultra realistic fleshy dildo, identical to the one I saw in Ruby's bedroom. I go home, lube it up, and just as it is about to enter my ass, I wake up.

I'm in a sweat, and my cock is throbbing hard, forming a tent in my blanket. I feel a hint of guilt, but now that I'm awake, all I feel is burning lust. I do the first thing I usually do when I get this horny. I poke my head out the door, to see if Ruby is home, then go into the shower to jack off. Something about the hot water usually makes me cum extra hard, which helps when I'm super horny like this. As I'm jacking off in the shower, I feel the hot water run from my shoulders, down my chest and back, over my cock, and in between my ass cheeks. The warmth turns me on, but after 20 minutes of jacking off the water begins to get cold, and I still haven't cum.

I can't stop thinking about going into Ruby's room and getting her dildo. I keep putting the thought out of my head, but I can feel my resolve slowly breaking. I quickly wash my ass with soap before the water gets too cold, and then turn off the shower. I grab a dry towel from the laundry hamper, quickly dry myself off, and slip on the panties. Then I peek out the door to see if Ruby's home, she's not, and then nervously go into Ruby's room. When I get into her room I see that her clock says 4:35. "That gives me plenty of time", I think to myself as I look under Ruby's desk. I don't see the dildo, and then begin to panic because looking for it has made me want it even more. I open the top drawer of her dresser and see all her panties, but no dildo. I open the second drawer and see thigh-highs and socks. "I never knew she had these" I say to myself as I pick up a pair of sexy black lace thigh-highs. I discreetly slip them on, and then put my towel back on over everything. I open the third drawer, "Aha!" I say to myself excitedly.

I see two realistic dildos, one inflatable dildo, a butt plug, and some different lubes. I feel like I hit the jackpot. I eagerly grab the dildo I saw in her room the day before, some lube, and run to my bedroom. I get onto my bed, pull my panties down, then lube up the dildo from its head all the way down to its silicon balls. Then, I get on all fours, poking my asshole right up into the air, and use one hand to reach back and stretch my ass cheeks apart. I put my face into the bed, and with my other hand I bring the wet dildo right up to my eager, puckered, pink, tight asshole. I get so horny I can't control myself, and without even putting the dildo in my ass I start to softly moan and talk dirty to myself. "I have such a hot little ass, such a hot little tight ass. Mmmf, oh my asshole is so tight your big cock will barely even fit. You'll stretch my little pink ass so wide with your nice big cock." I talk to myself like I've heard every porn star speak.

I keep rubbing the head against my ass, teasing myself. Then, I start to slowly push the dildo, feeling the resistance of my virgin ass. My horny moans quickly turn to muffled moans of pain as the head of the cock pops into my ass. I pull it out quickly, my asshole pulses with the pain from being stretched out so suddenly. I lay in bed for about a minute, telling myself it hurts too much. But, it starts to hurt less after a couple more minutes, so again I eagerly push the cock against my pink asshole. It pops in, and it hurts, my eyes water, but I can take it this time. I start to push in a little bit further, and further, feeling my ass pulse and squeeze on the silicon dick. It doesn't hurt as bad, I push it in a little, pull it back out a little, my ass starts to get used to the feeling. Once my ass has loosened up, it starts feeling better, it starts feeling good. Soon, or what felt like soon, the balls of the cock are against mine.