The Roommate

Those thoughts were all I needed, I felt the tingling sparks and knew I was close. "Cassidy!" I yelled, "I'm almost ready."

"I'm in your bathroom," Cassidy's voice replied, surprising me from just a few feet away. "I thought it would be easier to clean in here in case there was a mess."

"I'm coming," I said, rising to my feet while continuing to stroke my eager cock.

"I hope so," Cassidy responded with a giggle. It was good to hear her still making light and joking about all of this.

As I turned the corner into my bathroom, I found her kneeling in my bathtub, still fully dressed, eyes closed. Her pretty face and cute little nose, which I had been fantasizing about covering with my cum mere seconds before, was tantalizing. But the rest of it was.. awkward. The glaring bright lights of my bathroom and the cheap white porcelain of the tub made me feel uncomfortable. Even the sight of Cassidy submissively waiting for me was both arousing and confusing.

"I'm ready when you are," she said. "Please try to get it all in my hair, just to be safe." Even those words should have driven my libido crazy, but instead they reminded me that this was a task that I was no obligated to complete.

As I walked awkwardly towards her, stroking my cock furiously, the pleasurable tingles started to fade away. My erection was losing some of its rigidness. But I continued towards Cassidy's waiting body, and her long, smooth, red hair, steadily stroking my dick.

"Tell me when you're going to do it, if you can," she asked.

"Okay," I grunted in reply. Stroke, stroke, stroke. Stroke, stroke, stroke. I stood over her waiting face, admiring her flawless skin and the way her proud breasts pushed out against the fabric of her shirt. But the tingle of impending orgasm was fading.

"Is everything okay?" she asked, eyes still closed. I didn't know what to say in response, so I kept looking at her sexy little body kneeling before me, her big breasts pushing proudly out against the fabric of her shirt, and I kept beating my meat. Stroke, stroke, stroke.

"Do you need some help?" she asked. Again, I didn't know how to respond. "It's okay," she continued, "I'll help. You're doing me a favor after all."

Without opening her eyes, she grasped the bottom of her t-shirt and pulled the fabric up over her breasts. The sight of the creamy tops of her breasts, bulging out of the top of the purple bra which tightly encased them, sent a little tingle through me. But I had seen more of her firm, young tit flesh when she was passed out in her green bikini. Then she quickly reached behind herself, and her bra was falling away. As I continued to jack my returning erection, her big, round breasts were exposed all the way to her little, pink nipples. I could feel the tingling return.

"Does that help? I can show you my ass if that's better," Cassidy offered.

"No," I grunted, "That's great."

Still with her eyes closed, Cassidy reached up towards me with one hand. "Give me your hand," she ordered. "If you want, you can touch them."

I reached across my erection with my free left hand, and met Cassidy's soft fingers. Quickly, she guided my palm down to the top of her right breast. Her tit flesh was warm, and smooth. I squeezed just a little, and felt unbelievably firm fullness in her tit. I moaned softly, the tingles now building in my loins as I palmed Cassidy's little nipple.

"Mmm, you like that," she encouraged. "What else can I do to get you to pop?"

"Tell me to do it," I ordered.

"Tell you to cum in my hair?" she asked, and I moaned my response.

"Cum in my hair, Kevin," she pleaded.. "I know you would just love to empty your balls right into my hair, and I'm asking you to do it. Cum for me."

The rivers of pleasure were exploding inside me, flowing through my cock and getting close to overwhelming me. I reached down and gently took a handful of Cassidy's soft, straight, red hair. She did not flinch or move as I wrapped her silky strands around the tip of my member.

"That's it, cum for me," Cassidy whispered.

"Here it cums," I warned.

And then I was cumming, squeezing the tip of my dick through Cassidy's red hair, the orgasm bursting out of me in a sharp, pleasurable wave. Cassidy's eyes opened and she looked up at me as I came, electricity flowing between us as our eyes met while she watched me orgasm. Spurt after spurt of my hot jizz was pumped right into Cassidy's silky hair, and the visual was seared into my memory. Cassidy smiled, her blue eyes taking in the scene of me cumming on her, her big, creamy breasts on display for me as she knelt before me. My legs shook and I almost lost my balance as I came in her hair, finally having to sit back on the cold edge of the tub.

Cassidy quickly bundled up her hair with one hand to hold in the cum, pulling her shirt back down with the other hand.

"Thank you, I really mean it," Cassidy said as the afterglow of orgasm wrapped warmly around me. "That was really hot getting to watch your face as you came. And I hope you don't mind me saying it, but you have a nice, big dick. It's impressive." She was already getting to her feet. "Sorry if this was weird, but I have to run back to the bar for the hunt. I'll see you later, thanks again!"

And with one last smile over her shoulder, she was running out of the apartment. It took me a couple of minutes to clean myself up and process what had just happened. I couldn't fall asleep for a while, but I had dozed off in my bed before Cassidy returned.

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The next day, Cassidy didn't come out of her bedroom until almost two in the afternoon. I grew more and more nervous over the course of the day, wondering what she was going to say and if things were going to be really awkward between us. When she finally emerged, yawning and sleepy eyed, she barely acknowledged me as she headed straight for the kitchen and some food.

Then, as if the thought had just occurred to her, Cassidy yelled to me, "Hey, I really hope last night wasn't weird. I super appreciate it! My team won the hunt!" And that was all she said about what had happened. She went on for several minutes about how her team had never placed higher than third, and she really loved the fun of the scavenger hunts, and she met a lot of fun people at the party after the hunt.

That was it. Nothing about her asking me to cum in her hair, how she had encouraged me to feel up her bare breast, or how she had egged me on while I ejaculated right into a ball of her red hair. Nothing.

For the first couple of days, I wondered if Cassidy was avoiding the topic. Maybe she was embarrassed. Then one day I came back from a workout and Cassidy was in the kitchen.

"I don't know how a never noticed before that you have such a big cock," she told me casually. "It's not like you hide it."

To my incredible embarrassment, I could feel my face flushing bright red AND my cock growing a little from the attention.

Cassidy could see the reaction in my face. "Oh come on, there's no need to be shy about it. You saw my tits and I saw your cock. It's nothing to be ashamed about, especially in your case."

I laughed, trying to be light. Before I could think of an appropriate response, Cassidy was walking away towards her room.

And that's when I finally got it. Cassidy just didn't care. It wasn't a big deal at all to her that we had done something sexual, or that she had showed me her breasts, or asked me to jizz in her hair. She didn't really care.

And that's also when I finally understood that I was totally and completely screwed. Cassidy didn't think it was dangerous at all for us to have crossed some personal lines, or that we had ever crossed any lines. It was inevitable that something was going to happen again.

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Much like her surprise request for assistance with her scavenger hunt, the event that pushed me and Cassidy into the wild rollercoaster that would wreck us both came as a unexpected, chance encounter.

I was jerking off quietly in my room one afternoon. I don't remember much else about the day or why I was beating my meat, but I remember almost everything else vividly. I was watching some porn on my computer, and I was getting really close to cumming. I could feel the orgasm building, looking forward to the explosion of pleasure from a sweet, orgasmic release, when I thought I heard my bathroom door open.

"Hey, I was wondering if you have any..." I could hear Cassidy saying.

My mind raced with a thousand thoughts at once. My bedroom door had been locked, but my bathroom door leading to the hallway had been left unlocked. And the door between bedroom and bathroom was open. And I was sitting at my desk with only a t-shirt on and my fully erect dick in my hand. And Cassidy was walking into my bathroom. Why the hell didn't she at least knock?!!

Without thinking I jumped out of my chair and tried to slam shut the door between the bedroom and the bathroom. For half a second, Cassidy was looking through the doorway, her eyes going wide at the sight of me naked from the waist down with my dick in my hand, and then the door slammed shut in her face.

"What the hell?!" she yelled through the doorway. Without hesitation, she was turning the handle and reopening the door.

"What the hell yourself?" I demanded as the door opened. "Don't you knock?!"

I thought I would look less guilty if I at least let go of my cock, but as the door opened and Cassidy looked into the room, it still looked pretty bad to be standing with only a t-shirt on and a full erection pointing towards the ceiling. Oh yeah, and the porn was still playing on my computer behind me.

"You were jerking off," Cassidy said matter-of-factly.

"You can't just barge into my room, Cassidy," I replied, trying to deflect the topic but failing to inject the proper sound of irritation in my voice because I was so surprised and uncomfortable.

"Oh, don't worry about it, it's totally natural," Cassidy responded with a reassuring tone, continuing to walk slowly towards me. She was wearing a simple t-shirt herself and a tight pair of jeans. I finally noticed that her blue eyes seemed fixed on my cock, just before she said to me, "That might be the biggest dick I've ever seen in person. You mind if I touch it?"

"Cassidy, I don't..." I began to say, but before I could finish I felt her soft fingers slowly closing over my thick cock.

"Yeah, it's big," Cassidy said with some appreciation. "I maybe saw some bigger, but I've never touched one like this."

"Cassidy, you shouldn't be doing this," I tried, making no move to actually stop her.

"Why, you're clean aren't you?" she asked.

"Of course!" I responded somewhat offended.

"Then it's totally natural," She tried again. "Are you forgetting that you already wrapped my hair around this thing and came on me? I've kind of wanted to see what it felt like since I saw it." Her soft fingers were now closed around the head of my cock and began sliding gently up and down over the tip of my shaft.

"Cassidy..." I started, totally distracted by the warm feeling of her light hand job.

"What?!" she interrupted, playfully exasperated. She finally looked up at my face and her dazzling blue eyes met mine. "You jerk off, I use a vibrator. Sex is a totally normal thing, there's no reason to hide it." Her fingers were now gripping me more deliberately, my cock still lubricated from the lotion I had been using and the previous tingling from my near orgasm quickly returning.

I just could not believe what was happening. "Cassidy, what are you doing?" I asked.

"I thought it was obvious, I'm jerking you off," she responded with a bright smile. Her fingers were sliding around my cock head, jacking me more quickly and tightly. "What's wrong, don't you like it?"

"Ohhh," I moaned, "I don't know..."

"You don't know if you like it?" she teased, rubbing insistently at the little spot under the head of the very tip of my dick. Her big breasts were beginning to move up and down under her shirt as her arm rose and fell more deliberately with her effort. "That's too bad because I want you to cum for me."

"Oh Cassidy," I couldn't help myself. She was smiling at me, her blue eyes searching mine while her clever fingers teased and rubbed at my excited manhood. "I'm close."

"You're close already," she asked with a giggle, her blue eyes dancing with amusement. I didn't know if her girlish playfulness was an act, but it was working.

"I'm going to cum," I warned.

"Oh, you were serious," she responded, standing there in my bedroom, fully dressed, while her fingers softly milked my manhood.

"I'm serious, I'm going to cum," I replied, the familiar fire bubbling up inside my pleasure centers.

A thoughtful look crossed Cassidy's pretty face as she said, "Where are we going to put this?"

It was too late, the bubbling was boiling over, and the burst of pleasure was on it's way. "Oh shit!" I blurted uncontrollably.

With a sweet laugh, Cassidy simply closed her other hand over the tip of my dick while somehow still rubbing at that one sensitive spot under my cock head with her thumb. The orgasm seemed to fly up from my feet, shake my legs, and then burn its way through my loins and out of my pulsing member. I arched my back as I came hard, and I could actually hear my cock shooting spurt after spurt of hot cum into Cassidy's cupped hands.

This time, I didn't try to catch myself. I fell backwards awkwardly into a sitting position on the floor, with my eyes closed, while the after effects of my orgasm radiated through me. When I opened my eyes a short time later, Cassidy was standing over me with a big smile, her cupped hands full of my dripping cum.

"Didn't that feel good?" she asked.

"Yeah," I had to admit, "it really did."

"Good," she said. Then she walked away into my bathroom while I stared up at my ceiling trying to figure out what the hell had just happened. I heard the water in my bathroom sink turn on, and what sounded like Cassidy washing her hands carefully in my sink. And then as I lay there with my deflating cock out in the open, I was surprised to hear the water turn off, the bathroom door open, and the door close again as Cassidy left.

----------

It took me a few minutes to get cleaned up and get some pants back on. As I walked out into the living room, I wasn't sure what to expect. With the way Cassidy had mostly ignored our last sexual encounter, I sort of expected she would just blow right past this one too.

Instead, she greeted me with a smile as I entered the room, looking up from the food she was preparing in the kitchen. "Feel better?" she asked.

"Yeah... I do," I responded honestly.

"Good," she said with a smile.

I sat down on the couch, not really doing anything except letting the quiet stretch to see where Cassidy would take the conversation.

She seemed to notice. "I have an idea, and if you think it's crazy, we can totally forget that I ever mentioned it." She licked her fingers delicately, to clean off the remnants of the meal she was making, before giving me a slyly inquisitive look.

"Okay, what is it?" I asked.

"Just hear me out for a second," she began, leaving her food and walking into the living room, "and like I said, no pressure if you think it's crazy."

"Okay."

"I just think," she started slowly, with lots of pauses, "sex to me is like this totally natural and enjoyable thing. Everyone our age loves sex, so it's crazy that we're not supposed to talk about it. I mean, you're my roommate. I don't know if you want to know that I masturbate with my vibrator at least once a day, twice a day most days. But I don't care if you know, I think it's totally normal for me to want to orgasm at least once a day if I have the time and energy to do it. Who wouldn't, you know?"

"Makes sense," I admitted hesitantly.

"So instead of hiding it from each other like it's this dirty, mysterious thing, I think we should just embrace our desires and our physical needs and be open about them," she continued. "It wasn't SHOCKING to me or anything to find you masturbating in your room, of course you jerk off sometimes, every guy does."

That made me want to ask why she didn't knock if she knew that I jerked off, but I held my tongue.

"So what I'm getting at," she continued, "Is that we both know we do it. And you're a cute guy. I'm not a bad looking girl, and you seem to like cumming with... my help. So why don't we just, like, embrace it and help each other out, from time to time."

Despite where the conversation had been going, that was a total surprise to me. "What do you mean?" I ask.

She actually laughed a little at the discomfort in my response, her mischievous blue eyes and bright smile teasing me. "I'm not talking about us just having sex all the time, whenever we feel like it. I mean, I like you, but that would be a little weird with us being roommates and everything."

More than a little, I thought.

"And I don't really like you like that, and I don't think you like me like that. So, like, what I'm saying is, why don't we just help each other out sometimes. Here's what I suggest. No sex. No kissing. But basically, anytime you're feeling really horny and you want some help, if I'm around and not busy you can just ask me for help and I'd be happy to help get you off. Sort of like what I just did for you. I can give you a handjob, I'll give you a blowjob if you want. We can also do other stuff that you might like, just no sex. And if we're doing a blowjob or something like that, you have to wear a condom. I mean, I'm clean and you told me that you were clean, but it's always safer with condoms. If I'm feeling really horny, same thing. I can ask you to help me out. You can use your fingers, or your mouth if you're comfortable, and help me get off."

While my mind was still trying to digest what Cassidy was nonchalantly saying, she continued. "But I'm just a girl, and I know how boys are. So if we agree to this, I'm going to need you to help me two times for every one time I help you. I mean, it's not like I'm going to be, like, super strict and carefully counting or keeping records. But I, like, know how boys can be, and... I just want it to be fair for me too. So it's got to be about two times for me every one time for you."

My mind was spinning, overloading trying to process Cassidy's offer. Looking back, I wonder if my eyes were displaying that spinning hourglass icon from when computers are taking a while to process something. This was the OPPOSITE of what I had wanted when I had agreed to let Cassidy move in. That was my overriding thought. Fooling around with your roommate was even more dangerous than fooling around with a close female friend. Something was bound to go wrong.

But another part of me wondered whether Cassidy had been so logical about her scavenger hunt and helping me get off just moments before, that she could handle some sort of "friends with benefits" arrangement. And that other part of me that was doing some thinking was my penis. I mean, she had laid out the ground rules of this arrangement so precisely, maybe this would provide the dispassionate structure that would protect us. It also didn't help that she was sitting in front of me, studying my face intently with her pretty blue eyes, her curvy, young body awaiting my answer with obvious eagerness.

Then a question occurred to me: the precise arrangement. "How did you come up with all these rules? Have you done this before?"

Her face dropped so abruptly that I almost regretted asking the question. Her eyes shied away from mine, and she wrapped her arms around herself. Eventually she admitted, "Yes, once. I tried this once before, that's where the rules came from."

I couldn't tell if it was shame or hurt that was dragging down her pretty smile. But my regret at causing the emotion, plus the way she had sold her offer, won out over my better judgment. I should just be honest and say that my penis won the argument.