tagErotic CouplingsThe Roommate

The Roommate

byspaldan©

Life in my early twenties was great. My entry level job bored me to tears, and the paycheck wasn't anything to brag about. But I had my college degree, loads of free time, and just enough pocket money to get myself into all kinds of trouble. Plus I was young, and it seemed like the world had been made for me. There were bars where the drinks were cheap and the music was good, sweaty clubs where the girls showed off more shimmering, smooth skin than they covered, and shitty parties where the food was bad and the music too loud but the stories were always entertaining. Most important of all, I had one of my best friends from college as my roommate. He shared in all of my adventures, kept the trouble from getting too big, and helped keep the bills low.

That all changed when my roommate fell in love. He met this sweetheart of a shy and beautiful girl, and they became inseparable. The idiots got engaged at 24, and just like that my good times were over. But even when I realized how bad it was going to be for me when my roommate told me he was moving in with his fiancé, I had no way to anticipate the gut wrenching ride I was about to experience.

The serious trouble started a couple weeks before my roommate was due to move out. His fiancé told me she had heard I was trying to line up another roommate so I could keep my place, and she said she had a roommate who was now looking for a new apartment to share. I should have asked why I had never met her roommate, that would have been warning sign. But the question didn't cross my mind at the time.

A few days later when I met the roommate at a happy hour, I knew I was in a tough spot. The girl was gorgeous. Her name was Cassidy, which also should have been a warning.

She was clearly the type of girl who worked out a lot, standing atop long, shapely legs that were toned with muscle. Her whole body was lean and toned. She was pretty tall at about 5'7", and had fiery red hair that hung down in soft curls just below her shoulders. When she was introduced to me, her deep blue eyes twinkled, and her bright white smile lit up her entire face, all the way to her high cheek bones. She was wearing a low cut green top that clung to her large, C cup breasts. The way her creamy breasts were on full display was another warning.

Cassidy seemed very sweet. She knocked back her drinks faster than I would have expected from someone with her light frame, but other than that she seemed very nice and dangerously charming. That's why I really wanted to say no to her moving into my apartment. Even at 25, I had learned it was dangerous to get too close to a really attractive girl. If you spend too much time with a girl, if you became friends or roommates, and she was even moderately attractive, you were going to end up falling for her one way or another. Even if you didn't develop romantic feelings for her, you'd start to wonder what she was like in bed, how good she was at blowjobs or fucking. And the next thing you know, you'd be thinking about fucking her every time you were together. And you could never fuck her, because that would just mess up the friendship. So you were always royally screwed one way or the other in the end. It was best not to get too close to attractive women, unless you were trying to date them. And living with a hot girl was a recipe for disaster. Cassidy was definitely beautiful.

But as much as I wanted to say no, I was in a tough spot. Cassidy had learned that my apartment was slightly bigger than hers and in a better location. She really wanted to move into the place. And I didn't want to start off on a bad note with my best friend's soon-to-be wife. So I stalled for a couple of days before deciding I had to agree to the deal. It was better than interviewing replacement roommates, and how bad could it really be to live with a sweet, beautiful woman? Stupid decision

I knew Cassidy's sexy body was going to be a huge distraction for me the second she moved in. She showed up with her first few boxes of stuff wearing booty shorts and a tank top over a sports bra. When she was walking away from me, I couldn't stop looking at her impossibly shapely round ass. When she was walking towards me, I couldn't stop stealing glances at her large, round breasts pressed firmly against the tightly constraining fabric of her sports bra.

I tried to tell myself not to be a pig about it. She was much cleaner than my old roommate, which I liked, and she didn't constantly borrow my groceries. She also offered me leftovers from her dinners, and she was a pretty decent cook. We had separate bedrooms and separate bathrooms, so when I got a little too interested in her attractiveness, I would excuse myself and spend some time reading or watching tv in my room. She watched horrible reality tv shows that were all about drama between women, but other than that we got along okay. Still, it was easy to try to tell myself to calm the fuck down when Cassidy looked particularly sexy getting ready to go out at night, or even leaving for work in the morning. It was a different matter trying to hide my erection when she bounced her way onto the couch in short shorts and a virtually see through white t-shirt, flashed me her dazzling smile, and then changed the channel to something on the E network.

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The real trouble began very early one Saturday morning. I woke up to the sound of a woman's loud moaning and pounding on the wall. I decided to peek out my bedroom door to make sure everything was okay, because my bedroom and Cassidy's didn't even share a wall. So the pounding was crazy loud for it to have woken me. The light was on in the living room and some shoes and sets of keys were strewn around the place. It was close to 4 in the morning as I tip toed down the hallway towards Cassidy's door.

There was no mistake that Cassidy was moaning with arousal like she was losing her mind. The thing that really alarmed me is that it sounded like two distinctly different male voices were coming out of Cassidy's bedroom. The banging on Cassidy's wall was so loud that it almost sounded like someone was punching the wall with their closed fist. I considered for a brief moment that someone might be hurting my roommate.

Then Cassidy's voice came loud and clear through the doorway, dripping with delight and sexual energy, "Oh yes!" she cried. "Fuck me! Fuck me harder! Give it all you got!"

The last syllable of her encouragement was cut off with a muffling sound. If I had to bet on the cause, I'd have wagered that one of the two guys in there had shoved his dick in her mouth. Both seemed amused, their laughter ringing loudly through the doorway.

"Oh yeah? You like that baby?" One of the men inquired. Cassidy moaned her approval in response.

"Whatever" I thought to myself. I padded silently back down the hallway to my room and closed the door. After a couple of minutes trying to muffle the moaning and screaming with a pillow stuffed over my ears, I drifted back off to sleep.

I've never been able to sleep late, and despite the disturbance in the middle of the night, I was awake by 8 the next morning. I walked quietly out of my room and through the living room dimly lit with the early light of morning. On the way to fix myself breakfast in the kitchen, I noticed the strange shoes and extra pairs of keys I had seen a few hours earlier were all gone. Curious, I tip toed back down the hallway towards Cassidy's room to see if there was anything wrong.

Her door was half open, and through the doorway I could see that Cassidy was alone on her bed. She was passed out on her back, the sheets askew and the comforter half over her. There were small items lying around the floor of her room, like things had been tossed to the floor or knocked over during the night. But what quickly drew my attention was that Cassidy appeared to be naked and the comforter only covered her from her waist to her ankles. Her large, creamy breasts were on full display, little light pink nipples resting atop her round, pale mounds. Her breasts were magnificent, big and full with only a slight sag from gravity pressing them down onto her chest. I got hard just seeing her round breasts, and Cassidy's peacefully sleeping face framed by bright red hair. Her skin seemed smooth and flawless, pale with a light rosy glow that made me think of strawberries and cream. And topping off the pink and white colors of her body were her small, light pink nipples sitting atop her breasts. I still get hard, years later, remembering how perfectly smooth and round and flawless those breasts were. An hour later, I was spraying my cum against the wall of my shower, imagining what it would be like to have those soft, full breasts wrapped around my cock.

I went out to run some errands before Cassidy woke up. When I returned that afternoon, Cassidy was awake and cooking herself some eggs over the stove.

"Hey," she greeted me warmly. "I'm really sorry and I hope you don't mind, but I was out of condoms last night and I needed a couple." Well, I thought to myself, there goes any awkwardness about whether I should pretend to have not heard her sexual antics the night before. "I know you keep some in your bathroom, so I borrowed a couple. I went to the shop on the corner and bought you some replacements, and they're already back in your stash. I hope that's okay."

"Sure, no problem," I replied. I really didn't mind her borrowing my condoms, I just wondered how she had known that I kept some in my bathroom. And although you could get to my bathroom from both the living room and my bedroom, the door from my bedroom to my bathroom had been open the night before. How had she gotten the condoms without waking me?

---------

The following week, I met my old roommate for lunch. We spent most of the time talking about his wedding planning and how he was adjusting to life living with his girlfriend. But inevitably he asked how I was doing with Cassie. I related to him what had happened the previous weekend.

I knew something was wrong when he looked down at his plate, poked at his food with his fork, and then slowly looked back up at me. "Listen," he began, "I really wanted to warn you, but Kate told me it was impolite gossip and you didn't need to know."

"Tell me what?" I asked warily.

"Well Cassidy," he began uncertainly, continuing after a pause, "she's a bit of a partier. And well... I'm just going to say it, that girl has a hell of a sex drive. She used to bring boys back to their apartment and get caught in all sorts of crazy situations with them. But Kate never minded because she insisted Cassidy was a good roommate, and her wild flings were kind of entertaining. And Kate didn't think you would mind. You're not upset about it are you?"

"No," I responded quickly. Then after a moment, "But that's good to know."

A couple of weeks after that warning, I walked out of my room getting ready for work on a Wednesday morning to find Cassidy passed out on the couch. She was wearing a green string bikini that showed off the large, round swell of her breasts, and a string bikini bottom that hid very little of her shapely bottom and smooth legs. The green also nicely complimented her deeply red hair and fair skin. I couldn't figure out where she had gone on an early September night that required her to wear a swimsuit, or how she had gotten drunk enough to pass out on the couch on a Tuesday night. But I knew I was treading deeper and deeper into troubling waters when I realized with a start that I had been staring at the cleft between Cassidy's beautifully big breasts for several minutes. I was infatuated enough to spend minutes admiring Cassidy's body while she slept. Worse, by the time I got to work my erection still hadn't fully subsided after seeing Cassidy yet again with most of her hot young body on display.

----------

I knew there would be a breaking point one way or another, but I could never have anticipated how it would happen.

One Saturday maybe six weeks after Cassidy moved in with me, I got home around 1 am from a night out drinking with friends. I was making myself a little snack before bed when my cell phone rang. It was Cassidy.

"Are you home?" she asked. There was a lot of loud noise in the background and it sounded like she was slurring her words just a little.

"Yes, is everything okay?" I asked.

"Oh great! I have a HUGE favor to ask," she responded. Now I was sure from her speech that she had been drinking.

"Okay, what is it?" I replied.

"I'm on a scavenger hunt, I'll explain when I get there," she told me hurriedly, "Please don't go anywhere, I'll be right there." With that, she hung up.

Not sure what was going on, I went to use the bathroom, and by the time I walked out I heard Cassidy's keys in the front door. She entered the room in a hurry, dressed in a tight little t-shirt and shorts that somehow still displayed the swell of her round bottom and the curve of her hip. She flashed me one of her dazzling smiles as she closed the door behind her, and bit her lower lip apprehensively as she walked into the living room.

"What's up?" I asked.

She hesitated, looked through my open bedroom doorway for some reason, and then back at me. "This going to sound crazy..." she began, before trailing off.

I stood there silently, with no idea what she was about to say but allowing her silence to put together her thoughts. Finally, she surprised me by giggling, looking at me with a twinkle in her deep blue eyes. Then she continued.

"Okay, I'm just going to say it," she began, rushing through her words. "Some friends and I are in this bar scavenger hunt league, it's lots of fun and totally crazy." I remembered her mentioning this scavenger hunt team before, it sounded fun and just like the type of activity she would love. "Tonight is the fall championship, and they make you find really crazy things but the point totals are HUGE. I mean, you could go from fifth place to first place if you got all the points tonight. Anyway, one of the big things we might actually get is if one of the girls shows up with cum in her hair and a judge verifies it."

I laughed without thinking about it. It sounded like a ridiculous but intriguing challenge to me, but what came out of my mouth was, "That sounds a little gross." Cassidy paused and looked into my eyes uncertainly. "Unfair to the girls, I mean," I added.

"Yeah, true," she plowed onward hurriedly, "But it's worth a thousand points. That's huge, I mean really huge. Some things in a scavenger hunt are worth ten, some things tonight even are only worth fifty. And this one is a thousand, and it's totally doable, unlike some other things on the list where you either know how to find them or you're screwed... anyway, some of the other teams have couples on them, which is totally unfair. Some of them saw the list and rushed right off to the bar bathroom."

"That's unsanitary," I said with a laugh.

Cassidy ignored me and continued. "It's not fair to my team, we only have one guy on our team and he would just love to cum in our hair, but there's no way we'd let him, it's a long story... anyway... I reminded my team that I live nearby with a guy for a roommate."

It FINALLY dawned on me where this was going, and I was so surprised that it felt like the whole apartment spun for a second.

"And I told them you were cool and I totally trusted you..." she continued to explain.

"Wait," I cut her off, my mind still reeling, "Why me?"

Her blue eyes studied mine, uncertainty flashing across her pretty face. "Like I said, I trust you. And of course if we really wanted it, I'm sure some stranger in the bar would agree to do it, but I don't want to have to do that. That would probably be gross."

And this isn't?!! I thought to myself, but what I said was, "Are you serious?"

"Yeah listen, if you don't want to do it, I totally understand. But like I said, it's HUGE points. HUGE! And I thought, I'm not ugly. What guy wouldn't want to cum in a pretty girl's hair, especially if she was asking for him to, you know? And I don't mean to rush your decision, but we have two hours for this hunt. It's already been 30 minutes since it started, and I need to get back to the bar because there's other stuff we can do for points. So like... I just need to know if you'd be willing to do it."

I had no idea what to say. Looking at Cassidy, her blue eyes blazed now with something I couldn't quite place. Determination? Desire? If I hadn't been drinking earlier, if I hadn't been so turned on by seeing her naked before, if I hadn't found myself admiring her body so many times, I might have said no. But of course, if I had said no, I wouldn't be telling you this story.

"Am I hideous?" she asked, prodding me teasingly. "A cute girl is asking you to cum in her hair."

"Okay," I replied weakly. "How are we going to do this?"

"Yes!" she shouted triumphantly, a bright smile immediately lighting up her pretty face. She actually began bouncing on her toes in excitement. "I mean, I knew you would do it, and this is a lot of points... we can do this however you want, I just need you to make sure to cum in my hair. We talked about it before I left the bar, my team, and you could cum in a condom and just put it in my hair. But the scavenger hunt list says the guy has to cum IN your hair, so just to be safe it would be better if you could actually, you know, do it in my hair"

"It feels weird just sort of... whipping it out in front of you," I said.

"I could close my eyes if that helps," Cassidy offered.

"It might," I said, "It just... I don't know."

"Listen," Cassidy told me, trying to be reassuring but speaking with a rush of words that underlined her urgency. "You don't have to do the whole thing right here in the living room. You could, you know, get yourself going in your bedroom if you want and then I could come in and you'd just have to... finish in my hair. I don't mean to pressure you," she continued, "I know men don't do as well with this sort of thing under pressure, but time is important and it would be really helpful to me if we could do this quickly."

"I understand," I responded, and quickly decided to take her up on her offer. "Let me... go to my room an I'll call you when I'm ready."

Cassidy's pretty face looked up at mine, her eyes surprisingly full of gratitude. "Thanks, I really appreciate this."

My mind just had time to register how strange it felt to have a girl be so grateful that I was willing to jack off in her hair. The next thing I knew, I was sitting in front of my laptop watching some of my favorite porn, rubbing away furiously at my cock. I'd like to claim that my pecker was a solid, throbbing rock of manhood, but I couldn't get the thing fully erect. My eyes were watching some young porn star get nailed on the screen in front of me, but my mind was all over the place. Wasn't this crossing a dangerous line? What kind of girl asks her recently new roommate to jizz in her hair? Why did she even think of asking ME in the first place?

Beating half limp meat is not a lot of fun, but I couldn't get myself to concentrate. And then I focused on what was really happening here. Beautiful Cassidy was asking me, even convincing me to cum in her hair. Cassidy, with the big, beautiful breasts and the tight little ass, NEEDED me to cum on her. Cassidy, with the pretty face, and full, soft lips, wanted ME to cum on her.

My cock swelled with desire, and I realized how great it was going to feel to cum on Cassidy. The naked chick with the bouncing boobs in my video was arousing, but the thought of Cassidy waiting in the next room for my cum was electrifying. What I wanted was Cassidy's wet lips wrapped tightly around my cock. What I wanted was to feel Cassidy's smooth breasts in my hands, and to wrap them around my manhood. What I wanted was to deliver my steaming load straight up Cassidy's wet, tight pussy.

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