The Roommate

"You're still wearing your work clothes," I said. She looked so smart and sexy in that outfit, her red hair loosely falling over the shoulder of her black jacket. Her white shirt fell loosely over her chest, but with the drape of her jacket and the way her large breasts poked out through her front, it almost accentuated her round, firm chest.

"You said I looked sexy in these clothes," Cassidy replied with a slight smile.

"But you said you didn't want to mess up your clothes," I stated, confused.

"The point is to cum on my face, remember," Cassidy responded. Her eyes moved to my still engorged cock wrapped tightly in my hand. "Go ahead, honey, cum on my pretty face."

"You sure?" I asked, "I don't want to mess up your clothes." My hand began to slide up and down my cock, the pleasurable tingling returning as I looked down at Cassidy's beautiful, waiting face.

"Then cum on my face," Cassidy replied, her blue eyes moving up to meet mine. "Isn't that the point? Don't I look sexy for you dressed up like this? I'm on my knees for you, just waiting for your hot cum on my face."

"Oh God," was all I managed, as my hand slid up and down my cock and I looked at Cassidy's smooth, smiling cheeks. Seeing Cassidy's sparkling blue eyes looking up at me, the smile on her full, pink lips, I lost total control. The orgasm burned up suddenly through my loins and burst out in a surge of pleasure through my cock. I managed to keep my eyes open, transfixed by Cassidy's dazzling white smile as she closed her eyes, and my first thick, hot rope of cum splattered squarely over her smiling, pink lips. My cock pulsed again, and another rope of cum landed on Cassidy's smooth right cheek. Then another on her chin, and another drawing a while line on her soft, pink lips. Finally my cock sent a weak glob onto the tub between my feet, but the orgasm continued to light up and tantalize my body for several seconds afterwards, as I soaked in the view of Cassidy's sexy, pale face covered by my hot, white cum.

Finally, with her eyes still closed, Cassidy asked, "Did you get any on my jacket?"

"No," I said, trying to inspect her clothing, "But it's starting to run down onto your shirt." I reached for some toilet paper and tried to wipe away the little bit of my spunk that had splattered around her closed eyes.

"That's fine," she said with a smile, carefully removing her jacket while she kept her eyes closed. When I was done wiping, she opened her eyes and stood. "You enjoy that?" she asked me.

"Hell yeah," I responded with a beaming smile.

"Good, I'm glad," she said as she stepped out of the tub. "A deal is a deal. But now I have to go clean myself up. Thanks for not getting cum on my jacket."

"Thanks for letting me cum on your face," I replied.

"Anytime," she said with a smile, as she walked out of my room. Anytime?

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The following weekend, just a few days after spraying my jizz all over Cassidy's face, I was asleep in bed around 4 am on Saturday. I started to wake just as I realized that Cassidy was in the bed with me.

"What the hell?" I asked groggily. I was sleeping under a sheet in just my boxers, and I could feel Cassidy's firm young body pressed against me beneath the covers. I could also feel her hand on the waist band of my boxers, and it felt like she was trying to pull them off.

"I want you to fuck me" she whispered. I could easily smell the strong scent of alcohol on her breath.

As I rolled onto my back, Cassidy's hand closed around the base of my cock and pulled my manhood out through the front of my boxers. "You said no sex," I reminded her, still trying to wake my muddled mind. I felt one of her full breasts resting against my chest and asked, "Are you naked?!"

"I know what I said," she hissed, the smell of vodka almost overwhelming me. "But I need to get fucked tonight and I dream of feeling this cock inside of me."

Cassidy's soft hand was gently pumping up and down my mostly flaccid member. My mind was still confused but my cock was beginning to react and inflate on its own. "I don't know.." I began to say.

"Don't you want to fuck me?" Cassidy asked insistently. She threw a leg over my body and began straddling me, her hips now on my thighs and her hand still rubbing at my cock head. "What do I have to do to you? You make it seem like you don't want me. Do I have to throw myself at you? Why don't you want my body like other guys do?"

"Cassidy, you're hot," I tried, still rubbing my eyes and not sure if I should stop this or encourage it. "But you said no sex.

My cock was now mostly hard, between Cassidy's insistent rubbing and feeling her big, firm, bare breasts against my chest. "Then let me feel this big cock inside of me."

Cassidy lifted her hips and placed my cock head at the entrance to her wet pussy. I could feel the softness of her pussy lips and the slight moisture of her opening. She was turned on. Cassidy put her hands on my chest, sunk her hips down, and my cock head popped through the tight opening of her sex and slid a few inches into her hole.

"Ohhh yes," Cassidy moaned. She lifted her body up, letting my cock slide most of the way out of her tight, wet tunnel, and then settled back down on my erection. My dick was now fully erect, and she didn't quite make it to the bottom of my rod before she began sliding back up my pole again.

"So fucking big," she moaned, my big cock plunging back into the soft, wet embrace of her sex as she slid back down me. I couldn't resist anymore and shoved my hips upwards, plunging the last few inches of my cock into the warm, wet tightness of her pussy walls.

Cassidy's mouth formed an O as she sucked in air atop me and froze. "So full," she squeaked. She had asked for this and I was going to give it to her.

My hands reached up, cupping her breasts, and I began to rapidly thrust my hips up and down, shoving my hard cock in and out of her. "Oh yes... oh God," Cassidy moaned atop me. She tried to match my rhythm, but I was pumping up and down so fast that she began to just hold onto my chest as I rocketed my cock in and out of her tight hole. My palms were filled with her firm tit flesh as she held on while I rocked my cock rapidly back and forth inside of her.

"You want to cum?" I teased through gritted teeth as I fucked Cassidy hard.

"Yes!" she moaned.

"Then cum!" I demanded, never slowing as my long, thick cock plunged in and out of her pussy.

"OHHHHH FUCKKK!!" Cassidy screamed, and then her hips squeezed hard against the sides of my body. I never stopped plowing my hard meat in and out of her hole, my pelvis slamming against hers as I buried myself to the root, while the juices of her orgasm began dripping out of her sex and running down my pole. Her body shook and she closed her eyes as she came hard atop me, riding my stabbing cock into a deep orgasm.

"Fuck!" Cassidy finally exclaimed, throwing her leg back over me and falling off my cock like she was awkwardly dismounting a horse. "You fuck so hard," she complained.

"You said that's what you wanted," I responded.

Cassidy laughed, a soft, sweet laugh, the smell of booze still floating on her breath. "If I had known you could fuck like that, I would have jumped you sooner."

She placed a hand softly on my shoulder and nestled her head against my arm. Her red hair tickled the side of my body, but after a few, short, deep breaths she seemed to be fast asleep.

I couldn't believe it. She had woken me, gotten me hard, and used me to get herself off. Then she had gone right to sleep, leaving me with a rock hard cock still wet with the moisture from her pussy. This girl was incredible. I was very aware of her large, soft breasts pressed into the side of my body, and that I was still turned on. For a moment, I considered what I could do to bring myself to orgasm. But I had never fully woken up, and that time considering what to do was enough for my eager cock to start deflating. I decided to try to go back to sleep, and before I knew it, I was dreaming again.

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When I woke up with a start several hours later, the sun was coming in my window. I looked over my should to find Cassidy awake, her red hair a mess around her head, and her blue eyes looking back at mine.

"Sorry about last night," she said.

"You better be," I replied with a laugh.

"You mad?" she asked.

"No, but you're the one who said no sex," I responded. I threw aside the sheet that was covering me and began to get out of bed.

"I know, I'm sorry," she responded. "Where you going."

"I have to piss," I replied. Cassidy got out of bed, her curvy, young body still naked, and followed me. "You going to help me piss?" I asked.

"No, I just want to make sure you're not mad," she replied.

I left the bathroom door open, expecting that she would talk to me through the doorway, but she followed me all the way into the bathroom. With a sigh of resignation, I lifted the toilet seat and began to relieve myself in front of her.

"You don't respect any boundaries, do you?" I asked.

"Boundaries?" she responded. "You've cum in my hair, on my face twice, and now we've had sex. You've seen me naked and gone down on me more times than I can count. I think we passed through most of the boundaries a long time ago."

I thought about that as I concentrated on my aim for a minute, and as I finished up, I said, "Well I don't like you suddenly changing the rules. And I don't appreciate you attacking me in the middle of the night just because you need to get off."

"I know," Cassidy said quietly. "I told you, I'm sorry about that."

I wiped my cock head with some toilet paper, flushed, and turned to find that she had been watching me the whole time. "I think there should be repercussions when you do something like that," I told her.

"I agree."

"So what did you have in mind?" I asked.

"Anything you want," Cassidy responded coyly.

"What's that mean?" I asked.

She paused for a moment, and then her big, blue eyes stared straight into mine. "I couldn't resist, last night," she began. "For weeks I've been thinking about how that big dick of yours would feel inside of me. I've never sucked one so big, and I couldn't get it out of my head how it would feel stretching my pussy like it stretched my mouth.

"Anyway," she continued, "I still shouldn't have jumped you like that. So you tell me how I can make it up to you and I'll do it."

In truth, I had been contemplating this thought since Cassidy fell asleep next to me the night before. "First, the 'no sex' rule is done. If we're both up for having sex, then let's just do that instead of blowjobs and hand jobs."

Cassidy hesitated just a second before saying, "Okay."

"Second, you owe me sex twice, whenever I want it, within reason, since you just jumped into my bed last night," I finished.

"Okay," she replied. "That's fair. I owe you sex twice, whenever you want it." She looked at my cock, now standing stiffly straight with morning wood. "You want it now?"

"No," I said, with a smile. "You also owe me a blowjob."

Cassidy looked at me, her eyes questioning, and then dropped to her knees on the bathroom floor. I walked forward confidently, my cock pointed at her face, and stopped with my cock head just an inch from her soft lips. Looking up at me with her bright, blue eyes, Cassidy's soft, pink lips parted and she sucked the head of my dick into her warm, wet mouth.

I didn't last very long, especially with the activity from the night before. Cassidy's tongue swirled my cock head, and both her hands and her soft, sucking lips slid up and down over my sensitive cock skin. She milked me with her firm fingers and her wet, slippery lips. When I felt the tingling of my approaching orgasm, I quickly withdrew my cock from between her soft lips.

Cassidy's blue eyes looked up at me in surprise, as my hand grasped my dick and pumped up and down my swollen member just inches from her face. She didn't have time to close her eyes before I blasted the first spurt of my load all over her pretty, little mouth. Cassidy recoiled in surprise, but I was careful to aim my cock lower so it sprayed it's hot spunk all over the tops of her big breasts while I closed my eyes to enjoy the sensation of the orgasm flowing through my body.

When I was done cumming, Cassidy whispered, "Jerk."

"You deserved that," I said with a laugh, once again using toilet paper to help her clean her face. None of my cum had gotten in her eyes this time, though the tops of her full, round breasts were completely covered in my jizz. I was growing to love the look of Cassidy's pale but pinkish skin coated in my white juices. "No more attacking me in the middle of the night, at least without my permission.

"We'll see," she said as she stood to leave my bathroom.

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That week, Cassidy asked me to go down on her a couple of times. I got a blowjob on Thursday night in return. At first she seemed surprised that I didn't ask for sex immediately, but she quickly caught on that I was saving those opportunities.

Seeing her hot, naked body all the time, it was hard to resist asking. At one point she was watching tv in the living room wearing only just a pair of panties. Looking at her big, firm breasts on full display, I almost asked her then. I couldn't stop staring at how upright and round her big breasts sat on her chest. But I held off, at least for a little while.

That Saturday night, Cassidy once again did something I had not expected, and I surprised myself. We went out to drinks with several friends to celebrate our former roommates' upcoming wedding. Cassidy was wearing this short, tight, powder blue dress that showed off all of her fantastic curves. Her smooth, toned legs were on full display, with the hem of her dress ending well above her knees. The dress hugged her round, toned ass, and also clung to the swell of her big, round boobs. The front of the dress scooped low to show off the full tops of her smooth, perky breasts. And I was far from the only one to notice how amazing she looked that night.

When Cassidy went for drinks at one point late in the evening, two guys at the bar sidled up to either side of her and started chatting her up. Whatever they said worked like a charm, and Cassidy was soon laughing and patting the taller of the two guys on the arm. The twinkle was back in her blue eyes, and she looked like she was soaking up the attention.

To my surprise, I felt undeniably jealous. I hadn't ever thought of Cassidy as "mine." She was just my crazy roommate who made this awesome deal with me where we helped each other orgasm. I had no claim to her and she had no claim to me, even though we messed around several times a week. I was surprised that Cassidy was so comfortable flirting with these guys in front of me, but I was way more surprised that I wanted desperately to march up to the bar and haul Cassidy away with me. Had I developed feelings for her? What did I feel towards her? Or was I just being protective of Cassidy?

It was hard to name the emotions churning through me, but it definitely felt like jealousy. I was uncomfortable examining how I felt, particularly as I watched Cassidy laugh and smile brightly at these two strangers. But it quickly dawned on me that I had a solution.

I walked up to the bar with an empty glass, making it look clear that I wanted another drink. I stood at the bar just a little apart from Cassidy and her two admirers, and waited for the bartender to notice me.

Cassidy looked over and smiled. "You good?" she asked.

"Yup, you want anything?" I asked. The two strangers kept the smiles on their faces, but I could tell from their eyes that they were weary about my presence.

"No thanks, I'm good," Cassidy responded. She began to turn back to her two new friends.

"Hey," I said, as if the thought had just occurred to me. "You still owe me a couple."

Cassidy smiled back at me, clearly not comprehending. Then, after a couple of moments, her smile faltered just a little. "I owe you?" she asked with a sort of puzzled look on her face.

"Yeah," I said lightly, with the big smile still on my face. "You know, you owe me two."

Cassidy looked down for a moment in thought, then looked up at the two guys with a bright smile and said, "Can you guys excuse me for one second while I help my friend here?"

"Sure, no problem," one of the guys replied. The two moved off in whispered conversation, never looking back at me.

Cassidy came right up beside me so her shoulder was touching mine, looked back quickly over her shoulder to make sure the guys weren't close enough to hear, and whispered, "I owe you two drinks, or the other thing?"

"The other thing," I said with a mischievous smile.

"You want to collect right now?" Cassidy asked, her questioning blue eyes searching mine.

"Yup," I replied casually, "If now is okay with you."

Cassidy paused. "Why now? Why ask now?"

"Because you look amazing in that dress," I responded immediately, without hesitation. "You've been turning me on all night, and I want to do it right here."

"Right here?!" Cassidy replied skeptically. She thought for a moment, then her smile and the twinkle in her blue eyes returned. "You're bad!"

We had been to this bar many times before, and I knew there was a second floor bathroom that not many people knew about or used because the second floor closed when the dinner service stopped at 10:00. "Wait one minute, then meet me upstairs in the men's room. Okay?" I asked.

My heart skipped a beat for one desperate second, fearing that Cassidy would refuse me in order to stay with the two guys who were hitting on her. But after a quick second deciding, Cassidy replied with a big smile. "Okay."

I tried to walk slowly up the stairs, but it was very difficult not to rush or to look back over my shoulder to make sure that Cassidy was going to follow me. Once in the stairwell, I was hidden from the bar.

I made it to the men's room and was relieved to find the small space empty. Then I waited nervously in front of the sink for what felt like 20 minutes. I paced a little. Then I looked down at my watch. Only 45 seconds had gone by since I entered the stairwell. I paced a little more, for what felt like five minutes. I looked back at my watch. 65 seconds had passed. Cassidy wasn't coming, I had told her to wait only one minute.

The door opened and Cassidy quietly slipped into the men's room with me. I quickly bolted and locked the door behind her. When I turned back to face her, she was beaming, a nervous excitement in her eyes.

"I've never been in here before," she said with a laugh, "It kind of smells." She turned back to look at me. "So how do you want to do this?"

I opened my arms as if to hug her, and Cassidy walked into my embrace. She did look hot that night, the smooth fabric of the powder blue dress hugging her firm ass and big, round breasts. When she hugged me tentatively, I felt the firmness of her boobs as they pressed against my chest. I dropped my hands to Cassidy's waist, quickly and forcefully spinning her so that she was facing the mirror over the bathroom sink with her back to me. I pressed my groin against the back of her toned ass, pleased to feel my erection quickly growing.

"How about like this?" I asked, looking at Cassidy's blue eyes in the mirror.

Her eye twinkled back at mine and a smile lit her face. "You ARE bad!" she said again. "I like this." When I paused for a moment, trying to decide how to proceed, Cassidy placed her hands on either side of the sink and said, "Well go ahead, sugar. If you're in charge of this whole set up, you should probably start by taking my panties off."

My smile now stretched from ear to ear. It was disconcerting to see myself in that mirror, but I loved seeing the amused smile on Cassidy's face. I slowly and deliberately ran my hand up the outside of Cassidy's smooth outer thighs, slipping under the hem of her dress. I thoroughly enjoyed the way the tight cut of her dress pushed my hand against the smooth, firm swell of her ass. I hooked my fingers under the hem of Cassidy's frilly panties and began to pull them down her leg. She offered no resistance, helpfully lifting her high heels off the floor so I could pull her bottoms free when I got to her feet.