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The Hot & Horny Red-headed Roommate

Cassidy probably could sense the building arousal in eyes as she egged me on by saying softly, "Cum for me." When I smiled broadly in response, she said, "Go ahead lover, cum for me. Cum deep in between my breasts like that. Or if you want, push that tip through the top and shoot your load all over my face."

But this was probably going to be the last time for us, and there was so much more I wanted to try. Although my cock was ready for release, I wanted more than that.

"No," I responded, pulling my cock out from between Cassidy's round, delightful mounds, "not yet." I lifted my leg over Cassidy's body and stood next to her, looking down past my throbbing, twitching, fully erect cock at her pretty face and questioning blue eyes. "You said I could have whatever I wanted."

"So what do you want?" she asked me, releasing her big, round breasts and rolling onto her side so that her mountain of smooth tit flesh flopped slightly down to the side.

"I know you have a toy that you use on yourself. I want you to get it right now and then get on all fours on your bed," I instructed.

"You sure?" Cassidy asked me, "My toy?"

"Yes!" I snapped. "Right now."

"Yes sir!" Cassidy replied with a giggle, and she was quickly on her feet and running into her bedroom. I watched her toned, round bottom as she disappeared into her room and I slowly followed her.

When I got to the room, I remembered that we had set down the frame and the mattress in the middle of the room, but we hadn't moved it against the wall yet or put any sheets on it. Oh well. I entered just in time to see Cassidy toss a big, rabbit style vibrator onto the bed and then leap onto the bed after it, landing on all fours with a bounce.

I was proud that my cock was still rock solid, and walked to a spot behind Cassidy, whose toes were hanging down over the edge of the bed. She looked back at me over her shoulder, and I could read a wide range of expressions in her blue eyes and on her face: excitement, nervousness, eagerness and fear. They were all there, in her soft lips and her twinkling eyes, as she shook her firm, round ass at me.

"Play with yourself," I instructed. The toy was just barely within Cassidy's reach, and as she leaned over and her big boob hung down below her body, she looked back at me questioningly.

"You mean stick this inside of me?" she asked.

"No," I responded with a sigh. "Use the vibrating part on your clit."

"I don't know," Cassidy responded hesitantly, but she flicked on the vibrating rabbit ears as she continued, "I'm a little sensitive down there."

"Good," I told her, "Remember that you said this could be whatever I wanted."

I could barely hear the vibrating and guessed that she had it on a low setting. But I was still getting what I wanted, and I laid my hands on either cheek of her toned, bare ass. "Play with yourself," I said again, and was rewarded with a little gasp from Cassidy as I could hear the vibrating ears making contact with with the wet skin of her sex.

Cassidy's back arched, and with her body resting on two legs and one hand, her thighs were spread apart for me. I teased the outer folds of Cassidy's now dripping wet sex with the fat head of my cock and got an arousing and unexpected feedback from the vibrations that were just inches away on her clit. I teased open Cassidy's wet folds, enjoying the sensation of her skin buzzing with the vibrator, and then I sank the first few inches of my pole firmly into the tunnel of Cassidy's sex.

It felt good to be back inside of her, warm and wet on my manhood, as I thrust back and forth a few inches. Her pussy was dripping with her juices from her earlier orgasms, but her tight, wet pussy walls still gripped my sensitive cock skin as I plowed back and forth inside of her. The vibrations added a little extra sensation, and I grabbed her hips to pull her back onto me as I sank the full length of my long, rock hard rod into her body.

Cassidy was panting and moaning from the combination of my cock fucking her pussy and her vibrator on her clit, but I got the feeling she was barely touching herself with her toy.

"Press that thing into your clit," I instructed her, shoving my meet deep inside of her sex and feeling my hanging balls slap against the vibrator next to her clit.

"Oh... it's sensitive," Cassidy complained in an almost whiny voice.

I reached back with my left hand and slapped hard against the smooth skin of her ass. The slap sounded much louder than it felt, but it had the desired effect as Cassidy yelped and then pressed her vibrator more firmly against her clit.

I began to pound my cock hard into Cassidy from behind, and could hear her hanging tits sliding over the bare mattress beneath her as her body was rocked by my hard fucking. In and out I thrust rapidly, sliding the full length of my wide, excited dick inside of her wet, squishy tunnel, and I slapped her pale ass again hard.

"Ow!" she yelped, but the muffled sounds of the vibration made me think she had pressed the vibrator even harder to her clit.

"I told you to press it right against your clit," I said as I pumped my hips frantically back and forth, ramming my thick meat into her tight hole.

"I am!" she pleaded, her voice begging and moaning at the same time. "Oh FUCK! It's right on my clit!"

"Keep it there!" I demanded, punctuated by another flat slap on the soft skin of her bottom. My big pole was flying in and out of her hot snatch, juices dripping down her thigh as I fucked her hard.

"Oh God... it's RIGHT THERE!" she yelled back at me. But despite the protest in her voice, Cassidy was rocking her hot body back and forth in rhythm with my fucking, and the vibrator stayed on her clit.

"You going to cum like this?" I asked, my hips shoving my hard meat deep inside of her tight, wet hole.

"Yes!" she practically shouted in response.

"You going to cum with my dick in your pussy and your vibrator on your clit?" I demanded.

"YES!" She practically screeched. "Oh FUCK... YES!"

The tingles of my own orgasm were just starting, but the sight of Cassidy's sweaty, pale, naked body practically electrified with desire in front of me was driving me wild. "Then cum for me," I said softly.

"Oh... oh... I don't..." Cassidy panted in rhythm with my hard pounding.

"Cum on my cock for me, Cassidy," I said, never slowing down, just pumping the full length of my hard cock in and out of her hot, dripping wet womanhood.

"OH FUCK, OH FUCK, OHFUCKOHFUCKOHFUCKOHFUCK... YEEESSSSS!!" Cassidy screamed, her words blurring together as her back arched deeper than I had ever seen it and she orgasmed on my hard and pounding pole. The orgasm was so strong that I could feel her insides slowly contracting back and forth around the fullness of my dick, and her thighs shook violently. She froze with her big, round tits thrust out from her chest, the vibrator still gently buzzing her sensitive and over stimulated clit, and then she collapsed in a sudden heap on top of the mattress, practically throwing her vibrator off the bed.

My hard cock slipped from inside of her as she crumpled to the bare mattress, my manhood tingly and desperately aroused. But I knew there was nothing I could have done to stop her, she was fully spent.

I spent a moment admiring Cassidy's toned body and womanly curves. My eyes drank in the way I could see her bottom rib pushing out from her body, and then her frame curve gently inward to her waist, and then flared back out again to her very pale but toned hips. I admired the way her pale, round breasts were so full and so firm that, with her body lying partly on her side, it was like she was resting atop two big cushions of tit flesh.

When Cassidy finally opened her eyes and looked at me, her full lips curved upward into a sleepy smile and she looked almost exhausted. Her first words were, "Oh God, you're still totally hard."

"You look like you're ready to sleep for the night," I teased, still standing at the side of the bed.

"That was amazing.." Cassidy said softly eyes slowly closing as her words gently drifted off. "It was almost... too intense. Too much sensation." I let her lay there for a moment in silence, her chest gently rising and falling, her smooth, naked skin glistening with her perspiration, until I thought she might have fallen asleep.

Just when I was about to say something, Cassidy slid off the bed and stood on her feet. "I know you're probably aching to finally get off, but I need a minute to recover. And I need to clean up a little."

With that, Cassidy walked out of the room and I slowly followed her. She went into the bathroom, closing the door most of the way behind her but leaving it clearly ajar. I decided to stand outside of the bathroom and give her some time, though my excited cock slowly began shrinking on me. I heard the sink running, and then a toilet flush while the sink was still running, and then what sounded like splashing in the sink. When the door finally opened, Cassidy looked generally the same except that she had clearly splashed some water on her face and the edges of her red hair were wet.

"Okay lover," she said with a tired smile and one hand again on her hip. "You're the one who wants to be in charge all of a sudden, so what do you want?"

"I suppose you feel a little too worn out to keep fucking?" I asked more than stated.

"I'm a little worn out down there right now," Cassidy responded with a hint of sarcasm in her voice, "so if we could find something else to do I would prefer that."

"I can think of something else I might want to try?" I said slyly.

Cassidy's red eyebrows went up and she looked at me suspiciously. "What did you have in mind?"

I hesitated, but then said questioningly, "You willing to try anal?"

"Umm... maybe," she responded. Her blue eyes dropped to my half-hard dick and then she looked back up into my eyes and said, "It's really a compliment to you, lover, but I think your dick might be too big for my ass."

'We can take it very easy," I tried to convince her. "We'll go slow and as soon as it starts hurting you just say so and I'll stop."

"Well that thing is going to hurt at least a little," Cassidy said skeptically, eyes returning to my dick. But I could tell I had won when her hand dropped back to her side. "But if you PROMISE me that you'll stop if I tell you to, then I'm willing to try taking that huge dick of yours."

"Amazing!" I blurted out, followed by, "I promise, you just tell me if it hurts too much."

"So how do you want to do it?" she asked.

Moments later I had Cassidy resting her elbows on the bathroom sink, bent over at the waist with her legs spread. With her body in this almost L shaped position, she was looking into our reflections in the mirror and her round, toned ass was sticking out behind her.

Her blue eyes watched me apprehensively as I tried to get my dick all the way hard again. I had taken some baby oil we found in Cassidy's new bathroom, poured a generous amount into my hand, and then carefully lubricated the length of my long shaft. I was squeezing my pole tightly, my closed fist still sliding easily up and down my pole, getting myself hard and slippery. The sensation was pleasurable, especially after all the earlier excitement, and the view of Cassidy's smooth, pale ass just waiting for me also helped. But my cock was also getting a little sensitive from all the rubbing and stimulation, and it took me a little while to get my erection to full steam.

Once my cock had returned to a rock hard stiffness, I applied another big dollop of oil to the tip of my dick and then carefully positioned my fat cock head right up against the tightly puckered sphincter of Cassidy's ass hole.

"You ready?" I asked, looking into Cassidy's blue eyes in the mirror.

"As I'll ever be," she responded. I noticed for the first time that she had taken a hand towel and wrapped it tightly around one hand while holding the other end.

With my hard cock head practically dripping lube, and pressed right up against her tight little bung hole, I pushed. And nothing happened. I put a little more pressure, thrusting a little bit with my hips, and my fat cock head pressed hard against Cassidy's closed opening. And still nothing happened.

I was about to give up and ask if I was doing something wrong when Cassidy, looking into my eyes in the mirror, said, "Go ahead, you're going to have to push a little harder."

I thrust with my hips like I was trying to bury my dick in her pussy, and FINALLY my cock head popped past the resistance and through Cassidy's tight ass hole. The sensation as I slipped inside Cassidy's ass was remarkable. Her tightly packed sphincter muscles squeezed my cock head almost to the point of being painful, and yet squeezed it so arousingly and delightfully as I slipped into her rear entrance. Cassidy gasped loudly as the first inch of my thick cock slipped into her poop chute, so I pulled out just to the tip of my head and then thrust two more inches slowly past her ass hole.

Cassidy cringed a little in the mirror, biting her lip, but I was lost in the new, stimulating sensations. Once inside of her ass, the sensation of her ass passage around my dick didn't really feel that great. She felt looser through her back door than in her pussy, and I kind of missed the way her tight, slippery pussy channel slid against my sensitive cock skin. But the sensation of her asshole was amazing. That tight little bundle of muscle squeeze whatever cock skin I slipped past it. As I rocked my hips back and forth to send a few inches at a time sliding in and out of her rear door, her bung hole milked my thick rod so tightly it caused pleasure on the border of pain.

Added to the sensations in my dick, the view was just plain naughty. Cassidy's sweet, round bottom was right in front of me and there was my big dick, being shoved up the wrong hole. I slipped my slippery cock back and forth through Cassidy's tight sphincter, and I knew just from the sight of my dick disappearing up her ass that I was being bad and it felt really good.

The physical sensations and the mental feeling of naughtiness were starting to get my overworked cock back on the path to orgasm. I could feel the tingling starting in my groin and building up through my toes, and I was actually contemplating if I wanted to try the sensation of cumming deep in her ass. But then I looked up from Cassidy's round, firm ass and into her face in the mirror. She was gritting her teeth and had the towel wrapped around one hand so tightly that her knuckles were turning white.

"You okay?" I asked.

"It kind of hurts," Cassidy managed to say through her grimace.

"You want me to stop?" I asked, my cock still slowly sliding back and forth out of her ass.

"You mind?" she asked.

I immediately withdrew my cock from Cassidy's ass chute, my cock head sticking inside for a brief second and then sliding out through the very tight hole with a pleasurable little pop. "Of course not," I said, though popping my cock head out of her hole had provided a little burst of sensation that had brought me even closer to cumming.

"I'm sorry," Cassidy said, turning her body around and standing to face me, "but that is easily the biggest thing that's ever been up in there. Were you close?"

I looked down at my cock and seeing that it looked generally clean I closed my right hand over the tip and began to stroke up and down. "Yeah," I responded.

"I'm sorry," Cassidy repeated. "You want to cum now? I'll do whatever else you might want."

Seeing the towel still wrapped tightly around Cassidy's hand, I got a weird idea. I put my free hand on her waist and guided her hot little body until she was standing next to the tub. Then I took the free end of the towel and threw it up so it went over the top of the bar holding the shower curtain. Cassidy looked at me confused, with one end of the towel wrapped around her hand and the other dangling way over her head.

"You said you'd do anything, right?" I asked, as my hand continued to slide up and down my excited cock.

"Yeah," she replied skeptically.

"Reach up and wrap that other end of the towel around your other hand," I instructed. Cassidy did what she was told, and in order to wrap both hands in the towel, she had to stand right under the bar with her hands up a couple of inches above her head.

When she turned back to face me, I could see in her twinkling blue eyes that she was starting to catch onto the idea. Her hands appeared bound above her head , and her full body was on display for me, from her red hair still tied in a tight pony tail to her pretty face and dazzling blue eyes, to her big, full tits sitting proudly on her chest, down to her shapely, toned legs and her little toes.

"You may want to step into the tub for this," I told her, and she dutifully obeyed, stepping backwards over the edge of the tub while keeping her blue eyes focused on me.

"You said anything I want, right?" I repeated, as my closed fist continued to pump steadily up and down my hard, slippery pole.

"Yes, sir," she responded in a soft voice, and the "sir" sent a spark of pleasure shooting up my cock that drove me wild.

"I'm going to cum on your face, Cassidy," I informed her, walking so I was a little bit closer to her. As my hand slid up and down my still slippery dick, I realized there might be a little problem with the angle. Cassidy was shorter than me, but my cock was still at a level below her boobs.

"Yes, sir," Cassidy repeated, sending another little tingle up my spine from her submissiveness.

"I want you to beg for it," I told her, still trying to figure out how I was going to get my load on that pretty face. Her encouraging words and her beautiful, curvy, naked body just hanging there in front of me for my use was quickly driving me towards orgasm.

"Please sir," Cassidy begged, "Please cum on my face." He voice was so meek and yet hungry, her blue eyes looked up at me pleadingly. Her beautiful, creamy breasts swayed back and forth in front of me as she purposefully shook her chest slowly from side to side. "Please give me your cum, sir. Right on my face."

Her voice was driving me wild, and I finally decided to just go for it. I stepped up on the edge of the tub and looked down from well above Cassidy and she kept her eyes on mine.

"Please sir, cum on my face. Shoot that cum right on my face. Cover my face with your cum sir," she pleaded softly.

My whole body was a live wire and the energy was pouring straight into my cock. It was the build up from all the fucking before, and sliding inside her ass, and watching her hot little body in her tight clothes all day. It was her looking up at me with a little smile, begging for my cum.

When I finally burst, my hand tightly milking my dick, it really felt like a flame was shooting out of my penis. I had never felt something so sharp or intense from sex before. Maybe it was the crazy strong sensation or maybe it was the fact that I had cum so many times before, but as the orgasm tickled me to my core, I kept my eyes open easily for one of the first times in my life.

And as that orgasm blew out of me, I was treated to a lovely sight that I will never, ever forget. The first blast of cum caught Cassidy partly by surprise, probably because I had warned her almost every time before. It splattered very wetly right onto her smiling, pink lips, the excess dribbling down her lightly freckled chin. Her light blue eyes widened in surprise, and then she shut them tightly just before my second spurt hit her squarely over her right eye. The cum was so forceful that it splattered down her pale cheek, and the white cum made the red of her eyelashes stand out even more. At this point the orgasm was so overwhelming that I was just pumping my cock with my hand, and my cum was going wherever my cock happened to be pointed at the time. So the third spurt started at Cassidy's forehead and then went back over the top of her head. With her red hair in a pony tail, my cum seemed to be a glowing white line of contrast. My fourth spurt hit her weekly in the cheek, the jizz flowing down her neck. I was just beginning to recover my senses, and was surprised that I was still coming, but I had enough sense to point my dick squarely at Cassidy's face. The last spurt hit her directly on her little nose, the spunk running down over her lips.

As the orgasm subsided, Cassidy started to laugh with her eyes still closed. "You proud of what you did there?" she asked me, smiling through the white jizz covering her pretty lips.

"Oh yeah," I responded.

She laughed again and said, "Mind turning on the shower for me?"

Maybe fifteen minutes later we were both looking fresher, though I was back in my sweaty clothes. I paused awkwardly in front of her apartment door, turning back to look at her before I opened the exit.

"You are amazing, I hope you know that," I said, trying to fight back the emotions that were trying to bring tears to my eyes. "You'll always be special to me."

"You too, of course," Cassidy said with a sad smile, her blue eyes looking deeply into mine. "Thanks for everything, I really mean it."

I leaned forward to say goodbye, and Cassidy caught me off guard for one last time by planting a soft, light kiss on my lips.

We were never as close after that day, which surprised me a little at the time but looking back doesn't surprise me at all. I moved on to Kristen and Cassidy just moved on. We still saw each other while out with friends, but we never really got into each other's lives after that. We also had to be careful when out drinking together, because we would get really flirty. We even "rebounded" once a couple of years later and had sex one night. But that goodbye at her doorway was the real end to the story of me and Cassidy. She was simultaneously the best and worst roommate I ever had.