Free Erotic Stories
The Hot & Horny Red-headed Roommate
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.
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.
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.
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.
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."
"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.
"Okay, I'm in," I said, "Let's do it."
Her smile returned slowly, but was soon back at full glow. "You sure?" she asked, looking into my eyes. "You can think about it if you want. It is kind of crazy."
"No, if I think about it, I'll never make a decision," I admitted to her. "Let's agree to your offer now. I'm in. But what's in it for you?"
"Are you kidding?" she asked with a laugh, her smile now back to full glow. "It's SOOO much better with a partner. I get off so much quicker, I cum harder. Isn't it the same for you? Did you cum better with my hand just now, or did you prefer what you were doing before with your own hand?"
"It was better with you," I admitted.
"See, that's why this is going to be great." Without warning, while continuing to talk to me, Cassidy began unbuttoning and unzipping her jeans. "Even just doing it with another person is so much hotter. I rather you, like, even just be in the room and talk dirty to me than try to get off alone."
"What are you doing?" I asked as Cassidy pulled her jeans and underwear together over the swell of her hips and down her smooth thighs.
"I'm asking you now," she said with a smile. "If this is going to work, you have to be willing to hold up your end of the agreement. You have to be willing to do it when I want, not just when you want." She playfully kicked her jeans off over her feet and was suddenly naked from the waist down. "Besides, I got a little turned on feeling your cock pulse between my fingers and shoot all that hot cum into my hand. Now I want to see what you can do for me."
With that, she spread her legs, showing me her pussy for the first time. I'm not exaggerating, it was possibly the prettiest pussy I've ever seen. Her pale skin turned to a deep, healthy shade of pink at her pussy lips. Her sex was smooth and plain and totally bare of any hair. Her lips were small and neatly symmetrical. And she was spreading her legs for me.
I dove in head first at the invitation, leaping out of my seat. "Oh shit!" she exclaimed as my warm mouth closed over her soft pussy lips. My tongue slid up and down over her outer folds and I was greeted with a taste that was definitely feminine but much slighter than I was used to. My tongue bore into her hole, investigating the uniqueness of her pussy, and Cassidy's hands went to the back of my head, pulling me in as she moaned.
It wasn't just her outer lips, I confirmed with the tip of my wet, probing tongue. Her pussy didn't have the musky taste I was used to. I quickly found her clit in my explorations, and I circled it and rubbed over it with my firm tongue.
"Oh fuck!" she hissed from somewhere above me.
I was focused on that little nub, teasing it and rolling over it with my saliva. When I began to lick up and down insistently, Cassidy's body shuddered in response. My hands were now on the back of her bare thighs, pulling her pussy against my face as I eagerly explored her sex. My soft lips and warm mouth suckled on her womanhood as my tongue danced over her clit.
I sucked her little clit up between my lips and rubbed at it with both my tongue and my lips. Cassidy's back arched deeply, almost bucking my mouth off of her pussy as she moaned. She seemed to love it as I rubbed at her trapped little pleasure bud, so I did it again... and again... and again....
"Oh shit, I'm...." she moaned loudly. "I'm... cumming! I'm cumming! Don't stop!!"
I hummed as I held onto Cassidy's clit with my lips, rubbing gently and insistently, coaxing the orgasm out of her while her pale, smooth thighs shook around my head and brushed against my ear.
When her panting had returned to more normal breathing, I sat back down on the floor and looked up at Cassidy. Her face was flushed, and a big smile crossed her pretty face, framed by her red hair. Her eyes were closed, but as she felt me looking at her, she eventually opened them and her satisfied blue eyes looked back at me.
"That was quick," I teased.
"I thought you were going to use your fingers or something, most guys... don't like doing that," she responded.
"Well I do," I replied.
"Obviously!" she laughed again, her light, sweet laugh. "You're amazing at it. If I had known you were that good, I would have wanted us to do this a long time ago. Fuck, I came hard."
"Good," I said. "What do we do now."
She took in a deep breath and then retrieved her discarded jeans and panties from the floor. "Now we just keep doing what we normally do until one of us needs a little helping hand again."
The new "arrangement" did not start off easily for me. Cassidy behaved as if nothing had changed between us. We hung out in the apartment as much as we did before, and it wasn't like we suddenly talked about sex all the time, or even more than before. So I went back and forth between being somewhat wary that we had this new deal between us, and sometimes forgetting that we had even made a deal.
Worse, I felt embarrassed asking for "help" from Cassidy. There were a couple of times when she was around and I got horny, a couple of times even when she made me horny. One Saturday night I remember her getting all dolled up, wearing a shiny little dress and heading out to a club. She spent a few minutes chatting with me in the living room, waiting for her friends, and I remember thinking how sexy she looked. It was a classy but low cut top that highlighted her big, round breasts and left the creamy tops of her cleavage exposed. And her red hair was all smooth and silky straight, her pale, toned thighs fully on display. It really turned me on. But Cassidy was just casually chatting with me as if she was clueless to the effect she was having on me. I didn't know what to say. "Hey, can you give me a quick handjob before you go out, your outfit has me really turned on?" seemed inappropriate. How did I initiate my end of the deal?
So I just sat there, waited until Cassidy left, and then went into my room and jerked off to porn. The whole time I was thinking about how firm Cassidy's breast had felt in my hand, and how soft her fingers had felt as she rubbed the orgasm out of me. Just before climax, I was kicking myself for not having spoken up and asked for her to do something. And when I came, I pictured myself buried deep in her pussy, her curvy, young body spread out beneath me.
Cassidy, on the other hand, seemed to have no problems asking for my assistance. The first time was a weeknight, where I was predictably hanging out on the couch watching tv.
Cassidy walked into the living room and said, "Hey, can I ask you for a favor?"
"Sure," I said.
"Well, you remember our deal? If now's a good time, I could really use your help getting off?" she said. She was very polite about it, but also very much to-the-point in her typical way.
"Oh yeah? Sure," I responded, getting up off the couch. "Where do you want to do it?"
Moments later, with little more spoken, we were on her bed with my head between her legs. Cassidy still had her t-shirt but was naked from the waist down, and my fingers were spreading apart her pussy lips as my wet tongue lightly circled her clit.
It was almost a pleasure to eat her pussy. Cassidy had such a light, almost indistinguishable taste that I had to seek it out with the length of my exploring tongue. And after several licks and flicks of my tongue over her sex, by the time I had identified her essence, she was moaning near a scream. I looked up at her from between her smooth thighs, bore in with my tongue on her clit, and concentrated on rubbing and flicking her sensitive little nub.
In very little time, Cassidy's back was arched deeply, her round breasts proudly thrust outward, and her eyes tightly shut as she rode the electricity of pleasure flowing through her body.
"Oh, there..." was all she managed, and then she was nearly screaming. I slathered all over her pussy lips and clit as she came, her soft, young body trembling around me, her moans flowing like one continuous noise out of the back of her throat while she orgasmed.
Afterwards, Cassidy quickly changed and left to meet friends. I masturbated that night remembering the look of overwhelming ecstasy on her pretty face... and my cum spurting between her gentle hands.
The next day, Cassidy didn't emerge from her room until 1 in the afternoon. I hadn't heard her come in the night before, so assumed she was sleeping off a long night of partying. When I did finally see her, she shuffled out of her room in sweat pants and a baggy t-shirt and headed straight for our kitchen.
I was sitting on the couch watching tv, and a little surprised when she plopped down into the seat next to me with a cup of coffee.
"Rough night last night?" I asked somewhat jokingly.
"It was fun, but too much tequila," she responded with a half smile. "Hey... I know I just asked you last night but... well to cut to the chase, you ate me out so good that all I could think about last night was how hard I came. Any chance you'd be willing to do that again to help wake me up this morning?"
We exchanged a quick look, my eyes searching her blue sparklers, and within seconds her pants were gone and I was back between her legs. I admired how toned her legs felt, taut muscle just below the skin as I wrapped my arms around them. Cassidy seemed to love me going straight for her clit, no messing around with nibbling or sucking on her pussy lips. She was writhing, her back arched as my soft lips closed over her hard little button and I sucked her nub up into my warm, wet mouth. Her red hair was a mess, framing her pink face and falling over her shoulders as she twisted her head back and forth while I attacked her clit with my wet tongue. She tasted a little more musty this morning, but as I bore down onto her pussy with my tongue, I marveled that I could still barely taste her.
I was so focused on thinking about Cassidy's lack of any taste that I had failed to notice her breathing growing ragged, her back arching deeply. I just flicked my tongue over her sensitive clit over and over and over, trying to taste her, until screams finally made me realize that I had brought her to the brink of orgasm.
"Oh SHIT!" she yelled, and then a deep, low grunt of "Unnnnnngggggghhhh" as she came. Cassidy's hips bucked against my tongue, her chest heaving, large breasts bouncing under her shirt, as she came. I kept steady, slippery pressure on her wet clit while she orgasmed, drawing out her moans as her orgasm subsided.
"You have a talent," Cassidy told me afterwards, and she quickly pulled back on her sweat pants and headed for her room. "I'm so glad we made this deal."
And she proved during the week that she wasn't just trying to tell me what I wanted to hear. Two days later, on Tuesday night, I went out for drinks with coworkers and returned home a little after 8. I found Cassidy sitting on the couch in just a t-shirt and bikini briefs.
She turned and smiled at me with her perfect white teeth and mischievous blue eyes and said, "Can I ask you to go down on me again?" Less than five minutes later, Cassidy was pulling my face into her pussy as she came hard while riding my tongue. Afterwards, I looked up at her, a sleepy smile on her slightly sweaty face, her chest red with arousal, and thought she could not have looked prettier.
Friday morning, I was about to walk out the door for work and Cassidy hopped up on the kitchen counter in front of me. She was wearing a short but conservative grey skirt, and a white button up top that clung to her big, round breasts. As she spread her legs, I realized she wasn't wearing any underwear.
"Can I get another wake-me-up?" she asked with a coy smile.
It took a little longer with Cassidy wearing her work clothes, forcing us to pause half way through so we could hike up her skirt a little higher. But it was kind of hot eating her out while she was basically fully clothed, suckling on her hard little clit while most of the rest of her was covered. I held her firm ass cheeks in my warm hands, pulling her pussy against my face, as she came on my suckling lips and wiggling, wet tongue.
Her face was glowing as I washed mine in the kitchen sink. "I love going through the day knowing that I already came in these clothes," she said to me as she pulled on some underwear and smoothed out her skirt. She gave me a quick kiss on the cheek as she walked out the front door.
Cassidy's sex drive was insatiable. I wanted to ask her to take a turn helping me get off, but couldn't quite muster the courage. I was so turned on from watching Cassidy's huge breasts shake while tightly encased by her button down shirt that I was on the verge of asking her to give me a hand job that Friday morning. But she was out the door before I got the chance.
Friday night I went out for drinks with my former roommate and we ended up going dancing with his new fiancée and some of her friends to celebrate their recent engagement. Some of the girls out with us were fairly attractive, and it got my libido going to watch them dance and shake their asses against me. I didn't get back to the apartment until almost 2 am.
Feeling tipsy and more than a little horny when I got back to my apartment, I decided to do what I had done a hundred times before. I fired up my computer, surfed the internet for some porn, and started jacking off. The apartment had been quiet and empty when I walked in, so I assumed Cassidy had been long asleep. I had my fully engorged cock in my hand, stroking my meat, watching a busty porn star deep throating a big dick on my computer screen, when I was surprised by a soft knock at my door.
I was still wearing my clothes from clubbing, very aware of the bulge in the front of my pants, as I cracked open my bedroom door. Cassidy was standing in the hallway, her eyes looking a little sleepy, wearing a large, loose t-shirt as pajamas.
"Hey Cassidy, what's up?" I asked softly.
"You just get home?" Cassidy asked, stifling a yawn with her fist over her mouth.
"Yup, you need something?" I asked, careful to keep my pants-filled erection behind the door.
"The power went out here earlier tonight. I had to reset my clocks, and my internet wasn't working," she explained. "I can help you get the wifi working again with your computer if you want."
"No, thanks though. My internet is working fine," I replied with a smile, hoping that would settle it and I could get back to finishing what I had started.
Cassidy looked at me questioningly, her big, blue eyes suspicious. "You're already online?" she asked. "You just came in a minute ago. What are you doing in there?"
"Just needed to check some e-mails," I responded, the smile never leaving my face.
Before I could react to what was happening, Cassidy had thrown a shoulder into my door and was slipping into my room. "You can't check e-mail on your phone? What are you up to?" she demanded as she confidently bulled her way into my room.
"Cassidy!" I scolded her. "Personal space!" I was genuinely shocked by her intrusion.
"Personal space my ass," she responded, "I came with your tongue in my pussy this morning, remember?"
She had already walked around to my desk and was looking at my computer screen. Her blue eyes quickly flashed back to mine, and then lowered to the noticeable bulge poking up into the front of my pants.
"Oh honey," Cassidy scolded.
Prepare to defend myself against to usual accusations that watching porn was a dirty a deviant behavior, I responded, "Hey, it's a totally natural thing."
"Of course it's a totally natural thing!" Cassidy responded, her hands going accusingly to her hips. "That's why we made a deal, remember?! You help me and I help you. Why didn't you just tell me, as soon as I knocked, that you were trying to get off in here."
I was speechless. My brain was scrambling trying to catch up to the many unexpected turns in events.
"The deal means I help you too, when you need it. Especially a talented, big tongue like yours," she continued.
Overwhelmed by trying to think through to an answer, my brain just defaulted to the truth. "I didn't know how to ask," I replied dumbly. "I didn't know when it's okay... like it's pretty late tonight."
Cassidy flashed me her sparkling, white smile. Slowly, she reached out and closed her small, soft hand over my fingers. She guided me to my chair and asked, "Were you doing it right here?"
She patted the seat, looking up at me coyly with her blue eyes from beneath her red hair, and I sat down. Then she dropped to her knees in front of me, her small fingers fumbling with my zipper and pulling it down. I could feel her soft touch as her finger closed around my still stiff pole, and she carefully pulled it free of my pants.
"Cassidy," I said, unsure of what to say next.
"It's okay, sugar, you just keep watching your video and I'll just show you how much better I am than your hand, and why you should learn to ask."
She turned around briefly, pressed a few buttons until the porn started playing again, and then turned back to me with a smile. Her bright blue eyes were looking up at mine, her big smile full of sparkling white teeth on her face, and her small fingers wrapped around the base of my cock.
"You have a really big dick, I don't know if I've told you that already," she said, still smiling. And then she leaned down and my aching cock head disappeared between her soft lips.
Cassidy's soft, warm, slippery mouth closed over the head of my member, her tongue circling teasingly around the head of my cock. Then she plunged down, swallowing more of my long pole than any woman had even attempted before, slid her tongue back up over the underside of my shaft as her head rose, and then plunged back down again, tightly enclosing my meat in her warm, wet cheeks. For the first minute or so, I actually watched the porno blowjob on my computer screen behind Cassidy, my brain tantalized by watching a blowjob while also receiving a blowjob. And Cassidy was very good at sucking my dick. Her tongue swirled my tip and her soft lips sucked over my sensitive skin, and her hot, wet mouth enveloped me.
I eventually realized I was being an idiot. I had fantasized about Cassidy blowing me, dreamed about it, wished for it. And now it was happening right in front of me! Her long, fiery red hair hung over her face, hiding most of what was happening, but it was still a dream to watch her locks tumbled back and forth while her wet mouth suckled on my cock. She suckled noisily and hummed as her wet cheeks slid up and down my throbbing pole. Cassidy looked up and me from beneath her hair, her tongue swirling again around my cock head and she held just the tip of my cock between her full lips. She smiled when her blue eyes met mine.
Her soft fingers began sliding up and down my meat along with her mouth, exciting so much of my erection that I knew I wouldn't be able to hold off for long. As her warm mouth sucked me and her slippery, soft fingers slid tightly over my erection, I felt the familiar tingles starting again in my body.
"Cassidy," I tried to warn as her warm mouth continued to slide up and down my pole, "I'm going to cum."
She never stopped sucking, never stopped jacking me with her small hand. Her mouth and her fingers slid up and down my sensitive meat, and when her blue eyes looked up into mine again, I exploded.
The orgasm was so powerful, I squeezed my eyes shut. But I could feel that Cassidy' mouth never stopped sucking me, her tongue coaxing the cream out of me by lapping at the underside of my shaft as I sent burst after burst of cum flowing into Cassidy's mouth. My toes curled and my legs strained with the pleasure of orgasm as I blew my load between Cassidy's soft lips.
By the time I came back to my senses and opened my eyes, Cassidy was looking up at me with a beaming smile and a twinkle in her bright blue eyes. She had clearly swallowed all of my load.
"See," she said coyly, "Wasn't that much better than just doing it with your hand."
"Oh my God, you have no idea," I responded with a satisfied sigh, and a smile of my own.
Cassidy laughed her light, sweet laugh in response. She rose slowly, kissed me softly on the forehead, and began to walk casually out of my room. "Good," she said over her shoulder, just before closing my door behind her. "Maybe next time you'll ask."
The next morning I started my day with a shower. As I was washing away the sweat from the night before, I was completely distracted by thoughts of the amazing blowjob I had received. The blowjob was so good, I was still not completely sure that it hadn't been a dream. Any lingering doubts were washed away with the sweat when I was startled by the shower door opening.
Cassidy just stepped in, completely naked. I was frozen, paralyzed by shock. This stuff happened in pornos, it didn't happen in real life. Cassidy's deep, loud laughter, and the way her big, round breasts shook as she laughed, knocked me out of my paralysis.
"What the hell are you doing in here?" I asked.
"Oh relax," Cassidy replied, with a teasing slap of my shoulder. "Didn't you enjoy last night?"
"Yes, you were great," I admitted. "You can't just hop in the shower with me. We need some boundaries."
"Boundaries are bullshit," she replied. "Or didn't you enjoy how I got you off?" Cassidy's hand reached out through the warm shower water cascading between us, and she grasped my cock gently with her soft fingers as if to emphasize her point. She rubbed softly at my cock head, and my meat instantly began swelling. "Ahhh, even if you don't agree, your dick still remembers last night. You had so much cum, and you were such a dummy about just asking me to help, that I thought I would check on you."
Cassidy's fingers were running over the underside of my shaft, while her thumb circled my cock head. I quickly had a full erection, between her soft rubbing and the sight of her incredible, naked body.
"You do want this, don't you?" she asked quietly, her fingers never stopping their gentle rubbing on my slippery manhood. "We made a deal, and I still owe you one from what you did for me this week." Her blue eyes searched mine as her finger closed around my shaft and started jacking me in earnest. Her eyes were so beautiful, and her small, pink nipples were such a turn on for me to see.
"If you want me to stop, just say so," Cassidy said softly over the noise of the falling water.
"No," I replied quietly. "Don't stop."
"Then ask me for this," Cassidy instructed, her fingers tightening slightly as her closed hand slid up and down my pole. "Ask me."
"Jerk me off," I responded.
"Ask me to do it," Cassidy replied, color filling her cheeks. She was getting turned on by this.
"Cassidy, give me a handjob," I replied firmly as her fingers milked my shaft.
"Tell me to do it," she responded huskily, "Tell me so I know that you'll be able to ask me again."
"Cassidy," I responded, my confidence growing. My hands reached up and grabbed her soft shoulders. "Use your hands to get me off. Play with my cock until I cum."
"Ohhh," she moaned, a dreamy look now in her eyes. Her moan and her facial expression turned me on more than her fingers slipping up and down over my wet cock.
I slid one wet hand down off her shoulder, over her chest, and rubbed softly at one of her pink nipples with my thumb. The warm water cascading over her smooth breasts, flowing into a river between her perky cleavage, was so arousing to see. My cock swelled between Cassidy's fingers, and she grasped my pole with both of her hands. Her soft, closed fingers began gently squeezing me while turning in opposite directions, an amazing sensation of stimulation and arousal that is difficult for me to describe.
"You like my breasts?" Cassidy asked as my fingers slipped over the tip of one of her big, firm mounds. I was drinking in the sight of her pale, smooth tit flesh being washed by the water.
"Yes, they're amazing," I replied honestly.
"Tell me," Cassidy asked breathlessly. Her red hair was beginning to get wet from the spray and sticking to her neck and back. Both of her hands were softly and gently milking my long dick. "Tell me what you like."
"I love your breasts, they're so sexy," I responded as Cassidy's hands tugged upwards over my excited pole. "Your face is so beautiful... your eyes and your lips... You're so sexy!" I was losing control, both over my words and my body.
"Tell me what you want. Tell me what to do," Cassidy instructed, almost begging. "Tell me what you like."
"I love your breasts, I want to fuck them," I responded.
Abruptly, Cassidy released her grip on my cock and squatted down under the continuing spray of the shower. The warm water washed over her red hair, flowed down her neck, and between the valley of her cleavage. She put her hands at the sides of her big, round breasts, moved forward a bit until my raging erection was between her tits, and then closed her interlocking fingers over her nipples and my cock.
"You want to fuck my breasts," Cassidy replied. "Go ahead."
I thrust my cock up between Cassidy's soft melons. I LOVE tit fucking. It felt so soft and so firm at the same time, Cassidy's smooth, young tit flesh tightly enclosing my shaft as it slid up and down between her wet melons. As I thrust back and forth into her tunnel of tit flesh, I was also amazed that Cassidy would let me do this. She had to squat in the shower, with spray from the shower water running over her face, but she smiled up at me with her big, blue eyes as I pushed my cock in and out from between the tight tunnel of her breasts.
After only a few thrusts, the experience and the unbelievable sight before me began to overwhelm me. I felt the familiar pleasure of an impending orgasm.
"Oh Cassidy," I moaned, "I'm going to cum."
"Where do you want to cum?" she asked, her bright smile never wavering. "Tell me."
"Ohhh," I moaned as the pleasurable flows began to build beyond the point of no return. "On your face. I want to cum, on your face."
Cassidy paused, the smile faltering for just a second, before she replied. "Well go ahead then, cum on my face. Cum for me."
One more thrust between Cassidy's slippery and soft tit flesh, and I pushed my cock so the tip was sticking up above Cassidy's cleavage. I came hard, fighting to keep my eyes open as the orgasm burned like lighting bolts through me. A fat stream of white cum shot out of my tip and splattered from just beneath Cassidy's nose, down over her full, smiling lips, and puddling on her chin. My cock spurted again and again as I came, but the rest of my spunk struck Cassidy under her chin and dribbled down wetly over her neck and the tops of her breasts. By the time the tingling stopped, I was greeted by the sight of Cassidy's red hair plastered wetly to her back, a line of white cum over her smiling lips, the length of my shaft tightly encased between her big, beautiful, round breasts, and my cock head popping out of the tops of her breasts in a puddle of cum.
Cassidy slowly stood and carefully began to wipe the cum off of her face and chest with the aid of some soap and shower water. I tried to help her wash some of the cum off of her chest, then realized that my hands were also pawing at her round, firm tits
"Is this okay? I asked.
"You are a sweet one," Cassidy responded, and then gave me a little peck on the cheek.
As we were both drying off with towels a few moments later, Cassidy said, "Now I hope you know you better ask the next time you need a little help." Her accompanying smile was honest and warm, empty of any teasing or irony.
"I do," I replied.
I'm sure a lot of people will be exasperated by my timidity at this point in my story. All I can offer in my defense is that I really did not want to screw up my living situation, and I thought a good outcome was very unlikely. I was not the type of person who this kind of stuff happened to, and I knew all this fooling around between me and Cassidy could be dangerous if it didn't go well. It turned out that I was mostly right.
I'd like to say that, after the blowjob and the shower, I dove right into exploiting my deal with Cassidy. That's not totally true. We did fool around A LOT. I haven't met any women who could match her sex drive, so she was always asking me to pleasure her. She especially loved me going down on her, and that became almost all we did. She asked me almost every other day, mostly at night though sometimes in the morning before work. I began to catch on to when she was having her period, because she would be less interested in sex just before and during her period. But immediately after she was done, she would almost attack me as soon as I got home, and would ride my mouth and my tongue to screaming orgasm. I got very good at figuring out how she especially enjoyed me just tickling lightly over her clit with my tongue while she came, and she got so loud that I'm sure the neighbors heard us at least once or twice.
I also got better about asking for her "help," which was a blowjob most of the time. Cassidy was VERY good at blowing me, and she loved hearing that she could take more of my dick in her mouth than any girl I had met before. She tried deep throating a couple more times, but she would quickly start gagging if my cock was in her throat too long. Still, her soft lips and slippery cheeks made me cum quickly every time. But I didn't ask to fuck her tits again, and I didn't ask to cum on her face. I could tell that she hadn't been thrilled when I asked to cum on her face the first time. Sometimes a hand job was good enough, and I really enjoyed watching her big, full tits sway back and forth as her hand pumped up and down my dick. But her blowjobs were so good, I mostly just asked for that.
Cassidy also began learning what I liked. She knew I loved her breasts, and would be sure to take her top and bra off at the start, whenever she was going to give me a tug job or blowjob. And she encouraged me to touch and play with her big, soft breasts while she was pleasuring me. I learned that her smooth, creamy inner thighs were very sensitive, almost to the point of being ticklish. To get her going, I would run my fingers lightly over her soft inner thighs before I went down on her.
Still, that was all we did. Three or four times a week, I would eat her out and make her cum. Once or twice a week Cassidy would blow me. She started getting comfortable wearing just a loose shirt and bottoms around the apartment, or sometimes just the shirt. And she was so sexy she still turned me on like crazy every day. But after four or five weeks of helping each other cum, it almost got routine.
We may have eventually gotten bored of deal... maybe... if not for a couple of events that escalated our situation. Both were Cassidy's fault, of course. The first erupted over a scandal at the University of North Carolina, of all places. Cassidy had graduated from UNC, as had most of her family. She had grown up cheering for the school. So when news of a scandal broke, and the university was charged with allowing hundreds of athletes to take a fake class in order to inflate their grades, Cassidy insisted it couldn't be true.
One evening I was watching the news and a story came on about the UNC scandal. Cassidy blurted out, "You'll see! It can't possibly be true." She was normally so free spirited and laid back that it was the closest I had ever seen to her becoming angry.
"I don't know," I replied honestly and skeptically. "It seems like they have a lot of evidence. They're talking about firing people over this."
"There's no way it's true," Cassidy insisted loudly. "It's a respected institution! There's no way the university would let bad people cheapen the value of a degree from UNC just to help out some athletes. You'll see!"
"I don't know..." I responded carefully again. "I'm not trying to get you worked up, I'm just saying that it seems like they have a solid case. I don't want you to be stunned or disappointed when it turns out that they really did have this fake class for athletes."
"Well, you're wrong!" Cassidy snapped back. "You'll see, in a couple of weeks it'll turn out that this was some kind of hoax started by someone with a grudge against the athletic program. I don't know why you're even arguing against me anyway, you know how I love UNC."
"I do know," I tried to soothe her. "But I'm just trying to tell you that this thing looks real. Don't be surprised if it turns out to be true."
"You'll be eating those words and feeling like a jerk when this all gets disproved," Cassidy replied confidently.
"It doesn't look like it's going to get disproved," I responded, now getting a little irritated that Cassidy was so obstinate about this news story.
"Fine," she replied icily, "If you're so sure of yourself, then agree that you will wear UNC t-shirts and gear every Saturday and Sunday for a month after they admit that this whole thing was made up."
"No fucking way," I responded with a laugh.
"Because you know you're wrong!" Cassidy roared, her blue eyes burning with her own irritation.
"Calm down," I said. "I don't own any UNC clothes, and I'm not wearing that crap for a month."
"I have some jerseys and an old sweatshirt that would be big enough for you," Cassidy parried. "You just know you're going to be wrong."
"What do I get when it turns out this whole story is true?" I demanded.
"Whatever you want, because you know I'm right," Cassidy offered, her lower lip stuck out like an indignant child.
Irritated by her insistence on arguing, I thought over what I wanted for a moment. Looking at her pretty but angry face, the thought hit me. "You didn't like me cumming on your face that one time, did you?" I asked.
Cassidy paused cautiously before replying. "Not really. I don't hate it, but I don't really like it either, so I normally don't let guys do that."
"Fine," I said triumphantly. "That's what I want. If you're right and this story turns out to be wrong, I will wear your UNC gear every weekend, all weekend, for a month. But if I'm right, you have to let me cum on your face."
To my surprise, Cassidy didn't hesitate. "Fine, it's a deal." She extended her hand, and we shook on it, after which she said, "You're going to hate being wrong."
The days passed and the evidence began to build that the stories about UNC were true. One person resigned and others were fired. University officials apologized. The days turned into a week, and there appeared to be no doubt that UNC had permitted student athletes to attend a fake class.
Cassidy and I did not stop our deal during this time period. One night as soon as I got home from work, she jumped me and I ended up eating her out on the living room couch. She crushed my ears with her thighs as she came on my flicking, wet tongue. That Friday night, she came home from the bar a little drunk and horny, and I went down on her on her bed. She moaned loudly and deeply several times as she came, and fell asleep with a smile on her face shortly afterwards. On Saturday morning, shortly after I woke up, she rewarded me with a sloppy, wet blowjob while I lay in my bed.
But we never talked about the UNC scandal. I felt a little bad at even making the bet, knowing that the evidence on the news seemed so strong and Cassidy was blinded by her loyalty to her school. I decided not to mention our bet or try to redeem the prize we had agreed upon.
But Tuesday afternoon, when Cassidy got home from work, it was the first thing she mentioned when she walked in the door. Normally she got home before me, but that day I had changed out of work clothes and was drinking a beer while watching tv on the couch. The door had barely closed when she said, "Alright, you win. The stupid story about UNC allowing athletes to cheat was true."
I looked over my shoulder at Cassidy. She was wearing one of her tight little black skirts with matching black jacket over a white top. It always impressed me that she looked sexy and deliciously curvy no matter what type of clothes she was wearing.
"I'm really sorry about your school," I replied. "It really sucks, but it sounds like they're now trying to do the right thing by firing people." I felt genuinely bad for her.
"I know, thanks for saying that," she said dejectedly as she tossed her keys and her purse onto the kitchen counter. "But a deal is a deal. You can cum on my face."
"I don't have to, don't worry about it," I offered.
"No, no, no," Cassidy responded, shaking her head emphatically to emphasize her point, her smooth red hair waiving back and forth. "I was raised that a deal is a deal. You make an agreement, or you have an obligation, you live up to it and fulfill your part. I said you could cum on my face and you were right, so I'll let you cum on my face."
"You sure?" I asked. "I don't want to make this news story any worse for you."
"It can't get much worse," Cassidy said with a sigh, before putting her hands on her hips and fixing me with a smile. "But if it's all the same to you, I'd rather get this over with sooner rather than later. You think you could do it tonight?"
"Cum on your face?" I asked.
"Yeah, I rather just get it done with so I can know I lived up to my end of the bet. You can do it however you want," Cassidy offered, her bright blue eyes never leaving mine. "I can help you out, or I can come in your room, or you can go watch porn and just let me know when you're ready. I can get naked or whatever, I just don't want to mess up my clothes or any of our furniture."
"Well that all sounds reasonable to me," I responded with a laugh at how much thought she had put into this. I considered my options for a moment and then said, "Why don't I try to make this as easy for you as possible, to show there are no hard feelings over the bet. I'll go in my room and jerk off, and when I'm ready I'll yell for you and just finish on your face. Just go in my bathroom and we can do it in the shower so we don't make a mess."
"If that works for you, it works for me," Cassidy responded. "You want me to be naked when I come in your room?"
"Honestly, I'd prefer you look just like that," I said, "You look so sexy in those work clothes. But you said you didn't want to mess up your clothes, so come in wearing whatever is comfortable. You know I love your body, so naked works fine for me."
"Okay," Cassie responded with a smile. "That works for me. Just yell when you're ready."
Seconds later I was naked myself, sitting my desk chair, jerking off to an orgy scene from a hot, high end porn. I hadn't had to use porn much to get off, with Cassidy so willing to help when I needed, so there was something really hot about seeing those sexy bodies fucking. It was like my mind had forgotten some of the hotness of porn. My cock was rock solid in no time, and I felt the excited pleasure flowing through me like I could cum. The thought of cumming on Cassidy's beautiful face, her smooth skin and sparkling smile covered with my spunk, also got me turned on and ready to burst. But I remembered how I'd had a little trouble cumming in her hair the first time I came with her, so I took my time and made sure my balls were churning and I was really close to popping before I called her into my room.
"Cassidy!" I finally yelled, "I'm ready!"
Just a second later, my bathroom door opened and I heard Cassidy walking into my room. I was very distracted, so close to cumming. I was trying to walk from my desk to my bathroom with my aching cock in my hand, trying not to hold it so tight that I rubbed it and came prematurely. I was aware in the periphery of my vision that Cassidy was kneeling in my bathtub, but I was in for another surprise when I finally got to the edge of the tub.
"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 dr*pe 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?
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.
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.
"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.
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 bl