The Roommate

"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.