The Roommate

"I'm pretty close," I responded, Cassidy's slippery fingers continuing to milk my sensitive rod.

Frowning, Cassidy knew that meant I wasn't close to my orgasm. With her free hand, she reached behind herself and unclasped her bra. Cassidy's big and impossibly firm melons spilled into view, her pink nipples bared for my eyes, Cassidy lifted one of her big tits obscenely and said, "You can cum on my tits if you want to."

That caused a little spark of arousal to fire inside of me, sending me a little closer to the pinnacle of arousal.

Then Mary surprised us both by saying, "You can touch my breasts if it will help you."

Mary's blue eyes were on fire with her arousal, and her thin, delicate fingers were furiously working over her wet little nub.

I took a step forward, Cassidy careful not to lose my cock in her grasp as she slid up and down my sensitive pole, and I reached out towards Mary. The thin little blond did not flinch as my hand closed over her smallish breast, and I cupped it firmly in the palm of my hand.

"Ohhh," Mary moaned in response to my hand firmly cupping her little tit. Between Mary's moan and the erotic sensation of playing with Mary's boobs while Cassidy jacked my cock, I felt more tingles bubbling up inside me.

I could feel Mary's hard nipple poking out from beneath her wet t-shirt and bra, and I rubbed at it with my thumb. This elicited a sharper, "Ohh, yes!" from Mary, who began to writhe as I played with her nipple while she played with her clit.

"You going to cum, Mary?" Cassidy asked, her tight grip still milking my pole.

"Yes!" Mary panted.

"You going to cum, honey?" Cassidy asked me.

"Yes," I replied quietly, enjoying the soft squeeze of Mary's tit flesh and the insistent jacking of Cassidy's hand.

"You going to cum because you like playing with Mary's breast?" Cassidy asked.

I looked into Mary's highly aroused face and saw the burning lust behind her blue eyes. "Yes," I replied. Playing along, I added, "Her tit feels sooo good."

Mary squeezed her eyes shut and squeaked, "I'm cumming!" Her thin little body quivered and her skinny legs shook back and forth with the power of her orgasm as it washed over her.

"Oh God," I moaned, watching Mary cum beneath me, feeling her body shake through the little breast I cupped in my hand. The tingling sparks overwhelmed me and I felt the white hot pleasure of the orgasm explode in my body.

Sensing what was happening, Cassidy barked out, "Mary! Watch!"

I forced my eyes to stay open as Mary's blue eyes flew open in time to see the first white spurt of cum spew out from my swollen cock head. The cum splatter landed wetly across Cassidy's pale chest, coating the round tops of her breasts. Then Cassidy positioned her mouth obscenely over the head of my cock, looking out of the side of her eyes at Mary. My next three shots of cum spewed into Cassidy's waiting mouth, and Cassidy smiled around my dick.

"Oh shit!" Mary cried out, her eyes squeezing shut again, and then her body was shaking in another orgasm. Mary's fingers moved more slowly over her clit as the second orgasm flowed through her little body.

As my orgasm subsided, I looked down to find Cassidy already wiping her chest with a towel. "That was hot," Cassidy said with a bright smile, "Super hot. I don't think we could have timed or planned that better."

As Cassidy retrieved her bra, Mary followed her lead and went in search of her discarded bottoms. "It was hot, wasn't it?" Mary said with a giggle.

"Amazing," I agreed.

We gathered up our things quickly and were soon tip-toeing out of the pool room. I never saw Mary again.

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The next morning I woke up naked with a nude Cassidy in the bed next to me. My mind was clouded by a slight hangover, but I also recalled the incredible memories from the day before.

As I stirred, Cassidy did too, the sheet and comforter sliding off of her large, round naked breast as she reached up to rub her eyes with her hands. Her pink nipple popped into view, capping her firm tit flesh, her skin glowing in the morning light. Waking up next to Cassidy like that, I felt like I had never been happier.

Cassidy leaned her head back to look up at me, her blue eyes sparkling in the morning light, and she said, "Good morning, sunshine" with a beaming smile.

"What was that all about, last night?" I asked her. It was the first thought to pop into my head.

Cassidy rolled herself onto my body so her big breasts were pressed against my chest and she looked into my eyes from just a few inches away. "You didn't have fun with Mary last night?" The morning light set Cassidy's red hair aglow behind her pretty blue eyes.

"Yeah, I did," I replied with a smile of my own.

"So what's the problem?" she responded.

"Why did we have to do all that? We could have just come back to the room and fooled around the two of us. Why did we have to mess with Mary like that?" I asked.

"Come on," Cassidy replied, sounding slightly indignant. "Couldn't you see it from the moment she watched you cum at the table? Mary WANTED that. She was looking to fool around, that's why she stuck around at the pool."

A moment of silence passed between us while I considered her response. Cassidy seemed to take that as agreement and continued, "I thought it was hot, and you had fun, and Mary looked like she came pretty hard. I bet that was the hottest thing sweet, innocent little Mary ever did. So where's the problem with that?"

"I don't have any problem with it," I responded quickly. "I was just curious. Sometimes I like it when it's just the two of us having sex. You seem to like it... spicier, and I was just wondering why."

Cassidy's arm slid down my chest, her hand found my cock and gave it a playful squeeze. "We have SOOO much time for just the two of us to have sex. We have sex all the time now, whenever you want. I want to have FUN! I want to do things that I may never get to do again, while I still can."

Cassidy's thumb was gently stroking the underside of the crown of my cock, distracting me a little. But I had rarely seen Cassidy speak so passionately. I felt like I had hit a nerve, and I wanted to know more.

"Why are you so insistent on doing all this crazy stuff?" I asked. "I mean, don't get me wrong, I love it. I just want to know why you love it."

Cassidy looked thoughtful for a moment, but then her blue eyes and her pretty face took on the mischievous look I had grown to know so well. "When I was growing up, I always wanted to be super good. I grew up in a very religious family and I loved it, and I still do. I think my family is great. But there were all sorts of things I didn't do that my friends were doing. The biggest was sex. I'd get together with my closest girlfriends and they'd all be talking about sex, and pretty soon I was the only virgin. I thought they were crazy, fooling around like that. It was bad and it was dirty and you could get into serious trouble. And a lot of the time they didn't enjoy it, but they would giggle and whisper secrets and it was like they were all in on something and I wasn't."

"I really didn't mind, I totally thought I was doing the right thing," Cassidy continued. "But then I got to college, and one night I got a little drunk with this girlfriend of mine. And she was very cute and super sweet but also really super sexual. And one thing leads to another, and the next thing I know she's playing with my pussy with her fingers, and then she just went down on me. And it was the dirtiest thing I could do! Not only was I fooling around, I was fooling around with a girl! And she had her mouth on my pussy!! It was SOOO wrong."

"But she knew exactly what she was doing. I came so hard on her tongue, it was amazing. I don't think my body ever felt that good before. She made me cum hard twice that night, and then the next day it just wasn't a big deal to her. She did this kind of stuff all the time, and she was like, it happened and now we're cool. But it was a SUPER big deal to me."

"So then I started fooling around more," Cassidy went on. "Sex was FUN. Sex felt GOOD. I wasn't a slut or anything... you better NEVER think that I'm a slut. But I was more open to exploring that and letting sex happen. And I really loved it. Suddenly I realized all the things I had been missing. I didn't get to do all the stuff my friends had experienced and I never would. And that's why I don't want to miss out on ANYTHING anymore."

Cassidy's fingers were still lightly rubbing up and down my cock, and my member was starting to slowly grow through her attention. "What do you want to do right now?" I asked.

"I want to fuck again," Cassidy responded with one of her dazzling, bright smiles. "I want to fuck however you want to fuck."

Moments later, Cassidy was on her back with her eyes closed, my head between her legs and my tongue intently lapping at her pussy. "Oh fuck!" she moaned, "You always know just how to stroke my clit with that tongue of yours." I was rubbing the full length of my rough tongue over her most sensitive spot, lapping up her flowing pussy juices as I went, my fingers spreading her outer folds to fully expose her sensitive little button to my attention.

When I switched to very rapidly flicking just the tip of my tongue firmly against her wet clit, Cassidy cried out, "Oh, oh... I need your cock."

Unwilling to stop my onslaught as my warm mouth closed over Cassidy's pussy, I swung my body around so my knees were on either side of Cassidy's head and my cock was right above her face. Cassidy quickly grasped my hard shaft and slipped the head of my dick between her soft lips, where her hot mouth went to work on sucking the head of my member. As we 69ed, I slipped two fingers into Cassidy's tight pussy and began to finger fuck her deeply and quickly as my wet tongue continued to lash back and forth over her clit.

"Oh fuck, oh fuck," Cassidy began to pant awkwardly, mumbling around my dick as my manhood filled her hot little mouth. "I'm going to cum."

I bored down harder on Cassidy's pussy, my tongue flicking quickly back and forth while my two fingers flew in and out of her hot, wet, hole.

"MMMMMMMMMMMMNNNNGG!!" Cassidy groaned loudly as she came. She had closed her lips around my member and her moans were vibrating my cock in one of the most erotic ways I had ever experienced. Her hips bucked a little against my tongue as she surrendered to her orgasm and tingled my member.

I was so turned on, as soon as she was done cumming, I flipped Cassidy onto her stomach and lined up my cock head at her pussy entrance, ready to fuck her from behind. Cassidy raised herself up onto her knees, then looked back at me from beneath her red hair with a smile. "Go ahead, lover," she teased as she shook her firm, round ass at me.

I slowly and carefully worked the full length of my cock into Cassidy's tight, wet hole, causing Cassidy to arch her back deeply as my thick dick penetrated her. But as soon as I bottomed out, I grabbed Cassidy's hips and began ramming my cock in and out of her. Cassidy yelped as I fucked her hard, slamming my long cock into her hot little hole, her ass cheeks bouncing back and forth with my assault.

I could feel the pleasure of my orgasm building inside of me as Cassidy moaned from my hard fucking. Then I realized that beneath her body, Cassidy's big tits were swinging back and forth from the force of my pounding. I could hear her nipples sliding back and forth across the sheets beneath us.

Close to the point of cumming, I wrapped my hands around Cassidy's taut, young body and gripped her big melons with both of my hands. I pulled her up against my chest, burying my cock deep inside of her wet, slippery tunnel, as my hands mashed her big, round breasts against me. I felt her nipples pressing into the palms of my hands, and then I came.

The orgasm burst hard inside of me, and I blurted out, "Fuck yes!" as I felt my cock begin to deliver its hot load of cum deep inside of Cassidy's pussy. I held her body close to mine with my firm grip on her full, round breasts, and my cock twitched deep inside of her and squirt after squirt of my cum emptied my balls into her tight, soft pussy.

We collapsed into a sweaty pile on the bed together, both wearing big smiles and panting a little from the effort. I leaned forward and kissed Cassidy softly on the lips. When I drew back, it seemed she was wearing a look of surprise on her pretty face.

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The raunchy wedding weekend with Cassidy had seemed so absolutely perfect that I was totally unprepared for what came next. I settled back into my work week routine, but Cassidy was rarely around. We were both home only one night that first week, and while Cassidy wasn't cold or distant towards me, she also wasn't super friendly. With all the crazy sex from the weekend, I wasn't feeling particularly frisky or in need of some alone time with her. But with all her talk about "letting sex happen," I had assumed that we were headed to a wild, care-free level of hedonism that would make everything we had done before seem tame.

I might have caught on sooner that something was amiss, but my work was eating up all my time. As much as I complained, I kind of liked how busy I got. It kind of felt like being an adult for the first time, complaining about long hours and how exhausted I was when I got home late. My favorite part was the extra money, I started making a decent amount of overtime that padded my pay check nicely. It also helped that I was spending most of my work time with Kristen, as our bosses were working on the same project. In addition to being very cute, she was also a lot of fun to be around. She made the long work hours easier to bear.

Looking back, I think maybe I knew something was up after Cassidy and I didn't have sex at all the weekend after the wedding. I thought maybe she was on her period, because she didn't seem interested in being intimate and we had already established that pattern of never fooling around during her time of the month. But the alarm bells really started going off for me when Cassidy didn't come home one night early the following week. I was a little worried and texted her around 10:00, and when she didn't respond I started to get seriously worried. I was sick with concern, couldn't sleep, until my phone finally buzzed at 2am with the message "Hey, I'm great, spending the night at a friend's place."

I didn't see Cassidy the next day or night, I had to work late and she was already in her room by the time I got home. The next night I finally caught her in the kitchen when I came home. As soon as I walked through the door and saw her standing there, I blurted out, "Hey, I'm sorry if I come off as a little over protective, but I was kind of worried about you when you didn't come home the other night."

Then I stood there awkwardly, realizing that all the words had come out in one big jumbled rush. Cassidy fixed me appraisingly with her blue eyes, as if she was measuring me, and finally said in an even voice, "Sorry about that. I was hanging out with some friends and it got late so I just slept over at their place."

I took a deep breath, focusing on trying not to sound like I was in a panicked rush, and replied, "I'm sorry," even though I didn't really know why I was sorry. "I know you don't owe me a phone call or anything. I'm not in charge of you. I just got worried when you didn't come home." Trying not to sound too concerned, I left it there.

"Okay, I understand, that's nice of you to be concerned" Cassidy responded, still very even in her voice. "If I can't make it home for the night, I'll try to give you a call to let you know. Is that okay?"

"Absolutely," I responded quickly, even though the word "try" wasn't really okay with me. "Thanks."

I didn't see Cassidy again for the rest of that week, the weekend, or the following week. I came home pretty late a lot of nights, so I know even now that she probably wasn't purposefully trying to avoid me. I'd get home and Cassidy would already be in her bedroom. But that weekend I was home most of the day, and Cassidy wasn't around. Friday night I went out to happy hour with my coworkers to unwind after a long day at the office. Both Saturday and Sunday Cassidy left early in the afternoon and didn't get home until very late at night.

Having gone a full week without seeing Cassidy at all, I was in a strange mood that Friday. Four of my coworkers stayed with me until almost 8:00, working on our big project, before we finally called it quits. The one point of comfort was that our bosses were still in the office when we left. When someone suggested we all just go out to a restaurant and get drinks and dinner together, sort of like what we had done the previous Friday, it sounded like the obvious best thing to do.

Kristen was there, her chestnut brown eyes full of life and laughter. There was a lot of loud laughter around the table, unwinding after a very long week at work. We each had a couple of drinks before the food arrived, and a couple more drinks during the meal. We hesitated on ordering the second round of drinks for after the meal, but it seemed like the right thing to do. All those rum and cokes for me is why I don't remember much of what we talked about. But I do remember Kristen's bright smile, the cute little dimples in her cheeks, and the way my heart seemed to skip a beat when she was flashing that pretty smile and her eyes turned towards me.

After we settled the bill, we had that awkward moment of goodbyes where everyone stood outside the restaurant, chatting for a little too long and trying to figure out how we were all getting home. It turned out that Kristen and I lived in the same direction.

"I can walk you to your place if you want," I offered, "I don't mind." I looked at my watch and was surprised to see that it was after 11. "Plus, it's getting late."

"You sure?" Kristen asked. "You're going to walk the whole way home? It's pretty far from here to your place."

"Oh yeah," I responded, "too expensive to take a cab, and I could use the walk."

"Okay," Kristen responded with a smile. "That would be great."

I swear to you that I had no ulterior motive when I offered to walk Kristen home that night. I was fully planning to head straight back to my place afterwards, planning in my head to drink a little water before bed to stave off any hangover. The conversation was fun and pleasant, and I really enjoyed talking to Kristen. Still, it came as a surprise when we got to her building and Kristen said, "Hey, you want to come up and have a drink or something before you head home?"

The even bigger surprise was when I quickly responded, "I'd love that, if you don't mind." It felt like the words were coming out of my mouth before my brain even had a chance to register what I was saying. I'm still not sure why I said it. Part of me suspects that I was feeling lonely after spending all my time with Cassidy and then suddenly not having her. Part of me suspects I was just drunk and turned on by Kristen.

The biggest surprise (unless you remember where you are reading this story) was that five minutes after walking in the door to her apartment, Kristen was sitting on my lap and we were making out on her couch. It was an epic make out session: no words, no heading for second or third base, just 30 minutes of sucking face. Her lips were so soft and full, I couldn't help but start comparing everything about her to Cassidy. I tried to drive those thoughts out of my head, and focus on Kristen, but I couldn't help noticing all the new things that were different from Cassidy. For example, Cassidy liked to swirl her tongue around mine when we were French kissing. Kristen would dart her tongue between my lips and brush my tongue, and then pull her tongue back quickly, like she was playing coy. And Cassidy liked to move all over the place, sometimes she'd nibble on my neck a little and then go back to kissing me softly on the lips. Kristen held my face in her hands like she was trying to zero in on my lips and make sure she didn't miss a single kiss on her target.