Fuck My Roommates

College is usually the best time of your life. Sure, the workload is a lot more than you ever had to deal with in high school, but that's usually overshadowed by the new friends you make, the things you learn to prepare you for real life, and of course the parties. It was at one of the many college parties I attended in my sophomore year where I met Kim. We were introduced through a mutual friend and hit it off almost immediately. Pretty soon we were inseparable, spending as much of our spare time as we could together. Unlike me, Kim lived off-campus, in an apartment complex that rented almost exclusively to college students, although there were a few long term tenants there. As long as the parties didn't get too out of hand, there were no problems.

Kim had two roommates, Madison and Annie, that she had been living with since freshman year. Madison (or Maddy as she preferred to be called) was a petite brunette (although her hair was more of a deep black than a dark brown) with a tight athletic body, pale blue eyes that a man could drown in, and a smile that could light up a room. Annie was also a brunette, but was a little on the heavy side. Don't get me wrong, she wasn't fat by any means, but she wasn't exactly slim and trim like Maddy or Kim. She was a little shy because of it. However, I could see past that to see that when she smiled she also lit up the room, and once she got to know you and opened up she revealed a wicked sense of humor, and a sharp sarcastic wit that caught most people off guard.

Of course Kim was the focus of my attention. Stunning in every respect, a brunette as well (I've always had a weakness for them), her eyes kept me entranced when she looked at me, she had the perfect body, she was smart as a whip, and much like Annie, had a sharp wit and never was at a loss for words, whether she was talking about something serious or silly. She was also an animal in the sack.

Maddy had met her boyfriend Eddie at the same party where I met Kim (in fact I think they were introduced by the same friend), but unlike Kim and I, Maddy didn't click with Eddie right away, and there were almost always problems between them. Their relationship lasted only three months, and Maddy had jokingly sworn off all men after they broke up. Annie didn't date much due to the fact I mentioned earlier about her being a little self conscious about her weight. In fact, I think I only saw her with a guy once, but she never talked much about him, so if there was anything between them it wasn't serious. I spent a lot of time at Kim's place (since I couldn't have her over at my dorm all the time), so I got to know Maddy and Annie pretty well.

Which is how the whole situation I'm about to describe came about.

Kim and I weren't trying to hide the fact that one of the main reasons I came over all the time was to have sex with her. And Kim wasn't exactly quiet while we were getting it on. Now, I'm not saying I'm the world's greatest lover or anything, but I knew what she liked and made sure to do what she liked every time we fucked. One Friday night as we lay in bed basking in the afterglow she turned to me.

"Scott?"

"Hmm...?" I said, asked turning to face her.

"You'd do anything for me, right?"

"Within reason, sure." I said, "Why, what's up?"

"Well... I don't know how else to put this, so I'll just say it. I want you to fuck my roommates."

I blinked and raised an eyebrow. "Do what now?"

"I want you to fuck Maddy and Annie." she said matter-of-factly.

I waited for her to start laughing, I checked her face to see if I could see the serious look she was giving me start to crack, anything to tell me she was joking, but she remained serious.

"You're serious? You want me to fuck your roommates?" I asked, "You're seriously telling me I can go and fuck Maddy and Annie? No strings attached?"

"Yes, I'm serious." she said, "Look, I've seen the way you look at them, and I've seen the way they look at you, and I've overheard some of the things they've said about you when they thought I wasn't listening."

"What exactly have they been saying?" I asked pushing myself up to a sitting position.

"Well, since we're not exactly shy about the fact that the main reason you come over here is to fuck my brains out, they've been wondering what they're missing out on, and have both said they'd love to get you alone to see what all the fuss is about." she sat up as well, the blanket falling down around her waist, exposing her perfect tits. "The only reason they haven't is because of they're worried about what it would do to our friendship. But I've noticed they act differently when you come over. They bend over more... a lot more to give you cleavage shots and Maddy loves showing off that ass of hers."

Maddy did have a nice ass. I don't think I mentioned that earlier.

"So what, you want us to just march over to Maddy's bedroom and have me fuck her while you watch or something?" I asked, "I mean, I'm not opposed to the idea, I'm just trying to figure out the logistics of it here."

"Well..." she said, and I could see a look creeping onto her face, a look that said she was planning something devious. "I want them to think they're getting away with something."

"Okay, before I get all excited," I said, "This is your last chance to tell me you're joking."

"Not joking." she said reaching under the covers and grabbing my cock, "Besides, I can tell you like the idea."

I was hard as a rock and she was right. I did like the idea, and now that Kim had pointed it out, I did realize I saw a lot of cleavage when I came over to visit. Maddy seemed very fond of tank tops whenever I was over to visit, and while Annie wasn't one for skimpy clothes, she almost always had a v-neck t-shirt on.

"One last question. Again, not that I'm opposed to the idea, but why me? Why not find guys who are interested and try getting them together? One of our unattached friends?"

"Because that would make me feel like I'm pimping them out, and that's not what I'm looking to do here. They've both pretty much come out and said 'I just need to get laid', and I know and trust you." Kim said.

"So you'll pimp me out instead?" I asked.

"Well no," she said, chuckling which made her tits bounce. "It's not like there's money involved. I prefer to think of it as lending my friends my favorite toy."

"So what's this idea of yours?"

Fucking Madison:

Maddy was already home, we could music playing in her room as Kim and I ran upstairs to get it on. So, now we were just biding our time until she came out of her room. Eventually she was going leave her room to either head downstairs to get something to eat or go to the bathroom. Soon enough we heard the telltale squeaking of her bedroom door and then the sound of the bathroom door closing.

"Okay loverboy," Kim said smiling "That's your cue."

I got up, pulled on my boxers and waited by the door until we heard the toilet flush. I heard the sink run next as Maddy presumably washed her hands. Then I opened the bedroom door just as she exited the bathroom. I faked being tired, I let out a fake yawn, half closed my eyes and scratched my head and basically acted like I had just gotten out of bed.

"Oh! Hey, Scott." she said, jumping a bit. "You startled me."

"Sorry..." I mumbled, still playing half asleep. "I gotta go... yanno..." I said gesturing towards the bathroom, but I was drinking in the spaghetti strap top that was barely holding her tits in, and the skimpy black panties that showed off more of her than I'd ever seen. All the blood flowed right to my dick and made an unmistakable tent in my boxers. Maddy's eyes immediately focused on it.

I took a step towards the bathroom but Maddy didn't move, her eyes glued to the tent in my boxers. I followed her gaze. "Oh, sorry bout that..."

"That's okay." she said smiling a bit and finally bringing her pale blue eyes up to look at me. "I didn't mean to embarrass you. It's just kind of hard to miss. And... I've always been kind of curious."

I raised an eyebrow. "Really? About what?"

Maddy blushed and hid her face from me before brushing her raven locks out of her face.

"Well, I can sometimes hear you and Kim going at it... and I was wondering..." she lowered her voice "...if I could see it?"

I glanced back at Kim's bedroom door, I knew she was probably standing on the other side of it being as quiet as she could while listening to us.

"You wanna see my dick?"

"Shhhhh..." Maddy said.

"Ahh, don't worry about Kim, she sleeps like a rock." I looked back again, "Ahh what the hell, in there."

We ducked back into the bathroom and I pulled my boxers down and my dick sprung into view. Maddy's eyes grew wide. Now I'm not gonna lie and tell you I've got a huge 12 inch dick or anything (to be honest, I've never bothered to measure it but I'm guessing I'm about average), but I'm not exactly hung like an infant either.

"Wow, much bigger than Eddie's." she said, "The couple of times I saw it. Can I... can I touch it?"

I reached over her and pushed the bathroom door closed. She took that as a yes and took my throbbing cock in her hands, gently stroking it up and down. I reached into her top and set her tits free, they were slightly smaller than Kim's, but stood proud and firm on her chest, her small nipples as hard as rocks. She took the cue and let go of my cock long enough to take her top off, and went right back to jerking me off.

"God, I'm so wet..." she said, taking my hand and guiding it to her crotch, "See?"

I could feel the heat and wetness through her panties, and quickly pulled them off, and ran my fingers over her pussy lips. She was indeed soaking wet.

"Would you... would you fuck me? Please?" she said, "I mean I know you're with Kim and all... but..."

Now it was my turn to shush her. "Shhh... turn around and bend over the counter." Her eyes lit up and she turned around and bent over the counter. I got behind her and slowly guided my rock hard cock into her soaking wet pussy. She let out a squeal of pleasure and immediately clamped her hand over her mouth. I almost laughed because I knew if Kim wasn't still in her bedroom, she was probably right outside the bathroom door. The fact that I was fucking her roommate, with her blessing no less, made it all the more exciting. I waited for a moment for Maddy to get used to having me in her before I started slowly fucking her. There was no sound in the bathroom except for the squishing of my cock sliding in and out of her slick love canal.

She kept having to cover her mouth as she moaned in pleasure every few strokes. My eyes were going back and forth between our images in the mirror and my cock moving in and out of her.

"Fuck... feels so goddamn good." she moaned before covering her mouth again as I picked up the pace slamming into her now. "Fuck me, fuck me, fuck me, fuck me." she moaned throwing her head back, her jet black hair hitting me in the face. I reached around and grabbed her small but firm tits, gently pinching her nipples, as she gasped again, this time not bothering to cover her mouth, locking eyes with me in the bathroom mirror.

"You feel so fucking good," she groaned "So this is what it feels like to get fucked by a real man. I can see why Kim likes you."

"You're not so bad yourself," I said, "That pussy is nice and tight, and these tits..."

"Oh fuck, I think I'm cumming..." she covered her mouth and moaned loudly into her hand and her whole body shook as her orgasm hit. It dawned on me that we weren't using protection and I could feel the tingling in my balls that told me I was about to cum. I pulled out and stroked myself to orgasm, having to bite back my own groans of pleasure, as I shot several loads of cum onto Maddy's firm ass.

She slowly slumped to the floor, brushing her hair out of her face, and I leaned against the counter, my cock slowly going limp. Both of us trying to catch our breath.

"Oh my fucking god that was amazing." she said looking up at me. Then panic crossed her face. "Oh shit, I just fucked my best friend's boyfriend!"

"Shh... I won't say anything if you don't." I said kneeling down next to her, gently cupping her face in my hand, "It'll be our little secret."

"I hate keeping secrets from her..." Maddy said, "But I don't think I could tell her if I wanted to."

I grabbed our clothes. "I'm gonna get dressed and go back to bed, and I think you should too."

"I just need a minute here." she said grabbing a towel.

I stood up and slipped my boxers back on, and with one final look I left her to compose herself.

Kim was standing just inside the bedroom door. "Well...?"

"One down, one to go." I said.

"Good. Now, Annie's working at the coffee shop and since it's Friday night, she should be home in a couple hours. So you should get some rest if you're going to fuck her too."

"I still can't believe you're okay with this." I said, getting back into bed with her. Kim reached over and pinched my arm. "Ow! What was that for?"

"To prove to you you're not dreaming. Yes, I told you I'm okay with this. I trust you. Now, you remember the plan right?" Kim asked me.

"I remember."

Fucking Annie:

Annie worked at Hallowed Grounds, a coffee shop on campus that usually closed at 10 on Friday, then there was a half an hour of clean up after they had gotten all the customers out, and adding in her drive home, she usually got home close to 11. I had taken the opportunity after fucking Madison to take a quick nap to recharge. Kim shook me awake about 15 minutes before Annie got home to give me time to wake up and be ready. About ten minutes later we heard Annie's key hit the lock, and I got out of bed and moved to the door, this time deciding to be even more daring and step out of the room naked.

As we heard her come up the stairs she seemed to be talking to herself, and she sounded pissed.

"Fuckin' asshole... shoulda smacked you in your fuckin' face... I don't need a paycheck that bad..."

I stepped out of the bedroom, again playing like I was half asleep and needed to use the bathroom. Annie was still grumbling about something.

"...oughta tell you to shove your job straight up..." she noticed me staggering to the bathroom as she flicked on the hall light.

"Ah..." I mumbled, covering my eyes.

"Oh jeez Scott, I'm sorry. I... Oh..." Like Maddy before her, her eyes focused right in on my crotch, only Annie got to see my dick without my boxers obscuring her view.

"S'ok..." I said, still playing the barely awake version of myself. "Jus' goin' the the john. Whassa matter?"

She didn't say anything for a few seconds, but finally managed to pull her eyes away from my semi-hard cock and look at my face.

"Well for starters, you're naked. And second, I just had a really bad fuckin' night." she said, reaching behind her for the doorknob to her room, not wanting to take her eyes off me. "I just need to forget about this day." Her eyes dropped back down to my dick.

"Anything I can do?" I asked taking a step towards her.

"If you weren't Kim's boyfriend I'd say yes." she said, still focused on my now fully erect cock. Just thinking about what I was getting ready to do, made it stand up at attention.

"Why, what'd you have in mind?"

She finally turned away from me and went into her room. "Forget it. I can't..."

"Can't what?" I asked, taking another step toward her as she took off her jacket and tossed it onto her desk chair.

She turned back towards me and bit her bottom lip. "Ask you to... you know. You probably wouldn't want to anyway."

"All the times you tease me, and you think I wouldn't want to?" I asked.

"You actually noticed that?" she asked "You never reacted. I guess out of respect for Kim. But, are you saying you would? I mean, you're my best friend's boyfriend."

I followed her into her room and closed the door behind me. "It sounds like you need some stress relief, I've got, well, this." I gestured to my hard on, "And Kim's asleep. Plus I've always wanted to see what you've been hiding under that shirt."

"If this is a dream don't wake me up." Annie said, and whipped off her work shirt and tossed it off to the side, her bra quickly followed, and for the first time I feasted my eyes on Annie's tits. She was much larger than both Kim and Maddy, her tits had to be D's, maybe even double D's. They were definitely more than a handful (side note: anyone who says more than a handful is a waste, never had more than a handful), her nipples stood up like pencil erasers from areola that looked to be as big as quarters, maybe slightly larger. They weren't pert and perky like Maddy's were, but they were still a feast for the eyes. Annie couldn't get her clothes off quick enough, she fumbled with her belt for a second before she got it undone and quickly kicked off her shoes and shimmied out of her pants and panties. Like I said before, Annie was what some people might call overweight, but she wasn't fat. In fact, seeing her naked for the first time, she looked perfect to me. Filled out in all the right places, she was... I guess solid would be the best word to use, especially in those huge tits of hers, I couldn't wait to get my cock inside her. Neither could she.

She lay down on her bed and spread her legs for me, and I could see she shaved her pubic hair to what's commonly referred to as a landing strip. I widened my eyes in appreciation.

"You like?" she asked, reaching down and playing with herself. Like Maddy she was already wet. "I have to admit, when I hear you two going at it, I can't help myself and I just have to get myself off. I furiously masturbate while listening to you before I squirt all over myself. Again, if this is a dream, fuck me before I wake up."

This was a side of Annie I'd never seen before. Apparently hiding under her sometimes shy exterior was a nympho. I quickly got into bed with her and guided my cock into her, slowly like I did with Maddy earlier. Once I was all the way in I noticed how much tighter she seemed. Then I realized she was clamping down on me. Apparently kegel exercises do work.

"Oh my god, that feels so fucking good." She moaned, "It's been way too long. Fuck me, Scott. Fuck me hard."

I obliged and started slamming my cock into her, watching her huge tits bounce on her chest, grabbing one of them as I did and lowering my head to it to lick and suck on her thick nipple. I kept up the pace, fucking Annie hard, looking down at her now sweat covered face.

"You're a little animal, aren't you?" I gasped out as she wrapped her legs around my waist and dug her nails into my back.

"I may not have been fucked in a long time, but I think about it a lot." Annie gasped, "And I've been thinking about this for a long time."

For a long moment the only sound in the room was our heavy breathing and the sound of flesh slapping flesh as I slammed my cock into Annie's wet pussy.

"Make me cum, Scott. I want to cum on your cock. Fuck me, just like that... yes... yes..." she suddenly grabbed her pillow and bit into the corner of it, muffling her orgasmic scream as she clamped her pussy down on my cock and I could feel her get wetter as she came all over my cock just like she wanted to. I'd never been with a woman who could squirt before. She dug her nails into my back as she came.

"Holy fuck..." she mumbled as it gradually passed. "That was fucking amazing. Kim's a lucky girl."

I had slowed down a bit, but didn't stop. "Glad you enjoyed it." I said smiling. Annie smiled back at me.

"Now you need to cum." She grabbed her huge tits and pushed them together. "Right here. Cum on my tits."

I pumped her a few more times and then pulled my cock out and jerked off over her tits, my hand moving faster and faster as she watched with anticipation. It took about a minute before I felt the familiar feeling in my balls that told me I was about to cum. I groaned and used my free hand to brace myself against the wall as I aimed the head of my cock at her right tit, shooting cum onto it before aiming at her left tit letting loose with some more. Annie grabbed my cock, and rubbed the head over her nipples and what little cum I had left in me oozed out as she did.