My Best Friend Emily

Welcome to chapter five of this ongoing story. I have always tried to make my stories an exploration of sexuality, but I think this chapter takes things to a whole new level. There is a lot of straight sex, but there is also messy play, voyeurism, BDSM/role playing, and anal. Hopefully everybody can find something they like about this story. As always, any similarities to any people, places, situations, or anything you have seen or read before is a complete accident.

I didn't sleep well that night.

Emily and I watched the rest of the Cards game quietly. They lost. After it was over we went to bed. There was no more sex. Neither of us were in the mood. Before I went to bed I crept up to the door of the master bedroom. At first I heard nothing, but eventually I thought I heard the slow, calm breathing of Lisa when she was asleep.

"Come to bed with me," Emily said softly. Without a word I followed her into the spare bedroom. Emily climbed into bed, still wearing the tank top and shorts she had changed into. I quickly stripped out of my t-shirt and jeans and slipped into bed in my boxers. The spare bed was just a single and Emily and I had some trouble arranging ourselves until we got comfortable. We slept together in the bed last Saturday night, why was it so much harder to get comfortable this time? The last time we were exhausted, satisfied after great sex and snuggled up together. This time around we were both tense and anxious, trying to get comfortable but not too comfortable; worried that Lisa would come out of the bedroom in the middle of the night and... who knows?

Emily and I finally ended up lying back to back. I felt my butt brush up against her once or twice until we staked out our positions. "Goodnight," Emily mumbled, and I said the same. I listened to Emily for a while, trying to figure out from her breathing whether she was awake or asleep. Eventually I decided that she was asleep and rolled over onto my back. I stared up at the ceiling in the darkness.

Holy crap! What did I get myself into? I thought to myself. When this all started only a week ago I didn't think about potential consequences. Hell, could I have even stopped it if I wanted to? It was Emily that suggested the sharing, the threesome. Lisa was the one that agreed. My participation was tacit. Only an idiot would've said no, right? On the other hand maybe a wiser man would've thought it through. How would Lisa really react when she saw me with another woman? Especially Emily, my best friend for half of my life, who I harbored secret feelings for and wished I could've been with for as long as I could remember. Besides, Emily was right. Lisa was crazy. I never really was able to quite put it all together before. She was always weird. She was quirky. She liked to be by herself a lot. She talked to herself all the time. She enjoyed sex but she never wanted to try anything new, at least not with me. Suddenly Emily sets off this spark and she's having sex with me in the shower, on the living room floor, trying to deep throat me... ugh, why did I have to grab her hair? If I had just let her pull away from me, maybe she wouldn't have freaked out like that. I felt a rush of anger at myself, and forcefully rolled back over onto my side. I had forgotten I was next to Emily. I felt her stir, but she was still asleep.

And then there was Emily. What she had said to me a few hours ago stuck in my mind. 'I'm attracted to the wrong type of people, to adventure, danger' she had said. Was this even about me at all? Emily told me that she had spent years looking for a guy like me, but what if that wasn't entirely true? Was this all about some sort of weird attraction to Lisa, because she's crazy? Even though Emily was my best friend, she never really talked about her sex life with me. She always hinted at having a wild time in college but she never really gave details. What was in her past? Lesbian encounters? Threesomes? Gangbangs? What if she got off on stealing other people's boyfriends or husbands? Is that what was really going on here? I could suddenly see this playing out like some bad late-night soft-core B movie. Emily is some kind of black widow-type woman. She moves in on happily married couples, drives the woman crazy, and steals the man. Of course since it's a steamy fuck-all porno she seduces the woman too.

No, that was crazy, I thought to myself. Lisa and I weren't really happily married, and Emily hasn't said anything to me about wanting me all to herself, at least not yet. But that was one of the possibilities, wasn't it? What if somehow I end up with Emily? I guess it would be a dream come true, in a way. I could imagine a life filled with baseball, blow jobs, 80's movies, and wild, experimental sex...

I groaned. The grass is always greener on the other side, isn't it? Emily had bad qualities too. She had a knack for saying the wrong thing at the wrong time. She could be just as unpredictable as Lisa sometimes, maybe not in that typical emotional way that I'd come to expect from Lisa that men associate with PMS, but she could be flighty, callous, and downright bitchy when she was in a bad mood, however rare Emily's bad moods were.

On the other hand, I thought, my mind jumping, what if Lisa confronts me in the morning and says either Emily goes or I go? Wouldn't I have to try to save my marriage? What would it be like if I had to push Emily out of my life in order to save my marriage, especially now?

I'm getting too far ahead of myself, I thought. I started to wonder how much of the night had already passed. Was I lying there thinking for an hour? More? I struggled again to get comfortable. I accidentally brushed against Emily. She made a little noise but I think she stayed asleep. On a whim, I turned so that I was right beside her, my face right by the back of her blonde head, the exposed skin of her neck. I watched her sleep for a while, letting her steady breathing calm me down. Finally I felt exhaustion taking over, and I rolled back over, eventually falling into a fitful sleep.

...I was coming out of a hazy dream, the details already forgotten. I rolled over onto my side and felt myself bump into something. Touch memory told me that I was up against a female body. My cock was up against her buttocks, already hard from morning wood. I brushed it against the soft flesh. It felt good. My cock tingled and I felt my hips jerk involuntarily, pressing myself into the soft flesh. I felt the soft flesh respond, pressing back against me. Our bodies started to shift together. I moved a little, she moved a little, until I was spooning her. I ground my erection against her buttocks again, and I felt her push back. I swung my right arm over her and pulled her closer to me. I heard a soft moan, and I now knew that it was Emily beside me, but I didn't care. I didn't know what time it was, or where Lisa was at that moment. All I cared about was the good feeling in my groin. My right hand went to Emily's breasts, fondling and squeezing her small breasts as I continued to grind my crotch into her. I heard her breathing get heavier as her arousal grew. I felt her shift her hips and press up against me harder, trying to get some stimulation on her erogenous zones as well. I slid my right hand down her belly and into her shorts, feeling her shaved pussy. Emily spread her legs and let me slide my fingers between her pussy lips, feeling her wetness and sliding it back along her clitoris. Emily moaned as I began to rub my middle finger along her hard clitoris, occasionally sliding it down her pussy lips and back up again. All the while I ground my crotch into her buttocks, my thrusts getting more insistent as my arousal grew.

"I want you inside me," I heard Emily moan softly, but I had no intention of fucking her just then. As a response I slid my fingers down along her pussy and penetrated her with two fingers. "Ohhh... yeah..." Emily gasped as I began to move my fingers in and out of her tight, wet hole. I had snaked my left arm underneath her, and I wrapped it around her, pulling her closer to me, cupping her breast firmly with my left hand.

I could feel Emily's hips start to shake. She was grunting and pushing her hips against my hand, trying to get my fingers deeper into her. I curled my fingers and I continued to move them in and out of her, searching for her G spot. Emily suddenly gave a loud grunt and her hips jerked. I held her tighter and started moving my fingers in and out of her as fast as I could go. Emily was orgasming. She buried her face in her pillow to stifle her grunts and squeals. I held on for dear life as she thrashed around on the bed. Ten, fifteen seconds went by. Finally I heard her give a contented sigh. She grabbed my right wrist firmly and pulled my hand away from her pussy. She spun suddenly, pushing me down onto my back, and she sat up on her knees at my side, pulling my boxers up and over my erection. She froze suddenly, staring towards the doorway, and I almost panicked, following her gaze. No, Lisa wasn't there. Emily had a faraway look and I knew that she was listening for any sign of her. I didn't hear anything, and Emily didn't either. She reached out and grabbed hold of my cock, giving it a few strokes. Her hand was dry. My cock was dry. The friction was a little uncomfortable. Emily seemed to guess that, and I saw her reach between her own legs, into her shorts. She closed her eyes as I watched her hand move. She pulled it back out, her hand slick with her own juices, and she used it to lubricate my cock. My cock jumped at the dirtiness of Emily using her own come as lubrication, and I felt the beginnings of my orgasm. I started bucking my hips in counterpoint to Emily's hand job, and in less than a minute I came, spurting cum into the air and covering Emily's hand and my groin. She kept stroking me until my spasms stopped and I had to pull her hand away before it got too sensitive.

Emily slid down beside me in bed, and gave me a kiss on the cheek. Morning breath, I thought. She was contemplating the hand she just jerked me off with. Her thumb and forefinger were covered in cum. I watched her put first her thumb, then her forefinger into her mouth, and suck the cum off of her fingers. I watched her, fascinated by the sight.

When Emily spoke it was in a whisper. "I hope you didn't mind me using my own juices," she said, "One thing that always bothers me when I watch porn is the spitting. Women hocking huge globs of spit to lubricate things," Emily shuddered, "Really. Keep it in your mouth."

"No, I thought it was hot," I whispered back, "And I agree about the spitting." Emily had put her pointer finger back into her mouth, and I watched her continue to suck on her finger.

Emily noticed me staring at her, and took her finger out of her mouth. "Sorry," she whispered. "Cum is an acquired taste, but once you get a taste for it, you can't get enough." Emily maneuvered herself until her head was by my groin, and she proceeded to clean my penis with her tongue. I watched her work, using nothing but her tongue, cat-like, to clean the cum off of my penis and groin. My penis had gone flaccid after she had jerked me off, but the attention made it hard again. When Emily was done she climbed back up my body to bury her head in my neck, nuzzling me, with her hand running idly through my chest hair, and her leg draped across my thigh. I felt her groin, still covered by her shorts, press against my thigh.

Emily gave a contented sigh. "I wish we could just spend the whole day like this," she whispered. "Just kissing, licking, sucking, and exploring each other. Having sex until we both can hardly walk," she added with a giggle.

I was trying to figure out what time it was. It felt like the sun was just rising. It was 7, maybe 7:30am. For me that was late. I was usually up watching SportCenter already. I tried to remember what I heard about the weather for the day. It was supposed to be cloudy, rainy. Not a pleasant day. A good day to stay in bed and do exactly what Emily was describing. Thank goodness the Cards were on the road, I thought. It may not be raining in Cincinnati. Hopefully they can get the game in later.

Emily was still pressing her groin against my thigh. I felt her jerk her hips a few times in rapid succession and then sigh. "It feels so good in your arms," Emily whispered. "I wish I knew that..."

I kept waiting for Emily to finish her thought, but she had trailed off. Curious, I tried to get her to finish her thought. "Knew what when?" I whispered.

Emily froze. She realized she said something she shouldn't have. "Forget it," Emily whispered, "Just forget I ever said it."

"No, really," I said, a little louder. "What?"

I heard Emily take a deep breath. "Really, just drop it," she said.

I knew what she was going to say. She was going to say that she realized now that she should've been with me all along. If she only knew ten or twelve years ago that she would have felt so good in my arms? Hah! I thought to myself. She never tried. Somewhere deep inside me eighteen year old me was furious. That part of me that held onto my deep feelings for Emily all these years, the part of me that hurt a little every time she told me about another guy, the part of me that felt betrayed when she went away to college and thought she was never coming back. Old wounds that I thought were healed when I met and married Lisa, only Lisa wasn't really my one true love, whatever that meant. If it was anyone, it was Emily. It was always Emily.

And she was going to start talking about how, oops; she should've realized she should have been with me all along? I felt a fury rising up inside me that I struggled to keep under control. You mean you should've gone to senior prom with me? Eighteen year old me was screaming, instead of Steve Johnson, and I had to listen to him fuck you in the next hotel room where I was sitting in the bathroom holding up Chrissy Tompkins' hair while she puked?

I rankled at the thought of Emily saying something like 'you're the guy I should really be with.' I'd heard it a couple of times in my freshman year of college, while Emily was off flunking out of NYU, before I met Lisa. I was everybody's friend Joe. I was honest, reliable Joe. Just like I did with Emily, I kept befriending the women I would rather have been dating. They would hook up with one guy or another, and it was always disastrous. "Oh Joe," they would say after they got dumped, and were crying about it on my shoulder, "You're the guy I should really be with." And I would think, really? You're going to say that to me now? You're an emotional mess. Say something like that to me when you really mean it. I suppose a weaker man probably would've taken advantage of them in those vulnerable moments, but I had too much respect for women. Damn my upbringing.

I realized my mind had been wandering for some time. Emily probably thought that I had just dropped it, and not that I was a roiling cauldron of anger. She was sliding her leg up my body, brushing her thigh along my erection. She had that faraway look again, trying to figure out where Lisa was. "Oh, fuck it," Emily mumbled, and she sat up, pulling her tank top over her head, and her shorts down her legs. Completely naked, she straddled me, taking my erection in her hand and guiding it into her pussy. I wasn't completely hard, so she slid down onto my cock easily. She placed her hands on my collarbone and started to move up and down on my cock.

I found myself glaring up at Emily. The word 'selfish' bubbled up to the forefront of my mind. Yeah, Emily was selfish. She wouldn't care about all those years that I wanted her. She wanted me now, and she probably destroyed my marriage in order to have me. It was always about what she wanted. And me, boring old reliable Joe, just glad to be with her Joe, went along with everything she ever said or wanted me to do. I felt anger welling up in me to the point that I realized my molars were grinding together.

Emily seemed oblivious to everything except for her own pleasure. She was moving up and down along my cock, her eyes closed, enjoying the pleasure she was giving herself. I waited until she had bottomed out on my cock and pulled herself back up, and then I thrust my hips back up into her. Hard. Emily's eyes flew open and she gasped. I pulled my hips back and thrust up into her again, burying my cock deep in her pussy. I was rarely aggressive in bed. I wasn't an angry person, and all during my marriage if I was ever in a bad mood Lisa usually kept her distance from me.

Emily was looking down at me expectantly. I watched her lips curl into a smile. "Go on," Emily said softly. "I like it rough."

Something inside of me snapped, and I found myself bucking my hips upwards as hard and fast as I could. Emily was bouncing up and down on top of me, basically holding on for dear life. I heard myself grunting and the bedsprings creaking. There was a slapping sound when our thighs crashed together. My mind wandered off to a random memory of a movie I had seen the previews for but never actually watched. Kathleen Turner was saying something like 'Do you like angry sex?' and Danny DeVito of all people replied 'Is there any other kind?' The War of the Roses, yeah, that's what that movie was called. I was in elementary school when that movie came out. That line was one of the first things I had ever heard about sex.

A sound snapped me back to reality. It was Emily. She was grunting, panting, moaning. My eyes wandered to the sight of her small breasts bouncing. I reached up and grabbed them roughly, pulling and twisting her breasts and pinching her nipples between my thumbs and forefingers. The rough treatment only seemed to egg Emily on more. She had gotten the hang of my frantic rhythm and was pushing back against me. She was whimpering now. "Oh... god... yeah..." she whispered, and her whole body tensed. She was orgasming. She froze and shuddered. I kept thrusting into her, even as she lost the rhythm of our fucking, her hips jerking randomly. After several seconds her orgasm subsided, and she sighed and made a move as though she was going to lie herself down against my body.

But I wasn't done with her. Not by a long shot. I grabbed her and all but threw her over, nearly right off the narrow spare bed. I rolled onto my side and pulled her back toward the middle of the bed, beneath me. I lowered myself onto her and quickly found her pussy with my cock, sliding back into her with one angry thrust. My face was mere inches above hers, and I realized I was glaring at her as I fucked her, my jaw clenched, sweat running down my forehead. I was thrusting into her as fast as I could get my hips to go. My penis was tingling but it was also sort of numb, and I knew that my next orgasm was still far off.

Emily was grinning at me. It only served to make me angrier. Holy shit, I was thinking to myself, I'm trying to take my anger out on her by fucking the shit out of her, and she's fucking enjoying it! Emily wrapped her legs around me and locked her ankles together behind my butt. She pressed against me with each frantic thrust, trying to control the pace and drive me further into her. She was really turned on; her pussy was so slick I was sliding in and out of her with no friction at all. My dick was numb and getting very little sensation from her slick pussy. I could go on fucking her as long as my lower back could stand it. And I was starting to feel an ache, right in the small of my back.

I focused on Emily's face, watching her eyes as she stared past me to the ceiling, focused on the pleasure my thrusts were giving her. Her well-lubricated pussy was making little squelching noises now as I pistoned in and out of her. In order to ignore the ache in my back I let my mind wander. I started thinking about work. Did I submit the paperwork for the changes the Petersons wanted to make to their portfolio? I think so...