28 comments/ 402157 views/ 62 favorites How I Fucked My Best Friend's Wife By: Wpfister This story is pure fiction. It never happened. Although I admit that my best friend has a wife who looks like this and it MIGHT happen if I get my hands on her! ************** I've known Mike and Dawn since junior High School. Mike is my best friend and Dawn is his wife and also one of my closest friends. They've been together since we were all juniors at Warren Harding High School, way back when. My name is Randy, by the way. I guess I've always had a thing for Dawn, but Mike found her first and I stayed out of his way. It was one of those unrequited things, where I spent a lot of time jacking off just from thinking about her while she probably had no idea that I wanted her so badly. But I wasn't going to step on my best buddy's toes. They hit it off right away and started dating as soon as he mustered the courage to ask her out. They went to the prom together and had their first fuck, the first for either of them, that night. I was in the next room in the hotel fucking some slut I never saw again, wishing it was Dawn. They started living together as soon as they were old enough to leave their parent's homes. They've been married about ten years now. Mike and I played football together, me at Outside Linebacker and Mike at Free Safety. Dawn was a cheerleader. There was a lot to cheer for, for we had a good team and Mike and I were All City in our senior year. After High School, when many friends drift apart, Mike and I were drawn closer. We stayed in the area when many of our best friends joined the service and spread all over the globe. We both liked to work on our muscle cars. He's a Ford guy and I'm into Pontiac. We had the same hobbies. We had the same goals. The difference was Dawn. Mike had it good. I went through a string of psycho girlfriends and got married twice, neither time very successfully. Mike and Dawn seemed made for each other and they stayed happily coupled all these years. I envied him for that, and surprisingly, he envied me for the variety of women that I had sampled during this time. I suppose even Michelle Pfeiffer would become ordinary if you slept with her every night for almost fifteen years, but it seemed hard to imagine. I would have traded lives with him, anytime. Dawn is an Irish beauty. She is a bit tiny at 5 ft, 3 in, but she's long legged for her height and well proportioned. She doesn't have big tits, but they're perky, firm and a nice handful. They aren't going to be sagging around her waist when she hits fifty, and you couldn't help but notice the way her nipples pointed upward and the perfect shape of her tits when she wore a thin T-shirt. She has an hour glass figure and a heart-shaped ass that you could bury your face in and never come up for air. Her arms and legs are toned and shapely, even her feet are cute, with long toes and a high arch. I have a foot fetish and I'm pretty sure it got started because Dawn wore these insane fuck-me shoes the summer we graduated. Dawn's skin is an alabaster that was almost translucent, yet she had few freckles. Her eyes are green and her hair is a reddish brunette that had been much redder as a child. Her face somewhat reminds me of the singer, Amy Grant, maybe because they share the same bone structure or maybe because of the sexual innocence they both project. Mike is a little bit of a troglodyte to look at, a real odd match for Dawn if you measure just by looks. He's below average in height, but stocky, with a barrel chest and thick arms. Strangely, he has bird legs, so he looks like a beer keg on stilts. No one was going to mistake him for Robert Redford, but he was a decent looking guy and one of the nicest guys I've ever known. His only problem is that he likes to drink a bit too much and he doesn't always hold it so well. That didn't bother me in the old days, because I was usually just as hammered. As we got older, though, I slowed down and he didn't. I'm a decent looking guy myself. At least, I've never had a problem getting a date. I'm a little less than six feet tall, but I'm a muscular 215 lbs. I never stopped lifting weights after I hung up the cleats, and I have the chest, arms and legs to show for it. I guess I never stopped pumping the iron because I hate the way I feel when I stop and I like the way I look when I have a nice V shape to my torso. The clothes hang better, and the women are friendlier. Dawn and I weren't just friends because I hang out with Mike; we would be friends even without him. I can't recall a single argument that the two of us ever had in all this time. We're completely simpatico on so many things. Politics, religion, sex. Mike has opinions, but mostly he's apathetic about these things. He wouldn't even vote if Dawn didn't drag him to the ballot box every time. Sometimes we would have dinner together and Dawn and I would debate the next election and talk about world events all night. Mike would mostly sit and yawn and drink whiskey. Often, I brought a wife or girlfriend, and she would sit and stare daggers at Dawn all night while Dawn and I talked like we were two pages from the same book. I've never had another relationship with a woman that was so healthy, so I cherish her for that. This story really begins with the Consumer Electronics Show in Las Vegas a couple of years ago. When I'm not spending my time pumping iron or envying Mike, I work as an event manager for a large Hi-Fi hardware manufacturer, working trade shows and events all over the country. We usually didn't do the trade shows in Las Vegas, but one year the CEO decided to try it. It was a real break from the monotony for me. As soon as I landed I checked into the Rio and upgraded to a suite with a jetted tub. When I traveled on the company dime, I did abuse it a bit, I admit. But compared to the jerks in marketing, I was cheaper than a Scotsman. I decided to head down to the Casino to watch the crazy Mardi Gras parade the Rio throws about ten times a day. I was catching the cheesy bead necklaces they throw from the floats when I saw a familiar looking body nearby. I knew it couldn't be who I thought it was, but now I was intrigued. Her back was turned to me and I almost drooled at the sight of her perfect, tight little ass. I had to get closer. If her face matched the rest of her, I needed to make a move. I was still fixated on her ass, but her legs were pretty damn fine as well. I could see myself running my tongue up and down those legs, and then tasting her honey. Oh yes, she would be mine. I drew closer, and she turned to the side to catch a string of beads that someone tossed from a float. She missed, but I reached up and caught it. My football skills still served me and I already had about eight or ten of the damn things. And I also got a look at her face. It was Dawn. I walked up and said "Hello, gorgeous," and put all of the beads around her pretty, white neck. She seemed as surprised to see me as I was to see her. "What the hell are you doing here, Dawn?" I asked. "Where's Mike? Are you guys on vacation again, and you didn't tell me?" She laughed. "No, Mike's at home. I'm here for the company." Dawn worked for a company that distributed videos. "I'm here for CES – well, not exactly CES. I'm going to be at our booth at the Sahara." I knew what that meant, and it brought a smile to my face. Dawn was a tad bit of a prude. She's the kind of woman who blushes if her skirt rides up and she catches you looking. The kind of woman who never wore a bikini because she didn't think her body was very good, even though she was the only one who ever thought that. Well, the Sahara meant one thing; the porn convention. Every year, they held a porn video convention in the Sahara at the same time as CES. They liked to draw from the same crowd. I guessed correctly that Dawn's company was distributing some X-rated material, and sent her to man the booth. Just thinking of Dawn in a room full of porn stars gave me a woody. I had to turn sort of sideways while we spoke, so she couldn't see how tight my slacks had suddenly become. I mean, this is my best friend's wife, practically like a sister to me. A sister I've always wanted to fuck, but a sister nevertheless. I started to laugh out loud. "You're shitting me! You're going to be at the Sahara hawking porn videos with a booth full of half-naked bimbos? Oh my God! I will be there for sure, I have to see that!" She was already blushing a little bit. "It's pretty bad. We've got two porn queens who specialize in anal sex at the booth and a hairy guy, known for having a huge penis who keeps hitting on me," she said. "Well, hell," I said, "the hairy guy sounds just like your husband, except for the big dick part." That got a chuckle out of her. In fact, it was the kind of chuckle that got me thinking; did I hit a nerve right there? Does Mike have a small one? I thought back to our days of football and whether I'd noticed that in the locker room, but I honestly couldn't remember if Mike was well-endowed or unlucky. It wasn't the kind of thing I looked at, you know? "So are you staying here at the Rio," I asked? "Yep, I'm on the fifth floor. Where are you?" "I'm here as well, up on the top floor in a suite. I guess I took advantage of my company's generosity a little bit." I tried to keep my eyes looking into hers, but even with the gorgeous green peepers, I found them sliding downwards and staring at her tits. Like I said, they were perky and nicely shaped, and her blouse didn't do a hell of a lot to conceal it. She had an extremely low cut bra on, and I thought I could see a tiny bit of her pink aureole sticking out, though it might have been wishful thinking. It made me hard just thinking about the contrast of her pale, white skin and the shocking pinkness of her nipples! If there were a hell I'd just doomed myself to living there for eternity, because now all I could think of is whether her pussy was as pink as her nipples. I was almost shocked to see Dawn dressed this way. She was usually in shapeless, oversized sweatshirts and jeans. I hadn't seen her dressed like this since prom night. I figured she had a dress code to uphold for her company, and I was sure going to enjoy it while it lasted. "Really?" she said. "I'd like to see that. The rooms here are really nice. I can't imagine what the suites are like." "Come on up, anytime. You'll get a kick out of it. Maybe I can max out the expense report with a table full of room service food and some champagne!" Of course, my dick throbbed at the fantasy of Dawn in my suite, naked and covered with room service food. I could eat that all night. "Actually, I was about to go look for someplace to eat," she said. You want to go grab a bite?" Did I want to grab a bite? Oh, what a loaded question. I tried to play it cool, but I could feel my deodorant fighting back the sweats. We were just two old friends who were having dinner and shooting the shit. I had to keep it in perspective before my fantasies got the better of me. "Sure, let's do that!" We decided to head over to the New York, New York to Gallagher's Steak House. You can drop $60 on a steak there, but what the hell. Here I was, with my best friend's wife, in Las Vegas. There isn't a single person on earth I enjoy having a meal with and talking to more than Dawn, though we had never once done this without Mike and usually I brought a date for the night. I felt like living large, though not without a twinge of guilt. I hadn't done anything wrong yet, but it sure felt like it. I guess I was breaking one of the Ten Commandments right here, big time. I definitely was coveting my neighbor's wife. Worse, the wife of a guy I love like a brother. But I just couldn't help myself and I didn't really want to stop. I was fairly sure she wouldn't let it get very far anyway, but I still felt bad for the evil thoughts that ran through my head. I was having visions of licking her body all night. I'd start on the soles of her feet, work between her toes and slowly up the legs...I was killing myself. We sat down and had a fantastic meal. Exceptional aged beef and a bottle of Cristal. I wasn't going to be able to slide the Cristal on my expense report, so it was going to hurt a little, but who cared? I noticed that when we sat down, she choose the seat next to me rather than across from me. Was that a sign? No, couldn't be. As we ate and talked, we inadvertently touched a few times, and she never pulled away or acted as if I were in her space. I was feeling the Cristal and smelling her perfume, and it made the meal the best one I'd ever had. She smelled like a mix of forest and oriental spice. Albert Nippon, maybe? Expensive stuff, but well worth it. It was perfect with her skin chemistry, pure pheromones. As we finished with coffee and desert, I felt her leg brushing mine. Somehow, it was as intense as entering a woman for the first time. She was wearing a sheer red dress that fit perfectly, probably tailored. I wasn't sure if it was couture, but I suspect it came from one of the Japanese designers who are huge in Asia but relatively unknown here. It was very sexy, and rather avant-garde. It fit her form and accentuated her natural curves, as if she needed any help. The dress went to mid-thigh, and her legs were covered in red nylon stockings; not pantyhose, but stockings. I could see her garters when she crossed her legs. I didn't think anyone dressed like that in public anymore, but to be sitting next to a beautiful woman in kinky lingerie was very stimulating, to be sure. Her leg lingered against mine, and her foot rubbed against my calf. Somewhere along the way, she had shed her high-heeled, open-toed pumps. As long as I'd known her, I couldn't remember a time when she had dressed like this. It had to be a work thing. Those shoes and stockings were incredible; a treat for my eyes unlike any she'd ever worn before. Even as her foot slipped under my pants cuff to touch my bare leg, I was sure she couldn't be flirting with me. Not after all these years, and certainly not when she's married to Mike. Yet I could feel her exquisite toes stroking my leg and my dick was getting stiffer each time she rubbed my calf. I wasn't sure I'd be able to stand up, but I'd already paid the bill and there no excuses for sitting there any longer. I wondered, is this how women are? Do they flirt with old, platonic friends just because they feel comfortable and safe with you, or do they do it just to fuck with your head and make you crazy? Somehow, I stood, and escorted her back to the car. We headed back to the Rio, where I fully expected a peck on the cheek and a firm good night. Instead, she wanted to see my suite. I felt like picking her up and carrying her across the threshold, but that would be a little forward of me. So we took a quick tour and she was suitably impressed. I offered a nightcap from the mini bar as a desperate measure to keep her here. I just didn't want her to go, at this point. Even if we did nothing but talk, I was feeling something here and I didn't want it to stop. Surprisingly, she agreed and we mixed a couple of cocktails. We sat on the edge of the huge round-shaped King sized bed and sipped away. For a minute or two, we talked about Christmas plans and upcoming vacations and such. We locked eyes, and I gently pulled her closer, and we kissed. Her lips were the softest I'd ever felt. Our lips parted, and I felt her tongue, warm and soft, caressing mine. Her mouth was moist and she tasted clean and fresh. This girl was no smoker and I was happy to kiss a mouth that didn't taste like a pile of cigarette butts in a dirty ashtray for a change. I hugged her tightly and she held me firmly as well, and we locked lips for what seemed like ten minutes. I felt my arms moving on their own without conscientious thought, wrapping around her and slipping downward to stroke the curve of her ass. She had such a tight, athletic ass that it rippled with muscle rather than the flabby butt that most women possessed that would someday be covered in cellulite. We finally retracted our tongues; she sucked mine as it slipped out of her mouth. She pecked my lips a couple more times and spoke. "Why didn't you ask me out when we were in High School?" she asked. I was taken aback a bit. I hadn't expected this, but it was a topic that I had thought about over and over again for years. I didn't realize that she had thought about it as well. If the cards had played out a little differently we could have been together, instead of her and Mike. "I wanted to ask you out, badly," I said. "The first time I laid eyes on you I wanted you. And not just for a fuck, like all the rest of those hormonal, tight little bitches that ran around school – it was different. I saw the same thing Mike saw, I guess; that you were not cut from the same cloth as the other girls. But Mike met you first, and he said from the start that you were the one for him. I mean, one day he came to me and said, 'I just met my wife,' and he meant you. He introduced us later that day, and I wanted to shove him out of the way and step in. But he's my best friend, and I couldn't stab him in the back like that. So I stepped aside, and watched him chase you with every move he had. He had designs on marrying you right from the start, and we were, what, 14 years old?" Dawn nodded as if she had long suspected that I had fallen for her and never had the balls to do something about it. "I love Mike with all my heart," she said. "I will never regret marrying him and I don't want to hurt him." She looked into my eyes and I peered deeply into the green pools of her eyes. I was melting inside and feeling a connection with another person that I'd never felt before. She practically whispered to me, "But don't you know that all that time, you were the one I wanted?" I was stunned into silence, but even as she spoke, she was unbuttoning my shirt. What she had said to me felt like opening a door and finding Ed McMahon standing there with a check for a million dollars. It hit me like a hammer right then that the reason all of my relationships were doomed to failure was sitting right in front of me at this minute, removing my shirt and kissing my nipples. I love her. I had always loved her but I had done it in silence while my best friend reaped the fruits of her perfect body. It was an epiphany. I had been feeling guilty because I dream about fucking my best friend's wife. But maybe he's the one who's been fucking my soul mate all these years. Son of bitch, when I fuck up, I fuck up entire lives. I fumbled for her zipper, and then unhooked her bra. She shook her shirt and bra off and swept them to the floor. Her upper body was naked before me, a dream come true. My hands cupped her breasts, which were just as I had imagined. Her areolas were just the right size in proportion to her tits, and they were such as beautiful, light shade of pink. They were natural. No surgical help needed or wanted. Her tits were perfect, like the rest of her, unbelievably perky. We kissed again, as my hands stroked her tits and her back. She loosened my belt and unzipped my pants and then reached in to grab my shaft. Her eyes lit up as she pulled my member to attention. "You're a lot bigger than Mike," she said. I'm not Tommy Lee or anything, but I've got a healthy eight inches and a nice girth. She pulled my pants down to my ankles and knelt down and began sucking on my cock, taking in most of it with each stroke. I had reveled in how soft and moist her lips are when we kissed, but on my cock it was indescribable. It felt like I imagined it would feel the first time you shoot heroin into your veins; instant warmth, blood flowing, a fuzzy and powerful, euphoric high. Her tongue lovingly massaged the underside of my shaft. It was heaven. I laid back on the bed, with my eyes nearly shut in ecstasy. Her hands were not idle. One hand squeezed my balls lightly, and the other rubbed my asshole as she bobbed slowly up and down. In just minutes I was near a powerful orgasm, far too soon for the night I was now planning in my head. How I Fucked My Best Friend's Wife Thankfully, she stopped for a moment to pull my pants completely off, and dropped her skirt at the same time. I would have cum in two more sucks if we hadn't paused. Her stockings stayed for now, though the panties had to go. I stood erect in more ways than one, and she knelt before me and took my cock in her mouth once again. I ran my fingers through her hair as she slowly moved her head up and down, bringing me right to the edge of orgasm again. This woman could manipulate me like a puppet, obviously. She could make me cum in seconds or make it last all night. Her right hand played with my ass while her left hand kneaded my balls like two lumps of soft clay. It was almost too intense to withstand, and I moaned loudly in sheer pleasure. I looked down and watched her gobble my shaft, and admired the alabaster skin of her shapely ass and her stocking-clad legs. My dick pulled out of her mouth with a pop, and I lifted her upwards, until our mouths met for another deep tongue kiss. I could taste the slight saltiness of the pre-cum she had swallowed, but I didn't care. At this point, I would have licked her pussy after a gang bang and had no regrets. My hand caressed her tits and I bent down slightly and licked and sucked her nipples. I felt them hardening as I lovingly licked them, and she moaned lightly as I reached down and rubbed her clit. Her legs spread slightly, and I felt the warm lubrication on my fingers. We laid on the bed in a 69 next, and I parted the lips of her pussy with my fingers. She had a Brazilian bikini wax, to my surprise, and her pussy was naked and beautiful. Her labia were pink like her nipples and protruded only slightly. Her clit was already engorged, and I gladly ran my tongue around it in slow circles, alternating with long strokes the length of her slit and down to the perineum. She tasted clean, with almost no perceptible odor at all, just a trace of musk that was like ambrosia. I have never seen such a perfectly waxed pussy, with no blemishes or imperfections anywhere. Her moans became more rapid and loud, even as she stuffed my dick back into mouth and sucked voraciously, squeezing my balls until they were as hard as marbles and full to the brim with cum. I continued to lick slow circles around her clit, touching only gently with the slightest of pressure. I had two fingers in her pussy, which I slid down to her ass and used the sloppy lubrication of her own cunt to moisten her sphincter. I rubbed a finger around the rim of her ass before gently popping it into her rectum. I worked it down a couple of knuckles and then added another finger. My thumb was in her pussy now, rubbing her G-spot as I sucked her clit lightly and circled it with my tongue. I felt the walls of her vagina contacting and teased her by easing back on the clit. She shook and her anus grabbed my fingers in a vice grip as she came, furiously. Her breathing became a serious of harsh intakes and she moaned a muffled, "Ohhh," as she breathed out, still sucking my member like a straw. As I drank her juices I kept her orgasm going for an eternity by working her anus and G-spot as I only lightly flicked her clit with my tongue. Just as her body started to stop shaking and her moaning began to subside, I knew that I couldn't hold on any longer. My orgasm was a gusher, and she swallowed every drop, milking my rock-hard balls and sucking hard to get every bit of it. I felt like she was turning me inside out, and my legs straightened involuntarily until I could feel them cramping. I had never had such an intense orgasm in my life, nor enjoyed giving one as much. My sack deflated like a leaky balloon, and my dick softened from a girder-like hardness to a limp and sorry state. She turned around in bed to face me, and cum was smeared around her lips and chin like she had just wolfed down a creampuff. I drew her to me and kissed her lightly, the jizz dripping from her face. I wiped the cum from her cheeks. I had never done that before, I usually made it a point to face-blast whatever bitch I was fucking, and then I'd smear it all over for good measure. This was different. I didn't want this goddess covered in cum like a dirty, whorish bukkake queen. She giggled as I wiped the last drops off of her beautiful cheek bones. Her smile was like sunshine. I kissed her again, deeply this time. I was truly drained. But not finished, by any means. I knew there was more in the tank. I felt horrible in a way, because I had just shot what seemed like a pint of spunk down the gullet of my best friend's wife. How could I possibly betray him more? Well, I was about to find out. We lay there for a few seconds, catching our breath, and then I felt her tongue on my balls, licking from the base of my penis down the center vein and around my balls. She popped them into her mouth and sucked them gently for a moment, then moved down to my ass. She was rimming my ass and I liked it! I had spent the last 12 years thinking of Dawn as being somewhat prudish, and here she was licking my asshole like it was cherry flavored. I needed no further persuasion to return the favor. I ran my tongue around her o-ring, and pushed it in as far as it would go. It should have tasted like shit, I suppose, but it was divine! As we tongued each other's asses I felt my rubbery dick begin to stir again. Soon, it was standing on its own and eventually raging hard and waving angrily in the wind. She stroked it now, while still bathing my asshole with her tongue. After the intense orgasm she had just given me, I wasn't sure that I could go again, unless I had a few hours to charge my batteries, but she knew how make a dick stiff like no other woman I'd ever slept with. It was time to fuck the sweet pussy that no man had ever defiled before, except for my best friend; her husband. I was about to enter his wife's pussy, and do my best to turn her inside out, ravage her and ruin her for any other man, without so much as a condom or an apology! As bad as I felt about it, I also felt strangely excited, more than I ever had with a woman who didn't belong to another man. I turned around until we were face to face and French-kissed her again, with authority. My hands squeezed her perky tits, and then I moved down and sucked her nipples stiff. I moved down again, and began to lick her pussy, now as wet and sloppy as it could be. I drug her to the edge of the bed. The bed was tall enough so that when I stood beside it, she was at just the right height to enter her. When her ass was on the very edge of the bed, I held her ankles high and rubbed my cock up and down in her slit. She moaned as I slowly rubbed the head of my dick against her clit, and then eased it in to her slit. I pushed my dick into her tight, wet pussy with gentle, but firm, pressure. Once I had penetrated her just an inch or two, I eased it out again, all the way out. With my cock poised like a sword in front of her, I pushed back in, a little deeper this time. With each stroke I fully exited her box and then re-entered and went just a little deeper. Finally, my balls were slapping against her ass and my dick had reached new depths where Mike had never gone. As I pumped her I rolled her stockings down her leg and then pulled them off with my teeth, first the left leg and then the right. Her toes featured a perfect pedicure and were painted a deep, sexy red. They had just the slightest tinge of sweat and yet smelled sweet somehow. Her feet were shapely, with a high arch. My dick grew harder. I held her ankles above my shoulders and well apart as I fucked her with building passion. Slow at first, but stronger and faster strokes as I went on. I brought her foot to my mouth and sucked on her toes, one at a time. "Oh my God," she purred. "Your cock is huge! It feels like I'm completely filled up. Oh God, it feels good." Part of the reason I had thought of her as prudish was that she usually wears sensible shoes (meaning ugly) and I've never seen her in fuck-me pumps or high heels except that one summer back in High School. I could spend an hour just licking and sucking her toes. I placed her ankles on my shoulders and we fucked that way for the next few minutes, as I sucked on her toes and rubbed her clit with the other hand. She had her eyes closed tightly, and she moaned louder as she neared orgasm. She is a tiny woman, and I could see that the girth of my cock was stretching her to her limit. She felt so tight that I worried about causing pain. I used my thumb to rub the hood above her clit and teased it with gentle circles while I stroked as deeply as I could go, until I felt the involuntary clenching of her vagina against my prick and the spasms of another powerful orgasm. She gasped for breath and shook beneath me. "Oh my God," she said, "I can't stop cumming...ohhh, my God!" I was getting there myself. I thought her oral skills had emptied my balls for the night, but they were filling up again and I could feel them tightening. Finally, I exploded deep within her, spewing like a volcano once again with the hardest cum of my life. Even as I shot the last spurt into her, I realized that my dick was hardly softening at all. I just kept fucking until my shaft was rock hard again. I hadn't had this kind of recuperative power since I was 17, but this was certainly the time to experience it. I rolled her onto her stomach, without even removing my dick, and fucked her from behind so that I could look at her beautiful ass and watch my cock pumping in and out of her pussy. She was as game as I, and already I could tell that she was going to cum again soon. I reached around her thin waist and played with the neatly trimmed hair just above her Brazilian-waxed pussy. Slipping the fingers downward, I touched her clit, but ever so slightly. Her clit and pussy had to be getting sore by now, so my touch was like a feather, so gentle she may have thought she was imagining it. Not so for my dick, though. I was pumping her ruthlessly, absolutely violating her pussy and the trust of my best friend, Mike. I wasn't beyond caring, but I couldn't stop any more than I could fly. I had shit upon the friendship I have with Mike the very second my lips touched his wife's in anything more a friendly peck. I had longed for this night for over ten years, and now it was happening. It was even better than in my wildest dreams, yet I felt the pangs of guilt for what I was doing to this good man. I know that Mike wants kids someday, and here I am filling his wife's pussy full of my sperm without as much as the courtesy of wearing a condom. What If I made her pregnant? If I'm going to fuck his wife like a common whore, can't I at least leave him a shred of dignity? Can't I allow him the respect of his bare dick being the only one to ever touch the walls of her vagina? And for God's sake, can't I let his seed be the only seed that fills her? I couldn't even do that for him. I had to take her as nasty and dirty as I could. I could not stop myself. You can imagine, then, how bad I felt after what we did next. As we were fucking doggy-style like a couple of greyhounds, Dawn looked at me over her shoulder. "Randy, I want you to fuck me in the ass." My God! My fucking God! With those ten words she had just changed my world. "Are you sure," I said, praying that she was. "Have you done this with Mike? I don't want to hurt you, Dawn, I care for you too much to cause you pain." I pulled my dick out of her cum-filled pussy and she turned back over and sat at the side of the bed. She pulled me to her, and grasped my balls, tugging gently but firmly. She touched the back of my head and motioned for me to come closer. We kissed for a breathless minute or so. "No," she said to me. "I've never done this with Mike. He has never asked for anal sex and I don't think he ever would." I was perplexed. Do I really know this guy? I could swear that he's boasted about ass fucking and joked around with the guys about it. "You're kidding me," I said. "He comes home and sees this beautiful ass every night and he's never touched it? Is he fucking crazy?" "He probably talks like he does it, I don't know," said Dawn. "The truth is, if he says he's had anal, he's just putting up a front to be one of the guys. He's actually disgusted at the thought. He says that assholes are for shitting and farting. Really suave, huh?" I had to nod my head at that one. Not a smart way to talk if you're trying to get your woman in the mood for love. She continued, "He hates the smell and the sight of an asshole and he thinks it's disgusting. So much so, that I've always wondered what it's like because I was afraid I'd go to my grave without every having a chance to at least try it!" She looked at with those soulful green eyes again. "Will you fuck me in the ass, Randy? I'll tell you to stop if it hurts. But I want to try." Will I fuck her in the ass? Does the Pope shit in the woods! Jesus Christ, she was asking the right guy. I love to fuck a nice, round, clean ass. And hers was the most enticing I've ever seen. "Dawn, it will be an honor for me to be the first man to make love to you this way." The truth is, I could eat her asshole with a spoon, it was so good. "Then do it," she whispered. "Be gentle and teach me." She rolled over onto the bed and presented her sweet little ass to me. My cock was so stiff now that it was almost painful. My balls ached for her. I placed my hands on her rump and pulled her cheeks apart to expose the perfect rosebud of her sphincter. First, I licked the crack of her ass, up and down. Then I circled her rectum, licking the salty, puckered ring until she began to relax. My tongue darted around the rim of her asshole, and then plunged it in, until I was fucking her with my tongue. She was moaning now, getting used to new sensations. The sphincter has a lot of nerve endings, but it's an alien feeling at first. In time, it becomes familiar. A hot, moist tickle that leaves the skin tingling. You want more. I couldn't believe what was happening here tonight. Yesterday, I entertained nothing more than a fantasy of making love to Dawn, and now I was tossing her salad like we were filming a porn video. "It feels good, Randy. I kind of like it. Don't stop, baby," she cooed. I never travel without a tube of K-Y Jelly. You never know when you might get lucky. I reached for it in on the nightstand, removing my tongue from Dawn's ass only for a second. I prefer Vaseline for ass fucking because it is thicker and stays viscous when it gets hot. Doctors don't like it because Vaseline is not water soluble so it stays in the ass where it can foster bacteria. But what do doctors know about serious ass fucking? Those clowns are too uptight about germs to have any real fun. With my face buried in her ass again, I lubed up a couple of fingers with the K-Y. A few more licks around the rim and then I rubbed my lubricated fingers around her rosebud. She moaned again as I pushed gently against her o-ring, not enough to enter her, just enough to make her feel the pressure. Gradually, I pushed a little more and then one finger popped into her rectum. I moved it deeper into her anus, very slowly, and finger fucked her. She began to push her ass into my fingers, clearly enjoying the feeling. With my free hand, I played with her clit. As she loosened up and relaxed, I pushed a second finger into her asshole. She bucked a little from the sudden change in pressure, but she kept swaying against my fingers. "Mike has never even put a finger in my ass," she said as I pushed a third finger into her, this time with almost no resistance. "He would be completely grossed out at putting his finger in my ass because he might get shit on it." I didn't care if she shit on my forehead right now; I was having the best ride of my life. I was beginning to think that my best friend is a dumbshit. If he was any kind of man, would his wife be in my hotel room right now, begging me to fuck her in her virgin ass? I doubt it. I still felt like a perfidious bastard, but I was beginning to rationalize my way out of it. "Dawn, honey, I'm going to fuck you now," I said to prepare her for the shock. "At first you're going to feel like there's no way my dick will fit in you, but it will. There will be some pressure until your sphincter dilates and then my dick will glide right in. It will feel like you have to shit, but you don't, so don't push or try to hold it in, just relax. Whatever you do, don't panic and tense up. You have to stay relaxed and trust me. If you tense up it will hurt. If you relax you'll feel some initial discomfort but not much pain. As you get used to it, it will start to feel better. Most women can take it or leave it, but some won't fuck any other way. I hope you love it as much as I love being the first man to have the privilege." "I trust you, Randy. I know you want this to be good for me. Please be careful with me," she begged. So here it comes. I was about to break the final taboo. To cross the last line drawn in the sand. You do not fuck a married woman. You especially do not fuck a woman married to your best friend. And if you do fuck her, you do not fuck her in the ass. I guess I'm a shitty bastard, a piss-poor excuse for a friend. What a rotten fucking best friend I turned out to be. Poor Mike. If he walked in that door right now, he would die. He would never forgive me. And with that said, I grabbed my rock hard dick with my right hand and pushed it against the wrinkled little rosebud of her asshole. She went, "Ohh!" in surprise at the feeling of such a big object pushing against the tiny opening, but she only tensed for a second. I rubbed it up and down the cleft of her ass to get it lubricated with the K-Y I had smeared there, and then pushed again at her virgin asshole. It resisted briefly, and then opened up to engulf the entire head of my cock instantly. There was another, "Ohh! Ohh!" from Dawn, more shock than pain in her voice. Slowly I pushed more of my dick into her bowels, a half inch or less at a time. With each small gain in purchase, I would then pull it out almost completely before slowly pushing it back in. A little further each time. Her sweet asshole was like a finger and thumb wrapped around the shaft of my dick. It was like having your dick in a pussy, with a hand jacking your shaft at the same time. Her intestines were warmer than the rest of her, hot almost. I moaned with sheer pleasure as my dick continued to slide into her bowels. One thing about ass fucking is that everyone has different kinks and curves to their bowels, and sometimes you can slam your dick straight in while other times you have to slowly ease into her innards until your dick can work its way past any kinks. Dawn had curvy insides, and I had to be gentle as I pushed ever forward. She would flinch a little when I hit a snag, but she wasn't complaining so far. Finally, I bottomed out. My cock was a full eight inches into her rectum and my balls were tightly pressed into the crack of her ass. Her arms were shaking from the strain of holding herself up, and she dropped to her elbows, forcing her ass to tilt up a little more. I began to pump her rectum with slow, easy strokes. She was moaning now. "So this is what it's like to get fucked in the ass," she said. "Really, it's not so bad. It feels okay. I have girlfriends who bitch about it and say they'll divorce their old man if he tries it a second time, but this is nice." What an understatement. It was way beyond nice. "Are you okay, baby? Tell me if you feel any pain," I said. "You feel so good. You have the sweetest ass I've ever fucked, honey. I can't believe I waited over ten years to have you. I've wasted so much time." I was telling the truth. Her ass was hot, it had to be a hundred degrees in there, and it was exceptionally tight. Her sphincter was stretched around my thick cock, but still squeezing me in a fantastic grip, milking my dick like it was a cow's udder. I felt my balls swelling up with a huge load of spunk. It was not going to be long now. How I Fucked My Best Friend's Wife We were grinding into other passionately now. She was used to the feeling and it was bringing her pleasure instead of discomfort. She had figured out the rhythm of butt fucking, which is to squeeze your anus as the dick is on the outstroke, not as it's going in. It's counterintuitive for some reason, but squeezing pushes the dick out, so it feels great and you're not fighting against her and causing pain. She has to relax as it goes in, and not tense up. I was able to pump harder and harder and she was making noises like a tennis player, grunting each time I bottomed out. She was fingering her clit wildly now, and as I rammed her face into the pillow with each pump I found myself about to explode! I came just then, like a fire hose, pouring spunk into the depths of her bowels. She came at the same time, fingering herself with abandon. As I milked the last few drops out of my sack, I slid my still erect cock from her ass. Her asshole was ruined. It hung open like a slack-jawed mouth. I could see my creampie deep in her bowels. It was the best fuck of my life. We lay there spooning in the afterglow and talked as I stroked her hair and kissed her cheek and earlobe. "What are we going to do now, baby," I said. "I feel bad about Mike, but I love you. You're the only woman I would be monogamous for, Dawn. I would love you and treat you like a Goddess. Will you leave Mike for me," I asked? She sighed deeply and her brows furrowed. "Randy, I love you and I want you. But if Mike knew about this, it would kill him. I love Mike too, but not in the same way. Still, I can't hurt him like that. He would be more hurt about losing you than losing me, but to lose both of us would kill him." She was right. I was willing to chance it, but I knew that it would kill Mike and Dawn and I would be pariahs amongst our friends. This would not play well in the gossip community. "Then what will we do? I can't bear the thought of never having you again," I said. Whenever I am near you, my heart will pound like a drum. I will smell your perfume and taste your mouth and your pussy in my memory. I will not be able to stand next to Mike and pretend nothing ever happened." She rolled over to face me. "We can see each other. I mean see each other like this. We can make love almost anytime you want me," she said. "Mike is asleep every night by 9 o'clock. He drinks himself into a stupor. You couldn't wake him with a cattle prod. You could fuck me in his bed with him sleeping there, if you want to." I felt better now. As shitty as I felt about what we'd just done, I felt hope that we'd do it again. She rolled over and soon I could hear her deep, steady breathing. She was sound asleep. I was still fully awake. My brain was still a thunderstorm of thoughts. My mind recoiled from guilt and self-loathing because of the way I'd betrayed Mike's trust and friendship, and yet, I found myself making mental excuses for my behavior, and justifying it as if I was preparing to defend it in court. I looked at Dawn in the light of the bedside table. Her pussy was red and swollen and her ass was no longer gaping, but it looked like it had suffered terribly and there was a string of cum running from her asshole down her leg. Her face was covered with dried cum here and there that I had missed when cleaning her. Her tits were swollen and almost bruised. She looked like she had filmed a gang bang flick and nobody had used a rubber. She looked like a whore. And she looked like an angel. Her face in slumber was one of purity and innocence though her body reeked of illicit sex. Even in this condition she was still beautiful. I really do love her. I got up quietly and picked up my cell phone. I know that this sounds like a creepy thing to do, but I moved her legs apart, opened her labia to expose her pussy, and took several pictures with the camera in my phone. I wasn't about to tell her, but I was going to look at these pictures every night and jack off like a horny teenager. I put my phone away and finally felt myself drifting to sleep. In my dreams, I saw Mike. He pointed a finger at me, accusingly, and my cock shriveled at the knowledge of the grave betrayal I had committed. I had a lot to think about that night. In two days, we'd be home again. Would I be able to look Mike in the eye? Would I be a man and tell him what I'd done? I just didn't know. In the morning, I fucked his wife twice before we both showered and went to work.