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.