Amy And John Part Three – Amy’s First Anal

Amy Tells Of The First Time She Had Anal Sex


Amy and John have established a great relationship. Amy thought it wonderful that he was doing everything, and anything, she wanted, just to delight her. John is all she ever wanted in a man. At the present, they have just gotten engaged. Things are changing a little because they’re planning a life together. First, they are going to move in together. However, right now they both have their places. Amy has a marina condo, and John has a house at the marina. After careful assessment, they’ve decided to move into John’s house. Anytime two people agree to move in together, it creates a few concessions for both. Consequently, they have been having fun working things out.

Of course, Amy had to tell all her girlfriends that they were engaged. She had a wine and cheese get-together to inform everyone. She expressed they would all be bridesmaids, and her best friend since a little girl Noel will be her Maid-of-Honor. All the women were very thrilled for her. They started planning a bridal shower right away. Her friend Nancy, who is married, told her not to let John dictate to her, trying to take over everything. Amy just chuckled, saying she thinks everything is working out. They all had a lot of advice to offer her, the married and unmarried.

“The only thing I know John would like is if I’d try to be bra-less as much as I can,” Amy stated.

 They all had to laugh, “join the club. That’s all we ever hear, ‘why are you wearing a bra?’”

 “I have large breasts, and I need some support. I can’t go flopping and bouncing around. So we compromised, I’ll wear self-bras. That’s what being together is all about, working things out. Right?” Amy stated.

Amy then admitted that she always liked shelf bras, and should have been wearing them a long time ago.

 Her friend Karen, who also has double-D breasts put in, “I love shelf bras, you will too. Very comfy, and sensual.”

 Sarah stated, “next he’ll ask you to shave your pussy. And he’ll want to do it.”

 “Not John. He loves my red pubic hair,” Amy laughed. “Now, the big thing I have to ask you all about.”

 Amy told all the girls to gather around, she had something to say wanting their advice. Amy swore them all to secrecy.

 “I’ve decided to let John, be the first to fuck my virgin ass. I’ve never had anal sex before, only a finger up there. John’s an ass man. He has always wanted to fuck my ass. Now I want him to do it, especially after seeing him enjoy Sarah’s cute little ass. I could tell how much he loved it. So I’ve decided to try it. John loves a woman’s ass so much he thinks yoga pants were made so he can watch all the cute asses. I wear them whenever I can for him. He loves it. John is always playing with my ass. He loves to feel and squeeze my buns, he does it all the time. When we walk together his hand is right there, on my ass. Plus he was the first guy to ever really rim and tongue fuck my brown eye. I love it. The only one who has rimed me before, with any type of real love for anal tongue fucking is Sarah.”

 Then all the other girls, at almost the same time said, “we all rim. Just like you do it when you go down on one of us. Rimming is just part of eating pussy.”

 “I know. But getting rimmed by a guy is different than with you girls. John loves to do it to me all the time. Every time he goes down on me, he not only takes care of my pussy, but my asshole as well. Plus while we are making love, sometimes he will slide a finger into my ass, I love the feel of that too. The first time he did it, I was about to say stop, but I waited to see what it was going to feel like. I adored it. Now I think I’m ready to take it to the next level. Now I want to feel his cock in my ass,” Amy told them.

 Amy continued, “One other thing, I’ve decided, my ass will be only for him. No one but John will ever fuck me in the ass. Before John, all the guys I had ever fucked, only paid attention to one thing, my double-D chest. Trust me, tit fucking does nothing for me. I don’t think I have ever had, or will ever say to a guy, ‘hey come tit fuck me.’ That does not mean I don’t do it, I do. But for the same reason, every girl with large breasts does it. Because it delights her man. I do like it once we start, and when a guy comes on my nipples, especially if he licks them afterward. Even better, when we lick it off together, which John loves to do with me. But now, I want to add something, like anal sex. Am I right, Noel, Karen, Nancy, all of you have large breasts, don’t you just tit fuck because you have to?”

 “Speaking for all well-endowed women, you’re correct,” Noel replied laughing.

 Moving on, Amy wanted to plan everything, before first trying anal sex. Amy wasn’t very spontaneous when it came to that kind of thing. She was wanting her first time with anal, to be picture-perfect. So, she was wanting to find out everything she could, from her friends whom all engage in it. She knows, that they all do it, and all love it. All her girlfriends told her she was going to go nuts with how great it felt.

“I know that John loves me, the whole package. I don’t have to do this, I want to. A cute, funny thing about him is he loves my red pubic hair. I use to go bald a lot, mostly in the summer due to my swimwear, then when it’s fall, I let it grow out again. Keeping a bald pussy nice and smooth, is a lot of hard work. As you all know. However, now I keep it a little frazzled all the time, due to John’s love of my red pubis. I enjoy that about him. Then there is my ass, which people say is very cute, I must agree. He adores my ass,” Amy said.

 Next, in planning this encounter, Amy wanted to find a way to accent her ass, for John’s first time with her. Therefore, on the day of the big event, Amy had Sarah, come over to help her get ready. The best dressing and make-up person she knew, is Sarah. Amy is very, attractive, so Sarah had it easy. Amy is 5 foot, 5 inches tall, with long red hair, and sexy green eyes. There’s no doubt she is a real redhead, with her creamy white skin, with lots of freckles. Her large double-D breasts, also have some freckles and are topped with half-dollar size, dark areoles, with long, pointed nipples. She is about one hundred five pounds, with a hard athletic body, hard ass, and red full pubic hair.

 Amy, with Sarah’s help, decided to wear a red satin garter belt, red fishnet stockings, a red shelf bra, and no panties. The garter belt would frame her ass perfectly, plus her red, furry, pussy. Amy’s goal was to look, sexy, the best she has ever looked. She had her hair done, with large curls, flowing down her upper back. She wore a light pinkish, blush, with green eye shadow, along with long eyelashes, with little green sparkles on them. This accented her emerald green eyes beyond the imagination. Of course, bright red, glossy, lipstick, which John adores on her.

 Once Amy and Sarah, thought everything was perfect, Sarah took a full range of pictures, of Amy dressed to perfection. Sara being an erotic photographer, and adult film editor, knew what she was doing. These would be perfection. Sarah took every kind of photo of Amy standing, sitting, and bending over, even on the bed. Again on the balcony looking out to sea. Some with a shy look, some with her legs spread, fingering herself. Once Sarah was done, Amy took a few selfies to send to her friends because she looked so hot. The last thing Amy put on was a red silk half-robe. It came to just below the top of her thighs. Now all was ready.

 Sarah kissed Amy, telling her to sit on the chair. Amy did as told with a puzzled look. Sarah went and knelled between her sexy legs, and promptly started licking Amy’s dripping, wet, pussy, catching Amy by surprise. Amy just leaned back and enjoyed the great sensations Sarah’s tongue was giving her, with the spontaneous act. Within a couple of minutes, Amy had a mind-altering orgasm. As Amy came, Sarah kept licking her sweet dripping cunt. Only as Amy’s climax was subsiding, did Sarah sit back on her heels. Smiling up at Amy.

 “I thought you needed that to relax. I needed it too, and eating you out was the best thing I could think of. You don’t have to return the favor now. I don’t want you to mess up your make-up,” Sarah chuckled.

 Getting ready to leave, Sarah told her she wants to hear all about it tomorrow. She tells her she has to leave now because she is so wet, and horny. The last thing Sarah said as she left was, that Lisa, her live-in girlfriend, is going to enjoy these pics but, more than that, the sex they are about to have.

Amy placed some pillows around, plus Sarah had told her to make sure she had a few tubes of lube at the ready, within quick reach. Amy had a couple of bottles of wine on ice. On their life-size, seventy-five-inch TV, Amy had a DVD playing, which was about four hours long, of the best porn shorts. The shorts are linked together, soft jazz playing in the background. Sarah is a porn film editor, so she made sure there were a lot of wonderful anal scenes. They could listen to music and watch, as they played. All was ready. Amy was so horny waiting for the time, John was to come over, that she sat on the couch, and played with herself until she came. However, that only made her want more.

 Then John arrived. Amy’s heart was racing. She went to the door wearing her red robe untied. Opening the door wide, and seeing John, made her knees go weak. He looked at her standing in the doorway, open red silk robe, in red fishnet stockings, and red garter. Her hard, nipples, poked out from the red self-bra, which was pushing up her large mountainous breasts, into a perfect cleavage. Sarah had accented Amy’s nipples, with a little red lip blush. John looked at her smiling in awe. Amy jumped into his arms, kissing him, her tongue probing his mouth. She had no idea how long they stood there kissing, with the door open. Amy only knew she needed him. His hands were rubbing her perfect, firm rear as they kissed. She was brought back to reality when a car went down the street, realizing she was standing in the wide open doorway, fully exposed to anyone who wanted to look. Smiling at the idea that they might be being watched that very second. As they entered her apartment, she let the robe slide off, onto the floor.

 “Wow! You look so perfect, so stunning. I’ve never seen you dressed up like this before. You’re magnificent. You’re superb. Like I’ve always said, you’re the most beautiful woman I’ve ever seen,” John told her.

 Now calming down, Amy was feeling more like herself. In her mind, she was going over her plan in her head. She was thinking, I dressed how I thought you’d like. Turning around so her back was facing him, without a word, bent over slowly, exposing her hard firm ass to his gaze. She heard him sigh, as he stared at her perfect backside. Her ass is framed in by the red satin garter belt, and red fishnet stockings. Looking over her shoulder at John, smiling at him, she slowly bent lower, very slowly. As she lowered herself, her asshole and womanhood, became fully visible to him.

 Once Amy was fully bent over she asked, “see anything you like?”

 Then slowly, standing straight up, turning to him, putting a finger to her lips, licking it, then placing it on John’s lips.

 “I’m all yours, every part of me. I want you to be happy. I want you to enjoy my body. Every taste, every smell, every hole. All of me is for you.” Amy told him.

 Knowing he don’t fully grasp what she meant by, ‘every hole,’ she was more than sure he would grasp it soon enough. Standing in front of him, Amy started to unbutton his pants, pulling them down.

 “Let me see your, gorgeous cock.”

 With that, she kissed him while pulling down his zipper. When she did, he helped her by pushing his pants off. Amy dropped to her knees, engulfing his rigid, long, cock, in her warm, willing, mouth. Taking all of him down her throat, waited a few seconds, then pulled it out. Holding the base of his cock, Amy looked up at him with her sexy, accented, green eyes.

 “You taste so great. I can’t wait to swallow your creamy load. Your cum taste so yummy.”

 Amy went back to licking, and sucking, on his stone-hard cock. After several minutes Amy stood, kissing John on the lips, slowly moving over to the couch. Getting on it, her back to him, kneeling on the cushions. Her perfect ass pointed right at John. Looking over her shoulder, Amy saw he had pulled off his clothes. Now nude, John stood right behind her, his cock hard as a rock. She bent over further, exposing as much of her firm, hard, ass, and red furry pussy to him as she could. Her hands were on the back of the couch. Amy’s ass pointed directly at John, perfectly framed by the red, satin garter. Her pussy dripping, and a hint of red pubic hair could be seen from between her legs. Amy reached back with both hands, spreading her firm faultlessly hard-ass cheeks, as wide as she could. She knew John was watching, taking in her cute ass, and now fully exposed asshole.

 “Come over here and lick me. Lick my asshole. Do it the way I love you to do it to me. My ass is yours. Take it.”

 John leaned down kissing her turned-up ass checks, placing a hand on each side, as his tongue slowly moves around her cute, little, rosebud. Amy took in a deep breath as his wet tongue went around her puckered tight, virgin, asshole. She loved the sensation of it. Her nipples tingled, as more of her nectar dripped from her sensitive, pussy. Her hand went down to rub her clit, as John moved to kneel on the floor behind her. His face was now at eye level, with her firm appealing ass, and flawless pussy, all framed in red. Taking a hip in each hand, John moved slowly to run his hot, tongue, over her sweet asshole. His tongue moves down to her outer lips, then back up. The initial contact of his hot, wet, tongue, made Amy squeal from pleasure. John moved his tongue deeper into her sensitive, dripping, vagina. Licking up all her sweet nectar, savoring her aroma. It seemed like an eternity, that he was licking her pussy, before he moved his tongue back to her puckered virgin, tight, asshole. Then his tongue travels back down, to her clit. John opens his mouth so his upper lip is on her asshole, his lower lip on her clit. His tongue moved all over her inner folds, his lips going crazy on her asshole and clit. Amy doesn’t remember when it happened, but, she came with a shriek as he orally pleased her from the rear. Loving the sensation of her extreme orgasm, plus John’s hot mouth on her.


 After her climax subsided, Amy said to John, something she could not believe she would ever say to any man. She asked him if he would like to fuck her in the ass. She was so hot from him licking her pussy, while tongue fucking her asshole, she knew she was ready.

 Looking over her shoulder at him saying, “John, please do something for me.”

 “Anything. What?” he asked.

 “Be the first to fuck me in my virgin ass. I want it. I need it. I want to feel you shoot your hot cum up my ass. Please fuck my ass.”

 The room went silent for a minute, then she heard, “Are you sure? You sure you want me to fuck you in the ass?” John asked.

 “Yes. I’ve been fantasizing about it for a long time. Now I’m ready. Your tongue feels so good on it. Your finger is always a delight in my ass. I love it. Now, I want to have your cock up my virgin ass. Do it now. I’m more than ready. There is lube on the table.”

 “Wow,” he said, “you do mean this! Oh Amy I have been fantasizing about this moment too.”

 With that she got off the couch, and kissed him, getting on her knees, she bent over the couch so her body was on the cushions, her ass up, ready to be plowed into by his hard cock. John grabbed her, pulling her up.

 “Wait for a second,” he said. “Not like that.”

 “What? This is how we do it right? Doggy style? I’ve seen it done in films. That’s how you did it to Sarah. Now I’m ready for you to put it in my ass,” Amy stated.

 John smiled at her saying, “Not that way right now. Sarah was different. Sit on the couch facing me. We are going to do it from the front. That way you can watch everything. This being your first time, I want to make sure everything is perfect for you. I can tell by looking at your face if you are enjoying it or not. If not, I’ll stop. If you’re bent over the couch, all I’ll see is your gorgeous, perfect, ass. I want to watch you as I slide my cock into your sweet, virgin, tight, asshole for the first time. I want to watch your breast move, as I pump into your ass. I want to suck on your perfect nipples, as I slowly slide in and out of your tight asshole, for the first time. Kissing you everywhere I can reach. Most of all I want you to watch us do it too. You can’t do that doggy style.”

 Amy did as she was told, sitting on the edge of the couch. John knelt in front of her, again and begin licking her sweet, dripping, red, furry pussy, as he slowly moved a finger into her tight, virgin, asshole. Amy sighed as he continued to lick her all around her pussy, as he slowly finger fucked her asshole. Reaching for the lube, he put it on two fingers, then went back to licking her pussy, and clit. Slowly moving a lubed finger into her ass, lubing her, while loosening her ass. Amy sighed loudly.

 “That feels so great, I love it. Push it in further,” Amy demanded.

 John slowly started moving the other finger in her, then slowly pulling them out, then pushing them back in. Amy was breathing heavily, now pinching and pulling on her nipples, as John slowly fingered her tight, virgin, asshole. As he did, he concentrated on licking her clit. Suddenly he felt her asshole tighten, hard on his two fingers, as Amy suddenly came again with a scream. As Amy came, he pushed his two fingers as far up her ass as he could. Once her orgasm subsided, John slowly pulled his fingers from her tight, asshole. John sat back looking at her. He didn’t say anything as he reached for the lube, putting some on his stone-hard cock. Amy watched, her anticipation was great, as John lubed up his cock. Her nipples were hard, looking like cannons.

 “Keep watching. Watch my cock slowly fill up your ass,” John smiled at her.

 Pushing her knees towards her chest, he moved so the head of his tool was against her puckered little, virgin, tight, asshole. Amy moaned as John moved the head of his hard cock, in little circles all around her asshole. Amy was breathing deeply, eyes fixed on what was happening, her head spinning from the pure pleasure of it. Then his two, greased, fingers, slid into her tight ass again, lubing her up. Pulling his fingers out, John took hold of her breasts, pushing them together, so that he could suck both her nipples, at the same time. His cock was pushing against the opening of her virgin asshole, now and then, almost sliding into her wet, slick, pussy. After a couple of minutes, John bent down to kiss her wet, pussy. Amy grabbed his head pulling him up.

 “Don’t eat me, fuck my ass. I WANT YOU TO FUCK MY ASS! NOW!”

 John smiled replying, “that’s all I wanted, to hear you say. Now I know you mean it.”

 With that, he placed his greased-up cock at the entrance of her virgin asshole. To Amy, it seemed like hours, before he began slowly pushing the head of his rigid cock into her tight, puckered, virgin ass. Amy was sitting on edge of the couch, legs spread wide, feet on the cushions as she watched, wide-eyed as she saw the head of his cock moving, slowly, into her virgin ass. Just as the head went in her, John stopped a moment. She felt burning for a few seconds as he entered her, but it stopped when he quit pushing. John was staring into her green eyes, watching her as he slowly pushed deeper up her ass again. Amy’s green-eyed gaze was locked on watching, as she felt the length of him slowly traveling into her virgin, tight, asshole. To her surprise it didn’t hurt, she felt warm and full. When Amy felt his balls against her, she knew he was now fully in her ass. Looking down again, she saw her ass full of cock, her red pubic hair, covering an empty vagina. She loved it. His cock felt so good and warm in her. Amy was also loving the sight of his cock filling her ass, now no longer a virgin ass. She pushed her nipples together as John bent down to suck them. The sensation of him sucking both her nipples as one, while his hard cock was slowly moving in and out of her tight ass, was nirvana.

Amy began rubbing her clit, now and then sliding a couple of fingers into her slick, hot, pussy. As she fingered herself deeper, she felt John’s cock sliding in and out of her ass. Soon she had positioned her hand so she had two fingers in her vagina, and her thumb rubbed her clit. All of sudden the combination of John’s cock in her asshole, her fingers in her pussy, as he sucked her nipples, all of this, made her cum again, very loud and hard. As she came her ass tightened again, on John’s cock.

 Once her orgasm started to subside, Amy moved so she was again watching his cock slide in and out of her ass. Amy was obsessed with watching herself getting fucked in the ass, it was so wonderful. So exciting. Soon she could tell John was about to come, she felt his cock get harder and larger in her ass. Suddenly she felt the first shot of his hot cum go up her ass. As Amy watched, John pulled out of her, letting his creamy, hot, thick, semen spray all over her pussy, and red pubic hair. As he did he rubbed his cock, up and down, her pussy lips. All of a sudden, Amy came again, as his load of cum was being smeared all over her clit, and pussy lips, by his still-hard cock. Amy was enjoying the moment, the excitement, her multiple orgasms, and the whole experience. John was no longer in her ass, but her ass felt like it was on fire, nevertheless, it felt great. She loved the feel of his cum on her lower lips, dripping down over her sweet, first-time fucked asshole.

 Once John had stopped spewing man cum, he knelled between Amy’s legs and began to lick up and down her pussy lips and clit. Then he placed her legs on each of his shoulders, so he could better lick her freshly fucked ass, along with her sweet, pussy. The sensation of his wet tongue sliding all over her, probing her vagina and asshole, made Amy come again, even harder, in less than a minute. As Amy climaxed again, she pushed John away, she was so sensitive.

 They then lay on the floor relaxing, just talking, saying nothing important. John was on his back when Amy climbed on top of him. As they chatted, she slowly moved her wet pussy around on his semi-erect cock. After a while, she began to feel his cock growing harder, and harder. Amy sat up sliding his now hard cock, into her slick, wet, pussy. They lay there kissing, enjoying the sensations of slowly fucking. Amy leaned forward, so her breasts rubbed his face. John took a hard, red, nipple into his mouth, twirling his tongue around it, and then sucking gently. Amy adores a deep, slow, fuck, now with the added sensation of him sucking her nipples. She felt weak all over. Amy would slowly raise, almost off his cock, then slowly sink back down on him. After about ten minutes of this, Amy felt another orgasm building. Abruptly, she came one more time. As she did, she started kissing John, her tongue probing his mouth, as her climax ripped through her.

 After the waves of orgasm again subsided, she got off his cock, with a little fart-like sound from her pussy. They both laughed a little. Turning, Amy again sat on him, reverse cowgirl, her ass facing John’s face. She lowered herself so that his firm cock slid back into her wanting, dripping, pussy. Taking hold of his knees, she again began raising and lowering herself, slowly on his stiff cock. She felt John’s hands on her ass, as he spread her ass checks, watching his cock slide in and out of her slick, tight, pussy. Amy knew John loved watching, especially from that point of view. Then she raised off of him, grabbed his cock, and pointed it to her recently well fucked asshole. Once aligned she pushed down on him, feeling his hard cock effortlessly go into her rectum. It was perfection, as she moaned in delight.

 “Wow, that went right in. No wonder Sarah likes butt plugs. You just fucked me in the ass, so now I want it on my terms. I want control. I’m going fuck you with my ass,” Amy matter-of-fact told him.

Feeling his cock slowly going in and out of her sweet tight ass, was magnificent, also to John. She was still turned facing his feet, knowing he would want to see his cock fucking her cute, firm, ass from behind. However, she soon found out, that in this position, with his cock in her ass, she wasn’t as pleased with it as before. She had to lay back, placing her hands on his chest to get the feeling she wanted, so sit straight up. It felt much better. As she did, John placed a hand on each side of her ass spreading her ass checks, to watch. The stimulation in this position was sending sparks all through her, she loved it. Amy now sitting straight up, began grinding her hips around feeling, his cock which was now deep inside her well fucked ass. It was an incredible sensation for both.

 After a few minutes, Amy spun on his cock, so she was again facing him. She liked this way best. She adored the feel, the control. She reached down to play with her pussy, while they ass fucked. John sucked on her nipples. The sensation was mind-blowing. Once again Amy was close to coming, sitting straight up on his cock, her fingers running all over her pussy lips and clit. When they slipped inside her love tunnel, she again felt his cock on the other side of her vagina, it was so cool for her to feel it. All of a sudden she came one more time. This time harder, like a bolt of lightning going through her. As her ass muscles contracted around John’s hard cock, as she orgasmed, he started shooting his cum deep up her ass. Joining her in a magnificent mutual orgasm, as his hot semen flowed into her, she moaned from the pleasure of the feel of it.

 “Oh baby, that feels so good. Fill my ass with your cum.”

 Then she fell forward on top of him breathing heavily. Once she knew his orgasm had subsided, Amy slowly rolled off cock. It slid out of her ass with a pop, sounding like a loud wet fart. They sniggered again at that. As they lay there breathing hard, John took hold of her breasts, pinching her nipples, before sliding down between her leg to kiss her sweet, dripping, hot, pussy. Amy said nothing as he again placed her legs on his shoulders, before running his tongue up and down her lower lips, now and then rimming her now well fucked asshole. Amy just relaxed, enjoying his hot mouth and tongue. Shortly she came again, within a couple of minutes. Her legs tighten around his neck, arching her back as she came. She pushed him away, she was so sensitive, moving to lay on her side next to him.

 “I love the sensation of your cock in my ass. I love feeling your cum shoot up my ass. I love everything about getting fucked in the ass, it’s wonderful. I now find all anal play exciting. I’m glad you’re the first ever to take my virgin ass. Oh, no longer virgin ass. I’m so happy. Now I’m saying it’s only going to be for you. No one else will ever fuck my ass but you.”

 They held each other kissing side-by-side, just holding each other. John took one of Amy’s full firm breasts in his mouth, sucking a hard, nipple before falling asleep in each other arms. Not really knowing how long they napped, Amy awoke first. She moved down between his legs, taking his soft penis in her mouth. Slowly sucking on it, licking it, it began to grow in her mouth. John awoke to all the wonderful sensations she was giving him. Looking down, he observed the marvelous sight of his now fully erect penis, between her red glossy lips. As she orally pleased him, she looked up at him, her green eyes sparkling at him. 

 “I want your cum. I want to taste it. Come on Babe, shoot your cum on my face,” Amy demanded.

 Opening her mouth wide, licking the sensitive underside of cock-head, John started spewing hot, creamy cum. His cum hit her upper lip, then some hit her nose before she clamped her mouth on his spewing cock. Once his jets of cum subsided, she opened her mouth, cum dripped out covering his cock. Amy slurped it all back into her mouth, this time swallowing it. Taking a finger, she scooped up all the cum on her face. Slowly licking her finger clean, John watched. Then slowly, licking up and down his cock getting every drop of cum she could.

 “I love the taste of your cum. It’s good to the last drop. Thanks, for being the first to fuck my ass. And thanks for making sure I enjoyed it. I love you so much. My ass is only for you.

 Moving up kissing him deeply, she informed him they both need to go shower. So far he has been the only man to ever fuck her ass, that’s how special he is to her.