Grandma Millie’s Kinky Night

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Oca 13, 2023 // By:analsex // No Comment

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Redheaded twenty-three-year-old Danica had a thing for older men. It had begun when she was seventeen and was seduced by an older neighbor who was forty-two. After him, the boys her age didn’t seem satisfying for reasons she could never fathom. Her next older lover happened to be her uncle who was thirty-nine. That taboo fling hooked her on mature men. At first, this bothered her, then as she matured, she decided it is what it is, so why fight it?Her subsequent lovers ranged from forty-five to sixty-seven. She had also once given a blowjob to a seventy-eight-year-old guy. She was working as a waitress and he was a customer. They hit it off and when he finished eating, she took a break and met him at his car where she sucked him off. It was the first blowjob he had ever received. She was fond of the memory. He had tipped her one-hundred dollars, but she disassociated that from the sex somehow.After college graduation, she took a job at a firm in a new city and was assigned to an older man to learn the ropes in his department. His name was Jim Webb. Right off the bat, Danica, or Dani as she liked to be called, took a liking to Jim. He was fifty years old and still trim and good-looking. Almost made to order for her particular sexual desires. Unfortunately, he seemed to be very happily married to a woman named Jan.But things were about to change with Jim and Dani. Both of them were assigned to attend a work conference lasting a week out of town. And both of them were to fly out together and stay in the same hotel. It was inevitable that they would spend a lot of time alone together as it was just him and her attending from their office. Dani saw the possibilities in all of this and decided if there ever was a time to get closer to Jim, it was during this week.Jim certainly enjoyed his new trainee, Dani. She was smart, perky—in fact downright sassy, and easy to look at. Very easy to look at! Jim found himself staring at her tits, ass, legs, you-name-it when they were together. He found himself wondering what she looked like naked. She was rather earthy and flirty and by her very nature attracted his attention. Not that he would cheat on Jan of course, but if he did…well Dani would be a hot choice. Of course, when these thoughts occurred to him, Jim immediately realized that they were silly. Why would a hot, single, twenty-three-year-old want anything to do with a fifty-year-old guy in bed?When the work conference came up, he was secretly thrilled. Normally he loathed these things, but spending time with a sexy chick like Dani would make it very pleasant. Who knows? Maybe he might be able to push the marriage envelope a bit with her if he had a chance. He wasn’t sure what he would do, but he liked the idea.DAY ONEThe plane was crowded and Dani had a window seat next to Jim. She was dressed in a short skirt that showed a lot of legs. That alone made it pleasant to sit next to her. There was just a hint of perfume as well. Her red hair looked radiant. The conversation was fun and lively. When Dani had to get out to use the bathroom, sliding by Jim with her long bare legs and sexy body was quite…uh…enjoyable.After arriving at the hotel where the conference was to be held and getting settled in their respective adjoining rooms, Dani suggested that they get a meal together. Still wearing the mini skirt, she suggested they walk through the scenic historic district and pick from one of the restaurants there. It was very pleasurable for Jim to walk with this sexy girl by his side, though he figured most people would assume she was his daughter. Every so often she made bodily contact with him in the crowded street, enhancing the enjoyment.Finally, she selected a trendy eatery and they sat down for a meal together. More than a couple of beers later, the meal was finished, but the conversation continued. Jim asked Dani if she had a boyfriend. She told him she didn’t and added an intriguing statement.Dani told him in a rather lengthy monologue, “I think my problem is that men my age seem so immature. I have been out with a few older men and I much prefer their company. Like here right now with you. You aren’t preoccupied with your phone, your attention is all on me. You have lived long enough to have great stories and perspectives. And I like the way older men treat me, including you right now. I’m enjoying this evening with you—which goes to prove my point.”With that, Dani laid her hand on top of Jim’s as she looked him in the eye. It lingered there for was seemed like minutes to Jim, but was probably only a few seconds. It seemed to be a very personal signal, saying “I like you.”A bit rattled, Jim mentioned that they should leave, others were probably waiting for their table. And leave they did. But the walk back to the hotel was quite pleasant, and Jim could have sworn that Doni’s body made contact with his as they walked, far more than necessary in the crowd.At the hotel Jim walked his sexy redhead to her room door he stood for a moment with her as she unlocked it. It was almost as if he was saying goodbye at the door of a date.“I enjoyed tonight with you, Dani. You made it fun for an old guy like me,” Jim told her.“You’re not an old guy, you’re just right. I told you how I like men around your age. So I’m the one that should be thanking you. And I’m looking forward to the rest of the week with you,” Dani replied with a smile and a touch on his arm.“Give me a hug and I’ll go, Jim,” Dani asked.Jim gave her a hug, which only inflamed his ardor, and then walked to his room almost on air. Young Dani had turned him on with her sexuality and openness. Getting inside he was as horny as could be. Stripping naked he imagined fucking Dani. Next, he began to look at internet porn involving redheads. With his cock rock hard he decided to take a selfie of himself in front of the mirror. He wanted to send it to Dani but didn’t want to be creepy, so he sent it to his wife instead. It was late and he was hoping that Jan and he could maybe do some sexting. They had done it once before when he was out of town and both enjoyed it.Jim text/pic – sends a selfie photo of him naked with his cock mostly hard taken in front of the hotel room mirror.Jim text: “Wish you were here naked with me in bed.”Jan text: “Me too. I’m lonely without you. You look sexy my hot naked man.”Jim text: “I’d love to be sucking your tits right now.”Jan text: “Mmm, suck them, honey.”Jim text: “Are you naked?”Jan text: “I am now. Playing ankara travesti with my tits.”Jim text: “I want to see. Show me.”Jan text/pic – sends a selfie photo of her tits.Jan text: “Suck these.”Jim text: “Oh baby! I’m so hard. I want to suck those nipples.”Jan text: “Is your cock hard yet?”Jim text/pic – sends a selfie of his hard erect cock: “My cock for you to suck.”Jan text: “I want to deep-throat it until you cum in my mouth.”Jim text: “Suck me, baby. Suck my cock ‘til it cums.”Jan text: “Are you jacking off now?”Jim text: “Yes I am. I’m stroking my big hard cock thinking of fucking your pussy.”Jan text: “Fuck me, Jim. Fuck my pussy hard.”Jim text: “I’m fucking you hard right now. Feel my big hard cock in your pussy?”Jan text: “Yes! I’m riding your cock. It fills my pussy deep and full.”Jim text: “Take a pic of your pussy.”Jan text/pic – sends a pic of her pussy: “Eat me and fuck me.”Jim text: “So hot! Are you playing with your pussy yet?”Jan text: “Yes I am honey.”And it was true. Jan was laying in her bed, naked and fingering her clit. She had just made up her mind to get the vibrator out of the drawer. It looked like she was going to need it!Jim text: “Spread your pussy for me and take a pic.”Jan text/pic – sends a pic of her fingers spreading her pussy: “For you to eat and fuck.”Jim text/pic – sends a pic of his tongue sticking out: “I want to eat and fuck your tasty cunt baby.”Jan text: “You horny old bastard! Eat my cunt and lick my clit.”By now, Jim was stroking his cock, feeling the good feeling that comes from doing that. The pleasure rose from his balls to the tip of his dick. Enjoying the thrill of it as he looked at pics of his wife’s cunt spread for him.Jim text: “I’m going to eat and fuck that pussy of yours with my big cock and fill it full of my cum.”Jan text: “Fuck my cunt honey! Fuck me hard! I’ve got the vibe and it feels so good. Wish it was you.”Jim text: “Send me a pic of the vibe in your pussy.”Jan was feeling the glow and tingle from using the vibrator on her pussy. She read Jim’s text message but hardly wanted to stop and take the selfie. While she debated, she made herself cum. Shaking with the joy of it, she fell back on the bed. Finally, she had the energy to take a pic of the vibrator in her pussy and send it to her husband.Waiting for Jan’s next pic, Jim slowed his stroking, carefully edging himself to orgasm. When the text message tone sounded, he assumed it was his wife’s reply. He was wrong.Danica text/pic – sends a pic of her, taken in the mirror, in a thin, white t-shirt showing the outline of her boobs and her hard nipples sticking out, with her smiling face partially obscured by the phone: “Hi Jim. This is Dani. Thanks for the fun evening. I’m going to bed now as you can see, but let’s eat breakfast together in the hotel restaurant at eight am. Okay?”Jim was stunned. To be honest, the selfie was of her dressed. And you did have to look a bit close to notice her boobs and nipples. It was within plausible reason, but—it also did give a big sexual hint. Perhaps she just didn’t notice how she looked before she took the selfie. Or perhaps she did! One thing is for sure, it made him start stroking his cock hard again as he downloaded the pic to his photos.When Danica got back to the hotel room, she was hoping that Jim would make a move. When he didn’t she went inside and got ready to go to bed, if not to sleep. The air conditioner was turned rather cold and she noticed her hard nipples sticking out of her shirt. She was only wearing her thong beside the shirt. So she took a couple of selfies of herself in the mirror. Feeling naughty, she also took one with the shirt lifted up, exposing her boobs. Finally, she settled on sending Jim one that was subtle in its sexiness, but sent a message if you looked. She was hoping he would take the bait.Jim text: “I had a lot of fun tonight too. I’ll meet you at eight am for breakfast. P.S. You look good!”Jan text/pic – sends a pic of her pussy with her vibrator part way inside of it: “Wish it was your big cock honey.”Between the pic of Dani showing the outline of her tits and Jan’s pussy getting fucked by the vibrator, it was too much. Jim started jacking his cock hard and fast and soon his cum was spurting out and onto his glans, shaft, and belly. He quickly took a pic.Jim text/pic – sends a pic of his cock dripping cum: “Thinking of fucking your hot pussy or having you suck my cock made me cum.”Jan text: “Glad I made you cum, sweetheart. You made me cum too.”As they wrapped up their sexting session, Dani was next door, naked and using her little egg vibrator on her pussy. Imagining Jim was fucking her she worked both her fingers and the vibe until she, too, had a nice orgasm. Only a wall and a couple of feet separated the two naked bodies, each manually pleasuring themselves. It was a perfect case of “if only.”DAY TWOBreakfast was nice, mostly because of eating it with the sexy Dani. Jim tried to picture her tits but was partly foiled because she was wearing a button-type blouse showing little cleavage and a tight pencil skirt that were typical business attire. Her red hair was tied back in a bun. Her sexuality was well-hidden but still latent.The training session was boring. Jim kept looking at his watch, knowing that a coffee break was imminent. Dani sat next to him and was playing on her phone. He assumed she was texting someone. It was at that moment that his phone vibrated. Looking at his phone, he saw a new text message and scanned it rapidly with his eyes.[Danica] text: “I wish I was under the table now giving you a blowjob.”Jim was stunned! He knew Dani seemed to like him, and she did talk about liking older men, but this was beyond his wildest dreams! Sexy redheaded Dani wanted to suck his cock!Turning to Dani, he smiled at her and put his hand on her leg under the table, saying, “I wish you were too. Maybe after this is over we can do something about it.”While Dani didn’t do anything about his hand on her upper thigh, she did give Jim a quizzical look. Smiling back at him she said, “What do you mean?”At this point, the speaker finally ended his PowerPoint and the group was dismissed for a coffee break. Jim and Dani got up and stood to the side, away from the others milling around.“Your text to me, Dani. I’m talking about what you texted me,” was Jim’s reply.“Let me see your phone, Jim,” Dani requested.Jim showed her his phone and the text messages.Laughing, Dani said, travesti ankara “You didn’t read this very carefully. This text is from your wife, Jan. She wants to suck your cock under the table!”Jim was mortified, turning bright red. Speaking to Dani, he said, “Oh my god! I’m so sorry! I thought that it was you for some reason. I saw you texting and thought that you were texting me.”“So obviously you thought I was the one that wanted to suck your cock under the table, right?” Dani persisted.“Um…yeah. I did for some reason. I’m so sorry,” Jim answered.Dani saw her opening to seduce Jim and threw out some bait, “Well, I’m flattered that you would like that. It would be a better way to pass the time for both of us than listening to that guy drone on. It sounds like your wife is hot. I can understand why she texted you that. I wouldn’t mind doing that to a hot guy like you either.”Jim could hardly believe his ears. Was Dani saying that she wouldn’t mind giving him a blowjob? Or was she just talking theoretically, saying that she would like to give a blowjob to a mature guy like him? While he was pondering this, Dani patted him on the back and said, “I’ve got to go to the little girl’s room,” and left.The meeting started as soon as Dani returned and nothing was said. The session droned on with a PowerPoint safety presentation that they had all seen before and other boring stuff. Jim noticed that Dani again had her phone out. She gave him a little wry smile just before his phone vibrated.Danica text: “This is so boring. I wish both of us had someone under the table giving us oral right now (wink emoticon).”Jim looked at Dani and saw the little vixen grinning at him.Jim text: “You have a dirty mind. I love it!”Danica text: “So that is a yes? You wish that was happening?”Jim text: “Hell yeah! But when both of us had an orgasm, I don’t know if we could keep quiet!”Danica text: “Mmm, I’d like to see if I could!”Jim text: “Damn you. You are making me horny. I’m supposed to be paying attention to all this crap.”Danica text: “You like the idea, don’t you? How horny are you?”Jim text: “Horny enough.”With that, Dani gave Jim a sly sideways smile and reached under the table, putting her hand on Jim’s upper thigh.Looking at Dani, Jim mouthed a whispered, “What are you doing?”Whispering back, Dani said, “Just checking.”And with that, she reached further into his crotch and felt his hard cock down alongside his leg in his inner thigh. And then gave it a little squeeze.Jim whispered, “What are you doing?” with a bit of a chagrined smile.All Dani did was wink at him before she withdrew her hand. For the rest of the training session, Dani behaved and paid attention to the lecturer. Jim had a hard time getting his brazen redheaded protégée off his mind. Though he tried to dismiss his desire to fuck her because he was happily married, it was a losing battle. He decided to try and walk the cliff edge of sex with her if he could. No penetration of her vagina, but maybe do some other shenanigans. That wouldn’t be cheating, would it?When the day’s meeting was finally at an end, the vibe between Jim and Dani was sexually charged. Acting as if nothing sexual had passed between them, they decided on a restaurant to eat at. Although invited by some other co-workers to eat and drink with them, the pair demurred. A Thai restaurant was finally decided on, and the walk was pleasant. Once again, Dani would bump and touch his side as they walked. Jim enjoyed every second of it.Dinner was interesting. The conversation became Dani asking about Jan. What she was like and all that. Jim didn’t particularly care to talk about his wife when he had cheated on her in his mind. Nevertheless, he politely answered Dani’s questions. Again Dani talked about how she didn’t care for men her age. And again she emphasized how she was attracted to older men.“What are you saying, Dani? Are you talking about me and you?” Jim asked.“Okay. I’ll admit that I’m very attracted to you. I can’t help it. It’s just who I am. I’m not looking for a serious relationship right now with an older man, it’s just that I have certain, uh, desires sometimes,” Dani confessed.“I am happily married, you know. But I have to admit that I find you very attractive. I know it’s wrong. But I am,” Jim told her.“Let’s not think too much about it. Let’s just enjoy the evening together, okay? Just spending time with each other,” Dani opined.With that they relaxed and let the conversation get lighter, laughing about their texting during the meeting and just enjoying each other’s company as they walked back to the hotel.At the hotel room door, the scene was starting to play out like it had the night before. But this time Dani stepped in with an offer, “Why don’t you come inside for a minute? We can have one of those hotel mini-bottles from the ‘fridge and talk some more. I don’t want to be lonely tonight like last night.”With that, Jim stepped across the threshold into Dani’s room, and onto the jagged edge of cheating.If Jim would have known that while Dani and himself had been eating dinner, his wife had been having lesbian sex with Cathy Jones and talking about screwing Cathy’s husband, Mike, it might have made what came next easier. [See: “Jan And Cathy’s Lesbian Fun”]In the hotel room, there was one chair and a queen-size bed. Dani got out the booze and motioned Jim onto the bed where they sat and sipped the drinks she had poured.Dani broke the ice, “You know, Jim, I really would have given you a blowjob under the table today if I could have.”“Oh god, Dani. I don’t know what to say, other than I will admit that I would have loved for you to do that. I guess that is why I missed seeing that the text was from my wife, I was hoping it was from you. Am I bad?” Jim told her truthfully.“No, you’re not. I think there is chemistry between us. And pardon me for saying so, but I think we need to do something about it because we are both on edge. We know what we want, but we are a bit scared,” Dani told Jim, putting her arm around his shoulders and looking him in the eye.“Yeah…you’re right, Dani. Too much thinking…” Jim acceded as he moved his face close to Dani’s upturned face.The kiss was electric. It seemed as if a dam of passion had burst. The moment they started, it wasn’t going to stop. Their bodies craved the touch of each other and they quickly wrapped their arms around each other as they slid down the bed until their heads were on the pillows.Dani’s ankara travestiler young, fit body felt amazing in his arms. It was such an extreme turn-on to hold another woman in such a sexual way that he felt incredibly high. And it wasn’t the booze. No, it was the intense sexual excitement. At that moment he knew that despite his intentions only to go so far, he was going to fuck this beautiful redheaded young girl.Dani felt amazing. It was what she had been craving. Jim held her strongly and tightly in his arms as he gave her passionate kisses. Soon their tongues were exploring each other. She felt the first flushes of sexual pleasure course through her body. She knew that she need him on her and in her and surrounding her with his naked body against hers. She began to unbutton his shirt. He eagerly helped her, baring his chest.Next, it was her turn. She sat up beside him and raised her arms as he undid the blouse buttons and pulled it off, leaving her wearing just her green lacy bra. Her tits jutted out firmly, a beautiful sight for Jim. He began to kiss her neck and shoulders, pushing her back down onto the bed, climbing on top of her body, holding her arms down as his kisses ravaged her long slender neck and her bare shoulders, then lower to the upper mounds of her pale breasts.Dani closed her eyes and just enjoyed his kisses ravishing her upper body and neck. Jim knew the value of good foreplay so Dani let herself concentrate on the oral stimulation he was giving her as he dominated her on the bed.Opening her eyes halfway and gazing lovingly at him, Doni told Jim softly, “I’m all yours tonight. Anything you want to do, I’ll do. Anything at all.”With that said, she raised and undid her bra, letting it fall to expose her wonderful tits. And wonderful melons they were—perfect size and shape with enough weight to make them sag slightly. C-cup joys with delicious small pink nipples accenting them. Her skin was the pale of a true redhead that contrasted with his tanned torso. Deliberately Jim began to lick each nipple in turn, then suck each into his mouth. Dani moaned with the pleasure of it all, spreading her legs to let his leg fall between them, then pushing upwards with her pelvis to press her pussy against his hard leg.Jim moved his mouth to hers, engaging her in a deep French kiss as his hand fondled her tit. His cock was rigid now in his pants. As they kissed, he moved his hand down over her flat belly and began to rub her pussy through her stylish jeans. Her pussy responded, just like it had to her leg. Dani moaned and kissed him even deeper, holding him tight against her.Dani’s pussy was on fire and needed the direct touch of Jim’s hand and fingers on it. She reached down and began to undo her jeans. Jim was quick to help her, and before you knew it, she had raised her bottom and let him slide them down to her ankles. At this point, Jim’s lips left hers and once again moved to her nipples, sucking them in and making them hard. While he did so, his fingers went under her brief panties and began to massage her pussy lips, parting them to allow his fingers entrance to her wet beaver. While he did so, Danica reached both her hands down and slipped off her thong, giving free access to her pussy.Dani’s pussy was covered in trimmed pubic hair that was a reddish-blonde in color. It was trimmed in a wide stripe up the middle. Her pussy lips were small, pink, and delicate compared to his wife, Jan’s, and made him think of the girls of his late teens. Despite her being sexually active, he knew she would be tight. He began to finger her in earnest now, probing her wet pink cavity for her clit. It was surprisingly large and at his touch, she visibly jumped and moaned.“Oh god, yes! Oh yeah…mmm…oh yeah…oh god, that’s the spot,” she told her mature lover.As he finger-fucked her, she reached down and began to stroke his hard cock from the outside of his pants. Soon she was unzipping them and fishing out his cock, all the while moaning her pleasure. Jim couldn’t take it anymore and took a break from fingering her to pull his pants and then his shorts off entirely. While he did so, Dani did the same, removing the pants trapped by her feet. At last, they were naked with each other, and Jim drank in the sight of Dani’s naked body.And a beautiful naked body it was. Dani was in her prime with nice full tits and great shape. She was fit and her stomach was flat. Being ginger, she was very pale. She had the type of body that makes centerfolds and porn starlets. Curvy, sexy, and tasty. The kind of body that men love to masturbate to when they look at porn. The kind of body that makes their cocks hard and throbbing, until their hand gives relief and they explode with spurts of cum, dreaming of fucking this girl.But Jim now had the real thing, as unlikely as it was for a fifty-year-old. A naked redheaded, willing vision of sexual perfection, laying on the bed with him, telling him that she would do “Anything you want to do.” The very fact that been sucking those perfect jugs and fingering that tight, prime pussy, seemed unreal. But it wasn’t. He could even smell her sex, her juices emanating a musky odor.But Jim didn’t have long to think about it. Dani immediately patted the bed beside her and commanded him to lie down. Complying, Dani positioned herself above him, dangling her tits in his face as she rubbed her pussy along his turgid shaft.Her tits looked even more amazing hanging down. While he was used to big tits with Jan, hers were excitingly different. It had been around thirty years since he had experienced sex with another woman besides Jan and he was finding the experience heady beyond belief. It made him feel as if he were high. The thrill of cheating with this young woman was the ultimate drug.After sucking her glorious globes for a minute as she dangled them temptingly in his face, she laughed and said, “I knew you would like my girls. But now I’m going to do something for daddy. You don’t mind me calling you ‘daddy’ do you?”In Danica’s experience with older men, she had learned that calling them “daddy” seemed to turn most of them on. Evidently, there seemed to be an incestuous streak or fantasy that older men held. Usually men over forty. And calling them “daddy” seemed to turn them on even further. Dani also pondered why she liked doing this, or even why she liked older men. Was she looking for a “daddy” figure? Dani didn’t know and didn’t care. She just knew what she liked and damn the psychology.“Oh yeah, baby. You can call me daddy,” Jim replied as Dani slid her body down until her face was even with his cock.“Would daddy like his favorite girl to suck his cock?” Dani asked, continuing with the mock daddy/daughter fantasy.

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