Strictly Anonymous Confessions, page 2
CONFESSION I: CANDY
After completely reinventing herself at the age of fifty-two, the only thing sweeter than Candy’s name was her post-sex craving for sugary treats and her voracious appetite for significantly younger men.
Candy was on the traditional path for the first part of her life: grew up in a small town, met a boy after college, was married by her early thirties, and had two beautiful daughters. But Candy had a bisexual naughty side that she had repressed throughout most of her early life. Such behavior was not accepted in the community that she had grown up in. However, her husband welcomed Candy’s bisexuality, and after moving to the Bay Area, they got involved in the San Francisco swinging scene. They quickly found that having an extra woman was what they both liked best.
Life happens though, and after over twenty years together, the marriage had run its course. Candy took stock of her situation: she was over fifty, divorced, very successful, and unwilling to get married again. She didn’t need a man to support her. She tried to date, but unfortunately, it wasn’t very successful as she was often left bored by the age-appropriate men she met. She gave it up after a few years, wondering if that was the end of dating for her.
Her Young Stud
Unexpectedly, she discovered she wasn’t done, just as she was having the solar panels on her house cleaned. A small crew showed up, and one of the workers, a very young good-looking guy, caught her attention. She had butterflies in her stomach. As she walked by him, Candy locked eyes with the young worker. His muscular arms were hard to ignore in his tight-fitting T-shirt, and she couldn’t help but wonder if he had washboard abs too. She thought to herself, Oh, my God, I want to fuck him. It felt like no one else was around as the fifty-two-year-old stared and smiled at the tall twenty-five-year-old. They chatted briefly, until the young man calmly and confidently took the conversation in a very different direction. He leaned in, lowered his voice and said: “I think you’re really hot,” and handed her a piece of paper.
Candy was dumbfounded when she looked at the note and saw his name and number. She thanked him for the compliment, and as he left, tried to collect herself. Over the next couple of days, she couldn’t stop thinking about him. Even though he was so young, Candy couldn’t help but be impressed by his boldness. Fuck it. I don’t care how old he is, he’s fucking hot and I want him, she decided.
Candy reached out to him the next day and he quickly asked her out to dinner. Two nights later she was in a bit of a frenzy as she got ready for the date. She had never been out with a guy that much younger than her and had no clue what to expect. She also couldn’t believe how aroused she was when he picked her up in his truck.
As they sat together at dinner it was obvious how excited he was to be spending time with her. Out of curiosity, she asked him if he had ever dated an older woman before. He stated he had. When Candy asked how old he thought she was, he guessed forty or forty-one.
“I’m fifty-two,” she confidently replied, but wondered if the age gap would be an issue for him.
He quickly replied that he found her even hotter because of it.
After they had finished dinner, they headed to his truck to drive home, but Candy decided she had other plans in mind.
“I think you should kiss me,” she said as she moved closer to him.
He turned to face her. Wrapping his arms around her waist, he pulled her closer and they began to make out. The chemistry between them was intense. As the make-out session continued in his truck, his hand slid between her legs, and she whispered: “Let’s find a hotel.”
The minute they entered the room, they began to tear each other’s clothes off. He picked her up in his strong arms and threw her onto the bed. Then he climbed on top of her and pressed his hard, naked body onto hers. As they started to kiss, she felt his arousal and thought, My god he’s huge. As they continued to devour each other, she couldn’t believe how passionate and patient that young guy was. It felt like they had been making out for thirty minutes, and he still hadn’t tried to fuck her.
When she finally couldn’t take it any longer, she grabbed his cock and guided it all the way in. As his hips made contact with hers, she felt every inch of him that was inside of her, and every muscle in his body that was on top of her. She was in heaven as they fucked for the next three hours. His stamina and energy were impressive.
After they had finished, as she lay there on the bed, she realized that was what she had been missing. That was what she had been waiting for. She had just fucked a guy half her age and God damn, it was fucking hot!
For the next several months, they rocked each other’s worlds. Sometimes they booked a rental home for the weekend, sometimes it was just a night in a hotel. With her sex drive reignited and stimulated to a level she had never experienced before, Candy felt she was getting her groove back. When her cub finally decided to go back to school, and his availability significantly changed, the wild love affair ended. Candy had seen the light though: younger men were her jam. They were easy to hang out with and didn’t want to possess her like the older men did. Ditching older guys and vanilla platforms for good, she switched to naughtier apps like Feeld and FetLife. Consensual, no-strings-attached sex was exactly what she was looking for.
Her Cuck
The minute Candy posted her pics online she was inundated with messages from hot young guys. Candy was having a blast hanging out with various local studs when someone from San Diego hit her up. She was surprised by the interest from someone four hundred miles away, but he seemed cool, so they started video chatting to get to know each other. She liked him, and their personalities meshed well, so after a month of talking online, he flew to Northern California for an in-person meetup.
When she first met him in the flesh, she felt an instant connection, as if it were meant to be. He also had a lot more experience in the kink world, and she was eager to learn from him. He was a cuck at heart and therefore was completely supportive of her fucking as many guys as she wanted. That was something new for her, and she loved it. A man who not only supported her wild desires but was actually turned on by them. From there they began to develop a deep cuck-hotwife relationship.
He encouraged her to push her boundaries, and with his support, that’s exactly what she did. They started out in the swinger scene, meeting couples and singles in various arrangements. Then they began attending sex parties where Candy discovered she really liked getting fucked by a line of guys, one after the other, while her cuck stood by and watched; he loved seeing her being pleased by other men.
As Candy got more into the lifestyle, she started exploring her submissive side and discovered one of the hottest scenarios for her was to be treated like a “whore.” She enjoyed nothing more than showing up at a stranger’s hotel room and immediately dropping to her knees to suck his cock right in the doorway. It was invigorating playing the submissive whore, which was in direct contrast to who she was in her professional world. Living a double life only made it hotter.
One day she sent a naked photo to her cuck of her legs spread wide open. When he sent the photo back to her, he had edited it and wrote “whore” in the space between her ass and pussy, along with instructions: Why not make this your first tattoo?
Candy decided to go for it, and a few days later, she found herself spread-eagle on a table at a tattoo studio. To Candy’s delight the tattoo artist replicated the image exactly. The minute he was done she snapped a pic and sent it to her cuck.
How do you like my new taint-too?
Her cuck was elated. When she started posting pics of her new ‘taint-too,’ her online popularity instantly skyrocketed. Enjoying the body modification and the online responses she had gotten from it, Candy also added six labia piercings and a Christina piercing (a.k.a a Venus piercing, placed on the top of the vulva, where the outer labia meet on the pubic mound).
Her Girlfriend
While having regular hookups with one specific couple, Candy started to develop a deeper friendship with the wife, Jasmine. Being right around the same age, the two older MILFs had a lot in common—especially their colossal craving for younger men.
It was refreshing to find another woman who understood her hypersexual attitude while in her fifties and they fed off each other’s intense sexual appetite. At first, their hookups between the two sets of partners were just fun nights of vanilla swapping sex. But soon they started trying all different types of configurations for each other’s bodies. Candy would ride Jasmine’s strap-on while Jasmine lay on her back with her head over the edge of the bed and had her mouth stuffed with both guy’s cocks. Sometimes one woman would be forced to only masturbate while she watched the other get railed by both men. Another evening Candy lay on top of Jasmine with their asses stacked in the air as one guy alternated between them. They were having fun and the sexual freedom they felt with each other was intoxicating.
Candy also loved Jasmine’s taste in men: a killer body, with a beautiful cock, and mind-blowing stamina, and she always seemed to have a good one around. It meant that when hanging out with Jasmine, Candy never knew when a hot evening was going to happen out of nowhere. One night, they were just hanging out in the kitchen when Jasmine’s boyfriend returned home. After he hugged Candy hello, he bent her over the counter, pulled her panties down, and dove his face deep into her from behind. She loved the intense forward approach! A minute prior, she was just chatting with her friend, then she was stomach down, ass up, and legs spread, getting her pussy licked from behind. He was so good that it didn’t take long before she reached back and grabbed a fistful of his hair as she orgasmed.
When the show was over, Jasmine kissed her boyfriend and said how she loved smelling the scent of her friend on his lips. Seeing how aroused Jasmine was, Candy took her into the bedroom, pushed her on her back, and proceeded to give her a treatment of her own. Soon Jasmine was squirting like a firehose all over Candy’s face, so much so that there were juices dripping from Candy’s eyelashes. After Jasmine’s eruption, her boyfriend proceeded to fuck the two of them for hours before they all passed out on the bed.
At 4 a.m., Candy was awakened by the boyfriend fucking Jasmine. Smiling, Candy rolled over and went back to sleep. A bit later, she was woken again when she felt him spread her legs. Oh my God, here we go again! she thought as he began to pound her for a second time. After the second round was over, she lay there holding Jasmine’s hand and thought how kinky it was that both women were filled with cum as they fell asleep.
Things got especially delicious the next morning, when Candy was rummaging through the fridge looking for a snack. She noticed a can of whipped cream and decided a little food play was in order.
“Hey, why don’t we eat this out of each other’s asses for breakfast?” she suggested with a devilish grin as she waved the can in the air.
Jasmine enthusiastically offered to dine first. Grabbing the can, she motioned for Candy to once again bend over the counter and spread her ass. Jasmine sprayed the cream between her spread cheeks and the cold temperature made Candy giggle. Jasmine’s face and Candy’s ass were a mess in no time. Then they switched positions for Candy to have a taste. After they devoured each other’s whip cream-covered bodies, the boyfriend fucked both of them again, sticky asses and all. The endless pounding that weekend left Candy walking awkwardly the next day.
As Candy and Jasmine continued on their epic journey of sexual adventures, they racked up tons of raunchy memories. While most gal pals shared things like makeup, shoes, or purses, Candy and Jasmine shared men and sexual experiences.
“Let’s have a gang bang together,” Jasmine suggested one day.
Candy loved the idea and was immediately on board. They searched through their combined pool of partners and agreed on five men to invite to the double gang bang that night. The women took turns watching every inch of each other’s bodies get ravaged by the guys. But being on the bed together and holding hands while getting fucked simultaneously was the best. Candy was the first to experience the airtight seal, but Jasmine followed close behind. All in the name of keeping things fair between friends.
Among the many gang bangs they would share, the Vegas one was by far Candy’s favorite. Five, hot, young Black men with huge cocks spent five hours taking turns on the older women. It was truly an unforgettable night. As sore as her ass was the next day, she felt as if she had died and gone to heaven.
Her Double Life
Recently, Candy had a great hookup while in Arizona while officiating a vanilla friend’s wedding. She looked for a local playmate while there and wound up connecting with a Dom. He showed up at her hotel room with a bag full of gear and restrained her with a spreader bar and handcuffs. He proceeded to spank her and tease her with a vibrator for the next couple of hours. Her moans were muffled by the ball gag stuffed in her mouth while he completely used her like a living, breathing sex doll—and damn, she loved it. Her ass was red from all the abuse when he finally slid inside her. Just before he came, he removed her gag so he could finish in her mouth. She could not have been happier.
The next day she officiated the ceremony as if nothing had happened, and she smiled every time she felt soreness in her body. Sitting was especially uncomfortable, so she tried to stand as much as possible. The fact that nobody knew what she had been doing the night before made it all the more exciting. Doing ordinary things during the day and then being super naughty at night left her exhilarated. Candy could transform into whatever was needed—a hotwife, a whore, a business owner, living sex doll, or, as she had that weekend, a wedding officiant.
Candy genuinely liked being thought of as a sexual being. As a teenager, overtly sexual compliments made her feel dirty and weird, but she had reached a place in her life where she had no problem with the attention. She loved everything about sex: from watching people fuck, to being tangled in the middle of a bunch of naked bodies. Even though she considered herself a huge slut, she was selective about who she hooked up with, and predominantly looked for guys who were young, tall, attractive, and well-hung. But at the end of day, what excited her the most was fulfilling a younger guy’s fantasy of being with an older woman, so she occasionally settled for a guy who was considered “average.”
Variety was the spice of life for Candy and there was never a shortage of it thanks to her growing list of online playmates. Between Jasmine, her cuck, a handful of regulars, and posting ads when she traveled, the supply of partners was endless. She also continued to flaunt her kinkiness with several hardcore video clips on her newly created ManyVids account ranging from full-length gang bangs, to shorter clips that include toys, penetration, facials, blow jobs, creampies, and more.
Right from the get-go, Candy gained a huge following and became a minor celebrity. She began getting recognized in places like movie theaters and grocery stores. One day while at the airport she received an email that read: I love your flip flops! I’m in line behind you at the gate.
Looking over her shoulder, Candy saw a man waving at her. The guy, who apparently had a foot fetish, was overwhelmed to be in the presence of Candy and her lovely, exposed toes. She gave the starstruck fan a hug and joined him for a selfie, before getting on the plane. It was like being an amateur porn star and she loved the flattering attention.
At fifty-four years old, Candy was grateful to have found her sexual liberation and couldn’t imagine ever being monogamous again. The biggest difference between her younger and current self was that she no longer gave a shit about what people thought. She also had no shame about what she was doing sexually. She was living out all the fantasies she had ever imagined, and she couldn’t be happier. She was free for the first time in her life and planned to stay that way.
Based on episodes
650 - Candy Is a Hotwife MILF “Slut” into Younger Guys, Threesomes, Sex Clubs, and More
733 - Jasmine and Candy Have Had Gang Bangs, Threesomes, and Foursomes Together, and More!
CONFESSION II: SEAN & SAMANTHA
We all know that outward appearances can be deceiving— and that is precisely what Sean and Samantha thrived on. On the surface, Sean appeared to be the quintessential alpha male, but behind closed doors, he was secretly obsessed with getting pegged, wearing panties, and sucking cock. And, Samantha, his wife, was obsessed with it all too.
When Sean and Samantha met seventeen years ago, she was instantly attracted to his alpha male energy, rugged good looks, strong physique, and successful career. The icing on the cake was that Sean could go for hours in the bedroom. Samantha was in ecstasy. Dating turned into an engagement, and eventually, a marriage. For years they had an active and enjoyable sex life with Sean being very dominant and in-command, both in and out of the bedroom. They could never have suspected the turn that their sex life would take.
Opening Pandora’s Box
It began very innocently one evening a couple years back. The two of them were home having a few drinks and getting frisky with each other. After all those years of marriage, they had started trying to spice things up a bit by introducing toys into the bedroom. With a vibrator here, and a dildo there, they were making it up as they went along. On that evening, maybe it was the drinks coupled with a yearning to push boundaries, Sean was feeling a little more adventurous than usual. With Samantha’s gorgeous body spread out naked on the bed next to him, he picked up a dildo and said: “Hey, can I put this in your ass?”
Being in a playful mood herself, Samantha laughed and said the words that would change the course of their sex life forever: “Sure! But only if I can put it in your ass too!”
Sean’s mind froze, but his body reacted in a way he wasn’t prepared for. He instantly got hyperaroused. He had never considered doing anything like that before. But there he was, hard as a rock at the prospect. They proceeded to spend the rest of the evening playing with each other in a way that surprised them both.
