A3 – Younger Man with Older Woman

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All characters are over the age of 18.


Since Jeff’s mother, Rose, allowed her son to have his incestuous, sexual fantasy with her naked body, as promised, Brianna arranged for Rose to experience her sexual fantasy by having sex with Jason, a man half her age.

Brianna told her friend, Jennifer, about wanting to give her boyfriend, Jeff, his sexual fantasy with his mother. As part of that sexual arrangement, with Brianna becoming quite the sexual fantasy maker, as added incentive for her to go through with it, once Rose gave Jeff his sexual fantasy, Brianna promised to give his mother her sexual fantasy, too. As her sexual fantasy, one of the most common sexual fantasies of many women her age, Rose wanted to have sex with a man half her age. With Brianna already having sex with Jennifer’s son, Jason, several times, he was who she had in mind as Rose’s sexual, fantasy lover.

As much as it was the sexual fantasy of many older women to have sex with much younger men, it was the sexual fantasy of many younger men to have sex with a much older women, especially when the women were MILFs. Rose was over 50-years-old and Jason was only twenty-something-years-old. Yet, even at her age, keeping herself physically fit with swimming and tennis, not looking her age, she was certainly good looking, shapely, and sexy enough. Moreover, in the way that Jason’s mother did, a bonus for some men who love big breasted women, Rose had huge, D cup breasts, too.

Even though Rose wasn’t a member, since they were all members of the mother and son’s incest, swing club, Brianna knew that Jason would readily agree to have sex with Rose. Actually, always looking for new members, especially female members, she was hoping to enlist Rose into their private and exclusive sexual club. Not only open to just couples but also open to single women, but not to single men, single women were always welcome to join. Much easier to get single men to join a sex group, it was more difficult recruiting single women.

“Jason. Go with Brianna. She wants to introduce you to her boyfriend’s mother, Rose. Rose is looking to have sex with a hot, young man and, of course, we thought of you,” said Jennifer. “While hoping to recruit her to join our group, we want you to show her a good, sexual time.”

Jason smiled at his mother and gave her a long, wet kiss while groping her big breasts through her clothes, first one and then the other. Then, he turned to Brianna, his favorite MILF of fuckbuddy. He kissed her while groping and squeezing her perfect, tight, little ass. Out of all his mother’s friends and his friends’ mothers, and he knew because he had sex with them all, she may not have D cup breasts, but she had the best ass. Moreover, she was the prettiest of his mother’s friends, right behind Violet, Tyrone’s mother.

While he continued feeling her sexy and shapely ass, Brianna reached down to trace the length of his erection through his pants with her fingertips. Obviously, as much as Jason enjoyed having sex with her, she enjoyed having sex with him. Then, when she parted his lips with her tongue and kissed him, he returned her French kiss with his long, wet kiss. Ready to give Brianna sex, instead, she needed Jason to give Rose sex.

“Are you ready to meet Jeff’s mother and give her the sexual fantasy she dreams of having,” asked Brianna?

Jason smiled at his mother’s best friend.

“I’m always ready to have sex with another MILF of a mother. Lead the way, Brianna,” said Jason.

# # #

Brianna telephoned Rose to let her know that they were coming. With Rose living just a few streets over, they walked to her house. Eager to introduce Jason to Rose, Brianna rang Rose’s doorbell.

Expecting her to wear a skirt and a blouse, surprising Brianna and shocking Jason, Rose answered her door wearing a short, low-cut, sheer, and sexy nightgown without having the modesty to wear a robe. Her nightgown was so sheer that it was virtually see-through. As if she was wearing nothing at all, Jason could clearly see the size and shape of Rose’s big breasts, her trimmed patch of brown, pubic hair, and her naked ass through her nightgown.

“Oh, sorry, I didn’t think you’d be here so soon. I haven’t had time to change,” said Rose lying. “I threw this on old thing to be comfortable while watching TV,” she said staring down at what she could see of her naked breasts before looking up at Jason to see if he was enjoying the nearly, naked view of her beautiful body. “Well, since you’re here not, why bother changing,” she said with a shrug and a little laugh? Come in,” she said not covering her nakedness with her hands and still not putting on a robe.

As soon as he entered her well-lit home, trying not to be too obvious, Jason stared at all that he could see of Rose’s enormous breasts, her brown, erect nipples, and her perfectly symmetrical areolas. Rose escorted him to the living room and offered him a seat in her Queen Anne chair that was perfectly positioned opposite the couch. If Rose had intentions of deliberately Onwin flashing Jason while making her flashing appear accidental, the living room was where she’d do it.

“May I get you something to drink?”

As if she was standing before him naked, preoccupied staring at all that he could clearly see of Rose’s big tits and her trimmed pussy, mesmerized by the sexy sight of her nearly, naked body, Jason took a long second to respond.

“Oh, um, beer, if you have it,” said Jason peeling his eyes away from all that he could clearly see of Rose’s sexy and shapely body.

Continuing to sexually tease him, Rose turned from Jason and leaned forward at the waist to pick up an imaginary piece of lint from the carpet. As soon as she bent forward, her nightgown stretched across her shapely ass making her nightgown even more transparent. Clearly, Jason could see her ass crack and the complete outline of her naked ass. With her short nightgown raising itself higher in back, he not only saw her pantiless ass but also, he saw the back of her exposed, naked pussy.

“One beer coming right up,” said Rose.

# # #

Brianna cornered Rose in the kitchen.

“That’s some sexy nightgown, Rose,” said Brianna with a dirty laugh. “If I stare long and hard enough, I can count your pubic hairs.”

Rose laughed too.

“I wanted to dress for the occasion. It’s been a longtime since I’ve had the opportunity to wear something sexy. Having sex with a much younger man, a handsome man, who is half my age, and a man who isn’t my son, has been my longtime, sexual fantasy,” said Rose with a dirty laugh. “I’m so very sexually aroused, Brianna. Thank you for arranging this.”

Brianna returned Rose’s dirty laugh with her dirty laugh.

“I’m glad I could help your sexual fantasy come true. As I promised, Jason is your sexual fantasy for giving your son his sexual fantasy,” said Brianna. “Have fun.”

Rose gave her future daughter-in-law a kiss on the cheek.

“Thank you,” said Rose. “Jason is very good looking. I can’t wait to get better acquainted with him, if you know what I mean,” she said giving Brianna a sexy smile and a wink.

Brianna nodded her head and laughed.

“Trust me. Been there and done that, I know exactly what you mean,” said Brianna with a dirty laugh before changing the subject. “By the way, have you spoken to Emma, yet, about your daughter giving your son his sexual fantasy, too? In the way that he always wanted to see and feel your naked breasts while you masturbated him, he always wanted to see and feel his sister’s naked breasts, too, while she masturbated him.”

Rose smiled naughtily at Brianna while giving her a sexy look.

“I did, indeed, talk to my daughter about having sex with her brother,” said Rose.

While waiting for her to get to the good part and finish, with Rose delaying her response, Brianna rolled her eyes and sighed.

“What did she say,” asked Brianna impatiently? “Is she willing to strip topless and allow her brother to have his wicked, sexual way with her naked breasts while she strokes his cock?”

Rose laughed.

“Don’t worry, Brianna,” said Rose waving a relaxed hand. Suffice to say, like mother like daughter. In the way that I was eager to show my son my naked breasts while stroking his penis, Emma is eager to show her brother her big, naked breasts while stroking his naked prick,” said Rose. “I arranged a brother and sister get together for tomorrow night, if that’s okay with you and Jeff.”

Brianna smiled her sexual satisfaction.

“Tomorrow night is perfect,” said Brianna.

# # #

After Brianna left, Rose leaned over Jason while serving him his beer. As practiced in her bedroom mirror, the top of her nightgown fell open when she leaned lower. Remaining in that position longer than necessary, she made sure that he got a good, down-nightgown view of her huge, naked breasts and her erect nipples. Obviously, Rose enjoyed flashing her naked breasts and Jason, a big breast lover, enjoyed seeing her naked breasts.

With him sitting higher across from her in the Queen Anne chair, she sat lower in the soft comfort of the sofa. As if she was Sharon Stone in Basic Instinct, she parted her knees enough to give Jason a continual up-nightgown view of her trimmed, brown, naked pussy. Something she had never done before, this was her first time deliberately flashing a man her naked tits and her naked pussy, especially a younger man, and someone she had just met. With her nipples at full erection and her pussy already glistening wet from the exhibitionistic show, she was already as sexually aroused as Jason was, no doubt, sexually excited.

He stared at all that he could see of her nearly, naked body. As his sexual reward for being so sexually attentive, she continued flashing him her naked breasts and her naked pussy. While continuing to make her flashes appear unintentional, she continued sexually teasing him. Now, that she discovered how sexually arousing it was to flash bits and pieces of her Onwin giriş nearly naked body, she couldn’t wait to flash the delivery man, the maintenance man, and whomever else came to her door.

Obviously, thinking that she was the one sexually seducing him, she was unaware that Jason was a swinger. Nor did she know that he preferred having sex with older women, women his mother’s age or a little older, than having sex with women his age or younger. She was unaware that Jason not only was having sex with his mother, Jennifer, numerous times but also with his mother’s friends and his friends’ mothers while his friends had sex with his mother and with their mothers.

“So,” said Jason getting to the point and not wasting time with small talk. “Brianna told me that your sexual fantasy is to have sex with a younger man.”

Playing her role as the MILF of a mother of the house, she gave Jason a sexy smile and a naughty look.

“Yes,” said Rose. “I wanted to experience all that I missed when being married to a cheating, lying, and drunken man for most of my adult life. Now that I’m divorced, with my life quickly passing me by, it seems that men my age are only interested in women half their age. It’s sexually gratifying for me to know that there are still young men who appreciate older women,” said Rose.

Jason agreed by nodding his head while smiling.

“Well, on that note,” said Jason. “I like you, Rose, and I hope you like me, too. If you’d like to have sex with me, I’d love to have sex with you.”

# # #

Inviting him to sit next to her, she patted the sofa cushion with her hand.

“Come sit with me on the sofa where we can get better acquainted. Would you like to watch a movie? We can cuddle while watching a movie. I love cuddling. I miss cuddling,” she said with sadness. She looked at him as if daring herself to say what she was thinking. “While we’re cuddling, I don’t mind if you touch me and feel me through my nightgown,” she said giving him a sexy wink.

Jason continued staring at all that he could see of her sexy and shapely body through her nearly transparent, sexy nightgown before standing and sitting beside her. She was so beautiful. She was so sexy. Why someone who looked like her was without a man was troubling. Why someone who looked like her hasn’t had sex was shocking.

“Sure? What do you have for movies?”

Setting him up when she didn’t have to, she goaded him with her movie choices.

“Unless you want to watch Gone with the Wind, Casablanca, Breakfast at Tiffany’s, or Dr. Zhivago, I don’t have many movies. Jeff took most of them when he moved out to live with Brianna. Yet, I do have two of my son’s favorite movies that he left behind, The Secretary and Spanking the Monkey.”

She held up the videos for him to see the movie covers.

“I haven’t seen either of those,” said Jason. “What are they about?”

She turned the movie to look at the back of the Secretary.

“The Secretary has James Spader playing a lawyer and Maggie Gyllenhaal playing his secretary. James Spader was the star in Boston Legal and in Blacklist. In the Secretary, he sexually abused his secretary and she allowed him to sexually touch her and feel her. Then, he ordered her to lean over his desk. While standing behind her, he lifted the back of her skirt to masturbate on her pantyhose clad ass while standing behind her,” said Rose with a dirty laugh. “Maggie Gyllenhaal has been in lots of things and she always ends up naked,” said Rose with another dirty laugh.

She handed him the move and he read the back.

“The Secretary sounds hot,” said Jason. “What is Spanking the Monkey about? Judging the movie by the title, is that about what I think it’s about,” said Jason returning Rose’s dirty laugh with his dirty laugh.

Rose smiled sexily at Jason while nodding her pretty head.

“Spanking the Monkey is about a son caring for his mother who broke her leg. With him massaging her leg above her knee length cast daily, and helping her to shower presumably with his eyes closed, he continually masturbated over all that he saw and touched of his mother. After a while, especially with his mother horny and sexually interested in her son as much as he was horny and sexually interested in his mother, one thing led to another and, eventually, they have incestuous sex,” said Rose.

Jason flashed Rose a smile of sexual excitement.

“Well, in case you don’t know, since I’ve had sex with my mother, I’d love to watch Spanking the Monkey,” said Jason.

As if modeling for a men’s magazine, Rose inhaled a deep breath, arched her back, and sexily posed to show off the side of her monster breasts.

“So, tell me, Jason,” said Rose goading him to give her the answer that she hoped to hear. She lifted her breasts through her nightgown in her hands as if offering them to him. “Do you like tits, big tits?”

Jason stared at all that he could clearly see of Rose’s big breasts through her nightgown.

“Seriously?” He laughed. “I love tits, especially big breasts, like your big breasts,” said Jason with another laugh. “My mom has big breasts. Brianna doesn’t have big breasts but she has the best ass.”

Jason smiled at Rose as if he was the cat who just swallowed the canary.

“So,” said Rose. “You’ve had sex with not only your mother but with Brianna too?”

Jason gave Rose a sexy smile.

“I’ve had sex with all of my mother’s friends and with all of my friends’ mothers and they’ve all had sex with my mother and with their mothers too. We all belong to a mother and son incest, swinging club,” said Jason.

Rose gave Jason a shocked look that was mixed with sexual arousal.

“Oh, my,” she said. “You’re swingers, incestuous swingers.”

Jason smiled with pride.

“Yes, we are and we’d love for you to join out small, select group of mothers and sons,” he said.

# # #

Jason leaned in and kissed her and when he parted her lips with his tongue, she returned his French kiss with her wet kiss.

“Touch me,” said Rose. “I like having my breasts felt and my nipples fingered.”

Obediently obeying her as if she was his mother instead of soon-to-be lover, Jason felt her breasts through her nightgown while fingering her nipples.

“You have wonderful breasts, Rose, so big and so firm,” said Jason while continuing to feel and fondle Rose’s breasts through her thin and sheer nightgown.

Rose stared down at what she could see of her nearly, naked breasts through her nightgown before looking up at Jason.

“Would you like to see them? Would you like to see my tits?”

Jason watched Rose reach for her nightgown straps.

“Yes, please. I’d love to see your tits, Rose,” said Jason.

As if there was stripper’s music, Rose slowly removed her nightgown straps from her shoulders, first one and then the other. She allowed her nightgown bodice to slowly slide down to her waist. Then, she looked at her naked breasts to see what Jason could see of her before looking up at him.

“What do you think of my tits, Jason,” asked Rose? “Not bad for an old woman,” she said.

She turned one way before turning the other way. Then, she cupped and lifted her naked breasts in her hands while sliding slow hands across her erect nipples. Sucking one nipple, she sucked her other nipple while staring at him. She looked down at her naked tits again before looking up at him.

“They’re so big, firm, and shapely,” he said staring at her naked breasts. “And you’re hardly an old woman. You’re not much older than my mother.”

As if offering them to him, Rose continued cupping her breasts in her hands while fingering her nipples.

“Thank you. I love my tits,” she said. “Touch them and feel them while fingering my nipples. I love having my nipples fingered. Suck my nipples. I love having my nipples sucked.”

He felt her breasts while fondling her nipples. Pulling them, turning them, and twisting them, he leaned down to suck her nipples. Not stopping there, he reached beneath her nightgown to cup her naked pussy in the palm of his hand while continuing to finger and suck her nipples. While he fingered her naked cunt, Rose fingered the head of his cock through his pants. She allowed him to have his wicked, sexual way with her nearly naked body.

“Would you like to see my cock,” he asked ready to show her his cock for her showing him her tits?

She stared down at the bulge his erect cock made in his pants.

“I thought you’d never ask. I’d love to see your cock,” said Rose.

# # #

Jason stood, unbuckled, unbuttoned, and unzipped his pants. In anticipation of having sex tonight, not wearing any underwear, he allowed his pants to fall to his ankles. He exposed his naked, erect prick to Jeff’s mother, Brianna’s future mother-in-law.

Not wasting any time, she reached out her hand and touched his cock. Then, fondling the head of his erect prick with her fingertips, she slowly stroked him. In the way that Jeff wanted his mother to give him a hand job, Rose was giving Jennifer’s son a hand job.

Then, leaning forward she took his erect dick in her mouth and sucked him while stroking him. As soon as he had a big and hard erection, she moved on her back and allowed him to mount her. Kissing one another while making love, it wasn’t long before they were fucking. Jason banged Rose hard and fast. Humping her harder and humping her faster, she was ready to cum.

“Jason. My God, Jason. I’m cumming. I can’t believe I’m cumming. I can’t believe I’m cumming already, I’ve never cum during intercourse,” she said wrapping her legs around his back and holding him tighter. “Don’t stop. Fuck me harder. Fuck me faster. Fuck me, Jason. Fuck me.”

Jason fucked her harder and faster and as soon as she had her sexual orgasm and regained her strength from basking in the afterglow of sex, determined to have him cum in her mouth, she sucked his cock again. She stroked him harder while sucking him deeper. She stroked him faster while sucking him harder. Then, when he ejaculated a load of cum in her mouth, as soon as she released his cock from her lips, he ejaculated a second load of cum all over her face and across her naked tits.

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