Imprisoned Son's Last Wishes, Ch. 04

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Son has threesome sex with his mother and sister.
6.5k words
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Part 4 of the 4 part series

Updated 06/14/2023
Created 02/27/2023
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Anthony finally has threesome sex with his mother and his sister.

Hoping that they would give him plenty to masturbate over while in prison, Anthony's last wish before being jailed was to have threesome sex with his MILF of a mother, Emma, and his sexy, big sister, Sophia. He wanted to do everything to their naked bodies that he had imagined doing when masturbating himself while imagining them naked and having sex with them. He wanted to sexually do everything to and with his mother's naked body that a son should never do. He wanted to sexually do everything to his sister's naked body that a brother should never do.

Hoping the prison guard would allow him to keep their photos, other than having threesome sex with them, the only other thing that he wanted were photos of his mother and his sister in all manner of undress. Expressly using the photos to masturbate over them, he asked his mother and his sister to send him photos of them in their bras and panties. He asked them to send him photos of them in their sheer and sexy, low-cut nightgowns. He asked his mother and his sister to send him photos of them topless and naked.

Now, with his sexual fantasy coming true, hard for him to believe that this was really happening, he was finally going to have incestuous sex not only with his mother but also with his sister, too. He was going to have incestuous sex with them one at a time and both together. As shocked as he was sexually excited, he couldn't believe that both his mother and sister agreed to give him sex. He couldn't believe that they both agreed to allow him to watch him giving oral sex to one another.

# # #

Author's Note:

This is Chapter Four of Imprisoned Son's Last Wishes, the final chapter of a true story that was written for Anthony about what sexually happened to him, to his MILF of a mother Emma, and to his sexy, older sister, Sophia. Nothing has been changed. With him having their permission to use their identities in his story, all the facts and even the names of his mother and his sister are the same.

# # #

Imprisoned Son's Last Wishes, Continued from Chapter 03:

Sophia pulled away from her mother to sit up in her mother's bed. With her having a face full of guilt, she turned to look at her mother with embarrassment and shame. Afraid to tell her mother that she had sex with her brother, she wondered how her mother would react when she told her all that she needed to tell her.

Knowing her mother as a morally modest woman, she knew that her mother would never agree to have threesome sex with her daughter and her son. Too much to even ask of her, too sexually perverted to ask of an older woman, she knew that her mother would never agree to eat her pussy and allow her to eat her pussy while Anthony watched. What her brother wanted and expected them to sexually do was too much out of the realm of what her mother would ordinarily sexually do.

"What's wrong, Sophia," asked Emma with the concern of a worried mother hoping to ease her mental anguish with some kind words?

Filled with remorse, Sophia looked down at herself before looking up at her mother with humiliation. Indeed, again, she was embarrassed and ashamed for having had sex with her brother. Having regrets for something that she could never take back and her brother could never unsee, she felt so guilty for allowing him to see her naked. She regretted allowing him to touch and feel her naked body everywhere that a brother should never touch and feel his sister.

Going over their sexual interlude again in her mind, how could she do such a thing? How could she allow him to see her naked? How could she allow him to touch and feel her naked body everywhere? How could she have sex with her brother? What's wrong with her for her to have had sex with her brother? She felt like such a whore, an incestuous whore for stroking him, sucking him, making love to him, and fucking him. Literally, as if it was all her fault for just wearing a towel, she felt dirty. Now, no matter how many hot showers she took, she still felt unclean.

"It's not over, mother. It's hardly over," said Sophia slowly shaking her head from side to side. "It's just the beginning," she said with disillusionment.

Hoping that her mother would forgive her for having had sex with her brother, she paused to look at her mother with shame.

"Now that Anthony has had sex with the both of us separately," she said pausing to look at her mother again but this time with more shame and more embarrassment. "He wants to have sex with the both of us together and at the same time as a threesome."

# # #

Emma laughed out loud. When Emma laughed, she surprised her daughter. Her mother thought it was funny that Anthony wanted to have sex with them both together. Why would she think that was funny when Sophia thought that having threesome sex with her mother and her brother was over the top and sinful? How could he even ask such a thing of them. Not only that, he wanted photos of them in their bras and panties, in their sexy nightgowns, topless, and naked. Even though she had sex with her son, Sophia knew that her mother would never agree to be photographed in all manner of undress.

"That horny, little bastard," she said with another laugh. "Again, like father like son," said Emma with a dirty laugh. "With your father nearly, twenty-years older than me, when he could no longer get and maintain an erection because of his drinking and his diabetes, he dramatically changed in his sexual desires."

Before telling her the truth about their open, sexual relationship that she had with her husband, she looked at her daughter with shame. Emma looked at Sophia with embarrassment. Yet, wanting her to understand her brother, she had to tell her about her father. She had to tell her all that she sexually did with other men. If she didn't know already, she had to confess to her daughter that her mother was a whore. She took a big breath for courage before confessing her personal, sexual life to her daughter.

Your father wanted to watch me having sex with his friends, Vito, Angelo, Luigi, Mario, and Big Rocco, who's soon to be released from prison, by the way," said Emma.

Sophia looked at her mother with shocked surprise.

"He wanted me to allow them to gangbang me. He wanted me to allow them to give them anal sex. He wanted me to have sex with all five men at once. He wanted me to allow them to not only fuck them but also to suck them, and allow them to fuck me in my ass," said Emma with a dirty laugh.

Sophia continued looking at her mother with shock.

"What did you do, mother?" Sophia paused to look at her mother while imagining her being gangbanged by five men. "Did you allow them to gangbang you?" She paused to look at her mother while imagining her being fucked in her ass. "Did you allow them to fuck you in your ass?"

Emma made a sour face while nodding her head, no.

"No way. Fuck that. Just as I'd never allow any man to fuck me in my ass, I'd never have a gangbang. Instead of having five men gangbang me and/or fuck me in my ass, I agreed to have sex with them, but one at a time, while my husband watched and masturbated himself," said Emma.

# # #

Before continuing her sexual confession, in the way that Sophia looked at her mother to read her reactions to all that she had said, Emma looked at her daughter to read her reaction to her agreeing to have extramarital sex with five of her husbands' men separately.

"I made love to them. I fucked them. I sucked them and allowed them to cum in my mouth," said Emma. "Pretending that I enjoyed them having their wicked, sexual way with my naked body, I even allowed them to give me cum baths. With my husband's permission and under his watchful eye, while he watched and masturbated himself, I was their wicked whore for an hour."

Again, Emma looked at her daughter to see how she reacted to her sexual confession. When Sophia didn't show any reaction, she continued her secret, never told sexual confession of having forbidden sex with her husband's five, top men. She remembered feeling embarrassed for allowing the men to see her naked. She remembered that she felt humiliated for allowing them to touch and feel her naked body everywhere that a man should never touch and feel another man's wife.

Sadly, she remembered feeling guilty and ashamed for allowing her husband to sexually use her. When he supposedly loved her, and with her the mother of his children, how could he agree to allow her to have sex with five men while he watched and masturbated himself. What's wrong with him for him to do that to her? She remembered feeling like the whore that she was, has always been, still is, and will always be for submitting her naked body to her husband's henchmen.

"Carmen invited them over separately and, giving him a sexy show to masturbate himself over, I flirted with them and sexually seduced them while he watched. I made out with them while allowing them to touch me and feel me everywhere through my clothes. Then, I allowed them to slowly strip me naked while touching and feeling my naked body everywhere," said Emma. "Finally, while my husband watched and masturbated himself, I stroked them, sucked them, and fucked them."

Emma looked at her daughter with shame mixed with sexual arousal.

"Yet, having no regrets for having sex with five men while my husband watched, to tell you the truth, after no longer having sex with my husband, I welcomed the opportunity to have sex with his five, top men. Before having sex with them, masturbating myself all the time with my vibrator and with my dildo, I was so horny that I would have fucked a bedpost," said Emma with a dirty laugh. "With me more than willing to have sex with other men, we did one another a sexual favor by him wanting to watch me having sex with other men."

Sophia looked at her mother with shock mixed with sexual excitement.

"Besides, after his five, top men had their wicked, sexual way with the boss's wife, by allowing them to have sex with me, that kept them more loyal. As long as I continued giving them occasional blowjobs and fucking them from time to time, in the way that they'd do anything for him, they'd do anything for me, too," said Emma. "Wrapped around my finger, his men were as much my men as they were his men."

# # #

"In case you forgot or didn't know but, when I was younger, before I married your father, I was a whore. I was a wicked whore," said Emma with a dirty laugh. "I met your father while working as a stripper in one of his strip clubs. I had sex with your father long before we were married. Something that may shock you, but when I worked as a stripper, I had sex with as many women as I had sex with men," said Emma with a dirty laugh.

She watched her daughter's reaction to what she said about having sex with as many women as she had sex with men. Sophia stared at her mother with shocked surprise. Clearly, she was unaware that her mother had been a stripper working in one of her father's strip clubs. She was unaware that her mother was once a nasty whore. She was unaware that her mother enjoyed having sex with as many women as she enjoyed having sex with men.

"I didn't know you were a stripper. I didn't know that you were a whore. I didn't know that you had sex with women," said Sophia stunned.

Both women remained quiet until Sophia spoke again.

"Well, that brings me to Anthony," said Sophia.

Emma looked at her daughter with curiosity.

"Anthony? What about Anthony," asked Emma?

Sophia looked up at her mother with embarrassment and shame.

"Now that he's going to prison for us and now that he had sex with the both of us, he wants us to have a threesome," said Sophia.

Emma laughed.

"The apple doesn't fall far from the tree. He's just like his father," laughed Emma. "He has some cute friends, which friend does he want us to suck and fuck?"

Sophia stared down at her hands again before answering her mother.

"He doesn't want us to have sex with any of his friends," she paused to read her mother's reaction to what she was about to say. "He wants us to have threesome sex with you and with me. He wants to have sex with you again, and then, he wants to have sex with me again, too. Then, he wants to have sex with the both of us together," said Sophia.

She looked at her mother with embarrassment and shame.

"That's not all. He wants to watch you having sex with me and watch me having sex with you. He wants to watch me eating your pussy before watching you eating my pussy while he masturbates himself," said Sophia. "He wants to watch me fingering your pussy while licking your pussy. He wants to watch you fingering my pussy while licking my pussy. He wants to watch us masturbating one another while licking one another. He wants to watch us give one another sexual orgasms with our fingers and with our tongues."

Emma laughed again.

"That little pervert," she said. "Well, for him taking the rap for us, the least that we can do, let's give him plenty to masturbate over in prison. I can do that. I can make his sexual fantasies come true. I'm game if you're game," said Emma. "I'll eat your pussy if you agree to eat my pussy," she said. "I'll give you a sexual orgasm if you give me a sexual orgasm," said Emma to her daughter. "I'll even allow him to take whatever topless and naked photos of us that he wants."

# # #

Imprisoned Son's Last Wishes, Chapter 04:

Showing her daughter that she'd willingly and consensually have incestuous sex with her, Emma leaned forward and gave her daughter a kiss. Then, she parted Sophia's lips with her tongue while fondling her huge breasts through her nightgown and fingering her erect nipples. Sophia returned her mother's French kiss with her long, wet kiss. In the way that her mother fondled her daughter's huge breasts and fingered her erect nipples, Sophia fondled her mother's big breasts and fingered her erect nipples. As if they were lesbian lovers, mother and daughter made out.

"Tonight, after dinner, we'll surprise him by giving him what he wants," said Emma with a dirty laugh. "First, I need to shower," she said getting out of bed just as Anthony entered her bedroom with her breakfast tray.

Clearly confused, Anthony looked at his sister sitting on her mother's bed before looking over at his mother standing out of bed.

"Hey, where you going? Get back in bed. I made you breakfast, mom," he said carrying in a breakfast tray with eggs, bacon, fruit, toast, and coffee.

Emma obediently obeyed her son while laughing with glee. She climbed back in bed. Anthony put the breakfast tray table over his mother's lap. She ate her breakfast and drank her coffee before getting out of bed again to take her shower.

Only, as soon as she climbed out of bed, with Anthony still in her bedroom, she showed him the whore that she is. Giving him a sexual preview of what was to come, as if he was her husband, her boyfriend, or her lover instead of her son, she shamelessly turned to face. Then, as if she was still a stripper on stage instead of a mother standing in front of her son in her bedroom, she slowly, sexually, and seductively removed her nightgown in front of him. Giving him a good, long look of her beautiful, naked body, his mother, Emma, stood naked before her son.

Unembarrassed and unashamed, not covering her nakedness with her hands or her forearms, with her hands by her sides, she was completely naked and vulnerable. While he stood staring at his mother's naked body, she stood staring at her son ogling her beautiful, sexy, and shapely body. Clearly, Anthony loved seeing his mother naked as much as Emma enjoyed showing her son her naked body. No doubt, Anthony couldn't wait to have threesome sex with his mother and his sister.

# # #

That night, with mother and daughter ready to give Anthony what he wanted, Emma invited her son into her bedroom. Both his mother, Emma, and his sister, Sophia, were lying on their mother's bed fully dressed when Anthony entered wearing his nightly uniform of choice a T-shirt and pajama bottoms without underwear. His mother and his sister were fully clothed because Anthony had a sexual fantasy of slowly stripping his mother and his sister naked while touching and feeling them everywhere that he should never touch and feel his mother and his sister through their clothes while making out with them.

With his sexual fantasy of having threesome sex with his MILF of a mother and with his sexy, big sister about to be realized, Anthony eagerly, sexually, and excitedly climbed in bed between them. Then, while his sister watched, he turned to his mother first. He kissed her red, full, lipstick clad lips. He parted her lips with his tongue and French kissed his mother while feeling her big breasts through her blouse and bra. He made out with her while his sister continued watching.

Taking his sweet, sexual time while enjoying himself, he continued feeling and fondling his mother's big breasts through her blouse and bra. Then, he unbuttoned his mother's blouse, one slow button at a time while looking to see what each unbuttoned button revealed before unbuttoning the next button. When her blouse was completely unbuttoned, he opened it wide to expose her big, white, sexy, low-cut bra.

Not nearly done there, he felt her big breasts through her bra while fingering her erect nipples. Then, hooking his index finger beneath her big brassiere, he lifted the front of her bra to expose her naked breasts. He watched as her left breast slowly fell and her right breast followed. There they were, his mother's naked breasts.

Sophia was sexually aroused watching her brother making out with their mother while stripping her topless, and feeling her naked breasts and fingering her erect nipples. As if her hands were Anthony's hands, Sophia fondled her own breasts and fingered her own nipples through her blouse and bra while watching her brother having his sexual way with their mother's naked breasts. Then, not stopping there, with her as sexually aroused as she was horny, she raised the hem of her short skirt and rubbed her already swollen clit through her sheer panties.

While waiting for her turn to have sex with her brother, Sophia masturbated herself through her clothes while watching Anthony give their mother incestuous sex. With him all over his mother's big tits, Anthony leaned down to suck Emma's erect nipples, first one and then, the other. While continuing to have his wicked, sexual way with his mother's naked breasts, he moved his hand beneath her short skirt and between her shapely thighs to cup her black, trimmed pussy through her sheer, white panties.

He was cupping his mother's cunt. He couldn't believe that he was cupping his mother's cunt. He couldn't believe that she was allowing him to cup her cunt.

Then, pushing her panties aside with his index finger, he fingered her wet, swollen clit while fingerfucking his mother. In the way that his sister, Sophia, masturbated herself, rubbing her swollen clit through her sheer panties, Anthony masturbated his mother. Not wanting to rush things and ruin things, while kissing her, touching her, and feeling her through her clothes, he took his sweet time in stripping his mother naked.

While continuing to make out with his mother, he unbuttoned and unzipped her short skirt. Then, when she sat up in bed to help him undress her, he removed her blouse and her bra. Finally, he removed her skirt and her bikini panties, too. In the way that Emma was naked in front of her son earlier before she took her shower, she was naked in front of her son again now.

# # #

Anthony moved halfway down the bed to make himself comfortable between his mother's shapely thighs. He couldn't believe that he was about to eat his mother's pussy again. He couldn't believe that she was allowing him to give her oral sex again. Like mother like son, seemingly, she wanted him to give her incestuous sex as much as he wanted to give her incestuous sex.

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