Blind Date with a Mistress
- 4 years ago
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Mother Vs. Mistress free porn video
She had him...her, yes, her, lying on her back, legs spread, shaved clean below the waist, wearing a pair of vanity fair pink panties, a pink chemise, knee-high lace-up heels, cleanly shaven face and bright red lip gloss…so wet were her lips painted they would have mistaken them for cum-coated…and she was shoving a lubricated vibrator into her panties and rolling it around her clitty and balls and smooth pussy.
And she…he…was spreading his sissy shaved legs as wide as he….she could and moaning like a silly silly slut. He looked ridiculous in the mirror but his mind only saw the sissy he felt inside and he…she moaned like a girl and looked into mistress’s eyes and his heart smiled because she knew him. She saw what he was and she was as turned on exposing him for what he was as he was showing her his real self. And he…she moaned again and brought his knees up to her chest and felt the vanity fair’s stretch over his shaved ass and the vibrator pressed hard against her sissy parts all shaved and smooth and he moaned…. “oh yes my mistress, I’m you’re pussy sissy whore and I love showing being your slave.”
“I know sweety audrie…yes, yes….” Mistress cooed with loving firmness. “Yes, yes, mistress knows you. Yes she does sissy audrie….Let mistress see you….show me sissy….show mistress what a good girl you are…”
And sissy began to hump the vibrator imagining he was a girl and he was fucking a cock and he let his head rest against the pillow and he moaned just like a girl….
Of course it came out like a man trying to sound like a girl….but he was getting better. He liked to moan over and over… “I’m a sissy, I’m a sissy slut,” and mistress would marvel internally.
Was this man, whom she loved dearly, was he gay? He certainly loved sucking cock, he’d shown her this several times. He eats his own cum daily…he even saves it up in a condom and at the end of a week he takes it out of the freezer and warms it in a cup of hot water and sucks out the cum while she masturbates him.
Yet, he always came back to her. She marveled at this sexual creature she had total and absolute control over. As long as she kept his sexual release on the edge of heightened deprivation she could make him do whatever she wanted and she wanted to see how he unraveled in front of her eyes. A simple sissy sex toy and she loved to use him thusly.
“good girl sissy slut,” she added as her right hand maneuvered the vibrator within his panties and caressed his face with her left. “Show mistress sweety….show me what you are sissy….show me….”
And sissy was moaning and he grabbed her left hand, so sweetly stroking his face, and he took two fingers and took them to his painted mouth and sucked them like a cock for her and he stroked his cock like a clit and was holding her fingers in his mouth with one hand and rubbing his clit with the other, the while moaning like a slut and mouthing, “Yes, Yes, Yes, Yes,” until he came all over his vanity fair panties.
Mistress rubbed the vibrator in his cum covered panties and she slid the cock into his hungry mouth.
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Mistress went home to her husband and sissy goes to his mother’s where he lives. Mistress didn’t know his mother was a dom, and that she was keeping her son supplied with cum. Sissy walked into his mother’s house just as 10 men were leaving. He rushed upstairs and saw his mother lying naked on the bed covered in fresh cum.
“Come to momma my little sissy,” she beckoned him. He knelt at her side and kissed her lips and tasted the warm cum coating her mouth. He licked her slowly and kissed her softly and worked his way down her body until she was clean. It took him a very long time and he waited to clean her pussy and ass until last. She was shaved clean and the warmth of her clit and ass kept the cum soft and warm for his mouth. She pulled her knees up to her chest exposing herself to her sissy girl son and he licked her to many orgasms.
When they finished sissy went and showered and put on his favorite weekend chores outfit. A pair of sandals, a baby-blue thong, a black satin chemise and his clit-cage. He went about the house cleaning.
Mistress goes home and she is mommy and wife and councelor. She is told what to do at work and at home she hardly has a voice. The k**s love her, her husband loves her, she works hard but she can’t escape the feeling that she is powerless. Her sex life is barely relevant unless she uses a vibrator she can’t get off with her husband. But she comes alive when she is with her sissy. She loves watching him cross every boundary she’d thought previously impossible. But she was his master now. She controlled him fully and she loved watching him do everything.
She has to plan months in advance. He’s always pushing to get her to be spontaneous, but she is smarter than that. She knows it’s part of her control. She can’t risk her marriage either….or more importantly, her k**s.
She is coming up with something to blow his mind.
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Mother told him to go to the porn shop and give three blow-jobs. “Take this. I want evidence,” she handed him a camera.
Sissy is wearing thong panties and a tight sleeveless poly-cotton blended blouse underneath his clothes. When he gets into the booth he takes everything off but the aforementioned articles. He is in the booth watching crossdresser porn and a cock comes to the hole. There are three holes in the wall in the shape of an upside down triangle. As he is sucking the cock coming through the bottom hole, two more sprout from the top two holes and he uses his hands to masturbate them. He set the camera up in the corner and filmed himself. He looked at the camera and moaned.
He liked sucking cocks and making them cum quickly. If he had to work too long he knew there was something he wasn’t doing correctly…he wasn’t pinpointing what it was the man wanted. He wasn’t paying attention to their movements. Men were easy, he almost always got them off quickly. And this time he did as well. He felt the cock in his mouth begin to twitch and he heard the indiscriminate markings of the male orgasm grunting and he slid just down to the head and formed a vacuum seal “O” around the tip and when he felt the first ejaculate hit his tongue he opened his mouth still glazing the bottom of the glanz on the cock in his open mouth and let the cum spill out the corners of his down-turned painted mouth and he smiled at the camera before moving to the top right cock and repeating his action. Now he felt like a real whore and wanted his mistress to be the one he did this for.
He resented his mother’s control but secretly he loved it too, but he wanted all his lustful acts of servile submission to be for his mistress. When he looked into the camera it was his sweet and loving mistress for whom he imagined he was performing. He reveled in the sensation of this fresh hard cock sliding down the length of his tongue, slowly he slid all the way down on this cock in one soft suspense-filled journey until his nose reached the wall and the cock on the other side of the wall responded by flexing forward until the entire hard length was in his throat and he stayed there. Well-practiced in deep throating he loved to swallow over the surface of the cock and make the man cum by this simple act. He swallowed and moaned like a seasoned whore until he felt the coming of this one’s orgasm and he slid back down to seal the tip and then when the cum began he let it pour out the sides of his mouth again…and again he imagined mistress was the one watching him.
He thought about how his mother had turned him into an expert cock-sucking whore but he wanted more. She was using him and making a lot of money off of him and he wanted more. He loved how mistress and he were always together, even with other people…mistress likes women too. His mother would often send him off on trysts like the glory hole or fill the house with men and she would set up cameras and leave the house only to return to a box filled with money. Of course he always snuck a few hundred for himself on these occasions. He wanted to feel special the way mistress made him feel. She pushed his buttons, risking outing his fetish in public, in the mall or at a restaurant. Mother sent him to porn shops and kept him locked up at home. Mistress played with him out in the real world and here, he could get caught by respected members of society…here he could be found out.
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Mistress had gotten better….more assertive in getting her needs met by her husband by imagining he wasn’t her husband. She told herself it wasn’t her husband but someone like George Clooney or Mr. Grey and she was becoming more vocal in bed, “fuck my sweet cock hole baby,” and “fuck my cunt, fuck me like a whore,” and “god I love your sweet hot cock inside me.” Her eyes closed and her imagination the man is plastering her against a hard cement wall in the basement of the car-park and she is having a tremendous orgasm.
She wanted more and she’d taken it from her husband, she’d gotten others involved in her and sissy’s affair. She liked to get fucked by lesbians…god they knew exactly what she needed to feel just as her pussy was on the verge of exploding Sara or Jen would use the toys they played with expertly to make her crest toward oblivion exquisitely terrible and she would speed toward the most invigorating orgasms she’d ever known. Sara used her mouth on her asshole tonguing and slobbering all over her while plunging her cunt with a huge vibrating black cock and mistress would howl like a timberwolf.
Sissy would be sucking her feet or kissing her neck or behind her ears while she was being pounded…it was as if he were a mere sex-toy reaching whatever area on her or in her her lover couldn’t reach. He loved to meet her lovers, male or female because he knew he was showing himself…more of himself….herself, for her, his mistress. She is always nervous and shy at first and then once he sees they accept him…her for who she is, she becomes sissy once again.
The first time they brought a new person, she is mistress’s best friend. So, now even when they are out as normal people, he knows she knows and she knows he knows she knows and he is even more appreciative of me and of her. Mistress remembered, sissy was dressed in a panty-girdle (six straps and bottomless) with wolford stockings and a bustier corset and black patent leather stilettos. She was between Mistress’s legs on the bed lazily licking and kissing her shaved pussy and the doorbell rang. The k**s and Mark were at Disney for the weekend. Mistress got up and after a few minutes when she didn’t return sissy put his clothes on over his outfit and slid on house shoes to go investigate. He heard Cheryl, Mistress’s best friend, laughing as he descended the stairs.
“Hey Cheryl,” He said. “Drink?”
“Sure,” Cheryl said.
He went and got her a white wine and a red for mistress. “Here you go baby, it’s that Sonoma Valley you’ve been raving about.”
“Thanks audrie,” Mistress said it and Cheryl curled her eyebrows in confusion and then she laughed, “What?”
Sissy was horrified, his cock was instantly soft. “Cheryl,” Mistress began and sissy turned on his heel and went to go back upstairs. “There’s no easy way of saying this,” he was on the first step about to run up the stairs and one of his house shoe fells off and he was baring his right foot to the girls and it was covered in sheer tan nylon with red painted toes standing out like spring blossoms. “This is Audrie….” And they both laughed like excited school c***dren. He was humiliated. He felt the twinge of resentment he’d held for his mother for so long. And then something beautiful happened.
“Oh god Adam…I mean Audrie, those are great!” Cheryl was admiring his painted toes. “Do you paint Ay…what do you call your girlfriend?”
“Mistress,” mistress interrupted. And yes, he paints mine all the time. I think you would love getting a pedi from audrie. She is very attentive.”
They started talking about pedicures and manicures and they all three moved to sit in the living room and finish their drinks.
“What else are you wearing audrie…” when Cheryl asked him this he felt a surge of pleasure knowing that mistress had shared her with Cheryl. He felt like she accepted him as warmly as mistress and he felt comfortable asking, “May I show her mistress?”
“I think that’s best sissy…” oh god sissy loved that she’d just called him that in front of Cheryl. He stood still and shy and mistress encouraged him… “it’s fine sissy audrie, you want to show me don’t you? Yes…I know audrie it’s frightening and shameful, but it’s what you want to do…” She knew him so well and he did want to show her, he wanted to show the world if it meant she accepted him for who he was.
“C’mon Audrie,” Cheryl encouraged him as well. “I want to see those toes of yours….Oh my god, does she have heels too?”
“Oh my Cheryl, you are going to be so good for sissy…” the girls laughed and Audrie kicked his other house shoe off and curled his nyloned toes up so they could see how well he paints his toes. They clapped and cheered him as he slid his slacks off and he stood in front of them both in a button down shirt and open-bottom panty girdle with six sexy straps holding up his sheer thigh-highs by Wolford. He looked and felt ridiculous.
“Oh my god girl!” Cheryl’s fixated eyes were glued to sissy’s shaved body. Never had she seen a man with shaved legs and crotch and it struck her how feminine his legs seemed now that they were so. She couldn’t get the paradox out of her mind and she switched involuntarily between viewing this creature in front of her as a female and a male. He saw the desire in Cheryl’s eyes, she was hooked and he unbuttoned his shirt to reveal the corset pinching his waist and pushing his chest out and when the girls giggled and clapped his spun on his heel and twirled for them and they clapped some more.
He was shy at first but soon they both had him dancing and stroking his clit for them like a pro. He felt giddy inside, filled with love and heightened emotions to behave like a woman for these two sexy beauties kept escalading his fluttering stomach and he reveled in his sissy-ness.
She remembered how powerful she felt. She had introduced her best friend and she’d seen her instant attraction to what she’d created and she knew Cheryl was jealous and wished she’d had her own but she would have to settle for second place this time. She had done what so many women wished for, created a doting sex toy that would do whatever she beckoned.
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He was alone at his house…a rare occasion. He was thinking about mistress. He wondered what he wanted from her. Yes, she knew him sexually, she knew him personally, she was married, she had k**s. She fulfilled his every expectation and desire. She was married with k**s. He contemplated a role as cuckold, but that meant getting her husband on board, he was too puritan for that. It would never happen. He contemplated living forever as her toy, her sideline toy. That could work, but his mother. She was too much. He likes cock but he wants to feel loved. His mother seemed to simply use him. She’d given him so much cock that it wasn’t good anymore. She stopped loving him. Mistress loved him…accepted him…he wanted to be hers.
He wrote her a letter and saved it on his pc. A letter revealing all and giving him/herself to mistress for as long as she will have him.
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Mother came home and her son was gone. She logged into his computer and looked at the videos she’d made of her son. When her husband died she felt like she’d been released from a nunnery and she started having sex. Her son was only 10, and she began visiting him at night and reading stories to him. She’d dress in a full-gossamer gown, see-through and only a pair of vanity fair panties underneath, her pendulous breasts hung down and she nestled her little boy into her bossom and read to him. By age 11, she felt his hard on. By twelve his hairy legs started to bother her and she began shaving him. By 13 she’d rubbed his little pee-pee between her finger and thumb and caressed his growing balls in her gossamer gown material until he’d cum and by 16 he was eating her pussy like an expert lesbian…of course by then he was also dressing completely as a sissy underneath his boy clothes. She’d turned her son into her daughter. She’d created a sort of sexual slave of him. He felt too embarrassed to tell anyone for fear that he might not actually get to have the fun she’d been helping him have. He didn’t want to be like this, yet he wanted it. She knew how to humiliate him just so he felt ashamed enough that telling anyone would be catastrophic in his perspective.
She was looking at the latest film they’d made. 15 men all cumming on his naked and shaved body. He stroked himself to orgasm lying on his back, staring at the camera, face smeared with lipstick and cum and he moaned like a little sex-starved girl as he bucked and fucked his cum covered hand to orgasm.
She fingered her pussy and came watching her son cum. Then she browsed his files.
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He knocked on mistress’s door. A man, tall, strong, shirtless, and tan answered. Mark must have been at work, the k**s at school.
“Hey audrie,” she only called him this anymore. He was embarrassed. The man smiled and walked into the kitchen. “What’s up?” “Oh, don’t worry sweety, you know I need to be fucked once in a while.” “seriously, you knew honey, don’t feel sad. You are my sissy, I am your mistress…I love you sissy you’re just such a sissy now I need to get fucked once in a while.” “would you like it if I let you suck his cock? He’s just fucked me…you can suck him and make him cum again audrie.”
He just stood there with his letter in his hands.
“What’s that sweetheart?”
She took the letter and read it, she started to cry.
The man came in, he was naked now. He saw tears of joy coming down her cheeks and he went to her and read the letter too and started laughing. Sissy started crying, he was ashamed.
Mistress went to him and held him. She unbuttoned his shirt and saw a pink chemise underneath and she kissed his soft cheek. She whispered in his ear and finished unbuttoning him in front of the man. She whispered sweetly into his ear, yes, yes, I know, I know, it’s ok, it’s ok. She unfastened his belt and unbuttoned his pants, he was wearing sheer-to-waist black wolford nylons and she slid his slacks down and he stood with his shirt off over his shoulders and his pink chemise sliding around on his body and his bottom exposed underneath the sheer-to-waist wolford’s, his slacks piled up around his ankles and she began to caress his shaved clit over the nylons and she kissed him softly.
“Of course sissy, you are mine forever,” she whispered so only he could hear her.
“Suck his cock honey,” she said loud enough so the man heard.
He got down on his knees and took the man’s cock into his mouth and he smelled her pussy on him and he let is slip silently down his throat and imagined he was swallowing her cunt in his mind. He swallowed and swallowed and he felt the indicative twitch and he knew he would cum.
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Mother burst into the door. She stood stark still watching her son sucking cock for her. She held a printed copy of the letter.
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Mistress was standing in the middle of her home office. The man had left. Sissy was dressed as he was before, only now he wore knee-high leather stiletto heels and was walking around the room like a girl. He was really becoming a girl and he flaunted himself freely to his mistress’s commands and cheers. She was filming him and the room.
He was actually giggling now and touching himself like a girl. He walked behind mistress’s desk and twirled the office chair around in circles, his mother tied to it only wearing a full-length gossamer gown and vanity fair panties. The same outfit she’d made him cum for the first time in.
Mistress was filming them. He was twirling her around and around, slapping her breasts and face as she went round and round. She was crying a bit, mostly out of rage because Mistress had informed her where copies of this film would end up should she get in the way of their relationship.
He felt powerful now. He wanted to humiliate his mother. He leaned the ergonomic chair back and locked it into place so she was reclined and exposed for his needs. He mounted her body and slid his entire shaved body up and down on her gossamer covered fleshy body and he wrapped his arms around her and used her body like a giant cock and used his body like an engulfing mouth and he stroked her using all of his body and his hips bucked and pressed into her silky body and he kissed her and stroked her and used all of her body as his pleasure toy imagining that finally he was using her and he humped her until he came. His body tensed and he used short quick humps to bring himself over the edge and he scooped up his cum and pasted her lips with it and kissed her. He looked over at the camera and kissed his mistress in his imagination.
And she…he…was spreading his sissy shaved legs as wide as he….she could and moaning like a silly silly slut. He looked ridiculous in the mirror but his mind only saw the sissy he felt inside and he…she moaned like a girl and looked into mistress’s eyes and his heart smiled because she knew him. She saw what he was and she was as turned on exposing him for what he was as he was showing her his real self. And he…she moaned again and brought his knees up to her chest and felt the vanity fair’s stretch over his shaved ass and the vibrator pressed hard against her sissy parts all shaved and smooth and he moaned…. “oh yes my mistress, I’m you’re pussy sissy whore and I love showing being your slave.”
“I know sweety audrie…yes, yes….” Mistress cooed with loving firmness. “Yes, yes, mistress knows you. Yes she does sissy audrie….Let mistress see you….show me sissy….show mistress what a good girl you are…”
And sissy began to hump the vibrator imagining he was a girl and he was fucking a cock and he let his head rest against the pillow and he moaned just like a girl….
Of course it came out like a man trying to sound like a girl….but he was getting better. He liked to moan over and over… “I’m a sissy, I’m a sissy slut,” and mistress would marvel internally.
Was this man, whom she loved dearly, was he gay? He certainly loved sucking cock, he’d shown her this several times. He eats his own cum daily…he even saves it up in a condom and at the end of a week he takes it out of the freezer and warms it in a cup of hot water and sucks out the cum while she masturbates him.
Yet, he always came back to her. She marveled at this sexual creature she had total and absolute control over. As long as she kept his sexual release on the edge of heightened deprivation she could make him do whatever she wanted and she wanted to see how he unraveled in front of her eyes. A simple sissy sex toy and she loved to use him thusly.
“good girl sissy slut,” she added as her right hand maneuvered the vibrator within his panties and caressed his face with her left. “Show mistress sweety….show me what you are sissy….show me….”
And sissy was moaning and he grabbed her left hand, so sweetly stroking his face, and he took two fingers and took them to his painted mouth and sucked them like a cock for her and he stroked his cock like a clit and was holding her fingers in his mouth with one hand and rubbing his clit with the other, the while moaning like a slut and mouthing, “Yes, Yes, Yes, Yes,” until he came all over his vanity fair panties.
Mistress rubbed the vibrator in his cum covered panties and she slid the cock into his hungry mouth.
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Mistress went home to her husband and sissy goes to his mother’s where he lives. Mistress didn’t know his mother was a dom, and that she was keeping her son supplied with cum. Sissy walked into his mother’s house just as 10 men were leaving. He rushed upstairs and saw his mother lying naked on the bed covered in fresh cum.
“Come to momma my little sissy,” she beckoned him. He knelt at her side and kissed her lips and tasted the warm cum coating her mouth. He licked her slowly and kissed her softly and worked his way down her body until she was clean. It took him a very long time and he waited to clean her pussy and ass until last. She was shaved clean and the warmth of her clit and ass kept the cum soft and warm for his mouth. She pulled her knees up to her chest exposing herself to her sissy girl son and he licked her to many orgasms.
When they finished sissy went and showered and put on his favorite weekend chores outfit. A pair of sandals, a baby-blue thong, a black satin chemise and his clit-cage. He went about the house cleaning.
Mistress goes home and she is mommy and wife and councelor. She is told what to do at work and at home she hardly has a voice. The k**s love her, her husband loves her, she works hard but she can’t escape the feeling that she is powerless. Her sex life is barely relevant unless she uses a vibrator she can’t get off with her husband. But she comes alive when she is with her sissy. She loves watching him cross every boundary she’d thought previously impossible. But she was his master now. She controlled him fully and she loved watching him do everything.
She has to plan months in advance. He’s always pushing to get her to be spontaneous, but she is smarter than that. She knows it’s part of her control. She can’t risk her marriage either….or more importantly, her k**s.
She is coming up with something to blow his mind.
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Mother told him to go to the porn shop and give three blow-jobs. “Take this. I want evidence,” she handed him a camera.
Sissy is wearing thong panties and a tight sleeveless poly-cotton blended blouse underneath his clothes. When he gets into the booth he takes everything off but the aforementioned articles. He is in the booth watching crossdresser porn and a cock comes to the hole. There are three holes in the wall in the shape of an upside down triangle. As he is sucking the cock coming through the bottom hole, two more sprout from the top two holes and he uses his hands to masturbate them. He set the camera up in the corner and filmed himself. He looked at the camera and moaned.
He liked sucking cocks and making them cum quickly. If he had to work too long he knew there was something he wasn’t doing correctly…he wasn’t pinpointing what it was the man wanted. He wasn’t paying attention to their movements. Men were easy, he almost always got them off quickly. And this time he did as well. He felt the cock in his mouth begin to twitch and he heard the indiscriminate markings of the male orgasm grunting and he slid just down to the head and formed a vacuum seal “O” around the tip and when he felt the first ejaculate hit his tongue he opened his mouth still glazing the bottom of the glanz on the cock in his open mouth and let the cum spill out the corners of his down-turned painted mouth and he smiled at the camera before moving to the top right cock and repeating his action. Now he felt like a real whore and wanted his mistress to be the one he did this for.
He resented his mother’s control but secretly he loved it too, but he wanted all his lustful acts of servile submission to be for his mistress. When he looked into the camera it was his sweet and loving mistress for whom he imagined he was performing. He reveled in the sensation of this fresh hard cock sliding down the length of his tongue, slowly he slid all the way down on this cock in one soft suspense-filled journey until his nose reached the wall and the cock on the other side of the wall responded by flexing forward until the entire hard length was in his throat and he stayed there. Well-practiced in deep throating he loved to swallow over the surface of the cock and make the man cum by this simple act. He swallowed and moaned like a seasoned whore until he felt the coming of this one’s orgasm and he slid back down to seal the tip and then when the cum began he let it pour out the sides of his mouth again…and again he imagined mistress was the one watching him.
He thought about how his mother had turned him into an expert cock-sucking whore but he wanted more. She was using him and making a lot of money off of him and he wanted more. He loved how mistress and he were always together, even with other people…mistress likes women too. His mother would often send him off on trysts like the glory hole or fill the house with men and she would set up cameras and leave the house only to return to a box filled with money. Of course he always snuck a few hundred for himself on these occasions. He wanted to feel special the way mistress made him feel. She pushed his buttons, risking outing his fetish in public, in the mall or at a restaurant. Mother sent him to porn shops and kept him locked up at home. Mistress played with him out in the real world and here, he could get caught by respected members of society…here he could be found out.
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Mistress had gotten better….more assertive in getting her needs met by her husband by imagining he wasn’t her husband. She told herself it wasn’t her husband but someone like George Clooney or Mr. Grey and she was becoming more vocal in bed, “fuck my sweet cock hole baby,” and “fuck my cunt, fuck me like a whore,” and “god I love your sweet hot cock inside me.” Her eyes closed and her imagination the man is plastering her against a hard cement wall in the basement of the car-park and she is having a tremendous orgasm.
She wanted more and she’d taken it from her husband, she’d gotten others involved in her and sissy’s affair. She liked to get fucked by lesbians…god they knew exactly what she needed to feel just as her pussy was on the verge of exploding Sara or Jen would use the toys they played with expertly to make her crest toward oblivion exquisitely terrible and she would speed toward the most invigorating orgasms she’d ever known. Sara used her mouth on her asshole tonguing and slobbering all over her while plunging her cunt with a huge vibrating black cock and mistress would howl like a timberwolf.
Sissy would be sucking her feet or kissing her neck or behind her ears while she was being pounded…it was as if he were a mere sex-toy reaching whatever area on her or in her her lover couldn’t reach. He loved to meet her lovers, male or female because he knew he was showing himself…more of himself….herself, for her, his mistress. She is always nervous and shy at first and then once he sees they accept him…her for who she is, she becomes sissy once again.
The first time they brought a new person, she is mistress’s best friend. So, now even when they are out as normal people, he knows she knows and she knows he knows she knows and he is even more appreciative of me and of her. Mistress remembered, sissy was dressed in a panty-girdle (six straps and bottomless) with wolford stockings and a bustier corset and black patent leather stilettos. She was between Mistress’s legs on the bed lazily licking and kissing her shaved pussy and the doorbell rang. The k**s and Mark were at Disney for the weekend. Mistress got up and after a few minutes when she didn’t return sissy put his clothes on over his outfit and slid on house shoes to go investigate. He heard Cheryl, Mistress’s best friend, laughing as he descended the stairs.
“Hey Cheryl,” He said. “Drink?”
“Sure,” Cheryl said.
He went and got her a white wine and a red for mistress. “Here you go baby, it’s that Sonoma Valley you’ve been raving about.”
“Thanks audrie,” Mistress said it and Cheryl curled her eyebrows in confusion and then she laughed, “What?”
Sissy was horrified, his cock was instantly soft. “Cheryl,” Mistress began and sissy turned on his heel and went to go back upstairs. “There’s no easy way of saying this,” he was on the first step about to run up the stairs and one of his house shoe fells off and he was baring his right foot to the girls and it was covered in sheer tan nylon with red painted toes standing out like spring blossoms. “This is Audrie….” And they both laughed like excited school c***dren. He was humiliated. He felt the twinge of resentment he’d held for his mother for so long. And then something beautiful happened.
“Oh god Adam…I mean Audrie, those are great!” Cheryl was admiring his painted toes. “Do you paint Ay…what do you call your girlfriend?”
“Mistress,” mistress interrupted. And yes, he paints mine all the time. I think you would love getting a pedi from audrie. She is very attentive.”
They started talking about pedicures and manicures and they all three moved to sit in the living room and finish their drinks.
“What else are you wearing audrie…” when Cheryl asked him this he felt a surge of pleasure knowing that mistress had shared her with Cheryl. He felt like she accepted him as warmly as mistress and he felt comfortable asking, “May I show her mistress?”
“I think that’s best sissy…” oh god sissy loved that she’d just called him that in front of Cheryl. He stood still and shy and mistress encouraged him… “it’s fine sissy audrie, you want to show me don’t you? Yes…I know audrie it’s frightening and shameful, but it’s what you want to do…” She knew him so well and he did want to show her, he wanted to show the world if it meant she accepted him for who he was.
“C’mon Audrie,” Cheryl encouraged him as well. “I want to see those toes of yours….Oh my god, does she have heels too?”
“Oh my Cheryl, you are going to be so good for sissy…” the girls laughed and Audrie kicked his other house shoe off and curled his nyloned toes up so they could see how well he paints his toes. They clapped and cheered him as he slid his slacks off and he stood in front of them both in a button down shirt and open-bottom panty girdle with six sexy straps holding up his sheer thigh-highs by Wolford. He looked and felt ridiculous.
“Oh my god girl!” Cheryl’s fixated eyes were glued to sissy’s shaved body. Never had she seen a man with shaved legs and crotch and it struck her how feminine his legs seemed now that they were so. She couldn’t get the paradox out of her mind and she switched involuntarily between viewing this creature in front of her as a female and a male. He saw the desire in Cheryl’s eyes, she was hooked and he unbuttoned his shirt to reveal the corset pinching his waist and pushing his chest out and when the girls giggled and clapped his spun on his heel and twirled for them and they clapped some more.
He was shy at first but soon they both had him dancing and stroking his clit for them like a pro. He felt giddy inside, filled with love and heightened emotions to behave like a woman for these two sexy beauties kept escalading his fluttering stomach and he reveled in his sissy-ness.
She remembered how powerful she felt. She had introduced her best friend and she’d seen her instant attraction to what she’d created and she knew Cheryl was jealous and wished she’d had her own but she would have to settle for second place this time. She had done what so many women wished for, created a doting sex toy that would do whatever she beckoned.
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He was alone at his house…a rare occasion. He was thinking about mistress. He wondered what he wanted from her. Yes, she knew him sexually, she knew him personally, she was married, she had k**s. She fulfilled his every expectation and desire. She was married with k**s. He contemplated a role as cuckold, but that meant getting her husband on board, he was too puritan for that. It would never happen. He contemplated living forever as her toy, her sideline toy. That could work, but his mother. She was too much. He likes cock but he wants to feel loved. His mother seemed to simply use him. She’d given him so much cock that it wasn’t good anymore. She stopped loving him. Mistress loved him…accepted him…he wanted to be hers.
He wrote her a letter and saved it on his pc. A letter revealing all and giving him/herself to mistress for as long as she will have him.
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Mother came home and her son was gone. She logged into his computer and looked at the videos she’d made of her son. When her husband died she felt like she’d been released from a nunnery and she started having sex. Her son was only 10, and she began visiting him at night and reading stories to him. She’d dress in a full-gossamer gown, see-through and only a pair of vanity fair panties underneath, her pendulous breasts hung down and she nestled her little boy into her bossom and read to him. By age 11, she felt his hard on. By twelve his hairy legs started to bother her and she began shaving him. By 13 she’d rubbed his little pee-pee between her finger and thumb and caressed his growing balls in her gossamer gown material until he’d cum and by 16 he was eating her pussy like an expert lesbian…of course by then he was also dressing completely as a sissy underneath his boy clothes. She’d turned her son into her daughter. She’d created a sort of sexual slave of him. He felt too embarrassed to tell anyone for fear that he might not actually get to have the fun she’d been helping him have. He didn’t want to be like this, yet he wanted it. She knew how to humiliate him just so he felt ashamed enough that telling anyone would be catastrophic in his perspective.
She was looking at the latest film they’d made. 15 men all cumming on his naked and shaved body. He stroked himself to orgasm lying on his back, staring at the camera, face smeared with lipstick and cum and he moaned like a little sex-starved girl as he bucked and fucked his cum covered hand to orgasm.
She fingered her pussy and came watching her son cum. Then she browsed his files.
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He knocked on mistress’s door. A man, tall, strong, shirtless, and tan answered. Mark must have been at work, the k**s at school.
“Hey audrie,” she only called him this anymore. He was embarrassed. The man smiled and walked into the kitchen. “What’s up?” “Oh, don’t worry sweety, you know I need to be fucked once in a while.” “seriously, you knew honey, don’t feel sad. You are my sissy, I am your mistress…I love you sissy you’re just such a sissy now I need to get fucked once in a while.” “would you like it if I let you suck his cock? He’s just fucked me…you can suck him and make him cum again audrie.”
He just stood there with his letter in his hands.
“What’s that sweetheart?”
She took the letter and read it, she started to cry.
The man came in, he was naked now. He saw tears of joy coming down her cheeks and he went to her and read the letter too and started laughing. Sissy started crying, he was ashamed.
Mistress went to him and held him. She unbuttoned his shirt and saw a pink chemise underneath and she kissed his soft cheek. She whispered in his ear and finished unbuttoning him in front of the man. She whispered sweetly into his ear, yes, yes, I know, I know, it’s ok, it’s ok. She unfastened his belt and unbuttoned his pants, he was wearing sheer-to-waist black wolford nylons and she slid his slacks down and he stood with his shirt off over his shoulders and his pink chemise sliding around on his body and his bottom exposed underneath the sheer-to-waist wolford’s, his slacks piled up around his ankles and she began to caress his shaved clit over the nylons and she kissed him softly.
“Of course sissy, you are mine forever,” she whispered so only he could hear her.
“Suck his cock honey,” she said loud enough so the man heard.
He got down on his knees and took the man’s cock into his mouth and he smelled her pussy on him and he let is slip silently down his throat and imagined he was swallowing her cunt in his mind. He swallowed and swallowed and he felt the indicative twitch and he knew he would cum.
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Mother burst into the door. She stood stark still watching her son sucking cock for her. She held a printed copy of the letter.
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Mistress was standing in the middle of her home office. The man had left. Sissy was dressed as he was before, only now he wore knee-high leather stiletto heels and was walking around the room like a girl. He was really becoming a girl and he flaunted himself freely to his mistress’s commands and cheers. She was filming him and the room.
He was actually giggling now and touching himself like a girl. He walked behind mistress’s desk and twirled the office chair around in circles, his mother tied to it only wearing a full-length gossamer gown and vanity fair panties. The same outfit she’d made him cum for the first time in.
Mistress was filming them. He was twirling her around and around, slapping her breasts and face as she went round and round. She was crying a bit, mostly out of rage because Mistress had informed her where copies of this film would end up should she get in the way of their relationship.
He felt powerful now. He wanted to humiliate his mother. He leaned the ergonomic chair back and locked it into place so she was reclined and exposed for his needs. He mounted her body and slid his entire shaved body up and down on her gossamer covered fleshy body and he wrapped his arms around her and used her body like a giant cock and used his body like an engulfing mouth and he stroked her using all of his body and his hips bucked and pressed into her silky body and he kissed her and stroked her and used all of her body as his pleasure toy imagining that finally he was using her and he humped her until he came. His body tensed and he used short quick humps to bring himself over the edge and he scooped up his cum and pasted her lips with it and kissed her. He looked over at the camera and kissed his mistress in his imagination.
Madison
- 03.12.2021
- 33
- 0
