At first I had no idea what all this was about. I knew Sara didn't want me around for the weekend (she was sweet but very clear about it). I was going to spend the weekend away (like it or not), and like Sandra once told her, "He can't stay alone for a weekend, for obvious reasons."
I didn't know what Sara had in mind for this weekend. I assumed it had to do with a man, but the times I asked, she didn't answer me, just ignored me, changed the subject, or praised me for being "such a curious little man."
She dropped me at Jenny's apartment. I heard them talking on the phone on the way. Jenny is Sandra's daughter. When I understood that, my stomach turned upside down. I hated Sandra but considered her hot. She clearly despised me & had seriously contributed to me being demoted & emasculated in my own house. Maybe her daughter wasn't so smart or so intimidating. Maybe I could manage to sniff her underwear or spy on her in the bathroom. Surely her mom didn't tell her about all our issues! "Therapists can't do that, can they?" I asked Sara, clearly scared. "Jenny is a psychology grad student, dear."
When we got there, Sara gave her "my money," reminded her to please, please call if anything goes out of control, & thanked her 3 or 4 times. After 5 minutes, she just left, not even relating to me.
I was alone with Jenny. She was way hotter than I could have imagined. Tall with curly hair, a doll face with glasses, and chubby with a clearly defined waist.
A
Big-tits woman in her early 20s, clearly sex-positive & sexually active, who will spend the weekend with you without your wife present. For many men it would be a dream, and I did feel it was hot, but I felt really uncomfortable.
During the minutes Sara was there, Jenny ignored me, talked to her, told her many times she had nothing to be around for, offered to send me back in an Uber on Monday if she couldn't come, got the money, and said goodbye.
Then she turned to me. She offered me a Coke (with some molly I wasn't aware of!), and I could notice her tight top & jean shorts made her look so cheerful, smiling a lot. So different than her intentionally mean, men-hater mom or my now cold & distant wife. Jenny's voice was so sweet, but her tone was devastating.
"Do you know why you are here, Mr.?" She asked in a condescending way. I couldn't answer; I was petrified. She continued, "I am Ms. Jenny; my mom is Sandra. Do you remember who Sandra is?" I nodded. "Who is she?" Forcing me to answer "our couples therapist," I bubbled. "That's right!" "And why do you feel you need couples therapy?" I fully understand her mom told her at this point. The bitch just wanted me to say it. "Because my wife was frustrated & disappointed." My cheeks got so red.
"That's right. Poor woman is tired of being married to a man-child, isn't she"?
I didn't know what to do. During these 18 humiliating months, one of my biggest fears is other people finding out. & Here we are, with a young, sexy woman with a big ass to die for, making me admit all my shortcomings as a man. One by one
Jenny seems to know about my masturbation habits, porn consumption, erection issues, lack of job, body-related issues, weed consumption, & of course, about the fact that Sara sees other men & I am not involved at all but know it well.
After around an hour of peeling away the little male pride I had left, I felt the molly kicking in. Seriously. To the point my mind played me a game, I got the guts to touch Jenny's big boob and tried to pretend it was an accident. She slapped my face. Hard, no warning. She looked me in the eyes; I was terrified. Sara never hit me, even when she was super mad. Jenny gave me another slap, harder, with the other hand, landing on the other side of the face. Then her face relaxed, and her tone got sweet & condescending again. "Let's not get confused here. We aren't boyfriend & girlfriend. We aren't friends with benefits; this isn't one of your porn movies. You are an immature, inadequate cuckold & I am your babysitter…are we clear?" I didn't want any more confrontation. "Yes, Miss Jenny," I said, looking at the floor, aware it was a stupid mistake.
Jenny's apartment was a beautiful penthouse with an indoor pool, she went to her room, came back in a bikini, started talking to me like if I was 11 years old come on, u can swim naked, not big deal buddy" When I shook my head in fear & embarrassment, she asked me if I preferred another face slap. I started undressing. "It is small, I know. No need to hide it. Anyhow, I don't think we will be dealing with any unwanted erections or anything." She giggled.
We smoked some weed, and I was dying to jerk off, mesmerized by her bikini yet confused & intimidated.
"Sara complained a lot about you sexually; it has to be uncomfortable," she asked jokingly. "My mother had heard so many sad, sad, disgusting anecdotes about you. I am happy she is finally replacing you, dude."
"
What? What? What do you mean? "I asked, Really high, hypersensitive?"
"Take it easy, boy. I will explain it to you." She enjoyed my discomfort. "Sara dates men. You know that, right? "Not a surprise," I nodded. "& Sara wasn't just sexually starved; she was also emotionally & intellectually starved. I mean, look at you. You are more a dependent wuss than a partner." If not for Molly, I would have started crying. She stopped any answer and put her hand on my chin. "Right?" Again I nodded. She stepped back to another side of the pool, away from me. "Sara met many gentlemen in the past year. Some of them more than once." Since Sara never ever gave me details about her dates, I couldn't know this. I believed her. Ms. Jenny could see how uncomfortable I was; she kept pushing buttons mercilessly. Talking slowly, in a condescending tone. "Sometimes, when couples have good sex, often, emotions develop. Sara & Bryce started making love, not only fucking." "Bryce?" I asked, shocked. Yes, Bryce, You are a good listener. Sara & Bryce have a relationship." She looked at me. I was naked in the pool, horny but just half hard, and deeply embarrassed. The only thing I could say was "…a... relationship?"
"Yes, you silly! I mean, why not? She is tired & bored with you; he sees her more as a single mom with an overgrown child than as a cheating wife. So yeah, they are in a romantic relationship. & We all agreed you need to know."
After dropping that emotional bomb, she got up and walked out of the small, warm pool. I could see her big butt dropping water from close. I was really confused, horny but scared, and deeply emasculated.
Jenny brutally spanks the cuckold. Not written yet).
Suddenly her tone changed again. Sane, sweet, cheerful, popular college girl vibe from before I called her Mom & bitch. My ass was burning; I was almost crying, but she seemed really chill. "I guess that cleaned the air between us. What do you say, Mr.?" I didn't know what to do. Stayed quiet, bending over. "I mean, if you don't answer, I will understand you still need some more..." I answered immediately, "No... no... Miss Jenny is ok. Is that enough, please? I will behave." "Well, look at you, Mr.! So cooperative!" She was still mocking me. She just burned my ass mercilessly and now is still mocking me. I slowly got up and could face her. Was rubbing my butt cheeks and looking at the floor. Naked, crying a bit, high as fuck on molly. "Why did I just punish you, piggy?" I was too broken to resist her "for being disrespectful to your mom." I couldn't face her, but her thick, strong thighs entered my field of view. She was holding a beer. She gave it to me and said, "Enjoy your last adult drink for a while, piggy." I had no mental sense to ask her about that. I just started drinking. I was shaking with cold. She handed me my T-shirt, but nothing else. I was still bare waist down. My penis was so confused between the pain, the temperature, the molly, and her amazing behind walking around.
After some minutes I wasn't crying anymore. She handed me a joint. I smoked like 4 puffs in a row, trying to find a mental place less confusing & threatening. She took the joint away. "Easy, little man," she said in a really condescending tone.
"What would you like to play now, Mr. Macho Man?"
I was high and confused. "What do you mean by play? Can I be alone for a while, please?"
She thought about it for some seconds, which gave me hope. For the first time in the night, she sounded really caring and empathetic.. "I know this hasn't been a fun evening for you. And I know you really need emotional relief; masturbating & watching porn alone is an addiction for you, my mom says."
Which Sandra even said in front of me once. "But I really, really, really want to assure you..." Paused a second, "That it gets waaaay worse for you, Mr.!" Exploited laughter. Clearly under the effect of M, weed & watermelon gins. "Why, Jenny, really. Please, I need to be alone…" I'm trying to be clear but being extra careful not to be rude or anything.
Her beautiful brown eyebrows raised. "I know what you need! You need for me to pick a game for you! Of course, I had a class about that. Guys like you can't really make decisions." That last part she wasn't laughing anymore, cheerful but not joking. "We're going to play doctor! What do you say?"
"I want to go back. Really. Let me talk to my wife." For a moment I made eye contact with the crotch of her bikini; Miss Jenny had a bush. Just some seconds was amazing.
Jenny had totally ignored my last comment. She put on a white bathrobe with a big. Smile said, "I guess I am the doctor!"
I was still confused. Honestly. I really desired Miss Jenny, & I knew she was sex-positive & sexually active. But I was terrified about how easily she controlled me. & I was still processing that this Bryce guy was moving with us. The molly, the weed, and almost 20 hours with no masturbation. I was under stress.
"Obviously you will be the patient, since you are already half naked," she said as a matter of fact.
My ass was still sore. The couple of face slaps and the balls flick were more than enough to understand what Jenny says goes.
"This will be our checkup table," she said, putting both hands firmly on the massage table and leaning forward a little bit. I understood she wasn't wearing a bra under the robe. Her big, melon-shaped tits were so close yet so far away. She instructed me to get up on all fours over the massage table. I just wanted this night to end, and I did it. Open crack, little pink balls hanging, half erection. Still very sore. The spanking was very present in my mind. & Probably in hers too.
When I was finally in that humiliating position, he pulled a chair and sat down. Staring at me. Prolonging my agony a little bit.
"A little bird told me," she giggled at her own silly joke, "that you absolutely hate going to your prostate checkups or stuff like that. So now, this is our game."
She started rubbing Vaseline in my anus. Incredibly invasive. Sara would never ever put a finger even close to the area.
The adrenaline made me sober up for some seconds," Jenny I don't like my asshole touched..." I could finish. Jenny put a finger deep inside of me. "What did you say, dude?" I tried to start talking again when she slid another perfectly lubed finger, making me moan a little bit.
She put her free hand behind my head and pushed me down to the mattress. For a moment, or maybe it was my loaded brain playing a joke, I could smell her vulva on one of her fingers.
"Who is in charge, Piggy?" "You are...Miss Jenny."
"Smart boy!" She said. Pulling out her fingers, letting me raise my head. "Stay on all fours, please." I did; she went to wash her hands.
"Can I expect you to be more cooperative about medical checkups, Mr.? Or should we continue playing doctor?" My answer was swift: "Yes, yes, I am fine. I cooperate."
She smoked a bit and gave me some.
"There are a couple of things that need to happen to you," she said with a serious face, but the kind of serious face you look at a child with. "& It may not be really pleasant, but the sooner you understand your place, the better for everyone."
"Miss Jenny, you already spanked me, and I cried! And you even fingered me!"
"No, I didn't finger you; we were playing doctor! I checked your prostate, Mr."! Said and laughed. "Now, about the spanking. First of all, we both know you deserved it. And second, spankings will be so much a part of your new cuckyboy life, so who cares? This is your life now, dude."
I couldn't argue. Suddenly I imagined Sara having sex on what used to be my bed. Having their first night under the same roof.
"I am almost half your age. And here we are, right, Mr.PiggyPants?" She started lubing a weirdly shaped purple butt plug. It looked even worse than 2 fingers. "Next time you complain about the doctor checking you, I want you to remember this night." Swiftly inserted the toy in my already lubed and open rear entry.
Moaned, or yelled, I can't remember it. She waited around 5 minutes on her phone with my arms collapsed and my ass up, red & full. Then she pulled it off; the surprise made me squeal. "Get up, dude, we are done." She offered me some Gatorade & invited me to pass to her room. I followed , still feeling Vaseline in my ass crack. She sat on the bed and asked me to sit down in the high-back chair next to the bed. I sat down slowly, for obvious reasons. She got up, pulled out 2 pairs of metal handcuffs, and in no time, cuffed each of my wrists to an arm of the heavy wooden chair.
(Wait for the third chapter.)
I didn't know what Sara had in mind for this weekend. I assumed it had to do with a man, but the times I asked, she didn't answer me, just ignored me, changed the subject, or praised me for being "such a curious little man."
She dropped me at Jenny's apartment. I heard them talking on the phone on the way. Jenny is Sandra's daughter. When I understood that, my stomach turned upside down. I hated Sandra but considered her hot. She clearly despised me & had seriously contributed to me being demoted & emasculated in my own house. Maybe her daughter wasn't so smart or so intimidating. Maybe I could manage to sniff her underwear or spy on her in the bathroom. Surely her mom didn't tell her about all our issues! "Therapists can't do that, can they?" I asked Sara, clearly scared. "Jenny is a psychology grad student, dear."
When we got there, Sara gave her "my money," reminded her to please, please call if anything goes out of control, & thanked her 3 or 4 times. After 5 minutes, she just left, not even relating to me.
I was alone with Jenny. She was way hotter than I could have imagined. Tall with curly hair, a doll face with glasses, and chubby with a clearly defined waist.
A
Big-tits woman in her early 20s, clearly sex-positive & sexually active, who will spend the weekend with you without your wife present. For many men it would be a dream, and I did feel it was hot, but I felt really uncomfortable.
During the minutes Sara was there, Jenny ignored me, talked to her, told her many times she had nothing to be around for, offered to send me back in an Uber on Monday if she couldn't come, got the money, and said goodbye.
Then she turned to me. She offered me a Coke (with some molly I wasn't aware of!), and I could notice her tight top & jean shorts made her look so cheerful, smiling a lot. So different than her intentionally mean, men-hater mom or my now cold & distant wife. Jenny's voice was so sweet, but her tone was devastating.
"Do you know why you are here, Mr.?" She asked in a condescending way. I couldn't answer; I was petrified. She continued, "I am Ms. Jenny; my mom is Sandra. Do you remember who Sandra is?" I nodded. "Who is she?" Forcing me to answer "our couples therapist," I bubbled. "That's right!" "And why do you feel you need couples therapy?" I fully understand her mom told her at this point. The bitch just wanted me to say it. "Because my wife was frustrated & disappointed." My cheeks got so red.
"That's right. Poor woman is tired of being married to a man-child, isn't she"?
I didn't know what to do. During these 18 humiliating months, one of my biggest fears is other people finding out. & Here we are, with a young, sexy woman with a big ass to die for, making me admit all my shortcomings as a man. One by one
Jenny seems to know about my masturbation habits, porn consumption, erection issues, lack of job, body-related issues, weed consumption, & of course, about the fact that Sara sees other men & I am not involved at all but know it well.
After around an hour of peeling away the little male pride I had left, I felt the molly kicking in. Seriously. To the point my mind played me a game, I got the guts to touch Jenny's big boob and tried to pretend it was an accident. She slapped my face. Hard, no warning. She looked me in the eyes; I was terrified. Sara never hit me, even when she was super mad. Jenny gave me another slap, harder, with the other hand, landing on the other side of the face. Then her face relaxed, and her tone got sweet & condescending again. "Let's not get confused here. We aren't boyfriend & girlfriend. We aren't friends with benefits; this isn't one of your porn movies. You are an immature, inadequate cuckold & I am your babysitter…are we clear?" I didn't want any more confrontation. "Yes, Miss Jenny," I said, looking at the floor, aware it was a stupid mistake.
Jenny's apartment was a beautiful penthouse with an indoor pool, she went to her room, came back in a bikini, started talking to me like if I was 11 years old come on, u can swim naked, not big deal buddy" When I shook my head in fear & embarrassment, she asked me if I preferred another face slap. I started undressing. "It is small, I know. No need to hide it. Anyhow, I don't think we will be dealing with any unwanted erections or anything." She giggled.
We smoked some weed, and I was dying to jerk off, mesmerized by her bikini yet confused & intimidated.
"Sara complained a lot about you sexually; it has to be uncomfortable," she asked jokingly. "My mother had heard so many sad, sad, disgusting anecdotes about you. I am happy she is finally replacing you, dude."
"
What? What? What do you mean? "I asked, Really high, hypersensitive?"
"Take it easy, boy. I will explain it to you." She enjoyed my discomfort. "Sara dates men. You know that, right? "Not a surprise," I nodded. "& Sara wasn't just sexually starved; she was also emotionally & intellectually starved. I mean, look at you. You are more a dependent wuss than a partner." If not for Molly, I would have started crying. She stopped any answer and put her hand on my chin. "Right?" Again I nodded. She stepped back to another side of the pool, away from me. "Sara met many gentlemen in the past year. Some of them more than once." Since Sara never ever gave me details about her dates, I couldn't know this. I believed her. Ms. Jenny could see how uncomfortable I was; she kept pushing buttons mercilessly. Talking slowly, in a condescending tone. "Sometimes, when couples have good sex, often, emotions develop. Sara & Bryce started making love, not only fucking." "Bryce?" I asked, shocked. Yes, Bryce, You are a good listener. Sara & Bryce have a relationship." She looked at me. I was naked in the pool, horny but just half hard, and deeply embarrassed. The only thing I could say was "…a... relationship?"
"Yes, you silly! I mean, why not? She is tired & bored with you; he sees her more as a single mom with an overgrown child than as a cheating wife. So yeah, they are in a romantic relationship. & We all agreed you need to know."
After dropping that emotional bomb, she got up and walked out of the small, warm pool. I could see her big butt dropping water from close. I was really confused, horny but scared, and deeply emasculated.
Jenny brutally spanks the cuckold. Not written yet).
Suddenly her tone changed again. Sane, sweet, cheerful, popular college girl vibe from before I called her Mom & bitch. My ass was burning; I was almost crying, but she seemed really chill. "I guess that cleaned the air between us. What do you say, Mr.?" I didn't know what to do. Stayed quiet, bending over. "I mean, if you don't answer, I will understand you still need some more..." I answered immediately, "No... no... Miss Jenny is ok. Is that enough, please? I will behave." "Well, look at you, Mr.! So cooperative!" She was still mocking me. She just burned my ass mercilessly and now is still mocking me. I slowly got up and could face her. Was rubbing my butt cheeks and looking at the floor. Naked, crying a bit, high as fuck on molly. "Why did I just punish you, piggy?" I was too broken to resist her "for being disrespectful to your mom." I couldn't face her, but her thick, strong thighs entered my field of view. She was holding a beer. She gave it to me and said, "Enjoy your last adult drink for a while, piggy." I had no mental sense to ask her about that. I just started drinking. I was shaking with cold. She handed me my T-shirt, but nothing else. I was still bare waist down. My penis was so confused between the pain, the temperature, the molly, and her amazing behind walking around.
After some minutes I wasn't crying anymore. She handed me a joint. I smoked like 4 puffs in a row, trying to find a mental place less confusing & threatening. She took the joint away. "Easy, little man," she said in a really condescending tone.
"What would you like to play now, Mr. Macho Man?"
I was high and confused. "What do you mean by play? Can I be alone for a while, please?"
She thought about it for some seconds, which gave me hope. For the first time in the night, she sounded really caring and empathetic.. "I know this hasn't been a fun evening for you. And I know you really need emotional relief; masturbating & watching porn alone is an addiction for you, my mom says."
Which Sandra even said in front of me once. "But I really, really, really want to assure you..." Paused a second, "That it gets waaaay worse for you, Mr.!" Exploited laughter. Clearly under the effect of M, weed & watermelon gins. "Why, Jenny, really. Please, I need to be alone…" I'm trying to be clear but being extra careful not to be rude or anything.
Her beautiful brown eyebrows raised. "I know what you need! You need for me to pick a game for you! Of course, I had a class about that. Guys like you can't really make decisions." That last part she wasn't laughing anymore, cheerful but not joking. "We're going to play doctor! What do you say?"
"I want to go back. Really. Let me talk to my wife." For a moment I made eye contact with the crotch of her bikini; Miss Jenny had a bush. Just some seconds was amazing.
Jenny had totally ignored my last comment. She put on a white bathrobe with a big. Smile said, "I guess I am the doctor!"
I was still confused. Honestly. I really desired Miss Jenny, & I knew she was sex-positive & sexually active. But I was terrified about how easily she controlled me. & I was still processing that this Bryce guy was moving with us. The molly, the weed, and almost 20 hours with no masturbation. I was under stress.
"Obviously you will be the patient, since you are already half naked," she said as a matter of fact.
My ass was still sore. The couple of face slaps and the balls flick were more than enough to understand what Jenny says goes.
"This will be our checkup table," she said, putting both hands firmly on the massage table and leaning forward a little bit. I understood she wasn't wearing a bra under the robe. Her big, melon-shaped tits were so close yet so far away. She instructed me to get up on all fours over the massage table. I just wanted this night to end, and I did it. Open crack, little pink balls hanging, half erection. Still very sore. The spanking was very present in my mind. & Probably in hers too.
When I was finally in that humiliating position, he pulled a chair and sat down. Staring at me. Prolonging my agony a little bit.
"A little bird told me," she giggled at her own silly joke, "that you absolutely hate going to your prostate checkups or stuff like that. So now, this is our game."
She started rubbing Vaseline in my anus. Incredibly invasive. Sara would never ever put a finger even close to the area.
The adrenaline made me sober up for some seconds," Jenny I don't like my asshole touched..." I could finish. Jenny put a finger deep inside of me. "What did you say, dude?" I tried to start talking again when she slid another perfectly lubed finger, making me moan a little bit.
She put her free hand behind my head and pushed me down to the mattress. For a moment, or maybe it was my loaded brain playing a joke, I could smell her vulva on one of her fingers.
"Who is in charge, Piggy?" "You are...Miss Jenny."
"Smart boy!" She said. Pulling out her fingers, letting me raise my head. "Stay on all fours, please." I did; she went to wash her hands.
"Can I expect you to be more cooperative about medical checkups, Mr.? Or should we continue playing doctor?" My answer was swift: "Yes, yes, I am fine. I cooperate."
She smoked a bit and gave me some.
"There are a couple of things that need to happen to you," she said with a serious face, but the kind of serious face you look at a child with. "& It may not be really pleasant, but the sooner you understand your place, the better for everyone."
"Miss Jenny, you already spanked me, and I cried! And you even fingered me!"
"No, I didn't finger you; we were playing doctor! I checked your prostate, Mr."! Said and laughed. "Now, about the spanking. First of all, we both know you deserved it. And second, spankings will be so much a part of your new cuckyboy life, so who cares? This is your life now, dude."
I couldn't argue. Suddenly I imagined Sara having sex on what used to be my bed. Having their first night under the same roof.
"I am almost half your age. And here we are, right, Mr.PiggyPants?" She started lubing a weirdly shaped purple butt plug. It looked even worse than 2 fingers. "Next time you complain about the doctor checking you, I want you to remember this night." Swiftly inserted the toy in my already lubed and open rear entry.
Moaned, or yelled, I can't remember it. She waited around 5 minutes on her phone with my arms collapsed and my ass up, red & full. Then she pulled it off; the surprise made me squeal. "Get up, dude, we are done." She offered me some Gatorade & invited me to pass to her room. I followed , still feeling Vaseline in my ass crack. She sat on the bed and asked me to sit down in the high-back chair next to the bed. I sat down slowly, for obvious reasons. She got up, pulled out 2 pairs of metal handcuffs, and in no time, cuffed each of my wrists to an arm of the heavy wooden chair.
(Wait for the third chapter.)
