Mr. Henry 4 / for 'D'
You arrived back at Mr. Henry’s at 4:30 the following day, as he wanted to brief you a bit before the girl arrived at five.
“You remember Nancy, don’t you?” Mr Henry said, handing you a picture. “She graduated the year before you.”
Nancy was a shy, pretty black girl. You knew her more from your old neighborhood than you did from school. Nancy had lived only a couple blocks away, and while you didn’t hang out all that much, she’d been kind whenever you did interact. Nancy went on to college, and excelled - completing a law degree at a school back east, then coming back for a position at a local law firm.
“Nancy’s husband and I have a somewhat different relationship.” Mr. Henry explained. “They have a very happy, and healthy marriage. However, Nancy has a bit of a masochistic streak, and her husband doesn’t wish to jeopardize what they have by punishing her. Instead, he sends Nancy to me for discipline. We meet every other week.”
You were still trying to grasp the concept. “And he doesn’t mind you having sex with his wife?”
“That’s just it, D - we don’t have sex, and never will.” Mr. Henry explained. “That’s not to say she isn’t turned on by our sessions, it excites her terribly. She suffers her punishments in the nude. It’s as though the denial is part of her discipline. Your thoughts, D?”
“It sounds amazing, Mr. Henry.” You answered. While you answered in the affirmative, it was still unknown territory. If you’d been asked about getting spanked and caned by a high school teacher a week ago, you would have laughed out loud. The concept of involving another woman was foreign, but titillating. “I hope you understand I’m new at this.”
“I understand, D.” Mr. Henry reassured. “Just to warn you, I’m a bit more harsh with Nancy. Just remember, she’s doing this willingly, and has ‘safe’ words to let me know if I need to ease back, or stop altogether.”
Almost on cue, there was a knock at the door.
“Nancy!” Mr. Henry greeted her as she stepped in. “Perhaps you remember ‘D’? She’s going to monitor our session today.”
“Yes, Mr. Henry.” Nancy answered, smiling. “Good to see you again, D!”
“Expose, Nancy.” Mr. Henry’s tone shifted.
Nancy’s expression shifted as she pulled down her skirt and panties, revealing a shaved pussy.
Mr. Henry pulled out a credit card, and rubbed it directly on Nancy’s crotch. “I detect a little bit of cunt stubble, Nancy. You’ll need to do a better job of keeping yourself smooth. You’ll be punished for that.”
“Yes, Mr. Henry.” Nancy said, her tone simple and soft.
“Let’s see the letter, Nancy.” Mr. Henry ordered. Nancy responded by handing him a sealed envelope.
Mr. Henry opened the letter, and read out loud:
Mr. Henry -
Thank you again for your time and efforts in aiding in Nancy’s correction.
Nancy has made several violations this week which require your attention. She has admitted to masturbating at least 3 times since the first of the month.
At the store last week, Nancy bent over and flaunted her breasts to a young clerk. While Nancy claims the exposure was incidental, I feel that it would be appropriate for you to punish those breasts as you see fit.
One other thing - Nancy ate the last cinnamon roll the other day.
Thank you again for your help. Signed….'
Mr. Henry set the handwritten letter down on the table. Teachers had a way of making silence practically unbearable.
“Nancy.” Mr. Henry began in a measured tone. “Slutty Nancy. Playing with her cunt AGAIN. I thought we had talked about that before?”
“Yes, Mr. Henry.” Nancy said, her voice shaking. It became evident that Nancy was already in a high state of arousal. “I was bad, and played with my cunt.”
Watching Nancy interaction with Mr. Henry brought things into sharper focus. Nancy thought about being punished while she was masturbating. Knowing a punishment would result for that masturbation only fed the cycle.
“Nancy, show D how you masturbate.” Mr. Henry ordered.
Nancy licked her fingers, and placed them on her crotch and began rubbing.
“Doesn’t she look like a horny little whore, D? She’d give anything to suck my cock, or have me fuck her. But she knows she can’t have that.” Mr. Henry then began removing his belt. “She’s going to get her tits whipped for using them to tease that boy at the store. And Nancy, what happens to dirty little masturbators?”
Nancy continued to finger herself. “They get whipped, Mr. Henry”.
“That’s right, Nancy.” Mr. Henry responded. “Now strip.”
Nancy first removed her shoes, then removed her top and folded it neatly. The skirt was next, then the bra. You remembered that Nancy was well endowed in high school - and her tits were now even larger. The panties came off next.
“D, set that chair in the middle of the room, and help Nancy bend over the back of it.
Nancy’s hand felt warm to the touch. She was actually sobbing a little. She looked amazing.
“Nancy gets a bit loud when she is whipped.” Mr. Henry said, reaching over for what looked like a rubber bone. “Place this in her mouth, so she has a bite block.”
Nancy opened her mouth and took the bone in her mouth obediently.
Mr. Henry used a single-tail whip on Nancy’s bottom. The strokes were harsh, and direct. Nancy had a beautiful, ample rear and it almost hurt to watch it endure such punishment. Her groans were deep and muffled by the rubber gag. Her breasts swayed with each shot from the whip.
“Nasty Nancy! Just can’t stop playing with our cunt, can we?” Mr. Henry taunted. “Now, spread those knees like a whore.”
Nancy obeyed, pushing her rear back out and spreading her knees as wide as she could. The spread was met with an uppercut from the whip that landed directly on her pussy. A scream followed that caused the dog bone to drop from Nancy’s mouth.
“Did you drop your bit, Nancy?” Mr. Henry barked.
“Yes, Mr. Henry.” Nancy sobbed. “I’m sorry.”
“And what happens to sluts who drop their bones?” Mr. Henry asked.
“They get whipped again.” Nancy cried.
“And where do they get whipped?”
“Right on their cunts, Mr. Henry.”
“And how do they ask for it, Nancy?”
“Please whip me again on my cunt, Mr. Henry.”
Mr. Henry was practiced at making the very tip of the whip land with great accuracy. Nancy took 4 more strokes, asking for each one, and thanking Mr. Henry afterwards.
“Before we whip your tits, Nancy, we have a very special punishment for you. D, would you like to take my cock in your mouth? And maybe get fucked with it? Nancy isn’t allowed that sort of pleasure, but she’s a horny girl and likes watching.”
Fuck. The intensity had just gone up a notch or six. You didn’t even answer. You just began getting undressed, as Nancy shuffled painfully over to a couch and sat down. Mr. Henry slipped off his shoes and socks, unbuttoned his shirt, and lowered his trousers. He was already hard from performing the whipping.
“Hands behind, D. Mouth open.” You obeyed. You gave it a gentle kiss first, then Mr. Henry pushed it so deep in your mouth that you gagged a little. Nancy watched from the couch, nude, and eyes wide. She looked quite stunning for a woman who had just been whipped.
Mr. Henry grabbed your hair as he face fucked you. This was much different than yesterday’s ‘aftercare’ oral sex - but you somehow felt you were working to pleasure two people this time.
“Her mouth feels so good, Nancy.” Mr. Henry chided. “Don’t you wish it was your mouth? My cock is so hard. D is going to get fucked now, too.”
Mr. Henry lifted you up, and had you place your elbows on the seat of the chair where Nancy had just been whipped. You were staring directly at her.
“Ask me to stick my cock in you, D.”
“Please stick your cock in me, Mr. Henry.”
You felt Mr. Henry’s cock rub up, then down on your pussy before sliding in. No problem, you were already wet from watching. Mr. Henry began slow, then built up momentum. The fucking was intense. Nancy watched intently, slapping her pussy rather than rubbing it. It must have hurt like hell. You were actually getting fucked by your high school English teacher. That reality alone triggered an orgasm that was almost blinding, and left you unable to function.
“D, I’m going to cum in you.” Mr. Henry groaned. It was only a few more strokes before he spasmed several times, and you felt his cream enter you. Nancy was transfixed.
“Nancy, don’t you wish you were able to taste that load?” Mr Henry grunted, gathering his breath. You’ve practically begged to suck and fuck me in the past, and that’s not going to happen. But tonight, you’ll get a special treat. But first, it’s time to whip your tits, isn’t it? Lay down on the floor, Nancy.”
Nancy slid off the couch onto the floor, laying on her back, chest out. Mr. Henry reached for his belt, and doubled it.
“D, I want you to squat on Nancy’s face and let her taste my seed while I whip her tits. This is the only way she will be allowed to taste my cum”.
You looked at Nancy, and were met with a plea.
“Please, D - Please let me taste it - I want to taste it so bad.”
You squatted down on Nancy’s face as Mr. Henry began to use his belt on her chest. Each stroke landed with a hard slap, and caused Nancy to buck upwards, as she began to lick your pussy. Nancy’s face looked beautiful - a mix of pain and high arousal. Her tongue felt wet and warm on your pussy. You could feel her licking up the cream like a thirsty kitten as the belt continued to land on her chest.
“Every drop, Nancy.” Mr. Henry noted before bringing his belt down hard again.
You felt Nancy’s tongue drift down between your ass cheeks, lapping up the cum that had oozed out. There were a couple kisses mixed in with the licks directly on your asshole.
“Well, Nancy, aren’t you a lucky girl to finally taste some of my seed?” Mr. Henry asked.
“Yes, thank you, Mr. Henry.” Nancy responded.
“Continue to pleasure D while I respond to your husband.” Said Mr. Henry, sitting down naked at his desk, grabbing a pen to write on the back of the letter he’d read earlier.
In a way, this was Nancy’s aftercare. You rubbed your crotch over her nose and face, and she responded with moans and gratitude.
Mr. Henry read his response out out.
‘Nancy has taken her punishment well tonight. Her bottom has been punished with a whip for her continuing masturbation condition, and a leather belt was used on her tits for teasing the clerk at the store.
Nancy’s discipline was witnessed by a female friend.
As Nancy is a cinnamon roll thief, she was also allowed to sample some cream filling from the woman’s privates.
It is my suggestion that Nancy should fellate you upon her arrival home as thanks for her continued education.
Best Wishes,
Mr. Henry.’
“You remember Nancy, don’t you?” Mr Henry said, handing you a picture. “She graduated the year before you.”
Nancy was a shy, pretty black girl. You knew her more from your old neighborhood than you did from school. Nancy had lived only a couple blocks away, and while you didn’t hang out all that much, she’d been kind whenever you did interact. Nancy went on to college, and excelled - completing a law degree at a school back east, then coming back for a position at a local law firm.
“Nancy’s husband and I have a somewhat different relationship.” Mr. Henry explained. “They have a very happy, and healthy marriage. However, Nancy has a bit of a masochistic streak, and her husband doesn’t wish to jeopardize what they have by punishing her. Instead, he sends Nancy to me for discipline. We meet every other week.”
You were still trying to grasp the concept. “And he doesn’t mind you having sex with his wife?”
“That’s just it, D - we don’t have sex, and never will.” Mr. Henry explained. “That’s not to say she isn’t turned on by our sessions, it excites her terribly. She suffers her punishments in the nude. It’s as though the denial is part of her discipline. Your thoughts, D?”
“It sounds amazing, Mr. Henry.” You answered. While you answered in the affirmative, it was still unknown territory. If you’d been asked about getting spanked and caned by a high school teacher a week ago, you would have laughed out loud. The concept of involving another woman was foreign, but titillating. “I hope you understand I’m new at this.”
“I understand, D.” Mr. Henry reassured. “Just to warn you, I’m a bit more harsh with Nancy. Just remember, she’s doing this willingly, and has ‘safe’ words to let me know if I need to ease back, or stop altogether.”
Almost on cue, there was a knock at the door.
“Nancy!” Mr. Henry greeted her as she stepped in. “Perhaps you remember ‘D’? She’s going to monitor our session today.”
“Yes, Mr. Henry.” Nancy answered, smiling. “Good to see you again, D!”
“Expose, Nancy.” Mr. Henry’s tone shifted.
Nancy’s expression shifted as she pulled down her skirt and panties, revealing a shaved pussy.
Mr. Henry pulled out a credit card, and rubbed it directly on Nancy’s crotch. “I detect a little bit of cunt stubble, Nancy. You’ll need to do a better job of keeping yourself smooth. You’ll be punished for that.”
“Yes, Mr. Henry.” Nancy said, her tone simple and soft.
“Let’s see the letter, Nancy.” Mr. Henry ordered. Nancy responded by handing him a sealed envelope.
Mr. Henry opened the letter, and read out loud:
Mr. Henry -
Thank you again for your time and efforts in aiding in Nancy’s correction.
Nancy has made several violations this week which require your attention. She has admitted to masturbating at least 3 times since the first of the month.
At the store last week, Nancy bent over and flaunted her breasts to a young clerk. While Nancy claims the exposure was incidental, I feel that it would be appropriate for you to punish those breasts as you see fit.
One other thing - Nancy ate the last cinnamon roll the other day.
Thank you again for your help. Signed….'
Mr. Henry set the handwritten letter down on the table. Teachers had a way of making silence practically unbearable.
“Nancy.” Mr. Henry began in a measured tone. “Slutty Nancy. Playing with her cunt AGAIN. I thought we had talked about that before?”
“Yes, Mr. Henry.” Nancy said, her voice shaking. It became evident that Nancy was already in a high state of arousal. “I was bad, and played with my cunt.”
Watching Nancy interaction with Mr. Henry brought things into sharper focus. Nancy thought about being punished while she was masturbating. Knowing a punishment would result for that masturbation only fed the cycle.
“Nancy, show D how you masturbate.” Mr. Henry ordered.
Nancy licked her fingers, and placed them on her crotch and began rubbing.
“Doesn’t she look like a horny little whore, D? She’d give anything to suck my cock, or have me fuck her. But she knows she can’t have that.” Mr. Henry then began removing his belt. “She’s going to get her tits whipped for using them to tease that boy at the store. And Nancy, what happens to dirty little masturbators?”
Nancy continued to finger herself. “They get whipped, Mr. Henry”.
“That’s right, Nancy.” Mr. Henry responded. “Now strip.”
Nancy first removed her shoes, then removed her top and folded it neatly. The skirt was next, then the bra. You remembered that Nancy was well endowed in high school - and her tits were now even larger. The panties came off next.
“D, set that chair in the middle of the room, and help Nancy bend over the back of it.
Nancy’s hand felt warm to the touch. She was actually sobbing a little. She looked amazing.
“Nancy gets a bit loud when she is whipped.” Mr. Henry said, reaching over for what looked like a rubber bone. “Place this in her mouth, so she has a bite block.”
Nancy opened her mouth and took the bone in her mouth obediently.
Mr. Henry used a single-tail whip on Nancy’s bottom. The strokes were harsh, and direct. Nancy had a beautiful, ample rear and it almost hurt to watch it endure such punishment. Her groans were deep and muffled by the rubber gag. Her breasts swayed with each shot from the whip.
“Nasty Nancy! Just can’t stop playing with our cunt, can we?” Mr. Henry taunted. “Now, spread those knees like a whore.”
Nancy obeyed, pushing her rear back out and spreading her knees as wide as she could. The spread was met with an uppercut from the whip that landed directly on her pussy. A scream followed that caused the dog bone to drop from Nancy’s mouth.
“Did you drop your bit, Nancy?” Mr. Henry barked.
“Yes, Mr. Henry.” Nancy sobbed. “I’m sorry.”
“And what happens to sluts who drop their bones?” Mr. Henry asked.
“They get whipped again.” Nancy cried.
“And where do they get whipped?”
“Right on their cunts, Mr. Henry.”
“And how do they ask for it, Nancy?”
“Please whip me again on my cunt, Mr. Henry.”
Mr. Henry was practiced at making the very tip of the whip land with great accuracy. Nancy took 4 more strokes, asking for each one, and thanking Mr. Henry afterwards.
“Before we whip your tits, Nancy, we have a very special punishment for you. D, would you like to take my cock in your mouth? And maybe get fucked with it? Nancy isn’t allowed that sort of pleasure, but she’s a horny girl and likes watching.”
Fuck. The intensity had just gone up a notch or six. You didn’t even answer. You just began getting undressed, as Nancy shuffled painfully over to a couch and sat down. Mr. Henry slipped off his shoes and socks, unbuttoned his shirt, and lowered his trousers. He was already hard from performing the whipping.
“Hands behind, D. Mouth open.” You obeyed. You gave it a gentle kiss first, then Mr. Henry pushed it so deep in your mouth that you gagged a little. Nancy watched from the couch, nude, and eyes wide. She looked quite stunning for a woman who had just been whipped.
Mr. Henry grabbed your hair as he face fucked you. This was much different than yesterday’s ‘aftercare’ oral sex - but you somehow felt you were working to pleasure two people this time.
“Her mouth feels so good, Nancy.” Mr. Henry chided. “Don’t you wish it was your mouth? My cock is so hard. D is going to get fucked now, too.”
Mr. Henry lifted you up, and had you place your elbows on the seat of the chair where Nancy had just been whipped. You were staring directly at her.
“Ask me to stick my cock in you, D.”
“Please stick your cock in me, Mr. Henry.”
You felt Mr. Henry’s cock rub up, then down on your pussy before sliding in. No problem, you were already wet from watching. Mr. Henry began slow, then built up momentum. The fucking was intense. Nancy watched intently, slapping her pussy rather than rubbing it. It must have hurt like hell. You were actually getting fucked by your high school English teacher. That reality alone triggered an orgasm that was almost blinding, and left you unable to function.
“D, I’m going to cum in you.” Mr. Henry groaned. It was only a few more strokes before he spasmed several times, and you felt his cream enter you. Nancy was transfixed.
“Nancy, don’t you wish you were able to taste that load?” Mr Henry grunted, gathering his breath. You’ve practically begged to suck and fuck me in the past, and that’s not going to happen. But tonight, you’ll get a special treat. But first, it’s time to whip your tits, isn’t it? Lay down on the floor, Nancy.”
Nancy slid off the couch onto the floor, laying on her back, chest out. Mr. Henry reached for his belt, and doubled it.
“D, I want you to squat on Nancy’s face and let her taste my seed while I whip her tits. This is the only way she will be allowed to taste my cum”.
You looked at Nancy, and were met with a plea.
“Please, D - Please let me taste it - I want to taste it so bad.”
You squatted down on Nancy’s face as Mr. Henry began to use his belt on her chest. Each stroke landed with a hard slap, and caused Nancy to buck upwards, as she began to lick your pussy. Nancy’s face looked beautiful - a mix of pain and high arousal. Her tongue felt wet and warm on your pussy. You could feel her licking up the cream like a thirsty kitten as the belt continued to land on her chest.
“Every drop, Nancy.” Mr. Henry noted before bringing his belt down hard again.
You felt Nancy’s tongue drift down between your ass cheeks, lapping up the cum that had oozed out. There were a couple kisses mixed in with the licks directly on your asshole.
“Well, Nancy, aren’t you a lucky girl to finally taste some of my seed?” Mr. Henry asked.
“Yes, thank you, Mr. Henry.” Nancy responded.
“Continue to pleasure D while I respond to your husband.” Said Mr. Henry, sitting down naked at his desk, grabbing a pen to write on the back of the letter he’d read earlier.
In a way, this was Nancy’s aftercare. You rubbed your crotch over her nose and face, and she responded with moans and gratitude.
Mr. Henry read his response out out.
‘Nancy has taken her punishment well tonight. Her bottom has been punished with a whip for her continuing masturbation condition, and a leather belt was used on her tits for teasing the clerk at the store.
Nancy’s discipline was witnessed by a female friend.
As Nancy is a cinnamon roll thief, she was also allowed to sample some cream filling from the woman’s privates.
It is my suggestion that Nancy should fellate you upon her arrival home as thanks for her continued education.
Best Wishes,
Mr. Henry.’
2 月 前