Jeff rang Jennie’s doorbell with mixed feelings. Since his first visit a couple of days earlier he’d had sex with his wife no fewer than five times. He’d felt insatiable – grabbing Cheryl at every opportunity. For her part his wife had been both delighted and amused. She’d been desperate to know why he was suddenly unable to keep his hands off her. Of course Jeff couldn’t tell her about what her own sister was doing to him – effectively it was sexual blackmail.
He rang the doorbell a second time. Jennie was expecting him…she’d reminded him to be on time in a text message earlier in fact. Where was she?
He heard the sound of an upstairs window opening. Jennie popped her head out.
“You’re five minutes early,” she said brightly. “Wait there on the step. Don’t go back to your car.”
Jeff groaned inwardly. It was raining a bit, and he hadn’t brought an umbrella out of the car. There was a tiny overhang roof over Jennie’s cottage door, but it didn’t offer much in the way of protection.
Eight minutes later Jennie opened the door – Jeff was soaked and shivering by that time.
Ironically Jennie seemed to be wearing a raincoat! It was actually a lightweight black trenchcoat, some kind of shiny nylon material that glistened as she moved. She had black stiletto boots on, and black leather gloves.
“Come in,” she ordered. “Stay in the hall and take off those clothes – I don’t want you dripping on my carpets.”
Jeff did as he was told, and managed to hang his wet clothes on the coat hooks near the door. His clothes weren’t actually dripping, but they were rather soggy. Naked now, he followed Jennie through to the lounge, and found her sitting with her legs crossed on one of the armchairs. He saw now that the black boots stretched above her knees, and seemed to be sprayed onto her legs, they were so tight. Automatically his cock started to grow hard, even if the rest of him was shivering!
“Oh for fuck’s sake!” Jennie said. “You’re getting turned on already? According to Cheryl you’ve been screwing her constantly over the past couple of days, so where the hell do you find the energy? Well? Speak up!”
“Sorry, Mistress,” Jeff couldn’t hide a grin. “You do look very…dominant in that outfit.”
Jennie smiled, but then put a serious expression on her face.
“Put your hands on your head and stand with your legs apart. Yes, keep standing like that,” she ordered. She sat there playing with her gloves, pressing the leather down tightly onto her fingers. She was flexing one ankle, causing Jeff to stare at the leather as it moved.
“Right then,” Jennie said. “In a moment you can start your chores. But first I want you to tell me about each time you made love to my sister since we saw each other. Don’t leave any details out…you may begin.”
Jeff flushed in embarrassment, but then started to stammer out the details of the first love making session. It had been just a few minutes after he’d arrived home after seeing Jennie. Cheryl had been clearing up in the kitchen, and he’d literally carried her upstairs to the bathroom, stripped her naked, and they’d had sex while they were showering together. The second time had been an hour later, in bed this time after he’d recovered. Another two hours later she’d begged him not to make love a third time. But he’d teased and licked her pussy until she rolled him over and jumped on top of him.
The next morning he didn’t even have his normal wake-up hard on, he was so drained. But he called his wife three times during the day and the calls had become very suggestive indeed. When he got home Cheryl was waiting for him in a sexy bra and stockings set. They’d made love twice more that evening.
Jennie quizzed him on how many orgasms her sister had had each time. Jeff seemed unsure.
“OK…slave,” she said firmly. “You need to understand that from now on your sexual needs are secondary. Cheryl isn’t your Mistress, not like me obviously. But she’s my sister, and I want you to make her happy. Very, very happy, do you understand me?”
“Yes, Mistress!” Jeff said quietly.
“From now on you are not permitted to have your orgasm until Cheryl has come…at least three times. Three times! Do you hear me?” Jennie told him.
“Yes Mistress,” Jeff said, cringing.
“And another thing,” Jennie added. “You will not be permitted more than one orgasm each day. By all means make love to Cheryl as many times as you want, but you are not allowed to come more than once. So you might want to think carefully about quality, and not quantity in future. Is that clear?”
“Yes, Mistress Jennie,” Jeff agreed.
Jennie continued to give Jeff advice on how to please a woman, the pace of his lovemaking, being patient and caring.
“And you need to believe me when I tell you that Cheryl and I do talk about this kind of thing,” Jennie said, staring him in the eyes. “If you fail to perform, I will find out. And I’ll punish you in a way that you won’t like. It won’t be sexy…it will be very painful, and very humiliating.”
“I understand, Mistress,” Jeff said quickly.
Jennie looked at him for a few seconds. “I wonder if you really do understand?” she mused. “I think I need to give you a small taste of what might happen to you. Stay there.”
She got up from the chair and brushed past him on her way out of the lounge. He heard the click-clack of her boot heels on the wooden floor in the hall, then the sound of her going up the stairs. Two minutes later she was standing in front of him again.
“Recognise this?” she asked, holding up a tube of cream.
“It’s Deep Heat,” Jeff said hesitantly. In his youth he’d occasionally used it to ease sore muscles after rugby practice.
“Very good,” she chuckled. “And in the instructions it warns about putting it on certain sensitive parts of the body. Can you think of some sensitive areas that we shouldn’t put this on?”
Jeff licked his lips and tried to swallow. “Y…yes Mistress,” he said, his gaze locked on the tube.
“Well?” Jennie pressed.
“M…my penis, Mistress?” Jeff suggested quietly.
“Yes,” Jennie agreed. “And?”
“Err. My balls?” he added.
Jennie giggled. “Oh yes!” she said. “And?”
Jeff hesitated. “My…nipples?”
Jennie considered this. “Maybe…especially after they’ve been tortured I suppose,” she conceded. “Where else?”
Jeff was running out of ideas now. “My…eyes?” he tried in desperation.
“Oh for fuck’s sake!” Jennie said, rolling her eyes. “I may be a bit kinky, but I’m not a fucking psychopath…I’m not going to blind you. Try lower down.”
Jeff thought for a few seconds. “Oh!” he said. “Well…up my bottom I suppose?”
“Very good!” Jennie said, and leaned forward to kiss him gently on the mouth. “Slave gets a kiss for being clever. Bend over,” she said. “I’m going to give you a small demonstration.”
“Oh please, Mistress, don’t!” Jeff begged. “I can imagine it will be horrible…like after a really hot curry, but probably a lot worse. Please, you don’t need to show me. It’s not fair! I haven’t done anything wrong have I?”
“Maybe not, but I want to see what happens!” Jennie giggled. “Don’t worry. I’m only going to put a tiny dab on the very outside. It’s a demonstration, not a proper punishment. Come on! Do as you’re told; or I’ll get annoyed.”
Jeff bent over while Jennie pulled off one of her gloves. He felt a gentle dab on his anus, and then he was allowed to stand again.
Jennie looked at him with an expectant smile.
“Owww!” Jeff said as the cream began to burn. He squirmed and was desperate to put his hands down there…but he knew he had to remain standing.
“OK, is that like a hot curry?” Jennie asked, smiling.
“It’s worse Mistress! It’s more on the outside. Oh God; it really hurts!” he whined.
“And is it the kind of hurting that could be sexy?” she asked him.
“Not really,” he said without thinking.
“Excellent!” Jennie beamed. “I was right then…it’ll be a good punishment. Very good…now I’m going to show you a present I bought for you.”
Jennie walked over to a box on the table. Her raincoat swished as she walked, and it seemed to cling nicely to her body. Jeff wondered what she was wearing underneath.
She came back holding a black, rubbery object.
“This is a butt plug. It’s going up your arse!” she said, smiling.
“Oh no, please!” Jeff said, bringing his hands down defensively in front of him.
“Hands on head! Now!” Jennie said immediately. She swung her right hand and slapped him hard across the face. Jeff quickly resumed his position, hands on head.
“Sorry Mistress, but it’s…it’s so big,” he stammered.
“Actually it’s quite small as these things go,” Jennie said, grinning. “Some of them are huge. But I’ll need to get you used to this one first, before I start to really stretch you. Now just relax, it’s going to be quite pleasant for you I assure you.”
“But it’s…so…gay. Sorry, Mistress,” Jeff said quietly.
“Of course it is…but you don’t have any say in this,” she said, tapping the butt plug across his face lightly. “This is not your decision, is it?”
“No, Mistress,” Jeff answered.
“Good. Bend over then,” Jennie ordered.
Jeff bent over and grabbed his knees with his hands. Out of the corner of his eye he saw Jennie move back to the table. She took off her black leather gloves, and put on a pair of surgical latex gloves instead. He groaned inwardly. He hated the idea of somebody – anybody messing about with his backside…this wasn’t going to be pleasant at all.
Jennie turned around and he saw she was holding a plastic bottle with a clear liquid in it.
“OK, I’m going to put some of this lube into your bottom,” she told him. “It might be a bit cold. Is your ring piece still tingling from the Deep Heat?”
“It’s fading now Mistress,” Jeff admitted.
“Well if this had been a real punishment, I wouldn’t use lube on the butt plug,” Jennie explained. “I’d use Deep Heat. It would go all the way inside you, and I can assure you it’ll do more than just sting. You’ll wish you’d never been born…do you understand me?”
“Please Mistress, don’t!” Jeff gasped.
“It’s a punishment, stupid!” Jennie laughed. “I’ll use it if and when I feel it’s necessary. And even better, Cheryl will never know because it won’t leave any external marks. Isn’t that clever?”
“Yes Mistress Jennie,” Jeff groaned.
Jennie squirted lube onto her fingers and applied it to Jeff’s arse, and to the butt plug. With some difficulty, and after several requests for him to relax, she managed to slide the black rubber plug into him.
“Stand up! Hands on head,” she commanded. Jeff obeyed instantly.
“How does that feel?” she asked, standing in front of him.
“It feels horrible, Mistress,” he said miserably. “It’s not supposed to be there. Please can I take it out?”
Jennie chuckled. “No, my dear, you can’t.” She walked over to the table and stripped off the latex gloves, replacing them with her black leather gloves. Then she walked back to Jeff and stood in front of him again.
“If it’s horrible, why have you got a big fat hard on?” she whispered, brushing her lips against his cheek.
Jeff couldn’t think of anything to say. He allowed a small whimper to leak from his lips.
“Oh, poor baby,” Jennie whispered. She stroked his nipples gently with her gloved fingers. “Poor sweet baby. Do you like having it up your arse?”
“No!” Jeff almost sobbed the answer. “No Mistress.”
Jennie chuckled softly. “I think you do. Big, fat hard-ons don’t lie!”
“It’s just that I like seeing you in that sexy outfit, Mistress,” he told her. “That’s what’s turning me on…and you teasing me.”
Jennie sighed gently. “And you like having that thing up your arse…tell me how you like it.”
Jeff bit his lip. Actually it was…quite nice really. It felt weird, but it was a good kind of weird.
“Tell me,” Jennie teased.
“Yes, OK,” Jeff gasped. “It’s sort of nice.”
Jennie leaned down and sucked his right nipple gently. She allowed her gloved hand to brush very briefly over his cock.
“Good boy,” she murmured. “Now you can start your chores. There’s a wall to paint and about ten pictures to hang. I’ve marked the positions with post-it notes. Come and find me when you finish painting the wall because you can worship my boots as a reward. See how I think about you?”
“Yes Mistress. Thank you,” Jeff said, and he meant it. He was dying to touch her thigh length boots.
“Oh one quick thing before we start. Or you start I should say!” she said.
Jennie fetched her camera from the table. She ordered Jeff to pose for some photos, first of his naked body in his submission position. Then she asked him to bend over to show the butt plug sticking out of his bottom. She took dozens of photos this time.
“I want to make sure you know I have the goods on you,” she chuckled. “To keep you on the straight and narrow…now get on with your work.”