Disciplined for Peeping

Veronica (Ronnie) was in her late 40's. She was a very rich widow who felt bullied by her financial advisors. Her late husband had picked them years before he died and told them to be strict with Ronnie's handling of the inheritance, when the time came. Ronnie lived in luxury and had plenty of money to play with, but she hated that she had to submit to a bunch of old men on financial matters.

Ronnie was wearing a black knee length skirt, a white blouse and high heels. Tony was dressed in jeans and knit pullover shirt.

Ronnie and Tony walked up the stairs to the upstairs bedroom. "You will call me Ma'am while we are in this room. Is that understood Tony?"

"Yes Ma'am."

"Take off your pants and underwear, Tony."

"Yes Ma'am." He took off his pants and underwear

Ma'am sat down on the side of the bed and pointed to her lap. "Lay down across my lap." Slightly behind her to her right was a leather paddle.

Tony obediently laid down across her lap. Ma'am moved him slightly so he was positioned where she wanted him. He knew what was coming, so he braced himself.

Neither Ma'am nor Tony noticed as another person walk into the house next door. They thought it was an empty rental property, so never thought to close the drapes.

Ma'am started slowly. She spanked his bottom carefully.

Molly walked through the front door of the house next door. Molly was in her late 20's. She was the department manager for a team of engineers. She was very good at her job and always got results on time and under budget.

Molly had just ended an unsatisfying relationship of two years. He was a lovely man but just too vanilla for Molly's sexual tastes. He didn't like blowjobs, would never do down on her, and wouldn't do anything "different" because he considered it too kinky. Don't even think about spanking her which she desperately desired. It just wasn't going to work out, so she ended it, got a better paying job in another city and moved.

Molly had just rented this house, primarily because it was close to work and in a nice neighborhood. She walked upstairs to the bedrooms trying to figure out which bedroom she would pick as the master and where to put her bed and other furniture. The curtains were drawn, and there wasn't much light, so she she pulled the drapes slowly apart and was shocked at the scene before her. A mature woman was spanking a man laying across her lap on the bed. She could hear the skin-on-skin slaps from the house next door. Molly didn't pull the drapes any farther and was transfixed by the scene.

Ma'am kept spanking his bottom. First it got pink. The more and harder she spanked it started to get red. Then Ma'am picked up the paddle and got serious. Tony was doing fine until Ma'am started with the paddle. Tony's buttocks and upper thighs went from pink to red.

Although Molly was initially shocked, but she loved it. After watching awhile, she reached her right hand down to her crotch and started to rub. She wished it were her getting the spanking. Her focus was on the man's bottom and she didn't see Ronnie catch her watching. Ronnie finished spanking Tony, then stared across the gap between houses.

Molly no longer heard the spanking and looked up to see Ronnie staring at her. Ronnie had a slight smirk and motioned to Molly to come over. Molly looked away, but Ronnie walked up to the window and put her hands on her hips. "Hey!" That startled Molly. Then Ronnie motioned with her hand that Molly should come over. Ronnie raised her eyebrows and waited.

Molly didn't know what to do. She was embarrassed but couldn't resist Ronnie. Molly thought she would go next door, apologize and that would be the end of it. So she slowly walked next door.

Ronnie was at the door when Molly got there. Molly walked in and Ronnie shut the door behind her. "What's your name, and what are you doing next door?"

My name is Molly, and I just rented the house next door."

"You were watching us, weren't you?"

"Yes, but I didn't know what was happening and I stopped watching when I realized what was happening."

"Don't lie to me. You enjoyed it. You even started to masturbate. Don't you think peeping Tom's, or should I say peeping Jane's, need to be punished? Answer me, you naughty girl."

Molly didn't know what to do. She looked down but muttered "yes".

"Speak up girl."

"Yes, I watched. I need to be punished."

Ronnie led Molly to the upstairs bedroom. "You will call me Ma'am while we are in this room. Don't mind Tony. Do you understand?"

Molly saw Tony standing in the corner with his hands above his head clearly showing his very red bottom. "Yes, Ma'am."

Tony started to stuttter "uh, Ma'am..." Tony wanted to say he didn't know who this was, but Ronnie would have none of it. Ronnie said "shut up, Tony."

"Now Molly, take off your skirt and lay across my lap. Now!"

Molly started to protest but decided the sooner this started, the sooner it would be over. So she took off her skirt and laid across Ronnie's lap.

Ronnie held Molly firmly with her left hand on the small of her back. She leaned close to Molly's ear and said "Molly, don't forget, you are really the one in charge here. I know you want this, but you can stop it at any point. Just say the safe word 'red' and I will stop immediately. Say the safe word now to show you understand."

Molly quietly said "red".

"Now ask me to spank your bottom for being such a naughty girl."

"Please spank my bottom for being such a naughty girl."

"Where do you want me to spank you - on your bottom or your bare bottom?"

Molly hesitated a few seconds then whispered "my bare bottom."

"Speak up and use a complete sentence, Molly".

"Yes, Ma'am. Please spank my bare bottom hard."

Ronnie was a bit surprised. They hadn't discussed how hard to spank. Ronnie pulled Molly's panties down exposing her smooth white buttocks. Ronnie started lightly. Ronnie kept spanking Molly lightly for several minutes. Then she told Molly "get up and take the rest of your clothes off and get back over my lap. Naughty girls don't get to keep their clothes on while they are being punished." Molly did as ordered and returned to Ronnie's lap. The spanking started in earnest now and not lightly.

Molly started to feel the spanking now. It really hurt. "Oh, oh! Please stop, it hurts so much." Molly started to squirm on Ronnie's lap. She thought about using the safe word, but it felt too good. She had dreamed about being spanked but always thought it would be a man. In fact, she was getting turned on, and her pussy started getting wet. She didn't want it to stop. Ronnie reached down and felt Molly's nipple. It was enlarged and hard, so Ronnie squeezed it quite hard. Molly just squirmed a bit but said nothing.

Ronnie spanked Molly's bottom and upper thighs. She spanked harder and harder. She thought Molly would say "red" for sure. But she didn't. Molly started to cry.

Once Molly's bottom and upper thighs were bright red, Ronnie stopped. She gave Molly a moment to recover.

Once Molly stopped crying, she said "After Tony has been punished, I let him masturbate. Would you like to see Tony masturbate, or would you like him to fuck you. I guess he could even take your ass, if you like. Now Molly, what's it to be? I think the ass, don't you, Molly?"

Molly hesitated briefly and then whispered "my ass".

"You'll have to speak up, Molly, and ask Tony politely using a complete sentence."

"Tony, would you please fuck me in the ass?"

"Tony, get the lube and a condom."

Tony walked to the nightstand and got the lube and condom and handed them to Ronnie.

"Tony, take the rest of your clothes off. You look silly with a shirt on about to fuck this sweet girl in her ass."

Ronnie took the lube, put some on her finger, and spread Molly's ass cheeks. She spread more lube on Molly's ass, then pushed her finger into Molly's ass. Molly relaxed and let it happen. Ronnie then put a second finger in Molly's ass.

"Molly, put the condom on Tony and then lube him up."

Molly did as she was told.

Ronnie put two pillows at the end of the bed and positioned Molly on her back over the pillows. "Molly, you nasty slut, lift your legs so Tony has clear access."

While Molly and Tony were occupied, Ronnie had undressed. She lifted Molly's head and placed it gently on her lap. She began to fondle Molly's breasts. She began to rub then pinch Molly's nipples. Molly began to sigh and groan.

Ronnie rose to her knees, reached down and began to finger Molly's cunt paying attention to her clit. Molly gasped and moaned.

"Tony, kneel down and kiss Molly's cunt."

Tony knelt down and began to lick Molly's pussy. He kept at it until Molly started pushing up to meet his lips. Tony then took two fingers and slipped them into Molly's cunt. He finger fucked her until she came loudly screaming.

Ronnie rose up on her knees and placed her vagina over Molly's mouth and lowered her cunt to Molly's lips.

Tony stood and moved up against Molly's ass with his cock at her anus.

"Molly, grab Tony's hips and pull him toward you until his cock is at the entrance to your butt hole and let him in."

Tony slowly entered Molly's ass. After the head was in, he waited until Molly got used to it. At first, Molly gasped but soon smiled. This was just what she had dreamed of.

Tony started to slowly fuck her. Tony watched this and began to thrust into Molly's ass.

Molly thrashed about moaning and finally screamed out another climax.

Molly's orgasm triggered Tony's. He too had a strong orgasm, as did Ronnie.

Tony handed Ronnie a towel to clean up Molly. They waited awhile to let Molly recover from her experience.

Tony and Ronnie dressed. Ronnie looked at Molly and smiled. "Come downstairs when you are ready."

Molly got dressed and walked downstairs. Ronnie asked "Molly, would you like some water, beer or wine?"

"Yes Ma'am. May I have some water and then a little wine?"

"You needn't call me Ma'am any longer. We are no longer in the upstairs room. Call me Ronnie."

Tony got a glass of water with a little ice and a glass of wine for Molly. Molly drank all the water and then slowly started to sip the wine.

Ronnie smiled at Tony and said "that was the best experience so far! Thank you so much." She looked at Molly and said "I love your new protege. I didn't realize you would add someone to our scene. It was so very good. I left you a gift in an envelope on the table near the front door. Of course I added some to cover Molly. Again, thank you so much." She walked over and kissed first Tony and then Molly both fully on the lips. "I'll contact you to arrange another consulting session and experience. I'm thinking of buying another house, so will need your help making a decision. As for experience, I don't know what I will ask for next, but I definitely want it to include Molly. I'll let myself out. Bye, kids!"

Molly's mouth dropped and she just stared at Tony. "What happened here?"

"Well, Molly, it's a little complicated. Just be patient and I'll explain. One of my businesses is working with my clients to help them make decisions. Helping Ronnie decide on a new house is a good example - what location, what size, design details, should she should even buy another one. I don't make the decision; I just help them make an intelligent, informed decision. This is what they pay for, and what I report as income on my tax return.

"Some of my clients also like some kind of unusual experience after the formal consulting session. Usually this provides experiences to the rich and frustrated. It can be as simple as being an escort and taking them out for a lovely meal or more elaborate such as providing the experience you were just unknowingly part of. They don't pay directly for this experience, but they are free to leave a gift, totally at their discretion. I have a large and growing list of clientele. I've never advertised. It is only word of mouth, and they all sign a confidentiality agreement. They agree to never divulge any detail of what happens. It seems that you can be part of this if you'd like. I think the scene today touched you in a way that you wanted or needed. You can be a part of this, or I guess you could become a client. It's all up to you. I'm sure Ronnie will spread the word with her friends."

Molly was shocked. She didn't know what to think or say. She just started at Tony. "Can I have another glass of wine and think about it?"

"Of course. Why don't I fix us something to eat and we can talk. Ask me questions if you'd like. Oh, wait, let me get your share of her gift."

Tony went to the front hall and came back with an envelope full of cash. He took out two $100 bills and handed it to Molly. "That seems about right for this time. We'll discuss your share more if you decide to continue."

To be continued.