Spying on my Parents' Sexy Neighbor Pt. 02

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Blackmailer Doug, gets a surprise when Janet turns kinky.
8.8k words
4.75
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64

Part 2 of the 3 part series

Updated 06/09/2023
Created 07/04/2020
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Authors note: This is part two in the series. Original title Spying on my Parents Sexy Neighbor (Non-consent-reluctance). To better understand Doug and his past, I recommended you begin with part one of his journey.

After Lou and the fitness instructor, I had become Janet's personal toy. Whenever she wished she would call and I would rush over. Why? Because the sex was fantastic. She admitted it was because she couldn't get enough with Nick gone so often. Plus I was okay with the new arrangement we had. It made our old one feel like water under the bridge. I even started researching colleges for the next year, I figured better late than never, not as if 21 was old.

Janet and my mother, Lisa. Became good neighbors, Janet would come over and have coffee with my father Bill and my mother. My father always tried to invite her and Nick to their BBQ's or parties. A true salesman he always tried to sell something or find investors, I remember when they first moved in he didn't care. Until he discovered Nick made a lot of money and Janet owned a small business. When I was younger, I used to wish they would accept, so I could see Janet up close. Now he was just annoying.

Four months into our affair, everything seemed to even out, until Nick returned home one day. Janet flew out of the door and threw an arm full of clothes at him. She screamed at him in the driveway and rushed back inside. I remembered the tapes from eight months ago and my stomach turned. I just lost all the leverage I had. I went back to that moment I saw the service truck and wished it wasn't there.

I watched Nick pickup his clothes and run for the door. Desperate to hear, I open the window.

He stopped, banged on the door, and when I heard Janet's voice, I cringed.

"You've been fucking them all this time, prostitutes, strange fucking women, a whole fucking orgy. We are so done, I spoke with a lawyer, and he said I can get everything." She screamed as if to alert the entire community.

After the door slammed shut, Nick said nothing, he turnaround and got back into his car. Nick must have had his own blackmailer, or a whistleblower.

Twenty minutes later Janet messaged me. 'I need a hard fucking, 1 hour.'

Since then, things changed. Not wanting to piss her off, I now heed her beck and call as an obedient slave.

A week passed since that painful night with no word from her. But, my mother and father had returned home. She knew those times were off limits. On the last night they were in town my mother cleaned the house and my father went out to get refreshments. At 7:30 on the dot, the doorbell rang. My father, Bill rushed down the stairs to answer.

My father dressed up nice, dress pants and a polo shirt. My mother wore a knee high sun dress, low cut to where I could see her cleavage, and a beige lacy bra. She put her hair up, put on makeup and even wore high heels.

Lately she had been taking her figure more serious and asked me for fitness tips. The time she spent in our home gym increased three fold. She said she wanted to look good on sales trips. An underlying complained was about the new girls younger ages and how they were making huge sales. But I think it also came from hanging out with Janet more often.

To my surprise, Janet stood at the door. She wore tight blue jeans, a black tank top, and many pieces of jewellery. When my father and mother greeted her, she kissed Lisa on the cheek and Bill she gave a hug. When they turned she looked up at me and gave me a wink.

It was always our little secret when she showed up. One time when my mother and her planned to have a drink, my mother ran out to get mix. Janet and I fucked on my bed. She cleaned up before my mother returned and continued to have a drink with her on her back deck as if nothing happened. Since then, Janet has been much more flirtatious with me in from my parents.

She walked past me, gave me a smile and patted me on the stomach. "Oh my, your boy has been working out, Lisa I should hire him to come clean my pool now that I'm single."

My mother laughed it off and grabbed three wine glasses.

I couldn't stay that night, part of me wanted to, but I had a mini crisis. To be exact, a $3200 mini crisis. I had to meet a client and settle a dispute over a potential copyright issue. My employee unknowingly used a photograph on a web page and now she was being sued, who was now suing me.

Brandy was a single mother, she was part Spanish and part French. Which gave her an exotic appearance from her tan to her eyes even in her voice when she spoke. I felt responsible to take care of her. She worked a job, came home at night and made jewelry to sell after hours. With my help on her online store, she was selling more jewelry than before. But it helped Brandy was a natural-born saleswoman. Did I mention she was attractive? In her early thirties, long black hair, tanned skin, and large black eyes, yes? Well, it's worth noting a second time. She had a smile that could put you at ease and with it she negotiated 25% off her monthly fee.

That night she greeted me at the door, with a tight t-shirt and tight pair of jeans. Even though she was mad, she gave me that amazing smile. She poured us a coffee and each time she bent over, I could see down her shirt. She wore a black bra, lace trim, and kept her hair back from her neck. As a result, by the end of the night I paid the $3200, I remain the website admin, and I now only charge her $100 a month for her continued business.

To be honest, I thought I would get laid. But, I just got a kiss and a wink at the door with a thank you. Which was better than nothing. Brandy really was a pleasant woman and to be honest, I had my hands full with Janet.

When I returned home I had hoped for a nice quiet night. Crack a soda, do some last-minute changes on the brothel game I made, and release it to the public as a web game. When I entered the house, my father greeted me with a smile.

"Hey, Doug, I didn't think you'd be home tonight." He said in a loud voice.

"Why? I didn't have much to do, I just had to take care are a few things for client."

His eyes grew wide, and for a second he wasn't sure what to say. "Oh, I thought when you said Brandy you were talking about a girl."

"I was, she's a client of mine, it's actually the jewelry site that I work on."

My mother came from the living room and gave me a smile and brushed her hair behind her ears. "Hi Doug, we're just finishing up with Janet, would you like to join us with a last drink?"

She had removed her sandals and my father had removed his glasses, which was uncommon because he couldn't see much without them. Janet entered the room and leaned against the door.

She waved me over. "Of course he would, come on, you can sit with me."

When I went past her, she hooked her arm in mine and led me to the couch.

The three of them laughed and gossiped about other people in the community. Maybe that's just people were. 'This neighbor did that, that neighbor wore those oh-my, and Janet is fucking Lisa's boy, you know the one who runs everywhere.'

Rachel, my half-sister was a star athlete, grade A student and never had a problem finding a date. She hated this community and its people, couldn't wait to get out. I thought she was being weird, but back then no one seemed to take notice of me. Now I wondered what they said.

I used to fantasize over my sisters friends. All of them were the pretty girls back in the day, most still are. The rich girls who stayed in the community and never went to school, like me.

I watched Janet and my mother Lisa banter back and forth. Once, many years ago I caught my mother and father having sex. Repulsed and turned on, I couldn't take my eyes off her. How the muscles in her back moved and rolled while she gyrated on top of Bill.

After I saw her from behind I used the memory to imagine Janet riding me. Now here she was laughing and flirting, being best of friends with my mother. Unknown to my mother, this woman was fucking her 20-year-old son who had blackmailed her.

As per normal, before Janet took her leave my mother invited her to a party. Like usual, Janet politely refused. I had to give it to my parents for being the persistent type, but I guess that's how they both made their money.

THE FREE AND EVER KINKIER SINGLE JANET

After Nick left, I played escort to out-of-town dance clubs, dinner or nights out. This time Janet wanted to attend a beauty party and wanted me as her upgraded "boy toy". I tried to find a way out, because this was in the city. But she quickly reminded me, I owe her. See, over the past few months my little video camera got me in more trouble than her.

I've also been learning she's not the dumb bimbo my parents first thought she was. Over the past few months, she was proving to be rather shrewd. Not only that but frisky, I'm pretty sure every first I'll have, will be with her. Recently she's been asking me if I find random men at parties handsome or not. Which has been concerning.

After a hot, muggy day with ominous clouds in the distance, night arrived and I got dressed in a black dress shirt, charcoal pants, and dress shoes. These were the clothes she picked out for me.

When I picked her up, she greeted me in a short black cocktail dress, high heels, a small purse and a little diamond necklace. Still, after all these months when I saw her, my heart skipped. She gave me a giant smile, whisked the hair from her face and reached her arm out to me.

"You can drive." She handed me the keys and escorted me to the car. It was a snappy little Audi, silver with black leather interior. She won it off of Nick in the divorce. In fact, she pretty well took everything, their house, part of his monthly paycheck, she even kept his cufflinks collection, worth half a million.

She navigated me outside of the city to an impressive three story giant mansion built on 10 acres. Fenced in with stone walls and barred off with iron spikes on top. The only thing missing was a fountain, massive trees, and a gardener trimming the weeds. But if it was daytime, I imagine he would have been there.

"Oh, I almost forgot you have to pretend you're Lou tonight." She said.

"I have to pretend I'm Lou, as in Lou your other guy?" I said.

"No just Lou, they just knew him by name, it's what's on the invitation." She said.

"Names please" the intercom said with a feminine voice.

She leaned over me and called back. "Mr. and Mrs. Black."

"Great, we're glad you could make it, we've heard a lot about you. The garage is full but pull around the back." The woman's voice said.

I stared at her with wide eyes and shook my head, begging for an explanation.

She pointed to the gate and said. "You'll miss the gate."

The gate opened, and I pulled into the driveway. There were five other vehicles in the back and a large a garage.

Janet reached into her purse, pulled out a card and some black cloth.

"Okay, we have some rules, the first one is no fighting and the men wear these."

I held up the thin cloth to reveal a stretchy black hood. She reached into the back seat and pulled out a masquerade mask for herself.

"What the hell are we doing?" I asked.

"Well, this is something Lou, and I was going to try, I never wanted to, but now I'm intrigued. Oh, and we're going to have sex with other people tonight. It's kind of a mandatory plus one."

"We're at a sex party! What happened to the Tupperware, makeup or other multilevel marketing house parties? Oh my god, is this why you've been asking me about other men?" I half shouted.

"What kind of party did you think we were going to?" she said.

We stared at each other, both with blank faces. She amazed me with her question, the surprise party, and her look of blank innocence to the point that I didn't know what more to say. I glanced at the mansion and shook my head in disbelief. "Well, not one of these." I said.

The more I stared at the mansion and the people inside, the more intrigued I also grew. Janet was a beautiful woman and her patrons were all wealthy, attractive women. This started to not seem like a terrible idea and started to look forward to it.

She touched my crotch and squeezed me through the pants. "Awhile back one of my regular customers used to invite me and Nick to spice up our marriage. I confessed to her about Lou and her eyes lit up. But she never met him, she doesn't know who he was, and I never told her about you. Now I'm curious about fucking another woman's husbands with her permission. So that's where you come in." She leaned in close, opened her mouth and kissed me on the lips.

I touch the tip of her tongue with mine and she welcomed me in. Our tongues explored one another and when we parted ways, she put her mask on and smiled at me.

"Don't worry, we'll probably be the average looking couple if my client is any hint." She said.

I pulled my mask over my head and escorted her to the backdoor. A slender, tall redheaded woman welcomed us. She wore a tight red dress, red stilettos and had a red-feathered mask. She was in her mid-forties, but still just as attractive as Janet.

Her voice was the same as the intercoms. "Welcome Black. I am Red" She said. She held the door open and let us in. As I passed by her, she slid her fingers across my chest. "I think I may have to negotiate for this one tonight." She stopped us in the entranceway. "Did purple explain the rules?"

Janet hung on to my arm and leaned forward with a big smile "Oh yes she did."

"Ah, I'm a little hazy on how this works?" I said.

Red put her hands together and smiled. "Okay, well first this party is for open couples only, a member must invite you, and that was Purple. No fighting, no hard feelings, take it home, discuss it with your significant other. But do not do it here, it's all in the manual. We meet here once a month." She smiled and took my arms. "Before we go in, I'd like to add, when I saw your pictures I knew you two were a perfect fit." She glanced downwards towards my belt and smiled. "But also in description. So last month it was the men's turn to negotiate. This month it's the women's turn."

"Negotiate?" I said.

"Yes, we play different games each month but this one's our favorite. We exchange favors, money, and once a car. In my husband's defense, he really wanted to sleep with that woman."

My eyes grew wide and I'm sure my mouth hung open. What the hell kind of party did Janet bring me to?

I looked over at her and she gave me a smile and a wink. "I told you it would be fun."

It suddenly felt fitting to hear thunder rumble in the distance. What could go wrong? I played games like this, huge stone mansion, out of town, strange unknown group. Yup sounded like a perfect place to get sacrificed.

Red turned her attention back to us, "Sounds like it'll be an interesting night. Tonight the men go to the rooms, don't worry there's a bottle of wine. There you'll wait until you hear a knock. You can also watch all the action on a tablet and a camera so you can see what your partner is doing. Each lady will have a colored key. Oh except for pink, their a lesbian couple and they request only one room so if you negotiate with pink all four of you will be in the room. Do not use names, even if you know them. Once we have our masks on we are a color, but you may remove the mask once your in your room. There are condoms in each room and they are mandatory. We want to keep our little group healthy and safe."

I nodded my head.

"Oh, and foursomes are open after hours and only on party nights," Red said.

Janet squeezed my arm tight, "That's the part I was hoping for, I always wanted to see two men."

"Maybe we can talk in the grand room then, my husbands also open to such meetings." Red gave Janet a devious smile. She looked at me and motioned towards the side door. "The rooms are that way, Mrs. Black if you will accompany me I will introduce you to the other ladies."

Janet smiled, slid her arm from mine and took Reds. She looked back and waved at me before disappearing through a large archway.

Part of me wanted to run, but I was afraid this weird cult would hunt me down in the rain like a horror movie. The hallway reminded me of an old haunted house. It had hardwood flooring with a red carpet runner, candle lamps that barely lit the floor and large wooden trim.

Pink was the first room, I couldn't help but hope Janet would pick them. In total, there were seven colors. Towards the end, I found the door with a black tag on the knob.

The room was no less luxurious than the rest of the house. It had hardwood flooring, a giant carpet, a king-size bed, and a drink tray with two glasses of wine and a bottle. On a bedside table was a tablet. I turn the lights on, but the room remained dark. The only light in the room was a faint glow from the tablet. I sat down and looked at the screen. It was a small 9 inch tablet that I could barely make out.

There were eight women in the giant room, each dressed in the colors of their mask. There was Red, the hostess and Janet in black. The others were purple, yellow, blue, pink, white, grey and green. Each of them wore a different dress, most wore short cocktail dresses, but one lady wore a white kimono style dress. Pink was the only one in a miniskirt and a pink leather jacket. I zoomed in on her out of curiosity, she was young, pretty, and looked like she had blue hair.

The other women were mostly middle-aged, but all seemed attractive, nothing like what you would see in some homemade videos on the Internet. They carried themselves tall and stood confident like wealthy women. Each had respectable breasts sizes, but I imagine most were fake, and no bulging waist lines.

I zoomed in on purple, the mystery woman whom I figured invited Janet. She had wide hips and larger breasts. Wore an elegant mask made of purple feathers, which wrapped around the back of her head and fanned out backwards. Her purple high strapped heels came up to her knees like a Greek goddess. She was the 2nd of only two women who wore a dress past their knees, but it had a long slit up her right leg as high as her hip which gave tantalizing glimpses of her thick long legs.

Soon after Janet appeared she left pinks side and greeted Janet. Poor bastard I thought.

The grand room had no floors above it, instead it was open all the way to the 3rd floor where it turned to a vaulted ceiling that carried on into a triangular wall of glass. In the middle of the glass wall an enormous stone fireplace with a chimney that rose to the peak. Three black leather couches sat around a square heavy wooden coffee table. If this was the living room, I wanted to see the rest of the house.

In the corner was a wheel, like you'd see on a game show, I tried to zoom in but I couldn't read what they wrote on it. I took a sip of the wine which tasted sweet and continued to admire the women.

The women drank, nibbled at small finger foods and chatted among each other. I looked around, but all I had was wine. This continued for 30 minutes. The tablet had no audio and a very limited zoom. I guess for the viewer to build their imagination. Janet browsed the room, chit chatted with all the women but always returned to purple. Purple also did the same thing, so I was sure I knew who my partner would be tonight.

At exactly 10:30 P.M, Red raised her arms up and all the women turned and looked at her. She said something to them and most of them nodded their heads and looked at the women beside them. Janet and purple was close together. I had become entranced with how purple swayed her hips, flicked her fake feathers from her face and walked about the room. She was elegant, pretty, mature and had more curves than the other women.

Red spun the wheel and all the women looked on. When it stopped spinning the women looked at one another and smiled. Some laughed, some rolled their eyes, and two clapped. Purple put her hand on blacks arm and almost looked like she apologized.