Halloween Moms and Daughters

If you are new to my stories, I recommend that you read Neighborhood Moms and Daughters and then More Neighborhood Moms and Daughters prior to getting into this story. It will help you with the characters and their motivations.

Jordan’s activity is discovered by her mother leading to confrontation with Ray. It is resolved and leads Ray to a unique Halloween party with a servant auction.

There is less focus on some of the main characters from my first two stories. I will return to them in my next story. If you ignore the references to the old characters, you can read this more as a stand-alone story.

Many thanks to kenjisato who is my editor and made this better. This is my first story to have a total edit and it made an enormous difference. Kenjisato did quick work.

This is my entry into the 2021 Literotica Halloween story contest. Please vote, favorite, and/or follow me. I appreciate comments and feedback.

All characters are 18 years of age or older.

Chapter 1: Mom finds out what daughters have been up to.

I was back at work after a wild night of sex with Sarah, her sister Jordan, and Samantha. I was grinding through meetings with my sales and marketing teams. We were launching a new product next week, that would make us a much larger player in the aerospace industry. As head of sales, I was leading the charge with customers. I couldn’t take phone calls, but had received texts from all the girls that morning. During lunch, I caught up.

Samantha, my close friend Teena’s daughter, was heading back home to better understand what was happening with her parents.

Sarah, a model, and the older sister to Jordan, was flying to a photo shoot in New York. She was now shooting major fashion magazine covers and was on a short list to model for Victoria’s Secret. The image in my mind was of me tit fucking her and blowing my load all over her face and mouth. I don’t think I will see that on a magazine cover any time soon.

Jordan, the younger sister, had nothing going on today and texted me a lewd picture of herself with descriptions of what she wanted to do.

I had to shut down Jordan as it was a work phone, and I could lose my job over the image she sent. She sent a pouty face emoji and asked when she might see me again. I said that this week, I was traveling to meet customers and wouldn’t be back until next week. More pouty face emojis came back at me.

My other personal conversation today was with Teena who was having difficult times getting her husband, Rick, to accept the changes that she wanted. He was in denial of his own shortcomings and had not accepted Teena’s desire to leave the relationship. We were both worried about what he might do. If things got too hot in the house, she was open to stay with her friend, Denise.

I had also contracted with a security specialist, Jeff, to get information on Rick. Jeff was hopeful that he would have information within a week.

I was leaving for Seattle tomorrow. I left work early, grabbed dinner on the way home. Once home, I cleaned up from the night before with clean sheets and promptly fell asleep by 6:00pm, as last night had finally taken its toll.

At around 9:00pm, I woke up to knocking at my door, along with repeated ringing of the doorbell. I groggily got out of bed and headed downstairs in the shorts I had fallen asleep in.

I opened the door to be confronted by Marie, Sarah’s and Jordan’s mother, who was looking angry, holding onto Jordan’s arm, who had her head down. Marie stormed into the house with her diminutive daughter in tow without being invited in.

My stomach was doing cartwheels as I had done many kinky acts with her daughters the night before.

After entering, she turned in the entryway and said, “Ray, I know we don’t know each other well. Marnie, your daughter, was a good friend of Sarah’s until they went to college a couple of years ago. I know that you lost your wife recently and we are all sorry for your loss.”

I nodded in agreement, knowing this was not the reason for their visit.

Marie pushed on with one hand on her hip, “Samantha was with our girls last night. I could hear that they were up to something, but wrote it off to girls just having fun. I did, however, do a bit of digging today after I dropped Sarah at the airport. I grabbed Jordan’s phone at dinner and was horrified to see that they had all come here last night; and that there was clearly some sexual activity going on. What do you have to say for yourself?”

I was quickly waking up and getting my wits about me. Jordan still had her head down, so there was no indication of what Marie knew about the details. I went with a minimalist answer to see if she would reveal more information.

“Marie, Sarah, and Samantha did come over here last night and eventually, so did Jordan. Nothing illegal happened and they all did this without my encouragement.”

Marie stormed, “What exactly happened last night? Jordan sent some provocative texts today. She won’t say anything about last night, but I can read between the lines.”

Marie knew none of the details from last night and only had Jordan’s text messages from today. I racked my brain to remember what they had said. I remembered that she had repeatedly talked about my big cock and that she wanted it in all her holes. Jordan had also sent a nude selfie with a big dildo in her mouth. Just thinking about that lewd shot made my cock stir.

I was gaining some confidence and responded after thinking it through, stating, “What happened last night is between me and the consenting adults that were there.”

“Jordan lives under my roof and barely qualifies as an adult. We have had many challenges with her and don’t need neighbors corrupting her.”

I went back at her and said, “You are treating her like a child; it will only lead to more resentment and having her lash out with bad behavior. Look at how you are treating her now–dragging her over here by the arm and talking about her like she isn’t even here. Have some respect for her decisions and actions and maybe start a conversation–instead of accusing, spying, and demanding.”

At this, Marie took a step back and released Jordan’s arm. She wasn’t used to being confronted, and was now on shaky ground.

Jordan rubbed her arm where her mom had gripped it and finally looked up. She looked at me with the hint of a smile. I hadn’t betrayed her trust.

Marie said, “Okay, mister smarty pants. What would you do if you found similar messages and THAT picture on your daughter’s phone to a much older man?”

“First, I would never betray my daughter’s trust by snooping on her phone,” I said. “Secondly, if I had become aware of that, it would drive an adult two-way conversation with her. I wouldn’t storm over here and accuse a third party, at least not without talking to her first.”

Marie calmed down and took a big breath and looked at Jordan and asked, “So let’s say Ray is right, what do you have to say for yourself?”

Jordan was silent for what seemed like an eternity as she was clearly thinking. I was impressed by this. In pressure situations, it is always better to collect your thoughts before you speak.

Jordan finally looked at her mom and said, “Mom, you know that I have been having sex. Hell, you took me to your doctor to ensure that I am on birth control. I want a healthier sex life than dad and you have and want to get some experience–so I know what to look for in a partner. I want to make better choices; and to do so… I need to explore.

“I followed Samantha and Sarah over here last night, as I had heard what they wanted to do with Ray. We did some awesome things together. I can assure you that through all of it, Ray was a perfect gentleman and didn’t coerce any of us mentally or physically. You saw what I sent him, and you saw his response to stop it. Why are you attacking him?”

Marie was now looking self-conscious. She said, “I know you don’t have the best role models at home. I try to do my best, but I can only do so much by myself. Your father is always away and thinks of you as a child. Hell, he treats me like a child as well.”

Marie looked at me and said, “I am sorry that I confronted you like this, Ray. I saw those texts about Jordan offering herself and talking about your cock, and just went… ballistic.”

Jordan put her hand on her mother’s shoulder and said, “Mom, this might be the best conversation we have ever had. You can always ask me about anything. Just don’t let your temper get in the way of you listening. You have always had our best interests at heart. It just shows up in strange ways sometimes.”

Marie now had a tear coming down her cheek as she looked at her daughter in a new light. She smiled and then joked, “I will try honey, but it was hard to read you offering yourself to someone.”

Jordan responded, “If you experienced what I did last night, you would be in line offering the same.”

“Oh come on,” Marie responded sheepishly, “how would you know what is actually good in that department?”

“Don’t take my word for it, your eldest daughter is lusted after by most of the straight male population that she encounters.” Jordan continued, “She has sampled much more than I have, and if Ray sent her a text right now, she would leave her cover shoot and get on a plane back here to experience his love.”

Marie gave me a cockeyed look and asked, “Ray, what is your magic? I see you are in great shape and clearly you are a good listener. Do you have a magic wand in those shorts?”

It was now my turn to be at a loss for words.

Jordan spoke up as she moved to my side, “Mom, you have no idea. He has a cock that will fill you up to overflowing. He has stamina, creativity, and confidence to deliver you the best sex ever.”

I blushed a bit at Jordan’s assertion. She moved her hand which was close to my side and gave my cock a rub through my shorts.

Marie was wide-eyed. First, at her daughter’s bold actions; and then, at the outline of my cock.

Jordan kept rubbing and Marie’s jaw dropped as the head of my cock poked out the right leg of my shorts.

Marie exclaimed, “You have to be fucking kidding! That can’t be real.”

“It is SO real,” Jordan said, as she then turned towards me and pulled my shorts down to my knees. Jordan grasped me with her hand as she bent over to put the head of my cock in her mouth. She gave me a couple of pumps and then lifted her head to look at her mother.

“Can you blame me, mom? Look at this. It is much bigger than any toy you have in your pleasure box, and puts almost all men to shame.”

Marie was shocked, but then slowly… a look of lust started to penetrate her visage as she watched her daughter suck me.

“Why don’t you admit your desire and get over here to sample this yourself,” Jordan suggested.

Marie said, “Oh, this is so wrong… but that is so big.”

Marie was unsure, but I could see that familiar look of lust consuming her face.

I reached out and put a hand on her shoulder and guided her in front of me. I pushed down gently, and she descended to her knees as Jordan was still grasping me from the side and now pointing my engorged cock at her mother’s face.

Jordan put a hand on the back of her mother’s head and started to apply a bit of pressure.

Marie said, “This is so wro–”

At that moment, Jordan quickly pushed her mother’s head; Marie was cut short as she opened her mouth to accept my cock.

Marie gave out an accepting moan, as she got used to the size of my cock head in her mouth; and she started to use her tongue.

Jordan exclaimed, “Mom, look at you! You were mad at me for being a cock slut, and here you are on your knees servicing your neighbor. Now, you understand.”

Jordan went behind her mother, reached around, and started unbuttoning her blouse. Marie was a few years older than me, but still in great shape. She had a slim body and probably C cup breasts which would be soon exposed. She had alabaster skin, long and full raven black hair, and a signature small mole on her upper lip.

When Jordan had finished unbuttoning her blouse, Marie pulled off of my cock and looked up while she shrugged her blouse off of her shoulders. “Ray, this is amazing. I want it all. Can we move to your bed, as my knees are killing me.”

I smiled understanding her pain. I reached down and helped her up, giving her a kiss as she stood close to me.

Jordan had stripped down to her panties while her mom was rising and letting her blouse fall to the floor. Marie reached behind and unsnapped her bra which quickly joined her blouse. I reached out to caress one breast.

At the same time, Jordan reached around to grasp the other and tweak her nipple.

Marie, who had been focused on me gave a little start with the tweak and then a look of surprise that her daughter was fondling her breast. “Jordan, I have crossed a line for Ray,” she said, “but, you are my daughter.”

Jordan smiled, saying, “Mom, you have only started crossing lines. Get used to it. You aren’t just servicing Ray tonight.”

Anger flashed in Marie’s eyes–she was about to say something to Jordan that she would regret.

I interrupted, “Marie, let that go. We are going upstairs, and we will satisfy you in many ways. Give yourself over, or it won’t work. Your daughter can be a handful and hard to manage; but, she is right in wanting to explore. She enabled what we are about to do, and you need to respect her instincts.”

Marie deflated and grabbed both our hands and moved to the stairs.

We reached the bedroom and Jordan asserted herself again as she unzipped her mom’s skirt and said, “Mom, since you are bit hesitant, I am going to lead. Drop the underwear and lay on the bed with your ass at the edge.”

Marie complied.

Jordan dropped her panties, while I threw my shorts in a corner.

Jordan was next to her mom and got her to pull up her legs, which she held.

I approached from the foot of the bed, knelt down, and started kissing Marie’s thighs and then moving in to give her a quick lick up her slit to her clit.

As I moved back down, Jordan reached in to rub her mom’s clit while I inserted my tongue in her snatch. This sent Marie into orgasm as I felt her contract and then a flow of girl cum flooded my mouth.

I stood up and Jordan pulled her mom’s legs back further to expose her bottom.

Marie was panting as I lined up my cock to penetrate her sopping pussy. She told me, “Put that stick in me all the way, and don’t stop.”

I pushed in quickly and hit her cervix which started another orgasm. I started stroking in and out and thought I should show Marie some of Jordan’s tricks. I pulled out completely and Jordan dove down on my cock to suck it deep before I put it back into Marie.

Marie said, “Jordan, that is bad.”

Jordan said, “Mom, you haven’t seen anything yet. Wait until he pulls his cock out of your ass and I do the same thing. When he cums, he will either pull out to do it in my mouth, or… I will lick his sperm out of your pussy, and then feed you his cum with my mouth.”

Marie was panting. “Eww, Jordan, that is so… nasty.”

“Don’t knock it until you try it, mom; which is probably going to be later tonight.”

Marie may have pretended to be disgusted, but when Jordan implied that she would be doing it, it sent her off again.

Feeling that Marie was going to comply also sent me over the edge, and sent my load into Marie’s cunt.

Jordan had moved around to stand next to me. As I pulled out of Marie, Jordan pounced on my cock and quickly cleaned me. She then pushed me aside so she could dine on her mother’s cream pie.

Marie had a worried look on her face that melted as soon as Jordan started licking her. She gasped and then came again sending a combination of girl cum and sperm into her daughter’s mouth.

Jordan rose up with her lips pursed and approached her mother.

Marie had her lips closed and then said, “I have never eaten cum before.” Jordan nodded, pushed a finger in her mom’s mouth, and gently pulled down her jaw to open her wide.

Marie relented, and opened up to accept the combination of sperm and pussy juice into her mouth.

After Jordan finished her deposit, she could see her mother struggling with a mouthful of fluids and said to her, “Swallow the load, mom, like the cumslut I know you are. You think it’s repulsive, but your body said otherwise when I talked about it.”

With that, Marie gulped it down and exclaimed, “Wow! Jordan, what are you going to make me do next?”

Jordan said, “Don’t deny that you love this, mom. My guess is we’re going to revive Ray and he will likely want to fuck our asses. But, before we get to that… and to help excite him, I think you need to cross another line…” she said with a smile.

Jordan moved further up her mother and straddled her chest, pinning her arms down.

Marie was now looking directly into her daughter’s shaved pussy.

Jordan started fingering her clit and then put a finger in her pussy. After she withdrew the finger, she put it into her mom’s mouth.

Marie knew what was coming next, as Jordan moved her pussy onto her mother’s mouth.

Jordan’s assessment of what I wanted to do next was correct. I wasn’t sure which ass I should take, however. I grabbed the lube and a dildo out of the nightstand and applied lube to the dildo as I returned to the bed.

Jordan was encouraging her mom by saying, “I bet that this is the first pussy you have sucked. Get that tongue all the way in and then go to my clit.”

I approached Jordan from the side and held the lubricated dildo up to her and glanced to her backside. She nodded. I grasped the dildo in one hand and used the other to spread lube in the crack of her ass. As I started fingering her ass, I could feel Marie’s tongue in her vagina.

I pulled my hand out and then moved the dildo to Jordan’s ass. She arched her back as I plunged it into her. I grabbed Marie’s hand to get her to manage the dildo.

Marie was tentative, thrusting into Jordan at first, until Jordan reached back and grasped her mother’s hand forcing a faster pace.

I left Jordan to ride her mother’s face. I lifted Marie’s legs and put lube on two of my fingers and started greasing her asshole, first probing it with one finger, and then two. Jordan had indicated that her mother’s toy collection included butt plugs, so I figured that this was something she would be into.

Jordan announced that she was cumming. “Here comes my juice, mom!” She started shaking and yelling and she was grinding on her mom’s face while the dildo was still lodged in her ass.

Watching Jordan aggressively use her mother to get off was very erotic and had me hard again.

After Jordan finished, she swung off of Marie’s face which was glistening with Jordan’s juice.

Marie had a look of lust on her face and licked her lips after eating her first pussy. She yelped as I pushed two fingers into her ass up to the second knuckle.

Jordan commented, “He is getting you ready to take that huge fuckstick up your poop chute. He did me for the first time yesterday. Get ready to have your world rocked.”

Jordan then pulled the dildo out of her ass and brought it to Marie’s mouth. She now opened willingly to suck it.

I guided Marie to roll over and move up on the bed on all fours. As I approached Marie, Jordan moved to kneel beside her mom and then leaned over her ass and opened her mouth.

I stroked into Jordan’s mouth for a couple of strokes and then pulled out to put lube on my cock. Jordan guided my cock to her mother’s asshole. She then spread her mother’s cheeks as I pushed in.

Marie yelled out as my cock head passed her anal ring saying, “Oh my god, that feels huge!”

I kept pushing in and Marie was moaning and panting. I went slow and finally bottomed out in her bottom.

Jordan said, “Mom, that looks so awesome. Ray’s cock is spreading you in an obscene way, and he is all the way in.”

I pulled back and steadily increased my pace for about five strokes which drove Marie to an orgasm. I then pulled out to feed Jordan and demonstrate to Marie something that was a turn-on for me. I steadily increased my pace and was slamming into Marie who was moaning again.

Marie orgasmed again and this sent me over the edge.

Jordan had her head at the top of her mom’s ass crack with her mouth open as a target.

I pulled out and shot my first stream which landed across her face and mouth. I then moved forward, and she put her lips around my head to take the rest of my semen directly in her mouth. After I finished, she gulped it down.

Marie had rolled over to watch her daughter do the dirty deed. She sighed and said, “That was fucking amazing, literally. In all my years, I have never been fucked like that. I had five orgasms and that is four more than I have ever had in one evening. Jordan, I get you now… and am sorry to have beaten you up over this.”

Jordan said, “Mom, what a night! Welcome to your new life.”

“I have heard about this life and know of a few people who live a wild life. I always stuck with my boring frigid existence,” Marie added.

While I knew Marie through my and her kids, we had never interacted socially. She was in a higher-end social crowd; but, it seemed that the lonely wife issue existed there, as well. I asked, “Who are the wild side people?”

Marie said, “They are some people I knew before getting married. They have some wild parties. I will make a call and maybe we could all join in something fun.”

Chapter 2: Prepping for the party.

I left for Seattle the next day and worked there with customers for the week.

Marie had been talking to her old friends about their free lifestyle. Marie came from old money and had always traveled in different circles, and that the circles her old friends were in, were even higher up the food chain. She had a lunch tomorrow with Sybil, who was the ringleader of these wild parties; and she would let me know the details.

Marie texted me the next day and said she had lunch with Sybil, and she had welcomed Marie back into her friend circle without issue. Sybil had heard about Sarah and her modeling success and was looking forward to meeting her. She understood that Marie wanted some new experiences and would need discretion. That wasn’t an issue as all of Sybil’s friends had too much to lose if knowledge of their activities ever became public. Marie wanted me to send her a dick pic to share discreetly with Sybil. This would apparently help us getting status at their next party which was the annual Halloween auction.

I sent the pic that night from an anonymous email to Marie.

The next day, Marie sent me an invite to a Halloween party. The theme of the party was ‘Master and Servant’. People attending had to decide who was going to be the master and then come with servants; costumes and role playing would be encouraged. It indicated that after opening festivities, an auction of servants would occur. It sounded intriguing to see how the rich played.

Marie said that we would be a big hit at the party. Beyond the pic which was ogled by Sybil, she had ensured that Sarah and Jordan would join us. We would be the fresh meat at this party. Sybil indicated that there would be a few mother/daughter pairs coming to the party.

We formed a private group chat to figure out costumes and roles for the party which was two weeks away.

We talked about roles for the party and all the women demanded that I be the master. They all wanted to be servants, even Jordan who had turned a new leaf with better behavior. Amongst the girls, there was some hierarchy as well, with Sarah being most senior, Jordan being second, and Marie being the bottom. I was surprised with Marie’s desire to be the bottom girl, but she thought it would help liberate her.

On a private message, I asked Marie about her husband, Dave.

She said that they were largely estranged and that he was out of town on business meetings over that weekend. She added that the girls and her were tight and that they were okay with it all.

Costume ideas for the four of us started bubbling up.

Sarah thought we could dress in 1950s diner staff attire with me as manager, and the women in waitress attire. She thought that they could wear pull up stockings and very short skirts; I would be in cook’s attire.

Marie wanted a prehistoric theme with me as a dominant cave man and them as the family. She thought the costumes could be quite revealing with loincloths and cut-outs.

Jordan wanted to go with a high school theme. Sarah as a cheerleader, Marie as a librarian, me as a strict principal, and her in Catholic schoolgirl attire.

Just reading through the possibilities was getting me excited. I thought the school theme would be fun for the costume element and that the cave man theme was strong, based on revealing clothing.

Marie had shared the ideas with Sybil and her recommendation was the school theme as she knew of at least one other prehistoric-themed couple. Marie said that Sybil was disappointed that I wouldn’t be a servant for the party, as apparently I was someone she would have bid on.

As I was tied up with work, Marie led most of the organization of costumes. Sarah’s was easy as she had been a cheerleader. Marie made her shirt into a revealing crop top to showcase her midriff and breasts. Jordan bought an actual uniform with a white blouse and short plaid skirt. She bought all the clothes two sizes too small and was going to accent this with white pull up stockings, a garter belt, and no underwear. Marie had organized librarian glasses, a short pencil skirt, and black pull up stockings for herself. I was going to use an old black suit that was now a tight fit as I had muscled up over the past year. To complete the image, I was getting some wire rimmed spectacles and would slick back my hair.

The party would start at 6:00pm on the Saturday. We all agreed to meet at my place to get into costume at 4:00pm. I suggested that we all behave while getting ready for the party, to avoid tiring ourselves out before the main event. This was greeted by more pouty face emojis from the girls.

Work was hectic, but was interspersed with funny text and pics, as the costume pieces came together.

I got back from Seattle and quickly got caught up with Teena. There was still no resolution with Rick. They were in a holding pattern as she looked at getting legal help. I let Denise, Teena, and Samantha know about the Halloween plan. They were jealous and wished they could come, but other commitments precluded this.

The Saturday of the party arrived. I cleaned the house, made some appetizers, and did a bit of minor Halloween decorating to help set the mood. The women all arrived with bags and we started to get dressed.

Marie was stunning in a low-cut silk blouse that showed some lacy lingerie and cleavage. Her hair was in a high, tight bun accentuating her pure white skin and librarian glasses. Her skirt was obscenely short and her thigh high, black stockings were great. She had a copy of ‘Kama Sutra’ as a book to carry as an accessory.

Jordan put on her too small schoolgirl outfit. She wore no bra and the shirt stretched across her chest and had only three buttons done up. She wore pigtails with ribbons in her hair and had the white stockings and garter combo that she had planned.

Sarah had the cheerleader outfit with the crop top on. You could see the swell of her braless boobs under it. Her skirt was short, and she kept her perfect legs bare. Her hair was in a ponytail and she had pom-poms as accessories.

I wore the black suit with a white t-shirt underneath. My hair was slicked back with spectacles. I had a yard stick as an accessory.

None of us wore underwear and I noticed that the girls were all freshly shaven.

We grabbed some snacks and talked about what we thought might happen. Marie was unsure how many people would be at the event, or who they were. She said Sybil had some famous friends, including some sports stars and celebrities, but wasn’t sure that they would be there. She added that Sybil’s house was massive and had many rooms and huge private yard. We were all a bit giddy with expectation… when a knock came at the door.

Chapter 3: Halloween Party

I answered it and it was the bus driver I had arranged. We all piled into the short school bus which would help add to our entrance and headed to Sybil’s house.

We arrived at her mansion which had a roundabout drive. We were behind a limo and carriage.

From the carriage stepped a Cinderella entourage with people representing a stepmother, stepdaughter, Cinderella, and a footman. Cinderella was a stunning beauty; she was tall and slim. Her ball gown was partially see-through, so you could see her lacy bra and thong panties.

From the limo, came an Arabian prince and two harem women.

We made our entrance with me exiting the school bus with my ruler and small chalk board for counting out my students and the librarian.

Sybil greeted us at her door dressed as a slutty vampire with a form fitting, backless dress with slit up the side to her waist. She greeted us all kindly and suggested we grab a drink and mingle. She asked that all the servants don a silk band around their necks to indicate to everyone their intended role. Sybil commented to Marie as she took a collar and said, “Brave choice, Marie, you will love it.” She finally stressed the confidentiality of the evening and asked us all to deposit any phones we had in a secure locker area.

As we were heading in, she looked up to me and said with a wink, “Ray, you are a tall drink of water, but I think what makes you exceptional is now hidden. Talk to me before the auction for a bit of advice.”

We toured through the ground floor and saw a library, dining room, kitchen, and adjoining family area. The house was huge, and I noted some of the extra cushions and mats that were in some of the rooms.

We made it out into the backyard, which was lovely with some canopies set up, a couple of which were full tents with cotton canvas walls and doors .

Throughout the house were serving staff who were all attractive and scantily clad.

The ladies all grabbed a glass of white wine and I had a beer.

It seemed that we were a bit early as there weren’t that many people here yet.

Marie recognized a friend and guided us to him. We met Nick and his much younger wife, Isabelle. They complimented us on our costumes and Nick was unsurprisingly eyeing Sarah. Nick was dressed as a beast and clearly his wife was the beauty, Belle. Isabelle was wearing the collar tonight.

Nick tore is gaze from Sarah and asked if we had ever been to one of Sybil’s parties?

We collectively shook our heads.

Nick said that there would be a few opening events to encourage mingling and to display everyone to each other. There would then be an auction for masters to choose servants. He said that we would generate a lot of interest for three reasons: we were new, the women were all gorgeous and dressed for action, and there were many people who would get a thrill out of the incest angle with a mother and two daughters.

Belle was standing close to me and whispered, “Bid on me… and you can teach me any lesson you want.” As she finished, she licked her lips and gave my ass a firm pat.

People were starting to fill in. We saw a few superhero costumes with a Batman master and a Robin and Catwoman servants.

Sarah recognized a couple of minor TV stars and celebrities.

To prepare for the auction, I broke off from the ladies and went to tour the possible rooms. Downstairs had a dungeon area, a workout room, and a home theatre which had porn playing on the screen for possible excitement. Upstairs had standard bedrooms, some with four poster beds and ropes displayed.

While walking around, I ran into Sybil. She approached me with a sultry look where she noticed my growing erection and asked, “How are you enjoying it so far, big boy?”

“I am obviously getting excited for what may be in store tonight. You mentioned that you had some advice?”

As she ran a finger down my leg where my cock was hardening, she replied, “Patience in bidding is rewarded. Don’t blow your wad bidding high early. Celebrity is overrated. I do have one specific idea, though.”

“What is that?” I enquired.

Sybil asked how I felt about partnerships. She suggested that we form a bidding team. We would then acquire more servants and have more fun. She added that as the owner of the house, we could use her master bedroom to play in.

I was interested and responded, “That sounds like a good idea, but I see one problem. I only like women. If you only like men, we won’t be doing much combining when we get to your room.”

Sybil smiled, “Ray, I am bisexual and generally prefer women more than men. We might need to pick up a man or two, to spell you off for a bit, as you will be exhausted by the end of the night.”

I said, “It’s a deal then.” I sealed it with a kiss as I pushed my knee into her groin and pulled her close by grasping her ass.

After about thirty seconds, she stepped back to catch her breath. She said, “This is going to be fun.” She had a little wet spot on her dress where she had pressed her groin against my knee. “Come find me when the live bidding starts.”

I nodded and then asked who her servants were.

“I have two tonight. One is the blonde bimbo who does the local TV weather, and the other is a major league baseball player. They are both auction bait. People will bid high for celebrity. My advice is to look at the attitude. A creative and willing partner is more important than notching a celebrity.”

I know that I have brought my own minor celebrity in Sarah, tonight. “I can assure you that she has the attitude to match her physical beauty.”

“See you at the auction,” Sybil said, as she went to mingle with her guests continuing to arrive.

I made my way back through the house and into the garden to find my own harem. On the way, I noted a ‘pirate’-costumed threesome, and a ‘military’ pair with the woman as the general and the man, a private. Everyone was into looking their parts.

While looking for the ladies, I was accosted by some of the passing women and one man. I was flattered and kept the women in mind for the bidding, and kindly rebuffing the fellow.

I eventually spotted Marie and Jordan in a corner of the garden, talking to a very handsome fellow. I introduced myself and learned that his name was Andrew, and this was his first time, as well. He was relatively new to the city and had his own tech start-up; the ladies seemed interested.

I asked them where Sarah was, and Jordan just pointed to a gaggle of men surrounding her. No surprise there.

We were directed to all congregate near a makeshift stage in the garden. Sybil came to the stage and thanked everyone for coming and reminding us all about the discretion that was needed. She then introduced a professional MC who looked somewhat familiar.

The MC took us all through the bidding process. All the masters had been given an equal amount of ‘money’ to use in the silent part of the bidding. Making a silent bid on a servant would reduce the bid in the live section of the bidding. No one could bid on their own servants in the silent portion. The silent bids would then be totaled up and money would be distributed to masters based on the silent bids. This was meant to encourage everyone to bring desirable servants. Highly sought-after servants would result in more money for the master to bid with.

The MC then went on to introduce all of the servants to the audience. Sometimes they were introduced in multiples and sometimes as singles. Marie and Jordan would be auctioned as a pair and Sarah would be a single.

I moved to Sybil to get her analysis as they were introduced.

Sybil was disdainful of the celebs and sports stars. She commented highly about a mother/daughter pair, a petite Asian girl, the Cinderella woman we saw entering, and Belle who we had met earlier. I divided my silent auction money amongst her recommendations, as did she.

The MC came back to the stage and then introduced each master, giving the master the money that they had earned in the silent auction and let them choose a room which was on a map on the stage. I think Sybil was given the most and I was close behind with first Sarah generating a lot of interest and then having the kinky mother/daughter play with Jordan and Marie. Two-thirds of the masters were male, and I estimated that there were roughly two servants for every master in total.

The MC covered the rules between master and servant; masters able to make requests and servants accepting or denying. Any activity could be stopped at any moment if a servant felt uncomfortable. I looked around and there was general disdain for these rules. Everyone understood that this would be a wild night of unbridled sex, and all were looking forward to it. Wait staff would double as enforcement of the rules, but Sybil suggested that there had never been any issue in the past.

Servants would be auctioned in descending order of their secret bid value.

First up was Sybil’s hunky baseball star. This caused a stir as a male had never been the first to be auctioned. Each servant gave a brief intro where it was customary to indicate what you might do. The baseball stud mentioned that he was only into women and that he was sporting an eight-inch bat.

As the bidding started, Sybil noted the exuberance of her new guests for the celeb. The winner had to use all of her money to acquire his services for the night. Money coming off the table early was going to be good for us.

Sarah came up next to cat calls of many men. She strutted on stage and made a show of flashing her shaved pussy to the crowd. The bidding was fast and intense. In the end two guys combined all their dollars to get her. She was going to be in one of the upstairs bedrooms.

Jordan and Marie came up after the bimbo weather girl. Andrew, who they had been talking to, was the winner. He had a huge smile, as did the girls. They were going to be in one of the tents.

The second mother/daughter combo came up. I was able to win this bid as many had overbid for celebs. I also had more money than most, and still had half of my cash. I led them away from the stage and introduced myself.

Sharon was the mother and was a buxom redhead, while her eighteen-year-old daughter, Lottie, who sported the same fiery hair, but had a lithe, tight body. I was smitten and said so. They both blushed and they both moved to either side of me in the crowd. I told them of my plan of combining forces with Sybil. This got them both excited as her reputation in the bedroom was legendary.

Sybil was now bidding on the petite Asian who talked about her bisexuality in her intro. There wasn’t much racial diversity in crowd, so the exotic nature of her brought the bidding up. I estimated that Sybil still had half of her cash as well.

I acquired Cinderella next, who was a tall blonde goddess. She didn’t have large breasts which kept the bidding down. I liked breasts, but they were not the key physical feature that I looked for. Physically, I looked for athleticism and a beautiful face. Cinderella had this in spades. I walked up to collect her and leaned in for quick kiss. Her response was to reach down and grab my groin. When she felt my cock, she stepped back with surprise and then, a huge smile.

Sybil told me that many of the ladies and some of the men noted her discovery and were looking at me with lust.

I had less than one quarter of my money left.

Sybil was next to win and she won the services of the male army private. He had a huge smile on his face realizing that Sybil had chosen him. This would increase his value to all for next year and would likely make for a memorable evening.

Last to come up for me was Belle. She came to stage and talked about the lesson that she needed to be taught tonight. She was offering up submission to others, but was also repeating her earlier desire to me. I bid on her but ran out of money. Sybil came to my side and gave me enough to win.

Belle was jumping for joy when she saw that I had won. In jumping, her skirt came up revealing that she hadn’t worn panties and showing off her bare pussy with a small dark landing strip on top. I saw Nick scowl somewhat at her exuberance, but he quickly was distracted by his servant who was rubbing his leg.

Sybil made a very late purchase of the Cinderella’s footman. We discovered later that he was Cinderella’s brother. They weren’t sure of the incest thing, so were auctioned separately.

I gathered my servants and brought them over to Sybil and her group. This was going to be wild. Together, we were six women and three men. While I now had lots of experience with multiple women, I had never been a situation where there were other men involved. While I am quite prudish about any contact with a man; I did see how together, we could bring more pleasure to a woman.

Sybil took charge and led us all to her enormous bedroom. There was a king-size bed, a love seat, and lots of floor space with a soft mat in the middle of this. Once there, she made introductions. She talked about her partnership with me in the bidding and said that I would surprise most tonight with what Cinderella discovered on stage. She pointed out the available toys in her closet and offered each of the men a blue pill to maintain stamina for the evening.

As she introduced herself to everyone, she asked each what they most wanted to do tonight.

Cinderella gushed that she wanted to explore her first threesome with another woman and a guy.

The Asian woman, Jules, wanted to be dominated by both men and women and wanted to perform clean up duty by licking up any bodily fluids that were available.

Lottie, the young redhead, wanted to be forced to eat out her mother.

Her mom, Sharon, wanted to try anal sex while her daughter was eating her.

The army private, Mike, wanted to try anal sex with a woman tonight.

The footman, Ted, was very meek and said his desire was to service his sister. Cinderella looked shocked, and then gave him a brief smile.

Belle wanted to be made airtight tonight, preferably with real cocks.

I said that I wanted an eating fest where I would eat a woman while another woman deep-throated me, and a third woman ate my ass.

Sybil went last and commented that my deep-throat desire might be harder to get than people thought tonight. She wanted to be orgasmed on by men and by women. She looked at Jules and said, “And yes, Jules, you can lick it off after.”

She said it was time for all to start stripping. She paired us up to strip each other, with one threesome of the two princesses and the footman. Touching was encouraged, but no penetrations or orgasms were to be had… yet.

Sybil then came to me and started unzipping her black dress. I peeled it from her shoulders to reveal that she had a demi cup bra that held up her medium sized breasts with erect pink nipples. I gently touched them which elicited a moan. She wasn’t wearing panties, but had black thigh high stockings on. Her pussy looked perfect and had a small platinum landing strip on top to match her blonde hair.

Sybil then ripped off my suit jacket and pulled off my shirt. “Nice abs, big boy; but I am more interested in the package below your belt.” She then loosened my belt and unzipped my fly, reaching in to pull out my cock. She exclaimed, “Oh my!” when she saw it and started licking her lips.

I looked over at the others.

The footman had all of Cinderella’s and Belle’s clothes off and was fondling Belle. He was still dressed himself.

Private Mike and Jules were both naked and had their hands roaming all over each other. Mike was in great shape and Jules had a tight body with small breasts capped with brown nipples.

Sharon and Lottie were in matching garters and stockings. Sharon was behind Lottie who was staring at my cock with lust. Both had white skin with a pepper of freckles.

Sybil spoke up and suggested that we start in our auction groups.

My group whispered together and then gathered on the mat with Lottie in the middle, her mother behind her, and the princesses on either side. Sharon said, “Master, come to us. We want you to start with my eighteen-year-old daughter who has never been to a party like this.”

I went to the group and as I approached, Sharon put her hands on Lottie’s shoulders to guide her to kneeling. As I came into the circle, the princesses each put a hand at the base of my cock and another on my shoulder. They then pointed my engorged cock at Lottie’s face.

Lottie licked her lips once and then opened her mouth and took me in. Having four strangers focused on me was very hot.

Her mom said, “Good start, honey. You know he wants you to take him deep.” As she put both of her hands on her daughter’s head and pushed her head into my groin. My cock went to the back of her mouth. Lottie took about an inch into her throat before pulling back to gag and cough.

Sharon stoked her daughter’s hair, saying, “You will need to practice.”

Cinderella then dropped to her knees for a turn. I turned towards her with my spit-covered cock hitting her cheek. She quickly recovered and put me in her mouth. She bobbed for a bit and then tried to take me in her throat. She didn’t do much better than Lottie.

“I guess that slipper didn’t fit so well, Cinderella. How about letting me tame the beast!” Belle said with a grin.

I turned towards her and she dove onto my tool taking a few quick bobs and covering the shaft in spit. She circled my head with her tongue and then dove down to take three quarters of my meat into her throat. She held it there for a few seconds and came up for air. She tried again but didn’t get much further. She came up and said, “Oh my god, I feel inadequate. I have never had an issue getting a guy into my throat.”

Sharon shook her head as she dropped to her knees as well, and leaned over her daughter’s shoulder to take her turn. I moved back to the center and she opened her mouth.

Sharon licked the shaft first and then dove on to take me almost all the way to the base on her first dive. She came back up for air and then made her second dive all the way down until her nose was pushing into my lower belly. She held it there for about for a second and then came off to take a big breath.

Lottie, Cinderella, and Bella all started clapping while Sharon had a satisfied smile on her face.

I looked over to Sybil’s group. Sybil was laying on the bed on her side and her legs apart. Mike was laying behind her with his cock pumping into her pussy from behind. Jules was laying in front of her, licking her clit and Mike’s shaft as he fucked Sybil. The footman was above Sybil’s head where she had extended her neck to suck his cock.

The footman said he was going to cum. Sybil let him start in her mouth and then pumped his cock onto her tits.

Jules, the avowed cumslut, moved up to suck the cum off Sybil’s breasts and then the end of the footman’s cock.

We all ‘oohed’ and ‘aahed’ at the little show.

I said to our group, “How about some princess play time. Belle, get on your back and grab the back side of your knees. Cinderella should be good at cleaning if she is in character.”

Cinderella looked a bit apprehensive, but this was part of her stated desire, so I pushed on.

Belle got situated, while I guided Cinderella to her knees and guided her face to confront Belle’s juicy pussy.

I was behind Cinderella, Lottie and Sharon were on either side of her.

Sharon grabbed Cinderella’s bun and pushed her face into Belle’s pussy.

I was lining my cock up with her dripping snatch and put the head up to her vagina which elicited a moan from Cinderella.

Lottie was watching as I pushed into Cinderella with her mouth agape and look of total lust.

Cinderella was very tight, but I was able to go balls deep in her. Which sent out another moan while pushing her face deeper into Belle.

Lottie was now rubbing her pussy as she watched.

As I started to stroke into Cinderella, Sharon came back to be across from her daughter. “That is going to be you later tonight when he puts that huge tool in your tiny vagina.”

Belle announced her orgasm to us and I continued to pound Cinderella’s face into her cunt. This sent Cinderella over the edge and I held still while she was contracting on my cock. At the same time, I licked my thumb and pushed it into her ass and looked at Sharon, “Are you going to be ready for me to sodomize you?”

We both smiled and Sharon said, “I am so ready!”

I pulled out of Cinderella and Sharon said to her daughter, “Time for you to get a sample of pussy juice,” and guided her to lick off Cinderella’s girl cum on my cock.

I felt movement behind me and realized that Jules was between my legs and licking Cinderella after her orgasm. This sent Cinderella to another orgasm as her whole body shook.

Sharon was now on all fours next to Cinderella. Sybil had joined us and was putting lube in her ass crack while pushing two fingers into her anus.

I pulled my cock from Lottie’s mouth and said, “If you liked watching the pussy penetration, you should get a close-up view as I fuck your mom’s ass.”

Lottie just nodded and moved to her mother where Sybil guided her under her and lifted her head to start sucking on her mother’s pussy.

I moved over and immediately pushed my cock into Sharon’s ass and she yelled out, “Motherfucker!”

Lottie was wide-eyed as I split her mom wide. I took a few strokes into Sharon which was making it hard for Lottie to maintain contact with her mother’s pussy. On about my fifth push, she started orgasming. This resulted in a tightening of her anal chute and spray of girl cum onto Lottie’s face and mouth.

I felt Jules move behind me again to put her mouth to work cleaning the spays off of Lottie’s face and directly from Sharon’s slit.

Sharon’s orgasm also sent me over the edge. My first stream went into Sharon and then I pulled out. Before my third stream came, Sybil had my cock in her mouth while pumping my shaft. She then spat it out on Sharon’s back. Jules had come up from cleaning Lottie’s face and started licking my semen off Sharon’s back like a cat at a bowl of cream.

I looked around and saw that Belle, Cinderella, Mike, and the footman were all on the bed. The footman was on his back with Belle riding him. Cinderella was holding Belle’s head as Belle licked her. Mike was lining up to put his cock in Belle’s ass.

Normally, I would have been soft after cumming, but that pill was working its magic. I was a long way from an orgasm, but there was no lack of hardness. I went over to fulfill Belle’s desire, by taking Cinderella’s spot and feeding Belle my cock as Mike plowed in from behind.

Belle tried to scream but it just came out as a gurgle. We all got in sync and pounded her holes for only a few minutes until her eyes turned up and she started to shake all over. We stopped and she rolled away to recover on the side of the bed.

Jules tried to dine on her bottom, but Belle pushed her away as she was too sensitive.

Sybil climbed onto the footman’s cock and beckoned Mike continue his anal work on her.

Cinderella wasn’t sure what to do and I whispered into her ear to sit on her brother’s face. She smiled and lowered her stunning body onto her brother.

This quickly set of another chain reaction with the footman cumming in Sybil’s cunt after only thirty seconds of eating his sister. Sybil was next, cumming while being impaled by two cocks. Mike was last, pulling out of Sybil to cum on her back.

Jules licked all the cum off Sybil’s back, gave Mike a quick lick, and then ate the cream pie leaking out of Sybil’s pussy.

Lottie and Sharon were holding hands while Sharon commented on the action. The devouring of cum by Jules, had Lottie fingering herself.

We all took a breather and then Sybil said, “We have realized everyone’s fantasy this evening, except one,” as she turned to me. “That is the sign of a considerate master. He took care of his people’s needs and wants before his own. We need some volunteers to complete this.”

Sharon, who was clearly used to being in charge took the initiative, said, “There are only two of us that can throat him, so Sybil can choose there. We then need a woman to rim his ass and another to ride his face.”

All of the remaining women volunteered for both roles, while Sybil demanded the cock sucking duty, as she was a master.

It was decided with a quick random draw with everyone throwing fingers between one and five and then counting from one person. Cinderella was going to ride my face while Lottie was going to lick my ass.

Sharon talked to Lottie, who had never done this. She talked about leaving any inhibition behind and to use her tongue like she had on her earlier in the night.

I got on the bed on my back. Sybil was kneeling beside me with the top of her body on my abdomen. As Cinderella lowered herself on my face, Sharon and Belle pulled back my legs to expose my ass to Lottie.

I lasted less than five minutes. When I came, Sybil held my cock a couple of inches from her face and sprayed cum all over it. Lottie pulled back and Jules jumped in between my legs to lick off Sybil.

Sybil suggested a quick break. It was only 10:00pm. She suggested that we all wander around, to take in the sights, and return to the room at 10:30pm. She added, “Only looking and talking out there, please. Get inspired by the acts you will see and save your energy for our reunion.”

Everyone nodded and went off. Sybil came and grabbed my hand. “Let me show you around. I have an idea where the best action will be and love that I get to show off your big swinging dick.”

Sybil asked what I thought of the party.

“Your organization and structure are fantastic. Everyone is a willing participant and has freedom in choosing their role and what they will and won’t do. How long have you been doing this?” I asked.

“This is the third year, and it has gotten bigger and better each year,” Sybil said. “You should know that I do some smaller parties throughout the year with smaller groups. You were awesome upstairs, and I meant what I said about you putting the needs of others ahead of yourself. You are gentle, while still being commanding. It is an intoxicating mix. Every woman in that room would sacrifice anything to be with you.”

“I am flattered,” I said. “However, I can barely keep up with my current partners. My cock might fall off if I attempt to expand further.”

“I am not trying to pry you away from anyone you care about, but if you have any juice to spare or just some down time, call me and I will continue to blow your mind… amongst other things,” Sybil said with a smile.

Sybil led me to the basement where there were various acts of debauchery happening. In the center of the room was Cinderella’s stepmother who had a dildo sticking out from her mouth which was strapped around her head. She was bent over and sodomizing another woman while taking a large dick in her own ass. In the corner were two men and woman. I guessed that the men might be bisexual and didn’t want to look any closer as this was a turn off for me.

We went to the tent where Jordan and Marie had gone to. They had been joined by a couple of other groups including the two guys who had won the bid on Sarah. Sarah was close to the door and let us in. I greeted her with a kiss and asked how her evening had been.

“It has been great. My two masters took turns with me, but admittedly didn’t have much stamina. They are ones passed out on the pillows in the corner. After a first round, I wanted to see how mom and Jordan were doing. Jordan has been a sexual animal tonight willing to take whatever is offered. She has mom doing clean up and generally making her into a cum dumpster. I have seen her take cocks in all her holes tonight. When the lucky guy who is fucking her cums, he either pulls out and blows on Marie, or he cums in her and Marie licks it out,” Sarah explained.

We looked over to the middle of the room and Jordan was being spit roasted by two guys while Marie was obediently on her knees at Jordan’s side. Marie was completely naked except that she was still wearing her librarian glasses which had streaks of cum on them.

As we watched, the guy fucking Jordan’s pussy pulled out of her cunt and Marie instantly bent over to take him in her mouth.

The guy who just came exclaimed, “Oh my fucking god, I never thought I would be able to cum again tonight. Fucking a nymphomaniac eighteen-year-old and then busting my nut in her mom’s mouth was too fucking hot.”

Jordan saw me and Sybil and briefly disengaged from the cock in her face, saying, “Ray, there is an opening here for you.” She winked and then continued giving head.

Sybil answered, “We are just visiting and ensuring the guests are all having a great time. There is no way are you are getting Ray’s cock until this party is over, though. His mastery is needed elsewhere.”

Jordan gave a little pout, but understood.

We took our leave and continued to wander around seeing other partygoers going at it. I noted that the wait staff were disrobed as well.

Sybil seeing my gaze, offered, “They are active participants tonight with instruction to fill in where needed. If guys wear out too quickly, a male staff person will replace him. If a woman is worn out and needs a break, a female staff member will fill in. I would say it is more often that earlier issue, rather than the latter. We should get back to room. Our servants will be getting frisky,” Sybil suggested, with a nod of her head.

Our servants had all returned, and… while the cat was away …the mice did play.

Belle was on the mat with Mike and the footman, experiencing her second ‘DP’. Jules had her head on Belle’s back with her mouth open, hoping that Mike would put something into it.

Lottie was laying on the bed with her legs spread wide and Cinderella was on her knees eating out her pussy. I noted that Cinderella now had a butt plug in her ass.

Sharon was over at the dresser getting a strap-on dildo affixed to her waist; and she looked up as we entered. “About time,” as she came towards me. I had a look of apprehension on my face as the strong buxom redhead walked with purpose, the dildo bouncing from side to side. She saw my expression and laughed as she understood that I was worried that she was going to use the phallus on me.

“Don’t you worry,” Sharon laughed. “I intend to sodomize Miss Cinderella with this so you might do her the honor of taking her anal cherry. As a warmup, I am hoping to show my daughter what a real cocksman can do. She has only been with a couple of boys who have no clue. She will be very tight, but is very willing after your performance earlier tonight.”

Sybil had gone over to stand in front of Belle who was not doing a very good job of licking her as the continual pounding was moving her head around too much.

I thought Sharon had a great plan for me. Fucking her daughter would be great and the thought of fucking Cinderella’s ass was a turn on.

“Cindy wasn’t up for this until she saw you fuck my ass,” Sharon shared. “She wants to try it, but I expect that it will be a tight fit in that narrow body of hers. Lottie was asking questions about it as well, but she needs a lot of work before she will be ready.”