Halloween Moms and Daughters

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.