Halloween Moms and Daughters

We walked over to the bed and I leaned into kiss Lottie who was in the middle of cumming on Cinderella's face.

I laid down next to Lottie as Cinderella raised her moist face from Lottie's pussy with a smile.

"So I hear I have some work to do," I said to Lotte.

"Yes, master. I was hoping you would fuck my juicy, tight pussy," Lottie purred.

Cinderella, who clearly knew the plan, moved from Lottie's pussy to suck my cock before guiding it Lottie's slit. She ran the head up and down and said, "You are going to be so full when this enters you. If it hurts at all, let master know and he will go slowly. I have never felt so complete as when he was in me."

As Cinderella was helping me penetrate Lottie, Sharon was behind Cinderella and was stroking her ass as she tugged on the butt plug.

I pushed my cock head into Lottie who let out a moan. I stopped and let her get used to it and then slowly resumed pushing.

Cinderella gave Lottie's pussy a lick from where I was going into her and up to her clit.

As I got all the way in, Lottie had an orgasm making her pussy even tighter around my raging member.

Sharon had now removed the butt plug from Cinderella and reached up to insert it into her mouth saying, "All good anal sluts do ass to mouth."

Cinderella was initially repulsed, but as Sharon replaced the plug with her lubricated dildo, she relented and took the plug in her mouth.

As I stroked into Lottie, I said, "What do you think about your mother sodomizing Cinderella?"

"That is so hot..." Lottie continued, "I know I am not ready yet, but I want her to do that to me before you take my anal cherry. I want to show you, prove to you... I want to suck your dick when it comes out of Cinderella's ass for the first time. I know Jules has been doing clean up all night, but I thought you might want to see an eighteen-year-old do ass to mouth and eat your cum."

Lottie's nasty offer got me raring to go and I started to stoke into her aggressively which had her yelping as I touched her cervix at the bottom of each stroke. After a few minutes, she started shaking all over as I held still while buried in her pussy.

Sharon had stopped fucking Cinderella's ass for a moment while they both watched Lottie's orgasm.

After Lottie's muscles released, I pulled out of her. Cinderella grasped the base of my cock and licked all of Lottie's juices off. She said, "Time for you to replace Sharon. Your slipper didn't fit in my throat earlier, I am sure it will be a perfect fit in my ass. Just go gentle as you enter on the first stroke."

I crawled up to kneeling on the bed. Belle had now joined us as Sybil had taken her spot being double teamed by Mike and the footman. They had switched places and footman was being encouraged by Jules to take Sybil's ass.

I kneeled beside Sharon who took the dildo out of Cinderella's ass and then grabbed Belle by her hair and had her suck the dildo.

I took her place behind Cinderella and grabbed some lube which I applied to her ass crack and my cock. It was a tight fit going into her ass even with the loosening by the plug and Sharon's strap-on.

Cinderella let out a yell as the head of my cock went past her sphincter.

Lottie had recovered and was now at Cinderella's side. Belle was on the other side and they both watched as I pushed into Cinderella.

I kept pushing into the princess until I was balls deep. I pulled back until just the head was in her and squirted more lube on my shaft and around her asshole. I pushed back in at double the speed I had initially done.

Sharon, who had heard her daughter's offer to me, said, "Lottie, put your chin on her lower back and open wide. Show your master that you want to suck his dirty cock and eat his spunk."

Lottie did as she was told, and Belle mirrored her by putting her head next to Lottie on the back of Cinderella.

I rewarded initiative by feeding Lottie first, and then Belle, after getting in a few more strokes into Cinderella.

After doing this twice for Lottie and twice for Belle, my balls were boiling, and I wasn't going to last. I stroked faster into Cinderella's ass.

Belle had reached down and was stroking her clit as well, which then sent Cinderella over the edge. As her sphincter clamped down on my cock, I pulled it back and out of her convulsing ass, just on the verge of blowing my load.

Lottie moved like a cat and grabbed the base of my cock and moved aggressively to bob on the end of my knob.

I yelled out loudly as I erupted into the teen's mouth. She was true to her word and took all that came out of my cock.

Lottie then pulled back with pursed lips and raised her head. She opened her mouth to display the load of cum swirling around in her mouth and then gulped it down. She had a big smile and opened her mouth to show that she had swallowed it all.

Jules had come over and was scowling at Lottie for taking her treat.

Lottie smiled at her and said, "Sorry, Jules, I had to try this. It looks so hot when you do it and tonight is my first time swallowing."

The anger drained out of Jules and she came over to ask Lottie, "What do you think?"

Lottie answered, "I didn't mind it at all. I could feel him jerking powerfully into my mouth and knowing that I was giving him pleasure almost made me cum as well."

Jules smiled and grabbed Lottie's hand and pulled her back to where Sybil was getting double teamed. She said, "These studs are going to cum soon. I will hoover it up and then drool into your mouth for you to eat. If you are going to be a cum slut, I want to help."

Cinderella, Belle, Sharon, and I went to watch finale which lived up to the billing that Jules gave. We all gave a little cheer as each person came, with the footman going first and blowing on Sybil's back. Sybil came second and this set Mike off who pulled out to be sucked dry by Jules. Jules first fed Mike's load to Lottie and then returned to clean Sybil's back of cum and drooled that load into her protege's mouth as well.

Cinderella was standing next to me with her arm around my waist. She was almost six feet tall and whispered into my ear, "This has been the best night of my life. If you ever have time for me, I want to be involved with you in any way you see possible or desire. You might think that I just want your big cock, but that isn't the heart of my desire. You are a considerate and careful lover, and I am sure those traits carry over into your non-sexual life, as well."

I told her that I was honored by her interest and complimented her dynamic sexual performance tonight. I told her that I would have to give it some thought, as I was already involved with others and needed to respect them as well.

"I understand," Cinderella said. "If your circumstances change or if you can add me in any way, I am open to it."

Slowly, we put some clothes back on and discussed our evening.

Everyone had enjoyed themselves and all were thanking Sybil for creating such a great event.

As we talked about the evening, I was approached by Sharon and Lottie with an offer to get together with them again. Lottie talked again about losing her anal virginity to me. Jules and Belle were hopeful that I would come again next year. They were both in relationships and knew that this was a one-night thing. Most of the guests made their way into the main area to look on or find the people they came with.

It was just Sybil and I left in the room. I gave her a warm embrace and thanked her again. She said that she would be in touch for other events, but understood that I might not be available. Sybil said, "I saw you being propositioned by a few at the end of the night."

"Cinderella was very keen to start something," I said. "She is a spectacular beauty and seemed very nice. I just don't know if I can handle another woman. Sharon wants me to continue with Lottie, as well. Lottie was really sweet; but I must admit, Sharon scares me a bit. I was surprised that she was a servant tonight."

"Cinderella is a very nice girl from a very rich family. She is in her early twenties and just back from college. She is single and was here with her mother who you saw in the playroom. I should also mention that she has an identical twin sister who couldn't make it tonight. Let your imagination run wild with that if you want," Sybil said, with a smile.

"Sharon is a driven lady and recently divorced from her husband. She said that he complained about her domineering ways, so she thought it would be good to spend a night as a servant. I think her nature still came through, though, even if she was in a submissive role," Sybil added.

"I do seem to have a thing for mothers and daughters, so I may take them up on it," I speculated.

We strolled down to the back garden together until other guests kept coming to Sybil to say goodbye and thank her.

I found my girls sitting together on an outdoor couch in the yard. They had all put on some clothes and smiled when they saw me. They were all exhausted as me. I called the bus driver and asked him to meet us in the roundabout.

When we got back to my place, we all jumped into bed and promptly passed out.

I woke early the next morning and snuck out of bed to go downstairs and started assembling a breakfast of eggs, bacon, coffee, and toast. We all deserved a greasy spoon breakfast after our evening of hard work.

Sarah was the first to come down and hung out on a stool at one end while I cooked.

I asked her how her modeling was going?

"It is going really well," she said. "I have been asked to do Victoria's Secret Fall Show in New York. It is their big holiday launch."

"Wow, that is as good as it gets for modeling, I think. Congratulations."

Jordan and Marie came down wearing a couple of my old t-shirts. I served breakfast and we all tucked in. We all talked about the wild night we had. Jordan and Sarah each tried to start something up, but I wasn't responding. I think the little blue pill gave me stamina last night, but it was definitely robbing me this morning.

My mind was focused on getting caught up with Teena and seeing how I could help her. Sarah, Jordan, and Marie were great, and it was a wild distraction; but I had deeper feelings for Teena and Samantha.

We wrapped up breakfast and the girls departed. Sarah had a flight to catch, while her sister and Marie were doing a college tour to help Jordan decide where to pursue her degree. They all wanted to plan another date, which I was open to, but couldn't commit to--yet.

The end... for now.

This story was a bit of a sidetrack from the main plot. I have always enjoyed the Halloween-themed stories on Literotica and wanted to enter my own. Probably my favorite Halloween story over the years was a GOR-y Halloween Party by Tx Tall Tales. If you have read it, you will see that I took inspiration from his story surrounding the idea of an auction.

My next installment will get back to Teena, Denise, and their daughters.

Future stories that I thought of after writing this include:

1. Cinderella and her twin sister. This may involve the stepmother.
2. Sharon and Lottie: Lottie loses her anal cherry to Ray.
3. Sybil convinces Ray to come to a private party with some of her friends. I might use this device to execute the Cinderella or Lottie story elements. Hmmm.
4. Sarah is on the runway modeling for a Victoria's Secret show and invites Ray as her guest to the show and the after-party.

As I have done in my previous stories, here is an approximate porn star that would resemble each of the characters. I do this at the end of my stories, so I don't corrupt your imagination while reading.

Sybil: Skye Blue (without the tatoos)

Sharon: Bree Daniels

Lottie: Lottie Magne

Belle: Lexi Belle... this was a perfect fit for the name.

Cinderella: Anastasia Knight

Jules: Lulu Chu

Thanks again to kenjisato for editing.