Christmas orgy with the single moms

TL;DR: Had an orgy with my single mom friends, dressed as Santa and brought a special gift for them to enjoy resulting in numerous orgasms.

Since my wife's passing and being inducted into the secretive single moms' club, I've made it a yearly tradition to treat them to a flirty Christmas party that usually devolves into some sexual fun. The tricky part is finding time when we can get babysitters for our kids, but when we do, things happen on a moment's notice. Unlike in the summer, when I'd host them out at my wedding venue, for nights like this, I invite them over to my house, which makes it easier to stay warm.

Another part of the tradition is getting to play Santa for all of them. Initially, the agreement was that I'd help them get toys for their kids, and vice versa. What I didn't tell them was that I also got gifts for them. It's never anything special, usually some makeup, perfume and maybe a sex toy. Anyway, we had our fun on the 21st. I got a couple of food platters and dressed up as Santa, just in the robe and very loose pants, which, when erect, didn't hide much to the imagination.

Ready to go and everything laid out, the ladies started showing up around 7pm. Cassie was the first to arrive, and, seeing her from the street, you'd never know she was only wearing a red lace g-string, a see-through bra under her coat, and leggings. Once she was inside, we shared a quick kiss, then she stripped down, and I gave her her gift, which I forgot to mention came with a Santa hat. She then went to do some touch-ups.

Next came Nora, my late wife's twin, and Michelle, the youngest of the single moms who's still in her twenties. Like I did with Cassie, I greeted each of them with a kiss, and they revealed to this ol' saint Nick why they were naughty girls. They both had crotchless body suits on. Nora's was see-through and one I had bought her for Valentine's Day earlier in the year, and Michelle's was all red lace. They each got their gifts, and Michelle joined Cassie in getting ready, meanwhile Nora took me to the side.

We went into the kitchen, and I pressed against the fridge, and stuck our tongues in each other's mouths. It was during this time that she took the opportunity to reach into my pants, and worked on getting me hard. She was doing a very good job, and I was convinced she was about to get on her knees when the doorbell rang again. Having to cut our fun short, Nora started opening her gifts while I went to get the door.

Ashley, the single mom known for being fashionably late, greeted me with a smile and, while still standing on the porch, threw open her jacket to reveal she was completely naked, aside from three red bows taped to her nipples and one just below her belly button. She also had Santa's gift written on her thigh with an arrow pointing to her pussy. Dragging her inside and giving her a kiss, and a teasing spank. She got her gift while Michelle and Cassie joined us, and Nora wasn't far behind.

The first hour was pretty casual, we played some games, drank some wine, ate food, and the girls made sure to each sit on Santa's lap to tell me all the reasons they should be on the naughty list, and where they wanted their Christmas filling when the real fun started. Around 8:30pm, everyone was getting pretty handsy with each other, and they really wanted Santa to take his cock out, so I happily obliged their request with a little Santa striptease, but kept the Santa hat on.

Only, I hid a secret from the girls, and when I finished stripping, the doorbell rang again. They were confused, looking to cover themselves up, but I went to the door completely naked. For them, the mystery increased, and they weren't expecting another girl to walk in when I opened the door. It was Anna, and she was going to be an additional toy for the ladies. She took her clothes off, revealing the green lingerie to make her seem more like an elf, then I took her hand and brought her to all the other ladies.

"Ladies, this is Anna, my assistant I had during the summer, and my new little fuck buddy, and I was thinking you four might enjoy using her as well. She doesn't have any limits, but she has limited experience with women, so be gentle with her at first." I explained to all of them.

That's all they needed to hear as Cassie, the most dominant of the single moms, got up, walked over to Anna, and ordered her onto her knees. Anna obeyed, which all the moms seemed to like, but then Cassie went one step further and buried Anna's face between her thighs. Without needing to be told what to do, Anna started licking and was hitting all the right spots pretty effectively. Within a minute, Cassie was moaning, and the other girls gathered around her so that we were all looking down at Anna as she looked up at us. I was convinced Cassie was going to cum, but she pulled Anna away at the last second.

"Okay, she can stay. She's really good with her tongue, girls. Anyway, I'm horny, and I need to cum, are we fucking or not?" Cassie asked the room, and there was a unanimous consensus.

In the basement, I had set up four air mattresses, and they were all pressed together and would end up being our playground. The single moms went down first while I pulled Anna aside, filled her in on the communal safe word, and told her to let us know if she's uncomfortable. Only from the smile and wetness on her face, I think she was ready for everything we were about to throw at her.

Each girl took one of the air mattresses, and played rock paper scissors to decide the order I'd fuck them in. It went Michelle, Ashley, Cassie, and then Nora. Meanwhile, while I was doing one-on-ones, Anna was in charge of entertaining the other girls.

Joining Michelle, I started by eating her out. She was already pretty wet, making doing missionary a breeze. She's got such a nice pussy, that just swallowed me whole while we made out, and she wrapped her arms and legs around me so I couldn't pull away. I fucked her hard and slow, until her body started spasming from her orgasm, and her pussy clenched onto my cock, forcing me to erupt inside her pussy like she desired.

Upon pulling out of her, Anna took the initiative to eat her out, and Cassie and Nora assisted her. While they were busy with her, I joined the naked succubus Ashley. She's very much a doggystyle addict who likes having her ass played with. Filling her pussy, teasing her ass, and pulling her hair, she started moaning up a storm as she added her wetness to Michelle's that coated my cock. Like Michelle, she also wanted a creampie, and I happily delivered.

After that, I took a quick water break and left the girls to their own devices. I came back down, and they're all admiring Anna's pussy and playing with it. Things took a bit of a turn once I rejoined, and Cassie and Nora decided on a threesome since they couldn't wait any longer. Still going in order, I laid down, Cassie claimed my cock, and Nora sat on my face. The grip of Cassie's pussy is still insane, it's like a god damn vice, and without having a way to tell her I was close, since I was pinned under Nora, she also got a creampie. She didn't seem to be upset about it.

Then it was Nora's turn, and I stood up, picked her up, and fucked her against the wall right beside my late wife and I's wedding photo. Cassie and Ashley helped support her on the sides, and Michelle rubbed her hands down my back, but Anna stepped her game up, crawled between my legs, and started licking Nora's slit while I fucked her. Knowing Nora is an aggressive squirter, I may have forgotten to tell Anna that and only remembered when Nora erupted and screamed she was cumming.

Anna was drenched, and the girls took her to the washroom to get cleaned up. Meanwhile, I downed another water bottle, and used the time to relax. It took roughly half an hour, but they eventually came back, and a couple of things had changed. First they were all naked, second Cassie was carrying a worn out Anna on her back. She placed Anna down on the air mattresses, and her hair and makeup were a mess. Her body was glistening, and Cassie casually said, "We're keeping her; she got all of us off upstairs, but there's one last thing she needs to do to join the club."

I asked what it was, and Anna looked at me upside down and weakly said, "Breed me, Santa. Make me a single mom."

Her wish was my command, since I didn't want to bring the party down. Flipping Anna over, giving her a spank, and pulling her up into doggystyle, I grabbed her hips and filled her from behind. I didn't know if I had another load to give, but I fucked her hard as all the other girls squatted around us, all teasing Anna. Playing with her body, spanking her, twisting her tits, and degrading her. It was fucking hot, and Anna came twice, and during the second one, I finally burst and filled her insides.

When I was done with her, the girls each kissed my tip, thanked me for their gifts, then left lipstick marks on Anna and told her she could join in future club activities anytime. After that, there was a little bit more mouth and finger service, but nothing crazy, and by 10:30pm, the party was over. Michelle, Ashley, and Cassie all went home to relieve their babysitters, while Anna and Nora spent the night with me.

We were exhausted and had a quick shower together, then crawled into my bed. Nora joked about the three of us being a happy family and shared a kiss with Anna before they fell asleep on either side of me. I didn't last much longer, but woke up to them both giving me head, which ended with a shared facial, before I went and made them breakfast.