MamaBear Club: NYE Pt. 01

MamaBear Club: NYE with Stepmom, Part 1

"Ok ladies. I think it's time to get started now," a beautiful woman said as she stood up from the comfortable chair nearby. My stepmom, Sara, and I were attending a New Year's Eve party together. I'd known her for about 10 years now and we'd been living alone together for the past 5, after my dad had his fatal heart attack. She was a good stepmom, always doting over me, giving me everything I needed.

Even at 19, I was very shy. I'd grown up being homeschooled and now I was even attending college remotely. The only real interaction I had with people were my stepmom and those friends and their sons she chose us to do things with.

So I was a little surprised when she said we were going to a party this year for New Year's Eve. It was going to be the first real party I'd ever been to in my life. This party wasn't too large, with three other moms attending, each with one of their sons, too. So really, eight people in total.

"I'm Amy and thank you all for coming tonight to our MamaBear Club's New Year's Eve Party!" Everyone clapped in excitement, knowing this was going to be a fun night. "I believe two of you are new to the club and this is your first event, right?" she asked, nodding her head to get agreement.

Two of the women, my mom and another half raised their hands while the others clapped for them.

"Welcome, wecome," Amy said. "We're not a big club, only a half-dozen members or so in our little branch here in town. But there are other branches across the state and country, as well, that you can spend time with, now that you're members."

It was all really just going over my head at the moment. I didn't know my mom had joined a club... nor did I know this was some sort of club event. And I certainly didn't have a clue what this club was all about. What I thought was just a simple party was becoming more and more complicated.

"As I'm sure you're aware," she said, sounding just like any club president, "our goal in MamaBear is to cater to and help enhance the relationship between you and your son... who we call our cubs. We know it's difficult raising cubs. They offer special challenges and delightful... benefits... to those who want to explore them. We have the information online, but we have monthly meetings you can attend and we host these special parties 4 or 5 times a year to offer you a chance to learn more about your cub and about other cubs his age."

There was a murmer between the women as they started getting excited about the meeting opportunities.

"I do have to make it clear, though, that this is not a club for your cubs. It's a club for you, the mother... the mamabear. It is not expected nor desired that your cub makes friends at these events, other than friends with other mamabears. So please do not encourage him to."

"And so, with that all out of the way, lets start our New Year's Eve party!" Everyone clapped with excitement, ready to get things started.

"Just to be clear with everyone, I have verified all age and health documents, so we can have a carefree time," she said. "It's a closed party, so if your mom agrees, the cubs can even drink a little. But we will not tolerate drunkeness. That will get you ejected. As will any fighting. Ok?"

"Yes ma'am," all the boys murmured and nodded.

"So, what I'd like to do then is have each cub introduce himself and his mamabear to the group," the woman continued. "You might have already introduced yourself to some, but this will be good for the whole group. And then maybe have each cub thank and kiss each of the mommabears for allowing us to be here tonight. Sound ok?"

"Yeah," all the women agreed, nodding and clapping, two a little more excitedly than the others. They seemed to really want those kisses.

"Ok then. We can start right here... right with my little cub," she said, indicating the young man sitting beside her.

The woman sat down as her son stood. All the guys were wearing nice, button-down shirts and dress slacks, a look that I was used to wearing. My mom was pretty particular in how I looked when we went out.

"Hi," he said, looking shy. "Um... my beautiful mamabear is Amy and my name is Jay." He looked at his mom who blew him a kiss.

"Hi Amy. Hi Jay," everyone said, welcoming them both to the party.

"Ok, then. Go, go, go," Amy told him. Slowly, he moved to each mom in turn, thanked them for having the party, and then kissed them. The kisses were far more intimate than I'd expected and I even felt myself get a little jealous as he kissed my mom.

"Nice!" Amy said when he finally sat down again. "Ok, how about you," she said indicating me.

"Um... ok... well, my name is..."

"No, no. Please... start by introducing your mamabear," Amy interrupted me.

"Sorry... um... my, um, mamabear is Sara and my name is Vincent... well, um, Vince I guess." I heard the crowd saying hi to both of us and blushed because of all the attention that was now being directed towards me. I was never comfortable being the center of attention.

I looked at my mom as she smiled at me. "Ok... go," she mouthed, telling me to make the rounds to the other moms. I went to each one, thanked them for the party just as Jay had, and then leaned in for a kiss. I could feel myself getting more and more excited with each kiss, as each woman kissed me differently but... sensually.

As I completed the circle, kissing my mom last of all, I sat down and watched the last two young men introduce themselves and their moms. I could tell that all but one of the boys were probably in the same position I was... socially awkward, likely from being home schooled and a remote college life.

Jay was probably the least scared of us all. I had the feeling he'd been to parties like this before.

We were all sitting in the penthouse of the hotel, rented out just for this party. Each mom and son had their own hotel room as well, so the penthouse was just for the party.

"Be a doll and get me a glass of red wine, will you?" my mom asked. I nodded and moved to the bar area where several bottles of wine and liquor were set. Amy continued describing how the party was going to proceed as I poured a glass of red wine and brought it back to my mom.

"So each of the boys will get a hat to wear," she said, holding one up as an example. "As you see, each hat is decorated with a card suit: heart, club, spade, or diamond." She passed out the hats one at a time to Emmanuelle, who was sitting beside her, and the group kept them moving to the next couple until they were all distribued. I had the one with the heart on it.

"Our opening entertainment for the night will be a simple game of cards," Amy continued. "Over at the table here, we're just going to play a simple game called War. Hopefully you've played it before, but if not, it's extremely easy.

"As you'll see, the high card wins each hand, but occasionally there's a tie. A tie causes a 'War' so to speak. Each time there's a war, everyone drinks a shot. The winner of the 'war' then gets to have the handsome young cub with that card suit on his hat then stand with her. The cub that was behind her swaps to the other spot.

"The game will continue, no matter what happens, until 9:00 when the game will end. At that point, you get to have the cub at your side for a full 45 minutes to have any fun you would like. Please take no longer than 45 minutes. We'll then restart the game at 10:00 and then stop again at 11:00 for another round of fun.

"Everyone is expected back here by 11:45 to celebrate the ball drop. Then you are free to do whatever you'd like for the rest of the evening."

She paused for a moment and the whole thing started sinking in as the women started talking excitedly amoung themselves. Us boys were... prizes... in this card game, given away to any of the 4 women. I started getting a little nervous, and my hands were shaking. I'd never really been with a stranger before.

"Are there any questions or comments?" Amy asked.

"Any fun we want for 45 minutes?" Becky, the blonde stepmom of Simon asked.

Amy laughed. "As long as you don't break anything." The room erupted with laughter with her.

"I have a question," Emmanuelle asked. She was Carter's stepmom and she looked incredible with dark hair and dark eye-liner to make her look sultry and mysterious. "What happens if our own cub is behind us at 9:00 or 11:00 when the card game ends?"

"Good question," Amy said. "That will be for the group to decide when that happens. Our goal is to have someone... different... at those times. So I'm sure we'll swap as desired."

All the women made comments to each other, causing the room to get loud for a moment.

"Anything else?" Amy asked and everyone settled down again. She looked around but no one had any other questions or comments. "Ok... it's about 8:00... so let's get started."

Everyone slowly rose and walked over to a simple card table that had 4 dining room chairs around it. Each of the moms sat in a chair with her own son behind her or kneeling on the floor beside her. Amy took the deck of cards and shuffled it several times. Then she dealt the hands, one card at a time, moving around the table. Each of the women collected the cards and stored them in a pile in their hands.

"Ready?" Amy asked. "Let's go!"

At that command, all of the women turned over their top card with the high-card winner taking all of the cards and putting them on the bottom of her deck. They boys just watched as the cards moved around from one woman to another as each hand was won. This, then, continued over and over until, after several minutes, there was a tie.

"WAR!" one of the women said.

"Get the shots," Amy said, and each of the boys went and got two shots, one for their moms and one for them. We brought them back to the table and on cue, everyone drank. I didn't know what kind of liquor it was, but it almost tasted like cough syrup. It looked like water, but felt thick as it went down my throat. That was my first taste of liquor ever.

After we drank, I watched the two women lay down 3 more cards, face down, and then flip over the fouth to determine the winner. Since the winner was a 10 of hearts, I was directed to stand behind her and her son was moved to my spot.

The game then continued on and on. As one woman lost all her cards, the deck was re-shuffled and re-dealt, and the game continued. No one cared who won the game of War. All they cared about was which young man would be standing behind her at 9:00. The excitement was with which card suit the war was won... which young man would now stand behind the winner.

I don't know how many Wars there were, how many shots were drank, over that hour. But I do know that I was moved several times and just a little before 9:00 I was standing behind the sultry and mysterious Emmanuelle.

Amy's alarm rang on her phone at promptly 9:00 and all the women were smiling. Simon was standing behind my mom and she took his hand in both of hers as she smiled up at him. I felt nervous as Emmanuelle stood and took my hands, then leaned forward and kissed me.

"It's time," she whispered excitedly, smiling broadly. "Are you ready?" She held my hand possessively as she led me to the door to the penthouse and then down the elevator to another floor where her room was located. All the other women led their young man the same way, each going to their respective rooms.

Emmanuelle led me inside the room and let the door close on its own behind us. At the foot of the bed, she turned towards me and pulled me into her arms, hugging me lightly. Then she kissed me again, her tongue even sliding a little between my lips.

I was so nervous. I was trembling and was barely able to kiss her back. I'd kissed so very few women before and none how she was wanting to kiss. I was in over my head and I didn't know what to do.

"Are you nervous?" she asked, point blank.

"Yes... very."

"Have you ever kissed a woman before?"

I shook my head and looked down in embarrassment. "I mean, my mom... a little."

"Mmm... never, huh? I like that," she said. She put a finger under my chin and made me look at her. "Come on, talk to me. I'm a stranger, you can talk to me about things like this."

"I... I just... I just don't know what to do," I admitted.

"That's ok," she said gently. "These kinds of things do take introductions and practice. You need to find out what you like and what you don't like. Right? I'd love to explore that a little with you."

I looked down again. I didn't even know how to answer her.

"Tell me Vince," she said. "When you look at me... do you get aroused?"

"Oh... uh..." this was far more embarrassing of a question than the kiss one.

"You can look, you know," she said, smiling softly. "I like when you look at me. I want you to get aroused by looking at me." She reached to her side and grabbed the zipper tab, pulling it down to take off her dress. She lowered her dress to the floor and stepped out of it, leaving her only in a black bra and panty set. Her breasts barely captured by the bra. I had a hard time looking at her, but her hand under my chin directed my gaze back to her. She was encouraging me to look at her.

"Look at me. Have you seen a woman in lingerie before?" she asked.

"Yeah... my stepmom... sometimes," I said. My stepmom wasn't shy about me seeing her in her bra and panties. She sometimes relaxed that way on the couch, even, with a light robe over top. I thought it was normal.

I watched, feeling helpless as Emmanuelle reached behind herself and unfastened her bra. She covered her breasts with one hand and let the shoulder straps fall, then pulled her bra away in one sweep. I was now looking at her large, bare breasts. Her nipples were hard and pointed.

I felt my face flush in embarrassment but her hand on my chin redirected my gaze to make sure I was looking at her.

"Does seeing my breasts make you hard?" she asked.

"Yes," I whispered.

She reached down and grabbed one of my hands, setting it on her breast, her hand covering it. She pressed in, making my hand squeeze her breast. It was so soft and nice. I couldn't believe how good it felt. And her hard nipple was pressed into my palm, and then slid between my fingers.

"You like that?" She removed her hand, leaving mine on her breast.

"Yes."

"Good... I like your hands on them, too," she said.

I grabbed her other breast with my other hand and massaged both, squeezing and playing with them. Then I suddenly felt her hand touching me... touching my cock... and I jumped a little.

"It's ok," she said. "You touch me and I touch you." Her hand moved around the front of my slacks, her fingers finding my erection, measuring its length and girth. Then her hands started unfastening my pants and I felt them fall to my knees. Suddenly, she was tugging my boxers down, too, and they fell to my knees as well, leaving my hard shaft exposed.

I felt her hand wrap around my shaft and start sliding up and down, stroking it. "This is a nice cock. Do you masturbate?" she asked.

"Yeah," I whispered.

"How often? How often do you play with this lovely cock?"

"I don't know," I said, blushing in embarrassment again. "A couple times a day, maybe. There's probably something wrong with me."

"Oh, no, Vince. That's exactly what these kinds of events are for... letting you know there's nothing wrong with you. Just because you haven't had sex yet doesn't mean there's something wrong with you. Just because you masturbate doesn't mean there's something wrong with you. I think it's... delicious... that you're still a virgin."

We stood there for a second, barely a foot apart, with my hands massaging her breasts and hers stroking my cock.

"We'll go soft and slow," she said. "Tonight we'll start with soft touching. Just like this."

"Like this," I asked, squeezing her breasts a little.

"Mmhmm... that's great," she said softly. "It's ok to just caress. That feels good. You're making my nipples very hard right now. Does my touch feel good to you?"

"Yes," I whispered. "I'm really excited right now. I um... shit." Unfortunately, everything was throwing me into an orgasm and I got scared.

"What?" she asked, smiling as if she knew what was going on.

"I'm... um... I'm getting close."

"Yeah? Well, that's good," she giggled. "I want you to cum for me."

Suddenly I was overtaken by my excitement and I came, grunting. I felt it erupting again and again and seemed to be so much. I was barely able to remain standing.

"Mmmm... that's nice... very nice," she whispered as it pumped all over her hand, forearm, and stomach, with a good amount dribbling onto the floor.

It took me a minute to realize what I'd done. "I'm sorry," I said. I couldn't believe that I'd made such a mess.

She giggled. "Nothing at all to apologize about." She lifted one hand to her mouth and licked my cum from it, tasting me for the first time. "Mmm... you're delicious. And you're still so hard. Let's come to bed." She pulled my cock, using it as a leash to pull me up and onto the bed. I lay on my back and took my pants and underwear off. She took off her panties and lay beside me.

"And you shouldn't feel guilty that we're doing any of this," she said softly, stroking my cock yet again. "I want to do this with you."

She grabbed my hand and set it first on her abdomen, then slid it lower and lower until I felt the soft downy fur of her trimmed bush and her very wet folds. She spread her legs wider, giving me ample room to touch her. "You're not the only one that's excited." Her hand was on the back of mine still and I could feel her pushing a single finger harder, so that it slid into her wetness.

I'd never felt anything like it before. "Oh, that's really wet," I whispered.

"Mmm... and that feels really good," she moaned softly.

"I don't know what to do," I said, concerned that I was going to do something wrong.

"Oh... I'll help you... don't you worry," she said, grabbing my hand more firmly and using it, sliding my fingers in and out of her pussy and sliding my fingers over her clit.

I watched her close her eyes as the pleasure washed over her and felt so happy that I could make her feel this good. Then suddenly, she grunted, and pulled my hand away as she changed position. She bent over and held my cock with one hand as she leaned in and started licking it.

The pleasure was incredible... far better than her hand even felt. In seconds she had slid me into her mouth, sucking and licking on it. I watched as she used both her hand and her mouth on my cock stroking and sucking as she stared at me.

"Oh... oh my God," I whispered.

"Do you like it when I suck you slow like this?" she asked, sliding the head across her lips for a moment, then sliding it back between her luscious lips.

"Oh God... yes!" I answered more loudly. Fuck! I loved it!

"You seem to be pretty hard again," she whispered. "I like making you hard. You get so big. Can I see what it feels like... in my pussy?"

"Ok..."

She rose to her knees and kicked a leg over my body until she was straddling me. Her pussy looked so incredibly sexy sitting right over my cock.

"I'm going to show you how to fuck." She held my cock against her pussy as she moved her hips forward and back, sliding my shaft against her clit. "Fuck, you've got a very nice-sized cock."

I felt like she was teasing me, sliding the tip of my cock over her pussy lips and swirling it around her clit again and again. And I knew there was more... "Oh my God... can I put it in?"

She slightly changed the angle of my cock and the angle of her hips and let my cock slide right inside her pussy.

"Oh my God!" I was in heaven! Her pussy was so hot and wet, and it squeezed my cock so perfectly. I'd never felt anything like it before!

Emmanuelle moved her hips up and back, sliding my cock in and out of her pussy, fucking me so perfectly. She closed her eyes several times and smiled, feeling my cock inside her. Then she pushed me all the way inside her and ground her clit into my abdomen, slow and deliberate.