MamaBear Club: NYE Pt. 03

MamaBear Club: NYE with Stepmom, Part 3

Becky and I arrived at the penthouse first, this time, and Amy was there to greet us. She'd already turned on the TV to watch the ball drop and a band was playing. My mom and Carter came in next.

Five minutes late, Emmanuelle walked in, acting like she was practically dead. "Oh my fucking God!" she said loudly as the doors opened. Jay and Simon were on either side of her, helping her walk.

"Was that fun?" Amy asked as she grabbed the champagne flutes from the counter and opened two bottles.

"Fun would be an understatment," Emmanuelle said, acting flamboyantly worn out, as the boys let her plop onto the couch. They then went to get her, and themselves, something to drink. "I'm glad I'm a healthy middle-aged woman, because two strapping young boys like that can really take it out of you," she said, giggling. "You never get a moment's rest."

All the women giggled. I had a feeling they were all wondering what it would feel like.

On the TV, the bands played and the commentators talked all the way up to midnight. We boys handed out the champagne flutes right as the ball was coming down and all went to be at our mother's side.

"10, 9, 8, 7, 6, 5, 4, 3, 2, 1, Happy New Year!!" we all cheered, along with everyone in Times Square in New York City on the television. I kissed my mom, who was definitely feeling the effects of the alcohol tonight. She was frisky with minimal inhibitions. She grabbed my head and stuck her tongue deep in my mouth as we kissed and I could feel her hand grab my cock through my slacks.

Then the boys moved around, kissing each mom in turn, basically with the same outcome. The women might be a little worn down and a little drunk, but they were still horny. All the boys seemed to still have energy, too.

It was about twenty minutes after midnight that the mom's and their cubs started leaving the penthouse and going back to their respective rooms. I held my mom's hand as we went down the hall and into the elevator. Emmanuelle was the only one going to her room alone. Her son Carter was walking with Amy and her son Jay, one on either arm. She was going to get her 45 minutes of extra fun.

My mom used her keycard to open our door and we went inside. The room still reeked of sex, but I guess they all did. The bedspread was a little rumpled, but the bed itself seemed ok. I had no idea what my mom did during her two sessions, but at least she seemed happy.

We both took our time, taking showers and getting dressed for bed. She went first and came out of the bathroom wearing very frilly, thin shorts, and a top that matched with spaghetti straps. It barely held her breasts behind it and showed A LOT of cleavage.

When I finished showering, I dressed just in the shorts I normally slept in. I didn't even feel like wearing a shirt. I crawled into bed, at last, at about 1:00am. My mom was already there, lying next to me. She turned to face me, her bedside light still on, as I got under the covers.

I could still hear the occassionaly pop of firecrackers or bottle rockets as the parties outside wound down.

"Did you have fun tonight?" she asked, sitting up on her elbow so that she was a little higher than me. She didn't look the least bit tired and seemed very anxious to talk.

"Yeah," I said, smiling. "I didn't know what to expect, but it was... fun."

"I wasn't exactly sure what to expect either, but I thought Amy did really well in setting it up."

"Yeah, it was good."

"Who did you get to spend time with?" she asked, smiling at me, obviously very interested in my night. She knew this was my first experience with a woman.

"Um... Emmanuelle first and then Becky," I said.

"Ooh, how was your time with Emmanuelle?" she asked, her eyes flashing with interest. "She seemed like she'd be really exciting."

"It was nice," I said softly.

"So?" she asked, impatiently. "Give me some details! What did you guys do first?"

"We kissed," I said.

"And? Did you like kissing her?"

"Come on mom... yes," I said, embarrassed.

"Oh like there's something to be embarrassed about kissing. Come on," she said. "You don't mind talking to me about this do you?"

"Yeah, I guess it's ok... I just feel kinda..."

"Like naughty maybe?" she asked. "Like you're doing something you shouldn't? Or maybe thinking something you shouldn't?"

"Yeah..."

"That's ok. Those kind of thoughts are normal. You know you can tell me anything." I nodded. It didn't feel like I should be telling my own mother details about my sexual encounter with Emmanuelle. But maybe that was normal for boys to do. I didn't know.

"So... you kissed. How'd that make you feel? Good?" she smiled.

"Yeah," I smiled back. It made me feel real good, I had to admit it.

"And did kissing lead to other things?" she said, expectantly.

"Yeah... kinda," I said, hesitating.

"Yeah, kinda," she mocked my voice. "Look at you beating around the bush. You know we've known each other for a while now. We can talk, right?"

"I... I just feel like you'll get mad at me or something," I said. I knew we were close and I wasn't sure if talking about another woman would make her mad or not... especially telling her what happened.

"No... I won't. I'm happy for you. It's why we came here," she said.

"Ok... well... after we kissed we just... you know... touched each other some," I said.

"You did?" she asked. Her hand started stroking her neck and slid down inside her nightshirt to play with her breast, specifically to pinch her own nipple a little. "Some? So what does that mean?"

"Like... I... I touched her breast. And she touched me... down there," I said, still a little too shy to tell her what happened.

"Your cock?"

"Yeah... And I touched her... like... down there," I admitted, watching my mom tease her breast even more. Her nipple was almost visible now as her hand had pulled down the material a bit. Her finger swirled around it and occasionally pinched and pulled it.

"You touched her down there?" she asked. "What did you think?" She smiled as if knowing exactly what I thought. She adjusted her position, moving closer to me and suddenly her hand slid under the covers and she started touching my inner thigh that was closest to her. Her touch sent shivers through my body as her fingertips stroked up from my knee getting awfully close to my cock.

"God it was... so warm... and wet," I said as I remembered it. It was the first time I ever touched a woman's pussy. "I... I liked it."

"Did she taste you?" she asked. She smiled at me like she really wanted to taste me herself.

"Yeah," I admitted.

"Really? She sucked on your cock?" Her fingers were now dancing at the leg band of the shorts I slept in and it was giving me a hardon.

"Yeah."

Her hand went over the shorts and touched my cock through the material. Her fingers curled over it as best they could and she slowly stroked me over the thin material.

"Ooh, I see you're excited just thinking about it," she smiled. "You're very hard."

"I'm... I'm sorry mom," I said, blushing I was so embarrassed. I couldn't believe I was getting hard next to my mommy.

"No... It's ok. You're young," she said giggling. "Young men tend to get excited easily. I happen to like that." She looked at me for a moment, still stroking me, then pulled the blanket down off me so she could see what her hand was doing. "You know... I can help you with these things, too," she said. "I mean I used to do stuff with guys... maybe things you've never thought about."

I moaned softly, unable to answer her about that. I mean, I thought about it all the time. I fantasized about my stepmom all the time.

"So... what did you do next?" she asked, sliding even closer to me. Her body was so close I could feel the heat from it. She kicked a leg over mine, both holding me in place and keeping my legs apart a little. "Did you get naked? Did you get her naked?"

"Yeah... She took off her dress and was wearing really sexy bra and panties underneath," I said. I was starting to breath harder, my erection growing to full mast. "And she took those off, too."

"I assume she was a little... aggressive. Did she get on top of you?"

"Yeah."

"Mmm... Did she grind her pussy against your cock?" she asked. I could feel her leg sliding up and down mine. Her skin was so smooth and soft... and warm.

"Yeah. And her pussy was like really wet and she just slipped it inside her. And then we... had sex," I whispered.

"That's really exciting! Did you fuck her really good or did she fuck you?"

"I... I think I fucked her really good," I said softly.

"Did she cum?" she whispered back, her hand still stroking my shaft. The head was starting to peek out from the top now.

"Yeah... a couple times I think," I said. I didn't know for sure, but it seemed like she had a couple orgasms to me.

"See, you do like our conversations. You are so hard," she whispered, sliding her hand inside the waistband of my shorts and stroking my cock directly now. Her hand was warm and insistent.

"I... uh..." I was so embarrassed and excited that I could barely speak.

"It's ok," she said, sliding her hand up and down my long shaft. "It was fun, right?"

"Yeah... sex is pretty cool," I whispered.

She let go of my shaft for a moment and started pulling my shorts down. She got up on her knees and used both hands to pull them off my legs, tossing them to the floor of the hotel room. I was now completely naked. Then she slid between my spread legs and lay down, her face so close to my crotch. Her hand grabbed my shaft again, stroking it slowly, with a new closeup view.

"You don't mind, do you?" she asked as she licked up the side of my shaft and then nuzzled her face into my balls. "Do you like when I do this?"

"Yeah," I moaned. God... I loved it!

"Tell me... how did it feel when you were inside of her?" she asked, letting her tongue flutter around the head.

"Oh my God," I groaned, barely able to even think to answer her.

"Nice... and... wet?" she said as she took the head into her mouth, sucking in it.

"Yeah." Her mouth was so perfect and drove me insane with pleasure.

"Was her pussy nice and tight? Like this?" she asked as her hand squeezed my shaft as she stroked it, her mouth and tongue still working on the head.

"Yes," I moaned.

She slid my cock from her mouth and then sat up on her knees. She kicked a leg over one of mine and sat with her pussy grinding into my thigh as she stroked me.

"Do you like my boobs?" she asked and I nodded dumbly. She grabbed the bottom of her top and pulled it over her head, exposing her breasts to my feasting eyes. The were so perfect. "Do you want to touch them?"

I nodded and reached up with both hands and grabbed her breasts, squeezing and lifting them, playing with the nipples a little. "They feel so good mommy."

She moved again, sliding her pussy over to my cock, and then rubbing against the hard shaft. Her pussy was so wet and warm, very much like Emmanuelle's, and she used my hard cock to tease herself. She circled the head over her clit and moaned softly.

"Mommy?" I said as I looked up at her. I couldn't believe we were doing this. I must have had a strange look on my face, because she thought I wanted her to stop.

"Do you want me to stop, baby?" she asked.

"No... I... I don't want to stop," I moaned. Hell no I didn't want her to stop!

"Tell me what you want, baby," she said. She looked down and watched as she moved my cock around her pussy.

"Mommy please... please," I begged, panting, barely able to speak.

"What? Tell mommy what you want."

"I... I want to put my cock... inside you," I said. "I want to... to... to fuck you."

"You do?" she said, smiling down at me. "Watch baby... look down here," she said, telling me to watch where my cock and her pussy met. Slowly... teasingly... she guided the head to her hole... then dropped her hips... slowly... sliding me inside.

"Oh my God," I panted as I watched my cock disappear inside her, inch by inch.

"Is that what you wanted, baby?" she asked as she started grinding on my cock, sliding me in and out of her wetness.

"Yes mommy!" I moaned loudly. God it felt so good to have her pussy squeezing my cock like that.

As she pushed down onto me, I arched my hips up repeatedly, slightly fucking her. She pressed down on me when I was fully inserted, as if trying to push even that last millimeter inside. She then moved her hips forward and back, sliding me in and out of her wetness.

"That's the way... yeah... Did she ride you like this, baby?" she asked, looking down at me with half-closed eyes. She was feeling really good.

"Yeah, but... this feels so much better mommy," I moaned.

"Oh... fuck," she hissed as my cock filled her. "You like it when mommy does this to you?"

"Yeah... yeah mommy. But I... I think I'm gonna cum," I moaned again, breathing harder. The way she looked and the way her pussy was practically milking my cock made me so damn excited. I was far more excited than I'd ever been before.

"Yeah?" she asked, smiling brightyly in surprise. She was definitely going to love this... a young man that cums and is ready to start again. "Are you gonna cum already baby?"

She slid off my cock, and instantly grabbed it, stroking it, then bent down and began licking it.

"Mmm... baby... let mommy have it," she moaned.

"Oh God," I said, barely able to even talk. "I'm... Oh God... I'm cumming." Instantly I felt the cum jet from my shaft as her mouth sealed itself around the head. She moaned softly, obviously loving that I was cumming for her, and she swallowed every drop. It was the most amazing sight that I never, ever expected to see.

We locked eyes as she kept sucking, getting every drop from me, her hand stroking up and down with a firm grip.

"So much cum!" she whispered as if amazed.

"I'm... I'm sorry mom... I lasted longer with her. I'm sorry," I apologized over and over. I was so embarrassed.

"It's alright," she smiled, still stroking my shaft and kissing the head, her tongue flicking over it occassionally. "It's ok baby. I love to make you cum. And I love that mommy could make you cum so quickly. That's nice sometimes, too. You taste so good."

She took her time cleaning off my cock and making sure to get every drop of my cum. It felt so... motherly.

"Baby, did you taste them tonight?" she asked as she lay back on the bed.

"Down... down there?" I asked.

"Yeah."

"Becky... but not Emmanuelle," I said.

"Yeah? You licked her pussy?" she smiled as if that was important to her.

"Yeah," I said. "She showed me what to do."

"Mmm... well, since you got a nice cummy," she said, smiling and spreading her legs. "Then maybe I can have one now. I think we need to do that. Come over here."

"You... you want me to lick you?" I asked, a little embarrassed to see her laying back and so lewdly playing with her pussy.

"Yeah," she said as I got on my knees and moved between her legs. "Start up here," she said, indicating her lips for me to kiss. I was on all fours and leaned into her. She put her fingers on my chin and I followed her her into a deep kiss. She used her tongue to play with my lips and encouraged me to do the same, before sliding it into my mouth.

"Mmm... good boy... I love kissing you," she said. "It's all about enjoying the experience. Just take your time... and make it sensual. Every time you touch, every time you kiss... just take your time."

She used her hand to guide my mouth to her breast and led me to lick her nipple, circling it and then making long swipes over it.

"Yeah, that's nice," she said and then pushed my head lower.

I slowly kissed and licked down her body, stopping to flick my tongue over her bellybutton for a moment.

"Oh, that feels so good," she moaned, "watching you kiss my body like that. God I can't wait to feel your mouth on my pussy."

She spread her legs a little wider as I moved down between them and lay on my stomach. "Yeah... start licking... right there," she said, indicating a spot midway up her thigh. "And get closer... and closer. Tease me a little. Yeah... just like that."

I licked closer and closer to her pussy, my tongue finally sliding over the outside of her swollen labia. She was moaning softly as she watched me.

"Mmm... that's it... mommy likes long licks," she said excitedly. I started licking between her labia, delving into the wetness within, tasting her for the first time. My long licks ended with a flick over her clit and that definitely excited her.

"That's perfect," she moaned. "We'll keep working on this... maybe every day even. You'll be a master."

I licked and sucked a little, tasting her and doing everything that seemed to drive her crazy. Her clit was definitely a good spot to both lick and suck and I spent a bit of time teasing it.

"Mmm... you're getting so good at that... Oh, baby boy... mommy likes that... Mmhmm... yeah... right there... That's so good... Oh, my baby boy... I really like your tongue right there... just spread that pussy wide open."

She used her fingers to pull her lips open, exposing more of her wetness to my mouth, and I slid my tongue in as far as I could. She used her hands on my head to encourage me to tongue-fuck her a little bit before guiding me back up to her clit.

"Your mouth feels so good on mommy's pussy," she whispered, panting. "It's such a turn on to watch you do that... Right there... you got that... yes... I'm cumming... I'm cumming."

She grabbed and held my head still as I alternately sucked and licked her clit. It was just the right combination for her and I felt her body shake. Her legs clamped onto my head, holding me in place as she moaned more loudly, her pussy gushing over my face. And then she relaxed and released me.

"You did great, baby," she praised me, smiling as I kept licking. "Yep, yep, you got it baby," she said, grabbing my head suddenly. "Easy... go slow... My pussy's so sensitive."

In just a minute, she pulled me from between her legs and brought me up to lay beside her.

"I... um... I have a gift for you," she said.

"A gift for me?"

"A New Year's present," she said, handing me a small box.

"What is it?"

"Open it, silly boy. It's something to help us start the new year right."

I peeled the wrapping paper off and opened the box. Inside was a metal contraption that I could make nothing of. I held it up, turning it this way and that trying to figure it out.

"What is it?" I asked.

"It's a little... something... that the club recommends to keep us together." She took it from me and used a little key to unlock it, separating it into two pieces. "It's something to make sure that I'm the only woman you love. This part goes on like this..." She pushed one part onto my cock, sliding my balls through it. "Then this slides on like this." Then she put it back together, sliding my cock into a little cage. I heard the click of the lock before she let me go.

She held the key up. "I hold the key now... your cock is mommy's baby," she smiled. "You're my baby boy."

I looked at my cock, all caged and trapped. There was no way I could have sex with that thing on. I couldn't even masturbate. And she held the key. She was making sure that I could only fuck on her terms.

"Come on. Let's sleep for a while now," she said. "I'm sure I'll wake up in a couple hours wanting you some more." She grabbed my cage and I felt her fingers slide between the openings to touch my cock. "Mommy needs to use your nice, big cock."

"Ok mommy," I said, laying my head on the pillow next to her, facing her, hugging my arms around her.