Popping My Step-son's Cherry For Christmas

I suppose most boys my step son’s age were interested in sex. I mean, don’t all eighteen year olds think about it morning to night? I remember my own eighteen, having sex with my first boyfriend in the back seat of his father’s car. How could I forget? We made love in that car every chance we could. The old bench seat in his dad’s Chevy made for a great place to learn about sex. He and I had sex quite a bit before I found out he was sticking it into someone else on the side.

And then I met Billy’s father and he really taught me what good sex was all about. He took his time with me, being gentle at first until he knew I could handle his dick. After that, we fucked like rabbits. I lost count of how many times we made love after he proposed to me and we were married. Oh no. That man had a high libido.

We had a few rough spots, mostly due to his work schedule. He was an over-the-road trucker, hauling loads all over the country and being gone for days or even weeks at a time. It made for some lonely nights without him but I loved him and understood that his job paid well enough for us to have a nice home. So I took care of his son and waited for him to come back to me.

And being a good mother, naturally, I wanted to find out what sort of things Billy was interested in, maybe I would find a hint on his computer.

What I didn’t expect to find was his browsing history full of porn.

I tried not to dwell on it, telling myself it was natural for boys to be curious about sex. After all, boys will be boys. But, I found myself thinking about that more and more as I started watching some of the videos he had bookmarked on his browser. And that’s when I began to notice the type of girls he was interested in.

They were older, mature women with large breasts. Granted, some of them looked like they were in their twenties or thirties, but generally, I couldn’t help but wonder if he had a thing for older women. A niggling thought told me that the kind of women Billy watches looked suspiciously like me.

I knew I wasn’t a prude, even though my husband was a bit older than me. My body was still firm and tight. I still had curves in all the right places and I had the largest breasts of all my friends. In fact, I’d even been told by a couple of my friends that they envied my body, especially my large breasts. And I did enjoy getting compliments from men, even though I tried not to show it.

I found myself wondering if Billy was looking at these women and thinking about me. It was certainly possible since I did look a bit like them. I could be the same woman that some of the younger men in this town fantasized about. That was a heady thought but I was his step mother. That was supposed to make him immune to any sexual thoughts about me.

The idea that Billy might have thoughts about me sent shivers of both revulsion and excitement through my body. I was ashamed that the thought of my own step son possibly desiring me, lusting after my body, had my pussy quivering in response. I shouldn’t be having these kinds of thoughts. It was wrong. He was my step son, not a potential lover.

Yet, there I was, watching these videos and feeling myself become aroused at the idea that my own son may have jerked himself off while watching them.

And the longer I watched these videos, the more I found myself wanting to see how much Billy’s cock looked like his father’s. But it wasn’t something that a normal step mother ever thought about.

But, what would it look like? How big was he? Did he shave it like some guys do? That was what young men do nowadays, right?

I had a sneaking suspicion that Billy’s cock was very similar to his father’s and that excited me more than I wanted to admit. The thought of seeing my step son naked, stroking his hard cock, just made my pussy quiver more and I found myself becoming more and more aroused.

It took a long time before I realized that my fingers were between my legs, stroking my pussy, teasing my clit and rubbing my juices all over my fingers.

That’s when I knew that I had gone too far and pulled my fingers out of my pussy. I cleaned up and then turned off the computer and snuck out of his room. As I walked back to my bedroom, I couldn’t help but wonder how I would approach my son about what I found out about him.

It wasn’t too far gone after his curfew when I heard his presence come into the house. I listened as he went to the kitchen and grabbed a drink before going to his bedroom.

After a few minutes, I got up and walked out into the hallway, hesitating outside his closed door.

“Billy?” I called out. “Are you decent?”

“Yes Mom,” he answered, sounding a little confused.

I hesitated for a second before opening his door and looking inside. “I need to talk to you, honey,” I said.

“What about, Mom?”

“I...” I hesitated and then walked inside, closing the door behind me. “I found something on your computer.”

“Oh?” Billy said, suddenly looking nervous. He looked down at his hands.

“I...I’m not mad. But I do have some questions.”

“Okay, Mom,” he said, swallowing hard and looking back at me.

“I mean, I think it’s natural for boys your age to be curious about sex, but...” I looked at him, feeling myself blush. “I didn’t expect to find...well, what I found.”

“And that is?” he asked, still looking a little nervous.

“Well, you seem to have an interest in older women,” I answered, looking him directly in the eyes. “In fact, I’d say that you’re only interested in women that are a lot older than you.”

“Um, I guess I never really thought about it,” he said.

“I have,” I admitted, looking down at my hands. “I mean, I’ve been thinking about it since I saw the kind of porn you like to watch.” I took a deep breath and looked back at him. “And the truth is, I think you’ve got a thing for mature women with larger breasts.”

He nodded his head slightly but didn’t say anything.

“I guess, what I want to know is if you’re...if you’re fantasizing about me.” I knew that my face was flushed with embarrassment and I couldn’t believe that I was asking my son this question.

“Mom?” he said, his face now turning bright red.

“I mean, I’ve seen the way you look at me sometimes,” I said quickly. “And I’ve noticed the way you react to me when I dress in a way that shows my body.”

“Mom, I’m sorry,” he said, looking away.

“It’s okay, Billy,” I said softly, stepping closer to him. “Really, it is. You don’t need to be embarrassed.”

He nodded his head and looked up at me. “I can’t help it, Mom. I know that I shouldn’t, but...”

“Shhh,” I said, touching his lips with my finger. “I’m not mad at you. In fact, it makes me feel good.”

“It does?” he asked.

“Yes,” I answered. “It makes me feel desirable.”

“But you are,” he replied.

“Why thank you,” I said, smiling as I ran my fingers through his hair. “That’s very sweet of you to say.”

“It’s true,” he said.

“I’m your step mother,” I pointed out. “It’s my job to make sure that you feel loved and secure.”

“I do, Mom,” he said, smiling.

“So, can I ask you a personal question?” I asked.

“Sure Mom. Anything.”

“Well, I was wondering about your cock.”

“My...cock?”

“Yes. I’m curious if it looks like your father’s.”

“Um, I’m not sure,” he said. “I’ve never seen his. Why?”

“Oh, I was just wondering.”

“It’s just a little sudden, that’s all. But I guess I’m okay to show you, if you really want to see it.”

I felt my pussy quiver as he spoke. “Are you sure?”

“Yeah, why not?” he said, unzipping his pants and then pulling his pants down. “Here.”

“Oh!” I said, involuntarily bringing my hand to my mouth as I looked at his hard cock. “You are big, aren’t you?”

“Is that bad?” he asked.

“No, not at all,” I said, reaching out to touch the tip of his cock. “It’s just that...” I looked down at my chest. “Well, let’s just say that I was right.”

“Right?”

“Your cock looks a lot like your father’s.”

“Really?” he asked, looking up at me.

“Yes,” I said, smiling and nodding my head. “I mean, I can’t really tell you how many times I’ve been with him.”

“Mom?” Billy said.

“Yes dear?”

“Can I tell you something?”

“Sure. Anything.”

“I never been with a girl before.”

“Are you saying that you’re a virgin? A virgin with a cock like this?”

Billy nodded his head. “Yeah,” he said, looking down at the floor.

“Oh, honey,” I said, putting my hand on his arm and gently rubbing it. “Why didn’t you tell me?”

“I guess I was worried,” he answered. “I mean, aren’t guys with big dicks supposed to be confident and stuff?”

“Confidence can come in many different forms,” I said, lifting his chin up so he could look me in the eyes. “Don’t ever think that a boy being a virgin means that he’s not a real man.”

“Really?”

“Yes. Really,” I said, smiling at him. “There’s nothing wrong with being a virgin. It’s natural. But what I will tell you is that you need some practice.”

“What do you mean?” he asked.

“Well,” I said, stepping closer to him and running my hand up and down his arm, “I’d be happy to teach you how to please a woman.”

“Mom?”

“It’s okay, honey. I know that you’ve got all these feelings, but I also know that you don’t have any idea what to do with them. So, let me help you out. I’ll teach you everything you need to know.”

“But...you’re my mother.”

“And that’s exactly why I’m offering to help you,” I said. “You’re a good looking boy. You deserve to experience life, especially when it comes to sex. And since I love you so much, I want to make sure that you’re ready for when the time comes.”

“So you really think I’m attractive?” he asked.

“Honey, there isn’t a woman in the world who wouldn’t want to get naked with you,” I answered. “Now, let’s see what you can do with your tongue first.”

“With my tongue?” he asked, looking at me curiously. “What do you mean?”

I smiled and reached for the top button of my blouse. “Well, one thing you need to know is that women love to be kissed, licked and caressed. And one of the best places to start is with their breasts.” I began unbuttoning my blouse, revealing my black lace bra. “And it’s not just about sucking on them. Sometimes, it’s the thought of a man doing something so intimate that really turns us on.”

Billy stared at my breasts as I unbuttoned my blouse. He swallowed hard before speaking. “Mom, are you sure this is a good idea?”

“Trust me, honey,” I said, stepping closer to him and gently placing my hand on his face. “This is just between you and me. Consider it a secret Christmas present from Mom.”

He nodded his head and smiled. “Okay, Mom.”

I continued unbuttoning my blouse until all the buttons were undone. I opened my blouse and then shrugged out of it, letting it fall to the floor behind me.

“I know that you’ve been looking at me, honey. You’ve been checking me out, trying to figure out what I look like under my clothes. I mean, I know that I have large breasts.”

Billy nodded his head as he looked at my breasts. “They’re so big,” he said.

“Yes they are,” I said, reaching behind me and unzipping my skirt. I pushed it down over my hips and then stepped out of it, kicking it away with my foot.

“Do you want to see the rest?” I asked.

Billy nodded his head again.

I smiled at him as I reached behind my back and unhooked my bra. I held it in place, covering my breasts, as I looked at him. “Are you sure you’re ready, honey?” I asked.

Billy nodded his head and swallowed hard. “I’m ready, Mom,” he said softly.

I let go of my bra and let it fall to the floor. I stood in front of him, completely naked, waiting for his reaction.

“Oh wow,” Billy said, staring at my breasts.

“Do you like them?” I asked, lifting my arms up to cup my breasts, pushing them up and together.

“They’re so big and beautiful,” he said, reaching out to touch me.

“Mmm, that’s good,” I purred. “I want you to be able to touch me whenever you want.”

He nodded his head as he ran his hands over my breasts, cupping them gently.

“You can squeeze them if you want,” I said. “Just be gentle.”

Billy squeezed my breasts, gently at first, but then harder as his confidence grew.

“That’s it, honey,” I said, smiling at him. “You can play with them all you want.”

Billy began kneading my breasts, squeezing them and then letting go. His fingers brushed against my nipples, causing them to become erect.

“That’s nice,” I said, closing my eyes and enjoying the sensation of his touch.

“I’ve always wanted to touch them,” he confessed. “They’re so big and soft.”

I smiled at him and then took his hands in mine. “Come with me,” I said, leading him to the bed.

“What are we going to do on the bed?” he asked.

“Well, I’m going to teach you how to please a woman. But first, I want to see how good your tongue is. So, I want you to use your mouth and tongue on my pussy.”

“Use my mouth and tongue on your...pussy?”

“Yes,” I said, laying down on the bed and spreading my legs open. “Come closer and look.”

Billy walked over to me and then knelt down between my legs, looking at my pussy.

“It looks like a little flower,” he said.

“It does, doesn’t it?” I said, smiling at him. “Now, I want you to get real close to it and sniff it.”

Billy leaned forward and smelled my pussy. He took a deep breath, inhaling the scent of my arousal.

“That’s nice,” he said.

“What do you smell?” I asked.

“Something sweet and musky,” he answered. “It smells good.”

“It does, doesn’t it?” I said, reaching down and running my fingers through his hair. “Now, I want you to taste it.”

Billy hesitated for a moment before leaning forward and sticking his tongue out. He licked the lips of my pussy, tasting my juices.

“Oh yeah, that’s it,” I said, encouraging him. “Lick me all over, honey. Suck on my clit.”

Billy licked my pussy from bottom to top and then sucked on my clit.

“Oh yeah, that’s it,” I moaned, pushing my hips up against his face. “That feels so good.”

He was rather clumsy, but what he lacked in experience, he made up for in enthusiasm. And the very fact that is was my boy doing this, was driving me mad with arousal.

“That’s it honey,” I said, moaning and writhing on the bed. “Use your fingers too.”

Billy slid one of his fingers inside my pussy, feeling my wetness.

“Oh yeah,” he said. “You’re so wet and hot.”

“That’s because you’re making me feel good,” I said. “Now, keep licking and sucking on my clit. Move your fingers in and out, keep to a steady tempo”

Billy did as I asked and soon, I found myself climbing towards orgasm.

“That’s it,” I said, my hips moving up and down as I got closer. “I’m going to cum.”

Billy kept licking and sucking on my clit, his fingers moving in and out of my pussy.

“Oh yeah,” I cried out as my orgasm hit. “Oh God yes!”

My whole body shuddered as I came, my pussy clenching around his fingers.

“That’s it,” I gasped. “Keep doing that.”

Billy kept licking and sucking on my clit as I came, his fingers moving in and out of my pussy.

“Oh God,” I said as my orgasm subsided. “That was amazing.”

“You really liked it?” he asked.

“Yeah, you’re a natural,” I said, smiling at him. “So, are you ready for me to teach you the next step?”

“Next step?” he asked.

“Yeah,” I said, sitting up. “Now, I’m going to show you how to use that big dick of yours.”

“I’m a virgin,” he reminded me.

“I know,” I said. “But that’s not going to last long.”

“Are you sure about this?” he asked.

“Yeah, I am,” I said, smiling at him. “And trust me, it’s going to feel good.”

I stood up and walked over to the edge of the bed. “But first, I simply must taste it.”

I knelt down in front of him and slowly pulled down his underwear. His cock sprang free, standing tall and proud.

“Oh my,” I said, admiring his size. “You’ve definitely got a big dick.”

“Really?” he asked, smiling.

“Yeah,” I said, reaching out and wrapping my fingers around his shaft. “In fact, I think it’s bigger than your father’s.”

“I hope it feels as good,” he said.

“Don’t worry,” I said. “We’ll make sure that it does.”

I stroked his cock, feeling the smooth skin and the warmth of his flesh.

“That feels so good,” he moaned.

“I bet,” I said, smiling up at him. “Now, just sit back and relax. Let Mommy take care of you.”

I continued stroking his cock, watching the tip begin to glisten with pre-cum.

“Oh yeah,” I purred. “I can’t wait to taste that.”

I leaned forward and licked the tip of his cock, tasting his pre-cum.

“Mmm,” I said. “So sweet and tangy.”

I leaned forward and took the tip of his cock into my mouth, sucking on it gently.

“Oh yeah,” he groaned, closing his eyes and leaning back on his elbows.

I swirled my tongue around the head of his cock, savoring the flavor of his pre-cum.

“God, m-mummy...” he said.

I smiled and then slowly began to slide my mouth down the length of his cock. Inch by inch, I took more and more of his dick into my mouth.

“Oh fuck,” he moaned, his eyes rolling back in his head. “That feels so fucking good.”

I slowly bobbed my head up and down his shaft, taking as much of him as I could.

“Jesus,” he moaned. “Mom, I’m not gonna last very long if you keep that up.”

I pulled back, letting his cock slip out of my mouth. “It’s okay,” I said, smiling up at him. “You’re doing just fine. But, let’s not forget the other part of the lesson.”

I stood up and pushed him back onto the bed. “Lay down and let me ride that big cock.”

Billy scooted back and lay down on the bed, his hard cock pointing up at the ceiling.

“Oh yeah,” I purred, climbing onto the bed and straddling him. “That’s the perfect cock for me to break in.”

I reached between my legs and grabbed his cock, positioning it at the entrance to my pussy.

“Here we go,” I said, sliding down onto his cock.

“Oh fuck,” he groaned as the tip of his cock pushed past my lips.

“Ooh, you’re so big,” I moaned as his cock stretched my pussy.

“Oh God,” he groaned, his eyes closed. “That feels so fucking good.”

“That’s it,” I said, sinking down until his cock was fully inside me. “Oh fuck, that’s a big dick.”

I started moving up and down, riding his cock, taking him deep inside me, feeling his girth stretch against the inner walls of my pussy.

“Jesus,” he moaned, his hips thrusting up to meet mine.

“Fuck,” I moaned, picking up the pace. “That’s a big cock.”

Billy was gasping for breath as I rode his cock, his hips bucking beneath me.

“That’s it,” I purred. “Cum for me, baby.”

“Oh God,” he moaned, his hands gripping the sheets tightly. “I’m gonna cum.”

“Cum for me,” I moaned. “Cum inside your mother’s pussy.”

“Oh fuck,” he moaned as his body began to shake.

“That’s it,” I said, fucking him hard and fast. “Cum inside me.”

“Oh fuck,” he moaned, his voice trembling.

I slammed down on his cock, taking him all the way inside me.

“Yes,” I cried. “Yes!”

I felt his cock explode inside me, his cum filling my pussy.

“Oh fuck,” I cried as my own orgasm washed over me.

My whole body shook as I came, my pussy milking his cock, draining every last drop of cum from his balls.

“Jesus,” he moaned, his cock still throbbing inside me.

“Oh my God,” I panted, collapsing on top of him.

We lay there for a while, his cock still buried inside me. I let out a deep, satisfied sigh as I enjoyed the feeling of his hot cum deep in my pussy.

“Mom, that was incredible,” he gasped, his eyes closed.

“It sure was,” I agreed, resting my head on his chest. “And trust me, honey, that’s just the beginning.”

“Really?” he asked.

“Of course,” I said, lifting my head up and looking at him. “There’s so much more I need to teach you. You didn’t last as long as I would like, but thats absolutely fine.”

“I can’t wait,” he said, smiling.

“Neither can I,” I said, leaning forward and kissing him softly. I stole a glance at his bedroom clock on his bedside table. It was past midnight.

“Merry Christmas, Billy.”

He smiled. “Merry Christmas, Mom.”

Thank you for reading, please consider checking out my other stories on Smashwords. Merry Christmas!