Jeanie's Big Boy
by APerv2
Copyright© 2026 by APerv2
My name is Jeanie. Some months back, I started my Saturday morning like I start any other normal Saturday. I showered, made coffee, and began my usual chores. I’d gathered the dirty clothes from my room to put in the washer, and I was heading to Brian’s room to see if he had any dirty clothes to be washed. This is really where the story starts. I opened Brian’s door and stepped into his room. Brian was lying on his bed with his pajama bottoms pushed down to his knees, and he was jerking off.
Let me give you a little background before I go on―
I’m a 34-year-old single mom. I have one son; Brian, he’s seventeen. The last time I saw Brian’s father was the day I told him I was pregnant. He left me standing on my parents’ front porch in tears. I was sixteen. For the last 17 years, I’ve been working hard and devoted all my time to raising Brian and putting a roof over our heads. We’ve done OK on our own so far.
I’m a manager in a large upscale clothing store, Brian is doing well in school, and we live in a nice three-bedroom townhouse in a nice neighborhood. I can’t complain. I’ve dated a few guys over the years, but I never let anything get serious. Either they weren’t very interesting, or I was just afraid of actually letting it get serious. Regardless―It’s just me and Brian, and I’m perfectly happy with that.
If I had one complaint, I suppose it would be the lack of intimacy through the years. Like most other women, I have certain desires. I’m no prude; I’ve had a few one-night-stands over the years―The last one being when I was 30―but found that, all and all, trying to fulfill those desires wasn’t worth the trouble. Blind dates―Bad fix-ups―Guys that think they’re God’s gift―It became easier and less stressful to just do it myself.
I have the Internet, a little “toy”, plenty of batteries, and a very good imagination. I pleasure myself in the privacy of my own room whenever I feel the urge. And for years that’s been enough. Sometimes I daydream about being with this guy or that guy (I wouldn’t mind doing Brad Pitt) and maybe doing something a little ... I don’t know ... out of the ordinary, maybe a little naughty, but when everything is said and done ... I’m OK.
Anyway, back to the story―The fact that Brian was jerking off didn’t really shock me too much. I’d pretty much known he’d been jerking off since he was about fourteen. I do the laundry―It wasn’t too hard to figure out. I had nothing against masturbation. I mean, how could I without being a hypocrite? I certainly did it enough.
I’d had “The Talk” with him, telling him what I thought he needed to know at the time and letting him be. There were a few times, when he was a little younger that I’d seen him trying to hide an erection and a few times I’d had to knock on the bathroom door to make sure everything was OK because he’d been in there for so long―Nothing out of the norm.
Anyway―So him jerking off didn’t really shock me. What actually shocked me was Brian’s erection. When I walked in on him, we both froze―Me standing there at the door staring at my son’s dick ... and him lying on his bed with his dick sticking up in the air, staring back at me. It looked like a banana on steroids. His hand was wrapped around the base, half buried in his pubic hair, and there was still quite a bit sticking up past his hand, curving slightly towards him. It was very thick and the head was very red and it looked almost freakishly long on his relatively small frame. Brian’s not a practically big 17-year-old kid. He stands no more than 5’6” and weighs in at about 140 lbs.
I later thought that maybe it just looked so big because he was so small.
You might think that I noticed an awful lot in just a quick second, but the truth is ... I stood there for a good 5 or 6 seconds, glaring. When I finally gathered my wits, I quickly apologized, stepped out, and shut the door. I stood dumbfounded in the hall outside Brian’s door for a few seconds, then slowly walked to the laundry room with an armful of dirty clothes, thinking about what had just happened. Not only what had happened—but what hadn’t happened too. Brian lay there staring back at me for just as long as I stood in the doorway looking at him. He didn’t let go of himself, and he didn’t try to cover himself up. I chalked it up to the fact that he was probably just as caught off guard as I was.
Anyway...
For the next few days, it seemed that I couldn’t get the picture of Brian—Well ... His dick really—out of my head. Because of that, I suppose I was acting a little “unusual” in front of him. I guess I was kind of embarrassed that I’d been thinking about my own son’s dick so much.
Normally, we joked around and genuinely had a lot of fun together. But now I had a hard time making eye contact, and I seemed to keep the conversations kind of short; enough so that he finally called me on it.
He asked me what was wrong, had he done something to piss me off? I told him ‘No’, naturally. I couldn’t tell him that I couldn’t stop thinking about his dick and that thinking about it made me feel—I don’t know— “Funny”.
I mean ... Jesus. It’s not like I wanted to have sex with him—I just thought about his dick a lot. Not necessarily his dick, but maybe one like his. I wondered what sex would be like with a dick that size. I’m very small and unusually tight. My small vibrator barely fits. I wondered what a dick that size would feel like in my hand and what it would feel like ... inside me. I mean ... I would imagine something that big would feel “different”.
I wondered if something like that would even fit inside someone my size―I’m 5’1” and 105 lbs. ―And if it did fit―Well―I just wondered, that’s all. I thought about that quite a bit in the days after I saw Brian jerking off. I’d like to think wondering something like that isn’t so unusual.
Brian really caught me off guard at dinner a few days later:
“How come you seem so ... distant lately?” He asks me.
“Do I?”
“Is this because you caught me the other morning?” He asked.
“What are you talking about?” I acted like I had no idea what he was talking about.
I wondered if this was how he felt when I’d had “The Talk” with him. I was nervous and extremely uncomfortable.
“You know ... when you caught me jerking off.” He clarified.
I felt my face flush.
“Brian...” I started. I felt a little itch in my throat. “I ... I don’t care if you ... do that. We’ve talked about that ... All guys do it.”
I tried to be as nonchalant as I could but didn’t feel like I was pulling it off.
“Then why are you acting so strange?” he asked.
I sat at the table there just looking at him for a few long seconds trying to figure out how to answer that. What was I going to tell him―I thought his dick was really big and couldn’t help but wonder what it would feel like to have something like that inside me? I didn’t think so!
“Well?” He pushed.
“Well―I guess―I guess I was just a little surprised when I walked in on you I suppose.”
I shrugged my shoulder and hoped that he would drop it.
“ ... Surprised that I was doing that?”
I nodded my head ‘Yes’.
“That’s it?”
“Well, yeah. I guess...”
“Mom?”
“Well, yeah, I mean ... I guess I just didn’t realize that you’re...” I hesitated looking for the right words. “ ... You know ... That you’re not my little boy anymore. You’re growing up and I suppose ... I’ve just been feeling kinda ... kinda old the last few days I guess.”
Brian smiled at me.
“That’s it?” He says, sitting across the table looking at me like he expected more, but that might have just been me being paranoid, I don’t know.
“Well―Pretty much, yeah.” I answered him.
“You sure?” He tried to pry a little deeper. He was quite persistent.
“Well...” ―I couldn’t believe I was going to say it― “It just seemed like you’ve gotten kinda ... Well...”
He sat across from me waiting for me to just say it. “Kinda what Mom?” He urged me on with that silly smile of his. Frustrated, I just blurted it out,
“Kinda big for your age.”
{He was kinda big for any age, but I didn’t think I needed to say that.}
“Really?” He asked with this shit-eating grin. “Ya think?”
I shook my head and rolled my eyes, “I can’t believe I told you that.” I confessed.
“Why, what’s wrong with that?”
“Well, for one thing; that just doesn’t seem like something a mom should be saying to her son...”
He cocked his head and waited for me to go on with that little smirk on his face. He seemed to be enjoying this a great deal.
“And for another thing ... I don’t need you strutting around here like some-kinda rooster in the henhouse.”
“What―You think I might get a big head?”
I looked at him over the rim of my iced-tea glass.
“Afraid I might go knocking stuff off the tables?”
“I guess you think you’re pretty funny, huh?”
“Well ... Yes ... I ... I guess I do. At the very least ... I’m amusing.” He says to me as his smile grew even wider. And I guess he was―Amusing.
I have to admit, I felt a little funny about kidding around with my son about the size of his penis, but I just shook my head and smiled back regardless.
I think I was a little hesitant to continue the conversation. I was afraid of saying something else that would let him know that I’d been thinking about his unusually big dick. And I didn’t need his smart-ass going around knowing that. I’d thought I’d probably already said too much as it was―And I was right.
He seemed to get great pleasure out of teasing me since I’d made it known that I’d noticed his “package”. He had quite the sense of humor too. I commented on a rip in a pair of his underwear a few days later― “Jeez Mom, ya think I might have to get some special underwear made?” was his response. I just rolled my eyes.
“Yeah, special...” I agreed sarcastically.
I made the mistake of asking him what took so long in the shower a few evenings later― He told me, “ ... It takes me a little longer ... As you know ... I have more to wash than most people.”
It was all very amusing, but joking around about my son’s dick was weird, and it only made me think about it more. Deep down, I wondered if maybe that might’ve been his intent.
We went on with our lives. I thought that maybe a few odd looks might have been exchanged from time to time, but that might have just been my imagination. Everything seemed pretty normal ... Well ... Almost normal. Brian helped me clear the table and do the dishes a lot more than usual. I’d even come home from work a few nights to find the living room vacuumed and straightened up. One night, I’d even come home to find that Brian had cooked a nice dinner for us.
At the end of the night, after we’d watched some TV, Brian kissed me goodnight on my cheek and whispered, “You’re not old, and you look great...” I felt myself blush. “ ... For an old woman.” He added with his boyish smile. I slapped him on the arm and gave him a little shove towards the steps.
“Go to bed.” I told him.
As the days went on, I thought more and more about what I’d seen that morning and how it had somehow become such a source of amusement to Brian. Not that I minded. Truth be known, I kind of enjoyed his teasing.
Eventually, I found myself daydreaming about seeing it again and even let different little scenarios run through my mind: Catching him jerking off again. Walking in on him in the shower. Things like that. I even thought about what it would be like to spy on him; watch him jerk off. I found myself thinking about this stuff almost every night, while I tried to fall asleep. Then, of course, I even started to dream about it.
One night, I dreamt I’d just come right out and asked him, “Can I see it?” ... and he showed me! ―It was soft but still very long; hanging down between his legs. I watched it grow right in front of me into this monster hard-on. When I woke up from that particular dream, I was extremely wet between my legs and so turned on that I reached into my nightstand and got my vibrator out. I stuck it under the covers, pulled my panties to one side, and brought myself to an incredible orgasm as I recalled the dream. The orgasm I had came surprisingly fast and was unusually intense. It was no surprise I found myself looking forward to more dreams.
There was a time I would have thought that was pretty messed up ... But now ... I found it pretty―Well―Stimulating. I even thought about maybe getting a bigger “toy” to help satisfy my curiosity.
I didn’t consider anything I was doing bad or wrong. They were just thoughts and dreams. I was sure that plenty of people had ‘Impure’ thoughts all the time. I mean―It’s not like I was acting on them; trying to do anything with my son.
And then one Sunday morning, something happened that changed everything.
I woke up from a dream that should have really disturbed me, but it didn’t. I dreamt that I gave Brian a hand job, got him hard, and then ... let him fuck me. I’d woken up with my finger already inside my coochie, and before too long, I’d grabbed my little vibrator, spread my legs, and was fucking myself with that toy like crazy. I was in another world when I opened my eyes and saw Brian standing in my doorway.
I hadn’t heard him knock. If he did, he called me or even opened the door. I’d just happened to open my eyes ... and there he was. I can’t even tell you how long he was there. I froze, with my legs spread and my dildo still deep inside me. You could have heard a pin drop. As a matter of fact, it was so quiet ... you could hear the humming of my vibrator still between my legs.
I watched Brian, not really comprehending, as he walked right up to the foot of my bed. The big tent in the front of his pajamas ... registers ... but I’m too disoriented to put two and two together. I watched him climb up on the bed without any hesitation, still not believing it. As I watched him crawl towards me on the bed, I lay there dumbfounded, my legs wide open, my vibrator humming away. Unable to respond, thinking surely I must still be dreaming.
He reached between my legs and brushed my hand away from my vibrator. My hand fell away like a weightless feather. He took hold of my “toy”, moved it in and out one or two times very slowly. I remember thinking, “What’s he doing?” Then I felt it slide out of my wet pussy but had no idea what happened to it. I’m watching all this like a slow-motion movie, unable to move.
I feel his hands on my thighs and I’m watching him in shock as he slowly lowers his head down between my legs without a word, looking at me as if he’s hoping I won’t stop him.
I’m starting to finally come to my senses and react now. I’m pushing myself back with my hand and feet, scooting my ass back away from Brian, back until I’m up against the headboard. But Brian’s moving right along with me. I can feel his warm breath on the insides of my thighs and then, my mouth drops open, my eyes bulge out of their sockets, everything becomes clear, “Oh-my-god!” I can’t believe it ... I feel his mouth on me. “Brian?”
I’m digging my heels into the mattress, pushing with my legs but I can’t go back any further. I’m pushing on his shoulders with my hands but I haven’t any strength. The only thing moving is his mouth.
“Brian―Stop―No!” I’m telling him. It sounds like someone else saying it. There’s no conviction in my voice at all. It’s more of a halfhearted plea than an order; barely a whisper. I may not have even said it out loud.
I can feel his tongue moving inside me, his hot breath as he buries his face between my legs, a gentle vibration as he moans softly into my pussy, and I’m paralyzed. “What are you ... You ... You can’t, Brian...” I’m gasping. “You shouldn’t.” I hear myself say. “You can’t do this ... I’m ... I’m your mother...” I hear the words, but there’s no firmness to them; they’re barely more than a whisper; no potency at all.
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