Prequel to "My [35F] son [18M] manipulated me into letting him penetrate me": Just The Tip

Prequel to a story I posted about how my virgin son tricked me and penetrated me. This is about the first time I let him insert just the tip of his penis in me.

Please read my first story first: /2026/06/story-52772

FYI, someone else copied my story and reposted it under a similar title a few days later. I have no idea who that is. They later changed the author to the same name as me when people started calling out the rip off.

Recap:

I'm a 35 year old divorced mom, and I live with my son who just turned 18. He had a bad experience with a girl recently where he came in her mouth basically instantly, which resulted in her calling him a "pencil dick premie" and storming off. He does have a very small penis, about 4", and cannot hold his load at all. He went to a strip club after that and got kicked out for cumming in his pants, after which the stripper also said something mean to him. I felt terrible about this because it has wrecked his self-confidence.

Nonetheless, he is very interested in sex as a virgin and is always eager to learn about the female body. He asked if I would show him my body and I probably shouldn't have, but I agreed. That led to him begging to touch and lick. I try to be a positive role model for him and I don't stop him when he feels me up and asks me to show him parts of my body because I think as a healthy young man, he needs to be exposed to a biological female so he does not feel mystified. I tell myself that I'm just using my own body as the prop for my son's sex education.

I have been walking naked around him and I don't mind when he does the same. A few times I even caught him coming out of the shower with a fully erect cock and he dangled it in front of my face. This eventually led to me masturbating him. I put his penis in my mouth twice, but I wouldn't really call them blowjobs as he came within 10 seconds (the first time it was literally after 3 sucks, lol). We are not in a freeuse relationship and I made it clear early on that there would be no penetration, but I don't stop him from feeling me up or putting his fingers in my vagina. He did recently ask if he could put "just the tip" inside my pussy. allowed him to after a lot of begging on his part ("please mom! just the tip for a second so I can see what a pussy feels like!") on the strict condition that he would not go deeper than the head of his penis, that I would do the inserting, and my hands would be kept against his chest to make sure he doesn't "accidentally" go too deep. He stayed inside for a few seconds after which I pulled his penis out because I could feel it starting to swell and he came on my stomach. Since then, he has repeatedly asked to put the whole thing in but I denied him.

New story starts here:

This is how it happened that I let him put the tip of his penis in my vagina. We were cuddling in my bed facing each other. I was topless in a small g-string (see attached photo, that is a bikini but very similar). He had my body pulled over his as sucked my nipples and fingered me. Eventually he pulled the g-string aside and got more forceful with his fingers. Before I knew what was happening he was rubbing the tip of his penis on my lips with my panties pulled to the side.

"Be careful," I told him, "You know you aren't allowed to penetrate me with your penis."
"PLEASE mom! Just for a second, so I can see what a pussy feels like! You said you wanted to help me."

He looked so sad but his dick was like steel.

"Just rub it on mommy and fuck my thighs baby, it'll feel like just being inside, I'll close my legs tightly and you can slide the shaft against mommy."
"Just for a second mommy! I won't go deeper than the head! I just want to feel it for a second!"

We argued back and forth for a couple minutes and finally he agreed to try my suggestion. The thing is that I was already extremely wet. I realize now (since he turned out to be a manipulative little fucker, see the first story) that he probably did this on purpose, but I didn't realize it at the time. As he was thrusting, at one point, he pulled back a little too far, and his cock angled upwards, so instead of sliding between my thighs, his head was briefly snagged on my pussy lips, and then it popped inside for just a second. I immediately put my hands on his chest, shoved him out, and started yelling at him. He broke down and started crying which I realize now were probably crocodile tears. I felt so bad and reluctantly agreed to allow him to put just the tip inside for a few seconds if he still wanted to. And did he ever. He didn't even say anything, just climbed back between my legs, pulled me towards him and lined up his little 4" penis.

"Wait a second baby, you remember that it's just the head right? I'm serious, you CAN'T go any deeper than that. I'm going to put my hands on your chest, and hold your penis myself or I know you will get carried away."
"Yes! Fine mom! Just put it in! Please!"
"Ok mister! Hold your horses!"

I took hold of his cock with one hand and kept my other palm pressed against his chest. I slowly rubbed it up and down my pussy lips and then slipped it in.

"Holy fuck mom! Omg! This is the best thing ever!"
"Ok, calm down cowboy. That's enough."
"No! Wait!"

It had only been about 5 seconds but his penis was already beginning to pulse. I knew if I didn't pull it out now he was going to shoot his load in me. I am not on birth control and am a very fertile woman. My instincts were right and the second I pulled him out, his little cock exploded all over my stomach.

"Holy fuck mom that felt so good!"
"Ok, I'm glad you had your fun, but that's it, from now on mommy's vagina is off limits. Got it?"

A few minutes of arguing ensued, during which his cock got rock hard again.

"Hey! Listen to me! I can tell you want your balls drained once more so you're gonna do what I say, ok?!"
"Fine mommy, but can you suck it again? Like the other day? Your mouth feels almost as good as your pussy."

Ngl, that was a confidence booster. I bent down and ran my tongue from his ballsack, all the way up his small shaft, and around his cute little throbbing penis head. I even slid my tongue just under his foreskin which caused him to squirm and shake in pleasure, his load shooting out a second later. As he started to cum, I deepthroated him for the first time which caused him to scream out in pleasure. It wasn't really much of a deepthroat as 4" isn't really long enough to reach the back of my throat, but he certainly enjoyed it.

Anyway, since then we've ceased all sexual activity though he is still bugging me about it constantly. If you read my first story it explains why. I posted an update as well about how he fucked my mouth in my sleep after I came home drunk, which I am still furious about, so this won't be repeating. But it was fun while it lasted. Boys, if your mommy lets you into her panties, don't try to push things further. Be happy with whatever you get. She doesn't have to do anything for you. Respect her boundaries.