I watched him stroke his big young cock and now I'm confronting him tomorrow...

I need to tell someone what happened tonight because I'm losing my mind and I don't know what to do.

I'm Claire. I'm 41 years old and I've been divorced for about a year now. I work as a freelance graphic designer from home which pays the bills but doesn't quite cover everything, so I babysit on the side for extra cash.

I've been babysitting for the Morrison family for about three months now.

They have a seven-year-old daughter named Emma who's sweet and easy. They go out most Saturday nights and I come over around 6 PM, put Emma to bed by 8, and then I have the house to myself until they get home around midnight.

It's easy money and honestly I like having somewhere to go on Saturday nights instead of sitting alone in my apartment.

What I didn't expect was their older son coming home tonight.

His name is Ryan. He's 25 and he doesn't live there anymore, has his own place across town. I'd never met him before tonight because he's never been around when I've been babysitting.

But tonight he was supposed to leave for some camping trip with friends and apparently changed his mind at the last minute after his parents had already left.

I answered the door around 7 PM thinking it was a delivery and instead found this tall attractive guy standing there with a duffel bag looking confused.

"Oh, you must be the babysitter," he said. "I'm Ryan. I was supposed to be gone this weekend but plans changed."

That was four hours ago… and I ended up seeing something I absolutely should not have seen.

…

When Ryan first came in everything was completely normal.

He explained about the camping trip falling through, apologised for not texting his parents, said he'd just be in his old room and I wouldn't even know he was there.

He was polite and friendly and I tried really hard not to notice how attractive he was. Tall, probably 6'1", with dark hair and these green eyes and this body that was clearly athletic.

I reminded myself I was there to work and he was the son of my employers and I went back to playing with Emma in the living room.

Ryan disappeared upstairs to his old bedroom and I didn't see him for the next hour.

I put Emma to bed at 8 like usual, read her a story, and made sure she was settled. Then I went back downstairs to watch TV and wait for the Morrisons to come home.

Around 9 PM I realized I'd left my phone charger in my car. I went out to get it and when I came back inside I heard sounds coming from upstairs.

I should have just ignored it and minded my business.

But I didn't.

I heard sounds coming from Ryan's room. The door was slightly open and I could see light coming from inside.

I moved closer to see if everything was okay and that's when I saw him.

Ryan was on his bed, completely naked, stroking his cock.

I froze in the hallway, unable to move or look away from what I was seeing.

He had his eyes closed with his head tilted back and one hand working his cock in these long slow strokes.

And oh my god his cock was big.

It was thick and long and I could see it so clearly from where I stood.

I should have left immediately and gone downstairs quietly and pretended I saw nothing.

But I just stood there and watched him.

I watched his hand move up and down his shaft. I watched his abs flex with each stroke.

My pussy clenched and I felt myself getting wet just standing there in the hallway watching this man I'd met an hour ago jerk off.

I don't know how long I stood there watching. Maybe thirty seconds, maybe a full minute. But it was long enough to see him speed up his strokes. I knew he was getting close.

Then I heard Emma call out "Miss Claire?" from her bedroom and I snapped out of whatever trance I was in.

I moved away from Ryan's door as quietly as I could and went to Emma's room. She just needed water but my hands were shaking badly as I got it for her.

When I came back out into the hallway Ryan's door was fully closed and I could hear the shower running in the bathroom.

I went downstairs and sat on the couch trying to process what I'd just done.

I'd just watched my employer's son masturbate and instead of being horrified I was incredibly turned on by it.

I was so wet I could feel it soaking through my panties. My hands were shaking and my heart was racing and all I could think about was his cock, how big it looked… how his hand moved along it, and the expression, that goddamn expression on his face.

I'm 41 years old and I'd just perved on a 25-year-old like some creepy voyeur and I should have felt ashamed.

Instead I just felt desperately aroused.

….

Ryan came downstairs about twenty minutes later, showered and dressed in sweatpants and a t-shirt.

"Hey, sorry, I was just cleaning up," he said casually, like I hadn't just seen him naked and jerking off upstairs.

"No problem," I managed to say while trying to act completely normal.

"Emma's asleep, everything's fine."

He grabbed a beer from the fridge and sat in the chair across from where I was on the couch.

We made small talk for a bit. He asked how long I'd been babysitting for his parents and I asked what he did for work.

It was just a normal and polite conversation.

But I couldn't stop thinking about what I'd seen at all. I kept picturing him naked on that bed and I had to keep catching myself from staring at him.

If he noticed me acting weird he didn't say anything about it.

His parents got home around midnight and I gathered my things so quickly, I was desperate to leave before I did something incredibly stupid.

Ryan walked me to the door while his parents went upstairs to check on Emma.

"Thanks for tonight," he said. "Sorry again for the surprise of me being here."

"It's fine," I said while not meeting his eyes. "Really, no problem at all."

"See you around maybe," he said, and there was something in his voice that made me look up at him.

He was looking at me with this intensity that made my breath catch in my throat.

"Maybe," I said quietly, and then I left before I could say anything else.

….

I got to my car and just sat there for a minute trying to calm myself down.

My whole body was wound so tight with arousal from hours of trying to act normal while replaying what I'd seen over and over in my head.

I drove home and went straight to my bedroom and touched myself immediately.

I came in less than two minutes thinking about his cock and thinking about what it would feel like inside me.

I came again thinking about him catching me watching.

I was on my third orgasm when my phone buzzed with a text from an unknown number.

I almost ignored it but something made me check it.

The message just said… "I know you were watching."

Below it was a photo.

A photo of Ryan, shirtless, with his hand wrapped around his hard thick cock.

His face wasn't in the frame but I knew it was him immediately. I recognized the room, the body, and that cock I'd watched him stroke earlier.

My pussy clenched hard and my hand stilled between my legs as I stared at the image.

Another text came through immediately… "Liked what you saw?"

I just stared at my phone with my heart pounding, completely speechless and frozen.

I should've deleted the messages and pretend this never happened.

But I didn't do any of those things at all.

I just kept staring at that photo of his cock and felt myself getting wet all over again.

A third text came… "You there?"

He was waiting for a response from me.

I typed and deleted about five different responses before finally just closing my phone without answering at all.

I lay there in the dark trying to figure out what the fuck I was going to do about this.

I texted Mrs. Morrison this morning asking if I could stop by tomorrow to pick up something I forgot. She said Ryan would be there in the afternoon if that worked.

Which means I'm seeing him tomorrow.

Alone.

I need to confront him about these messages and tell him this is completely inappropriate and can never happen again.

That's what I should do.

That's what a responsible adult would do.

But god I keep looking at that photo he sent and all I can think about is how badly I want that cock inside me.

I'm 41 years old and I'm fantasizing about fucking the 25-year-old son of the family I babysit for.

I have until tomorrow afternoon to figure out what I'm going to say to him.

I'll let you know what happens tomorrow.

...

Welcome to The MILF Diaries. This is a collection of stories inspired by real confessions from women aged 35 and above. They come to me with their secrets, the things they've done, the desires they hide, and the moments they can't tell anyone else about.

I change names and details to protect them, but the core of each story? That's REAL . The diary is growing, and this is one of the many entries I'm sharing publicly. There's many more to come!