:-) :-) :-)

Dear Penthouse,

I was homeless at the time (big shocker, i know) and staying in an overnight only shelter.

This biggo, old, fat (and wealthy) woman came to the shelter looking for me and my father after reading a story that was written about me in the local paper. (i had written a paper about what it's like being homeless and titled it "Welcome to the Jungle", a local journalist would then read it and write a story about me. Yeah i plagiarized Guns N Roses, i was like 10 years old, so fuck off)

She made a deal with him that we could stay at her house (me inside the house with her grand kids, him in a trailer next to it) so long as he agreed to take care of her 1 acre property.

She ran a daycare out of her house, but sometimes she'd need to go run an errand or whatever, so she had this 16 y/o neighbor girl that she paid to come help her. Cute little 16 y/o white girl from a few houses down. I don't remember enough to go into full detail. (or i should say, i dont remember her face well)

Anyway, when she'd come over, she'd sit the littlest kids down in front of the T.V and pop in their favorite Disney VHS. (Lion King was all the rage the time).

Then, she'd take me to the old lady's bedroom, shut the door and strip down to her underwear. No shorts, no bra, no shirt. She'd lay down and have me massage her all over. Her favorite was to have me scratch her back. So at that age she was flashing me tits...i got to rub her legs, back, mount on top of her with her ass pressed against me as i worked her shoulders etc.

And unlike my previous story i FUCKING LOVED IT because i actually did wanna fuck around with this girl and it was TOTALLY a sexual thing, for me at least.

Every once in awhile she'd also invite in the old lady's eldest grand kid, who was a year younger than me at the time, and we'd tag team the massage on her. Or he would sit there playing Sonic 2 while i mounted her and massaged her. She loved it, we loved it, it was great.

Here's the part where you're gonna hate me though.... maybe we kinda said a little too much as we were way too excited about it, let the cat out the bag and then we never saw her again.....MOVING ON NOW....
[Reply]

That is a much better story!!
[Reply]

Damn...then there's that other time when i was 14 with that 20 year old girl....jesus fuck....:-)

...I never really thought about it like this....wtf, Detoxing? :-)
[Reply]

At 13, I’d probably had screwed any human member of the female species.
[Reply]

Thinking about this one....this one is actually kinda hot and i actually got to fuck. Imma have to share this one next.
[Reply]

I had a sexy 15(?) y/o baby sitter that had waist long thick black hair and she taught me various ways to braid her hair.

She would sit in a chair watching TV as I stood behind her braiding it, taking the braids out, brushing it, and starting over...

Heaven.
[Reply]

If we're telling stories.....I barely dodged the bullet of catching the clap at 11 yrs old.

The neighborhood whore (16 yr old) was always hanging around my house and my 3 older brothers. She was always trying to tease me, rubbing her titties on me, kissing me and basically being a huge prick tease. I guess one of my brothers gave her the go ahead to pop my cherry. They had it all planned out for the coming weekend when my mom would be gone all day. She'd stop by during the week with previews of what I was in for on Saturday. The big day comes and nothing, no visit, no phone call, nuttin. And anytime after that she never acted the same towards me. I didn't find out until years later when my brother told me he found out the day before that she had the clap and called it off.
I'd loved to have seen the look on my mom's face when I came to her and said "mom, it hurts when I pee".:-)
[Reply]

First month into my freshman year of HS a beautiful senior took a liking to me and made me her boyfriend. She didn't have 1st period as a senior and her parents left home to work early so least to say I skipped 1st period a lot my freshman year.

Well one day were out very late at the bird sanctuary after it's closed fooling around in the back seat of her 72 dodge. Car pulls up behind us with headlights and it the cops. Long story short she was 18 and I was 14 which means I was a minor while she was an adult. The cops had to call my mom at home via their radio/dispatch (this was the early 90's when no cell phones) and I can hear their dispatch eventually come back and say that everything is fine as the mother states she is the girlfriend. That's about as close as come to having an older relationship thing.

My senior girlfriend looked very similar to this picture. She looked like such a full grown woman when I was a freshman.

[Reply]

Does it start with, "Dear Penthouse Forums" ? :-)
[Reply]

Teachers got it bad, got it bad, got it bad, for the Toxing.
[Reply]

When I was 17 I was dating a 22 year old. That drove my Mom crazy, she hated it.

Then it got worse, as I dated 27 year old, 34 year old, 36 year old and then a 43 year old when I was in my late 20's.

I always loved older women and the one time I broke my rule and dated a younger woman by 13 years, she was mentally fucked up from being molested by her father and abandoned. It was the WORST 9 months of my life and the ONLY women I ever dated that I fought or argued with. She caused me financial problems, legal issues, physical problems and mental stress beyond anything I ever dealt with.

Give me older....
[Reply]

37 times

pic.twitter.com/iMFrQSuUwi

— Your typical local man (@LocalBateman) April 2, 2023

[Reply]

Whew.
[Reply]

[Reply]

[Reply]