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1
Anonymous
@confessions
29 Oct 2025 2:03PM
• 97 views • 0 attachments
[ − ] thread [ 3 replies ]

The night I fingered a crackhead and why I remember it fondly. 

A used to assist a friend in throwing some epic parties 15ish years ago. One night, after a few too many, I fucked a short portly blonde. She wasn't ugly by any stretch of the imagination, but she wasn't a stunner. She sat firmly in the 6-7 range. You know? Attractive enough to fuck sober, but you worry they'd get clingy and want to be a thing. Even now, at 37, chatGPT rates me an 8.5 for conventional attractiveness, even after I told it to be harsh, so you know... I've got that goin' for me. BUT, to my shock, she pulled a switcharoo and didn't want people to know she fucked me. ME!? 

Fast forward 12 years, and we reconnect on FB. Her husband just died, I just got a divorce, and it was nice to have someone to talk to. Her condition was evident in the photos that she was a user, but we weren't "talking" like that, so it was whatever. We hung out once, and it was a buddy hang, not a fuck buddy hang. 

Months go by, and I start receiving texts. The government took her sex trophies and she was homeless. Not like this was an ongoing situation, this had all happened within the last 5 hours. She had a ride somewhere later that night, but was spending some downtime at a casino. I thought, "Well, damn...I could bring her food and toss her 50 bucks, seeing as how she's broke and probably hasn't eaten all day." I get there, and after a while we decide to head to my car to continue our very lengthy conversation. It's, like, 2:30AM.

It was here that she started to fall asleep while I rubbed her boney shoulders. No exaggeration, she is 4'11 (jail records confirm this) and at the time MAYBE 85lbs. She coils into my lap, so I slide my hand towards her hips and continue rubbing. I'm a stand up guy. A saint, really. So, I ask permission to slide into her panties and I get the okay! I'm using both hands to grip her hip bone, and I might as well have been gripping a prop skeleton. I slide my hands in and started to rub her pussy. She lets out this raspy crackhead moan... You know the one. She honestly sounded like she was on death's door, which is actually why I'm telling this story, as it occured to me today that I should Google whether or not she was still alive. This went on for about 15 minutes. 

The pros, and why I remember it fondly: No ass cheeks. Everything was easy access. No thighs to move out of the way... it was just pussy and bird legs. Her little body curled up in my lap next to my hard dick made me feel massive! 

The cons: Dehydration. She couldn't get wet and her pussy was a walking swiftly into "don't touch it" territory smell-wise. These crackheads just don't care for themselves the way they should. 

The end. 

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Anonymous
@confessions
25 Dec 2011 8:53AM
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I messaged my mother-in-law and and she slipped into a half sleep state and I would every now and then rub her across belly and drift across her mound. As she didn't respond I rubbed between her legs just below her boney area and she just relaxed even more! After the message she told me it was the best message she had ever had and would always be ready for another, smiling from ear to ear.

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