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The Caught Compilation 19

The Caught Compilation 19

Oscar-Worthy Anal

Oscar-Worthy Anal

Rotten Crotch

Rotten Crotch

Get Bent

Get Bent

A Random Act Of Kindness

A Random Act Of Kindness

Insecure Slut Tries Anal

Insecure Slut Tries Anal

Board Posts

-1
Anonymous
@confessions
11 Nov 2014 10:14PM
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I ran into a prostitute the other day. 40ish white suburban stay at home mother looking woman. She was standing at a crosswalk and I stopped because its the law or something. She walked up to me and said she needs a date, and did i want to date her :)

Yesterday I went back and she was at the same spot. I rolled down my window, she started on the same speech but I stopped her. I told her i had a gift, I handed her a thong i had bought for my wife but she didn't like the style, still had the tags on it and everything. Nice flashy thing. I said she would get more use out of it than my wife. She laughed and I drove away.

I wonder if she just threw it away or if she kept it?

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@random
06 Apr 2018 6:40AM
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Today I played the hitchhiking game. Get on a bus to a random location, have no money and trying to hitch my way back home. The trick is to wear something a bit flashy, like tight pants, but not so that you look like a hooker. Soon enough I got a lift from a cute young guy who was on his way back home after dropping off his wife and her best friend at a local market. He told me that the road I was walking wasn't all that safe, with most cars speeding and no sidewalk. Hidden underneath a blanket I noticed a wheelchair. When I asked him about it he said that he has a muscle illness and needed it for longer distances. I felt a bit bad for him, but knew from my experience with other people with a disability that petty isn't something they like to receive. So I told him that it's awesome he can drive a car, to which he replied: "Driving makes me feel free."

When we arrived at my place, I asked if he wanted to come upstairs for some cookies I baked the day before. Maybe it was his naïveté, but he agreed, saying that he was a bit hungry anyway. Haha, he fell for my trap. When we got to my apartment, I told him he could sit anywhere and I'd bring him something to eat. Out of his sight, in the kitchen, I quickly undressed completely, grabbed some cookies and walked over to him. The look on his face was priceless. He looked at me from top to bottom as I walked over and sat on his lap. I could feel his boner poke me through his pants, I said: "Do you want cookies now? Or do you want to keep them for desert?"

He was dumbfounded, so I put the cookies down, slid off his lap and undid his pants. "You don't need to say anything, I know what this guy wants": I said as I started to suck his cock. Haha, poor guy came almost instantly. Of course I gobbled it all up. That is what good girls do.

I grabbed his hand and guided him to my bedroom, where I laid on the bed, spread my legs and asked if he could do me too. He shuffled over timidly, got onto the bed and started touching me. First my inner thigh with his fingers, slowly inching forward towards my vagina. Another hand reached for my right breast. He was good, but the best was yet to come. He started to kiss my belly, my pubic area and finally my clit. A finger went inside my vagina, then another one, all while he was teasing me with his tongue. He was a hidden gem! How can there be such a talented guy stuck with only one girl? Life isn't fair. His rhythmic movements were synchronized with my body movement. It was like he could read my mind and by god, the orgasm that I had left me dazed for at least half an hour.

When I recovered I noticed he had a boner again. Time for round two! I pushed him onto his back, pulled down his pants and straddled him without hesitation. He had a surprisingly big penis, but that has never been a problem for me. I held his arms down over his head and moved my hips to make his cock slide inside my wet and dirty pussy. "I'm going to fuck you till there is no more cum inside your balls": I said as I started to thrust away. How often did he come? Not sure, but in the end he was in tears and my vagina filled with his sperm.

Now if you think I over did it, I beg to differ. He is coming over again tomorrow and wants the same treatment. As for now, it is only noon. So there is time for another hitchhiking game today. I hope my next victim is as fun as my newest fuckbuddy.

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@funny
02 Feb 2013 3:59PM
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Top 10 Fun Lesser-Common Hobbies


#10: Observe your neighbors. Run a website to post every documentation anonymously.

#9: Pretend to be a wizard or witch and curse people that look suspicious to you.

#8: Pretend to be german.

#7: Leave your windows open an let the neighbors see what you're watching.

#6: Act paranoid.

#5: Pretend to be a pony. From Equestria.

#4: Be russian.

#3: Pretend to be russian.

#2: Wear flashy clothing and pretend you're being observed by a secret agency, solely invented to observe you and only you alone.

#1: -TOP SECRET-

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Anonymous
@random
08 Jun 2018 8:03AM
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About a year ago, I was trying to talk my wife into telling me any sexual fantasies that she's ever had, or still has. She pretended not to have any at first. After much prodding and reassurance, she finally admitted that she's always wondered what it would be like to fuck a black guy. I was like, okay, I'll find some porn with black guys in it and we'll watch it together. I tried it out with her, but she wasn't into it for some reason. I tried again and again, but she always shut me down. I really wanted her to get into it, but it did nothing for her.

Like a good husband, I didn't give up. I figured it was just a matter of finding the right actor. There had to be someone that she'd take a shine to, there just had to be! I devoted myself to the cause, every night staying up late trying to find the perfect actor in the perfect scene. I amassed a huge number of bookmarks and subscribed to a number of black guy-centric websites. I downloaded so many scenes, I had to go out and get a 4 TB external storage thing to hold it all. My wife wondered what I was up to, but I didn't want her to feel pressured or uncomfortable about it, so I just fibbed and said work was busy, blah blah blah, whatever.

She started getting really suspicious after a while, though, so I decided that instead of doing research at home, I would buy a laptop and go to a motel. I found a cheap one on the edge of town and used it often. It was a sketchy neighborhood, with drug users and prostitutes of every sort frequently making noise in adjacent rooms. There was a cheap soda machine out in the parking lot that I used every once in a while to refresh myself after a long bout of furious jerking off. It was there that I was approached by a flashy, cologne-wearing young white guy with tattoos. After a few minutes of being interrogated by this guy, he managed to extricate the real reason behind my frequent visits. He nodded and laughed, but wasn't off-put or dissuaded. He promised to "hook me up". I went back to my room and resumed my research.

30 minutes later, there came a knock on the door. I swung the door open and couldn't believe my eyes; a big, strapping black man stared back at me, smiling. He was much, much taller than me, with big, rippling muscles barely contained by his t-shirt. "How's it goin, man?" he asked off-handedly and walked right in. "I'm Taireek, Victor's friend. He said you were doing some research for your wife and might want to see what all the fuss is about." I nodded, barely able to speak for some strange reason. "All right, cool. How about...' he grabbed me by the arm and guided me to the bed. The next thing I knew, his dick was in my mouth and I was naked and greedily working it over like the girls in the videos. It was incredible!
I went home that night and told my wife everything. I was sure she would want a turn with Taireek. To my utter surprise, she was furious and took off in the car to her mother's house 3 hours away. I was stunned. But then I realized: I had the house to myself, and her full wardrobe at my disposal!

I hopped in the shower and shaved my whole body, then dressed up as pretty as I could with perfume and makeup and everything. Taireek came over every night, even bringing a friend or two on occasion. He liked my new look and treated me like a sexy lady, cumming on my face and slapping my ass with abandon after getting his fill. My wife called and I just let the machine get it. She returned to find me in her red sequin dress, sucking 2 black dicks on our bed.

"You're missing out!" I called after her as she ran crying out of the house. "Thank you, honey! I would have never found this without your help!"

"Shut up and suck it, fuckin' white boy"

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Anonymous
@confessions
20 Aug 2023 11:58AM
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Gotta tell somebody.

I stopped by my church a couple of weeks ago to drop- off coffee and office supplies from the local box store. My pastor's wife was there, catching up on some bookkeeping. I always have a sympathy for her. Our pastor's a great guy. Very humble. Very unassuming. A lot of the things that a pastor should be but most of them aren't, you know? Not a flashy man but always ready to get up in the middle of the night to sit up with sick congregant or to rush out to the scene of an accident. At the same time, if you see him on the street, he doesn't make an effort to be seen as what he does for a living.

On the other hand though, being as pious as he is, he makes all the decisions at home. One of those decisions is based on the idea that sex if for procreation only. He and his wife have three children, born in the first three years they were married so they're what, 7, 8, and 9. They have their brood and he feels that his fatherly duties are fulfilled and that's enough. We're probably not supposed to know something so personal about their relationship but it's common, if whispered, knowledge. They don't even sleep in the same room as he doesn't want her to have to wake up when someone calls in the middle of the night.

She's not a raving beauty, doesn't wear make-up, always wears skirts, your standard conservative evangelical wife. Tall, slender, willowy is how I'd describe her. And she's as nice as he is in person. Always willing to chip in. So when I started to bring things in from the bed of my truck, she grabbed a couple of bags and helped, chatting all the while. Asked me how I was doing, thanked me for running the errand, and then asked me about my wife. She'd mistaken me for someone else. I don't have a wife. Never have. I have a friend though, same age as me and same name, so she was probably thinking of him. I said something flirty back to her like, "Oh, that's not me. I think you're thinking of the other _____ and his wife, Amy. They're just fine. But Mrs., if I was thirty years younger and you were single , , , , " She blushed and laughed and swatted me on the arm. "Oh you. Always flirting. You're a sinful man to know."

We set the bags down in the office, it took two trips. Then she closed the door and standing in front of it asked me, "If I was single, what did you mean by that?"

I had just been being playful and I told her so and started to apologize.

"Please, don't apologize."

Then she lifted her skirt, hooked her thumbs into the waistband of what I was surprised to see was a tiny black thong, and stepped out of it.

"Um, excuse me," I asked

"I know everyone knows I don't get it at home. He's a lovely man but in that one way, he fails our marriage. I trust you'll be discrete, and if you don't want to, please, say so. But I need a man and you're here." Then she leaned over the desk and flipping her skirt up, bared her ass.

I don't date much, being almost sixty. Sometimes I'll go to Denver and hire an escort for the evening. I have no problem paying for it. And here was a woman with a cute ass, a peach of a hairy little pussy, and she was asking me to split that peach for her.

So, of course, I did. I lowered my trousers and boxers and after stepping up behind her and fingering her to see if she was ready, and boy was she, I slipped all the way into her with one slow stroke.

I could see her fists balling up on the blotter of her husband's desk. As I began to stroke, I could hear her begin to grunt and say softly to herself, "fuck, fuck, fuck". She wasn't the tightest I've ever been in although she may have been the wettest and when she came, she clenched up so hard that I could barely move inside of her, which triggered my own orgasm much sooner than I would have liked.

"I'm going to cum," I whispered and she replied, "It's okay. I'm on the pill." So I let go and filled her to the brim.

As we were rearranging our clothes, I asked, "If you don't get this at home, why are you on the pill?"

"An essential part of faith is hope. And so I kind of always hope that he'll change his mind and I want to be ready if and when he does. Besides, you don't think this is the first time I've done this, do you?" She chuckled a little. "It's actually only the second time. But if you won't want it to be the last, I could see this happening again. How would you feel about that? You fit inside of me nicely."

"But you're a pastor's wife and this is sin, isn't it?"

"Yes, it is. But if you don't sin, you have nothing to be forgiven for."

So even though I'm thirty years older and she's not single, I'm going to be helping paint the church basement tomorrow while he's out of town and the kids are in school. I'm going to need to be forgiven. More than once, I hope.

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