WTF?

8 Uncomfortable Moments

8 Uncomfortable Moments

You Mother Fucker

You Mother Fucker

The 18-Second Man

The 18-Second Man

Mom Watches Daughters Blowjob Audition

Mom Watches Daughters Blowjob Audition

Husband Of The Year

Husband Of The Year

Fucking Hipsters

Fucking Hipsters

Board Posts

-1
Flipthefallen
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@hookups
09 May 2024 9:22PM
• 260 views • 1 attachment
[ − ] thread [ 1 reply ]

Looking to experience my first threesome with two beautiful women (one night fling, fwb or even an ongoing thing).  I'm a 32 white male. 5'8" 180lbs. I am std free, 420 friendly, with a high sex drive and a wide range of fetishs and kinks. 

I'm looking to enjoy the company of two ladys willing to have an exotic night! I would like to record and take photos of the night. I prefer not to wear a condom so birth control or tubes tied is a plus.

If interested please send age, location, a picture of the two of you. A picture of yall in Clothing and atleast one picture of both yall naked (underwear and bra is ok)  preferred.  A list of what yalls limits are would be nice as well. Hope to hear from yall.

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Anonymous
@confessions
13 Apr 2015 8:54PM
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I like trannys. I love the taboo of lifting up a skirt, seeing a dick and the sucking it.

Saturday night, being alone, horny and bored I surfed the casual encounters section of Craigslist under T4M. Found a tranny in my area who was looking for a no strings attached hook up. This one was also a VERS (top and bottom) and that was something I had been wanting to experience. Wasn't sure if I was ready to get pounded, but I at least wanted the option.

I got there, was invited in and as we talked, tranny told me that there was a spouse. I was nervous at this point and that said spouse was home. I was nervous. No advanced warning, I wasn't exactly quiet. The marriage is open and the spouse was told that I was coming over and why. So I was a bit calmer. Then I was asked "Do you want to meet my wife?" I wasn't expecting that question, but I agreed because I know some people in an open marriage want their spouse to meet their fling as a sign of honesty or something.

She entered the room and come to find out, the spouse was another male to female tranny. That was also unexpected, but what ever. So the three of us talked, then the spouse asked "Aren't you here to fuck my wife?"

I answered "Yes, I just was waiting for you to leave."

"You think you two are going to have sex and I get nothing?"

By this point my dick was about to tear through my pants. I thought she was still screwing with me, but part of me knew she was serious. I was about to ask another question when she said "Either get on with it or leave."

That's when I felt a pair of lips on my mouth. The tranny I met on line and I started kissing and undressing each other while the spouse watched. I have been watched before, but those were times when I was having sex with a woman. Here someone was watching me, and stroking themself while I sucked a dick.

This was suck a turn on that I came while I was on my knees. I was rubbing myself while sucking and getting dick slapped. I wasn't ready to be done just yet, and neither were they. I stood up and was ordered to bend over the arm of the couch. I watched as the tranny picked up the bottle of astroglide. Her spouse was now in just a bra. Her nightie was removed sometime before and her dick was in her hand. She was passable transvestite, no hormones, perfectly working dick.

I felt the dick head against my asshole and slowly my asshole opening up to accept it. I was getting it, my first time, bareback. My dick was hardening again.

I felt the dick slide out of me and felt the cum on my back. I then looked up to see the spouse come towards me, stroking her dick. I watched as she came over my face.

I laid on the couch, stroking myself as they watched. I asked them to call me a "cum covered faggot", and as they did I came on their floor.

I drove home in a bit of shame...and still get hard thinking about it.

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@confessions
10 Mar 2012 6:32AM
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I like to jack off into pill bottles and other small containers and then take a couple of them with me when I go out. It's awesome to dump it out on some whore's seat at a cafe when she goes to the bathroom or fling it at some dumb cunt walking down the street. It's funny as hell and it turns me on too.

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@confessions
29 Mar 2019 11:40AM
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I confess I the only reason I agreed to bring my sons new fling on vacation was to see her in a bikini.

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Anonymous
@confessions
19 Nov 2011 4:59AM
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I confess I want to fuck my 2nd cousin and she wants to fuck me. I wrote out this long boring ass story sob story explaining our lives but realized you all wouldnt give a fuck. We're flirting. We've discussed fucking but decided it would be weird but the other night we got on a good drunk and made out. Im bound by morals and so is she. Where I'm from incest isn't exactly unheard of but MY direct family would probably disown me. I swear though this girl.. This isn't just some fling someone I just want to get my dick into. She's more. I've never related to a person on this level. I never thought I'd even be considering it. But it's like finding the perfect person but it's just too taboo to have it and it drives me nuts. I know this is probably a terrible place to find actual advice but on a serious note what would you do. Put yourself in my shoes. Is a moral dilemma passing up something that could be great?

Also I probably should mention I met her about 6 months ago. It's not like I was raised around her I didnt even know she existed until then. We started talking online one day and we just hit it off. She's also beautiful. But to keep this private I need to keep pictures off limits I'm sorry. I'll describe her if you'd like.

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@confessions
08 Jul 2015 11:30PM
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I confess I met this girl working out on campus a few years ago and she had a bf but we had a fling anyway. Now I live 400 mi away and she has another boyfriend but still sends me pics and asks me if I'm going to visit her when I go home next. Today she told me she wanted to sit on my dick and sent me this pic she had her bf take.

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@confessions
28 Feb 2023 12:21AM
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My white wife(45) caught me having a long time affair some time ago and decided to make me her cuckold as payback.  She's seen other men for years and actually spent this past weekend with her black bf who is only 35yo.  They went on a road trip to attend his old friend's wedding.  Yes, my wife of twenty years was another man's date to a wedding.  Everyone assumed she was just the guys new fling

She sent me a pic of her pussy telling me it was his all weekend  I should be jealous and mad but I find it all so hot. 

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@chicks
29 Dec 2024 3:33AM
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short fling

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@random
23 Nov 2021 1:41PM
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Student - Professor - Instructor story

I just became an instructor at a university on the west coast. Before starting, my friends joked that students would hit on me but i vowed they'd be met with rejection. That was naive of me...

This beautiful freshman of mine (slender, toned, used to play soccer, minimal makeup, 20) started attending my online office hours for genuine reasons and we really got along. At the end of one online office meeting she mentioned how she'd come to my next in-person office hours (which was last week). Despite finding her very attractive, I kept telling myself to get a grip and to stop fantasizing. That was also naive of me...

True to her word, she attended my in-person office hours last week. While we still have to wear masks, and while I'd never met her in person, I could instantly tell it was her walking through my door. She was wearing a tiny pair of short shorts that failed to completely cover the bottom of her ass and a crop top. Despite students normally sitting opposite me, she sat down on the chair closest to me. We conversed, joked about where we both grew up/accents, and then she decided to show me a picture of her parents' house on her phone... As she scrolled through her pictures, she rested her phone against my leg and leaned forward. I immediately panicked at the idea of a colleague walking through the door and I quickly moved away. I then asked her to sit opposite me as "those were the rules" (they weren't really rules, I was just afraid). I instantly felt like an idiot, and i still kind of do. I'd have done anything to have her little hands under my pants.

She consumed 45 minutes of my office hour and as she stood up to leave, I noticed her left short had risen/folded up, revealing half of her tight ass cheek and better yet, part of her crotch. As she was flinging her bag onto her back and making her final comments, my heart stopped... The action of slinging her bag had revealed part of her pussy lip as a result of her left short being raised even further (I could literally see a tan line). As I starred, I quickly realized she was unfortunately wearing nude colored panties, and there wasn't quite as much lip showing as I first thought. Nevertheless, the thought of this tight bodied 20 year old being (seemingly) oblivious to what was on display to my older eyes sent my heart into overdrive. All of those fraternity boys who have probably flirted with her in hopes of seeing her tender pussy, and here I was effectively being paid to spend time with her and gawp at her body. I couldn't help but imagine what her parents would think about their girl being looked at like that while they're at home paying her tuition. Their beautiful smart daughter parading her tight ass around campus as students and faculty looked.

She emailed me yesterday about meeting in person after Thanksgiving break along with a comment about how she enjoyed our chat. I have no idea what to do... If I could do what I wanted and she consented, I'd bend her over my desk and spank her tight, athletic butt cheeks that she happily parades around campus. I cant help but fantasize about pushing my face into her crotch, sweaty from walking around campus all day... before sliding into her warm pussy that she seems to obliviously display. All i want to do is lick her (probably) tiny butthole.

It is worth risking my job? What if the 'phone on my leg' thing was totally innocent and she has no interest in me? What if she's just after a good grade? Obviously I wouldn't do anything without her consent, so surely I have to wait for her to initiate things? Did I scare her off by asking her to sit across from me instead of next to me? What if she's a completely innocent ditsy girl, oblivious to what she's displaying to the campus?

I hope to be able to update this post after Thanksgiving with developments.

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@confessions
12 Jul 2024 12:00PM
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Meeting up with an old fling from years ago. Wife of my best buddy in college. We had a 2 year long affair. Wonder how it will go. Anyone with similar experiences with any advice. I’d love to have a one night thing with her while we are together. Her hubby will be there but it was commonplace for us to fool around with him right there. Even fuckedone night with both our spouses in the same tent. Should I text? Or just show up?

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@confessions
27 Feb 2016 1:54AM
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I confess I can't stop cheating on my beautiful girlfriend.

I'm a foreigner living in China and I fuck girls of all nationalities, but I have to say, without a doubt, Asian pussy is smaller, feels better, and typically looks better on average.

We've all seen so many posts of girls talking about how much they love big cocks, whether it's for a short-term fling or a part of some kind of fetish, but I feel like there's a lot less discussion on how different pussy can be in how it looks and feels.

It's definitely not uncommon to hear from big cock loving girls that black guys are bigger on average, which seems to have some truth to it and is cool; I support people exploring different parts of their sexuality...

but this discussion goes both ways and it doesn't seem to be happening. I have a decent size dick, but wouldn't say I'm huge... but with Asian pussy, you're definitely smashing cervix waaay easier compared to white and black girls on average.

Chinese girls in particular are typically thin, silky smooth, and aggressively searching for men. Being a foreigner also makes you a bit of a rockstar here, especially if you're decent looking, make good money, or speak some Chinese.

My girlfriend is beautiful and an amazing person, and I really am a piece of shit for cheating on her as much as I do. I've told her that we should try an open relationship because of my struggles, but she's not into it. I actually don't care that much either if she was fucking some other dudes because that would only make it fair and I'm assuming she has or would.

Anyone have any thoughts to add or share? I'm curious if any guys or girls are in a similar situation where they have someone wonderful, but are also controlled by their impulse for variety.

If you're just going to make some racist comment about black people or asians, please just do the majority of us a favour and swallow a knife instead. Intelligent people don't want to hear about your insecurities disguised behind your racism.

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openforbusiness
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@random
07 May 2019 7:16PM
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So it’s been awhile unfortunately but the wife has finally found another potential fling. They matched on Bumble and have been flirting for about a week including sending nudes. She’s going out tonight to meet him for a drink or two. She’s also wearing a long skirt for easier access “just in case” according to her. Hopefully some good updates to follow.

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