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sick_o
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@random
08 Mar 2015 4:20AM
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Craigslist Story #1

So I've been using craigslist for about 15 years and started using the hook up section about 13 years ago and I'm still going strong! Let me tell you about my first casual encounter.

I was browsing through the casual encounters like I had been doing for a while and finally decided to answer an ad looking to get their cock sucked. The pic in the ad was a nice looking average sized dick with a pretty straight forwardly written ad, he wanted his cock sucked by another dude. I was in the mood and sent him a response, almost immediately I had a new message in my inbox! He sent me his address and I told him I was on my way. I get up and grab my jacket and cellphone and run right out the door to my car. I hop in my car and hit the highway. He lived a city over up on the hill or at least that what was the address told me. I drove for about 15 minutes then hoped of the exit and up the windy roads until I reached the house.

I pulled into the driveway of this massive modern mansion built into the cliff, it was pretty fucking impressive. I turned the car off and pulled my phone out of my pocket and put my earpiece in, it was corded one that went in a single ear. I look down and dialed this chick I had met on AFF the month before, she a massive 375lb disgusting whore of a woman, I really miss her... Anyways the phone begins ringing and after only one ring she picks up the phone but before she even says hello or what's up instead she says... "Come fuck me". My response was just as classy... "Shut the fuck up and just listen", She asks "What?". What I MEANT WAS "I cant talk so just listen to what's about to happen". I explained myself better just as I was opening my car door and immediately she asks me "Are you going to suck some cock? Please tell me you're going to suck cock ( )". I tell her "Ssshhh, just listen", I step out my car and shut the door. As I look up there is a man standing at the gate staring at me, so I stuff my phone into my pocket and walk toward him. Just as I get in earshot of him he says "Nice car, you must do well for yourself", at the time I had a pretty swanky ride. I answered with "I do ok, you must do pretty good by the looks of this place.". The guy smiled and tells me he is just house sitting for a fiend. I follow him into the house and he shuts the door behind us...

As he leads me to the lower level of the home the chick is in my ear talking up a storm saying shit like "Oh my god ( ) you're going to suck some cock" and "Swallow all his cum", she was so turned on. As I get to the lowest level where I'm about to put this strangers cock in my mouth I look up and see the entire wall facing out toward the urban sprawl at the bottom of the hill is a giant panoramic window. I turn and walk up to the window and take in the view but when I turn back around I see him sitting on a couch facing me he has opened his robe and has his rock hard cock out. I walked right over and got on my knees without saying a word! I leaned in and slid his stiff cock into my watering mouth and he immediately let out a moan which the girl on the other end heard sending her overboard. She loses it and starts rambling aggressively "Suck that fucking cock! Take it all" that gets me salivating hard as I bob up and down on his cock deeper, wetter and faster. All this causes the guy to start gyrating his hips and trying to fuck my mouth as moans and says "Oh my god you have super head". That pushes me over the edge... I pull back a little and grab his cock with my hand then slide it out of my mouth so that the head is barely touching my lips, I'm staring him in the face but his head is leaned back.

Well he must have felt me looking at him because he looks down and our eyes lock. I get so turned on that I grit my teeth and tighten my lips as I let out the most nasty, disgusting, filthy growl just before I lower my lips and start licking and sucking on his balls. Without breaking eye contact I move back up to the head of his cock while I still have his shaft in my tight grip. I clench my mouth tight again and slap myself on the lips with his stiff piece of meat a few times. He moans and I let out a deep breath then slide it back into my mouth almost taking it all down. At this point my friend sounds like a cheerleader at a high school football game, she is going crazy and can't stop cheering me on but in a disgusting sexual manner... Which gets me going harder. I must have been bobbing up and down on his hard cock for five minutes straight when he begins wiggle and thrust his hips, just then in a loud moaning voice he spits out "Oh, I'm going to fucking cum.

She hears that and her voice drops real deep and she talks through her gritted teeth... "You better swallow all that cum! Don't waste a single fucking drop" Just as she says that he grunts and I feel the first warm spurt in my mouth and I let out the loudest, deepest groan that I possibly could with a cock in my mouth! I grab his wet slippery cock with my hand and slide my mouth up to the head as I start jerking him while I suck the his hot cum right out the split in the head of his dick. I drink down his hot, salty jizz while my friend listens in bliss on the other end of the phone. I suck out every last drip then pull my mouth of the head of his cock and squeeze the tip getting a small drips worth off cum to surface... I lick it up and say thanks as I stand up to leave. He looks at me and says "that was amazing". I make my way to the stairs and he hops up closing his robe following me up the stairs. As we reach the door I open it and he grabs it by the wood holding it, I turn toward him and all in one motion I reach into the robe and grab his semi erect cock giving it one last stroke as I say "Thanks" then turn and walk out.

I go up the driveway and get in my car its so quiet I forget I'm still on the phone with my friend. She blurts out "That was hot!" and I say "You're welcome" jokingly. I start the car and back out the driveway then head down the hill. Before I reach the bottom of the hill I tell her to jerk off so I can listen, without a single word spoken I can hear her breathing heavy and moaning. When I get to the bottom of the hill at the stop sign I immediately get my pants down enough to get my big hard cock out and without letting her know begging jerking off. As I head toward the freeway I'm stroking myself slowly but once I get on the highway I start stroking hard and fast as I fly down the road. It's about 2 am on a weekday so nobody but me is on the highway and I'm zoned out listen to her jerk off and trying to drop a load myself. She is moaning like crazy and I'm getting close myself. I feel it coming so I start stroking like mad and out of nowhere she say says "Fuck yeah! Come for me ( )", she knew I was jerking off. I'm on the verge of squirting a huge load so my focus is only on my dick and the road in front of me. My cock is tingling and I feel the cum rising into my shaft ready to spray everywhere. I can feel that there is a car next to me at this point and they are keeping pace, I feel there eyes on me but I don't give a fuck because I'm ready to cum. Just then the tingle hits the head of my cock, I let out a growl and yell at the top of my lung "I gonna' fucking cum" and the first spurt of hot seed sprays out...

It is a huge thick stream that comes right at my face! I spray myself right in the face and over my head. The second is another fat rope and straight in my face again. I feel the third come out like a puddle of water all over my hand... The wetness does it and I let go and start licking the cum off my hand like the sexual deviant I am! I can feel the eyes of the person in the car next to me and I smile knowing I gave them a hot show. I mumble "Fuck yes" and my friend says "That was hot", I say back to her "You know what's hotter?", "What" she says... "The person in the car next to me just watched my cum all over myself", "Really?" she says. "Fuck yes" and I turn to look at the person driving the car and its a fucking ******* patrol... I turn white as a ghost and he slows down then gets behind me and hits his lights. I say "oh shit" out loud which gets my friends attention. She ask what's wrong and I tell her it was *** watching me and he's pulling me over now. The first thing out of her mouth is "Tell him you'll suck his cock", I tell her to shut the fuck up because its not funny, I'm going to go to jail. I throw my blinker over and cross the lane to my right to pull on the shoulder. He comes on the speaker and says...

"No! Pull off the exit up ahead"

To Be Continued...

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@random
23 Nov 2021 1:41PM
• 694 views • 0 attachments
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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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@random
01 Apr 2025 7:53PM
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Lips that grip.           

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@confessions
08 Nov 2025 10:50PM
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This is my ex girlfriend. She made this video when her friend sent her a video of me fucking her cousin. The moaning you can hear at the start is her playing the video of me and her cousin. I would regularly cheat her,and her on me. I would spend all weekend out on the sesh and fucking anything that even smiled at me. I was over confident and my ego was a monster I would be blatant with my intentions and tell girls I have a girlfriend and I just want to fuck. Now we had a great sex life. Well I say great. But it was more the frequency of the fucking. But if we only knew how filthy each other really were. We would just give each other relationship sex. Enough to make a mess but nothing exciting. I would be filth with these ohlther women treating them like sluts and have the wildest sex. Only to come home and have the old-fashioned couple sex. I knew she was cheating and I that's why I always stepped it up a gear. She would go have a quickie with some dealer in the back of car. I would go take copius amounts of party bits and have group sex orgyies with my mates and random woman from nightclubs. Her cousin was there one night and I vaguely remember when I slid it in to that tight pussy the moan "I can see why she likes you, but she's fucking so and so. Just so you know". At that I thrust hard deep inside. I felt her 19 yo lips grips hold of my 7 inch. (Granted not the biggest, but 2.1 inch thick. She bucked and rode like a rodeo rider. I didn't last long before my friend and his piece of fun come the room. They laughed and just sat on the bed. The cousin started to clean me up, gently guiding my jizz covered tip to her mouth. Her friend but in. And said she wanted some I looked at my friend to see if they was any problem I just gave me the wink. ( his lengths bigger than mine but skinny like a pencil like 9.5 long but 3/4 thick. They were competing to get me hard again. And as I got lost in the moment I failed to see the phone recording. I've since seen the video and she started with herself sucking me and then her friend taking turns. I got excited and grabbed the phone began to watch it back and and seen it had been sent.... well im not a half's kinda guy so. I got the phone, flash on. Talking filth the the two sluts in front of me. They had started rubbing each other by then. Video rolling. I turned full director mode. Talking filth. The party bits took over I got brash. ( praise my cock.tell her much you loved it inside you l. Tell her how wet it made you.) Her friend turned to me licking her fingers and put me back in her mouth. The cousins was giving her hole perfect attention. They way a woman knows a woman, they squirmed and riggled. They both started whaling the cousin enjoying her hole. While the friend was giving me the sloppiest, naughtiest blow job ive had to date. Any way of my friends joined in and the party had died down. So the girls friends came to see where we all went. The shock of their faces and almost nativity as they giggled and gasped. They soon realised that the girls where all involved and having good they stripped off and the other girl left the room. We all took turns recording. And swapping round. The mattress was damp for a week. I sent the extended edition to the ex girlfriend and told I know what she has been doing and who with. Oh and that your cousin likes my length alot. She didn't reply for 20 minutes or so. But we all continued. I woke up in the living room naked the cousins head on my chest. And the friends head in my lap. Is was stroking my peniss absent mindedly. As  people started to get the next day they was a mischievous yet almost guilty air in the house we all smirked as we passed each in the house trying to find our stuff. I checked my phone to see several missed called and video chats from the ex. The cousin came to me and said "she's sent this" I watched it... we all did and recognised our own moans in the background. I was rock hard instantly it was throbbing so much it hurt. Underneath there was a message say I filmed that to warm me up for ******. One of many lads she had on the side. I didn't feel angry or jealous. I was horny but didn't feel the expected heart break of having done to me. What had been done to her. I was disappointed.. for one, if I had known how filthy and kinky she was I probably wouldn't have wondered. But I also think she hid that from me. We patched things up and i got a slice of the filthyness. We even watched the video while we fucked. But the damage was done. We couldn't be together after that. True love is unconditional she knew i was horny filthy man slag, and I knew she had a slut inside her, she justbdidnt give me it. It came out from time to time when she would call after a nught out. We met up a few years later and she looked unbelievable. I did too. Although still had a massive ego. It soon led to us fucking when she landed at mine one morning after some stranger had dumped a load in her down an alley. She would come in put my cock straight in her mouth and started ratching the cum out of her licking of her fingers like the pink dildo. She lives the taste of cum. Hers, mine, anybodies. We often sneaky link im married now and so is she but nobody knows how to fuck each other like we do. But my wife gives better blow jobs. I joke about it with her while she's trying to drain me. She tell me her husband is thicker than me . She knows the narcissist in me makes me fuck like  point to prove.I lost the video i sent her and i thought this was gone too. Its my go to video for a quick release. 12 mins when she makes those little noises drives me insane. She's has a few other videos on here ive found. Few webcam and selfshot videos. I don't miss her but i do miss the pussy

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