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...

So... Has anyone ever given/received a creampie surprise?

I'm not proud of this one, but here goes...

I met a girl online and drove to her house to hookup.  She was... Out of my league, to say the least, even though I feel pretty confident in myself.  Tall, skinny, brunette, and more confident than me.   When I was texting her that I arrived, she told me to go through the backyard gate and come around.  I felt a little weird about it, wondering if it was too good to be true, but I did so.

She was in the jacuzzi next to her swimming pool, and I was awkward meeting her for a moment, because I was never told to bring a bathing suit.   She just laughed and said "join me naked", and she turned a bit and stood up to wring her hair out, giving me a view of sideboob.  I did as she asked and started to get in with her... It was cold, and I was hoping she wasn't looking, because I'm definitely a grower-not-a-shower... She totally was, and didn't look disappointed, so either she picked up on that or didn't care.  

She suddenly got a little awkward too and cuddled into me, taking my hand and moving it to feel her tits.  I started kissing her neck and she reached down to start playing with my junk... I got hard for her right away.   She sort of got on top of me, her ass against my cock, and I played with her tits from behind... They were probably b cup, but that was totally ok with me.

Then she balanced herself and bent over for me.  I started getting on top of her, having to grab the edge because I slipped.  I think she was trying to initiate more foreplay, but I really, really wanted her.  I was fully aware that the condoms in my pants pocket outside the hot tub were neither in reach nor useful in the water.  I didn't care at the moment, I wanted to fuck her.  

It was hard getting inside... She was so, so tight and small down there that my thick tip wouldn't even go in.  After her help and some maneuvering, I was inside.   I started pounding into her from behind, and it felt really good... It was far from the best fit for my cock, but it was pussy and it was amazing.   I was just watching the way she arched her back and picking up the pace... Getting more and more into it.

We'd hardly gone at it for a minute when I felt myself getting close.  I was really inexperienced at the time, and it was embarrassing to not be able to keep up.  I slowed down considerably and squeezed her tits from behind, telling her she was so sexy... I was trying to bide my time and recover, but it wasn't working.  She was so fucking sexy that I was going to cum whether I liked it or not.  

I really wanted to cum inside her, but I knew it was potentially risky and I was so embarrassed.  To be fair, we had talked dirty over messages, and one thing I mentioned was filling her with my cum, but it was in passing with other dirty suggestions, and she didn't give it any reaction in particular.  Having this in mind, I ended up giving in.

I felt my orgasm build and I picked up the pace considerably.  I bit my tongue as I kept thrusting, determined not to give myself away, as I started cumming inside her even as I fucked her.  I can't describe how it felt, because deep down to my dirty inside, I wanted to knock her up just because she was beautiful, and I just kept going, never intending to tell her.

She truly did not seem to notice.  

I, however, needed a moment to recover and felt myself deflating as I was thrusting.  Luckily, I think I lasted longer after cumming than before, and I think I shoved it far enough inside that she didn't know.    I pretended to lose my balance off the edge and blamed that.  

After that, we moved to some lounge chairs put together and started making out for a bit. She was playing with me, and I was taking annoyingly long to get hard again, but I blamed the cold air.  Once I was ready, I got on top of her and started fucking her again.  This time, we went at it for a little while.  Halfway through, she told me she wanted to suck my cock and swallow my cum.  As she was stroking it, I asked "So... since I've at least been inside you, are you on the pill or something?". She laughed and told me she had an arm implant.  She sucked me to completion as I pleasured her and made her cum on my hand.   It wasn't awkward anymore, but once we were finished we agreed to do it again.   Neither of us ever ended up reaching out though for a bit, and once I did, she didn't live there anymore.  

My cousin pushed me in the bathroom, “I’ll show you mine if you show me yours,” she said grinning.
In that “what the fuck” moment she shut the door behind her, and exposed a perky B cup which made my mouth water and instantly gave me wood.
I’ve always been kind of flirty with my cousin, but never thought anything of it because she’s family. Perhaps the last instance of truth or dare we played put us over the edge?
“I dare you to kiss Sandra,” my sister suggested. No, not cool sis, what is this high school? We were drinking and started acting like idiots.
“What are we living in a trailer park in the south?” I asked.
“You forfeit?” my sister slurred in her drunken stupor.
I leaned in to kiss my cousin Sandra who was flush with either alcohol or embarrassment, perhaps both. I moved in for the cheek but she turned at the last second and kissed my lips.
Maybe it was that kiss that did it, but Sandra was off the hook.
She stood there, looking at me with her tit exposed and smiling. I didn’t know what to say or do so I tried my damnedest to undermine the conversation.
“It isn’t that big, nothing special,” I said.
“Let me see it,” Sandra pleaded her breast still exposed.
I pulled my shorts down so she could see the tip of my erect cock.
“The whole thing!”
My penis was so fucking hard, pulsating, anticipating Sandra’s touch. I slid my underwear down to reveal myself to her and blushed.
“It’s bigger than what I’m getting,” she said as she looked at it.
Sandra is an Italian beauty, dark black hair, golden brown eyes, B sized tits with a slim waist and her lips are soft and pucker perfectly. She’s engaged to a cop and I’m married to a teacher, I had to put a stop to this or we both risked a shit ton of drama that neither of us could afford.
I pulled my pants back up, “listen cuz, you’re hot as hell but we can’t do this.”
“Do what? I just wanted to see your dick!” she said seemingly offended that I would think that we were going to actually fuck.
She put her perfect tit away blushing.
“Sorry, I didn’t mean to offend you Sandy,” I said looking into her eyes. She moved towards me, and hugged me tightly. Surely she felt the bulge between my legs throbbing against her stomach with anticipation. She looked up at me, and her lips touched mine. Her tongue passed between my lips and intertwined with mine.
“Bill is working tomorrow if you want to come over and help me move some furniture,” she whispered.
“You’re going to cheat on him with me?” I asked.
“He’s fucking every prostitute and woman he can. He’s always coming home smelling like a French whore house. Like I wouldn’t notice.”
“If our family finds out, your mom and my father… holy shit, you know the consequences.”
“They won’t. I’ve always wanted you. I need this. I’m on the pill, so we can do whatever,” She said.
Now SERIOUSLY. My cousin, holy fuck. My mind is still blown away. I’m married and so is she but I don’t know how to even approach this shit. I mean, yeah – I’m a guy and my cousin is a perfect 10 in my book. If I wasn’t related to her I would have railed her right then and there in the bathroom and bragged to my wife about it. I work at a job where I can easily take off and do whatever I want. I don’t think I’ll ever have the chance at being with a prettier woman in my life – unless I pay for it by using a high priced escort lol. What should I do? I know many are going to be like “bang her!” but seriously – put yourself in my situation for real. This is my first cousin.