The Craigslist Chronicles: Chapter 1:

The Craigslist Chronicles: Chapter 1:

In this series you will find no incest, rape, drugging, coercion, serious violence, sci-fi, fantasy, bestiality, scat, necrophilia or anything of very offensive nature, including underage sex. The focus of this series is on characters, storylines, humor, and it happens to be set in a sexual environment. Please enjoy it in this context. If you are familiar with my previous work, you are in for more of the same.

Note on format: These chapters will be interconnected, but there will be many different characters, some may reappear. At the beginning of each chapter will be a brief introduction and description of the character, and it will then jump into the point of view of that character.

The Craigslist Chronicles: Chapter 1
Cynthia, 24, short curly brown hair, perky large b-cups, skinny. Cynthia looks like a girl/woman, someone who slept with stuffed animals well into her teens, and engaged in endless sessions of “no I love you more” types of phone calls. While not religious, she certainly is conservative, modest, and a frequent critic of those who sleep around. She is a college graduate with a good job, and her own apartment. She is currently single, and has not had a boyfriend since she found out that her lover was cheating on her six months ago. Though she is typically meek, quiet, shy, etc, she will not tolerate cheating and kicked his ass to the curb.)

Saturday Afternoon
I’m getting hornier than I ever thought possible. I’ve had a vibrator since I was sixteen, but never have I had to replace the batteries this frequently. For the first time in my life, I’m considering the fact that I might need to get laid. Wham-bam, thank you sir, and move on. I’ve always mentally castigated people that did such things. Sex outside of a relationship? That’s just asking for a disease or an unwanted pregnancy or other undesirable consequences. I’ve always felt myself to be of higher morals or values or self-control or some such bullcrap. But now, with my fingers numb and forearm sore from this mornings vibratathon, and having to fight off the urge to find the nearest phallic object and jam it inside myself, I feel like I just might understand the desire for sex overcoming the lack of a relationship and resulting in two people with little connection just doing the deed and parting ways.
I keep hoping that if I jerk-it the urges I feel will subside and I can return to my normal day. I decide it’s time to watch that porno that my ex left here when we broke up. It’s called Rockin the Bed, and has a photoshopped picture of a blonde with huge fake tits and a muscly man with a huge cock that looks more painful than fun. Tim tried to get me to watch this while we did it once, I made him turn it off, because, well, it was creepy. Why would it make sex better to have this fake crap on the tv. It made me feel undesirable I suppose. I pop in the DVD, close the blinds, and lay down on the couch. I jam my hand inside my sweat pants, but above my panties as I wait for the credits to end and the fun stuff to start. It’s always surprising how warm and moist my panties are when I wouldn’t think I was wet, but apparently I am.
Varying sex scenes are shown, its standard porn, we’ve all seen it I suppose. I slowly rub my fingers up and down my panties until I can’t stand it and I have to put them under the panties. Wow, she is wet! My middle finger pushes its way between my wet lips and I push it down to the opening of my vagina, and then slowly up to my clit. My fingertip reaches my clit, and with a little pressure, moves above the clit, giving her a little bit of a flick, and then the fingertip goes once around the clit, then back down and slightly in and around my vagina. Repeat. Oh my, repeat. On screen, two blondes are taking turns sucking off a huge cock. They’re on their knees and they look like they just are aching for him to cum all over them. I’ve never been a fan of the hand grabbing the back of the head, the domination kind of thing that men have over the women in porn. It’s degrading. But for some reason, right now, I think I get it. I wish I could grab a man by the hair and jam his head between my legs and feel him suck my clit. There’s something about the desire and the animal nature of it.
Soon the man is lying on his back, and one woman gets on him and rides his cock hard, while the other girl sits on his face. The first girl is jackhammering on him, I don’t see how that is physically possible. I’ve been on top, but I’ve always gone slow, and done more grinding than jackhammering. For me, it’s always slow and sweet and love-making. I’ve never liked it when a man used the F word, or took any kind of dominant tone or anything like that. I would never let him cum on my face or breasts. And no slapping my ass while we’re at it. Sex is an expression of love, not domination. At least, that’s what I’ve always thought. Right not however, I think I might understand the other side of it. Maybe sex can really be just about sex and having fun and, well, cumming, and fucking. My middle finger is now firmly jammed in my pussy, and as I frantically start fingering myself, my palm keeps slapping against my clit and I love it. The moans had started a while ago and were now getting beyond my control.
On screen, the man is doing one girl doggy style while the girls are in a sixty-nine. So one girl is getting fucked hard and getting licked at the same time. I never liked doggy, I like contact, face to face, kissing, maybe a little neck sucking, but when he is behind me, I feel distant and objectified or something like that. But right now, I want to get fucked from behind. I want a dick ramming in and out as hard as he can manage. The man fucks a little harder and cums. He pulls out and his jism drips out of her pussy as the girl below licks it up and sucks her clit all at once. My left hand has subconsciously grasped at my right breast, rubbing and squeezing it. I moan loudly as I cum, and I feel my vagina contract around my middle finger, and the pleasure waves move out and away from my pussy and I begin to shake and smile uncontrollably. I feel like passing out.
Minutes later, I sort of come back to regular consciousness, feeling a bit like a lump of jello, without muscle or bones and only capable of jiggling here and there. My hand is still planted on my pussy more out of procrastination than anything else. My eyes are blankly fixated at the sex on television. I wonder about my ex-boyfriends. They all eventually got around to trying to get me a little “wilder.” I always felt weird and embarrassed when attempting dirty talk, or in any position where we weren’t face to face. The F word was off limits. I don’t know, maybe I just feel like I was trying to be someone I wasn’t and they would see right through me and realize I wasn’t a crazy and wild sexual being, but a prude who was just pretending. Maybe because they knew me already as that prude they wouldn’t believe my wildness and so I get embarrassed just thinking about it. I wonder if I was with a new man if I could be wild from the beginning. I remember thinking this about first going to college. It was all new people, I could totally reinvent myself. You couldn’t just go from being a cheerleader to being a nerd in high school, they all already know you, it would seem artificial and fake and ridicule you. Same kind of thing. And with that, and a little more thought throughout the day, I decided that A. I wanted to get laid, and B. I would reinvent myself, get wild and crazy and C. for the first time in my life I would FUCK and not make love.

Casual Encounters
Woman needs some sex - 24
Dear Craigslist,

I am a 24 year old woman. I am horny and need to get laid. No Strings Attached. I am slim, and five foot six. I have a serious job, so must be discrete. I don’t want guys that sleep around a ton, must be drug and disease free. I typically only have sex inside of serious relationships, but for now I’ve decided that it’s been long enough and I want to get some and would like a man who is in a similar situation.

I posted this ad Saturday night and went to bed. Sunday morning I checked the e-mail of the address I just registered specifically for posting this ad. I was shocked. I had more responses than I would care to count. Luckily hotmail informed me that there were 34 new messages in my inbox. I’ll spare you the boring details, but I got all kinds of replies. A creepy old man who continued to send me emails for another week, even though I never responded to him, that consisted of sexual poems describing what he wanted to do to me. I got a lot of pictures of cocks. Not exactly the right message to send, so I never replied to them. I picked some that sounded like nice enough guys that didn’t get around a lot, replied to them, and slowly narrowed it down over the course of a week to one guy. I had two others as backups, just in case. His name was Ben

Here was Ben’s first message:

Hello there,

I’m 23, and also have a good job. I graduated a year and a half ago, and my main college girlfriend and I parted ways for practical purposes when this happened ( I got a good job in a different city), and I have been single ever since. I’m kinda shy around people I don’t know, but around friends I’m not shy or meek. But I do have problems meeting new people, mainly just that I don’t like bars that much or clubs or whatever, and don’t think the girls who frequent clubs that sleep around a lot are really my type anyway. I also don’t really think sex outside of relationships are a good idea, but have gone a long time without sex and am starting to rethink this stance. Really keeping a low number of partners is a good idea, maybe a fuck buddy is what I really need, it sounds like you might be thinking the same thing. Well anywho, let me know if I’ve stayed below the threshold of creepiness for you to reply to.

P.S. here is a picture of my huge cock in case you were wondering.
(and here was a picture of a rooster)

After a few e-mails, we started talking on instant messenger, and we had a similar sense of humor and got along fairly well and seemed we’d be meeting soon. He seemed a little shy about it and I ended up being the first to suggest that we do meet. Every day at work I got excited when he sent a new e-mail and I looked forward to going home and talking to him online. Thursday night, less than a week since the post, I suggested that we meet tomorrow. A Friday night date sounded like fun. We both agreed in a stilted conversation that we would meet in a public place, have dinner at a fairly nice restaurant, then head back to his apartment to watch a movie and take it from there, with the option to end the date at any point in there. Basically we just want to make sure the other person isn’t psychotic or a pathological liar or anything like that, and that we get along sufficiently and then we would probably get it on and then go our separate ways. We both kept making sure the other person was with us on the same page that this was about sex and not to get too attached or think this is a serious thing, it’s just a fling.


After a nice date, we hit it off, we’d eaten, and ended up back at his apartment. It was nice and clean, and we sat on his couch and turned on a movie with the provision that we were going to spend a little more getting to know each other time before we did the deed. He turned it on and then went into his kitchen to get us drinks. He put the drinks down on the coffee table and sat down. I instantly jumped on top of him with passion. I laid on top of him and we made out vigorously. His hands were a bit shy and I grabbed them. I planted one hand on my ass, and the other on my breast. I ground my hips into his and his hands began squeezing and rubbing with confidence. I sucked on his tongue, lightly bit his lip, sucked on his neck, and rubbed his chest. I sat up a little and nearly ripped my blouse off. My right hand traveled down to his crotch and rubbed his bulge in his pants.
He was losing confidence a little again, and I grabbed his hand that was rubbing my ass, moved his hand underneath my skit, and underneath my panties, and onto my bare ass cheek. His other hand gained confidence back and undid my bra and then he sucked on my tit.
“Fuck me Ben,” I moaned. He grabbed me and we rolled onto our sides on his couch. He pulled his shirt off while I worked on undoing his pants. I pulled his pants off and his boxers pulsated with his throbbing cock sticking straight out. He kissed passionately down my chest, sucking on each nipple, and rolled me onto my back as his hands reached under and gripped the back of my panties and he tugged them down my legs. He felt my feet and up my legs, giving light kisses along the way, and giving my pussy a little kiss and suck before coming back up on top of me. He grabbed a condom from his pants on the floor and put it on real quick. He was on top and ready.
“Fuck me Ben,” I demanded. He pushed his cock into my waiting pussy, she was so wet and ready. I nearly came just from the realization that a big man cock was penetrating me. He thrusted slowly at first, seemingly to feel me out, see what I was comfortable with. Something I would have appreciated before, but now it felt patronizing.
“Fuck me harder!” I groaned. “Harder, harder, harder,” I moaned to him as he started to fuck me with ferocity. His balls were slapping my ass and I wrapped my legs around him as he fucked me.
“Oh Cynthia,” he moaned.
“fuck me harder you bitch,” I demanded through gritted teeth. My pussy loved every second of it, and my clit was getting pounded by him as well, and she was building toward an immense orgasm. I could tell I would be sore tomorrow, but didn’t care at all.
“Oh!” I screamed out as I knew orgasm was just around the corner. “Cum inside me, fill my tight pussy! Give me all your cum!”
He moaned and I watched his face as his eyes closed and his hips delivered the hardest pounding so far. I came hard, my pussy squeezed him so hard it nearly pushed his cock out, and surely felt good, because he came instantly. He collapsed on top of me as I lay in ecstasy and I actually wished that there was no condom and I could feel his cum oozing inside me. Oh, I was so satisfied.


I awoke to realize that my glorious and orgasmic encounter was just a dream. It was 2 a.m. and my date with Ben was still a workday away. I could feel my pussy juice dripping down between my ass cheeks and soaking the bed. I was so incredibly turned on. I debated for a second whether I should save myself for some good sex tonight (hopefully), but couldn’t fight the urge. I jammed my hand down and rubbed furiously on my clit, making circles on my clit with pressure. I thought about Ben’s O-face, about him filling me with his cum, about his hips thrusting harder and harder, about getting fucked like never before, and soon I was cumming.

I’ve never had a day of work seem so long in my life. I couldn’t wait for seven o’clock. When I got off work I went home and tried to will the clock to move on, and tried to occupy myself by cleaning my apartment and then showering, making myself look pretty, smell nice, all that stuff. I wore the skirt I was wearing in my dream, that and a blue blouse, with my favorite pink bra.

At seven I met Ben in a Wal-Mart. Not classy, I know. But it’s a big place, with lots of cameras and people, perfect for meeting a stranger from the internet. We met in the book section. He looked nice. Not really tall, kinda shy looking, but not reclusive, cute. He saw me from the next aisle and smiled and I smiled and we both knew we had found each other. I stayed in my aisle, looking at a book, and he walked around the corner and next to me. He picked up a book and still pretended that we didn’t know each other.
“Was it good for you too?” he asked while reading the back cover of a book.
“What?” I asked.
“That was good, we should do this again sometime,” he said with a smirk.
“You hungry?” I asked.
“Oh so it’s your turn for oral already?” he said with a kinda goofy voice. “What ever happened to chivalry?” he asked. I couldn’t help but crack a smile.

We went to Applebee’s, shared some nice conversation, ate some food, and were too excited about what was coming later that night. Soon enough I was following him back to his apartment in my car. Time for me to shine, time for me to become the sexy, aggressive, moaning, dirty-talking, bucking cowgirl. Time for me to show him how wild and crazy I could get.

We parked and walked into his building together, riding the elevator up with a mixture of quiet awkwardness and excited, wanting to hump…ness.

His apartment was nice, and clean, not quite as clean as the dream, but clean for a guy’s place. He lived alone and I sat on his couch and put my purse down. He asked if I wanted a drink and I said I did and he went to the kitchen to make one. I, spur of the moment, decided to go into the kitchen. I walked up behind him slowly and quietly. He yelled at me in the other room, but I wasn’t in there. He was pouring two cokes and then opened a bottle of rum, and started to pour. As soon as he put the bottle down, I sprang, reaching around, grabbing him, hugging him from behind. He was only a few inches taller than me and whispered, “fuck me,” in his ear. I felt his cock hardening in his pants. He turned around, and I started to undo his belt.
He had a look of total shock as I got on my knees and whipped his cock out, giving it a little stroke and kissing the tip ever so gingerly. He was cut and about six and a half inches long. I stood up and demanded that he fuck me immediately. He smiled, looked me over, licked his lips. Shook his head a little, with this huge smile plastered on, as if he was savoring this moment and coming to grips with this hot woman basically fulfilling his fantasy. He reached around and picked me up by my ass. This surprised me a little as he wasn’t a big muscly guy, and not much taller than me, and probably only thirty pounds heavier than me, but he carried me, and groped my ass, as I hugged onto him and sucked on his neck. The next thing I knew he was sort of throwing me on his bed and climbing on top of me.
“Fuck me Ben,” I said. I felt weird and almost embarrassed, a little like I was in a movie or not really myself. A part of me was shocked that these words were actually coming out of me at all, yet I had no problem letting loose and becoming the wild and crazy girl. “Give me your huge cock, fuck me until you explode,” I moaned at him. The clothes started flying off and soon his cock was penetrating me. I rocked my hips at him, grinding my pussy into him, wrapping my legs around him as I demanded he fuck me harder. I instructed him to fill me up and his hips bruised mine. He bit my neck with just enough force to make me want him more.
I wanted to be wild, I wanted to be crazy and the epitome of male desire, the perfectly crazy woman. I wanted to be over the top. I came and exaggerated it, screaming and yelling obscenities. The funny thing is, I’d always thought the orgasmic shrieking of other women was so fake and forced, and as I was doing it, exaggerating, it also felt like I was just unleashing another part of me. Even though I thought it was forced, it felt like it had really come from me, it was genuinely me screaming, “fuck!”
I wanted to be so over the top crazy, and I grabbed him and demanded that he lay on his back. I climbed on and became the bucking wild cowgirl, jackhammering my pussy and his cock together. I fucked him until my legs burned and I fucked him some more. “Slap my ass!” I moaned and he did. He did it too soft and it didn’t make much noise. “Harder” I demanded and he did it harder. We repeated this several times until I could feel a red handprint forming on my sweat soaked ass cheek, and I loved it. I came again and collapsed on top of him. I wanted so dearly to be wild and crazy that I refused to let myself stop moving. Instead, I whispered, in a deep sultry voice, “fuck me from behind.”
“Yes mam,” he said with a smirk and got up and did me from behind. I loved it. I pushed back and groaned and loved how his hands gripped at my tits. I laid forward, on my stomach and he was on top of me, fucking me from behind. My hands gripped his tight ass and pulled him on me.
“Cum in me you bitch,” I demanded of him.
“Oh I’m close,” he moaned. I planted my hands on the bed and pushed up. I turned around and laid on my stomach, and pulled him towards me. His knees were on either side of my stomach and his cock stuck right at my face. I ripped the condom off and threw it aside. I sucked his cock, and stroked with my hand and looked right in his eyes and say his orgasm begin in the dropping of his jaw and tasted him cumming in my mouth. I kept the first blast of cum in my mouth, closed my eyes, and pulled him out and jerked him off, licking at the end of his cock as he let his load of jizz loose all over my face, neck, breasts, and hand. I just moaned and licked all around my lips. My hands rubbed it in and I savored every last drop. I gave his cock one last good sucking and then let him lay down beside me.
After a long while of heavy breathing, he said, “you’re not a pornstar are you?”
I just laughed and said, “no.”
“So…you want to get married? I’m free tomorrow,” he said. It sounds a little creepy as I type it, but he was obviously joking, and was expressing how perfect and hot I was, I loved it.
“I think I’m busy tomorrow, actually,” I said.
“Doing what? You can cancel,” he said,
“Fucking your brains out.”

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