Confessions From a Craigslist Slut Volume Two
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We’ve all seen the ads and we’ve all thought about it even if just for that fleeting second. Some of you probably don’t want to admit that you’ve thought about it but I’d wager that if you were being honest with yourself than you have. I suppose you couldn’t have thought about it if you’ve never visited the website or don’t know what it is, but if I send you there and tell you all about it, you will think about it. What is it you ask? I’m talking about Craigslist of course and one day I did more than just think about it. This is the story about how I became a Craigslist slut.
This all started about a year ago on my twenty-first birthday. I had broken up with my boyfriend three months earlier and was feeling very lonely and sorry for myself. Greg and I had dated for 4 years. We were high school sweethearts, had gone to prom together, he was the only man I’d ever been with sexually, and we were engaged to be married. That is until we had ‘the talk’ where he claimed he had changed and we had grown apart. The truth was he had dumped me for Carla Wright.
I was of course devastated. I mean Carla Wright? If you are going to dump me at least dump me for someone who is better looking than I am. Someone better educated, with a better personality, or someone with a better job. But not Carla Wright. I guess there is no accounting for some peoples taste and I realize now that I am probably better off without him.
Back to my twenty-first birthday. I had declined all offers from friends and family to go out that night. I was depressed and just not in the mood to be celebrating. The only thing I wanted to do was order in Chinese and curl up with a good book. I finished my book by eleven that night and was extremely horny. Yes it was one of those smutty romance novels. It had been a long time since I had any intimacy or sex. Greg and I really weren’t doing it a whole lot towards the end and I was getting to the point where my dildo just wasn’t cutting it anymore.
I don’t even remember where I had first heard about Craigslist. Maybe it was overheard from guys at work or maybe it was online somewhere. Craigslist is basically a website that replaces the buy and sell ads of a newspaper. It has all sorts of different categories where people post ads for things they are selling or buying.
The seedy side of Craigslist happens in the personals section. These are sections where you can meet people to date but those aren’t used a whole lot. The real action happens in Casual Encounters. You can look at ads that are from males looking for females, or couples looking for females or males. Basically any combination of man, woman, couple, or transexual.
At this point in time I wasn’t posting my own ads so I went to the ‘m4w’ section. I answered a few ads that had pictures with hot guys but the emails that came back wanted me to sign up for websites and weird shit. After a while you learn to pick out the real ads from the spam.
I saw an ad where the title said ‘Lost My Job Need Something Good Tonight'. The text of the ad went on to describe how he had the worst week of his life and was just looking for something good to happen. He was a forty-five year old man which at that time I would never had gone for, but I suppose misery loves company and I kind of felt sorry for him.
We corresponded back and forth a bit through email. I’ve learnt that this part is a bit of a game where you learn how serious someone is about actually hooking up. A lot of people just don’t follow through. We didn’t exchange pictures as neither of us were comfortable doing that. It was lucky that we lived in close neighbourhoods but neither of us wanted to use our houses. I also told him that this was my first time on Craigslist and I didn’t think I could have sex but I would give him a blowjob. In reality I really did want sex but I wasn’t yet ready to start fucking strangers. I think it was really just the intimacy that I was looking for that night. He was happy with a blowjob and we agreed to meet at a nearby coffee house.
After the last email we agreed to meet in 30 minutes and I remember panic setting in. What the hell was I doing? Was I really going to go? Was I meeting with a psychopath who was going to kill me? I changed out of my pyjamas and put on jeans and a shirt. It was late and I didn’t have the time for anything fancy. I don’t believe I’ve yet described myself for you. Basically I am tiny and I am short. I’m a half-inch over five-foot-two. And yes that half-inch is very important! I weigh in at about 105 pounds. I have blue eyes with long blonde hair and what many have called a cute button nose face. My breasts are on the smaller side so we don’t need to go into detail about those. When I gave myself the final look over in the mirror I thought I looked pretty damn hot.
I don’t have a car so I walked to the coffee house that night. It took me about fifteen minutes and my heart felt like it was beating a million times a minute the whole way there and my senses were on high alert. There is an adrenaline rush I get from doing something dangerous or doing something I know I shouldn’t. I definitely had that rush going that night. It was a huge contrast from the loneliness and depression that I had been in for the months prior. Maybe the rush is the reason I became addicted to doing this, maybe it was the feeling of basking in sunlight after being stuck in darkness for so long that got me hooked, or maybe just maybe I really am a slut and like hooking up with strange men.
I got to the coffee house and there were only two tables with people at them. One of them was an older guy with a red baseball cap and a blue jacket. Just like he said he would be wearing. It is an odd feeling to both want and not want something so much at the same time. The fact that he was there was absolutely thrilling to me. And the fact that he was there was absolutely terrifying.
I sat at his table and we exchanged awkward pleasantries as we checked each other out. He wasn’t ugly but he wasn’t someone I’d pick out of a crowd to go home with. He was a little over weight and probably balding under his cap. I was half his age and I could tell he was very happy with me. He told me I wasn’t at all what he expected, that I was hot and a very pleasant surprise.
When he asked me if I wanted to go to his car I nodded my head yes and we both got up to leave. One of my issues is that I hate making people feel bad. I don’t like saying ‘no’ to people and I don’t like disappointing them. I guess I’m what they call a pleaser. This wasn’t the case with this guy as this was my first time with Craigslist and I was buzzing from that but in my time doing this I’ve met some guys that I had absolutely zero attraction to but I went ahead and fucked them anyway because I didn’t want them to feel bad. This is where screening becomes very important because for me if I commit to meeting them I’ve pretty much committed to fucking them.
His SUV was parked in the back of the parking lot and we walked to it in silence. I’m glad my first time was in an SUV. If you ever plan on doing these kinds of things in cars, bigger is better. I may be tiny but sex is not fun in a compact car.
That walk to his car was one of the longest of my life. I was convinced that he was going to kidnap me, rape me, and murder me. My heart was thudding and my breathing was laboured. He got into the driver side and I into the passenger side and we just sat there with neither of use saying anything until the dome light went out.
He reached down and undid his pants. I still remember the sound of his zipper. His cock came out and he was stroking it. It was only the second cock I’d ever seen live and it was much thicker than Greg’s. He reclined his seat back to give me full access.
I leaned over and he let go of his cock so that I could take over. My hand closed around the base of his shaft and I ran my tongue over the head. I never really enjoyed giving Greg blowjobs and it was just one of those things I did. Maybe thats why he had moved on to Carla Wright. But that night, in that moment, my feelings on blowjobs changed.
The feeling of a strangers hard cock in my hand, his musky scent in my nose, and his taste in my mouth is a very powerful one and I could feel my pussy get immediately wet. Sometimes now when I’m sucking I don’t even care who the guy is. It is just about me and his cock. I don’t care about anything else.
As I took him into my mouth and began to bob my head up and down his shaft I could feel his cock grow harder and harder. The harder he got the wetter I got. I got so turned on that I had to undo my pants and slip a hand between my legs to rub while I blew him.
I felt his hand on my head and he began to guide me. I like it when guys show me how and where they like to be sucked. Each time I learn how to please a man I add it to my repertoire to reuse on someone else another time. His cock began to ooze precum in my mouth and I happily reapplied it to his shaft with a mixture of my saliva. I loved how slick and wet it got.
When he was ready to cum he held my head in place and filled my mouth. Holy shit there was a lot of cum. He must of been holding off for at least a week. With Greg I never swallowed but I have found a new appreciation for it. Lets be honest, at best it tastes just okay, at worst it is putrid. But the prize is in knowing that I was the one who made him cum and for that I now swallow it all.
There was another awkward silence as I moved up from his lap wiping my mouth. He offered me a weak ‘thank you’. I got the feeling that he wanted to get the hell out of there quickly. I only nodded my head and got out of the car. Our agreed to deed was done. I never saw him again but I will always remember him fondly as he was my first.
I walked home that night with an odd sense of satisfaction even though I didn’t get off. I was happy for the first time in a long time. It felt good to get someone else off. I slept more soundly that night than I had since the breakup and although I can’t remember the dreams I had I got the feeling the next morning that they were wild and amazing. My sleep was kind of like that blissful feeling you get when you sleep in a lovers arms for the first time.
The only difference was that when I woke up I was still alone. I went about my morning routine getting ready for work all the while replaying the previous nights activities in my mind. By the time I got to work I knew I was going back out that night and this time I wanted to go all the way.
Thank God for smartphones as I was able to surf Craigslist all day without anyone else knowing or seeing. I didn’t get much work done as I corresponded with a bunch of ads. I decided I wanted to see pictures first this time but this usually means you need to send one as well. Lets be honest here for those of you thinking you want to get into this life, pictures aren’t a guarantee as many people will send fake ones just to get you to show up and I’m ashamed to admit that ploy does work on me so I probably contribute to the problem.
Into the bathroom stall I went and used my phone to take some half naked pictures of my body. I had to wait until there was no one else in there as I didn’t want anyone seeing the flash going off. Classy right? Well other than both words starting with the letter ‘C’, Craigslist and classy have little in common.
I’d settled on a guy whose picture had abs to die for. He was able to string more than two sentences together in his emails, he was around my age, and he seemed more or less normal. I was on a high for the rest of the day. My mind was buzzing with things like what he would really look like, what we would do together, and my mind always wonders if I’ll be walking into some kind of trap. I think I enjoy the buildup just as much if not more than the actual act itself. The anticipation is kind of like the feeling you get with Christmas or your birthday. You never know if you are going to like your presents until you open them up and see what is inside. Sometimes you are horribly disappointed and other times your mind is completely blown.
We had agreed to meet at his place at eight that night. I knew I didn’t want to do it in a car again. I also knew that I didn’t want this guy to know where I lived. So that left his place. Dangerous but risk is part of the game. I took a long hot bath when I got home from work and took the time to shave my legs and pussy. I hadn’t been seeing anyone for long enough that I had let my grooming go.
I enjoy the ritual of preparing myself for the men that I meet. I inspect and prepare my body all the while imagining their reaction when they see me. Shaving, lotions, makeup, perfume, hair. I want everything to be perfect. You hope that they will be blown away when they see you and appreciate the effort you put into getting ready. Sometimes I wish the guys would put the same effort in on their end or at the very least shower before we meet. Often I get so worked up with the thought of what is to come that I need to masturbate while I get myself ready.
It was a beautiful summer night and I decided to wear a short white summer dress. I often wish my breasts were bigger but sometimes in situations like this I can get away without wearing a bra. They aren’t going to be falling out or flopping all over and I think it is kind of hot when you can see the silhouette of my erect nipples poking through my dress. I put on a lacy white thong that wouldn’t show through the dress and I was on my way.
I knew I was looking good during the cab ride when the driver kept checking me out in his rear view mirror. He dropped me off and I walked up to the apartment building and those now familiar butterflies were flapping madly in my stomach. I punched in the buzz code and the buzzing of the door unlocking went off without us exchanging a word. There was an agonizing wait for the elevator followed by a heart thumping walk down the hallway and finally the wait to gain enough courage to knock on the door.
The door opened and a smiling guy wearing only shorts opened the door and invited me in. He obviously worked out and those abs were indeed the ones I had seen in the picture. Things were looking good.
The door closed behind me and I took in the scene in front of me. The first thing I noticed, probably due to the noises coming from it, was that there was porn playing on the TV. The second thing I noticed was that there were two other guys on the couch, naked, and jerking off to the porn.
I always thought that most guys were squeamish about being around each other naked or seeing each other hard but I’ve found out that there are pockets of them that love jerking off together and fucking girls together.
I froze with my back to the door. I was only expecting one guy and this curve ball had me thinking I should turn around and bolt. The one with the abs must have seen the fear in my eyes and reached out to gently take my hand. He told me it would be okay and if I wanted to only fuck him the others would only watch.
I let myself be led into the living room and escorted to in front of the TV. He slipped off his shorts and took his place on the couch with his friends. There I was standing in front of three strange men who were buck naked and hard and all eyes on me. I knew when I saw the desire in their eyes, the desire for me, that I would be staying. Mr Abs suggested that I should strip.
I wish I could say that I put on a good show for them but the truth is I don’t like being in the spotlight and aware that all eyes are on me. If I did maybe I’d be making money as a stripper instead of doing this. Believe it or not I’m actually quite shy. I took my dress off and they expressed their pleasure at seeing me with no bra. The only thing left was to slide my panties down my legs and I stood there watching them watch me. A five second strip show. Mr Abs spread his legs and motioned me over.
I was instantly wet and glad that I had come. I don’t remember moving but there I was on my knees between his legs with my right hand on his hard cock and my mouth sliding up and down his shaft. I heard the other two cheer me on which only encouraged me. I was starting to get used to seeing different cocks and I have since found that I enjoy the variety. When I walk down the street I find myself imagining what kind of cock each man that I pass possesses. Some are short, some are long, some thick, some skinny. Some men are circumcised and some even have a wicked curve when they are hard. I can’t say that I have a preference for a specific kind. I just love cock.
Mr Abs soon urged me to move down the line to suck his friend and I complied. It looked like his friends weren’t going to be just an audience tonight. I spent a few minutes on friend number one before moving on to friend number two. I rarely get or give names and prefer it that way. For me Craigslist is like the Bic lighter of fucking. Once it is done you throw it away and move on to the next one.
While I was engrossed in the sucking of friend number two I felt a pair of hands on my ass urging me to move it up and stick it out. I felt his cock sliding over me and he slowly pushed it in. Alarm bells went off in my head as I didn’t even know if he was wearing a condom or not. I know I should have stopped him to find out but once he was inside of me I was too turned on and lost in the moment to care. I just went with it.
I consider myself educated and I know the importance of safe sex but I’m ashamed to say that I don’t always practice it. Unless the guy is absolutely filthy or has something visible on him I will usually go along with however they want to do it. I do get tested regularly and so far so good.
I don’t condone or suggest this for anyone else. I will say there are nights afterwards when I am alone with only my thoughts when I can feel their cum dripping out of me that I’m terrified and disgusted with myself. The time between when you go to the clinic for the tests and wait for the results to come back are equally unbearable.
Who do I do it you ask? I ask myself that question all the time. Maybe it has to do with the thrill of having sex with strangers. The risk of it all, the thrill of the unknown, the need for that adrenaline rush of doing something you shouldn’t. It is all of that and more. The truth is that bare sex feels better. The safe sex ads will never tell you that. When a guy is inside of me I can’t always tell if he is wearing a condom or not. But when I know it is bare, when I see it or guide it in with my hand, when I know it is skin on skin, it is huge turn-on. And oh my God do I love the feeling of a guy cumming inside of me.
Where was I? Oh yes. On my hands and knees sucking the cock of friend number two. Mr Abs was behind me with his hands on my hips and I had the first cock other than Greg’s to ever be inside of me. I think it was more the mental realization of what was happening than the physical stimulation but I orgasmed almost immediately. I had to stop sucking as my body shook and all my muscles tensed. I wonder if the neighbours heard my screams. I don’t think I’d ever been so wet in my life and a gush of juices flowed out of me to meet Mr Abs’ thrusting cock.
They all cheered at the site of it and began telling me what a fucking hot slut I was. I have since come to terms with it but that was the first time I realized that I might indeed be a slut. Really the guys that I meet are just as much a slut as I am but the label doesn’t seem to apply to them the same way.
I think it was friend number one who grabbed a bottle of lube and put a generous amount on his finger. All I know is a felt a slick finger pushing into my ass. I had never had anal sex before in my life. Greg used to ask from time to time and we did try once or twice but have I mentioned that I’m tiny? That means I also have a tiny little asshole and would always stop him once he started to push in.
I was in a room with three jocks and I knew I didn’t really have much a chance of stopping them from doing anything to me if they really wanted to do it. That was part of the thrill of all of this, right?
Mr Abs pulled out of me and friend number one moved in. I could feel his cock head rub up against my little asshole. He began to push it in and my whole body tensed in fear of it. I even had to stop sucking friend number two. He told me that I had to relax and it would be much better for me if I wasn’t so tense. I tried my best to relax as he suggested but I don’t care what anyone says, anal sex hurts.
I had never felt so filled as his cock head pushed into me and stretched me. He did it as slow as he could. My eyes were shut tight and I was biting my bottom lip as I tried to relax and take him into me. He pushed in slowly and I could soon feel his body pushed up against my behind. He was in me all the way. Finally I exhaled. He slowly pulled out a little and pushed back in. He stretched my insides and my body began to expand to take him.
I’ll admit that it actually feels pretty good once you get past that first little bit but because of that initial discomfort it isn’t something I always look forward to. I also have this fear and worry that I’m going to end up shitting all over whoever is in my ass. Most guys don’t seem too worried about that though.
As he picked up the pace my body twitched and reacted to his fucking and I even let out a moan or two. The bunch of them cheered when they saw and heard it. It seemed I was now their new favourite slut.
He pulled his cock out of me and I was lifted up off the ground. It is a little concerning and yet so fucking hot when you realize that the group of them can man handle you with such ease.
Mr Abs laid down on his back on the floor and I was lowered down on top of him. This time I was able to get a look and they were fucking me bare. His cock easily slid into me as I was still sopping wet. His hands went out and grabbed my ass cheeks. He spread them wide as he held and steadied me.
Friend number one moved in and lined his cock back up to my ass and repeated the process to stretch me as he pushed inside. Most times when I’m double penetrated I think that my skin is going to split and they are going to ruin me. Luckily that has never happened. But there really is no way to describe the feeling of being so completely filled. It is so dirty. It is so wrong. And I so love it.
Friend number two walked around to my head and offered me his cock again. I got the feeling that these guys were well practiced and this wasn’t their first rodeo.
Being in this position with the three of them reminds me of a locomotive starting up. There are a lot of pieces that move slowly as they get coordinated and build up steam to get to a faster and faster pace. And really being in that position there isn’t a whole lot I can do as I’m just there for the ride.
I don’t know how long we were in that position but I do know I came multiple times as they thoroughly used every one of my holes. If the neighbours hadn’t heard me the first time they would have to be deaf to not hear our screams and moans of passion this time.
It was friend number one who came first. I felt his cock harden as he pushed deep into my ass and held it there. He let out a scream as he unleashed inside of me. I felt his cock twitch and shake. Mr Abs must have felt it too because he let out a loud ‘Oh Fuck Yeah’ and I felt him unload in my pussy immediately after. I was paralyzed in the throws of my own orgasm when friend number two stroked his cock inches from my face and covered it with his hot sticky load. This was also something I never let Greg do but now I actually look forward to the warmth of it when it splashes on my skin. The slimy feeling as it slides down and even the look when I see myself in a mirror.
Friend number one pulled out of me and lifted me off of Mr Abs. I was placed on the edge of the couch with my legs spread and my ass and pussy hanging off the edge. They wanted to see me push their cum out of me. I thought they had watched one too many pornos but I still did it. They scooped it out of me and fed it to me with their fingers. It was all mildly disgusting but they really seemed turned on by it so I did it.
These guys were young enough to have the stamina to go multiple times. We fucked throughout the night and I’m pretty sure they each used all of my holes at least once. It was four in the morning when I called the taxi for the ride home. They even pooled some money together to pay for my cab fair. How nice of them.
I washed up in the bathroom as best as I could before leaving. My makeup was a mess and I did the best to get the cum out of my hair. Nobody knew what happened to my panties and I suspected one of them pocketed them. I must of been quite the sight for the cab driver and I apologize to the next person if I left any cum on his back seat. Not my fault they took my panties.
I drew a hot bath when I got home and I spent a long time soaking in it. I phoned in sick to work the next day. I didn’t get a lot of sleep that night and my whole body was incredibly sore. Muscles that I didn’t even know I had were burning. My ass had never been so abused and felt so raw. I knew I was walking funny and didn’t want anyone to see me that way.
Those first couple of months I was meeting guys almost every night. Sometimes I’d even answer multiple ads on the weekends. Even the night after the gangbang I found I couldn’t resist finding someone who wanted a blowjob. I was too sore for anything else.
I don’t go as often anymore. Sometimes it’s once or twice a week and sometimes I’ll go a whole month in between. But it is always in the back of my mind and I am always reading the ads even if I’m not answering them. There are some guys that have become regulars but I have found for the most part the second time around isn’t as good as the first. If I already know what is waiting for me than I just don’t get the same thrill and exhilaration from it.
I know my story probably shocks you. It shocks me when I sit down and really think about it. But this is how I became addicted to being a Craigslist slut.
This all started about a year ago on my twenty-first birthday. I had broken up with my boyfriend three months earlier and was feeling very lonely and sorry for myself. Greg and I had dated for 4 years. We were high school sweethearts, had gone to prom together, he was the only man I’d ever been with sexually, and we were engaged to be married. That is until we had ‘the talk’ where he claimed he had changed and we had grown apart. The truth was he had dumped me for Carla Wright.
I was of course devastated. I mean Carla Wright? If you are going to dump me at least dump me for someone who is better looking than I am. Someone better educated, with a better personality, or someone with a better job. But not Carla Wright. I guess there is no accounting for some peoples taste and I realize now that I am probably better off without him.
Back to my twenty-first birthday. I had declined all offers from friends and family to go out that night. I was depressed and just not in the mood to be celebrating. The only thing I wanted to do was order in Chinese and curl up with a good book. I finished my book by eleven that night and was extremely horny. Yes it was one of those smutty romance novels. It had been a long time since I had any intimacy or sex. Greg and I really weren’t doing it a whole lot towards the end and I was getting to the point where my dildo just wasn’t cutting it anymore.
I don’t even remember where I had first heard about Craigslist. Maybe it was overheard from guys at work or maybe it was online somewhere. Craigslist is basically a website that replaces the buy and sell ads of a newspaper. It has all sorts of different categories where people post ads for things they are selling or buying.
The seedy side of Craigslist happens in the personals section. These are sections where you can meet people to date but those aren’t used a whole lot. The real action happens in Casual Encounters. You can look at ads that are from males looking for females, or couples looking for females or males. Basically any combination of man, woman, couple, or transexual.
At this point in time I wasn’t posting my own ads so I went to the ‘m4w’ section. I answered a few ads that had pictures with hot guys but the emails that came back wanted me to sign up for websites and weird shit. After a while you learn to pick out the real ads from the spam.
I saw an ad where the title said ‘Lost My Job Need Something Good Tonight'. The text of the ad went on to describe how he had the worst week of his life and was just looking for something good to happen. He was a forty-five year old man which at that time I would never had gone for, but I suppose misery loves company and I kind of felt sorry for him.
We corresponded back and forth a bit through email. I’ve learnt that this part is a bit of a game where you learn how serious someone is about actually hooking up. A lot of people just don’t follow through. We didn’t exchange pictures as neither of us were comfortable doing that. It was lucky that we lived in close neighbourhoods but neither of us wanted to use our houses. I also told him that this was my first time on Craigslist and I didn’t think I could have sex but I would give him a blowjob. In reality I really did want sex but I wasn’t yet ready to start fucking strangers. I think it was really just the intimacy that I was looking for that night. He was happy with a blowjob and we agreed to meet at a nearby coffee house.
After the last email we agreed to meet in 30 minutes and I remember panic setting in. What the hell was I doing? Was I really going to go? Was I meeting with a psychopath who was going to kill me? I changed out of my pyjamas and put on jeans and a shirt. It was late and I didn’t have the time for anything fancy. I don’t believe I’ve yet described myself for you. Basically I am tiny and I am short. I’m a half-inch over five-foot-two. And yes that half-inch is very important! I weigh in at about 105 pounds. I have blue eyes with long blonde hair and what many have called a cute button nose face. My breasts are on the smaller side so we don’t need to go into detail about those. When I gave myself the final look over in the mirror I thought I looked pretty damn hot.
I don’t have a car so I walked to the coffee house that night. It took me about fifteen minutes and my heart felt like it was beating a million times a minute the whole way there and my senses were on high alert. There is an adrenaline rush I get from doing something dangerous or doing something I know I shouldn’t. I definitely had that rush going that night. It was a huge contrast from the loneliness and depression that I had been in for the months prior. Maybe the rush is the reason I became addicted to doing this, maybe it was the feeling of basking in sunlight after being stuck in darkness for so long that got me hooked, or maybe just maybe I really am a slut and like hooking up with strange men.
I got to the coffee house and there were only two tables with people at them. One of them was an older guy with a red baseball cap and a blue jacket. Just like he said he would be wearing. It is an odd feeling to both want and not want something so much at the same time. The fact that he was there was absolutely thrilling to me. And the fact that he was there was absolutely terrifying.
I sat at his table and we exchanged awkward pleasantries as we checked each other out. He wasn’t ugly but he wasn’t someone I’d pick out of a crowd to go home with. He was a little over weight and probably balding under his cap. I was half his age and I could tell he was very happy with me. He told me I wasn’t at all what he expected, that I was hot and a very pleasant surprise.
When he asked me if I wanted to go to his car I nodded my head yes and we both got up to leave. One of my issues is that I hate making people feel bad. I don’t like saying ‘no’ to people and I don’t like disappointing them. I guess I’m what they call a pleaser. This wasn’t the case with this guy as this was my first time with Craigslist and I was buzzing from that but in my time doing this I’ve met some guys that I had absolutely zero attraction to but I went ahead and fucked them anyway because I didn’t want them to feel bad. This is where screening becomes very important because for me if I commit to meeting them I’ve pretty much committed to fucking them.
His SUV was parked in the back of the parking lot and we walked to it in silence. I’m glad my first time was in an SUV. If you ever plan on doing these kinds of things in cars, bigger is better. I may be tiny but sex is not fun in a compact car.
That walk to his car was one of the longest of my life. I was convinced that he was going to kidnap me, rape me, and murder me. My heart was thudding and my breathing was laboured. He got into the driver side and I into the passenger side and we just sat there with neither of use saying anything until the dome light went out.
He reached down and undid his pants. I still remember the sound of his zipper. His cock came out and he was stroking it. It was only the second cock I’d ever seen live and it was much thicker than Greg’s. He reclined his seat back to give me full access.
I leaned over and he let go of his cock so that I could take over. My hand closed around the base of his shaft and I ran my tongue over the head. I never really enjoyed giving Greg blowjobs and it was just one of those things I did. Maybe thats why he had moved on to Carla Wright. But that night, in that moment, my feelings on blowjobs changed.
The feeling of a strangers hard cock in my hand, his musky scent in my nose, and his taste in my mouth is a very powerful one and I could feel my pussy get immediately wet. Sometimes now when I’m sucking I don’t even care who the guy is. It is just about me and his cock. I don’t care about anything else.
As I took him into my mouth and began to bob my head up and down his shaft I could feel his cock grow harder and harder. The harder he got the wetter I got. I got so turned on that I had to undo my pants and slip a hand between my legs to rub while I blew him.
I felt his hand on my head and he began to guide me. I like it when guys show me how and where they like to be sucked. Each time I learn how to please a man I add it to my repertoire to reuse on someone else another time. His cock began to ooze precum in my mouth and I happily reapplied it to his shaft with a mixture of my saliva. I loved how slick and wet it got.
When he was ready to cum he held my head in place and filled my mouth. Holy shit there was a lot of cum. He must of been holding off for at least a week. With Greg I never swallowed but I have found a new appreciation for it. Lets be honest, at best it tastes just okay, at worst it is putrid. But the prize is in knowing that I was the one who made him cum and for that I now swallow it all.
There was another awkward silence as I moved up from his lap wiping my mouth. He offered me a weak ‘thank you’. I got the feeling that he wanted to get the hell out of there quickly. I only nodded my head and got out of the car. Our agreed to deed was done. I never saw him again but I will always remember him fondly as he was my first.
I walked home that night with an odd sense of satisfaction even though I didn’t get off. I was happy for the first time in a long time. It felt good to get someone else off. I slept more soundly that night than I had since the breakup and although I can’t remember the dreams I had I got the feeling the next morning that they were wild and amazing. My sleep was kind of like that blissful feeling you get when you sleep in a lovers arms for the first time.
The only difference was that when I woke up I was still alone. I went about my morning routine getting ready for work all the while replaying the previous nights activities in my mind. By the time I got to work I knew I was going back out that night and this time I wanted to go all the way.
Thank God for smartphones as I was able to surf Craigslist all day without anyone else knowing or seeing. I didn’t get much work done as I corresponded with a bunch of ads. I decided I wanted to see pictures first this time but this usually means you need to send one as well. Lets be honest here for those of you thinking you want to get into this life, pictures aren’t a guarantee as many people will send fake ones just to get you to show up and I’m ashamed to admit that ploy does work on me so I probably contribute to the problem.
Into the bathroom stall I went and used my phone to take some half naked pictures of my body. I had to wait until there was no one else in there as I didn’t want anyone seeing the flash going off. Classy right? Well other than both words starting with the letter ‘C’, Craigslist and classy have little in common.
I’d settled on a guy whose picture had abs to die for. He was able to string more than two sentences together in his emails, he was around my age, and he seemed more or less normal. I was on a high for the rest of the day. My mind was buzzing with things like what he would really look like, what we would do together, and my mind always wonders if I’ll be walking into some kind of trap. I think I enjoy the buildup just as much if not more than the actual act itself. The anticipation is kind of like the feeling you get with Christmas or your birthday. You never know if you are going to like your presents until you open them up and see what is inside. Sometimes you are horribly disappointed and other times your mind is completely blown.
We had agreed to meet at his place at eight that night. I knew I didn’t want to do it in a car again. I also knew that I didn’t want this guy to know where I lived. So that left his place. Dangerous but risk is part of the game. I took a long hot bath when I got home from work and took the time to shave my legs and pussy. I hadn’t been seeing anyone for long enough that I had let my grooming go.
I enjoy the ritual of preparing myself for the men that I meet. I inspect and prepare my body all the while imagining their reaction when they see me. Shaving, lotions, makeup, perfume, hair. I want everything to be perfect. You hope that they will be blown away when they see you and appreciate the effort you put into getting ready. Sometimes I wish the guys would put the same effort in on their end or at the very least shower before we meet. Often I get so worked up with the thought of what is to come that I need to masturbate while I get myself ready.
It was a beautiful summer night and I decided to wear a short white summer dress. I often wish my breasts were bigger but sometimes in situations like this I can get away without wearing a bra. They aren’t going to be falling out or flopping all over and I think it is kind of hot when you can see the silhouette of my erect nipples poking through my dress. I put on a lacy white thong that wouldn’t show through the dress and I was on my way.
I knew I was looking good during the cab ride when the driver kept checking me out in his rear view mirror. He dropped me off and I walked up to the apartment building and those now familiar butterflies were flapping madly in my stomach. I punched in the buzz code and the buzzing of the door unlocking went off without us exchanging a word. There was an agonizing wait for the elevator followed by a heart thumping walk down the hallway and finally the wait to gain enough courage to knock on the door.
The door opened and a smiling guy wearing only shorts opened the door and invited me in. He obviously worked out and those abs were indeed the ones I had seen in the picture. Things were looking good.
The door closed behind me and I took in the scene in front of me. The first thing I noticed, probably due to the noises coming from it, was that there was porn playing on the TV. The second thing I noticed was that there were two other guys on the couch, naked, and jerking off to the porn.
I always thought that most guys were squeamish about being around each other naked or seeing each other hard but I’ve found out that there are pockets of them that love jerking off together and fucking girls together.
I froze with my back to the door. I was only expecting one guy and this curve ball had me thinking I should turn around and bolt. The one with the abs must have seen the fear in my eyes and reached out to gently take my hand. He told me it would be okay and if I wanted to only fuck him the others would only watch.
I let myself be led into the living room and escorted to in front of the TV. He slipped off his shorts and took his place on the couch with his friends. There I was standing in front of three strange men who were buck naked and hard and all eyes on me. I knew when I saw the desire in their eyes, the desire for me, that I would be staying. Mr Abs suggested that I should strip.
I wish I could say that I put on a good show for them but the truth is I don’t like being in the spotlight and aware that all eyes are on me. If I did maybe I’d be making money as a stripper instead of doing this. Believe it or not I’m actually quite shy. I took my dress off and they expressed their pleasure at seeing me with no bra. The only thing left was to slide my panties down my legs and I stood there watching them watch me. A five second strip show. Mr Abs spread his legs and motioned me over.
I was instantly wet and glad that I had come. I don’t remember moving but there I was on my knees between his legs with my right hand on his hard cock and my mouth sliding up and down his shaft. I heard the other two cheer me on which only encouraged me. I was starting to get used to seeing different cocks and I have since found that I enjoy the variety. When I walk down the street I find myself imagining what kind of cock each man that I pass possesses. Some are short, some are long, some thick, some skinny. Some men are circumcised and some even have a wicked curve when they are hard. I can’t say that I have a preference for a specific kind. I just love cock.
Mr Abs soon urged me to move down the line to suck his friend and I complied. It looked like his friends weren’t going to be just an audience tonight. I spent a few minutes on friend number one before moving on to friend number two. I rarely get or give names and prefer it that way. For me Craigslist is like the Bic lighter of fucking. Once it is done you throw it away and move on to the next one.
While I was engrossed in the sucking of friend number two I felt a pair of hands on my ass urging me to move it up and stick it out. I felt his cock sliding over me and he slowly pushed it in. Alarm bells went off in my head as I didn’t even know if he was wearing a condom or not. I know I should have stopped him to find out but once he was inside of me I was too turned on and lost in the moment to care. I just went with it.
I consider myself educated and I know the importance of safe sex but I’m ashamed to say that I don’t always practice it. Unless the guy is absolutely filthy or has something visible on him I will usually go along with however they want to do it. I do get tested regularly and so far so good.
I don’t condone or suggest this for anyone else. I will say there are nights afterwards when I am alone with only my thoughts when I can feel their cum dripping out of me that I’m terrified and disgusted with myself. The time between when you go to the clinic for the tests and wait for the results to come back are equally unbearable.
Who do I do it you ask? I ask myself that question all the time. Maybe it has to do with the thrill of having sex with strangers. The risk of it all, the thrill of the unknown, the need for that adrenaline rush of doing something you shouldn’t. It is all of that and more. The truth is that bare sex feels better. The safe sex ads will never tell you that. When a guy is inside of me I can’t always tell if he is wearing a condom or not. But when I know it is bare, when I see it or guide it in with my hand, when I know it is skin on skin, it is huge turn-on. And oh my God do I love the feeling of a guy cumming inside of me.
Where was I? Oh yes. On my hands and knees sucking the cock of friend number two. Mr Abs was behind me with his hands on my hips and I had the first cock other than Greg’s to ever be inside of me. I think it was more the mental realization of what was happening than the physical stimulation but I orgasmed almost immediately. I had to stop sucking as my body shook and all my muscles tensed. I wonder if the neighbours heard my screams. I don’t think I’d ever been so wet in my life and a gush of juices flowed out of me to meet Mr Abs’ thrusting cock.
They all cheered at the site of it and began telling me what a fucking hot slut I was. I have since come to terms with it but that was the first time I realized that I might indeed be a slut. Really the guys that I meet are just as much a slut as I am but the label doesn’t seem to apply to them the same way.
I think it was friend number one who grabbed a bottle of lube and put a generous amount on his finger. All I know is a felt a slick finger pushing into my ass. I had never had anal sex before in my life. Greg used to ask from time to time and we did try once or twice but have I mentioned that I’m tiny? That means I also have a tiny little asshole and would always stop him once he started to push in.
I was in a room with three jocks and I knew I didn’t really have much a chance of stopping them from doing anything to me if they really wanted to do it. That was part of the thrill of all of this, right?
Mr Abs pulled out of me and friend number one moved in. I could feel his cock head rub up against my little asshole. He began to push it in and my whole body tensed in fear of it. I even had to stop sucking friend number two. He told me that I had to relax and it would be much better for me if I wasn’t so tense. I tried my best to relax as he suggested but I don’t care what anyone says, anal sex hurts.
I had never felt so filled as his cock head pushed into me and stretched me. He did it as slow as he could. My eyes were shut tight and I was biting my bottom lip as I tried to relax and take him into me. He pushed in slowly and I could soon feel his body pushed up against my behind. He was in me all the way. Finally I exhaled. He slowly pulled out a little and pushed back in. He stretched my insides and my body began to expand to take him.
I’ll admit that it actually feels pretty good once you get past that first little bit but because of that initial discomfort it isn’t something I always look forward to. I also have this fear and worry that I’m going to end up shitting all over whoever is in my ass. Most guys don’t seem too worried about that though.
As he picked up the pace my body twitched and reacted to his fucking and I even let out a moan or two. The bunch of them cheered when they saw and heard it. It seemed I was now their new favourite slut.
He pulled his cock out of me and I was lifted up off the ground. It is a little concerning and yet so fucking hot when you realize that the group of them can man handle you with such ease.
Mr Abs laid down on his back on the floor and I was lowered down on top of him. This time I was able to get a look and they were fucking me bare. His cock easily slid into me as I was still sopping wet. His hands went out and grabbed my ass cheeks. He spread them wide as he held and steadied me.
Friend number one moved in and lined his cock back up to my ass and repeated the process to stretch me as he pushed inside. Most times when I’m double penetrated I think that my skin is going to split and they are going to ruin me. Luckily that has never happened. But there really is no way to describe the feeling of being so completely filled. It is so dirty. It is so wrong. And I so love it.
Friend number two walked around to my head and offered me his cock again. I got the feeling that these guys were well practiced and this wasn’t their first rodeo.
Being in this position with the three of them reminds me of a locomotive starting up. There are a lot of pieces that move slowly as they get coordinated and build up steam to get to a faster and faster pace. And really being in that position there isn’t a whole lot I can do as I’m just there for the ride.
I don’t know how long we were in that position but I do know I came multiple times as they thoroughly used every one of my holes. If the neighbours hadn’t heard me the first time they would have to be deaf to not hear our screams and moans of passion this time.
It was friend number one who came first. I felt his cock harden as he pushed deep into my ass and held it there. He let out a scream as he unleashed inside of me. I felt his cock twitch and shake. Mr Abs must have felt it too because he let out a loud ‘Oh Fuck Yeah’ and I felt him unload in my pussy immediately after. I was paralyzed in the throws of my own orgasm when friend number two stroked his cock inches from my face and covered it with his hot sticky load. This was also something I never let Greg do but now I actually look forward to the warmth of it when it splashes on my skin. The slimy feeling as it slides down and even the look when I see myself in a mirror.
Friend number one pulled out of me and lifted me off of Mr Abs. I was placed on the edge of the couch with my legs spread and my ass and pussy hanging off the edge. They wanted to see me push their cum out of me. I thought they had watched one too many pornos but I still did it. They scooped it out of me and fed it to me with their fingers. It was all mildly disgusting but they really seemed turned on by it so I did it.
These guys were young enough to have the stamina to go multiple times. We fucked throughout the night and I’m pretty sure they each used all of my holes at least once. It was four in the morning when I called the taxi for the ride home. They even pooled some money together to pay for my cab fair. How nice of them.
I washed up in the bathroom as best as I could before leaving. My makeup was a mess and I did the best to get the cum out of my hair. Nobody knew what happened to my panties and I suspected one of them pocketed them. I must of been quite the sight for the cab driver and I apologize to the next person if I left any cum on his back seat. Not my fault they took my panties.
I drew a hot bath when I got home and I spent a long time soaking in it. I phoned in sick to work the next day. I didn’t get a lot of sleep that night and my whole body was incredibly sore. Muscles that I didn’t even know I had were burning. My ass had never been so abused and felt so raw. I knew I was walking funny and didn’t want anyone to see me that way.
Those first couple of months I was meeting guys almost every night. Sometimes I’d even answer multiple ads on the weekends. Even the night after the gangbang I found I couldn’t resist finding someone who wanted a blowjob. I was too sore for anything else.
I don’t go as often anymore. Sometimes it’s once or twice a week and sometimes I’ll go a whole month in between. But it is always in the back of my mind and I am always reading the ads even if I’m not answering them. There are some guys that have become regulars but I have found for the most part the second time around isn’t as good as the first. If I already know what is waiting for me than I just don’t get the same thrill and exhilaration from it.
I know my story probably shocks you. It shocks me when I sit down and really think about it. But this is how I became addicted to being a Craigslist slut.
Makenna
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