Craigslist experiences (or similar)

sinkingsoundly

Experienced
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Dec 11, 2018
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Around 10 years ago I was almost addicted to these types of meetups. Almost always involved fucking moments after meeting. Neither of you knew anything about each other. Never knew if a significant other was going to walk in. Didn’t know if they were clean.

I had some super intense experiences during these times. What are some of your favorite experiences like this?

I don’t even know how I managed to come out clean. It’s crazy years later when you end up working with some of them or st least crossing paths.
 
Around 10 years ago I was almost addicted to these types of meetups. Almost always involved fucking moments after meeting. Neither of you knew anything about each other. Never knew if a significant other was going to walk in. Didn’t know if they were clean.

I had some super intense experiences during these times. What are some of your favorite experiences like this?

I don’t even know how I managed to come out clean. It’s crazy years later when you end up working with some of them or st least crossing paths.

It never worked for me beyond some online action.
 
Living in the UK there didn't seem to be any real people anywhere near my area. I did discover Gumtree personal ads, before they dropped them, and met a few women. There were an awful lot of timewasters and men pretending to be women. I pulled out of a few meets as they didn't feel right, couldn't put my finger on it but don't regret pulling out.

I made a couple of penpal friends, still chatting to them 6 or 7 years later.

There were a couple of women that I enchanged fantasies with and did some roleplay, lasting a couple of years. One of those we did meet up a few times, sex was good but really we wanted different things.

I met a couple that we didn't progress to sex, the "spark" just wasn't there and one that turned into a one night stand, some of the things she said put me off (sounded almost stalker like lol).

Two became good friends, I had a FWB arrangement with one of them on and off for about 6 years.

So I'm probably not that typical in that I wasn't just looking for sex but I had mixed but OK results.
 
In Town for 2 days

When traveling, I would occasionally post to C List. Here is an example of one I posted a few times. This one was in Texas...lol

I've always gotten some real responses and have had some good times.

"Looking for someone to enjoy dinner and conversation with either night or both. Only non-smokers please. Drinkers ok but please no drunks. While eye candy is dandy, the ability to engage in stimulating conversation is more important.

If you voted for your Jr. Senator, we probably have less than nothing in common.

I'm white but if that is important to you, see comment about your Jr. senator.

Preference would be for a very active, outdoors type of woman - run, bike, sail......?"
 
I had several cuckold experiences on CL. Most of the time it was the husband who would engage me to fuck his wife. I had one regular couple for a while, but the husband became erratic and wanted to text me 24/7 and was always freaking out about this or that.

The sex with these wives was always hot as hell. They all wanted to let out their inner slut!
 
I had one successful CL experience where I met up with a guy a couple of times. It was pretty good but our schedules fell out of synch and that was the end of it.

I tried different times with other guys but it never panned out, or I got cold feet.

I have recently tried kik and wonder if it might lead to anything.
 
Hubs and I used it once or twice when they still had the classified section. Lots of fun and usually had some real people. Be surprised the folks you may find on there. Lots of weirdos but also lots of regular people just like you wanting to have some NSA good times
 
My experience (as a guy) with Craigslist personals typically went something like this:

You read a "W. f. M" ad that sounds enticing. Cool, someone local who shares the same sexual interests!

Then you send her an introductory greeting. You get a reply that goes something like "If you are still interested, check out my profile on (some other adult personals dating site)!!! I will not be checking back here."
Then, you actually go to that site and of course you have to sign up and become a paying member just to respond to an ad (Even though it's a supposedly "Free" site.) And of course if you do sign up (I never did) the person who you connected with on Craigslist isn't actually on there, but instead you find it's 99% guys just like you, desparatly horny suckers each and every one of them.

Oh but wait...sometimes you get lucky. Sometimes you actually get a real online dialogue. Now you are getting somewhere. But then, usually a few e-mails in, but before you EVER ACTUALLY GET TO MEET FACE TO FACE (or even have a voice conversation over the phone) comes the inevitable request for money. She needs money for this or that, or to prove that you are "Serious" and not a flake. Guess what happens once you actually send the money (assuming you are desperate and/or naieve enough to actually do so.)

So, literally EVERY SINGLE ONE of my attempts to meet women on Craigslist have ended up as one of the two above scenarios. So you can understand why I am so cynical about online hook-up sites, especially that particular one. And also why I wasn't particularly dissappointed when the Craigslist personals went away.

It sounds like some people have actually had success with actual hookups with real people on there, but from my experience, it would have to be a rare exception.
 
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My experience (as a guy) with Craigslist personals typically went something like this:

You read a "W. f. M" ad that sounds enticing. Cool, someone local who shares the same sexual interests!

Then you send her an introductory greeting. You get a reply that goes something like "If you are still interested, check out my profile on (some other adult personals dating site)!!! I will not be checking back here."
Then, you actually go to that site and of course you have to sign up and become a paying member just to respond to an ad (Even though it's a supposedly "Free" site.) And of course if you do sign up (I never did) the person who you connected with on Craigslist isn't actually on there, but instead you find it's 99% guys just like you, desparatly horny suckers each and every one of them.

Oh but wait...sometimes you get lucky. Sometimes you actually get a real online dialogue. Now you are getting somewhere. But then, usually a few e-mails in, but before you EVER ACTUALLY GET TO MEET FACE TO FACE (or even have a voice conversation over the phone) comes the inevitable request for money. She needs money for this or that, or to prove that you are "Serious" and not a flake. Guess what happens once you actually send the money (assuming you are desperate and/or naieve enough to actually do so.)

So, literally EVERY SINGLE ONE of my attempts to meet women on Craigslist have ended up as one of the two above scenarios. So you can understand why I am so cynical about online hook-up sites, especially that particular one. And also why I wasn't particularly dissappointed when the Craigslist personals went away.

It sounds like some people have actually had success with actual hookups with real people on there, but from my experience, it would have to be a rare exception.

Back in the 80's, my roommate signed up for some dating thing. This predated VCRs and the Internet as we know it. So it was snail mail dating. Women could do it for free. The person who signed my roommate up, begged me to join as very few women ever joined. I declined.

My roommate was older than me and had totally different interests than me. She wanted to be married. I didn't.

The way it worked was to get 5 profiles at a time.

Guy number one came to our house and began demanding sugar. We had none. No candy or OJ either. Turned out he was diabetic and having a bad hypo. He began getting violent. We finally found something in the kitchen (can't remember what) to bring his blood sugar up but by then, she didn't want anything to do with him.

On to guy number two. He appeared to be wealthy. Owned a convenience store, sports car and lavished gifts on her. Proposed marriage after two weeks. She accepted and showed me her ring. Another friend invited us all over for dinner. The guy started being a real ass. Controlling everything she did. He told her that after they married, he expected her to cook, clean, run the store and do whatever else he told her to, for no pay. She would have to quit her job. Said she wouldn't need money. He would decide what she needed. She threw the ring back at him and we all told him to get out.

Guy number three! I did not know it at the time but my roommate had gotten pregnant by a male friend. The two of them eloped in Reno that weekend, but she didn't want to announce the marriage until afterwards.

She kept telling guy number three that she couldn't go out with him but wouldn't tell him why. I'm not sure what all else she said to him except that her roommate would go out with him and then handed me the phone.

I was elbow deep in a large bowl of sugar cookie dough. I was using my hands to mix it so that was awkward. I tried to talk some sense into the guy. Said that if he was matched up with her based on interests, it would not work out well with me. He began pleading with me and went into a rant about how the guys had to pay $20 for five profiles. He had paid repeatedly and kept getting the same three profiles. Apparently they only managed to get three women to sign up. None of them interested him but he decided to try anyway. He began guilt tripping me. In my mind, I could see my mother hovering over me, screaming at me, telling me that I was too picky and I should give the guy a chance.

I finally said I would go out with him. But seeing as how I was an unknown quantity, he refused to drive to my city. Told me to meet him at the Denny's in his city. I had been to his city a few times to go to a fancy restaurant but beyond that, I knew nothing about it. My dad told me where the Denny's was. Turned out there were two Denny's and I went to the wrong one.

This pissed the guy off. I got there late so we missed the movie that he wanted to see. I was relieved though because I didn't want to see the movie and it was a really long one.

So he told me to meet him across the street at a jazz club. I can handle jazz in small doses, but two hours of it is rather torture for me.

Everything went bad from there. He hated everything, everything about me and was most vocal about it. He was a butcher. I was a vegetarian. I smoked. He hated smokers. He drank. I didn't. The list went on and on. He also demanded that I stay there for two hours. I did. Not sure why. For the most part, I blotted the whole bad date out of my mind. I kept my eye on the time then left.

More recently, my daughter said that my ex joined a dating site. We tried to look to see what lies he was telling about himself but it made me sign up. I did but only long enough to look at the male profiles in this area. Ex must have blocked me as we couldn't see his profile. All but two of the guys looked like they walked into a wall and didn't recover from it. Now looks aren't everything but the information they provided about themselves was dismal. The two that looked normal were in their very early 20's I reckon they hadn't walked into that wall yet! Oh I am bad! But... That is what I thought.
 
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My first time fucking a CD off CL

A few years back I got super horny decided I really wanted to get a blowjob. I found a older cd who lived relatively close by and decided what the hell. Sent a message and sure enough I got a response a few minutes later. I ended up driving over, when I parked he flashed his house light so I’d know for sure which one was his. I walked into a darkened living room, we said hello. I then dropped my shorts and boxers and pulled out my uncut cock. He was wearing a wig, makeup and sexy lingerie and needless to say I got hard quickly as he started aggressively and expertly sucking my cock. I thought I was gonna bust after a little while, but then he paused to ask me a question I wasn’t prepared for. He asked me if I wanted to fuck him? Sure, I’d let a few other dudes play with my cock before but never anything more than jerking and sucking. This was a whole new experience. I said yes, he promptly turned around and bent over, presenting a glistening, smooth, lubed asspussy for me to fuck. I don’t think I lasted more than a minute or two. I was so damn turned on. I pumped my seed into his asshole, put on my underwear and shorts and went about my day. I still get turned on thinking about that day but don’t know if I’ll have another experience like it now that cl personals is gone.
 
hey...

A few years back I got super horny decided I really wanted to get a blowjob. I found a older cd who lived relatively close by and decided what the hell. Sent a message and sure enough I got a response a few minutes later. I ended up driving over, when I parked he flashed his house light so I’d know for sure which one was his. I walked into a darkened living room, we said hello. I then dropped my shorts and boxers and pulled out my uncut cock. He was wearing a wig, makeup and sexy lingerie and needless to say I got hard quickly as he started aggressively and expertly sucking my cock. I thought I was gonna bust after a little while, but then he paused to ask me a question I wasn’t prepared for. He asked me if I wanted to fuck him? Sure, I’d let a few other dudes play with my cock before but never anything more than jerking and sucking. This was a whole new experience. I said yes, he promptly turned around and bent over, presenting a glistening, smooth, lubed asspussy for me to fuck. I don’t think I lasted more than a minute or two. I was so damn turned on. I pumped my seed into his asshole, put on my underwear and shorts and went about my day. I still get turned on thinking about that day but don’t know if I’ll have another experience like it now that cl personals is gone.

If that first guy lives alone---, knock on his door (?)
 
I used to use craigslist years ago. Didnt get many good experiences out of it. I seem to fall into the same rut, you spend some time sending emails back and forth for a couple of weeks, send a picture, meet in a public place, mainly coffee shop. I met around 6 or 7 women. Only went further with one of the them. Out of the others, some had provided a photo were obviously out of date. With one woman it was clear the photo wasnt of her. Not sure why you would do that.

On one occasion, the woman didnt turn up. Or turned up saw me and left :eek: I sent her a couple of emails afterwards and never received a reply.
 
We used a friend finder site and had good luck with that. 4 out of 5 lead to me watching her have sex.
 
for me it always worked if I was honest
I always wrote ad
never replied to ads
weeded out a few replies
and presto
insta sex!
 
no luck

Never had any luck on cl. But on the new double list gotten lucky 3 times. One guy I hooked up with new I enjoy cross dressing so he asked if I would wear stockings and panties. He came over I gave him a beer he chugged half of it down said ok give it to me. As he was sitting I walked over to him standing. He pulled my panties down under my balls went right to town on my cock. He had me hard to cumming down his throat in about 3 mins. He chugged down the rest or the beer said thanks and left.
 
hey...

re: OP

One day I couldn't find any relief---, masturbating wasn't working, porn wasn't working. The wife was ALWAYS working but never in the bedroom.

I thought I'd try this Craigslist thing I had heard about. Read the rules, guidelines and all the rest of the bullshit. Figured out something to write that wasn't a total crap story. And then posted, it took about a day and a half, a guy in my town had his own business and like that, we texted for a bit and then he asked if I was new to this '....whole thing'. I said yes, he asked me then if I would like a blow job---hell, I couldn't even type "yes" I was shaking so hard.
He told me where he was located and what time to be there, I was there about 10 minutes early. We talked a bit then he walked over and flipped his "open" sign to closed and he locked the door and we walked into his office.

He told me before he went to his knees, to let him know when I was ready to cum-, that was his only rule. He also had NO GAG reflex, he said I could take his mouth and slam it down on my dick, I ask him how hard? He said as hard as I could take it. He had my finger prints on the back of his bald head for days after that. I would still be going back but he wouldn't wear a condom, while I tried to learn to 'throat cock'. I already knew how to suck a cock good enough to make 99.9 percent of the male populations eyes roll back in their head, lose their breath and all control of their musculature--, but it don't mean a thing if they don't put on that rain jacket.
He just passed on my offer to return the favor, muttering some shit, something about a perceived and noticeable reduction in sensitivity and it takes too long.


The only other experience with Craigs brought me to the house of a guy who had a dick BIGGER AROUND THAN A FUCKN BEER CAN. It was like he had a fire hydrant in his pants. 6 inches long and damn near that big around... fuckn thing gave me lockjaw.
 
hey...

re: OP

One day I couldn't find any relief---, masturbating wasn't working, porn wasn't working. The wife was ALWAYS working but never in the bedroom.

I thought I'd try this Craigslist thing I had heard about. Read the rules, guidelines and all the rest of the bullshit. Figured out something to write that wasn't a total crap story. And then posted, it took about a day and a half, a guy in my town had his own business and like that, we texted for a bit and then he asked if I was new to this '....whole thing'. I said yes, he asked me then if I would like a blow job---hell, I couldn't even type "yes" I was shaking so hard.
He told me where he was located and what time to be there, I was there about 10 minutes early. We talked a bit then he walked over and flipped his "open" sign to closed and he locked the door and we walked into his office.

He told me before he went to his knees, to let him know when I was ready to cum-, that was his only rule. He also had NO GAG reflex, he said I could take his mouth and slam it down on my dick, I ask him how hard? He said as hard as I could take it. He had my finger prints on the back of his bald head for days after that. I would still be going back but he wouldn't wear a condom, while I tried to learn to 'throat cock'. I already knew how to suck a cock good enough to make 99.9 percent of the male populations eyes roll back in their head, lose their breath and all control of their musculature--, but it don't mean a thing if they don't put on that rain jacket.
He just passed on my offer to return the favor, muttering some shit, something about a perceived and noticeable reduction in sensitivity and it takes too long.


The only other experience with Craigs brought me to the house of a guy who had a dick BIGGER AROUND THAN A FUCKN BEER CAN. It was like he had a fire hydrant in his pants. 6 inches long and damn near that big around... fuckn thing gave me lockjaw.
 
I never used CL but I hooked up with a guy from Reddit. It was a hot first meeting and we had an FWB thing for a bit.
 
I usually posted ads. Most ads I saw there didn't appeal or were too far away (I live in a pretty rural area).

I had lots of "women" respond to my ads—even to ads for men. All were SpamBots.

I had a fair number of men respond too. Most were creeps and I didn't meet them. A couple of conversations seemed interesting, but didn't lead anywhere. Then there were three men I did meet.

  1. I sucked him for a while, then he fucked me. I left. No human connection at all, and something seemed weird about him. I never went back.
  2. Seemed great. Instant friendship. We fucked only a few times, after that the sex lost its energy. I think he wanted a top, which I definitely am not. We remained good friends for a couple of years after we stopped having sex. Not sure why he drifted away, but the connection was good while it lasted, even if the sex petered out.
  3. Bingo! Great sex, immediate friendship, and bonus, he had (has) such a fine cock. 8" at least, and real thick. We're not having sex anymore because I'm trying to get back together with my wife. But we remain good friends and talk regularly. I miss his cock and want him to fuck me every time I see him. But I'm trying to be good...

That's my experience. Three hits out of 20 or 30 ads posted. Of those three, two were genuine connections; of those two, one was incredible sex too. Not bad, really.
 
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Cl

We really miss CL. We had some great successes. We met and made some great connections. We began by email and phone screening and were pretty successful in weeding out the fakes and real mismatches.

MF4F was a complete flop for us.
F4F wound up being foreplay for my wife several times. She never made a real connection but had fun with initial interactions.
MF4MF we met many couples for drinks and maybe dinner. Usually it didn't go beyond that but the verbal interaction. The sexual edgeplay that something might be there even if it wasn't would still lead to a great night of sex between my wife and I. Many nights when there was a connection between the women, the women would take the bathroom together. My wife knew that it was a turnon for me to know that the two of them would stand in front of the mirror, kiss, make out and feel each other up until they were well and truly caught by someone else coming into the bathroom. She loved to keep that tight hug and lip lock so that the fact that the two of them were making out was unmistakable to whoever "surprised" them. The best times were when they would come back from the bathroom disheveled and with makeup a little smeared.
MF4M was a great connector. We regularly posted for guys with big cocks. The very act of meeting at a bar or restaurant was foreplay. We would talk about interests, experiences, desires and expectations. She would feel them up in public to get them hard and to see if they were packing what they were claiming. sometimes it led to more.
We also met a few panty collectors and let them remove them themselves.
We also met a few that were into other kinks that I won't go into here.
All told. CL is sorely missed!
 
replacement?

I have had a couple of fun encounters with CL. I miss it. Has anything been able to replace it?
 
I used to use it regularly ( a couple times a year ) when I had a couple of days free. Generally, I'd just advertise for guys who were into whatever perversion I was into at the time. It's funny how many replies you get if you offer to let someone spank you while you suck them off.

About 50% of the replies were real and workable. About 20% were trolls who just wanted to see how long they could draw things out before disappearing. The rest seemed real but were not local enough or could not match my free time.
 
A few experiences, Craigslist itself only ever led to virtual/online fun. Mainly due to no one local.

From memory, I've had 4 meets via other site. Barely speak, instant gratification.
 
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