Taking the CraigsList Plunge

Have you ever had one of those days where you just wanted to be somewhere other than at work? This was one of those days, and for the life of me, I can’t figure out why all I wanted to do was get laid. I have a solid network of girls that I could call almost any day of the week and be having fun that night. With enough time and enough “friends with benefits”, anyone can accomplish this task. Often times, it takes only two girls, in college, with plenty of free time to meet. At that time, I was only involved with one college girl and she was busy with school in her junior year so she had time on weekends, but not during the week.

As it was, I was having one of the drearily slow days at work where nothing much was happening and there were no big demands of me at that time. I had completed my work and was just going through the daily grind that day. With all this free time, my mind began to wonder, and of course I started thinking about sex. It’s not that I think about it all the time, it’s just that if I have nothing to focus my attention, I can drift easily and will quickly go to that place in my head.

I decided to take a gamble. I had been using CraigsList with success to get new furniture when I moved down there as well as to unload some old gaming equipment that began to bore me. I had heard from friends about the “Casual Counters” section, but I had never really explored it for two reasons. First, I had enough experience on how to get a group of “friends” long before I ever learned the benefits of CraigsList. Second, I thought it was something a little desperate that people did if they could not go to a gentleman’s club and talk a dancer into giving ablowjob, which is my tyical desperate move.

I went to the site and stared at the home page screen for South Florida for a while. I looked at the “Encounters” section and tried to decide if I should open it or not. I continued to toy with the idea in my head for quite some time. I was at work using a work supplied laptop and would get into serious trouble if it was ever discovered that I had entered that section. I also realized that I worked for a very large employer as an intern and that our IT department was not exactly the most “on top of things” as far as employee monitoring.

I knew people who were spending hours on Facebook. I also knew of secretaries and administrative assistants who shopped or played games on addictinggames.com while at work. In fact, I had caught several myself by chance. Still, this was much different. I would be crossing a line and I knew it was wrong. The others had been exploiting a “grey area” of work computer use while I was clearly violating any policy that existed.

I decided to take the chance and just look at the section and read some of post subject lines to begin with. After all, I was only looking and I would not be using the site to actually meet up. So I clicked the section and was taken to the sub-page of “casual counters”.

This place was incredible and absolutely unbelievable. There is a part on the bottom below the disclaimer where a visitor can select what type of postings he or she may want to view. Now this seems logical for someone who is a heterosexual male looking for heterosexual women and not wanting to see postings by homosexual men or women.

The unexpected part of this page comes from the additional listing selections. There is a section for heterosexual men looking for multiple women and heterosexual women looking for multiple men. There is also the same for the homosexual crowd as well as a section with a “T” for trangendered in search of “M” or “W”. Now to the uninitiated, like me at the time, this is if you seek a trans person, you can find one. If you are a trans looking for a couple, you have that option too. I did not know this and was completely floored by the listing option. It makes sense if there is a group of people that want listing options and do not fit into one category or the other. The problem I have is if “casual” is going to be like this, should not the more traditional romance section be the same way as well? That is, in the traditional encounters section, should there not also be a listing for tranggendered people or is CraigsList assuming that transgendered people only want to "hook up"?

At any rate, I clicked in the M for W section and browsed some of the listings. I was disappointed to see that so many listings had either locations at the end of listing that were not in South Florida which immediately means a false post and most likely a “spam bot” or a lack of location listing which means exactly the same thing. I browsed through 2 pages and saw this in most of the postings which made me think that the section is mostly just hackers, thieves, and spammers.

I decided to check that sub-section against another and browsed both the M for M and the W for W. It seems those sections had postings be real people and were not populated with some much spam, but the hetero section was. I checked the W for M and found that it was populated with mostly real postings as well. Additionally, most of the postings were posted that day so apparently there are many men looking for something and only spammers posting for the hetrosexual men.

I was disheartened by this and decided I should go ahead and leave the site. There was little reason to be on there anyways now since the sub-section I wanted was false postings. I went back to some of my work as well as checking on some sports and entertainment. I forgot about the “encounters” section and went about my day until lunch time.

At lunch, I sat alone eating a sandwich and started thinking back to the “encounters” section. I realized that perhaps I could check on the few remaining hetero sections just to be sure. I figured that these would have actual postings more so that the singles sections because it was less likely to be visited. I went back to work and after a while of doing some more work, I went back to CraigsList.

I checked the hetero sections for multiple partners and saw that the postings were real which was good news. The problem was that few postings were present and so the possibility of getting something at that time was diminished. I did find one real posting in the multiples section of a girl wanting many guys.  The problem was that I was only one guy and I had never done any of that nor did I have any good friends that I could call that would go with me to meet a girl.

I was stuck arguing with myself about answering the ad. I decided that I should try it, but in order to avoid problems with work, when I clicked to respond to the ad, I wrote the email address down and physically typed into my personal email on my phone instead of copying and pasting or ever clicking on it at work or using a work supplied machine. I know now that this was stupid and would not have mattered since I opened that ad, but at the time, I was not thinking clearly and figured it would be enough to cover me.

I responded a quick reply to the ad, and I went back to work and looked at some upcoming games to pass time and not seem so anxious. When I checked my email again, she had not yet responded. I went through the remainder of the work day jumping between work, staving off boredom, and checking my email. 

By the time I left work, I figured that I would receive no response and let it go. I got home, turned on my personal laptop and let it boot up. As I got out of my work clothes and got into my gym clothes, I checked my computer and I had two new email messages. I checked them quickly and realized that the second email was a response from the CraigsList posting. The girl had actually responded. Maybe there was something to this CraigsList thing.

I read her email and she asked if I had any friends that would be interested in coming with me. I told her I did not. She was disappointed because she was wanting to have two or more guys. I asked her what she meant by “being used” and she told me what she wanted. It was some of the many things I had seen on multiple pornos I had seen over the years but quickly forwarded through because I wanted to get down to the actual exchange parts.

I told her that I was willing to try some things and she responded that she did not just want to meet alone. I told her that when she found another person to let me know and I would consider it depending on the guy she selected. This was a lie and the first time I had actually lied to a girl about sex. I did not want to give a false impression but I did want to continue to talk to her because she was the only lead I had.

She actually was not that cute and was a bit heavier than I would normally do, but all my other options had been shot down and with no prospects on the horizon that night, I was looking at another lonely night. I figured that to at least keep talking to her, I should exchange numbers and that way I could text at the gym and getting dinner. You know, just in case. She quickly replied with her number, which I saved and headed off to the gym.

I texted her on my way and she responded back. She told me she was really in the mood and was mad that she could only find one good guy to meet. I asked her if she had received other responses and she had, but they were all much older men who seemed very creepy to her. She said a few had offered money, others gave their numbers, and still others sent compromising photos of themselves to her trying to persuade her.

I responded that maybe she should just rub one out herself and wait. She responded that she already had masturbated that day but wanted more. My response was that I was available and if she could stand it, we could meet alone. She did not respond for a long time but finally came back with the response, “fine I’ll meet you, but under one condition”. I read as I walked towards the front doors of the gym. I replied, “what’s that?”. As I was near the front doors and about to reach them, she replied back “you have to face fuck me”.

I stopped dead cold in my tracks. She was actually saying that I had to be not only aggressive but borderline abusive towards her. I had never done this and never considered it, but the thought in my mind was that it would probably be fun. I looked at the gym and then back at my phone. I then asked her where she lived. She replied that she lived down US1 from school, but no more than a 10 minute drive.

I turned right around just in front of the doors of the Wellness Center at UM and headed straight for my car. Once I got inside and quickly left the parking lot. I then grabbed my phone and called her.

“Hey.”

“Are you at your apartment?”

“Yeah, why?”

“I’m coming over. Where is your apartment?”

“You’re coming over now? I’m not really ready and I was going to eat soon.”

“Where is your apartment?”

She told me the name of her place, her apartment number, and how to get there. She was a little shy, but she was ready enough to trust the one picture I had exchanged with her. I began second guessing myself because I had only seen a few pictures and how could I really trust those? She could have taken those a few years ago and lied about her weight. I would find out soon enough.

I arrived at her apartment complex and saw where her apartment was almost immediately. I did not see her looking out the window or anything so she was probably getting ready. I placed my wallet and watch under my bag on the floor of the back seat of my car. I checked my phone and then locked my car and walked up the stairs to her apartment.

I knocked and she answered the door. She was wearing pajama pants, a t-shirt, and a robe. Her hair was wet and very curly. She had showered.

“Hey, you got here fast.”

“Yeah, it did not take long.”

“Come in.”

“Thanks.”

“So this is my place. You want something to drink?”

“No,” as I walked over to the couch and sat down.

“Okay.”

“Why don’t you come over here?” And I patted the seat next to me.

She came over slowly, almost too cautiously. She sat down and I reached over and helped her get out of her robe. She looked at me and did not know what to do so she just sat still. I smiled and she giggled slightly. I leaned back and said, “we’ll have fun,” and I started to pull down my shorts.

She leaned over to help me out of my underwear and began sucking my cock to get it hard. She took her time and was very thorough at getting it sloppy wet. It did not take long until I was at full mast and she was attempting to get all of it down her throat. It was not long after that that she stopped to take off her shirt and pants. I also took the opportunity to get naked and I stood over her as she continued to suck on me.

After a few more minutes I told her to stand up and then lie on the couch. I then stood over her face and positioned myself so I could slide down her throat. She took it like a champ and in no time was getting my balls hitting her nose. I then began to hump her mouth and giving her exactly what she asked for. I know she was enjoying it because she started to use her hands to rub herself and was oozing her fluids onto her couch. I pulled it out and dipped my balls into her mouth and she sucked on them and kept her tongue out to get them wet.

I went back to humping her face and she loved every minute of it. I had to pull out a few more times to keep myself from climaxing too early because I was enjoying the feeling so much. I then went back to humping and quickly reached climax. I pulled out and got it all over her mouth. She began rubbing herself very fast as I did this and let out a long moan that went up in pitch to let me know she climaxed as well.

She got up and went to her bathroom and came back with a white wash rag for me to clean up, the frosting still on her face. She then went back into her bathroom to clean up. I sat down on her couch and she came back out and we talked for a bit.

I asked her about school and what she planned on doing with her life. She told me also about her ex-boyfriend who turned out to be physically abusive but he always gave her great sex. I felt sorry for her in that she was wanting something very different in the relationship and in bed and all he could give was the same abusive treatment all the time. After a while, she asked if I wanted to go again and I said that she could start by giving my cock some attention.

After a few more minutes of this, I made her stop. Then I got up and made her stay in her bent over position and I got up right behind her. I then inserted myself and began to thrust quickly. I did not take my time with this because I had just completed one round and was going for another.

It seemed like I was behind her for 30 minutes because I was trying so hard to keep pace that I began sweating. I had to take a break so I laid on the couch and told her to climb on top. In this position, she was able to do the work and when she got close, she used her hand to rub her clit quickly until she climaxed.

After that, I bent her over again and went back to thrusting. The lying down gave me the repreieve I needed so that I was close to climaxing after only a moment or so of continuing my previous activity. When I was about to finish, I stopped and began stroking quickly and told her to come get it again. This time, she opened her mouth and I made sure my tip was inside her lips as I blasted my second round all in her mouth. She looked up at me and opened her mouth for me to see. I smiled and then she closed her mouth and swallowed it all in one gulp.

We have since met up a few more times, though none as strange as the first time we met. I am allowed to try new things with her regularly, though she tries to date other guys as well so will be unavailable to meet for months at a time. She does, however, always respond to my text messages.