The Odd Couple

Happy Memorial day. Enjoy.

As you may well know, Miami is a favorite destination of northern people in the early spring when it can still be quite cold in many parts of the country. Honestly, I can’t even imagine snow on the ground for an entire winter where the lawn just disappears in November and reappears in late March. Living in Miami certainly has its privileges.

We who live down here can always tell when the season of tourists begins in many ways. One of these ways is the increase in the number of completely pale bodies appearing on the beaches. These people have been bundled up all winter long and their bodies have not seen the sunlight. I don’t mean to mock anyone, it’s just a dead giveaway if you have ridiculously white limbs and a weird accent, we know you are not local. Also, cameras hanging from the neck are another indication.

One time, I was at the beach on a weekend and a tourist couple walked up and plopped down near me. They had a bag with towels, sunscreen, books, and sunglass cases. They each had a towel mat in their arms as well as sunglasses and hats on. I was alone because a friend of mine had just left. She had some family drama and wanted an afternoon to clear her head and talk with someone about it. I answered her phone call and met her at the beach.

This couple was enjoyable to watch. They were in their late 30s or early 40s and were so happy to be at the beach. The woman was in particularly good shape, but the man had the beginnings of a beer belly. They also commented on damn near every person they saw on the beach, discussing how good looking, sexy, and tanned or ugly, fat, and hairy people were. They noticed that I could hear most of their conversation and began including me in it.

I was happy to give my opinion of some of the people, but I was not really commenting on any guys. The man of the couple would say something about the guys just as the woman would, so I quickly surmised that they were a bisexual couple. Fine with me, just not really my style.

After a few more minutes of conversation, they asked me about getting lunch. I suggested a place they could go and they asked if I wanted to join. I declined and they headed off. I then got up to walk down the beach before I left to go home. I took a long time because I did not have anyone waiting on me and I was hungry even though I declined lunch with the couple.

When I returned the couple had returned. I was surprised to see them there but they had actually gotten the lunch to go and were going to eat it on the beach. Also, they had stopped by Wet Willy’s because they had walked right by it and witnessed someone taking some drinks out of the bar and down the street. They decided that they should do the same and had returned and even been so kind as to get me a piña colada.

I thanked them for the drink and told them that I was going to head home. They were a little disappointed, but the man gave me his number and said that I should call them later if I had time this weekend. I asked them what they wanted to do because I was very put off by this and he replied that his wife wanted to have me.

I was staring at her and she was staring at me. She was definitely hot, but for her husband to just come out and say it was weird to me. I asked what he thought and he said that the two of them had done some swinging and that he quite enjoyed watching his wife with other men. I guess he could see the confused look on my face because I looked at him as if he had both grown a horn out of his forehead and tentacles had emerged from his ears.

I had heard about that but I had never actually met any couple that enjoyed watching one partner be with another. Perhaps I am just a jealous lover or maybe too selfish but any girl I am with, I am not about to share her with another guy while we are naked together. She can do what she wants if we are just “friends” and I expect such behavior from a number of my network, but I am not going to watch another guy go at it with her while I just watch.

I left confused, dumbfounded, and completely estranged. I thought about it all night, how a guy could honestly say he wanted to watch his wife with another man. It is just an anathema to me. I am not saying it’s wrong, it’s just not me in any way.

The next afternoon, I was thought about it again and decided, what could it hurt to at least talk to them a bit about it. I called the number and he answered almost immediately. I asked him if she still wanted to play and that if he was good with just watching. He told me that he would also participate if I let him, but if not then he would just watch. I asked what she was into, and he told me the normal stuff, different positions, and no pain. I asked about using protection and he said that they always used condoms, no exceptions.

I wrestled with the idea for several minutes and decided that I should try it because I did not know if any other opportunity like this would ever surface. I was not too keen on wearing protection, especially if the woman was middle-aged, but with him being there, I was not going to try and discuss it. Besides, they had done some swinging so there was potential that they were not as discerning with other partners as much as they had not been discerning with me.

I drove over there and parked away from the hotel, just in case they wanted to watch me enter or leave. I got in the elevator and went up to their floor. I walked to their door and knocked. He answered with his shorts on and welcomed me in. He asked me if I wanted anything, which I declined. He then pointed me to the rubbers and we walked into their hotel room.

His wife came out behind me from the bathroom wearing a negligee. She looked good, too. I had to turn around to look at him. He was seated in the corner chair, looking intently at us. I turned back to her and she began rubbing my body. She pulled up my shirt and began kissing my chest. She then stood up straight and removed her shoulder straps so that her nightie fell to the floor, revealing her nude body. It was exquisite. I bent down and lightly kissed her breasts. I then put my hand down and rubbed her shaved pussy and tapped her clit with my finger.

She then crawled onto the bed and turned on her back. I got down on my knees and went to lick her well. She enjoyed it, but when I finished I looked up to glance at him and he was still sitting there, watching intently as a statue. I then stood up and she climbed over and helped undo my pants. She then slid my semi-boner into her mouth and began working on that. She was decent, but too slow. I could tell she was not going to focus on it too much and wanted pounding.

I let her go until she wanted to stop and then she laid back down on the bed in her original position. I climbed my knees onto the bed and slid into her. I noticed that he had shifted in his stance and became animated. She cocked her head back to watch him as I began to drill her. He looked back at her and began rubbing his crotch.

This was too weird for me. I could not watch her so I had to close my eyes or look up at the ceiling as I drilled. She moaned loudly and continued to look at him. I would occasionally look down at our intercourse, trying to concentrate on that and not think of him being in the room. After a few more minutes, she put her hand on my belly button and said that she wanted to turn over.

 I stopped and backed off and she turned over on all fours and put her head and shoulders on the bed so her ass was sticking straight up. I then moved forward and got on my knees to position behind her. This made it easier for me to stare straight down. I was able to give her a really good ride because with protection, my sensation was way down and it always take so much longer when wearing if you have gotten used to not wearing. Again, I stress the importance of being tested, but it was something I enjoyed so paying for testing was enough for me.

After a few minutes of this, I looked out at her and to see him. He had moved to position himself looking straight at her. He was looking into her eyes and she was looking into him. I could see him mouthing things to her and I imagine she was doing the same. She also gave out a few good moans and light screams to enhance the effect. I was really uncomfortable by this and was ready to finish. I looked down at myself going in and out to speed up the process.

It did not take long after that and I pulled out, stripped the condom off, and stroke as I was about to blast. She turned over and brought her face up close to my cock and opened her mouth, begging for it. I blasted and some went on her chin, some on her cheek, more up on her forehead, and some dripped down her chest. The guy said aloud, “that is so hot, oh baby you are so hot.”

I could not help but smile at how ridiculous this was. I was then introduced to how gross it could be. After I had finished, I stood up and backed away to catch my breath and calm down. The man got up out of his chair, his hard cock pitching a tent in his shorts. He then walked over to his wife who turned to face him, still covered in sperm and smiling. He then bent over and kissed her full on, the cum spreading to his face.

I was not so much grossed out about the cum, just watching them make out as if it were not even really there was what was so weird to me. I guess I should not have thought about it too much since he offered to join, but I told him that would make me uncomfortable. Either way, what was going on was definitely not for me. I grabbed my clothes and walked to the bathroom to clean up. I then walked into the bedroom, said thanks for the experience and now I’m gone.

Let me just say in case you are wondering...never again.

Let’s Go Play in the Park

This little episode is about an encounter with a girl that I had previously written about. She was a cute Latina with the big, beautiful backyard that enjoyed a domineering man. Anyways, this will be much shorter because I do not have to set the story up with any background information. For more about the girl read “Head at the Gym” and you will get a good indication of the type of girl I was with.

This time, I had been out drinking late with my friends. There were many of us and all our extended friends out that night, but I was going from bar to club to bar with a core group of two other guys. We had successfully gotten numbers for the night, but it was still early so we were in no rush to head home with any girls.

As the evening wore on, we were chatting more with each other and hanging with other friends and taking shots all night. Eventually, we were not chatting with many girls or running any game. I realized around 1:30am that I had no good prospects to go home with and I was not in the mood to go home alone. I decided that my best course of action and most probable targets would be the girls that I already had as my network of “friends”. I texted 3 of them simultaneously with an anonymous “hey, what you doing?”

The first one responded rather quickly and said she had a headache. Liar. She was somewhere else with someone else and instead of telling me what she was doing or even trying to talk to me for any reason, she just responded with the universal “headache” response. Fine. I’d give her another chance in the future, but if I get the same response, I can just delete her out of my phone and move onto the next one.

The second said that she was out with friends at a bar further north than where we were. She was a good candidate, but I was not really wanting to wait all night for her to come meet me and then take a cab home. I’d keep in touch unless the last girl had a better response.

The third girl said that she was out on a date and just getting out of a movie. She had plans to go get a few drinks with this guy but she would let me know in a bit if I could come over to her place.

Freaking great. I had to go back into my phone book and select a few other girls to send the same “hey, what you doing?” line. These girls did not answer me as quickly, though one was out and asked where I was. Problem with her was that she was in Coconut Grove and was already really drunk so she was in the mood but by the time I got to her place she could pass out and be fast asleep. The other two never returned my text message.

I decided that I would get in the car with my friends and act like I was going home but always keep up with where the first two possible candidates until I was home.

When we got to the car, as we were leaving the parking deck on South Beach, I texted the two candidates. The Latin honey said that she was with her friends coming to meet me. The other said she was still out but did not know how much longer she would be there.

I had a decision to make, would I stay in South Beach or would I go home? I texted the Latina to ask how many people were with her. She said that she was in the car with 3 other friends but that they were just dropping her off.

Perfect.

I replied back that she should just head on home and that I would meet her at her apartment. I then texted the other girl to tell her to be safe and maybe later in the week we could meet.

I then replied to the Latina that she should just ride with those girls back to her apartment and that I would meet her there. She then responded that she wanted to do something different but she did not know what, just that she was in the mood for something freaky.

This sounded like fun, and was honestly music to my ears since it was keeping it fresh and fun and not more of the same. I have had my share of freaky girls, but one who suggested it and left the door open to my imagination was just so much more fun. I told her that I had an idea but I would not tell her until I went to pick her up.

After another 20 minutes of driving, we arrived in front of my apartment complex and my friend let me out of the car. They called me some names because I did not want to go to Taco Bell with them at 2:00am, but I had better plans and I was certainly not sharing that until after it happened.  Whatever, I was going to have fun and they had no idea.

I walked up through the front door of the complex, past the elevators, and towards the stairwell and headed down the stairs to the garage and my car. I got in, and quickly drove over to the Latina’s apartment in Brickell. She came from a wealthy family and they were only happy to pay for her ridiculously posh apartment.

I had to wait for about 10 or 15 minutes, but I saw her friend’s car pull up to the front. She got out and went into her purse for her phone to message me. I got her text and immediately called her. She answered and asked if I would be much longer and I told her I was already there and that I could see her. She walked out to the street and then saw me in my car. She walked up and immediately climbed into the passenger seat.

As if the after effects of the drinking were not enough to hinder safe driving, this girl was not about to sit idly in the seat and wait until I parked somewhere. She leaned over and began kissing my neck.

She said softly, “I want to do something freaky.”

I responded, “I know, I have a plan.”

She continued kissing and was beginning to rub my chest and my thighs. “What is your plan?” She asked.

“You will see in a minute.” I replied.

“Tell me know,” she said impatiently.

“You’ll just have to wait,” I returned.

“Sure you can’t tell me now?” As she began undoing my belt and my fly.

“I’m sure.” I said, trying to stay as stone cold as I could.

She put her face down and got to work. She was definitely wanting a good time tonight and we would probably have two, maybe three rounds. “You sure?” She asked again, almost slurping her own spit of my cock. “Yes.” I replied and did not say another word until we got where I wanted to be, even though she kept her mouth on my cock the whole time. What? Was I going to tell her and give her the opportunity to stop?

When we stopped, she looked up to see where we were. She did not recognize it immediately and looked at me. She was wondering where we were and what I had in store. I had crossed the bridge for Key Biscayne and driven over the big bridge until I got to Crandon Park. There, I had pulled in until I was near the locked gate. There was no way to get my car in, but I could hide my car against the side of the entrance and we could walk into the Park towards the beach.

“What did you have in mind?” She asked. I told her that I thought we could go play in the park and take some pictures of ourselves as well. “What?” She asked again, trying to wrap her head around the idea. “Just get out. Let’s go play in the park.” I said and hopped out of the car after redoing my pants.

She slid out hesitantly and she walked slowly. She was nervous on the walk over there and was wondering if it would be safe. I said it was Crandon Park which had very few, if any, late night guests. She then asked about the cops coming up and seeing the car. I told her that we would use the park benches and that if a cop drove up, we could see his lights and make up a story about being there and not get into trouble.

With some reluctance, she agreed and we sat at the first picnic table we came to. To make her feel more comfortable, I began to kiss her neck and rub her body up and down. She finally relaxed and threw her purse onto the table and began feeling me up and down. I then pushed her away and took out my small camera. I told her to get on the table and look at me. She obeyed and I started taking pictures. She seemed to get into it and before I knew it, she was giving me a strip show while I was taking pictures.

She got down to her panties and I stopped and walked over to her. I undid my pants and pulled out my hard cock. She was already on all fours and began sucking. I took two, maybe three pictures of her doing this and then tossed my camera by her purse.

We then proceeded to have a good session, though the table was not comfortable and a towel or blanket would have helped tremendously. We were reduced to a few positions while using some clothing for her knees or her ass. Because I did not have any rags to clean up any mess, I made her squat down and catch all of my cum in her mouth. Even with my extensive viewing of porn and the camera being mere feet away from me, I did not think to take a picture of her like that until after she started getting dressed.

We walked back to my car and drove to her place. I stayed the night and was going to leave when I woke up the next morning. When she woke up, she asked me what we did and I asked her if she remembered the park. She said she did not so I asked her what she did remember. She remembered only up to the point of getting into my car the previous night. I told her some highlights but did not want her to ask too many questions so as I was talking, I reached over and began fondlingbetween her legs. She got quickly in the mood and went down to work on the shaft some. We ended up having much more comfortable session in her bed. I then showered and left.

As far as the pictures go, I remember looking through them the following day and noticing some were not very good. I erased those. The remainders I kept for a while but deleted them, to my everlasting regret, when she got her most recent boyfriend.

The Divorced Coworker

While working at my internship with my employer, I met many people. The funny part about this is that over 60% of our entire office was women and most of them were between 30 and 50 years old. There were quite a few good looking ones walking around who loved to wear wonderfully tight clothes. One of these women was a divorced woman with a 3 year old daughter. She and I had worked on a few projects together and she was always a good looking woman in my opinion. I often thought about what having her in bed would be like, and with the right opportunity, I was going to find out.

The problem with constantly thinking about sex is that you often romanticize it and think that it will be so much better than it really is. I believe this is what happened between me and Mrs. Rivera (not her real name). She and I had a decent working relationship and had spoken often enough that if I ever saw her outside of work, I would not feel at all uncomfortable speaking with her. With one month to go until the end of my internship, I would get my chance but only because she wanted to find out about me exactly what I wanted to find out about her.

I was working on a project for my boss and need some of Mrs. Rivera’s expertise on the process for legal reasons, just to protect our company and ensure I was not forgetting major steps in compliance. One day I emailed her late in the work day and expected a return email by the next day. She, however, wanted to give me a way to contact her when she was not at work. That day, she had left early for a doctor’s appointment with her child’s pediatrician. She received my email on her BlackBerry. Instead of replying to the email from that account, she replied from her personal email.

This was perplexing to me at first. I was always professional while I was at work. I had done some things by phone on my lunch break or even on work grounds, but as long as I was working, I was only working. Secondly, I had never tried any moves on any of my coworkers. I thought many were quite attractive and some just downright hot, but I never let them know that on the job or off. It just was not a line I was willing to cross. Until now.

You see, I only had less than a month in my internship. I had already discussed my departure date with my manager and he had wished me luck and offered any sort of help in the way of referrals or endorsement letters. I already had my full time job lined up, but I did not want to spend time at home doing nothing for the remainder of the month so I decided to continue working as an intern until the start date of my full-time job.

I noted the email address she had used and when I got home that evening, I replied to her email to thank her for the quick response and start up a friendly conversation, you know just to see if she was doing what I thought she was doing. She replied quickly. Thank heavens for smartphones. We began discussing things outside of work such as my future plans for work and plans on moving if I ever do. She said that she would miss me and that was nice for the time it existed to have a cute, young guy around the office. She said it was a good change and complimented my physique. She was doing exactly what I thought.

I complimented her and said that I thought she was lovely and I was particularly impressed with her physique and that she was so committed to working out and staying fit. She replied that she was thankful someone noticed and that she was trying to have a social life as well but that having a child made that possibility almost non-existent. I said that I absolutely noticed and loved it when she wore the sexy almost-too-short-for-work skirts and loose blouses. She thanked me and that was the end of our conversation that day. There was no need to press further, we had just begun and I wanted to build up the anticipation with her. Women love that for those who don’t know.

The next day, she wore a skirt and white blouse. The skirt was tight fitting, but came down past her knees. That was unfortunate but I was happy she had listened to my suggestion. That night, she emailed again to my personal email asking if I noticed, to which I replied that I did. I also told her that though she could not tell, I was wearing some small boxer briefs all day as well, powder blue. This gave her a good image for her to think on and opened the door to more descriptive and work-prohibited discussions.

We began discussing what we found attractive in the opposite sex. I told her of my penchant for round-assed Latin honeys, of which she sort of fit the bill, and she told me about how she loved a rugged man. She said her ex-husband was no such man and that he was unable to last long. If a guy was smart, he would take notes. I typed the information into my phone under notes so that I would commit it to memory.

The next night, a Thursday, we discussed some more steamy details and desires and we even exchanged a few pictures. These were of the safe for work kind since she had not had any compromising photos taken of her and I was not going to share any that I had if she did not have any. We also discussed a few of our more memorable sexual exchanges in the past and I was certain that soon I would be crossing the line from coworker to “friend” with her. I just thought it would happen after I had left the company, and I was wrong.

That weekend, I woke Saturday morning from a fun night out with friends and checked my email before I ran a few errands. Mrs. Rivera had emailed me and left me her phone number. I decided to save it in my contacts and send her a text message when I was out later. After lunch, I simply composed a “hello” message and this is what I got: “Can’t wait anymore. Daughter with ex-husband. Call me.”

Fucking sweet.

I called her after I finished lunch and she said that she had been thinking about it since we first started emailing. I told her I had been thinking the same and thought we could do something yet remain professional in my last few weeks of work. She asked me to meet and of course I obliged. She told me directions to her home and I left immediately, my errands half completed.

I got to her house and she answered the door in a long t-shirt and underwear. Nothing else. I said hello and she replied hi, smiling devilishly. I asked her if we could go sit over on the couch and she grabbed my hand and pulled me over there. I sat down and she stood up in front of me. She then pulled off her t-shirt, revealing her perfect, enhanced breasts. She sat down in my lap and we began making out.

In little time, I was taking her undies off and began playing with her recently waxed pussy. She was quick to start moaning which surprised me a little, but I shrugged it off as someone who had not had anyone else doing anything like this for her in a while. A few more minutes of heavy petting, rubbing, and light kissing, and she squeezed her legs together and grabbed my shoulder and gave her “O” face.

That was quick, but no matter. It’s not the first time I have given a woman a big orgasm. And it certainly was not any reason to stop.

We continued and she helped me out of my clothes. She then got down on all fours and put my cock in her mouth. She began sucking and was doing a good enough job. I took the opportunity to reach behind her and use my fingers in her pussy. I even teased her ass a bit and she gave a low moan again. I wanted to experience more than her mouth so I pulled her off my cock and turned her around and over. I then slid in and began thrusting. To give her more sensation, I reached down after a few moments and lightly tapped her clit. Within 15 seconds of beginning to tap she flexed her legs again and twisted into a new “O” face.

I then turned her over and went at it doggy style using her hips to thrust very quickly. Within a few minutes of this, she had a third orgasm. I was kind of dumbfounded, but I knew at this point that I had given her more than she expected and felt I was free to do what pleased me. I then pulled out, spit on her ass, then slid inside. She was tight there and the feeling was great for me. She put her face in one the floor and reached back with one hand to rub her clit. I felt her stiffen as she had her fourth orgasm.

It was such a distraction because I could not enjoy the position I was in for any good length of time. She kept cumming and there was nothing I could do to stop it. I decided that I was going to just let her work on me so I pulled out again and walked around to her head. I then pulled her up until she was on her knees and she began to suck.

She was doing a decent job again, but it was not really great. I got close enough to where I could pull out and stroke while she used her tongue on my balls. She understood what I was doing and was quick to put her face underneath my cock. Finally, I was close and when I looked down to watch myself and look at her, I noticed she had been rubbing herself again.

Finally, I was close to climaxing. I pushed her face back and positioned my cock right in front of her face. Just as I was about to blast, she looked up and had a fifth and final orgasm. I spilled myself all over her lips and in her mouth. When I finished, she looked at me then at my cock and back at me. She said, “you were just intent on wearing me out today.”

“Yeah, I guess I was.”

“That was wonderful,” she proclaimed with a large grin on her face. “I have not cum like that in a long time.”

She then got up and walked into her bathroom to clean off. Afterwards, she emerged in a robe and I went in to clean myself off. I showered as well and said good bye and left quickly.

I felt weird after leaving because she said I was intent on wearing her out. I hardly did any earth-shattering things. She had given herself two of them and had helped on a third. She was just an easy climaxer and instead of enjoying the romp, it distracted me.

She ended up texting me a few weeks after I left my internship asking if I was free and wanted to meet. I told her I was going to meet someone else in a bit but would be willing another time. One lie, then another. I was not going back unless I was desperate. She was decent at best and had been a distraction with her actions. No thank you, but I have others who fuck better.

A Quick Break from Work

This incident picks up with a blonde that I used to see on an occasional basis. She was cute and had a great body, but she was not as available as I would like with any “friends” I have due to the fact that she had quit school in the middle of her Junior year and had been working since that time. She was just a year younger than me though she had been working longer due to dropping out and the fact that I went to graduate school.

She and I met initially at a friend’s party. I knew someone who was from Miami whose parents were wealthy and he would throw large parties at their house occasionally. She had friends that had friends that knew about these parties and she decided to tag along with them at one of these parties. When we initially met, she was not that into partying because she had recently broken up with her boyfriend and her friends were dragging her out to get back into the scene and forget about him. Our conversation went nowhere and we never exchanged information.

A few months later, while on South Beach on Ocean Drive, I went to this bar called Wet Willies. This is a place where one can purchase a mixed, slushy type alcohol drink from a huge array of mixing machines they have running. At all times, they have rum runners, belinis, piña coladas, margaritas, 180 octanes, mudslides, the works. My friends and I would often pick a spot on the beach that was a short walking distance to this bar so that we could go and get drinks and then walk back to the beach to enjoy their slushy, alcoholic goodness.

While I was waiting to order my drinks, I noticed that this blonde girl was at the bar. I immediately recognized her from the party and remembered some highlights of our uneventful conversation. She was intrigued that I remembered her and it probably helped that she was now over her ex-boyfriend and I was in a sober state of mind, unlike our first meeting. We chatted a bit about the party and I asked her if she would be going out this weekend. I told her if she wanted to meet up, just go to this and that bar the coming evening, if not, no worries.

I was a bit surprised she showed up that evening, and even more surprised that she was alone. She told me she was supposed to meet a friend so that she could not stay long. I guess she did not want to look desperate. We chatted for a few minutes and had some fun dancing. Before she left, I gave her my number. We ended up not exchanging messages for almost a week, but once we started, we were going full speed.

Eventually, we broached the subject of sex and I got from her hints that she was a bit of a freaky girl but was not exactly as loose as I wanted. She was going to take a little more time than usual. We ran into each other at bars over the next few weeks, and eventually, we started kissing and heavy groping. One more of those sessions later, and she was taking me to her apartment.

She thought that she was a bit of a freak, but not as much as she would like to have everyone believe. She was convinced though because her ex-boyfriend was not one to try anything other than missionary and rarely was into oral. I was able to let her experiment with that much more than he ever had and she was enjoying the new freedom she had found. We kept it simple though, at least I did, because I did not hide the fact that I had been with other girls since I had met her and she told me she went on a date once with a new guy, but was not that into him.

Eventually, we were discussing as “friends” often do and I started texting this to her on my lunch break and she would do the same when she was free. One time, while discussing it, she said she had really gotten in the mood and was wishing we could meet somewhere. I suggested that we could try to meet at an hourly motel, there are plenty of those in and around the Miami area, but she did not like the idea. I then said that unless she was willing to do something in public or a car, then it would not happen until we could meet this weekend.

She replied back that she had always wanted to try something in a car but was afraid of getting caught. She had a spacious SUV even though she was a single woman of approximately 27. She had purchased dark tints on her windows many years ago and they were dark enough for me. I suggested that she come over and meet me at my work. I could get her car into the parking deck and we could find a secluded spot to play a bit.

She liked the idea and took a long lunch to come and meet me. I had originally suggested a lunch together so when she arrived, she parked and met me. We then walked to the restaurant I had suggested but it was quite busy and her drive to my place of employment took longer than she expected. I could see that getting lunch would take too much time for her so I told her that we need to just get to business and she could get something on her drive back.

She agreed and we walked back to her car. I used my parking pass to get her car into the garage and we pulled up to the second highest level because it was the highest level with a roof on it. Then, we pulled her car in backwards and put her windshield sun shield up so we could maximize privacy. We then climbed into the back and pushed her front seats as far forward as possible including leaning the seatbacks forward.

I wanted to do a whole bunch of things with her but there were two problems. First, she did not have a condom as she said she did and she was not a pill taker. This meant that normal sex was out because I was not about to push my luck with that. She was not interested in gettinganal without doing many other things and no lube because she was particularly tight and had only done that twice before, both times with me. That left oral and her hands.

These were nothing new to me in such a situation so I was quite ready to do it. She was, however, much more of a give and take type in bed so I would have to do for her what she did for me. I pulled her pants down and then her undies. I got to work and did not try to do much more of the other foreplay with her. I ended up finger blasting her until she screamed. She, in turn, started to suck me.

She had learned a bit with me, but was not willing to go down continually and she would get tired very quickly. She did not mind, however, stroking between the times she used her mouth and she ended up stroking me off. It shot straight up and landed back on the tip and the rest poured out onto my pubic stubble. She was prepared in one way, however. She had always kept a set of wet wipes in her car because she would often eat in the car and did not want to rely on napkins from fast food restaurants.

She wiped me off and I tried my best to not look disheveled. She then open up the back door on her side of the car and tossed the used wipe towards her back tire. I got out of the back seat and into the front seat and she did the same. We then pulled out of the parking space and drove down to the bottom floor and I let her out of the garage.

We ended up meeting only once more about a month later. After that, she got back with her ex-boyfriend because she swore “he’s changed, he’s not like that anymore”. I deleted her number and have not spoken to her since, but I would not be surprised to hear from her again in the future. Afterall, the only thing he enjoys is missionary.

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.