Online Fun Becomes a Nightmare

It started out like must on-line meetings. I had found the woman’s handle and profile in a Yahoo group and sent her a message asking her if she wanted to chat sometime. I was pleased to see her pop-up on my screen one evening as I was working and started chatting. As usual, we share some general information about each other and learned that we both lived in the Washington, DC area. She lived in the Virginia side while I was from the Maryland side. We also shared our ages and marital situation. She was a bit younger then me at 42 and like me married. Each of us had come to explore and flirt online because our respective spouses where not very sexually adventuresome. It was an enjoyable first discussion; we joked, laughed, share a few of our sexual interests and added each other to our buddy lists. We would have talked longer but I had to finish some work.

A few days later when I logged on to Yahoo IM I found my new friend, “SweetFlower” online and quickly sent her a friendly greeting. We both had more time and spent over an hour talking. This time we delved deeper into our sexual interests and experiences. We both told stories about our first sexual experience and I shared my love of making oral love with women and masturbating for people. She showed great interest in both of these topics and we immediately dropped into a role playing session about me making oral love with her. As I typed feverishly about making passionate oral love with her she let me know that she was so turned on that she was masturbating as I typed and told me not to stop till she had an orgasm. Needless to say this was a very exciting hour and after she came we calmed down to talk about her orgasm and other sexual experiences. She confessed that she rarely had an orgasm with her husband and had to masturbate for sexual satisfaction.

As we talked we also shared information about our lives, the kind of work we did, the type of organization we worked for, our educational background and what we looked like. As this discussion progressed, I had the nagging feeling that I knew “SweetFlower” and so I decided to not be as honest with her as I usually am with online friends. As we talked I became convinced that SweetFlower worked in my office and that I had been in meetings that she had attended. My company had close to 2,000 staff and so I suspected that I was wrong but the idea that I knew who my new on-line friend was excited me greatly.

On Monday, after our weekend on-line chat, I made it a point to find out where the person who I thought was SweetFlower was stationed and then found an excuse to visit her side of the building to take a good look at “SweetFlower” so that I would have a stronger mental image of her the next time we met online.

When I walked into her department I noticed the woman I though was SweetFlower talking with a colleague who knew me. He greeted me and I walked over to be introduced to Jill. We shook hands and exchanged small talk. I felt my pulse quicken and struggled to keep from staring at Jill as she stood across from me. She was an attractive woman in her early 40s with a quick smile and whit. Her eyes flashed with humor as we exchanged small talk. I made an excuse to leave because I couldn’t trust myself to not get too excited and quickly left their department.

That evening I found SweetFlower online and after our friendly greetings I asked how her day at the office had been. She told that it had been okay. And I casually asked her questions about what she did. She eagerly shared information about her work and company and as she talked I became increasingly convinced that she was in deed the Jill from my office. She had to leave quickly because her husband had returned home suddenly but we had agreed to meet on-line again tomorrow evening.

The next day passed slowly. I had to struggle with the desire to go back to Jill’s department to talk with her, but realized that this could be dangerous. When 5:30 finally arrived I rushed off home to get on-line.

About two hours after getting online at home “SweetFlower” appeared and expressed happiness with finding me online. She told me that her husband had gone out with some male friends and asked me to share some real life sexual experiences with her. She was especially interested in how I came to enjoy masturbating for women. As I shared stories from my days in college she didn’t hide the fact that she was massaging her pussy as I talked and she asked questioned. She kept telling me that she found it so exciting to think of having a man masturbate for her and to be in total control of the experience. I was lucky to also be alone that evening because my wife and daughter had gone out shopping so I also started masturbating. When I told SweetFlower this she became very excited. I asked If she would like to watch me masturbate she was stunned and said yes but didn’t know how to do that. I quickly told her about Yahoo’s web cam capabilities as I set up my cam and clicked on the video button. I didn’t show her my face, but my rock hard cock as I stroked myself. She accepted my invitation and started typing wildly as she watched. She asked me to zoom in close and then to show her my balls which were tight to my shaft. Then she really got into telling me to stoke my cock faster and harder. It didn’t take me long to reach my climax and I stood up and positioned the cam at the best angle so that she could see me explode. On the chat screen the word “Cum Cum Cum..” started appearing in rapid succession. I held on as long as I could, pausing and starting stroking again in the hopes that I would produce a gusher. As I stared at the image of my cock on my computer screen I struggled to time my orgasms so that it would be captured. Finally I released my orgasm and was pleased by the result; my first explosion produced a fantastic heavy spurt of cum that was nicely caught on screen. I jerked my cock like crazy now and continued spurting till the last few drops of cum were squeezed from my cock. I noticed that SweetFlower had stopped typing and suspected that she was masturbating feverishly. I quickly cleaned up my mess and returned online to see SweetFlower thank me for such a fantastic experience she had indeed masturbated and had a quick orgasm.

She wanted to just look at my cock as we typed so I positioned the cam and continued chatting about different experiences and about our current life. It didn’t take long before I was fully erect again which please SweetFlower greatly. Unfortunately, I then heard the garage door open and had to quickly pull up my pants, disconnect the cam and hide it and say good bye to SweetFlower. We agreed to chat again tomorrow and quickly exchanged online kisses before closing Yahoo.

The next evening when I came online SweetFlower was there waiting for me. As we exchanged small talk I asked if she had a picture of herself she could share. She said that she did and asked me the same thing. I told her that I only had pictures of my cock would be glad to share these with her in exchange for her picture. After some gentle teasing she finally agreed. I held my breath as I waited for the image to download. I was hopping that SweetFlower was Jill, but had no idea of what I would do if my dream came true. As soon as the download was complete I quickly click on open button and held my breath. I felt my cock stir and my pulse quicken as I realized that I was looking at Jill. Her hair was a bit different in the picture then the way she wore it now, but it was the same person that I knew from my office. Her smile was open and pleasing and her eyes were mesmerizing. It took me a while to realize that she was asking me if I received it okay and to send her my picture. I quickly wrote back that it was a very attractive picture, that she was a very sexy woman and that her husband was one lucky man! She sent me a shy smiley face in return and thanked me for the compliments. I then quickly sent her a picture of my hard cock and told her that this was what her picture was doing to me at that moment. She giggled in reply and asked me if I was alone. I sadly told her that I was not alone and she sent a pouting smiley face in return.

As we talked I nearly made the mistake of using her real name in one of my messages! I realized that I needed to be really careful with what I said and that I also needed to plan how I was going to handle the fact that I knew who SweetFlower really was. I was called away by my wife and had to regrettably say good night to Jill. We again agreed to meet on-line the next day.

I arrived earlier than usually and positioned myself in the small coffee shop near our office’s entrance in the hope of seeing Jill come to work. I was soon rewarded for my patience as I noted her walk toward the office. She was wearing an attractive white blouse and blue pleated skirt and medium pumps. The overall effect was very very sexy and I found myself fully erect by the time she reached the door and walked in. I nursed my coffee as I waited to turn to normal and then entered the office. The day dragged on and I found it difficult to concentrate.

Toward the end of the day I logged on to Yahoo IM and was excited to see Jill online. She was faster than me and greeted me with happiness. I returned her greeting and thanked her again for letting me masturbate for her the other day. She told me the pleasure was all hers and that she couldn’t wait till I was alone and could jackoff for her again. After we chatted for a while I casually asked if she had ever met someone in person who she had first met online. She told me that she hadn’t yet but had been fantasizing about such a meeting. She then asked me the same question, and I told her the truth about the four different women I had met in person after meeting them online. She showed great interest in these experiences and asked me for details. We started talking intensely about these experiences, but a phone call interrupted her and she apologized about having to rush away.

Soon after reaching home I went online and waited to see if Jill would join me. After about 45 minutes looking at some porn Jill appeared and I quickly greeted her. She evaded my initial greetings and asked me for more details on my face to face meetings. I quickly told her about the time I met the business woman who had come to DC for work. I explained that she contacted me online and asked me to come to her hotel just before she left to return home. I explained that I had left early from work and rushed over to the hotel. Typing quickly I started telling the story… “I called her room from the lobby and she told me to come to her room. After letting me in she returned to the chair in the middle of the room and sat down crossing her legs so that her skirt slid up her thigh seductively. As I stared at her with excitement she told me to strip quickly and start jerking off because she didn’t have much time. I did as I was told and removed all my clothes. I was rock hard by the time my socks were off and started stroking my cock and massaging my balls as she stared. She ordered me to come closer and I complied. She held up her hand to stop me when I was about one foot away from her.”

I could tell by the intermittent and sloppy typing that Jill was masturbating as I typed my story. I cursed the fact that I wasn’t alone but was really enjoying sharing this experience with Jill knowing that she was having a good time. When I came to the part of the story where I had been told to lay on the floor as the woman stood over me with one leg on either side of my head so I could look up to see that the wasn’t wearing panties, the words “I’m cummmmmmmmmmmm” appeared on the screen. Followed by “Oh god yessssssssssssssssssssssssss!” Realizing that she was having a powerful orgasm caused me to shorten my story and describe the story of my own orgasm in that hotel that day! She just kept typing “god yes god yes” on the chat screen as I described my own intense series of explosions on that wonderful day.

The screen when still for a few minutes as I chatted by myself till Jill returned apologizing that she had to clean up and change her panties. We talked more as Jill stated how much she would love to have such an experience. I couldn’t let this opportunity pass and commented that I would be up for a meeting if she wanted to. Before she could comment I explained that we could start by meeting in a very public place and then if she wanted to we could find a place for a more private moment. Jill’s side of the screen stayed still and I worried that maybe I had moved forward too quickly and cursed my eagerness when she finally came back explaining that she would like to think about this after we got to know each other a bit longer. I was relieved and told Jill that I would be more than glad to wait.

Weeks passed as we talked online almost every day and on many days several times a day. I would occasionally wait at the coffee shop to watch Jill come to work and fantasize about masturbating for her and making oral love with her. We arranged to find mutual time alone when I would masturbate for her. I finally convinced her to buy her own cam and then one Saturday afternoon while her husband was playing golf she let me watch her as she masturbated. I nearly came in my pants as she experienced her intense orgasm and I found it hard to type because I was so excited.

One day when we met on line she told that that she had upgraded her Internet connection to Cable so that we could watch each other. A few days later we found a good time and have a fantastic masturbation session. Watching her as she watched me was powerful and she had one of the most powerful orgasms I had ever witnessed. She just seemed to keep cuming and cuming till I followed her lead and exploded making a wonderful mess all over the place. After cleaning up and chatting a bit, Jill blurted out “I have to see me in person! I want to be close to you when you cum! I want to see, smell and feel your orgasm!” I quickly responded that I also wanted this more than anything to lay between her legs licking and sucking her as she masturbated and to taste, feel and smell her as she climaxed. We then agreed to set up a meeting the next weekend.

The days passed slowly, she gave me the name of a coffee shop where she wanted to meet me and we settled on meeting at noon. As the rest of the week passed I grew increasingly nervous about meeting her fearing that she would be angry that I had hidden the truth about knowing who she was.

On Thursday evening I decided to let her know who I was. Soon after chatting I told her that I finally had a head and shoulders picture that I could share with her. Jill was excited by this and eagerly asked me to send it to her. My hands were shaking as I moved through the steps to send her the file then waited as it was uploaded. Her screen stayed empty for several minutes as I asked her if she received the pictures.

She finally type her reply commenting that she had received the picture and then she complimented me on being handsome. I thanked her for the compliment and asked her if everything was okay for Saturday. Again there was no reply. I asked if there was a problem and again silence. I grew nervous that I hand blown my chance at an exciting weekend and that my work and personal life were now in jeopardy.

As my fingers shook I repeated my questions asking her if anything was wrong. Finally the Yahoo message that Jill was typing a reply appeared. It was clear that she was either typing a long message or taking time to compose her message. I kept still and waited as my fingers nervously clicked on the keys without typing. Finally a long message appeared.

She started out using my real name, “Eric, it appears that we know each other and that we work at the same company! I also suspect that you have known this for quite a while now even though you didn’t tell me and that you haven’t been completely honest with me. Why didn’t you tell me this? Why did you keep this a secret? Why have you hurt me like this?” Then without warning Jill went off line.

My heart sank and I regretted not sharing the truth sooner. I didn’t know what to do and started to close down Yahoo when Jill suddenly appeared back online. She messaged me quickly asking me to explain myself. My heart jumped as I started typing an apology trying to explain that I had been scared to tell her the truth earlier because I thought that she might stop talking with me. There were no replies as I typed and explained my motivations. I begged her to forgive me.

Like before she suddenly logged off as I was madly typing. I cursed under my breath and waited hoping she might come back on line. This time her screen name remained dark. After about 20 minutes I closed Yahoo and went to watch TV in an effort to get the situation out of my mind.

Sleep didn’t come easy and my wife pestered me with questions about why I was so upset. I passed it off to problems a work and with the help of a mild sedative I finally fell asleep.

The alarm returned with the memories of the night before and I nearly decided to stay home from work. In the end I decided that it was foolish to call in sick and dressed and left for work with out any breakfast. I positioned myself at the coffee shop to see if Jill would come to the office and was surprised to see her arrive. She was dressed casually as was common for Fridays and was chatting cheerfully with two friends as she entered the building. This gave me hope that things would be okay.

In the middle of the hectic day there was a knock at my office door and when I turned around to invite the person in I was stunned into silence when I saw that Jill was standing there with a tight grin on her face. I stammered a greeting and asked if she wanted come in. She cut me short explaining that she didn’t have much time but wanted to tell me to meet her after work at a bar across town and that if I didn’t come I would regret it. She didn’t wait for my reply and just turned and left. I jumped out of my chair to follow but a stern stare from Jill halted me. I just nodded my head and watched her walk casually down the hall till she turned the corner toward the elevators.

After a few moments I called my wife and told her I would be late because of a business meeting. She wasn’t very happy since we had already made arrangements for dinner out. I asked her to move our reservation up an hour and that I would get home as soon as possible.

I had no idea what I was in store for and felt a wave of nervous excitement wash over me. The last few hours of work seemed to last forever. I finally finished my last e-mail and closed down my systems and left the office. I grabbed a cab and headed for the bar. I had never been to this place before and was glad that Jill had picked a place that our colleagues would likely not be at.

I reached the bar before she did and took a table in a secluded table with a view of the front door and waited. I ordered a beer which I nursed as I waited. About 30 minutes later I saw Jill enter the bar. She stood near the entrance waiting for her eyes to adjust to the dark interior and I waved to her and rose from my seat. She saw me but didn’t acknowledge my greeting and strode over to my table. On the way she ordered her drink. She pushed me aside as I tried to hold her chair for her and sat down. I was left standing awkwardly by her side and finally returned to my own seat and sat silently. She just sat there staring at me with a hard stern face. Her drink came and she smiled and thanked the waiter and after a sip returned to stare at me her eyes sparking with anger.

I didn’t dare speak first, I figured that this was her show and I should just wait. As time passed I fidgeted and played with my glass and looked away from her hard stare. She finally spoke, “Don’t look away you fucking bastard! Look at me and apologize to my face!”