First Online Cyber Affair

The internet was new and exciting. I was on AOL and was researching a trip to Chicago, so I went into a Chicago area chat room. I wanted to find things to do and places to see while there for a hockey game.

It was tough getting people to talk to me in the chat room because I was new to the room. Finally, a person with the screen name TRISH1950 suggested that I stay downtown and told me a few of the good spots to hit at night. I sent her an IM thanking her and asked if I saw her online could I IM her again. She said yes, but that she was married and might not be able to talk. I told her I would send an email asking if she could talk and then she could IM me first. It sounded like a plan.

I went to the hockey game the next weekend and the places TRISH1950 recommended were great spots and I had an epic trip to Chicago. I started to look for Trish online to thank her and finally one night I saw her online. I sent her an email and in a few moments she IM'd me saying she was home alone and could talk.

I thanked her for the recommendations on things to do and see in Chicago. The conversation with Trish was easy and fun. She asked if I was married and I said yes. She said that she had been married for many years, but things were not like she wanted. I told her that my marriage isn't always that exciting, but it was okay. We talked about a variety of subjects. We found out we were the same age, married for the same number of years, both had two daughters and both liked the same music. We talked for about 2 hours and we said good night with the agreement we would talk again.

Of course, we both were online the next night. Again, my conversation with Trish was fun and time flew by. At the end of the conversation, I asked her what her favorite "make out" song was when she was dating. I told her to think about it and I would talk to her tomorrow and share my favorite "make out" song with her. Once we divulged the song, we had to tell why and give the details. She agreed.

I couldn't wait for the next night. Trish was online when I signed on and she IM'd me immediately. Her husband was in bed sick and she could talk as long as she wanted. I told her my wife was out with the girls for the evening so let's discuss our favorite make out song. We agreed to email each other our favorite songs and then talk about them. I sent her my choice and I received hers. We both started laughing when the only song was Unchained Melody by the Righteous Brothers.

I asked her to describe the first night she made out to that song. She was driving with her boyfriend and the song came on. She said she started rubbing this thigh and he pulled into the first dark area they could find and started kissing passionately. She asked me about my first make out session and I told her we were already parked when it came on. My girlfriend moaned how much she liked this song and how it turned her on. I asked Trish how graphic she wanted me to be and she said go for it. I told her that my girlfriend reached down, undid my pants and proceeded to give me my first blow job. I got an "LOL" from Trish and she said that she gave her first blowjob that night to her boyfriend. I was so turned on by this; I had my cock out and started stroking it. In a few strokes, I shot my load all over my stomach. We signed off with the agreement that we would talk again tomorrow after the spouses went to sleep.

The next night couldn't come soon enough. We met online and discussed the previous evening. I confessed that I was very turned on by our conversation and Trish surprised me when she said she was also turned on. She asked me what I did about it. I again asked how graphic she wanted it to be. She said to tell it like it is. I told her that while we were talking, I dropped my pants and was playing with my cock. I told her that when she confessed giving her first blowjob that night, I shot cum on my stomach. I told her that I only had a robe on at the moment and it was open. My cock was rock hard.

She asked me to jack off for her and describe it for her. I learned it was tough to stroke your cock and type at the same time. I told her to give me a moment, let me jack off and then I would give her all the details. So, I started to slowly stroke my cock. My other hand reached down and lightly touched my balls. My finger traced down between my balls and my asshole. I loved to rub my anus when jacking off. I started pumping my cock hard and as the orgasm built up; I inserted my finger into my ass and blew my load all over my stomach again. I rubbed the cum on my stomach until it was gone.

When I was done typing my first cyber orgasm for Trish, she said it was her turn now. The night before she was online in her nightgown, which came down to her knees. She said that while I was telling her about my first blowjob, she opened her legs, lifted her nightgown to her waist and was finger fucking herself. She said that she had two full scale orgasms while we were talking. I asked her what she had on at the moment and she said she was also naked under a robe on in case the hubby came in the room. And she said she had her favorite toys with her. I asked her to masturbate for me and describe it. She said she already finished and told me to sit back and enjoy.

She slid her hand down to her pussy and started to rub her clit. She said she opened her pussy lips with the other hand and put two fingers in. She then reached for her dildo and pushed it slowly into her cunt wishing it was my cock. She pushed it all the way into herself and turned the vibrator on. She then reached for her vibrating egg and pushed it into her asshole and turned it on high. She returned to the dildo and started pumping it in her pussy until she came. She told me that both vibrators were still in her and still running. She said she was pleased that I like anal play like she did. I said I was pleased she was willing to masturbate for me. We signed off with an assignment. We were to tell each other with a "what would I do" scenario for the next night.

Our assignment was to describe "what I would do" if we were in the same house and the other one was on the computer. When she came online, I told her to sit back and just read. I was ready to tell her "what I would do" if I came into the room and she was on the computer. It went as follows:

As I was passing the computer room, I saw Trish online. The room was dark and I slowly entered. She was engrossed with the computer, so I reached down and started running my fingers through her hair, lightly rubbing her head. I could feel her relax as I started to massage her neck. I bent over and kissed her ear and felt her moan. I nibbled her ear and used my tongue to lick it. I was still massaging her neck. My mouth moved to her neck and I started to kiss her gently. My hands now reached down her front. She had on a blouse that buttoned down the front and a bra on. My hands gently caressed her breasts while I was still kissing her neck. I started unbuttoning her blouse until it was fully opened. I took one finger and slid it inside her bra until I could feel her nipple. My finger rubbed her nipple until it was hard. I turned the chair Trish was sitting in around so she now faced me. I took her blouse off. I lowered one bra strap and then the other. I slowly lowered her bra until both of her beautiful tits were exposed.

I knelt in front of her and resumed kissing her neck, while my hands caressed her tits. My mouth worked its way down to her nipples and I softly bit them, first one, then the other. My hands were now working on getting her slacks off. I unbuttoned them and she lifted her hips to help me. I stood back to take in the view. She looked beautiful sitting there in just her panties. I took off my clothes allowing my cock to swing close to her mouth. She reached for it, but I wasn't done. I started to kiss her tits again, and worked my mouth down her stomach. I pulled her panties off exposing her trimmed pussy. My mouth finally reached its goal. I found her clit with my lips and started sucking it. My hands were lightly rubbing her pussy and pulling her lips open. I then took my tongue and found her juicy slit. I sucked on her pussy until she came for the first time. I took her from the chair to the desk and bent her over the desk. It exposed her opened pussy and her asshole. Again, my mouth found her wet cunt. I licked and tongued her to another orgasm. My tongue went to her butt. I started licking her asshole and fingered her pussy. After another orgasm I reached down and took my cock in hand. I slid it into her pussy and started stroking. I reach around and played with her tits and rolled her nipples with my fingers. I slow fucked her with my cock going all the way into her pussy and slowly coming out. Now that my cock was wet, I pulled it out of her pussy and put the head against her anus. I waited to see what would happen and Trish pushed against my cock until she took all of it up the ass. Then she started fucking my cock. Her ass was tight as she rocked against me. She liked me to pull out and shove it back in. Her last orgasm brought me to my orgasm. I pulled out and she turned around. She opened her mouth and asked to shoot my cum into it. I did what she asked. Strings of cum went into her mouth and she swallowed it. We then spent the next hour kissing and caressing on the floor.

It was now Trish's turn. She said she was breathless from cumming while reading my story. She said to sit back and enjoy.

It was early evening when I saw you still working online. I thought to myself, it would be nice to see if I could release his stress. I went into the bedroom and put on my silk robe and nothing else. I went back into the computer room. You didn't notice, so I turned your chair around, opened my robe and said it was time for some stress relief. I could see your cock starting to get hard, so I bent over and started kissing you while opening your shirt. I pulled it off and removed your tee shirt. My mouth moved down to your nipples as I rubbed my tits against your hard cock. My hands were now getting your pants off. I made you stand up and stripped you naked. You then sat back down as I started kissing your nipples again. I took my tits and wrapped them around your hard cock. I moved my tits up and down until I saw that first drop of precum. I continued to titty fuck until I felt you wanting to cum. I backed off and opened my little bag of goodies. I pulled a silver egg out of the bag and put some lube on in. I then knelt back in front of you and started sucking your cock. My tongue rolled around the tip, feeling it getting even harder in my mouth. My hands were playing with your balls.

You slid your ass to the edge of the chair and opened your legs allowing me full access to your asshole. I took some of the lube and rubbed your asshole. I could feel your cock jump as I put a finger in. Once I lubed your asshole, I put the egg in and turned it on. Not wanting you to cum yet, I quit sucking your cock. I now got my wet pussy over your cock and lowered myself slowly onto your cock. I lifted and lowered my pussy. I could feel the vibrating egg with my pussy and I came hard. I put my titties in your mouth and told you to suck, which you did. I got off your cock, turned around and lowered my asshole on to your hard cock. Your hands were now playing with my titties from behind. I squeezed my ass cheeks and fucked you until you almost came. When you started breathing like you were going to cum, I pulled off and pumped your cock with my hand until you came all over your chest. I proceeded to lick your cum until you were clean.

Needless to say, I had been stroking my cock the entire time and did shoot my load. Trish and I both agreed on two things. First, we would do this again, but not every night. The second was to meet some time and turn fantasies into reality.