When I was younger and chatrooms were still popular, I spent some time on Yahoo in local, state chatrooms. I chatted with a few women over the years, but had never worked up the courage to actually meet one in person. The internet still had a stigma attached to it back then and I guess I was just afraid of the potential consequences.
When I was 22, I began having a conversation with a 40 year old, married mom whom lived about an hour and a half from me. Her children were older so they were rarely home and her husband was deployed to Afghanistan. She told me that their relationship had been slowly deteriorating for months. She said the few times that she would get to talk to him, it often ended in an argument and that they were most likely headed for divorce once he returned home permanently.
She was a beautiful woman. She told me that before her husband had left, she was a bit heavier, but had worked her tail off to lose the extra weight. By the time we began chatting, she was down to I’d guess around 130 pounds—perfect for her five foot, seven inch frame.
We chatted for several weeks and would occasionally use the webcam. Webcam technology was still pretty new and the image was always laggy and blurry with no sound. As our conversations became more intimate, I would ask for her to show me different things. She was hesitant to show me her breasts. She explained how the weight loss had taken its toll on them. Reluctantly, she showed me. While I thought she was gorgeous either way, she was right. The radical change to her body had done wonders in other places, but the opposite was true in others.
One day, after having been absent from Yahoo Messenger for a few days, she hopped on and said that she was sorry that she had been away. She said that she had had some surgery and wanted to show me something. She turned on her webcam and proceeded to take off her shirt and bra to show me that she had gotten breast implants. Like I said, I thought she was beautiful before, but now every inch of her body was perfect. She would definitely be causing heads to turn everywhere she went.
She told me that I was the first to see them and that she hoped I would see them in person someday. We exchanged phone numbers and within a day or two she texted me to tell me that she was in town to pick up her husband from the airport. His plane would not be coming in until the next day. She had gotten a hotel room downtown and had nothing to do so she wanted to know if I would want to meet to have coffee or something. I agreed to the meeting, despite being nervous as hell.
We had planned to meet at Starbuck’s. It was my hope to get their first simply so she would have to come up to me as I was scared to death to have to come up to her. When I arrived, I was too late. I could see her standing at the counter waiting for her order, but I could really only see her from the side. As I approached the counter from behind her, I heard the kid working the register tell her how beautiful she looked. She said thank you and turned around to see me standing there nervously. My jaw nearly hit the floor. She was stunning! She wore a tight tank tope that amplified her already amazing cleavage. She was also wearing those sexy, cat-eye glasses that I absolutely love on girls.
We awkwardly hugged and I placed my order before joining her out on the patio. We made small talk for well over an hour. It was getting later in the afternoon—early evening. I asked if she wanted to go somewhere and get some dinner. She agreed so we walked a few blocks to a nice Italian restaurant where we had a nice dinner and a few drinks. We continued to make small talk for another good while before I finally paid the check and waited to see where things went next.
I nearly jumped for joy when she asked if I would like to go back to her hotel room and order a movie or something. We walked to her hotel and as we were going up the elevator, yet another guy commented on how beautiful she was. He looked at me jealously as if he knew what was going through my mind.
We entered the room and we both made ourselves comfortable on the bed. She turned on the TV and began searching the pay-per-view titles for a movie to watch. She could’ve turned on anything at that point—I didn’t care. She picked a movie and we began to watch. While I do remember the name of the movie, I couldn’t tell you anything about it as my mind was racing a hundred miles an hour.
We lay there for about forty-five minutes to an hour in silence—except for me getting up to go to the bathroom every ten minutes because I was so damn nervous. Finally, I figured it was now or never so I gently began to caress her cheek with the back of my hand before leaning over and kissing her. This lead to a very passionate make out session before I asked if I could finally see the work that she done.
She lifted her shirt over her head and I wrapped my arms around her back to unclasp her bra. I threw it to the floor, exposing the biggest, most perfect pair of breasts that I had ever been this close to. I asked if I could touch them or if they still hurt too much for them to be handled. She said that she had taken some painkillers as soon as we returned to the room so it would be fine. I gently placed my hands on them being very careful not to be too rough. However, she insisted that she was fine and such delicate care was not required. I continued to fondle her as we kissed, our tongues swirling in and out of each other’s mouths. I lowered my head and carefully licked her breasts, churning my tongue around her nipples.
She told me to lie back and relax. She removed her shorts leaving on the lacey, pink panties that she wore. She undid my belt, unbuttoned my jeans and slowly slid down my zipper. She was somewhat surprised by the fact that I wasn’t wearing underwear, but this only slowed her a second as she took my cock in to her hand. She stroked it gently before lowering her head to give it a lick. She slid her tongue down the length of it stopping at the base to take my balls in to her mouth. She slid back up and whirled her tongue around the head before finally taking the whole thing in to her mouth.
It was pure ecstasy! I had never felt anything like this—the things she could do with her tongue! I desperately tried to recite baseball statistics in my head to keep from cumming too soon so that I could enjoy this for as long as possible. I gave the best effort that I could before finally exploding in to her mouth. It was the most intense orgasm I had ever had. She swallowed it all and smiled as she came up and rested her head on my chest. She must have been able to feel how fast my heart was racing.
We laid there for a few minutes. The entire time she was gently playing with my now soft cock in her hand. After a few minutes, I was hard again and she began stroking me harder. I tried to slide my hand into the front of her panties, but she cut me off and resisted my advance. I told her how bad I wanted to fuck her. She said that she wanted me too, but unfortunately, it was just not a convenient time of the month to do so. So she continued to just stroke my cock for a few minutes.
I was as hard as a rock; throbbing in her hand when suddenly, she stopped and excused herself to the bathroom. I hedged my bets and assumed this was simply and excuse to make preparations as she wanted to fuck as badly as I did. I reached down and took my wallet from my pants that were still lying on the end of the bed. I removed one of the condoms that I had bought on my way to meet her in hopes that something like this would happen. I had been so nervous about what this encounter would be like that I bought those condoms with the desensitizing lubricant to help ensure that you can last longer. I took one and placed it on the corner of the nightstand.
A moment later she returned from the bathroom, having removed the pair of panties that had blocked me from getting to her pussy earlier. She was ready, and so was I. She noticed the condom that I had placed on the nightstand. Standing next to the bed, she took the condom and unrolled it down my penis before climbing on top of me and guiding me in to her pussy.
We fucked forever—in every position imaginable. If it hadn’t been for the extended pleasure condom; I know I only would have lasted a couple of minutes, if not a few seconds. I eventually reached the point where I desperately wanted to cum, but the condom was working all too well. I knew that if I kept it on, I was never going to climax.
Remembering one of our more intimate conversations from Yahoo, I knew that doggy style was her favorite position so I asked if we could do that next. She happily climbed up on all fours and I took my position behind her, discreetly removing the condom in the process. We were facing the mirror so I could see the look on her face as I slid my now naked cock inside of her. She could tell right away what I had done, but didn’t seem inclined to care. I began thrusting harder and harder and told her that I was going to cum. In the slightest whimper, she said, “I want you to cum inside me, baby.”
That was the moment of no return as I thrust my cock one last time and pulled her as close I could by her ass. I unloaded inside of her before we both finally collapsed on the bed. We continued to lie there, now in the dark; kissing and fondling each other before finally falling asleep in each other’s arms.
We spent the entire next day texting back and forth about the encounter and how incredible it had been for both of us. Later that week, she told me that she was going to be coming back to the city to return her husband to the airport. She asked if she could stay with me once she was rid of him. At this point in time I had just returned home from college and was still living with my parents. I was too embarrassed to tell her, so I essentially just dodged the question and explained that I would be busy. Our messages became fewer and fewer over the next couple of days before just finally ending altogether.
To this day, I still think about this night and recreate it in my mind. About a year ago, right before my own wedding, I decided to see if I could find her. All I had to go on was a first name, an old cell phone number that was no longer in service, and the screen name she had used on Yahoo Messenger.
After some creative Googling, I managed to find her Facebook profile. I discovered that she was now living in another state as her husband had been reassigned. They were still married; apparently living much happier than she was at the time of our meeting. I sent her a friend request, but she never responded. I took this to mean that it was best to leave well enough alone. I still check in on her Facebook page from time to time. I have since learned that her son is right around my age and that her daughter, only a couple of years younger than me, is as gorgeous as her mother.
I wish that I could simply tell her how much that night meant to me, but I wouldn’t want to risk jeopardizing her marriage or my own. I am left with the lasting memory in the back of my mind and very few days pass that I do not recall that evening and wish that I would have met her again the following week like she wanted to.
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