This story is 100% true. Some of the details have been changed to protect the guilty. I recently began documenting all my past sexual exploits. This is the fourth story in my saga.
So, when I was in my mid-20’s I lived in the suburbs of one of the world’s largest cities. Most of my coworkers were married but I had one coworker, Max, who like me, was single. So, we ended up heading into the city every weekend in search of tail.
On a random Wednesday night, I had just finished dinner at my condo when I heard a knock at the door. It was my friend Max. He lived about 5 minutes away from me. He told me we wanted to run something by me. I invited him in eager to hear what he wanted to share. He sat down and began to explain that he had been talking to a woman he met online a few weeks ago. He wanted to go meet her tonight but he wanted me to go with him so that he would behave himself. He knew that we both had work tomorrow so, neither of us could stay in the city all night. I had no interest in going and playing the third wheel. He eventually convinced me by promising to pay my train fare, pay for my dinner, and to take me to watch a lounge band at my favorite cigar lounge. The offer was too much for me to refuse. “Ok, I will go but, I am taking the condoms out of my wallet, just in case”. I thought that if I didn’t have condoms, I wouldn’t try to hook up with anyone (and in hindsight, boy was I wrong). As we rode the train into the city, we both vowed to ensure we got on the last train back home. The last train left around midnight. And if we weren’t on it, we would be stuck in the city until almost 6 am.
We got to the cigar lounge and met his date for the night. She was a 30 something Filipina with a very curvy body. I let them get to know each other and I tried to stay out of the conversation. I focused my attention on the nice cigar, the nice glass of scotch, and the hot lead singer of the lounge band. The time slowly ticked away and before I knew it, the time came to head to the train station if we were going to make the last train. My friend Max didn’t seem to be wrapping up his conversation. And for some reason, I didn’t interrupt him. A few minutes later I knew our fate was sealed. About 20 minutes later, he acknowledged it as well. In hindsight, this may have been a premeditated plan.
Since we had missed the last train, he asked his new friend if she had any ideas where we would stay for the night. She said we couldn’t stay at her place for some reason but that she had a friend who lived in a penthouse apartment just around the corner. So, Max settled our bill and then we started the walk to the penthouse apartment. As we walked, Max’s friend explained that her friend had a husband who was an executive for the Burberry clothing company. He was always off on business trips and left her alone at home often. “She is really going to like you”, she said to me. “That’s a weird comment”, I thought to myself. We arrived at the 80-story high-rise and the doorman let us into the building because he recognized Max’s friend. We got into the elevator and soon we were on the top floor.
We walked to the end of the hall and soon were greeted by a tiny Filipina woman who couldn’t have been taller than 5 feet. She was slim with nice curves. She welcomed us in and began showing us around. This was by far, the swankiest apartment I had ever seen. She took us out to her wrap around balcony that had panoramic views of the city. She then brought us into the living room and make us drinks. Then she turned the lights down and asked us if we wanted to watch some tv. We said sure. For some reason she decided to turn on some really cheesy porn. Max and I looked at each other and gave each other the, “this is weird” look.
After about 20 minutes of it, Max had seen enough. He grabbed his girl and disappeared into the kitchen. So now, I was stuck with the wife. “Do you want to keep watching?”, she asked. “No. Turn it off”, I said. “Ok, I’ll turn on some music instead”. She turned on some music and then we made pointless small talk. While we awkwardly talked, I heard a sound coming from the kitchen. It was the distinctive sound of a woman moaning in pleasure. I looked over and I could barely make it out but I could see enough to tell that Max has his girl sitting on the kitchen counter and he was in between her legs eating her out.
After a few minutes of this, I saw him run off with her down the hallway into one of the bedrooms. The sound and the thought that they were probably going to have sex turned me on. So, at this point, the wife next to me was in my way. At best, I was hoping she would go to bed so I could stay on the couch and jerk off while listening to them fuck. I told the wife I was pretty tired and asked if I could get some blankets so I could sleep on the couch. She went off and grabbed me some blankets and then she disappeared into her bedroom.
I turned down the music so I could better hear the moans. I took off my jeans, laid down on the couch and started jerking off under the covers. A few minutes into this I heard someone coming down the hall. I put my dick back in my underwear and pretended to be sleep. “Did you turn down the music?”, she asked me. “I guess I did not convince her I was sleep”, I thought. “Yes”, I said. She went over to the stereo and turned the music up again. “Do you like the music?”, she asked me. “Yes”, I said, “its very relaxing. Who is it?”. “It’s me”, she said. “No, I mean, who is the artist?”, I said. “It’s me, she said again”. I thought it was getting lost in translation since English was not her first language. I imagine she saw the confused look on my face. She then explained that she had always wanted to be a singer so, her husband paid to have a professional demo tape made for her. For some reason, I found this interesting, so I wanted to learn more about her singing career. Also, the combination of hearing this information about her and my dick already being hard made me start thinking about fucking her.
As I inched closer to her on the couch, she must have picked up what I was thinking. “Are you horny?”, she asked. “Yes”, I said. “Well, you should go wake up my friend who is sleeping over”, she said. Apparently, she didn’t like staying in her swanky apartment alone so, she had another female friend who was asleep in one of the guest bedrooms. “But, I like you”, I said. She kind of looked me up and down like she was deciding her next move. “Well, I’m married, she said. “And I need to get to bed. If you are horny, wake up my friend”. She quickly got up and went down the hallway again. I once again got up and turned down the music in the hopes of hearing sex from the other bedroom.
A few minutes later, I heard someone coming down the hallway towards the living room again. It was the wife again. “Did you turn down the music?”, she asked. “Yes”, I said. “I was trying to get some sleep.” She went and turned the music back up again and sat on the couch next to me. “So, your horny, huh”? “Yes!”, I said. “Well, you should go wake up my friend.” “But, I want to get to know you better.”, I said. “I want to hear you sing”, I told her. “But, I don’t have a mic”, she said. I repeated, “I want to hear you sing”, and once again, she said, “but, I don’t have a mic”. I told her a third time, “I want to hear you sing”. And, she was more direct this time. “But, I need a mic”. As she said it this time, she pointed to my crotch. I realized I had forgot to cover myself up with the blanket this time, so my hard bulge was very visible in my boxer briefs.
I got the hint this time and pulled out my cock. She had it in her mouth within seconds. She stopped sucking every few minutes to look down the hall to make sure nobody was coming. It was all clear now. She wanted the music up so no one could hear us fucking. While she sucked, I fondled her ass and her breasts through her clothes. After a few minutes, she wanted a change of venue. She stood up and I stood up as well. I dropped my boxers to the floor. She grabbed me by the cock and started leading me, cock first, into the kitchen. She went into the cabinet and got a few throw pillows and laid them on the floor. Then she stripped off all her clothes and lay on the pillows on her back. I took her cue this time, and got down on top of her. “Don’t cum inside me, I’m fertile”, she said. I felt her warm pussy and she was soaking wet. She was also incredibly tight. “Her husband must have a really tiny dick”, I thought to myself as I struggled to fit inside her. Luckily I went slow. The combination of her stretching, her wetness, and me going slow meant that after a few minutes, she was able to take my full length. I was fucking her missionary at full stroke and she was taking all of me. She was wrapping her legs and arms around me and breathing heavy.
She felt amazing as her tight pussy grasped my cock hard with each stroke. I knew I wasn’t going to last long. Before I knew it, I hit the point of no return and tried to pull out. However, the death grip she had on me with her legs and arms made it incredibly difficult for me to pull out. I was in the process of pulling out when the first rope of cum came. I’m not sure if any of it went inside her. Most of my load went on the pillows that were below us. She quickly realized that I was cumming and a look of horror came on her face. “Did you cum in me”, she said. “No, it all went on the pillows”, I said. She jumped up, and ripped the covers off the pillows and grabbed the pillow covers and ran down the hall. I heard the washing machine start. “Destroying the evidence”, I thought. Then a few minutes I heard her running again and then a shower coming on. I assumed she didn’t fully buy my story that I pulled out before I came.
I grabbed my clothes and went back to the couch to try to get some sleep. However, by this time, the sun was starting to come up. Just as I laid down, my friend Max emerged. “Hey man, time to go”. He didn’t get into details but, apparently it had gotten weird with his girl. We left the apartment and headed for the train station. I shared my story and we both had a good laugh. We got on the train and headed back home. It was a long work day for both of us since we both didn’t get any sleep. We both never contacted our sex partners for the night ever again!
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