I met Madam M from a Craigslist ad sometime in the summer of 2006. After a couple of emails, she texted me some days later and asked if I wanted to meet up with her. She was going home later in the evening, and asked I pick her up from a street corner in Richmond. I drove us to her rental on Bridgeport. It was a large house that was being rented to multiple people. Upon entering her room, she quickly put her things down and asked me to make myself feel comfortable, as she went out the door again. After awhile, she came back into her room, and closed the door gently while facing me the entire time. She was wearing a teddy-top and pajama pants. I noticed in the light, that despite just showering, she was still dolled up. Her eyelashes were longish, and she had shiny pinkish lipstick on. I pondered whether she put on a new layer of blush too. While Madam M was on the heavier side, she later claimed that she was also born big boned, and she was taller than me about an inch. Her body was quite firm and her skin was well kept. She had a nice complexion and soft feminine skin.
After she finished organizing a bit of her room, she leaned up against her corner desk and stared at me like I was prey. I smiled at her and she smiled back. Our conversation continued and I checked her out of course. She had large bountiful breasts and a decent figure even when being overweight. Also, the clothes she wore were feminine. She knew how to put on make-up, put on the right type of jewelry, and styled her hair suitable to the occasion.
As the evening went by, I ended up lying down on her bed facing upward while she laid down beside me on her stomach. Our conversation went from her fake marriage to help some dude from China get his green card into Canada, to some random stuff about him, to how I felt about casual hook-ups. For a time, our faces were super close to each other, at times, our cheeks touched, and the corners of our mouths caressed each others’ faces. Her teddy-top wasn’t buttoned and her cleavage was very noticeable. She asked if I liked big boobs, which I told her that I didn’t have much experience with them, but I liked what I saw.
The night went on and she outright told me she thinks it’s totally okay for two adults to have a consensual sexual relationship without the romance. We ended up exchanging a few light kisses a few times over the two hours I spent there. She also caressed my my hard on inside my pants and I gently thumbed her bare nipples every time we kissed. She ended up putting my cock in her mouth. She licked and sucked extremely well. Honestly, I had never felt so much pleasure from receiving oral before. While other women had given me blowjobs before, almost all of them didn’t feel half as amazing as when Madam M sucked me. Unfortunately, my emotional vulnerability stopped me from letting her continue, even though I really wanted to cum into her throat. Foolishly, I wanted to get to know her better, before having sex with her. I apologized while my dick was still erect, hanging out of my pants, drenched in a mixture of my pre-cum and her saliva. She thought I had came to the realization she was unattractive, and that’s why I stopped myself. I assured her it had nothing to do with that, but didn’t know how to explain myself properly. To try to help not make her feel bad coinciding her interpretation of what happened, I gave her a kiss on her lips, hugged her, and smiled at her before I left the front door of her house.
Over the next few years, we communicated primarily on the phone for about an hour or two at a time. Usually it’s about the corruption in her church, the idiots at her workplace, the unfairness she had faced, and the constant sexual harassment she experienced mostly where she worked as a chef. In the uncommon times we met with each other in person, 60% of the time was hanging out. 40% of the time was sex related. She was extremely slutty and vulgar which always turned me on like crazy. Most of the swearing and vulgarity was spoken in crisp Cantonese. One time, she called me up in the middle of the day asking if I was busy. Before I could respond, in Cantonese, she said, “My pussy is fucking gushing. When can you come over to fuck my brains out?” It took me a quick, but decisive driving to get to her place within 30 minutes. The literal moment I knocked on her door, she pulled me inside, slammed the door shut, and knelt down in front of me to get me hard. Then I proceeded to pound her in her living room. She could never cum through penetration alone. So after I creamed inside of her pussy, I continued to fuck her, and licked her super sensitive nipples while she rubbed her pussy to an orgasm. I stayed hard primarily because she looked and sounded so horny. She also shared stories of her other exploits and experiences, which were pretty fun to listen to, like the threesome experience and other naughty rendezvous she had with other men over the years. Plus, having a feminine voice made it all quite arousing. In the nearly five years we were friends, we had penetrative sex four times. The rest were just a mixture of molestation, masturbation, and oral sex. I wish I had made sex videos and pictures of her. I would definitely watch her yumminess today.
The main reason we only had intercourse four times in the five years we were friends, was due to the fact I was mostly turned off by her attitude and behaviour. From 2006 to 2011, she attended a church full of pretentious toxic assholes. She also came from an emotionally abusive family. Through that upbringing, even though she was an independent career woman, she was also indecisive, emotionally naive, and often spoke over people – over me. Like she didn’t really listen and processed what I said. Instead, it often felt like whatever I said went in one ear and immediately went out the other. Unless we were talking about sex, almost everything else I said was met with hollowed responses. There were of course positive aspects to her. For example, she was considerate of people’s needs when they are in front of her. She will go out of her way to make you feel ‘at home’, make sure you’re fed, you’re not thirsty and generally, I think she had her heart in the right place, even if it was ultimately misplaced. For example, she had the belief that all she has to do is accept a man into her life, love him, and things will just fall into place. Even if she knowingly acknowledged those men are using her for everything other than love and romance. She wasn’t a terrible person, but she can be super judgmental and hypocritical. During those five years, I have spent on average about 1-2 hours on the phone with her, for almost every single call. After the endless phone calls in those five years, where she vented the same miserable experiences she kept having, on top of asking me for advice she never took, I finally decided that I could not deal with such a miserable person, because I was dealing with my own shit at the time too. I cannot continue to have people who allowed themselves to live in toxic environments, to permeate that toxicity into mine. So after blowing up on her one evening, I stopped talking to her. She texted me a couple of times after that, but stopped when I didn’t respond.
From 2011 to 2019, I did think about Madam M from time to time. While we were no longer friends, I still cared about her well being. I just didn’t want to be involved in that relationship. However, I decided to reconnect with her and contacted her through LinkedIn in mid 2019. She gave me her phone number and through a phone call, I apologized for my behaviour in the past. For the next two months, we spoke with each other through Whatsapp and phone calls. This entire time, nothing related to sex was every spoken about.
One night, after having dealt with a series of repeated issues in my relationship with Amber, combined with the growing depression that waxed and waned, I messaged Madam M and told her that she looked really good in one of her pictures. She responded in a voice message to me, “I didn’t realize you still thought of me that way. I mean, it’s not like we haven’t had sex before.”
So I thought that was an invitation to meet up with her for at least, a one night stand. However, instead of driving over to see her, I drove over to my old neighbourhood, and parked my car there. While I was horny for Madam M, I was also aware enough to know that I could be making a huge mistake. So while my cock was driving me to Madam M, my brain deterred me from making the biggest mistake of my life. Note that this was before Amber and I started our non-monogamous relationship.
To cut this part of the story short, basically, the messages that occurred between Madam M and I that late night, was less a conversation and more Madam M lecturing about me how we shouldn’t be talking about sex related topics because we’re both married to different partners. She told me that she didn’t want to disrespect my wife Amber, even though she doesn’t know her. In her long lecture, like usual, she wasn’t actually listening and processing what I said to her. That’s why it wasn’t a conversation but a lecture. We ended our one-sided conversation with some light conversation about my brother, her sister, and then said our good nights. I thought that our night ended up on a positive note, despite my original intention.
A month had passed and I did not see nor hear a peep from Madam M. I thought perhaps she was busy. By now, Amber and I were going through the transitional stage of opening up our marriage. She asked me to ask Madam M if she would be interested in showing her how to suck cock. I told Amber that Madam M most likely will reject the idea, as she seems to have become a different person than she was about a decade ago. However, Amber insisted. So I messaged Madam M on Whatsapp. After a short intro, I asked Madam M if she would be interested in teaching Amber how to give oral sex either on me or with her partner. To cut a long story short, Madam M told me the reason she stopped contacting me a month ago, was because she felt I was bringing our conversation back to sex. I interjected and reminded her that I only brought up sex once. She ignored that and continued by saying that my proposition is offensive not only to her as a mother to a child, but also the fact she is married. I was quite mind boggled to her reasoning because her marriage was a marriage of convenience. Clearly, it seemed they stayed married for the sake of their young son. Whatever family photos she puts up on social media is all an illusion to show their friends and family members, they don’t have to worry about their broken marriage. She even mentioned a month before this, that if her husband finds out she sex chats with other men, she wouldn’t care.
After that hypocritical bullshit, I blocked her. What’s further humorous about all of this, is that as of December 1st, 2020, over a year after we ended our friendship for the last time, I found out that Madam M and her husband had divorced. So much for respecting her marriage eh?
Now, to be clear, I reconnected with Madam M because by 2019, eight years had already passed. I was in a life stage where I was ready to reach out to old and broken relationships, to see if things can evolve from them. Eight years is a long time. Considering what I had known about Madam M, I thought perhaps in those years apart, she would have finally matured emotionally and refined her personality. While I wasn’t fully sure of her sexual alignment, I gave her the benefit of the doubt. I had hoped she became as sex positive as I have. Alas, she was clearly nearly the same person as she was eight years ago, except without the sexual openness and she finally had the guts to remove herself from toxic people. My biggest issue besides her hypocrisy, is that she didn’t address me as a mature adult. She accused me of bringing our friendship back into sex, when I only mentioned it once before, and if the current situation made her feel she didn’t want any sex between us, all she had to do was say, “Leeman, I must decline your proposition. Thanks for asking me, but from now on, I would prefer we not take our conversations into sex again. I am a totally different person than I was when you knew me back then.” If Madam M had said that to me, you can be sure I will respect her wishes, and never bring up sex or propositions of sex toward her ever again.
It’s a shame really. Madam M could have been an interesting teacher of all that is sexual. When her mind wasn’t clouded with judgment and hypocrisy, she was actually a decent friend too.