My Encounter With a Sociopath 3


This is the first of 4 pieces about an encounter I had with a sociopath. The rest are here:


I met Chicago Man last November on OKCupid. He represented himself as single, never been married, no children, and looking for a long term non-monogamous relationship. He sent a lengthy, forthcoming and very articulate letter of introduction. On paper, our kinks matched quite well. He lived in Chicago, but assured me that I shouldn’t be concerned about that, because he could live anywhere he wanted to; he traveled for work. From the start he said he didn’t have much time to offer; his career was in full swing, and was always his priority.

We began to get to know each other. We clicked. He told me his name and the field he worked in. I looked him up on the internet and found his business website and many mentions of him for conferences, consulting and various projects.

He came out to meet me in January. Our connection was an unexpected level of incredible. He said he was enthralled with me. The feeling was mutual. A flurry of texts followed his visit. Every time I talked with him we had this instant connection, and I always hung up feeling happy. I liked him. A lot.

I started writing about him. Always with his permission, and with a certain thrill in my words, because I was falling for him. We handled the distance with sexting, and sometimes I had control over his orgasms, which was a thrill for us both. He’s a brilliant man, and I am a sapiosexual. That added to it. But he also listened when I spoke about emotions. He responded when I expressed needs. I felt understood and cared about.

The lack of time he offered was ever-present, and I tried hard to work with it. I figured that since I wanted to be non-monogamous, perhaps there was a space that Chicago Man could fit in my life, even with the lack of time.

He came out to see me again in April. We enjoyed an extraordinary visit. He arranged for me to get into the hotel room early. I was ready and waiting for him right when he walked through the door. Our time together was so joyful, erotic, and intense. We just seemed to fit.

He continued to speak in terms of a serious relationship with me. He asked me what would need to happen for him to be considered my primary. He expressed unconditional support of me and my goals, always encouraging me and offering occasional business advice. He would tell me of his meetings in the high powered business world he traveled in, and I would encourage him to go to those meetings confidently, with all of his brilliance. He even spoke of job possibilities out in California that we were both excited about.

The lack of time he offered began to wear on me. He rarely seemed to have more than 15 minutes to talk with me, even though he spoke of going on dates occasionally. I complained about that. I felt like I was being managed, like I always came last in his world. We talked. He reassured me and promised to make changes.

He said beautiful words during that conversation. He said no other woman he’d ever known held a candle to me because I was world class. I wasn’t the cream of the crop; I was the whole fucking crop. He even said ‘I love you’.

A couple of days ago, I sent a text. I sent another one 14 hours later. Then, recalling that sometimes he didn’t receive my texts, yesterday I sent him an email.

The email bounced back – no such email account.

I called his phone. Disconnected.

I looked at his FetLife profile. Gone.

Chicago Man had fucking ghosted me.

Wow. I didn’t see that coming. It pulled the rug right out from under me.

I went to the gym and worked out hard to take the edge off my angst, and still cried all the way home.

Today I went to his business website and sent him an email from the contact link. My email said that since he’d eliminated every channel I’d ever used to communicate with him, that his actions spoke louder than words. I called him cowardly and said it was a shame he couldn’t have been honest with me. I pushed the send button. I wondered what would happen if a secretary received the email and not him. I didn’t care. I had no illusions of hearing back from him.

I began to look up ghosting to educate myself. It’s such an emotionally cruel thing to do to someone. I wanted to understand the usual repercussions so I could take care of myself from a place of knowledge. I felt stupid, like a fool. I felt used, and a part of me felt like I should have known it was happening. It shook me to my core.

Instead of doing the research on ghosting, though, I satisfied my urge to do some cyber research on Chicago Man, finally forking out $10 for some information.  It turned out to be well worth it.

Chicago Man is married with children.

Wow. That was like a punch in the stomach on top of the rug thing.

I was amazed at the amount of information I got. Home address, phone, wife’s name, the year they bought their house, car registration, kid’s names, where they go to school. The wife has a facebook page with lovely pictures of their cozy, very religious family. Many pictures of family trips had been posted since he first contacted me in November of last year.

I was seething with anger.

I went back to his business website and called the mobile number listed there. I used Google voice so my number wouldn’t show up in caller ID. I didn’t have a plan. I was angry.

He picked up.

“Hi, this is Steve…?” (not his real name)

I was silent. I didn’t know what to say. I was shocked that I’d actually reached him.

“Hello? This is Steve…?”

“It’s Ruby.”

“Excuse me?”

“It’s Ruby.” My tone dripped with accusation.

“Okay, look. I don’t have a whole lot of time to talk…but please don’t call here anymore.” The slight note of fear in his voice gave me great satisfaction.

“Because you’re married with kids?” No point in beating around the bush.


FUCKYOU!” I yelled, and hung up. That was the best I could manage in the moment with no plan.

His level of dishonesty leaves me speechless. Thinking back, the lies seemed to roll off his lips effortlessly. How does one even do that? From all appearances, he was a man quite comfortable with himself, with nothing to hide. Kinky as hell, and not anxious for the business world to know that part of him, but that’s true for 99% of kinky people.

He used me for as long as it was convenient, and then discarded me. I’m so fucking angry. Angry enough to where it’s tempting to message his wife, I must admit. And I haven’t decided whether to do that or not. The thing is, my intention would be to wound him, to fuck him over like he fucked me over. I don’t want that negativity. I don’t want to hold onto it like a cancer inside me. And as always, my anger is covering up pain.

Pain because now I’m not sure what part of our relationship was real and what was a lie. That fucks with my head, as well as my sense of self-worth. The foundation I thought was there turned out to be non-existent. I’m a trusting person. I showed up in that relationship. I was honest, open, willing, and communicative. The only red flag was his serious lack of time.

Instead of obsessing about what was real and what wasn’t, though, I prefer to find solace in how I experienced what we shared, because that is all I can be certain of.  And honestly? I savored what we shared like fine champagne. It was real for me. I was all in. It was magnificent. I’m not sad that I trusted him. I’m not sad I let myself fall for him. All I did was believe him.

So what now? In each and every moment, we all have a choice, to contract with fear or expand with love. I refuse to let this experience shut me down or make me fearful and suspicious. I still want to walk around in the world with trust and openness as my default.  I choose to stay open with love. I choose to let go of the bitterness, work through the pain and move on. The sociopath will not win.

Someday, when I feel ready to have another relationship, I will resist the urge to require a questionnaire, personal referrals and 3 forms of supporting documentation. Because I believe the sociopaths are few and far between, and it was just an unfortunate chance that I encountered one.


21 Responses

  1. My heart aches for such a loving gentle heart as yourself to go thru such heartache I know not much can help but know that all of us listeners and followers truly appreciate what you do for us day in and day out and we are here to support anyway we can. I hope you find your one true soul mate soon I promise he exists you just have to stay positive and keep searching.

  2. OKCupid is full of functional sociopaths, unfortunately. It’s like a buffet for them. On top of that, OKC and fetlife are also both full of broken, damaged people which the psychopaths feed on–and we get caught as collateral damage. I’m no expert, but I’ve had my experiences with those people.

    Definitely the three things to watch out for is anyone from out of state who say they “visit” your area a lot on business or whatever, severe lack of time, and what I call “mirroring”, which entails them asking you lots of questions about your likes and dislikes and spewing them back, so there’s a false sense of connection. And emails and texts are hot and heavy, but they can’t talk on the phone or Skype on a regular basis.

    I know your grief and anger intimately. The unfortunate result of being used and discarded is a pervasive lack of trust in any future relationship. I think this may be the worst of the damage these monsters inflict. The pain eventually dissipates, but this remains.

    Thing is, as you obviously know, vanilla dating sites such as are distasteful to a person looking for kink in any relationship. And there’s no guarantee that those sites harbor any less amount of sociopaths or damage cases than any kink site–it’s a lot less visible too. It’s a horrible quandary.

    Here’s declaring to the Universe that we both find men worthy of our attention, who fulfill us emotionally and physically, and they will in turn reap the benefits of our love.

    1. Here’s declaring to the Universe that we both find men worthy of our attention, who fulfill us emotionally and physically, and they will in turn reap the benefits of our love.


  3. Sad.
    But you met someone halfway across the country by way of a online dating service and saw them in person like 2 times and you had the audacity to entertain the idea that you found someone desireable.

    1. Wow – perhaps audacity in your eyes. Not in mine. I knew I’d found someone desirable. I knew I wanted to see more of him. But I didn’t know if what we had would work or not. Do me a favor and try not to sound so superior.

      The last thing a person who just got fucked over wants to hear is you were stupid to fall for it.

  4. Unbelievable! I had the “audacity” to find someone special online and to travel 5000 miles across the world in order to meet her. In reality she travelled to my country first so we met in person precisely twice last calendar year. Where you see audacity I see faith and trust. No one should be treated in the manner Ruby has.

    I’m so sorry that this has happened to you Ruby and I’ve never wanted to believe in karma more than I do right now. Thank you for choosing to share this with your faithful listeners/readers.., In fact let’s just call us fans. I’m a fan of what you do. If this post manages to guide at least one other person through the potential pitfalls of online connections then you have once more selflessly given some wonderful advice through experience and knowledge.

    My opinion should mean little to you, just one more faceless voice in print, but one of the reasons I return here is that I recognise some of the extraordinary qualities you possess. By sharing this experience your generousity and strength have me floored. Your story has angered both myself and my partner. How sad that with new ways of connecting it simply offers new ways of deceiving others. You deserved none of this and I hope it hasn’t soured you to the potential of online relationships. I got lucky. I thank my lucky stars every time I remember that fact.

    Please take care of yourself.


    1. That’s one of the reasons I shared this – in the hopes that it would help even one other person.

      So happy that you got lucky! I have heard many stories like yours actually and I remain positive that when the time is right, it will happen. I’m not soured on relationships, I will always desire and welcome love and companionship in my life. Just going to take a break from the search for a while to heal.

  5. Ruby,

    My heart quietly resonates to the psychic pain this shallow man inflicted upon you. I know you will move on in life and find the scar of this injury slowly fade with time. I share the thoughts of the many others in wishing you loving energies as you continue your life quest toward greater fulfillment of all the people you meet, both in physical reality and our shared virtual reality. Your strength of conviction empowers us all to be better human beings and in exchange we offer our energy in support of you.rumel
    Good Vibes to You !

  6. OMG Ruby so sorry to hear what happened to you. What an A-hole that guy was! Seems like the usual hypocrisy of respectable family man while wanting to live a secret other life. There is nothing wrong in living another secret life and sometimes it is highly necessary when you have a partner who would never understand. But the brutality which which he discarded you when he decided he no longer wanted to proceed further is what angers me. Lets hope he never decides to run as a Senator or Congressman and gets up on the podium to proclaim family values otherwise I think you might have to come forward and tell your story. ;o)

    You are a beautiful giving soul Ruby. May you find healing and peace and a return of your inner joy.

    Much love from across the pond.

    Peter x

    1. Thanks, Peter. I appreciate your kind words. I completely agree about fully divulging if he ever decides to run for public office. I don’t think there’s any chance of that, though. WAY too many skeletons in his closet.

      My peace is returning, I can feel it.

  7. I really feel for you Ruby. So easy for a person to be something they are not on the internet. It has been my experience that meeting someone on the internet is always problematic. Think about this what drew you to him ? Only you know ,but remember whatever you were looking for he pretended to have it. Maybe it is best that it happened now and not later. Keep this in mind the world of fetishes is full of people who have trust and boundary issues. What you do is in demand and most women won`t even come close to what you do .If other women would do it maybe their men won`t be looking around for someone who will. Think of this you are strapping men,that is why you are sought out. Many men who get pegged are confused somewhat. Try not to invest some much in these relationships that revolve around pegging maybe meet someone somewhere that is not into it but will let you do what you like. Consider that what you do is quite unusual and men shell out big bucks to be pegged. Just place an ad on backpage or craigslist and just count the responses. There is a strong demand and very small supply of women willing to peg men.

    1. Thanks for your well-intended advice. I have indeed thought about pretty much all of those things, and tried to plan accordingly in terms of how I navigate the dating world. I do not believe that all online connections are problematic. The world is full of successful love stories that started on internet dating sites.

      Try not to invest some much in these relationships that revolve around pegging maybe meet someone somewhere that is not into it but will let you do what you like.

      I have tried withholding my kinks until the second or third date with men from vanilla dating sites, and every single time (so far) they run for the hills when I divulge. I lay my kink cards out on the table right off because I don’t want to get hopeful and attached and then find out I’m with a man who considers his ass ‘exit only’ and/or would never be okay openly dating a sex educator. So much of my life is all about teaching, writing, podcasting, etc – that holding back these details in the beginning presents another problem – being okay with a high profile sex educator is not for everyone. I need someone who can welcome me into their life fully, without fear of repercussions should their family and friends discover what I do. Another issue – I do not want to be a facilitator, teaching someone to be sex-positive, teaching them to open up sexually. Nope, I want them to already be there. At my age, I don’t need a project for a partner.
      It’s a conundrum.
      But I remain positive.
      When it’s right , it will happen.

  8. I just thought of something else also. The pool which you are drawing potential dating prospects from is very shallow. In that small pool is a concentrated group of people that may have trust and or boundary issues. I mean more than general population. Think about it before you started pegging what was your opinion about people who want ir ? Ask some vanilla friends what they think of it . Most will laugh or condemn it. So be prepared and check thoroughly any men who you meet through your site. A man who can find a wife who will peg him has found a diamond. Women don`t usually get into this kind of stuff because they have so many other opportunities. Women can be vanilla and still have men standing in line, provided she looks good.Men have to be rich or shell out big bucks to get pegged .Think about it supply and demand.

    1. Again, I appreciate your suggestions – but I DO NOT WANT A VANILLA MAN!! I want a man I can beat and peg and order around in the bedroom. What you don’t seem to understand is that by the time I find out a vanilla man is not suited or unwilling to go along with my program, I have already wasted a bunch of time and gotten hopeful and perhaps even gotten attached when he decides to bail. No thank you.

      I have no interest in trying to turn a vanilla man kinky. I facilitate so much in this part of my life, helping people learn about pegging and navigating the path to it. If I have to also facilitate in my relationship I will just scream. When is it my turn? I’d rather be single with fuck buddies.

      Remember the part about – HIGH PROFILE SEX EDUCATOR? Vanilla men might be intrigued, but they want to hide me away. Again – no thank you.

  9. Ok just voicing my opinion. Make sure your motives are pure look inward deeply. Make sure you are not motivated by material reward or possible deep seated resentment of men. If a man said he just wanted a woman he could beat ,screw in behind and order around the bedroom we would probably think differently of him. Search your heart and see besides pegging and domination what are your attributes ? I mean what can you offer in the way of love,compassion,respect ,. It maybe that men who want to be pegged and dominated only want that a small fraction of the time. Just saying. I enjoy giving women facials and having them go to public places i.e. hair salons and ,dental appointments,meeting with real estate agents etc. Many women don`t have what it takes to do this and the few that do have other problems i.e. want money or have issues. The world of kink can be disappointing. Seems hard to get kinks in sync sometimes. I`ve been trying to find a girl who will do bukkake and go to an upscale salon for hairstyle so I`m in same boat.

    1. You are not just voicing your opinion – you are telling me what to do. When you use words like: “Make sure you..”, “Think about it…”, “Ask your vanilla friends…”, “Be prepared and check thoroughly…”, “Keep this in mind…”, “Try not to invest…”, and “consider what you do…”, you are telling someone what to do. And you need to stop.

      You infer that I am a single-minded woman who’s all about pegging and dominance and nothing else. You don’t know me! Until you have read my dating profile, please don’t make assumptions about how I put myself out there in the world. Do you really think that’s all there is to me? Do you really think I am not a well-rounded person with plenty to offer besides pegging and domination? LMAO

      You need to stop changing my words and giving me advice.
      I never said ‘just’ want a man I can beat, fuck and order around the bedroom. YOU put the word ‘just” in there.

      You are coming across as someone who seems to think you know what’s best for everyone, in this case including me. I’m going to give you the benefit of the doubt here and assume you were well-intentioned and trying to help. Stop trying. you are pissing me off by telling me what I should do and making assumptions about me.

  10. Sorry about the misinterpretation . I had a man recently tell me don`t buy a car with this type transmission. I never thought he was telling me what to do he was saying if he were me, I knew what he meant there would be no benefit to him of telling me what to do. I was just speaking from different perspective. One think that has helped me is to consider my motive why do I do x or why do I feel why etc. Not sure what you place on your profile but maybe men want pegging others want something else and they have everything but that in current relationship. So maybe they are happy where they are at except for pegging. What strikes me is why so few women into kink compared to men ? Look at population about 50 percent men 50 percent women but probably less than 3 percent women into kink compared to 20 percent or more men. Seems many women who are into kink are not into for fulfillment many that is their occupation. I would screw women all day long for free . Women most women not all I suppose would not do that. Strange world .I wasn`t telling you what to do but was kinda saying be on the lookout. People say consider this ,or try not to or make this to me all the time and I don`t think they are telling me what to do. Maybe they are and I don`t pick up on it. I was just I would look at the numbers of men into kink and wonder what importance is hold for them is it their whole lives or just something they enjoy.

  11. Many men have fulfilling lives except for kink .Women seem less likely to accept kink and if things go bad they do publically say stuff about screwing them in the ass or telling their family about what he has done to her. I just reverse roles and see if I would want them to do that to me kinda Golden Rule. Hope that helps never meant to tell you what to do or hurt your feeling or anything. Just wondering how many men who want to be pegged but don`t want to give up current relationship because divorce is costly. I think men would more easily divorce if it didn`t cost anything.Like I said women who indulge in kink are much rarer than men and many only do it for money. When money not there many don`t indulge where men sometimes or most times would do it for free.I can`t for the life of me figure out why I can`t find a woman who wants to be bukkaked and go to a upscale salon on my dime afterwards .Even with money seems hard to find women makes me think they are not as many that are into it or they have other options. The heartbreaking part is some many women into kink for money instead of the love of the kink.I always look inward to understand my motives like the pegging motive for you ? How do you benefit ? How does it make you feel ? Those are the questions I ask about my kink

Leave a Reply

Your Source For All Things Pegging

Information and resources for anal sex, bdsm, strap-ons, intimacy, and female domination. Let Ruby know what you think! Leave a comment, register for erotica, or catch a webinar.

More Articles