Prologue Part 3: Almost Fell for Lola

I begin to turn to Craigslist to see what is out there. I’m really testing the limits at this time, I don’t think I’d ever seriously consider having an affair. We are about to begin our descent down the rabbit hole here, this is where I imagine I’ll alienate a good a number of you nice folks who have been following me (hell if I know, I can’t tell what’ll offend people anymore). But, I’m laying bare my soul here, as ugly as it is. Porn pushed me to more diverse interests. For some reason, I get in my mind that perhaps a homosexual liaison would be more palatable to my moral senses (which were clearly breaking down at this point). It sounds stupid, but the idea of doing something with a dude didn’t really feel like a true betrayal of my wife so I was much more comfortable with it.

I was fascinated at the thought of sucking a dick, but I was always super grossed out whenever I looked at another man naked (homosexual stuff was fun to imagine, but I couldn’t stand to watch actual porn of it). Transsexual stuff turned me on though, so I started looking in the t4m of casual encounters to see what was out there. Most of the “girls” were not very fem though. Those that were, were always prostitutes I’d come to find out.

I finally succumb and shell out $50 to suck a fairly feminine-looking black girl’s big black dick. It was big, circumcised and corkscrew like, and I had to suck her manly nipples to get it hard. It was kind of fun, but she was pretty rough and throat fucked me before I was good and ready to deep throat a cock (especially one that big, I’m surprised I didn’t gag much). Afterwards, I was kind of like ‘meh’. I didn’t really feel guilty, but decided it wasn’t really for me. I’d explore with another transsexual prostitute a few months later including bottoming, this was a Mexican one with a tiny dick, and it did kind of feel nice in my ass, but once again, didn’t seem worth it. Then I thought I’d suck a masculine guy’s penis hoping to save cash on prostitutes (I was totally grossed during the whole experience, but finished him still since I like to finish what I start), but after that I figured I had all the homosexual stuff out of my system, deciding that it really didn’t excite me or arouse me, it was as alien to what I considered ‘sex’ as could be. No, I decided, I’m really attracted to women only, but I still had a strong feeling that having sex with another woman would be going to far.

At this point, my adherence to Christian morality was an illusion, I was letting my emotions guide my moral sense, which is a dangerous place to be. After a severe argument with my wife, I could easily see myself cheating on her, but then after an enjoyable evening talking and making love, I couldn’t imagine being comfortable with that. My moral compass was broken and the north it pointed out changed moment to moment on the rolling seas.

I’m surprised at how casual this post came off. It was a really big deal for me to perform homosexual acts at the time (I knew I was sinning according to my Christian upbringing and at the time it was quite the hurdle). My wife would have been appalled if she knew I’d done any of this stuff (no question, she’d leave my on the spot). But, in hindsight it feels so minor, just a bump in the road. Perhaps I’ve become too jaded and unfeeling? Or perhaps I just judge the gravity of my sin by the seriousness of the consequences and the fleeting pleasure it brings me.


6 thoughts on “Prologue Part 3: Almost Fell for Lola

  1. Almost fell, eh? Interesting 😉

    You know, your bicurious tag is the reason why I landed here. 🙂
    I am glad I found you. I am quite intrigued. 🙂

    I get what you mean about feeling that doing it with tranny’s and guys might seem like less of a betrayal but it really isn’t…(yeah stating the obvious) LOL with that said I think it’s really cool and adventurous that you explored this.
    Maybe you would be turned on (and excited) if you were involved in a threesome or a couple? You know everything is so much easier when you and your partner(s) are sexually excited . 🙂

    I am rambling… better stop now. 🙂


    1. Seems to me there is a hierarchy of intimacy which involves gender and number of persons. For example, if I hang out with two friends, a guy and a gal, all cool, it is somewhat intimate, but certainly my wife won’t have any issue with it. If the gal leaves, it becomes more intimate, but nothing that would concern her. If the guy left me alone with the gal, this would suddenly become intimate (even if we were just keeping it platonic, it is merely the proximity to a sexual situation that makes it more intimate) and would make my wife uncomfortable.

      I’ve had couples on CL try to get me involved in threesomes before, and I’ve thought about it, and similar to the homosexual stuff I’ve tried, it seemed like it would be less of a betrayal because of the intimacy factor involved. But I realized, what I really want is that intimacy factor. Not that my AP would be totally monogamous with me, but that when we are together it is just us two, only us sharing that one experience together, the height of intimacy. I realized that is what I was really seeking. Hard to explain, so I’ll give an example. One of my AP’s turns into a totally different person with her clothes off, and I find it incredibly rewarding that I’m one of the few individuals who gets to see and experience this, that’s what does it for me, sharing that intimate experience with that one person. This one person is here and they are completely focused on me, and me on them, our bodies joined, interacting, feeling the same experience. I feel like, in those brief moments, that I matter in the world.

      Liked by 1 person

      1. I am sorry, excuse my ignorance, what’s an AP?

        I totally get what you are saying regarding intimacy between two people and only two people. That’s so very special and makes you feel like you are on top of the world. 🙂 Glad you have that now. 🙂
        But I wanted to share that I also experienced one-of-a-kind-intimacy when I was the third or we let a third joins us. Very different but still so much fun.

        I guess it’s all about experiencing what we are seeking and the gratification of said activities. 🙂

        Makes me want to write a post about it and my experiences. 🙂

        Anyway, thanks for the comments and chit chat. 🙂


        1. Gosh, I hate when people use acronyms in writing intended for public consumption, tacky 😛

          Sorry about that, I need to either post acronym glossary or stop doing that, AP is affair partner.

          Thanks for sharing your experience, I’ve had several people relate something similar in regards to threesomes and I might try one someday. You are right, we are all seeking certain gratifications and everyone is a bit different. I appreciate all your comments, I’ve found that these comments really help me make sense of it all and understand what I’m truly feeling.

          Liked by 1 person

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