Anal sex… Sorry for the pause, just needed to slowly ease into this post. My general assumption is that most women have had or at least tried to have anal sex at some point in their sexual journey. Certainly, a woman’s anal status isn’t something I typically ask about before or after experiencing her in such an intimate way either. Perhaps this is why it came as a surprise to learn Sienna was still an anal virgin and wanted me to remedy this situation. Of course, being a gentleman, I readily agreed to relieve her of this burdensome label. Given her anticipation of this deflowering, I couldn’t help but wonder why she hadn’t already done this before and why it was feeling so hot for her now.

“I’m still trying to figure out what anal means to me emotionally. I have always felt like it would be degrading, but the thought of you taking me this way is now making me so wet! It’s confusing!” ~ Sienna

Why the cognitive dissonance? Perhaps Sienna’s Catholic upbringing contributed to her feeling that allowing a man to bend her over and fuck her ass would be dirty and wildly degrading.

If she allowed this happen or, even worse, wanted it to happen she would be a “bad girl”. Anal sex isn’t inherently degrading, but it was in her mind. Beyond her generalized sense of moral shame, Sienna seemed to experience a counter-balancing erotic swirl flowing through her decadent thoughts. Her sense of arousal flowing from being “degraded” means she would likely experience anal sex as a form of erotic humiliation.

🔎 I wrote an essay called Exploring the Layers – Erotic Humiliation that digs a little deeper into the psychology of humiliation play.

Sienna’s anal revelation and her deeper erotic layers ignited my mind and soul (along with my cock). She had never been able to safely express and explore her submissive desires with any man before, and it felt incredibly special for her to be opening up to me about these long-repressed sexual fantasies. I felt honored (and extremely aroused) to be the man guiding Sienna through her sexual awakening. It was truly a gift.

Then, Sienna took our anal discussion even deeper…

So, I’ve had this thought in my mind about you the last couple days…I can’t shake the thought of you taking me from behind…slooowwwly working your strong, beautiful cock in my tight space, mmmm!!! As you sink deeper and deeper inside, encourage me and call me a good girl for taking your cock. If I whimper, spank my ass and tell me to take it! Once you are allll the way inside me, I will reach under and hold your big, heavy balls…pleading with you to cum in my ass. “Please Sir, your girl needs it! I want your full creamy load in my ass! Cum in your girl’s ass and mark your spot. I want it and need to feel owned!”

Fuck!!! Thinking about you having me this way has made me cum so hard the last couple days! 💦🔥😘 ~ Sienna

Whew, just reading her thoughts again has me rock hard. I always loved the way she would reach underneath when bent over doggy style and handle my large balls. Her desire to be handled firmly while having her ass taken is clearly coming through as an element of her D/s fantasy. Her desire for me to call her a “good girl” while gaping her ass and filling her with my essence is certainly a form of reassurance she will need from me to overcome her own “bad girl” association with anal sex.

In the post 30 Days – Sienna’s Fantasies, Sienna revealed her desire to explore her submissive side. Submission was a new experience and she was framing anal sex within the framework of that submission. I’m sure it would have been even hotter for her if I had brought up the topic, but I was all the way in now. From this moment forward, taking her ass at every opportunity would become a top priority.

As we sank deeper into anal exploration through a lens of submission, I realized Sienna had responded to my fantasy of wanting to watch her with another man (Introducing the Cuckold Fantasy to Sienna) in the same way. She said she would do it as an act of submission. I owned her pussy, and if I wanted her to fuck other men, it was my decision. My sweet, naughty angel said, “I will do it…for you”.

I find the parallels in Sienna’s framing of these two situations (anal sex and cuckolding) fascinating. These scenarios along with countless observations of submissive women have led me to a somewhat ironic conclusion that women often find sexual freedom in submission. They are able to set aside any guilt or shame they might typically feel when doing something naughty because they have no “control”. They are only doing what their Sir (often the man they love) wants them to do. In doing so, they are being a good girl by doing naughty things. The mental judo is spectacular and quite alluring. It is also a key part of the archetypal energy I think of as the “Naughty Angel

At this point in our loving, erotic journey, taking Sienna’s “tight space” was taking on new meaning. Sliding my cock inside Sienna’s hot, tight ass would now activate far more than superficial physical sensations. Now, the experience would reach far deeper, add extra intensity to the sensations, and be far more fulfilling. With our mind, body, and unified souls connected to the experience, we just might be able to reach a state of transcendent ecstasy – the Dionysian experience.

Looking Ahead

In the near future, I will share what happens when we finally connect after being apart for thirty days and with Sienna’s anal virginity in play. This reflection also sets the stage for an intense moment about one year later during our first cuckold experience with Jalen (the first Bull to fuck Sienna). Having already fucked her into a state of complete sexual delirium, he picks her up off the bed like she is his personal fuck doll and bends her over on her hands and knees. The conquering ebony warrior reaches down and slides his huge, swollen head up and down between his trophy’s slick pussy to lube his meaty cock. He then presses his thick, dripping head against her asshole…eager to claim it for himself. Would I intervene? Did she even want me to or was this truly her deepest, darkest fantasy? Stay tuned.

Suggested Reading

  • Sensual Shadows – Index, brief description, and links to my loving, erotic journey with Sienna (including cuckolding)
  • Cuckold Psychology: The Essentials – Links and brief description to essays exploring the exploring the erotic layers often found in cuckold play

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