Sensual Shadows: Introducing Sienna to Cuckolding

In the afterglow of my first night with Sienna, it feels like our souls are united. Unfortunately, we live a thousand miles apart and our next chance to see one another was a month away. In the interim, we have spent a lot of time talking and getting to know one another on a deeper level. I am falling fast for Sienna. In my eyes she is the most beautiful woman in the world and sexy beyond my wildest dreams. Yet, even the splendor of her sexy, sensual curves pales in comparison to her inner beauty and sensuality. Time after time and in countless ways, she takes my breath away. Her spirit illuminates me.

With our sensual, sexual energy flowing so powerfully and my encouragement, Sienna opened up to me about her deepest, unfulfilled sexual desires (30 Days – Sienna’s Fantasies). Now it is my turn. Time to reveal my cuckold fantasy. How will she react when she learns my #1 sexual fantasy is to watch her being fucked by another man…a more endowed man? It’s a risky revelation and a lot for a woman to take in. It will no doubt be surprising…perhaps even shocking. At worst, it might change the way she looks at me and bring our flowering relationship to a screeching halt. 

There is a lot riding on this conversation, and I want to do everything I can to set us up for a successful reveal.

🔍 Sharing the cuckold fantasy with the woman we care about can feel like daunting revelation, and it should feel this way. Cuckolding is a lot for a woman to take in, and we (cuckolds) need to be thoughtful about how we share this fantasy. In the post, Speaking With Our Lover About Cuckolding (coming soon), I explore female-centered considerations and approaches that should be top of mind when discussing cuckolding.

After considering various approaches, I decide that weaving the fantasy into a sexy story might be best approach. Sienna and I spend almost every lunch on the phone having steamy discussions, sharing erotic stories, and getting each other off. I’ll reveal my fantasy one layer at a time while gauging her reaction. If she reacts negatively at any point, I can pull the plug before sharing everything. 

It is a beautiful sunny day as I slip out of the office and into my car for a little privacy to call to Sienna. She is also in a private place where she can speak freely and touch herself. I love how hot and responsive she is to my stories and voice as she undresses in her car and cums for me on a daily basis…often multiple times. 

We catch up on our day before slipping into some sexy talk. I describe how amazing it feels to touch and hold her close, whispering deeply how beautiful and sexy she is, and speak of the energy swirling around me when I’m in her presence. I’m loving her and ensuring she knows I feel like she is the most amazingly sexy woman in the world. Every single word of it is true and comes from my soul.

I then begin spinning a sexy vignette and introduce a dildo into the scene. I describe its size and make a point of mentioning it is “much larger than my cock”. It is a gift of pleasure from me. She moans with excitement as her voice drops into her more sultry register. I encourage her to accept and savor this gift free from any guilt or shame. I want this for her.

After confirming she is touching herself, I provide more direction. “Close your eyes, baby. Slip two fingers in your pussy.” I can hear her gently moaning. “Good girl. How does this big cock feel?” Sienna is vague about what she is imagining so I press her a little. “Sexy girl, you’re imaging this is another man’s bigger cock, right?”

Sienna is hesitant. “No baby, I’m fantasizing you are fucking me with your strong cock. I love my man’s cock and don’t need another man.”

I love that she feels this way, but it works against my fantasy. I gently guide her deeper into the fantasy by focusing on contrast. “Maybe this is because you are only using two fingers. Slip three fingers in your pussy so you can feel his thicker shaft.”

I can hear her reaction to the extra fullness as she works herself to an orgasm. She whispers sweet, naughty things about how crazy hot she finds the fantasy, how his big, thick cock fills her up…and how much she adores me. She is managing a delicate balance – fantasizing about the physical pleasure of another man while reassuring me how much she cares for me. I’m engulfed in erotic fire knowing, for the first time, Sienna is fantasizing in my presence about another man’s cock. I open up my pants and grip my straining, slick shaft. “Mmmm that’s right baby, tell me why that cock can’t be mine.”

Sienna’s voice is dripping like erotic honey from my phone. “No baby…it can’t be your cock because it is sooo much thicker and longer. Only another man with a bigger cock can stretch your girl’s pussy like this, but I love you for giving me this pleasure.”

My heart is pounding as I pump my cock a few more times to edge my rising orgasm. “Mmmm, that’s right. There’s also another reason that can’t be my cock.”

Sienna is hot and curious, “Baby, tell me why…”

My cock is leaking heavily. “It can’t be my cock because it’s so thick, long,…and black.” I pause.

The silence is soon filled with sounds of Sienna coming hard. “Oh fuuckkkk!!!”

I encourage her, “Keep working your pussy baby, you love the way his big black cock fills you up!”

Sienna cums again, “Ohhhh my god, FUCK!!!”

I can imagine her twitching and trembling while fingering herself through a string of toe-curling orgasms…while thinking about fucking another man. Slowly, Sienna’s breathing begins to settle down. “Mmm baby, you made your girl cum so good!”

I defer some of the credit and suggest that I had a help from our new friend. She pauses for a moment…before innocently asking, “Baby, you want your girl to have…a big black cock?”

I’m surprised she knows that phrase and wonder if this was a secret fantasy she hadn’t shared. Maybe she was worried how I would respond? These questions flash through my thoughts, but I’ll save them for another day.

I answer her question by slowly describing how sexy she would look lost in ecstasy with her hands gripping his thick, muscular ass with her little pussy stretched tight around his huge dark cock as he thrusted deeply between her legs. On the other side of phone she is still rubbing and working her fingers inside her sweet little pussy with soft moans of affirmation. I go on about how much I want to see her cum on his thick, dark cock, how he is aching to fill her pretty little pussy with his creamy seed…and how turned on she is making me.

Now she wants to make me cum and continues the story. “Baby, I want to satisfy your every desire and it makes me sooo, sooo hot thinking about you watching me being stretched wide and filled so deeply by a black man. I will do it…for you.” Sienna’s breathing becomes more pronounced and erratic as she says, “I want it too, baby…I have always fantasized about it.”

I run my hand up and down over my rock-hard cock as her sexy, sweet voice transports me. She will do it – for me. With visions of our first cuckold experience mind-fucking both of us, the universe is burning with erotic energy as we cross the orgasmic threshold together! Our shared orgasmic moans fill the space between us as I blast a seemingly endless supply of thick, creamy white ropes up on my stomach….heavy pulse, after heavy creamy pulse.  

In the stillness of this simmering afternoon, Sienna is playful and laments how she wishes she was with me to lick up and swallow my cum. It seems like a dream. How can a woman embody my every desire on so many levels? Awash in fiery burn of romantic love, I am beginning to think Sienna is perfect for me in every way – the very personification of my immaculate dream.

Michael, I am so drawn in to your fantasies. I love, respect, and honor your fantasies, my Love. I will be your Hestia AND your Aphrodite! ~ Your Sienna

Additional Reading:

• Key explorations around the psychology behind cuckolding – Cuckolding Psychology – The Essentials
• Sensual Shadows – Chronology, links, brief descriptions of my loving, erotic journey with Sienna
• The Dollhouse Studio – My Patreon site which includes exclusive posts, uncensored digital art, and sexy poll questions