In Introducing the Cuckold Fantasy to Sienna, I was early in my relationship with Sienna and shared a few of my fantasies with her. My big revelation was the desire to watch her being fucked by another man. Sharing this with the woman I was falling in love with was a big step. However, I did hold back on one little fantasy. Even now, sharing this with you, it feels a bit embarrassing to reveal. It excited me to think imagine Sienna teasing me about have a little cock. This is a form of erotic humiliation which some men (myself included) find extremely exciting.
🔍 I explore the psychology erotic humiliation in Erotic Humiliation – Exploring the Layers.
When I think about Sienna with another man, I imagine a man with a bigger cock and knows how to use it. I want her to experience physical pleasure like she never imagined possible. This would be a gift of pleasure I provide for my girl…even if it comes from another man’s cock. She will be able to experience this guilt-free pleasure within the emotional safety and commitment of our relationship. Her expressed desire for another man’s larger cock and any subsequent teasing about my smaller size would be off the charts hot for me.
Sharing this desire will be a big step. While I do enjoy this kink, there are challenges associated with it. On one hand, I aspire to be the most amazing lover Sienna has ever experienced – heart, mind, body, and soul. On the other hand, my kink is driven by being “less than” and my lover’s desire for “more”. Her desire for a bigger cock plays in mind as the release of her primal desires and sexual liberation.
Is it possible to create a loving space where a woman can break free from social constraints and embrace her wild physical nature while retaining the emotional safety of a loving relationship? Free of emotional angst and what society deems as appropriate behavior, can Sienna accept the experience of another man as a “gift of pleasure” from me – the man that truly loves her? I believe a woman’s desire for “more” exists in the archetypal dreams of many women and is likely already within her. I only need to awaken it, and remove the barriers that are suppressing her sexuality.
There are, of course, sexual benefits for me too. Sienna’s sexual liberation and craving for more would also ignite a competitive wildfire of lust and passion within me that makes me want to fuck the hell out of her…to fuck her like she has never been fucked before. I explore the underlying psychological and biological drivers of male competition in the Sperm Wars post.
Currently, I find myself in a bit of dilemma. Sienna isn’t actually craving “more” because she loves my cock and our sex life is already off-the-charts amazing. Honestly, it is a great “problem” to have, but it doesn’t work well with my sexual kinks or her sexual liberation. She has lived her life within the paradigm of how things are supposed to be. This has led to an endless cycle of disappointments in past relationships, sexual guilt, and the repression of her sexual fantasies. I would love to open her mind and body to a whole new realm of naughty possibilities.
When I first shared my desire her to watch her with another man, she reacted in a very hot manner. Since then, she has become increasingly intrigued by the possibilities and loves the new big black dildo I introduced into our sexual play. Now, it is time to get her mind around the relative size of my cock so she will have a frame of reference for small penis teasing. Women think they know the size of their man’s cock but how many have actually seen their lover’s cock against a ruler? How many would dare make such a request of their man? I think most men would freak out. Sienna is convinced I have a big cock and repeatedly tells me cock is “perfect” for her. She would never ask me to do this.
I decide to help her out. I send her a message and let her know that I have the urge to put my manhood to the measuring tape and take some photos.
Sienna – ICFY!!!
Michael – What is ICFY? I Can’t Feel You?
Sienna – ICFY = I’m crazy for you!!!! Baby!!!!!!! You are making me crazy!!!!! Send them!
I thought Sienna might try to discourage me by saying she doesn’t need to see the measurement, or that it doesn’t matter because she loves my cock. Instead, she is very enthusiastic and wants to see the photos. I know men are more “cock centric” than women, and it strikes me as very naughty that my sweet little girl wants to know the actual size of her man’s cock. As hot as it would be to send her a photo, it’s a big step. After she sees it, there’s no going back. I’m hesitating and doubt is setting in. I stall by sending her other photos of me in various states of undress.
Sienna – That pic of you in the mirror!!!!!! My beautiful hard, sexy, yummy Man!!! Okay, so you teased me with more pics… Hmmmm, are you going to send the others??????? Craving you!
She isn’t deterred by my attempts to distract her with other photos. Sienna is dialed in and wants to see my cock against the ruler. Oh god, my heart is racing! I ask again if she is sure she wants to know?
Yes!!!! Baby! You have me so crazy intrigued! Mmmm, You make MY ❤ race! Michael, your cock fits so tight and perfectly in your girl’s pussy… Mmmm and YOU can touch OUR spot and make me cum so crazy in the most amazing way!!!!
I think Sienna is beginning to feel my genuine angst and offers plenty of encouragement about my size and how I please her. I’m starting to regret even bringing the ruler photo up. I let Sienna know how sexy she is and remind her that this cock is hers. The size may not be what she is expecting, but it is her cock now and does fill OUR spot perfectly.
Of course Love!!!! Mmmmm, you make your girl so wet and yummy! Baby, are you punishing your girl by withholding pictures from her????
She affirms me but still wants the photo. Whew, I’m feeling a ton of erotic tension and so savoring the moment. For a man with fantasies like mine, this is erotic gold. I’m looking at the photo, my fully engorged cock extended along the ruler…the objective truth free of emotional subjectivity. Sienna is relentless…and asks again.
You are so naughty! Mmmm Baby…I’m waiting!!!
I look at the photo one last time. I attach it. My heart is pounding! I hoover just above the send button with my hand shaking and…press send.
I’m flushed and shaking with excitement as I wait for her reply.
Baby, you need to see where five inches is on me!!!!!
Sienna’s nurturing instincts come rushing forth in her reply. She continues to respond in a series of texts that are full of love and point to our incredible sex as evidence that my cock is perfect for her. She has ever made me feel like I have a small cock or in any way lacking in ability to fully and deeply satisfy her. I was hoping for some erotic teasing but do appreciate her kind sentiments.
Sienna – Baby!!!! Do you see where 5″ comes up on my stomach?!!! Mmmm Baby, I love that you have this fantasy but you need to know…your girl is little!
This was actually a very hot reply. I think it was accidental but she is saying that even though I do have a little cock, it works great for us because she has a little pussy. At this point, I’m also feeling bad for putting her in a tough situation. I was just wanting to have some hot mind play but it may be too real for her. I can tell she is uncomfortable about how to respond. I assure her that I know how amazing it feels for us to make love and that I am absolutely crazy about her.
Mmmmm, I love your words and I do love the way you love me! About your size, okay, fair enough. It’s smaller than I imagined, but that’s because you work such magic with it! Just as long as you know I feel so pleasured and fulfilled by your little cock!!! ❤❤❤❤ So, should I feel inadequate since I feel pleasured and fulfilled by a little cock?! ❤❤❤❤ I do like it too though when you get turned on and control fucking me with the BBC toy!!!!
This was a new erotic layer to share with Sienna. I wasn’t sure if she would go with it or not, but I knew she wouldn’t make me feel bad about it. Her comment about feeling inadequate herself because she is satisfied by a smaller cock strikes me as interesting. I have always wondered if a woman takes pride in the size of her man’s cock or if there a level of psychological satisfaction – in addition to pleasure – that comes with being able to handle a larger cock? I would file this question away and come back to it in the future.
🔍 I have two interviews with women from my Cuckold Corner series that explores these very questions: One currently available post discussing these very questions is available here: Cuckold Corner – Amanda on Cock Size and Lilah on Cock Size.
For now, I simply let her know that small penis teasing is a really hot mind fuck for me but I never want her to do anything that makes her uncomfortable.
OMgosh Baby, I love how you are so thoughtful in sharing things with me, helping me understand, and loving me. It is so healthy and good for me. I so want to fulfill your innermost desires and fantasies. I find it all to be such a turn on because it speaks to your confidence and self-assuredness. It says, “Baby, I trust you and I’m putting it all out there…is it okay?” What a gift!!!!!!!!! A DREAM COME TRUE!!!!!!❤️
I took a big step (or little) sharing my deep desires with Sienna. As the old saying goes, progress is sometimes measured in inches.