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.

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51 thoughts on “Sensual Shadows: Measuring My Cock for Sienna

  1. I love the way that you are teasing her, keeping her in suspense. I do the same to Tis. The build up makes the end result (seeing the picture) that much more exciting and wanting. I do have to admit that I think you are a good looking guy in that picture. Looking forward to the next installment of the story.

    1. Thanks for the love, brother! 😉 Your comment on building excitement is so true…it is part of the journey and makes the destination even sweeter! One of the things I love about blogging is the whole experience of actually living the moments and then being able to revisit them in stories and share with friends.

    2. The teasing is so hot and sexy…yet brutal at the same time! Thanks B…. Michael keeps me on the edge…Always! 🙂

  2. Sorry I didn’t read past the picture of you and your happy trail. 😉 Yummy!

    Okay, not true. I did read the rest. And laughed, because like B said he does that to me too as I do to him! Love the tease, the build-up, the anticipation…

    BTW, nice shirt. 🙂

    1. Thanks Tis! 🙂 Have to preserve the happy trail even when doing some serious manscaping, ha!

      It was fun going back and reading this. Sienna was so excited to see the photos, but I was really not sure about sending them. I was hoping she might get distracted and forget, lol!

      1. Sweet Love, you always distract me…but you know how focused I am…Never forget! Ha! That would be MY happy trail! xoxoxoxoxo
        Forgive me for not commenting sooner, you know how buried I’ve been! Not the kind of buried I’d like to have going on right now…which is your face, buried in my pussy!!!!!!! Yummy!

  3. Mr. Modigliani

    Hey you two gorgeous people. Thanks for the invite.

    1. Thanks Mr. Modigliani! 🙂 Keeping up with WP can be a full-time job so we’re trying to scale back to a smaller group of friends and spice it up as well…

  4. Michael & Sienna,

    Thank you for inviting my wife I to join your private blog. This is a subject I’m very familiar with and enjoy it as much as you do. The motivation and psychology behind it is fascinating. As you pointed out, sperm competition and sexual competition are at the heart of it, and your wife or girlfriend (if they understand it) can fuel your desire for this and it can add a lot of excitement to a relationship like it has ours. While it’s understandable why a man with a truly small penis would like this, it might be difficult for some to understand why men of average or above average endowment want this, but as my wife astutely pointed out, “Small Penis Teasing” can work with any cock size, because no matter how big you are, there is always someone bigger.” So Michael, whether you’re “statistically” average or not is irrelevant, especially if Sienna’s “fantasy cock” is larger. All she has to do to keep you “wired” is to remind you of this fact frequently and your desire to not only compete, but to compensate for your “shortcomings” will go into overdrive, and will make you wild with desire to satisfy her like nothing else. If she wants any hints on how to do this, have her contact my wife who has perfected the heart of small penis teasing. 🙂


    1. Thanks for coming along, Steve! 🙂 You guys cover this brilliantly in your blog. I appreciate the comment too…hopefully, you’ll expose some additional folks to the thoughtful, loving way you and 1Hotwife explore this subject. As you know, Sienna and I explore your blog often and it never fails to generate stimulating conversation. For anyone that may be reading this comment thread, what I love about Steve’s blog is the positive, teasing, playful and erotic way he and his wife explore this within a deeply loving relationship. There’s no negativity or mean-spiritedness at all…just super-hot fun and all love! Thanks for staying with us on our journey…as we will with yours! 🙂

      1. Michael…I KNOW what a small penis looks like so I say “Drop the towel!” and let ME be the judge…lol…as Steve said thanks for including us on your journey. You and Sienna are truly a beautiful couple and we enjoy you both.

        1. “Drop the towel!” haha, love it! 🙂 Oh, I am going to drop the towel soon but just like the post, I want to savor the build up 😉 Thanks for joining us on our journey, we are honored to have you both with us and so enjoy your journey as well.

    2. It was hard for me to wrap my head around at first, yet when I realized what this did for Michael and the way it sparked such a crazy fantasy for him … it was easy to then wrap my heart around this to please my Love! And then wrap my pussy around his “little” cock!

  5. Such a fascinating kink to me. Keep writing about it. It’s so much fun to watch you two explore, and if you can actually pull it off, the story will be worth good money to read. In the meantime, thanks for the entertainment.
    I can’t quit this comment without congratulating you on your body. I know you work hard at it. You might even make me consider switching sides, but only if there’s an audience to watch. 😉

    1. Thanks JK! I can appreciate that this kink doesn’t connect with everyone but, as you know, that’s why we call it a kink, ha! I had a lot of fun preparing this and always have a lot of angst and excitement around posting on this topic. Hmmmm, there is the contrast theme again…

      Thanks for the photo comment too, truly appreciated. 🙂 As for the switching teams, LOL! I was resting in the bed the other day recovering from the flu and enjoying a Sienfeld marathon…one involved switching teams–hilarious! And, having an audience can make everything hotter 😉

      1. I happily volunteer to be in this audience!!!!!!! Good heavens above — I would be in heaven to have B, ‘Tis, JK, Sofia, Michael and Sienna in the same room with me!!! Now that is one helluva fantasy!! 🙂
        And Michael — NICE body. Truly.

        1. Mmmm, that is quite a gathering you have placed before our fantasy-filled, dreamy eyes…the possibilities!!! 🙂 That would be a fun story to write one day…everyone filling in different desires and fantasies to be quenched as the evening or week unfolds–soooo HOT!

        2. I think audience participation would be mandatory at this kind of event. You are not getting off that easy girl. Just sayin’


        3. Tis, if the thought of being a part of that gathering could make me cum, how on earth could I handle actual participating???? 😉

        4. I don’t think you would have to handle a thing. Leave that up to the Men! or us ladies, if you are good with that. 😉


    2. JK I have to say on the switching sides comment … you’d have to arm wrestle me over that one! LOL
      I may have to start feeding him bon bons and lots of junk food to derail your fascination with his perfect and yummy body!
      xo Sienna

      1. You look super-fit, Sienna. I’m not arm wrestling you. 🙂 I’m sorry, Michael, it looks like it just can’t happen between the two of us. I know, I know, it could have been good, but I’m sure you’ll get over the disappointment. 😉

        1. Hmmmm, disappointment… maybe, now I’ll have to distract him with something more enticing! JK, you’re killing me! LOL

    3. Baby, I LOVE your sense of adventure and your willingness to try something once or (as you said) considerer it.
      It makes my life fllled with such sexyness as you make my fantasies come true.
      AS for having an audience… seems your wish can come true from the eager responses of D and T… Luv it. Count me in (but you knew that already.)

  6. Here I need the LUST button, ’cause Like just doesn’t do it. 😉

    1. Wow, thank you! 🙂 I’ve been hesitant to post when our blog was open to the world, but I felt more comfortable in our sexy little group. Your comment is both encouraging…and hot!

      1. You didn’t feel comfortable sharing YOUR body?? Bloody hell, Michael. What makes you think I’ll ever share mine then!!! (I will say that there is a lingerie clad shot of me on my blog that many of you missed — not ‘Tis, though. She is the only reader that commented on it!!! LOL)

        1. Wait what???? Lingerie shot.

          Damn girl I have to entice ‘Tis with some special kisses to give me that info because I am sure I won’t ever find it… 🙂

        2. and can I just tell you all that Sofia has the softest, fullest lips…..

          Fuck, her kisses are like nothing I’ve ever experienced before. I couldn’t help but spill. Which of course benefits you all, so thank Sofia for this one.

          and Desiree, sorry they’ve all had long enough to try and find it themselves.

          without further ado, the beautiful, the gorgeous, the talented and voluptuous Desiree G.


        3. Lingerie shot????? Where? I missed this…. and I went on to look???? Some help Pleeeeeease 😉

        4. I remember that picture Desiree, Red lingerie, Great Tits!

          Yep, the rest of you guys don’t know what you missed out on. 😉


        5. Now I feel even more deprived — ‘Tis and Sofia have kissed?? Where exactly was I? And ‘Tis — you just had to make it easy for them, huh?? 😉

        6. I couldn’t help myself, it was the most delicious torture. You’ve seen those lips right????


        7. Desiree, not sure how I or any of us missed that one…you must have sent it out early or late and then had spurt of creativity with several posts that moved it down the reader, ha! We won’t miss it this time!!! And, I’m with you on Tis and Sofia…I don’t seem to recall that story!!! If we don’t get details, we’ll need to start a WP riot, lol!

  7. Yep, mmmm, hmmmm! That is most definitely more happy trail in that picture.

    Fuck Me! You are HOT Michael! I mean, I was sold with your ass alone. But now you go and show off those side muscle thingies that head down below and DAMN!

    Whew! I need water now. 🙂

    Thank you for sharing you! xoxo

    Sienna, you are one lucky woman! xoxo

    1. Whew Tis, I think I’m blushing, ha! 🙂 Thank you! 😀 The side muscle thingies–love that! A guy has to stand just right to get them to pop a little…oh the things we men must deal with…

      Your mention of water has me thinking a long hot shower would be a great way to end the day and with a video and camera on the tripod 😉 Hopefully, Sienna will drop in soon and join in on the fun (she’s been slammed lately).

      1. I got a blush out of you! HAHA – I love it!

        You are killing me with your, “a guy has to stand just right to get them to pop a little”. LMAO!

        Sienna, I know the feeling girl! Hope your schedule frees up soon. Apparently your man wants a hot shower, with video rolling. 😉

    2. WOW, I think I missed the party bus on this one… towels dropped, steamy showers, tripods, Lust buttons, switching sides, audience participation… Climbing out of a long week of non-fun! I need a reprieve!!!! In the meantime, love sharing my sweet love (in little bits) with all! Blessed? For certain!

      1. Definitely blessed! You are killing me with your “little bits” comment. haha

  8. LMAO!! U two are INSANE(ly in love)! great stuff! 😀 -oh, and i absolutely appreciate the invite as part of your special friends 🙂 thank you

    1. Haha! Glad you enjoyed it! Thanks for coming along into our more intimate group setting. 😉

  9. errantsatiety

    Deeply sensuous and deliciously exciting, thank you for sharing your sexy stories both of you. Heaven.

    1. Thank you, this was one of the few comments actually about the story, ha! We’ve touched on this theme briefly in other posts but I never really described the mental layers at play for me. Glad you enjoyed and thanks again for the comment. 🙂

      1. errantsatiety

        You are very welcome! And believe me I very much enjoyed the pics 😉 I have been thinking of sharing what I actually look like but am shy. I understand what you say about feeling more confident to share in a deeper way with the blog being private. Food for thought.

        1. Thank you for the compliment! 🙂 As you can tell here, people (especially those you have interacted with) are so very supportive and encouraging when you post photos. I think you will also enjoy the folks in this group and a lot of them will really enjoy your writing! Feel free to add a link to a post on your blog in any comment now or in the future. 🙂

  10. cpmandara

    Well? We’re waiting, too… Fess up, how long is he Sienna? 🙂 PS. feel free to share more pictures 😉

    1. Mmmm, I like your curiosity! Sienna, don’t give up the answer or I will spank your sexy, hot ass! Wait, if you give up the answer, you won’t get spanked…yes, I think this is the better motivator, ha! 🙂 Glad you enjoyed our naughty fun with this. And, there will be more photos… 😉

  11. I had to smile at ‘sperm wars’ because it has only recently come to mind after being with my lover and shortly thereafter my husband. I have always kept a lover but there had been that latex barrier between us – this is the first lover I do not use protection with- not so strangely it is not so complicated to deconstruct but a huge turn on knowing there is competition going on inside my body: I wonder who wins?

    I will most certainly take your recommendation on the other blog and read it forthwith which is a great part of the more intimate back and forth you are creating here.

    1. Whew, that is a hot, naughty comment! 🙂 I need to find and read some of those stories… Feel free to leave a link if you have favorite you’d like to share

  12. Sorry I am late to the party but I am glad I am …. this way I can read everyone’s comments and say Ditto.

    Seriously, you two are just too hot and sexy for words… perfectly made for each other.
    Love that you are lovingly exploring. Good luck, I am sure it will turn out great!

    1. Hi Sofia, better late than never that’s for sure! Glad you enjoyed the post…at this point, I think we have about 15 different stories going on in the comments, lol! 🙂 We’re excited to have you and JK with us…we truly identify with the magic, love, and journey you share with one another! 🙂

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