Guest Post – Cinnamon, My Sissy Journey of Humiliation

The more I’ve explored my sexuality and the more I’ve opened up about it, it’s made me realise how many unusual different kinks people have, but also the lack of tolerance there is when anything differs from “the norm”. In a bid to try and discover more about the world of sex, sexuality and what it means to different people, I want to get in touch with people who enjoy kinks of all different manner and that you probably wouldn’t read about in a glossy magazine (though it’s a shame they can’t be written about in mainstream media, as I’m sure more people identify with these things than not).

Today, I have Cinnamon from My Sissy Journey of Humiliation who is a Sub Sissy male and would like to be identified as a she/her in this post. Cinnamon has kindly agreed to answer some questions about her sexual identity and kink for me.

What is your kink?

I’m not sure I have just one kink; I seem to be discovering new kinks and fantasies quite frequently, submission is my major one I guess. I have a thing for makeup and lingerie, being controlled by women and feminised. Recently I’ve been led into the world of orgasm control and developed an even stronger fetish for humiliation. Hearing the laughter of women especially when it’s aimed at me just leaves me weak at the knees. I’m not overtly into the pain side of kink, however I do deserve a punishment every now and again,

When did you first get into your kink? How did it start?

I think I first started having fantasies when I was fairly young, but didn’t really explore them for years, for fear of being ridiculed. This may sound weird as humiliation is now one of my fetishes, but I live in a society where not so long ago a young girl was killed because she liked to dress like a goth (Sophie Lancaster Foundation). I’m submissive, not stupid I want to stay safe for one thing.  A couple of relationships I had made me realise how much the humiliation effect could have on me. The laughter I heard the first time they saw my “manhood” only made me more excited. I’ve always known how small I am, although it really hit home at the end of my teens when women started clearly pointing it out whereas around the age where teens start experimenting nothing was really said.

I had an illness a few years ago, and it made me look at things differently. I started to explore some of the fantasies I’d had through phone sex because I thought if I didn’t start to now I’d only end up regretting it later in life. Eventually that led me to where I am today. I have my normal life, but I also explore my other side through being Cinnamon, that probably no one in my normal life knows about. I do think that social media and an increasingly online society have helped. When I started having these fantasies I had no idea there were other people who had similar ones. It has developed over the last few years into what it is now, for instance it was only last year I was given the name Cinnamon.

Did you always know you were a sub sissy, or was it something that developed?

I think I’ve always known I’m a little bit different from the normal stereotype. I can vividly remember lying in bed as a kid dreaming of being captured by girls and being forced into wearing makeup. It was something I never really shared and throughout my teenage years probably tried to forget whilst I tried to “fit in”.

Once I’d finished college and the Internet started taking off, I found a few sites that seemed to cater for some of the feelings I had. I think I got my first pair of panties and lipstick about that time, although sharing a house wasn’t the best environment I did get chance to indulge in private. Since then as I’ve said I have had a couple of illnesses; after the first I started using twitter where I could explore a bit more in a way, anonymously. I was using some phone sex services then but they always seemed to follow a script. After a few months I was chatting to a Mistress who ran a “12 humiliations of Christmas” set of assignments, which I took part in and enjoyed. We often spoke until one day she disappeared.

In my private time from then I’ve always known and tried to explore my kinks.  I had another relapse with my illness, once I got the all clear last I explored more than ever with some of the tasks I’ve had set. I’d say its now developed in that I’m now online as Cinnamon most days, and when I’m at home alone I get to indulge in lingerie and makeup (while doing any tasks I’ve been set).

What does it mean to you being a sub sissy?

To be honest, it just feels like I’m being honest with myself, being able to express myself in my private time really helps with my normal life. I know if this got out I’d probably lose a lot, from friends to family, but I get that that’s the society we live in. I do wish there was more tolerance around. Now I seem to understand myself a bit more and have accepted this, I’m probably happier than I have ever been. Sometimes I don’t feel like a real man, but more and more I feel like I am finally me.

How do you broach the topic with potential partners?

This is possibly the most embarrassing thing to admit, I never get close to anyone to even consider broaching this topic with them. The last 3 or 4 women I’ve been involved with have been brutally honest when they’ve seen me naked (I can’t hide the fact I have a very small penis). Things have often fizzled out fairly quickly after that.

I can get on with women quite well but when things begin to get romantic I start getting nervous. Part of me would love to meet someone I could share this with, don’t get me wrong, but the last thing I would want to do is make someone uncomfortable. It’s hard to even think of how I would describe some of my fantasies to someone. I’d say anyone I’ve told about this has been either a phone sex operator whose profile says they cover these subjects, or an actual Mistress (although I’ve never visited one).

There is one exception, while at university I told a girlfriend I thought I was submissive. She did try to take charge but it didn’t work, she didn’t really have a clue, subsequently we didn’t last long as a couple

Who are the MeanGirls?

Who are the MeanGirls…. Ahhh Miss Erika and Miss Vicki. I’d been following them on twitter for a while last year, knowing that they use Niteflirt as a phone sex platform. They also seemed cool with the things they posted on twitter about books/movies current events etc. We chatted for a bit, then one night last summer I called them and the rest is well history I guess!

What do they mean to you?

They’re brilliant, they took the time to find out what made me tick, and they figured out all these little buttons they can press that leave me so weak for them. They’ve taken me out of my comfort zone with some of the tasks they’ve set for me, especially some of the shopping ones. I also like that they don’t follow a script.

Some of the first few times I called phone sex lines saying I was submissive the operator kept following a line that was of no interest to me (forced-bi/fandom – financial domination). It was a script they followed as though every caller was the same.

The calls with the MeanGirls seem more organic and natural and I really appreciate that. Sometimes I wish they weren’t a whole ocean and a continent away (they’re based in America). Don’t get me wrong they really do humiliate me like crazy on a call, but at the same time they always make me feel lucky, imagining that in a real life scenario would be my dream. Luckily we do chat online a bit too, as I never get to call as often as I would like to, what with the time difference. Since last summer they’re the only ones I’ve called and they assumed control of my orgasms fairly quickly. Thanks to them, my real life and fantasy life have been more blurred than ever and I’m in awe of them daily. They gave me the name of Cinnamon *blushes*.

Does your sub personality go beyond sex? How does your sexual persona interact with your everyday persona?

I’d say lately I’m exploring my sub side; it does affect my normal life. Before my illnesses a lot of the time I was probably trying too hard to fit in as “normal”. I got stressed a lot and probably acted like a dick sometimes.

Since I’ve been properly exploring my other side I’m so much more relaxed. I rarely care what others think and just feel more chilled out. There are a few things I have to take a “dominant” role in and seem to be able to do that ok still thankfully.

In my everyday persona I like to think I have good manners around people, maybe my sub persona influences that although I’d like to think I’ve always been that way. Sometimes I have to bite my tongue at places such as work when there’s a girly chat in the dining room, especially when its something I’ve learnt about. I’ve once joined in a conversation about a (makeup) primer, and faced an inquisition as to how I know about it; it’s part of the constant hiding. I guess its the same if I’m expecting visitors at home, I have to rush around checking all the evidence of Cinnamon is hidden, my submissive persona gives an edge of paranoia on occasion, however knowing I’ve always got that persona to get home too gives me excitement *blushes*.

Have you ever switched? 

Not really. I have been asked on twitter by a supposed sub guy but when I was trying to establish some base rules he wasn’t very respectful and it transpired he was Mistress Chasing, so it never happened. Switching is something I can’t really see at the moment, but who knows what the future will bring…


I’d like to thank Cinnamon for her honesty and asking my questions.

You can find Cinnamon’s blog here.

The Mean Girl’s website is here.

If you’d like to share your story, get in touch!

Leave a comment

  1. April 6, 2016 / 2:03 am

    What a great blog post! We really enjoyed reading what you and Cinnamon both had to say. Thanks for the shout out. 🙂
    And Cinnamon, thanks so much for your kind words. You know we love teasing, laughing at you, and of course, giving all the sissy humiliation phone sex you need.
    Vicki and Erika

Leave a Reply

Your email address will not be published. Required fields are marked *