Interview With Jessica Dee

Monday, March 3, 2014 (You can find our follow-up interview in Issue #94 of Transformation Magazine)

It was Jessica’s Twitter profile that led me to the link to Jessica Dee on Tumblr.  I loved her writing and found that she’d been featured on two of my favorite websites.  I asked her a few questions via Twitter and the rest is history.  I hope you’ll enjoy my interview with Jessica Dee of the UK.


Caramel: You have been living the fetish lifestyle for over two years and blogging about it for just as long. Congratulations! What are some of the things that turned out different from the way you first anticipated?

Jessica: Thank you. I think the biggest thing I found out once I really started exploring bdsm was that most Dommes are very friendly, and quite often happy to chat. This sounds a bit stupid, saying this now, but years ago I used to think Dommes were just really mean all the time and constantly looking to dominate guys. I soon found out that was far from the case and have been lucky enough to meet quite a few Dommes that are some of the friendliest people I know within the scene, in fact I think people within the scene are friendlier than out. Also I used to think being part of the ‘fetish lifestyle’ was something different and strange because I wasn’t sure if I ever really would be a part of it, now though it’s just the norm.

Caramel: How did you meet the beautiful professional Dominatrix Governess Ely?



Jessica: I first saw Governess Ely on a femdom website years ago and never thought we would meet in person let alone become friends or that she would become my Mistress. We first made contact through a website called Fetlife were I was in contact with a friend of hers. He suggested I message her which I was more than happy to do and we exchanged a few messages back and forth. I would love to say and the rest was history but not the case, Ely made me work before we met. We ended up chatting on Facebook a little, and then a lot, and then every day, and after about 4 months of me asking, Ely agreed that I could come to visit. I was doing a blog post interview with Ely at this time and we said it would be easier to finish in person. I drove over to hers and spent the day with her and we clicked straight away, that was over a year ago now and she hasn’t been able to get rid of me since!

Caramel: I love Fetlife and your profile there is fantastic. What influenced your decision to blog not only on WordPress, but on Tumblr as well?


Jessica: Well it wasn’t actually my idea to start my blog, and I was quite reluctant in the beginning. At the time there was a Mistress I was friendly with who I used to meet up with most week, mainly to chat and drink lots of tea. She taught me a lot and gave me a lot of advice, some of which I followed…… She asked me to start a diary and write down any thoughts and feeling I was having as I was starting to explore bdsm more. I wasn’t very good at using the book and the Mistress already had a blog of her known on WordPress so she ‘suggested’ I scrap the book and do it in the form of a blog online, mainly so she would keep a better eye on it. I still didn’t post very often and wasn’t really sure what to post about at the start. I soon got into it however, and soon people started reading it and I was getting the odd message saying people enjoyed reading, which encouraged me to continue. Its kind of just grown from there. I own that Mistress quite a lot for that.

Tumblr was very different, I only started this recently. I basically was getting told from friends that every now and then they would see my picture pop up on Tumblr, so after a while I decided I would like to see for myself so I joined up and re-posted anytime I saw myself. To be honest Tumblr is okay, but the jury is still out on if I will keep that going or not.

Caramel: Were you flattered when you saw that fans added captions to some of your photos?

Jessica: Well I wouldn’t go as far as calling them fans but actually to start with I was annoyed. I didn’t like the idea of people using my pictures. Then I thought about it and realized it’s actually a compliment. Now I quite like that someone might see one of my pictures and like it enough to write a caption. I like reading them and seeing what people fantasize about when looking at the pictures, it also makes me smile knowing what actually was happening at the time of the picture compared to what was captioned. It’s always very different.

Caramel: I understand the initial annoyance. The photo thing is very personal. However, I may never understand why people publish their photos online completely unaware that people will have their way with them. I’ve seen some of mine and yours used in ways I could have never imagined. Sometimes it’s weird for me, but mostly it’s flattering. So, how old were you the first time you dressed up as a girl?

Jessica: To be honest I’m not really sure on this. I didn’t start getting fully dressed till quite late. I got my first pair of heels when at university so was about 22 and I got my first wig about the same time. Before that I started with lingerie in my late teens and got the occasional item of clothing and an occasional dress. I don’t think it was pretty though! I guess I was quite a late starter in that sense. I’m still not good at makeup either, I much prefer having a Mistress do it for me, it’s a hard life sometimes.

Caramel: You’ve successfully managed to keep family and certain friends from discovering Jessica. Is there a plan in development of telling them about this part of your life?

Jessica: I still don’t think there is a plan, I have kind of just gone with the flow so far and that seems to be working for now.  I like the fact that the two are very separate. Some of my friends know I’m kinky and some of my family know a little bit, that’s enough for me for now. Who knows what will happen in the future, but at the moment I’m happy with how things are.

Caramel: You’re very young still and I’m curious to see how things develop in the next ten years. You seem to be as in touch with your submissive side as you are with your feminine side, yet you don’t identify with the label of “sissy”. What is the distinction of a submissive tgirl and a sissy?

Jessica: To be honest, I think I’m still trying to fully work out my submissive side and my feminine side, although I know that both of them are strongly linked. Yes I really don’t like the label ‘sissy’ and it’s a strong enough feeling to say something 99% of the time if it’s used to describe me, even if it’s a Domme using it. I think it could mainly be something I have needlessly built up in my head, but for me ‘sissy’ is largely a derogatory thing. It makes me think of guys dressing for humiliation, not caring so much how they look. Sissy also makes me think pink, fluffy, frilly, satin, ideally that’s not me, given the choice I prefer a more feminine look. That’s not me at all, when I dress I want to look good, well as good as possible, I prefer being called a crossdresser to anything else. I think basically what I’m saying is, I dress to look as much as possible like a girl, not like a guy in a dress. For me that is not being sissy but crossdressing, and you can definitely be a submissive crossdresser without being sissy.


Caramel: What is the difference between a crossdresser and a transvestite? There was no Internet when I was learning about adult issues as a teen. Books I found in the library had me believe that a crossdresser was someone who dressed in clothing of the opposite sex because it simply felt more natural. I read that it was the transvestite who sexualized it. Yet I always get different definitions from crossdresser and transvestite friends.

Jessica: I wouldn’t say I dress because it feels more natural, for me it’s more because it feels good and is a lot of fun but yet calling myself a crossdresser has always seemed the best fit for me. The way I see it is a crossdresser, like me, dresses occasionally but spends the majority of the time in male clothes. A transvestite in my mind dresses more, maybe would go out dressed for normal day to day things. I don’t see it as one being sexualised and one not. Also for me it is incredibly rare to dress without any bdsm being involved so that could be slightly different to most. It is difficult to define because as you say, everyone has different definitions and opinions on it, but that’s also a good thing in my opinion.

Caramel: I got the nickname “Mistress Caramel” for a reason *wink* and one of the things I love is spanking. What do you love about it?

Jessica: The short answer everything, I love spanking. I love the whole thing, having my dress pulled up (or trousers pulled down), having my underwear pulled down (or up), the warming up, slowly building up the intensity, the changes of speed and rhythm, the differences in how each implement feels, the closeness and intimacy of an over the knee spanking, the after care and of course the glow I have afterwards both in colour and how I feel.


Caramel: Is it okay if your ass looks like a road map of Chile a few days after a spanking or flogging?

Jessica: I definitely didn’t have to look up the shape of a map of Chile on Google just then…. It’s not only okay if my ass looks like that after a spanking or flogging. I would be disappointed if it didn’t. I love the marks after a spanking/flogging/caning. I’m quite lucky in that respect as I bruise like a peach. haha

Caramel: I really like that you bruise easily and I love the Vintage Cross Dressing website (as well as Lady Annabelle’s sister sites). What was it like and how did you originally get in contact with Lady Anabelle before shooting with her?


Jessica: I got in contact with Lady Annabelle through FetLife again. I commented on her pictures and sent her a message saying how much I liked her pictures and her websites. I remember being very surprised when I got a reply saying thank you, I in turn asked how she decides who appears on her site and she said I would be ideal. I didn’t really think it was going to happen at the stage as I had never done anything like that before, but before long I was there meeting her in the flesh. I was incredibly nervous but the whole day was a lot of fun and Lady Annabelle was great at putting me at ease. We did a few sets of pics and one short video and I really enjoyed myself. I also really liked it because I had an opportunity to meet a well known and experience Domme and ask her a few things and get some advice, I was very inexperienced at this stage and I think it did me a lot of good.


Caramel: I love your work on the fantastic website The English Mansion. Had they seen you on Vintage Cross Dressing when they requested you for their site?




Jessica: Yes, I think I remember them saying they had seen that I had been and done some stuff for Vintage Cross Dressing. I think the first time I went to The English Mansion, I was asked because someone had dropped out and they wanted a tgirl/crossdresser to do some filming. I live quite local so I think it was a lot of right place right time situation. I must confess although I had seen the site before I didn’t realize just how big a site it actually was, I almost passed up the chance to go. It was Ely that made me realize when The English Mansion comes calling you don’t say no! I’m so glad I did go because I would count it was one of the most enjoyable things I have done within the kink world. Mistress Sidonia and everyone that works on that site are amazing, so friendly, happy to chat and happy to give advice. I was then very lucky to go back again a few months later as Ely was doing some filming. I got to dress up on camera with Ely, at The English Mansion. What more could I ask for? I was smiling for days after that and I was so happy with the pics from both visits.

Caramel: You’ve recently experienced Governess Ely using a strapon. I remember the first time a GG (genetic girl) did that with me. I was pretty scared before it actually happened. How did things turn out for you?

Jessica: This wasn’t actually the first time I had played with a strapon with a GG, but this was the first time with Ely. It was something I had wanted to do for a long time with Ely and I loved it. I’m not very experienced with this, but I would love to be able to explore a lot more of this in the future. I had been in chastity for Ely for a long time before this, so I think that intensified the feeling of it all, it’s safe to say I didn’t want to stop.

Caramel: Speaking of chastity, I’ve had submissives wear devices like the CB6000 as a ritual humiliation and denial of orgasm. What I love about is condemning a sub to constant frustration and anticipation until I allow release. Chastity has produced some of the most explosive climaxes I’ve ever seen. What do you love most about being in chastity and can you endure it for long periods of time?

Jessica: Chastity has been an interest of mine ever since I started to find out about bdsm. What I love the most is the control, or more accurately the lack of control, this is actually the main thing I like about bdsm in general and I think it’s the first aspect of bdsm that I discovered that I really liked. Giving control to someone is very liberating and I think handing someone full control of your orgasms can be a very intense experience. I also really like the fact the Domme is really enjoying the fact they have control, that’s a big part for me, I wouldn’t do it with someone unless I know that they really liked it. I also enjoy the tease and denial as well and the way it actually makes me feel more submissive and can push me to do new and exciting (and sometimes a lot filthier 😉 ) things. I’m lucky with Ely because she is a big chastity fan so lots of this in the future I think. This year Ely and I are actually planning to do a few blog posts on my blog on this topic, from both a Domme and sub point of view which I think could be quite interesting.

As with a lot of bdsm though I feel I’m still learning and have a lot still to learn about chastity. In terms of can I endure long periods locked, my long period might be considered short by some, but I would say yes I can endure relatively long periods. It’s amazing what you can do if you have a Mistress that you really want to please. Plus if she has got the keys then not much choice either way haha.

Caramel: I think that with any sort of bondage, the subconscious mind sees a helpless person who can be easily taken advantage of sexually. That’s what I most love about it. I don’t think that it’s born in hardwired programming to rape and that B&D (Bondage and Domination) can be warm and loving if I’m in the mood to make it that way. What do you like about B&D?

Jessica: I one hundred percent agree that bondage and domination can be warm and loving, I think if it was just cold and clinical then I don’t think I would want to do it. Also in my opinion it should be fun, there is nothing wrong with it being fun and less serious at times. In-fact it’s rare that I am that serious, even during a caning more often than not a cheeky comment or two slips out. Then I have to try looking cute and innocent so that I’m forgiven, it never works but I never learn! What I love about bondage again comes down the control. Giving control of my body to someone as they tied me up is one of my favourite feelings. Knowing that when tied or restrained I’m there’s to do with as they like, it’s is hard to beat that, especially if they have some wicked things planned for me. When in bondage I often can go very relaxed, very calm, and very happy, I love that feeling and I get that from rope bondage more than anything. That’s something I really would like to explore a lot more.

Caramel: Have you ever fantasized about being penetrated by a real live human cock?  If so, do you think you’ll ever do it in real life?


Jessica: I have experimented in the past, I will always prefer Mistress’s, but I do have a very open mind 😉

Caramel: On that note, thank you so much for your candid replies and I’m looking forward to an update in the future!

Follow Jessica Dee on Tumblr, on Fetlife, and her Twitter page is @JessicaDee25. I’d also like to thank Jessica for our interview in the 3rd Annual Sexy Swim Issue (#94) of Transformation Magazine!

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