In the ever-growing landscape of transgender visibility online, some voices cut through the noise not just with honesty, but with a quiet kind of courage. Jessica Tiffany, a 27-year-old video blogger from Canada, is one of those voices. Known to her followers on YouTube as “cuteypietiffany,” she’s been documenting her transition for nearly two years, sharing vulnerable truths, small victories, and the sometimes messy process of becoming who you truly are. Her vlogs are unfiltered, often funny, and always heartfelt. What started as a spontaneous post on Reddit soon grew into an online chronicle of self-discovery that has touched countless viewers around the world.
In this candid conversation, Jessica opens up about the complexity of gender identity, the tension between kink and authenticity, her journey with hormones, and the emotional rollercoaster of coming out. We talk about everything from Sailor Moon to psychological assessments, Chelsea Manning to self-bondage, passing to Pride, and the moments that made her feel most alive, and most seen. Jessica doesn’t pretend to have all the answers, but she asks the right questions, and that’s what makes her story so deeply relatable. Let’s dive into our chat with a young woman who reminds us that being true to yourself isn’t always easy, but it’s always worth it.
Monika: Today, I have the pleasure of interviewing Jessica Tiffany, a young and inspiring video blogger from Canada who has been documenting her transition on YouTube. Hello Jessica!
Jessica: Hi Monika! Thanks for interviewing me for your site!
Monika: Could you share a bit about yourself and your journey?
Jessica: I’m a 27-year-old transgirl, I started on hormones almost 2 years ago and I’ve been living full-time as a woman for over a year. I’m much happier now than I was before, I love being female.
Jessica: I’m a 27-year-old transgirl, I started on hormones almost 2 years ago and I’ve been living full-time as a woman for over a year. I’m much happier now than I was before, I love being female.
Monika: Many transgender people document their transitions online, but few do it as openly as you. What inspired you to record and share your very first video?
Jessica: I’d watched a few random transgender video blogs before I decided for sure that I was going to transition. I used to frequent /r/transgender and /r/asktransgender on Reddit quite often, and at the time, people were posting videos occasionally to show what they looked and sounded like.
I had been putting serious thought into whether to transition or not for months, and one evening I decided that I was going to go for it and transition. I was waiting for a friend to pick me up that evening, so I decided to record a quick video myself to post to Reddit, to say hi, to say I was planning on starting the transition process, and so I could have a record of myself before I started.
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| At a friend's wedding. |
Monika: That first video sounds like a very spontaneous and personal moment. How did it evolve into a full video blog series?
Jessica: I didn’t intend to start making a series of vlogs, but I got a lot of nice messages from people and a lot of interest, so I decided to keep making videos following my transition.
Monika: Can you share where you are in your transition journey at this moment?
Monika: Are you involved in politics or any lobbying efforts? Do you believe transgender women can make a significant impact in the political landscape, and if so, how?
Jessica: I’m waiting to get my second psychological assessment so that I can be approved to get GRS. It has been taking a very long time to hear back from the psychologist who needs to approve me. During this time I’ve thought about it a lot and sometimes I feel like maybe I would be OK with having a penis the rest of my life and other times I get extremely envious of girls and can’t stop thinking about wanting a vagina. This is sorta similar to what I was going through before I transitioned so I think I should listen to the more intense thoughts and go for the surgery.
Monika: How do you feel about the results of your hormone therapy? Are you satisfied with the changes you've experienced?
Jessica: Yes, I am very satisfied. I seem to pass 100% of the time, even when I’m with other Tgirls who are more visibly trans, people still think I’m a cis girl.
My face has changed, my skin is softer, my boobs are a pretty good size (I actually get a lot of compliments on them when people see them haha), and I just feel more comfortable within myself.
Monika: You've shared some powerful reflections about your early life. Can you take us back to your childhood and talk about how gender first became a source of confusion for you?
Monika: How do you feel about the results of your hormone therapy? Are you satisfied with the changes you've experienced?
Jessica: Yes, I am very satisfied. I seem to pass 100% of the time, even when I’m with other Tgirls who are more visibly trans, people still think I’m a cis girl.
My face has changed, my skin is softer, my boobs are a pretty good size (I actually get a lot of compliments on them when people see them haha), and I just feel more comfortable within myself.
Monika: You've shared some powerful reflections about your early life. Can you take us back to your childhood and talk about how gender first became a source of confusion for you?
Jessica: I talk about my childhood in detail in my 27th vlog. I did not understand my trans feelings when I was a kid, I was confused. I had learned at a young age, like most people, that boys were supposed to be one way and girls were supposed to be another.
I was into Sailor Moon when I was a kid, and I had a friend (also a boy) who liked it too. We pretended we were characters from the show a couple of times, and I absolutely loved pretending to be a girl. He told some of the other boys at school, though, and they started making fun of me. That was sort of the beginning of me hiding any sort of feminine interest and making sure I didn’t do anything feminine. It was very restricting. I started to feel like I had to be someone I wasn’t, and I didn’t realize it was because I should have been a girl, I just felt awkward. Also, I was quite often mistaken for a girl when I was under 14. It was always very embarrassing because I knew I had a boy’s body.
Monika: Do you remember when you first started to consciously question your gender identity?
Monika: Do you remember when you first started to consciously question your gender identity?
Jessica: The first time I questioned my gender was when I was 12 or 13, I think. I had started trying on my sister's clothes a bit around that time.
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| "Speaking with a Girl's Voice" via YouTube. |
Monika: That’s such a vulnerable age for self-discovery. Did any specific moments stand out to you during that period?
Jessica: One day, I noticed a line on myself that looked like stitch marks between the scrotum and the ass. I didn’t know what it was, and I thought that it might be a vagina that was sewn up: “What if I used to be a girl and something was done to me when I was born to make me into a boy?” I knew in my head that the idea seemed unlikely, and I didn’t think my parents would hide something like that from me, but I wasn’t sure. I was afraid to ask my parents because of what their answer might be, and in the back of my head for a few years, I was afraid that it would be true.
Monika: In your early teens, how did your exploration of gender expression intersect with other emerging aspects of your identity?
Jessica: When I was 13-14 and my sex drive started developing I started getting really into self-bondage and I would usually wear a girl’s one-piece swimsuit while I tied myself up. It was from this point on that my desire to dress like a girl merged with kink and became one tangled thing in my mind. I just thought that it was a fetish, or a phase I was going through, or that maybe I did it because I didn’t have a girlfriend and I was curious.
Jessica: When I was 13-14 and my sex drive started developing I started getting really into self-bondage and I would usually wear a girl’s one-piece swimsuit while I tied myself up. It was from this point on that my desire to dress like a girl merged with kink and became one tangled thing in my mind. I just thought that it was a fetish, or a phase I was going through, or that maybe I did it because I didn’t have a girlfriend and I was curious.
Monika: When did you begin to see those feelings as something more than a passing phase?
Jessica: I kept doing it until I went to university when I was 18, and then stopped because I didn’t have enough privacy. I thought I had gotten over it, but the feelings of wanting to tie myself up and dress like a girl started to come back four or five years later. This time, the feelings of wanting to dress like a girl started overpowering the bondage aspect, and then I started dressing like a girl at home and yada yada yada, now I’m living full-time, lol.
Monika: For many transgender women, school, college, or university can be the most challenging period due to discrimination and struggles with acceptance. Did you experience similar difficulties during that time?
Jessica: I wasn’t really discriminated against unless you count the expectations and generalizations that people make about you if you’re a male. During most of my school years my true transgender feelings were so repressed I wasn’t aware of them, I just felt very awkward, it’s like I was learning the rules of “how to act as a person” from watching how everyone else acted instead of just being myself.
People could only get to know me to a certain point and I wouldn’t be able to fully open up with them. I think they’d sense this and it made it hard to have a close relationship. The thing is though, I didn’t know what I wouldn’t open up about, it was so buried. So when people told me to open up, or I thought they wanted me to open up, I felt like I couldn’t because I had nothing in me to share with someone.
Monika: Are there any transgender role models that you follow?
Jessica: I have a lot of transgender friends that I’ve met in real life that gave me the strength to go for it and transition, but I wouldn’t really say I have a specific role model, I just try to be me.
Monika: For many transgender women, school, college, or university can be the most challenging period due to discrimination and struggles with acceptance. Did you experience similar difficulties during that time?
Jessica: I wasn’t really discriminated against unless you count the expectations and generalizations that people make about you if you’re a male. During most of my school years my true transgender feelings were so repressed I wasn’t aware of them, I just felt very awkward, it’s like I was learning the rules of “how to act as a person” from watching how everyone else acted instead of just being myself.
People could only get to know me to a certain point and I wouldn’t be able to fully open up with them. I think they’d sense this and it made it hard to have a close relationship. The thing is though, I didn’t know what I wouldn’t open up about, it was so buried. So when people told me to open up, or I thought they wanted me to open up, I felt like I couldn’t because I had nothing in me to share with someone.
Monika: Are there any transgender role models that you follow?
Jessica: I have a lot of transgender friends that I’ve met in real life that gave me the strength to go for it and transition, but I wouldn’t really say I have a specific role model, I just try to be me.
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| Some of my friends and I at Burn in the Forest. |
Monika: Coming out can be deeply personal and emotionally complex. What was the most emotionally difficult part of that journey for you?
Jessica: The hardest thing about coming out, for me, was worrying about what people would think of me after I told them. I’d built up this male persona that they knew me by, and I was going to shatter it and start acting differently. I spent most of my life hiding this from everyone and feeling shame about liking to wear girls’ clothes. It was sort of an embarrassing feeling. To be honest, when I go back and watch my vlogs about coming out at work, I feel it again, I feel a little embarrassed and an “omg, I can’t believe I did this” kind of feeling.
Monika: How did the people closest to you respond when you finally came out?
Jessica: Most of my coming out experiences were really good, everyone I have told took it really well, and I haven’t lost any friends or family over it. Coming out to my parents was definitely the hardest though. I felt sick for the whole week before I told them, I was insanely nervous. But it all went fine, they were very supportive, and things are great with my parents.
Monika: What is your overall perspective on the current situation of transgender women in American society?
Monika: What is your overall perspective on the current situation of transgender women in American society?
Jessica: I live in Canada but our cultures are pretty similar. I think that the general view of transwomen is getting better but we still have a long way to go. You often see on TV a man wearing a dress or doing something feminine as the butt of a joke, I think that things like this really need to change, but it does seem to be getting better. More and more, we’re seeing trans women portrayed with depth and respect, and that’s a sign of progress. It's important for the next generation to grow up seeing us as just people, not a punchline.
Monika: We're seeing an increasing number of transgender women publicly embrace their identities, and many of them have risen to prominence in various fields, Lana Wachowski in film directing, Jenna Talackova in modeling, Kate Bornstein in academia, Laura Jane Grace in music, and Candis Cayne in acting, to name a few. Do you believe we'll continue to see more transgender women achieve recognition in these fields and beyond?
Monika: We're seeing an increasing number of transgender women publicly embrace their identities, and many of them have risen to prominence in various fields, Lana Wachowski in film directing, Jenna Talackova in modeling, Kate Bornstein in academia, Laura Jane Grace in music, and Candis Cayne in acting, to name a few. Do you believe we'll continue to see more transgender women achieve recognition in these fields and beyond?
Jessica: Yes, definitely! I think there are a lot more trans people out there than people think. We’ll definitely have more famous people transitioning or just being transgender when they become famous. As society becomes more accepting, I believe the spotlight on trans individuals will only continue to grow, and we’ll see more of them in all kinds of professions. It’s exciting to think about how representation will continue to evolve.
Monika: Are you involved in politics or any lobbying efforts? Do you believe transgender women can make a significant impact in the political landscape, and if so, how?
Jessica: I am kind of disillusioned with politics these days, I think that the “democratic” systems of the western countries are totally broken and mainly serve corporate interests now.
I recently made a video about Chelsea Manning to try to raise awareness of the leaks she made that show some of the war crimes that the US has committed and also to show support to Chelsea by asking my audience to write her letters. Did you know that they kept her in solitary confinement without any clothes for 10 months? It’s horrible. I figure that it might not be possible for us to get her out of prison, but we can at least show her that she’s not alone and forgotten by sending her letters.
I think that transgender people can make a difference in politics, we just have to start getting a lot louder about things. Gay and Lesbian people have been very vocal about their right to marriage, we need to be vocal about our right to equal opportunity to work, bathroom rights, etc.
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| "SRS Psychological Assessment" via YouTube. |
Monika: Do you have a passion for fashion? What types of outfits do you typically wear, and are there any specific styles, colors, or trends you gravitate toward?
Jessica: I love having nice clothes, but I’m not a huge fan of shopping. I find that it takes a lot of work for me to find clothes I actually like but I guess it’s worth it when I find something that suits me and is unique. I tend to go for more classic, timeless pieces with a bit of an edgy twist, and I’m always drawn to bold colors and patterns.
Monika: What are your thoughts on transgender beauty pageants?
Jessica: I don’t really know much about them, but they sound fun! I think it’s great that they provide a platform for trans women to celebrate their beauty and confidence in a supportive environment.
Monika: Are you actively engaged in your local LGBT community? If so, in what ways?
Jessica: I go to Pride and to gay clubs occasionally and am fairly open about being bisexual but I don’t do any activism or anything. However, I always try to support my friends and be a safe space for those who need someone to talk to.
Monika: Do you envision getting married and starting a family? Could you share your thoughts on the role of love in your life?
Jessica: I don’t want kids and I’m not sure if I’ll get married, I don’t really see why I need to get the law involved in my relationships haha. Love is very important in my life though, until I was 24 I only had one relationship for 8 months, I was so starved for love…
But in the last few years since I started going out dressed as a girl and being myself, I’ve gone on lots of dates, been in a few relationships, and now I have an amazing partner (who is trans too) who I have so much fun with and love so much. We’re in an open relationship so I have been continuing to date others, I’ve been seeing a cute girl for the last couple of months.
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| Calling the psychologist.. again! |
Monika: What advice would you give to transgender women who fear transitioning early, facing discrimination, and dealing with hatred?
Jessica: If transitioning is what you think you need to do to be comfortable in your own skin, you have to do it. You aren’t truly living if you’re afraid to be yourself because of what other people might think.
Personally, almost all of the fears that I had of what would happen if I came out to people and transitioned never happened. I know this isn’t true for everyone, I’ve been lucky, but I honestly don’t think it will be as bad as you think.
Monika: What are your next steps right now, and where do you see yourself in the next 5 to 7 years?
Jessica: I’m just waiting for my psychological evaluation for getting the surgery! I’m so excited about getting a vagina!! It’s just taking forever for the psychologist to call me back to schedule an appointment, frustrating!!
Monika: Would you say that you are a happy woman now?
Jessica: Oh yes, I’m a very happy woman! I am so much happier now than I was before. I was just thinking about it earlier today actually – I was remembering what I felt like 4 or 5 years ago when my trans feeling all came bubbling to the surface. Before I would go to sleep every night I’d lay in bed and whisper “I’m a girl” over and over, I just wanted it so badly to be true… And now it is true! And it just feels so amazing to finally be myself.
Monika: Jessica, it was a pleasure to interview you. Thanks a lot!
Jessica: Thanks so much for the great thought-provoking questions!!
All the photos: courtesy of Jessica Tiffany.
© 2013 - Monika Kowalska
