I became friends online with Kelli Smith on X (formerly Twitter) a wonderful person in the sissy community. We started chatting a bit and thought it would be refreshing for the readers to have an honest interview with someone who has like her.
Annabelle: I have been following you Kelli for a while on twitter, you are one of the first sissy accounts on the site that I found to be consistent. You also share a lot of yourself online and make no excuses for who you are. You are the real deal. When did you find out about crossdressing? When did you start dressing?
Kelli: Thank you for the kind words and I appreciate you following me too.
I’m glad that you mentioned how I share a lot about myself online. In the early years of my account I just posted sort of randomly about nothing in particular. But several years ago I made a concerted effort to open up about myself as much as I could. To be honest with not only others but with myself too. My motivation was two fold:
By being honest with myself I could use my account as a sort of a therapy. A place where I could confront my emotions and feelings. In this lifestyle when you have no one to talk to or share your emotions and feelings with, you can feel alone and a sense of self loathing can take over.
It was and still is very therapeutic for me to say the things I say and post the things I post. It’s helped me immensely to come to a place of acceptance in my life. I now know who I am. That doesn’t mean I don’t have doubts and fears, because I sure do but acceptance has allowed me to manage my emotions rather than run from them.
My other motivation for the way I manage my account was hoping I could connect with and help others. To be a voice for those that felt alone. To let them know that they weren’t alone and that there were others out there going through the same things as them. It means so much to me to hear from someone who I’ve genuinely touched. That means the most to me.
As far as where did this lifestyle first enter my life? When did I first start dressing? The honest answer is for as long as I can remember. One of my earliest memories was being alone in the bathroom of our house and seeing my mother’s bra and slip hanging in the bathroom.
I don’t know what it was but something compelled me to try them on. Something deep down in my soul. It wasn’t a sexual thing. It was a desire to be the person who I knew I really was on the inside.
Shortly after I had managed to try her things on and while having a sense of peace and comfort wash over me, my mother opened the bathroom door saw me standing in her things. I can still see the look of shock and disappointment on her face. I felt ashamed and I hated myself in that moment.
Of course that left a horrible impression on me and one that indelibly linked dressing to being a bad person. Oh how it hurt to want to be a girl so bad but then simultaneously feeling like a broken failure because of my desires.
Annabelle: Did you know there were more crossdressers out there?
Kelli: This was in the 1970s when I first started and I was so young. There was really no way of knowing. People weren’t honest about these things. Certainly not publicly and certainly not young children. As far as I knew I was completely alone. And broken.
I fought to repress my emotions as hard as I could. I’d succeed for weeks or months at a time but something would always cause me to “relapse.” If I think hard enough I’m sure I could list all of the things that triggered me but in reality it doesn’t really matter.
As I moved from childhood to adolescence and into my teenage years I became terrified that someone would find out about my secret identity. Teenage boys could be so cruel and the way I’d hear my friends and classmates talk about “gays” and “faggots,” I knew I’d be ostracized terribly if anyone found out that I wanted to be a girl.
I worked so hard to repress my feelings and pretend to be a man. To like girls. To want to brag about being a “real man” and score as much as possible with as many girls as possible.
I don’t know if girls sensed I was different or what but most of my life I was too awkward and the women didn’t materialize easily for me or in the same quantity as they did for friends of mine.
Annabelle: How has it affected you? Have you felt conflicted? Have you come out to your family?
Kelli: I’m still coming to grips with this on a daily basis. I certainly understand myself better now then I did then but I’m not at a point where I really know what direction my life is heading.
No one in my daily life knows who I really am or the things that I’ve done. For all of the casual, anonymous sex that I’ve had with men and for as much as I’ve shared online about myself from pictures to videos to my words, no one in my life knows the truth.
How much has the world changed for people like us? Names and labels keep evolving, especially more now than ever. What do you like to call yourself other than Kelli.
One of the things that has helped me more than anything, especially in recent years, is not to get hung up on labels.
I remember at a young age thinking that I must be gay. Why? Because all I knew then was that men were men and acted like men and had sex with women. Anything else meant you were gay.
But even back then the label gay didn’t exactly feel right either to me. Gay seemed to be men who were men who wanted to have sex with men. While having sex with men certainly held an appeal for me I didn’t want to have sex with men as a man. I wanted to have sex with men as a woman.
One of the breakthroughs over the more recent years has been coming to grips with and understanding who I am.
I’m definitely not gay. I am definitely attracted to men or at least a certain type of man. And the sex I’ve had with men has been the best and most fulfilling sex I’ve ever had in my life. But I don’t feel that makes me gay.
Others may think I’m crazy but to me I’m a heterosexual woman. Anything else doesn’t explain the person I am.
If it weren’t for the discovery of so many other people out there, either openly living their lives as they see fit or at a minimum sharing their feelings on line then I’d still feel incredibly alone and isolated like I did in my younger years.
It’s allowed me to view my life not just in a mirror but through a prism. A prism that shows the incredible complexity of human behavior and sexuality.
I used to view sexuality as very black and white. You were either gay or straight. Black or white. But I’m convinced sexuality is many shades of gray.
Now you’d be correct to point out that I’ve referred to myself as a sissy. I don’t know what the official text book definition of sissy is. To me it’s a label I’ve used to describe the lifestyle I live. One of a trans woman who is sexually promiscuous.
I do consider myself to be part of the trans community and I know that’s incredibly controversial to some. And I’m very much aware how hard most openly trans people work to shed the sexual part of their identity so as not to be viewed as a fetish.
I try and manage my account to not lump all trans people into the sissy lifestyle. I work hard to make sure my account steers clear and doesn’t involve or fetishize people who don’t want to be. I have trans friends on Twitter but I never like or post comments to any of their posts for fear others will descend upon them in an unwanted manner.
Annabelle: I'm sorry you have gone through so much hardships on your way to better understand yourself. For men, masculinity is everything and deep down men suffer from a lot of insecurity. The men who you have been with, do they understand that about themselves?
Kelli: Thank you. I try and not dwell on the hardships but look at them as formative steps to get to where I am in life. Which is a place of understanding who I am. Which escaped me for so long.
For so many of the men I’ve been with I don’t get to interact with them much beyond some hastily exchanged messages and if things go really well up to an hour of physical intimacy with them. For many I never see or hear from them again so I can’t answer for most of them.
I think a lot of the men I’ve been with are looking for someone to fill a void of loneliness in their lives. Maybe they’re in between relationships or in many cases, sadly, their partner at home is unwilling to provide them the intimacy they need.
They seek someone like me out to one, feel like a man and two, to experience, even if it’s only briefly, some level of intimacy. For men sex is more than physical intimacy even though at times it only feels physical. There is real emotional intimacy tied into it as well. Men have a hard time expressing their emotions but for them sex is their primary way.
Annabelle: Do they keep their intimate encounters with you also a secret?
Kelli: In general, Yes. I don’t know who they tell. And in general I keep my privacy largely intact so it’s not like anyone can out me. I think for most men they want a similar no strings attached encounter where I’m not betraying their trust either. I always tell men that discretion is a must for me too and I’m not looking to ruin anyone’s life.
Annabelle: When did you started sleeping with other men? and how was that experience?
Kelli: It was about 9 years ago exactly the first time I was with a man. Truthfully my first time with a man was awkward. It was all largely pretty innocent as physical encounters go. Nothing more than some touching and petting and the like. But I was so nervous and so was he. He was a very nice and sweet man though and I felt comfortable at least. When he left though I was an emotional wreck and swore that I’d never do it again. But I do remember it was probably less than a day later where I had the urge to do it again and realized I’d never be able to quit it.
I often tell people who are about to be with a man the first time that it may be more awkward than magical but that’s ok. It’s normal. They’re often surprised to hear me say that. But I remind them that sex between two strangers or even sex between two people that are just getting to know each other can be that way. Men and women who have sex together would admit that. So it isn’t much different for us.
Annabelle: Kelli, you bring up something that has gotten lost in the community of crossdressing or is overlooked, that this is a form a therapy for many of us. By releasing and expressing out how we feel on the inside. It can be a very healthy thing to do. Its not like something that we woke up one morning and "felt" that way. No one put these feelings into us. Its easy from an outsider perspective to see this as a form of a fetish, but its complex as you have shared, it can be many shades of gray. Do you see things changing for the better in acceptance in society?
Kelli: That seems like a really complicated question to answer in today’s world. While I feel like society in general is more open and accepting there is an undeniably more hostile level of un-acceptance as well.
I’d like to believe that we can’t roll back the progress we’ve made. But it certainly seems like there is a very vocal minority that feels empowered to try. I can only hope that those that aren’t against us will still stand with us rather than let the hate win.
A few years ago I was with a much older man and after we were done having sex we were cuddling and chatting. He told me about some of his experiences of being gay while growing up in the 1960s. And it was terrifying. Stories of being arrested. Stories of being disowned by family. It was so sad.
It’s people like him that laid the groundwork for where we are today. Some people have literally paid with their lives. We just can’t go back to how it used to be.
In the end I don’t think we will but I do sense there are some very difficult times ahead.
Annabelle: Thank you Kelli for this interview to visit Kelli on her social media pages, her links are below:
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