31 Days 31 Trans Voices | Day 27: Jamie Riley Fillingim, From Dress Socks to Vaginas

Jamie Riley Fillingim upon first connection appears a somewhat shy person. She doesn’t seem quick to exchange personal details or jump into heavy conversation. You get that after she gets to know you a bit. That Jamie is willing to cherry-pick the profoundly layered complexities of her transition and serve them to us, slice by slice, via spoken word is not only a pleasant surprise; it is a gift.

Jamie, who lives in St. Louis, Missouri, has agreed to share with us work that she completed while participating in a trans-centric writers’ workshop with Joan Lipkin, Artistic Director of That Uppity Theatre Company, then read as part of the St. Lou Fringe Festival 2019. Jamie reprised her presentation for the Metro Trans Umbrella Group’s 2019 Live Telethon.

The words below may resonate with some of you. The words are from Jamie…

I’m a trans woman and I’ve been fully out for 5 years. I started transitioning roughly 4 years ago, but I knew that I wasn’t a boy since the age of 5. I did my best to bury who I truly was for most of my life, but I eventually learned to accept who I truly was at the age of 25. When I came out, my entire family rejected me. And as a result, I’ve been on my own for about two to three years. 

I do plan on writing more short stories about my trans experiences now that we’re all in lockdown. During this time, I’m hoping to expand my skills as an orator; in order to improve my in-person storytelling. I sing from time to time, and I also play rhythm guitar. Every now and then I’ll sing at an open mic night, but I prefer to stay at home and avoid the transphobia that singing all too often brings.

Jamie Riley Rillingim

I’m a board member at the Metro Trans Umbrella Group and I’m the leader of the Strategic Planning Committee. My responsibilities include, creating MTUG’s Strategic Plan, attending board meetings, and volunteering at various events. I also help out MTUG’s Grant Committee from time to time as well. MTUG has been with me throughout the past 4 years and this is my way of giving back.


Screaming, itching, annoying, painful…The men’s dress socks feel coarse and invasive. Like nails on a chalkboard or lemons in my eye. The necktie choking me constantly. Like a boa constricting harder and harder. My life lay in a death grip waiting to be devoured whole. Day in and day out, the male dominated corporate world demands conformity. It demands life. It demands MY life…The dress pants plain and boring. The dress shirts much the same…No character, no beauty, no life…Expressionless…dead… hollow…This is what life as a Wells Fargo Data Conversion ‘specialist’ is like? Why? Why did I sign up for this!? …*Sigh*…For most of my employment, I have felt that something is wrong inside of me; like a piece of a puzzle that just doesn’t seem to fit…Am I losing my MIND!!?? …Never before have I been forded to wear male dress clothes with such frequency. Never before have I been subjected to a dress code that borders on the edge of insanity. This feeling of hollowness, aka Gender Dysphoria, keeps swelling and swelling and swelling!!! …It’s simply gotten to the point that I CANNOT DEAL!! This experience has been one of many that have made me feel trapped, and unable to breathe. Like a xenomorph I want desperately to shed my host’s skin, and violently burst out of the cocoon that is my ‘male’ body. Testosterone poisoning has determined my future thus far. It has determined how I am expected to present myself, how I am expected to move, and how I am expected to speak…As a child, I wished to wear short shorts, dresses and makeup. I wished to transform like Ariel from the little Mermaid or like Timmy Turner from the Fairly Odd Parents… I wished desperately to wake up as the beautiful woman that I felt like inside…But *Sigh*…Wishes don’t’ come true…So, I guess my point is this…I have never understood how male dress clothes work… They’ve always felt like a shell that just didn’t fit right… A foreign form of expression that has constantly left me feeling like nothing but a disappointment… Never tough enough… Never masculine enough… too baggy, too plain… too…BLAAAH! Give me glitter, give me bliss. Give me anything, but death’s kiss. Screw male clothing!! And SCREW CAPITALISM!!!

Girl Dick:

The relationship status with my girl dick is… Well, how shall I say it? … complicated…. Earlier in my transition I struggle to find ways of  “Aghem”… taming the beast; or tucking it if you will. I tried using everything from tube socks to duct tape. Until finally, I settled upon wearing extra tight Spanx. The testosterone coursing through my veins was of no help and constant erections left me grimacing in pain as my girl dick screamed for freedom. But alas, just like beauty, gender affirmation is pain!

Jamie Riley Fillingim performing at the Metro Trans Umbrella Group LIVE Telethon 2019

Anyway, as someone who dissociates with having a penis, I can assuredly say this it is weird as fuck! Like, what do I do with this? Rip it off? Can I just swap body parts with some trans guy in a clean hospital and avoid the dank back ally body shop filled with screaming stray cats pleading with Satan to me them into real girls? *Sigh*…*

I guess it’s not all that bad… I mean, at least I can pull in the chasers pretty well! You know, cause trans women are really just gay men looking for hookups and no meaningful connections whatsoever… *Sigh…* If only they knew the truth. That girl dick isn’t like guy dick. Not one bit. I mean, sure! It’s still a phallus shaped fleshy microphone with a German helmet. But it’s not much similar past that. For one, the skin is sooo incredibly soft… To the point that it practically tears itself most days! And it shrinks. Holy moly does it shrink!! So that thing about me fucking someone with it, yeah. That’s not gonna happen. At least not in my case anyway. …Personally, I just want to forget that it’s there and move on with my life. I mean, don’t get me wrong. Some trans women like have a girl dick. And that’s totally awesome! But for me, I’d rather just have a vagina.

Terry Willits

Trans Speak's Editor-in-Chief is an international mixed media artist, writer, LGBTQ advocate, coffee snob, dog dad, and FTM transgender - but not necessarily in that order, who practices what he posts. A native of Cedar Rapids, Iowa; he now does the writing thing from St. Louis, Missouri. You should check out his work - it's recommended by 4 out of 5 people that recommend stuff.

2 thoughts on “31 Days 31 Trans Voices | Day 27: Jamie Riley Fillingim, From Dress Socks to Vaginas

  • March 27, 2020 at 12:08 pm

    Jaime is such a love! Thanks for sharing her reflections. I long to read more!
    ps Have you shared yours here? or did I just miss it???💞

    • March 27, 2020 at 12:37 pm

      I am glad Jamie shared with us. I am not putting mine on the series. There are so many people out there all over the world that are doing and creating that can be shared so I wanted to spotlight them this month.


Leave a Reply

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