Once a biker, always a biker. Though these days, I prefer a little speed to Harleys and MC’s 😜3yr ⋅ Skyler1090 ⋅ r/lgbt
One year sine the pride parade last year! The wig is gone, boobs are here, and I’m getting my feet wet in modeling next week. It’s been the best year of my life!4yr ⋅ Skyler1090 ⋅ r/lgbt
Had jury duty the other day. One of the girls working at the courthouse asked if I was related to *deadname*. I’d say things are going well!4yr ⋅ Skyler1090 ⋅ r/lgbt
Once a biker, always a biker. Though I ditched the Harleys for something a little faster 😜3yr ⋅ Skyler1090 ⋅ r/transtimelines
Night out two years ago vs a night out last night. Safe to say I’m happier, more confident and have a lot more fun these days :)4yr ⋅ Skyler1090 ⋅ r/lgbt
13 years later... finally living happy and confident instead of needing the photographer to make me smile 💕3yr ⋅ Skyler1090 ⋅ r/lgbt
I told myself I was done with throwbacks but Facebook reminded me what I looked like exactly 2 years ago. Some things change. My love of leather didn’t apparently. Happy Thanksgiving all! 6 months HRT4yr ⋅ Skyler1090 ⋅ r/lgbt
One year later, I’m finally starting to see the body I want. Too bad I can’t figure out how to uncross my eyes. One year on HRT!4yr ⋅ Skyler1090 ⋅ r/lgbt
While I’ve been trying to get away from these timeline posts, I know it gave me hope seeing them when I was first coming out. If the cranky bearded wonder can do it, so can you. 🖤💜🖤4yr ⋅ Skyler1090 ⋅ r/transtimelines
Would I have guessed 3 years ago I’d be modeling? No effing way. I kinda wanna slap that guy for his poor fashion choices.3yr ⋅ Skyler1090 ⋅ r/lgbt
Since high school, I’ve wanted to enter the world of modeling. Now at almost 30 years old, I finally have a shoot scheduled for next Friday. Cannot freaking wait! 😍4yr ⋅ Skyler1090 ⋅ r/transpositive
Happy Memorial Day weekend! Coming up on one year of HRT and feeling super confident in a swimsuit finally. Can’t go to the beach but I can catch a tan from my balcony :) 🌞4yr ⋅ Skyler1090 ⋅ r/lgbt
Feel like I’m slowly reaching the point where I can no longer pull off boy mode at work. Full time date is set, just waiting to schedule training for my coworkers so they understand the ins and outs of having a trans coworker. Also, would you believe I’m almost 29?? Ugh last year of my 20s 😫4yr ⋅ Skyler1090 ⋅ r/lgbt
Coming up on a year on HRT in a couple weeks. So glad to have ditched the wig and heavy makeup.4yr ⋅ Skyler1090 ⋅ r/transtimelines
One year between pics. 11 months on HRT now. Truly living my best life now ————>4yr ⋅ Skyler1090 ⋅ r/lgbt
One year in on HRT! Just bought my “new to me” bike. Definitely fits my personality (29 she/her 53 weeks HRT)4yr ⋅ Skyler1090 ⋅ r/transpositive
Crossed the 4 month checkpoint on HRT! Honestly I’ve lost a lot of relationships over the last week or so but I love the relationships I’ve gained and I am so happy to look in the mirror and finally see “her” even with little to no makeup for a change!4yr ⋅ Skyler1090 ⋅ r/lgbt
Just about 18 months separate these pictures. Left was November of 17 on my way to a friends wedding (denial beard and all). Right was June 30 this year at Pride. 1 month HRT on the right. Finally feeling more confident with everything I do 😊5yr ⋅ Skyler1090 ⋅ r/transtimelines
At my 3 week point on HRT, I have to say, im so much clearer. My family still thinks I’m just taking anti depressants. I guess in a way they are. Haven’t been depressed or had an anxiety attack in about a week and a half now and it feels amazing. Oh and elevator selfie cause denim is cute AF5yr ⋅ Skyler1090 ⋅ r/transpositive
Off to a job interview. 29 ~5months HRT and a couple laser sessions in. How am I doing?4yr ⋅ Skyler1090 ⋅ r/transpassing
Today’s Transformation Tuesday is brought to you by the color red. Same flannel, 22 months apart 4 months on HRT. Got the call today that my levels have reached and stabilized at cis range so I’m pretty pumped :) Happy Tuesday!4yr ⋅ Skyler1090 ⋅ r/transtimelines
Funny how I feared coming out at work. I worried what people would think and after hearing horror stories, feared loosing respect or my career. In reality, since coming out, I’ve been promoted and my opinion is so well respected that I’m now an interviewer for new applicants! So grateful!4yr ⋅ Skyler1090 ⋅ r/transpositive
It’s been exactly one year since I started growing my hair out. On HRT for 6 months now and couldn’t be happier with the doors I’ve opened in my life. Since coming out, my confidence has blossomed and my career has taken off. So happy to live authentically ❤️4yr ⋅ Skyler1090 ⋅ r/lgbt
So I came out to my parents earlier this week. It sucked. They insist I’ll never be a real girl and they will never treat me as such. I’ll always be their son to them. But you know, going out for the first time without a wig and I realized, I don’t give a F**k I what anyone thinks. I am a REAL girl5yr ⋅ Skyler1090 ⋅ r/transpositive
Coming up on 6 months HRT next week. Estrogen is a miracle drug 😊 exactly 6 months between pics4yr ⋅ Skyler1090 ⋅ r/transtimelines
Coming up on that 4 month point! Also coming up on that birthday point too.. ugh 29 is sneaking in under a month!4yr ⋅ Skyler1090 ⋅ r/transpositive
Well, it’s been a wild 21 months.. coming up on my 3 month check up this week. So thankful to finally be living authenticity. 28yo 14weeks HRT. Pic 1-November 20175yr ⋅ Skyler1090 ⋅ r/transpositive
After a little over a year into transition, I think I’ve got a good handle on hair and makeup. 3 days till my first professional headshots!4yr ⋅ Skyler1090 ⋅ r/transpositive
After my coming out to my parents last week didn’t go as well as planned, went to an impromptu cocktail party. Out with friends (and people I’ve only met as the old me) and was finally comfortable and not a social hermit. Transitioning is the best decision I’ve ever made5yr ⋅ Skyler1090 ⋅ r/transpositive
In spite of the snow and ice I woke up to and the rough phone call I had with my brother last night, having hair and makeup on point makes it a good day! ❤️4yr ⋅ Skyler1090 ⋅ r/transpositive
Wig, check. Makeup, check. Cute outfit, got it. Amazing fiance (not pictured) assuring me coming out as trans doesn’t change our love for each other? Yeah that happened. Can’t wait to spend forever with her!5yr ⋅ Skyler1090 ⋅ r/transpositive
Two years ago, had you told me this would be my life, I would have laughed. This was something only achieved in my dreams. Still can’t believe Ive come this far so quick! 💕 29 5.5mo HRT4yr ⋅ Skyler1090 ⋅ r/transtimelines
Spent the day at the Harley Museum with my fiance. The moment she says “I know your a woman and I love you regardless”. It was also nice to be called by proper pronouns and not judged all day 😁5yr ⋅ Skyler1090 ⋅ r/transpositive
I’ve been letting my hair grow out for exactly a year today. It was shaved on sides and back with an inch and a half on top. Had a friend shape it and throw in some highlights today so it grows a little mire even over the next few months. Absolutely elated about how this turned out!4yr ⋅ Skyler1090 ⋅ r/transpositive
Positivity is when your friend calls you aside at a get together just to tell you “Your face looks positively feminine. Oh and I’m stealing that dress.” 4.5 months on HRT and can’t wait to see how far I’ll come in a year :)4yr ⋅ Skyler1090 ⋅ r/transpositive
So how do you come out to your parents? Me, 28, with wife and son. I think my method will be to dump the contents of my mind out on their kitchen table (figuratively) then move to the other side of the country. Sounds good right?5yr ⋅ Skyler1090 ⋅ r/traaaaaaannnnnnnnnns
Trans, lesbian, mother, former USCG Reserve. Keep your head up and smile. You’re all beautiful.5yr ⋅ Skyler1090 ⋅ r/lgbt
Still pre HRT. A lot has changed I. 18 months. Specifically my disdain for pants. @skyler_anne_905yr ⋅ Skyler1090 ⋅ r/transtimelines
Out to an impromptu cocktail party at my best friends house last night. I could have themed my outfit to “Prohibition era” a little better but oh well. (28 2.5 months HRT)5yr ⋅ Skyler1090 ⋅ r/MTFSelfieTrain
Pre HRT still nervous about passing. Thought a semi confident smile would help. Opinions?5yr ⋅ Skyler1090 ⋅ r/transpassing
10,287 days wearing pants in public. Broke that streak today! Winter in the Midwest demands tights still.5yr ⋅ Skyler1090 ⋅ r/transpassing
I’m just starting my journey again. Wanted to start in high school but was too afraid to come out. Came out to my fiance and best friend last week finally and they have both vowed to be by my side through everything. I’m 28, pre HRT. Left was 2.5 years and +50 lbs ago.5yr ⋅ Skyler1090 ⋅ r/transtimelines
That was seriously a half hour debate about how he refuses to accept transgender individuals as normal. Cannot wait to tell my parents. Definitely think my fiance and son and I will be moving to the other side of the country afterwords. @skyler_anne_905yr ⋅ Skyler1090 ⋅ r/transpositive
Feel like I’m passing better now but still unsure of myself a lot of the time. CC welcome5yr ⋅ Skyler1090 ⋅ r/transpassing
