Interview: Tattooed Trans Bombshell Angelina Please

Interview: Tattooed Trans Bombshell Angelina Please

We have recently had the pleasure of interviewing Tattooed Trans PornStar Angelina Please. Angelina is a 23 year old Transsexual Adult Entertainment Model, currently nominated for two Transgender Erotica Awards including, “Best New Face.” In her short career she has shot with Grooby (and associated websites such as, Bob’s T Girls, GroobyVR, etc.), Evil Angel, Devil’s Film, Transangels, Gender X, and more.

Angelina grew up in Chicago, where she was born in the late nineties, and lived a rough life of constant relocation. When she was in her early teen years, it became obvious to Angelina’s family that her brother and her were different. Her brother (then her sister) was the first to transition when Angelina was around 12 years old. When she was 17, she had a framework to transition as well, finally transitioning halfway between 17 and 18 years old.

Once she turned 18, Angelina started using Chaturbate to fund her move to New York City. Angelina spent lots of time with friends, living in a completely new area with a completely new identity, enjoying herself and sneaking into clubs to party. That all fell apart when she was about to turn 20. At the age of 20 she had started doing full-service sex work. She was really great at it, and while living in New York City hotels and traveling back and forth to L.A. and Chicago, she was able to afford her boobjob and facial feminization surgery before turning 21.

Angelina settled in with her boyfriend (Luke Hudson) who is also a FTM Porn Model in Chicago afterwards in the spring of 2018. At the time, he had just gotten out of a relationship with Domino Presley, who is like an icon of this current era in trans porn. Between him and her, she definitely had an idea of what she wanted to stick her toes into. It wasn’t until Omar Wax of Grooby hit Angelina up in July of 2019 that she was ready to start a career in porn and she is so thankful she did. She quotes, “It has been a blast ever since!”

How long have you been in the Adult Entertainment Industry and when was your first mainstream scene?

I have been in the adult entertainment industry for about 10 months now, I started out with some scenes on Grooby, but my first “mainstream” scene was in ‘Transsexual Girlfriend Experience 9’ for Devil’s Film.

Have you ever attended an award show or convention? If so, which is your favorite and why?

I have not. I was nominated for “Best New Face” and “Best Girl on Girl Scene” (with Chelsea Marie) at the most recent TEA awards, but those were canceled/postponed, so I did not get to attend. Luckily, they will be live-streamed this year, so I might still win! I am most excited about going to the AVNs next year though!

Who was your biggest inspiration when making the decision that you wanted to be in the Adult Entertainment Industry, and if you could please elaborate a bit on how they inspired you?

My  biggest inspiration regarding my entry into the adult entertainment industry was probably my boyfriend, Luke Hudson, who – in my opinion – galvanized the newest generation of trans men in porn and brought them a greater level of visibility. As for other inspirations in the adult industry, I have a few – Chanel Santini, Domino Presley, Aubrey Kate, and Bailey Jay.

Being the tattooed beauty that you are, could you tell your fans and the readers of this, which is your favorite piece, and which one was the most intense?

My favorite piece is probably the demon girl on my left shoulder because she looks like some sort of ancient warrior priestess but was tattooed specifically so when you look at her from the opposite perspective, the demon visage becomes a lot more apparent. It’s an optical illusion. The most intense one was probably my chest piece, I had to do it in three separate sessions, including the original which was covered up on session 2 and 3.

Out of all the scenes you have filmed, what would you consider your best shoot? Which one did you really enjoy filming the most?

My best shoot was probably with Daphne Dare for Joey Silvera’s ‘Trans-Active 3’. We just vibed really well, and it was the first time I got to fuck a cis girl and her first time with a tranny. I think I enjoyed filming that one the best, too.

Outside of Industry work, what are some of the things that you enjoy doing? What kind of hobbies do you have? 

I do a lot of writing (prose & poetry), sometimes I pick up the guitar and play a little but not nearly enough to feel like doing it in front of others (other than my boyfriend). Before all this crazy Coronavirus drama went down, I used to enjoy walks and other forms of exercising – especially swimming. I’m looking to get into painting, too.

So you’ve been in the Adult Entertainment Industry a few years now. Would you have any advice for the fans and for the readers who want to get into this line of work?

Always be grateful for every opportunity you get, and don’t be afraid to ASK for opportunities. 50% of the work I have done was because I was casted, the other 50% was because I asked. And 100% of the work I’ve done has been a reflection of my attitude. I believe in being nice to everyone. That’s how you get asked back – no matter how talented or sexy or cool or trendy you are. Always be nice!

What are you some of your kinks? Let the fans know what really gets you off!

I’m really into being cucked, which makes it really convenient for me to play camera woman when my boyfriend is out shooting trade content with other models. I love watching my partners get fucked. Other fetishes/kinks include, but are not limited to, feet, latex/leather, pee, fucking men while they wear nice lingerie (not to be confused with fucking crossdressers, although there’s a warm spot in my heart for turning out a sissy crossdresser as well), cum-eating/felching, fisting, etc. 

If you could let your fans know a little bit about yourself, what would you tell them?

I’m just a simple midwestern girl with a New York spirit and a West Coast sensibility, who loves fucking and getting fucked equally, and who definitely needs to get more tattoos – STAT!

I’ve seen your work and have been following you for awhile and you push out some really great content. Out of your experience in the Adult Entertainment Industry, could you give the readers a few of the do’s and dont’s in this line of work?

Thanks. Some do’s, like I’ve said:

Be nice.

Be early, or at the very least, be on time.

Always ASK for more opportunities.

Be courteous of your partner’s comfort levels and limits before every scene.

Make friends with the make-up artist and other people on set.

Support each other’s Onlyfans!

Go out of your way to make people feel comfortable.

Some don’ts:

Don’t be fucking late, dude.

Don’t be a brat.

Don’t expect anything, but be grateful for everything. 

If you’re a dude, don’t put your lubey hands in a girl’s hair.

Clean up properly before a shoot.

Do you plan on getting anymore tattoos in the near future? If so, share with us what you are thinking of getting.

I’m getting tons as soon as these tattoo shops open up and the world gets back to normal. I’d like a diagram of an owl skeleton on my leg, ‘FAKE CUNT’ on my knuckles, a king snake going down my arm to connect the future parts of my sleeve, a burning castle by my heart, palm fronds on my shoulders, some Silence of the Lambs reference material, the ransom letter Mary Alice Young received in Desperate Housewives that made her kill herself, a matryoshka on my groin, etc. I have a lot of ideas.

What are some of your goals and aspirations? What do you strive for?

Some surface level goals are probably to be as tatted and surged out as possible and to be financially steady as a sex worker (which I suppose I have been, but I’d like to have even more financial assuredness). As for aspirations, one day I would like to be a CEO of a company and after that, maybe a mother. What do I strive for? A personal sense of peace.

When you made the decision that you wanted to transition, who was your biggest supporter and also who was your biggest influence?

My brother was probably both of those, seeing as he had transitioned before I did. My family overall was a great support system. Aesthetically, in terms of influence, I would have to say Trace Lysette is goals.

What kind of movies do you like and what are some of your favorites?

‘Silence of the Lambs’, ‘The Exorcist’, ‘Parasite’, ‘The Shining’, ‘Hereditary’, ‘The Cook, the Thief, His Wife & Her Lover’, ‘The Devil’s Advocate’, ‘Fatal Attraction’, ‘Taxi Driver’… I have a lot, but the most common theme they share is they are all horror or horror-tinged.

Drop your links and let the readers know where we can find your work.

To see more tattooed hotties, make sure to follow us on TwitterInstagramYouTube, and Facebook. Also, don’t forget about our annual celebration of these amazing inked performers in the adult industry at the Inked Awards. For more info please visit


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Transgender Adult Performer. Grooby Model, BadGirlMafia Model, Webcam Model, InkedAwards 2019 Best Ink Nominee. . Content Creator. Solo/Self Producer.

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