September 27, 2016
This is perhaps one of the easiest interviews I’ve ever done because Lola Long is a local trans girl I have a lot in common with and also because she’s so easy to communicate with. She has her own hot website tslolalong.com. We’re going to jump right into our conversation and I hope you’ll enjoy it:
Caramel: I’ve been living in Florida for 14 years now. How long have you been living in the Sunshine State and do you still like it here?
Lola: I’ve lived in Florida all my life. As the eldest sister, I feel almost bound by duty to stay here, but I know for a fact I will have to ride the currents to a place with more opportunities. I love my city though.
Caramel: I understand the family obligation. I moved here to live near my mother and that’s why I’m still here. But I live further north in the rural area of this enormous state and you live in the more metropolitan Orlando. Is that where you hang out mostly or do you travel to other parts of the state also?
Lola: I’m starting to travel to Ft. Lauderdale a lot more. I would love to visit several northern cities next year.
Caramel: I always have more fun further south. Congratulations on your new website tslolalong.com! What made you decide to launch a site on your own?
Lola: Thanks, babe. When I first started, I studied a lot of girls that I admire and it seemed like a membership site was apart of creating a stable platform. So I always knew I would eventually get a membership site. I really want to build it into something popular.
Caramel: Are you interested in doing major studio work as well? If so, are there any particular producers/photographers you’d like to work with in the future?
Lola: Yes, 1000 times yes haha. I’m looking for the chance to work with a big studio. I really think that’s going to happen around next year. I don’t have any particular photographers in mind, but I would like to film with Kink.com. Maybe become a Grooby Girl.
Caramel: I would have suggested sending photos to those particular studios/networks myself. How’s your webcam work going? Which website works best for you and was it tough deciding on which platform to go with?
Lola: I haven’t been camming as much as I used to, but I do plan to offer private shows for members soon. So if your a member at tslolalong.com, you can look forward to that. I’m already collecting a lot of cute outfits.
Caramel: There’s a funny story behind the way we first started talking. I had a friend who modeled for a major adult trans website who seemed to have all the potential to go straight to the top of the industry. But she had some personal problems and needed more money to move out of her home quickly. She decided to escort for a living instead of going the porn route, but with no experience, I asked you to help point her in the right direction. You were a huge help to her. How long have you been escorting now?
Lola: Yeah, I always like to help another girl out. I feel like we can be so standoffish towards each other at times. TS woman need to stand together, especially sex workers because it can be dangerous. I’ve only been escorting for coming up on a year and a half. It’s been one long lesson. I’ve grown a lot as a woman and a person in general.
Caramel: Escorting is something I’ve always been apprehensive about, especially in Florida, so I just stick with being a lifestyle Domme. Call me a chicken, but isn’t it dangerous here in terms of law enforcement for a black trans woman? Our common friend who became an escort and she warned me not to and she’s white. She said I’d be treated much differently than she is if I got myself arrested. Have you ever had any run-ins with the police?
Lola: Yeah, I would say the legal grey zone that escorting tends to fall in it can be hit or miss at times. I’ve found that law enforcement tends to be on the watch for street walkers and sex traffickers more than escorts. Let’s hope I continue to be right about that. I’ve never had a run-in with law enforcement. I would say as a trans women of color (in general) the best thing you could do is to not run around in circles that draw a lot of attention. Screen! Screen your clients like your life depends on it….. Because it does.
Caramel: Were you nervous at all in the beginning?
Lola: I was very nervous. Most of my sexual experience comes from escorting. So it was completely new ground for me. However it seems I’m a natural.
Caramel: So you’re a beautiful escort with an enormous cock, so the answer to my next question might seem obvious, especially when one sees your Twitter feed @TS_LovelyLola and on tslovelylola.tumblr.com. But I’m going to ask anyway. What do you services specialize in for your clients?
Lola: Now you’re making me blush. I would say most clients love my cock ,so that’s what a lot of them want. I think I can fuck with the best of them and I cum tons (as of now at least). However, most of my clients see me a second time, sometimes in one day. It’s because I’m just a good time and a good person overall. I like to provide 360 degrees of service haha. Okay no more shameless plugs but really, I don’t lie about what I can do, or how I look and I think that says a lot in this line of work.
Caramel: You can be as shameless as you want here. So what happens in a normal session with a client?
Lola: You name it. I have my boundaries on what I’m willing to do (simply because it’s healthy to have boundaries) but, besides that I just make their fantasies come to life.
Caramel: How long does a session usually last?
Lola: Most of my sessions are from 30 minutes to an hour. I don’t really like short sessions unless they’re worth it.
Caramel: How many sessions do you do a week?
Lola: That depends on the city really. I tend to travel so I’m usually only in town for a certain amount of time and I can get a bit popular at times.
Caramel: No doubt. Do you ever feel persecuted for what you do?
Lola: I do at times. I do sometimes fear that my work as an adult performer and sex worker has cast a shadow I may never be able to step out of. But then I’m like fuck it. It’s cool in the shade. Let those “morally” upright bitches bake Haha. I once read a Reddit AMA featuring an escort and she said something along the lines of “I feel like I can do anything I put my mind to…I’m doing this right now.”
Caramel: Do you get close to your clients?
Lola: Not necessarily. I do have some clients who would probably propose to me if they weren’t scared. I’m only half kidding. As I mentioned, I have a lot of return clients who I’ve seen several times and we kinda build a rapport. I wouldn’t say as friends, at least not most of them, but kinda like a guy and his waitress.
Caramel: Going back to your beginnings, when did you first begin to realize that you were trans?
Lola: For me it took a while. The first stage was learning the word and the second stage was saying it out loud. I always knew I was different and growing up in a hyper masculine black community all of the things your ordinary trans youth would do where off limits. It wasn’t until just after my 18 birthday, I found a video of this guy dressing up like Lana del Rey. It blew my mind and I wanted to try it. That scared me a lot, but once I dressed up the first time, I started to cry because I realized this was what I was missing. Why I wasn’t happy. I look like my mom, so when I was little, people used to always ask me if I was a girl. However my uncle quickly trained me to respond negatively to such words.
Caramel: When did you have your first sex experience?
Lola: This may have funny, but I like to think I have several first times. My first would be when I was a kid. It was with the teenage son of my mom’s friend, but that was just kissing. My first time getting pussy giggidy was when I was 15. My first official time with a guy was soon after I came out. It was horrible.
Caramel: How would you describe your sexual preference?
Lola: I think the easy mode answer would be bisexual. However, I can display some pansexual qualities at times.
Caramel: What attracts you in others including men, cis females and other trans women?
Lola: I like people with a sense of integrity. I understand everyone has their price, but at least put of a fight dammit. Let’s see…. An open mind is a sexy mind. My ideal would be taller than me for men. I have no strong preference toward penis size, but some are more fun than others. When it comes to cis and trans women, I like them all different shapes and sizes. I think everyone has an aesthetic that works for them and brings to best out. I don’t care about color like at all.
Caramel: What obstacles did you face with friends and family?
Lola: I was really lucky my mom is young and I’m the oldest, so we are really tight. I haven’t seen much of my extended family, but I’m sure I’ll slay a family reunion in the next few years. In terms of friends, I don’t have many. So the ones that I do have were cool with it.
Caramel: Does everyone in your life know that you’re a sex worker and are they okay with it?
Lola: Not everyone. My mom knows and she’s cool with it as long I stay safe. When it comes to stuff like this, my mom knows I’m different, but I have a really good head and heart. So she just prays and let me do me.
Caramel: What sort of music do you listen to mostly?
Lola: I listen to a lot of different music. I mostly like House, variations of Dubstep, and Rap. I love Pop music for a long trip.
Caramel: Do you have any favorite books and movies?
Lola: One of my favorite books “Redefining Realness: My Path to Womanhood, Identity, Love & So Much More” by Janet Mock. That was the first book to ever make me cry. I’m more of a comic book type of girl though. (shame what Marvel is doing to X-Men). I don’t have an outright favorite movie, but I do like mostly action, comedy, and campy horror. I don’t like movies that make me cry. I have my own issues lol.
Caramel: Haha, sometimes I’m like that with Horror. Real life can be scary enough. Janet Mock makes me cry, too. In a good way. Describe yourself in five words.
Lola: Real, Funny, Focused, Nurturing, Goofball.
I agree with the last four, but I see nothing goofy about Lola Long. You can follow her on Twitter @TS_LovelyLola and on tslovelylola.tumblr.com with more previews, and I strongly urge you to join tslolalong.com! Thank you for reading our interview. 🙂