Kylie Sinner: Still A Virgin!

Captain Jack Interviews Kylie Sinner

Kylie is a beautiful brunette who has made quite an impact in her short time in the industry. You see, she only does anal because she’s still a virgin. Is she saving it for the right person or is there another reason? We get into that and Kylie was very open and insightful. This might be the most interesting interview I’ve ever done and I say that in a good way because I actually learned something. Kylie is a very sweet girl and I hope you get as much out of this interview as I did!

Kylie Sinner

Captain Jack: Tell me about Kylie Sinner.

Kylie Sinner: I grew up in Miami. I was a huge nerd in high school. I was a band geek. I graduated top 10% of my class, classic nerd. Overachiever. I’m still an overachiever but in high school, I was quite socially secluded. I had my small little niche of friends and that was it. They were pretty much all band kids and that was my high school thing. I started college early so my junior and senior year of high school, I went to a community college. Then I moved straight to the University after high school. I like playing piano too. I haven’t played in a while because I don’t have a piano out here in California. I just bought a few new camera lenses so I’m getting back into photography as well. I love to cook. I’ve been a vegetarian for 5 ½ years now. I was vegan for a year. My very first year of vegetarianism, I was a vegan as well. But then I decided I need cheese in my life so I converted to just vegetarian. So I haven’t had any meat except for cock since then. (laughs)

CJ: How old are you?

Kylie: I just turned 20 three days ago (as of this interview).

CJ: How long have you been in the industry?

Kylie: I shot my first scene April 13 of this year. That was my first shoot for Exploited College Girls. I was an amateur before I signed with Motley Models. I did that gig on my own.

CJ: For lack of a better term, I will call what you have as a condition. Can you explain what you have? Are you still technically a virgin?

Kylie:  I’m a virgin, yes. The condition I have, if you go to WebMD, you can type this in, it’s called Vaginismus. It will bring up an article about women who have a muscle contraction problem. Probably about 30% of women have this. It’s either mentally where you have anxiety and your muscles contract where you can’t have any type of penetration or physically, you just have muscle spasms and you have to go to physical therapy. You can work through it that way. Once you find what’s comfortable, you can learn to relax and train the muscles and do it that way. That’s the way I’ve been doing it. I’ve been using a dilator kit and starting with something small, like the size of my pinky. And I’ve worked my way up to about 3 or 4 fingers, average joe size fingers. Nothing too crazy, nothing Manuel Ferrara sized or anything like that. (laughs)

Kylie Sinner

CJ: You said it could be anxiety. Did you see a psychologist first to determine that wasn’t the problem?

Kylie: I went straight to a gynecologist. They asked me if there was any reason I would have anxiety and I couldn’t think of anything. I wasn’t raped or anything so I couldn’t think of a reason why I would have anxiety. They prescribed me a dilator kit, although you can get them online as well. They even sell them at sex shops now! I was at a sex shop looking for a sex toy and I saw a Vaginismus Dilator kit! I did a scene for Girlfriends Films and they told me they were inspired by my story. I got to play the role of the girl who couldn’t have vaginal sex because she was too tight and they had the same dilator kit that I have! I use it almost every day!

CJ: You say you can get four fingers in there now. Well, before you worked on it, if I was with you and I tried to finger you, could I even get a finger inside you?

Kylie: Um, if you did that 5 months ago, you could probably get a pinky finger in there. I couldn’t even use tampons before I started porn. I had to force myself to start using sponges. I’m not on birth control because I don’t need to be on birth control. But I still get regular menstrual cycles and porn doesn’t stop for periods. One day, I was scheduled for a shoot and my period comes and I can’t use a tampon. They told me I had to put a sponge up there so I wasn’t bleeding down my leg. My heart dropped. I was so terrified. I was, ‘Shit! Kylie, you have to figure this out!’ I had to either go home or use the sponge. I guess they could have rescheduled it but I don’t want that reputation. This particular shoot was in San Diego so I had to take a train out there and it was an all day thing. I said to myself, ‘Are you really going to go home and lose all this money because I’m too afraid to put a sponge inside me?’ The day I had to overcome my fears, I think 50% of it was mental. Yeah, it hurts, but I think if I can get over the mental barrier that something is not going to fit inside me, I can work through it. Once that went it, I really started working on it. It’s gotten better. There are still times on set where they’ll want me to finger myself and I’ll get anxious and can’t do it. Sometimes, I’ll get really sensitive. The majority of the time, I’ve learned how to work through it. Hopefully, sometime in the future, I can get some regular boy/girl scenes. I don’t know yet but maybe one day.

CJ: Since you’re working on it and hopefully one day will be able to fit a dick inside you, are you going to lose your virginity on camera?

Kylie: I think about that a lot. I don’t really know what I want to do yet. Part of me wants to go ‘fuck it’, I would have lost it to a regular Joe Schmoe anyways who wouldn’t give two shits about me if I could have so it doesn’t really matter who I give it away too now. I might as well do it on camera and make some money. Then the other part of me is, ‘Gosh, I waited this long, maybe everything happens for a reason and Prince Charming is going to come and I should just wait for him.’ I was playing the cards to see how long I can do anal and I think that will be the determining factor whether or not I will do my first vag scene on camera. If I get really sick of anal or anal is dying down for me a little bit, I’ll have to do it. If I’m pretty consistent with the anal scenes and I decide I don’t want to do it on camera, then that will probably be key. You’re just going to have to stay tuned. That’s the most ambiguous answer I could have given you. (laughs) I’ve also thought of auctioning it to an Arab man who will give me a million dollars for my virginity.

CJ: Just an FYI, my nickname in some circles is Prince Charming, so there’s that.

Kylie: (laughs) So this is destiny!

Kylie Sinner

CJ: So since you’re a virgin, how did it go back in high school when you lost your anal virginity? Did you try it in the pussy first and then say ‘fuck it, take my ass?’

Kylie: I already knew that I wouldn’t be able to have sex especially since I couldn’t even use tampons. At a young age, I already knew I had an issue. And over time, I think it got worse. It’s that psychological anxiety that builds up from multiple tries. I finally gave up. I stopped trying and gave up on myself. I said, ‘Fuck it. I’m never going to have sex, I’m never going to have kids.’ I thought I was going to have to have surgery. So in high school, I was a serial nerd anyways. I never even dated in high school. My parents were that strict that they wouldn’t let me date or hang out with guys or anything. The first guy that I had anal sex with, we already knew anything happened that I could do anal only. I used to just stick toys in my butt because I figured that if guys couldn’t use the vagina hole, they’d have to use the butthole. So, meanwhile, I’m prepping my butt while I was in high school. I didn’t have a boyfriend or anything but I was stretching out my ass JUST IN CASE. And so the first guy I had anal sex with, we already talked about it. We knew prior to doing it, that was how it was going to go down. He didn’t force anything on me. It’s interesting going on dates in college where guys want to come over for a one night stand or they want to take you on a dinner date and have sex afterwards. I can’t do dinner! I’ve been fasting all day. You don’t understand! If you want me to have anal sex, I can’t have dinner! Dates were always interesting for me.

CJ: How many guys were lucky enough to get in your ass before porn?

Kylie: Somewhere around 15 to 20.

CJ: Were you with girls before porn?

Kylie: Nothing too crazy just some makeout stuff and that’s about it. I think I ate pussy once but I was drunk.

CJ: How and why did you decide to get into the adult industry?

Kylie: I used to watch porn like every single day. I used to type in porn and would watch porn and get off. I clicked on this video for Exploited College Girls and I figured I was in college. Now I know how porn works, you don’t have to be a fucking college girl to play a college girl. (laughs) So I thought that I could do this. I could totally get that gig. I typed in their website and at the bottom, it said, ‘Models Wanted’. It was that simple. I sent in a few pictures and they contacted me within 3 or 4 days. They told me to come out to San Diego and I was like, ‘Shit, this is really happening!’

CJ: Does your family know what you do?

Kylie: It’s a really interesting story how my parents found out. The most simple way to put it was when I was in San Diego, I told my sister and my two best friends for safety reasons and told them not to tell my parents. Long story short, after a long day, I was on set for 10 hours and my flight got delayed so I was a little loopy. And I left my phone at the airport in San Diego. I was so tired after such a long day. My mom called my phone and some lady that works in the airport answered it. My mom said, ‘Why are you answering my daughter’s phone? She should be in Florida, not in San Diego.’ My mom thought I was stuck in traffic. Later that night, the guy I shot the porn with, said we could go to the hotel and grab dinner. I checked my laptop before I went to bed because I have a Mac Book and all my messages usually load onto it but there was an issue. So I didn’t see the messages that my mom was sending me. The next morning, I open it up and I had messages from EVERYBODY! My friends told me that my mom was about to file a Missing Persons Report and she was going to come after me. There was about 50 messages from my mom. She was concerned and made me Face Time her to prove that I was ok. It was a mess. That’s how my mom found out. She didn’t talk to me for a while. And once she told my dad, he was a little ‘uh’ about it too. They thought it was going to be a one time thing and they got over it. Then I told them I wanted to do it full time and they were even more pissed off at me. They eventually got over it and now they’re pretty cool about it. My dad actually drove me to a shoot the other day. I call my mom from set all the time!

Kylie Sinner

CJ: Did you take your name from Kylie Jenner?

Kylie: Yes. My agent picked that one out. ‘You should be Kylie Sinner because you look like Kylie Jenner.’

CJ: I think you’re much hotter and much more intelligent, personally.

Kylie: Yeah. (laughs)

CJ: Do you have any favorite scenes?

Kylie: I think the vaginismus one was pretty cool just because it’s my true story. And I got to be fucked with a strap-on by Phoenix Marie.

CJ: A lot of the guys in porn are older. Does it ever bother you to work with older men?

Kylie: Funny story, actually. I like older guys more than younger guys. All the guys that I fucked in college, I never felt super turned on by them. I had a guy that was like 45. He was the first guy that I had anal sex with. When I went to college and fucked guys that were 19 or 20, it was weird for me. They’re not on my level, I feel like. The conversations I like to have, they’re not interesting. I feel more comfortable around older guys. I feel less comfortable around younger guys.

CJ: What do you like sexually? What gets your motor running?

Kylie: I like neck kissing a lot but I think I have chronic wetness. I’m always wet. (laughs) I’m always ready for sex even though my vagina doesn’t work. I like to joke that it overcompensates. It overproduces wetness because it knows it’s small. Pretty much anything gets me horny. I could be watching some girl down the street and see her boobs bouncing and that would get me horny. I could watch some dogs humping and that would probably get me horny. (laughs)

Kylie Sinner

CJ: Do you have anal orgasms?

Kylie: If I rub my clit, yes. But just from anal? I don’t think I’ve ever had an orgasm just from anal unless you include a vibrator in my butt. I put a vibrator in there and played with it and the vibrations went to my vagina.

CJ: You said you watched porn, so what was your favorite genre of porn to watch?

Kylie: I like anal stuff. I don’t know why. I don’t know if it has anything to do with the fact that it’s all that I do but I like watching butts going up and down. (laughs)

CJ: Do you have any fantasies you would like to live out on camera?

Kylie: I know peeing is illegal but if I’m going to do a dom/sub scene, I’d like to be peed on.

CJ: So you’re submissive then?

Kylie: Yeah. Definitely submissive.

CJ: Don’t sound so sad about that!

Kylie: I say it with a little blush on my face. I take pleasure in being chained up.

CJ: If you were with a guy and he does titty slapping, pulls your hair, slaps your face, spits on you… you get into that?

Kylie: Yes. As long as it’s not too extreme to the point where I’m dizzy or something that would leave a scab or a scar. If I’m bleeding, I’m not into that. A slap where it stings a little bit, I find that hot.

Kylie Sinner

CJ: Smooth91 from the ADT forums says that you used to have a blog that was pretty insightful. It’s been discontinued, do you ever think you’ll get it going again?

Kylie: I stopped writing on my blog because I was going to make my own website. The website that I’ve been using has just been a pain in the ass to do that I haven’t started it up yet. I don’t know. I really want to keep writing because I like writing. I’ve also been really busy with jobs on the side and outside of modeling, I’m pretty busy. By the end of the day, I’m popped. I don’t have time to relax and reflect on my day any more. It sucks.

CJ: You told me about some of your hobbies before, what kind of music do you like?

Kylie: Depends on my mood but the majority of the time, I’ll listen to rap or EDM. If I’m feeling extra intelligent or inquisitive, I’ll listen to classical music.

CJ: Do you have any favorite movies?

Kylie: I never watch movies. Everyone that knows me jokes that I never watch movies and I never watch TV. I never know what’s going on because I can’t sit through commercials.

CJ: What’s your favorite thing to cook?

Kylie: If I’m having a sweet tooth, I make really good tiramisu. I fucking love making it. It’s so good. If I’m making regular healthy food, maybe egg plant parmesian or something.

CJ: What does the future hold? Where do you see yourself in 5 years?

Kylie: I really want to be done with school in 5 years. I want to be working in medicine in my own practice.

CJ: What are you going to school for?

Kylie: I want to be a registered dietician.

CJ: And how can the fans get ahold of you?

Kylie: On Twitter, I’m @Kyliethesinner. My Instagram is @kyliesinnerofficial

Kylie Sinner Movies, Photos, Talk

Kylie Sinner


Pornstars, set up an interview with Captain Jack – message him through any of his forum posts (envelope icon,) or hit him up on Twitter.

3 Comments
  1. “It’s that psychological anxiety that builds up from multiple tries. I finally gave up. I stopped trying and gave up on myself. I said, ‘Fuck it. I’m never going to have sex, I’m never going to have kids.’” – – –

    That was really sad to read. Kylie is so fucking brave to seek help and deal with it.

    To have all of this extra anxiety and still do porn is just unthinkable to me. I’d still be crying in my childhood bedroom. Definitely the most awesome new star this year.

  2. So natural and nice ..
    as a medical student I know well what she’s talking about..
    and her story is very nice and inspirational!

  3. Well, she’s just a virgin in her left ear now. Every other hole has been plugged and delightfully so.

Leave a Reply

This site uses Akismet to reduce spam. Learn how your comment data is processed.