Introducing Madison Sky

Madison Sky Talks with Captain Jack

Madison is a sexy porn newbie with a great personality. We had a nice chat and actually did this one over two phone calls! We talked about her life and career and got her story out to the masses. Enjoy!

Photo courtesy of Grand Design Boudoir

Captain Jack: Tell me about Madison Sky.

Madison Sky: I was actually born on the West Coast but I come from a Navy family. My dad was in the Navy for 24 years so I’m kind of a brat. I lived on the East Coast my whole life. I left Washington State when I was one years old and didn’t move back to the West Coast until I was 20. I mainly grew up in Georgia, Virginia and Florida. I went to school in Florida from 12-19. I grew up on the beach in north Florida. Jacksonville, not Miami, very big difference! (laugh) I grew up as a beach bum. My high school was 2 streets over from the ocean. The last two weeks of school when you’re done with testing and you don’t really have to be there, we all just went to the beach. I had a pretty relaxed time growing up.

CJ: You moved around a lot, was it tough making friends all the time.

Madison: Yes, I ever struggle with it now. I’m very much a homebody and I would have a friend and then 6 months later, someone else would move in. A lot of my friends are online. It’s the easiest way to keep up with them. I don’t have very many but I learned how to be happy on my own. I’m happy in my own space and it’s really nice.

CJ: How old are you?

Madison: I’m 24. I just turned 24 in March.

CJ: How long have you been shooting now?

Madison: Not very long. I just signed with Coxx Models in April of this year. I just got started. I’ve been on kind of a transition for myself ever since I moved to California. I used to be the fat kid in high school so I had to form a personality first. When I moved to California, I was a size 14 in pants and I’m currently a size 4 so that should give you a little bit of a reference. I wanted to do porn since I was 18; I wanted to do this forever. It’s always been an outlet that I wanted to get into. Getting in straight out of high school was not an easy transition so when I moved here, I just started doing a lot of hikes; finding some cool areas to explore and it made it so easy to lose all that weight. Now, I go to the gym a couple times a week. I had a couple of personal trainers at one point which helped so much. Once I started getting comfortable with my body and stuff like that and confident, I reached out to a couple of different agencies.

CJ: You have some nice breasts, what size are they?

Madison: Fuck, 32, 34 C.

Photo courtesy of Grand Design Boudoir

CJ: Being a fat kid and now you’re hot, is it weird for you to post nudes online so everyone can see you?

Madison: No, I’ve always been hypersexual. I was just not outwardly hypersexual in person. I used to use online as an outlet when I was younger as well. I’ve always enjoyed taking nudes and being more comfortable naked than clothed. (laughs) When I finally realized that I could do them on Twitter, that was great! That was a turning point! Doing this has built my confidence by far and just feeling more comfortable in my body. I think the hardest part now is seeing people in person. I’m a very sweet person and I’m trying to get past the awkwardness but it’s still a little difficult for me.

CJ: When did you lose your virginity?

Madison: I was a freshman in high school and, fun fact, we were watching Scrubs. I had a little boyfriend who was about a year older than I was. I was about 15 and he had gotten “sick” and he stayed home for lunch. And his apartment was right next to my high school. You know, lunchtime and the next two periods after that, I was a little busy!

CJ: After you got the first one out of the way, did you start exploring your sexuality?

Madison: No, before I turned 18, I had only had sex twice. Afterwards, well, I got kicked out at 18, so I have been on my own since. Having to work and having my own place, then I became more of an adult about it. I started messing around a little bit; I had a couple friends with benefits here and there; I had a lot of boyfriends after I turned 18.

CJ: Do you have a count of how many guys you were with before porn?

Madison: No, I try not to. I used to live by Fort Benning and I definitely made my way through that. (laughs)

CJ: Were you with girls before porn?

Madison: I love girls. I think I’m more attracted to girls physically than I am men but that’s ok. The first time I was with a woman was with my ex-best friend, after a concert.

CJ: Is she an ex because you had sex?

Madison: No, it was because she was very petty.

CJ: After high school, did you go on to college or have any regular jobs?

Madison: I had so many regular jobs. I never went to college. I’ll tell you a couple of my favorite ones. I was a debt collector for a little bit and, honestly, that was one of my favorite jobs. It was really interesting, I only cried twice. I was one of the top recruits and trainees coming out of the training class and I was even nominated for MVP of the floor in my second month of doing it. I was pretty good at it. I tried the nice approach. Too many debt collectors are freakin’ assholes. You get more with honey than vinegar. And I worked with disabled people I was a nanny for 5 years and I have a sibling that has autism so I worked one on one with people with disabilities and autism for a quick minute and that was another one of my favorite jobs.

Photo courtesy of Grand Design Boudoir

CJ: How did you come up with your stage name?

Madison: I was actually talking to a small agency that I was looking at joining. We were talking and I had a nickname when I was younger of ‘Mouse’ so I was going to go with something mousey related. But we were talking about it and started to go by Madi. And Madison Sky is really pretty, and smooth, it rolled off the tongue. I like it, it’s nice.

CJ: So, what was your first scene like? You were sexually experienced but it’s different with all these people around. Were you intimidated? Nervous? Turned on?

Madison: So, my very first shoot was for Net Video Girls and I was very nervous but I had a lot of fun with it. The crew was really good at making me feel comfortable and being very goofy. Everything was obviously professional but they weren’t too serious so it was a lot easier for me to get comfortable on set. It became a lot of fun. The physical aspect of fucking on camera is so fun to me. I love it!

CJ: What’s your favorite position?

Madison: There’s one where I’m on my back, feet up, ankles to Jesus and I have a fondness for my Hitachi so I like using my wand and the guy is in between my knees. And the good old classic doggie style.

CJ: Have you ever been in an inappropriate sexual relationship?

Madison: No, not really. I try to respect people’s boundaries. (laughs) Sometimes things happen but I’ve just never been in that scenario. I’ve never been approached in that manner. I never had the opportunity.

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

Madison: Nah, that doesn’t bother me. Honestly, I don’t like guys my age near as much.

CJ: What’s the oldest guy you’ve been with off-camera?

Madison: That’s a great question. I don’t typically ask age. I’ve never been with a 90-year old but it’s pretty up there!

Photo courtesy of Grand Design Boudoir

CJ: What do you like sexually? What gets Madison wet?

Madison: I like intimacy. Intimacy is a big part of sex for me. It doesn’t have to be serious intimacy, it can just be sweet, soft kisses, touches and when that grows into a heavier petting. When it has a really nice build, that gets me absolutely wet.

CJ: Are you submissive or dominant?

Madison: With guys, I’m definitely a brat sub submissive but with females, I’m a switch. I like being dominant with women but I also like being submissive with women.

CJ: How often do you masturbate?

Madison: (laughs) Pretty often. My whole life. That’s something I figured out when I was way younger. I was masturbating way more often than I was having sex. I probably learned to touch my bean when you learned to jerk yours.

CJ: Favorite method?

Madison: Hitachi. Definitely Hitachi. I have a lower sensitivity so, for me, even most toys don’t work. The only one I’ve had consistent luck with is the Magic Wand because it’s magic.

CJ: You wanted to get into porn since you were 18, I assume you watched porn before you got into the industry?

Madison: Yes. I used to watch a lot of porn.

CJ: What was your favorite genre?

Madison: Don’t come for me for this but I used to watch a lot of creampie gangbangs.

CJ: Did you have any favorite stars?

Madison: I think every woman can recognize the beautiful outfit of Owen Grey. And I used to call him two-tone because he has a two-tone cock but I really liked Bruce Venture.

CJ: When a guy pops, where do you prefer it?

Madison: Honestly, I like being painted. Paint me like one of your French girls. I love it anywhere; chest, back butt, sometimes on the face. I’ve gotten it straight up the nose. That is not fun. And in the eyes is obviously not fun.

CJ: Are you a swallower?

Madison: Maybe. It depends on the taste.

CJ: Will you do creampies on camera?

Madison: I don’t do that in my professional life because I have a partner in my private life. He is comfortable with what I do but that was one of his requests.

Photo courtesy of Grand Design Boudoir

CJ: Are you a size queen? Do you like huge cocks?

Madison: Yes and no. I have dabbled in size queenery and I like to test bounds. I like being filled, I like seeing how big we can get it. But I also like it both ways. I don’t have to be a size queen.

CJ: Are you going to do anal on camera?

Madison: Probably not, at least definitely not anytime soon. I used to wear a plug and it used to be fun. I even wore a tail and everything that I would wear around. But I can’t even put that in comfortably anymore so I have to do some personal things to get myself to the point of doing that on-camera. However, I will trade you off and tell you I’m a squirter.

CJ: When was the first time you squirted?

Madison When I first started flicking the bean. I thought I peed myself and I was very scared. But, I went and explored that and that’s definitely something the Magic Wand brings out a lot.

CJ: Can you do it on command like if you’re in a scene that requires squirting?

Madison: Yes, for me, as long as I’m well hydrated. That’s the key. I’ll put the Hitachi out and pretty much squirt on command, sometimes multiple times.

CJ: What about the opposite, they don’t want you to squirt in a scene, can you hold back?

Madison: Sometimes. If it’s a really heavy orgasm, no. For the most part, I have a couple of different types of orgasms. I have a cream one as well that I’m not squirting with. It’s more of a light squirt.

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

Madison: I don’t know. I’m really excited just to try different things. I don’t even know what to expect fantasy-wise yet. I filmed with Agatha Delicious and that was very interesting and definitely opened my horizons on what to expect or even think of. I id a vore cannibal scene with her which was very interesting to film but very fun. And I did a boxing scene with her so we were topless boxing. That was super fun. I definitely want to try the teacher fantasy and try different things.

CJ: What do you look for in a guy off camera?

Madison: I don’t really have a type. I don’t like really skinny guys. Especially since I was a bigger person, I always had this role for myself where I didn’t like being with someone smaller than me. I like husky boys. I like dad boys. Tall but not ripped. I used to date a lot of strong men.

CJ: How tall are you?

Madison: I’m 5’1”. I’m small.

CJ: What’s your type of girl?

Madison: I like women. Women are pretty and soft. I very much love alt girls. I think that’s always going to have a soft spot in my heart. I was a fellow emo kid so they always call to me. There are a couple of girls online that I am absolutely obsessed with and if I ever get a chance to work with them, it’d be a dream. I like redheads, I like dark, black hair. I like different combinations. I like the pale skin and tattoos; that’s gorgeous to me. I like really dark skinned girls too. They are absolutely stunning to me.

Photo courtesy of Grand Design Boudoir

CJ: You sent me some boudoir photos. Is that one of the good things about doing porn, all the photo sessions and getting glammed up?

Madison: It is! Honestly, it’s really cool because I get random photographers that come out of the blue. It’s good and bad because you have to be able to distinguish the weirdos from the legitimate photographers. I’ve had a couple of instances where a photographer did a couple of shoots for me and everything was good then after the last shoot, he ghosted me and he took all my pictures with him. Things happen. But, overall, I get a lot of opportunities for random photo shoots and cool little set-ups. These particular photos were taken by Grand Design Boudoir (@grand_design_boudoir) at FD Photo Studio (@fdphotostudio)

CJ: Is it tough to hold the pose so that they can get the right picture?

Madison: (laughs) It’s definitely a little acrobatic. You have to be able to hold in certain poses and it builds muscles. (laughs) You have to hold your abdomen, it’s like doing planks sideways holding your degree to the right in a 40 degree angle.

CJ: Is it tougher holding a pose for photos or holding an angle in porn when you’re also getting fucked?

Madison: Honestly, holding a pose in porn is harder when you’re actively moving. An example, I just did a scene with Lethal Hardcore, it was mostly mish but my back was on the end of a couch, like the couch arm. And it was a very squared off couch arm. I had to balance on there the whole time. That was definitely not easy.

CJ: I call porn stars sexual athletes because you have to hold certain positions, open up and make everything look good.

Madison: Exactly, it’s about seeing all the angles. Even in mish, if you’re doing mish at home vs. mish in a scene, you have to open yourself up more as a woman more so that the camera can get a good angle of all the goods; your vagina and everything going in and out and all that. They have to be able to see that.

CJ: Saying all that, is it difficult for you to cum on-camera?

Madison: No. I might be weird but I just have fun with it. I have fun in porn anyways, don’t get me wrong, I have a great time. It’s athletically inclined but I have a great time doing it. I also have a magic wand, that’s my go-to for everything. As long as I have that, it’s guaranteed. And even when I don’t have that, I’ve kind of gotten the hang of it. I know my body more. Porn has helped me for sure learn my body. It’s pretty cool.

CJ: What are you like off-camera? When you have free time, what do you do for fun?

Madison: I go hiking a lot. And I do tide pooling. I like taking a huge light, the black light, and taking it to tide pools because there are a lot of little creatures that glow in the UV light. A lot of people don’t know that. I’m very much of a history nerd, I like learning things so I go into deep dives about various topics and subjects.

CJ: What kind of music do you like?

Madison: I listen to everything. I don’t listen to a lot of modern rap but I listed to a lot of EDM, I listen to dad rock, heavy metal and a lot of rock music. Indie and alternative music as well.

CJ: Do you have any favorite movies?

Madison: I’m always a Disney kid when it comes to movies.

CJ: What’s your favorite TV shows?

Madison: The Midnight Gospel is one of my favorite shows. It’s a play off of a podcast. Duncan Tressel has a podcast, Duncan Tressel’s Family Hour and the producers of the show heard his podcast and wanted to make it into a show. It’s very thought provoking. You should definitely watch it when you’re open minded, we shall say. It goes into various topics, anything from substance abuse to how to deal with grief. It goes about it in very interesting ways.

CJ: What’s your favorite food?

Madison: Pasta. Indian food or Italian food.

CJ: What’s the wildest or kinkiest thing you’ve ever done?

Madison: Let me answer that in about a year. I haven’t done anything wild!

CJ: And how can the fans follow you on social media?

Madison: On Twitter, I’m @MadisonSkyxoxo. Instagram is @Madison_sky_xoxo. And OnlyFans is maddiemous3xx.

Photo courtesy of Grand Design Boudoir

Madison Sky Movies, Photos, Talk

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