Jesse May Talks with Captain Jack
Jesse is a newbie in the industry who shot her first scene at 32. And it wasn’t just any scene, it was a DP for DP Diva! It was so good that she’s never going back! Jesse loves the porn industry and wants to make a career of it!
Captain Jack: Tell me about Jesse May.
Jesse May: I love to garden, I have 3-4 gardens at my house, if you count the little ones. I love to cook, I like to spend time outdoors, I like to camp, hike, fish, I’m a mom, I love to read.
CJ: How many kids.
Jesse: Just one.
CJ: How old are you?
Jesse: I’m 32.
CJ: How long have you been shooting now?
Jesse: In 2020, I started camming. My first scene was in 2021. I shot some amateur/indi productions but have only shot the one professional scene.
CJ: Were you a very sexual person before you started sex work?
Jesse: I was but I didn’t realize just how sexual I was until I was able to unleash the beast, so to speak. (laughs) But now that the gates are open, I’m an uncaged animal. There’s no going back. I used to be a behavior therapist, there’s no going back to that life.
CJ: We’ll get into your love of older men in a minute but even back then, before porn, were you into older guys?
Jesse: Yes. (laughs) I haven’t dated someone my age since probably middle school. Everyone I’ve dated has always been older.
CJ: Were you with girls before porn?
Jesse: I always wanted to be but I live in a very small town and finding girls that like girls isn’t the easiest thing to do. But, when I started shooting, the opportunity for collabs came about and I had the opportunity to work with ladies and now I’m hooked. (laughs)
CJ: So, you had the professional job, when did you start camming?
Jesse: I ended up losing my job due to Covid and that whole hot mess that happened. And when I did, I took a little hiatus and tried to get my ducks in a row. One of my friends told me that I have a good personality and I like talking to people that I would be really good at doing this. Eventually, I went full throttle with it.
CJ: How was it the first time you cammed, even though you were in a room by yourself, was it frightening to get naked?
Jesse: Terrified. It was absolutely the most terrifying experience of my whole life. I used to be a theatre kid in college so I like to perform. But performing in front of just a camera and not knowing the reaction of your audience—you don’t know if you’re doing good, you don’t know if you’re doing bad, you don’t know if they like it—it was nerve wracking! It was terrifying!
CJ: Then you had to masturbate. The first time, did you even do that?
Jesse: So, the first time that I cammed, I saw that they had to pay to get certain services, which is the way that it works. So, I was being cocky and saying, ‘If you want this, then I’m going to need this…’ and it just wasn’t getting me the amounts of money that I was asking for. (laughs) I was very naïve. And someone said, ‘You know, in a brothel, we get to examine the goods that we’ll be paying for so you should just get naked and show us.’ And me being naïve, of course I do it. And then afterwards, I got a sick feeling in my stomach. That guy just got a full need circle for free! (laughs) So, long story short, I did not end up masturbating that day but I did end up doing a nude spin. I did end up sitting there nude at some point but my first show was not a masturbating show. I think my second show definitely was. It was still nerve wracking but I think at that point, I think I got over it. I knew what I was there to do and I had really good feedback from the people that were in my room. It was just a bad feeling that first time. It was that horrible anxiety feeling!
CJ: How did you like the guys jerking off to you?
Jesse: Definitely a turn on. That was when all the nervousness went away was when I started realizing that people liked it. At the time, I didn’t have the ideal body that I do now so I was self-conscience a little bit too. I started to have to talk to myself and tell myself, ‘They’re paying for you! It doesn’t matter if you have a little extra whatever it might be.’ (laughs) At some point, I realized, they’re jerking off, they’re having a good time and that got me super excited.
CJ: What was the strangest request you’ve ever received?
Jesse: Oh my goodness, so the strangest thing that I had put up me and it wasn’t just one person, multiple people have an enema fetish! They like it if you do an enema and hold in the water as long as you can and then release. They enjoyed watching the process; they enjoyed the whole thing. That was one of the weirdest things I was asked to do. Also, a lot of people have pee fetishes but you’re not allowed to pee on Chatterbate. But this one time, it was at the beginning of my camming journey, I was camming at my best friend’s house because she had high speed internet and at the time, I didn’t. I would stay at her house occasionally to have these shows. And this guy asked me to be. I thought, ok, but I don’t have a toilet right here, I’m all set up, what do I do? Well, she was sleeping so what do I do? I pee on her floor for $20! Of course I clean it up. But when she wakes up in the morning, I tell her this. She was very angry and she’s a very prudish individual. I handed her the other half of the money! Fair is fair, everything’s good! (laughs)
CJ: She’s a little prude but she still let you cam at her house so there’s that!
Jesse: She did after that too. She’s supportive of my work even if sometimes, she’s a little scary.
CJ: Did you start an OnlyFans after that?
Jesse: I started an OnlyFans sometime during my camming career. Someone said, ‘Hey, even just selling your nudies, people here would enjoy seeing it.’ It was a user on Chaterrbate that told me that, it wasn’t even someone in the industry. I thought it was a good idea and I started putting my work on there. And when I started modeling, it gave me a place to put those photos as well.
CJ: Finally, why did you take the next step into professional porn?
Jesse: I needed something more than guys on a computer screen or girls on a computer screen. I needed more interaction. It wasn’t enough for me. I wanted someone to touch me, I wanted to touch somebody, I wanted to be there with the people. I got to know the people I was interacting with on a regular basis and they become your friends and, at some point, you just want to touch somebody. And working with other individuals, although they don’t necessarily become your friends all the time, it kind of fills that need.
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?
Jesse: Oh my gosh, that was the easy part. The scary part was doing the photo shoot, alone with the photographer. In the pro scene, working with Maestro, you do the photo shoot first and it’s just you and him. He’s a professional. He’s shot girls way bigger than me. And there’s an expectation that your body can move a certain way and it was just so intimidating. I never had someone before that cared how I posed. I think that’s what it was. (laughs) Because every other time, it was ‘Look like a hot girl and I’ll take your picture!’ But this time, he had a certain look he was going for and it makes fabulous work but it was just different than anything I’ve done in my modeling career before that. For good reason, because it’s pro. That was the most intimidating part. Working with the boys and even having him and a behind the scenes guy on set as well. Working with all the people, the lights…that’s the easy part. That’s the part I love. I love modeling as well but it’s a different gig. You don’t get to get out of your head like you do in a scene.
CJ: Who was your first scene for?
Jesse: DP Diva.
CJ: What’s your favorite position?
Jesse: I love doggie because I love it from behind.
CJ: We established you love older men, what has been the biggest age gap you’ve had?
Jesse: 33 years. And that was a 3-year relationship.
CJ: How old were you then?
Jesse: I was 24.
CJ: Where do you find these guys/? Do you go to a bar and if an older guy attracts you, you just go for it?
Jesse: A lot of times, it’s whatever I’m out doing. I try not to pick up bar people these days but we’re all guilty sometimes. (laughs) I just interact with somebody if they tickle my fancy. I have a very flirty and charismatic attitude that a lot of people just enjoy talking to me I feel like and a lot of times, it is the elderly or the old or the older than me.
CJ: What is desirable about older men?
Jesse: I think it’s definitely the maturity that plays a part in it. Having a kiddo, I don’t have time for immature mindsets. Even if it’s a fuck buddy, I still need that person to be on the same page. I have responsibilities, I have things I have to do and I feel being around older men, it’s understood. But even before that, I don’t know what the draw was. They actually care about what you think. Guys my age really don’t. (laughs) I also like to do wholesome things and I feel a lot of younger people don’t like to do wholesome things any more. People don’t want to go to Farmer’s Markets, people don’t like to go out to a nice restaurant. I like to do a lot of those old school things.
CJ: What do you like sexually? What gets Jesse wet?
Jesse: Being told what to do; I’m a submissive to the max. I like it rough as well. Anyone that wants to slap my face, grab my hair, I’ll even do a little walk, I’ll do whatever you ask. Nothing gets me more excited; I’m very submissive. I like to serve the people that I’m with be it men or women.
CJ: Have you ever received a golden shower?
Jesse: I’ve done both. I’ve given one and I’ve definitely gotten one but not in the mouth. I’ve never drank pee yet. I don’t know if I will to be honest. Maybe with a trusted partner who agrees to only drink water.
CJ: How often do you masturbate?
Jesse: I used to be an everyday, sometimes more than once a day, kind of gal but haven’t a kiddo, sometimes I’m exhausted so probably every other day at this point. I’m turning into an old lady right before my eyes. (laughs)
CJ: Favorite method?
Jesse: Oh my God, I have a magic wand and it rocks my world. It’s ruined my life! (laughs)
CJ: Did you watch porn before you got into the industry?
Jesse: Definitely. I watch it way more now. Twitter is just a porno all day long. My friends will make fun of me and say, ‘All you do is watch porn all day long!’ And I tell them it’s market research. (laughs)
CJ: What was your favorite genre?
Jesse: Obviously, age gap is something I look for and it doesn’t matter if they’re grey or white haired, I’m into it. I’m just a creepy girl. (laughs) I also like submissive/dom type of play. And I’ve been watching lesbian porn since I was a girl.
CJ: Did you have any favorite stars?
Jesse: I don’t even know, there’s so many. What I look for in a performer is if they’re having a good time, that’s what matters to me. And also, if they’re moans are not annoying.
CJ: When a guy pops, where do you prefer it?
Jesse: In my mouth because I like to eat it and I’m greedy. But anywhere on my body just not inside. Creampies are good on occasion but they mess up your pH balance.
CJ: Are you a size queen?
Jesse: I am not. I can handle a decent sized dick but when it comes to a gnormous cock, they terrify me. I had a scene in my indi/amateur days and I couldn’t walk afterwards. I think I ruined something with my pelvis. Even though I had a kid, I had her by C-section so my downstairs is pretty intact! Ever since then, I’ve been kind of hesitant. But in my DP Diva scene, those guys were pretty large and I didn’t need a walker or anything so it was pretty good!
CJ: Now, your first scene was the DP, when was your first anal experience?
Jesse: Probably when I was doing porn, about 2021 or 2022.
CJ: How did the DP feel?
Jesse: Oh my God, it felt amazing! It was like heaven on earth!
CJ: Was that your first DP?
Jesse I had never done a DP, not even in my personal life. The most I was able to was simulate it with toys to prepare for the scene but, aside from that, I can’t find two guys around here that want to be that close to each other.
CJ: Would a double anal or a double vag be in your future?
Jesse: I don’t know. We were discussing whether or not that was something I wanted to do last week and I declined at this time just because I’m not sure if I’m ready for that yet. I’m not sure where I want to go next. I kind of started at the penthouse starting with the DP but that doesn’t mean I’m not going to go back down the escalator and see what’s down in the normal anal world, the normal boy/girl world where everybody else is hanging out.
CJ: Do you have any fantasies you would like to live out on-camera?
Jesse: I just lived it out. My biggest fantasy in life was always a threesome with two guys and a DP on top of it was the cherry with the whipped cream right on top of the sundae. Since then, now I want another guy. I want to know what three guys and me would be like.
CJ: You like older guys, what else do you look for in a guy off camera?
Jesse: Somebody that is smart. I like smart people. Somebody who has kind eyes. Somebody who likes to fuck.
CJ: What about girls?
Jesse: I like 2 types of girls; the girly girls, the cutesy girl and I also like the more masculine, short hair girl and I think that appeals to my submissive side because I want them to dominate me.
CJ: What’s the wildest or kinkiest thing you’ve ever done in your personal life?
Jesse: I recorded this custom from this gentleman who wanted an outdoor peeing video. I was on vacation when I got this request and I’m thinking I should record it now so I wouldn’t have to do it in cold Pennsylvania. Well, finding time to record a custom while on a family vacation is easier said than done, my friend. So, we took this boat to this remote island and I thought, ‘This is the time!’ We were going to go shell hunting and I thought I could distract the family long enough. I ended up having my best friend, who I peed on her floor, watch out for me while the rest of the family went shell hunting. Meanwhile, we’re on the boat with other people; there are other people perusing this island looking for shells. She watched out for me while I was going to town with my pee all over, having a good time. (laughs)
CJ: And how can the fans follow you on social media?
Jessie: On X, I’m @JesseMayxxx. Instagram is @MamaAlwaysProvides. OnlyFans is JesseMayxxx.
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