If Wisconsin Tiff’s origin story sounds like something out of a movie, that’s because it practically is. A small-town stay-at-home mom who spent years cooking meals at an elementary school, Tiff swapped lunch trays for a laptop—and never looked back.

Five years into her career, the 38-year-old content creator has carved out a fiercely loyal fanbase by doing things her own way. Known for her love of older men, her enthusiasm for gangbangs, and her disarmingly honest personality, Tiff brings an authenticity to the screen that money simply can’t buy.

Our resident Q-and-A guru Captain Jack recently sat down with Wisconsin Tiff for the latest installment of Jackin’ Around—and as you’ll quickly discover, the former lunch lady held absolutely nothing back.

Enjoy!

Captain Jack: Tell me about Wisconsin Tiff.

Wisconsin Tiff: I am from Wisconsin and I’m just a normal girl who does normal everyday stuff except for the work that I do. (laughs) I travel a lot and I do a lot of fun things. This industry gives me the opportunity to indulge in things that I wouldn’t be otherwise.

CJ: How long have you been shooting now?

Tiff: I’ve been in the industry for almost 5 years. I was doing mostly solo content and it wasn’t until 2023 that I actually started shooting videos with guys.

CJ: How old are you?

Tiff: I am 38.

CJ: Were you a very sexual person before you entered the industry?

Tiff: Not really. I was married and I was mostly a stay-at-home mom, worked at the elementary school as the main cook. I was the lunch lady. (laughs) I was just regular mom and I did the mom things that my ex-husband would want to do but nothing like this. (laughs)

CJ: When you were just mom, did you have desires to hook up with other people?

Tiff: No, when I had left, I didn’t have money. I started an OnlyFans and was told that I didn’t even have to do anything. I didn’t even post any nudes my first year. I had no desire to. I got so nervous; I remember posting a photo where I was wearing a bra and underwear and the underwear was lace and you could kind of see through it and I freaked out. I was looking at it and thought, ‘Oh my gosh!’ Now, I look at that and that’s nothing! (laughs)

CJ: That’s the main reason you started this, because you needed money?

Tiff: I needed a way to leave my situation in a timely manner. Honestly, when I was looking at it, I thought there was no way I could live on my own and I wanted to do it on my own without his help. It wouldn’t have happened because he didn’t want it to happen!

CJ: How long were you married for?

Tiff: We were together since high school and got married in 2014. We were high school sweethearts.

CJ: Is he the only guy you were with before you started all this?

Tiff: He was my first everything. I haven’t been in a relationship other than him.

CJ: Wow! You were with one guy then, BAM!, you’re doing all this?

Tiff: Yes. (laughs)

CJ: And now you’re shooting more mainstream stuff too?

Tiff: Yes, I do some mainstream here and there but my main thing is shooting content for OnlyFans. I do shoot for Tadpole here and there. I know this year, I want to get back into it a little bit more. I’ve had a couple pretty big companies reach out to me and I told them that once I’m ready, I would love to do that for them.

CJ: You said when you started OnlyFans, you freaked out a little bit at that picture of you in a bra. How long did it take you to start feeling comfortable?

Tiff: It took me a year and a couple of months to get used to that. I had a video go viral of my bedpost and I had more subscribers coming in. And when I saw the subscriber count going up and they’re asking me to post nudes and they wanted more, I figured I want to keep them. I had never seen that many subscribers before so I started posting nudes. It did well and then they wanted more and more and more so it took me another year for me to film an actual video. I wasn’t ready yet but I’m glad I did it the way I did because of the way it built up. I wasn’t planning on doing that so it worked out perfect!

CJ: What’s your favorite position?

Tiff: I like it when a man is on top of me. (laughs)

CJ: You are really into older guys. How did that start?

Tiff: I had started TikTok and wasn’t doing really well in getting followers and, one day, I decided to make a TikTok about older men and it did really well! I had a lot of older guys follow me who were in their 40s and 50s and they were gifting me stuff and being so kind. And, honestly, I was in a really lonely time because I had just lost my ex-husband and it wasn’t easy. It was really, really hard and I had a really hard time dealing with it. And so, these men were so nice to me and the video went so well that I decided to keep catering to older men. They were so kind to me and they actually helped me leave a bad situation. I was still with my ex for just a little bit and when I told them what was going on, they started giving me extra money and tips. And I was able to leave.

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

Tiff: Gangbangs. (laughs) I actually had a fantasy about a gangbang in 2022 and then, in 2023, I’m going to start doing them. I didn’t know where to go or how to set it up and then Rebel Rhyder’s husband got me in contact with Tadpole. He said, ‘this guy’s great!’ So, I did that in 2023 and I didn’t know it was going to become a thing! I love gangbangs! (laughs)

CJ: What’s the most guys you had at once?

Tiff: The most guys was for a backdoor challenge and that was 50 guys. I was at a 100-guy gangbang for Rebel Rhyder and I was just a fluffer. And afterwards, I wanted to know what it was like to have a gangbang not on-camera so I did and it was 5 or 10 guys. I loved it so I did my first one on-camera. I never sold that video; I just did it for fun. It was my first time.

CJ: Have you ever had any other gangbangs in your personal life?

Tiff: Always on-camera.

CJ: Have all your gangbangs been for Tadpole?

Tiff: Now I know how to do them myself. I’ve learned from him and what I should do. I’ve learned about the testing stuff and how to get tested. For the longest time, I didn’t know how to organize it without them listening. Tadpole told me how to do this so it’s organized well. Now, it’s just easier and the way I do it makes the time wasters not waste your time so much.

CJ: Are you submissive or dominant?

Tiff: Both, depending on the situation. Sometimes, if I’m having a hard day, I want to be dominant. I have this guy on my Snapchat that pays me to be mean to him and he does video calls. I love that because whenever I’m really frustrated, I can take my anger out on him. (laughs)

CJ: Being submissive, you like hair pulling, spanking, slapping, all that?

Tiff: The hair pulling when they’re behind me. When I’m submissive, it’s moreso the gangbangs. I just want them to all take advantage of me.

CJ: How often do you masturbate?

Tiff: A lot. (laughs) I don’t have a boyfriend. I live alone and I’m worried about having a boyfriend in my home state because if we break up, I’m afraid they won’t leave me alone. (laughs) If you want to be my boyfriend, you have to move to Chicago. (laughs) Or not come to my house. (laughs)

CJ: Favorite method?

Tiff: I have a reputation of letting all my vibrators die and then I can’t find the cords so then I buy a new one. (laughs)

CJ: Did you watch porn before you got into the industry?

Tiff: Never. My ex-husband did all the time and I didn’t really understand. The funny thing is that I was actually in a movie with Private Society, one of my first mainstream shoots. And I later found out that was his very favorite one and I ruined it for him.

CJ: What does your ex say about your career now?

Tiff: He doesn’t like it but I try to avoid the conversation. We get along but I try not to step on any toes.

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

Tiff: It depends on the situation. If it’s a gangbang, I want it all over, I want it messy. That makes the video go really well. If it’s one-on-one, creampie.

CJ: Are you a swallower?

Tiff: Yes. Sometimes, it depends on if I’m trying to make it look good, then I’ll take it in my mouth. (laughs)

CJ: Are you a size queen?

Tiff: Gosh, the big ones hurt! I like average sized.

CJ: When you started doing gangbangs, is that the first time you did anal?

Tiff: No, I’ve been doing anal for many, many years. Way before porn so I have a lot of experience with that.

CJ: You’ve done a lot so do you have any other fantasies you would like to live out on-camera?

Tiff: I feel like I’ve done so much so now it’s doing what works. I’ve really fulfilled those fantasies. (laughs)

CJ: We’ve talked about your love of older men. Where do you find these guys?

Tiff: I find them from FetLife and find them on Twitter. If it’s on Twitter, I tell them to go to FetLife. Sometimes, they’ll go, ‘What’s your FetLife?’ And I’ll tell them Wisconsin Tiff but they’re so old that they don’t know how it works. I have to guide them like they’ve never used the internet before. Even though they found my Twitter! (laughs)

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

Tiff: On X, I’m @Wisconsin_Tiff. My Instagram is @Wisco.Tiff. And you can just google me.