Hello and welcome to episode 3! While my first two-episodes were sort of world-building, this episode is going to be about one very specific event: The trip that Dave I took to Tampa, Florida in May of 1998. I will also be including photos. They’ll be censored but, keep that in mind if you’re consuming this episode in a way other than simply listening to it.
Around the same time I took over the reins of the website, Dave started exchanging messages with another early amateur webgirl who I’ll simply call O.
If you know who I’m referring to, please don’t reveal her full name, real or stage, in a comment or anything like that. I am very much an outlier, not just in how early I got started in all this but also being in a position to still feel comfortable talking about it publicly. Others, though, moved on and would rather not have a spotlight on that time in their lives. So, her name for the purposes of this is O. That’s all you need to know anyway.
Also like most, the website only had her stage name attached to it, even though she had a partner. Again, we were an anomaly, using both our real names and including Dave in the title.
O and her partner “Lance” (also not his real name) were living in Tampa, Florida at the time. O and Lance are no longer together but they were for many years. They were also *much* wilder than we were. They would host these parties where anyone and everyone could come and meet up with O and any other webgirls they could get together.
At first, we thought that was nuts! How does she know some axe murderer isn’t going to show up? Quite a few years later, I had a very similar reaction to the concept of Uber.
She eventually convinced us to come down for a party weekend, though. She had done many of these without anything terrible happening, so we decided to give it a whirl.
We did have one thing we had to do first, though: We had already bought tickets to one of those big seminars with a lot of different motivational speakers at the Baltimore Civic Center (or Royal Farms Arena or whatever they’re calling it now.)
Dave had been given Brian Tracy tapes by his Mother in the past and he was suitably impressed enough to insist we check it out. We’re not quite as enamored with self-help gurus these days… it was kind of a phase… but we did take some valuable lessons from that time. The seminar took place just a few days before we left for Tampa, and we listened to the cassette tapes we bought there from Brian Tracy all the way down and back.
Between speakers, Dave would go outside to smoke a cigarette. He has since quit but he smoked for a long time so there are a lot of stories that involve smoke breaks. I have never smoked… well, cigarettes… but I would often stand out there with him.
During this one, we were chatting about the speakers we had seen: Brian Tracy (of course), Zig Ziglar, Faith Popcorn… even Colin Powell! It was certainly interesting.
It was then that Dave finally shared with me the extent of the negative messages he had received in the beginning, and how that had shaped his views about running the website.
I then said to him, “What would we do if we won the lottery and never had to worry about money again?” Almost in unison, we both replied, “Make the site free again.”
It finally clicked in both of us, but especially Dave who had been so tormented, that yes, we were doing what we had to do to pay the bills, but that didn’t mean we didn’t love what we did and couldn’t be ethical about how we made money.
I still value the message that I took from the Brian Tracy tapes of how caring about other people isn't just “the right thing to do,” but can actually be the key to your own success.
We still weren’t entirely sure about O and her parties, but we packed up the Saturn, dropped our dog Spot off at the vet for boarding, and hit the road!
Spot was his real name, by the way. He was a border collie mix that was 5 months old when he entered the shelter but we didn’t get to him until he was 8 months old. The shelter named him Spot and he seemed to be attached to the name, so it stuck.
Anyway, for some reason, I chose a hotel that was approximately 45 minutes away from her house. I can’t remember why; I think it had to do with price, but I don't know why I was being so cheap; We were doing pretty good with money again. However, like every misstep, it just gave us more stories!
One of the first things we did after getting settled into the hotel, was to go to the mall. It was right across the street (I think that might have been part of why I picked it) and I wanted to see if I could find anything new to wear to the party.
Showing off my new dress, in typical "Jen n Dave" fashion.
One of the places I wanted to visit was Victoria’s Secret. We went in, and I found what I was looking for: this sheer white bra with matching panties.
Here’s those same bra and panties taken off of me by O during an iFriends show. We’ll talk about iFriends more later.
I was all ready to head to the register when a very friendly but aggressive salesgirl pounced on me. She insisted I go into the fitting room to try on the bra.
Dave then asked if he could go back with me and she said, “Sure!” Six-foot Dave with a mullet halfway down his back and a big Nikon SLR camera hanging around his neck followed me into the fitting room with the staff’s blessing. Florida, man.
Despite the camera, there ended up being no photos of this encounter because Dave was simply too dumbstruck. As I finished putting the bra on, the sales girl came to the door and asked if she could come in. I was surprised but said, “Sure?”
She begins explaining how the underwire is specially designed for... blah, blah, blah, something. I can't remember exactly what she said, because as she’s doing this, she is very lightly touching my breasts through the bra.
After she left the dressing room, I put my clothes back on, and we left the store (after I bought the bra and panties, of course). As we’re heading back to the hotel, I remember asking Dave, “Why didn’t you take any pictures??” He could only respond, “I froze!”
After we had dinner that night, I went down to the hotel pool. It stayed open late and I love swimming at night. I love it any time of day, but it is somehow different at night.
I remember floating there and feeling like I was exactly where I should be at this moment in time.
When I went back up to the room, I found Dave poring over a bunch of the little brochures I had grabbed in the hotel lobby, when we first arrived. He had been trying to find something we could do during the day to pass the time until the party the next night.
He suggested we go canoeing. I said, “Have you ever been canoeing?” He said, “Not really.” Neither had I but as I often do, I said, "Sure, why not?"
Looking back, that was perhaps the craziest thing we did that whole trip. We went to the place on the brochure, paid our money, and the “guide” drove us out into the wilderness. He gave us a quick tutorial on what to do… he tells us not to worry about the gators; it’s not mating season yet… and Dave and I were pushed out into the river!
It was truly one of the most exhilarating experiences of my life. I’m sure it has something to do with adrenaline, but I have never felt more alive than when I was scared I might die.
At one point, the thought occurred to us, “What if we accidentally bothered the gators?” We could see their little eyes poking up in the water and, while they seemed to be staying far enough away, I couldn't stop imagining one of them swimming under or too near the boat and one of us accidentally hitting them with an oar. How do you say, “Whoopsiedoodle” to an alligator?
Actual photo of a gator we passed.
Everything was gorgeous, though, so as much as we tried to remain focused on rowing appropriately, we kept getting distracted by the scenery. Not long into it, I just went ahead and took my top off while we rowed because who was going to see? We were deep in the wilds of Florida and there were no sign of humans anywhere.
Taking a break from rowing to pose for photos. Because of course...
At one point, we saw what we thought was a giant crane or some other large white bird, just down the river from us. We were in awe. The only thing that tore my attention away, was when I suddenly realized we were heading for an embankment with a big black snake on it, raised up and clearly saying, “I know you’re not coming over here.”
Paddle, paddle, paddle.
Despite the snake incident, though, a little further down, we spot the perfect place where I could get out and pose for a few pictures.
I take off the rest of my clothes and get out of the canoe.
We got a couple good snaps in.
Immediately after taking that last photo, though, I look over and notice that there’s another couple in a canoe coming up behind us on the river. They were still pretty far off but obviously, photoshoot over!
I hop back in the canoe, put my clothes back on, and we paddle, paddle, paddle our asses out of there.
We made it back safely to our guide who was waiting on the other side, to take us back to our car.
We drove back to the hotel, got freshened up, and then headed out for the party!
Oh, to have the energy I had at 23. There would be no way now. "Sorry we missed your party, we just survived doing the dumbest thing we’ve ever done and we are beat."
There were already several people there, although not nearly the crowd that would soon make its way there.
Everyone was so warm and welcoming. I got all these compliments on these snow pics I had done a few months before. Everybody already knew who we were.
More and more people showed up. There was even a band in the dining room. It was a true house party.
Early on, there was a group photo taken of all the webgirls there: one “nice” and one flashing. Later, one girl was smoking in the garage, talking about how her boob job was still healing, so that's why she was the only one that didn't flash for the group photo.
I did plenty, though.
My arms got tired from holding my shirt up, so these guys were nice enough to help a girl out.
As the party went on, I got it in my head to just take all my clothes off.
It’s one of my core memories. As I was just standing there naked, it felt a little weird at first; Had I gone too far? Nobody was complaining, though, and the weirdness quickly faded away.
Can you believe all the seats were taken?
Then Dave, O, and I snuck off to a back bedroom where we could shoot a few pictures of me and O alone.
It was still just posing but definitely more than I had done with Raven.
In fact, I do often refer to it as my first “girl-girl” experience.
We finished the photoshoot and rejoined the party. The band is no longer playing and there are full-fledged orgies going on in every room of the house.
We did not join in but were chatting with some people in the living room. At one point, we decided to simulate a photo of me having sex with a guy that seemed nice enough.
Look, I have no reason to lie. If his penis was inside me, I would tell you! However, he had boxer shorts on. I know, I’m always ruining the fantasy by telling the truth.
I don't know if you can see it in my eyes or not in this photo, but after this, I was ready to go. Not because I was having a bad time but because I was exhausted! So, as much fun as we were having, and as much fun as I'm sure went on after we left, we decided to call it a night.
I drove because I had not been drinking that night, but I only got about halfway back to the hotel before I asked Dave if he felt sober enough to drive. I could barely keep my eyes open. He said he did. He had stopped drinking long enough before we left that, by the time he took over, he was OK; Certainly better off than I was, at least.
The next day, there were plans to meet up with everyone at this beach bar for brunch. I had yet to hear the term, if it had even been coined yet, but it was my first experience with being “hangry.” I mean, I had barely eaten the day before. Can you blame me?
We were having a hard time finding the group. Then we find everybody, but getting a server’s attention is impossible. I finally do and it still takes an hour for the food to come out. I did not act out, but even I was surprised by how mean I was feeling!
After I was finally able to eat, though, I felt much better.
The pleasant look on my face brought to you by food, glorious food.
I did briefly flash there. Dave likes to tell the story of these guys that were looking over and bumping each other and going, “Look, look… she’s gonna show her boobs!” And when I did, there was much rejoicing.
As the beach bar hangout broke up, we made plans with O to meet up at another bar in Ybor City later that night. That's when I wore that black dress I had bought earlier in the trip. Why nobody took any pictures there, I’m not sure. Probably because nobody was getting naked.
I do know that I drank way too many Long Island Iced Teas. O and I talked about our childhoods… how we both broke our arms at the same age… classic icebreaker stuff like that. The whole night, I’m just happily girl-crushing on her. I just thought she was so cool.
I then drop my last, only half-drunk Long Island Iced Tea, and Dave says, “Jen’s pretty wasted, I should probably get her back to the hotel.” I was so offended and tried to argue “No, I’m fine!”
Then we walk outside and I throw up in the bushes.
And on the side of the road halfway back.
And when we got back to the hotel.
The next day I slept in for a while. Then we went to O’s house one last time. She showed us how to do iFriends, which was an early camming service that I just discovered is actually still around. This was before video streaming, though. Computers couldn’t handle that then. They were refresh cams, like the famous JenniCam, where a new picture would be uploaded like every 30 seconds or so. O and I put on a little show for her iFriends audience.
Are you not entertained??
Afterward, we shot a few more pictures, including of me and O on Lance’s motorcycle in the garage.
Don’t be like me boys and girls. Always wear a helmet.
Then we say our goodbyes and the next day, Dave and I decide to do one last thing before heading home: Go to Busch Gardens.
Now it's a business trip.
I don’t remember the rides all that much but I do remember the zoo. Seeing the alligators in their pen seemed so boring now.
I also had this amazing, and kinda disturbing experience coming face-to-face with a gorilla. She was sitting right against the glass and when I leaned down to get a better look at her, I caught her eye and immediately felt… embarrassed.
It felt so much like looking into a human’s eyes, that I felt like I had invaded someone’s personal space. Instinctively I apologized and backed up.
I’m not about to get into the discussion of whether zoos are a good thing or not. There are plenty of pros and cons to be debated… but, that was perhaps the first moment that I felt conflicted about them.
However, one thing we liked to do while traveling was to visit any zoos or aquariums that might be in the area. Weirdly, it’s tough to get people who have been partying naked all night to get up and go to the zoo with you in the morning but somehow we convinced people to join us at times.
On the way home, Dave and I discussed doing our own parties. Maybe not quite like O’s but our own version. We remarked on how natural it felt; How unjealous Dave felt even as I’m naked and talking to other guys. It was a pivotal moment for sure.
OK, well, that’s it for now but I’ll be back next week with more. This was the first of many crazy stories… and yes, some even get crazier than this, so be prepared. In the meantime, though, like, subscribe, all that good stuff… let me know in the comments what you think or if you have any questions… and I’ll see you next time!
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