Show notes
Sometimes it doesn't work out.
Transcript
Welcome to the Pineapple Pin-Up, the Hot Wife Life Podcast. On this episode, I want to talk about fails. When you're in the lifestyle, there are plenty of reasons why things don't work out. It can be very stressful and anxiety-producing when you're trying to set something up. Agreeing to meet a stranger in today's world, as any true crime podcast or documentary or TV show will tell you, is tantamount to filling out your death certificate and hoping it doesn't get stamped.
Fails are especially painful when you have been building them up in your mind, embracing a scenario that you're building together via messaging back and forth, and creating what you fantasize will be this epic scenario that will change you fundamentally forever. We have high hopes and belief when we are texting back and forth that our words are connecting in a way that both parties are fully engaged and when you feel fully engaged in the conversation for it to end up in a failure is doubly disappointing a time that this happened to me, we'll call him Wolf. And I were texting back and forth.
He was a dom and in my heart of hearts, in my tiny little kinkster inside, I truly want to be submissive because it is such a turn-on so impossible to achieve but such a turn-on and Wolf was of course hitting every one of my buttons because he is in his little kinkster inside, truly a dominant. So as Wolf and I were texting back and forth, scenarios started to come together. And I will tell you the one that basically led to us agreeing to meet up in real life. He was very interested in the dynamic of cuckolding my husband.
And he wanted to dominate me and vicariously dominate my husband through that act. The scenario was that my husband would bring me to a location wearing a leash and a collar, and then he would escort me to the wolf, hand over the leash, and then go sit in the corner and wait for the wolf to do what the wolf wanted to do.
And in the scenarios that we ran through together, it would, of course, start with a blowjob, a deep, hard, face-fucking blowjob, where I'm held down on the cock until I am choking and drooling, and I can't breathe breathe and there's tears running from my eyes and then when he felt like I was about to pass out he would let me go. That would then of course lead to me being thrown across the bed and having him fuck me hard from behind before ultimately taking my ass. This scenario was played out minute by minute in text text, between he and I.
Certain areas were polished, certain ideas were formed, and ultimately we had the scenario that we wanted to build in mind. We decided we were going to meet and make it happen. We, my husband and I I arranged for a hotel room we paid for it and had the date and time all set up and four hours before we were supposed to meet we got a message stating that he was sick. Now, post-COVID times, that's not something you can easily ignore, especially if it's compromised in your immunity. So we had decided that we would try to reschedule.
Of course, when something like that happens so close to the moment that you were actually supposed to make it happen, it starts to give you doubts as to what you were thinking and what actually their situation is because when you're texting back and forth, a lot of people lie.
A lot of people tell stories about how they're in a relationship and this is all very like allowed and appropriate and okay for everyone and it turns out that it's really not so sometimes it leads to questions about what their true motivation was i truly am horribly disappointed that i never actually got to meet Wolf in real life.
He and I had such a deep connection in that texting, building that scenario, creating that scene from imagination to actual description and I mean I knew what I was going to wear I had a collar all picked out the whole thing and sometimes in your brain you make these things so epic that it really can't even live up to it in real life. So there's your trade-off I guess. Scenarios that are presented that aren't necessarily reality, those can be a little bit harder to suss out.
For example, if a man says that he is single when in fact he's married with children, they can tend to have a hard time getting away at the allotted time and therefore they have to cancel at the last minute. Our next story comes from Pipe. Now, Pipe and I had messaged back and forth and he was from the north and had to drop his children off in the south on the weekend. So it was very easy for him to stop here in the middle in my wasteland area to have a play date.
So the first time we tried to get together, he had a problem dropping off his children and an hour after we were supposed to meet, an hour after I was at the hotel room, he messaged and let us know that he wasn't going to be able to make it. So the next time we scheduled a meet, we contacted him before we headed over to get the hotel room and he answered and was basically too drunk or high, I'm not quite sure which, to actually meet us.
After we put a kibosh on the whole thing and just went home, he contacted us maybe 30 minutes later and said he was with a buddy and wanted to know if both of them could come fuck me. Now, in imagination, that could be very, very hot. But in reality, whiskey dick is real. Weed dick is real. And having two men that are there and two beyond to actually be able to perform is not what I call a good time. It's really difficult on the ego to make it happen so that was a big no. I do not disrespect people by being too drunk to properly consent or too high to properly consent.
I believe that in the tenets of safe, sane, and consensual, you have to be sober too. Not necessarily sober in your whole life, but sober enough to consent to what it is you're about to partake in. Because this isn't normal behavior, and you have to truly be mindful and present to fully give consent for what you're about to take on. So therefore that one was a fail that repeated and my husband and I learned a lot lessons from that one. The next epic fail we'll call The Chef.
We had arranged to meet south of here because we were always trying to go south to make connections because traveling south is so much easier than traveling north in our area so we we were trying to make those connections we had made arrangements to meet the chef down in the south area and he had apparently forgotten about an hour before we were supposed to go over there. We contacted him and he was like, Oh, yeah, come on over. So we headed over. And because of the fact that he had forgotten that this was set up, he didn't mentally prepare for what he was taking on.
You have to be mentally prepared to take on having a couple come to your room and the man sit there and watch you fuck his wife. There has to be some mental gymnastics that you go through in order to be prepared for that scenario. So because of the fact that he was ill-prepared he was also ill-prepared in the fact that he was exhausted he had spent an entire day working and setting up a banquet that he was chefing for and was not able to actually have anything in the tank for playtime to actually commence.
So for an hour and a half, we sat around chatting about his work as a chef and I tried very hard to encourage him to rise to the occasion, but it just wasn't going to happen. So because of that incident, the chef decided that he wanted to have a do-over. So he threw, quote unquote, a party. The problem with the party is that three people showed up. The basketball player, the chef, and I, with my husband in tow. The chef had obviously taken some enhancements and was a little bit high, a little bit, not quite 100%. So he was able to perform and that was nice.
We, but he was so distracted by what was going on what he was metabolizing that he wasn't actually able to fully focus and be present the basketball player and I ended up oh my god fucking so hard over the edge of the bed that it was insane I could feel him the next day. He was so fucking deep inside of me. He pounded me like I was trying to foul him on a court. That basketball player took me to town. He really did a great job. I sprayed all over him. It was messy and fantastic.
And because of the fact that I was having such a good time with the basketball player, when we took a break, the chef would come over and literally do that thing that men do when they're trying to, I don't know what they're trying to do but they come over and they press their penis against you so it's like they're pressing their hard cock against you in a normal everyday average setting and you're trying to figure out why is this man's dick on my shoulder blade kind of thing I don't understand what that is, but it happens to me quite a lot.
And I don't know if that's weird or if that's something that men do normally to people. So it didn't last long that particular, because of the fact that it was getting very awkward, and the chef was getting more and more manic, so we took off early, had a great time with the basketball player, would love to do that again, but I still consider that whole thing a fail. The arrangements that are made with one specific person to have a good time when that falls short, it can be very disheartening.
I've also already told you about another party that I went to that was an epic fail I had a man who had catfished me there who was making me feel very uncomfortable and I told him so that I'm sorry I don't feel comfortable with you please don't touch me and then the party host and then one other guy who was so busy trying to wrangle the date that he brought that it he couldn't even concentrate long enough to give me an orgasm so that night I went back to my hotel room with my husband and I made my husband get me off several times in exchange for the fact that this party was such a dud.
That failure turned into quite a bright spot for me of course like they always do because I am a greedy girl. I get my orgasms. Come hell or high water this girl is gonna come. Because of the tendency we had to fail at making connections in real life after messaging for a while back and forth, we decided to cut out that aspect. Make it so that our first in real life meeting wasn't happening one-on-one.
We went and did our first party, which led to a play date, which gave us the idea that maybe the best way to meet potential partners would be from the parties, taking their number, making contact, connecting via text, setting up a play date. They already knew who I was. I already knew who they were. We knew that we were compatible. We knew that we had chemistry.
We knew that we played well together and we were a cooperative team that got everyone to the finish line and it was something where that allowed us to get rid of a lot of the guessing game that happens when you don't know who it is that you're meeting. So because of the fact that we found parties to be such a great harvesting of play partners, we decided that's how we would meet people from now on. People message me a great deal and ask me to meet up. And my answer is always, I meet people through parties.
The problem that you have in the wasteland is that a lot of the people who live in the wasteland don't go north or south to attend events because they're just trying to make connection via text because they know better than to assume that there's anything close by that they can attend. So I miss out on a lot of local dick, if you will, because of the fact that I kind of require that we meet at a party. It has worked so incredibly well to meet my friends at parties and then set up dates with them beyond that, that it's very hard for me to imagine a different way of finding play.
And right now, I just, I'm impressed with my roster, if you will. I have great friends that meet with me, and we can talk, and we can have fun, and we can fuck, and it is amazing. And I don't have any problem, because we have spent so much time together at this point that we find it just easy to be around one another.
so while it kind of sucks for some that I don't play just one-on-one because some men are just not prepared for parties and they're not interested in trying to find out if they could perform at parties they're just that's not something that they're into and everybody has to know their kink limits and this just happens to be the easiest way for me and my husband to create the kind of kink without wasting hours of our lives and weekends trying to find something that was probably never going to happen because somebody lied about being married.
that is a huge weight off of my husband and I, to be able to simplify our kink connecting in a meet-a-lot, at-one-time kind of happening. so today's question is from Jay Osh. I'll call him Josh. Different Josh than I've answered questions for before. He asked, since I live in a kink wasteland, how do I find most of my playmates? Well, considering that most of this entire episode was showing how I don't know. pink wasteland, how do I find most of my playmates?
Well, considering that most of this entire episode was showing how much of a wasteland and how easy it is to fail at this, Um, I do find, I'm going to say 95% of the Playmates that I have, I found at parties, 100%. Some came from my actual life. And the majority, though, I located going to parties, exchanging numbers, deciding that we had a connection that was fun and effervescent and was worth taking to another time and another place to have even more fun. I can't say enough about how the party scene has truly enabled the rest of my life I'll see you next time.
I can't say enough about how the party scene has truly enabled the rest of my life, the rest of my kink life, to function fluidly. I can make a phone call, send a text, do what I have to do, and find something that will give satisfaction to both me and my husband. I have been truly blessed to find the kink friends that I found in the way that I have. It's low pressure. It's high fun. It's no expectations. And just such a relaxing endeavor that I can't speak highly enough of going to the events, going to the parties, even if you don't play.
You can watch and you can make connections with the other people who aren't playing and you can talk and you can maybe spark that connection that will say, hey, I may not be comfortable doing this here, but I would love to meet you somewhere else. Can we exchange numbers? It is without a doubt the best way to limit the amount of time you're wasting on people who are just not going to show up. You know that they're going to show up because you have a relationship and you have made time for that relationship. That doesn't mean that you don't get flaked on still.
I met a guy at a party just recently who, he didn't play at the party, but we did take him back to our hotel and oh my god it was phenomenal that man's mouth is a goddamn miracle we'll call him bald he was amazing with his tongue he had a tremendous dick I was in awe I was a gushing geyser of yes please more so we had arranged we'd exchanged numbers and we had arranged to meet up a different time and he of, had something come up and was unable to meet us. So it still happens, you still get stood up, you still have connection issues, because I mean, this is real life.
And sometimes I agree to go to a party and then I'm not feeling well. So I say, I can't, I got to go home. I wish I could. And it's fine because you have the adult conversation and you say, this is why I cannot do this thing. So because just because I'm doing it this way, it cuts down the risk, but it doesn't eliminate the risk that I'm going to fail at this. And it does help to mitigate the wasteland effect that I happen to currently live in.
It would be awesome if the people nearby to me would actually participate in parties and events, but we've had somebody schedule parties close by and they just didn't happen. So I'm really hoping that one day the wasteland will bloom a little bit and the kink will become a little more part of the experience. But anyway, here's to hoping. thank you so much for listening to The Pineapple Pinup, The Hot Wife Life. If you are having a good time, please like, share, subscribe, anything you can. I'd really like this to be a success.
If you have questions or comments or suggestions, please don't hesitate to hit me up at pineapplepinuppod at gmail.com. I look forward to hearing from you.
