This morning I was going through the archives looking for some of my Colorado speedo experiences to share with you guys. It was a fun ‘Jerk down memory lane’.
Here is an experience that was unique for me which I wrote about back in 2019. There were two more ‘experiences’ with this guy but due to discretion I was only allowed to write about the first time I met him.
Enjoy….
I told you guys that I had a crazy weekend here in Colorado and finally I’ve gotten a minute to sit down and tell you guys about it. I’m still in Colorado but headed back to Australia early next week after Kip’s (my host and work colleague) now famous Speedo Only Party. Keep an eye on my blog next week to hear about the shenanigans that are bound to happen.
Back to what happened last weekend.
It started on Thursday night when Kip asked me if I wanted to go to Aspen for the weekend? I have never been (Kip lives in Breckenridge and Aspen is a two hour drive). Of course I’d love to snowboard Aspen but I had looked at it in the past and it is phenomenally expensive, accommodation and ski lift passes. I expressed that financial concern to Kip who said he had an offer for me.
We had a free place to stay, free lift tickets and all we had to do was let this guy watch us Kip and I fuck.
I love watching and being watched so that part didn’t bother me. Who is the guy?
The guy is a last fifties, married (to a woman), Wall Street guy who has a monster house in Aspen. He also has a condo on the snow. Super rich, like crazy rich. Some Denver friends of Kip’s that I have met go out there and perform for him a few times a year when the Wall Street Daddy is in town. Wall Street dude is in town this weekend but the Denver guys can’t make it so mentioned it to Kip to see if he and I would be interested.
Kip was told that the guy would come over each day and we would be expected to fuck while he sat and watched us, Wall Street Daddy may or may not jerk off but we didn’t have to sexually interact with him. Other than that, Kip didn’t know anything more about it other than discretion would be paramount and that we would have to sign a non-disclosure agreement (I asked and me writing this isn’t in breach of it).
The whole thing sounded awesome to me. I definitely have a little bit of exhibitionist in me (maybe that is where my speedo fetish comes from) and of course I would love to snowboard Aspen for a weekend. Kip felt the same way so we agreed to give it a try.
Next step was Kip and I sending a copy of our passports through to the Denver guys (they were going to be facilitating this), along with the non-disclose agreements signed. Those guys asked if they could mention that I am Dave Speedo Evans (from my blog Aussie Speedo Guy) which I agreed to. We could check in to the apartment on Friday night and Wall Street Daddy would see us that night and tell us when he would visit over the weekend. He would give us the ski lift tickets when he saw us on Friday and we could check out any time on Monday.
Little bit of back and forth and it was a green light.
About twenty four hours later, nearly to the hour, Kip and I were in this beautiful, ski-in, ski-out apartment right at the basin of Aspen Mountain. Not a huge apartment but it had a hottub on the deck and I can’t even imagine what it cost. We were told that Wall Street Daddy would be by around eight o’clock and he was due any minute.
After a little bit of consultation with the Denver guys, Kip and I had come up with a little bit of a plan on our part.
There was a knock at the door.
When I opened the door the Wall Street Daddy was greeted by seeing me wearing just my new tiny Asian style Arena speedos. I got these when I arrived in Colorado a few weeks ago and I love them. They sit low on my hips and are far too tiny to be worn swimming but look great and everything fits in. The lycra material stretches enough that it can contain my cock when erect which is what Wall Street Daddy saw when his eyes moved down my body to the front of my little speedo.
What I was greeted with when I opened the door was a well dressed, late fifties guy that I totally recognised from watching the business channel on TV. Not a commentator but someone that they have on to interview. I wouldn’t have known his name off the top of my head but I knew who he was.
We shook hands and he entered the room.
Wall Street Daddy was saying that he was just swinging by on his way to dinner and might see us later when he noticed Kip. Kip was wearing a jockstrap and was tied to the couch with his arse in the air, with a butt plug inserted in it.
I asked Wall Street Daddy if he had a few minutes to spare as I was about to plow Kip’s arse.
Wall Street Daddy sat down on the chair that Kip and I had put out with a birds eye view of what we were about to do.
That is all I’m going to publish about this in public. I feel like I’ve shared too much already.
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This is the kind of thing that I created the members only area for. Things that I can’t really publish in too much detail in public that I still want to write about. Without the members area I wouldn’t be able to write about this at all in the interests of discretion. I hope you guys understand this and even more, I hope you support me and this blog by becoming a member.
