Performing for Aspen Sugar Daddy
Introduction:
Kip and I were offered a free weekend in Aspen, we just had to let a rich Wall Street Daddy watch us fuck. I love being watched so we thought we’d give it a try.
Back to what we got up to 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, both 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 fuck.
I love 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, a young gay couple 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 Daddy is in town this weekend but the Denver guys can’t make it so asked Kip 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.
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.
After a little bit of consultation with the Denver guys, Kip and I had come up with a little bit of a plan.
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. 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 (I’m not sharing what channel but there are only two). He is 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.
I slowly removed the butt plug that was inside Kip and he let out a little moan. I pulled my cock out of my speedo and rested the head at the entry to Kip’s well lubed arsehole. Then I began my first thrust.
Kip hasn’t been fucked in a while and he was moaning loudly as I slid my cock into his arse. Listening to him moan and knowing that we were being watched was a super turn on. With a couple of mini strokes I got balls deep inside Kip and rested for a minute.
I looked over at the Wall Street Daddy who was rubbing his cock through his jeans. Should I fuck him hard and fast or slow, I asked Wall Street Daddy? He opted for fast and I happy complied.
My cock started pounding Kip’s tight arse and he was moaning. A little bit of pain but mostly pleasure and Kip was telling me to fuck him harder. I leaned back, holding on to Kip’s jockstrap and my hips trust back and forth. The view that the Wall Street Daddy was getting must have been amazing.
Kip and I have only recently started bare backing (sex without a condom) after we both got tested when I arrived in Colorado. Being more of a top Kip has been bare backing me over the last week but this was my first time fucking him and I was about to cum. My first spurt of cum was deep inside him, my second was half way out and by my third cum spasm the head of my cock was just inside Kip. I let it rest there a little bit before pulling all the way out. The view of my cum oozing out of Kip’s shaved smooth little man hole was a sight to behold.
I tucked myself back in to my speedo, the insides of which would be a mess of my cum and Kip’s arsehole.
Wall Street Daddy stood up and complimented us and said that we were going to have a great weekend. He said that later on he wanted to see if I could take it as well as I just gave it. I said I think I could handle it and I said that he was more than welcome to have a turn as well which raised his eyebrow.
The last instructions from Wall Street Guy were that we should grab dinner and then grab a drink at the Little Nell (I hadn’t heard of it but famous in Aspen circles) around 9pm. We were not to approach him but he might approach us. Then he left.
I need to relieve the strain on the front of my speedo as I sit here writing this. The weekend old got hotter and the snowboarding was pretty amazing as well. I might write more about it later this week.
