Performing for Aspen Sugar Daddy

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 now famous Speedo Only Party (Kip is my host and work colleague) . Keep an eye on my blog next week to hear about the shenanigans that are bound to happen.

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.


That is actually all I’m going to publish about this weekend in public.  I feel like I’ve shared too much already.

There will be more available for members.  If you aren’t a member – click here – to join now for just $5.

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.

Horny and Not so Horny

I find it strange how sometimes I’m super horny, like jerking off half a dozen times a day horny.

Then other times I’ll go two or maybe sometimes three days without cumming.

I think the factor for me is how busy I am.  Lately I have been busy (hence a lack of blog posting) and I have not been horny.  So today, I am dedicating myself to working here on the blog.  My first task was to setup a new Movie of the Week.

How I choose the Movie of the Week is by going through the movie archive on my site SpeedoFetish.com and finding something that I like.  Usually it is something I haven’t watched for a while, there is over 100 hours of speedo porn there.  Today I starting watching a movie I added earlier in the year titled Hottub Bear.  It is really fucking hot!!!

Very cute twink and a old bearish guy in the hottub. Twink is wearing a cute pink speedo, bear is wearing classic red speedos.

The bear is a top and after sucking his fat cock, the twink bends over and takes an arse pounding for the ages.

I got two minutes and forty-three seconds into this movie (where the last screen shot of the bear with his hand sliding down the front of the twinks speedo) and I was 100% horny again.  Since I haven’t jerked off for a couple of days I know I have a huge load building up and I want to share it.

So I texted my Married Guy “Wanna fuck me?”

His reply came through in seconds “I thought you’ve never ask, I’m knocking off early today, will be at your place around 1pm.”

I think my non-horny spell is over.  I’m going to see if I can make a run from my place to the ocean with my cock straining the front of my speedo and cool down a little bit.

If you are feeling not very horny, I can guarantee that looking at the movies on SpeedoFetish.com will help you out.

And for blog members, I’m feeling horny and want to share it with you so here is fulltwenty-two minute movie for you guys.  If you want to watch this click here to join now or swing over to SpeedoFetish.com.

Hot Tub Bear and Speedo Twink

Cold here in Australia

When I got back from Colorado I had hoped to get some speedo friendly weather in but it has been cold here in New South Wales (that is what we call the state that Sydney and where I live is called).  There was a little bit of snow yesterday out west which is pretty crazy.

I feel like I should get my snowboard out and find a hottub.

Sounds like you guys loved reading about my orgy last week, it was amazing!!!  I’m not sure if non-members got to read about when Adam (Alex’s boyfriend) asked me if I was up for some DP (double penetration)…. I have never tried it either as the top or the bottom but it could be interesting.

Next week I have some pretty hot DP movies for you guys which I’ve been using for research purposes of course.  Have any of you guys had DP?

Weather forecast says that Tuesday could be a potential beach day, if anyone wants to come and hang out in speedos drop me a line.

Beach Speedo Day

Orgy Invitation

I caught up with Alex and his boyfriend a couple of weekends ago for a Sunday barbie and the three of us speedo’d it up but everyone had to work on Monday so nothing naughty happened.  It was pretty cool just hanging out in the backyard with two other speedo guys, who both look amazing by the way.

Three Speedo Guys

That is the only time I’ve seen those guys since I got back….

Today I received a text message from Alex “Adam, some friends of ours and I want to see if we can destroy your arse better than the Married Guy.”

Firstly, Adam is what I call Alex’s boyfriend (not his real name). and secondly, Alex was referring to what I wrote a few weeks ago about the Married Guy fucking my brains out while I wore a jockstrap he had bought just for me – click here to read that story.

Thirdly, I have no idea who Alex meant by “some friends of ours”.

So, after a bit of back and forth during the day I figured out what Alex was proposing…..

Sounds like Alex and Adam get together with a group of guys every month or so, usually 6 to 8 guys, mostly couples but some invited single guys.  I can’t believe Alex had never told me about this because it sounds fucking hot!!!  This Wednesday, Alex and Adam are hosting the event at their place, they have 7 guys confirmed already and right now there is only one true bottom among the group (Alex is versatile as are a couple of the other guys but only one guys who could really take a pounding).  Alex said that they were going to invite me anyway, but now my arse was in demand – hahaha.

I’ve never been to anything like this before or had sex with that many people before but I think I might be up for the challenge.

It is in just over 24 hours time.  Alex asked if I could wear the new jockstrap that the Married Guy gave me.  I think I’m going to have to spend some time with my butt plug between now and then just to make sure I am ready.

Butt Plugs and Jockstraps

During April I had an amazing number of new blog members which is awesome and I really appreciate the support.  I’m going to be writing about what happens tomorrow night in detail but I’m going to keep it for members only.

The idea of the ‘members area’ of the blog is so that I can write a little more freely without worrying as much about discretion, it is a place where I post more of my own photos and some of my selfies.  If you are thinking about joining, this week might be a fun week to join if this orgy is as hot as I’m anticipating it will be.  Joining costs $5, you can pay by credit card or PayPal, nothing adult in nature comes up on any statements (it comes up as Gocah Limited which is an old shell company I setup for discretion).

And I’d really appreciate your support – click here to join now.http://www.AussieSpeedoGuy.org/join/