OK guys – I’ve just come in from some riding and I’m going to sit down and write about how I got my roommate Will down to his speedos for some horny fun.
Will moved in at the end of November and we share a room in a 3 bedroom condo. Will is 19yo from Melbourne and plays a fair bit of AFL (Aussie Rules Football). He has just finished his first year of uni and is spending his summer break (yes it is summer now in the southern hemisphere – you can’t believe how many people don’t understand that concept) in Canada for some snowboarding.
So far I think that Will looks up to me. I ended up shagging this ski instructor chick that I knew from last year and Will thinks she is hot. And since this is my second season of snowboarding I’ve been able to help Will out with his riding and show him around. I’ve also taken him to different parties and stuff so he has gotten to know a few people in town.
But, Will hasn’t shown any inkling of being keen on some speedo play. I have seen a pair of black speedos in his gear and he does wear them under his boardies but I haven’t had the chance until now to get a good look at him wearing them.
During the first drink Will started talking about Julie (he liked her more than I do) and I thought that maybe there was still a chance to get Will down to his speedos for some fun. I started telling him about sex with Julie… and in detail. We were both on the couch and as I told him about how Julie and I first fucked in our room (our room being Will and my room) while Will was asleep… Will then admitted that while he was asleep when we entered he soon woke up and heard the whole thing.
Will then admitted that he had jacked off while Julie and I were going at it.
That was when I realised that speedo action with Will was ON!!!!
I was getting horny with all this sex and masturbation talk and I could tell Will was as well. So I suggested that we go for a hot tub (it is locked at this hour of the night but we can climb up the railing and get in no probs). Going to the hot tub made sense as we didn’t want to wake up the other housemates. I already had a pair of black AussieBums on under my jeans so I didn’t have to change but Will went into our room. I didn’t mention speedos just yet (I didn’t want to scare him off) and I know that Will always wears speedos under his board shorts anyway.
Will came out of our room in his boardies with a couple of towels, I had already poured 2 more drinks and we left the condo for the hot tub.
So Will and I finally get up to the hot tub. It is coming up to 1am and nobody can bother us in the hottub as it is locked and we climb in from the balcony. I'm wearing what I wore to the party (jeans and a t-shirt) with my black AussieBum's underneith, Will is wearing a t-shirt and boarding which from past experiences I know he is wearing a pair of navy speedos underneith. And we had 2 rather strong scotches as well.
Will took off his shirt and started moving into the hot tub - I had to move quick and dropped my jeans before Will even got his boardies wet. That stopped Will in his tracks. I could feel Wills eyes trying to figure out what I was doing in the small amount of light that was there. But he didn't say a word (I think he though I was just stripping down to my underwear). I pretended nothing was amiss and took off my shirt - now I was standing above him on the side of the hot tub wearing nothing but my speedos and I was still sporting a semi hard on from all the sex talk in the lounge.
Then came the biggest surprise of the night, Will got out of the hot tub just as I was bending down to pick up my drink he started undoing the drawstring to his boardies.
It was time for me to be dumb struck with silence - which was a very cold silence as I was wearing nothing but my black AussieBums at nearly 1am, outside, in a Canadian ski town in early February. But I just stood there wondering what Will was going to do.
Then he spoke... "I much prefer being in speedos too Dave but I've never been game with anyone from the house."
The ice was broken - which was fast forming around my now freezing feet. I slowly got into the hot tub and I enjoyed the show as Will, with his back to me, removed his boardies and bent over giving me a birds eye view of his amazingly hot arse as his ankle got caught on the leg of his boardies.
I was just lowering myself into the hot tub as Will turned and got in - he was a little more than semi hard still and my semi hard state was changing by the second as I had finally gotten my 19yo room mate down to nothing but his speedos. And this is just the beginning.....
As we sat there Will started telling how he grew up wearing speedos and preferred wearing them over boardies. He told me that in his AFL (Australian Football) team he always wore speedos under his footy shorts and most of the team did as well.
As a side note to those North American readers - we don't wear jock straps much down under. To be honest I've never worn one and I've never seen one being worn. Not sure why but just thought I'd mention that. I'd imagine they would be great to wear while being fucked.
I said that I agreed completely and that I would love to wear them all the time but not the polite thing to be done at all times. Being a junior lifeguard growing up I was used to wearing speedos at the beach and when doing any swim training I always wear a speedo. We continued the conversation along the same lines and as I felt my boner dying a little I decided to turn the conversation sexual again.
"You know I've had some fun with Julie wearing these speedos?"
Will sat up a bit in the hot tub (I've commented before on how hot he thinks Julie is). "Does she like you wearing them Dave?"
Now it was time to see if the str8 Will could possibly be bisexual Will.
So I told Will the story about Julie, Matt and I and our New Years. I started the story slow about the three of us at the hot tub - Will had seen Matt but hadn't really spoken to him as Matt was only in town for a week. I was really trying to gauge Will's reaction as I started to tell him that Matt and Julie both started sucking my cock. Will didn't seem to fazed so I continued.
Man I was getting worked out telling this story and one hand was holding my glass (plastic glass being in the hot tub and all) with one hand and the other hand was rubbing the outside of my speedos. By the looks of Will he was doing the same and he was not just holding onto his cock but he was also holding onto every word.
When I finished the story I asked Will if he wasn't freaked out that Matt and I had sucked each other off?
"Nah Dave, that was such a hot story I wish that I was there. To tell the truth I have been sucked off by a guy once myself."
"Wow - that is hot Will." I replied. "I'd love to hear about it!!!"
Will then told me the story about how just 4 months ago he and a football friend had ended up getting drunk and horny and his friend sucked him off. That was his only guy on guy experience and Will didn't do any sucking. He said that he was a little weirded out about it and it was really uncomfortable with the guy who was one of his best friends.
That was part of the reason why Will had come over to Canada for the ski season he was that weirded out about it.
As he finished up explaining it he said that he had thought it was weird to be bisexual but that my story of my threesome with Julie and Matt seemed completely normal.
I started saying that I felt the same after my first guy on guy experience and that it is kewl. Perhaps I overdid the Dave likes girls more (which you guys all know I like guys in speedos way more) but I wanted Will to feel assured that even if he likes girls more that he can do what he wants with a guy and he isn't committing a 'sin'.
With that side of the conversation ending I had to get back on horny topics. "If you are keen Will - I reckon that Julie would be in for a threesome with us two if you are keen."
That got Will going indeed!!! "Man would you do that really?"
I would be more than happy to see this hot 19yo, blonde Aussie guy fucking Julie. So for the next while (we had a fair bit to drink so time doesn't matter that much) we talked about a threesome with Julie, the how and where. With all this kind of talk we were both getting really really horny!!!
And it was getting late so I had to make the move.....
"Hey Will, man I'm so horny I'm going to have to do something about this." I probed - hehehe. Without giving Will time to response I sat up on the edge of the hot tub. My raging hard on was at eye level with Will.
I expected Will to say something but he didn't say a word - his eyes were fixed on the front of my speedos. No matter what there was no way I could hold back - so I pulled my black aussiebum speedos aside and pulled out my newly shaved cock (yeah I shaved it the day before).
Odd for me I know, but I didn't start pumping my cock. I just let it stand tall as Will sat mesmerized and I played with my balls. Ow guys - you can't imagine how horny I was at that moment.
"Feel free to join me Will if you want. It is kewl."
With that Will slipped out of the hottub. His navy speedos looked like they were about to explode with the pressure that was building up behind the lycra. Mirroring my cock removal technique, Will pulled his cock out the side of his speedos.
"Ahhhh - that feels better."
And I tell you what - that looked a lot better as well - hehehe.
Will's trace state had now passed and he asked me about being shaved down there. I told him I liked it more and of course that Julie liked it as well.
"You should definitely try it mate."
"Yeah I think I will hey. How do you do it."
I explained how I shave myself - it was definitely weird as the two of us were both sitting on opposite sides of the hot tub, wearing nothing but speedos, our cocks tucked out the sides AND by now we had both started to stroke slowly.
Watching Will stroke his cock I just needed to get it into my mouth. After my shaving lesson I turned the topic back to Julie and the proposed 3some.
"Will, would you be kewl if Julie wanted us to suck each other?"
"Yeah I would be OK with that mate."
There comes a time when you have to take that big step.... and I did.
"Do you mind if I suck you now?" I said as I let go of my own cock and slipped into the hot tub moving towards Will.
"Dave, I am so horny there is just about nothing I wouldn't do right now." It was that moment when Will took his hand off his cock and I attached myself. His cut cock was rock solid and I sucked it like there was no tomorrow. I don't think I've ever sucked cock with such ferocity!!!
As expected, Will didn't last long and he unloaded in my mouth. Spurt after spurt of hot creamy Will was pumped into my awaiting mouth. I swallowed it all and I stopped sucking as I know how sensitive my cock gets immediately after I cum. Removing myself from Will cock he asked me what cum tasted like.
That was Will's first time kissing another guy.
I tucked his still hard cock into his speedos and moved up his smooth stomach and as I got to his lips I could feel his breath on my nose.
Then we kissed.
Will had been sitting out of the water now for a good 5 minutes and as my hands moved to his speedo clad arse I could feel how cold he was and without our lips separating we both moved down into the warm water of the hot tub.
Our kissing lasted 5 minutes or more without a break. I rubbed Will's butt the entire time and he worked his hands down to my cock which was still outside my speedos. I finally broke off the kiss and I stood up and with my cock at eye level Will didn't need any introduction and started licking my cock. It was his first time so he took it slow - which was agonizing as I wanted to cum on the spot.
Finally Will got some rhythm and it wasn't long until I was on the edge. Being his first time I didn't want to unload in his mouth so I pulled Will off at the very very last minute and unloaded on his chin and then his chest.
And that is how I first got it on with Will. I'm sure there are going to be many many more stories in the next couple of months of what Will and I get up to.