I dug this out of the archives on my blog because last week I hooked up with a guy who was doing some naughty things in his speedos for money and it reminded me of this experience I had a few years ago.
I saw an ad online looking for "Exhibitionist Waiter for Private Party". It was coming up to Xmas and I really needed the money. I was feeling pretty happy about my twenty year old body these days, I was training for some long distance swimming events which involved spending a lot of time in the pool. With all that training I was starting to tan up nicely and I had lost about ten kilograms which put me in the slim category.
Let me quickly explain a bit about myself, I'm twenty years old and mid way through my college degree, I'm 6″1′, dark hair with some blonde through it and reasonably tanned. I've had a little bit of guy/guy experience but not much -- although it always gets me hard. I've fooled around with guys but never to the point of orgasm, I know that sounds weird but the few times I've fooled around I've gotten close then cut things off and jerked off thinking about it for months and months afterwards. So I've very inexperienced.
Back to the story...
So I'm feeling pretty confident with my body these days and this ad for an `Exhibitionist Waiter' sounds like it could be interesting and I won't knock back the money.
I replied to the ad with some of my favorite selfie pics of me in my speedos which were all taken by mates just goofing off after swim training. I received a reply within a couple of hours outlining my `duties' if I was to accept the position. The guy who placed the ad, Kyle, explained to me that he was having a party at his place for a group of mainly gay friends and thought it would be fun to have some cute young guys being waiters in speedos. Kyle was looking for three or four waiters and was willing to pay each waiter $250 for the night plus all the alcohol and food they wanted.
After reading this I got a hard on straight away, sounded perfect. I love speedos (my few guy/guy experiences had always started from scenarios where I was with other guys in speedos, and speedos have always been a fetish of mine). Kyle and I corresponded over the next two weeks and all was sorted for the Friday night. The details were that I was to just rock up at 6:30pm and people would start to arrive at 7pm for the party. Kyle would provide the speedos and I was to wear tennis shoes and socks with them.
Friday finally came and I left my place at 6:15pm. For sure, I was nervous but excited at the same time. Kyle had told me that there would only be two waiters, another guy my age and myself, but he said that he would pay us $350 each for the night because of the extra work load. I arrived at Kyle's and walked up to the front door. Kyle's house was impressive, a huge house that could nearly be called a mansion. After knocking on the door I heard foot steps and the door opened. With the door opened I was faced with a good looking guy of about thirty years old. The guy in front of me quickly introduced himself as Kyle and welcomed me in. Kyle led me through the house to the kitchen where he was making last minute preparations. As we entered the kitchen Kyle began to introduce me to the other `waiter' Martin who was already in his uniform, a tiny black speedo, and nothing else. Before Kyle could say my name the other waiter greeting me.
"Brad, is that you man -- how the hell are you?"
"Martin, mate how are you? Long time no see." I replied as we shook hands.
Martin went to school with me and was the first guy I had ever fantasized about. He was in my class and I had thought he was good looking, but then we had a semester of swimming classes and since it was an all boys school, speedos were compulsory. I remember Martin's tight arse in his little black speedos. I jacked off to that thought for years. I didn't know Martin had any gay inklings but I had masturbated many a time thinking of Martin in his speedos.
"You guys know each other?" asked Kyle.
"Yeah, we went to school together." Martin replied.
"I'll let you take Brad upstairs and get him into his uniform. I've got some stuff to finish down here so take your time. Don't forget, when the guests arrive you are to greet them at the door and lead them out the back."
Martin lead me out of the kitchen to the main staircase. Ow my God his ass was amazing. In the tight black speedos it was tight and moved smoothly as he walked. I could hardly keep my eyes of it.
"So Brad have you done this before?" Martin asked as we approached the top of the grand curving staircase.
"No mate, my first time. But I have to admit a soft spot for speedos so I jumped at the chance. How about you?"
"Yeah I've been doing a little bit of escort work, nothing heavy or anything just the odd nice older guy. Pays better than McDonalds and I've got some regulars now that are really pretty easy going."
"For real? I didn't even think you were gay?" I replied with a good pinch of shock in my voice.
"Yeah, never really mucked around with any guys my, I mean our, age, its only really for the money I suppose. I'm not complaining though. Anyways, your `work' gear is on the bed." Martin said pointing to the pair of size 12 (28″ waist) black speedos on the bed. By this time my cock had stirred and I was half hard and really looking forward to getting into those speedos.
I undid my belt and the button on my jeans, Martin seemed to make himself comfortable on the bed. Evidently, he was going to watch me get changed and didn't think anything of it. I wasn't quite that confident.
I grabbed the speedos and told Martin, I'd be back, as I headed towards the en suite.
As I quickly changed in the bathroom I looked at myself in my tight black speedos and thought, darn I look hot!!!
It was time to try it on Martin and walked out of the en suite dressed only in my tiny black speedos. Sitting on the end of the bed Martin was fixated on my speedos. "Wow Dave, you look fucking hot!!! Your cock is huge too!!!" Speedos have the effect of getting me aroused.
"Thanks mate, you look darn hot in yours as well." I said as I sat on the bed next to Martin. It was only 6:45pm so we had time before anyone arrived.
"We'll we can't go down stairs with only one of us hard." I said and I put my hand on Martin's semi hard cock. Martin looked into my eyes and we moved forward and began a deep kiss. We kissed deeply and our tongues lashed. I had been looking forward to this for years but never thought it could possibly come true. Martin lied back and I was on top of him with my thigh rubbing his now rock hard cock through his tiny speedos.
Just as we lied down on the bed, we didn't notice but, Kyle had walked into the doorway. It must have been an amazing sight the two of us making out on the bed in nothing more than our tiny little black speedos. Kyle enjoyed the view for a minute or two before discreetly interrupting us.
Cough, Cough, "Excuse me boys."
We jumped to attention, totally surprised at Kyle's sudden appearance in the doorway. We both began apologizing.
"It's alright, looks like you two have some catching up to do from school. There will be time for that later. If you guys can come downstairs and start to get some drinks ready, people will start arriving any minute."
"No problem at all," we replied, relieved that Kyle wasn't upset about his two speedo waiters going at it.
"And the erections are a very nice touch boys." Kyle commented with a cheeky smile as he headed down stairs.
Martin and I smiled and decided that we would finish what we started later in the evening. We jumped up off the bed and headed down stairs (with our rock hard cocks bulging in our speedos). On the way down stairs I gave Martin the pleasure of following my speedo clad arse.
After getting some stuff ready behind the bar, the door bell rang. Martin was still getting some ice in the esky's outside (that is a cooler for my non-Australian readers) so I grabbed a glass of champagne in each hand and went to the door. The door wasn't closed (the lock and handle were pulled back but people rang the bell anyways). As I approached the door I asked the guests to come in.
A mid thirties guy pushed the door open and took a step inside the house.
"Evening Sir, and welcome to the party." I said, however it was apparent that the man, who was very well dressed in black trousers, a black shirt and a black jacket with some visible gold jewelry wasn't that interested in what I had to say as to more what was in my tiny black speedo. "Kyle is out the back just finishing off preparations, I'm Brad, one of your waiters for the night."
The man's gaze finally broke and he looked up at me. "Hi there Brad, nice to meet you I'm Jack, a business associate of Kyle's. You are in a bit of a precarious position there, with your hands full and all."
Jack was implying to the glass of champagne in each of my hands. Without giving me time to respond, Jack moved his right hand down to my semi erect cock and began to rub it. With his free hand Jack began massaging my speedo clad ass. It was odd but I can't say that I resisted at all, it was like two seconds before I was rock hard again.
After about thirty seconds of rubbing from Jack on my now rock solid cock we could hear another car arrive. Jack removed his hands, somewhat reluctantly I'm sure, from my speedo and took a glass of champagne.
"I'm sure I can help you with that later on Dave. And I must say, you are a wonderful waiter."
"I'll lead you out the back" I replied. As I walked through the house to the back yard I knew that Jack would be admiring my arse and I was loving it!!! I left Jack at the door to the yard and got back to my duties of welcoming everyone.
The party went great, Martin and I were busy the whole time but received lots of compliments and had our speedos rubbed an many occasions. Early in the evening Kyle came up to us in the kitchen, he said he saw someone grab Martin's arse and wanted to know if we were OK with that or should he put a stop to it. Both Martin and I were totally fine with it, two twenty year old guys in speedos waiting on a bunch of gay guys who were drinking... what else was going to happen? Kyle appreciated that we were so cool about it.
By 11pm the party had wound down, Martin and I were getting on top of cleaning everything and Kyle and about five of his friends were the only ones left. Kyle again came into the kitchen, thanks us for working so hard and told us our job was done. We could go home or we could hang out and have a drink if we wanted. We opted to hang out.
"You guys can put on some clothes... if you really want to."
I think the `if you really want to' meant that Kyle would like us to continue to hang out in our tiny speedos.
We poured drinks for ourselves, grabbed another bottle of wine for the table and headed out to join the guys. Even though it was summer, it was getting a little cool so when we came out to the outdoor table, Martin asked Kyle if he minded we sat in the hottub which was right next to the table. Kyle thought it was a great idea.
Martin and I slipped into the hottub.
Neither of us could keep our hands to ourselves under the water although we were trying to be discrete since there were six men sitting within three meters of us.
It came up that Martin and I had gone to school together. "Did you guys fool around at school?" one of the guys asked. "No, not even close" I replied.
Kyle interrupted the conversation saying that we were catching up though and told everyone that he had caught us making out before the party. There were hoots and hollers from the guys.
I started to blush but Martin had a completely different reaction. "Want us to show you guys?" More hoots and hollers and before I knew it, Martin was standing up, pulled me up and we were taking out again. This time our audience wasn't just Kyle, but Kyle and five of his friends who were giving us a lot of encouragement.
Once I got over the shock and embarrassment I started to enjoy it.
Martin pushed me back against the side of the hottub and began to lick his way downwards. This was totally out of the box for me and I looked at Kyle for approval which he gave with a nod. I distinctly heard one of the guys saying "Suck Brad's cock you naughty boy."
Taking his time, Martin's lips and tongue finally made it to the waist band of my tiny black speedos. He was playing up to the crowd. He grabbed the front of my speedo with his fingers on the inside as if about to rip them down but he paused... "Want me to suck him off?"
This was greeted with lots of approval and instead of ripping down the front of my speedo, Martin pulled it down slowly, really slowly, revealing my cock to all these guys. He tucked the front of the speedo under my balls. I was surprised at myself for doing this but I was incredibly horny. Martin then started to lick my cock. He was being slow and teasing but I was just too horny.
"I'm going to cum!!!"
With that, my cock exploded.
The first few spasms felt amazing but then I was ashamed at cumming so quickly. I went to pull my speedo up even before I had finished spurting my cum on Martin. He didn't let me, Martin took my cock in his mouth and got the last couple of shots down his throat.
The audience was enjoying it but I felt horrible and really embarrassed at cumming so quickly.
I tried again to back out but Martin wouldn't let my cock out of his mouth. Being twenty years old, I didn't even get soft before I turned on again. No kidding, it was a minute later and the shame was replaced with horniness. I was getting into it and Martin was demonstrating some mad blowjob skills.
Then, I was cumming again. I enjoyed this orgasm a little more than the first but still felt ashamed at cumming so quickly. Martin took my entire load and there more cheers for the guys.
This time Martin released my cock from his mouth and I slipped back into the water as I tucked my cock back into my speedos.
When I was adjusted again I made an excuse to get up and top up my drink. Being so embarrassed I grabbed my clothes and snuck out, I felt horrible.
On the drive home I received a text from Kyle saying I had no reason to be embarrassed and that I had put on a great show. In my rush to get out of there I hadn't been paid but Kyle said he'd leave the money in an envelope under his door mat with some extra for the show that Martin and I had put on.
Martin also sent me a text message making sure I was OK. He was focused on how hot it was blowing me in front of those guys. Over the next few days I would learn that it ended up being a seven person orgy with Martin being the center of attention and it resulted in Martin getting some more escorting clients.
I've never worked as a speedo waiter since that night but Martin and I ended up being fuck buddies for a few years and he taught me some of his skills.