It was a slow day at work, I was going around to the empty cabins at the holiday park and re-filling the coffee and sugar sachets, nobody ever monitored me, and a lot of the time I strolled around looking for things to do, killing time and talking to people who were staying at the resort, it was the easiest job in the world.
The privacy of the cabins was great, I was allowed to browse the net anytime I wanted.
I probably spent half of my working day browsing the net and the other half talking to people.
The solace of the job allowed for plenty of time to think, think about sex and I often jacked off in the cabins, simply because I could, it allowed me to relieve myself and focus on other tasks.
I received a text from Colin on this particular afternoon and felt the elastic cock-ring slowly apply pressure and grip the base of my shaft, akin to how a blood pressure machine does to your arm.
It wasn't your average vibration, I never once found it alarming, only pleasing because the tension came on so slow, slow enough that enough blood could flow through my cock and cause an erection, as the pressure from the elastic device increased, my cock hardened seemingly at odds with it. Because Colin was in complete control over it, he was in control of my cock which created a sense of trust and ownership.
The device put me on edge because I never knew how much tension was going to be applied and the thought of the possibility of it cutting off my circulation if it malfunctioned, as daunting as that may sound, only turned me on further and made my heart race slightly.
It was exciting! I'd experienced it so many times now and completely trusted Colin, I always knew the result of the process and that the device eventually began to decrease the pressure after a little while which I also found pleasurable and relaxing and ALWAYS masturbated afterward.
Because I worked on my own, there was never a chance of being 'caught out' during the experience and I always had a backup plan had I been talking to someone when the device was triggered.
The contraption was pretty much silent, there were times it went off mid-conversation and I had to divert my focus and often made out I had an incoming call and walked away.
I liked the idea I was 'flirting' with danger, like getting an erection in class, most of the people I spoke with were old holiday-makers, so it was the least of my worries.
Colin usually messaged me once a day and never made any demands, usually, he just sent through a cool illustration of an erotic image or a sexy gif and occasionally a time and date, that's if I never planned something first! I didn't consider him a pest or burden in any way, I had so much free time in my life as it was.
I eventually reached for my phone and opened the text in anticipation, a 'giant' cartoon devil illustration was displayed and over the crossed legs of the devil were many sets of young gay men who appeared ant-like in comparison to the scale of the 'giant' devil and were all involved in homo-erotic acts.
I'm not sure what it meant, maybe it was the idea of 'sin' or maybe I just found the image hot, however, it immediately turned me on.
Below the image said 'Saturday 8 pm, Just the 3 of us?'
I was down, I knew Saturdays were good money, it wasn't out of the ordinary to leave Colin's place on a Saturday night with a minimum of five hundred dollars depending on the event.
I began to consider myself a young Gigolo and was enjoying it, Saturday would be no different.
I spent most of the day chilling out at home, I'd done some clothes shopping and watched a movie then decided to take a shower and get ready. I put on a black jockstrap with random white lettering, a pair of loose-fitting black denim shorts with a few thin slashes in the thighs which displayed skin through the slashes, a black 'fishnet' top that was reminiscent of a woman's stocking and a pair of light pink vans with white socks that didn't show. I wore wore my hair out; long dark brown, beyond shoulder-length, naturally straight locks which were quite thick.
A week prior I decided to get both of my nipples pierced which looked perfect for this top, my fashion sense was becoming much more metrosexual which I loved!
Experimenting with fashion was amazing, I was enjoying feeling liberated whilst wearing whatever I liked without small-minded assholes bringing negative attention and slander towards me judging my attire and ironically calling me 'gay!' Yet here they were judging another guy's clothing, I had a new circle of friends in my life now and had started shedding my old life and distancing myself from these type of losers.
I wore a 90s style chain around my neck with silver beads which I thought complimented the piercings. I then grabbed my keys and started to head over to Colin's feeling the sexiest I'd felt since the night of the strip show for the masked men, there truly was a sense of stardom I carried into my new world, along with a new-found swagger.
I walked into Colin's and was greeted by Colin wearing a maroon bathrobe.
'Here he is, the man of the hour!'
I sheepishly grinned and brushed my hair over one ear.
"You look gorgeous!" He said, which made me feel incredibly confident, the reassurance was great because it was still a daring move, for me anyway! I'd spent the majority of my life wearing what society told me I should wear.
"There's someone I'd like you meet," he said
''Jordan, I present to you, Lucy'' Colin continued.
I loved being called Lucy, It made me feel like a rebel! As I was going against the grain of what hive-minded idiots were accustomed to.
Once I gazed upon Jordan, my bubble almost burst, I immediately felt like he was stealing my thunder. He looked like a model cut straight out of a magazine, He looked so good, almost like he 'wasn't real.'
Jordan almost looked synthetic and too good to be true, like he was an angel from a Michelangelo painting.
What instantly struck me about him was his incredible ass! An amazing bubble butt! He had a better ass than any girl I'd ever seen! I literally couldn't take my eyes off it, admiring this amazing specimen.
If I had to compare him to someone, I guess you could say a young Justin Bieber but with sharper bone structure and gray eyes, he had zero facial hair, not because he shaved, but his face was smooth like a boy as if he didn't grow facial hair yet at the same time looked like he was in his early 20s. I would later uncover he was indeed only 21.
He was wearing a white jockstrap with random black lettering, the polar opposite and inverted version of mine which created a duality theme. He had a great body, like a water polo player and completely smooth. Jordan was a fraction shorter than me at 5ft 8, he was probably 5ft 7 which suited his boyish good looks.
Usually, when I see a nice ass, I avoid looking to save bringing attention to it, however, it was impossible with Jordan! I was completely mesmerized.
Colin presented him as if he were Adam, the perfect man, and Colin was God.
I didn't feel jealous at all, I was comfortable in my skin, at this present point in time I was just in awe and becoming excited thinking of what lay ahead.
I was becoming seriously horny over this motherfuckers ass! It's all I could think of and couldn't keep my eyes off it.
He stood there and barely spoke, he didn't have to, he knew what I was there for, I knew what he was there for so we decided to spare the small talk!
Jordan, sensing my lust and desire kind pivoted and posed like a trophy. He knew he looked good! Colin's lounge room had become a human art gallery.
At that very moment, I couldn't wait to fuck him! I'd never had sex with a guy before, not given anyway, only received.
I knew Colin had been grooming me for it with the anal flesh-light a few weeks prior.
On this occasion, Jordan was to be the receiver, we instantly knew our places, with an ass like that how could he not be! There was a sense of 'purity' that radiated from him, enforced by the white jock.
I'd become confused with my sexuality lately; however, right now, at this very moment, I was gay!
I wanted to see him bent over doggy style, his big cock and smooth balls on display like a fruit bowl!
The word 'fruit' began to turn me on given what it was slang for, it was amazing what words could do! They had serious power.
Colin then began to pour some bourbon and coke which settled my nerves and I began to relax and enjoy the evening.
I slipped off my black fishnet top, shorts, shoes, and socks and stood there in my black jockstrap.
Jordan began grazing his eyes over my body and was attracted to me.
On a silver plate besides the bourbon bottle was Colin's Viagra, Jordan and I were semi-hard yet relaxed from the bourbon and I thought it would be fun to take one so we did, just for kicks!
All I could think of during the next half an hour? Fucking Jordan's ass! As we slowly sipped our drinks and shared a spliff around and admired each other's bodies.
We then felt the Viagra kick in quickly! About the same time as the Mary J! And we all began to share a laugh at how hard our cocks were becoming within our jockstraps which provided a playful and fun atmosphere; along with the strong sexual tension in the air, the viagra, and marijuana eased us into things.
Jordan and I remained standing whilst Colin sat down and gestured him over, calling for the spliff.
