I have previously posted this here before, but will post it again as it seems appropriate.
Well, for me it started when I was about 17.
I live in a small town called Morisset, in NSW Australia. I was young, slim willing and horny, with little outlet other than my hand where I lived.
I used to buy a return train ticket to Sydney most Saturdays and travel up to Darlinghurst, the gay part of Sydney to get in to the glory hole venues, which I absolutely loved.
There was an older guy, not too good looking, Sicilian I think, who slipped a $50 bill through the hole to entice me to let him blow me. I happen to be very well endowed in the cock department. So on impulse I took the money and let him suck me off.
He was surprisingly good, sucking my cock, using his tongue well, sucking on my balls and even slipping his finger up my arse to encourage me to blow in his mouth. I didn’t think much of him as a guy but enjoyed what he did through the glory hole.
This became a regular thing each Saturday afternoon, when I travelled up to Sydney. I would play, suck and fuck the younger guys who were my regulars at the glory holes or at the beaches for free where we met, but would always get $50 from this particular guy who was willing to pay me to let him suck me.
Some of these younger guys I met with were rent boys out for some fun, I willingly went home with them for group sessions of sucking, fucking and being fucked. There is nothing like being on a covered floor with five other naked young guys, all of us oiled up, lubed up, lights out, total dark and suck and fuck like whores in heat, (which some of us were!) until sun up next morning, then home by train feeling the cum loads in your arse squish about.
These guys gifted me with passed on clothing I could not get for myself. G-strings, g string swimwear, custom cut shorts, which showed off my arse beautifully, cropped off t-shirts, thigh hi stockings and garter belts, as well as teaching me how to use light makeup to enhance the lines of my face and make me more alluring, which worked.
I used to travel from Morisset to Sydney central station in my normal cloths, with my sexy cloths and swimwear in a backpack, rent a locker at the station, change into my swimwear and shorts and head down to one of the beaches with a few of my friends for fun and sun.
We usually touched up our faces a bit at the beach to see if we could get a reaction from the other beach goers or attract a guy who liked somewhat feminine guys.
In my case this worked. I was approached by a nice guy in his 20’s who asked me to go swimming with him. He took me around the point of the beach, hugged me close, squeezed my bottom (which was on open display in my g-string), kissed me and asked me if I was up for some fun.