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After years of cold feet and fantasising I finally had my first bottoming experience and I have very mixed feelings.
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Note: Im using one of my many alt throwaway accounts.

Hey everyone,

I thought I might as well share my experience with experimenting with bottoming and gay sex earlier this year since I have no one else to share it with in my personal life.

Background:

I am a 30 year old 5'5 young looking Asian 'straight' (let's not kid ourselves I'm bi) male living in NSW Australia who has been having gay fantasies ever since I was in high school. Now why didn't I just date men like every other bi/gay guy especially when gay rights was finally becoming mainstream ?

I can ONLY bottom when wearing an extremely OCD school uniform outfit being a school polo shirt with three buttons all done up, shorts and running shoes. Til this day I have no idea where this fantasy came from and I'm sure a lot of tops would be weirded out by that. Also I was more attracted to women then men, I only wanted men for their dicks.

When I turned 18 I went crazy buying school polos form different schools, plugs and dildos but stopped at just meeting other guys because I lived at home in a conservative Asian household. My fantasies ranged from being a school boy anal slave, wearing a plug to school with my ass full of cum, free use anal and even being tied up and fucked in the ass. At one point I even considered being a 'gay for pay' escort/sex worker but every sex worker and gay man told me to stop getting ahead of myself and actually have gay sex first before considering going down that path.

Experimenting:

I finally moved out of home at 29 for work and made a Grindr account to finally live out my fantasies. Since I was living in a rural town being Asian I stood out and I got more attention on Grindr within minutes compared to the years I have been on tinder seeking women. I mainly attracted older men with a Asian fetish sending me dirty messages and you know what ? I enjoyed the attention and the dirty talk, it was the theme I was going for. I also liked that men complimented me on my appearance, something women never did and for once I actually felt desired even if it was just for my ass.

The sex itself on the other hand didn't live up to my expectations. I didn't hate anal and it wasn't painful or uncomfortable but it wasn't the sexual awakening nirvana I thought it was going to be. It just felt like something going in and out of my ass, if anything I enjoyed being pluged more than anal. Also having a guy cum in me (don't worry I was on prep) wasn't as hot as I thought either, I didn't feel the warmth spread through me nor did I feel the load move around me after I put my plug back in. Even having regular fwb eventually became monotonous, I arrived with my ass plugged, he took the plug out and fucked me (with a condom), plug went back on and I went on my way. If anything I got more turned on by the idea of being used than the actual sex itself.

Current thoughts:

I eventually moved back home to Sydney and got rid of all my uniforms and toys after finding out that my decades long fantasy didn't live up to hype. I don't regret it and glad I finally got it out of my system but I was hoping for more. I still get a bit horny thinking about the idea of being used again and even entertain the idea of being an escort or finding a sugar daddy but when that happens I quickly masturbate so post nut clarity kicks in and come to my senses.

I'm 30 now and though I know that doesn't make me 'old' or undesirable I don't feel like a young twink schoolboy or look feminine like a femboy so I'm not really feeling the school boy character. I'm not against it and open to the idea in the future but I'm not rushing back in either and if anything I would rather find a woman who takes my role as the submissive school girl anal slave but knowing what dating as a man looking for a woman is like, that is going to take a long time.

Anyway I hope you enjoyed my incoherent rabbling. Thanks for your time and have a good day.

Take care gentlemen and enjoy your next happy hour.

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Posted
9 months ago