Growing up i always avoided the few tickling situations that arose in my life through a fear of being outed. I remember one very prominent time when a girl who liked me playfully blocked a door i wanted to get though and said id have to 'tickle my way through' and as much as i wanted to tickle her i froze and then ran away lol
My very first experience came when i was on a college trip in Spain (uk college & we were both 18). I was getting friendly with a stunning brunette, we'd just come back from a bit of shopping and we'd gone back to her room to wait for dinner. She was laid on the bed with her friends chatting about the clothes she had bought and i was sat next to her. I don't know what came over me, it was almost my subconscious controlling my movements, but i just reached down and ever so lightly poked her side once. She gigged and flashed a playful look at me and said 'hey im ticklish there' ... and then i froze and ran away lol
As silly as it sounds that poke changed my life like a weight being taken from my shoulders. I had tickled someone! Ironically i didn't know it'd be nearly a full decade before id get to tickle someone in a fetish capacity lol but i was happy!