Hey,
My 1st gay experience happened in high school and involved my favourite obsession- swimwear!
so a bit of background, i went to a mixed boarding school. Basic kit stated swimming trunks, so every guy needed them, but most still wore
shorts, the school had its own pool too. A fav hobby at weekends when people were away home was to go to their rooms and borrow their trunks to wear and have some fun in, before returning them.
There was a lad the year above me who i’d snuck in to borrow his trunks, after a weekend of wanking myself stupid i returned them, only for him to catch me at it.
obviously he wasnt very impressed and threatened to grass me in to the staff. I kept apologising, trying to come up with an excuse, but he wasnt having it. I told him id do anything, which got his attention. He told me to tell him the truth about what i was doing with them, so i did nervously, hoping he wouldnt spread it to everybody!
After some thought he told me to put them on, confused as hell he had to tell me several times before i got the hint. He got me to strip fully naked before getting dressed in the tiny black adidas 3 strip trunks. He picked up my clothes and locked them away, then pulled out his cock and told me to get on my knees. He was getting aroused, it wasnt a massive cock, but it certainly opened my eyes! I gripped its shaft, as he pulled my head towards it, pressing his tip against my lips, i yielded, letting his hard shaft slide into my throat, at first i gagged and coughed but soon got into a rythme of sucking and licking, very quickly i felt what i now know was his precum shortly followed by his big sticky hot creamy load, pulsing hard into my mouth, trying not to choke as he got me to keep working it, it was everywhere, all over me from where id dribbled it out. I stood to ask for my clothes back but he wouldnt let me go, not until he had watched me wank. To say i was quick was an understatement, i slipped my hand into the trunk and started working its shaft, hard and fast, soon my cum was squirting through the material, making so much mess!
I stood there afterwards, unsure, until he passed me my clothes. He told me to leave the trunks. As i dressed i felt shame at what had happened, but also horny at what id just done, id never done ANYTHING like that before.
we hooked up quiet a few times over the next few months, he would always have somebodies trunks for me to wear, i got him wearing them too! But thats another story.