7 years
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Hi, so Im at the end of my first year of University and a small group of friends went out drinking. I realy like one of the girls on the cource and we get along like a house on fire. Here is the thing, that night she took me aside and we danced and drank on the dancefloor, she told me that she realy liked one of the other guys on the cource, saying she just wanted to get it off her chest. That is’nt all though. I found out from another friend, later that night, that this person I rely like and am attracted to is trans. They used to be a girl but now have a d***. I’m not sure weather they did’nt like/trust me enough to tell me that or if they just thought it was common knoladge. Furthermore I’ve always considered myself straight but now I’m having a bit of a personal crisis as IDK if liking them makes me bi.

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When I was younger, about 16, I was insatiable and as a result of having my first anonymous hookup with another kid that was 16 (off omegle of all things) I sought to have more.
In this effort I downloaded Grindr and lied about being 18, eventually finding someone who hosted an anon darkroom not even 5 minutes away and who was more than happy leaving their door unlocked and a** ready. After I was invited over and tentatively entered their place I immediately set about u*********, going to nothing in a minute and slowly started up the steps to his room. Once in his room I was approached in the dark by him – a 30-something yr old man who was equally as naked but twice my size – and he reached down and started to blow me once he settled on his knees. Within minutes once I was sufficiently erect I prodded him onto the bed and had him bend over, eventually sliding in without any additional lubrication and begun to – at the age of 16 – f*** this older mans a**. I went for about 20 minutes by my estimation and slowly over the course of the f****** went from doggy, to sideways to having him lie fully down whilst I went to town on him.
Eventually I finished in him and got up and left. Once home I gushed to him about how much fun it was and how I appreciated him taking a chance with me, with some more conversation eventually leading to my age being revealed and – to my own surprise – him revealing that he’d prefer it if we kept going in spite of it. I’d meet him continuously, probably once to 3 times a month or even multiple times in the same week until I moved away at 18. I never saw his face but I remember being inside him so vividly.