7 years
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My neighbour on the apartment other side of the hallway is a skinny white man. He is politeand I never thought anything of him. There was a condo party on I wanted to check the time for so gave him a knock.He said “Yeah come in” and he was looking at his phone in the middle of the room wearing bra and p******. I was OMG he was wearing mascara. No way am I gay but oh s***. A lot of things happened and it must have been the drink. I fucked his a** with my BBC. I f****** hate myself. I’m not homosexual. I f****** hate that s***. He’s a t***** or a woman or whatever he wants to call himself so it’s not homosexual. He’s five times prettier than most of the rough b****** who live here. I told him not to touch my a** because I’m not a woman and that’s homosexual. Women go on bottom you know? Nobody else knows and he said we could do dinner next Friday evening. He/she wants to wear a dress and all that s*** because he/she says he/she wants to feel good. We don’t live together and its just s** so…? He/she is tight and it felt good. F*** I can’t believe it. That b****** mascara is so pretty.

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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.