Disclaimer: I might not be the best storyteller, but I'll try at least. This story also involves racism, cheating and a top putting his bottom in panties, so if that's not your thing you shouldn't read.
To understand this story, you need to know I've always been a bit gay, though I've tried to hide it and I've been insecure over the effeminate behaviour that I've tried to repress (even though I've never been fully successful). This insecurity is also compounded by the fact that I happen to be a 19-year-old 5'7 Asian guy, which is basically the stereotype of a non-manly guy. Nonetheless, I dated a few girls in secondary school (high school) and even had sex with an exgirlfriend a few times.
On this Saturday, I decided through a mix of horniness, boredom and opportunity (my mum was away on business) to download Grindr, and messaged a couple guys in the "Jock" tribe, not quite sure whether I wanted to fuck or be fucked. I guess fate decided that I should be fucked: all the guys who messaged me back were tops. I invited one in particular round to my house - he was white, handsome in a kind of preppy way with a swimmer's body and an average length but thick dick. He was also "straight", and lived with his girlfriend. I spent the next hour in alternating terror and horniness as I prepared for his arrival.
Then he did arrive and oh my god he was so much more handsome than I anticipated. He shut the door behind him, and brought my face to his to make out by placing his hand on the back of my head. (I'm glad he did - it set the tone for our encounter and I'm also not sure that I would have been able to make out with him solely of my own accord.) His other hand he placed on the small of my back, and I decided to reciprocate by feeling up his abs. The hand that was on my back inched its way down my jeans, and eventually his finger began to probe my asshole. He broke away from the kiss. "You weren't lying about being a virgin," he smiled. "That's one tight, fresh pussy." Before I could say anything in reply, his finger suddenly penetrated my hole and I groaned. He smiled further, and then added another finger. His other hand took one of mine and placed it on his bulge. "Feel that," he commanded, and I did. It was much bigger than mind, and it seemed firmer than mine had ever been.