My very first? There was a guy that I was friends with in high school, used to ride with him on the weekends and stuff, I’d sometimes sit a little closer to him and twirl his hair with my finger. He had short, dirty blonde hair and it was a little curly, I thought he was so cute but he had no idea I was bi or a dresser.
So forward to being out of school. He’d got married, I wasn’t. It was rocky for him/them, she was very hot in the ass which is why I guess he was so attracted to her. Things didn’t work out though… So one day I’d went over to his house to just hang with my buddy. We went riding and again, I was a little too close on the seat of that pickup, found myself wanting to play in his hair again…
We end up at a video store and renting some porn, go back to his place and start watching it. He gets worked up and needs to jack off, he didn’t tell me but the all of sudden “I’m sleepy and need a nap” was a giveaway. I took the chance and said “is a nap all you need or do you need some help with something else?”. To my surprise, he said “you go both ways don’t you?”, naturally yes was my reply.
So off to his bedroom we go and I asked him if his wife had left anything to wear there, told him I loved to dress up and I’d dress up for him. Lucky me or us, haha, she’d left a lot of stuff there, especially some lingerie that he’d bought her. Even more lucky, some of it fit. So dressed in his ex-wife’s lingerie, up on the bed and between his legs, I was sucking my first cock. I offered my pussi to him but he wasn’t ready to go that far I don’t guess. So I sucked his cock, his balls, I did my very best considering I’d never sucked cock before that.
He called me by her name and said he was about to cum, I kept going and then he filled my mouth and throat with his warm cum. I swallowed it all, kept sucking him to clean him up and then I laid down beside him and up on his side. Nothing was said for awhile, then he told me how good I was and how much he appreciated it. I told him he was very welcome and I enjoyed doing it for him, that I would any other time he needed it. But.. that was the only time it happened and I didn’t even get to keep the nightie I had on, darn it.