I grew up with Janine. She was one of the first girls I did anything sexually with. A rail thin blonde. Cute face. Tiny little tits. The perkiest nipples. Incredibly horny. This story is about an ‘arrangement’ we fell into one summer.
I was home from university. She’d never left home. We’d loosely stayed in touch but had a big circle of mutual friends. I encountered her in a nightclub one night. We flirted and made out but other than some brief gropes in the corner of the club, things didn’t go any further that night.
We started texting. One night she gets in touch. “I’m bored. Nobody’s home…”
I’m sure we all know what that message means. I hot foot it around there and we pick up where we left off years previously, namely her laying back and letting me do all the work. She had a tight pussy, waxed to perfection. Each time my length went all the way inside her she’d yelp, a red rash forming over her tight chest giving away home much she enjoyed it.
Janine wasn’t a skilled lay but she was fun to fuck. She’d try a few new things but had some hard limits (no anal – I asked more than once).
The first time I asked to cum on her face it was a no. She asked me to shoot over her tits instead. Me being young (and a bit of an asshole), it was a shame when one shot ended up hitting her chin. “It’s not that bad, is it?” I asked her as we cleaned up. Apparently not.
A few days later and we’re at my mum’s house (home alone) but Janine was on her period. She still wants to suck me. She’s kneeling on the floor, topless, her jeans and socks still on, bobbing away when I feel I’m getting close. I let her know. To my surprise, just as I’m starting to cum (I was pretty vocal: it was really good head!) she pulls my dick from her mouth and lets me cum on her lips and chin. It dribbles onto her chest. A big grin from her. A big grin from me.
The next night, it’s the same routine but at her place. Her head game was strong: a blur of blonde going back and forth. This time, she pauses briefly to tell me some good news: “I want you to cum on my face…”
She resumed sucking my cock. After her announcement, it didn’t take me long. I took charge, taking my dick in my hand and spraying her whole face with whatever I had. She flinched when the first rope hit her, impressively thick and white, causing the next two ropes to catch her hair and forehead. I was impressed with my work. Janine was less so, though only slightly.
When done, I asked her how it was for her. She laughed and said it felt good but she’d been worried about it going in her hair. She let me do it that time because she had time to wash it afterwards.
“So can we do it again in the future?”
Janine was smiling. “If you’re lucky!”
I was lucky that summer (and a number of other times in the following years), as we’d hook up if I was in town and we were both out of a relationship. Turned out she really got into guys cumming on her and she’d sometimes ask for it when I was fucking her. What kind of gentleman could then say no?
Source: reddit.com/r/gonewildstories/comments/11bkaz4/earliest_friend_turns_into_a_fwb_with_a_love_of