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I met A in freshmen year of highschool, and within a few months she became my first girlfriend, and first kiss. Then as most highschool relationships go, we broke up over stupid reasons. We saw other people, and then ended up getting back together for a time in junior year. She’d be that point lost her virginity, and she took mine. We dated another eight months or so but again broke up before the school year was over. After that she actually moved away and I didn’t see her again until graduation. Apparently she’d never enrolled in a new school, just went to homeschooling through our district, and so I got to greet her as an old friend, both of us happy the other managed to graduate. She looked beautiful, and not to be to vain, but I know for a fact I looked my worst in freshman year and had gotten better looking each year, so I’d like to think she also was impressed by how much I’d grown.
A few months later I get a call. Her boyfriend and her had gotten into a fight. Apparently they’d gotten to the point in the relationship they felt comfortable disclosing their kinks, and whether they’d be comfortable with this or that. A was into some pretty intense but also ironically vanilla bdsm stuff. Like, it was the basics, tie her up, smack her around, use her. Classic goth girl shit. He however was into piss fetish stuff, and she said she wasn’t comfortable with that. His response was, “If you don’t want to do my stuff, we won’t do yours.” “Alright. Fine by me. Just regular sex then, like we have been doing.” “No, this isn’t fair. You’re shaming me for my kinks. If you won’t at least try this for me then we’re not having sex at all.”
What a fucking idiot. She laughed in his face, pulled out her phone, and texted me to come pick her up. We hadn’t spoken since graduation, so I was confused. When she told me what had just happened however, and that she wanted me to pick her up because, “If he won’t fuck me I knew you’d be happy to.” Cocky, and I always loved that about her. Plus it was too funny to say no. About ten minutes later I was parked in front of his house, waving goodbye to him as she got in my passenger seat. He waved back funny enough, somehow not understanding what was going on. I took her back to her house and folded her in half as she whispered into my ear how badly she’d missed me.
This already qualifies as a cuckold story, but we’re not even a third of the way done. The weekend later she reached out asking if I’d like to spend the night. I accepted.
After we were done she was laying on the bed and I was drinking a glass of water, and I felt that moment would be the perfect moment to ask if her ex had said anything to her since.
She got all quiet and said, “So… He’s not my ex.”
I was confused by what she meant. She explained that somehow he was that seriously dense that he didn’t understand he’d been broken up with, that she’d literally left him to get her guts rearranged within ten minutes of leaving his house. He thought they were still together, and had just had a fight.
“Ok, I didn’t sign up to be the other man here. If this is going to keep going you need to properly break it off with him.” She agreed and I went home.
We hooked up a few more times, and to my frustration, each time she had an excuse for why they hadn’t broken up. What was supposed to be a “Dude, fuck you for trying to force this girl to do something she isn’t comfortable with” had turned into an affair. It’d gone from something fucked up but justified under the circumstances to just a regular affair with some weird extra steps. Eventually I ended things with her over this, as it just wasn’t how I wanted another relationship with her to start. I didn’t like the cheating (ironic) and the fact she couldn’t commit to leaving him was enough for me.
However, before it became clear she wasn’t going to leave him, there was a day that we were at the mall on a date. Just walking around reminiscing on the terrible dates to the same mall back when we were broke highschoolers. We were talking about how different things were now that we were adults with jobs, responsibilities, and most importantly… Privacy. No more fooling around in a back seat or trying to sneak off on some trail.
“You could spend the weekend if you want.” She said, looking over her shoulder at me. “Put your stamina to the test.” She gave her hip a little half shake.
I walked up behind her, and seeing no one in the aisle would see, pulled her hips against me. “God that sounds nice.” She grinded into my crotch. “But, I’m really sorry I have something going on Saturday, I can’t.”
She leaned in against my chest and said, “Oh that’s too baaad. I was looking forward to it.” She pulled away, and as she walked out the front of the store she said back over her shoulder, “I wonder if (Name of my best friend) is free?”
If you’ve read my other submission, I’d alluded to the fact I have a long history with my longest friend. Maybe one day I’ll get into all of it, but all you need to know is I’d secretly fantasized of either a threesome with him or getting cucked by him for years. It even nearly happened with one of my exes. However I hadn’t told her this. I’d been open about my many fetishes and fantasies, but I’d never suggested anything like that to her.
I was stunned. She’d said it not as a threat, but with the purr of a treat being dangled in front of me. After a moment I composed myself and hustled to catch up with her.
I tripped over my words and stammered, “Hold on. When you said… Did you mean…”
“Oh yeah. Maybe I’ll even let you know when it’s happening to make it even more agonizing for you.” She smiled at me.
“How did you know-“
“I was your first. You think I don’t know everything about you?” She said it like it was common sense, but the idea she’d somehow extrapolated this secret fantasy of mine from my behavior over the years still felt insane. “I’m already texting him. He hasn’t come over yet, but he’s just waiting for a good day. I’ll text him, see if he’s free Saturday.”
“Are you, are you for sure?” My head was spinning. I know I should be mad. I should’ve been angry. Instead I felt like I was being offered a million dollars, and I had to make sure I didn’t misspeak, fuck it up, make her change her mind. Any other man would’ve been saying anything to make her take it back, apologize, promise they would be faithful. Instead I was desperate that she’d go through with this.
“Maybe we can make it a regular thing? He comes by, and after I give you a call, have you come over, let you towel the cum off me, or lick it off?” I’d never spoken about this sort of thing. Maybe she’d researched this fetish? “I can imagine it now, you pop by unannounced, I let you come in but say that you’ll have to leave soon as I’m expecting company. You ask for a quickie and I tell you no, I’m keeping myself clean for (friend), you can have the seconds if I’m feeling generous.”
Mind you, she’s saying all this in the middle of a public space, quiet enough only I can hear, but not a whisper, said confidently like it was the simplest thing I the world. Meanwhile my heart was going a million miles an hour, and I felt like I was vibrating, my hands literally shaking. I felt ravenous, like I could’ve torn her clothes off right there.
“Ok, we need to go back to your place. I’m about to lose it, I need you so badly.”
“Too bad, you said no. This ass is for (friend).”
“You can’t be serious.”
“Oh I’m serious. Next person to fuck me is (friend). You better pray he’s available this weekend or you’ll be waiting a while.”
After that she teased me frequently about the idea of turning my best friend into the owner of her body, with me only ever getting the leftovers, and the right to clean her if I was good. Sometimes I regret ending things when I did. My friend wasn’t YET comfortable being a bull, and I wish I’d held out at least long enough to experience everything she’d promised. Thankfully I got my wish eventually, which you can read about in my other post. Hope you enjoyed the tale!