queer advice #52: a MILF of MILFS
"I played/sang to her an original song on guitar. she cried, asked to hug me, and whispered, 'I want so much more of you' into my ears."
It’s Thursday and I’m back with another queer advice column. Today’s question is from “a slut and a flirt with a lot of confidence“ experiencing long COVID and a tortuous, prolonged flirtation with their neighbor, a married MILF.
If you’re new to this newsletter or catching up after a break, there have been so many good questions lately!! Check out: ”I'm a 33-year-old dirty slut who loves to be alone and go to bed at 10 pm” and "It's so rare that I find someone that I'm interested in, and when I do, it's never great." Oh, and “I am a bisexual (she/they) who’s really struggling with internalized biphobia and setting really high expectations for myself when it comes to relationships.”
If you have a problem for this here advice column, send it my way :)
xo,
Maddy
hi hi hi big fan of the newsletter!!! ty! you are a great writer!
ok so, this is a classic tale of should-i-or-shouldn't-i with a MILF. i moved to seattle a year ago (from boston! hi boston! tbh miss you, boston, something i never thought i would feel!) and think i'm going to be in this neighborhood for a while. i live below my 80 yr old aunt, and the plan is that i'll help her move out and into assisted living when the time comes and i'll buy her house from her. we've built a really cool relationship over the years and i feel beyond grateful to have landed here. also, wow yes generational housing wealth.
i'm totally a community queer and love getting to know my neighbors. i am 100% a knock on your door with fresh cookies queer. i have met and become friends with many neighbors since moving here, and it's been a life-saver because i came down with covid and then long covid in april/may of this year and it's hit me extremely hard. i can't currently work and often spend days in bed (with my lover who also has long covid, fucking wild stuff) unable to do much.
one of these neighbors that i met early on and who has shown me the ropes of the neighborhood is a MILF of MILFs named audrey. classically, her kid is a nonbinary teen and this MILF very respectfully and sweetly asked me for some support thinking through how she can support her teen who wants top surgery (and who is under 18). this request obviously led to me lending audrey the book I was reading at the time, Lou Sullivan's "We Both Laughed In Pleasure.” it’s the extremely gay erotic diaries of Lou, a transman who lived in SF at the start of the HIV/AIDS crisis and who stunningly chronicled both his progression and feelings with his gender and physical body; as well as the super super hot gay sex and fantasies he was having.
this is a wild book to lend the neighborhood MILF because it is really just porn at many stages, but i'm a slut and a flirt with a lot of confidence and i made it very clear that this was for audrey to borrow (not her teen) and that it was explicit erotica. audrey responded (wearing a robe, holding a mug that said "BOSS," on the front steps of her large house with countless unfinished landscaping projects), that it sounded great and that the most sexual contact her and her husband have these days is “air high-fiving on I-5 as [they] drive opposite directions on the freeway.” she was excited to read queer erotica.
early on in our budding friendship, she was (obviously) gutting and renovating a lake house her and her husband had just bought, and would spend weeks at a time at the lake house, alone, hauling lumber and working on the house. she sent me a pic of her bruised forearms, palm-side up, in such a sexy and submissive way that I could not function for many minutes after receiving that picture. once, after we both opened up about some mental health struggles and progressions we’ve made over time toward healing, I played/sang to her an original song on guitar. she cried, asked to hug me, and whispered, “I want so much more of you” into my ears.
we texted a lot, and a month or so in I realized that I was getting a bit obsessed with her and would talk about her to my friends and lovers in a very sexual way, as if she and I both actively knew what was going on. audrey has a husband and a kid, has never mentioned being in an open relationship, wanting me sexually, or anything of that nature, and it felt weird to be fantasizing about her and very actively flirting in her direction without a clear understanding on the relationship.
things faded a bit because I came down with aforementioned long covid (and literally could not speak for 4 months because of a viral-induced paralysis of one of my vocal cords—I cannot stress enough to be vigilant in trying to avoid covid because it has fucked me and my lover up so hard and obvi the US gov’t doesn’t give a shit about supporting disabled ppl). ok anyway anyway.
I made cookies two nights ago, like massively decadent chocolate-on-chocolate cookies and I called audrey at 9pm and asked if I could bring her one and it was so flirty and forward and she came over right away and texted me later: “that wasn’t a cookie; that was a fucking orgasm in my mouth” with the hot lips emoji etc etc and I wrote back: “omg processing this text and blushing hard!!!” etc etc. my lover is like COME ON there is ABSOLUTELY SOMETHING THERE from both of you and she’s like, go for it if you want! but i’m like…..this is a MILF who seems sexually unsatisfied by her husband and who is, whether she realizes it or not, flirting hard with her hot nonbinary neighbor 15ish years younger than her.
I do not know what to do!!!!!!! I want to live here for a long time and I think that getting involved in sexual neighbor drama is a bad move given that I think it’s quite clear that she’s not in an open marriage. but also it feels somewhat strange to flirt so strongly and not acknowledge what that is???? I just want her to go to her lake house for a week, get PCR tested, and invite me down (also maybe my lover to if she wants to be involved)???? i’m usually a very communicative person because unclear sexual boundaries are not healthy for me and I like to be more upfront than guessing. also with long covid I have such deeply minimal energies and emotional convos (and even just hanging with people) have been so draining.
what do I do? I know there are many ways to go about it, but i’m a bit stuck on: address attraction and what kind of relationship this is head on and see what comes of that; or having waves of flirting which is probably deeply harmless but also I might get a bit too obsessive about at times? ok. that’s a lot of detail. i’d be very grateful for you thoughts/advice!!! also also for context, I am very into MILFs and that age and power dynamic and there is a lovely long-distance MILF in my life in which there is clear communication and boundaries and It’s a very good dynamic for me.
xo MILF-lover, 31
You’re very queer, MILF-lover. You’re committed to doing right by your friends, lovers, and wider community; you’re open to sex and relationships of different stripes, but only if there’s genuine care undergirding every interaction. As honorable as this sounds, it’s a relationship philosophy that would put most straight people into a coma. If Audrey were on your level, you’d already know. She’d be telling you, in no uncertain terms, that she’s down to fuck. Instead of feeling frustrated and conflicted, you’d be discussing boundaries and processing to your heart’s content. You’d be having a lot more fun.
I spent a lot of time writing and rewriting this response, and I kept coming back to the question of good crushes and bad crushes. Like, what’s the difference between feeling gobsmacked and pleasantly sweaty in the presence of a hottie and something that feels draining and miserable, like a fixation? In my own life, I’ve had crushes that were chill and crushes made me feel like shit. It wasn’t necessarily about the person returning my feelings—I’ve had crushes that ended in disappointment where I was able to disengage and move on, and crushes that resulted in lingering heartbreak and bitterness. I think, for me, it comes down to communication. When you’re talking to someone and they’re being forthcoming and direct, it’s easy to take that conversation, put it in a little box, and store it in the pantry of your mind until you need it next. When you’re dealing with someone who’s sending mixed signals, withholding information, or generally being a bad communicator, you can’t just put the conversation aside and move on with your day. You have to keep thinking about what they said and how they said it.
It takes time and energy to decode how someone really feels about you, which might explain the fixation you feel towards Audrey. She’s not telling you what’s up, so your brain is working overtime to parse her. For me, it’s clarifying to stop giving people the benefit of the doubt. If you like me back, I would already know. If you want to fuck me, I would already know. I want to acknowledge that life is complicated and there are exceptions to every rule, but I find that when I’m on the precipice of a positive romantic development, it doesn’t feel messy or like there are a million obstacles to clear. I start talking to someone and everything comes together via clear communication and mutual availability.
Next I want to affirm that Audrey is a horny, sex-deprived MILF. This is a real fantasy for you but from everything you told me about yourself, I really don’t think you want to participate in an honest-to-goddess affair. You would feel miserable if you fractured Audrey’s marriage, or had to avoid her and her husband for the rest of your life. You’re into clarity and boundaries, and being ~*the other person*~ or even sleeping with someone who just opened up their marriage would be like, the opposite of that.
I agree with your lover that Audrey is purposefully flirting with you. But I think you’re wrong to assume that if she’s sending the texts, she’s either down to fuck or too naïve to know what she’s doing. I think she’s somewhere in the middle—she might like the attention you give her, or feel attracted to you, but isn’t willing to transgress the boundaries of her marriage to sleep with you. Some straight women (It’s not for us to say whether or not Audrey straight, but I use queer as a political alignment and not like, the simple fact of feeling attraction to people who aren’t cis men) approach lesbians and other queer people with a lot of entitlement and malintent. It’s also worth noting that women have to navigate a lot of safety concerns when they express their sexuality around men. Maybe Audrey wants to share cute pics of her bruises and not have to manage the expectations of a sad, angry dude. She might also feel like it’s okay to flirt with you because you don’t threaten her husband. I don’t want to project too much onto Audrey, I’m just saying that there are a lot of reasons to flirt. You can decide for yourself if you’re into it. But if you’re in bad crush territory and stressed about “unclear sexual boundaries,“ you owe it to yourself to stop giving Audrey the benefit of the doubt and shut down the texting.
I know that was a lot. I hope that in the future, your crushes are 100% fun and full of clarity. I also want you to know that I showed your question to Boston and he/they say hi back. We’re sending you all our best!! I’m slamming a Dunkin cruller and watching road rage incidents on Mass Ave in your honor.
I've been learning a lot about limerence lately as a person who loves to crush. The understanding of good crushes and bad crushes through that concept has helped me a lot to navigate feelings and set boundaries with myself around them. When I get that high and motivation to be the best version of myself, I ride it because it helps get my energy up and be more creative and productive in my day to day life (though I know productivity can also be toxic, but this is more like spiritual productivity). This crush sounds like a 'ride the high' crush but likely not a 'we will fuck' crush. Great advice, I'm curious to see how things progress for the question asker ♡
hi you are so helpful this is so helpful ty ty. xoxo milf-lover !!!