Love the show. It’s so refreshing to hear these things spoken about without shame, yet with empathy for others. I enjoy that your show has a respect for reveling in pleasure rather than bragging about conquest tales. Hearing your advice, your empathy yet honesty, and your episode with Mistress Jay led me to write, thinking you might have the perfect perspective to aid in my silly recent hook-up dilemma.
I have an unusual/unique sexual background. I’ve been making myself come for as long as I can remember. I’m incredibly open and in touch with my sexuality, despite having had relatively few sexual partners and being very shy and humble outside of the bedroom.
You see: I’m a fat girl. I’m pretty. I dress well and flatter my shape. My face, tits and ass are usually enough to distract from the flaws. I identified with your description of Mistress Jay’s way of carrying herself. But I only hook up with men I’m interested in who pursue me. While I do “own it”, as you ask us to, I am very turned off by my weight being fetishized. I want no part of a man who is “into bbws”, because this way of being isn’t healthy and it’s something I’m working to eradicate. Don’t get me wrong: I work what I have, I just refrain from pushing it on others since I know it’s not what society is generally attracted to.
While I know I’m a strong force to deal with sexually, I’ve never been with someone where I felt like I had the upper hand— until last week. We met at a work-oriented happy-hour. We clicked like old friends and I ended up having an outrageously fun, hilarious night with a shy but fantastic man who unfortunately ended up very, very intoxicated, and somewhat intimidated by me (professionally & sexually). He was fantastically open about this fact and enthusiastic to participate.
The night ended with no penetration due to whiskey dick. He begged me to stay the night with him and he got very cuddly. In the morning I tried to bail quickly, but he encouraged me to stay in bed several times, coaxing me with great conversation and unending laughter. When I left, I wrote my number down for him. Despite the night’s mishaps, it was not an awkward morning after in the least.
He’s a complete dork. Most women wouldn’t look at him twice physically and I could run circles around him in the bedroom. But I want to fuck him. So badly (just fucking & perhaps friendship— he’s aware that I’m committed to an open, somewhat long-distance thing). I have a ridiculous urge to please him. For a thousand reasons, I feel like he deserves it. With less alcohol involved, I suspect he would be a great time.
It hasn’t been long but I haven’t heard from him. Normal enough, and I’m not desperate for it but I’ve never been in the position where I thought I might need to let someone know that I do indeed want them. But I figure even dorks might regrettably take a fat girl home and would prefer to leave it at that.
Does any man who regrets drunkenly bringing a fat chick home keep her around to hang out the next day? Would one text suggesting we hang out be too forward? I would NEVER do this normally, but his personality suggests that perhaps I should take charge. Should I wait until we run into each other again to attempt flirting? My far less sex-positive friends feel that a lady should never put herself out there and act like she wants it. This is pretty antiquated, but alas, I don’t want to seem like a fat predator.
I realize this is anxiety and probably silly, but despite being in my late twenties, I’ve never experienced this kind of hook-up dynamic. I would appreciate any insight.
Horny Unfucked Naked Girl, Eagerly Ready
Wow, so many things catch my eye when reading your email.
Your crappy friends should not be allowed to vote, hold public office or own land. I think this is really, really important. If they want to say that women categorically should not be aggressive, forward or “put themselves out there”, then they are not allowed to be upset when they’re not paid the same as a man. Let the progressive and intelligent women like yourself collect the extra 22% left in that wage gap! I hate when women (and men!) play games. They really just get in the way of an honest relationship. If a man wants to make a move, he should. If a woman wants to make a move, she should. It’s fine if someone personally doesn’t like making a move or showing interest first. But it infuriates me when they say they “shouldn’t” because of their gender and that everyone else of their gender shouldn’t do that either.
A big woman can totally be attractive, not despite being or because she is large, but just because she looks great. You don’t have to fetishize BBWs to think a particular BBW is attractive. So you’re not “pushing it on others” if you pursue someone. If they’re not interested, they’ll indicate it and you both move on. Just because “perceived convention” says fat isn’t fuckable doesn’t mean you can’t hit on men. Go hit on them!
Aside from your actual questions, there’s a relationship you have with your weight that pains me to read. I’ve had my own struggles with body image and wanting to be a conventionally sexy man (I still do). It’s fine to want to lose weight and achieve a body that you think is healthier and fitter and makes you feel sexy. But you seem to have this demonizing view on being fat that I really think is holding you back. Not every guy likes the ‘model’ body. Not every guy only likes that body. Every person, fat skinny black white gay queer hetero big nose missing finger weird mole tiny penis has the right to be a sexual being. You do not have to worry about “burdening” a guy by hitting on him just because you don’t think he’s into you. News flash: men hit on women all the time who have no interest in them. It doesn’t mean they can’t approach. Fat predator? Fuck that! If a guy isn’t into you, he’ll say so (and if he doesn’t, then he’s a wuss who is scared of being a communicative adult). Don’t go stalk anyone, but you have just as much a right as anyone else to make a pass at someone. So long as you don’t mind hearing no, they shouldn’t mind being asked.
So now to address your actual questions regarding this totally fuckable dorky dude you want to please for 1,000 reasons (one of which being that you think he deserves it). I won’t say that weight can’t be a factor in someone disappearing on you. However, I don’t think weight is a factor in your situation. So I’m going to strike the word ‘fat’ from your questions because all that matters here is that you’re a chick who went home with a dude and you want to go back over and devour his cock in some hole of your choosing. If he drunkenly brought home a chick and the next morning wants to keep her around, he is not regretting it. There’s something about you he likes and wants to learn more. As you said, he seemed shy and might be thinking similar thoughts about if you’d even be interested. H.U.N.G.E.R., two texts wouldn’t be too forward. Reach out. Say hey. Say you had fun and would love to do that again with a little less whiskey. Throw in a winky face. See what he says.
You could wait till the next serendipitous moment you run into him to flirt, but why wait? You have his number, right? Call him you dork!