On Questioning Our Feminist Intent

Q: I crossdress and I am planning to eventually transition, MTF. The issue is money. I have heard women can earn extra cash selling their underwear online. I don’t know if it actually is a good money making idea but ethically speaking, do or should I tell the guys I’m still male? Not sure on this point, but if I can earn more income, does it matter? Or am I glorifying women’s bodies (even if it’s my body) to be objectified by creepy men? Why does it feel like I’m being a traitor to womenhood?

Saying that being a woman is complicated is an understatement. There are so many messages women get on the right way to be, think, feel. Even from other feminists. I really enjoy the book Bad Feminist by Roxane Gay. If you haven’t read it yet, or if you’re not familiar, I highly recommend you check it out. The general idea is that there is no such thing as the perfect feminist. All women are imperfectly perfect.

I would also check out Kate Bornstein who you should wiki if you do not know her. Here are a few suggested reads from her writings:

A Queer and Pleasant Danger
Gender Outlaw
My New Gender Workbook

Bottom line: Follow your gut and your instincts. If something does not feel right, don’t do it. But I don’t think you’re under any obligations to not do it, either. If it doesn’t make you feel good, if you feel unsafe doing it, I would advise not to do it.

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Three Quick Ways To Ease The Tension In Your Fight

So, we fight. It’s not very often and it’s not what I imagined it would be like. The longer we’re together, the better we’re able to work together. Here are some tips I think are pro. Try incorporating them into your next disagreement or serious conversation.

1. Pull A Goof

You’ll have to time the pause right for your fight, but there’s nothing to bring a couple closer together than a gentle eyebrow wiggle in the middle of a tense moment. Play this card wrong (or too often) and you’ll be accused of being unable to have a serious relationship talk. Don’t avoid difficult subjects with humor, but use them as a playing card when you want to remember that you and your partner are actually fighting together, not against one another.

2. Say “You’re Right”

Or “I didn’t say that the best way I could have” or “I said some things I did mean and some things I didn’t mean.” When you’re angry you often get defensive. If you don’t get defensive, you probably get some other emotion that doesn’t feel too hot. Whatever that emotion is can lead you to say some things that aren’t strictly true. You have to learn when to say you’re right. You don’t want to be right all the time, but it’s hard to remember that when you’re in the heat of it. Sometimes you should want your partner to be right, because it means they were able to see something you didn’t. That’s what a partnership is.

3. Ask Your Partner What They Mean

When you don’t quite understand what your partner is saying, ask them what they mean by repeating it back to them. In therapy this is called mirroring. Repeat what they said back to you word for word. When they hear it coming out of your mouth, they might realize that they didn’t quite phrase it exactly right. It might give them the opportunity to add more clarifying details. Be sure you don’t put words into your partners mouth, which I can at times be guilty of accidentally doing. Sometimes saying the same thing in a different way can help both partners come to an understanding about what you’re actually talking about. Best way to fix a misunderstanding in a relationship? Communicate.

Did you end a fight and things don’t feel totally 100% okey dokey yet? The cool down period is a good time to think about how your partner is feeling. At the end of a fight you’re fully feeling your own emotions. You might feel hot, you might be crying, you’re probably pretty emotional. Consider after a breath where your partner was coming from and approach the conversation a second time with as much understanding as you can muster. Not all arguments find light after one conversation.

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How Do You Arrange a Heterosexual MMF Threesome?

Q: How do you go about having a 3some? With 1 girl, 2 straight guys

I like this question because a lot of conversation tends to focus on the two girl / one guy threesome.

My advice for having a successful threesome is very simple: you cannot expect perfection; learn to seek adventure and fun between the lines of what you imagine perfect sex to be and the actual experience you’re having. Expectations for an experience can often ruin that experience. Prepare as best as you can for shared goals, general compatibility and safety.

One common issue in threesomes is that three is an odd number.

That means that one person is often left to be the circling participant. They are either watching or meandering around the outside of the action. That’s perfectly okay if they are aware of that, prefer that, or are comfortable making their way back in.

Another common way to handle this balance is by making one person the center of attention.

In a two straight guy one girl threesome, it’s likely that the attention is focused on the girl.

There is some difference of opinion on how to arrange a threesome. Should it be people you’re really close to and comfortable with? Should it be people who you’re just kind of friends with? Should it be people you don’t know very well and don’t see again? Different people are going to have different opinions on this. How you form your threesome depends on what part of the threesome you are, and whether or not you’re in a relationship.

Each participant matters (!)

Generally I would go into the planning process with the understanding that everyone in the threesome is sharing an experience, so everyones experience matters. So, if you’re planning the threesome, take everyones feelings into consideration.

One size doesn’t fit all 

Because threesomes vary so much, it’s difficult to give advice that’s one size fits all. Are you in a relationship and looking to plan a threesome? Are you single and looking to have a threesome? where in the world do you live? What is your age range? Do you feel like you’re generally surrounded by pretty sex-positive friends? Are you in a pretty sex-positive community? Are you looking for a one-time threesome? Do you want to really plan it out to hopefully achieve a certain scenario or are you looking for something more laid back and relaxed with no agenda?

Think about these questions and how they apply to you and if you have additional questions on the subject, let me know, and we’ll talk more!



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Should Your Partner Be Your Best Friend?

holding seashells up in a heart

Jason is my best friend. By any and all qualifications that matter in a friend, let alone a best friend, he ranks supreme. He is the first person I text when I want to share news. He’s the first person I text when I have nothing to say. And he’s the only person that I’ll actually use my phone to call – except the government, my healthcare provider, and very rarely with some shame, Comcast.

How I communicate with him makes him my best friend. Not just when and how I communicate, but also what I say.

At the start of a relationship we tell each other whispered secrets as tests of loyalty. In bed at night, those first sleepovers, we stay up later than we’re used to, running on pure adrenaline. We tell each other secrets. I feel this way, I’ve never told anyone else before. We wait for them to scream. They don’t. We fall into the honeymoon period, we rock back and forth, we fall in love. And then, deep-seeded security, comfortable and content, it becomes all too easy to stop sharing these things. More often than not it’s because these feelings we used to share are now about this person. We wonder if it’s safe to share. I am afraid, are you afraid too?

A best friend says yes, a best friend says, lets be afraid together. Then maybe we won’t be so afraid anymore. The relationship you have with your partner, because of the depths it seeks, is one of the most important relationships you have.

The problem with articles that ask this question, this big question: who is your best friend? is that they work off of, and often value, outdated modes of relationships. Antiquities of culture. This perception that you will have a soul mate of a best friend, the same way you have a soul mate of a partner. Maybe you have a best friend, just one, the very best. The person who you have rated and graded, who floated to the top, the science experiment of all your people. I look at my friends and I see too many. I know that the work I put into these soul mate-friendships is what makes them special. No arbitrary grading scale will do.

Putting people into these boxes of best or worst or most valuable isn’t fair to me and it’s certainly not fair to my friends. I steal from polyamory, I steal and I don’t care. They’re all important to me in different ways.

Learning how to express this, learning how to value your friends so they feel best, that’s what’s the most important thing.

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When To Say I Love You

when we moved your mattress out of your apartment it got stuck on the stairs

and I looked at you and said that one day we’d find this funny

and I still remember the look on your face because we were already halfway down

and when we made it outside, it started raining

so I sat in the bed of the moving truck and laughed

and told you to sit next to me

and the canvas of my shoes got wet

and my hair got all frizzy.

we’d just been dating for six months when we held hands on that same old walk

still in that phase, you know, exploring each others palms like fortune tellers

and I said “when you want to move in with me, I’m ready”

and you said “I think I’ll end my lease early”

and we rationalized the cost of


ending your lease

that trip to ikea

those new appliances

because when you say something out loud and it sounds right

when it just sounds like the thing you’re going to do

the perspective changes and

everything flips all upside down, you know

what used to be down is up and what used to be up is down

and I think that’s love

that dizzy feeling I get when

you dance in the kitchen

or read me harry potter

or call the cat pet names, we both answer.


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How We Set Up Our Joint Checking Account

We did it, guys. We set up a joint checking account. We are sharing our finances. I’ve had a couple people ask how we set it up and how it’s been working since we started so I’m sharing a pretty detailed breakdown of what we do. It’s easily customized based on what your expenses are! How do you and your partner handle money?

1. List your recurring shared expenses

Our recurring shared expenses are:

  • Rent
  • Electric
  • Comcast
  • Netflix
  • Hulu
  • Apple iCloud
  • Spotify

For each point we broke down how much each person would pay for that thing. For everything except rent we split it 50/50 down the middle.

2. List your recurring shared expenses pt 2

The above items are fixed and recur every month, on an automatic basis in most cases. But there are a lot of other things we spend money on together that aren’t on that list.

  • Groceries
  • Eating Out
  • Entertainment
  • Shared Home Purchases
  • Our Kitten
  • Gifts for Friends
  • Laundry
  • Gas

3. Set a Budget

For part two we set a budget. We looked at how much we usually spend on groceries per month and then determined what would be a good place to try and stick to. Then we figured out, for each bullet point, how much each of us could contribute to that budget. Sometimes one partner might care more about one category than the other. Sometimes one partner might make more than the other so it makes more sense for them to add in a bit more money. Discuss until you come up with numbers that feel pretty fair on both sides.

Between these two lists, and after discussing a budget, you should each have an individual number that you will be contributing every month to your joint expenses.

4. Optional: Savings Account

I really liked the idea of putting aside a set amount of money each month for shared savings goals. Big ones for me are travel/vacations, an emergency fund, and larger house items (furniture.) You can tuck this money aside and watch it build until there’s enough stocked away for x-emergency or x-fun thing.

5. Budget What’s Left

After I had a number for our joint account, I subtracted that from what I make each month. Whatever was left was “my money” and I created a separate budget for that. This is where my money usually ends up:

  • Individual bills
    • Health bills
    • Credit card payments
    • Phone bill
    • Other various payment plans
  • Books
  • Craft supplies
  • Blog fees
  • Happy Hour with friends (when J isn’t with me)
  • Eating dinner or lunch out (when J isn’t with me)
  • Snail mail (stationary, pens, greeting cards)
  • Gifts for J

6. Set up a Recurring Transfer

You could go straight to your workplace and have the direct deposit go to two different accounts. I’ve gone the other route and have all of my money deposited into my personal account and then transfer over to our shared account. Because I get paid every two weeks, I divided my share by two, and make two transfers each month.

So far our system has worked very well. It’s nice to not have to think about who paid for what and when and have to transfer money back and forth through Square Cash. It also created a really nice feeling of partnership. We’re working together to save money, we’re working together to spend smarter, and we’re enjoying the money that’s in our account, together. Ultimately this step into togetherness is why I was interested in the shared account, to begin with. The fact that we share mostly similar ideas about money and are both working full time made a big difference.

I always thought people who fought about money were silly. Money isn’t worth an argument. The older I get, the more I see how important creating clear ideas about money is. It’s wrapped into how we want to live our lives, how we want to grow old, how we feel about being prepared.

Don’t belittle these conversations and don’t run away from them. Think of them as multi-faceted conversations about what you feel is most important in your life and what kind of life you want to have with your partner. Then start preparing to make that happen as best as anyone can.

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Q: New Partner Struggles with Erections?

I’m a 31 year old female who had been seeing a guy for a few months. The relationship has been fairly happy with some minor bumps in the road. He’s 29 and I’m his very first girlfriend. Sounds weird, I know. My problem is, we’ve been intimate several times with less than spectacular results. Being his first partner, I thought he’d have little trouble becoming erect and/or climaxing. I have been with several virgins in the past. I sadly have an extensive sexual past. I have no trouble getting him hard, it’s getting him to stay there us the trouble. Also, when we give up on intercourse and ultimately settle on separated masturbation, he gets super close but can’t finish. I have no trouble finishing whatsoever. Dont know if this is relevant but we are both overweight. Please help because my libido is incredibly high and I’m getting tired of my own hand.

It’s often the case with new partners. Sometimes you orgasm too quickly, sometimes you orgasm too slowly. It’s an extra curveball when your new partner is also new to sex, period.

My best guess is that he’s just nervous.

I don’t mean that he’s necessarily actively feeling nervous. When we’re not totally in-the-zone during sex, it can be difficult to get and stay aroused. If he’s not used to the flow of sex, being naked with someone else, or fooling around in general, he may be struggling to stay in the right mindset to stay that maximum level of arousal. Once you struggle to stay hard once, that fear that it will happen again can be self-fulfilling.

For me, the answer rests within this question: when he masturbates by himself is he able to orgasm fairly easily?

If yes, there’s something holding him back when you’re together. Maybe he is anxious or stressed or nervous or maybe he just hasn’t quite found his groove yet. I’d remove any pressure to have intercourse and I’d remove any pressure to actually orgasm. Take a step back and just be naked together and explore what does or doesn’t feel good. It may even help to encourage him not to orgasm, and rather see how many orgasms he can give you prior to his own.

That puts the attention back on you, gives him something positive to focus on, and likely results in a relaxed atmosphere that is more conducive to orgasm.

It could also be that there’s something you two are doing together that is mentally or physically turning him off. Maybe the thing doesn’t feel good, and he’s unable to communicate clearly that it doesn’t feel good. You’ll have to consider this and see if you can pinpoint how clear your communication has been thus far. Of course, sometimes people also have very specific fetishes or kinks, and if he’s been living 29 years in the head of those fetishes/kinks it might be an adjustment having actual real physical sex without those things. Have you brought up kinks or fetishes yet? He could have one very specific thing he’s doing when he gets himself off that he’s not doing when he’s with you. Whether it’s a kink, or the way he plays with himself.

Finally, and I don’t know if this is what you meant by sad, but I hope you know there’s no shame in having a lot of partners. All of that experience can make you a great fit with this new partner. While it’s possible to have weight-related issues in the bedroom, from what you described, I wouldn’t jump to that as the root cause. Knock it back a few steps and start over, more slowly. Whether you’ve been dating for a few weeks or a few years, it’s never too late to get to know each other all over again.

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My Ultimate Fall To Do List

What’s on your list? Have suggestions to make any of mine better? Leave ’em in the comments! (Crossed out means I’ve done them this year!)


  • Get a new pair of rubber boots [1]
  • Go pumpkin picking[1]
  • Get hot apple cider
  • Make mulled wine [1]
  • Make pumpkin bread
  • Create a fall door wreath[1]
  • Finish re-watching Stranger Things S1
  • See a horror movie in theaters 
  • Take a long walk in the rain
  • Watch the Swifts fly in [1]
  • Re-watch the original IT mini series
  • Gather pinecones from the park for free decorations
  • Make roasted vegetables
  • Watch all the fall television    
  • Do a corn maze
  • Throw a football
  • Make fondue 
  • Make pumpkin pie 


  • Make pecan pie
  • Throw a classic thanksgiving dinner
  • Write ‘thankful’ letters to friends
  • Plan a 29th birthday party 
  • Create a cozy blanket bed to cuddle in with the windows wide open
  • Go to the coast
  • Make butternut squash soup
  • Go to a winery 
  • Re-learn how to knit
  • Break out the wool socks
  • Journal (regularly) at night with hot tea
  • Go to a haunted house 
  • Hand out halloween candy to kids
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Ways to Prevent Your Coworkers From Finding Out You’re a Scared Little Girl Hiding in Adult Costume

Buy Adult Pants

Drive to the furthest Banana Republic, Gap or J.Crew from your home. Turn off your phone so you can’t be tracked. Find a salesperson and with hushed voice, ask what the most adult pair of pants they sell is. When they direct you to the pants, make up a lie like “these aren’t quite as adult as my last ones I bought on my business trip to Guatemala but they’ll do.” Guess your size. You gotta get the fuck out of dodge.

Drink black coffee

Proclaim loudly throughout the day the following series of coffee related phrases:

  • I totally can’t work until I’ve had my coffee
  • This is only my fifth cup
  • I don’t even know what creamer is
  • I have a tattoo of an aeropress on my left asscheck
  • I need to make my late afternoon coffee run
  • I prefer a light roast because it has more caffeine

Have a desk plant and a photo of yourself and your significant other (your ex-boyfriend or platonic male exchange student friend works) in a custom frame from an actual frame shop where you know the name and beard style of the man who opened the store

If someone asks you what kind of plant it is, just laugh hysterically like they’re the biggest idiot you’ve ever seen. Swivel your chair in the opposite direction. Practice swivel first so you don’t accidentally swivel all the way around to face them again.

Utilize words like Utilize, and the following

  • life plan
  • retirement
  • ira
  • accomplishments
  • scope
  • direction
  • contract
  • client
  • management style
  • due process
  • google calendar
  • document
  • warmly
  • connect
  • partner
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Thinking About Gender Identity in Dating

I am new to dating as a closeted CD.planning on eventually transitioning MTF, and an interesting guy is communicating with me, online dating. I like men, but he’s dated other cd/tg and cd himself. Not sure how I feel about that, I like masculine men, here’s his last message: “Ooohhh the dating questions!! 😄😄 well, I am open right now and hope I can find a serious LTR. And in terms of dating history I have dated some women, but mostly TSs, TVs and CDs since I was a teenager, in fact, I have done (and still do regularly) some CDing myself with bad to mild results at best LOL! Logest relationship I had was with a pre-op TS that took me to live at her house (with her 2 brothers, sister, nephew, brother in law and mom) and for 2+ years we were a big happy family. So, what about you?” Should I give him a chance? I feel like a hypocrite, but fear STDs with his attraction to cd/ TG peopleand his sexual attraction to CD himself. Does this make any sense? I guess I want a masculine man without the urge to cd himself. I don’t want to be a fetish. my gender feelings are not related to clothing. I am making a moutnain out of a molehill?

Go with your gut. If something doesn’t feel quite right, you shouldn’t force it to fit. Do you feel the heart flutter? Are you attracted to him? If no, life is short, on to the next one!

If you are into him and he does seem to be legit, try coming to him with these concerns. Ask him about his sexual health history and how often he gets tested. Be clear about what kind of person and relationship you’re looking for. He’s already given you a little bit of that himself and it can be an ongoing and evolving (over the span of months, or years!) conversation. Express your concerns for being fetishized. Does your experience and your gender identity play a role into why or how he’s attracted to you? That might be one thing. But does it feel like it’s all he sees – and all he thinks about? That’s another thing entirely.

If you think you feel a little something for him, you should give it the opportunity to flesh itself out a bit more. I don’t think you’re making a mountain out of a molehill – you have every right to be specific in what you’re looking for, and you deserve to be loved and respected as an complex human being with many facets.

Dating is hard, and dating when you’re flourishing in your identity and sense of self is even more difficult. Stay true to who you are and what you want and make sure to have fun in the process.

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