As I continue to “get out there” and date, I am finding myself meeting some interesting women. The ultimate goal is to find a wife and have a family together, but I don’t think there’s anything wrong with flings or “friends with benefits” in the meantime. I feel that most women just aren’t up to my level of “family orientation” anyway.

By far the hottest butch woman I have ever met recently is also 19 years old. We met on OkCupid. She is 5’4, short brown Justin Bieber style hair, great body shape, good teeth and nice smile, beautiful brown eyes with luscious eye lashes, and that amazingly intriguing butch attitude. She is friendly and funny. She has in the past identified as transgendered, but currently identifies as a lesbian. Although my first girlfriend was underage, this isn’t normally my style and I do not generally seek out younger women. And for the record I would never have a romantic relationship with someone significantly younger than me again. My age range is typically butch women 25-35.

I am 28 years old by the way. Don’t judge me.

We’ve met up twice now and had one sleep over. She’s very confident in herself and her sexuality, and it’s absolutely sexy. She is no relationship potential though, come on, she’s way too young. She’s also emotionally damaged, which just reminds me of Queen. This 19 year old has been through a lot of trauma throughout her entire life, and still continues to experience devastating life situations. For instance, she’s been through foster care most of her adolescent life, molested by people she loved and trusted, recently experienced a substance abuse by using bath salts, has been an alcoholic since she was 12 years old, and has lived most of her adult life so far being homeless and currently squatting.

But she’s a great kisser, knows exactly how to fuck, likes to cuddle, and is willing to drive over an hour to see me. She also keeps my mind off Queen. Any woman who can help me keep my mind off Queen is a good thing to have around even if temporary.

So, I want to share with you some important things to keep in mind when “seeing” someone significantly younger than yourself. These are kind of general guidelines that I keep mindful of and maybe it’ll help you if you’re ever in a similar “fling” or “friends with benefits” situation.

  1. The only expectation should be NO expectation. You have already established this isn’t going anywhere significantly meaningful, so don’t loose yourself!
  2. As difficult as it may be sometimes, DO NOT make judgmental comments on their own personal choices. Even if you’ve been through the same difficulties, choose your words carefully and remain unbiased. You may only get resentment for taking a seemingly “parental approach”.
  3. If you’re dating other people, they should be too. Encourage her to date others if she’s not so she doesn’t get clingy. Don’t blow up her phone with a million text messages and calls either, because that just sends mixed signals.
  4. I wouldn’t advise letting her meet your friends since it may give her the wrong impression of your “fling” situation. But if you do, just keep it at a minimal. Nights out when there’s a group of 5 of more are good because you can both socialize without feeling obligated to entertain each other.
  5. Be careful having sex! I think it’s normal to feel more “connected” to someone once you have sex, just don’t get those feelings mixed up with false hope for a relationship.


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