Allison M.

A crossdresser's thoughts on life, fashion, fabulousness, and (oh yeah) dressing up

Thoughts on love and crossdressing


The big romantic commemoration known as Valentine’s Day occurred earlier this month, and if you’re a single person like me, the below picture is a probable representation of how your day went:

Obvious dramatic depiction of my Valentine’s Day

Yeah, just like that round-headed kid, I didn’t get any valentines this year.  As a matter of fact, a day like Valentine’s Day finds me sending more valentines than receiving them.  I’m the proud uncle of four nieces, and I’ve always felt a responsibility to express my love, support, and admiration to them on any significant holiday or occasion, regardless of whether or not I can deliver it to them in person. (Valentine’s Day is no exception, which is why each of them received a card from their proud uncle.)  Whether my nieces are able to reciprocate that affection through the mail, phone, or whatever doesn’t affect that either; knowing they’ll still shower me with their own love the next time I visit them makes me happy just the same.

While I have blood relatives I can shower affection to, Charlie Brown has always pined for any potential source of love, especially that little red-haired girl; hence, Charlie Brown is the type of kid who’d camp underneath a mailbox all day, waiting longingly, impatiently for a valentine that may never arrive.  Unlike Charlie Brown, I never really showed unrequited love toward anyone else when I was younger, and if I did have a crush on someone, I never acted out on those feelings.  I suspect admit that having shy awkwardness, as well as a thin skin and guarded outward attitude — the result of the occasional bouts of teasing and bullying I encountered back then — prevented and/or discouraged me from making any affectionate overtures.

Though I’m not as thin-skinned as an adult as I had been as a youth, my complacency of single life has continued.  My male side has never been one to just go up to someone and just say, “Hey, I like you” or even, “You’re pretty cute.”  But that’s not to say that I’ve never taken the initiative. (Heck, even Charlie Brown has made at least some effort to woo that little red-haired girl.)  I have gone on a few dates, I did have a girlfriend for a year or so when I lived in Green Bay, and I’ve even tried speed dating.  The net result, however, is my all-too-single status.  No, it’s not fun being single, but I’m used to it; and if I die an old spinster, so be it.

If I ever do go steady with someone (do people still use that term anymore?) and things start go get serious, there’s something that I will have to bring up with him or her — my feminine side as Allison.  Just as I’ve never shared my crossdressing side with my family, I never did so with the girlfriend I mentioned in the above paragraph.  I dated her during a time when I was still not open about my crossdressing as I am now open about it online (the internet was in its infancy back then).  I was living with my sister at that time, which led to making sure my feminine side was covert (i.e. no dressing up in her clothing when she was around).  Just as I didn’t want to take chances revealing my dressing-up to my sister, I felt the same way when dealing with my girlfriend.  I gauged her to be someone who may not have been understanding about a guy with a girly side, though who knows if it was a false gauging (perhaps she could’ve been accepting, but I just didn’t feel it right to consider that possibility).

The intimate phase of the relationship between that girlfriend and I lasted for about a year or so; come to think of it, it may not have been for that long of a period.  We went through a brief “just friends” phase after that and eventually fell out of touch.  I’m not sure how she’s doing these days, though I like to think she’s still living in the Green Bay area and is married to a wonderful gentleman… with whom she probably shares all her deepest secrets with.  I say that because although I did not disclose to her my deeply secret feminine side when the two of us were intimate, she did share one of her own secrets to me.  I will not share it on this post as I promised her when she told me this secret that I would never share it with anyone, not even my family members.  Let’s just say it’s a secret that deeply affected her before I ever met her, but it’s also one that, I sincerely hope, hasn’t adversely affected her in the long-term. (I will say it’s also a secret my sister may have suspected at one point, but I never confirmed it with her.  Yeah, I’m that good at keeping a secret.)

But, to regain my train of thought, to the likely need to disclose “Allison” to the next person I date….  I think the fact that I am more open and confident about my crossdressing (online, at least), and the fact that I’m in a town (Madison) with a generally progressive, open-minded atmosphere leads me to this thought:  Should I ever find myself in a serious relationship some day in the future, I will want or probably need to disclose to that woman or man my side as Allison.  For sure, I probably won’t blurt out on our first date together, “Oh, by the way, I dress up as a woman.”  Rather, what I will seek to do is feel things out with that person: How open-minded is that man or woman?  Will that person understand that Allison has been and will always be a part of me, though not a side of me that defines my entire life?  Would they perhaps like to see and/or be with Allison?  To be succinct, would they support Allison?

Those serious questions about my crossdressing side are ones I must consider if I were to date someone in the future.  Of course, I’ll need to have another steady date (oh, there I go with that antiquated-sounding term again) in order to put those questions into play.  When I feel the time is right, I’ll dive back into the dating pool that I’ve been out of for so long.  Once I find that right woman or man to date and perhaps become intimate with, I’ll take the “go slow” route in regards to disclosing and introducing Allison to them, gauging how that person would be accepting (or *shudder* not) about my feminine side.  If things don’t work out between the two of us, well, perhaps another supportive person will be out there who’ll want me to be their valentine. Because, after all, even a lovelorn person such as Charlie Brown has been someone’s valentine.


Author: Allison M.

A part of the trans community ("cross-dresser" is the term that applies to me) who finds themselves much more expressive and somewhat more confident when presenting in a feminine persona. An admirer and supporter of those who are fashionable, fabulous, and friendly (LGBT or otherwise). Someone who tries to be witty and unique, but is not even remotely perverted or a pariah (I am a real human being, just like you). Using various writing styles on this blog to communicate thoughts and feelings concerning my life experiences, fashion sense, and the world at large (and maybe impressing my high school creative writing teacher who deservedly gave me middling grades).

8 thoughts on “Thoughts on love and crossdressing

  1. I was terminally single before I met my boyfriend.

    I think we did just about all the things you’re not supposed to do on a first date and due to a failed attempt at sex, he told me about his crossdressing on the first date.

    In some ways I’m glad he did because it’s an important part of his personality and there wasn’t an emotional investment to lose.

    Do I wish he’d waited? Nope. It immediately made us closer and I knew exactly what I was getting myself into. Fortunately I absolutely adore both his masculine and feminine sides and it’s a real pleasure to watch someone truly start to enjoy who they are.

    I wish you all the luck in the world! I know how single feels. I hope you find someone who can appreciate all that makes up you! Be straight up honest in the early days. This is who you are, it seems harder in the short term, but it will most definitely be harder in the long term.

    Liked by 1 person

  2. Very good points. I think my main concern is not how a potential significant other will feel about Allison the first time we meet, but rather how they’ll feel about her as our relationship goes further. I’ve heard stories of other crossdressers whose dressing up became a serious impediment in their relationship/marriage. Perhaps their significant others were originally supportive, but over time gave the cold shoulder to their mate’s feminine side.
    Maybe there could be a balance about the timing of disclosing Allison’s existence to that PSO. I am more for waiting for the right time to telling them about Allison, whether that time may be our first date or our fifth or our fifteenth. What’ll be more important for me, though, will be telling them (or reminding them?) about Allison once our relationship is on firmer ground; sure, they may think my dressing up is cool that first time I may tell them, but will they remain warm to Allison later?
    Thanks for your well wishes. I hope that someone somewhere will embrace the many (male and female) facets that make me the person I am.


    • I understand your points. Most of those questions are going to be answered differently by every person you encounter. One of the beautiful things about humanity is that we’re all so different, though it can a curse too!!!

      Maybe, given that this is such an important part of you, you should perhaps try a different tact with dating as a whole. Try it with your crossdressing out in the open. It’s going to come up one day.

      I think if I had made an emotional investment before finding out about Paul’s tendencies then the love I have for him would make me want to try to understand it, try to fulfil his needs etc, but would my heart truly be in it? Would I truly accept this new part of someone or would I just be trying to accept it?

      My view is going to be different to a lot of the people you have been speaking to. Obviously being the girlfriend of a crossdresser is way different to being the crossdresser. I fought to be who I wanted when I was in my late teens and never gave up (again, different because I was a female goth, not a crossdresser, still wasn’t easy and this was 20 years ago!). I also love people who are different, who be themselves and embrace it.

      So for me, first date worked. I had time to think about if this is what I want, if I could be the support he needs, if I could sustain his tendencies, if I’m happy to be seen with him when dressed, am I prepared to give any psychological kind of support, am I ok with living with this? Will he want to transition later on in life?

      This was all stuff I could think about and research before I got too emotionally attached. Stuff I could ask him about if I wasn’t sure. If I wasn’t someone who was ok with this and I’d been on several dates and decided it was great, I really liked him and was starting to fall hard, told friends and family about this exciting new guy etc, I’d be completely devastated to find out it was a waste of time because I couldn’t handle this new aspect to the relationship. It would break my heart and spirit.

      So that’s the other side of the coin.

      Paul is a lucky guy. I’m not a normal girl. I also know that I’m not the only girl like me, there are more of us out there.

      I passionately believe that you should live in the manner you choose. My hope for this world is that we can all be our fantastic, weird wonderful selves. It’s a futile hope, I know 🙂

      You must not feel shame for who you are. You need to embrace it, own it and live it. It’s the only way you’ll find happiness, whether that’s on your own or with a partner. If you’re straight up about it you’ll have more chance of finding the right person for you and not have to live your life in hiding.

      We’re out there. Don’t give up. xoxo

      Liked by 1 person

      • I understand. With my concerns about mainly keeping my crossdressing private, and even though I’ve been to public places and been in groups that were CD-friendly, I never considered a first-date situation when I was dressed up. Or, barring that, if the person I am dating knew in advance of our meeting that I do dress up, even though I may not be en femme on our first date. I’ll have to consider those possibilities. Thanks!


      • Doesnt have to be first date, get a feel for who youre dealing with. (Paul and I had been emailing daily for 2 weeks prior) But let them know early and then they can decide if they want to see you dressed up.
        But they do need to know this part exists!
        This is important to your happiness. Don’t settle. 🙂 xx

        Liked by 1 person

  3. On a completely different note, I’d just like to say that the American valentines day kinda weirds me out!

    Australians (of which I am one) tend to keep Valentines strictly to romantic partners. Giving valentines cards to friends, family or teachers etc just seems very foreign to me!


    • *LOL* Here in the U.S., there’s a term known as “Hallmark Holiday,” in which some consider Valentine’s Day, Sweetest Day, Boss’s Day, et. al. only as an occasion totally made up for commercial purposes, (i.e. buying Hallmark greeting cards to send to the ones you love and care about, regardless of how they are or are not related to you). If a person gets so verklemped by such a day that they need to buy and send a very sugary greeting card, then I’m so guilty as charged. *blushing*

      Liked by 1 person

  4. I missed this post in my feed somehow, but I just read it and wanted to say … yeah. I can understand exactly how you feel. But you should know that there really are lots of women who couldn’t give a rat’s ass about whether or not you are a crossdresser. They are out there, and there’s more of them than you might think. Some of them will even be kinda into it.

    This always sounds crass, but have you considered online dating? Just put it right out there in your profile. You might be surprised!


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