I try to imagine the world through others’ eyes. It makes interesting fodder for thought. We see things differently than other men, women, too. We are the crossdressers and transgender MTF that the world despises. And… yet… we are the spouses, parents, friends, colleagues, and neighbors to those who sometimes tolerate and sometimes understand us. Really… nope. Only another crossdresser understands what we go through. Likewise, it is unfair of us to assume the world sees or will see as we do.

So… let’s have some fun with this post. Valentine’s Day is approaching, and I started thinking back on what it meant to me and how my perspective of certain past moments is completely different today from what I once thought. I’ll go first:

One of my first memories was back in high school, during my senior year. I had a girlfriend that I was “promised” to. On a side note: Life might have been better if I’d stayed with her… For Valentine’s Day, she told me my gift was upstairs in her room. When we got there, she took off her jeans and top to show me the white corset and stockings (gartered in place). She slipped on the low heels she had to complete the look. This was the same girl who bought me a Playboy subscription for my birthday. It was a great Valentine’s Day. I’d already had a fascination with lingerie at that time, nylons and heels, experimenting at home with them and hiding my mini stash well. My reflection back has more to do with later seeing those same items in her bathroom and me wanting to wear them, struggling against those urges.

Today, I see it for what it was, that part of me that is feminine and was crying out to be heard and not eradicated. The me then believed it was a shameful fetish and could be stopped. The girlfriend was the one who might have accepted me, but in another year I had begun to move on from her for other reasons.

Join Our Community-cdh

My ex-wife’s birthday and Valentine’s Day were 12 days apart. I know many of you will relate. Valentine’s Day is a “Crossdresser’s Hope Day.” We had the green light to shop at Victoria’s or in my case, browse the pages of Fredrick’s of Hollywood catalogs that made their way to our house (and would have been relegated to trash by the ex if not for the heroic saving by me!) Back then, I thought I was doing the newlywed, husband thing, buying my wife special lingerie that she would gratefully and willingly wear… for my benefit. Once having it tossed back in your face by never being worn and eventually disposed of was enough to learn my place. Some women appreciate the thought, mine did not, and she let me know it in many ways… another story… should have married the girlfriend…

Looking back, I see it for what it truly was… to me. That magical chance to shop without fear in the greatest place on earth. I relished that time, spending not one but multiple visits there for the sake of buying my ex something for Valentine’s Day. The rest of the story, as Paul Harvey would say lies in the fact that the first visit was for her and to scope out the other options. On the second visit I chickened out, and the third had me buying for the imaginary wife who was of similar size to me… Cash only… as the ex did the checkbook and monitored the credit card…

And… the items didn’t look as I anticipated on me, and I didn’t care. Lost in the feminine reflections of the mind that we all know. I know that I did, and I’m willing to bet most of you have, too; bought items for that SO that you wish you could wear and justified it by thinking it would make them happy as well. Not one thing that I bought my ex did she like. It might have been her. I came home from a business trip and loaded with Bath and Body Works items when they were first getting started. Her reply wasn’t “Thank you,” but “You were gone for three days, and this is what you brought me?” Later, she couldn’t get enough of their items, but what I gave her then was thrown in the trash.  Yeah… that hindsight is indicative of the true relationship we had and would have been best not to. A refresher… she found me in her Prom dress during our first year of marriage and I now believe that set the stage for our Shakespearean tragedy of a play.

The next year, same business trip, and this time I went all out, thinking only of her. I bought a beautiful Anne Taylor dress and matching 3-inch heels. I took her picture to show the sales clerk. At home, the ex only snarled when I gave them to her. “What made you think that I would look good in this?” After a few days of silent treatment, she at least acknowledged the “cost” of the gift. I think she consulted with a friend and found out how much I’d spent. She did try it on to show me. It was absolutely stunning on her, not her personal style, but if another woman had told her how great she looked in it, she’d have worn it until it fell apart… like some of her other, not-so-flattering outfits. It hung in the closet with an “I’ll wear it someday” until it was sold at a garage sale for $5. The shoes were never worn (by her). I did my best trying to fit those size 8 on my size 13 feet. Maybe she suspected and that’s how they disappeared without my knowing… A crossdresser never lets things like that go by.

Valentine’s Day shopping has lost a little of the luster with the availability of everything online. In my last relationship, I was with a special lady who didn’t wear makeup, didn’t have her ears pierced, and was rarely out of her jeans in a dress. A down-home farm girl. I think after some time went by I realized that I needed to step back and figure out me and quit trying to fit the mode of male normality… it wasn’t working. I know what I want in a relationship and the chances of finding it near me aren’t likely, so I set it aside. With Valentine’s Day coming up, I’ll go do some shopping for that imaginary and much younger, provocative spouse that I don’t have. I still have an old wedding ring to wear to give off the illusion. It’s been too long since I last saw Victoria and visited Bath and Body Works…

May you have a memorable Valentine’s Day. And… if you have an adoring significant other, may it be special for the both of you… wink… wink…


Until next time…


More Articles by Sabrina (Brina) MacTavish

View all articles by Sabrina (Brina) MacTavish
The following two tabs change content below.

Sabrina (Brina) MacTavish

Brina is from Iowa. She is currently the Managing Editor of CDH and TGH. When she isn't busy on-site, she spends her time writing--more than a hobby, but still seeking that 1st bestseller. Under her male guise, she has 5 published works of fiction and one short novella under Brina's deplume. A recently completed CD novel should be ready in the next year and Brina hopes it can become a series with fun characters.

Latest posts by Sabrina (Brina) MacTavish (see all)

5 1 vote
Article Rating
Inline Feedbacks
View all comments
12 days ago

Well, I have always waited for a special Valentine’s Day. When I was young I have always given as gifts. Without anything in return. And I haven’t given him clothes in a while. I never get the gift right.
Kisses from Carla 

12 days ago

Since it hadn’t occurred to me to buy clothes, I did want him to buy what I liked and then wear it. But she has very basic tastes, not like me in feminine. I was looking forward to trying on her new clothes. Kisses from Carla

Active Member
9 days ago

I have some stories much like yours. I married wife1 when I was 20. Our first Valentines I bought her 2 things. I was out to buy her something VERY revealing. She dressed conservatively due to her upbringing. I looked for over an hour. 1) she was tiny – 5’3″ and 80″ soaking wet (as we say in the south). 2. her build was such that most things I saw would hang off her (not sexy). I finally found something fitting and very sheer. As I was walking to the checkout, I found another very long and flannel nightgown I… Read more »

Chanel Dubois
8 days ago

So many excellent observations here…my favorite “if another woman had told her how great she looked in it, she’d have worn it until it fell apart”….for some reason women seem to value those (frequently false) compliments from others more than any from their husbands…

Elizabeth Stone
8 days ago

Thank you so very much for your wonderful and encouraging article!❤️

Jennifer Friendly
Active Member
8 days ago

My wife and I married very young, I was only 18, she 16. We came from the same kind of background, small coal mining town in the Appalachian mountains, although she did live on the other side of the canal. (I was from the other side of the tracks) While most thought it would never last, we fooled them all and lasted until her passing, just 4 months short of our 50th anniversary. I think our similar upbringing, values, and growing up together as one unit instead of as 2 independently created individuals contributed to the longevity. I’m not saying… Read more »

Would love your thoughts, please comment.x
Subscribe To Our Newsletter

Subscribe To Our Newsletter

Join our mailing list to receive the latest news and updates from Crossdresser Heaven.

You have Successfully Subscribed!

Log in with your credentials

Forgot your details?