A Boyfriend's Perspective

A Boyfriend's Perspective


There have been plenty of posts and blogs in the past regarding everyone’s stories about how and why they started their journeys into the crossdressing world.  Everything from raiding their sister’s panty drawer to stepping into mom's high heels and strutting their stuff around an empty house, so I don’t need to tell that story, because we all have our stories.  But here’s the rub, everyone made sure that no one was around when they decided to explore their feminine side. While I completely understand it, and yes, I did the same, but who do you decide to open up to when you get into personal and intimate relationships?  Is it safe? Will you be judged? Do they give you “the look” and head out the door faster than you can say lace panties? Then the questions between your ears fire back up again, is this right, am I normal, is this really ok? 

I have since I can remember always had a fascination with women’s underwear and lingerie.  The colors, the fabrics, the styles, the sexy look that it provided. When I was married to my first wife, I can guarantee that I spent more money at VS then she ever did.  I think it would be fair to say that I enjoyed it a whole lot more than she did. Secretly, I wish some of the things that I bought for her; I wish I was purchasing for myself.  But that would be wrong, so I thought. Never in a million years would I ever have told her how I felt, I knew how that would have gone over. There are some things that you just know.

Fast forward a few years after the divorce, and freedom, and the opportunity to do what I want to do.  While out doing “market research” in the dating world, starting out the conversation of “so, what are your thoughts on wearing lingerie?  Oh, sorry, I wasn’t talking about you”, might not be the best way to start the evening. In dating one girl, and sharing more intimate thoughts on a weekend, I got the guts to bring it up.  I got “the look”, and that conversation was never brought up again. There go those thoughts again……. The relationship ended soon after. 

But, as we have read in other blogs, and in Angie’s case, there are women out there who not only open enough to see another side but actually find it attractive and play an active role in having their SO crossdress.  For some, it’s panties, for some its bras and panties, and for others, its girlfriend night full-on getting dressed up and out on the town.  

When I started dating my girlfriend for some reason, I just felt safe in letting her know.  Now, for the record, it wasn’t an oh, and by the way over Sunday Brunch, it took a little time and a shitload of courage to bring it up.  After my marriage, and my last girlfriend, I was a little, or a lot hesitant, but for some reason, I just knew that I had to, or I would never have the freedom to be myself. So, one night I started talking around it, she asked more questions, I danced, she says spit it out, I skirted (no pun intended), I finally said it, I like wearing women’s panties.  Then, the pause, and couldn’t see “the look” because we were on the phone. Then she says, “I would like to see what that looks like on you.” “Really?” I say. “Yes, I would like to see how that looks on you in person”. Needless to say, I was in a bit of shock and awe. A woman who is accepting of this side of me. Although I was still on the fence about telling her, it was such a freeing feeling that the secret was out, I didn’t have to hide it anymore.   It did spur on a lot of thoughts and emotions, and the excitement brought on my first purchase on XD and shared that with my girlfriend. Panties, bras, garter, and stockings, I finally got to make those purchases for myself.

When we finally got together, as she lives in another city, it was time to actually make this happen.  Time to pull up the bootstraps and give her what she was asking for. So, there I was in my panties and a bra, raw, real, and vulnerable, waiting for “the look”.  Well, the look that I got, was not at all the look that I received in the past, it was a completely different look. It was one of acceptance, excitement, and holy shit, do you look f%$#$% sexy.  Words that I never thought that I would hear.

Since then, we have gone on shopping trips buying lingerie for both, having great fun with the staff helping us, it’s so fun to play.  Going out for romantic dinners when she is the only one knowing what I am wearing underneath. Making her breakfast in panties and a babydoll, only because she requested it (not just the eggs).  XD has now become a household name, well in our conversations anyways. 

I will be honest, that reading the blogs on XD have been incredibly helpful in discovering that I was not alone.  That there were so many men out there discovering an outlet to quiet the voice between the ears. As a heterosexual male, with a lot of female energy, I wasn’t weird, or alone, or have no one to talk to.  Now, my world has opened up, and I have the freedom to be myself.

I would love to hear your thoughts from a boyfriend’s perspective. Everyone has a story, what’s yours? 


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This is an interesting topic of which I would like to add another perspective. I started crossdressing in my early 30’s at the request of my dominate girlfriend. She demanded and enabled me to dress in panty and bra as a way of showing my submissiveness towards her. She continued with my behavior modification and eventually had me in make up, wigs and heels. This I did, and I grew to love my feminine dressing, and embraced it with her blessings. After we separated, I continued with my cross dressing and made further enhancements to my new found lifestyle. Now to my perspective. I had always been bi-sexual, with a few experiences in the past. Now I began to date men who admired and wanted a feminized male with all the female trappings. So for several years this is how I lived my lifestyle. I also belonged to crossdresser group who were very supportive and educational. With this group I was able to meet these special men. Wow! This was a very exciting and special adventure. I became the “girlfriend” to these men. Going out to dinner, movies, parks, beaches and parties were part of my dating scene. These men were the kindest, most considerate and respectful people I have ever met. Always treating me well and providing gifts which were very appreciated. These men really loved “gurls” like me. Anyway, this is just another perspective that I wanted to share with my fellow XD’s. Im sure some have experienced this lifestyle, so please share your stories as well.


So glad to read this story! I have also been lucky enough to find a woman who accepts me, and think my butt looks good in thongs! We both wear them when we fool around ;) I admitted to liking wearing women’s underwear (thongs, stockings, corsets etc.) before she moved in. In the beginning it was a lot to process for her, as I could understand. Now we have been together almost 3 years, and are engaged! :)


I loved reading this, I certainly can relate. For me; shortly after moving in with the woman I would marry, I decided I needed her to know. I didn’t have the guts to just bring it up in fear of her rejection or leaving because I love this woman so much I couldn’t imagine my life without her. I purposely left a pair of panties where she would find them. Oh boy, did she ever find them. She immediately assumed they were another woman’s, I could see the fury building in her. Yet, when I calming told her that they were mine, that anger turned to a causal “oh?”, “why haven’t you just told me?”, she said. I couldn’t believe it there wasn’t “a look” or judgement. This lead to 13 years or acceptance and encouragement. Shopping trips and nights out etc. Now, we evolved into a polyamorous couple, I’ve a girlfriend whom I’ve had a serious relationship with for almost two years. I told her much sooner and had the balls to come right out with it. Her response so inquisitive. She wanted to know what I got out of it mentally and physically, etc. it felt so amazing having her deep interest and support. She loves when I’m wearing something in front of her now. The three of us are in a triad relationship now (my wife, girlfriend and myself) we now have gone on shopping trips for the 3 of us and it’s never felt more amazing or accepting to have two women love and encourage me to be myself. Plus, having matching sets between the 3 of us is something that really thrills. My most recent XD purchase has been a huge hit with them and I cannot wait to see what the future holds with XD and me.


TA I applaud you for your love and acceptance of your partner. They are just clothing and women can wear what they want Where are our girlfriend jeans? The dresses we can wear? Anyway this lingerie from xdress is made for men so is it even crossdressing? Something to think about. Some people like boobs some legs some feet gets them off, if its lingerie then so be it
Where something pretty today i did


That’s awesome Stevie! I agree with you. When you find someone who accepts you for who you are, appreciate and enjoy them. I know I do WB.😘
Lotsa Satiny Hugs!


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