Allison M.

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

Allison at the beginning: How I started dressing up


As I first mentioned in my introductory post, I wanted to use this blog to share my stories and thoughts on life, fashion, and crossdressing, including some thoughts I’ve disseminated on other sites and journals but want to expound and embellish further here.  One of those stories I am eager to share again is the tale of how I discovered a spare bedroom and its magical contents.  It’s been decades since it happened, but this is how I remember the story goes…

My family is from eastern Wisconsin; I spent almost all of my adolescence in that region, and it’s where my mom, my stepfather, and one of my sisters still reside.  I use the term “region” as we moved quite a bit around eastern and northeastern Wisconsin when I was a kid, moving from one town or house to another.  One such house was here:

Farm houseThis photo, taken several years ago, is of a house on a former farm located somewhere in eastern Wisconsin (to be vaguely specific, about 10 or 12 miles from the town where my mom and sister now live).  Just before I turned 11 years old, our family had to move out of a house my mom and stepfather purchased after they became engaged.  It was a nice home in a quiet neighborhood of a small town, and though it needed a couple of improvements, we thoroughly enjoyed living there.  But Mom and Dad’s purse strings began to tighten, and with both facing uncertain job situations and a new baby on the way, they felt they could no longer afford payments on the house.  Luckily for us, a “white knight” arrived in in the form of the ex-wife of my stepfather’s boss, whom I’ll call Ms. Brown.  She was of the well-to-do set, owning several properties and businesses in the county where we lived, including a small farm way out in the country where she kept 4 or 5 riding horses.  For a reduced or free rent (I cannot remember which), Ms. Brown allowed us to live on the farm and the century-plus-old stone house you see pictured above.

Ms. Brown was generally a demanding person, so our stay on the farm came with conditions, primary of which being we had to maintain upkeep on the farm and care for the horses.  It was hard work for sure, but we didn’t mind it too much; horses are beautiful creatures and my sisters really loved them.  Another caveat was that we had to accept the farm the way it was.  Ms. Brown made all decisions on any improvements to the property, a right she didn’t seem to exercise very much; for example, my bedroom was the only room in the house without any electrical outlets.  Plus, my stepfather also had to perform work and personal errands on Ms. Brown’s behalf, making him her unofficial manservant (for sure, he didn’t relish that part of the bargain).

Understandably, Ms. Brown took a pretty close interest in us; she wanted to make sure those living on her farm and caring for her horses were trustworthy.  She wasn’t above making unannounced visits to the farm, even at the most inopportune of times.  One summer weekend, for example, we returned from visiting my grandparents, only to see that Ms. Brown was already in the house, master key in hand, impatiently waiting to hear how her horses were doing.  Occasionally, we had to make reciprocal visits to her palatial home on Lake Michigan (think Lorelai’s Friday dinners at her parents’ mansion on Gilmore Girls, only not as frequent).  While visiting Ms. Brown, we had to withstand the awful odor of her cigarettes (she smoked like a chimney *gasp*), withstand the evil eye of her dog (he never took kindly to strangers), and listen to her talk up all kinds of gossip and stories.

Ms. Brown was quite an opinionated woman who offered up her good share of blunt opinions, most of which were in a conservative, politically incorrect vein.  Ms. Brown’s family and her assessments of how they should live was a common topic.  One member of her family that stood out in my mind was one of her nephews; I’ll refer to him here as Daniel, as I cannot recall his actual name (forgive me, it’s been over a third of a century) and Ms. Brown only discussed him once or twice.  When she did bring Daniel up, though, Ms. Brown described him as if he was the black sheep of the entire Brown family.  I do recall talk of Daniel having serious personal and psychological problems, including issues with sexual and/or gender identity, as well as issues with self-mutilation and possibly suicidal thoughts.  While Ms. Brown always seemed to think her family was good seed, she felt reactionary, dismissive, and even frustrated over Daniel and his identity issues.  Simply put, her mind couldn’t compute how and why he didn’t become the fine, upstanding man she had hoped he would be.

At this point in the story you’re probably thinking, “Gee, Allison, is Daniel gonna play a big part in this story?  And when are you going to get to the dressing up part?”  Well, Daniel does play an indirect yet big part in my feminine side, and here’s how:  The first year or so we spent on the farm, Daniel was undergoing treatment, including spending time in a psychiatric facility.  During his convalescence, Daniel kept most of his belongings on the farm.  His beige 1968 Dodge was parked next to the barn, loaded with footlockers of his personal effects; as well, more of his belongings were kept in a spare bedroom in the house.  (I’ll point out the bedroom in the above photo: It was the upper northwest corner of the house, to the right as you see it; it was one of four upstairs bedrooms in the house.)

Almost from the moment we moved in, I was of the understanding that the car, the spare bedroom, and their contents were Daniel’s possessions, that they were none of our business, and that they were not to be disturbed unless absolutely necessary.  Even though going into that bedroom was verboten, this 11-year-old boy was always curious about what was in there.  Heck, for all I knew, that room could’ve been painted black or have been used for a meat locker or a dungeon.  So, one spring day, with everyone else tending to farm chores, I opened that bedroom door and here’s what I discovered:  Some old furniture, a couple of lamps, a mattress, a disassembled bed frame, and, underneath the window on the far end of the room… paper sacks full of women’s bathing suits and feminine undergarments.

The clothing in those bags included sets of leotards, shorts, and exercise tops, all in matching colors (blue, black, and teal) and made of sleek nylon/lycra spandex fabric.  I vividly remember how magical the material felt in my hands.  They felt smooth and sleek, they looked almost satiny, and they looked… well, pretty sexy.  By this time in my maturity, my brain had long since formed its “what looks sexy” subfolder, and lumped in it were disco pants, bathing suits, exercise leotards, and silky shorts just like the pair I had in my hand at that moment.  I had seen such women’s clothing on TV or in magazines and thought, gee, those things look downright sexy on a woman.  Yeah, I’d dare even use the term “arousing” to describe how I viewed them.  What’s more, they certainly weren’t the type of clothing I had seen on anyone else outside of TV or magazines.  The women in my family and in the area where we lived were usually seen in clothing either dowdy and conservative in nature or, more often than not, something to do a lot of farm work in.

That first trip to that spare bedroom ended abruptly when I heard noise outside the door and feared someone was coming upstairs.  The feeling of Daniel’s clothing in my hands lingered, however, and a day or two later, I sneaked back into the spare bedroom, being very cautious to not arouse anyone’s attention, and explored his belongings a little further.  I discovered some bikinis, bras, panties, and other pieces of lingerie.  They looked thrilling, but but my attention went back to his bathing suits and shorts.  At this point, a voice in my head was telling me, “Why not try them on?”  So, I grabbed a pair of shorts and sneaked back into my bedroom to try them on.  Not only did they fit nicely, they felt so magical, so alluring, and, yeah, it was just a little bit of a turn-on for this adolescent.  It was an amazing feeling, one that lasted in my mind for some time and one that I can still happily recall today.

As the ensuing days became weeks and the weeks became months, I would make more clandestine trips back to that spare bedroom to examine and try on some of Daniel’s other feminine attire:  Boyshorts, bikini bottoms, negligees, camisoles.  I would either try them on in that spare bedroom or sneak them into my own bedroom.  Every now and again, I would wear an item underneath my boy clothing with nobody at home being the wiser (or so I tend to recall).

As indicated above, I made it a point to keep my dressing up hidden from my family, and I never wore any women’s items when going to school.  I want to highlight that last part about school especially:  I was quite the wallflower as a kid, struggling to build friendships with classmates as much as I struggled to keep up my school grades; hopping from one school district to another only exacerbated that.  My shy, guarded stance made me an easy target for teasing, ridicule, and, yes, a bully’s wrath. (Oh, if you think my being teased and bullied was due to any outward gender or sexual identity, perceived or otherwise, that wasn’t the case.)  I feared that if a teacher, administrator, or classmate ever discovered in one way or another that I was wearing women’s clothing and undergarments, my school problems would increase tenfold; and if they told my parents, those fears would only augment exponentially.

Despite the fears of my dressing up being uncovered and the repercussions that would result, the more I did it, the more I felt comfortable about it.  Oh, for sure, I knew the clothing I tried on wasn’t what boys like me were meant to wear.  And, for sure, I would be disciplined in some form if it was discovered that I was wearing them.  But even so, while I was wearing Daniel’s garments, things felt different.  It wasn’t quite a feeling of wanting to be a girl all the time (I still felt comfortable with my general identification as a male), but it was a sense that all my troubles (family, schoolwork, classmates) tended to melt away for a while when I was dressed up.  I also felt a sense of personal strength and security, a feeling that, despite the difficulties surrounding me, a part of me knew that things were going to be all right.

But all good things must end, and those trips to that secret wonderland we called a spare bedroom didn’t last long.  I returned home from school one late October afternoon to find Daniel and his parents at the farm.  Daniel had just been released from his treatment and he looked… quite nervous.  I quickly gained the understanding that Daniel’s treatment had concluded, and judging from the forced smile he had on his face, the nervous “hello” greeting he gave me, and his twitchy appearance, I wondered to myself… Gee, he looks so ill at ease.  What kind of treatment did they put him through?  Is he going to be all right?

Daniel and his parents weren’t at the farm for any chitchat; it was clear he was retrieving all his belongings — his ’68 Dodge, his feminine wardrobe, everything.  Naturally, my mind turned to concern about his stash of clothing from the spare bedroom.  Yes, I had been trying on and wearing his wardrobe up until that point; and, yes, I took every precaution to leave that room the way it was, including putting every piece of clothing back to into their bags after I was done wearing them.  But I still worried that even the slightest tear of a paper sack or a misplaced box would raise suspicions.  Luckily for me, nobody raised any concerns, least of all my parents.  Daniel and his parents just took all of his stuff, bid us adieu, and let us be.

Of course, I never told Daniel that day (or anyone else then or since) that I had been secretly wearing his women’s clothing.  Was I tempted to tell him?  No, absolutely not.  Those clothes were as much Daniel’s property as his ’68 Dodge; he held deed and title to them, and my wearing them constituted an encroachment over those boundaries.  Had I told him then… well, who knows what would’ve happened?  If our paths were to cross today, I still wouldn’t tell him about all I had done, even if a distance of 33 years would have soothed any concerns on Daniel’s part… although I admit I would be tempted to give him a big “thank you,” for were it not for his wardrobe, my feminine side would probably not have developed the way it has.

The day Daniel retrieved his belongings was the only day I ever saw him.  I do wonder how his life turned out, though I’ll never know the outcome as Ms. Brown never discussed him in conversations afterward; Daniel was still persona non grata as far as she was concerned.  Even though Daniel’s clothing was no longer available to me, my curiosity into women’s clothing did not end; instead, I just gravitated toward the wardrobes of my mom and sister (of course, I still kept it on the down low).

Our stay on Ms. Brown’s farm had an abrupt ending the following July: My stepfather had long grown tired of being at Ms. Brown’s beck and call by that time, and he was always looking for a better job that paid him better wages and much better respect.  He would find that next “better job” as an over-the-road truck driver through a freight company based in far northeastern Wisconsin.  Upon hearing of this, Ms. Brown gave us until the end of that July to leave the horse farm, even going so far as to have everything we had just planted in the vegetable garden that spring dug up, a move that left my mom greatly upset.

This summer will mark 33 years since our family moved away from that farm, and that property’s outward appearance has changed greatly in the years since:  The horse barn and adjoining silo are both gone.  A machine shed and a ramshackle shack we used as a garage are both long gone as well.  And a better constructed garage now sits in the spot next to the house that was once used as a horse corral.  The stone façade house still stands, however, and it looks almost the same as the day we moved out.

I seriously doubt my family has given second thoughts about that farm; they likely think of their time there as just another chapter in their lives.  I, however, have drove past it a couple of times (it’s not too much out of my way to and from Madison), and I’ve even snapped a couple of photos of it.  When I do have the chance to drive past that farm, I tend to slow down and give it a long hard look of fondness.  I especially tend to gaze towards the windows on the upper northwest corner of the house — where a room that was chiefly used to store one man’s property was another girl’s private, quiet birthplace.


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).

9 thoughts on “Allison at the beginning: How I started dressing up

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