The Twenties to Forties

Off to college I went, to a military school several thousand miles from home.

Being in a military college with no women around, panties were inaccessible.   But when I went home that first Christmas I made sure that I had a pair of my sister's panties to take back with me.   Indeed, I wore them back, under my uniform.   Although I didn't wear them at college I found their presence warm and reassuring.

In my last year I attended regular university where I had a room of my own.   This was the time I started to buy panties which I could call my very own.  It was an exciting time for me, and I went wild with panties, accumulating well over two dozen by the time Christmas holidays had come again.   I wore them full time while my male underpants sat unused in my dresser drawer.   That is, I wore them full time except when I was out on a date.   Still I had the nagging feeling that what I was doing was wrong.   That feeling became so great one night during the last term that I laundered them, bundled them all up and left them, in a paper bag, at the side door of the YWCA where I hoped that someone could make proper use of them.  Never again was I going to engage in such a filthy habit.   I cried myself to sleep that night.

Yet, less than a year later I was at it again.   I had been in a department store to purchase some shaving items.   The route to the men's toiletries department led right past the lingerie section.   As I passed through a very elegant pair of panties caught my eye.  They were so beautiful, a pale pink with a lacy leg edge.  I became quite agitated, and my heart started pounding.   I hurried my step.   I had to get out of there before temptation got the better of me.  I was in a sweat when I reached the men's department.   And while making my purchases I could not stop thinking about those very sensuous panties.   It was driving me crazy, and after accepting the bagged items from the sales clerk I just had to go back to those panties.

I bought three pairs, pretending that they were to be a gift.   The sales clerk wanted to know if I wanted them in a gift box, and I accepted.   My hands trembled as I paid for them.

Exiting the store quickly I almost ran back to my apartment room.  Once there I opened the box and held the silky panties to my face.   My heart was pounding and I was trembling with excitement.   I removed my pants and underwear and slid a pair slowly up my legs.   As the sensuous nylon caressed my excited being I climaxed profusely.   The panty front was soaked, but I didn't care.   I was once again in panties!

By the time I met my wife-to-be I had again accumulated several dozen pairs of panties, mostly the full sized, waist high type.   Bikinis were just coming into vogue then, and were just starting to appear in lingerie shop windows.

Soon after my marriage I again disposed of my collection.   It was just as difficult as the last time, but I kept telling myself that it was 'for my dear wife'.

In my early thirties I was driving home from work one day when I spied a lady hanging out her 'daily dozen' on a wash line to dry.   The sight of those dainty items fluttering in the gentle breeze set my emotions into turmoil, and I was back at it again.  I knew it was wrong, but I turned the car around and headed for the nearest shopping centre.  There I went on a splurge and bought half a dozen pairs of panties, all different colours.  Four were of the full sized, waist high type, and two were sexy bikinis.   At home I kept them hidden in a secret place in the basement, and I wore them whenever I could, (which meant most days).  Within a year my tastes had changed somewhat, and I found myself buying full and half-slips as well. Then came lacy garter belts and seamless nylon stockings.   Bras were last, as I felt less than properly dressed without boobs under my slip.  It was so exciting to 'get dressed' and drive around in my car.   I did it at least once a week.

By the time I was forty I had disposed of everything again.   It was a bad, degrading thing that I was doing.  I knew it was wrong to want to dress like a woman.  I felt so guilty.  And yet, why did it always feel so good, so freeing?   Why did I feel so comfortable dressed like that?  I didn't want to BE a woman, I just wanted to dress like one.   Within two months it had started all over again.   I don't remember what exactly triggered it off this last time, but whatever it was has left me in a state of turmoil ever since.  It was at that time that I started to shave my body hair, save for my arms and my head, and a little bush above my penis.  In addition to clothing I also had bought some long black false eye lashes and a set of deep red plastic fingernails to try.  One day, while my wife was out of town, visiting with one of the kids, I took one of my wife's skirts, a very short, white, pleated nylon skirt, and a white sleeveless top from her closet and put them on over my own feminine underwear.  I used a wide white leather belt of hers, which cinched in my waist considerably, far more than comfort would allow.  I slipped on a pair of open-toed white sandals and the brunette wig that she hadn't worn in years.  Then, with a little makeup on and my false eye lashes and fingernails in place I thought to "step out".  Taking one of my wife's white purses and putting my wallet, house keys, and a clean handkerchief in it I headed out to the car for a drive.

I got feeling so confident as I drove around I felt like really stepping out.  The more I thought about it the more emboldened I became.  I parked the car in a quiet residential neighbourhood and went for a walk around the block.  I did my best to 'walk' as femininely as I could, whatever that was.  About half way around the block, I guess just about as far away from the car as I had planned to get, a car with three men in it passed from behind.  They tooted the horn and gave me really big smiles and waves as they went by.  I was scared shitless.   I headed back to the car as fast as I could, pretending that I hadn't seen the guys.  By the time I was safely locked in my car my heart was just pounding.  What if they had stopped?  What a mess I would have been in!   After several minutes to calm myself down I thought it best to head for home.  It was the last time I ever did anything like that!

Later that week, upon my wife's return, I mentioned that I was wearing a pair of her white nylon bikini panties.  I told her that they really felt good and, what's more, I felt that they looked good on me.  I asked her if she would like to see for herself.  Her reaction was so negative that I immediately went up to the bedroom and changed into regular men's underwear.

After that I kept the entire subject of cross-dressing completely to myself.  It has been only recently that things have changed.

Back to Samantha's History Back