Tips & Tricks
First of all let me set the time and conditions when my “other me” began to emerge. From the very beginning I never wanted to have SRS and actually become a female. This is as true today as it was then. It was long before smart phones, the internet, and even television. It also took place during the Second World War. (Yes, that's how old I am.) Living conditions were tight as everyone was still recovering from the Great Depression. As a result, we had a very crowded house and I was forced to sleep in my grandparents' bedroom. It was a very loving household and everyone contributed to make everything work.
With all that in mind, my very earliest childhood memories are of watching my grandmother getting dressed in the morning. Most of what I write here occurred long ago, so the detail into which I go may be influenced by what I imagine must have happened. I never saw her naked, as she always appeared with her “foundation” garments on while she continued to get dressed for the day. As I recall, I was intrigued as she rolled her hose carefully up each leg and fastened them to the garters which hung from her corset. A full slip usually went on followed by a pullover dress of some kind. A housedress if she planned to work around the house, or something nicer if she was going “down town.” Next she sat down at her vanity and applied her makeup. This was particularly interesting to me as the fragrance of the talcum powder, nail polish and her perfume wafted across the room and was very pleasant. (Something I would pursue later.) Lastly, she slipped into her heels as, during this period, every woman wore heels, a dress and hose every day.
Although we all lived in a crowded home, everyone except my grandmother and I went to work fairly early each morning. This left me to my own devices, especially if grandmother was doing the laundry. This task, in those days, was arduous and time consuming and offered me a chance to investigate some of the feminine things I witnessed almost every day. I know I opened some of the drawers and felt some of the items inside. I remember that I was afraid of being discovered, but I wanted to at least open her lipstick tube and apply a little to my lips. And I did...! I quickly untwisted the tube and put the cap back on. I went into the bathroom and shut the door. I looked into the mirror and saw a pathetic image with a red mouth staring back at me. I grabbed some toilet paper and wiped the mess from my lips. Not a very successful first experience.
I soon started school and my “play time” was practically nil. That was ok as there was plenty to do at school and after school. Things kind of stagnated until I was eight when my father re-married and we all moved into an apartment nearby. My new “mother” was very nice and we all got along very well. When she moved in with my father and I, she naturally brought her bedroom set and all her clothing. Space being at a premium, she put most of her things in a spare bedroom, which unknown to me at the time, would soon be my room. I inherited her bed, one chest of drawers and part of the only closet. Her vanity had lots of makeup items on it as well as perfume, dusting powder, etc. Inside the drawers were many underwear items; things I couldn't wait to explore. The closet had quite a few dresses, blouses and skirts. On the floor were many shoes, many of which were high heels of every description. Throughout the room there was a subtle aroma of perfume. I didn't know if I should be offended by all the girly things because, after all, I was a boy...! I quickly put that thought aside as I was anticipating becoming more acquainted with everything I had seen. Finally the ideal occasion was at hand. My mother left me at home and went to visit her mother and would be gone most of the day. After I was sure she was gone, I went to my room to explore to my hearts content. The first thing I did was put on a bra and some panties. I was so excited that my hands were shaking. The feeling of the panties rubbing against my “maleness” is indescribable. I stuffed some tissue in the bra cups which gave me a nice bust line. Next came a garter belt and hose. I remembered watching my grandmother put hers on so I tried to emulate how she carefully rolled them up her legs and fastened them to the garters. It took me a little while to get the hang of how to do it properly, especially the ones in back, but I finally succeeded. Again, the feeling of the nylon material on my legs was wonderful and very exciting. A white silk full slip was next and then finding a suitable dress became the next decision. Or maybe a blouse and skirt...? So many decisions; how does a girl choose? I finally picked out a sleeveless dress (I think it was referred to as a jumper.) It was royal blue and came to just below my knees. It seemed like there was something missing so I chose a white blouse from the closet and put it on under the jumper. Next I picked out a wide black belt and chose some black open toe pumps. Now it was time for some makeup and accessories. I went over to the vanity and sat in front of the mirror. A little powder to cover the shiny spots on my face. Then some blush on the cheeks (it was rouge then) a little mascara and then lipstick. This time a little better result than the first time I tried. I found a bracelet and a ring and went to check my image in the full length mirror. I remember thinking that I didn't look too bad. I wish I had a wig, but I hadn't seen one in my mother's belongings. It was a little difficult walking over to the mirror in the high heels, but I could practice that. The sound of my heels on the hardwood floors was exciting, but I would have to be careful not to twist my ankle and possibly break a heel. (Or my ankle.) Obviously a lot of practice would be in order.
Everything I have described so far occurred when I was too young to have known what an orgasm was let alone have experienced one. That would come in a couple of years, and open new horizons for me...! On that memorable day I was in my room anxiously anticipating getting “dressed” in, what I now referred to as my clothes. I selected a pair of pink panties; panties were always first. Next came a matching bra. While putting on the bra, my movement must have created some friction between the panties and my penis as I was in the process of getting an erection. It felt so good I applied a little additional friction with my hand. Suddenly, without any warning, I had my first orgasm...! My knees were weak and I was trebling all over.
I also had a “situation” as my panties had a prominent wet spot in front. How would I clean up my mess without mom knowing? Maybe if I hid them she wouldn't miss them!?! And if I hid them under my mattress I could put them on after I went to bed. That thought painted all kinds of fantasies in my mind. I did just that and enjoyed many enjoyable “bedtimes” thereafter.
Inevitably, the exposure to “discovery” caught up with me. One Saturday my mom and dad left to visit some relatives and I begged off siting some sports activity or another. After they left, I hurried to my room to do my “dressup” thing. I should have waited a little longer...!
I suddenly heard the front door open and the unmistakable sound of my father's footsteps on the
stairs. I had no time to undress and nowhere to hide. I hadn't even had time to shut the bedroom door and he walked right in. I'm sure that my brain “froze” and I can't even remember what he said, but I know I mumbled something about just wanting to see “what it felt like.” To this day I have no idea why he came back, but that event triggered another first. I vowed that I would never ever even touch anything feminine again. Thus the first of many so called “purges.”
Contributors' stories about getting caught in interesting situations...
If you have a fun or interesting story about happenings while wearing womens' clothing that you want to share, Email them to email@example.com and I'll post the best ones.
“Early when I was still becoming proficient, at being out in everyday public settings, I was very happy with my clothes, my hair and my gestures. Taking hints from the internet, I felt my make up was just okay, and I was just getting started working on my femme voice. So one evening I decided to go see a movie en femme. When I got to the theater box office, I said “Julia” (for “Julia and Me”) in a convincing enough voice, and gestured “one” with my finger. The teen ticketing person, gave me an odd look, turned around, opened the door and said something to a teen girl working there too, that dashed off into the lobby. When I walked into the theater, the (teen) ticket taker giggled. The (teen) clerks behind the concession counter were all staring at me; I was pretty rattled by this. When I finally got seated, and the movie started I was so relieved. But partway into the movie, a (teen) usher came in with a flashlight and was looking for something on the floor. When he spotted me, he left, but returned with others (teens) that stood along the wall alongside my row, peering in the dark at me. I tried to melt into the seat. Luckily, they left before the movie ended, and when it did end, I walked out the door that led right outside, very relieved. I figured out it was most likely my makeup that gave me away, since the ticket taker only saw my upper body. So, I arranged for a makeup lesson at a transformation shop, where the owner knew how to deal with beard shadow, thick eyebrows, etc. Then I practiced for the next month putting my make up on as often as possible until it felt like a “routine”. I’ve never had a similar bad experience since – it's one of the best investments I made. Then subsequently developing my femme voice completed what I felt I needed to be confident in everyday settings.”
One evening I got dressed up, and some TG ladies that I had met suggested that we go to a club. We had a great time and met some of the ladies who were associated with Girl Talk Magazine at that time. I had my usual one mixed drink. And talked and danced. Eventually, it was time to go and I went back to my car and started to drive off. After no more than one block, the flashing red lights came on from behind!
I think that I had two heart attacks one after the other! Me in a long blond wig, slightly shear clubbing dress and a rental car! OMG! I pulled over and one of the officers in the car came up to my window and I had at least two functioning brain cells so I had my driver's license and car rental contract out. Although my arms felt paralyzed at the time and I was hyperventilating, I clearly remember him looking at me and then my license and then very quickly, his head snapped back to me with a very startled look and a slight gasp. And then he went back to his car and I waited and waited for hours it seemed while he looked me up in the computer.
Then both he and his younger partner both got out of the car. The younger guy seemed to be enjoying things a little too much, as he ordered me to get out of my car, spit out my gum, and go over to the sidewalk. I really didn't want to litter so I looked for a place to put the gum, and he said, "Get rid of the gum, NOW" Yes Sir!!! And somehow, I walked over to the curb, walked a straight line, and didn't fall over in my 3+ inch heels on the very rough sidewalk. And I learned the fine points of doing a breathalyzer test.”
Fortunately, I passed and the senior officer followed me back to my car and said some soothing things and, "Sorry to bother you Miss, but you started up a little fast from that last stop sign. Please drive carefully." And after he left and my heart rate dropped below about 150, I drove back to my hotel and screamed!!! What an experience!
This happened a while ago, my spouse was visiting our daughter stationed in Germany and I had a week to be Kris. I went out one night no where in particular wearing a white linen skirt and a black top with black high heel sandals. As I pulled into a gas station (in my spouse's SUV) i cut the corner to tight hit the curb and blew out a tire. I pulled into the parking lot and reviewed the damage. The sidewall was completely ripped, and i looked down at myself and said there is no way I can change this tire in a white skirt. I was about 3 miles from home looked at my high heel sandals and realized there was also no way for me to walk home without some intense pain. So I faced the moment of truth and called AAA. While I awaited my fate with the AAA guy, several lovely gentleman stopped to ask if they could render assistance, which I politely declined explaining AAA was on the way. So the AAA guy shows up, I give him my card with my male name and he promptly and professionally changes the tire. As I am signing the paperwork, he shyly asks if he can ask a question. I thought ok here is comes I have to explain why I am dressed as I am. He was so polite i agreed to the request. To my astonishment he asked me if i had a partner. I told him yes I was married. He looked up at me and said "Shucks"..I was stunned. I gave him a generous tip and thanked him for his help. I was elated and also a bit scared of the prospect, in retrospect more elated than scared.
I thought I would share a experience I had Dec. 16th this month. This is something I suppose could be a nightmare for many of you. The reason for telling you this story is not to boost about it or to brag about it. But to make you aware this could happen to any of you and you need to know what to do if any of you experience it. I have no doubt some of you may have already had this happen to you. But I wanted to share this with some of you that has never had this happen to you.
I went out and took my hair Stylist out for a Christmas Dinner as a thank you for always doing such a great job on my wigs. It was around 1130pm and I was taking her back to her Shop. When I was getting on another freeway and merging to the right lane to enter the Freeway, I ended up swiping the back bumper of a Mazda SUV. I was driving my Corvette and fortunately I didn't experience any damage to my car. Anyway this was the first time I have ever had a accident as Diana. When we both pulled over, I asked her if she was okay and she said she was fine and said she had called the Highway Patrol. I was pretty nervous about this but I was calm and just waited for the highway patrol.
When the CHP came, I gave them my license , my registration and proof insurance. At this time, they weren't aware I was a transgender girl and I just didn't say anything. I just kept quiet and I figured they would figure that out once they saw my license. They never did questioned me about my gender. They just asked me to describe what happen and so I did. They did ask me if I had anything to drink and I told them I had one glass of wine which I did. The officer did give me a test me to see if I was drinking and asked me to follow his finger. I didn't have problem and then he said they might ask me to take a breathalyzer test and I didn't say anything . I just kept quiet. He came back and gave back my documents and gave me a card with information on how to get a copy of the collision report which would state who's fault it was and that was it and then I went on my way. While this was all going on, there was a total of 4 highway patrol officers present. That made me a little nervous but none of them said anything to me except the one that was taking report. Maybe they were just observing what was going on as protection to their fellow officer or was just curious and had never seen a Transgender girl in a accident before. All went well except for two factors. None of my family are aware of the other part of me as a girl and I was very concerned because of the Collison report that I would be found out.
I emailed a friend and gave her the whole story since she was a retire law enforcement officer to get some info from her on how all this goes. I also called another friend who is a insurance agent and told her what happened. They both stated that officers are not allowed to say anything about your gender if you are dressed as a girl in a report unless it was one of the factors that caused the accident which this wasn't the case in my accident. I was still a little panicky about all this since I had never experienced a accident as a girl every before. When I did receive a copy of the report, there was nothing said about me being dressed as a girl or even had any indication that my friend Laura was in the car. I was very relieved to have a positive ending to this incident. That said, I doubt my wife would have ever seen the report but I was concerned also about what my insurance agent would have said if these factors were in the Collison report.
So my point to you all: Don't drink or drive! Or if you ever experience a accident while you are your femm self. Don't mouth off or say much to them. Just do everything they tell you do. These officers were all polite to me and very respectable. They conducted themselves very professionally and was just doing their job. When the officer handed back my license, Insurance card, and registration, he said thank you ma'am.
Also when you are out and about , please drive more cautiously than you would as a guy. Just be polite to the officers and don't panic. Just keep calm.
I never got caught myself, in person, that I know of, but I remember when I was a preteen and early teen pretending to be sick so I could stay home to dress up too. I almost got caught a couple of times when my mom came home from work early for lunch, but I dashed into my room and quickly changed clothes. I know she wondered why I was out of breath and seemed a little flustered when she came to check on me. I thought she might have seen me once through the large living room window as I ran across the house when I heard her car door shut, and I saw her in the yard heading to the door. I also once went to let our dog out, and the dog turned and ran back in knocking the door wide open leaving me standing in the doorway in a dress and pantyhose open to the world. Fortunately, I don't think any of the neighbors saw me.
I was at a club in Pasadena with my girl friends all dressed to the nines – short black leather mini skirt, nude stockings, 5” stilettos, tight black sleeveless top (it was summer) and my longest auburn hair. Dancing, drinking lightly, laughing, enjoying being a girl.
Several fellows were asking me to dance or buying drinks for myself and my girl friends… All in all, a great night… so far.
Someone asks me to dance with him and I agree and we are off on the dance floor dancing to some old rock and roll song… as soon as the music turned to a ballad we began to close dance. That’s when my dancing partner was tapped on the shoulder and the fellows asked him if he could cut in because we were “old friends.”
I looked at this new fellow and my heart stopped. My body froze as he took me into his arms. He pulled me close. We danced or swayed to the music. He said nothing. But, I was in sheer terror. THIS WAS MY CURRENT BOSS AT THE TIME!
The music stopped and he led me to the bar and ordered me a champagne. He looked into my eyes and quietly said, “You are so beautiful. I do not know where you have been all my life but I want you now.”
I was speechless. We drank and I continued to be dumbfounded and said nothing. He chatted all about himself – what he did for a living and what he loves about me and I realized he maybe did not know who I was.
We finished our drinks and then he took my hand and wrapped his arm around my waist as he led me out of the club to his car. I still said nothing… He opened the door for me and then got in on his side. We sat in mute silence for what seemed like forever.
He turned to me and kissed me deeply. As his tongue was seeking entrance to my mouth his hand was seeking entrance to my crotch! I broke apart from him and said in my most female voice possible “NO!!”
He grabbed the back of my head and tried to force it down on his crotch… I refused… and the lot security guard tapped on the window with his flashlight… I opened my door and fled back to my girlfriends.
They assured me that he did not know who I was… after all he was in a gay / lesbian / Transgendered Bar. So even if he did, would he tell anyone?
Next day at work, I saw him and he said nothing about it to me and continued to treat me normally. After several hours I asked him what he did last night ( we were alone) and he said “watched a football game and went to bed.”
Wow! That was ridiculously close call!!!
Now it is 20 years later and he hires me again and tells me that I am the reason he is married! That he saw how in love with my wife I am and it was and has always been something of deep meaning to him.
So on our job together we end up in Honk Kong and he takes me and several of our co-workers to Macao for the weekend – his treat. (He’s very weathly now). He buys us all hookers* (which is another story) but the one for himself is a CD… the next day he claimed that he did not know. But was surprised and kicked her out. We all knew she was… and all our rooms were on the same floor – we owned the entire floor – and I saw her leaving at 10am the next morning.
At Brunch we all talked about transgendered and he gave no indication that he knew it was me all those years ago. And as we got into the Hydrofoil boat that was taking us back to Hong Kong he grabs my hand and says, “All last night I was dreaming about a girl I met in Pasadena 20 years ago!!!
*(Just so you know, I sent my hooker home before we got to the elevator – she cried and I told her to consider it a paid vacation – but that’s another story).
Last year I did a tour of our Southern California dessert. It was my first time being en femme for several days, even checking into hotel in Palm Springs en femme. I handed my (male) ID to the desk clerk with my heart in my mouth. But she simply looked at the ID and at and then at face which had just been professionally made up- lipstick, eyeshadow blush etc., but just gave me my key and showed no reaction. But checking out she was again at the desk and gushed at how beautiful I looked.
Well I drove away, still en femme to the northern dessert and spent several days in Nevada near Death Valley park. Coming back at night from a day and evening touring and having a great time as a wild lady in that wild place, approaching my room I had the moment we all dread. Red lights began to flash behind me. I pulled to the side with my heart pounding and thinking it was horrible end to a glorious trip. The seemingly tough redneck cop walks up and tells me he had pulled me over because I went through a stop sign and asked for me license. I handed it to him and told him I was trans, before he had to ask me. His response: "That's ok. I have no problem with that. This is America. We can dress anyway we want. He was obviously enjoying it and asked me a few questions about when I "made the change" and so on and I answered honestly and politely. He was the nicest fellow you could meet! Then without any explanation he simply handed me back my license and walked away. Far from source of disaster, being trans saved me from a fat ticket. When you hear that truth I is stranger than fiction, believe it!