It was February 2020 just before COVID changed everything. I was driving to Florida for two weeks to go golfing with relatives and then with friends. I initially believed all thoughts of being feminine would have to be abandoned for that time period. None of them know me as Jocelyn.
But then I realized I would have two days driving down and two days driving back when I could be en femme. With all the details of what 48 continuous hours would entail, I was both excited and scared. I finally decided to do it. Videos and blogs of crossdressers show confident women out and about, so I thought I could too.
I would go casual, with my leggings and a sweater or t-shirt, and minimal makeup. Before I left I purchased a pair of red US Keds ladies running shoes.
Unfortunately, going down I did not put on my wig. Leggings (shown in a previous post), a matching burgundy sweater, taupe pantyhose, the running shoes and panties and bralette. I used the family washrooms at the highway rest stops. I’m not sure how people “took me” at restaurants, gas stations and motels.
But, two weeks later on my trip back to Ontario, I put on makeup, wig, teal coloured t-shirt, leggings, running shoes, panties and bralette. It was obvious I was looking womanly. I used the women’s washroom at the highway rest stops. I was a little nervous the first time, and the other women didn’t notice, or look, or say anything. I felt wonderful just being one of the gals in the ladies washroom. At the fast food restaurants I was called ma’am, and at the gas stations the attendants seemed more friendly towards me. There were no issues checking into motels. I was just considered another person. The whole trip back I was just viewed as another “senior” woman
Crossing the border coming home, I did take my wig off.
Of course I don’t know what some people thought, if anything, but no one made comments to my face or behind my back. I was Jocelyn, and made to feel feminine. What a marvelous time. I’m glad I did it. I think my casual attire made me look like a regular tourist.
I received this in the form of an e-mail and I thought it was the best way to present this (with Jocelyn’s permission).
Kandi, I don’t know why, but getting the chance to communicate with you makes me feel very happy and comfortable. So, here is what has happened these last two days. (It pleases me more that you know.)
As I mentioned before I was getting a two hour window Monday morning to be out in the neighborhood. For days in advance I was thinking about what to wear and where to go. I enjoy doing some planning for an adventure.
First thing Monday morning I get my body ready and put my makeup on (I enjoy that). I thought I would be low key with leggings, a sweater, shoes and a gender neutral jacket. I thought about going somewhere quiet and take a few pictures and then back home.
BUT, then I thought “what would Kandi do?” (Readers, thinking what would Kandi do will generally result in trouble). So on goes the pantyhose, skirt, front zip sweater, ballerina flats and a scarf.
Well, Kandi wouldn’t go to a quiet place, so I drive to the nearby town and into the Post Office and mail a letter and check my mailbox. Next a walk down Main Street to the bank to take out some cash. Saying hi to people as we pass by.
Back to the car and off to Walmart. In I go to buy a small tripod to hold my phone camera in order to take better pictures of myself. I asked a sales associate for help in finding the tripods. He was very helpful and courteous. I found exactly what I needed.
Before leaving I thought I would get another bra; something one size bigger (42 to a 44). I wasn’t happy with the selection so I went to self checkout.
I prefer paying cash whenever I buy stuff, so there is a SA specifically there to handle self checkout cash. She was very good with my purchase and helped get a bag for me to carry out my tripod. I then proudly walked across the inside of the store to the exit and out to my car.
I usually like to try my new purchases to see if they work, so I unwrapped the tripod, put my iPhone in it and mounted it on the hood of my car in the Walmart parking lot. I made a few videos of me walking out front of the car. Some people close by in their vehicles must of thought I was crazy for taking pictures out front of Walmart. (How great!).
It was then time to go home and cleanup. What a wonderful morning.
I have attached a picture I took before I headed out. It is probably my worst look, but it is feminine! I think my best look is in the first pictures I sent you wearing the red scarf.
Thanks for letting me tell my latest adventures.
Be safe and happy. Always, Jocelyn
How great is this! Out in public, interacting with people, feeling wonderful. I am blessed to know this beautiful lady!
This post means quite a bit to me. It is the reason I keep doing this blog. I have recently considered shutting it all down, I do that often. The truth of the matter is, this is work. And it is work that I get paid nothing for. I get no direct human feedback, from real people in the real world. E-mails, comments, all wonderful, but they are virtual. But this is a labor of love. This place also apparently means something to some beautiful people. Jocelyn is one of them. She reached out to me through the “Contact” page on November 28 and here she is, sharing with out little community. She is a genuinely beautiful person and I am privileged to run this post.
Since getting back into crossdressing, after decades since a mid-thirties purge, I was contemplating the order of restocking my closet. Should it be shoes and a dress first, or get a wig and then go shopping for a wardrobe? I do not like shopping online since I prefer to see the item, try it on, and then purchase it if it all fits and the price is right. But a girl shopping for shoes and clothes with short grey hair is not good, but wig shopping in a dress isn’t a good look either. I also thought I could not go in a skirt, nor in regular jeans or slacks. So a few days before, I went to Walmart to look for some leggings; which I thought would be more feminine looking. I tried on various styles and sizes and eventually settled on maroon Jordache leggings. They look good on my legs, but I don’t have the hips and derrière to fill them out appropriately. Oh well.
I made an appointment at a wig store in a nearby Town that specializes in serving cancer patients and cosmetic customers. They do wig fittings by appointment only. So, Monday Jocelyn was to see a lady at the shop.
On Monday I got dressed in the leggings, a bralette, a sweater, flats, and a simple gold colored chain necklace. I only had foundation makeup on. I drove to Town, and because it wasn’t a cold day, I walked up the street like that carrying a pink wallet.
I was nervous when I approached the shop and went in. There were no other customers there and the shop owner was very welcoming and friendly. She asked if I was Jocelyn, and I was! My short grey hair was a dead giveaway that I was an “old man” looking for a wig.
We went to the back room and for the next 45 minutes I had a marvelous time trying different styles and colors of hair. The sales lady was quite helpful and she offered a few makeup tips as well. Her best advice was to color my eyebrows to match the color of the hair. When I looked in the mirror with the brunette hair, the grey eyebrows made the whole face look odd.
It cost quite a bit more than I hoped, but the quality is good. Of course I had to get a wig stand, shampoo, cleaner, and brush. And paying for it all on a credit card with a different name didn’t seem to matter.
This experience was my first, spending so much time with a stranger, and just being Jocelyn.
A few days later I took a number of pictures with my new hairdo. I’m not sure I made the right choice. Maybe the look will grow on me.
How lucky am I to make these connections, get to know beautiful people like Jocelyn?
I also received the following message this past Saturday on one of the forums I monitor (I made some edits to respect her privacy):
Hi Kandi. Thank you first off for accepting my friend request! Thank you also for your blog. It’s wonderful! I just found it a few days ago and have been enjoying it immensely. (Except the part where the Browns beat the Eagles-but hey, not YOUR fault-everyone beats the Eagles these days).
I surmise from your one post that you’re a practicing Catholic? Me too. I would LOVE someday to attend Mass as Jennifer. Unfortunately right now I’m struggling even to get out of my closet. My wife is not very accepting yet. Perhaps that’s why I’ve so enjoyed your blog. You show me that maybe someday I can embrace my femme side more fully and more meaningfully than is possible now. Thank you for that most of all.
September 26, 2020 – I worked the late shift at the event and didn’t get back to the hotel room until almost 9:30 PM. Too late for any outing, but I had other outfits that I wanted to put on. Time for a photo shoot!
First, I was able to mix and match this new dark red sweater with both skinny jeans and a gray skirt. The sweater is quite warm, perfect for a crisp fall day. The first necklace is also part of the package that my friend Samm had brought to me the day before. I tried the snake print heels again, and they were only marginally better. Walking was still painful, but I could stand for a photo. I changed back to my black heels with the skirt for a more classic look.
Then I put on a black and white leopard top with the same gray skirt. This is a spring and summer office outfit and was my second choice for the dinner Samm and I had the previous evening. I’m glad I went casual, as I hadn’t realized that I needed to iron the skirt!
The next dress is a navy blue number from Venus. I also got this style in hot pink at the same time last year, two dresses for less than the original price of one! I like the gold belt-like detail to define my waist, although it does show me what I need to do to get back in shape. Thanks to the virus and my work schedule, I haven’t been able to get in a power walk for weeks.
The final dress is a real favorite of mine, I love the floral pattern and the fabric is very soft and slimming, especially on my arms. The gathers at the middle of the chest give me a really nice shape. Once I work out how to show more cleavage, I’ll be sure to attract attention and compliments for it. I did have to switch to a lower heel for these pictures, but these are very cute!
The week of the event was a lot of work, but I did have a good time. Getting to go out dressed was wonderful too, I’ve missed that feeling of happiness over the past year. I can only hope that it won’t be another year before I get a chance again!
September 25, 2020 – I finally had a weekend where I was volunteering at an event and would be staying in a local hotel several towns to my south in Massachusetts. I hadn’t been out dressed since November 2019 for many reasons, including the current pandemic. I wanted to get together with my friend Samm, as well as shop at Ulta for some new makeup items. I had a slight delay in getting ready, as after I had showered and shaved, the event needed me to come back for 30 minutes to deal with a couple of questions. I put my male shirt and pants back on over my female unmentionables and drove back to the facility.
Once that was settled, I went back to the hotel and put on a light blue cold shoulder top and a denim skirt with black heeled booties (and no hose as it was warm) to remain casual. I used my new eyeshadow palette to try and highlight my eyes, as I wasn’t going to put false eyelashes on.
I shopped at Ulta, asked for assistance from an SA, and came out with a new lipstick, primer, and brow pencil. I met Samm along the plaza with a quick hug (we both were masked) and we chatted for several minutes before deciding on where we would go for dinner. We did have to wait for about 15 minutes outside the local restaurant we chose before our table was ready. Wearing masks makes a big difference in how we were perceived! We had a lovely dinner of salads (watching our girlish figures!) and I treated her for holding a package for me since February. She took a picture of me and emailed it to me.
We went to her vehicle and retrieved my package, talking some more before saying goodbye with another hug. I promised to send her pictures of the new items, plus ones of the additional outfits I had brought with me. I drove back to the hotel, walking through the lobby to the elevator and greeting the desk attendant as I went by. After I got up to my room, I opened the box and spread out the purchases. They all looked great and I couldn’t wait to try them on.
I first figured out how to set up my phone to take better pictures with the lighting in the room. I took some more photos in my casual outfit before changing into the red dress and new snake print heels. The heels were quite stiff and tight, and the 4.5″ stiletto squished my toes painfully forward. I could barely walk, and standing was a challenge as well, even after putting on hose to help my feet fit. So I switched to my standard black 4″ heels for the rest of the night’s pictures.
I realized afterwards that the red dress’ sweetheart neckline needs some more defined cleavage. I’ve been looking at possible ways to do that using the little movable flesh I have on my chest. Experimenting with that will have to wait for another day.
I had one more night where I could get dressed, but I decided to stay in the room as I was working the night shift at the event and didn’t get back to the hotel until after 9:00. More about that night and plenty of pictures in my next post!
I’m telling a bit of my history here, but I feel it’s worth the time to understand what changed in my mind about crossdressing and how I reached the decision to go out in public.
I started dressing around the age of 10, wearing my older sister’s and my mother’s things when I could. But I had a different reason for wearing them, one I will only say involved a specific kink. This drove my dressing for many years, where I never had interest in looking female from the neck up. No wig or makeup, but I would always fill out the bra with socks or pantyhose. I wanted my body to look feminine, as I would think of myself as a woman while dressing. But going out dressed was the furthest thing from my mind.
I found the courage to buy some of my own things in male mode in college and when I started living in my own apartment. Living near Boston, I discovered the existence of the Tiffany Club of New England, a support group for CD/TG/TS people. But since I did not want to go out, I did not connect with them (yet). When my wife-to-be and I decided to live together, I purged the few female clothes I had. I did try on many of her dresses and heels when she was out, as she was similar in size to me at the time, and continued even after we got married. After the birth of our daughter, she had difficulty losing the pregnancy weight and went up in sizes. I also found many of her heels didn’t fit me well, being slightly big.
I began buying my own female clothes again, just a couple of skirts and a sweater to start. Then it was panties and bras and dresses, I already had my own pantyhose. The final step was buying my first heels, which I did online. By that point in 2003, I had established Tina in an online community and joined many groups of people with similar interests. I did join the Tiffany Club’s email list, but did not become a member of the club.
I communicated with a few people from the other groups and wrestled with whether I could get up the courage to meet someone in person. It took quite a bit before I was ready, even though I knew some of the people were trustworthy. I bought a cheap Halloween blond wig and used some of my wife’s makeup to see what I could look like. After some practice, I met another CD in male mode and agreed to another meeting en femme in April 2011. She brought me another wig, much nicer than my old one, and I saw how much better I looked with it on.
This was the first time I seriously thought about going out dressed, but I only went to the Tiffany Club, as I had no confidence in my makeup skills. Clownish puts it mildly. I didn’t get out again for two years, although I started working more with makeup and buying my own limited supply. I went back to the Tiffany Club in July 2013, feeling a little bit better about myself, but still not ready to step out into the “real” world.
It took almost another three years before I had the chance to go out again. This is where my earlier post about my 2016 adventure comes in, and is my true tipping point. I had been buying clothes in male mode and online with no issues, and I had recently joined crossdressers.com to find more people who shared my approach to dressing. With amazement, I read their stories (including Kandi’s!) of going out dressed with confidence, and I started wondering if I could get up the nerve to do the same. As I wrote in that earlier post, I went shopping in androgynous mode and had no trouble. I dressed fully for another evening at the Tiffany Club and got a makeup tutorial on bringing out my eyes. Even though I did not go out elsewhere, I felt so much better about myself and knew that the next time, I would not be so timid.
Of course, that event didn’t happen until 2017, but by then I had lost most of my fears about going out and was so happy with my days fully dressed. Getting a manicure, being called “this lady” and “her”, shopping in many stores, and visiting the Tiffany Club again were all wonderful experiences. Since then, it seems like I have to get out when I dress. My feelings have changed so much in the past decade, when I originally felt I would never go out in public, to knowing the joy and happiness I feel when I go out as Tina. I no longer feel the need to go to the Tiffany Club, but prefer to meet others in public places and just be seen as women enjoying their day. I do keep to myself or with one or two others, as I tend to avoid large groups.
It has been a long road to get to this Tipping Point, but I’ve now seen the same response that so many others have. I realize how much more fulfilling being out as Tina is then my early dressing forays, and heartily recommend taking that step out your door.
With my wife away for the weekend, the big deal for me on Saturday was going for my first makeover. I had made the appointment at Ulta on Friday, although I had a possible crisis when my wife called Friday night and told me that my daughter might come home from college (in Boston) to get a few things for her senior week and graduation later that month. It would have meant cancelling my appointment to pick her up at her job, come home, then back to school. I texted my daughter late Saturday morning to find out, and she told me because of her projects and exams, she couldn’t spare the time to come home. Crisis averted!
So I went to Ulta, was greeted warmly by the MUA (actually the salon manager), and I sat in the salon where at least three other women were getting their hair done, with mothers and friends all around. No one gave me a second glance, I was just another woman getting her makeup done. The MUA was wonderful, she drew perfect eyebrows, actually applied false eyelashes to help with my hooded eyes (which I had failed at several times before), and gave me a beautiful look that I was extremely happy to see in the mirror. I asked her to take pictures for me, of course, as I couldn’t stop smiling the whole time!
With the makeover done, I went home to get dressed for meeting two other sisters from crossdressers.com at the Tiffany Club. I put on my new blue floral sleeveless Calvin Klein dress from Dress Barn, my favorite 4″ black stilettos, and a thin black cardigan sweater (for night travel as it would get cooler). I drove to TCNE and met the ladies, they are both beautiful. We sat and talked with the other TCNE members at their open house for almost 3 hours. The three of us had all been there before, just not at the same time. It was great to meet them both, and we’ve stayed in touch with each other in the two years since.
Sadly, I had to go home, but I spent some time taking more pictures (into early Sunday morning) before I had to strip off everything (makeup and nail polish included), and pack Tina away for a time. But I thoroughly enjoyed the days that I got to dress. This journey took a surprising turn for me over the three years from 2016-2018, and I am much more comfortable with myself and my presentation to be able to get out and interact with people. Thank you Kandi and all the readers of this blog who have shown me how to get over the fears and just go out!
My sincere pleasure! I am sure the readers were happy to hear a different voice.
I dropped my wife off at the airport Wednesday morning, hurried home, and pulled out my duffel bags from their hiding spot. I quickly got dressed in a forest green top with a silver necklace, new Gloria Vanderbilt Amanda jeans in silver grey, and black Christian Siriano flats (no hose as it was 90° F!). I had left my wig for cleaning the previous week and needed to go pick it up from the wig shop. I did some light makeup and tied a silk scarf around my head to hide my baldness. I had hoped to get there to have time for wig shopping as well, but the traffic was horrible due to a major accident near the exit I needed. So I wound my way through the back roads and only picked up the wig. I put it on in the car, then drove back home with a lot less worry. Later that night, I went out to Walgreen’s for a new mascara and lipstick, then stopped at a convenience store for lottery tickets. No issues whatsoever, as I deliberately made an effort to talk with the cashiers.
Thursday, I put on a fuchsia top, grey skirt and black Siriano 4″ pumps (again, no hose due to the heat in New England). I went to the nail salon I had visited before for a manicure with a bright fuchsia color, then I went shopping fully dressed! I did put my flats on again for shopping, as I didn’t know how much walking I could do in the heels. In Dress Barn, the SA immediately greeted me and started a changing room with my name (!) as soon as I picked out one Calvin Klein dress to try. I ended up with three dresses (2 CK, 1 Roz & Ali) to try on. The coral CK was a size 14 and felt just a little big. The blue floral CK was a 12 and fit like a glove, so I bought it (on sale for $39.50). The Roz & Ali size 12 didn’t come close to fitting, and they didn’t have a 14 to try. I also got unsolicited compliments from both the SAs and another customer on the CK dress I ended up buying.
Then I went to Famous Footwear, an off-price shoe store like DSW. I went straight for the clearance racks to just browse the 9 1/2. My eyes were drawn to a pair of black booties, and I’ve never been a fan of boots or booties before. So I tried them, they fit great, and then I saw they were Fergalicious Purge booties, retail $70, for $17. Sold! The fuschia top and grey skirt is what I wore all day.
Then, it was off to Kohl’s for more clearance rack shopping. I found tops, dresses, pants, and sports bras to bring into the changing room. The cute LBD has a chiffon overskirt and nice belt to cinch my waist. The striped top is a size medium and it drapes well. I also bought a sports bra with these two items and put back the rest. After all my discounts and Kohl’s cash, I spent just over $20.
After the shopping was done, I put the heels back on and went to a quiet casual restaurant for a late lunch, sitting at a high-top table with my legs crossed in a skirt, a heel hooked over the chair rung, enjoying a salad. I even went to the ladies’ room after eating and did my business in the appropriate manner (seated). No sirens, flashing lights, or angry bar patrons to be found. I even took some of the salad home, feeling more feminine than ever.
Friday, I put on a JLo cold shoulder top and GV jeans with the new booties and went to Macy’s and DSW. I didn’t find anything I liked in Macy’s, even in the clearance racks. There were lots of great shoes at DSW, but my budget wasn’t going to let me buy any more, and I had a delivery coming of dress sandals and a pair of western style booties. I called an Ulta north of Boston that afternoon and asked if they did makeup for TG women. They immediately said “yes”, so I was not feeling timid at all about making the appointment for Saturday afternoon before going to the Tiffany Club.
While I had been out dressed prior to 2017, it had always been limited to going to the Tiffany Club and at night. I shopped in drab all the time, and was androgynous the previous year. I just decided that there was no reason to be timid while my wife was away. She was taking two extra days to visit a friend in Texas after the conference, so I planned for a couple of outings.
Wednesday and Thursday I had dressed only at night after work and did not go out. Friday was a test run of my confidence, I put on my women’s jeans, a black tank top, scoop-neck black sweater, and black wedge booties. I put very light makeup on (no lipstick, just clear gloss), fixed my wig, and out the door I went. Drove out to Western Massachusetts for the morning, I had to wait for a plumber at my in-laws’ house (they are deceased, but my wife and I were managing the house at that time). I took off my wig, sweater, forms and booties and put on a male shirt and sneakers. The plumber came, did his work, then I took my brother-in-law’s three dogs out for a walk (one at a time, large Labs) before packing up to come home. After I stopped for lunch, I put the outfit back on, re-did my makeup and wig, then drove home for the night.
Saturday was one of the best days ever. I called a nail salon for a manicure, got dressed in black leggings, pink ribbed camisole, forest green top with attached silver necklace, and a black open cardigan. I did full makeup (I tried to keep it light for daytime), put on my wig, and drove off. I stopped at a Target and bought some new panties with a gift card I had, no one batted an eye. I then went to the salon, where I was warmly greeted, even though, not thinking, I had given my male first name when I called. The American woman doing my nails was so pleasant and we chatted easily about many things, including dresses. But I got the biggest surprise when the Asian owner came over to let the nail tech know about her next client, saying “you will take her after this lady” – meaning me!! She said it again, “once you are finished with her”, and I was soaring for the rest of the appointment! I got a lovely pale pink polish that was hardly noticeable, but I was feeling even more feminine when I left the salon.
I drove to a Payless store in a big mall, parked the car, and just walked into Sears to get to Payless. I know at least a couple of people read me as I went by, but I didn’t care anymore. I greeted the SA’s at Payless, walked to the women’s 9 1/2 racks, and started pulling down shoes to try. I was looking for another black high heel and found both the Karmen and Christian Siriano Habit black heels. They both fit perfectly, but the Habit were on sale, plus I had a 25% coupon, so those were the ones I wanted to get. I paid at the register, softening my voice a little, but I knew they knew I was not female. I walked back through Sears to the exit, back in the car, and drove to the nearest Kohl’s. I had a return from my online order, faux-leather leggings that were too big, plus $10 I earned for the order. I found clearance racks and browsed all of them. I pulled out tops, skirts, jeans, dresses – then it was time to try them on. Into the women’s fitting rooms I went, the first side was full so I went to the other side and claimed a room. Tried everything on, some fit, some didn’t (a great black lace dress was one size too small), but I was in heaven. I decided on three tops and a skirt, went to the register line, then was called “ma’am” by the young man opening a register. After my credit, a 20% discount, and my Kohl’s cash was applied, I paid a whopping 25 cents for everything.
Finally, it was time to decide on what to wear to the Tiffany Club’s Saturday night open house. I was originally going to wear a new forest green suede dress from my Kohl’s order, but I decided to wear the new magenta top and gray skirt with the new heels. I re-did my makeup for the evening, but then I sat anxiously on my couch for almost an hour as it was still light out at the end of the day. I finally said to myself, “Get out the door, Tina!”, drove to the meeting, and had a good time with the small group there. When I came home, I realized I needed pictures of this outfit. Not wanting more selfies, I set up the digital camera and tripod, then posed many times. I even took a close up, as I was pleased with my look. The pearl jewelry was borrowed from my wife’s collection.
Unfortunately, I didn’t get out again as I had hoped, but I did have some good time to relax at home. Sunday, I wore my new purple sleeveless top with a lavender miniskirt and my new black JLo pumps with a silver stiletto. Monday night I tried to dramatize the eye makeup (not entirely sure I succeeded). I was wearing my new green suede dress and my nude platform peep-toe pumps. I decided to try some different poses with the dress and figured out how to orient the camera for the picture on the couch.
I had hoped to go to the Tiffany Club on Tuesday night, but I had to clean up the house and put everything away before going to the airport to pick up my wife. Once I had dressed on Friday night, I didn’t wear male clothes again until Tuesday night. My ability to get out dressed has been limited due to hiding it from my unaccepting wife, but I believe that year I got over the majority of my fears.
The whirlwind of feminine times started on Wednesday evening when I got home from work. My unsupportive wife had flown to a meeting and would not be back until Sunday evening, and my daughter was still at college. I hastily stripped off my male clothes, hauled my duffel bag of female clothes out of its hiding place, and started sorting through everything. I knew that I needed to wash a lot, so I put on panties and a shelf-bra camisole with my homemade forms, then a short-sleeve nightgown and brought the laundry downstairs. I also needed to wash my good wig, so I put on an old Halloween one instead. I started the wash, got the wig washed, rinsed, and hung, then went back upstairs to watch TV. Two loads later, I put the dry clothes in my drawers and hung the dresses, tops, and skirts in my closet, along with lining up my five pairs of women’s shoes on the closet floor. All of the male clothes were pushed to the sides, although I was still going to the office on Thursday.
Thursday morning, I showered and shaved my legs, chest and underarms, underdressed in beige panties and nude pantyhose, and headed to work. When I got home that night, off came the male clothes and on went a beige bra with forms, hip and butt padding, a peachy-orange split-neck sweater, beige miniskirt and mid-heel peep-toe pumps. My wig was still drying, so I stayed inside relaxing without any makeup. At bedtime, after putting my nightgown back on over a soft-cup bra and panties, I painted my toenails a bright pink.
On Friday, I was working from home, so I shaved my hands and forearms and touched up my chest before starting the day in pink panties, black pantyhose, black leggings, a pink tank top, black cardigan, and black wedge booties. Mid-morning, I changed into a pink bra, a black floral slinky JLo dress and my 5″ black platform stilettos, adding a high-waist control panty to really hold me in and give me a female shape. I did have to go out in the early evening in male mode, so the dress, forms and heels came off, I shaved my face and went to the short event. When I got back home, I put the same dress on and attempted to put on makeup. My face and lips were okay, but the eyes were not good (practice time was needed!). I also put on some amethyst jewelry to match the dress, some clip earrings, a necklace with an amethyst drop, and a ring along with a gold shell bracelet. I felt really feminine even with the eye makeup disaster.
Saturday was the day I had been anticipating (and dreading) the most. I wanted to go shopping, but couldn’t yet bring myself to go in full female clothing. I was very androgynous, wearing black leggings, a black tank top under a male black shirt, white ankle socks and sneakers. No wig, but I put on some blush and clear lip balm before finally heading outside. I browsed the clearance racks at Kohl’s and found a forest green top with an attached silver necklace and a short black-and-gold flippy skirt. I also needed a pair of male pants, so I found what I wanted and took all three items into the men’s changing room to try them on. I wasn’t going to rock the boat by going into the women’s, not with my bald head! Everything fit great, so I went right to the checkout line and had no problems. Then I went to Wal-Mart because I needed some new bras. I found two that I liked (a black t-shirt underwire and a pink push-up) and I went up a cup size to a 38C because my homemade forms are a little bigger than a B. I also found a new crossbody purse in a neutral print, which I was much happier with than what I had at home. The final stop was at the mall, I walked the entire length to get to Payless. I found a perfect pair of Christian Siriano black pointy flats, size 9.5, tried them on in the back of the store without comment, and brought them to the register. The SA asked calmly if they fit OK, to which I replied “Yes, they do, thank you.” She rang up the shoes, and I was on my way back through the mall on a pink cloud.
I opened the shoe box in the car, took off my sneakers and socks, and put on the flats to drive home. What a great feeling! I brought my purchases in the house, took off all the tags and went upstairs to try on the bras. OMG, the forms fit perfectly and I couldn’t believe the difference in my look, just with the bra change. I decided to wear the black bra and black thong with black pantyhose under a diagonally striped black-and-white dress for the open house evening at the Tiffany Club, a New England CD/TG support group. It was only the second time that I had been out fully dressed to TCNE. I put on my black cardigan sweater, my new flats and some basic makeup (foundation, blush, lipstick). The makeup items went in my new purse, along with my license, glasses (which I don’t wear as Tina), and phone. I carried my black 3″ pumps to the car, wearing my sunglasses and wig, and off I went, changing into the heels before I was greeted at TCNE and whisked into the changing room for my eye makeup tutorial and application. Meghan was so gentle and explained everything as she did it, and I was so happy to see the result with my eyes brought out (they are hooded) without looking dark. I stayed at the club until about 9:30, had Meghan take my picture, then headed home. I was still fully dressed and bouncing at 1 AM! Then I finally took off the makeup and wig, put my nightgown on and tumbled into bed.
Sunday I wore the new pink push-up bra, pink lace panties, and nude pantyhose under a male shirt and jeans for the morning. I went and got some new makeup to match what was described to me. Then I came home, put on a floral bodycon dress and heels, and worked with the makeup for a couple of hours. Photos followed as I had a little fun! I had to clean everything up and hide it away before picking up my wife at the airport that night.
That four day stretch was my first real foray into dressing and getting out without any feeling of guilt or shame, except for hiding everything from my wife. I overcame a lot of fears and realized how much I enjoyed it and how much I wanted to do even more.