I wasn’t sure if Kandi would want to post this story. It is not about my crossdressing and mixing in public. But I believe every once and awhile we have to think about our health. I think my situation here is different than most.
Being born gender male I have a prostate, like all males. And when we get into our 50s we should have it checked regularly. In my early 50s I was experiencing enlarged prostate symptoms, so after a digital exam and a PSA blood test my doctor prescribed medication to help shrink it. A daily pill for the rest of my life.
As the years went by I had the annual digital exam and PSA test. One year the diagnosis wasn’t good so I had a biopsy performed (not pleasant) and the good news was it was benign, no cancer. Continued taking of the medication kept my condition in check and I have had no further problems and none of the earlier issues related to an enlarged prostate (see Clint Eastwood at the start of the movie “Trouble With The Curve”).
But the medication I was taking may cause gynecomastia, male breast enlargement. Now for a crossdresser that is not a bad thing. I can now comfortably fill an A cup bra. And with a little help I can achieve my goal of looking like a B cup woman. Unfortunately, like most women serious problems may occur in our breasts. Last year I noticed a lump in my left breast. Upon seeing my doctor he ordered a mammogram for me. So there I was at the hospital getting a mammogram and an ultrasound to determine if I had breast cancer. Once again, good news it was benign.
And the bottom line; whether you are male or female, or somewhere in between, please get yourself checked regularly for cancer. As the saying goes “the life you save may be your own.”
As a woman I tend to think a lot about my appearance, as I’m sure all of you do. But I am not overly fashion conscious as you can tell from my previous pictures posted here in Kandi’s Land during the past two months. I really want to make sure the world that sees me immediately thinks that I am a woman, knowing that any second look will reveal the real story.
Last summer, on two different occasions, I had comments from strangers that illustrate my point. The first occurrence was when I was taking a short walk on a hot summer day. I was trying out a new dress and heels and I just wanted to be out and seen (see picture of me standing on bridge). The comment I received was “I love the early 1960s vibe of this outfit/look”.
The second occurrence was a few weeks later when I was in shorts, a tee shirt and flats. It was a nice day for a walk and to show off my new hairdo (see head and shoulders picture). The comment was “you resemble the wonderful actress Patricia Neal! Just amazing”.
Now both comments are flattering and I am sure that is what was intended. But on second thought, they both infer that I have the fashion sense and look from fifty years ago. If you don’t know who Patricia Neal is you will have to Google her. Hopefully the comment to me was looking like Ms. Neal while she was in her 40s/50s, lol.
Back to my hairdo. In this first instance you can see my hair had quite the upturn curl on the sides and back, which I did not prefer. The “Neal” look is smoother with some wave, which I do prefer.
So, no matter how I/you look, the public will immediately have an opinion about you, even if they don’t share it. I just went with it all and enjoyed the moment. I am who I am, just me.
When I was in my early thirties (1980’s) I had my first desire to wear women’s clothes. I wish I could tell you why this feeling came over me, but I don’t know why. I purchased lingerie, a dress, pantyhose, heeled slingback shoes, wig, purse and makeup. I modelled them at home a few times and experimented with different makeup styles.
But I never wanted to just sit around the house, I had to walk the sidewalks of neighboring towns and be seen by people (but not noticed)! Not only did I walk around, but I ventured into a couple of stores to buy gum or look at women’s clothes. I was very, very nervous, but determined to do it. Most people I passed made no recognition of me, but sometimes I did hear some laughs after I passed by. One time out I was called a “faggot” and laughed at. Another time out I was laughed at and I heard someone say about me: “there goes one that needs an operation”. I was also chased down the street once, but got away in my car. I really enjoyed the feeling of presenting as a woman. I also did not tell my wife. Eventually I pressured myself into purging it all and tried to suppress that urge.
A few years ago (2018) I was “surfing” the internet and came across pictures of beautiful crossdressers and Tgirls. Feelings came flooding back to me. I also went on YouTube and saw videos of many people presenting as women. I knew I had to resume my feminine presentation. One such mature YouTube Tgirl I noticed was on sidewalks I had walked decades ago. She was very well dressed and poised as she walked. I thought she was very classy and beautiful. Her name was Alison.
I started to stock my closet again with lingerie, a skirt, a few tops, pantyhose and flats and pumps. I was able to make contact with Alison. This was very special to me because I had someone from my neighborhood who I could share my thoughts and get expert advice. This was Jocelyn‘s “tipping point”. Alison initially said she had been dressing since an early age, but never ever thought she would have a friend or acquaintance. She was also unsure if she wanted any. We did exchange many emails over the months and sent pictures of each other back and forth. Alison gave me many tips on wigs, makeup, dresses, shoes and presentation style. She also told me about blogs such as Kandi’s and Stana’s Femulate and about YouTube dressers I should see and learn from. [Editorial comment: wow!]
I ventured out many times over the next year with none of the issues that I came across decades earlier. I was filled with joy as people accepted me for the woman I was.
I wanted to meet Alison face-to-face, and Alison agreed to meet in a safe and open environment. What a thrill for me to actually be out in public talking with someone like me. We met in a park by the water of the bay. Both of us were dressed very casual in leggings/jeans, running shoes, light tops and carrying purses. A brief walk on a path, passing many people, and then sitting on a park bench. We talked for two hours, sharing a lot about each other. Alison was surprised that we had spent that long together.
We went our separate ways back home. It was then I realized we hadn’t taken a picture of ourselves. How frustrating! But pictures of each of us are shown here. My picture is a closeup selfie taken shortly after our meeting. The two pics of Alison are showing off a coloured skirt and a “rockabilly” swing dress she has just purchased.
Alison and I acknowledge how wonderful it was to get together and we plan on doing it again soon. I have friends over the internet, email and blogs, but nothing compares to sitting next to a friend and just talking. Thanks Alison, dear friend.
Well!!! I do have Alison’s permission for the story content and the two pictures of her.
That is what we do here at Kandi’s Land! Bringing beautiful people together since 2017.
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!
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.