Crossdressing Storieslatest

My First Walk as a Woman

My First Walk as a WomanThe day was remarkable for me, when I first strolled down the street as a lady. I had yearned for this, yet experienced it only in my dreams. After a long consideration, I finally had the courage to reveal this close guarded secret to one of my close female friend. I was very nervous on how she would react, but she was very kind with her response. What’s more, with a caring and loving understanding, she was eager to assist me to go out in public as a woman.

It didn’t take a lot of planning, as I was accustomed to wearing exquisite ladies’ garments and clothing secretly. I was also familiar with feminine posture and body movement because I was constantly practicing at home.

I knew I needed some lessons from an experienced woman to polish my feminine image and my friend was all in to help me with that. She gave me some really helpful tips on makeup and feminine etiquette.

Then, she gave me a complete makeover and even helped me pick up the outfit that I would be wearing for my first time out as a woman. When she was done with the makeover, I couldn’t believe how pretty I looked. The makeup was subtle and simple, just enough to accentuate my feminine features.

After the makeup was done, I finally put on the outfit that my friend picked for me. It was a chiffon white blouse, a nude pantyhose, and a black knee length skirt. For the accessories, she made me wear pearl earrings, a simple chain with a cute butterfly pendant and a silver bracelet. Lastly, a pair of black high heels to complete my look.

When the moment finally came to leave the house, I felt uneasy and super nervous but my friend noticed this and comforted me that it was going to be great. It was around the evening when we left the house. I clearly remember how scared I was taking the first few steps outside.

Having my friend really made it possible to step out in public, otherwise I doubt I would have been so courageous after all. We walked through the streets and I was holding my friend’s arm like a baby. After walking for a few minutes, I felt more relaxed. I was so happy to finally present myself  as a woman to other people. The joy, the sensation of being a woman was unbelievable.

I noticed that a lot of men were staring at me while passing by. It made me feel quite nervous. So, I asked my friend if they knew I was actually a guy. She told me that women usually get a lot more attention and it was pretty normal for guys to stare. I knew it was going to take some time for me to get used to that but I tried my best not to let the stares bother me very much.

While walking down the street, my friend recommended that we could go to the movies. I agreed and we headed to a near by movie theater. There weren’t many people hanging around when we reached there.  We got the tickets and stepped inside.

While we were getting some snacks and drinks, a group of guys passed us and one of them accidently bumped into me. I was so frightened but he gave a smile and apologized.  I nodded and smile back.

It was such a fun experience watching a movie as a woman. I really enjoyed it. On the way home, I could feel the eyes of men trying to make an eye contact with me. I did my best to avoid but it was making me feel more feminize somehow. When we finally reached my home, I hugged my friend and thanked her for providing me with such an amazing evening. It was really exciting and fun to be among strangers and to be able to express my feminine side.

My friend asked me if I was open to hanging out with one of her friends for dinner. I was hesitant but she told me her friend was cool with people like me. So, not knowing where things would lead, I said okay and then we went to a restaurant, where her friend was already waiting for us.

My friend introduced me to her friend. I was bit nervous but as we started talking, I felt more comfortable. We order some wine and food and we had a nice conversation. It felt great to express my feminine side with another person. It was amazing that I felt as a woman among women in that moment of time.

I happily got home and dreamily reflected on the things I did that evening for many hours. It was truly a remarkable experience for me.

Submitted by Rachel 

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  1. Great story, and I identify myself with much of what you say. I am sure it was a wonderful experience for you, and hopefully only the first of many times going out as a woman… It is delicious!

  2. Very nice story! I am still planning my first time in public. I also have a female friend who knows, we are planning something.

  3. i’d love to do the same

  4. I am crazy about women,and being one. It would mean so much to me! If I could find a man who wants me as well, life would become complete! I so want to become his wife!
    Miss Roxanne Lanyon

  5. My first walk as a woman was with a group consisting of boy-cousins as well as other buddies of sea resort. I was dressed with my mother’s tennis-dress; I wore summer beach shoes elevated with full sole cork soles, a large straw hat with a feminine ruban and for accessories an assortment of bling-bling bracelets and earrings plus a large pair of shades (à la Breakfast at Tiffany). I’ve narrated this ‘first walk’ in previous posting. I was sweet ‘Françoise’,who was my secret and undeclared girly-name until just a few days ago as publicly disclosed onto my internet’s coming-out.
    The thrill resented is always unforgettable. You become a very pretty girl, ogled by guys in an instant! That says it all! What I remember from that ‘first time walk’ was the regret, as well as the sigh of relief when returning to ‘normal’. This is one of my remembering’s. When I removed this tennis-dress, all the ‘guys’ seemed very interested to ‘see what was underneath the cloth of the girl’. Alas, I had only my boy’s chest to show. I also felt some relief, as being again back on the ground after that ‘flight’.

    My real ‘First Walk As a Woman’ was a lot more dramatic, than the one’s just told above, which indeed was a safe joking play by teen-aged boys. During that real ‘First Walk’, I went alone. I was dressed-up as a ‘Kelly-Girl’, that is a tight (red) leather jacket with a scarf and a matching color berret over the Vidal Sassoon’s hair cut style wig. I had a mini-skirt of a dark color, thigh-high leg-warmers of a matching color also, which revealed the whiteness of my thighs. I have a fetish of being a ‘white girl’ while is bad places. I wore mini boots (red color) half-highheels. It was foggy, and was glad to have those warm clothes, because, although the San Francisco weather is rarely cold, I trembled with fear. It was about 11pm and mid-week.
    From my residence of Nob-Hill, I had decided to walk all the way to the Power-Exchange, which long walk included passing through Polk Street, the tranny hookers’ turf & workin ground, then descending Van Ness Avenue while passing in front of the Opera House, finally crossing Market Street, to then entering unto the sex-club located at the foot of the Castro District. A daring ‘First Walk’, but this is San Francisco. SF in fact is a very provincial town during mid-week. Some cars with single passengers, some cop cars (the SF cops are cool). Quiet! I walked very easily descending the hill. The sex-workers did not pay attention to me while I walked. Some men, in search of the whore, slowed down, but quickly understood that I was not selling, so the walk went fine, except when approaching the sex-club when the inevitable car packed with ‘bridge & tunnel guys’ did some verbal hazing to me. (the term ‘bridge & tunnel’ is attributed to the Bay Area residents who have to take a bridge or BART to have fun in SF. This term is derogatory). Hazing from juveniles is always unpleasant, but when a woman, it goes with the territory. Woman you chose to be, woman you will suffer, and femme you are: the higher you go, the more painful is the fall. Tranny you are, and you take the risk of been humiliated! Right?
    At the semi-deserted Power Exchange, I got my first warm welcome right at the gate. Free entrance for the ladies! Inside the club, the usual familiars sado-masochists, and the fat naked lesbians alternatively inflicting pains to themselves. The routine… which never stops, even during the dead-moments of mid-week. Some men, (bridges & tunnels?) were here wandering in quest of free pussy, or just voyeurism. I confess having offered some mild show to those looky-loos. I won’t tell more of what I did, because it goes beyond the scope of the telling since it is about the “First Walk as a Woman”. I was a dressed-up woman, and remained dressed-up as a non-slutty tramp during this entire coming-out.
    I left the club around 1am, alone. No one offered a ride, nor even proposed to ‘take me home’. I guess it was mid-week, and perhaps, I failed at being ‘desirable enough’. That, I don’t want to know!
    I saw back again some of the sex-workers, who were at their ‘prime-time’ for clients. No ‘client’ slowed down for me. Regret? Yes! I wished a car had stopped and rolled down its widow, but no, it did not happen for that ‘First Time’. It did later, so do not be sorry for me.
    It is when back in Nob Hill, at home, when I returned to ‘normal’ that I remember the most. I truly felt like ‘landing safely’. It felt the usual little death, such as the Ciderilla ending her dream-come-true of being an object of dazling desiarbility, but also it felt good, and reassuring to be without high heels with the sole solidly planted of the floor.
    As having had ballet training, the fact of walking on high heels has never been a problem of balancing, but for that ‘First Time’, when back to ‘normal’ with feeling of safety, this is when I realize that this First Walk was very very intense.

  6. Going out dressed as a lovely woman is one of my fondest desires. Perhaps one day it shall come to pass. And hopefully, so will I.

  7. Love, love high heels and vintage patent purses, my gf and I used to play dress up and she loved it even buying me outfits from local department stores, she always wanted me in sexy high heels and so did I.
    Early on I found 4 or 4.5 heels where pretty easy to wear and walk in most of the day, when she started encouraging me to wear 5 inch heels that’s where it took a lot of practice to get it just right and also a few hours and my feet would start to get tired, I was informed by my gf you’ll get used to it and she made sure I did.


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