I do want to go out, I do, I do, I do!

[Jenny22]

I've thought a lot about this. One day I will go 'out,' possibly to a dept store. My plan is to use a shopping cart, one from the parking lot, if possible. Then my walk will not be too noticed especially wearing flats. I will put my purse (I have four) in the cart. Many women do this rather than carrying it. My outer fashions will not be too bright so as not to attract attention. My jewelry will be minimal,a simple necklace, a bracelet, and a ring on each hand (nails possibly a very light pink .. toes not polished, maybe). I plan to wear skinny jeans and a tunic with light makeup. Stand erect, no slouching. Knockers up (small inserts). Avoid most eye contacts and kids / teens. Smile when needed. Browse a bit. Shop a bit (I do need a woman's wallet), and use the self-checkout so I don't need to use my male voice. Pay in cash so there's no credit card evidence.

What can you add for me to make my first outing a success? I DO so want to do it, but I'm almost scared to death to do it. Thanks, ladies.

[Teresa]

Jenny,
I've checked your age, all I can say is what are you waiting for, go and enjoy it while you still can, as you say keep it casual I'm sure no one will take any notice, and you'll kick yourself for not doing it sooner.

[Krisi]

Why would you not carry your purse? Why not just walk in the mall without going in the stores and buying stuff? Or walk in the business or tourist section of town?

Start slow and then work up to the buying things. Why are you worried about credit card evidence? There's no record of what you were wearing when you make a purchase.

[Kimberly Adams]

Just go out and do it already. I know it's nerve-wracking the first time but so exhilarating! Everyone's eyes are glued to their smartphones anyway so you can blend right in.

[Rachael Leigh]

Jenny yes it's scary but so was learning how to drive or the first time you drove by yourself, but you were not about to not do that. Ok now I know it's not like anyone would really compare the two but I think you understand. If you even pass at first glance that's usually all it takes for anyone who sees you to register your a women and then they move on.
And those of us who do go out all had a first time and well I would say we all made it.
Hope you can experience it and have a super great time
Leigh

[Pattie]

Just do it!

[jennifer0918]

Wear sunglasses,I would go out around the hours of 10am to maybe 1pm less people in the store on one of my missions(when I go out enfemme)I went to the mall and the mall closed at 9pm so I made sure to be there by 8pm gimme and hour or so to walk look around a little. I wasn't really out to shop but just to have a day out in public no problems.I also went to McDonald's used the drive thru did my best girl voice and had fun.You will do fine,I prefer after the holidays the malls are empty.If ypu need a sister to go with you gimme a shout out. Hugs

[CDTiffany]

OK Jenny. I saw that you joined the forum in 2016. I am going to guess that you are young. Teresa seems to think that you are young.
Hopefully I will not get in trouble. But there are plenty of gurls on this site that could recommend groups for you to go out with.
Safety in numbers. The OC has plenty of groups that go out and have unbelievable fun.
If you are brave enough to go out by your self for the first time.... Rock on!
I would really suggest that you find a group near you. and go out for your first time with other special gurls.
XOXO Tiffany Amber Rhoads.

[Lana Mae]

Jenny, just do it!! You have a plan, do the plan!! I had a plan to drive dressed(no wig or makeup), I just did it!! Walked to the car, took the drive I planned, took an unplanned ride thru a local park!! Was seen by a few people-nothing!! Unplanned flagman-nothing!! Back home walked (not run) into the house!! It was such a confidence builder!!!! Work your plan!! As stated in the "A Team", "I love it when a plan comes together!" LOL Hugs Lana Mae

[Helen_Highwater]

jenny,

You didn't mention a wig but I guess that's a given. The only other thing I'd suggest is park away from the shop you want to go to. That way you'll have a few minutes as you walk across the car park to settle your nerves. Other than that your plan is a good one. Dress to blend, practice the mannerisms and your walk and if you have need to speak to someone, just soften your voice a little, look them in the eye and just make the same normal conversation that you would if in drab.

[Jenny22]

I just turned 81 !! Check my "about me". Still young at heart. I'm going to PM you, Tiffany.

[Majella St Gerard]

Just realize that nobody cares but you what you are wearing. Just do it.

[suzanne]

You're way over thinking the whole thing. Every one else who responded to you is spot on. Just get out there. The first time is the scariest, but also the most memorable. Good luck. We're all cheering for you and waiting for you to come out on the other side.

[grace7777]

Learn to do your makeup well. There are YouTube videos to help you out. You may want to even get lessons from a professional makeup artist, depending on your makeup skills. I did get lessons and it was some of the best money I spent.

[Teresa]

Jenny,
I checked your age , just go for it, I hope I can still have an interest and need to go out and I'm still here to talk about it in my eighties !

I felt I was getting too old in my sixties till I joined the forum, the more mature members certainly taught me a lesson in never giving up !

[Vikky]

Hi Jenny

Just do it. Adventure before dementia.

Vikky

[leannejacobs]

A word of warning with the shopping cart, if you place your bag in it remember to pick it up, I did what you're planning one time, got spooked a little and left the store in a hurry with the cart, I got to my car with the cart and jumped in and drove away, a short time later I realised I had left my bag in the cart, complete with my wallet and iPhone, fortunately it was handed into the local police station, I quickly changed into male mode and went to collect it but during the process I had to come clean to the police officer and tell him I was a crossdresser, very embarrassing but he wasn't phased and was very professional, I won't be doing that again lol

[Tracii G]

Its really not all that hard Jenny.
Nobody will be watching you and they are too busy doing their own thing.

[Krisi]

1) Leaving your purse in a shopping cart increases the risk of it being stolen. Keeping it on your shoulder is much safer.

2) Walking in a nearly deserted mall makes you pretty obvious. In a crowded mall, you are more likely to blend in and not be noticed. The same goes for other places like city streets.

3) Sunglasses are good in the daytime. Outdoor malls are perfect for this because you can leave them on. Same for city streets. Sunglasses hide a lot of eye makeup mistakes as well.

[BettyMorgan]

I agree with all the comments. The first time I ventured to a mall was in winter so I was pretty covered in clothes to "hide myself". I was scared to death. Parked far from the mall thinking that was best - nope, can't say that was the right move. I walked into Sears, walked around one rack of clothes (can't remember if it was even men's or women's) and then quickly walked out with a lot of adrenaline in my veins. Hustled back to my car through a very dark parking lot. HOWEVER, less than two years later I love dressing up and going shopping. No one really notices me in my local city and its way better trying on clothes when you are wearing forms and a bra. Believe me. Go for it.

[Jenny22]

Many thanks to all of you for your thoughts and ideas, You're all fantastic girls!

[Barbara Jo]

FWIW...
I always wear either a skirt or a dress when appearing in public en femme.

I have found that best time to either walk through town or the Mall etc, is form about 9:00 am to noon on week days .
During those hours kids are are in school (except July to Sept) and, most other people are just going about their business.
Of course, you must dress accordingly to the morning hours. and your age .

This first time can be a bit scary .
However, when you realize that no one will laugh or point, etc, it become much more enjoyable.
The key is to keep in mind that you are wearing clothes that are no different than any other woman would wear / are wearing, and no one thinks that you are not a woman.

[Lauren Richards]

Jenny,
Great idea to plan out your first trip to a store. May I recommend one of the Target stores you will find in The OC. Most have self check, however, even at the self check, there is someone watching you as you make purchases. No biggie. They have seen crossdressers before, and are happy to have you as a customer. And as noted by others, most people are too busy with their own shopping to pay attention to you. Sorry, but it is unlikely that you will raise many eyebrows, except maybe a few who wonder why an elderly person is shopping in the Juniors section. ...

A trip or two en drab to scout out the location would also be something to consider. Grocery stores like Ralphs and Albertsons also have self check aisles, and are quite safe for the casual crossdresser. If concerned about being spotted by someone you know, about 10 miles from home is a good rule of thumb.

The most important thing you can carry with you, in addition to your purse, is confidence. If you carry yourself with confidence, there is nothing you can't do, and no place you cannot go. Well... maybe Pluto is off the list, but other than that... slip into something comfortable, slap on some lipstick, and go enjoy some Jenny time. She deserves it! You have earned the right to simple pleasures. No need to hold back any longer. Be safe. Enjoy.

And, yes, while on this adventure your heart will beat faster, and your hearing will improve; and when you get back home, you will wonder why you waited so long...

And... we want to hear all about it!!

Lauren

[DIANEF]

Like you I'd love to go out but the thought terrifies me. I did manage a couple of late night drives and found the experience of being in the open, so to speak. so exhillerating. Hope it goes well for you.

[Rhonda Jean]

Jenny,

This really brightened my day! To be 81 and going out for the first time... Sorry it took you so long, but it's SO AWESOME that you are driven to do it now!

As others have said, you're WAY overthinking this. It's like overthinking a golf swing. Overthinking will make you appear unnatural and forced. Just enjoy it, be unafraid, and the smile will come naturally! Have fun!