Fun convo with random GG

[Sometimes Steffi]

I was waiting for my order at 5 Guys when this cute girl with a super cute dress walked in It was kind of like a sundress but with wide straps, a boat neck and a mid-thigh length. I was kind of in the stereotypical predicament, "Do I want to be the girl or be with the girl?" No, not really; she was almost young enough to be my granddaughter.

I was feeling very open, so I told her that "I really like your dress." She thanked me and then said, "I really like it because it has pockets." She stuck her hands in her pockets to show me. I said, "Those are really big pockets. You don't even need to carry a handbag." She said "I don't, but these pockets are so big that I can't find anything."

Then she said "Pockets in women's jeans are so small." Don't we all know that. I said, "That's what I understand." I stuck my hands partway down in my pockets, and said, "the pockets in women's jeans are too small to be useful. I said that it should be technically possible to sew a man's pocket liner into women's jeans." She said, "Yes it's easy to do, but it wouldn't work because woman's pants are tight and don't have room for pockets. Men's jeans are loose and have plenty of room for pockets." I said, "You could buy 'boyfriend' jeans."

After the conversation was over, I thought to myself, "Steffi, you really gave yourself away. You knew way too much about women's clothes for a typical guy."

Nonetheless, it was fun to have an interesting convo with a random GG. And it is possible to complement a girl without getting hit in the head with a large object. In my experience sincerely make the complement about her clothing choices, not about her body.

[Crissy 107]

Steffi, Yep you knew a bit too much but it worked out well.
I loved the last line in your post, good idea!

[rachellegsep]

Steffi I do it often with women and sometimes get that strange look when I give a compliment on clothing. I mention a certain style of cut might suit them such Princess, A Line and Peplum etc, until I mentioned I sew and show a few pics of items I've made. That often starts a conversation. I had a full on conversation in a material shop with a lady dressmaker the other day when I asked her if she had seen a certain weave of material I was looking for. I mentioned it was for a corset project . She was quite taken aback by my range of knowledge on the subject. We even traded phone numbers and I sent her links to a free pattern site for a period style dress she was looking for.

[bridget thronton]

Sounds like a nice conversation Steffi

[CarlaWestin]

I love those random conversations. As I keep my nails at a nice length, filed and clear coated, I love telling women how nice their nails look. And I don't push but then I don't mind if the conversation leads to my crossdressing.
At my age I just don't have anything to hide.

[Sandi Beech]

I have had many similar conversations which would never have started were it not for my crossdressing. It really has made it easier for me to talk to women, or at least break the ice. Of course I am often at bars where the conversations go on for a while. It is kind of shocking how much they spill to me about their relationships, sometimes a little too much information, haha.

But yea, like Carla as well, I love the interactions whether I am dressed or in drab.

Sandi

[Stephanie47]

I don't think you gave yourself away because you possessed knowledge. My wife and daughter have complained about the "non-pocket" pockets on women's pants. In the past both have worn men's jeans. Our granddaughter, because she has no hips to speak of, buys her jeans in the young men's section. The three generations of women have abandoned carrying large purses and have gone to slim wallets that carry the essential identification and credit/debit cards and fit into a pocket.

[Marketa]

I love when you compliment girl's/women's dress and she says "Thanks. It has pockets!" and then they put their hands in them and proudly show you. Happened to me twice, although I compliment only women I'm good friend with.

[NancySue]

Because of our small, nosy, gossipy town, I?ve chosen to be careful, it?s difficult, but when part of a women?s clothes conversation, many times, I smile to myself thinking ?I know that? or comment that my wife says the same thing. I don?t want to give myself away, either. I, too will compliment a good friend, usually the wife of a good friend. I can?t help it, but sometimes my mind wanders to things like is she wearing an underwire bra, etc. I?m often underdressed when out. Sometimes I want to show my bra straps, hose, but resist. Frustrating but kinda fun.

[Sometimes Steffi]

I, too will compliment a good friend, usually the wife of a good friend. I can't help it, but sometimes my mind wanders to things like is she wearing an underwire bra, etc. I'm often underdressed when out. Sometimes I want to show my bra straps, hose, but resist. Frustrating but kinda fun.

I usually compliment random strangers who I see in the grocery store, on public transportation, and now restaurants. It's more dangerous than complimenting friends, because it is a little bit forward, almost to the point of hitting on them.

I once complemented a woman on her braids (extensions, I don't know what they're called) as we were both getting off the train.

Her response, "Thank you. You made my day. Actually, you made my week."


Steffi I do it often with women and sometimes get that strange look when I give a compliment on clothing. I mention a certain style of cut might suit them such Princess, A Line and Peplum etc., until I mentioned I sew and show a few pics of items I've made. That often starts a conversation. I had a full on conversation in a material shop with a lady dressmaker the other day when I asked her if she had seen a certain weave of material I was looking for. I mentioned it was for a corset project . She was quite taken aback by my range of knowledge on the subject. We even traded phone numbers and I sent her links to a free pattern site for a period style dress she was looking for.

From Legally Blonde

Elle: It's impossible to use a half-loop stitching on low-viscosity rayon. It would snag the fabric. And you didn't just get it in - I saw it in the June Vogue a year ago. So if you're trying to sell it to me for full price, you've picked the wrong girl.

[docrobbysherry]

U sound like you're quite outgoing, Steffi. I'm not.:sad:

Yet, when I'm out in drab, (I only shop for Sherry in men's clothes), I never give a thot to what a stranger mite think about my dressing. So, I talk freely about all aspects of women's things, and/or my dressing, with female SA's and shoppers.:battingeyelashes:

Why would u care if a young woman you'll never see again wondered why u knew so much about women's things? If she was all that curious wouldn't she have asked u?
And, if she had, would u have told u crossdress? I would without a care just to see her reaction!:heehee:

[danniUK]

I think a conversation like that with a random stranger is the ideal time to "give yourself away" - if you're likely to never cross paths again... I think I'd happily thrown in a line like "Yeah, none of my mom jeans have deep pockets"!

That said, I'd not be likely to be in the same position... I'm usually a bit shy about complimenting women like that! At least when in drab.

[SylphDevine]

I work in retail part time and mostly women shop in the store. We sell gifts and socks, cards, makeup and all kinds of oils creams lotions etc. Part of my job was to learn how all the makeup and skin emollients work. I am constantly interacting with women about what works, looks good on them, etc.

What I have found is when I tell a woman "I really like your outfit" they glow and smile. They always say "thank you" and then talk about where they bought it and how t feels to be wearing it. The next thing I usually say is "it's super cute". After that they start asking me my opinions on this brand of night cream or face lotion and they always end up buying things. But there's always a friendly connection. The crossdressing never comes up, but I become very aroused by the interactions and usually throw off my clothes as soon as I get home and dress top to bottom until I calm down. My wife can always tell when I've been interacting with women at that level at work, because I'm usually flushed and grinning while fully dressed. Leads to some interesting conversations and situations with her.

I love my job.

[Sometimes Steffi]

U sound like you're quite outgoing, Steffi. I'm not.




That said, I'd not be likely to be in the same position... I'm usually a bit shy about complimenting women like that! At least when in drab.

Boy me is an introvert. Steffi is and extrovert. I know that Myers-Briggs say that your personality is fixed. Maybe they didn't interview enough crossdressers.

But, when I'm out in boy mode, Steffi is on my right shoulder egging me on.

- - - Updated - - -

So, I'm out today doing some banking business and I end up parked next to a truck advertising their environmental work. I need some environmental work on my home. The old me would have just walked right by. But Steffi has passed some of her extroversion on to me. I just walked up to the guy in the truck and asked if he could do some work for me.

[CrossKimmy]

I've wanted to do this many times. I used to do deliveries and one of the girls working at the reception had the cutest manicure ever and I so wanted to ask her where she got them done.

[Sometimes Steffi]

I've never had a bad reception (from a GG). I highly recommend talking to them. Some say that girls dress for other girls, but when a guy takes a notice, it is a whole other level.

Once on the bus, I complemented a girl about her green nails. She actually closed her mobile phone, and we talked half an hour to the end of the line. She closed her mobile phone. The old boy me would never get that kind of attention from a young, attractive GG!

Sometimes, I'll even be open enough to show some pics of Steffi. I have one recent one of Steffi in a full-length burgundy evening gown, with sequins top to bottom. I always get a very positive reaction from that pic. I often get the feeling that they really want that dress. One SA said, "I don't even have a dress like that." Something to smile about.

When I was in the hospital, I opened up to one of the GG nurses and showed her some pics. She was really into it. It turned out that she had a number of close friends who were trans. It got me to wondering if she was trans also, but there were no obvious tells.

And if you want to ask a GG about where she got it, you can always tell her, "It's for her." When I say that, I usually mean that the "her" is Steffi.

[Sometimes Steffi]

Another day, another compliment. The hostess at the restaurant we went to today was wearing a "very Florida" necklace. It was a chain neckless with starfish and other sea life sculptures attached. I complemented her about within the hearing range of my wife and didn't get busted for it.

Of course, the hostess appreciated the compliment.