Betty Pearl's Sissy Stories 20.1
Sissy Story Archives (older stories) => 2011-2018 Sissy Stories => Topic started by: Alana on August 07, 2017, 02:38:13 PM
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"I Don't Think He Knows!" by Alana
So, there is a site which I won't mention, but I'm sure you've heard of it, where I like to post photos of myself in various dresses, as well as other photos I think are sexy. I like to post pictures of Susanna Reid, the TV presenter from the UK, not just because she's sexy and gorgeous, but because I just adore her tight, colorful dresses. You just don't see women wearing beautiful dresses like that any more. I got an email which said:
Hi,
I saw your photos of Susanna Reid this morning - she is gorgeous - my perfect woman. Can I ask who the other newsreader is you have a photo of, I didn't recognize her - is she on network TV?
Simon
ps. Just realized I should have said which photo - it's the close up of her, she is wearing a blue dress.
Looking through my photos, it seemed that he was actually talking about a photo of me! I wasn't sure, so I emailed him back.
I'm not sure which photo you mean. Is it this one?
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He replied:
Hi there,
Thanks for replying. That's the girl, she looks stunning - she has that natural look that I wish more women would go for. Is she a newscaster or a TV presenter?
Simon
He really was referring to me. I thought to myself, wow, I don't think he knows! Then I thought, oh come on, he has to know. He's just kidding, just putting me on. Well, I can play along. I emailed back:
No, not a TV presenter. That's me. Thank you for the compliment. Here's another close-up to remember me by.
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Here's the rest of our conversation that day:
Oh wow, I'm really sorry - I hope I didn't make you feel uncomfortable. You have a wonderful style, thank you for the link to that other photo.
Simon
Oh yes, you made me terribly uncomfortable by calling me stunning. The only thing that could make me more uncomfortable is if you said something nice about my legs.
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You are just so cool - I wish more women were like you and would accept complements gracefully.
Thank you for that non-close-up photo - you look stunning with legs :-) Your legs are perfect - I guess you work out a lot? I know most women work very hard to try and get a figure like yours, even if they achieved it, they don't have your advantage of such a pretty face!
I'll keep sending you photos if you keep complimenting me. I don't work out. I'm just naturally that thin, although the girdle helps a lot. Here's a little cheesecake shot:
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You are amazing - both in looks and attitude!
I love that shot - you have the cutest smile in it. (I'm at work at the moment, so can only look on my phone - but will look properly at it when I get home tonight)
I'm amazed you don't have to work out to look like you do - though I've never met a woman who wears a girdle - doesn't that hurt - I thought that was some 19th century thing?
Does every woman you meet immediately lift her skirt for you? I assure you, there are a lot of girdles out there.
If you think I'm beautiful, you should see my little sister:
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Sorry, I didn't mean literally every woman I met, that I immediately checked for the presence of girdles!
That is a cute photo of you and your sister - she obviously looks up to you a lot, and follows your sense of style.
As cute as your sister is, you are definitely the more beautiful of you two. It must have really frustrated her when you were younger that all her boyfriends would show a greater interest in you when they came around the house.
You are so sweet! Though of course, you have it exactly backwards. She's the one who gets all the attention. We fight all the time. She's always trying to borrow my dresses. I remember when we got in a big fight over a dress:
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That is a fantastic photo - I assume you were planning to do a properly modeling shoot (hence the white background).
I have two sisters and they fight so much - having them both round for dinner at the same time is just a timebomb waiting to go off.
So who won that fight?
Oh, she won. She always wins. I let her wear the dress, and even zipped it up for her. And I must admit, she looked fantastic in it.
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You are just a big softie, letting her win and wear the dress.
You look so cute in that petticoat - and you definitely have the egde on looks over your sister - you definitely have a much sweeter, delicate face.
Thank you. We fight a lot, but we love each other. I remember the time she got so angry at me she pulled my dress down in front of everyone! She was just a schoolgirl back then.
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Gosh, she has quite a scary look on her face there - I wouldn't want to meet her in a dark alley.
Cool action shot though - who took the snap? As much as it is cool to see you in your petticoat again, I couldn't take my eyes of your legs in that shot.
Do you mind if I ask if you are married, and if so, is your husband OK with you sharing these photos with me?
No, I'm not married. I'd like to go on talking with you and basking in your wonderful compliments, but I have things to do. Here's a little picture of me playing secretary to remember me by. I hope you add a few comments to some of my photos sometime.
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I was actually just going to write and say that I really need to get on with some work - I've been too distracted by you this morning.
I'll have a look at the picture when I get home.
ps. Amazed, but pleased, you aren't married :-)
I didn't know what to think after all this. Could he really not know? I thought I'd better set him straight. I sent one last email for the day, directing him to my profile page, where it stated I was a heterosexual crossdresser living in Northern California. I waited patiently for his response the next day. And it was a very strange response.
Hello Alana,
I've been wondering all evening whether to email. I read your profile when I got home and didn't know what to say.
I've never heard of someone transitioning to male, all the popular media is of men becoming female. That must make life very difficult for you. Thank you for letting me know about that part of your life. I assume you have another anonymous Flickr profile for when you get the chance to be the guy you are inside.
I really hope things work out for you and that one day you are able to live as a man full time (even though that means we will lose an incredibly beautiful woman).
Best wishes,
Simon
Wow! At that point I was really starting to think, I don't think he knows! I really don't think he knows! What woman refers to herself as a crossdresser, anyway? A woman who occasionally dresses as a man would be called a woman. Women can wear whatever they want, as we all know. He was clearly confusing crossdressers with transsexuals. Well, I hated to bust his illusions, but I had to tell him the truth, even if it meant the end of our flirting. I emailed:
You have it backwards. I'm a man, and I like to dress like a woman, sometimes. I'm not transitioning, I'm just an occasional crossdresser. I kind of thought you knew and were just playing along. Anyway, I don't want to make you uncomfortable. I enjoyed flirting with you, but it was just playing around, and that's all.
And then I didn't hear from him for two days. I felt bad about the whole thing, so I sent him another email, changing the subject line to "I hope you're not upset":
I haven't heard from you since I had to tell you that I'm not a woman. I hope you're not angry or embarrassed. If you are, I want to apologize. I'm sorry. I should've told you sooner. I honestly thought you knew, and you were just kidding me and playing along. So I played along, too. I'm sorry. Please email me back and tell me that I'm forgiven.
And he replied:
I'm sorry for not replying sooner - it was just a lot to take in. I've just woken in the night and realized it was very rude of me not to reply. I don't blame you, I just feel very foolish (though I guess there was no way I could guess).
I have to say that for someone who says they are an occasional crossdresser, you do it very well - you certainly have a better sense of style than most women. You should run courses for women!
Best wishes,
Simon
I thought it over and sent him back one last email. I have never been so complimented in my life, and I thought of him looking at my photos and probably pleasuring himself, and I couldn't help but think of him fondly. He never responded. I think of him sometimes, and I wish him well. Here was the final email between us:
Well, I don't want to be some kind of stalker, so this will be my last email to you, unless you respond. I just want to tell you that you are so sweet! I've never received so many wonderful compliments in my life! If I were a real woman, I would be yours, because you've just about charmed the pantyhose right off me. I can just imagine looking in my closet and picking out a dress to wear on a date with you, looking forward to you seeing me in it, looking forward to you taking it off me later. But I'm not gay and you're not gay, so there it is.
So before I go, possibly for the last time, I just want to ask you one question.
Do you think I look cute in this dress?