Betty Pearl's Sissy Stories 20.1

Sissy Story Archives (older stories) =>
2011-2018 Sissy Stories
=> Topic started by: Alana on August 22, 2017, 06:16:46 PM

Title: So, Now He Knows
Post by: Alana on August 22, 2017, 06:16:46 PM
"So, Now He Knows," by Alana
A sequel to "I Don't Think He Knows!" by Alana


I didn't expect to hear from Simon again, so it was a surprise when he emailed me. The last thing I can remember writing to him was pointing out that I'm not gay and he's not gay, so there it is. We started getting into another email dialogue:

Hello again,
 I hope you don't mind me writing again. I've woken up early again this morning and I've been thinking quite a bit about your email.
 I was thinking that "being gay" has nothing to do with it. I'm not gay, but that is exactly why I found you so attractive - if I had been gay, I wouldn't have - does that make sense?

I've just seen you uploaded a new photo of you in your blue dress - you do look stunning in it - whether you are a guy or girl!
 I hope you are OK with me writing, I understand if you would rather not hear from me,
 Simon

Actually, I was more afraid you'd rather not hear from me. I don't regret our emails. You've made me feel more feminine and wonderful than I have in years with all your compliments. When you thought I was a woman who wanted to be a man, I thought of playing along. I thought of saying things like: every time I put on my pantyhose, every time I put on a tight dress, I always think to myself that it's really a man putting on this dress. But I couldn't lie to you that way.
 Anyway, if you want to go on flirting with me, I won't tell anybody. I'll even send you some more photos of me. This is one of my favorites:
Title: Re: So, Now He Knows
Post by: Alana on August 22, 2017, 06:20:53 PM
Gulp! You really are playing with my mind with that photo.
 I'm now not sure whether you have been playing with me when you said you were a man. That photo is so incredibly sexy, you look stunning. Legs to die for and that amazing look on your face.
 Are you just teasing me and you are really a woman - I totallly fell for it, I guess the joke is on me.
 Simon

Well, I could always drive to your apartment and take off my dress and my pantyhose for you, if you want proof. I don't think you'd like what you found when you got off my girdle, though. And yes, I do wear a girdle.
Title: Re: So, Now He Knows
Post by: Alana on August 22, 2017, 06:25:38 PM
Oh god, I can see your Adam's apple in that photo - you are a guy.
 That is amazing, I can only be impressed by your ability to change into a beautiful woman. I really think you are an amazing woman, but if it is OK with you, I'd rather not think of you as being a guy. Does that offend you?
 Simon

No, I'll be a girl for you. After all, I like to wear pretty dresses and show off my legs. That's not a thing that guys do. So I must be a girl, right? If you saw someone lying on the ground, wearing this dress, you wouldn't think, "Well, I'd better help that man up." Would you?
Title: Re: So, Now He Knows
Post by: Alana on August 22, 2017, 06:30:19 PM
You look so cute in that photo. I love the dress, the color really suits you, I especially like the cuts in the sleeves giving a glimpse of your arms.
 And as usual you have that smile - you do have the most fantastic smile.
 Simon

So tell me, what's it like being a man? It must be so handy getting to pee standing up, not having to deal with pantyhose or a girdle. I'll bet it takes you no time at all to pee. But I don't know if I envy you or not. I don't know what I'd do if I wasn't allowed to wear a pretty, feminine, girly floral dress to work. Like this one.
Title: Re: So, Now He Knows
Post by: Alana on August 22, 2017, 06:34:53 PM
Being a guy is pretty great - yes there are peeing advantage, but also things like strength and height are great! I'm 6'2", so I'm always helping women get items from top shelves in stores.
 That is such a pretty dress, your arms are just so slender and feminine; that look on your face is also very mischievous!
 Do you have many female friends, to go shopping with, etc.?

Well, there's my sister Sierra. We do things together, and we take photos together. I'm jealous of her because of her beautiful smile. My teeth are kind of bad news, so I keep them hidden away when I smile. Her teeth are gorgeous. She's always borrowing my dresses and looking better in them than I do. She just seems to have an inner glow of femininity about her.
Title: Re: So, Now He Knows
Post by: Alana on August 22, 2017, 06:39:56 PM
It's funny you should mention your sister. When you first showed me her photo it actually passed through my mind that she was a bit too masculine - but I dismissed it as being ridiculous. You are much more feminine than your sister, ironic isn't it?

Well, she can be a bit aggressive, sometimes. There was that time when we were wearing the same dress. She got so mad, she grabbed my dress like she was going to rip it right off me!
Title: Re: So, Now He Knows
Post by: Alana on August 22, 2017, 06:44:19 PM
She looks scary in that photo - and even more masculine (please don't tell her I said that).
 Shame she didn't rip it off you though ;-)

Well, there was that time when I was wearing a lovely tight pink dress that I love, and she ripped it right off me. I showed you that photo. But I never showed you how I looked when I was actually wearing it.
Title: Re: So, Now He Knows
Post by: Alana on August 22, 2017, 06:48:30 PM
Oh wow - you look soooo cute in pink - and that tight top really shows off your sexy arms.
 Lovely pink shoes, too.
 Do you normally need glasses or was that just a prop - to look sexy?

I needed them because my little sister was being naughty that day. I needed to spank her. You need to see what you're doing when you're spanking a girl.
Title: Re: So, Now He Knows
Post by: Alana on August 22, 2017, 06:53:09 PM
You two are so silly! That is such a fun shot.
 Have you ever spanked someone for real? I once dated a girl who liked it, I enjoyed doing it, but really didn't enjoy being spanked. I couldn't sit down for ages!

Well, maybe when I come out to your apartment, you can spank me and I'll see if I like it!
Let's talk about us. If I came over, and I wore the tight blue dress you like so much, and you saw me over against the wall, in this position, what would you do to me?
Title: Re: So, Now He Knows
Post by: Alana on August 22, 2017, 06:57:35 PM
You look so beautiful in that photo, I would first be stunnd when i saw you, but then would take your hand and intertwine my fingers in yours. Then push your hand up level with your shoulder, holding you there as I kissed you slowly.
 (Are you sure it's OK for me to say that, I really don't want to freak you out)

Why would I be freaked out? I'm a girl, you're a man, it's the most natural thing in the world. Go on.
Title: Re: So, Now He Knows
Post by: Alana on August 22, 2017, 07:01:52 PM
If you are OK with it, then I think I am.
 You look so sexy sitting there in that photo. I would want to start kissing you up your arm, you are so smooth and slender, and when I reach your dress, I would move on to kissing your neck and then nibbling gently beneath your ear.

Well, then I would make things easier for you, by lying on your couch in a way that would make you want to put your hand up my skirt.
Title: Re: So, Now He Knows
Post by: Alana on August 22, 2017, 07:06:28 PM
This is really embarassing, but I've become sexually aroused (in that way that is very obvious on a man) seeing your photos and chatting to you - I'm so, so sorry. I think it started when you sent me the photo set against the red background - I'm really really sorry.
 Simon

Don't be sorry. I'm a woman, and I'm aroused by this as well. Do you think we women don't get aroused? But you're probably at work now, so maybe we'd better stop for the day. Besides, I'm having such a problem with my girdle, today. My girdle is killing me.
Title: Re: So, Now He Knows
Post by: Alana on August 22, 2017, 07:11:19 PM

And that was it. I guess he got scared. I log on every day, hoping to hear from him again, because our little talk really turned me on. So far, nothing.

Where are you, Simon? Are you out there?

I miss you.




 
Good story? Or room for improvement? Please review!