Annie's Room

Thinking about my early crushes and such...

Oh what might have been. I refused to admit it to myself but I had crushes on a few girls early in my sexual development. I had countless ways to explain how I felt that never included being bi or gay but that's a whole other sorry tale.

My cousin, Amanda, was one of my first crushes. She's three years older than me and developed earlier as well so she would visit and was like a goddess of femininity. (I later was blessed with larger breasts than her, nyah nyah! ;) ). I just loved hanging around with her and always wanted to do sleep overs. I would watch her change or find reasons to go in to the bathroom when she was showering. Early on, we'd share a bed during a sleep over which prompted masturbation sessions after she left. Sadly, that was only the first few times, after that she wanted to sleep in her own bed. I'll never forget the perfume she wore or the way her hair smelled (straight, black hair chin length). I had no idea what I wanted I just knew I wanted more... I wanted to touch her... somehow...

I still think of her from time to time. We haven't seen each other in person since I "came out" to myself but I'd love to. She's become a beautiful woman.

Love the way you write!! Gets me so turned on!!!
 
Perusing that lingerie site a little more... the models are pretty flat-chested and the items are small so probably won't work for me but there are some sexy items...

Baby Girl Teddy

Thank you cum again panties

An odd bra but I love how the model tells us exactly what she wants to do ;)

Naughty Bra and Panties

I love how some items have a gallery of photos customers have sent in wearing the item. They seem like an edgy company vibe. Wonder if they would post sissies in their product? ;)

Oh, my. Love that "Thank you, Cum Again" thong!!
 
Quick update originally posted on another thread: Regarding my hubby's begging to be released from chastity for the last week:

I have in fact refused her until tonight. Gary is coming over for me. Hubby will be dolled up to the max, breast forms, make-up and all. She will have mounted a large cock dildo attached to the seat of a chair. She will be tied to the chair in the bedroom and have to watch us. If she cums like that, then she obviously doesn't need to be released. If she can restrain herself, I'll let her out of chastity. It should take a few hours for Gary and I to enjoy ourselves so it's a real challenge. If she starts bouncing on that cock, she'll cum for sure.
 
Quick update originally posted on another thread: Regarding my hubby's begging to be released from chastity for the last week:

I have in fact refused her until tonight. Gary is coming over for me. Hubby will be dolled up to the max, breast forms, make-up and all. She will have mounted a large cock dildo attached to the seat of a chair. She will be tied to the chair in the bedroom and have to watch us. If she cums like that, then she obviously doesn't need to be released. If she can restrain herself, I'll let her out of chastity. It should take a few hours for Gary and I to enjoy ourselves so it's a real challenge. If she starts bouncing on that cock, she'll cum for sure.

Such sweet torture for her. How she can keep from squirming will be a miracle.
 
Quick update originally posted on another thread: Regarding my hubby's begging to be released from chastity for the last week:

I have in fact refused her until tonight. Gary is coming over for me. Hubby will be dolled up to the max, breast forms, make-up and all. She will have mounted a large cock dildo attached to the seat of a chair. She will be tied to the chair in the bedroom and have to watch us. If she cums like that, then she obviously doesn't need to be released. If she can restrain herself, I'll let her out of chastity. It should take a few hours for Gary and I to enjoy ourselves so it's a real challenge. If she starts bouncing on that cock, she'll cum for sure.

Drooling here;)
 
Such sweet torture for her. How she can keep from squirming will be a miracle.

That's about it. I want to let her enjoy the torture of chastity which for being in it for ?5 months, she hasn't experienced much of since she wanted to be in it and felt it made her more feminine. It's really up to her if she wants to torture herself by resisting the perfect set-up for her to orgasm or to torture herself by cumming and earning another week in chastity. :devil:
 
Quick update originally posted on another thread: Regarding my hubby's begging to be released from chastity for the last week:

I have in fact refused her until tonight. Gary is coming over for me. Hubby will be dolled up to the max, breast forms, make-up and all. She will have mounted a large cock dildo attached to the seat of a chair. She will be tied to the chair in the bedroom and have to watch us. If she cums like that, then she obviously doesn't need to be released. If she can restrain herself, I'll let her out of chastity. It should take a few hours for Gary and I to enjoy ourselves so it's a real challenge. If she starts bouncing on that cock, she'll cum for sure.
That's almost too nice of you, she needs to deserve to be let out of chastity for any length of time. Make her really work for it.
 
Quick update originally posted on another thread: Regarding my hubby's begging to be released from chastity for the last week:

I have in fact refused her until tonight. Gary is coming over for me. Hubby will be dolled up to the max, breast forms, make-up and all. She will have mounted a large cock dildo attached to the seat of a chair. She will be tied to the chair in the bedroom and have to watch us. If she cums like that, then she obviously doesn't need to be released. If she can restrain herself, I'll let her out of chastity. It should take a few hours for Gary and I to enjoy ourselves so it's a real challenge. If she starts bouncing on that cock, she'll cum for sure.



God that is so hot! I’m drooling right now. I’m buying my chasity once I catch up on my debt. My clitty is so hard just thinking about this 😉
 
That's almost too nice of you, she needs to deserve to be let out of chastity for any length of time. Make her really work for it.

Hi Salina, I understand your view which is fairly "hardcore sissy", if that's a thing. She will be tortured either by resisting the pleasures of cumming as she watches us or by not resisting and being kept in chastity for another week. I'm very curious if she'll elect to 'fail' each test and effectively keep herself in chastity even when I give her a way out.
 
Quick update originally posted on another thread: Regarding my hubby's begging to be released from chastity for the last week:

I have in fact refused her until tonight. Gary is coming over for me. Hubby will be dolled up to the max, breast forms, make-up and all. She will have mounted a large cock dildo attached to the seat of a chair. She will be tied to the chair in the bedroom and have to watch us. If she cums like that, then she obviously doesn't need to be released. If she can restrain herself, I'll let her out of chastity. It should take a few hours for Gary and I to enjoy ourselves so it's a real challenge. If she starts bouncing on that cock, she'll cum for sure.

God, that my cock hard! Love to be a fly on the wall and the action! It like a double feature! Can’t wait for the hot details!!!!
 
God, that my cock hard! Love to be a fly on the wall and the action! It like a double feature! Can’t wait for the hot details!!!!

Neither can hubby. She left work early to go home and feminize every way she can.
 
Both!!!! My cock is leaking like crazy thinking about the whole thing!

It would definitely be fun to watch. Might even want to be locked up. Or at least some very tight panties. But not the same torture as that sweet sissy.
 
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