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Annie's Room

Jenna2641 said:
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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I’m pretty sure I would cum right away after I got the toy all the way in!
 
Jenna2641 said:
I certainly like the idea. Just have to pull it back, before things go over the edge. You know, make it last! ;)
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I’ve been making it last all night here! Now I need to cum! Just need that right thing to get me there
 
SweetAnnie40 said:
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.
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Hi SweetAnnie40, thank you for you response.
As a sissy it is a personal knowledge of how it started for this sissy and how great it was to discover the true sissy within.
This sissy owes all the gratefulness to Her for keeping this lowly sissy on the path to becoming the sissy that was meant to be.
 
O my Heavens...

Back from travels. Sounds like that sweet Annie is gonna bless her sissy with such a thrill! I bet 5 gets U 10 that sissy cums all over her cage! I just wonder if Annie will let her clean up the cum she craves!!!
 
Well, it was a hell of a lot of fun last night. Gary came over around 8pm and we tortured my hubby a little by just making out on the couch for a long time. We finally went upstairs and I made hubby stand there until Gary was naked. Hubby has sucked that cock many times now and I know her mouth was watering. I attached the dildo to the chair seat, aimed it for the special hole in the back of her panties and helped her work herself down on to it until she could sit. I checked her cage to ensure she hadn't already cum and then pulled her panties back up.

Then I got to really enjoy Gary. We made out more as he slowly undressed me and I played with his cock. When I was down to bra and panties, I knelt to give him a blow job, right in front of hubby. She was whimpering and squirming a little. After I enjoyed swallowing his first load, we got on the bed proper and his mouth got to work on me. Excellent tongue talent there and I really let myself go, multiple times.

At that point I'd almost forgotten hubby as I wanted Gary's cock in me, first in pussy but pretty quick in my bottom that really drives me crazy. I made sure to tell Gary over and over how good his cock felt, how big it felt, bigger than hubby's. He slipped his hand around and rubbed my pussy until I came twice with him deep in my bottom. Second time sent him over the edge.

We relaxed at that point and I went to check hubby. She'd cum big time, twice, soaking her panties so it's another week in chastity.

We talked about it this morning, away from the sex play of it all. She still wants to get out of the chastity and thinks last night was too big of a test but she'll do what it takes. She's okay with needing to pass a test for release, she's enjoying that part of the whole thing.

So the adventure continues. Time to check her chastity and undies before we head out to run errands.
 
SweetAnnie40 said:
Well, it was a hell of a lot of fun last night. Gary came over around 8pm and we tortured my hubby a little by just making out on the couch for a long time. We finally went upstairs and I made hubby stand there until Gary was naked. Hubby has sucked that cock many times now and I know her mouth was watering. I attached the dildo to the chair seat, aimed it for the special hole in the back of her panties and helped her work herself down on to it until she could sit. I checked her cage to ensure she hadn't already cum and then pulled her panties back up.

Then I got to really enjoy Gary. We made out more as he slowly undressed me and I played with his cock. When I was down to bra and panties, I knelt to give him a blow job, right in front of hubby. She was whimpering and squirming a little. After I enjoyed swallowing his first load, we got on the bed proper and his mouth got to work on me. Excellent tongue talent there and I really let myself go, multiple times.

At that point I'd almost forgotten hubby as I wanted Gary's cock in me, first in pussy but pretty quick in my bottom that really drives me crazy. I made sure to tell Gary over and over how good his cock felt, how big it felt, bigger than hubby's. He slipped his hand around and rubbed my pussy until I came twice with him deep in my bottom. Second time sent him over the edge.

We relaxed at that point and I went to check hubby. She'd cum big time, twice, soaking her panties so it's another week in chastity.

We talked about it this morning, away from the sex play of it all. She still wants to get out of the chastity and thinks last night was too big of a test but she'll do what it takes. She's okay with needing to pass a test for release, she's enjoying that part of the whole thing.

So the adventure continues. Time to check her chastity and undies before we head out to run errands.
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Excellent, I'm glad things are progressing in a favorable manner.
 
SweetAnnie40 said:
Well, it was a hell of a lot of fun last night. Gary came over around 8pm and we tortured my hubby a little by just making out on the couch for a long time. We finally went upstairs and I made hubby stand there until Gary was naked. Hubby has sucked that cock many times now and I know her mouth was watering. I attached the dildo to the chair seat, aimed it for the special hole in the back of her panties and helped her work herself down on to it until she could sit. I checked her cage to ensure she hadn't already cum and then pulled her panties back up.

Then I got to really enjoy Gary. We made out more as he slowly undressed me and I played with his cock. When I was down to bra and panties, I knelt to give him a blow job, right in front of hubby. She was whimpering and squirming a little. After I enjoyed swallowing his first load, we got on the bed proper and his mouth got to work on me. Excellent tongue talent there and I really let myself go, multiple times.

At that point I'd almost forgotten hubby as I wanted Gary's cock in me, first in pussy but pretty quick in my bottom that really drives me crazy. I made sure to tell Gary over and over how good his cock felt, how big it felt, bigger than hubby's. He slipped his hand around and rubbed my pussy until I came twice with him deep in my bottom. Second time sent him over the edge.

We relaxed at that point and I went to check hubby. She'd cum big time, twice, soaking her panties so it's another week in chastity.

We talked about it this morning, away from the sex play of it all. She still wants to get out of the chastity and thinks last night was too big of a test but she'll do what it takes. She's okay with needing to pass a test for release, she's enjoying that part of the whole thing.

So the adventure continues. Time to check her chastity and undies before we head out to run errands.
Click to expand...

Mm, yes please.
 
SweetAnnie40 said:
Well, it was a hell of a lot of fun last night. Gary came over around 8pm and we tortured my hubby a little by just making out on the couch for a long time. We finally went upstairs and I made hubby stand there until Gary was naked. Hubby has sucked that cock many times now and I know her mouth was watering. I attached the dildo to the chair seat, aimed it for the special hole in the back of her panties and helped her work herself down on to it until she could sit. I checked her cage to ensure she hadn't already cum and then pulled her panties back up.

Then I got to really enjoy Gary. We made out more as he slowly undressed me and I played with his cock. When I was down to bra and panties, I knelt to give him a blow job, right in front of hubby. She was whimpering and squirming a little. After I enjoyed swallowing his first load, we got on the bed proper and his mouth got to work on me. Excellent tongue talent there and I really let myself go, multiple times.

At that point I'd almost forgotten hubby as I wanted Gary's cock in me, first in pussy but pretty quick in my bottom that really drives me crazy. I made sure to tell Gary over and over how good his cock felt, how big it felt, bigger than hubby's. He slipped his hand around and rubbed my pussy until I came twice with him deep in my bottom. Second time sent him over the edge.

We relaxed at that point and I went to check hubby. She'd cum big time, twice, soaking her panties so it's another week in chastity.

We talked about it this morning, away from the sex play of it all. She still wants to get out of the chastity and thinks last night was too big of a test but she'll do what it takes. She's okay with needing to pass a test for release, she's enjoying that part of the whole thing.

So the adventure continues. Time to check her chastity and undies before we head out to run errands.
Click to expand...

Oh very nice!! I can’t imagin anyone making it through that without cumming multiple times!! So hot!!
 
SweetAnnie40 said:
Well, it was a hell of a lot of fun last night. Gary came over around 8pm and we tortured my hubby a little by just making out on the couch for a long time. We finally went upstairs and I made hubby stand there until Gary was naked. Hubby has sucked that cock many times now and I know her mouth was watering. I attached the dildo to the chair seat, aimed it for the special hole in the back of her panties and helped her work herself down on to it until she could sit. I checked her cage to ensure she hadn't already cum and then pulled her panties back up.

Then I got to really enjoy Gary. We made out more as he slowly undressed me and I played with his cock. When I was down to bra and panties, I knelt to give him a blow job, right in front of hubby. She was whimpering and squirming a little. After I enjoyed swallowing his first load, we got on the bed proper and his mouth got to work on me. Excellent tongue talent there and I really let myself go, multiple times.

At that point I'd almost forgotten hubby as I wanted Gary's cock in me, first in pussy but pretty quick in my bottom that really drives me crazy. I made sure to tell Gary over and over how good his cock felt, how big it felt, bigger than hubby's. He slipped his hand around and rubbed my pussy until I came twice with him deep in my bottom. Second time sent him over the edge.

We relaxed at that point and I went to check hubby. She'd cum big time, twice, soaking her panties so it's another week in chastity.

We talked about it this morning, away from the sex play of it all. She still wants to get out of the chastity and thinks last night was too big of a test but she'll do what it takes. She's okay with needing to pass a test for release, she's enjoying that part of the whole thing.

So the adventure continues. Time to check her chastity and undies before we head out to run errands.
Click to expand...

Omfg that almost made my clitty squirt and I wasn’t even there. God that is hot as fuck
 
What an amazing experience for all involved. I knew she was going to cum, but she came twice while caged & on that dildo??? The excitement in that room must have been amazing! Thanks for sharing the details!
 
Jenna2641 said:
What an amazing experience for all involved. I knew she was going to cum, but she came twice while caged & on that dildo??? The excitement in that room must have been amazing! Thanks for sharing the details!
Click to expand...

You're welcome and thanks for all the comments. I told her I was blogging our adventures and she loves knowing that others know.
 
My, such developments....

SweetAnnie40 said:
Well, it was a hell of a lot of fun last night. Gary came over around 8pm and we tortured my hubby a little by just making out on the couch for a long time. We finally went upstairs and I made hubby stand there until Gary was naked. Hubby has sucked that cock many times now and I know her mouth was watering. I attached the dildo to the chair seat, aimed it for the special hole in the back of her panties and helped her work herself down on to it until she could sit. I checked her cage to ensure she hadn't already cum and then pulled her panties back up.

Then I got to really enjoy Gary. We made out more as he slowly undressed me and I played with his cock. When I was down to bra and panties, I knelt to give him a blow job, right in front of hubby. She was whimpering and squirming a little. After I enjoyed swallowing his first load, we got on the bed proper and his mouth got to work on me. Excellent tongue talent there and I really let myself go, multiple times.

At that point I'd almost forgotten hubby as I wanted Gary's cock in me, first in pussy but pretty quick in my bottom that really drives me crazy. I made sure to tell Gary over and over how good his cock felt, how big it felt, bigger than hubby's. He slipped his hand around and rubbed my pussy until I came twice with him deep in my bottom. Second time sent him over the edge.

We relaxed at that point and I went to check hubby. She'd cum big time, twice, soaking her panties so it's another week in chastity.

We talked about it this morning, away from the sex play of it all. She still wants to get out of the chastity and thinks last night was too big of a test but she'll do what it takes. She's okay with needing to pass a test for release, she's enjoying that part of the whole thing.

So the adventure continues. Time to check her chastity and undies before we head out to run errands.
Click to expand...


What fun! Both you and sissy getting off!! Did you ever give Hubs a piece of your ass before you and him started femming him up? The last tryst was so good for all! Got me hard hearing about it, as usual. I would keep the bitch caged until you devised a proper test to see if she is totally femmed. I spose one test would be to have sissy dress up slutty and take her to a gay bar; but who knows? The gayboys wouid not hit on you (at least they shouldnt) but sissy might find some nice gay cock.
 
Oh my God Annie. That story is so damn hot.

I'm at work, caged and in some pretty red panties and reading that she came twice while riding her dildo made my clitty drip.

I would have loved to have been in hubby's place watching Gary take your sexy ass.
 
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