Annie's Room

Okay, so I try not to buy things online in general and if I do I don't buy things whose sizes only go up to XL. The XL will run small and the creator doesn't understand bigger sizes.

Then I see something like this and just take the plunge. It is tight on me but damn it looks great. Hubby was impressed (and naturally wanted to buy one for himself)...

https://www.boutiquefeel.com/produc...f712-088c-4220-93d4-4498d382b877.html?gf=~~10
 
So, I had another call with Ashley last night. We've been chatting a few times a week. We have some different things in common outside of my sissy hubby but the conversation always gets around to sex eventually. It actually gets kind of flirtatious so I'm sure she's interested in more than my hubby (glee!).

Ashley is a few years younger than hubby and I. She has light reddish-brown hair she wears long, usually in a pony tail. I find her to be very pretty and appreciate that she is quite curvy (girl of my own tribe!). I don't know many people at all in real life who are kink-comfortable so it is refreshing to be able to talk to her about things.

We're going to meet up a little later today, just some coffee outside. (Trust me, the surging pandemic, masking and precautions don't bode well for a lively social life but I try to be as safe as I can be). Now that we've talked about a lot of intimate stuff I want to see if she's as flirtatious in person. I'm rather excited at the prospect so I'm sitting here in the bedroom getting ready. Just showered and trying to figure out what to wear....
 
So, I had another call with Ashley last night. We've been chatting a few times a week. We have some different things in common outside of my sissy hubby but the conversation always gets around to sex eventually. It actually gets kind of flirtatious so I'm sure she's interested in more than my hubby (glee!).

Ashley is a few years younger than hubby and I. She has light reddish-brown hair she wears long, usually in a pony tail. I find her to be very pretty and appreciate that she is quite curvy (girl of my own tribe!). I don't know many people at all in real life who are kink-comfortable so it is refreshing to be able to talk to her about things.

We're going to meet up a little later today, just some coffee outside. (Trust me, the surging pandemic, masking and precautions don't bode well for a lively social life but I try to be as safe as I can be). Now that we've talked about a lot of intimate stuff I want to see if she's as flirtatious in person. I'm rather excited at the prospect so I'm sitting here in the bedroom getting ready. Just showered and trying to figure out what to wear....

Hey hope it goes well Annie x

What to wear, sexy, flirtatious but not too obvious … how long have you got to decide?
 
Have fun, Annie!

Don’t do anything I wouldn’t do. :rolleyes:


BTW, that is a really cute little blue teddy. ;)
 
Okay, so I try not to buy things online in general and if I do I don't buy things whose sizes only go up to XL. The XL will run small and the creator doesn't understand bigger sizes.

Then I see something like this and just take the plunge. It is tight on me but damn it looks great. Hubby was impressed (and naturally wanted to buy one for himself)...

https://www.boutiquefeel.com/produc...f712-088c-4220-93d4-4498d382b877.html?gf=~~10

Oh tell me about it, I always check the sizing charts when buying things made in China.....they run, no kidding, 4 sizes too small. but once you figure out how their clothing runs you can find some real inexpensive outfits...a place calle "Light in the Box" sells a lot of CosPlay outfits and they sell their dresses in a wide range of sizes and will also custom sew them also....I bought a really girly dress and I was very please to find it fit nicely


https://encrypted-tbn3.gstatic.com/shopping?q=tbn:ANd9GcRFjIfvr3OQpWuvg5tM5DLEVZemowsGTrInImw97EIFEg4lDPnnfui-BIN6kV6tYx-kFMHLumHU4HP_A4VlBJM_REGm5sNWusNtwkxTtn_4SRHliDYjt9t4&usqp=CAc

Princess Sweet Lolita Vacation Dress Dress

Check out the sizing chart and you should be able to find something that fits....order a tad larger just to be safe, you can always make it smaller.

Trish
 
So, I had another call with Ashley last night. We've been chatting a few times a week. We have some different things in common outside of my sissy hubby but the conversation always gets around to sex eventually. It actually gets kind of flirtatious so I'm sure she's interested in more than my hubby (glee!).

Ashley is a few years younger than hubby and I. She has light reddish-brown hair she wears long, usually in a pony tail. I find her to be very pretty and appreciate that she is quite curvy (girl of my own tribe!). I don't know many people at all in real life who are kink-comfortable so it is refreshing to be able to talk to her about things.

We're going to meet up a little later today, just some coffee outside. (Trust me, the surging pandemic, masking and precautions don't bode well for a lively social life but I try to be as safe as I can be). Now that we've talked about a lot of intimate stuff I want to see if she's as flirtatious in person. I'm rather excited at the prospect so I'm sitting here in the bedroom getting ready. Just showered and trying to figure out what to wear....

I'll admit I was hoping for our flirtation to go to the next level and dressed appropriately but it turned out she really needed to talk to me about her marriage, much of it focusing on their non-existent sex life. When her husband was at our back yard barbecue, he seemed to be listening very carefully to our story and looking at hubby a lot, but once he got home, he said he didn't like what we were doing, that it made him uncomfortable. Ashley wonders if he's gay or bi and feels he is very turned on by what we're doing but can't let himself enjoy it. She also worried that if he is gay he'll leave her and she'll be raising their daughter alone. Some strong psychological barriers there. Not much I can do to help them get through it.

But! We did agree that Ashley wanted to explore more. I invited her over tonight to be a voyeur to some sissy play with hubby. Hubby is very excited. Son and his girlfriend will be out of the house with friends all evening. Maybe she'll watch. Maybe she'll join in. Maybe she'll join me in bed while hubby watches. It all has me very aroused and excited. Difficult to wait until this evening...
 
I'll admit I was hoping for our flirtation to go to the next level and dressed appropriately but it turned out she really needed to talk to me about her marriage, much of it focusing on their non-existent sex life. When her husband was at our back yard barbecue, he seemed to be listening very carefully to our story and looking at hubby a lot, but once he got home, he said he didn't like what we were doing, that it made him uncomfortable. Ashley wonders if he's gay or bi and feels he is very turned on by what we're doing but can't let himself enjoy it. She also worried that if he is gay he'll leave her and she'll be raising their daughter alone. Some strong psychological barriers there. Not much I can do to help them get through it.

But! We did agree that Ashley wanted to explore more. I invited her over tonight to be a voyeur to some sissy play with hubby. Hubby is very excited. Son and his girlfriend will be out of the house with friends all evening. Maybe she'll watch. Maybe she'll join in. Maybe she'll join me in bed while hubby watches. It all has me very aroused and excited. Difficult to wait until this evening...
Beautiful possibilities there. I hope all of you get to have an evening of your dreams. I also hope you will share all the details with us when you can.
 
I'll admit I was hoping for our flirtation to go to the next level and dressed appropriately but it turned out she really needed to talk to me about her marriage, much of it focusing on their non-existent sex life. When her husband was at our back yard barbecue, he seemed to be listening very carefully to our story and looking at hubby a lot, but once he got home, he said he didn't like what we were doing, that it made him uncomfortable. Ashley wonders if he's gay or bi and feels he is very turned on by what we're doing but can't let himself enjoy it. She also worried that if he is gay he'll leave her and she'll be raising their daughter alone. Some strong psychological barriers there. Not much I can do to help them get through it.

But! We did agree that Ashley wanted to explore more. I invited her over tonight to be a voyeur to some sissy play with hubby. Hubby is very excited. Son and his girlfriend will be out of the house with friends all evening. Maybe she'll watch. Maybe she'll join in. Maybe she'll join me in bed while hubby watches. It all has me very aroused and excited. Difficult to wait until this evening...

I find all very intriguingly erotic...Oh my I hope hubby wears something really girly and sissy like...with the accent on "pink" to set her self apart from the two of you. Oh man what a rush this is going to be for him....I hope Ashley does watch and join in helping here or there....Maybe hubby and you can get a read on what blows her skirt up and give her an evening she will remember forever.
.
 
Okay, so I try not to buy things online in general and if I do I don't buy things whose sizes only go up to XL. The XL will run small and the creator doesn't understand bigger sizes.

Then I see something like this and just take the plunge. It is tight on me but damn it looks great. Hubby was impressed (and naturally wanted to buy one for himself)...

https://www.boutiquefeel.com/produc...f712-088c-4220-93d4-4498d382b877.html?gf=~~10

Now... I would like to believe you bought it, but a picture tells a thousand words "whistles innocently"....:devil:

Loving the plunge between cheeks!
 
I'll admit I was hoping for our flirtation to go to the next level and dressed appropriately but it turned out she really needed to talk to me about her marriage, much of it focusing on their non-existent sex life. When her husband was at our back yard barbecue, he seemed to be listening very carefully to our story and looking at hubby a lot, but once he got home, he said he didn't like what we were doing, that it made him uncomfortable. Ashley wonders if he's gay or bi and feels he is very turned on by what we're doing but can't let himself enjoy it. She also worried that if he is gay he'll leave her and she'll be raising their daughter alone. Some strong psychological barriers there. Not much I can do to help them get through it.

But! We did agree that Ashley wanted to explore more. I invited her over tonight to be a voyeur to some sissy play with hubby. Hubby is very excited. Son and his girlfriend will be out of the house with friends all evening. Maybe she'll watch. Maybe she'll join in. Maybe she'll join me in bed while hubby watches. It all has me very aroused and excited. Difficult to wait until this evening...

Oh my, I really hope you have all the fun you want, I hope hubby does too. Evidence that there are people out there with our kinks and are willing to explore.... am only a teensy bit envious, but not sure of whom... all three of you at some point I suspect!!:devil::heart::kiss:
 
I find all very intriguingly erotic...Oh my I hope hubby wears something really girly and sissy like...with the accent on "pink" to set her self apart from the two of you. Oh man what a rush this is going to be for him....I hope Ashley does watch and join in helping here or there....Maybe hubby and you can get a read on what blows her skirt up and give her an evening she will remember forever.
.

Thanks, honey. As long as she can put aside her home issues, I'm sure we'll have a lot of fun. Hubby is swimming in the pool (in his one-piece of course) and will pick out his play outfit next. Then an enema before play time.
 
Hi all, just a quick update. Ashley came over to play with us and it went pretty well. Hubby was dolled up maximum-sissy when she got there and she was very complimentary to him. After grabbing some water, we headed up to the bedroom. I'd prepared a comfy chair for her to watch. I did strip-tease down to my lingerie focusing on Ashley and was feeling pretty excited. Hubby got down to business with his mouth between my legs on the bed and I watched Ashley watch me be pleasured and cum. By then she was touching her panties under her skirt.

I put on the strapon and had hubby kneel to give 'me' a blow job. He puts on a good show and Ashley was getting more excited. I put hubby on the bed on his knees and chest. I added a little surprise and cuffed his wrists and locked them together behind his back. He was pretty hard in his ruffled satin sissy panties. I pegged him and he was very vocal until he finally came in his panties.

So I helped Hubby off the bed to stand there in his dark-cum-stained panties and his cuffs. He begged to play with us and I gagged him with my panties. I cleaned off the strapon and tried to be erotic about it and then led Ashley to the bed.

She and I explored each other on the bed. I very much enjoyed that part with no limits. She came quickly and later again on my strapon.

By that point Hubby was hard and straining again but Ashley and I were pretty sated. I retrieved my panties and Ashley asked hubby all sorts of questions. He was very excited to talk about what he desires, how he feels dressed up feminine, etc. She eventually stroked him in his panties until he came again.

After releasing hubby, Ashley and I went to have some drinks and sit by the pool and talk. She really liked it but a lot of her worries were bubbling up so we talked a couple hours before she went home.

I hope she will come again but she hasn't decided if she will tell her husband or not. I urged her to tell him as I really don't want to be part of breaking up their marriage. I'm uncomfortable with secrets so I really hope she does.

It was a great night and I hope you gurls enjoyed my quick summary. :)
 
Hi all, just a quick update. Ashley came over to play with us and it went pretty well. Hubby was dolled up maximum-sissy when she got there and she was very complimentary to him. After grabbing some water, we headed up to the bedroom. I'd prepared a comfy chair for her to watch. I did strip-tease down to my lingerie focusing on Ashley and was feeling pretty excited. Hubby got down to business with his mouth between my legs on the bed and I watched Ashley watch me be pleasured and cum. By then she was touching her panties under her skirt.

I put on the strapon and had hubby kneel to give 'me' a blow job. He puts on a good show and Ashley was getting more excited. I put hubby on the bed on his knees and chest. I added a little surprise and cuffed his wrists and locked them together behind his back. He was pretty hard in his ruffled satin sissy panties. I pegged him and he was very vocal until he finally came in his panties.

So I helped Hubby off the bed to stand there in his dark-cum-stained panties and his cuffs. He begged to play with us and I gagged him with my panties. I cleaned off the strapon and tried to be erotic about it and then led Ashley to the bed.

She and I explored each other on the bed. I very much enjoyed that part with no limits. She came quickly and later again on my strapon.

By that point Hubby was hard and straining again but Ashley and I were pretty sated. I retrieved my panties and Ashley asked hubby all sorts of questions. He was very excited to talk about what he desires, how he feels dressed up feminine, etc. She eventually stroked him in his panties until he came again.

After releasing hubby, Ashley and I went to have some drinks and sit by the pool and talk. She really liked it but a lot of her worries were bubbling up so we talked a couple hours before she went home.

I hope she will come again but she hasn't decided if she will tell her husband or not. I urged her to tell him as I really don't want to be part of breaking up their marriage. I'm uncomfortable with secrets so I really hope she does.

It was a great night and I hope you gurls enjoyed my quick summary. :)

Wow, this sounds like the golden ticket that links Sissy Hubs future and yours. I’m really happy for you, that you seem to have found a girl who digs you, and who can allow you all to play together
 
Hi all, just a quick update. Ashley came over to play with us and it went pretty well. Hubby was dolled up maximum-sissy when she got there and she was very complimentary to him. After grabbing some water, we headed up to the bedroom. I'd prepared a comfy chair for her to watch. I did strip-tease down to my lingerie focusing on Ashley and was feeling pretty excited. Hubby got down to business with his mouth between my legs on the bed and I watched Ashley watch me be pleasured and cum. By then she was touching her panties under her skirt.

I put on the strapon and had hubby kneel to give 'me' a blow job. He puts on a good show and Ashley was getting more excited. I put hubby on the bed on his knees and chest. I added a little surprise and cuffed his wrists and locked them together behind his back. He was pretty hard in his ruffled satin sissy panties. I pegged him and he was very vocal until he finally came in his panties.

So I helped Hubby off the bed to stand there in his dark-cum-stained panties and his cuffs. He begged to play with us and I gagged him with my panties. I cleaned off the strapon and tried to be erotic about it and then led Ashley to the bed.

She and I explored each other on the bed. I very much enjoyed that part with no limits. She came quickly and later again on my strapon.

By that point Hubby was hard and straining again but Ashley and I were pretty sated. I retrieved my panties and Ashley asked hubby all sorts of questions. He was very excited to talk about what he desires, how he feels dressed up feminine, etc. She eventually stroked him in his panties until he came again.

After releasing hubby, Ashley and I went to have some drinks and sit by the pool and talk. She really liked it but a lot of her worries were bubbling up so we talked a couple hours before she went home.

I hope she will come again but she hasn't decided if she will tell her husband or not. I urged her to tell him as I really don't want to be part of breaking up their marriage. I'm uncomfortable with secrets so I really hope she does.

It was a great night and I hope you gurls enjoyed my quick summary. :)

That’s so hot!!! Your so lucky!!! Can’t wait to see what cums next!!!
 
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