Annie's Room

[dacoach44]

Thats Super, Annie...

So, quick update. We're still packing for our road trip tomorrow but hubby and I discussed his fantasies about going out in public with me as a woman. We've been playing with this for awhile now and slowly buying him things. He's become slender in the last year and I think he can really pull it off. So I've arranged a surprise for him at our destination. A full spa and makeover with a woman who knows about his 'situation'. And then we go to a restaurant together that night. I'm hoping he has an amazing day as I know I will. Wish us luck!

You are both gonna love it! Just dont put him in 4" heels...

 

[SweetAnnie40]

You are both gonna love it! Just dont put him in 4" heels...

But he's a total heels whore! (He's gotten good walking in high heels but we're taking more sensible ones as well)

 

[dacoach44]

Mmm

But he's a total heels whore! (He's gotten good walking in high heels but we're taking more sensible ones as well)

Sooo aggressive!! Is she gonna wear nylons, garters, and flash the boys in a cafe?

 

[Sclovers]

So, quick update. We're still packing for our road trip tomorrow but hubby and I discussed his fantasies about going out in public with me as a woman. We've been playing with this for awhile now and slowly buying him things. He's become slender in the last year and I think he can really pull it off. So I've arranged a surprise for him at our destination. A full spa and makeover with a woman who knows about his 'situation'. And then we go to a restaurant together that night. I'm hoping he has an amazing day as I know I will. Wish us luck!

Can’t wait to hear all the juice details!

 

[Wkd_Macey]

I'd meant to opine longer on the experience but got interrupted yesterday.

It was a lot of fun and while we didn't go back to a room and go further, it led to some beautiful masturbation for me that night (and frankly every night since). It was very interesting to make out with another woman and feel the differences with my experience with Carol. The basics are the same but everything is different too. Ashley was more forward than Carol and I really thought we were going to spend the night together but it just seemed good to stop after enjoying each other the way we did.

Out of the blue she did give me her panties before we left each other. Wish I'd thought to do the same but there wasn't a real opportunity. Needless to say they are a little treasure for me.

We've texted a little since that night but I get the feeling she isn't comfortable with me being married even with my assurances. I didn't get into all the "sissy" stuff about hubby with her but I don't know if knowing that would change anything. At this point I don't expect to see her again but she's a lovely memory.

You know what you ought to do, don't you Annie...

 

[jhenry922]

They're damned expensive. I would just get the cheapos, Amazon, for $25 or so. I know a sissy who got drunk, lost them, $350

Envy makes nice feeiing ones up to a fairly large size for around 70

 

[SweetAnnie40]

Envy makes nice feeiing ones up to a fairly large size for around 70

We went with these: https://www.thebreastformstore.com/teardrop-breastforms.aspx Size 6. They look amazing on him and we've worked out how to do the adhesive properly. A nice healthy c/d cup that fills out his lingerie fully.

So far we've done full dress-up here in the hotel and he's gone to the lobby to pick up a copy of the local paper and hurry back, heart racing. Maybe tomorrow night will be our 'date' out.

 

[stargame]

We went with these: https://www.thebreastformstore.com/teardrop-breastforms.aspx Size 6. They look amazing on him and we've worked out how to do the adhesive properly. A nice healthy c/d cup that fills out his lingerie fully.

So far we've done full dress-up here in the hotel and he's gone to the lobby to pick up a copy of the local paper and hurry back, heart racing. Maybe tomorrow night will be our 'date' out.

Very HOT, how do they feel?

 

[SweetAnnie40]

Very HOT, how do they feel?

Very real...

 

[stargame]

Very real...

omg.....I want!
Touch me too?

 

[Paris54]

We went with these: https://www.thebreastformstore.com/teardrop-breastforms.aspx Size 6. They look amazing on him and we've worked out how to do the adhesive properly. A nice healthy c/d cup that fills out his lingerie fully.

So far we've done full dress-up here in the hotel and he's gone to the lobby to pick up a copy of the local paper and hurry back, heart racing. Maybe tomorrow night will be our 'date' out.

OMG! I'm so jealous... Those are Beautiful.

Her first time out? You could probably hear her heart beating from out in the hallway. I'm so happy for both of you.

Paris.

 

[Paris54]

I might add that she's going to have dreams tonight like she's never dreamed before... You're going to have one very horny girl on your hands tomorrow morning. Waking up with Boobies is game changing.

I'd give her a good milking before breakfast. She'll be eating out of your hand for the rest of the day.

Paris.

 

[SweetAnnie40]

I might add that she's going to have dreams tonight like she's never dreamed before... You're going to have one very horny girl on your hands tomorrow morning. Waking up with Boobies is game changing.

I'd give her a good milking before breakfast. She'll be eating out of your hand for the rest of the day.

Paris.

She's caged though has been begging for me to unlock her this whole vacation. She's vibrating with arousal and her clitty has been wanting to be free. I edged her tonight and then had her tongue me as she played with her breasts. She's in the hotel bed, enjoying how her bra fits her big day tomorrow.

 

[BiTodd]

That sounds so fun! I am bi, and date sissies as well as femmes. I am also a gay bottom for ONE lovely cock.

I have huge sissy tendancies and fantasies. I dress super slutty and want to be used as a slutty/sissy so of course i want to hear about your real life experiences. Purty please.

 

[BiTodd]

We went with these: https://www.thebreastformstore.com/teardrop-breastforms.aspx Size 6. They look amazing on him and we've worked out how to do the adhesive properly. A nice healthy c/d cup that fills out his lingerie fully.

So far we've done full dress-up here in the hotel and he's gone to the lobby to pick up a copy of the local paper and hurry back, heart racing. Maybe tomorrow night will be our 'date' out.

Such a lucky sissy. I want to experience that.

 

[dacoach44]

Big date out...

Such a lucky sissy. I want to experience that.

What dress are you gonna put her in, Annie? Are you gonna use femme wiles to help find sissy a cock?

 

[SweetAnnie40]

Such a lucky sissy. I want to experience that.

Tonight is the night. Hubby was begging to be uncaged this morning and to cum but I know leaving him "needy" will be the best motivator for him to go through with our "date night" tonight. The spa was wonderful and Alicia was very understanding, treating hubby like one of the girls, telling 'her' what beautiful skin and tone she has, what a pretty figure, ignoring the little pink caged cock that was leaking the whole time. She did a cute little perm on hubby so 'her' hair is definitely femme. Tried some new makeup and got hubby and I ready to put it on him today. Teased us about meeting us when we went out tonight. (Hubby doesn't know that she probably will, again, treating hubby like a total girl friend and enhancing his experience. Sadly, Alicia is just a good friend and not interested in going to be with me.)

 

[dacoach44]

So true, Annie...

Very real...

All the CD's and sissies I play with really love nipple play. Esp the ones on HRT. Keep it up; you will have that sissy leaking like a queen just with nipple play. Hubs may even progress to the place where he doesnt get hard, just comes with a soft sissycock.

 

[Jerseyshore]

*Sipping Irish Breakfast tea, enjoying an Oliva sunshade, and taking notes*

 

[stargame]

Tonight is the night. Hubby was begging to be uncaged this morning and to cum but I know leaving him "needy" will be the best motivator for him to go through with our "date night" tonight. The spa was wonderful and Alicia was very understanding, treating hubby like one of the girls, telling 'her' what beautiful skin and tone she has, what a pretty figure, ignoring the little pink caged cock that was leaking the whole time. She did a cute little perm on hubby so 'her' hair is definitely femme. Tried some new makeup and got hubby and I ready to put it on him today. Teased us about meeting us when we went out tonight. (Hubby doesn't know that she probably will, again, treating hubby like a total girl friend and enhancing his experience. Sadly, Alicia is just a good friend and not interested in going to be with me.)

So wonderful, I love reading about you two.
.....in love for sure

 

[dacoach44]

So interesting....

So wonderful, I love reading about you two.
.....in love for sure

Fun to watch this. How exciting! May be wild events ahead....what if sissy finds a BF?

 

[SweetAnnie40]

Well, last night went extremely well. I was a little nervous but no where near as nervous as Jenna (hubby's current femme name). I had to calm her down a couple times. But let's start at the start.

We made an easy early day of it yesterday, going for a run together, having a light, nutritious lunch. From time to time I would quietly reach in Jenna's women's running shorts and fondle her caged cock until she would get close and then I'd stop.

Around mid-afternoon, she couldn't wait any longer to start getting ready so she had a nice long soak making sure she was sexy smooth everywhere. Afterward I did a little touch-up on her new hairdo but it had held together well overnight. I supervised her makeup but she wanted to do it. We attached the cleaned breast forms very carefully so they were positioned just right. The skin tone is about a 95% match to hubby so you have to look to see the edge of them.

That's when I presented her with a gift: a new set of pink satin panties and bra. We hugged and she was emotional and then slipped them on. I couldn't stop her from admiring herself in the mirror. She loves filling out the cups in lingerie now and feeling things fit like they should. She added her favorite thigh highs with a satin garter belt.

We'd bought her a dress for this special night, knee-length summer dress that I think works well because it is ~similar to her skin tone so subconsciously it makes her look a little naked. You can just see the hint of her lingerie through it as well. It fits her well but not overly tight so her lack of hips, etc. is hidden enough. Finally her 3" ankle-strap heels completed the look.

We hugged for quite a while, talking about how far we've come in the last year. I told her that I would love her if she was my husband or my wife. Jenna got quiet after that but thanked me.

Finally, I realized that she'd slipped into stalling so I 'dragged' my girl friend to the car to "go out". We drove down to the waterfront of the town we're staying near. I'd chosen the location partly because it is home to a university and has a thankfully pretty liberal/progressive reputation. We needed friendly territory for her first time.

We went to the Guild Tavern where I'd made a reservation. I took the lead in interacting with the hostess and the waitress and we were soon seated at a nice table. Jenna looked like she was going to faint. I took her hand and stroked it to calm her down. I told her no one was looking at us any more than they should look at two hot babes. (wink) She calmed down enough.

When the waitress came to get our order, she didn't bat an eye at Jenna. I just ordered for the both of us (his voice is one of the many things hubby thinks will 'out' him). A light meal, some wine for both of us. An after dinner drink. That's when Alicia stopped by and we chatted for a while, letting Jenna enjoy being part of the "inner circle of girl talk". Alicia introduced us to her date before they went back to their table. I think the date had been briefed as he made a point to compliment all the 'lovely ladies'.

We left soon after. As soon as we got in our car, Jenna couldn't stop talking about it. She'd been terrified, thrilled, amazed, crazy aroused, so many more emotions and sensations. It really had been everything she'd hoped for as a first time and she was so thankful that I'd made it happen for her, last night and the in last year. We kissed and quickly realized we needed to get back to the hotel... fast!

The rest of the evening was passionate and sensual play. I let her out of her cage, the strapon got a good work out (Jenna put it on too and used it on me). It was late when we finally went to sleep together.

 

[dacoach44]

So sweet, Annie...

Well, last night went extremely well. I was a little nervous but no where near as nervous as Jenna (hubby's current femme name). I had to calm her down a couple times. But let's start at the start.

We made an easy early day of it yesterday, going for a run together, having a light, nutritious lunch. From time to time I would quietly reach in Jenna's women's running shorts and fondle her caged cock until she would get close and then I'd stop.

Around mid-afternoon, she couldn't wait any longer to start getting ready so she had a nice long soak making sure she was sexy smooth everywhere. Afterward I did a little touch-up on her new hairdo but it had held together well overnight. I supervised her makeup but she wanted to do it. We attached the cleaned breast forms very carefully so they were positioned just right. The skin tone is about a 95% match to hubby so you have to look to see the edge of them.

That's when I presented her with a gift: a new set of pink satin panties and bra. We hugged and she was emotional and then slipped them on. I couldn't stop her from admiring herself in the mirror. She loves filling out the cups in lingerie now and feeling things fit like they should. She added her favorite thigh highs with a satin garter belt.

We'd bought her a dress for this special night, knee-length summer dress that I think works well because it is ~similar to her skin tone so subconsciously it makes her look a little naked. You can just see the hint of her lingerie through it as well. It fits her well but not overly tight so her lack of hips, etc. is hidden enough. Finally her 3" ankle-strap heels completed the look.

We hugged for quite a while, talking about how far we've come in the last year. I told her that I would love her if she was my husband or my wife. Jenna got quiet after that but thanked me.

Finally, I realized that she'd slipped into stalling so I 'dragged' my girl friend to the car to "go out". We drove down to the waterfront of the town we're staying near. I'd chosen the location partly because it is home to a university and has a thankfully pretty liberal/progressive reputation. We needed friendly territory for her first time.

We went to the Guild Tavern where I'd made a reservation. I took the lead in interacting with the hostess and the waitress and we were soon seated at a nice table. Jenna looked like she was going to faint. I took her hand and stroked it to calm her down. I told her no one was looking at us any more than they should look at two hot babes. (wink) She calmed down enough.

When the waitress came to get our order, she didn't bat an eye at Jenna. I just ordered for the both of us (his voice is one of the many things hubby thinks will 'out' him). A light meal, some wine for both of us. An after dinner drink. That's when Alicia stopped by and we chatted for a while, letting Jenna enjoy being part of the "inner circle of girl talk". Alicia introduced us to her date before they went back to their table. I think the date had been briefed as he made a point to compliment all the 'lovely ladies'.

We left soon after. As soon as we got in our car, Jenna couldn't stop talking about it. She'd been terrified, thrilled, amazed, crazy aroused, so many more emotions and sensations. It really had been everything she'd hoped for as a first time and she was so thankful that I'd made it happen for her, last night and the in last year. We kissed and quickly realized we needed to get back to the hotel... fast!

The rest of the evening was passionate and sensual play. I let her out of her cage, the strapon got a good work out (Jenna put it on too and used it on me). It was late when we finally went to sleep together.

Such a sweetwife. I take my sissydates out all over, but since I am a guy, I spose its easier. We may get a few stares, from women usually, but I sure dont care what anybody else thinks. Never had a problem, even here in the Midwest. Maybe for a lark, next outing you remove Jenna's cage, fondle her a bit, and make her leak in her pretty pink panties, in a cafe or bar? I bet if you slipped a cute waiter a 5 spot, had him give her a wink, she would totally blow her sissy load...

 

[dacoach44]

It is!

i know everyone has said it...but this is such a hot, well written story!

Isnt Annie such a peach?

 

[SweetAnnie40]

Such a sweetwife. I take my sissydates out all over, but since I am a guy, I spose its easier. We may get a few stares, from women usually, but I sure dont care what anybody else thinks. Never had a problem, even here in the Midwest. Maybe for a lark, next outing you remove Jenna's cage, fondle her a bit, and make her leak in her pretty pink panties, in a cafe or bar? I bet if you slipped a cute waiter a 5 spot, had him give her a wink, she would totally blow her sissy load...

Good ideas. I wanted to get much more sexually daring but I knew this was already overload for her to tried to keep it simple.