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Annie's Room

SweetAnnie40 said:
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.
Click to expand...


Wow ! That’s wild!
 
SweetAnnie40 said:
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.
Click to expand...

My Heart is Melting...

Paris.:kiss:
 
So we've had a few days to sort of soak it in. It really was amazing how well she passed in a light social situation. Her adam's apple is not prominent at all and she just needs to develop a feminine voice and I'm not sure what else we could do to improve. Practice, really, is what she needs now.

We've discussed having a date night once a week where we go out as girlfriends. We've talked about places not overly far from where we live where she would feel comfortable that she wouldn't run into people from her office. Going out as a woman once a week will give her good practice. She's started dressing the whole way at home (well, she was usually in some sort of sissy-wear when we were home but now she's dressing up like she would be going out, practicing the makeup, wearing flattering dresses a real woman would wear, not the overly fetish-ized satin sissy dresses.)

We've also discussed having her see a therapist regularly and talk through some things. She knows this has been very thrilling and fulfilling for her but what does it really mean? Is it just a fetish? Does she want to undergo a gender reassignment? Go partway and take hormones to develop her own bust but keep her clit? Does she want to be she 24/7 or be he at times?

If I was betting, I would say hubby does not want to become a full-fledged woman. Everything is fetish-ized and sexualized. Going out as a woman gave him a delicious cocktail of embarrassment, thrill, sensualization in the feminization, and sexual stimulation. If she hadn't been caged when we went out, there would have been a noticeable bulge in the front of her dress pretty much the whole time. Her panties were pretty wet when we got home. Anyway, she might want hormones to feel more curvy and beautiful but that's a guess.

So, the journey continues. Our next step is to shop for corsets this week before we head home from vacation. The right corset would do wonders for her figure (and we're both stumped as to why we didn't think of it before).
 
You know I've been following your updates, and I'm proud of you for deciding to go on this journey together. A strong support system is what everyone only dreams of.

The big question is how are you after all of this???



SweetAnnie40 said:
So we've had a few days to sort of soak it in. It really was amazing how well she passed in a light social situation. Her adam's apple is not prominent at all and she just needs to develop a feminine voice and I'm not sure what else we could do to improve. Practice, really, is what she needs now.

We've discussed having a date night once a week where we go out as girlfriends. We've talked about places not overly far from where we live where she would feel comfortable that she wouldn't run into people from her office. Going out as a woman once a week will give her good practice. She's started dressing the whole way at home (well, she was usually in some sort of sissy-wear when we were home but now she's dressing up like she would be going out, practicing the makeup, wearing flattering dresses a real woman would wear, not the overly fetish-ized satin sissy dresses.)

We've also discussed having her see a therapist regularly and talk through some things. She knows this has been very thrilling and fulfilling for her but what does it really mean? Is it just a fetish? Does she want to undergo a gender reassignment? Go partway and take hormones to develop her own bust but keep her clit? Does she want to be she 24/7 or be he at times?

If I was betting, I would say hubby does not want to become a full-fledged woman. Everything is fetish-ized and sexualized. Going out as a woman gave him a delicious cocktail of embarrassment, thrill, sensualization in the feminization, and sexual stimulation. If she hadn't been caged when we went out, there would have been a noticeable bulge in the front of her dress pretty much the whole time. Her panties were pretty wet when we got home. Anyway, she might want hormones to feel more curvy and beautiful but that's a guess.

So, the journey continues. Our next step is to shop for corsets this week before we head home from vacation. The right corset would do wonders for her figure (and we're both stumped as to why we didn't think of it before).
Click to expand...
 
So far going well...

SweetAnnie40 said:
So we've had a few days to sort of soak it in. It really was amazing how well she passed in a light social situation. Her adam's apple is not prominent at all and she just needs to develop a feminine voice and I'm not sure what else we could do to improve. Practice, really, is what she needs now.

We've discussed having a date night once a week where we go out as girlfriends. We've talked about places not overly far from where we live where she would feel comfortable that she wouldn't run into people from her office. Going out as a woman once a week will give her good practice. She's started dressing the whole way at home (well, she was usually in some sort of sissy-wear when we were home but now she's dressing up like she would be going out, practicing the makeup, wearing flattering dresses a real woman would wear, not the overly fetish-ized satin sissy dresses.)

We've also discussed having her see a therapist regularly and talk through some things. She knows this has been very thrilling and fulfilling for her but what does it really mean? Is it just a fetish? Does she want to undergo a gender reassignment? Go partway and take hormones to develop her own bust but keep her clit? Does she want to be she 24/7 or be he at times?

If I was betting, I would say hubby does not want to become a full-fledged woman. Everything is fetish-ized and sexualized. Going out as a woman gave him a delicious cocktail of embarrassment, thrill, sensualization in the feminization, and sexual stimulation. If she hadn't been caged when we went out, there would have been a noticeable bulge in the front of her dress pretty much the whole time. Her panties were pretty wet when we got home. Anyway, she might want hormones to feel more curvy and beautiful but that's a guess.

So, the journey continues. Our next step is to shop for corsets this week before we head home from vacation. The right corset would do wonders for her figure (and we're both stumped as to why we didn't think of it before).
Click to expand...


Of course you know hormones are a big step. Be sure to read up on it, esp with some of the trans girls here. Yassssssss, a therapist may not be far off if you head down that path.
 
Scotty13 said:
You know I've been following your updates, and I'm proud of you for deciding to go on this journey together. A strong support system is what everyone only dreams of.

The big question is how are you after all of this???
Click to expand...

Hi Scotty,

I'm doing okay. It has been a tremendous amount of change but we've been doing it together. She has gotten more supportive of me seeking women to be with, rather than just tolerant of my experimentation. I feel like we're evolving and so far we're doing it together. I mean we aren't having sex 24/7/365. We have plenty of normal life just with hubby dolled up in erotic lingerie underneath and me having to watch how much I ogle other women. We still have a good deal of the life we'd developed over the last 22 years. I'm starting to think that our marriage will become even a little more 'open' as we progress. Hard to predict. I think the biggest decision will be hubby's and how far she wants to go. Will she be satisfied with false breasts she takes off in order to go to work as he or does she want real breasts? Most everything else can be hidden or removed. Anyway, we're researching therapists to find someone who has experience in this area to help her and both of us.
 
Paris54 said:
Being and Living Together...

I Love It.

Paris.:kiss:
Click to expand...

That really is the crux of it all... love... and sharing our lives together in our true selves whatever that evolves to be. Never letting the sex games harm that or break rules of trust.
 
dacoach44 said:
Of course you know hormones are a big step. Be sure to read up on it, esp with some of the trans girls here. Yassssssss, a therapist may not be far off if you head down that path.
Click to expand...

If there are any trans members who wouldn't mind sharing their stories or advice with me in PMs or here in the thread, I would be very grateful.
 
Annie Says:

How do you turn it on and off?

Paris Says:

I get up in the Morning and There's a Cock in my In-Box.

How do you turn that off?
 
Last edited:
Paris54 said:
Annie Says:

How do you turn it on and off?

Paris Says:

I get up in the Morning and There's a Cock in my In-Box.

How do you turn that off?
Click to expand...

Sometimes a cock in my "in-box" is just what I need to start the day... just not a virtual one. ;)
 
A little sissy tart named Paris. Have you seen her? I believe she was wearing a pink satin sissy dress to get my attention...
 
SweetAnnie40 said:
A little sissy tart named Paris. Have you seen her? I believe she was wearing a pink satin sissy dress to get my attention...
Click to expand...

You've always complemented me when I wear this dress.

Should I take it off now?

I wouldn't want to get Cum on it.

Paris.:kiss:
 
Paris54 said:
You've always complemented me when I wear this dress.

Should I take it off now?

I wouldn't want to get Cum on it.

Paris.:kiss:
Click to expand...

Here, let me help you... no, slip your wrists through here... don't worry... there, let me get it nice and tight... can you move your arms? no? perfect! See the dress becomes a bondage dress, that's why I gave it to you. Now your arms are secured behind your back, each hand at the opposite elbow. No silly second thoughts or resistance once I decide what I'm going to do with you.

Now, walk over here on your stocking-covered knees. I'm taking off my panties and you have work to do...
 
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