Annie's Sissy Help Line

[Jenna2641]

I'm formulating a plan for another outing. The question is just how far will I go. I really want to wear my black lacy padded bralet under a dark blue sleeveless Mock turtleneck I have that really gives me some curves.

I hope you have another positive experience from it. Sounds like a cute outfit!

 

[SweetAnnie40]

Thank you Annie for your reply. Actually my wife hates anything to do with gay males or cds. And yes no sex with her for a few years now. My choice. I will not consider a divorce afte 30 yrs of marriage. I am sexually attracted to male cocks and no longer pussy. Call me bi or gay if you need a label. I don’t think I am so unusual for the aging male population. As for discussion of my desire to crossdress with the wife, that will not happen. Thanks again for your advice.

I wish you well within the parameters you're dealing with. I understand the commitment of marriage and if you can live in your limits and she doesn't need to know what you're doing, you can enjoy yourself.

(Cute knickers in your avatar!)

 

[OpenMouth]

I love wearing camisoles and bralets out in public. Under thick t-shirts or sweat shirts usually but when I go out of town I have worn them under thin ladies t-shirts. I have a nice Burgundy V neck that looks great with my pink lacy cami layered underneath. I wore that with tight low rise girl jeans and walked around Piedmont Park (Gay area) in Atlanta. I felt so sexy/exposed/scared/and somehow more myself than ever. It was nice to not get any strange looks there. I had lunch at at Gay friendly restaurant and was treated like a lady.

That was my one and only real outing.

That sounds so lovely. How wonderful it must be to go to a city where nobody knows you, during one of these events. To wear what you like and relax in it, pamper yourself in a hotel room. I'd love to show a bit of nylon and lace, paint my lips, flirt and generally show I was available...

 

[shawnavinyltv]

I just wanted to say a quick thank you for posting this! I've been dressing for years, but I know I get a lot of guys who are interested in dabbling in their feminine side. Also, plenty that want to get spouses or significant others involved. I may have to start directing them to this as a comprehensive treatment on the sissy and the sissy lifestyle!

Very wonderful, thank you!

 

[SweetAnnie40]

I just wanted to say a quick thank you for posting this! I've been dressing for years, but I know I get a lot of guys who are interested in dabbling in their feminine side. Also, plenty that want to get spouses or significant others involved. I may have to start directing them to this as a comprehensive treatment on the sissy and the sissy lifestyle!

Very wonderful, thank you!

You're welcome, Shawna. Feel free to ask anything you like. If I can't answer from my perspective, perhaps some of the "girls" here can help.

 

[irishblade]

Hi all. I need help. I’ve never done any sissy play but I’m home alone this weekend. I bought a pure romance toy called backstage pass. And I stole a pair of panties from my girl that I haven’t touched in ages. I really want to do some sissy play while she’s gone but I don’t know how. I imagine it’s just clean, lube and go but I’ve never done any backdoor play so I’m equally nervous and excited. Any help would be greatly appreciated. Thanks.

 

[Willieceedee]

Back door play is fun. Especially all dolled up. But please, please please go slow and use lots of lube, and work from small to large. Dont know how big your toy, size does make a difference!.

Since you have the time, make sure you are clean. Take the time to relax and enjoy the experience. Like love making, fore play is fun. Use your finger(s) with lube to relax, then try the toy. If it doesn't fit, or fit well, or if there is pain...STOP! Again go slow. You might also find trying different positions.

With me, it took multiple tries with a small plug and lots of lube. I finally was successful by inserting it when kneeling over it cowboy riding style and pushing down on it SLOWLY. After that I got the hang of it I tired different positions.

I am sure many LIT members on this site have their own techniques and enjoyments, but almost everyone that has offered advice say to take it slowly with lube.

Enjoy your experience. I am sure it will leave you wanting more.

 

[OpenMouth]

I agree, anal masturbation is wonderful while dressed as a woman. Smooth, moisturised, holdups, heels, wig and makeup - mmmmmm

 

[irishblade]

Back door play is fun. Especially all dolled up. But please, please please go slow and use lots of lube, and work from small to large. Dont know how big your toy, size does make a difference!.

Since you have the time, make sure you are clean. Take the time to relax and enjoy the experience. Like love making, fore play is fun. Use your finger(s) with lube to relax, then try the toy. If it doesn't fit, or fit well, or if there is pain...STOP! Again go slow. You might also find trying different positions.

With me, it took multiple tries with a small plug and lots of lube. I finally was successful by inserting it when kneeling over it cowboy riding style and pushing down on it SLOWLY. After that I got the hang of it I tired different positions.

I am sure many LIT members on this site have their own techniques and enjoyments, but almost everyone that has offered advice say to take it slowly with lube.

Enjoy your experience. I am sure it will leave you wanting more.

Thanks! I did it this morning. And it was fantastic!!

I have basically vibrating anal beads. I did my cleaning and prep beforehand. I started naked on my back and lubed up the toy and myself. I slowly inserted the first ball and got to the second. I turned the vibrator on medium. I rolled over into all fours as I wasn’t feeling much more than pressure. I could feel it more but not great just due to the angle. So I turned it on high and tried to crouch on top of it. That was the money ticket. I rocked back and forth on that thing and boy, did I cum! Now I want more toys. Hopefully Mrs. Blade is accepting of my newfound fun time!

 

[Willieceedee]

Thanks! I did it this morning. And it was fantastic!!

I have basically vibrating anal beads. I did my cleaning and prep beforehand. I started naked on my back and lubed up the toy and myself. I slowly inserted the first ball and got to the second. I turned the vibrator on medium. I rolled over into all fours as I wasn’t feeling much more than pressure. I could feel it more but not great just due to the angle. So I turned it on high and tried to crouch on top of it. That was the money ticket. I rocked back and forth on that thing and boy, did I cum! Now I want more toys. Hopefully Mrs. Blade is accepting of my newfound fun time!

I am glad you enjoyed your special time. Its fun to explore, try new toys, positions, , new clothes or lingerie too. You are well on your way, Welcome to Annie's Sissy Gurls club!

 

[irishblade]

I am glad you enjoyed your special time. Its fun to explore, try new toys, positions, , new clothes or lingerie too. You are well on your way, Welcome to Annie's Sissy Gurls club!

Thanks! It was nerve wracking but I thoroughly enjoyed it. Especially once I crouched down.

 

[SweetAnnie40]

I am glad you enjoyed your special time. Its fun to explore, try new toys, positions, , new clothes or lingerie too. You are well on your way, Welcome to Annie's Sissy Gurls club!

Thanks for being so helpful in my absence. Glad it turned out as well as she'd hoped.

 

[irishblade]

Thanks for being so in my absence. Glad it turned out as well as she'd hoped.

Nah...it was better than I’d hoped lol. Totally unexpected.

 

[BiMale4KinkyFun]

Here is a recent adventure I had. I posted this in another thread but I feel it fits here also.

To a have a special day in panties today, I put in a vibrating plug and turned on medium. I kept it in while doing all my shopping today. This plug can be controlled by my phone. So when I saw this gorgeous black man at the hardware store. I set it to high and looked at items behind him. I was so horny I nearly cam before he walked away.

 

[SweetAnnie40]

Here is a recent adventure I had. I posted this in another thread but I feel it fits here also.

To a have a special day in panties today, I put in a vibrating plug and turned on medium. I kept it in while doing all my shopping today. This plug can be controlled by my phone. So when I saw this gorgeous black man at the hardware store. I set it to high and looked at items behind him. I was so horny I nearly cam before he walked away.

Sounds like a lot of fun! Did he notice you or your bulge? Hear your vibe?

I wonder what it would take to get a remote vibe with thrusting motion that a sissy could wear in her panties... a nice firm strap between her legs to keep the base in place and then motorized cock thrusting. I bet that's make you cum dreaming about the pretty black man.

 

[SweetAnnie40]

Well, this year won't be like usual years with the pandemic but hopefully some of you sissy girls are taking advantage of Halloween to do more dressing than you might otherwise be permitted or dare to do. What are your Halloween plans? What will you dress up as and where will you go?

I think I'm stealing my husband's princess dress for our walk around the neighborhood. He hasn't decided what "jenna" will wear but I'm sure she'll be saucy!

 

[dawndavis66]

Well, this year won't be like usual years with the pandemic but hopefully some of you sissy girls are taking advantage of Halloween to do more dressing than you might otherwise be permitted or dare to do. What are your Halloween plans? What will you dress up as and where will you go?

I think I'm stealing my husband's princess dress for our walk around the neighborhood. He hasn't decided what "jenna" will wear but I'm sure she'll be saucy!

Excellent question Annie. I hope to be a French Maid this year.

 

[Bittersweet1215]

Well, this year won't be like usual years with the pandemic but hopefully some of you sissy girls are taking advantage of Halloween to do more dressing than you might otherwise be permitted or dare to do. What are your Halloween plans? What will you dress up as and where will you go?

I think I'm stealing my husband's princess dress for our walk around the neighborhood. He hasn't decided what "jenna" will wear but I'm sure she'll be saucy!

I wish Annie. I certainly wish.

If I could? I think I'd be a real slutty nun. I don't know why. Maybe it's the sin.

 

[Jenna2641]

I'm formulating a plan for another outing. The question is just how far will I go. I really want to wear my black lacy padded bralet under a dark blue sleeveless Mock turtleneck I have that really gives me some curves.

Sounds pretty sexy. Hope you get to pull it off!

 

[stargame]

https://cache.sharesome.com/file/sharesome/uploads/user-images/u382084/a9qrbs-tk2y8ytzt6-p.webp

 

[stargame]

https://cache.sharesome.com/file/sharesome/uploads/user-images/u382084/a9qrbs-sneo1xitiy-p.webp

So me.

 

[stargame]

https://cache.sharesome.com/file/sharesome/uploads/user-images/u382084/a9qrbs-0ixdajy0yy-p.webp

And be a rich man's trophy wife.

 

[SweetAnnie40]

https://cache.sharesome.com/file/sharesome/uploads/user-images/u382084/a9qrbs-tk2y8ytzt6-p.webp

Well said. In addition to our marriage, our family, and our love for one another, that acceptance and encouragement from a woman was the thing my husband so desperately needed when he first confessed to me.

 

[BlackSatinKnight]

So frustrated today. I was going to meet a gentlemen I had been communicating with. I went yesterday to get some new panties, pantyhose and other things for our first meeting. I took the time to make sure I was properly groomed, dressed in a nice pair of pink panties and some sheer shiny hose with a new but plug in for him. Of course he cancelled. Yesterday his wife was out of town and was going to be out of town for a couple of days, today they are out running errands. If you are going to lie to me, then don’t bother stringing me along.

I’m in a sexless marriage, once in the past year and I’m tired of being turned down. No physical contact except for a morning hug and a good night kiss. This is so frustrating.

Guess I’ll just give up on sex for a while.

 

[dacoach44]

Never easy to find cock........

So frustrated today. I was going to meet a gentlemen I had been communicating with. I went yesterday to get some new panties, pantyhose and other things for our first meeting. I took the time to make sure I was properly groomed, dressed in a nice pair of pink panties and some sheer shiny hose with a new but plug in for him. Of course he cancelled. Yesterday his wife was out of town and was going to be out of town for a couple of days, today they are out running errands. If you are going to lie to me, then don’t bother stringing me along.

I’m in a sexless marriage, once in the past year and I’m tired of being turned down. No physical contact except for a morning hug and a good night kiss. This is so frustrating.

Guess I’ll just give up on sex for a while.

I dated CD's; they all have these disappointing stories..........