Sissy Appreciation Sex

Coming Soon My Pretties.

Soon!

Pleasure and Pain

Strange bedfellows.  But my wife's boss had a way in delivering each.  I could finally understand how she fell under his spell.

Understatement

See this photo?  This Caption?  

 Ten minutes?  Seriously?  I'd say more like ten seconds.

Pearl Necklace

"Hi sissy," my girlfriend whispered.  "Do you like my pearl necklace?  Well guess what?  My boyfriend is on his way over and he's going to give you one too.  Only yours will taste a lot better."

The Preparation

This had become our Saturday evening ritual.  I would dress in one of my pretty French maid's outfits, and then I would help dress my wife for her date with some man.  And all of the lingerie she wore was of my choosing.  And I had learned better than to dress her in anything frumpy.

But even my wife looked like she thought I may have outdone myself with this evening's selection.

Premature

Once a month my wife would release from my chastity cage and let me fuck her.  If - if - I could last long enough through any preliminary teasing.  The moment she wrapped her stocking clad feet around my clitty, I knew I'd never get inside of her this month.  And I also knew that in a matter of moments I would be licking my cum off of her stocking covered feet.

Which One Is The Sissy?

Ponytail

The first time one of my wife’s boyfriends grabbed my hair like this when I was fluffing him for her, it scared me. After my wife explained it was a good thing when the man took charge, I didn’t mind when it happened in the future.

Decisions, Decisions - What To Do?

My wife was getting dressed for her dinner date with her former boyfriend from college, who was in town for business.

"What do you think sweetie?" she asked me.  "Should I bother wearing the panties?  I mean, they're sexy and all.  But why bother?  Ya know?"

Which One Is The Sissy?

Hi Big Fella!

"Meet my boyfriend sissy."

Leeanne's Pollyanna Sissy Gift Exchange

I love the various TG Cap sites that I've been discovering around the Internet.  They have a really cool sense of community.  As my part of the Pollyanna Sissy gift exchange, I'm featuring particular blog entries from several of the TG Cap community, as a way to share their excellent work with others who may visit my site.  So, with no further ado, and in no particular order of importance, start opening your gifts.

Kaity's Fantabulous Captions

So, what does this Cap do for me?  Well, first off, being a sissy, the idea of using tampons is one of my fantasies, because, that is just one step closer to being a real girl.  But Kaitlyn Renee takes it a step further for me by pointing out that sometimes, we should be careful what we wish for.  I love it!

Caitlyn's Mask's

Caitlyn was inspired by a blog entry she saw on Saragirl's Sissy Confessions to write up this Cap.  I agree with Caitlyn that Sara's short line gave this photo a little zing, but I also love how Caitlyn took the image and turned into a great story that any sissy would love.

'Dee' lusions of Grandeur

Dee Mentia gets credit for the idea of the Christmas Gift Exchange.  She was kind enough to let me be included even though I'm not a Cap blog.  I love all of her Caps, but this one really caught my fancy because, once again, as a sissy, I'm totally into the sexy lingerie of the fifties era.  Walking into a situation like this would make me forget all about my fear of the bomb, since I'd now be a bombshell myself.  

Alectra's Playground

  I probably don't really need to explain why I like this Cap Alectra did so much.  I mean, duh, I'm a sissy.  And every sissy loves training.  This Cap sums up the conflict within every sissy, I think.  We long to be feminized, and wish for a woman who take us under their wing.  But then, when we find one, we quickly learn that the path to complete feminization is sometimes difficult and rocky.  But in the end, when are fully sissified, it is worth it.

Anne Oni Mouse sTumbles

Anne Oni may be the most prolific TG Capper out there.  She has several blogs, including a tumblr blog that is very active.  Then, she takes what I suppose she must think of as her best Caps and puts them on Anne Oni Mouse sTumbles.  I love the one I've featured above.  What sissy would not be thrilled to be placed in a position to have to whore oneself out simply to escape a torturous sitiuation?  I know that I would.

Jennifer's TG Caps of Defiance

 

Another prolific Capper,  Jennifer's Caps routinely get my sissy blood boiling.  And this one in particular is one of my favorites of hers.  I think every sissy longs for her wife to take charge and to, as this lovely wife hints, perhaps cuckold her.

And Now For Something Completely Different 

 Martha has a great TG Cap blog.  One of my favorites is this one.  Using only a few words, she expresses what a lot of sissies sometimes feel.  We're filled with all of these feminine thoughts, but aren't completely equipped to navigate the world as girls because we don't have a lifetime of experience and have spent so much time fighting against our nature.  But, then, we find ourselves in a situation like this one.

Annabelle's Family Tradition 

 I love Annabelle's site!  And this Cap is one of my favorites.  I don't know if you've read the early posts on my blog, but if you have you know that I am married to a woman who I had a crush on in high school when she was the head cheerleader.  So, it would be a sissy dream of mine to be able to be a cheerleader as well. 

Lexie's Library of TG Captions 

 How great would it be to be able to "poof," and become her?  Lexie shows you how in this excellent Cap!  Check it out!

One Of My Favorite Desserts

Strawberries and Cream

Sissy Santa

She prefers to sit on your lap.

Which One Is The Sissy?

Merry Christmas!

She's Looking For A Man To Fuck

And her sissy husband approves.  How do I know?

She's a Swinger.

Which One Is The Sissy?

Something in Common?

So Do Sissies!

From PicknickBasket

She Can Have Any Man She Wants

But this is her biggest fan.

Don't Just Stand There

Suck them.  Then wear them.

The Second Time

The first time my wife let a man fuck her, at my suggestion, I had to coax her and convince her it was something worth trying.  The second time, not so much.

Why Blondes Have More Fun

It's pretty simple really.

 Credit to "Sparks My Imagination"

Sissy Pollyanna

Dee Mentia, of 'Dee'lusions of Grandeur has proposed a really great idea for a holiday gift exchange.  Caitlyn, of Caitlyn's Masks, has jumped in with both feet as well.  They are two of the premier TG Cap sites on the Internet.  And while my blog is not a TG Cap blog, they are willing to allow me to participate in their cool idea for a gift exchange.

So I'm going to follow Dee's idea also and set up a blog post for sometime Christmas morning, probably around 11:30 AM Eastern Standard Time, where I will feature (hopefully) a bunch of TG caption sites that agree to do the same in exchange.  I'll take any people that agree to do so here (by commenting below), as well as those that respond on Dee's and Caitlyn's blog.
 

RULES / GUIDELINES

1. You post below that you wish to be involved in the gift exchange, saying that you want to participate and reciprocate.
2. I will go to your TG Captions, Sissy or other Blog and pick a caption I like, posting a thumbnail copy in the post and a link to that caption below it. Depending on how much time I have and the number of people participating, I might give a sentence or two about why I like the caption or why they should head there to the individual blog.
3. You do the same thing for me. You'll have a thumbnail and a link to a caption of mine in your post.
4. This step isn't required, but I think it'd be great if you could post this on YOUR blog, looking for others to trade with. I think it'd be a nice gift for people who are just READERS of Sissy or TG Captions to see how many blogs are out there, and give them exposure to some they might have missed.
5. Make your post on either Christmas Eve or Christmas Day.
6. I will not link to sites that ONLY snag other people's work. This is for the actual creators only. 

So if you have a blog that might enjoy some extra traffic, feel free to sign up below!!  See you on Christmas!

Sissy Kiss

My wife and her sister each feminized their husbands.  Sometimes, when they let us play together, they make us do what they like to call a Sissy Kiss.

It's a little embarrassing.  But it's cute too.

200 Sissy Lovers! We Know What That Means!

Sissy Appreciation Sex!  That's right!  According to the consensus, I will provide various acts of sissy sex to my second 100 Sissy Lovers.  Beginning soon!

My Fall To Grace - Chapter 28

I've just posted on Fictionmania a new chapter to my story being shown there - My Fall To Grace - Chapter 28

 Grace Andrews is a beautiful, confident, successful woman. She could have any man she wanted. She chose Dan Thompson, a successful Washington, D.C. attorney. This second story of mine, that will be released in installments, chronicles their relationship as it grows and flourishes, developing into something perhaps neither one could have envisioned the first night they met in a D.C. bar.  I hope readers enjoy my effort. Readers Note: This is a long story, but it is nearing conclusion.  I'll keep installments coming.  I love getting reader feedback.

For A Man

I'd never seen my wife look so, so sultry.  So slutty.  As if reading my mind, she explained, "This is how men like their women to look baby.  You wouldn't understand.  But Tyrone appreciates it.  And I like to please him.  You understand that?  Right?"

Smooooooth

That's how my wife prefers me.

Braless

She always wore bras to work, because that's what ladies did.  But she rarely wore bras when she was "going out with her girlfriends," because, as she explained it, "What's the point?  It's coming off sooner or later anyway."

Her First Shopping Trip Alone

Leeanne had never been out shopping alone.  Today was the first time since she received her breast implants that she went out in public, dressed en femme, without her wife.  She had so much fun nearly buying out the store.

You could say she "lost her head."

Boyfriend? Or Girlfriend?

There is an excellent photo blog on Tumblr called "Panties Only."  Panties Only posted this photo with the question, "Is there any woman who would like a boyfriend like THIS ?

It's a fair question.  But regardless, I know this much - I know a sissy who would love to have a girlfriend like that.

Oh! Hi there!

 It seems my Sissy Lovers have spoken.  The second 100 followers should receive some show of appreciation, but not necessarily a blowjob.  So, I suppose I must deliver.  And as much as I'd like to protest, I won't because I love providing pleasure.  I suppose it's my sissy nature to please.  So, the countdown begins when, or if, I hit 200.  Not there yet.

My Fall To Grace - Chapter 27

I've just posted on Fictionmania a new chapter to my story being shown there - My Fall To Grace - Chapter 27

 Grace Andrews is a beautiful, confident, successful woman. She could have any man she wanted. She chose Dan Thompson, a successful Washington, D.C. attorney. This second story of mine, that will be released in installments, chronicles their relationship as it grows and flourishes, developing into something perhaps neither one could have envisioned the first night they met in a D.C. bar.  I hope readers enjoy my effort. Readers Note: This is a long story, but it is nearing conclusion.  I'll keep installments coming.  I love getting reader feedback.

Which One Is The Sissy?

Whoever it is, she's a lucky sissy.

The Whisper

My wife was entertaining her boss in our bedroom.  She hadn't told him about me being a sissy yet, but wanted me to watch her.  So I was hiding behind a curtain leading into her dressing area.

 He'd just finished fucking her for the third time when she got up to use the restroom.  That's when she whispered to me, "Sissy!  I think he's gong to fuck me all night!  You may as well go to sleep in the guest room."

Most Popular Class At Sissy School

Advanced Cocksucking was an elective at The Vera Wang Institute for Male Modification, a/k/a "Sissy School," and the sissies only received one credit hour for attending, even though the weekly lab lasted three hours and two days per week, but it was by far the most popular course offered at Sissy School.  

The word among the sissies is that the professors are the best.

Which One Is The Sissy?

The sissy is the modest one.  You know, the one wearing appropriate clothes?

The Charity Auction

My wife insisted it was for a good cause.  That's why I agreed to let her feminize me for the annual Stepford Charity Auction.  I was a little embarrassed by the pre-auction inspection.  It was explained to me that the bidders were going to pay top dollar, and expected each "slave" to be clean.  "Slave?!" I asked my wife.  "I'm going to be someone's slave?!"  "Just for a week," she replied off-handedly, as if that would make me feel better about it.

NOTE:  This post was inspired by a story, "Slave Auction," I read on a blog called Sharon's Musings, run by a wonderful woman named Sharon Lawson.  I highly recommend her erotica.  There is another story on her blog called, "Don't Read This...," which Sharon cautions you not to read.  I encourage you to read it.

Man vs. Sissy

This pretty much sums it up.

What Do You Think Sissy?

Will my boss be able to keep his hands off of me tonight?

I hope not.

The Moments That Mattered

It was difficult sometimes.  Listening to my wife when she was being fucked by some man for hours at a time in our bed.  But no matter how often she did that, these were the moments that made me know I would always worship her.