Daddy's Dilemma: Monday

This is one I've been working on for a week or so. i wanted the layout to be something more interesting than what I normally do. As you can probably tell this story will last a week and I'll post a new part each day so be sure to be here everyday.

This is the first multi-part story I've done about Chrissy. I like the idea that that character is younger than Bobbi so he's more comfortable in his role as a sissy because he grew up with that being considered normal.

The model was the real inspiration for the story. She's an amazingly hot transsexual escort from Russia but there aren't many pictures of her - really just enough to complete this series. I hope you all enjoy!

Tipsy MILF Sissy

Claimed

While you enjoy this new caption, take a look to your right and vote in the new poll. I'm planning on doing another caption contest in a week or two so help me decide what the theme should be this time so I can start gathering photos for you. If you have any thoughts on how I can improve the set-up for the next contest - prize changes, rule changes, whatever - post a comment or send an email to popov2424@aol.com.

Peer Pressure: Part 2 of 2

Here's Part 2. I hope everyone enjoyed this one.

Peer Pressure: Part 1 of 2

Private Lessons

Sissy Tamer's Contest Prize and "Bonus"

I'm continuing to post my "prize" captions for the contest winners and today are the captions I made for Sissy Tamer. Now, even though two of his captions were winners, I was only supposed to do one caption for him. But, I liked his caption about the Tyra Banks Show episode so much that I wanted to do a sequel of it for him in addition to his custom caption.

So first, part two of his winning caption:

And for his actual prize, Sissy Tamer wanted a caption with a teenaged-looking transsexual as Bobbi. he wanted it to be about his father being humiliated because he's in chastity and accepting a future punishment to get unlocked because of how turned on he is by Bobbi. With direction like that the caption wrote itself:

Once again, congratulations to Sissy Tamer. I hope you guys like these as much as he did.

PS: I'll get back to posting my non-custom stuff tomorrow. Jenny, my other contest winner has asked that her prize remain private.

Elena Starz' Contest Prize

This is a caption I made for contest winner Elena Starz, operator of the amazing Elena Starz TG Stories/Captions. Elena's contests are what I based my contest on so it's only fitting that she get a prize. And coincidentally she started a new caption contest today so go check it out if you had fun with mine.

For her prize she gave the direction of a bimbo-type blonde, MILF sissy having trouble explaining to his son why he's giving-in to being a sissy. I decided to use a photo of Summer Brielle because she's my favorite blonde bimbo right now. This is how it turned out:

Nikki Jenkins' Contest Prize

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St Patrick's Day Party

Contest Winners

Well, my first caption contest is over and in my opinion it was a huge success. I hope you all enjoyed reading the great captions as much as I did. The winners have been posted on my new "Contest" tab so check them out and leave a comment congratulating the winners, debating the choices or even leaving feedback on how I can improve the next one. Thanks again to everyone who participated and be sure to check your email if you're a winner so I can get working on the prizes!

-Wes

Who Fucked Trevor's Rabbit?

Just over a full day left to vote in the caption contest. All the great entries are one post down and you can cast your vote on the right.

Enjoy this new caption. My next post will be late Saturday night when I announce the winners.

Caption Contest No. 1: The Voting

Alright, the submission deadline has passed and now the voting can begin for my first ever Caption Contest!

I'm so excited for the turnout. You guys made some fantastic caps and I'm sort of overwhelmed with how many were turned in. I received 33 captions from 13 different captioners - that's just awesome. And they really cover the entire spectrum of my little niche. We have some captions from complete newbies doing a spectacular job with their first ever work done for public viewing, and we also have captions from famous veterans with their own blogs. We have some more subtle, almost sweet, humiliations for our sissies, and then we have some straight-up filthy humiliations that are not for anyone with delicate sensibilities (but if you had those you wouldn't be on this blog, right?) Really awesome stuff all around.

Anyway, with the quality and quantity you all provided, I've decided to step it up and offer another prize. Instead of only two winners, now there will be four! You all will vote for two in the poll to the right and I'll pick my two favorites. But only one prize per person. 

Voting is open until Saturday and then I'll post the winners and contact you via e-mail about your prizes.

Please only vote for THREE (3) captions in the poll (you're on the honor system!)

Finally, I know there are a lot to read, but they really are worth it so be sure to take your time and read each one before voting - they deserve it.

Now vote!

Brittani 1

Brittani 2

Elena Starz 1

Elena Starz 2

Elena Starz 3

Elena Starz 4

Elena Starz 5

Elena Starz 6

HJ 1

HJ 2

HJ 3

HJ4

HJ 5

Nikki Jenkins 1

Angelica 1

Angelica 2

Angelica 3

Vinciini 1

Vinciini 2

Vinciini 3

Vinciini 4

Candy 1

Jenny 1

Jenny 2

Ian 1

Ian 2

Holly 1

Holly 2

Sindy 1

Sissy Tamer 1

Sissy Tamer 2

Sissy Tamer 3

Beatcat 1