Ian's Custom Caption Prize

Today's custom caption is for Ian who wanted one where a sissy gets his penis-enlargement cream switched out for itching powder by black men and then gets caught "icing" himself by a girl. Very original and a lot of fun to make. I hope you all like it as I enjoyed making it.

Lolly Pop's Custom Caption Prize

Up today is Lolly Pop's custom caption. Lolly wanted me to caption this picture of Whitney Cummings and make it about Petra Lix on the red carpet of the AVN Awards show.

Ask Me Anything

Anonymous asked: You got. the names wrong in your Last caption its bloswell not valentine

Me: Thanks but I've been away so long I don't know which caption you're referring to. If you remember which one it was let me know and I can edit it.

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Anonymous asked: Would you consider expanding to tumblr?

Me: Someone asked me this before. I'll ask you the same thing I asked then: What do you think tumblr would offer me as a blogger or you as a reader that I don't offer now? I'm curious because I don't know much about tumblr. If there's something they do better I would be open to the idea.


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Anonymous asked: There should be a focus on Holly with Bobbi and Chrissy. Every sissy needs their mom right? does Britney even have parents?

Me: No, Britney was made from a test tube in a lab that was attempting to make the perfect sissy...j/k.

I probably should do a story that involves Holly. I don't think I've mentioned her once in any of my captions, only in custom caps I've done and haven't posted. I guess I just haven't really been inspired by an idea that involves her yet. As for Britney, she has parents but I've been trying to think of what would make her parents different than Nick and Holly before I write a story about them.


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Anonymous asked: Hi Wes - thank you for posting my question! I am such a fan of this blog - what would you say to us exchanging links? I've already posted a link to your blog on mine - would you return the favor? Thanks! http://sexyyoungtranny.blogspot.co.uk

Me: Of course, babe. Your link is now posted.


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Anonymous asked: Tattoos tend to mean very specific things. An example in real life and sometimes used on your blog is a spade tattoo or a queen of spades tattoo that shows that the woman who has the tattoo is open to interracial relations or is exclusive to interracial relations respectively. If you were to tattoo a sissy with more than one tattoo design what tattoo would you give them and what would those tattoos mean.

Me: I like that spade tattoo because it's a simple little icon with so much meaning. I especially like to use it on this blog because of the reluctant nature of my sissy characters and the fact that being forced to have a visible tattoo like that with so much meaning behind it would be very humiliating. If I was better at photoshop I'd probably use forced tattoos more on this site. As for coming up with my own design, I've never really thought about it. Off the top of my head I'm imagining a small black heart with pink lips in the center to signify a sissy had been properly trained in oral service. That's a good question I'll have to think about some more.


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Anonymous asked: Do you remember that time five years ago when you were extremely upset? Does it really matter now?

Me: Upset on the blog? It didn't exist five years ago. Upset in my personal life? I remember and it still matters.

Candy's Custom Caption Prize

Hey everybody. So I've been kind of quiet on the web site for awhile, it's because I've been really sick for over a week. I'm getting better now and should be responding to the emails I've received in the interim. I'll put up an AMA tomorrow probably to answer all the AMA questions I've gotten in that time. I hope you all have liked the posts I've put up recently, I tried to get one up whenever I was conscious.

Today will start the posting of the custom captions I made for the winners of the Cosplay Contest. We'll start with the one I did for Candy. Candy gave me a photo and asked for a caught with consequences caption of someone dressing for a party.

PS: Missy Sissy, if you read this I still haven't heard back from you on what you'd like for your custom caption so be sure to contact me to claim your prize.

Taking Notice

The Rules

When No One Is Looking

Drinks After Work

Canceled Plans

For Old Time's Sake

Bathtime Buddies

Ask Me Anything

Anonymous asked: I'd like to see another cap like Shooting Sissies in a Barrel. One of my all time favs

Me: I liked making that one. It didn't really get much of a response from readers. I also did a poll once asking what people wanted to see more of on the site and that type of caption got the least votes. But, it's been a long time. Maybe it's time to give it another shot.

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Anonymous asked: Hi Wes - love your blog! Mine is: http://sexyyoungtranny.blogspot.co.uk

Me: Thanks, babe. I've visited your site a few times before and really like what you've done with it. We seem to have the same taste in what makes for a beautiful T-Girl and your personal pics have definitely gotten my imagination going a few times.


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Anonymous asked: Would you be willing to make a non-incest (for lack of a better term) tag? I love your captions, but some of them involving fathers and sons step a bit outside my comfort zone. If not, that's okay too, but I'd appreciate it. Thanks!

Me: I definitely understand your point, but I'm probably not going to go back and re-tag my roughly 400 captions on this blog. But, there already are two tags that can help steer you clear of those types of captions. "Groped by Dad" is what I use whenever a dad is being inappropriate with hiss sissy son - not specifically just "groping". And the "Sindi Sweetcheeks" tag will steer you away from any of Sindi's captions where the son is the one who wants to do the groping. That's not 100% full-proof - I've forgotten a tag here and there - but it should give you a pretty good guide to help you avoid the captions that aren't your cup of tea.


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Anonymous asked: The burning, emasculating, finely detailed and obviously painful humiliation that Cara pours on her fairy pussyboi "boyfriend" is electrifyingly sensual. Mre, more much more PLEEEEAAASSSSEEEE! Rape the panty fairy w/his head crammed in a toilet!

Me: More like this is coming for sure. I'm glad you like what I've been doing so far.


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Anonymous asked: could you make captions for races other than just black and white

Me: I have an Asian sissy character. I use lots of Latina models in my captions. If you mean will I get away from interracial captions? I've answered that one before but the short answer is "probably not." That's kind of the niche that I've carved out for this blog. If you'd like to see my non-interracial captions check out my contest entries on Elena Starz's blog..


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Anonymous asked: How about one were a man's 4-5 sons get feminized, one after another by different people, before being forced himself!

Me: How about one where a man's two sons get feminized, one after the other by different people, before he is forced as well? You can find that story right here.

(Sorry, I couldn't resist).


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Anonymous asked: Would you feminize Steve Buscemi?

Me: I can't imagine a scenario where I would ever want to see him feminized. It'sprobably something you can never unsee.

Proof

Just What He Needed

Special Guest

Tough Market

Ask Me Anything

Anonymous asked: bennyboi was the tru winner of the cap contest fuk u

Me: No. He lost the voting. Don't be rude to the people who won.

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Anonymous asked: I'm a sissy, would you chat with me online?

Me: Sure. I'm on Yahoo Messenger as Wes Mantooth702.

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Anonymous asked: would u forcibly feminize vince vaughn and make him ur lil sissy bitch?

Me: No, that seems like it would be way too much work. I'd feminize Justin Beiber and make him my bitch.

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Anonymous asked: Can a match box?

Me: No.

Talent Scout

Being Taken For a Ride

Learning a Trade

Winners for the Cosplay Caption Contest have been posted on the winners page and will be notified about claiming their prize late tonight or tomorrow. 

Ask Me Anything

Anonymous asked: I don't have a question but I just wanted to say congratulations on the new job and I hope it goes well for you. I'm such a huge fan of your site. Thanks for all your sexy captions.

Me: Thank you very much. The job is going very well but it's a job where i don't have set hours or set days even (for now). It makes getting up a daily post pretty difficult but I'm trying my best and when I miss I'm trying to do something special the next day.

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Anonymous asked: Hi

Me: My parents told me not to talk to strangers. But technically I just did....so, hello!

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Anonymous asked: "PERFORMING FOR AND AUDIENCE" nice grammar u dingus how about u go back 2 school

Me: Thanks for catching my typo. I've corrected it so that now you can enjoy the caption without getting so angry.
Also, since we're correcting grammar:
"Perfroming for and Audience"? Nice grammar, you dingus. How about you go back to school?

You're welcome.

Cosplay Caption Contest Winners!!!

Hey everybody. Caption contest winners are now posted on the Winners Page. My thanks to everyone who participated, this one was a lot of fun for me. I enjoyed reading each and every one of them. A quick rundown of the winners:

Grand Prize: Megan Gwynn 1
Megan crushed it. Seriously. This caption was far and away my favorite. I even had reservations about choosing the same person twice for the grand prize but Megan's take on a "comic book recap page" about a sissy superhero in peril was just too damn good. Such a great concept.

People's Choice 1A: Lolly Pop 3
Lolly turned in three stellar captions this contest but #3 was the one that got everyone's attention. A really cool idea of having a sissy be accosted by a black man and spanked into begging for it right in front of the girl he was flirting with earlier....so hot.

People's Choice 1B: Shilpa Sleazy
Shilpa is a long-time fan of the blog and caption contest participant. Not only did Shilpa win this time around but actually finished tied for first place in the voting with Lolly Pop. Shilpa's series uses all three sissies in the Luvcoxxx family to tell an awesome story with a little nod to my caption layout in the first two.

People's Choice 3: Candy 1
Candy wrote a novel - jk. Candy had an awesome story involving a black biker gang kidnapping and enslaving a cosplaying sissy. How could that not do well on a site like mine? Plus the inventive layout using both Catwoman pictures really added to the story.

Wes's Choice* 1: Jenny Jenny
Jenny did a caption with a sexy little sissy theater story, but the main thing i liked about it was the cool layout and design. Simple but effective and, because of the story, reminded me almost of a flyer someone might get handed. to come watch Billie's "performance.".

Wes's Choice 2: Missy Sissy 2
Missy nailed it with the "less is more" approach. Simple, to the point captions with a great impact. Missy's Scooby-Doo cosplay themed caption caught my eye immediately. A perfect story for the expression the model has in the photo and a hilarious and sexy ending.

Wes's Choice 3: Ian 1
It's no secret I like my captions dirty and humiliating for my sissies and Ian's entry definitely did it for me with a picture that seemed to be begging someone to do this type of story with it.


*Excluding captions that won in the voting or were by someone who did win in the voting

Leaving a Message

24 hours left to vote. It's a pretty close race so be sure to read their great captions and help your favorites get a prize.

Rest and Relaxation

This summary is not available. Please click here to view the post.

Exclusive Invitation

Performing for an Audience

Still plenty of time to read through all the great entries in the Cosplay Caption Contest. You can see the entries here before voting in the poll to the right.

I've been super busy with a new job so I didn't get a chance to post anything yesterday. So, hopefully this multi-part caption makes up for it. Enjoy.

Edit: I corrected the typo in the title.

Ask Me Anything

Megan Gwynn asked: I love this contest (and all your contests) and I'm so glad people decided to turn some in at the last minute. But, in looking at the images, I can't help but wonder what awesome and dirty things you would have done with these pictures if you had captioned them. Have you ever thought about going back and captioning the images from your contests or do you consider them used already?

Me: Actually I have thought about that quite a bit but I've never made a decision about it. I'm really on the fence. On the one hand, I have thought of some good ideas for some of those pictures (a lot of them inspired by the great work all of you have done in the contests) on the other hand I don't want to bore readers by giving them images they've already seen captioned by multiple people. Another thought I've had is captioning the images that no one has chosen. What do all of you think? Should I toss the images that I've used in the contests and stick to all-new stuff or would you like to see me put my take on some of them?

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Anonymous asked: more sissys forced to wear thongs

Me: Not a question....but ok.

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Anonymous asked: would u fuck vince vaughn in a dress with makeup?

Me: Would he have his perpetual 5-o'clock shadow?

Lost in Sissy Thoughts

You should have noticed the poll to the right for the current caption contest by now. Read all the captions that your fellow readers created right here. Then go vote for your favorite four.

Lunch Break Sexting

All the entries for the Cosplay Caption Contest were posted last night - and hot damn they are good. Be sure to check them all out right here. Then you can vote for your four favorites in the poll on the right.

Caption Contest 5: The Voting!

Well, guilting you all into turning in more captions definitely worked. I call it "The Grandma Technique." Those extra couple of days I added more than doubled the amount of entries. They're all amazing. So many creative approaches to cosplay images. I'm really blown away.

As always be sure to read ALL the captions. Because I have so many submissions I'd like for you to vote for your favorite four (4) captions in the poll. I'll also pick my favorites and award the prizes when the poll closes.

READ!!!

Megan Gwynn 1

Megan Gwynn 2

Cici

Lolly Pop 1 

Lolly Pop 2 

Lolly Pop 3 

Shilpa Sleazy Series

Sissy Tamer 1 

Sissy Tamer 2

Missy Sissy 1 

Missy Sissy 2 

Missy Sissy 3

Alice Sissy 1

Alice Sissy 2

Bennyboi

Candy 1

Candy Series

Dandy Cane

Elena Starz 1 

Elena Starz 2 

Elena Starz 3 

Emily Daniel 

Ian 1

Ian 2

Jenny Jenny

Jessica Rivera

Logan

Panty Princess 1

Panty Princess 2

Panty Princess 3 

Panty Princess 4

Panty Princess 5 

Panty Princess 6

Panty Princess 7

Panty Princess 8 

Sissy Rica Dee 1 

Sissy Rica Dee 2 

Sissy Rica Dee 3 

Slutty Eve 1

Slutty Eve 2