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Ian's Custom Caption Prize

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Working Bois is over and it's back to regularly scheduled programming. It's time to let everyone see the custom captions that were won after my last contest. 

I did this one for Ian, who has been in every one of my contests so I was happy to get an opportunity to make one for him. He asked for a story about a boi who refused to go full-blown sissy during high school but ends up working as a sissy maid once he graduates. Enjoy!


I've reposted the poll in the hopes that it works this time. I'll give it 24 hours and if it's still not working we'll move on to plan B.

Slutty Eve's Custom Caption Prize

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Slutty Eve wanted a sequel to the caption she made for one of my previous contests (check it out here). She wanted me to explore what would happen to Trevor next and she suggested it involve a gangbang. And I just happened to have some pictures of the same model.


Plan B

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Okay, so polls seem to be broken on blogger, so that's not an option anymore. But I still want you all to be able to pick the theme of my next caption contest. So I'm going to give you three avenues to "vote." You can email me at popov2424@aol.com with your vote. You can cast your vote anonymously through my "ask Me Anything" box to the right. Or, you can cast a vote in the comments section of this post.

Your options are:

- Sissy nurses
- Gym sissies
- Sissy cheerleaders
- Bikini bois
- Sissies in bondage
- Sissies in tights or yoga pants

Please vote!

Sissy Alice's Custom Caption Prize

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Alice wanted a caption using this photo of Bailey Jay about a sissy and his master going on a honeymoon.


PS: Remember to vote in my makeshift poll for the theme of my next caption contest. Details are one post down (Plan B). So far it's basically still a 6-way tie.

Elena Starz's Custom Caption prize

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Elena wanted a caption that focused on a sissy being forced to go to the salon for a make-over, with most of the focus on the salon experience.
We had just completed "Working Bois" when I made this for her so I wanted to do something cool or unexpected with the layout that I've been using. I used beauty care products as my corner markers but I think it looks cheesy - like I just pasted in clipart - so I made a more simple one as well. I'll post both. Which one do you like better?




AND DON'T FORGET!!!!!!
Scroll down a few posts to "Plan B and be sure to vote for the theme of my next caption contest. It's seriously super close right now with five of the options separated by a vote or two. Make sure your opinion is heard.

Ask Me Anything

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Anonymous asked: Is that supposed to be part of a caption at the beginning that picture of a girl/guy?

Me: I'm not sure what you mean.

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Anonymous asked: Would you rather invent a cure for cancer or a cure for AIDS?

Me: Wow...You know I just make porn and put it on a blog right? Um...I have no idea. I wish I had an intelligent or funny answer but I have nothing. I guess I flip a coin?

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Lolly Pop asked: I LOVED Working Bois. The story was amazing but I especially loved the design and all the cool little stripes in the corner. It looked a lot like what you've been doing on your new captions. Did you do all the designs or did Elena do hers?

Me: The entire series was a total collaboration. Lots of back and forth emails and running ideas past each other on every detail. So she and I both decided on the layout and look we wanted and then I did the actual design but only because I was using photoshop and she was using paint (I think). We just wanted to keep it uniform. I'm glad you liked it.

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Anonymous: Hi.

Me: Hi, anonymous stranger!

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Alexis Deep's Custom Caption Prize

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Alexis wanted a hardcore, total domination/bdsm caption with heavy metal music/Judas Priest as a thematic inspiration and possibly Sasha Grey as the model. What are the odds I would have a photo that would match that? Pretty good, actually...


And remember to vote for the theme of our next caption contest. We've got about 36 hours left in the voting. It still really close. Whatever theme wins is going to win by a vote or two. Details are a few posts down ("Plan B").

Master Crocker's Custom Caption Series Grand Prize

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Master Crocker, my grand prize winner of a full series, asked for a story about a white male working as a bdsm master, who gets caught and sissified into a "pneumatic-titted, humbled, degraded faggot," with an emphasis on the contrast between the before and after.








Lolly Pop, my other caption winner, has asked that her custom caption remain private so I'll be back to posting new original captions tomorrow.

PS: today is the last day to vote for the theme of my next caption contest. There are now four options still tied (and the other two are very close behind) so every vote matters). It's as easy as popping your choice in my "Ask Me Anything" box over to the right of this page. Details are found here.

Meet Suki

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A lot of people have asked for this so here it is - my Asian sissy character. Enjoy!


And the voting is closed for the theme of the next caption contest. The results are:

Winner: Gym sissies - 15 votes
2nd: Cheer Bois - 14 votes
3rd: Yoga Pants and Tights - 12 votes
       Bondage Bois - 12 votes
5th: Sissy Nurses - 8 votes
6th: Bikini Bois - 7 votes

As you can see it was VERY close. I'll have pictures up for the contest soon.

This Sissy is Maid for Dick

Ask Me Anything

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Anonymous asked: I'm a "white" middle-aged. closet tranny. more than anything I want to become a black she male. some people tell me that others have actually done this. do you know if that is for real?

Me: Become a transsexual? Yes, definitely. Become black? I'm not a doctor but...No, not at all.

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Anonymous asked: The first question in your recent AMA is referring to the Kimber James banner at the top of your blog. i believe he was asking if she was part of any actual caption with the same photo. Can the next contest also feature an asian

Me: Thanks for clearing that up. No, I haven't used that picture in any actual captions. But there are plenty of Kimber James captions on my blog. As for an Asian in the next contest, now that I've done my introduction caption for Suki, I'll try to include an Asian model in my contests when I can.

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Anonymous asked: I like your blog but I think your sometimes to mean to the TS girls in your captions. I think it objectifies people who are struggling with their identity. They are always weak and dumb and submissive and treated like dirt. They are just sex objects to you. I think it would be better if sometimes they like being with men. Or they end up being treated like real women. Thank you.

Me: I respect you opinion but I do disagree. I think that my captions objectify everyone. I marginalize black men, white transsexuals and white males. I'm ok with that because this is just porn. It's meant for people to get turned-on by, not to discuss social issues. There are lots of great blogs that actually deal with real life transgendered issues. There are even lots of great erotic caption blogs that I think handle the whole issue very responsibly like feminizationstation.blogspot.com. Nikki does great captions that really capture the struggle for transsexuals to find their identity and come to terms with it - to be treated with respect (while also being very sexy captions). I've never claimed my blog did that. I just make porn and specifically submissive sissy porn.

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Anonymous asked: What is your favorite food?

Me: Haha, I really love the diversity in the questions I get. After a tough one like the last one, I like a nice softball like this. I'd say steak. I like nothing better than grilling up an awesome ribeye.

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Anonymous asked: have you ever considered doing captions of say larger sissies? Such as fat and or chubby ones?

Me: Probably not. It's just not something I'm into.

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Anonymous asked: Wes, would you mind doing an Indian Sissy for Black men.Like a NRI in US gets crazy for black men? 

Me: I'm not opposed to it. I don't really have any pictures of Indian models.

The Amazing Comic-Con Cutie

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I'm really proud of this one. I hope you all like it as much as I do. Nikki Jenkins did a caption of this pic over on her blog and was kind enough to send me the original photo. I'm a hug comic book fan and this model is so damn sexy I knew I had to make my own caption of it and I wanted the layout to be worthy of the photo. As for the story, it's a sequel to this caption. Enjoy!


Balls in the Pocket

The Bat Boi

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I was thinking about starting the next caption contest on Friday or Saturday, but with the blogger polls still busted I'm not sure how to work that. If you have any ideas, you can leave them in the comments section or in my Ask Me Anything box.

In the meantime if your yearning for some contest action, go take a look at the entries in Elena Starz's current "contest." She's getting around the current blogger bug by just avoiding voting altogether. But, you should take a look at the great entries, including 5 new captions from me.

And finally, here's today's caption. This is another one I'm really happy with.


Differing Opinions

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Sorry I didn't have a post up yesterday. Internet issues have kept me off line for almost 48 hours - Bleh. Hopefully it's all fixed. So to make up for it here's a two-part caption for you. Enjoy.




Personal Ass-isstant

Ask Me Anything

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Elena Starz asked: What is your favorite non-interracial sissy theme for TG caps and have you considered writing any caps in this style (or any other non-sissy theme)?

Me: My favorite non-interracial sissy theme is cuckolding. I like it especially because (outside of my blog) I don't think I've ever seen captions about a sissy being used by an alpha male to reluctantly cuckold a beta male. A close second would be sissy bimbos. My favorite non-sissy is probably also cuckolding. I've written some non-sissy cuckold captions in the past. They were lost on my old computer but I think I saw them on imagefap last year or so - they weren't any good. As for bimbo captions - I've done a whole bunch and they can all be found EXCLUSIVELY on your blog, Elena. Haha, you gotta love that cross-promotion.

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Anonymous asked: You enjoy grilling your own ribeye but do you have any steakhouse recommendations?

Me: You bet I do. I could go on forever but unless you live in Las Vegas it won't be very helpful for you. In Vegas my top recommendation is Carnevino. It's a Mario Batali restaurant and they're famous for dry-aging their steaks. It's amazing. Next would probably be Michael Mina's Stripsteak. Third would be The Circus Circus Steakhouse (The casino is a shithole but the restaurant is classic, Rat Pack era steakhouse with great food.)

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Anonymous asked: Will there be more captions of girls getting off on their boyfriends being used anytime soon?

Me: Yes, but i'm not promising how soon. I've mentioned I have a lot of captions that are already finished and waiting to be posted. In that pool of finished caps there are definitely some more femdom ones.

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Anonymous asked: Can I really ask you anything?

Me: Absolutely. If it's super personal I'll try to answer as best as I can without being too specific. The only things I won't post on the blog are duplicate questions and just outright racist or homophobic rants - which I get about once a week.

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Anonymous asked: Nothing to ask, i just want to say i love your blog (L). I'm a big fan from Argentina :)

Me: Wow, that's cool. Thanks.

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Anonymous asked: Sissy cheerleaders should be your Plan B

Me: You were a few days late. Gym sissies was the winner (and the contest is coming soon-ish)

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Anonymous asked: Would you rather eat poison ivy or a handful of bumblebees?

Me: Hahaha, you guys are so weird. I don't have enough information to answer this question. Can I cook the poison ivy? Are the bumblebees alive? How much poison ivy would be equal to a handful of bees? There are a lot of variables here.

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Anonymous asked: what's the best way to find a white sissy to fuck?

Me: I guess it depends on what city you're in. Every major city should have a T-friendly bar. But probably the best way is online.

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Anonymous asked: What's your stance on gun control and do you think the reemergence of Russia (in that it's pushing it's border to resemble something of what it looked like in between the two world wars) should have any bearing on the issue?

Me: This is still a porn blog, right? Is google linking my blog to a CNN chat room? Anyway, my stance is that gun laws should be much stricter in the US and I think rifles for hunting and handguns for home defense are all that should be allowed to average citizens. The military and police are a different issue. As for Russia affecting my stance, not at all. While Russia should be a cause for concern in US foreign policy, the odds of a land invasion in US by Russians is about zero percent.

Only Teasing

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Hey, the new contest might go up tomorrow (maybe). I have some friends in town and we've been partying pretty hard so I've put no work into finding any photos yet. We'll see what happens. Enjoy this caption in the meantime.


Ring Boi

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Here's another one I'm really happy with. I think the story is sexy - and probably something I'll revisit in the future - and I love the way the layout turned out. It's a little different than my normal layout buts still in the same vein. Let me know what you think.


I'll post the caption contest tomorrow so start thinking of a sticky situations for our sissies to get in at the gym.

Caught After School

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I lied. The contest will be up tomorrow*. Just read this caption for now.




*Maybe. I'm not making any promises.
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