Sunday, April 19, 2015


Caption contest. Prison sissies. Wednesday deadline. Details here.

New caption.

Saturday, April 18, 2015

Welcome to Paradise

Still waiting on more participants for the caption contest. Entry window is now open until Wednesday. All details can be found here.

Thursday, April 16, 2015

Sin City Sissies

Well, at least 767 of you read my post yesterday and completely ignored my instructions. I take that to mean that you're all furiously toiling away on your captions for the prison sissy caption contest and you just needed a bit more time to finish. In that case, I have heard your implied cries and I grant you all until next Wednesday afternoon (April 22) to get your captions to me. You're welcome.

In all seriousness, I only have a handful of entries in this contest so I was going to give everybody another day or two, but I'll be out of town this weekend and unable to do anything but post a few captions I've prepared ahead of time - so why not just extend it a full week? But I am curious why the sudden drop off from the most entries ever to the fewest. Is prison sissies not an appealing topic? It won second place in the last topic poll but maybe I could do a poll before each contest just to make certain. Is it caption contest overload? I try to space them apart by a month and a half but maybe it could be longer. Are we not friends anymore? I just told you I liked your shirt. caption:

Wednesday, April 15, 2015

Getting Waxed

Hey, you - yes YOU, I can see you - stop looking at porn on the internet and make a caption for my current "Prison Sissy" themed caption contest. All the details you need are right here. When you've emailed it to me, then you can come back here and read this new Nikki caption. Also, clean your place up. Also, I like that shirt.

Tuesday, April 14, 2015

Roadside Assistance

Still very little action on the caption contest. I hope you're all just procrastinators. If you need to see all the fun details, check out this post.

Monday, April 13, 2015

Prude Shaming

The newest caption contest is up and running and so far we're off to a really slow start. But, I know a lot of you like to take your time and make your submissions perfect, so no worries yet. You can see all the details right here.

Friday, April 10, 2015

Caption Contest 9: Prison Sissies

Last contest was a huge success in terms of turnout and quality. Hopefully, this contest will match or surpass even that. For the ninth caption contest, the theme - as chosen by you the readers - is prison sissies.

Here's the fine print:

The Rules
1. Choose one of the images below to caption.
2. You can submit as many captionas you like but you can only submit one caption per photo.
3. Captions, like the captions on this blog, should be about forced feminization and interracial in nature (but I'm not strict at all, just have fun).
4. Submit your captions to For anyone who doesn't know how to make a caption, you can just email me the text and the photo you want and I'll make it for you.
5. Submissions will be taken until late afternoon on Thursday, April 16. All captions will be posted for voting that night.

The Prize
Four to six winners will be selected based on the number of entries. Two or three will be chosen by me and two or three will be chosen by readers in a poll. If there is any overlap between the two, I'll select a runner-up.
The prize will be a caption by me. You can send me a photo, a theme or both and I'll make you a custom caption hitting any fetishes you'd like to see represented.

The Grand Prize
Since it worked well the last few times, The Grand Prize will be a custom caption series! That's right, the top winner will get a set of four or more captions telling a complete story. (The actual amount will be decided by me based on how much story I can get out of the winner's idea for their custom caption.) 

Character Guide
You DON'T have to use my character names, but for the people who like to:

Robert/Bobbi Luvcoxxx - Reluctantly feminized highschool-ish age main character

Christopher/Chrissy Luvcoxxx - Bobbi's younger feminized brother
Nick/Nikki Luvcoxxx - Bobbi and Chrissy's humiliated cuckold father.
Sidney/Sindi Sweetcheeks - MILF sissy with an unfeminized, horny teen son, Daniel
William/Billie Blowswell - Very reluctant teen sissy who doesn't realize/admit how much he's been feminized
Brian/Britney Valentine - Bobbi's best friend who loves being a teen sissy
Cameron/Candy Luvdarc - Force-feminized MILF sissy teacher at Bobbi's school
Peter/Petra Lix - A sissy pornstars who claims to be straight when the camera isn't on
Jack/Jackie Jizzbucket - Empowered punk-rock sissy who teases Trevor
Erik/Erika Diketer - Sissy nurse at the local hospital
Sukutashi/Suki Fukumore - Asian teen sissy, with a girlfriend pushing him to be more feminine
Trevor Limpley - White cuckold who can't help falling in love with all the sissies
Cara Vixen - Billie's female femdom girlfriend who used to date Bobbi
Angelica Cockteese - Suki's "girlfriend" who loves feminizing white bois
Holly Luvcoxxx - Bobbi and Chrissy's mother and ex-wife of Nick
Belinda Spanksboiz - Femdom Vice-Principal at the local highschool
D'Angelo Blackwood - Bobbi and Chrissy's stepdad. Holly's new black husband.
Malik - Black teen stud who torments Nikki
Mr. Blackstone - Bobbi and Nick's black boss. (Possibly also Trevor's boss. I kind of use the same names over and over)
Mr. Blackwell - Bobbi and Chrissy's black principal
Coach Blackburn - Coach of every sport, apparently
Cary/Carrie Cumdump - Sissy superhero known as Power Boi

The Images

Monday, April 6, 2015

Personal Tutor - 500th (ish) Caption!

Just like the last milestone, this one is sort of subjective. It's not counting custom captions of series I've done. I just wanted to celebrate something I felt was a big deal for me by doing another series for you guys. I hope you enjoy it and continue to visit the site and interact. Thanks to everyone who visits regularly and to everyone who leaves comments.