Gotta say, despite the whole tumblr debacle, this was a pretty good month for captions. This one just edged out the others. The stakes are too high, the girls too humiliating, and the sissy's panties too perfect!
Thursday, January 31, 2019
Caption of the Month - XIX
Gotta say, despite the whole tumblr debacle, this was a pretty good month for captions. This one just edged out the others. The stakes are too high, the girls too humiliating, and the sissy's panties too perfect!
Wednesday, January 30, 2019
Monday, January 28, 2019
Friday, January 25, 2019
Cap of the Week - LXXXII
I fucking love this caption! Her stunned disbelief in his sissydom...almost as if she couldn't quite believe what she was seeing up until this point...when the cum started to pour...
Thursday, January 24, 2019
The Game - 1
I'm going to have to go with J. Law, right here. Especially with that knowing smirk she's wearing...
Aubrey Plaza. She's got that dour no-nonsense vibe that can really put me in my place when I need to be controlled (which would be always). Plus, I feel like she'd really enjoy feminizing me, and turning me into the Lipstick Lesbian Sissy Girlfriend she wants.
Wednesday, January 23, 2019
Monday, January 21, 2019
Friday, January 18, 2019
Cap of the Week - LXXXI
I love this story. So much humiliation...such a sissy slut...so much riding on the line!
Thursday, January 17, 2019
Retro Caption - 29
Here's an old favorite that I've had for so long I honestly don't remember where it came from. I still love it to this day. It's just a classic chastity and sissification story.
Wednesday, January 16, 2019
Monday, January 14, 2019
Friday, January 11, 2019
Thursday, January 10, 2019
The Interview... - 1
So, now that I'm finished with the Sissy Biography, I'm going to try something new. Supposedly this questionnaire has 500 questions, and I'm going to be answering them over the course of 12 months. That's going to be 42 questions a month.
...
Sounds fun! Let's get started.
About Me:
-What is the size of your penis/breasts?
My sissy-cocklette is around 7" and change.
-Does your penis have a curve?
No.
-Are you circumsized?
Yes.
-Have you ever had an STD?
No.
-Have you ever been pregnant/gotten someone pregnant?
Yes, I've gotten someone pregnant. They miscarried, though.
-What type of underwear are you wearing?
Pink Satin Hi-cut Briefs.
-What is your favorite type of underwear?
String Bikini Panties, with black stockings and garter-belt.
-When was your last erection/arousal?
Yesterday.
-Have you ever had an erection which someone noticed?
Yes.
-Has anyone seen your private parts other than yourself?
Yes.
-Explain your ultimate fantasy.
Highlights include:
Me in a black maid-uniform, while in a pink chastity cage, forced to suck and be fucked by a sexy lady-friend's boyfriend, while my hottest co-workers watch, and my sexy lady-friend records the whole thing. She then forces me to anally masturbate with a vibrator (still caged) to the video she just made of me, while the co-workers taunt me and start making out with each other.
-What are your turn-ons?
Chastity, forced femme, panties, submission, cum-eating, humiliation, garter-belts, high heels
-What are your turn-offs?
Basically, anything to do with bodily waste.
-What is the strangest thing you’ve ever been turned on by?
Sometimes, just the right inflection in a woman's voice in an otherwise innocuous sentence is enough to get me going.
-Have you sent a sexual ask to someone on tumblr (Anonymously or Not)?
No.
-Have you sent a nude photo or video to someone?
No.
-Did it include sexual acts?
N/A
-Have you ever posted a picture of image of you in the nude on a website?
I sent in a nude image of myself to an online mistress. Does that count?
-Did it include sexual acts?
Yes, I was in lingerie and fucking myself with a 6" blue dildo.
-Have you ever anonymously sent/posted a picture or video of yourself in the nude?
No.
-Did it include sexual acts?
No.
-If someone you knew asked for a nude image, would you do it? What about a tumblr follower?
Yes. Maybe.
-What was your latest sex dream about?
I sucked myself off to completion in front of my wife. I may have had a wet dream.
-Have you ever had a sexual fantasy about someone?
Umm...yeah, who hasn't?
-Was it about anyone other than your lover?
Umm...yeah, who hasn't?
-What was the last fantasy about?
Which one? There was the above fantasy of servicing a friend's boyfriend while acquaintances watched thing.
-Have you ever fantasized about someone older/younger than you? How much older/younger?
Well, when I was a teenager, I fantasize about teenagers. The oldest person I've probably fantasized about was in her 60's. An older college professor. I find intelligence to be profoundly sexy.
-Have you ever told any of these people that you fantasize about them?
No.
-Do you have a favorite person or few people to fantasize about?
I still fantasize about Paige from time to time.
How often do you fantasize about other people?
I'd say 1-3 times a week.
Have you ever showered with someone?
Yes. Two exes and Paige.
Have you ever confessed you were aroused by someone?
I don't think so.
Are you open about your sex-life and sexuality?
Mostly. I leave to sissy stuff in the closet. All of the vanilla-ish stuff is pretty open.
Do you orgasm easily?
It's about half and half.
Have you ever played “7 minutes in heaven”? Explain the experience.
No.
Have you ever played “spin the bottle”? Explain the experience.
No.
Have you ever played “Truth or dare”? Explain the experience.
Not over the age of 10.
Have you ever played strip poker/strip beer pong/etc?
No.
Do you shave your pubic hair?
No.
Have you ever had your pubic hair shaved?
Yes. It was part of an online domination program.
Do you prefer clean shaven or unkept?
On myself? Unkept. It's easier.
What is your favorite type of underwear for the opposite sex?
String bikini panties and a black stockings and garter-belt combo.
Do you own any lingerie?
Yes.
How much lingerie do you own?
About 40 pairs of panties, 7 bras, two garterbelts, 6 pairs of stockings, a corset, and a couple of negligees.
Whats your favorite lingerie outfit?
Pink panties, pink bra, black stocking and garter-belt.
Do you like the way your genitals look?
Yes.
Are you comfortable naked?
Yes.
...
Sounds fun! Let's get started.
About Me:
-What is the size of your penis/breasts?
My sissy-cocklette is around 7" and change.
-Does your penis have a curve?
No.
-Are you circumsized?
Yes.
-Have you ever had an STD?
No.
-Have you ever been pregnant/gotten someone pregnant?
Yes, I've gotten someone pregnant. They miscarried, though.
-What type of underwear are you wearing?
Pink Satin Hi-cut Briefs.
-What is your favorite type of underwear?
String Bikini Panties, with black stockings and garter-belt.
-When was your last erection/arousal?
Yesterday.
-Have you ever had an erection which someone noticed?
Yes.
-Has anyone seen your private parts other than yourself?
Yes.
-Explain your ultimate fantasy.
Highlights include:
Me in a black maid-uniform, while in a pink chastity cage, forced to suck and be fucked by a sexy lady-friend's boyfriend, while my hottest co-workers watch, and my sexy lady-friend records the whole thing. She then forces me to anally masturbate with a vibrator (still caged) to the video she just made of me, while the co-workers taunt me and start making out with each other.
-What are your turn-ons?
Chastity, forced femme, panties, submission, cum-eating, humiliation, garter-belts, high heels
-What are your turn-offs?
Basically, anything to do with bodily waste.
-What is the strangest thing you’ve ever been turned on by?
Sometimes, just the right inflection in a woman's voice in an otherwise innocuous sentence is enough to get me going.
-Have you sent a sexual ask to someone on tumblr (Anonymously or Not)?
No.
-Have you sent a nude photo or video to someone?
No.
-Did it include sexual acts?
N/A
-Have you ever posted a picture of image of you in the nude on a website?
I sent in a nude image of myself to an online mistress. Does that count?
-Did it include sexual acts?
Yes, I was in lingerie and fucking myself with a 6" blue dildo.
-Have you ever anonymously sent/posted a picture or video of yourself in the nude?
No.
-Did it include sexual acts?
No.
-If someone you knew asked for a nude image, would you do it? What about a tumblr follower?
Yes. Maybe.
-What was your latest sex dream about?
I sucked myself off to completion in front of my wife. I may have had a wet dream.
-Have you ever had a sexual fantasy about someone?
Umm...yeah, who hasn't?
-Was it about anyone other than your lover?
Umm...yeah, who hasn't?
-What was the last fantasy about?
Which one? There was the above fantasy of servicing a friend's boyfriend while acquaintances watched thing.
-Have you ever fantasized about someone older/younger than you? How much older/younger?
Well, when I was a teenager, I fantasize about teenagers. The oldest person I've probably fantasized about was in her 60's. An older college professor. I find intelligence to be profoundly sexy.
-Have you ever told any of these people that you fantasize about them?
No.
-Do you have a favorite person or few people to fantasize about?
I still fantasize about Paige from time to time.
How often do you fantasize about other people?
I'd say 1-3 times a week.
Have you ever showered with someone?
Yes. Two exes and Paige.
Have you ever confessed you were aroused by someone?
I don't think so.
Are you open about your sex-life and sexuality?
Mostly. I leave to sissy stuff in the closet. All of the vanilla-ish stuff is pretty open.
Do you orgasm easily?
It's about half and half.
Have you ever played “7 minutes in heaven”? Explain the experience.
No.
Have you ever played “spin the bottle”? Explain the experience.
No.
Have you ever played “Truth or dare”? Explain the experience.
Not over the age of 10.
Have you ever played strip poker/strip beer pong/etc?
No.
Do you shave your pubic hair?
No.
Have you ever had your pubic hair shaved?
Yes. It was part of an online domination program.
Do you prefer clean shaven or unkept?
On myself? Unkept. It's easier.
What is your favorite type of underwear for the opposite sex?
String bikini panties and a black stockings and garter-belt combo.
Do you own any lingerie?
Yes.
How much lingerie do you own?
About 40 pairs of panties, 7 bras, two garterbelts, 6 pairs of stockings, a corset, and a couple of negligees.
Whats your favorite lingerie outfit?
Pink panties, pink bra, black stocking and garter-belt.
Do you like the way your genitals look?
Yes.
Are you comfortable naked?
Yes.
Wednesday, January 9, 2019
Monday, January 7, 2019
Friday, January 4, 2019
Cap of the Week - LXXIX
Starting the New Year off right, with an important message to sissies everywhere!
Thursday, January 3, 2019
New Year, New...Something...
While Girl A is more my preferred body-type, I've got to say that submitting to Nasty, Kinky, Rich Older Men is goddamn arousing as hell.
Wednesday, January 2, 2019
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