Caption of the Month - XX

Re-Blog Wednesday - 89

Difficult Choices...

I think I would probably go for the one on the far right.  After all, it's in the name of the blog.

Cap of the Week - LXXXVI

I love this one!  She's letting the sissy know that she's not worthy of grabbing her sissy stick.  NO!  She has to masturbate like a gurl!  Consequently, this is how I like to masturbate, when I'm en femme!  Excellent work Chaste Pantyboy!

The Game - 2

Jennifer Connelly.  She has a quiet intensity about her that I would be powerless against.

Olivia Wilde would peg me.  I feel like she would be up for anything, so she would fuck me until I begged for mercy...and keep fucking until she had had enough.

Lauren Cohen would milk me as Olivia fucked me, barely touching my cock, making sure I receive as little pleasure as possible, as I oozed out all the cum she could want.

Re-Blog Wednesday - 88

My Life as a Sissy Maid XXXI

Cap of the Week - LXXXV

Happy V-Day!

Re-Blog Wednesday - 87

Sissy Games

I don't know why, but I've personally always loved these things.  I guess I'd just love to live this life  for a year.  So, here's what I would do in this situation (I rolled an 80 for starting points)

First, I would get the Girly Room (50, down to 30).  Not for the color, or the bed, but because I refuse to have a second rate bed!  Also, I'm completely unwilling to have a second rate shower, so that means I'm getting the Luxury Bathroom (20, down to 10 already!). 

I don't look forward to a diet of bread and water, and I don't want to go too far into the re-earning credits, so I'd get the cook for hire (10 down to zero).  I figure I can live with the "One small sexual favor" for decent meals on the cheap.

I guess my first punishment would be doing the 3-hour strip shows (+10 credits, up to 10).  That way I can keep in shape, and know my place as a sex object.  Of course, I'm going to squander this immediately on the "Audience Favorites" clothing option (8 down to 2).  I imagine I'll get to look constantly cheap, and slutty on the cheap!

Of course, I would want the Creative Kit for Entertainment (15, which means I need 13).  I guess, for this, I could submit myself to Bad Sissy's daily spankings, if I displease my audience (up to 7), and wear a Corset 24/7 (14, buying the kit, and taking me back down to 1).

I would definitely want that Toy Chest.  I mean, I imagine I'll have plenty of sexual frustration to let out (meaning I need 9).  So, I guess I could submit myself to the daily Glory Hole (5 bringing me up to 6), and I might as well, swallow their cum in case I need to buy something later (2 bringing me up to 8).  I guess I could also go for a Daily Milking (plus 5 bringing me up to 13, buying my Toy Chest and Taking me down to 3).

Now, I'd want that Cosmetics Cupboard to complete my daily sissy look (20 meaning I need 17), but I'm running out of  the cheap stuff I'd want and/or be willing to do.  Well, I would want the Futa Dominatrix anyways, she just seems right up my alley (adding 15 giving me 18), and I would guess I'd be willing to drink from the Milk Saucer.  I mean, I'm already drinking this much cum, what's a bit more (giving me another 15 for a total of 33, buy my Cosmetics and knocking me down to 13).

Of course, after all this fucking and sucking and cum drinking, I'm sure there would be days where I would just want to veg out and not move, so I'd want the Entertainment System (30 credits meaning I need 17 credits).  There's a couple of moves I could make to make this relatively painless, but what's the point?  Fuck it!  I'm going to go for the Interdimensional Tentacles that appear out of nowhere, that'd I'd have to avoid in order to keep from getting tentacle-raped.  It'd make for a suspenseful show, that would be immensely pleasureable to watch!  (This adds 20 bringing me up to 37, knocking me back down to 7).

I think that's about all I'd want, to be honest.

So, basically, I would wake up, get spanked, get milked, suck-off a cock from the gloryhole, eat breakfast (suck off the chef), get dressed and do my striptease, take a shower, drink my cum-milk saucer, eat lunch (suck off the chef), then have free time until 8 pm (when my Futa Mistress arrives) and submit to her until it's time to go to sleep and start it all over again!

Unless the rape-tentacles appear, at which point I'll be in the corner crying until they go away!

Cap of the Week - LXXXIV

I've always loved this theme, of high-stakes, long distance domination.  She's got to be ready at a moment's notice, or else her wife is going to make sure there are consequences!

The Interview... - 2

About My Masturbation:

Do you masturbate?
Yes.

How old were you when you first masturbated?
12

How often do you masturbate?
Once or twice a week, though it's mostly once.  My work schedule's weird, and I spend a lot of time with the wife.

When is the last time you masturbated?
Last Monday.

Do you masturbate to any stimulus?
I've always believed that I'd rather be over prepared than under.  I've got pictures, captions, texts, games, videos, hypno's...there's not a lot of stimulus I don't use at some time or another.

What do you think about masturbating?
It's a natural phenomenon.

What is the last thing you thought of or masturbated to?
A voiced story with pictures.

Have you walked in on or caught someone masturbating?
Yes.  A friend, back in college.

Have someone ever walked in on or caught you masturbating?
My mother, and my wife.

Have you ever had cyber sex?
No.

Have you ever had phone sex?
No.

Have you ever had a wet dream?
Yes, several.

What is your method of masturbation? (i.e. Hands/Toys/Lotion/etc.)
Depends on the mood.  I might just use my hand, or my toys, or I might stimulate my tucked clitty through my panties while working my nipples (it makes a mess in my panties, but, god, it gets me off!).

Are you loud or quiet when you masturbate?
Quiet

Has anyone ever watched you masturbate live online?
Not yet...

Has anyone ever watched you masturbate in person?
Just girlfriends...that I know of...

Have you ever masturbated with someone? (Mutual masturbation)
Just girlfriends.

Have you ever watched someone masturbate live online?
Yes.

Have you ever watched someone masturbate in person?
Just girlfriends.

Have you ever masturbated to someone?
Does that mean mentally, or in person?  Either way, the answer is yes.

Who do you like to think about when you masturbate?



 If I'm going through my typical fantasy, it's usually a gang of my old colleagues.  There were some beautiful women at that old place...and I'm usually sissified and pleasuring one of their boyfriends as they watch and cheer me on...

Have you ever told them you think about them while you masturbate?


No.

Whats your most embarrassing masturbation story?
Probably when I was around 13 or so, I was starting to get into my mom's lingerie drawer and I heard the car door slam.  I had to place everything back quickly and jump in the shower to cover my tracks...leaving a pile of my (thankfully male) clothes in the living room for her to find.


Whats your funniest masturbation story?


I honestly have no idea.

Have you ever used something unique or strange to masturbate?
I've used a shot glass as a makeshift buttplug.

Is it easy for you to orgasm or do you have to work for it?


Depends on the situation.  It's usually not hard, but sometimes it's like running up a steep hill.  Once I get over the top, the down hill run is a lot easier, but getting up there is almost a chore!

Whats the easiest way for you to get off?


Tucking my clitty into my panties, and pinching my nipples while rocking my clitty into my panties.

Is there only one way you can get off? (i.e. Vaginal/Clitoral/Toy Use)


Nope.

Does anyone know you masturbate? How did they find out?


I think everyone knows.  We're adults.

Have you masturbated because your partner wasn’t around to help? Where were they?

Nope.  I masturbate because I want to masturbate.

Have you ever masturbated to a fictional character?


Watching or mentally?  Either way, yes.

Are you able to achieve orgasm through only non-conventional or indirect methods? (Breast Play/Hands-Free/Anal)

I have actually managed to milk myself...thought I don't know if you'd count that as an orgasm.

What is the strangest object you’ve used to masturbate vaginally or anally?


A bicycle pump (it's a hand pump, don't get any ideas).

Do you ever double penetrate while you masturbate?




Two toys, one hole, or spit roasting?  No to the first and yes to the second.

Do you ever suck on a dildo while you masturbate?

Well, I am a sissy...

Do you edge when you masturbate? (Get to the point of orgasm and stop repeatedly to enhance the experience)

Yes, of course.  I often deny myself orgasms afterwards.

What position do you typically masturbate in?
Sitting upright.

Describe a typical masturbation session.

I don't know if I have one, but it's usually after a morning of teasing and denial, usually dressed to some extent, and to some form of porn I have.

How often do you usually last?


When I finally go for it, after a morning of teasing?  Not long.  Not long at all.

Whats the quickest you’ve ever been brought to orgasm?



I'd say about 30 seconds.

What’s the longest masturbation session you’ve had?


Several hours.

What’s the most amount of times you’ve cum in a day?
 5

The Apology Caption of the Week - LXXXIII

So, after about 18 months, it finally happened: I missed a deadline.  I write up a lot of these posts in advance, but the CoTW's I usually do in (reasonably) real time.  I don't know what happened.  I had everything about 90% laid out and the date came and went, and I didn't even notice.  Well, here's the caption.  I'm sorry to everyone out there in the internet.  I'll try to have this happen on as few occasions as possible.  At least you'll have an extra update this week!

Re-Blog Wednesday - 86

How much of a sissy am I?

Really, I think I could only take about 6, but I would hope there would be 10+.  I would want them to push me beyond my limits.  I would want to be a mere pleasure hole for them to use endlessly.  I would want them to keep at it, well after I started begging them to stop.  I would want them to keep going until I passed out from exhaustion...and then keep fucking me.  I would want to come out of that room covered with dried cum, so there would be no mistaking what had transpired.  Everybody who saw me on my walk of shame would know me for the gang-banged sissy-slut I was...all on film, of course.