58 christmas (click on the picture to view)

entry for the rachel's haven contest.

staff four Life guard

What the fuck is going on here? Did you fuck with my drink, you bitch?!

Relax, Shannon, you're my new lifeguard.

What did you call me?

Before you get worked up, cum inside and let me explain the perks of the job.

These had better be worth MY COCK!?

Oh this is definitely a fair trade. You will have room and board, food, clothing and all other necessities provided for you.

What's the catch?

You have to enjoy yourself.

I don't understand.

Let my friend explain.


OOOOO-OOOOO

You like?

Yeah-y-YEAH
YES YEEEEESSSSS























I like.

Staff three Bus Driver

What the hell happened!? Why do I have breasts?

I needed a bus driver for my new sissy school.

And what if I don't want to? What do I get out of this?


Something very nice...
































Where to, boss?

57 Change of heart

Today, I tf'd a person who was very distressed by the description of her new life. I made a proposal. If she could have vaginal sex and still wish to return to her previous life, I would allow it.
Here are links to videos of what she did.
1
2
3
4
5
6
What do you think she said?

What would you have said?

Staff two teachers

These are our newest pleasing females 101 students


















The class is taught by Sophia and Era
Sophia (above) and Era (below) take our newest sissies, so new they still whine about their cocks, and make them into horny, moaning sissies.

Staff one

These are my newly hired nurses for the school.
I gave them this position as they were all doctors in their former lives.

They will run our own mini hospital in the school. They have had no IQ loss since their change, so they are fully fledged doctors.

However, smart girls can have fun too...















These are them trying on the new uniforms that we had made specially for the school. Features include; built in vibration action for down time, matching under drawers and of course they look great. The girls are very excited about their new jobs.


Note that Pink denotes a fully trained doctor while blue clad girls are nurses.

Sissy U- A feminization heaven

I have been working for quite a while. I need to find a place to put all my sissies, as the seperate houses are becoming very difficult to manage. I am creating a university of sissies! It will be built to house a maximum of 1000 sissies. I have already bought the building and my girls and I are currently working our cute little butts off with renovations.

At the same time, I have trained a staff to accommodate all these sissies. This is going to be big.

56 Holiday bon(er)us

Sissified in; 1999
Sissy name; Belle
Former name; Bill
Reason for change; One of my first changes. An accidedent
Enjoys; Doggy style, anal, feeling pretty and serving the other sissies

She was one of my first sissies. She loves her new life so much, she acts as a maid and servant to the sissies. She claims it is to repay me. This is the uniform she normally wears.

55 Vid

Blonde; Sissified in; '06
Sissy name; Jasmine
Former name; Jerry
Reason for change; Accident
Enjoys; Dildos, lactation and oral sex

Brunette; Sissified in; '08
Sissy name; Haley
Former name; Hank
Reason for change; Stole a purse
Enjoys; Submission, Spanking, fingering

Location; Bathroom in sissy house # 54, in Washington
Situation; Haley was brushing her teeth in her panties, when she dropped her tooth paste. Jasmine walked in and saw Haley's ass in the air...

54 Red

Change me back

I can't

I know you meant well, Rory, but I DON'T want to be a woman. I liked my life.

Let me make it up to you.

What could possibly make this better?

This










OOOOO

AH




I knew you'd like it.

OOOO

I'll leave your clothes on the table.

Sure su-OOOO















This is really GOOOOOOOOD

O

OO

OOO GOD

OO GOD O GOD

O GOD!!!!!!



OOO

oo

ah

o, that was GREAT!!!












I think I can live with this...

52 Sex slave reversed

I can't believe I'm a woman!

Oh, don't worry my mistress, it's not so bad.

Mistress?

Yes. Lady Rory told me that I am to serve you as compensation for the... mistake.

Show me... the bright side of my new body.

*gasp* Your milk tastes orgasmic, my mistress.

It feels ooooo great!!!! Ah

Any other ways I may service you, mistress?

Call me Natasha.






OOooOOOoo That is- AHHHH!!!!

Natasha, you are flowing!!!!

I'm c-cumming!!!!



I can see that!!!




Oh, Zacharia, you have serviced me so well. What can I do to please you?

Well...

OOOOOO NATASHA!!!

Now who's flowing?

51 Bean counters

Well, the web site has been getting very complicated, but I found a solution. I recently sissified a group of japanese bankers. I just introduced them to their offices.
This one is Anita
Ooooo

You like the spandex, huh?

Oh my gosh, I love it Rory!

You ready?

Hold on, please. Let me break into these.

Not a problem












OOO, it's rubbing my pussy!

I hardened that area a bit so you could keep yourself happy during your work

How long before my sex break?

One hour

This could be tough

I'm sure you can do it.



All right, Sally, are you ready?

You promised me a good fuck as a reward.

So you want it now?

My panties are wetter than a rainforest, I want sex NOW.

Sure.












OOoooooo

You like?

OOO, YEAAAAAAHAA!!!!
How did I ever get anything out of sex as a man? This is SOOOOO much better!!!!
OO OOOOO OH GOD OH GOD!!!!


Is this compensation enough for your hour of work today?

Sure, just keep me cumming.

What do my sissies want?

I want to please my loyal sissy readers. So tell me what you want to see in my next story. Just leave a comment on this post with the details.

50 Losing my virginity again

Taken from a recording of a new couple in the "cherry popping" chamber.

Listen, I don't care if I'm still with a woman, I don't want anyone touching my pussy. I am a MAN, not a sissy! I am supposed to ha-

OH ungh

You see, Ben, I think we can get used to it.

Shh-shhut up just keep GOING

Ooh, see I told you.

Aaaah













OH! Look, they left some DILDOS! I bet we can have a LOT of fun with those!

You seem to be enjoying yourself, Zeke.

And you aren't?

49 Beach distractions

The sissies and I went on a big beach trip today. We are having a great time. The problem is, I can't find Trixie, the new girl. I told her to go put her new bikini on, and that was 2 hours ago! I hope she didn't try to escape again...

41 Pool mistake

I was at the public pool in my town recently, when I made a big mistake. I got a bit too excited when I saw a very attractive guy. I drop of milk got out of my breast and mixed with the pool water. The pool is no longer co-ed. At least not for a while.

40 Fucking machine

I have constructed the ultimate training device for my sissies and they have started fighting over it. Here is Alissa, formerly Andy, using the machine for the first time.

39 Video

Former name; Josh
Former job; Health inspector
New name; Eve
Favorite things; Anal sex, panties, dildos

38 first milk

Nina is very excited today. She ran into my room a moment ago to spray some milk on me. I'm very happy for her. She finally lactated, and that means that she can graduate and recruit sissies of her own. Here is a picture of her shooting her very first drops.

37 Upset

Lindsay, formerly Larry, was very upset about her change. Normally, a new sissy forgets this angst when shown the pleasures of her new body. Lindsay had to be held down as my veteran sissies pleasured her. I may need to resort to spankings. Perhaps even memory wipe.

Sissy contests!

In honor of what will soon be 1000 profile views in under a month (currently 923), I am hosting two contests.

Kinky sissy captions
Find the hottest pictures for me to caption and email them to me. I will select the best three and make captions based on them. No limits per sender, so send away!!!

Kinky sissy story
Write a hot sissy story about me making a sissy out of a man. He must drink my milk, as many of my readers know. The two best stories will be posted on the site.

Remember, sissies who do not enter will be spanked.

-Rory

36 School

Ralph and Ned recently were caught peeking in the girl's locker room in their school. The principle sent them to me for punishment. Now, they have to live with the concept that their pussies are available for the world to see. Rhonda and Nadine are very unhappy about this publication. However, they will be very unhappy about what will be in them tomorrow.

35 cam extra

This is Emilia, slurping the cum from her friend, Trish.
Emilia asked me to make her a sissy. Not a problem. Trish tried to steal my identity. I gave her a female identity of her own

They now enjoy lesbian sex, orgies, anal sex and being covered in cum.
Former names
Martin and Tony

34 web cams

Well, you've heard of them. Now, you can see the web cams of my sissies in action. Every week, a new cam feed.This is former chef, Janine, helping her friend and former stock broker, Alina.

The two enjoy anal sex and lesbian sex the most.

Former names

Gregory and Arty



This is Ailine. Former bus driver, Allen had asked me to make him a women.

Former name Allen

Enjoys masturbation, panties, stockings and posing.

33 Accommodating more

So the movie theatre is free?

Yes. I have an entire stock of films dedicated to teaching my sissies how to enjoy their new lives and new bodies.

Sounds like fun.

It is. Many of the techniques you will learn can enhance your pleasure exponentially.

Oooh. I'm wet! Oh, you told me about this feeling! I feel... excited. I- I need to see a film. I want my first sissy orgasm to be perfect.

Here. This video should prove quite... helpful.


Ah. I'm so comfortable like this. Wow, my pussy is burning. Oooh, that looks heavenly! You must let me try that! Look at her face! I want my experience to be just like that!

32 Accommodating

So I get a pool, too?

Yes, I take good care of my sissies.

Free?

Yes.

I love the bikini. I feel so pretty.

You're becoming in touch with your inner woman.

How do you pay for it?

There are cameras watching all of my sissies at all times. They are linked to my blog and paying viewers can see you.

Are they watching right now?

Yes.




Let me thank them.

31 sissy scout

What's happening? Why am I in this house, in these clothes and in this body!?

Hello, Janice.

My name's not Janice, it's... I can't remember. What's happening!?!?

Let me explain. Yesterday, you commented that girl scouts were whores. Well, today you are a whore of a girl scout. I put you in this body and this house. This home will be your sissy training ground. There is no escape, Janice. Now, you will enjoy your new body. Show me how much you enjoy being a sissy.
















You love your new body, don't you?

It feels great!

Let's see it...










Oooooyes Ha Ooooo


Do you feel better, now?

Oh Rory, I don't even remember what I was upset about.

Good. Now, keep practicing. Remember, the guys will be here to see you in an hour...

30

What drugs did you slip in my drink, bitch? What did you do?!

No drugs, Sophie. I-

What did you call me!?

Quiet! Now, I did put something in your drink, Sophie. However, they weren't narcotics. This is your new body. I am your master now. You are my newest little sissy girl. Your job is to fuck and enjoy it.

And if I say no?

You don't really have a choice. The moment you touched that woman's butt, you agreed to this sissy life. Ah, there is Jim, by the trees over there. Come, Sophie.
Suck him, Sophie. See what it is like from the woman's side.

It must feel humiliating. You've demanded this treatment from many women before. Now you'll learn to do it yourself.



Now, bend over. It's time to officially start your new sissy life in the traditional way.




Tomorrow you shop for panties.

The day after, I'll get creative.