In Character

 

Office Policy

 

Make It Happen

 

Therapy - Part 6

 Therapy - Part 6

Shelly's Therapy to cure her of her crossdressing compulsions continues and now expands! She's done so well with her Special Encounter Therapy sessions that Dr. Wilson declares her ready for even more! Shelly is intent on proving that she is a normal, straight, heterosexual man and not some homo and is determined to obey her doctor! And being cured of her crossdressing is what they're both after, right?

Part 6

I really tested myself that weekend.  I dolled up from one outfit to the next and tried one hairstyle after the next and did my face up pretty in one way after another and left myself gaping from all the toys I had up my sissy pussy.  Through it all though, I took care to stick to my special diet that Dr. Wilson – my wonderful Doctor Wilson – had prescribed to me.  That and do all the in-home exercises in time to the special fitness CDs he prescribed as well.

 

Those were super fun!  Getting ready for those meant entirely different outfits!  I really like the 80s disco bunny “vibe” of the spandex tights and leggings and even the way the midriff baring top fit.  I liked to pretend it was a sports bra keeping my gorgeous titties in place.  But it was just a midriff sort of cutoff tank top thing in hot yellow with another one in hot pink.  They were absolutely normal things for guys to wear when they still had some flesh to work off on their chests.  The sweat bands for my head and wrists just completed the look.

 

Stepford Sissy Housewife Problems

 

Kiss

 

Milking Sissy

A gurl's dreams and her Master's desires combine in a truly wonderful and rather extreme way. Nothing to fear for her as she always wanted this for herself and the voices her Master plays into her ears just confirms all that, right? What she eventually becomes leaves her wonderfully feminized and gorgeously submissive with a beautiful set of very ample breasts that are overflowing with their milk. Milk that has some truly wonderful properties to it. What more could a gurl want in life than to have found a strong, and dominant man who shapes her into the vision of a submissive feminized milking sissy she always yearned to be?

Milking Sissy

The bondage wasn't necessary.  The straps are there really as more of a ritual and now something I took comfort in due to its familiarity.  My make up wasn't necessary either.  Well, not really.  But I no longer face the day without having at least some lipstick on.  Thanks to what my Master had tattooed, I usually don't need much more than that.  When it's time for my milking however, I like to make sure I'm as pretty as I can be.  Especially if my Master decides to make use of me while I'm being pumped.  I love that.

The milking cup on my beautifully shrunken sissy clitty isn't really necessary either.  It's been a long time since anything came out of that other than my watery precum.  But that too is there out of ritual and familiarity.  The gentle suction though does feel nice.

What feels heavenly though - aside from my Master's cock sliding past my collagen-puffed lips or filling my sissy ass, that is - is when the pumps start running and my milk lets down.  I've been so pickled with all the hormones and lactating drugs for so long I can hardly remember a time back when my breasts weren't full to the point of bursting.  It's gotten to the point he's putting me here in the milking stall twice a day.  Recently, he's been talking about upping my dosages to get me milking three times a day!  I don't know if I could stand the bliss from that.  I sure am willing to try it.  I love pleasing my Master.  In any way he wants of me and especially if he wants me to yield that much milk, then I will!

The Gift

A sissy sextoy would make such a lovely gift.  And being a sissy sextoy is such a lovely gift as well.  Combine the two and…

(This is a quick little fantasy piece I wrote some years ago as an actual gift to an individual I'd chatted with. We both "met" online in the Second Life online virtual world where we shared our TG transformation fantasies.)

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The Gift

I shift my weight around again.  I'm not uncomfortable in this position but nor am I comfortable either.  I wish I could see what was going on around me.  Or hear what was going on.  The only thing I can see are the images being played on the goggles strapped over my eyes.  The only thing I can hear is the voice of my master.

The images are of beautiful cocks and handsome men and beautiful tgurls pleasing those cocks and those men.  Over and over and over.  My master's picture is among the images.  My picture is among the images.  There are too many other men included for me to pick out any single one for me to figure him as my man for this time.  There are women in the images to.  Women being served by beautiful tgurls, beautiful sissies, beautiful shemales.  I'm in those images to.  I'm also in the images of the tgurls serving all those sexy shemales as well.  All about service.  All about submission.

The headphones covering my ears are telling me that.  "Submit," "Serve," "Pleasure Your Superiors" my Master keeps telling me.  His voice is so wonderful.  So powerful.  So commanding.  So dominant.  Just hearing him speak turns me on.  Knowing that in my pleasing others I will be pleasing him turns me on as well. 

I yearn for my trip to be over soon.  Over so that I am "delivered."  Over so that my Master's "gift" is received.  For that is what I am now - a gift.  A gift all nicely packaged and ready to be received by whomever my Master has given me to.

It has been a while getting me to this point.  

Playing the Part - Chapter 6

Diana gets invited to a party with Natalie and Jayden only it's Mistress Natalie and Master Jayden. Diana learns more about her dear Ms. Cambrai. And Diana learns more about herself in the process. Frightening things about herself and powerfully seductive things about herself as well.

Day 557:

Oh my!  Where to start?  I’m still reeling from it all.  Natalie showed me an entirely different side of herself.  I love it but was amazed to see it.  I’m flattered that she shared it with me.  It’s also helped with my perspective on things.  That, not to mention how ecstatic the whole experience has been.  I hope she invites me to another one of those parties.  I’m afraid that she will invite me to one of them too!  The idea of losing myself like I saw so many of the other people there lose themselves is a frightening one.  And one I simply can’t get out of my head as it turns me on so very, very much.

So, Natalie asked me to come over in the late afternoon so we could get ready for the party she was taking me to.  I was hoping for maybe and dinner at some quiet little place and then she and I could spend some quality time together we my worshiping her flower until she purred and then howled.  That and her holding me close like I love so much.

No, not this night.  She’d asked me to be sure I was super hairless and perfectly smooth before I showed up.  So, another trip to the spa on Tuesday.  It’s gotten actually quite fun heading over there.  As I’m sitting in the lounge waiting for my appointment I chat with the other ladies there.  They’ve no idea and I do nothing to dispel their assumptions.  I don’t know why, but I enjoy such “girl talk.”  And Greg, he’s such a sweetie, doesn’t bat an eye now when I’m there in all of Diana’s glory.  He is kind of cute too.  Nice perky little buns and, as Louann say, a “nice box” too.  Not as gorgeous as my leading man but, just the same, he cute in his own way.

Therapy Part 3

 Dr. Wilson's cross dressing therapy treatment continues! Shelly, our favorite patient in the first two installments, relates how her therapy treatments have not only progressed but have gotten so advanced that she's now ready for her first first Special Encounter Therapy session!

My therapy to treat my cross dressing problem was working.  Well, more accurately, it was therapy to help me address my sexuality issues my cross dressing was causing.  I’d been undergoing treatment by Doctor Wilson for over a year now and every day and in every way I making fantastic progress.  Doctor Wilson assured me of this in every therapy session.

 

The way he smiled at me as he looked down at me as I knelt in the Power Dynamics Enhancement Position before him and he filled my mouth with his wonderful cock assured me that my therapy was working.  Or the way his hands held me so tightly as his wonderful cock spasmed deep inside of me when it was time for one of my Prostate Expressing sessions.  I knew my therapy was working as it made Doctor Wilson happy and making him happy made me happy.  Doctor Wilson is a wonderful doctor and I am so lucky to be treated by him.  Doctor Wilson is a caring and professional doctor.  Doctor Wilson is always right and I can trust him to always help me and know what’s best for me.  Doctor Wilson is a wonderful doctor.

 

Positive Reinforcement

 Another step in a man's becoming the sissy fucktoy of her dreams. Well, they certainly seem like they're her dreams. That's what her Master has told her they are and that's what the little voices in her ears keep telling her they are. And being a sissy fucktoy certainly feels so wonderful! So, of course being a sissy fucktoy is what she's always dreamed of being!

Lisa’s head swam.  She was so damn horny it was difficult for her to think straight.  Every inch of her skin felt alive and sensitive.  Her puffy and extended nipples even more so.  Her cock ached with pleasure even as permanently limp as it now was.  Even her balls, shriveled and atrophied as they now were, also ached with pleasure.  Her ass was even worse.  It felt empty now that Master Carl had removed the plug.  Not that the plug helped much with that horniness.  Oh, it filled her up and stretched her out wonderfully and if she could only have moved around more it would’ve rubbed on her prostate enough and she’d have climaxed.  But Master Carl had strapped her down too securely for her to have moved like that.  So it only served to frustrate her and make her even hornier.  Now that he’d taken it out, the emptiness made her ache.

Change In Management

Every new technology comes with its own risks and advantages.  While the technology may change, people are still people.  Some are ethical, some are not.  And how they make use of that new technology is up to them.  Some do so aware of those risks, some do so only thinking of the advantages...

Change In Management

Richard Dawes turned in minor aggravation at the latest alarm notice to pop up on his computer screen.

 

"What now?" he grumbled.

 

This alarm though was different.  Flashing repeatedly in bright red to orange to violet it was impossibly eye catching.  And worse, he couldn't click it off.  He had to enter his company ID and password to get into it.

 

"That's different..." he mused, still annoyed at the interruption to work as BetaDyne's CIO.  "This is so not my job." he continued grumbling to himself.

 

Playing The Part - Chapter 4

Diana comes ever more unto herself as her previous life disappears ever more. Now she is finding even more possibilities as Diana than she ever thought could be. And more and more in her life are joining her in being with Diana.

Chapter 4:

Day 461:

Sorry, I had to stop there.  I actually had to stop several times when writing about what happened that night with Jayden and Natalie.  Finally, after “relieving my womanly needs” twice, I was able to finish composing my account of that night.  I had wanted to write about what happened the next morning as it all just flowed wonderfully together.  But I was so exquisitely aroused from composing it all that I simply had to stop. 

Playing the Part - Chapter 3

 Playing the Part

Chapter 3

Diana continues to learn ever more about herself. Once again she learns that, when it comes to being Diana, Ms. Cambrai is right. Ms. Cambrai is always right. In particular, Ms. Cambrai is right about things which Diana had never even imagined herself doing. Things which make her previous life seem ever more distant as being Diana feels oh-so-very, very good...

Day 430:

Great news!  They not only found a new manufacturer for the clothing line here in the US but this new company can get in operation a whole month faster!  Yay us!  Good thing I didn’t wait any longer than I did for me surgeries!  Mr. Simms is such a smart man!  He’s made such good decisions for me.

Day 433:

I was so bubbly about the news of the production starting sooner that Ms. Cambrai said we should go out and celebrate together.  This being “together” with her, me and Jayden.  We’ve gotten back to doing dance lessons together now that I’ve healed up. I’m still stretching a bit. So it’s been super helpful for me.  And Jayden has been such a sweetheart about it.  His moves with me dancing are just as powerful as ever and I’ve come to relish the way he handles me on the dance floor.  Ms. Cambrai seems to relish his effects on me and teases me about how I was letting Jayden steal me away from her.  Not a chance!

Playing the Part – Chapter 2

 

Playing the Part – Chapter 2

Jake is now "Diana" full time in order to "stay in character." But Diana suddenly faces even more challenges than merely maintaining "her" poise under Ms. Cambrai's tutelage. Challenges which draw Jake ever further away from himself and ever deeper into playing the part of Diana. Challenges which he can only overcome by becoming Diana ever more completely. And becoming Diana more and more just seems so right and feels so very, very good...

/////////////

Day 290:

Wow.  I didn’t intend for this to turn out like I was writing some porn story.  But Ms. Cambrai said I should be detailed in writing down what I’ve experienced.  Detailed, specific, and heartfelt.  So, I shouldn’t be embarrassed or hesitant about it when my emotions come out like that.  She asked me if she could read my journal.  I don’t know how she even knew I was keeping one.  I must’ve mentioned it in passing some other time.  I was a bit hesitant but, Ms. Cambrai is right.  I started this journal as a way of keeping notes to help me with this role.  And as she is in my life now to also help me prepare for this part I am playing, then it only makes sense for her to also read my notes.  That way she can help me gain better insights into my character, Diana.  Besides, how could I keep any secrets from Ms. Cambrai?

Playing the Part - Chapter 1

 “Playing the Part”

How far would you go to “stay in character” in order to play a part?  How far is it acceptable for others to go in “helping” you to “stay in character” in order to play a part?

Jake Stevens is a down on his luck aspiring actor and model.  His best friend and roommate comes up with a part which could really help Jake make it big.  Problem is, the part involves modeling women’s clothes for an upcoming major new fashion line.  Jake accepts the “gig” as he needs the work and it will help his friend as well.

But for Jake, a guy, to pull off playing the part of a woman means a lot of dedication to “staying in character” on his part.  A dedication that the people around him seem exceptionally helpful in providing.  All too helpful, in fact.  Jake soon finds he’s losing himself in the character who’s part he is playing but can’t help himself from doing so.  Can he stop himself from losing himself?  Should he even try?  Especially when it all feels so right and feels so good.  Feels so very, very good…

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This is the longest tale I’ve worked up to date.  This first “chapter” doesn’t even reach a third of what I’ve currently written and even that isn’t finished yet!  Jake has lots of adventures here.  And faces lots of “challenges.”  The X rating applies to the tale as a whole.  It’s appropriate for this first part but it does take a bit to build up to where it fits appropriately.  The “Mind Altered, Hypnosis, Brainwashed” and “Identity Death” categories very much apply here!

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Playing the Part – Chapter 1

Day 1: 

Keeping a journal? Keeping it daily?  Seriously?  Sounds more like a “diary” than a “journal.”  And the whole thing seems more egotistical or what some chicks would do than what guys do.  But, Paul said it helped him when he was getting into acting and his boss recommended when he started with his latest gig.  So, if it worked for him.  Seems kinda girly but what the hell.  He asked me about it a couple of time now so, just to shut him up – ha!  I’ll do it. I, Mr. Jake Stevens, am now keeping a daily journal.  So there.

Day 10:

I really appreciate Paul’s helping me out like he has but, damn!  He got me all spun up about doing this “vintage fashion photo shoot” thing.  I thought it’d just be for one day’s photography - a “shoot” – not a month’s long campaign thing.  And he never said anything about it being in girl’s clothes.  Or as he made a point of pointing out – in “women’s clothes.”  

It Was Always So Easy...

Board Meeting

For this one, I had the image of a hypersexual bit of elegant debauchery and objectification in mind.  I've long liked playing around with the inherent power disparity in a corporate / business setting.  The boss - male or female - taking advantage of their subordinates and using their power over the helpless man to have their way with him.  Women in suit dresses are a major turn on for me to start with and the idea of a female or male executive feminizing and emasculating one of their subordinates and turning them into a sexual plaything for their pleasure only ads to that turn on.

Here, I wanted to explore just how far that "turning them into a sexual plaything" could go and how to take the objectification even further.  I like how it turned out.  Please leave a comment to let me know how you think it turned out!

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What price is too much to pay for becoming the real life realization of your deepest fantasies and dreams? And if you'd become that vision would it really matter whether or not you'd ever actually had those fantasies and dreams? And wouldn't objectifying yourself further only add to that perfection and bliss?

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Board Meeting.

Her Mistress ran her fingers along Jennifer’s cheek and then lightly flitted them over Jennifer’s nicely puffed and well glossed lips.  She smiled at the gurl.  It was a wicked and leering smile as well as a proud and reassuring one.  Jennifer was already in such an enveloping haze of lust and arousal that she barely registered her Mistress’s touch.  She did however, register the tug on the leash clipped to the collar around her throat as her Mistress, Carol, led her forward into the Board Room.  Jennifer eagerly minced along behind the wonderfully shapely ass of her Mistress.  Carol looked so very commanding and sexy in that over the knee length black skirt, tailored business jacket over her fitted white blouse, and her seamed Cuban heeled stockings ending in the five inch heeled stilettos.  Jennifer would’ve happily followed her Mistress anywhere – were she wearing such an outfit or not but especially when she was.  Considering Jennifer’s current state, it was apparent she’d already followed her Mistress to some truly life altering places.  Her Mistress was proud of that.  And Jennifer loved making her Mistress proud.

The Gift

I actually wrote this as a spur of the moment thing as a result of a chat session I'd had on Second Life.  I'd found SL (as it's called by those on it) to be very stimulating when it came to feeding my feminization desires.  As the whole virtual reality thing involves choosing your avatar with no reality limitations required, you could - and I did - choose to be whatever gender or state of gender you wished.  Lots of fun!

One of the encounters I had got into some mutual fantasies and that spurred this little story.

~~~~~~~~~~~~~~

A sissy sextoy would make such a lovely gift.  And being a sissy sextoy is such a lovely gift as well.  Combine the two and…

~~~~~~~~~~

The Gift

I shift my weight around again.  I'm not uncomfortable in this position but nor am I comfortable either.  I wish I could see what was going on around me.  Or hear what was going on.  The only thing I can see are the images being played on the goggles strapped over my eyes.  The only thing I can hear is the voice of my master.

The images are of beautiful cocks and handsome men and beautiful tgurls pleasing those cocks and those men.  Over and over and over.  My master's picture is among the images.  My picture is among the images.  There are too many other men included for me to pick out any single one for me to figure him as my man for this time.  There are women in the images to.  Women being served by beautiful tgurls, beautiful sissies, beautiful shemales.  I'm in those images to.  I'm also in the images of the tgurls serving all those sexy shemales as well.  All about service.  All about submission.

Time To Move On

Time To Move On

This one is something a bit different.  I've wondered what would happen when the dominant partner realizes that it's not transformed submissives he - or she - is really into but transforming submissives.  And what, then, becomes of those transformed submissives?

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Lisa began to slowly wake up.  It was as if a heavy fog was slowly receding all around.  She rolled over on to her side in her bed and that was when she began to realize something was wrong.  As her anxiety swelled it forced her to become even more awake and she rolled over on to her back again.  It took her a seeming eternity of near panic over the wrongness she felt before she realized what had happened.