A Caitlyn Story

So while driving home I got into Caitlyn's headspace a bit.

Now before I get into this, some of this post will be a bit.... TMI.  I'm going to talk about masturbation a bit.  It won't be graphic, but if that's not something you want to read about then by all means, skip this post.

OK... so driving for 16 hours between Texas and Michigan gave me plenty of time to let my thoughts wander.  I thought about family, my future, work, future jobs, relationship.... a whole mess of things.  I didn't really make any headway or come upon any new conclusions so I won't go into those.  But I did come up with a story idea.

I think the reason that I got into this story was simply due to me being horny.  Yeah.. I had just visited with a family for four days which means I didn't masturbate at all.  I just find the idea of wanking it in someone else's shower kinda off putting.  Add in the day's driving down and I was now about six days without an orgasm.  For comparison's sake, I normally masturbate once a day.  That has held steady before I found Caitlyn, all throughout Caitlyn's time, and after I lost Caitlyn.  Hell... it's been that way since high school.

So needless to say, the urge struck me when I had plenty of time on my hands and nothing to do but watch the road.  When I get this way, I'll often just think of 'sexy scenes'.  Sometimes they'll be part of a narrative.  Sometimes I'll have a part in this scene (mostly now a days as the man, but sometimes still as the woman), and other times I'll just enjoy imagining a man and a woman having sex or being part of a scene.


One particular scene that kept running through my head was a woman laying her head across a man's lap as they watched a movie.  At first, I was the man.  I was enjoying watching a film while strokng this beautiful woman's hair.  My other hand would stretch out and explore the rest of her body laid out to my left.  My hand would find her breast and cup it a bit, rub across the nipple gently.  It would stroke across her side between her panties and her bra (yeah... she was only in her panties and bra by this point of thinking).  That hand might cup and rub lightly over her ass.  It might even dive into her panties and gently rub over her pussy.

As I was initially considering this scene the woman was happy to be loved and touched.  But then Caitlyn came in.  She flipped the script.  I was the woman.  I had my head in some man's lap.  His hand was wandering over my body.  And while it hadn't been a part of my consideration as a man, I realized that as a woman I was lying right over his rising erection.

At this point the scene changed from a merely erotic happen stance, to a TG porn story.  I immediately thought of several caps where a recently transformed man had his head in some other guy's lap... and of course those always involved the blow job.  But I didn't want this thought to go into that direction.  Not because it wasn't sexy and erotic... but because it was too much so.  I really didn't need to be speeding down Interstate 44 with a raging erection and get lost into this thought exercise.

But at the same time I was enjoying the scene and didn't necessarily want to just focus my attention fully elsewhere.  So I kept the scene from getting directly XXX rated.

OK.. so I'm a recently transformed woman with my head in a man's lap.  Why am I there?  What are we watching?  Why aren't I running away screaming?  It's not as though I was making this for someone else... this was firmly in my own personal fantasy/wheel-house, so willing was out the window.  This was forced.  This was humiliating.  This was a guy that was either recently transformed into a woman or a guy cross dressing and trapped into this scene and trying not to let the man know he has a twig and berries in his panties.

OK... why was a little tricky... let's go with what they were watching.   This recently transformed guy has been forced into taking training on being a woman.  Part of that training was exercising.  No... dancing.  Yeah... ballroom style dancing.   Without his knowledge these lessons were filmed and now he has to watch it with his assigned 'boyfriend'.  But who is this 'boyfriend' then?  If he were part of this forced transformation he'd know that it was a guy in his lap... so that didn't work.  Well, what if they were both being transformed?  The guy was getting 'buffed' up.... bigger muscles, stronger chin, learning how to be more assertive with women.  They were 'partners' and the boyfriend just assumed this beauty in his lap was all woman.

OK... so the scene has to change a bit.  She's not in her bra and panties.  But she's in a flimsy clingy dress.  Does she have breastforms for his hand to wander on, or has she been given breasts?  Not important but we'll come back to that.  So she's being forced to how to learn to be a woman... let's go back to why?

Well if this place can change men into manly men as well as women, then that's easy.  He came there to be buffed out.  But how does a mixup like that happen?  I'll need more time on that, so let's move on to other possible scenes.

There would of course be the 'practice' scenes.  Where she was forced to dance.  Oh... and she could be forced to be a cheerleader.  And a secretary. She could be practicing her 'flirting' lessons.... on women as well as men.  She could practice kissing.  Hell she could practice giving a blow job on a dildo (and while watching it with him, she's become so nervous knowing damned well a quick zip of his zipper and she would be doing it again on the real thing!).  It could even be more basic... they could be watching her learning how to style her hair, how to put on makeup, how to pick out and put on clothes.  Dresses, skirts, tight sweaters, stockings, heels... oh walking in heels!...

She wouldn't start out by meeting her 'boyfriend', because I'd want to build up the tension.  I'd want to have her do these practice sessions without her realizing that she'd be watching it with a man.  But at the same time these tasks should be set up to the boyfriend's fantasy.  Hmm... but if they were were her fantasies... the fantasies she had of a girlfriend before she was transformed INTO the girlfriend,... that would be far more humiliating.   And squirmy.

I got it!

So he/she goes to this firm.  She wants to be big and buff.  But they offer her something special.... she can fill out a form for the 'perfect girlfriend'.  One of the package deals means that if they find a suitable match of a girl going through this transformative process, they would match the two of them up.  He'd be trained in how to be her perfect boyfriend (as well as get that awesomely handsome strong body), and she'd be transformed into his perfect girlfriend.  There's a mix up and instead of taking his desires, they start making him into his perfect girlfriend's image.  And at this point he wouldn't realize it, but they also found a match and are training him to be some guy's perfect girlfriend.  So there would be minor differences that he couldn't put together... like say he wanted his girlfirned to be a good dancer but he's trained to be a perfectly feminine and sexy ballroom dancer instead of the club dancing he really wanted.  He wanted her to be submissive, but they also train him to enjoy being spanked (he'd consider all the spanking to be punishment, but it's really to get that into his head).

Hmm... but that doesn't work.  If this is a legitimate company wouldn't he just complain?  I mean let's say the majority of this transformation happens while he's unconscious.. he'll eventually wake up and and tell someone that they had made a mistake.   I mean I AM talking about fiction but I want that 'trapped' feeling to really work here.

So how about another option.  He's lazy and doesn't want to work out.  So they have a plan that works with people like that... the Carrot and Stick plan.   He basically agrees to working out, but if he doesn't do it they can 'punish' him.  It would even work for some of the kinkier stuff they do on the side... people who are submissive and want that dominating transformation.   So when he wakes up with longer hair on his head, no hair on his body, small budding breasts, smooth skin and plumped lips he'll complain but they'll see he's on the Carrot and Stick plan and just keep 'forcing' him.

It's not much... continued complaining would still get through.  But it would get the story started.  So eventually he sits down with his counselor/salesman/technician.  Let's say it's been a month of forced feminization   I want to drag this out so let's say the planned transformations normally take a full year... this place would be a resort for the rich and while they are getting their bodies done they'd be treated like royalty.... except for when they don't follow along and are on the Carrot and Stick plan.  He was hoping for a resort experience and instead is stuck in a feminization hell.

So the salesguy is just as surprised as our heroine, but also quite screwed.  If he admits to the mistake, the company would certainly fire him.  Plus he sees that our heroine's 'boyfriend' is a former athlete.  His transformation is less about physical change and more mental.  He's secretly gay and wants to get into acting or sports broadcasting and figures if this place can change him to have a perfect girlfriend, he'll have it made.   So he's paid a LOT of money and is already going through the training to be a perfect boyfriend.

So the salesguy wheels and deals.  He tells our heroine that of course he can undo anything that's been done, BUT if our heroine would simply go through a few more months of this he could get out of it and save everybody's ass.   At that point he'd meed his 'boyfriend' and would have the option of backing out.... I mean it's not like they are making forced weddings.  At that point the athlete could get another girl assigned to him, our heroine could go through the process over and get his big buff masculine body, and the guy would make this all go for free.

I don't know... that's the stretching point.  Would someone do this for money?  Maybe he's not really rich and was spending ALL of his money on this transformation.  Say maybe he just won the lottery.  Now he could get that body, possibly a girlfriend (and he now see's just how perfect the girlfriend would be), AND get it all for free.  Maybe there's another sweetener, but for now that gets the story moving.

So now he goes back into the process.  He's told that he has to take to at least some of the transformation as the entire staff is worried that she's really not enjoying her time at their resort.   Now we have a set up.. he's trying to fool the people that are feminizing him into beliving that he wants to be feminized.  The sales guy even adds into the herine's file that she enjoys struggling, but really does want the change.  Their plan goes on and he gets further feminized for another month before meeting up with the sales guy again.  Our heroine is at wits end and is almost ready to just demand to get out of this but the sales guy convinces him to try at least one more month.

Further feminization.  There would be a lot of scenes that I only have partial ideas for.  He'd be assigned both a 'friend' and a 'sister'.  Both of these women would be responsible for getting him to think like a girl.  The friend would be the sexy carrot and get him to flirt and be sexy with her... and then use that as training to get him to be sexy and flirt with guys.  The sister would be the carrot and get him to act prim and proper and feminine.  Walking, talking, voice control, How to let a man open doors and pull out her chair.

During this month our heroine is starting to be trained in sex.  So there would be scenes of him watching porn with his 'friend'.  There would be lingerie and style lessons with his 'sister'.  He'd have to  have his first dance with a man.  He'd have his first 'date' with a man.  He'd have that scene I described earlier as he learned how to give head to a dildo.

At this point something woudl have to be done about his penis and scrotum.  I figured he'd either be put into a chastity cage or some type of gaff (pulling his penis up and behind him).  Both have their story advantages.  The cage would keep him frustrated.... especially as one of the 'carrots' they'd use would be milking him.  Giving him an orgasm without the further release and erection.  So do badly, and get spanked or othersie punished.  Do well and get bent over as they stick a thin dildo up and rub his prostate to a less than satisfying climax.  The gaff would allow him a more feminine profile... so a guy could rub down his dress and not notice a cock in a cage.  It could also be part carrot and stick... say it would vibrate giving him pleasure when he's doing well but give him light (or not so light) shocks when he's doing bad.   Imagine  him on his date... he tells a guy that he doesn't want only to get shocked.  Eventually he goes out to stop the shocks but by accepting the dance he now gets aroused while dancing with a man.  Oh the delicious humiliations either way.

All the while he's being filmed.

When he next meets with the sales guy our heroine is all ready.  He doesn't care about the money or other sweeteners, he just wants to get his old body back and to be let go.  At this point I need it to be more overtly forced.  So the salesman has been found out.  Not only has he been fired, but he's been replaced by a woman with the task of making sure that our heroine completes the transformation no matter what.   This new sales person (for the hell of it I pictured the new salesperson as a woman), tells him that he has no other option but to go through everything.  She's even going to up the training so that he can fully fool the athlete.  She even threatens him with a full (possibly unrecoverable?) sex change operation if he doesn't go along.

She give him only one little bit of hope.  That if he doesn't want to be this athlete's girlfriend at the end, then she'll honor the agreement he made with the previous salesman.

So the feminzation continues.  Now she's introduced to her boyfriend.  The boyfriend has of course been going through his own mental transformations, but they are based on being a boyfriend to this girl.  He's polite and chivalrous everywhere 'public' but wants sex and is more forceful and demanding in private.

Our heroine has a tough time for the last few months.  He has to show interest in her boyfriend but at the same time not admit he's a woman until the contract ending so that he can get out.  But at every turn she realizes how their training works together.  How she's been turned on by spanking and he loves to spank her.   How certain music and touches turn her on and how he seems to unconsciously know the same things.

Finally at her wits end she wants to not simply rely on her stating she doesn't want a boyfriend, but wants him to join her in denying a desire for their future to continue together.  So on the eve of the point where they can back out, she shows him that she's still a man.  Yes she has breasts (they'd be real at this point), yes she is full of feminizing hormones, and yes they've stopped her penis from being able to get hard, but she still has one and is still a man.

For a while during my drive, I figured that would be the end.  It would be the cliffhanger ending that I really like.  That let's the reader take the story into their own direction.  After playing around with various scenes (one where she has to go out on a date and the guy is about to force her to felate him, but her 'boyfriend' breaks in and save her, one where she chooses to go to a lesbian bar to test our her flirting ability but ends up with a bull dyke that treats her very girly and make our heroine treat her like a man and ends up using a dildo to fuck her).

But near the end of the drive I also figured I couldn't leave it there.  I think if I wrote this there would be a final scene before the new saleswoman.  The girlfriend and boyfriend are there and 'she' says that she doesn't want to continue their relationship.  But instead of also denying it he says he wants it to continue BECAUSE she's really a guy.  He and the saleswoman discuss what it would cost and what would be involved in ensuring that our heroine continues her act out in public.  Forever.

Of course if I ever wrote this it would be a perfect place to break it up.   This would be long enough to be multiple parts on it's own, but if I could imagine up a continuation there could be an entire second serialized story.  Say 'Carrot and Stick - Chapter 1 - 12' and 'Carrot and Stick II - Chapter 1 - 12'.

But then reality comes bursting in.  If I had ot put it out, I think this would be the fourth '/good' story idea I've had.  There of course is Language Barrier, there's the one I talked about back on Caitlyn's Masks called 'Oh, The Wicked Webs We Weave', there's the one about the virus that changes men into sex starved bimbos and two scientists who make a cure but only in that it changes one of them into a woman with his non sex starved mind.... and he's forced by society to 'accept' being a sex starved bimbo, and then there's the re-telling of 'Point of No Return' where a man is changed into a female assassin.  Sure, it's easy and even enjoyable to make up outlines like this, but I don't have any faith that I can take the next step and write it all out.  I don't seem to have the patience, and even when I do write something out I don't like how my writing turns out.

So... this will probably just go into the pile of 'story ideas that will never happen'.  But after thinking about it for the majority of a 16 hour drive... I just had to share it.