Caitlyn; comfortable in my own skin

This is a continuation of my Spring Renewal post.  I initially wanted it to be the same, as a single read through, but I think this deserves to be pulled out and added on it's own.  I think all of you followed me initially from Caitlyn's Masks, so I figured this would be of particular interest.  If you want to read through the entirety of my thought process, how I'm coming out of my winter funk and the other things that I'm doing to change and evolve, you're welcome to read Spring Renewal.  But you don't have to read it to get what I'm saying here.


Accepting Caitlyn.  Being more comfortable in my own skin.

Note the sentence structure there.  Yes, I consider these things linked, but at the same time they are two different things.

Accepting Caitlyn is something that's been happening to me ever since I gave that side of me that name.  Not fearing that side of me, not being embarrassed (online at least!) of that side of me, realizing that it's not a side of me but instead a part of me, and more recently realizing that it's okay to give up the more masculine sides of my physical self.

I am Caitlyn.  I am Calvin.  But those are not mutually exclusive.  I'm Calvin with some Caitlyn.  I'm Caitlyn with some Calvin.  I'm Caitlyn/Calvin and Calvin/Caitlyn.  I've had times where I felt I lost touch with Caitlyn, with my feminine side, but looking back at D+X, I can see that the last time that happened was almost a year ago.  It was late April or early May.  It lasted awhile, but that feminine side of me hasn't gone away that completely since.  I think Caitlyn is integrating into my core self more and more.

That integration shows on the outside as well.  It doesn't show with other people, at least not that I can tell, but I'm just more accepting of my feminine impulses.  For example, games have more and more recently been giving players the choice of playing a man or a woman.  With only once recent exception, I've been picking to play as a woman.  Fallout 4, FarCry 5, Assassin's Creed Odyssey.  I've been a woman in each of those and not just in the "Look, my avatar has tits!" kind of way.  The game story of FarCry 5 and Assassin's Creed Odyssey feel very different in the feminine role.  The one exception?  Tom Clancy's The Division 2.  You're allowed to build out a female character but so far as I see, there's no difference.  You don't speak or truly interact with others.  This is a big shoot'em up game.  AND I play this game with my brother and cousin, and I'm not THAT integrated that I want to share my Caitlyn self with my brother and/or cousin.

I'm not sure if I'll slip up or fall off the wagon, but I'm going to try and speak of Caitlyn/Calvin/me in a different way going forward.  Most recently, I thought of myself as two sides on the same coin... my Calvin side and my Caitlyn side.  But now I'm going to just refer to my Caitlyn self and my Calvin self, and even those will simply be standing in for what I really feel;  My Feminine Self and my Masculine Self.

Okay, so with that in mind, how exactly do I feel more comfortable in my own skin.  Well, feeling this way online is easy.  It's just an extension to whom I've been all this time.  It's been a long LONG road to get here, but each step seems small and easy.  Online I can feel comfortable with someone looking at me as a complete woman.  I can admit that I'm attracted to both men and women in different ways.  I want to love and protect a woman.  I want to be loved and protected as a woman.  Imagining having sex with a woman is with me as a man.  Laying her down, naked, on a soft bed and crawling between her spread out legs.  Pleasing her orally and maybe even bringing her to climax.  Crawling up, kissing her navel and breasts and throat and finally mouth, before inserting myself into her and making long passionate love.  Imagining having sex with a man is with me as a woman.  Kneeling before him as I take him in my mouth.  His hands in my hair showing me his love and guiding me without forcing me.  Having him explode inside of me and swallowing it down, before moving to my hands and knees and him entering me from behind.

The only thing in those scenarios that's a little back and forth between masculine and feminine... and I'm sure this is from years and years of having forced femme fantasies... is when the man takes me from behind I sometimes imaging him taking me vaginally and sometimes imagine him taking me anally.  When he does so anally, I sometimes get that warm, squirmy, blush inducing, humiliated feeling.  But honestly, that 'forced' feeling is the exception and not the rule.  More often than not (when in my feminine sense of self), I imagine having sex AS a woman and not merely as a man pretending to be a woman.

But again, that's all online.  Playing at D+X, I'm "Miss Caitlyn" and am engaged to Sean.  We make love and are desperately looking forward to our marriage.  In my own writings for caps and obscuras I can comfortably make sexy stories with forced feminization but not always imagine myself as the victim.  I can play games and think of myself as a female character.  But there's only one way that this 'comfortable in my own skin' reflects in my real life.

Fair warning, this next part is about masturbation.  I masturbate.  I assume many, if not most or all, people do whether they're in a relationship or not.  It's private and more often than not, should be left as private.  This next part will be about the HOWs of my masturbation not not merely discussing me watching porn and imagining what's going on.  So if you don't want to read through that, skip down and don't read what's in the breaks:







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Okay, so if you're reading this, then you know I'm going to talk about masturbating.  Overtime, my masturbation has moved from a more masculine method to a far more feminine method.  When I started masturbating I would be standing in the shower, gripping my slicked cock (yeah, I'm going to call it a cock as writing 'penis' over and over makes me feel like I'm writing nursing notes.  Deal with it!), gliding my hand up and down until I finally orgasmed.  There's many varieties on this... standing, kneeling, in and out of the shower, with or without some kind of lubricant, and at times with or without anal stimulation... but I gripped, I stroked, I came.

In the last couple years, that's shifted.  At first it was just out of a need and desire for privacy.  I was most often at my computer watching/interacting-with/reading porn.  I could open my pants, lean back, and go at it like normal but if I wanted to make sure and not catch sensitive parts of myself in my zipper I had to pull my pants really wide open or even down some.  But I live with two people... my Mom and my Brother. Mom never enters my room without express permission.  If she wants my attention she may knock and call my name, but I have to get up and open the door to see her.  My brother, on the other hand, will knock hard a couple times and then walk in.  I don't blame him as I do the same thing to him in his room, but I don't want to be caught masturbating.  When I go into his room there's a dresser between the door and where he is either sitting at his computer or lying on his bed.  He'd have ample time to tell me to stop before I saw anything.  While he (and I) would still be embarrassed, I'd at least leave without 'seeing' anything.  When he comes into my room though, there's no such thing to obscure his view.  If I'm in my chair at the computer and he walks in I have a literal split second to cover myself, change the computer screen (if I want to hide the TG porn I'm looking at), and tell him to not come in.  The fear of getting caught like that kept most of my masturbatory sessions in the shower.

But one time while looking at porn I reached down to adjust my growing cock and it felt good.  My pants were fairly tight and I was growing against my thigh.  I couldn't grip myself, but using a few fingers I could rub myself and press myself more forcefully against my thigh.  And yes, I quickly learned, I can do that for awhile and orgasm in short order.  So if I were 'enjoying myself' and my brother gave his quick two loud knocks, my hands could fly up to the keyboard and/or mouse and obscure what I was looking at... and could turn my head and see him enter without having myself exposed.  My room is constantly dark and shadowy and I'm not nearly large enough for someone to notice my hard-on against my thigh unless they're looking for it.

So that solved the privacy issue, but it soon became clear to me that this method also felt far more feminine.  I wasn't gripping and stroking and cuming as fast as possible,  I was leaning back and rubbing and instead of shooting my cum out it was leaving a wet spot on my pants and thigh.  Oh.  My.  God.  It felt so girly at times.

I started that around 7 or 8 years ago and except for the rare masturbation outside of home (in a hotel shower) or rarer home shower masturbation, I haven't "gripped and stroked" myself while masturbating at all.  It wasn't always about masturbating in a feminine way, but it certainly helped me feel feminine when that urge struck me.

It's been long enough that I have a fairly standard pattern.  I start looking at porn.  Almost exclusively, masturbation porn is either videos on pornhub or videos I've saved to my hard drive.  Only rarely do I masturbate while reading.  As I grow and get harder I reach down and adjust so that I'll grow comfortably against my thigh (and adjust my pants so the seam of my jeans doesn't cut into the activity).  As I get more aroused I'll reach down and give myself a few rubs.  The video will either work to continue to arouse me or it will go in a direction I don't find as sexy.  A non sexy direction example would be a woman giving head and making that overt "trying to speak" repeated gagging as she takes him into the entrance to her throat.  Gah Gah GAh GAh Gah Gha GAH GAH.... nope, I find that to be a turn off.  But as I zero in on a video that I find completely arousing at that moment, I start reaching down and giving myself more and more rubs.  It's slow.  It's gradual.  But it's also muscle memory and it's still me giving myself pleasure and that can take me out of the action on screen.

Recently I've been especially enamored with women kneeling and giving head.  It's just so damned sexy from both a masculine and feminine perspective.  Masculine is looking down and seeing a woman lick, kiss, and suck on your cock.  As she bobs up and down, the rubs I perform match her actions and I'll eventually orgasm, imagining myself spurting into her mouth or onto her face.  Feminine is imagining myself being the woman and taking my man into my mouth.  Pleasuring him as the pleasure flows through my entire body.  It's especially sexy when her hands are up helping her... gripping his cock, holding his balls, or just rubbing up and down on his thighs.  But in that circumstance.... watching 'me' give head... the muscle memory of occasional rubs works against me.  I'm getting very direct and powerful stimulation that doesn't match the action on the screen.  It makes me feel less feminine and at that moment, that's conflicting.

So a few weeks (maybe a couple months?) ago I figured out a way to enhance that feminine feeling.  Years ago, when I had that chance years ago to wear panties, one thing that enhanced that feminine feeling was tucking my cock back between my legs.  It didn't always work as standing up and walking around, especially when I'd grown fairly soft, meant that my cock would slip out and start to work it's way back up into it's normal position.  It could have been enhanced if I had an actual gaff (remember, I had thong panties and they didn't give me much 'hold' for my cock) or wore my pants very tight (like a woman would!).  So tucking didn't help me much then, but what about now?  I'm doing this exclusively while sitting down.  Tucking would mean more or less sitting on my own cock.  It would force my cock back and hold it there even as it moved from hard to soft and back.  And as for arousing myself?  It would be completely internal.  Watching the video would be sexy and make me feel feminine, and just like in the video my hands couldn't directly touch and arouse myself.  Even with my muscle memory trying to rub... there's no cock there to rub.  Even reaching between my thighs, the head of my cock is so far back that I can only reach it by sitting up a bit and 'pulling' it free from the tuck.

Now it's a physical fact that as a man gets aroused, his cock engorges.  He gets harder, thicker, and longer.  This action ensures I'm VERY aware that I have a cock, and as it grows it's actually giving itself additional stimulation.  It's basically rubbing it's way between my thigh, my scrotum, and over my perineal area.  It's actually hard to lose that level of arousal as even when I start to soften and withdraw, my cock is rubbing its way in a very tightly confined space and arousing itself again.  And just like that woman giving head, I'm getting more and more aroused without being able to give myself any direct stimulation.  She squirms and moans while pleasing her man, and I squirm and moan as I imagine pleasing my man.

Let me tell you... this has added a whole new dimension to masturbating and is a wonderful way to express my feminine self.  About half of my masturbatory sessions involve tucking myself for awhile and imagining I'm a woman!!  And I've had one session where I actually orgasmed in that position.  That was incredibly powerful as it built up so slow and while it was still focused around my tucked back cock, that orgasm spread out to every part of my body.  I'm normally quite when I masturbate (again, I don't have extreme privacy), but I had to bring my hand up to muffle the near scream/moan/cry that came out of my mouth.  That may be the most feminine I've ever felt physically.

And that tucking has moved beyond masturbation.  No, I don't tuck myself when out and about or even when moving around the house.  The previous points of not having something appropriate to hold myself back while standing still apply.  BUT, when I'm writing about something sexy... an obscura, a cap, this very post right now... I tuck myself back and it prevents me from turning arousing creativity into an eventual deflating masturbatory exercise.

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Okay, so that was long winded.  If you didn't read the above, the only thing you need to know is that I masturbate in a different way that helps make me feel more feminine.  Enough said.

That's the only way my feminine self has become more comfortable in my own skin.  I walk and move like a man.  Not because I always feel like I should be walking and acting like that though.  There are times that I'd like to walk in a more delicate manner.  A more feminine manner.  But I don't want to give that impression to others.  Deep down, I know that nobody would probably notice.  But I'm not comfortable enough with even the possibility, to allow myself to let my feminine side get more comfortable in my own skin.  My skin... more or less... is masculine skin.

And then there's the psychological way of being comfortable in my own skin.  Psychologically speaking, I'm either feeling masculine and showing that side of me to the world, or I'm feeling feminine and hiding from the world.  In my old parlance, I'm feeling like Caitlyn but am wearing a Calvin mask to hide it.  I do that around my family.  I do that around my friends.  I do that around my co-workers.

Earlier today when I started writing this up again, I logged onto Discord and almost immediately started catching up with some D+X friends.  I told them I was going to check in with D+X today as I haven't been there in more than a month, but before that I had to get my head around a question regarding me feminine self:  What is my goal in that area?  Set that goal, figure out where I am in relationship to that goal, and then work on getting from here to there.

If my only goal is to be comfortable with feeling feminine in an online and private way, then I've already met that goal.  If that's the case, I should certainly return to D+X and resume playing (less than I was before because the job keeps me away so much).  But if my goal is to share my femininity with others around me... then doesn't playing at D+X hinder that?  I mean, I LOVE being at D+X.  I of course love the players and character and storylines, but none of that would hinder me from being more feminine in the outside world.  What does hinder me is being able to satisfy that itch.  I WANT to express myself as feminine and if I don't allow myself to do that at D+X, then maybe that would push me to express myself in a more feminine way in the outside world.  Maybe it would force me to confess my feelings to my family and/or friends.

I'm not sure I'd ever confess how I felt to people at work.  Wait... let's get straight what I mean and lets start with things I feel or don't feel and things I want or don't want.

I DO feel feminine.  I feel that in some degree or another most of the time.

I DO feel masculine.  I feel that as my default position... but only out of habit.

I DO NOT want to experience sex.  Not as a man or as a woman.  I'm not sure why I'm not physically attracted to the thought of having physical sex, but there it is.

I DO want to have more relationships, but...

I DO NOT feel that I'm ready to have a romantic relationship.  Not with a woman nor with a man.



Okay, so that would be an awkward as hell conversation to have with my brothers.  Except for mentioning that we've HAD sex, we never talk about it.  Me telling them that I'm not physically interested in having physical sex would be the longest conversation about sex we've ever had.  And I can barely get my head around how I feel regarding romantic relationships, so how could I expect my brothers to deal with it?  My younger brother is married and has been so for almost 20 years.  My older brother is a bachelor like me, but I have no idea how he feels about romantic relationships.

I think this would be easier to 'come out' to with my friends.  A and E.

Yeah.

The more I think about it, the more I can imagine that conversation.  I don't think either of them would want anything for me other than my happiness.  Me being 'different' than them wouldn't speak anything about them, where with my brothers they might wonder what's wrong with their family.  My ability to speak about this is incredibly fragile right now... not online in my feminine world, but even thinking of having my brothers look at me sideways makes my chest hurt.  I don't know that I could handle their disappointment, even if it was brief as they try to absorb what I'm telling them.

Okay, so I'm going to set a goal.  I'm not fully committing myself to this goal just yet as I want to sit with it for a week or two and make sure it's not just the build up of writing this out giving me false courage.  But my goal is:

This year I will tell either A or E or both that I feel and can identify as both masculine and feminine at any given time.  I will do this this year if/when we meet in person.

We're actually at the beginning stages of planning a trip together like we took to New Orleans, so we should meet up this year.



Phew.... setting that goal is such a relief.  It both makes it so that I'm acknowledging the road I've traveled and makes is so that I'm going to move forward and let myself be more feminine.  It lets me know that I'll be more Caitlyn.  And that also means, I have no reason to stay away from D+X.

Sean... I'm on my way back!