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SubCaitlyn

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9/7/2013 10:15:55 PM

Journal Entry#4
Written: 9/5/2013
Posted: 9/7/2013

    Hello again, Journal.  Well, I spent another night with SirHalligan.  Not the whole night, I had to leave at a depressingly early time due to work obligations, but at least I could get together with Him.
    Upon arrival, I stripped and was inspected.  I had arrived plugged as it seemed like something which would please Him.  I had to confess that I had again broken His rule that I not masturbate.  He said He must punish me again, I knew I would be, I knew it would be worse.  It was.  I got up on the bed as instructed on all fours at first, then I was commanded to assume the “submit” position on my knees head on the bed, hands in front of me.  I had placed my palms up, he corrected me, they are to be palms down.  He spanked me by hand at first striking each cheek with blows that were sharp and purposeful.  Line by line, I was asked to recite the mantra He had given me to memorize when last we met.  I heard him remove something from the toy bag.  I got to the fourth line of the mantra which is “my body is not my own for it belongs to Him”.  I was struck by the wooden paddle.  Again I was asked to recite the line.  Again I was struck.  Over and over, this was repeated until I ached so badly I could not retain the position.  He told me to straighten my back, the way the position should be held.  I was scared, how long would this go on?
    He showed mercy on me.  I was off the bed and made to kneel in front of Him, then to bend forward and finally, He asked me to hug Him.  I did.  He hugged me back explaining that He wasn’t mad, the was no malice in His actions.  He was just punishing my indiscretion.  It was only disappointment that He felt at the time.
    He told me to dress in the clothes I had brought, my purple bra, the panties I had worn over, a plaid mini-skirt and a grey and black stripy top.  I turned around as He told me to do.  I bent over as instructed.  Back when we met, He had asked me to watch some videos on how to walk more effeminately.  I had watched them and had practiced some, not as much as I would have liked, but a little.  He told me to do the walk, from His bed to His door.  Again.  Once more.  I think I’m improving. At least I didn’t fall over or anything (barely).  I was then told to sit at His feet with my head leaned against His knee.
    We talked and he caressed me.  I liked it, all of it.  We discussed how we would move forward.  With my place here, my transition, things we would like to do.  I admitted that I feel less sure about being a full time slave than I used to, but I am still keen on being trained.  He told me that he would like to go out with me, just let me be Caitlyn somewhere I don’t know anyone, maybe dinner, maybe dancing.  A date.  I like this idea.  I’m not sure how comfortable I’ll be when it happens, but I like it.
    My memory gets a bit fuzzy here.  I think my brain might have shut off from overload at this point.  I know we got on the bed.  I got on first I think.  I laid on my back fully clothed.  He embraced me, stroked me, caressed me, fondle me.  At some point my top and bra were gone.  I found them when I left, but at this point I have no clue where they went to.  My nipples, he played with them as we kissed, my chest, abdomen, my whole body had electricity going through it, a fire through my veins.  I couldn’t stop shaking. We moved.  His tongue met mine.  A blur.  At some point the plug came out and He was in.  My feet on His wall again.  Shaking.
    When I - think - I finally got my senses back, He was holding me tightly.   I felt small and weak. We talked again.  Once more, I’m still so glad He does this.  He told me something important.  Something I have to share.  He told me I am His slave and I am His property but I am also his girl.  His girl.  I felt so happy to hear that.  His girl.  Finally, I was getting somewhere.  At long last, I was really becoming a girl.  His girl.
    I had to leave.  No, just s few more minutes.  I had to go, work stood between me and being His girl for the rest of the night and I hated that. I hate that.  I drove home thinking about what I had gone through that night.  I haven’t really stopped thinking about that.  Electricity.  Fire.  Shaking.

I am His slave, His property and His girl.  He is my Master and my Owner.



    ~Caitlyn

 

P.S. as I typed this into my journal tonight, I notice that SirHalligan was the most recent person to view my profile here.  Awesome.


8/27/2013 5:51:46 PM

Journal Entry#3
Written: 8/23/2013 - 8/24/2013
Posted: 8/27/2013

    I spent Wednesday night with SirHalligan.  I had a great time.  I am eager to get together with him again.
    I now see more clearly what it is to be a full-time slave, though I am still unsure if this is indeed what I want.  I certainly am curious to continue exploring this aspect of my submissiveness.
    When I arrived He and I discussed what the night may bring and what I may be looking for in a D/s relationship with Him.  I was asked to strip then told to get on my hands and knees on His bed.  I was punished for breaking His rules, I had cum without his permission, I deserved what I got.  Next, I was ordered off the bed and to stand.  He tried a maid’s outfit on me, it fit and it was arousing to wear it.  I was then collared and put in cuffs, which I also found exciting.  He then had me get up on the bed on all fours while he inserted a plug into me, I haven’t much experience with plugs, but I believe that is a thing of the past.  I was told to sit on the floor and was handed a folder containing my new mantra which I am to memorize, protocols and a list of positions I must learn.  I don’t believe I’ll have any trouble with the mantra, the protcols or learning the positions, but these are wholly new things to me and I am nervous because I don’t want to disappoint Him.
    I was the told to remove the maid’s outfit and told to return to my position on the bed.  My face in the pillows, wrists affixed to ankle by the cuffs, I couldn’t see much but I heard as he collected some items from around the room.  It was a little nerve-racking but I was exhilarated.  SirHalligan used a violet wand on me for the first time.  I have no idea what I thought a violet wand felt like before that night, now I know.  Now I know I’d like to try it again.  Maybe see how far I can go with it, see how intense it can be.  He only did this for a little while, I think He just wanted to introduce me to it lightly.
    I was then released, my hands disconnected from my ankles and made to lie on my back.  I  was completely turned on at this point, my head was swimming.  He laid down next to me, caressed me, played with my body, aroused me like i’ve never been before.  He removed the plug and in went the dildo I had brought.  In and out as he fucked me with it.  Oh, god it was overpowering, he told me to tell him when I was about to cum, I told him and he forbade it.  I’ve never held in an orgasm before, until that night the goal was orgasming.  I managed to, though I’m not sure how I did.
    Then it was time for Him, my legs were pushed up over my head, I could feel my feet on His wall.  He entered me, deep and strong.  He fucked me like Iv’e never been fucked before.  I didn’t cum - I couldn’t.  When He finally gave me permission I think I felt like I was put on the spot, I’m not sure though.  I had wanted to so badly and then something inside of me blew it.  Though it was still satisfying to know I had pleased Him.  I don’t think I’ll feel any need to cum if the feeling of satisfaction is this overpowering to know I have pleasured Him.
    I was then allowed to dress, my panties, bra and a t-shirt I had brought were what I was told to wear.  We then went to bed, at first I assumed we would go strait to sleep, I was - very happily - wrong.  We talked for hours - I mean literally - hours.  About everything, beer, travel, food, our jobs and so much else.  I’m so happy He did this, it made my immensely more comfortable.  When we finally did go to bed, I couldn’t sleep, a combination of my electrified nerves and my own uncertainty.

I am His slave and His property.  He is my Master and my Owner.



    ~Caitlyn


8/20/2013 7:17:11 PM

Journal Entry#2
Written: 8/16/2013 - 8/17/2013
Posted: 8/20/2013

    I spoke with SirHalligan again tonight.  We chatted for quite a while and I am more intrigued than I was before.  He has asked me to continue with this journal so this is my second entry.
    I should perhaps illuminate some things I mentioned in my first entry.  I would like to try some serious bondage in the forms of heavy irons and of shibari.  Especially pertaining to positions which make me uncomfortable and those which may make me more flexible.  I have always been interested in the more challenging forms of bondage, upside-down, asymmetrical, painful and trying positions.  I have yet to try any, but I am hopeful that SirHalligan will help me explore these in-depth.  I am also interested in circumstances which leave me vulnerable and not under my own control.  Wrists tied to ankles, head-down-ass-up, feet held as high as they will go and similar poses.  These sorts of positions have fascinated me ever since I first learned of BDSM far more than a pair of handcuffs or a ball-gag ever will.
    I also wrote, in my fist journal entry, that I would also like to pursue sensory deprivation.  I don’t really know what it is about it that makes me so curious about it.  I think it scares me.  I have been blindfolded before, and I found it arousing, however I felt that it could have gone further.  I would like not to be able to see or hear anything, it would be like being trapped in my own body, only being able to feel the pain or pleasure I was experiencing at the moment.  Unable to know what is going on until it - maybe literally - hits me.
    SirHalligan has asked me to write in this entry about who he is to me and what I feel about him.  To me, he is my master.  I shall call him this whenever I address him.  I know he is interested in getting to know me better and helping me become the submissive trans woman I need to be in my heart.  I feel that I may have found the Dom man I need to help push me toward my goals.  He may be strict, but I know that is for my own benefit.  He has shown compassion for me and that isn’t something I was expecting so openly when I first met him, I am pleased to have found someone with these qualities to help me transition.
    I am still unsure if a full TPE relationship is what I need, I think it is but I’m not really sure what the would entail.  On one hand, if someone had power over me 24/7 I couldn’t backslide, I couldn’t falter on my path.  On the other hand, I am fairly ignorant of what that sort of a life would require of me - what SirHalligan would require of me.  I have an uneasy feeling that it would be too much for me.
    He and I are meeting again on Wednesday and I am excited.  He has assured me that I will come to know what my life will demand of me when we do.  I am only spending one night with him so I’m sure it will only be a small taste of things - whatever they may be -  to come.  He has asked me not to cum until he commands it as I am his property and therefore so are my genitals, I will do as best I can at this.
    Finally, I have been considering coming out to some friends.  This shouldn’t be a very serious issue, people mistook one of my friends - of the same apparent gender - and I as a couple for years, so there shouldn’t be any sort of negative backlash from him.  I am also considering coming out to my brother, he’s a bit more tricky.  I want to come out to him but I think he would feel that I was either lying or - if he believed me - that I was trying to play the victim and take advantage of the hand that life has dealt me.
    Anyway internet, that’s journal entry number two, number three should follow Thursday or Friday night.



    ~Caitlyn

 

P.S.  I could not help myself, I came.  I came on Saturday night while waiting for friends to call me.  I know I have made a mistake, I couldn't help it I haven't gone without an orgasm for more than a day or two in the past few years and I was excited about meeting SirHalligan for something more serious than dinner.  I know I will be punished, SirHalligan has told me so, I only hope confessing my indiscretion my lighten it a bit.


8/15/2013 6:36:55 PM

Journal Entry#1
Written: 8/14/2013
Posted: 8/15/2013

    Okay, umm, I don’t really know how to start this thing, so I’m just gonna jump right on in.  Last night I met with SirHalligan and we had a little talk about what He and I might want and he asked me to keep a journal of some things, especially those regarding a D/s relationship with him and those of my transition.
    I had a nice time last night and I am excited to see where things my go from here.  I am truly serious about transitioning and I think SirHalligan could be very helpful in my doing so.  He very much seemed to want this for me as much as I do.
    He was fun to talk to, not that I said a whole lot of anything.  I was too nervous.  But I did manage to get across that I want more.  Plus he had some great dog stories.  Who doesn’t like a good dog story?  If you can show me someone that doesn’t, I’ll show you someone you should have never met in the first place.
    I am more curious than anything about BDSM in general, I’ve done some stuff like handcuffs and rope harnesses and similar things but nothing I really consider to be very serious - or frankly - exciting.  I am looking for something more challenging, more thrilling and more stimulating.  I would like to get my feet wet with someone who is willing to have his way and is creative about it.
    Maybe something metal?  Maybe suspension?  Maybe sensory deprivation?  I don’t really know, but I am interested and open-minded and willing.
    I know I’m turned on by some pain, i’ve been spanked and whipped before and I have savored it.  That said, I know that too much won’t do anything for me, blood, permanent - or provocative - marks or pain for it’s own sake aren’t really my thing.  I’d be much more interested in the occasional caning, a difficult position while bound, a thorough enema or perhaps some clamps placed artfully.  Maybe dangerously is the right word?
    I know that I absolutely am interested in giving and receiving pleasure.  I would like to try E-Stim, water stimulation and I would love to be able to cum solely through penetration alone, I’ve never been able to do so and I’ve been jealous of others who can.  I don’t know if I’m good at giving head, no-one’s ever said anything one way or the other.  I’ve gotten head and - honestly - really I was just fine getting head and didn’t need to comment, so I don’t blame anyone for not telling me if I’m good at it or not.  But practice can’t hurt.  Or can it?  I don’t know if I’m a good fuck either - probably for the same reason.  What I do know is that I’m not good enough at either.  I hope I will be someday, but what does that really matter to me?  A lot.  I want to be someone who is more than just “there to be fucked”, I want to be a real part of it.
    On to the topic of my transition.  I feel about the same as yesterday, happy to be getting on with it at last.  For so long it felt like I just had to sort my shit out and this was how my brain needed to do it.  However, I’ve known for quite some time that that’s just bullshit and I was making excuses to not move forward.
    I feel like I now sit more femininely with my back strait and ankles crossed.  I don’t know if that’s true or not, but I’m optimistic that it is.  My green dress - my favorite dress - is clean so I’m wearing that, a pair of floral print sheer panties with my purple bra.  I know I’m not supposed to wear a bra with this dress - it shows too much-  but I can’t help it, a bra makes me feel more whole.  No makeup tonight, it’s too late and I’d get outed if I couldn’t get it all off before work tomorrow.  I am wearing a necklace though, a big silver and turquoise one that makes a lot of noise when I move.
    Moving forward, I would like to just be OK with me as me.  I would like to be able to walk down the street as myself and have no-one - especially myself - think anything of it.  If I could, I would go tranquilly, unremarkably and comfortably about my business without even having to think about whether I am being watched or not.  And I would cry with joy when I got home.

    ~Caitlyn


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subamber66
 
 Age: 39
 Ft. Lauderdale, Florida