Chronicles of a Masturbator

I had an interaction with a subby over email. Here was his email:

Hi,
I am Johnny, I'm 25. I am reading your blog in these days. You are very nice and your blog is wonderful, but are you sure you are not a fake profile? I have seen so many men acting as girls just to laugh at boys, lol. I am not sure you are a man but I have some doubts. Wanna bet? Take a photo showing a three with your hand or just part of your body to prove that you are a girl and a paper with written "Strict Julie Spanks" on it :D You can obviously not show face. If I loose you choose the punishment. It can last as much time as you want. I could take a video as proof. If instead you are a man just say it and I would not tell anyone but you would have to do a dare of my choice. Oh and it will be difficult, of course. Please be honest. :)
Let me know, lol.
Johnny

Well, normally I would ignore this type of question, having already posted various pics of myself, and it being actually pretty impossible to both maintain anonymity and "prove" I am a woman (and who gives a flying leap anyways?), but I thought it would be fun to respond with the requested pic, set him a punishment, and see if he would actually carry it out. So I sent him this by way of response.

He did email back clearly acknowledging I am a woman (duh!), but so far he HAS NOT carried out his punishment. Who knows. Maybe this post will SHAME him into actually following through?????

Then I got to thinking. No fair that doubting johnny should get to see a pic of me that you guys have not, so I decided to post it. While I'm no incredible beauty, I kinda figured some of you at least might want to masturbate to it?

I was pretty sure that my loyal and faithful lil sketch slut, lil josephine, would, especially since I can order him to do so. But I got to wondering, what naughty thoughts pass through the male subbie's mind as he masturbates? So I thought I would centre the post around that thought, and get lil jo to chronicle his own personal masturbation.

Would it be possible for you to masturbate to my picture, imaging me Domming you in various ways? I would love it if you did, and then emailing me back with what thoughts and images danced through your mind as you did. Maybe even illustrated? ...

And here is his response (which, as you will read below, is wonderful stroking for my ego!).

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What an invitation! What a photo, a privilege! Like a boi needs an invitation for that. What does a closeted sissy think about when masturbating to a photo of Ms Julie, the epitome of Dominance:

I am honored with Ms Julie's picture to contemplate? Having your picture Ma'am just heightens the 'possible-ness' the nearness. Adding the fact of it being a picture from someone that 'gets it'. an instruction from a domm. I can't resist 

You asked about my actions, technique, but it is pretty boring. i have done things like spank or plug myself, or femme up a bit, even put pegs on my tits. But mostly its just get comfortable and bring in some favorite fantasies. My mind likes to put me in the scene.

(I'd like it to be like this: I am in a full Maids uniform summoned into a living room full of ladies giggling and deriding me. I have to go round and curtsy to each one in turn and kiss their toes first, then i lower my panties to my knees. Perhaps I have to put in a large challenging butt plug first while the ladies egg me on. As i struggle to finish one lady jumps up and pushes the plug home to the applause of the other ladies, Then I put on my 'performance'. I am totally humiliated but as my focus returns to Ms Julie I imagine a few 'encouraging' words from her: 'If you don't come soon I'm gonna tie your cock and balls back between your legs and beat them blue josephine! - you obviously have no use for them.' I become a total whore at this and i don't care or notice whose in the room anymore, I just want to release. This is the point where I would actually cum, as I soon do to mocking laughter. Of course I have been trained to catch my cum and eat it.)

But I prop up my picture of Ms Julie.

I imagine i am in her absolute control. At last i am going to get used and punished like a real sissy bitch by someone who 'gets it', who isn't going to hold back or stop the second i say 'ow!'. Even if i stupidly put my hand back to cover my ass Ms Julie will just whack it out of the way, or say menacingly 'Do you want me to restart the count josephine?'.

To make it more real I go beyond the photo. I imagine I have a business trip to the eastern US and Canada. I find I can get away for a couple of precious days. Amazingly spending a couple of days with Ms Julie becomes possible! So many things i want to experience. I want Babette's (Femme and flogging) Feast!

So here are fragments of an imagined hit-n-run visit to Ms Julies place. The order is random and overlapping - hey its masturbation:

• Before i fly in to the airport I have been instructed to wear a pink shirt and at least two other visible pink items I have two pink socks on, barely visible under my jeans. I explain this to Ms Julie who is unimpressed at my cop-out. Ms Julie motions for me to stand close directly in front of her. She pinches both my tits eye-wateringly hard through my shirt and doesn't release them. I try not to react in the crowded airport. You really need to learn to do as your told and properly josephine'. 'Shit' I hiss as Ms Julies grip continues... 'Mmm a potty mouth too...'

• (or) I pause a little awkwardly. How to greet Ms Julie? i move to kiss a cheek but Ms Julie pulls back slightly. 'Nuh-aah' she waves a finger. 'Where's my curtsy?' this takes me by surprise. we are in a crowded airport after all. Ms Julie is waiting. I put my hand luggage down and bob a barely noticeable curtsy... 'Well that was crap.' Ms Julie says loudly. 'Do it again and hold it for 10 seconds...' I'm blushing now, but I do it. Surely people must be staring. Ms Julie smiles...

• (or) Ms Julie Is waiting for me at the airport holding a pink sign saying 'josephine' with some very feminine bows and a big pair of pink lips drawn on it. Ms Julie greets me loudly as 'Josephine' when I go near her. I am blushing as a few faces turn and smile, or frown. (Do people still hold up signs with mobile phones now??)

• After my welcome spanking Ms Julie decides I need to learn a no-potty mouth lesson. I get to sit on a hard stool with my panties down. Ms Julie has a light-bulb moment and returns with a sheet of sandpaper to put under my red backside. And I am ordered to write: "I must not use bad words" 100 times with a disgusting tasting bar of soap in my mouth. Mistress says: 'Write carefully jo. if there's any mistakes you're writing that line again 10 times...' 'Efth Biftweff (Gak)'.

• I couldn't resist, what an idiot, I had to bring that fucking bent wire coathanger along. Already sore from my arrival spanking, I failed to mention the coathanger. Ms Julie spies it in my backpack.  'Oh look!' Ms Julie smiles in recognition. 'When were you going to tell me about this josephine?' 'I ... uh ... I.' 'Was josephine a widdle scared?' (Ms julie uses a condescending babying voice as she playfully swishes it through the air)  'Ahm ...  ah well  um ... well yes Ma'am, a little.' 'Why don't you give me a little demo of how you spank yourself josephine. 20 nice firm strokes...' (a little later) 'fascinating! Do you fantasize that I'm doing that when your alone joey?' (I'm a bit breathless even from this short self spanking. That coathanger stings!) 'Y ... yes Ma'am.' 'Well lets see how reality stacks up shall we?' '*gulp* yes Ma'am.' 'I'll try 20 myself ...' the first strike takes my breath away... i'm an idiot bringing that thing!' I think...

• Ms Julie is acquainting me (orally) with Adam, her famous strapon/punishment-pegger. I am on my knees, feminized and blindfolded. Hands bound, maybe clipped to a sissy collar.  'Just a second josephine...' Ms Julie withdraws Adam, seemingly to grab for something. I take the opportunity to stretch out my jaw. I hear some quiet movements, a cupboard door maybe?, but Ms Julie has returned. 'OK, open up again darling.' Ms Julie seems to be back with Adam. I open for my mouth to be refilled. I am entered, but immediately there is something different. It's softer, smaller... crap its a real cock!!!. Instinctively I pull back. 'Josephine. Relax. Stop and think. How long, how often, have you thought of this, longed for this?'  As my panic quickly subsides. I take in her words. 'This is a gay friend of mine, Keith. Just think now Josephine. You are with friends...' My mind swirls to catch up. A real cock. No ... but a real cock ... I take 3 - 4 - 5 deep breaths and slowly open my mouth... 

• Ms Julie says: 'I really wanted to do the plum thing with you josephine and show Sue.' jo: 'I ... I don't know Ms Julie I...' Ms J: 'Oh, I'm sorry josephine (laughs), that sounded like a request didn't it. silly me. It wasn't a request.' jo: 'Yes Ma'am'.  ... jo later gets beaten on his balls also but with a small leather flogger with many tails. Sue thinks this is hilarious and has to have a go...

• Ms Julie has shared with david that this visitor is responsible for some of the humiliations and punishments david has suffered. jo is trussed up gagged and mortified to be revealed like this in front of david without even an introduction.

david punishes jo with some gusto when he understands how jo has contributed to some painful humiliating past moments. Ms Julie is struck to see a dommy side of david and has a thought: 'david did you want some oral attention from this bitch?' ... jo's eyes widen and he tries to protest into his gag. david looks uncertain. He's thinking about it ... ('Mmm two birds with one stone!' Ms Julie thinks...)

• there is a figging of course: 'Twenty minutes with the fig jo, remember? only 12 to go.' but being figged with this horrible humbler on I have to concentrate hard not to straighten and hurt my balls. I'm dripping sweat! '11 minute's darling. ...' (Fuck!!!! I scream in my head.)

• I'm impaled on Ms Julie's punishment stool filled by 'Adam', sandpaper under my balls and a spanked ass. Ms J: 'I didn't think we'd have time for this joey. Aren't you glad we found the time?' jo: 'yeff mfffteff'. I manage breathlessly into my gag. Ms J: 'Oh, I almost forgot to touch up those inner thighs. oooh! I can use your coathanger for that! (gleefully)' ...  'I loved that photo you sent me a while back, how wonderfully the coathanger marked up your inner thighs.' I wimper. Ms J: 'Stay right there joey.'

As I masturbated, looking at Ms Julie's light frame (but obvously fit-n-healthy. I would put it that Ms Julie has that 'I've got my shit together how about you tubby?' type of body. Is Ms Julie 5'8"? I can't remember)

I imagine a scene, or I imagine events, specific toys. realities from my fantasies? This is a beautiful, fit, strong dominant lady. I imagine I'm there with her. I am reminded how I love the idea of a smaller lady dominating a larger man. it has something surpassing any physical dominance, the usual starting point for male domms. I am tallish, just under 6' but not heavy or muscular. A bit loose skinned in places, like my arms, lower belly if the truth be known. but I would bend over backwards, forwards, anywards to maintain submission to this lady. to feel physical pain harsh instructions, scolding, mocking and humiliation. how I'd love to be spanked epicly with all the implements. like chapter after chapter of a good book. Or movements of a symphony from a maestro perhaps. dreaded whacks and forceful intrusions of dildo, plug. There are surprises too: a pinch, a face slap, a position I can't hold/I must hold. Ms Julie doesn't even need to restrain me but she can if its what she feels like. She laughs at my predicaments. I don't have to top from the bottom now. I want/I have all of it. as I wank away a pathetic sissy wannabe.

• I would want to strip down to bra and panties and heels as soon as I arrive. I want to be femme and sub the whole time. no hint of male status.

perhaps there is no small talk. Perhaps it has been agreed that I must be punished on arrival before anything else for all the annoyance, topping from the bottom and whineyness I have inflicted on Ms Julie over a couple of years. Not to mention a few punishments I have inspired on david that should rightly have been inflicted on me.

• When I am stripped I am blindfolded. I haven't seen Ms Julie yet. I've only heard her commands. her voice as forceful and confident as I had imagined. Ms Julie finds the heels I have brought along and puts them on my stockinged feet. I feel leather cuffs go around my wrists in front of me. I am led blindfolded and teetering through to another room. Something seems to be attached to the cuffs. My wrists are pulled above my head. a spreader bar is attached between my legs. I wait...

• I want to be a maid between punishments, peggings etc. serving constantly, bobbing curtsies, mincing about, doing dishes, ironing, etc. Being commanded, corrected... Will i hang the washing on the line? take the bin to the curb?

• at the end of the first (long) day I am put in a pink babydoll with beautiful pink satin panties that feel cool on my well spanked bottom. I also have pink mittens on to stop me misbehaving (I know what Goddess Gretchen wants here too) Ms Julie adds the final touch of a pink dummy. I cant stop myself from starting to cry at that point.

• When it comes time to leave I'm gonna ball my eyes out and beg to stay... 

• I say: 'Umm I did bring this present for you Maam. um its a strap on with a clit and anal stimulator attachment. 

I always thought pegging left all the work with the domme Maam. and not much physical fun. So ... people seem to rave about this thing. you can either set it to various levels or it can vary the intensity to the clit stimulator based on how hard you ... ahm ... use the strapon Ma'am. you can try it later with david if you like Ma'am?...' Ms J: 'Oh no josephine. Get on the bed with your pussy ready right now. Where's that lube...'

(45 minutes later) '... 'Oh! that's orgasm number 3 for me! I've gotta try this on David!...'

This would be heaven Ma'am. My pussy and my spanked ass would be killing me, but if I could please you this much... This is the stuff that sets me spurting.

• I'd love to insert a scene of orally servicing Ms Julie but this seems out of bounds - david territory. Maybe david could beat my ass and flog my balls during and after me servicing Ms Julie's ... or any time he thinks i'm getting any enjoyment.

But what gets me over the top? Most of all I think about a long, luxurious, thorough spanking, paddling, strapping and *gulp* caning from a Maestro. and then being led bawling and sniffing to the corner by the ear by a small woman. I stand on trembling knees in heels. my thigh backs inner thighs, my butt crack have all had their share. even my cock and balls have been colored by a flogger.

Sue walks in: 'Woa good job Jules!' she seems genuinely taken aback. Ms J: 'Well he really needed this didn't you josephine?'   'Yes Maam!' I say, a little too loud and emphatically. my voice breaks on the next in-breath... 'Thank you Ma'am' I say a little more evenly... Ms J: 'Am I a bad mistress if I peg him again right now Sue - he ... she looks so pathetic?' I wimper despite myself. Sue: 'Oh no darling. I think she'd be disappointed if you didn't.' (both giggle. jo wimpers).

This is the stuff. The thought of being spanked past that point of control into crying and begging and then instead of stopping you pause only to come back with the cane. or perhaps some creative humiliation comes to mind. A spanking is a spanking but there are so many more possibilities for humiliation. Sooo many! E.g. I am in the corner, well spanked with my skirt pegged up to display my ass. You walk past and say 'Stand on one leg josephine'. A little discomfort a little humiliation. it is just a tiny thing, another delightful mouthful at the feast.

• when I leave Ms Julie gives me a top-up spanking (I must be black n blue by now i think my face is teary and screwed up.) and gives me a parting present of a pair of hessian panties (another idea i have mentioned that is coming back to bite me) to wear on the flight out so that 'I will keep her in mind' she says. (later the stewardess asks: Are you comfortable Sir?...

When I finally come, There is a physical relief. But I feel guilt too. I think I can honestly say if I was with Ms Julie for the weekend I don't think I would be bothered about coming! (Maybe I'm kidding myself but I think this is true). I want all the other stuff, I can have a wank any time. I'd much rather give Ms Julie an orgasm as Ms Julie sat on my face (presumptuous).

Presumptuous indeed!!!