Dear Mistress Gail,
I caught my 21 year old son masturbating in the bath the other day and noticed that he lacks
the skills to um… polish his knob. I was wondering if Mistress would be interested in showing him the proper way – under Mistress’ expert supervision.
Yours sincerely,
James (Senior).
Dear James (Senior),
Thank you for you’re email. I would be delighted to do so. Please Contact Me on My cell to discuss session details, dates,and times.
Wicked regards,
Mistress Gail.
James (Junior)
gets a “Pull your wire masturbation boy” lesson
James Junior arrived at my Dungeon last Saturday morning promptly at 10. When I heard him knock, I opened the door to see a nervous young man standing in the drive stuttering as he looked up at Me: “Mmy ffather sent me to You for mmy ffirst lesson.”
“Well hello there, you must be James Junior, come inside,”I say, giving him a wicked grin. “Your father and I have discussed how you are to be punished. Then, you will be taught how to pull your wire and polish your knob the proper way, by Me!”
“Yes Mmiss,” he mumbles, unable to hold my gaze.
“Well,” I shhoot back at him, “what I require from you young man is to take all your clothing off, hang it neatly on the hanger, and then wait for Me on your hands and knees, bum in the air. You’re going to get it on your bare bottom today young man!”
“Yes Miss,” he answers nervously, eyes still downcast.
I decide to torment him. “See you in five minutes young man,” I say, closing the dungeon’s back door with a thud and laughing at his adolescent fumbling.
But I didn’t leave. I watched him voyeuristically through a tiny crack in the door frame. With anxiety hanging over him like a dark cloud, he got undressed and started to walk around My dungeon, nervously eyeing the paraphernalia hanging on the walls and the intimidating ‘furniture’ that looms over the space like a bird of doom.
“I’m sure this is the Mistress Gail in the photograph my father caught me wanking to in the bathroom,” I heard him say out loud, no hint of a stutter now. Instead of waiting for Me with his bare bum in the air, he becomes aroused by his thoughts and I watch as his cock grows to full erection. It’s pointing straight up at the shiny steel restraints dangling from the ceiling. A stray sunbeam lands on the swollen little head. It glows purple and I notice a drop of pre-cum glistening in his pee-hole. Is there a devil in my little mouse?
Caught up in his own excitement he’s clearly forgotten that he was instructed to wait for Me on his knees with his bum in the air. “Your father mentioned to Me that you were hot-headed with a will of your own, and following instructions is not one of your strong suit,” I bark at him, watching in satisfaction as he jumps at the authority in my voice. Assume the position!”
He is down on his knees in a flash tightly clutching his stiff prick in one hand.
“Hands off you’re cock young man,” I command. “Your penis is now Mistress Gail’s toy and no longer yours to entertain yourself with when in My presence. Your dick is now My property, and is there for My entertainment! Is that understood?”
“Yes Mmiss, understood,” he mumbles at my feet.
His bare virgin ass hangs in the air. I cannot resist. A loud thwack echoes round the dungeon and I stand back to admire the hue of warm red heat spreading across both his bare ass cheeks.
“Count young man,” I give the instruction as I caress his red bum with the tip of my riding crop.
“Yes Miss,” he yelps, as the crop lands another stinging blow across both bottom cheeks. “One, thank You Miss.”
That’s better young man,” I reply, lovingly caressing his burning bottom. “You’ll be getting another four of these. I want your bottom warm, red and tender for the session. Next time I give you an instruction, make sure you follow it to the letter! Understood?”
“”Understood, Mmmiss,” the thwack of my crop almost drowns out his stuttered reply.
“You have permission to turn round and kneel in front of Me with your hand on My toy,” I say, the cropping over for now. No playing with it young man. Holding only, until Mistress gives you permission.”
“Yes Miss,” he answers, and I notice that his cock is now even stiffer.
“Show Miss how you pull your wire and polish your knob,” I instruct, after watching him struggle not sneak in a tug.
”
“Yes Miss,” he answers and I can hear the humiliation in his voice. But his eyes light up with sexual excitement as he starts to stroke his cock, with Me watching.
“Is that all you got young man?” I ask mockingly, after letting him enjoy a few wank strokes. “I see why your Father has sent you to Me. You only know one style of masturbation and watching you pull your wire as fast as you can is monotonous.
Mistress requires you to learn variation to spice up your masturbation sessions. Remove your hand from My toy masturbation boy, and fetch My strap-on harness from the rail on the wall, to the right hand side of you.”
Is this what Miss wants?” He asks, uncertainly touching the giant pink dong.
“Yes, bbring it over here,” I say, chuckling at his embarrasment.
I instruct him to get back down on his knees. Then I buckle the harness in front of him, the big dildo slapping him in the face.
“Eyes on My prick, boy,” I instruct. “Mines a cock. Yours is a My toy. Now pay attention.”
He watches as I stroke My giant sch-long. “Now, I want you to give your shaft four long strokes like this,” I tell him. “And Mistress will be counting them very slowly, so no rushing masturbation boy. Let’s get some action going in here. But no rubbing over the head, yet.”
I bend forward from the punishment bench and place a generous amount of lube onto the tip of My toy. I can feel his cock throb as I’m doing it. I sit back to enjoy the the sights and sounds. I do enjoy the delicious squishy noises a masturbation boy makes jerking a well lubricated cock in front of me.
I light a cigarette and a haze of white smoke fills the room with the smell of the tobacco. It arouses James Junior and I laugh salaciously as he pulls in front of me with his tongue hanging out.
I warm to this exhibition as I realise how much he enjoys playing with himself in front of a mature dominate women under guided masturbation instruction. “Give Miss a few long slow strokes,” I say, watching how his eyes light up with pleasure. “Now rock Your hips back and forth while you stroke, pretend you’re fucking a tight little pussy in front of me. Hmm, you’re getting the hang of it now masturbation boy. I see you are starting to leak. How does your cock feel now?”
“So good Miss,” he replies. It does seem like my mouse is turning into a lion. “Now give Mistress a few long fast strokes, from the base of your shaft all the way over your little head.”
“Yes Miss,” he answers. “And may I say how much of a turn on it is to masturbate in front of Mistress. Your green eyes shine like a emeralds in the dungeon and the wicked smile on your lips is every boy’s masturbation fantasy.”
“Hands off My toy young man,” I say in response. “You’re not yet forgiven for ignoring the instruction to wait for me with your ass in the air. For that I have chosen an exquisite little humiliation to remind you that this is My realm, dear boy.
Looking me directly in the eyes with a shimmer glint in Her green eyes and playful laugher cascading from her lips.
I will be requiring you to lick kiss and clean and sniff Mistress’s starfish for Her as Miss stepped off the punishment bench removing Her strap-on harness and placing it to the side and bending forward in front of me for me to have full frontal view of her lovely feminine bottom.
Pulling Her G-string aside, I hear Miss say get your tongue in there and lick Miss starfish clean with your tongue masturbation boy can’t have you coming your coco coco so soon young man as that would simply spoil all Mistress’s fun.
Wiggle that tongue of yours more on Mistress’s starfish young man I want to feel that tongue stretching up and down and working overtime on Miss starfish young man.
As at the moment it feels only like a flickering tickle down there. Yes Miss as I slowly started to work my tongue up and down on Miss starfish.
Keep going masturbation boy I’m wanting lots of tongue action out of you from down there boy Yes Miss.
Ah that better young man feels like a soft breeze and a cool moist tongue working simultaneously on Miss starfish that’s delightful pleasurable young man.
You’re diligence boy has earned you a reward from Mistress Gail and permission is granted to kiss and worship Miss gorgeous derrière masturbation boy.
Make sure you hands remain at the sides of your body at all time while doing so masturbation boy. Yes Miss.
Word of warning boy no biting Miss exquisite feminine bottom Young man I will be requiring soft butterfly kisses from you on my well rounded shaped derrière boy. Yes Miss.
The view of Mistress exquisite bottom from behind was a breathtaking sight and I felt my toy grow even harder as I leaned forward to place soft caressing butterfly kisses on Mistress feminine bottom slowly and gently I kissed each cheek lingering from one bum cheek to the other making sure to give both bottom cheeks equal attention loving every second of begin beneath her exquisite feminine bottom.
That enough for now masturbation boy as Miss turned round to face me what I will be requiring from you is for you to stroke you shaft up in one full lengthy stroke from the base of your shaft to the top of your shaft and then to polish your knob three time to the right for Miss and then three time to the left is that understood masturbation boy. Yes Miss as Mistress bends forward to place another generous amount of lube onto my toy shaft rubbing the lube into my toy as I groaned in ecstasy and Mistress giggled in delight as She tormented and teased Me with her hand
Mistress removed her hand . Commencing now young man Yes Miss as the intensity of the masturbation training increased one two three fast strokes now polish your knob masturbation boy as Miss turned her wrist in a circular motion three times to the right and then in a circular motion three times to the left Mistress eyes lit up once more encouraging me to pull my wire and polish my knob faster that its perfect masturbation boy and then I heard Mistress say Stop glancing down at my toy to see so much pre cum dripping from my head.
Looking up I noticed that Mistress has her back turned to me and then bends forward saying get your nose back into my starfish and sniff it like a good puppy for Miss as your toys tail wagging super-cal-fragilistice-xpialidocious for Miss and more direction is required to take charge of your orgasm. Yes Miss as I inhaled in Mistress feminine aroma of her starfish. Keep sniffing masturbation boy. Yes Miss.
That enough young man Mistress turns round to face me placing a small red towel down on the carpet in front of me.
Last two strokes young man and there’s a catch you are to stroke your toys shaft for three strokes and then to presence your little head to Mistress Yes Mistress one, two three presenting my little head which Mistress whacked with a rubber looking shoe sole again young man stroking one two three times presenting my little head again which is whacked once more. Enjoying my masturbation lesson immensely.
Lube up boy as a tube of lube is given to me yes Miss.
Its Cum shot time masturbation boy and Mistress wants to see all those cum shoots of yours on Her red towel.
Yes Miss you have permission to pull your wire till you blow your load masturbation and lets see how far those cum shot go masturbation boy Yes Miss. Oh my word they shot quite far well done masturbation boy.
