by Ruby Madden
pup – ethan: I can do that. As painful as that may be
Mistress Cherry: good, exactly where you need to be
Mistress Cherry: I'll let you know when you are allowed to touch your cock
pup - ethan: Yes Mistress. I won't disappoint you
Mistress Cherry: good boy
Mistress Cherry: If I made you web-cam your hard cock to confirm you're not touchy-touchy, would you?
pup - ethan: Yes I would
Mistress Cherry: okay, then. Do it
I turned on my mobile web-cam and placed it on top of a file cabinet next to me, where I sat at my desk. It was at a height and angle that would allow her to see her property. Me.
pup - ethan: Mistress, can you see me?
Mistress Cherry: Yes, I can. Well done.
pup - ethan: Thank you, Mistress.
Mistress Cherry: Okay, I would like to visually stimulate you. Sound fun, pup?
pup - ethan: Yes mistress. It sounds very fun!
Mistress Cherry: perfect
Mistress Cherry: Mistress is always capitalized, puppy.
pup - ethan: I'm sorry Mistress. It won't happen again.
I marveled at how easy it was for her to find an innocent enough slip-up, to chastise me. I equally marveled at how I liked what it meant. Which only made me harder.
Mistress Cherry: hands off your cock, pup?
pup - ethan: They’re not Mistress, I promise. They’re on my lap top.
pup - ethan: It is VERY hard Mistress.
pup - ethan: Almost painful
Mistress Cherry: giggle... good
Mistress Cherry: imagine you're kneeling
Mistress Cherry: I'm circling you
Mistress Cherry: admiring your hard cock
Mistress Cherry: taking my time thinking about what to do next
Mistress Cherry: or not do
Mistress Cherry: how to make you suffer
Mistress Cherry: beg
Mistress Cherry: plead
Mistress Cherry: whine
Mistress Cherry: whimper
Mistress Cherry: every little twitch, I notice
Mistress Cherry: (no touchy-touchy)
Mistress Cherry: right?
pup - ethan: No touchy. I want to so bad though
Mistress Cherry: nope
Mistress Cherry: not yet
Mistress Cherry: you'll get to touch
Mistress Cherry: but ONLY how I say so
Mistress Cherry: WHEN I say so
Mistress Cherry: Capiche?
pup - ethan: Yes Mistress.
Mistress Cherry: good boy...
Mistress Cherry: what's the longest you've stayed hard and erect?
I had to think about this a bit…
pup - ethan: I don't know Mistress. For a very long time though. I have an extremely high libido
Mistress Cherry: good
Mistress Cherry: can you rebound quickly?
pup - ethan: Yes. Usually within 15 minutes I am ready to go again.
Mistress Cherry: you're doing so well....
Mistress Cherry: good, I like the sound of that
Mistress Cherry: one of the fundamental aspects of my Topping is I 100% get off on your cock, making you hard for ME. I will use it and abuse it. Sometimes, 2 to 3 times a day… once you’re trained.
Mistress Cherry: sometimes only once a week
pup - ethan: I understand and willingly obey.
pup - ethan: As much as you want, whenever you want, as long as you want Mistress.
Mistress Cherry: good boy...
Mistress Cherry: The idea of cock-caging is very appealing to me, pup…
I wondered when she would lock me up in a cock-cage? I both dreaded and craved it, contradiction of my desire all too blatant for me to ignore.
Mistress Cherry: still really hard, pup?
Mistress Cherry: (Mistress is licking her lips...)
Mistress Cherry: (I'm also aroused)
Mistress Cherry: No touchy-touchy
Mistress Cherry: giggle
Mistress Cherry: I know you're dying right now
Mistress Cherry: but please me
Mistress Cherry: by suffering a bit more...
pup - ethan: Yes Mistress. I am so hard! I am so horny! My cock is pushing against my pants painfully.
Mistress Cherry: good
pup - ethan: Yes Mistress. Whatever you wish.
Mistress Cherry: you may allow your cock out of your pants
pup - ethan: Okay.
Mistress Cherry: allow it to spring out and delight your Mistress
Mistress Cherry: minimal touching
Mistress Cherry: let me know once it's out
pup - ethan: Yes Mistress. It’s fully out.
Mistress Cherry: describe your hard cock to me pup
Mistress Cherry: don't get shy
Mistress Cherry: I'm a cock admirer
pup - ethan: Its very erect Mistress. Standing straight up to the point of vibrating slightly. The veins are standing out firm against the shaft. It stands at 8 inches, long and thick. My cock-head is swollen and pink.
Mistress Cherry: accept the image I just sent, pup
Mistress Cherry: this isn't me, but isn't she sexy?
Mistress Cherry: that big ass
Mistress Cherry: bent over
Mistress Cherry: stay hard for me
Mistress Cherry: god, I love that my new pup is hard and vibrating for me…
Mistress Cherry: it's equally difficult for me to resist the temptation
Mistress Cherry: of such a sexy tool
Mistress Cherry: for Mistress
Mistress resists temptation too? The temptation of me? Suddenly, I got it! She has to hold her desire in check too when she plays with her subs. Fascinating…
pup - ethan: Yes Mistress I shall stay hard for you. Thank you for the image, Mistress.
Mistress Cherry: I think she is a fabulously sexy pear BBW type
Mistress Cherry: love that booty
Mistress Cherry: still hard pup?
pup - ethan: I agree Mistress. Her ass makes me a bit crazy!
pup - ethan: Very Hard
Mistress Cherry: okay, you may take your forefinger and very slowly go around your ridge SLOWLY, three times (3x)...
Mistress Cherry: let me know if/when pre-cum starts to accumulate
Mistress Cherry: but enjoy the touching I'm allowing
Mistress Cherry: go slow
pup - ethan: Thank you Mistress. Oh my God. It feels amazing. I don't want to stop. I have a small amount of pre-cum escaping from the top
Mistress Cherry: once done with ridging yourself, take your finger down the length of your vein, up and down three times (3x)
Mistress Cherry: no gripping
Mistress Cherry: just the tip of your finger
Mistress Cherry: tell me how it feels (when you can type)
Mistress Cherry: then around your rim again... three times (3x)
Mistress Cherry: don’t cum!
Mistress Cherry: not yet!
pup - ethan: It feels like heaven Mistress. The excitement it brings is mind-numbing.
Mistress Cherry: good boy
pup - ethan: As you wish Mistress
Mistress Cherry: imagine ME still walking around you
Mistress Cherry: I reach out, with the tippy-tip of my heels and touch your cock-head
Mistress Cherry: you flinch with need
pup - ethan: Mmmmm... Yes Mistress! I feel it
Mistress Cherry: that hard, big cock twitching for me!
Mistress Cherry: just for ME
Mistress Cherry: no one else
Mistress Cherry: but ME
Mistress Cherry: right?
pup - ethan: Just you Mistress. Only you.
Mistress Cherry: still hard puppy?
Mistress Cherry: pre-cum dribbling out of you...
/>
I was about the hardest I’d ever recollected. Painfully so… Exquisitely so.
pup - ethan: Yes. I'm watching it now
Mistress Cherry: Imagine that I take hold of your shaft
Mistress Cherry: slowly pumping you...
Mistress Cherry: would you like that puppy?
Mistress Cherry: if so, beg for it NOW
pup - ethan: Yes Mistress.
pup - ethan: Please… Please…
pup - ethan: Please stroke my cock
pup - ethan: I yearn for your hands
pup - ethan: I want you to take hold of your property
Mistress Cherry: beautiful...
Mistress Cherry: you may grip your cock
Mistress Cherry: and very SLOWLY start to pump yourself
Mistress Cherry: focus on breathing
pup - ethan: Yes Mistress. The pre-cum is on my hands
Mistress Cherry: I SO wish I could watch you in person, working your tool...
Mistress Cherry: good
Mistress Cherry: use it to lube up your cock
Mistress Cherry: I hope there was enough?
pup - ethan: Yes Mistress. There is enough to get one side
Mistress Cherry: Okay, you may use another aid for lubrication
Mistress Cherry: Mistress takes good care of her pups and their tools
pup - ethan: Yes Mistress. I applying the lube now. You’re such a wonderful master
Mistress Cherry: You're welcome, pup
Mistress Cherry: now... you may stroke yourself to completion
Mistress Cherry: firm and fast
pup - ethan: Yes Mistress!
Mistress Cherry: I'm still circling you
Mistress Cherry: and you can smell the scent of my aroused pussy
Mistress Cherry: my need for sex
Mistress Cherry: to be fucked
Mistress Cherry: but not today
Mistress Cherry: today, we are training you…
Mistress Cherry: right?
Mistress Cherry: besides, I have other ways to use you
Mistress Cherry: right?
pup - ethan: Yes Mistress. I am not worthy of your pussy yet. Training to be completed. Yes Mistress. Use me in any and every way
It occurred to me how tenderly and sweetly she tended to my needs. Feelings and emotions typically denied a man in this modern-day, male centric world.
The way she dived into my mind, my psyche. The entrenchment of her enchantment. How my desperation was both at peak for her, eager to please, and eager to satisfy. Wildly alive within the ache and denial that she used to toy with, on me.
Caged freedom.
Mistress Cherry: good
Mistress Cherry: such a good pup
Mistress Cherry: goodness
Mistress Cherry: let ME know when you are there...
pup - ethan: Almost. May I use your picture?
Mistress Cherry: yes, you can use any images of ME that you want including the one I just sent you…
pup - ethan: Yes Mistress. I shall use that one and cum to you.
Mistress Cherry: good, I have one very unique request that you may decline, for now...
Mistress Cherry: once you cum
Mistress Cherry: contain it in your hand, as much of it as you can
pup - ethan: Yes Mistress I shall
Mistress Cherry: still stroking yourself pup
Mistress Cherry: while Mistress circles you
Mistress Cherry: smelling like sex
Mistress Cherry: wearing something sexy
Mistress Cherry: her heels clicking
Mistress Cherry: a small riding crop in her hand
pup - ethan: Oh God Yes Mistress
Mistress Cherry: a naughty grin on her sweet face
Mistress Cherry: good
Mistress Cherry: and when I tell you to come NOW
Mistress Cherry: will you?
Mistress Cherry: puppy?
Mistress Cherry: can you?
pup - ethan: yes!
Mistress Cherry: cum for ME
Mistress Cherry: now?
Mistress Cherry: be a good, good boy...
Mistress Cherry: one firm strike to your thigh
Mistress Cherry: and a wink
Mistress Cherry: a pleased, naughty wink from your new Mistress?
pup - ethan: Yes Mistress! I have cum like you asked
Mistress Cherry: good boy...
Mistress Cherry: this you may decline
Mistress Cherry: BUT
Mistress Cherry: it would please me greatly
Mistress Cherry: if you took a taste of your cum,
Mistress Cherry: since I love knowing
Mistress Cherry: I caused it to come out of you
pup - ethan: Yes Mistress if it pleases you.
Mistress Cherry: please do
Mistress Cherry: and then you may dispose of the rest
Mistress Cherry: How are you feeling?
pup - ethan: Relieved Mistress. Relieved of sexual tension.
Mistress Cherry: Awesome...
Mistress Cherry: take a shower if you like and enjoy the rest of your day
Mistress Cherry: I pat you on the head and undue the cyber-leash
Mistress Cherry: you are free to continue your day. Remember, no masturbation, no porn, no sex, understand?
pup - ethan: I understand and thank you for the pleasure
Mistress Cherry: You're very welcome, pup
Mistress Cherry: This pleases ME very much.
Mistress Cherry: ttyl!
Mistress Cherry: xxx…
I sat back in satisfaction. All of my pent-up longing, need and desire for her – satisfied. I felt sane again.
Whole. Content.
Sitting there, I savored these hard-won feelings for a long while before heading to the shower to start my day.
{ MISTRESS }
Settled into a favorite spot at one of my preferred coffee shops, I was working my way through the manuscript that Sir V had sent me.
The shop was a cacophony of tech sounds, clicks and beeps between my laptop, smartphone and other patrons in the shop. My ear-buds were in place, alternating between listening to Pandora and iTunes while I worked.
Since my life was often isolating with the type of work I did, the way my days were structured, and the fact that I did it from my home; I’d learned long ago to get out the condo frequently.
I’d managed to escape fairly easily into reviewing the movie manuscript Sir Vlad had sent my way and was busy typing out notes. The work I did for him provided me a similar type of escape from my real life that I provided to my submissive clientele.
My thoughts, as usual, oscillated back and forth amongst my clients, but every time they landed on Ethan, I sucked in my breath.
I felt him to my core.
Inside.
In a sweet, possessive way I’d yet experienced.
I was always affectionately attached to my clients, but this was different and I knew it. This wasn’t solely a physical sensation. It was deeper than that. It was tender, more emotional and new for me.
Was this love? The beginnings of love?
Laying claim to Ethan was a thrill I could barely describe. Although I’d cock-caged, and collared many a client over the years, nothing compared to the delicious pleasure I was experiencing of training a sub-puppy whom was to be my very own. The illicitness of it wasn’t lost on me. I was learning so much temperance with Ethan. Somehow, I was managing to pace my claiming and training of him.
That’s why, when Damien’s text pinged my smartphone, I was pulled out of my sweet and satisfying reverie with a startle, almost spilling the remaining contents of my nearly empty paper coffee cup.
I felt like the woman who has had a wonderful meal and doesn’t know which dessert to order. Instead, she just gives in to her appetite and orders both, not feeling guilty in the least
.
Damien or Ethan?
Ethan or Damien?
Both. I wanted them both.
I giggled. Wow… I really was hungry.
‘Cherry, does this Sat eve at 8 still work for you? ~ D’
I tapped my manicured nails on the tabletop of the café I was sitting in. I needed to figure out how to make this happen. How was I going to lasso both men and play, for keeps? I quickly texted back my response.
‘Sounds wonderful Damien. 8’ish is best for me. Shall we meet at a restaurant of your choosing? ~ C’
I resumed reading Sir Vlad’s movie manuscript on my laptop, waiting for his response. I typed and as I did, my thoughts wandered… I needed to ensure that I could wiggle out of having Damien picking me up at my high-rise condo complex. I didn’t flaunt my financial success in the face of vanilla men or those outside of my clientele list. Sadly, most were simply too insecure to handle the success of an Alpha woman. Money brought out the worst in people. I strongly disliked greed and the insincerity it brought out in others.
‘The Black Bottle? I can be a gentleman and pick you up. My Mama raised me right that way. I’ve got manners, promise. :P’
I smiled. Of course I knew he was well-mannered, I would never have accepted his invite for a dinner-date otherwise. How to finesse this?
‘Damien, of course you do! I’ve no doubt… Call me modern or independent, I prefer my own methods of transport. Can you forgive me? I promise to be a proper lady and a good date the rest of the evening.’
I waited for his response, holding my breath a bit. I went back to reading the movie manuscript and soon found myself absorbed again.
Certainly, I can follow your lead. Looking forward to it, Cherry.
I smiled. Follow my lead will you?
I wondered what Damien would do if he knew I was conspiring to see if I could make a cuckold fantasy of mine actualize – with his help. Although Ethan was adequately endowed, I found that I wanted to torment and torture him somehow. I was wondering if I could.
Now, to figure out how to make this happen…
* * *
It was almost time for Ethan’s next session. I laid out, on an ottoman, the gorgeous collar and cock-cage that I would be putting on him tonight. Admiring them, I thought about what Sir Vlad had texted me earlier in the week. About the way to trust…
