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Rosa’s thumb and three of her fingers crawl and probe down over my hard cock, my tight tender testicles, and down between my legs with her oiled middle digit kept apart from the rest.  Her slender extremities quickly find their way to their target.  With my eyes closed I focus on every tickling touch happening down there.  With her index and ring fingers she parts the butt cleft wider to either side of my back door.


I let out gasp as the middle finger touches me where nobody had touched me before.   Squeezing my eyes tighter I push deeper into her soft breast.


Rosa is gentle.  There is no jabbing or penetration.  She simply touches it at first, placing the pad of her finger against my sphincter and just holding it there still as she allows me to relax.


“Quin?”


“Yes?”


“Are you getting tired?”


“No.”


“Are you having fun baby?”  She teases and strokes my hair.


“Yes.”  I grin.  “Oh yes.”


“Mmm, I could just eat you up you’re so cute.”


“Thank you.”


“You have such a beautiful body.”


“Ohhh.  Thank you Lady.”


“You are so pure.  So soft.  Such a good boy.”


“Ohhhh.”  This unabashed praise was as foreign to me as far off Alexandria.  It just wasn’t how affection was expressed where I came from.  I squirm and try to snuggle closer, my legs opening wider.


Her finger begins to move in a slow circular motion, massaging the oil into my anus.  Reactively it clenches against at the new motion but once more Rosa is in no hurry.


“And you are so…fucking…sexy.”


“Hnnngh.”  Her rubbing felt nice.  A new kind of nice.  It sort of tickled, not in the way to make me laugh though.  The caressing of this most tender of places sent pleasing tingles into the base of my cock as well up the rest of my loins.  It felt good in its own right but it was so much more than the raw physical arousal.  I felt…vulnerable.  Exposed in a way I’d never experienced.  Yet also safe and cared for in Rosa’s embrace.  It echoed the thrill of being tied up and under her control but even more intimate.  Gradually, as if by some magic, Rosa slow massaging finger coaxes my entrance to relax.


“Open your eyes.”  She whispers.  “I wish to see this.”


Opening my eyes I glance up at her to see her staring back down at me with doting care.  In the warm dim light of the of the waning fire she exuded a pleasant dusky glow.  On seeing me look up her tapered ears rise just a little.  After a moment I pull my eyes away.  As if looking at the midday sun I could only handle so much, she was simply too beautiful to bear.  My Lady does not allow me to escape this time however.


“Look at me Quin.”  Her finger very gingerly begins to apply pressure.  My body obeys her on its own, my anus opening up for her.  But she lingers at the entrance.  “Look at me Quin.  Let me see those lovely eyes of yours.”


I swallow nervously then look up at her.  She cradles my head close, no longer allowing me to turn away.  And then…the gaze.  As her eyes meet mine she doesn’t simply look at me, she looks right down into my very soul!


“Shhhh.”  She soothes as she feels my breathing pick up.  “Good boy, good boy.  Shhhh.”


She wouldn’t allow me to look away.  She held my gaze in her own by the force of her dominant will.  It was deeply unnerving.  I could stare to eye to eye with another man no problem at all, my Dad had taught me that lesson well, but with a woman it was different.  I don’t know why, but it was.  Once more showing her control and great patience she holds me tight and waits for me.  Summoning all of my nerve I lay still and focus up into her gorgeous magenta eyes.


Rosa was as cute and perky a girl as you would ever see.  But in her eyes I see the strong and courageous woman within.  A woman who had seen things, experienced things and done things.  I see a woman who has known hurt and grief yet come through it with an even stronger resolve and optimism.  At a glance she appeared roughly my age, but her eyes revealed the truth.  And that truth, that I was being held in the arms of an older woman, made a world of difference.  Had she truly been my age I’m not sure I could have settled for her, as it was I inevitably melt to her will.


As she feels my tension ease she smiles.  “There we go.  Good boy.  You are such a good boy.”


“Ohhhhh!”


“Are you ready my boy?”


“Yes!”  I plead.  “I want you inside of me.”


Her smile fades, her eyes widen with intense interest, and with a careful yet firm motion she enters me.  Her finger presses in a short way then slows as it passes through a sensitive section.


“Ah!”  I gasp.


In one smooth thrust she buries her finger to the knuckle and holds it there.  “Does it hurt?”


“Mmm!  Um, a little…kind of.”  Hurt wasn’t the right word for it.  It sort of pinched but mostly it just felt…different.  “Not so bad.”


“Relax baby.  It will feel better soon, I promise.”


Just hearing those words were enough to allow me to ease up my clenching anus a little.  And, as promised, the more it relaxes the better if feels.  Her eyes search mine, watching me intently as I have my first anal experience.


“Goodness my boy.  You are so tight!”  She says.


“I’m sorry!”


This makes her smile.  “I didn’t say I didn’t like it.  You have nothing to apologize for.  We have some work to do before you can handle the real thing, that’s all.”  Her finger begins to move.


“OH!  Oh gods!”


“Mmm.”  She hums as her digit glide back through my gripping ass just an inch or so before going back in.  There is a pause before she does it again.  Then she goes again.  With each stroke it gets a bit easier.


“Ohh!  Oh wow.”


“Is it feeling better?”


I nod.  “Yes!”


“Good boy.”  


She settles into a slow steady rhythm as we gazed eye to eye.  Very quickly it graduated from slightly uncomfortable to not so bad to feeling pretty damn good.  Rosa’s finger didn’t simply move straight in and out.  She curled her finger upward to rub that area with firm repetitive strokes.  The spot below my belly button was already smeared with precum but now I could actually feel it trickle in little rivulets down one side as my dick leaked steadily.


“Ohhh wow…ohhhh wow!”  Rosa’s incredible finger just felt better and better and better.  “Hnnnmmm.  Oh this feels good!  Ohhh!”


“Good boy.  Gooooood boy.”  Her other hand strokes my hair.


My cock throbs and flexes with rising potency even though Rosa wasn’t even touching it.  The sensations she is drawing from me are definitely sexual in nature though in a completely different way than I was used to.  It was a gradual building of a pleasure both familiar and novel.  The growing pressure was one I was accustomed to experiencing in a certain external way but stimulated from inside of me instead.  It wasn’t as direct but it is no less powerful.


“Ohhhh!  Oh gods my Lady.  It feels so good.  Sooo good.”  I whimper and writhe.  A touch, all I needed was a touch and I knew I would explode. “Touch my dick.  Please!  Ohhh please!”


“Shhhh.”  She coos.  Her finger goes faster, the rubbing harder and more focused.  She had found a spot inside of me and had zeroed in on it and DAMN if it didn’t feel great.


“Hnnnngh!”  I am dizzy from pleasure.  The rising pleasure within me hitting a blissful yet infuriating high just shy of release.  It was like a strange type of torture.  My cock lurched and strained, precum drooling from it in a steady dribble.  “Please!  Please Lady.  Let me cum!”


“Shhhh.”  She hushes me again in the same soft tone.


“Ohhhhhh!”  I let out a long high moan.  This was feeling so good!  I didn’t know anything could feel like this.  Completely new cravings seized me.  I wanted…I wanted another finger.  Yes, two fingers!  Even three.  I wanted her to thrust faster…and harder…and deeper.  I wanted more!  My hips move with her and push against her both with rising pleasure as well as with frustrated neediness.   “Oh gods!  Yes!  Yes!  Lady…!”


Before I could beg again for climax Rosa shifts me in her arm to bring my mouth to her breast.  Without even a conscious thought my lips lock onto it.


“Mmmm.”  Rosa grins.  “That’s my boy.”


“Hmmm!  Mmmm!  Nnnnn!”  Like a babe fresh from the womb I suckle on Rosa’s teat.  It felt so soft in my lips, the nipple stiff and textured against my tongue.  The joy it brought is me every bit as nourishing to my soul as mother’s milk.  “Hmmmmm!”  My lilting whines become desperate.


The pressure builds.  Still she wouldn’t touch my aching twitching manhood.  Hovering as I am at the very cusp of release I think I might go mad with pleasure.  The NEED to orgasm overwhelms everything.  Just an accidental brush of her arm or a graze of my tip against the blanket would be enough.  Hell, a long hot breath would probably do it!  But holds things in such a way that I am denied these things.  There is only her finger.  That glorious thrusting rubbing finger.  With one slender little digit this petite slave had a strapping grown man grovelling and completely at her mercy.


“Come on baby.”  She encourages me.  “You’re so close.”


It is only then I realize she is trying to bring me to release with anal stimulation alone.  Was such a thing possible?  Given her experience I had to assume she knew better than me, and the feelings she had already brought out in me made me a believer.  As I lap and suck at her tit I let go of my preconceptions and allow myself to think beyond my dick and bask in all facets of my carnal joy.  There is a rush all through my body, my ass was the focal point from which it all emanated but the effects wash through every inch of me to accentuate all of the other pleasures.  Rosa’s soft skin against my cheek, her warm body next to me, her small supple breast in my mouth, her teasing fingers through my hair, and even this feeling of connection as I stared into her eyes felt amplified.  With no expectation I give myself over to the experience and let my body lead the way.


“Hnnngh!  Hmmm!”  My mouth of breast I moan and whine like my Lady liked to hear.  “Hnnnmmm!”


Her excited eyes urge me onward, her thrusting finger strong and sure.  She knew exactly how to touch me!


There is a distant roll of receding thunder as I feel something change.  A great wave pulses through my body lifting me even higher.  True thick cum begins to seep from throbbing cock as the pressure reaches the bursting point.  The actual moment of climax was here yet still somehow building!


“HMMM!  HMMM!”


“That’s it my boy.  Cum for me.  Cum for your Lady.”


A moment of hard thrusting later and it hits me with the force of an erupting volcano.  The release comes from within in powerful pulses, my muscles contract and grip around the finger had brought me to this state.  At no point had either her or I touched my dick yet jerking and spasming on its own thick ropes of cum start spewing out onto my stomach.  I kick and quiver and mewl, helpless against the raw force of the rapture that follows.


“Ohhh!  You did it!  Good boy!  Yes Quin!  Good boy!”


My lips come free from her breast as my body arches back over her thigh.  My hands claw at the floor and my hips thrust.  From my open mouth comes incoherent groans and grunts.  Her finger keeps rubbing and rubbing and rubbing as I keep cumming and cumming and cumming.  The neverending orgasm engulfs not just the cock and balls but the whole area then flows to every corner of my shaking flesh.


“Ohhhh!  Ohhhh Rosaaaa!”

Chapter 26 

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