A Graduation Like No Other

Towelled off, Emily announced "for Julia's first anal with your big cock she and I need to take a few minutes to make sure she's ready, so we'll do an enema. David you go wait in the bedroom -- you can think about what's to come, and make yourself really hard." An easy suggestion to follow; a couple of strokes had me gloriously tumescent, thinking about my tight destination, Julia's intriguing rosebud...

Soon Emily and Julia joined me, and Emily placed two pillows midway down, said that she was first up, and prepared to climb onto the pillows, face down. Julia said excitedly, "let me show you what spanking implement I've chosen," and opening the cupboard door she selected the heavy rattan cane, 30 inches long with a handle that allowed a tight grip. "I tried them all, and this one seemed the best."

"Oh Julia," exclaimed Emily, looking a little alarmed, "that one's the most painful and frightening of them all! Are you sure? Because after it has whipped me, and David, it is your ass that will be its last victim tonight!"

"I'm sure," replied Julia. "I want to give, and receive, the most extreme pain possible before my asshole receives David's huge hard cock. So if you'll lie down and offer up your ass, Emily, we'll get you ready." Emily did so, the grip of her hands on the bedsheet betraying her tension. Julia and I spent extra time kissing and massaging Emily's ass, licking and penetrating its lovely crack and her rosebud.

Then Julia stood back, and I moved to Emily's head where I reached for her hand, put it on my cock, and told her to hold tight. The cane swooshed through the air in a long arc before it made contact with a huge WHACK!! Emily gasped and stiffened. Then another swoosh! WHACK!! And a third WHACK!! Three angry red welts, three livid stripes across Emily's prostrate ass.

"My turn now," I murmured to Julia, relieving her of the heavy cane. "Go up and hold Emily's hand while I whip her." I did a couple of practice swings -- the cane's weight made a long swing necessary, and the impact extremely painful. Julia took Emily by the hand and indicated that they were ready.

Swoosh! WHACK!! Avoiding the weals already crossing Emily's ass, my first stroke went high, marking her where her ass just began to rise from her back, at the top of her crack. She responded by clenching her ass cheeks and pushing them downwards towards the bed. I waited a moment. "Raise your ass" I ordered her. Slowly, hesitantly, Emily lifted her buttocks a little, off the pillows.

Swoosh! WHACK!! my next stroke was on my favourite place, the one I knew from experience stung the most, right where the backs of her thighs met the rising globes of her ass cheeks. Emily whimpered a little, shuddered, and then lay still awaiting my final stroke. I decided to vary my usual habit, and I shifted down towards Emily's knees. I knew that after this whiplash, I would be the helpless subject on the bed, face down, and I knew that no mercy would be shown to me. My final stroke was a two-handed WHACK!! that landed diagonally across Emily's ass, leaving its angry weal cutting across the five previous welts that she displayed.

Emily struggled to her feet, gave us a huge hug while we massaged her angry welts. "That was a whipping like I've never had before!" she exclaimed. "Only thing kept me down there was knowing that David's lovely ass is next. On the pillows, David, for the beating of a lifetime. Julia, again you go first with the cane."

Obedient, I lay down with my ass raised over the pillows, trying to keep my scrotum out of the range of the angry cane. Emily chimed in with her loving promise, "instead of holding David's hand, I'm going to reach under and hold his gorgeous big cock, so he keeps being excited." The very thought made my cock swell.

Swoosh! Nothing, just a practice swing I guessed.

Swoosh! WHACK!! White-hot pain slashed across my buttocks, as Julia's first stroke hit me right in the middle of my ass, at the highest point. I writhed and groaned a little, and then was still, raising my ass once more into position while the comforting hand, Emily's, caressed and squeezed my cock.

Swoosh! WHACK!! Again, white-hot pain, more intense than before -- Julia's second lash laid itself across my buttocks in exactly the same place as her first stroke. My ass stung with the shock of the second hit, as the first had not subsided. I was moaning and lying there dreading what I knew was to come...

Julia said "the third will lash in the same place -- I want to see how multiple hard strokes of the cane increase the pain. Ready?"

I nodded, reluctantly, grabbed the bedsheets, and welcomed Emily's strong hand on my cock. Swoosh!! WHACK!!" Oh!! white-hot, unsustainable pain, racked my body, and I bucked and writhed and moaned for several minutes.

Emily withdrew her sensuous hand from my cock, and said "my turn, Julia -- give me the cane, while you go and hold onto David wherever." I felt a new hand insinuate itself under my tummy, grasping and caressing my cock and balls. "I won't whip you on your serious welt, David -- relax if you can..."

Swoosh! WHACK!! Emily's first slash came with white-hot pain across the bottom of my ass, where my thighs met my ass. The most painful place! "Unnggh" I groaned and stiffened, while Julia squeezed my ball-sack and brought me close to orgasm. "Two more quick ones, as hard as I can like always -- I want to get on to the main event!" WHACK!! WHACK!! Two almightly blows across the upper part of my ass, the white-hot pain making me wince and shudder.

I slowly became capable of movement again, got to my feet, and embaced my two tormentors, while they rubbed my burning ass with their hands. I held them in my arms, realising that Julia had given me a new idea that I was about to try out...

"Ok, Julia, your turn!" I chirped cheerfully, as Julia apprehensively arranged herself face down, her lower tummy raised on the pillows, her firm globes separated by her enticing ass crack. "First a little preparation is in order..." Emily and I covered Julia's ass with kisses, licks, nibbles -- I concentrated on her rosebud, which quickly became juicy with my saliva and my probing tongue.

Emily took up the cane, and swished it around menacingly a few times. "David go up and steady Julia as you do best." She waited until Julia had a firm grip on my rock-hard cock. "Now you'll find out why I called this cane the most painful and frightening...are you ready?" Julia nodded.

Holding the cane in both hands, Emily swung WHACK!! WHACK!! WHACK!! -- three sharp and quick lashes at the top part of Julia's throbbing ass, leaving three deep red welts. Julia had no time to respond during Emily's individual spanks, but her sobs and tears afterwards as she writhed and groaned and squeezed my cock were testimony to the pain she was feeling.

After Julia collected herself I disengaged her hand from my cock, which was swelling even more at the prospect before me. I collected the cane from Emily. "I want to offer you, Julia, two choices for my caning. I'm going to be preparing you and then entering your tight asshole very soon (lovely prospect), and I don't want the pain of my three strokes on your cheeks to interfere with your enjoyment of your first anal intercourse. So, the choices. Either I cane you now, not on your ass but on the backs of your thighs, or we leave your final cane strokes, on your ass, until after we fuck."

Julia thought about things for a long minute, then replied "I really want the experience of your cock fully into my asshole to be the crowning first-time experience -- after that, there's no first times left, no matter how many more fucks I have! So, I'll take your three strokes on the backs of my thighs now."

She shifted a little, drawing her legs together a bit to make her thighs a better target for me. I only needed one target -- I aimed my blow about an inch and a half below her buttocks, and brought the cane down with a mighty two-handed swing, WHACK!! Julia responded by stiffening, and driving her body down onto the pillows, as if she wanted to disappear into the bed. But it was not to be -- I waited for her to resume her position, with her ass raised a little and her thighs curved and prepared.

With another mighty two-handed swing, WHACK!! I hit her in exactly the same place as before, adding to the angry welt that the first blow had raised. Julia bucked and writhed, and cried out for mercy. I replied, "Julia, I got this idea from you, and now you are going to experience it, as I did, to the full."

My third swing, two-handed, harder than the first two, landed with a swishing WHACK!! on the raised welt, angry and red, left by the first two strokes. Julia dissolved into hysterical tears, her body jerking and shuddering from the pain she was feeling. Emily and I stroked her shoulders and back, reassuring and comforting her while her tears subsided.

We helped Julia to her feet, and enveloped her in a group hug with both of us employing a free hand to massage Julia's thighs. "Wow!! She exclaimed, "that was my first time with the cane, and I hope it will be my last!"

I gave her a big hug, and explained, "when we spank, what we inflict is what we can expect to suffer when it's our turn. But let's get you ready for the main event, that you've been waiting for -- take the pillows away, lie down on your tummy, and Emily and I will ease you open and get you prepared." Julia lay back down flat on the bed, and Emily and I gathered around. "Maybe a little salve on that welt would make Julia more comfortable?"

Emily brought a tube of salve, and spread some on the backs of Julia's well-muscled thighs. "That feels much better, cooler -- thank you!" She squeezed her thighs together, in response to the relief.

Then Emily suggested "before you invade Julia's lovely asshole, which I know she is eagerly awaiting, I'd like to stick my oar in, so to speak. Julia, if you'd like please roll over on your back, and I'll do you, as you did me, Edinburgh style."

In a trice Julia was on her back, legs raised, and my lovely sensuous Emily was kneeling over her, calves pinioned, while Julia's legs were raised behind Emily's shoulders, making her as totally available as Emily was to Julia. They commenced their enthusiastic sensuous licking -- I might have felt a pang of envy at their pleasure, but instead I had a new idea.

Positioning myself at their sides, I was able to penetrate both of their assholes at once with probing and insistent fingers, right hand for Emily, left hand for Julia. They both responded with shrieks of pleasure, and their simultaneous orgasms were immediate.

"Oh, David!!" cried Julia, when her orgasm had subsided, "I have to have your cock in my ass this minute!!" as she turned face down on the bed, raising her buttocks. And Emily, having paused to give me a warm kiss filled with her saliva and Julia's cunt juice, took up a position on Julia's other side, and we both began to minister to our recumbent lover.

I began with my tongue, insistently probing and exploring Julia's rosebud, while Emily absented herself for a moment to get us a tube of lube. Julia's nightly wearing of the butt-plug, size three, had stretched her sphincter and made her ready -- just as (I knew) my own asshole was to undergo the same conditioning over the next nine nights.

Emily returned with the lube, and I smeared it over my fingers before inserting one, and then two, into Julia's willing rosebud. I twirled my fingers around and ensured that her sphincter was well-coated.

"Oh David I am so ready for you!" sighed Julia, raising her buttocks a little to give a better angle. Emily inserted one, and then two of her coated fingers, and then we did a little dance of supple fingerings, probings, plungings, getting her slick with the lube. Julia groaned, "please, please, your cock -- my ass is begging for you!!"

What to do when a beautiful lover begs?? I withdrew my fingers and mounted Julia from behind, drawing her hips up so she was at a perfect angle. Emily scooched down and ensured that my cock was wet with her saliva, along with my pre-cum. "You've watched Emily and I do this before, so you know that the first entrance is probably going to be a little difficult...but bear up and soon I'll be in." I applied a little pressure with the end of my cock; to my delighted surprise Julia didn't flinch, but pushed back a little. I pushed harder, slowly, insistently.

"Slowly David, it's not comfortable yet" squeaked Julia, "but keep it coming!" I gathered her by holding onto her hips, so she was primed, aimed and ready. Relentlessly, slowly, I pressed onward, inward...then my cockhead was past her sphincter, into her anal channel, so tight, so hot!! Deeper...deeper!

"Oh!! Aargh!! Julia groaned, "that feels so big, so hard -- keep going! Fill me up -- make me your own!! You're like a huge hot post up my ass -- go deeper, go deeper!! Aahhh!"

I slowly, relentlessy pressed in, and in, and then I said "Julia, you can feel my crotch against your ass, my balls tickling against your cunt. I'm in all the way, all nine inches!! Now I'm going to slowly withdraw a little, and then begin to thrust into you."

I slowly pulled back about four inches, and just as slowly pushed myself into Julia's hot tight hole. I repeated this, and repeated this, and I sensed Julia beginning to answer my thrusts by pushing her asshole back against me. This was my cue to up the pace, and I began to fuck her with all the might of my cock. "I'm going to fuck your lovely ass off now!" I grunted into her ear as I plunged and thrusted, urged on my Julia's groans of pleasure.

Then I felt Emily's lively finger insistently pressing itself into my asshole, driving me to even greater ecstasy -- at the same time I felt her other hand between my swinging balls and Julia's cunt, and I guessed that she was, lovely expert in sensual stimulation, working her wonders on Julia's clitoris. I could sense Julia stiffening with excitement, at the same time as I felt my balls boiling with the need for surging relief.

"Uunngh! Uunngh!" cried Julia, as a huge orgasm overtook her and she shuddered, stiffening, on the bed. At the same time I roared as huge ropes of semen -- three, four, five six! spurted out of me, flooding her anal channel with surges of semen.

We lay, exhausted and breathless, as my cock slowly softened and withdrew from Julia's asshole, which was steadily seeping with semen. "Wow!!" said my fulfilled Julia, "that was something else!! You've now been in all of my holes -- cunt, mouth, asshole -- and in all of them you've given me unimaginably fabulous orgasms, the more so because I've always sensed they were wonderful for you, with that huge cock of yours pumping me full of your cum. Wow!! So my first times are all completed, except one...I'm looking forward to your birthday, when both Emily and I will possess your asshole with your own lovely big cock."

What to say to that? We showered again, I experienced for the first time butt plug number 3 (the huge monster!) and we cuddled and slept, with a beautiful naked lover pressing on each side of me. Bliss! And my birthday still to come...

Friday came, and Friday went, but the big Friday was looming in my future -- not that it would be a significant birthday (I would be 41) but it would be a most wonderful and memorable experience. First time! As I cuddled Emily, after our fuck on the Thursday, I shared some of my misgivings. "What about tomorrow? What if I can't take myself? I've never had anything in my ass except that little dildo, and it's tiny compared to me!"

Emily snuggled her soft breasts against my side and massaged my cock with her hand, making it spring to attention. "All your life, since you realized you have one of the biggest cocks in the world, you've loved to make me, and now Julia too, fulfilled with its size and vigour, but never hurting us, never commanding. Now you'll have the chance to experience how you've made us feel when your tremendous size possesses us. We will be very gentle, like you are, until you are fully engaged and responding, and then we will fuck your ass off!!"

"I'm not sure I'm reassured by that," I laughed, "but since you've been talking about it, and stroking it, you've made me grow wonderfully stiff and eager, and ready for another go. Are you up for it?"

Emily responded by giving me an ardent kiss as she mounted me, straddled me, found the end of my rampant cock and urged it into her eager opening. "Just try me!!" she exclaimed, "I can't get enough of the wonderful feeling of you in my vagina!!" She plunged herself down onto me, into her luscious warm tightness, and began to pump herself up and down on me. I steadied her by holding on to her pert breasts, helping them to ride up and down until we mutually orgasmed, crying out with pleasure as her cunt muscles strongly milking me and I spent myself into her eager vagina. Whew!! Nice to know, with 41 looming, that we could still manage two deeply satisfying fucks, so close together.

Then to the shower, and next to sleep -- need my strength for the big day coming tomorrow!

I awoke the next morning to find not one beautiful woman cuddling next to me, but two! -- Julia had at some time in the night crept in beside me, so I had the delightful sensation of two hands caressing my growing cock.

"Happy birthday to you!" Emily and Julia chorused in unison, and then Julia went on to say "we want this birthday to be the most special one you've ever had, so we took the liberty of consulting with your office, and you have the day off. No need to get out of bed all day unless you want to!!"

Emily cuddled in, taking my hand and placing it on her moist sex. "We are totally at your disposal all day today -- we'll gratify your every wish, and as well we have some wishes of our own. But with two conditions: you must spend the whole day naked (as we will be), and you must not have an orgasm before the climactic moment tonight, when your cock, with Julia driving, is filling your ass."

Julia chimed in, squeezing my cock delightfully under the sheet, "we hope you'll come close to lots of orgasms today, so you'll be really charged up!! First thing we'd like, please, is for you to eat us so we can each have a morning orgasm. Me first! Edinburgh style, except you won't climax, although I sure will! And next, so will Emily!"

Whew!! What a birthday this was promising to be!

The day passed, like a dream...I spent the day without a stitch on, and every time either Julia or Emily passed me by I was caressed, licked, sucked...they invited access to their cunts by spreading their legs deliciously and rubbing their labia against me. I lost count of the number of times I had a lithe strong finger stroking the inside of my sphincter.

I felt on the edge of orgasm again and again, pre-cum leaking from my cock, but no orgasm -- their ministrations stopped before that could happen. I mused about locking myself in the bathroom and relieving myself by jacking off in the shower, but I figured that would be cheating on the two women I love, and who were preparing me so lovingly. Whew!! Life was hard, and so was I!!

Finally came the time for my birthday dinner, and we sat to the table totally naked -- another first time for all of us! My lovely sexy wife Emily had prepared my favourite dishes, and we accompanied them with a bottle of Champagne. Sitting was sometimes awkward for me, because my erect cock kept banging against the table top, unless I sat far enough away that it could roost upright between me and the table's edge. Problems, problems...

When dessert time came, Julia had prepared a surprise -- she came in from the kitchen while they both sang "Happy Birthday", and attached to a platter was an enormous cock, covered with whipped cream and some icing covering the glans. My cock!! Or at least the enormous dildo that had been cloned from Julia's birthday present.