1. Debbie Do

1 Prologue

 

Debbie was my go to girl at the office. When I needed a session booked, she was the one who could do it. Even better, she would lean over at her desk revealing cleavage that went all the way from Chicago to Cleveland, She was that special kind of woman. Five foot two, with 38DD breasts always barely restrained in a low cut fashion. My eyes always wavered between her large brown eyes and incredible tits. Debbie knew it. She kept her black hair cropped short so as to never obstruct the view with distracting tresses that would thwart admiration of her magnificent breasts. When she would rise to walk to a file cabinet her tiny ass was often sheathed in fabric that would reveal panties lines if worn. Often they were not. This was in the pre-thong days. She was the best. Debbie could get me booked where others would fear to tread.

 

One Friday night after work the whole crew retired across the street to our favorite watering hole. I could only have a few because I still had a cut to do and clients were coming in first thing Monday. I didn’t want to work over the weekend so I left early. I tossed my credit card to Dave the bartender and said “My treat.” and went back to the office to do the rough cut on my KEM.

 

I had spent an hour or two and had the rough cut knocked. I was doing the last playback when I saw Debbie standing in the doorway. She held two cocktails in her hands. “Finished yet?” she asked in her low and soothing voice.

 

Debbie was wearing a sheer orange dress that accented her olive skin impeccably. The plunging V of her neck line barely constrained her overflowing breasts. I wanted to dive into that cleavage. The way the fabric flowed and simultaneously clung about her body was a sight to behold. As she poured into the room and handed me one of the cocktails I didn’t care what was in it. I wanted to be in her. I noted that she had closed the suite door and locked it so I was already plotting, but mindful because we were colleagues.

 

“Show me what you did.” she asked. So I lined up the pix and track and hit the right button and the rough cut played.

 

After the grease pencil fade out Debbie said, “Let me see it again.”  

 

I obliged. As all good editors do, I watched Debbie’s face, not the screen to gauge her reaction. It doesn’t really matter what people say, it is the way they react that counts.

 

I turned and hit the stop button at the end of the spot. When I rotated my chair back to Debbie I asked, “Well?”

 

Debbie had moved close behind my chair and when I turned I was eye to orange silk covered tits. As I tilted my head up to peer past those unbelievable boobs I saw her short cropped black mane and soft brown eyes smiling down at me.

 

“I think the clients will love it. That reminds me.”  She tossed the credit card and the signed bar tab in my lap.

 

“Oh, thanks.” I said and put the receipt and card on my desk.

 

“Now I have something else for you.” I heard her say.

 

When I turned back she began to peel the orange fabric off her shoulders. The dress fell to the floor unveiling Debbie before me in white bra and panties. The contrast between her dark olive skin and the white fabric of her undergarments drew my hand like a magnet. But Debbie slapped my hand away and she said “Uh uh, my treat now.”

 

 

There was nothing for me to do but admire the full figured woman in front of me. Such a compact yet voluptuous womanly figure deserved adoration. The short cropped hair framed a strong jaw line, soft delicate shoulders that supported her full and astoundingly firm white clad breasts that lead down to a flat tummy resulting in pristine white panties. The legs were sturdy and shapely. Compact femininity at its best.

 

“Well this is a treat.” I stammered. “Thank you.”

 

“Oh no, thank you.” Debbie said reaching  for my zipper while dropping to her knees. As she pulled it down she deftly undid the buckle on my belt with her other hand. With one stealthy movement my hips went up, my pants were pulled down, and she was running her tongue up the length of my cock which was already hard and reaching to the sky. The only hitch was at the knee where she had to work the jeans over my prosthetic leg. She knew of it and it didn’t phase her as she looked at the knob on the tip of my shaft as it bobbed in the air before her shimmering brown eyes. She reached up with both hands and  ran her fingers from base to just below the tip. Being a petite woman, except for those magnificent tits, her small hands made my average sized shaft seem longer and thicker to my visual delight. Of course when her hands reached the knob all bets were off. The head of my cock resembled a tennis ball in her small hands.

Debbie rose up on her knees just high enough to maneuver her mouth over the top of my cock and ever so slowly let her lips part as she slowly slid my dick into her mouth and as far down her throat as it would go in that position. I felt her tongue work teasingly side to side almost reaching my balls till I felt her throat open a bit with a reflexive gag.

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Debbie raised her head slowly leaving a stream saliva along the shaft as her tongue slid up the length to the tip releasing the now shimmering orb. She looked up at me with watering eyes. She swirled her tongue around the large knob and murmured, “I have heard about this,” as if speaking to a microphone, then wrapped her lips around the engorged head and sucked on it like a Tootsie Pop.

 

She paused just long enough to look at me and say, “I guess I have my work cut out for me.”

 

Debbie then proceeded to fuck me with her mouth as I have never been skull fucked before.  She was slurping, humming, and making quite a spectacle as her short black hair began to glisten with perspiration. She worked me mercilessly with lips, tongue and hands till I could contain myself no more.

 

As I spurted wildly in her throat she slowly raised her head gliding her lips tightly along my ejaculating length. When her mouth freed me she gave a last flick of her tongue to gather a bit of semen from the tip. She looked at me with her deep brown eyes while using her pinkie to pull the last bit of come from her lips to her mouth and said, “Now you owe me one.”

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When Journals End

December 31

 

Memory is indeed a funny thing. As I read the journals I noticed that it was the narrative I tell myself when I reminisce about those days. It was weird. I did get really spooked after that Halloween night. My life did take a different direction after I left the warehouse job.

 

Here I am on the cusp of my marriage.  Up until now the real events of the Halloween “concert” alluded me. Now not just marriage but with a bonus child coming seven months later. Sure I had only seriously dated the woman for eight months before this. Four months before I decided to commit and stopped fucking the other two women in my life.  But she fooled me. She stopped taking her birth control pills without telling me two months before.

 

She said she did not have the money. But she made a good living.  Since we had for all intents and purposes living together these past few months I might question her expenses. Other than keeping her tiny studio apartment I estimated them to be minimal.

 

But I am a fool in love.

 

Her big blue eyes and bigger soft as a bunny tits, thin waist, and curvy behind had won me. Really it was her simple southern ways and homeyness that she displayed that made me forgo the pleasures of my more experienced, adventurous, and sometimes tandem two toned lover’s beds. The prospect of monogamy and “settling down” seemed more likely with Toni.  The years since Rene I had much sowing and reaping of wild grains on my part; but I was pining for the fiords of a deep, meaningful, and possible everlasting  love.

 

The  romantic in me will out every time.

 

So as I go through things that I may not want to drag forward into this new relationship I found those journals from my past. Out of the pages of scribbles and typed pages on the boat anchor weight Underwood typewriter ensconced in my coach house it raised questions within me.  Why that journal? Why from that year?

 

The long forgotten events of a long forgotten Halloween night. Here is more baggage I need to remove before I start my new life with Toni.

 

What is most troubling is what was forgotten and now remembered with today’s clarity.  What happened that Halloween night has been revealed to me in High Definition that was not possible then. The events of the spring and summer of my shipping clerk days flooded back to me. It all seemed to make sense now. Those events are freshly etched in my soon to be family man psyche. I need to exorcise these memories and move on.

 

I will do it on the pages to follow along for myself and see if it is still clearly defined once written down.

 

First memory that flooded back was how that Halloween day started. The minute I got to the warehouse I was immediately sent over to work with Ellen Joy.

 

We started our day together as always. Three bong hits each. No more. No less. Today she was wearing her, what I can best describe as floppy hippie hat. It was perched atop her long flowing brown curls. This was no perm. This was hair she had been growing a long long time and it shimmered in the morning light.

 

Perhaps the dope made it shimmer more. I knew creeper weed and this was creeping up slow and steady.

 

Soon I was being ridden by this full figured woman who was chanting,  “Deeper. Deeper. Deeper.” Her floppy hippie hat above open blouse with a black silk scarf slung low around her waist were all in motion. She was perspiring platinum. Breast’s lost their fleshy bounce once fully out of her blouse to become still beacons in the morning light. She glowed. Oh, how she glowed.   I marveled at how my cock disappeared into that full curly bush . I was pushing up on my feet, lifting her on my pelvis and arching my back high off her sloshing slapping water bed.

 

As I pushed repeatedly into that thick black bush. I began to feel I was being swallowed up in a deep lush forest. Except what was once warm wet and wonderful, was becoming wiggly, wormy, and dank. I could swear the black curly hairs, once soft and inviting, were becoming constrictive and stifling. I could not breath and my cock felt coaxed by thick black tentacles and powerful suction.

 

The hairy black tentacles grasped and entwined me and Ellen’s crotch opened wider and wider as if it were a gaping maw. It pulled me up into her gaping box by my balls. Her unholy twat pulled my balls within her as if to swallow them up like Rocky Mountain oysters. Her usually hot wet cunt was cold as icy death itself.

 

Her voice husky and breathy repeating over and over , “Flesh of my flesh. Bone of my bone ….”

 

It was then that the metamorphosis of Ellen Joy transpired. She became the youthful and bouncy boobed Jo Jo. The same Jo Jo I knew only in passing and who was to accompany Tami with me to the concert tonight. But why am I fucking Jo Jo now. Tami was to be my date tonight I thought incoherently. As I was mesmerized by sweat shimmering bouncing brown tipped tawny boobs it was….

 

Fade to black for me.

Thanksgiving

Rene and I spent a great holiday weekend together. I could tell she was burned out from University. I hope after this weekend she is not burned out from me, We were at each other like the two healthy nineteen year old animals we are. For a change Rene was as hungry as I. I liked it. That pursued damsel giving in to her boyfriend’s base desires can get old.


From the time we woke up en-wrapped in each other Friday morning until this Sunday afternoon it seemed if we weren’t fucking, we were either eating or bathing in my homes claw-foot tub. OK, we had fucked in that tub a lot before this. Who ever placed that tub in the center of that tiny bathroom was a genius. It became a prop as all the scant furnishings in my coach house abode had for this holiday weekends grunting, groaning, moaning fuckfest.


The only break was Fred’s annual Holiday party on Saturday night.  He has thrown one for years. His house was always the one with the scantest adult supervision and the tradition continues. Time was  Rene and I would have stayed overnight after party to make use of the upstairs spare bedroom. But now that I have my own crash pad we left that to be used by others this year.


With all the old friends and flames of mine at this party it was a test of my new found vow of fidelity. I must admit some women of my past, fact and fantasy, life might have crossed my mind as Rene serviced me upon return to the coach house that night. But the view of her long blond hair as it fell across my stomach as Rene took me into her soft wet mouth would banish all but adoration for Rene and Rene alone. Not to mention the sight of how intently she studied my dick with large blue eyes as she slowly stroked it and brought me to full attention. That was as alluring as any old phantasms that flounced in my head. Visions of girls I had lusted after previously. Some which had even satiated that lust. Far to few in reality.


Looking back at the party now I have to shake my head in wonder. Not only did the usual suspects, from Helen’s friend Eileen to Fred’s younger sister Judy seem to be drawn to rubbing against me like cats in heat whenever Rene was otherwise occupied. Each young woman was generously blessed with large breasts and seemed to want to make the point that Rene was not. Where were such attentions when I went stag to these occasions? Even Helen was more touchy feely with me than ever, until she remembered herself with the aid of my fidelity to my best and oldest friend Fred. All this in spite of the chemical enhancements available at this party. I have done alright with women in the past, but on this night there were open invitations from places where doors had always been shuttered tight before.


So as I positioned myself behind Rene’s deliciously upraised heart shaped rump for a final multi-angled ravishing of the day; her only comment was, “So are you going to fuck me into oblivious slumbers yet again tonight.”


“I shall do my best sweet Rene.” I said with firm resolve and impaled her again and again upon my rigid staff until that post coitus black curtain fell.

 

 

Samhain Rustling

It was then I began hearing sounds from the attic. JoJo was still working the floor with some help from Little Red Riding Hood. Little Bo Peep was shepherding some of the stray lost sheep out the door.

Finally Brunhilda took charge of those that did not succumb to subtlety and the party was cleared.

The soul cakes and colcannon had been devoured and only a few crumbs of the barmbrack were left on the plates.  These were not typical here in America on Halloween and I really enjoyed the touch of the Celtic Samhain JoJo had brought to the evening. She never failed to surprise me with her tricks and her treats.

Still I heard noises from her attic. I knew there was an attic, but in spite of the time spent in her home I’d be damned if I could even tell you how to get up there. But clearly there was someone up there. Or something!

Deciding to make myself useful I began tidying up party central. JoJo approached and took my hand and said, “Remember I told you there would be more rules.”

More Rules:

  • No cleaning.
  • No touching yourself.

Well alright then I thought to myself.  While I was still in hand she led me along with LIttle Red Riding Hood and Brunhilda in tow to the rear of the house and through a door I had never before noticed. It was such a small and inclined stairway I feared for Brunhilda’s ascent. But she gracefully climbed the stairway with ease me being urged up the disorienting stairway with JoJo before me and Little Red Riding Hood behind.

It was an attic alright, but spotless. The raw wooden floors had been scrubbed and the bare rafters were immaculate. There were beautiful weaved tapestries between each raft placed with a precise symmetry. The fabric made what could be a stark skeleton of a peaked roof  feel warm and very inviting.

A single bare bulb hung in the middle of the space. Rather than being harsh it radiated a diffuse and pleasing light. But what it hovered above grabbed my attention most of all. There on a platform, resting upon what appeared to be a feathery mattress, in the literal spotlight epicenter of this otherwise shadowy attic was the glistening black machine from JoJo’s closet. On the other side of the platform sat a chair. Well, also being on another platform it might best be described as a throne. For effect there was a  hanging behind this throne, but in the shadows I could not decipher the pattern upon this tapestry.

If I had felt disoriented coming up the staircase to this next level, my head was swimming with questions, curiosity, uneasiness, and excitement. Like little fish these impressions were swimming around my head and then scattered as the predatory lust fish swam to the surface of my consciousness.

Here I was the only man with three women, Little Bo Peep, LIttle Red Riding Hood, and Brunhilda, all dressed in provocative Halloween’s slutty slant costume regalia. I only knew for sure the identity one of these women. JoJo. As alluring as her already compromised attire was, the fierce rams head mask gave an edge to this developing late night tableo.

Well, make that four women as the Leather Nun appeared out from the attic shadows pushing a cart filled with colorful bottles of lube and phalluses of  sizes and shapes to strike any ladies fancy, adorned with various strategic placed nubbins and protrusions designed and designated for her pleasure. The predatory lust fish was skittish and looking for a dark place to hide for a moment.

But Bo Peep and Little Red took my hand and led me to the chair rather than the mechanized feather bed so little lust fish began to peek out even if still intimidated by the out manning display of phallI on the Leather Nuns cart.

 

Annie

“What was the name of your home town?” I gasped trying to divert and delay.

Annie was looking at me with her startling blue eyes which peered out from under her ratted blacker than black hair. Cut short with a single curl for a side burn on either side of her rouged cheeks, she seemed to me to be the last of the mods from Great Britain. No doubt she once screamed for John, Paul, George, and Ringo in her day. Now it was the late nineteen seventies and she smiled at me and said, “I’m from Kaddiff,” in that accent that always made my nineteen year old cock stiffer than it usually was. She was the poshest women I had ever met. Or at least that is how I felt as she was giving me a handjob in the warehouse office where we both worked. The way her tits had the ski slope swoop from the braless seventies fashion and came to a point of reserved British ecstasy while pulling apart the unbuttoned flimsy fabric of the polo shirt had me smitten and bitten. The view was bringing me off fast. Just like the kitten liked it when working my dick with her mittens. I would last a little longer when she mounted me after business hours. These were the best work breaks ever.

But if Donna, the other “woman of a certain age” I was intimate with at my fun house warehouse job found out all hell would break loose. With that I broke loose and with perfect as ever timing Annie’s mouth covered my cocks top and slurped up every last drop. Only strands of my cum saw the light of day as she threw her head back and swallowed my load with her incredible sense of bravado.

“Well done my boy.” Annie said as she took out her compact to inspect her lipstick and face for any telltale signs of my seed.

I opened the office door and nearly walked right over Tami. Tami was at best five feet tall. She was my age, had long brown hair which fell past her shoulders in a frizzy perm that nature had given her. She was lucky it was the seventies because that was the style. Other decades might be more problematic, but for me her hazel eyes, extreme tan, and tiny butt captured what desire was left within me after Annie’s vigorous stroking. That was of course when I was not negotiating a pot and fucking deal with Donna, or finding stories to tell Rene, my long term amour, about why I had to cancel a date. Donna she would understand about because one thing Rene liked almost as much as me was pot. Maybe more than me. But good dope at a cut rate was something Rene would accept. Even if I came home smelling of middle aged pussy to get it. Rene was a pragmatist.

Tami was not. When she went into Annie’s office after me I wondered if she would get some Kaddiff as well. Annie used her management role as well if not better than any man did in those days of disco. This was the land before sexual harassment was recognized as a crime. So we were all fucking like bunnies in the workplace. As I recall it was mostly consensual.. Not being in a role of power I was not a predator and if Annie was a predator, I was willing and eager prey. That woman fucked me blue while II worked there and I am forever grateful.

Gathering Samhain

JoJo and I have been dating since April. April 1st to be exact. She had given up on relationships. So had I. Over the months I learned she had a special machine tucked away in the back of her closet. I was fascinated by it, but discreet when the topic arose. It rarely if ever did, other than her insinuation she was enjoying her new found toy of late. I will say I am one grateful and lucky toy. But still….

She had a full regalia costume Halloween Party for the past couple years. October was here and she would parse out her holiday party rules to me.

Rules:

    • Costumes had to include at least a mask of some sort.
    • Real identities cannot be revealed through out the party.
    • Don’t ask Don’t tell.
    • More rules would follow

The first part of the evening was hors d’oeuvres and cocktails while candy and treats were handed out to the Trick or Treaters. All the little ghouls and goblins were treated well. Some of the party attendees did not answer the door because their costume selection was to risque for this sleepy suburban cul-de-sac community.

Through the evening the party goers would come and go. Some were clearly in for the duration, others recycled and refreshed, would go on with their Halloween revelries elsewhere. Some of her neighbors I recognized, costume and all. Others I did not.

JoJo made about as lascivious a Little Bo Peep imaginable. Her lithe body belied her status as GrandMaMa. The skimpy costume was just the wrong side of decency. But the rams head mask complete with horns that she wore above the sexy Bo Peep branding gave me the shivers. No cute cuddly lambs head for JoJo.

I was intrigued by a diminutive little red riding hood who would occasionally speak in an odd sort of affected Cardiff, Welsh, Scottish accent. Clearly an artifice for the occasion. Childlike in size the voice was that of a woman nonetheless. I found myself watching her move about the room in flowing scarlet robes and a black veil under her riding hood had efficiently obscured her features.

A cameo appearance was made by Peggy,  JoJo’s next door neighbor, sufficiently liquored up early and often while dressed in the Naughty School Girl Uniform. Disheveled enough from the boozing to make it less sexy and more victim of a misspent youth in appearance. No attempt was made by Peggy to obscure her identity because, well, that’s Peggy.

Then there was the other person with the genuine Cardiff accent. The leather nun costume was formidable.  Voice did not betray gender. The habit had the addition of black leather mask making the striking visage intimidating. The nun emanated command from the corner with the stance of a sentinel assumed. I could not tell if it was to be near the mulled wine or perhaps to remind those to practice restraint from consuming too much mulled wine. But the nun was a presence with a capital P.

There were early Trick or Treaters. The young ones that would look amazed when all they had to say were three magic words and then candy would appear in their sacks. Children bringing their parents around begrudging because they knew they were old enough to go on their own, but the parents disagreed. Then came the teens, Brooding, still young enough to want the candy, but really out to just roam the streets with impunity and scare up just enough trouble to be dangerous. To others and themselves.

Since I had followed JoJo’s strong suggestion that I dress as Gladiator, she tells me I favor Russell Crowe from time to time, I was excused from door duty.  Even with mask in place and loins girded it still was not a PG costume. If I had known I would have spent more time at the gym and less at Slammies were JoJo is the bar wench. Oops. Don’t tell her I wrote that.

Although the party had healthy circulation and turn over I noticed  Little Red Riding Hood and The Leather Nun were in for the duration. It was toward the end of the evening when Brunhilde made a grand entrance.

Every bit the grand operatic legend. From her prodigious size to her bawdy and booming voice. She took up the room. Unabashedly revealing costume worn well and to great effect, Viking horns with obscuring face guard she was ready for battle. Where the Leather Nun was tall, Brunhilde was wide and massive.  Folds of flowing flesh that moved about the room with grace as she embraced those she knew as well as those to whom she had just been introduced with equal joy. Clearly comfortable in herself and the space she owned.

Peggy clearly was enjoying her wine, and apparently my costume was having an effect upon her.  As next door neighbor our interactions had always been cordial, but between the mulled wine, the vodka tonics, her day drinking ways, and my costume she seemed to be sending more than her usual attentions my way.  JoJo noticed too. But her rams head mask did not allow me any sort of read on her feeling about this attention. But slutty school girl signals Peggy was sending were not lost on anyone in the room. Luckily her husband came to collect her after doing his kiddie trick or treat duty and all was well in the neighborhood again as the party cleared.

Beloved

“My beloved one.” I speak clearly as if into her ear. I cast my eyes upward to see swimming pond green eyes above jiggling boobs. Her half bitten lip in ecstatic dreamy smirk. Her head is thrown back in wild abandon as a low lacivious moan escapes from deep within her being.