Erotic Adventures of Jack

By ian wylde

Published on Nov 8, 2014

Encounters

The obligatory disclaimer: This is a work of fiction. As such, all characters are figments of the author's twisted and deliciously dirty mind. Any resemblance to actual people is strictly an unintentional coincidence. If you are under eighteen or are offended by things of a decidedly sexual nature, you shouldn"t be reading this. For those under eighteen, experience has taught me, as it will teach you, that life will mess with your mind enough after you reach adulthood. You really don't need a head start.

Now, without further delay, back to the story!

17

Sex in the Storeroom

Frank – dear Francine – had changed into a black business suit, complete with Oxfords on her feet, a tie around her neck, and a Fedora on her head, beneath which she'd stuffed her long red hair. Her shirt appeared to be (and I later found out was) the same periwinkle blue one I'd worn into Cloth Dreams. She'd even gone so far as to paint on a pencil-thin mustache with eyeliner.

And in between lay the bulge.

To suggest it was noticeable would be like saying Everest was a hill. I'm astonished she hadn't caused a scene or gotten herself arrested. It could have been mistaken for nothing but what it was – except, perhaps, that in this case it was made of foam latex, rather than flesh. I could live with the exception. After all, I still had Connie's tent.

Frank spun the dead bolt closed (she'd taken Connie's keys with her) and dropped the bag she'd been carrying then strode with purposeful intensity to and through the back of the store, ignoring us completely (except for the strained expression on her face showing her struggle to keep from laughing) as she pushed open the door to the storeroom and disappeared.

My special lady friend and I looked at each other with curiosity and a delicious degree of unbridled lust. "It would appear the game is afoot," I observed.

"Let's go get this gorgeous ass of yours fucked, shall we?" came the reply, accompanied by another playful squeezing of my posterior.

"If we must," I said, using sarcasm as a just-shy of Hillary Clinton method to forestall the possible embarrassment of premature ejaculation. Breathing deep to steel my nerves, we headed toward the storeroom.

??

We entered into what would have appeared to be like every other retail storage area in the known universe if not for one fact: Frank had turned out all the lights, except for a single small lamp sitting upon a desk at the far end of a corridor created by two long shelf-units. The concrete floor felt cold against the bottom of my stockings and the air smelled of dust and fabric as we ventured inward. About halfway along, Connie (behind me) released her hold upon either side of my waist and gently pushed me toward whatever my lesbian friend and her delightful, dirty mind had planned.

I reached the end of the aisle, but could see no sign of Frank. I peered around the end of both shelf units to no avail then looked back toward where Connie had been. She had disappeared. I was alone.

Interesting...

I saw nothing. I heard nothing.

Very interesting...

And then someone seized me from behind, slammed me face-first into the shelf unit, and damn-near caused defibrillation. Arms wrapped around my waist and chest, and fingers pinched my nipple through the thin material of my black blouse as lips nuzzled my neck and something long and hard pressed against my panty-clad rear-end.

A hoarse whisper hissed into my ear. "You're mine now, you little slut."

The arms swung me around a half-turn and brought me face-to-face with a vision. Connie perched on the corner of the desk, leaning on her hands, her legs spread, her pleated skirt gone. The previous cause of her maddening, tempting tent jutted outward and downward, like a "C" lain on its ends, the gorgeous head separated from her full scrotum by maybe four inches.

Saliva poured forth, as if someone had opened a valve on the mainline between my libido and my mouth. I swallowed to keep from drowning.

"You want to suck that nasty cock, don't you?" came the whispered question from behind me.

"Yes," I croaked, my heart hammering against my breastbone like a steam engine.

"Do it," my captor commanded. "Bend over and suck that nasty thing."

What else could I do?

Connie slid sideways along the edge of the desk to make room. The hand at my nipple slid away and came to rest between my shoulder blades then pushed me forward. I braced myself on either side of my new friend's sumptuous thighs as my best-buddy, the newly-created drag-king, forced my face to within an inch of the beauty between those magnificent legs.

I breathed upon the tip as Connie let out a deep moan and then a deeper "Ohhhh," as I kissed her there. My lips parted. My tongue darted outward, tasting, exploring. I scooped her into my mouth.

Behind me, I heard the "clink" of a belt being unbuckled, the arm around my waist pulling and releasing with uneven rhythm as Frank struggled to remove her masculine pants one-handed. I knew an astounding, erotic something was about to happen, and I waited in aroused anticipation, but chose to concentrate on the glorious hardness in my mouth, instead.

It swelled and pulsated as I sucked like a pig at the teat, rolling my tongue along the underside, pushing my head downward until I had her all the way in my throat. She gasped in sensual delight, grabbing a handful of hair at the back of my head.

Frank released her grip on my waist and in one rough move clutched my new panties with both hands and ripped them toward my ankles. "Put your legs together, bitch," she commanded. I did as she directed, pulling my balls out of the way so I wouldn't crush the damn things and shatter the delicious moment. I then used the same hand to grip the base of Connie's tasty shaft and cup her warm, hairless testicles, sucking her with ever-growing frantic intensity, wanting her cum, needing the salty goodness.

I felt cold, silky moisture against my anus, and then sharp penetration as a lubricated finger entered me, followed by a second, and then a third, amidst a jangling of nerve endings and electric pulses shooting straight to my untouched manhood. I could have cum then – almost did – but just as sudden as the fingers pushed in, they pulled right back out again, breaking the spell. I grunted from the back of my filled throat – half in frustration, half in absolute lust. If I wasn't at that moment the perfect candidate for a good, hard fucking, then no one in the history of the world ever had been. Good, dear God, I wanted this! Frank gave it to me.

I felt the hard, yet yielding foam latex head press against my opening, push inward, and stop. She was all the way in, but not moving; at rest, but at full fucking potential. She stayed this way for several moments as I lost myself in swirling sensation, my mouth and throat filled with cock, my ass filled with what had to be at least an eight or ten-inch dildo. I neither knew, nor cared. I just wanted to be pounded.

She pulled outward, an inch at a time, sliding back until only the head remained. She paused, and then with a grunt from both of us that must have sounded to Connie like stereo, she slammed it back in, the bones of her hips crashing into my flesh with a solid, resounding, slap.

"Oh my God, that's hot!" I heard Connie exclaim, and then I knew nothing but pure erotic power as the fucking began in earnest. Frank pounded me from behind as Connie grabbed both sides of my head and did the same to my mouth. Like a trip-hammer seesaw, the two ladies worked me; one in, one out; both in, both out; slamming me from each end. I was a toy for their pleasure, a receptacle for their use and enjoyment, an instrument for whatever they wanted, and I loved every second of it.

Connie started twitching, her breathing sharp and shallow, her moans sounding a staccato beat as she drove my mouth toward her orgasm. With a deep, groaning "Ahhh," she yanked me back by the hair, popping her cock out of my mouth, and screaming as she came in thick streams, splashing her pleasure across my face, coating me, anointing me with her love.

I had little time to revel in the decadent, sensual, sexual, astonishing delight of her facial, as behind me, Frank's rhythm went off the rails amidst the throaty cries of her ascent toward ecstasy. I'd heard her cum before, had given her more than a few orgasms during our many and varied spanking sessions, but I'd never heard anything to compare to the raw, animal growl with which she rushed toward this one. Its effect on me defied description. Without touching myself, without any direct stimulation from anyone or anything, save the repeated contact between her dildo and my prostate, I came with the power of a water-cannon, shooting my sperm all over the floor at my feet, as my body exploded into spasms of orgasmic energy strong enough to have ripped a hole in the space-time continuum, had this been a science-fiction story.

As it was not, I had to be content with a buckling of my knees as I fell to the ground in a tangled heap with Frank, who spared me the potential for bodily injury by removing her latex probe from my backside at virtually the same moment my legs turned into the anatomical equivalent of Silly Putty. She lay across me, half on my side, half on the floor, breathing as if she'd just completed a marathon.

"Holy shit, Batman," I croaked, when my own respiration had slowed enough to allow conversation.

"Wow!" she agreed.

"Are you guys okay down there?" I heard Connie ask from somewhere above. I cracked a single eye and stared up at her. Her cat-who-just-ate-the-canary smile said everything she needed to.

"I have a question," Frank began, with a throaty in-bed-afterglow mumble. "Are we still on Earth, or were we abducted by aliens from the planet Sex-O-Tron?"

"I'm gonna go with option two," I replied.

"That's got my vote," Connie chimed in.

"It's unanimous," Frank declared.

"I'd say `Take me to your leader,'" I offered, "but that would mean we'd have to move, wouldn't it?"

"Can't have that," Frank mumbled into my ear as she slid off my ribcage and snuggled up against my back. "Although," she hedged, "This floor is pretty fucking cold."

"And it's a little messy," I added, eyeing a glob of cum situated about two inches from my nose.

I heard rustling from above as Connie moved. "Okay. That's it. Everybody up!" Her foot landed right next to my left hand as she slid off the desk and stood. "I'll go get some towels." And with that, the most erotic experience – by far – of my life was at an end. All that remained was the kissing.

??

Following a cleansing trip to the bathroom for all, and after returning to the clothes I'd worn into that wonderful den of all things feminine, we stood together at the door to Connie's shop, three friends joined by erotic experience and forever altered because of it. I pulled Frank to me with a single arm and planted a warm kiss on her lips – no tongue, nothing sexual, but filled with every ounce of love I felt for my friend.

The kiss I gave Connie, on the other hand, was a horse of a different color. I released Frank and pulled Connie in with both arms, my hands wasting no time in finding her firm, round ass. Grinding my loins into hers, I kissed her, long and deep and sensual, our tongues doing an affectionate Samba for what could have been hours but lasted only moments. I could feel the response between her legs almost as much as I could feel my own. Oh my! The possibilities swirling around in my head would have made the most jaded professional turn a deep scarlet.

The spell broke when Frank chuckled, "Should I leave you two alone?"

We pulled apart and I gazed into Connie's smoldering green eyes. She waggled her brows at me and gave an inviting smile, but a concern for my own cardiac health brought me up short. "We go any further tonight and I'm gonna need a pacemaker," I said, releasing her and stepping away.

"That's my Jack," Frank joked. "All show and no stay."

I gave her the stink-eye and threatened, "I've still got enough energy to give you a spanking, young lady."

"Ooh," she said, but then added: "Maybe later." And with an audible "click," pulled back the dead bolt and opened the shop door, the bell at the top sounding a jangled refrain; a fitting end to a delightful evening.

I gave Connie a quick smooch on the lips and a swat on the behind and said: "I will see you later," with obvious sexual intent, and then departed with my lesbian.

I would be seeing her soon – the very next day, in fact. But first, I had to do something extraordinarily stupid.

18

Abject Stupidity in the Afterglow

We strolled along the sidewalk, past the boutiques and restaurants and cocktail bars, not quite holding hands, but close enough to brush them in a friendly caress. The spring air must have felt warm to the other people wandering the streets of Frank's granola neighborhood, clad as they were in minimal, yet socially acceptable clothing, but after our strenuous efforts in Connie's shop, to us, it seemed a bit chilly. Frank wrapped the suit coat around her once-again femininity. I wore the Fedora and carried her bag (and her strapon!), dealing with the relative temperature. We walked in silence.

One of my favorite aspects of tru friendship has always been the ability to say nothing and remain comfortable in the presence of another: a simple enjoyment of the other person's existence. No need for the nervous façade of small talk. No requirement to fill the air with inconsequential chatter, content to bask in the other's glow and call it good. We had shared many such moments in the past. This one, however, felt different.

An indefinable something hung between us, emanating outward from my best friend. I held no reservations about what we'd done, no regrets, no confusion; only love and a deep, abiding affection for my favorite person on the planet. I couldn't say the same for her.

I don't always know what to say to people, don't have all – or even most – of the answers, but in this case, I think I did okay. "I love you," I said. It would be pretty much the last thing I got right.

She did not, at first, respond, save for slipping her hand into mine and giving it a gentle squeeze. I gave her time, didn't push; didn't feel the need for validation or reciprocation. The situation called for neither. I wasn't in love with her, not in the traditional sense, at any rate, and I knew she wasn't in love with me. I didn't want that; didn't need that.

Logistically, technically, a relationship between the two of us was a physical and philosophical impossibility. I was a man. She was a lesbian. She and I would never be "boyfriend and girlfriend;" would never be "lovers" or "partners" or any of a dozen other labels. We were friends. We would always be friends. Nothing more was needed. Nothing more was wanted.

This did not stop me from loving her with all my heart.

??

Thinking back on all the years I've known her (which by that point was four and by this point – the spot on my personal timeline where my fingers are busily playing along the keyboard of this laptop – is almost fifteen) it strikes me as fitting that the person I love most in the world is the one person with whom I can't have a "traditional" relationship. Tradition has its place, I suppose: the gathering of friends and family on Christmas or Thanksgiving, the throwing of the first pitch by some athletically-challenged dignitary at the start of baseball season, the wearing of white by a bride so far beyond her virginity she may or may not remember losing it. These things matter. Why, is anyone's guess and the more appropriate subject for tales other than this one, but they do – just not to me.

During the preceding however-many 365-day increments, my life has been anything but traditional. This is not to say "special" or "uncommon" or anything setting me "above" or "better-than" the rest, just not "normal" – whatever that is.

And so falling for the one person in my life with whom I couldn't possibly have a "normal" relationship fits like (or at least better than) the glove OJ tried on at his trial. It would be entirely too easy, and therefore must be summarily cast out the window.

In any event:

??

As we turned the corner onto her tree-lined street, I heard her give a deep, soulful sigh. "I love you too, Jack," she whispered. "But sometimes it ties me up in knots."

"Well, if it's bondage you want..."

"Shut up, asshole," she laughed, releasing my hand and swatting me upside the head. "Can't you ever be serious?"

"I seriously love you. Does that count?"

"It counts for a lot, but it's just..." she couldn't seem to finish the thought.

"Yeah, I know," I said, saving her the trouble. "You're a leapin' lesbo and I'm a man and never the twain shall meet."

"Yup," she agreed.

"You know I don't give a shit about any of that."

"I do," she confirmed.

"And you know I don't want anything extra from you."

"I know that, too."

"So where's the problem?"

"You mean aside from the fact that I just fucked you up the ass with my strapon?"

"Oh, that."

"Yes, that," she replied. We stopped in front of her apartment building. She turned to face me. "Look, dipshit," she began. "I know sex for you is like breathing for normal people. But not everybody is like you. I'm not like you. Sex for me is special. It means something."

"Means something to me too," I insisted. "No matter who I'm with, no matter what the circumstances, it always means something. Sometimes it means a little, sometimes it means a lot. With you, it means everything."

"Get it through your thick skull, Nimrod," she said, resorting to her standby defense mechanism of sarcasm and insults. "I'm not bi-curious. I'm not experimenting. I'm gay. I'm queer as a three-dollar bill. This is who I am. This is who I always have been and always will be."

"Me thinks thou dost protest too much," I replied, quoting Shakespeare and demonstrating my pompous idiocy.

"Fuck you."

"Brilliant comeback! Did it make your brain hurt to think up something so original?"

"Stop making jokes!" she snapped. "This isn't funny. This is my life." She seemed on the verge of tears as she continued. "You know, Shakespeare said something else: To thine own self be true. That's what I've been trying to do my whole life, and it ain't been easy. I've been struggling my ass off to make it work, to be who I am in a world that doesn't like people like me. Do you have any idea what it was like to be a thirteen year-old girl in Iowa who was only interested in other girls? To be told your entire life what a pretty girl you are and how you'll make some nice boy a good wife, and to have no interest in it, whatsoever? To feel the eyes of your parents and your teachers on you and the suspicion as you get older and graduate high school and still have never had a boyfriend? Do you have any concept?"

Her face had turned near as red as her hair. Had I been paying attention, had I not had my head firmly up my ass, I might have been able to pull this back from the brink, but as it was, I was too fucking stupid.

"I've never gone on a date with a boy," she continued. "Never. I've never had any interest. Do you know what that cost me?"

And that's when my abject stupidity reared its ugly, moronic, absolutely full of shit head. "A buck-fifty?" Sometimes I'm too smart-assed for my own good – or anyone else's.

"You are such an asshole!" she shouted while commencing to pummel me about the head and neck. "Why do I put up with your bullshit?"

This had degenerated to a place I had neither wanted, nor expected. And it was my fault. As I stood there getting justifiably bitch-slapped in front of her apartment building, amidst the stares and scowls of several passers-by, as well as a few people sticking their heads out of nearby windows to see just what in the hell was going on, it occurred to me that she was absolutely right. I was an asshole. Now all I had to do was figure out a way to fix it before it was too late, which of course was the exact wrong way to go.

I grabbed her flailing arms in an effort to stop her beating the shit out of me long enough to speak a few syllables. In retrospect, I think I'd have been better off allowing her to kick my stupid ass.

"You're right," I began. "You're right, you're right, you're right, you're right, you're right," I continued in rapid fire acceptance of my utter wrong-ness. She responded by kicking me in the shin. Okay, I deserved that. "Ow!" I barked. "Please, stop." She smacked me upside the head one more time for good measure then pushed away from me.

"What are you going to say, Jack?" she blurted as she paced back and forth, her arms crossed over her chest, her face a mask of hurt and anger and tears. "What kind of greeting card platitude bullshit are you going to throw at me this time?"

"Well," I began. "I was going to say I love who you are. And I accept who you are – everything about who you are: the good, the bad, and the bizarre mutant lesbo, but since I've already proven myself to be a mental defective of monumental proportions, I think I'll just repeat that you're right. I don't know what it's like. I can't know what it's like. And I'm sorry from the bottom of my heart that you've had to go through that not-so happy horseshit," I continued, and thus far, I think I was doing pretty well, was saying what needed to be said. And had I stopped there – had I kept my idiotic mouth shut – I might have been okay. Or maybe not, and in any event, the point is moot, because I then added: "But what does it have to do with the price of tea in China?"

Yes, I am the stupidest man alive.

She answered with a look that should have caused my head to explode, and then without saying a word, she turned and went inside, leaving me out in the cold, with only my idiocy to keep me warm.

...To Be Continued...

Dear Reader: Okay...Here's the deal: I can't tell if anybody's even reading this, since I haven't gotten a single response past the 3rd installment. I hate to sound petulant, but there isn't much point in continuing if nobody's reading it. Please let me know what you think. e-mail to wyldenights at yahoo dot com and whatever else you do, please support Nifty.

Next: Chapter 9


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