Vivian's Best Kind of Girlfriend Ch. 03

"Hey, you! You missed one! Get it right!" said one free-range citizen of our fair city. I shrugged, and stabbed up another piece of rubbish; he laughed, and sped off. I looked over my shoulder, back down the highway, towards the warden in charge of all us inmates out on trash detail. Oh well, at least it was nice to be outdoors.

What led me there was an unfortunate misadventure—one begun by Vivian.

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We sat across from each other on a leather loveseat in her apartment. We'd had a great evening out, and at last, I had her all to myself. She leaned her head back, stretched, and smiling with her eyes, secured my cock between the stockinged arches of her feet. We were together again; I was happy to be with her, rubbing her toes, my cock rolling between her silken foot bottoms.

I was dressed as her girlfriend Lorraine. I looked every bit a lady, in full fashion black stockings, sultry evening make up, and a flowing blonde wig. I massaged her cock-pleasing feet, pausing to adjust my impressive breast forms—they bobbled about, threatening to spill over the top of my lacy black brassiere.

Our eyes met; she flashed me her best mischievous grin. She lowered her chin to her chest, and exhaled while grasping the lapels of her silk dressing gown. In a single motion, she splayed open her robe, and brought her elbows together, lifting her naked breasts up into prominent view.

I gasped at the bold display of ripe pink nipples cresting the milky flesh of her quivering tits. My cock head flared between the soles of her feet. A clear drop of precome emerged. She noticed.

Vivian sighed, "Nasty girl tonight, eh?" Shaking her head, she slipped off the loveseat to stand in front of me. I sat on the edge of the seat and blushed, feet on the floor, facing her. I chose to stare at her thighs, thick captives of embroidery—voluptuous within heated black silk.

"Lorraine." She lifted my chin to gaze into my eyes. "Lorraine," she repeated. "Cross your legs, and put that thing of yours away. Oh, you're bad."

I did as I was told, concealing my rearing erection down between my stocking tops. More hot, slippery clear essence pulsed out onto my skin.

"Here," she said, straddling my midsection. "Kiss my titties." I groaned with pleasure, reveling at the strength in her legs. Her shoe heels dug into the sides on my legs.

I buried my face, luxuriating in her cleavage, nuzzling, licking and sucking with total abandon. The heat of her pussy lips intensified against my waist. She ground against me, pumping her hips, as I sucked her tits.

The second I came up for air, she put one hand behind my head and directed my lips onto an engorged breast bud. I swirled my tongue around it; I pulled a mouthful of her ripe tit flesh inward, and gently, ever so gently, squeezed my lips together. Her intimate arousal—losing myself in the moment—her scent, her passion; I'd never been so wanted, so fulfilled.

She moaned in response to my hands cupping her buttocks; caressing her lovely bottom delighted us both. Shuddering when I released the suction from her bulging tit, she drew a stuttering breath in through her slack red lips—her teeth chattered. Viv smiled down at her breasts, fully consumed in the blush of sex.

"Why Lori!" she exclaimed. "Look at my nipples! Just like two little cocks for you to suck!"

Cocks. Cocks for me to suck. I must admit my legs shook.

We moved into the bedroom, where we resumed our position. Viv rose up far enough to allow her hand to slip down under her panties' waistband. Her titties juddered—two rock hard nipples dancing, bobbing, grazing my flushed cheeks. Her tits swung, rebounding off beat to her masturbation.

With her weighty thighs off my lap, my trapped cock snapped upright, and slapped her ass. I bucked upward; my cock, slick and trembling, touched the lace guarding her pussy.

Even with her approaching orgasm, amid feverish handling of her sexy snatch, she acknowledged my staff—poised, wanting to fuck.

She sank down, rocking onto it, trapping it between us. With her heated pussy folds tensed around the underside of my cock, with her fingers swirling her clit, she latched her mouth onto mine. I kissed her; her tongue darted into my mouth, fluttering against mine.

"Lori!" she sighed, "Come for me! I love you! Come! Come now!" She came; her spine undulated under my palms. Collapsed and crushing me in her arms—how she shook and sobbed.

I shuttled my cock along the silk between her legs. My glans caught just under the barred entrance to her sex. I pushed into her, near to tearing through the silk barrier, up into her convulsing vagina.

I thrust once more; I missed, sending my cock to slide up along her sex lips—jamming it, trapping it once again between us. "Viv!" I cried out. "Let me inside."

She reached behind to grasp my legs above the knees, and leaned back, nipples pouting. Staring into my eyes, lips trembling, she encouraged me. She licked her lips, and looked down, fascinated to witness my masturbation. Sweat broke on my upper lip; I focused on the rise and fall of her beautiful breasts. Pearly jets rushed out of me. The first stream squirted her plump white belly; the rest seared the blackness of her panties.

"Good girl. Good girl, Lori," she said. We stretched out together on the bed to embrace, warm under the covers.

I held onto her for the longest time, my face burrowed in the bend of her neck—warm curls of perfumed hair so gentle and soothing. I hid there with eyes shut and stinging. Her breath slowed; she murmured something before kissing my cheek, before drifting off in bliss.

The love word burned away at the dark, and the badness in me. Smoke clouds plumed in my mind's eye, dank and vile. I stared into the growing light; I never once turned away. In time, elation spread though my being. I had my Vivian, and would have that moment forever, no matter what.

Pity. Hunger. Need. Now love. Good girl, good girl Lori.

The next morning was business as usual. Although I harbored a deeper attachment to her, I acted much the same. She said she loved me. I had never before been so close to entering her with my bare, spunk shooting cock. I was so distracted.

"Well, the day has come. It's time to visit the library," said Vivian. The thought of going out in public dressed as Viv's girl Lorraine had lost none of its novelty—it, in fact, felt more natural all the time. I had overcome my initial awkwardness, and looked forward to the exposure. I was showing the world my true self; my life as a male seemed false and superficial. And I owed it all to her.

"Turn for me. Let's get a good look at you." I finished slipping into my stilettos, and stood with head held high for her approval.

"Brilliant! Just beautiful!" she said. "Just wait 'til they get a load of you."

"Well thanks, I'm glad you like what you see."

"I love watching men look at you. You've dealt out a fair share of trouser bulges, you foxy thing," smiled Viv.

I swallowed hard. Viv stepped forward, beaming as she adjusted the top of my dress, neatly concealing the top of my breast forms. "You're a knock out, you know. Your bust looks great. As does your bottom." She said this while reaching around, giving my latex padded bottom a firm squeeze. My cock tensed inside its sheath, pulled up firm back between my legs. I struggled to calm myself, and my burgeoning erection.

We parked a block from the library, and set on our way. I loved the way my breasts jiggled as I walked beside her. My reflection in the passing windows pleased me greatly, as did the sensation of my stockings cavorting together within my vintage black slip.

It was a good thing the slip was a short one, as my hem rode just shy of the point where my stockings changed color. It was a tight fit as well, like my dress—red satin gathers strained around my curvaceous derriere. Bumps under reflective red hinted at the location of my garter straps.

On arriving at the library, a man gave us both a generous smile and held the door. We nodded him a thank you, and shared in a coy smile. I was her secret—her special project and lover.

At first we wandered the aisles, discussing this and that, all about the books. Viv halted mid sentence in front of an elaborately carved, antique step stool. She traded glances between it and myself, quite taken by the sight of it.

"Now Lorraine! Now that's something, isn't it!" I nodded in agreement. She pulled me back when I stepped away from it.

"Follow me to the back girly. We need to talk."

What proceeded was a plan to—well to be frank—to pull a heist. I was to get the step stool out into the alley, via the back door by the washrooms. I was to sneak it past the security guard, to where she would wait in her car. My mouth went dry. She couldn't be serious. It was crazy.

"And just how do you think the security guard is going miss that?" I asked.

"What? Him?" she whispered. "He's been ogling you the whole time. Use your imagination Lori." She winked and stepped in close. Squeezing my hand, she added, "Use your imagination. Do this and I'll repay you. Do whatever you must. Do it for me."

She left; I feigned interest in a book high on the shelf. I rolled the step stool to the bookshelf nearest the washrooms. On the way, I noticed the blinking red lights on each security camera I passed by. Things didn't look all too promising. Visions of me hit by a police tazer, writhing around out of control, wetting my panties, raced through my mind.

Still, onward and upward, as Viv would say.

I started on my way up the steps, and cringed—I had left my shoes on—not the greatest shoes for climbing. Seated on the stepstool, I crossed my legs and gingerly removed my stilettos. That finished, I looked up into the eyes of a tall black security guard.

"Excuse me Miss, may I be of some assistance?" he asked.

I peered up, flashing my long lashes. "Oh, you're very kind, but I'll be okay now."

"I don't know how you ladies walk in those things." He hiked his belt, and smiled; keys jingled at his side. The subtle outline of his cock head ridge played along the rising fabric of his trousers. I licked my lips, and shifted my attention back to his face. I was taken aback by his longing stare, directed deep within my cleavage. Turning aside, I raised a deft hand to my chest and blushed. I sat there, examining my painted toenails through the translucence of my hosiery.

"Good then," he said, "Feel free to ask. That's what I'm here for." Blood coursed through me, pounding in my ears, and swelling my captive erection.

I waited until he was several feet away; I spoke in sultry tones, "Pardon me, but could you direct me to the ladies room?"

He turned and pointed to the sign around the corner. My stomach lurched; I winked and nodded.

I got my shoes back on, and strode to the washroom, making sure to roll my hips the way Viv taught me—a sight, when viewed in the mirror, never failed to leave me breathless.

Standing at the sink, I leaned in and peered into the mirror. My heart pounded like a jackhammer; my mouth was dry. I stared at my image in the cold glass. I had a plan.

My heels clacked, announcing myself behind the door. I opened it just a crack, no more. As I suspected, the guard loitered nearby. Our eyes met; he was panting and wide-eyed. I turned my back to him, and bent over to tend to my garter stays. I raised my hem to treat him to the sight of my long lady legs, and the expanse of flawless white sex flesh emerging above the lace. I smoothed my calves, and plucked at the dark seam up the back of my stockings—drawing it up, straightening it between my red tipped fingers.

He watched; I could feel his eyes devouring me—boring into the meeting of my taut, naked thighs. I imagined our heartbeats in sync; I knew what he wanted to see. And I definitely knew what I wanted. My heart froze—he said, "Just a second."

He didn't venture inside; he left for a moment, and returned. He rapped gently on the door; he cleared his throat. I opened the door as before, and assumed the position. Bent over again, I put on a show for my horny admirer. I reached back in between my legs to rub my frilly crotch, nudging my captive cock with the heel of my hand. All the while I ensured my slip was well out of the way, as to not hinder his view.

Tendons high on my inner thighs tugged under my ivory skin with ever prodding stroke of my fingers. I shifted my weight from side to side, providing him with a slow, erotic dance. I stroked harder, on hearing the rapid jingle of his keys. He was busy with his cock while viewing my slutty upturned derriere—it framed by my tense garter straps. I pictured my ass swaying from side to side—a hypnotic cobra rhythm summoning his release.

What an erotic show it must have been, with my girlish moans in place of music. My free hand, and forearm cradled my breasts; the corners of my mouth formed an impassioned smile all on their own. Beads of precome parted my cock slit, flooding my shaft inside its slick enclosure. I drilled my fingers into my crotch; my legs trembled; I moaned, "Oh fuck! Oh fuck me!"

He inhaled a startled, "Oh!" He shut the door, leaving me shaking, and alone with my lust. No time to finish—time to make my move.

A quick peek outside confirmed my suspicion: no more security cameras were blinking. I ducked back inside to tighten my cock sling. Viv would have her stepstool; I would have her promise.

Stepping out again, I kept my back to the wall—no one was around. I edged along, finally reaching the stepstool. I scooped it up in my arms, and rushed to the alley exit. I took quick little steps, causing little noise, save for the clicking of my heels.

Fresh air washed over my flushed cheeks; I'd made it outside.

The door clacked shut behind my back. "Viv! Viv!" I called. With her nowhere in sight, and me locked in a blind alley with an antique stepstool, I considered tossing it in the dumpster, but no. She was there in a flash, in her powder blue Benz, tires screeching, backing down the alley. I could hear her cackling as I opened the trunk. The stepstool secured, I took my place beside Viv.

"Oi, Lori, you did right well!"

"Thanks, Viv. Use it in good health." What a curious thing to say—adrenaline was to blame.

She laughed, and rolled her eyes, "Whatever you say Lorraine!" We'd left the downtown when she spoke again. "So, Lori, I have to know. Did you..." She formed a pulse-quickening circle with her crimson lips, and poked inside her cheek with her tongue. Pumping a half closed fist towards her open mouth, she arched her brows. "Well?"

I straightened in my seat. "What?" The image of the guard's engorged phallus flashed before me. It dawned on me he could have pushed for more than just watching. He was a strong man too—what if he had insisted on more? Oh no! Had I really said, "Oh fuck me"? I shook my head, dispelling the thought.

"Oh hell no! I just put on a little show. That's all it took."

Back at her place, she rewarded me; she soothed my straining inches between her hot pillowy tits. She insisted I lick up every trace of come I'd shot anywhere near her nipples. I complied—anything for my Viv. Any lingering trace of my exotic flavor, she shared, swirling her tongue in my mouth. "Lori, ever taste anything like that before?"

I hadn't.

It was one, no wait, two days later when I next heard from her. We decided it was best we 'lay low' after the heist. I returned to my own home, and my male role in life, quite lost in my own skin. I ached to hear from her again.

The phone rang. "Lorraine get over here. Everything's set." Just the words I'd been dying to hear! I repeated them over and over again as I ran every red light on the way over. My cock was every bit as stiff as my truck's stick shift. At last, I would be with her again.

I raised my hand to knock on her door, but never got the chance. She opened the door wide, and pulled me inside. We held each other tight—she burrowed her face into my chest. "Lori. Lori honey, I've missed you so."

I closed my eyes, and kissed her forehead. "I missed you too. And I love you." My voice sounded so strange—quaked in my ears—distant thunder from a foreign land. My first 'I love you.'

She never answered—a tearful nod would do.

She led me to her bedroom, to where she indeed had been busy. Soft music played, candlelight shimmered. And there was the stepstool. Viv stepped in behind me, where she massaged my chest and cock.

"So what do you think Lori? Has your Vivian done well?"

"Oh yes! Looks great."

"Well good. Get dolled up. Tonight will be special."

I went about making the rightful changes—my transformation into Vivian's girl Lorraine. It was pretty much second nature by then: the shave and shower, the foundation with thick makeup, the wig, the false titties and eyelashes. My favorite part in this was always the lingerie.

I chose a short frilly slip, to match my black stockings. My black satin panties satin cooled my throbbing cock pulled back nice and snug, in its clear plastic sling. And, as usual, a glimpse of me in the mirror caused my cock to tingle and twitch.

"My sweet little wench, come show Vivian how you've done," she said. I posed for her, one high heel in front of the other, hands on hips, proudly displaying my firm breasts. I was one prime lady. She smiled, "Very nice. Really very nice."

"Here, help me into this." She produced a black latex corset, the kind with a lace up back. It looked so good on her, compressing her full figure just perfectly. And oh, her new thigh boots—they too laced up, to within a hand width of her panties' frilly leg elastics.

I was happy to see black stockings under them; I got down on my knees to do up her garter hooks, with my hot breath on her belly. I loved seeing her in her new things.

I took some time to perfect my lipstick; she waited in the bedroom. On my return, I was surprised again at how romantic she'd made everything. And all for me.

Normally, we'd begin with her seated on the edge of the bed; this time she posed on the stepstool. She wore an ankle length black robe; its slick texture contrasted with the black velvet curtains spanning the closet behind her. My heart skipped a beat, as now she was stood taller than me, more commanding in her posture. She regarded me with a haughty leer—so quick to avert her eyes.

She climbed down. "Turn around girly! I'm going to tie you." She brought her knee up from behind, hooking one leg around me as she lashed my wrists together. Her rear-laced boot buttons rasped against my stockinged legs.

I stood shaking, listening as she remounted the platform.

"Come here! Down on your knees! Down now!"

My will gone, I obeyed. I knelt in front of her, lowering my bottom to rest my crotch on the hard polished backs of my stiletto heels. My cock slipped over to one side under the pressure. I waited.

"Go on then. Kiss. Lick. Worship. Start at my feet and take your time."

Struggling to keep my balance, I crawled to her on my knees. I saw my blushing face reflected in her boots.

"That's it, take it all. Get your lips around it. That's it, lick, suck." I looked up, batting my eyelashes at her, sucking the end of her boot, obeying her. I was her pleasure. One at a time, she fed me her spiked heels.

Daring to act, I rose up, sliding my tongue up the length of her boots, one, then the other, stopping just above her knees.

"Wait there girly. Not so eager!" I closed my eyes; I pushed my forehead into her confined leather curves. "That's better. Good girl Lori."

Vivian moaned, releasing a guttural sigh, bending at the waist. She swiveled her curvy round hips, legs tightly together, slightly crossed. The musky scent of her arousal caused me to tremble before her.

"Now!" Reaching down, she pulled me up, squaring my face directly in front of her panties. "Kiss my pussy!"