Just a Friendly Rough Encounter

Just a Friendly Rough Encounter

Man meets woman, woman has more than a little extra

Millie Dynamite

© Copyright 2023 by Millie Dynamite

This is a work of fiction and not intended to promote a lifestyle. The names, characters, places, and incidents are products of the author's imagination or used fictitiously. Any similarity to any person, living or dead, is merely coincidental.

Just Friendly Rough Encounter

Time -- Yesterday: Place -- Anywhere

The bar packed shoulder to shoulder with customers inside, and I could only find a table for two, with a girl already sitting. Well, she appeared to be a lovely young woman. Slight build, maybe five foot or maybe five one, couldn't have weighed over 100 pounds, long blonde hair, bright, brilliant blue eyes, and pouty full lips. A natural beauty, so I approached her with more than a bit of trepidation.

"Excuse me, miss, would it be alright if I sat? " I asked, beer in my hand.

"If you don't mind buying me a drink, we might as well have a friendly drink together," she said in a soft, slightly husky voice. "And if you don't mind sitting with a transgender."

"I don't mind," I said, sitting in the chair. I adjusted it some, moving closer to her. "Never met a real live transgender in person, well, that I know of."

I motioned for an attractive server to come over.

"Some of us are quite secretive," she said. "Not me. See, I'm open and above board."

"I like honesty," I said. Which was only half a lie. I like the other person, but to be honest, I usually get caught in my lies pretty fast.

The young waitress came to us, holding one hand on her hip. In the other hand, she held a tray filled with empty drinks. She struck a pose, and I couldn't tell if she tried to look sexy for my new friend or me.

"Whatever the lovely young lady wants?"

"Shirley's no lady. She proved that to me recently." The waitress giggled. "Vodka tonic, sweetie?" she leaned down to her and whispered in Shirley's ear.

"Not tonight, baby," Shirley said. Adding, "Vodka tonic is fine, June."

The server walked away, her hips swinging in a sexy Marilyn way.

"Don't mind June. She likes my big girl cock." Shirley slid a cube of ice from the glass into her mouth. She rolled it around, drilling a commanding gaze into me. "Are you wondering if you'd like girl cock?"

"Never thought about a penis other than my own before. Not sure I'd like to find out about yours, to be honest." However, I pondered the possibility that I might like her dick.

Her jaw moved, snap, crack, crunch, crunch. She devoured the ice. Something sexy about how she ate the ice. While she ate, she gazed at me innocently from the azure pools of her beautiful eyes for something, my approval, desire, or surrender. I wasn't sure what.

Cutting through my defenses, "I think you want to find out about me, my cock, what it's like to belong to someone whose power isn't physical." She reached over and touched my hand.

This simple gesture took me off guard.

Her touch was warm, gentle, and tender. I was thinking I'd already made a mistake, a serious blunder. My heart skipped a beat. More than one beat. My head spun as I felt my blood pressure increase. I felt dizzy. I'd never had this happen from anyone's touch before.

"I am not as innocent as I appear," she said. "You're thankful for one of us not being innocent in this type of thing, aren't you? Let me usher you into a first time, a new world, as it were."

"That's good," I said, "But I like to be the first one to violate innocence. Not the one who has his innocence taken." I thought I might decline her invitation and get out of it, hopefully without her becoming upset. She leaned into me and ran her hand up to my biceps. Like any man, when a sexy girl touches their arm, I flexed.

"Your eyes are brown because you're so full of shit, baby. Why don't you touch me, where you want to touch me," she said.

Following her suggestion, I reached under the table, eased up her skirt, and cupped her cock in my hand. My god, it was massive. It was hot, throbbing with blood, and pulsed in my hand. Each rush of blood was a new heartbeat. I felt it expand in my grip.

Without having ever touched another penis besides mine, I developed a new realization of what a cock was. The cock was firm, granite-hard, and masculine, which took me aback, as Shirley was so feminine and petite.

"Do you know what you are doing?" she asked.

"I have some idea," I answered. "Though it's unfamiliar territory for me."

"I'm not a Barbie doll," she said. "I'm not sure you have a clue what you're doing," she said.

June, the waitress, brought Shirley's drink. She asked me what I wanted.

Removing my hand from Shirley's crotch, I'm sure, appeared guilty as sin, which I was, of doing something wrong. "Another beer, sweetheart," I said.

The glance she gave told me she didn't like me.

When she was gone, Shirley said, "She's a sweetie, isn't she? I have all kinds of girls and boys, but June, she's just a sweetie. When I fuck her, she pants and wiggles around like a puppy, whimpering with every rough, deliberate thrust. When I fill her tight pussy or ass with my hot cum, she purrs like a minx and begs me for more."

"If you wanted to excite me, you should be pleased," I said, squirming. My eyes darted about, worried someone would overhear. This tiny voice, barely audible, inside my brain told me Shirley would make me wimp faggot.

"When she brings your beer, drink it like a good boy so we can go to my place. Don't doddle away time, sipping."

"Yes, ma'am," I said, unsure of my next move. The one thing I wasn't thinking about any longer was getting away from her.

****

Shirley led the way to her house. I followed, not precisely with a sense of urgency. Hell, I wasn't sure what my next move was.

The pull that she had on me was incredible. I felt like what a schoolboy must feel for his first crush. My heart raced like a rabbit. Sweaty palms and knees that wobbled. My stomach was in knots.

She left me at the door of her home while she got ready. She made me wait, which I guess was part of my test.

While I waited, I prepared myself for the moment. I wouldn't be at the bottom, that's for sure. Shirley would find herself on the bottom. I'm a straight man, make good money, have an ex-wife, several girlfriends, and family. I was a top, not a bottom.

"Come in," she said. This nagging fear took me; I hadn't a choice between top and bottom. In fact, choice was something I hadn't enjoyed since I sat down with her.

Opening the door, I forced my foot through the threshold and closed the door behind me. Candles burned on a mantel on one wall. They drew my gaze to them, flickering a dim glow around the room. But she wasn't there.

"Over here," she said.

My eyes followed her voice. Shirley stood at the foot of a grand, curved staircase, leaning against the banister. She wore a black lace teddy, her magnificent prick hid her belly button, and the frilly lace pattern against her alabaster skin took my breath away. Dangling from the index finger of her right hand was a pair of handcuffs.

I stood, frozen in place, confused by her beauty and the contrast between feminine and masculine, so jumbled together.

"Why are you quiet? Have you forgotten how to speak?"

I was afraid that if I spoke, my voice would shake. I was worried about what I might say for the first time in my life. The person I was only a few moments ago seemed a lifetime ago. I wanted to impress her, not make a fool of myself. I clung to a single shred of dignity and didn't want to turn into what I would need to become to be with her.

"I'm speechless," I said, feeling a bit wobbly. I sipped my beer, trying to calm myself, but my hands wouldn't stop shaking.

Walking to me, Shirley patted my hand and said, "There is nothing to fear," and slid her smooth, soft hand over my forearm. A sharp, musky scent that made me want to sniff the air, the fragrance of a great cat, the male lion before it attacks, the female in heat. I breathed deeply, aroused.

But knew full well that in our relationship, the lioness was the attacker, and the lion would submit or devoured. As much as I didn't want to, I eyeballed the cuffs. And my eyes followed that bit of metal until it disappeared behind her in the dim candlelight. Before I knew it, the handholding the cuffs was back and at my wrist. With a quick movement, she flipped the cuff over my wrist.

"Now, sugar, I have a couple of questions," she said.

"Ask away."

"Are you really chaste and virginal with someone like me?"

"I've never touched another person's penis, before yours, never been around a person like you. What about you? Have you ever introduced anyone like me to, you know?"

"Yes, many times," she said. "A little about me. I grew up in a household with three older sisters. Like bullying older sisters are want to do, they dressed me in their old dresses and nighties at home and often made me wear panties. In time, I preferred dresses, preferred being a girl with a bit more."

"That's fascinating," I said.

"Turn around," she said.

Turning my back to her.

"Kneel."

I kneeled, and I'm not sure why, but I hung my head.

Her lips brushed by ear, "Put the other cuff on your wrist, my pet."

I did so. Shirley's hands played with my hair and ran over my face. She bent down, her hair tickling the back of my neck, as her hands grabbed my shirt. Clutching my shirt, she ripped it open. The buttons fell to the floor, making a clatter with each landing. The hard plastic buttons bounced and scattered over the hardwood floor. My shirt's tail pulled free, and she pulled my shirt back over my arms.

Long thin fingers tangled into my hair, clutch a thick hand full. Shirley yanked my head back. The thick redolence of her perfume, hair, skin, heady like clove and spice, assaulted my nostrils. Not a violent attack, but a seductive strike, which moves inside you, taking control.

"Now, my lovely prisoner, ask to suck my girl prick."

"May I please suck your dick, Shirley?"

"Mistress Shirley, to you, Glen," she said, with her mouth hovering at mine. She moved her breath into my mouth and nose, it warmed my lips. Her hair fell over me like a veil, soft and sensual, covering my eyes, toying with the flesh on my temple. Her tongue snaked into my mouth.

I lost myself in her kiss. My head spun with her scent, the taste of her tongue, and the power she held over me. With some urgency, my cock surged, straining against the heave denim fabric of my worn jeans. Pushing up, trying to get closer to her, I squirmed against my restraints, wanting to take control.

As I struggled, trying to stand, Shirley put a thumbnail deep into the front of my shoulder and her fingernails into the back and dug into the flesh. She broke our kiss and hissed at me.

"Stop trying to top from the bottom," she said.

She stepped in front of me, pulled her stupendous dick free, and pummeled my nose, cheeks, and lips. The dick I once thought of as magnificent now seemed colossal and monstrous. Its veiny texture rippled and pushed the entire length, veins and all, against my face. Each time she hit me, it sent ripples through my brain.

Her dick is the most beautiful thing I'd ever seen. The shaft is pink and veined as if each pale blue vein was thick, the cockhead darker than the shaft. Her balls are large and loose, hanging. Her cock is perfect. Open my mouth, eager to learn how to please her.

Wasting no time, she thrust her hips, filling my mouth with her thick tool. The girl prick was salty but sweet. The girl's balls slap my neck with each stroke, the cockhead hitting my lips, the back, and the roof of my mouth, gagging me. Slowly, she increases the length of her strokes. The helmet invaded my throat.

She clasped her hand on the back of my head and pulled forward. Her fat cock went deeper, gagging me more. Her grip gripped my head, and I struggled to inhale. Shirley quickened her pace, increasing the intensity.

At first, I let shame boil up, but the more fucked my throat, the more I realized I didn't desire anything but pleasure. As Shirley's cock filled my throat, embarrassment vanished, and I relaxed and focused on my task.

With each thrust, I gagged and choked and wanted more of it down my throat. Shirley's pick was warm, erect, vibrating, and pushed down my gullet about Adam's apple deep. Sweat breaks on my forehead. I struggle to breathe. My heart pounds, I'm light-headed, and my cock twitches and jumps. The scent of her perfume smothers me.

The aroma of perfume and sex was overpowering.

As she plunged faster, stronger, forceful, the head of her dick slammed into my throat. More and more, her cock goes into my mouth. The harder she pushes, the harder I struggle. The more I gagged, the harder she shoved her cock into my esophagus. The more I battle to breathe, the more she enjoys my predicament. As she thrusts her hips and hisses at me.

"Good boy, you know your place, don't you?"

The taste of her precum fouls my mouth, and I stop struggling. Surrendering to her strength beyond physicality. She pulled control from me, and Shirley filled my mouth repeatedly, pushing her cock inside me repeatedly. Her hips lunged, and her dick slid deep down. The waves of pleasure wash over me.

From the back of my throat, I gag and cough. My arms pull and strain against the handcuffs. My legs tense and tingle, my toes curl, and my legs clench. She yanked her cock from my mouth, rubbed it on my cheeks and forehead, and held my head against her belly.

Somehow, I came, and the fiery blast of semen soaked my pants.

Stepping back, she held my head, her fingernails dug into my scalp, and she blasted several thick streams of semen, painting my face. Shirley removed my shoes, pants, and underwear.

Shirley jerked me to my feet and led me to a small table. I was afraid she was going to beat me. No, that's a lie. I hoped she beat me. As she hauled me to the table, my cock hardened and ached, unused to being so stimulated. She pushed my face down onto the table. There was a hole, and my cock went through it.

"You like wearing my cum, don't you, boy?"

"Yes, Mistress Shirley, I love your cum."

As she moved about, I wondered what she was doing. I heard a drawer open and close. When she returned to me, she clutched my hair, lifted my face, and ran her hand around my face, collecting the cum. My eyes opened to her hand cupped in front of them. Shirley held globs of her cum in her palm.

I blinked, and she pushed her hand in front of my lips. There was no way to avoid it, no way to run. I had to obey. Sticky my tongue out, I ate the goo, whitish, nearly transparent, tasting like salt, sweat, and sugary spiced flesh.

"You've been a bad boy, not cleaning your face," she said, pushing my head toward the cushioned leather-covered table. "Now, clean up this mess."

The cum was a thick, heavy cream and filled my mouth as I lapped it from the leather. The taste was perfect and pure, like Shirley's orgasm filled my mouth and sent me into ecstasy. It amplified my senses. The world went silent except for the pounding of my heart and my breath.

With a dry, coarse cloth, Shirley mopped my face and leather clean of any remaining cum or slobber. Shaking my head, she whispered in my ear.

"Bad boys get spanked."

As Shirley moved away, I turned my head sideways, craning my neck to follow her. Throwing the towel into a trash can, she opened a drawer, pulled something out, and turned back to me. Her cock, now limp, hung twice as low as mine. In hand was a wooden paddle. Shirley smacked the paddle sideways into her other palm while walking back to me.

"Nasty boy's ass can't move away while he gets his punishment."

With a few soft blows, she warmed up my ass. Alternating between my right and left cheeks, Shirley hit me a little harder each time. I peek back over my shoulder, watching. Her flagellation of my ass was a blur of the red and black of the paddle. Her hands were a blur, the way they moved fast and distinct. She was an angel of pleasure and pain.

With each blow, the paddle makes a wet thwack, crisp, my ass being branded as the mistress marks her slave. The smack of the paddle meeting my skin, the air pushed out of my lungs in grunts of pleasured pain.

I cry, bawling like a blubbering baby. This pleases her.

"You like getting paddled?"

"Yes, mistress."

"Say, please."

"Please."

"Say I want more."

"I want more."

"Say I need more."

I nod my head, but fear she cannot see. "I need more."

"Beg for it."

"Please, mistress, I want more. I need more." Shirley was only getting started.

My ass was burning. When I peeked over my shoulder, I was glad I wasn't being watched by her. The look on Shirley's face, her bright smiling eyes cutting into me with a wicked grin. I could see her hand moving back, the paddle arching through the air.

Again, I blubber into the leather and bury my face as she pummels my ass.

"That's right, cry like the little BITCH you are." She tells me to pray. I pray to her, to her strength and her dominance. That She likes me and will not punish me too hard. I beg for her mercy.

"Oh, Goddess, I pray you'll find mercy for me, your slave."

She spanks me. She spanks me again. And again, muttering to herself, "what a dirty, nasty boy."

She stops. Nothing. No more blows from the paddle. Her hand? No. She is done. Or is she? I hold my breath, waiting for her to strike me again. The drawer opens, a dull thud, slides closed. Gazing up, I see her holding a tube of KY jelly. She squeezed the tube hard, causing it to make a squelching sound, almost like someone was choking or gagging.

After a moment, Shirley rubbed her cock with the jelly. Her prick gleamed and glistened with the lube. Each vein pulsed as she stroked the monster -- the head expanded and contracted. The elephantine penis grew hard again.

"Don't fight what happens next. I won't have to hurt you more than necessary," Shirley said, moving to the table. Something flung over my waist. After this, Shirley moved to the other side. A zipping sound, and what lay on my waist got tight. Like any suitable restraint, it's strong and unyielding.

"Time to lose your ass, cherry," she said.

She shoved the tube into my ass and squeezed out some. She yanked the tube from me. With a plop and slosh, the lubricant trailed out of my ass. Cold and oily the slime ran over my balls.

"That's better," she said. "Now, ask me to fuck you."

"Please, fuck me, Mistress Shirley," I said.

Her knees pressed into my thighs, she forced my ass higher, and then the mushroom head pushed against my asshole. The pressure built, and my ass resisted. With more force, my sphincter clenched. With one swift shove, she drove into all the head and an inch or two further forcing entry.

Grabbing the chain between the cuffs, she rocked into me deeper. Thrusting more cock went in. Shirley pulled back, the head almost exited, and down harder now, further, in and out. She fucked my ass hard, yanking my arms back, using her grip between my wrist. Fucking, fucking, fucking my ass.

My eyes closed. The blackness behind my lids became a blur of dull pain and intense pleasure. My cock, half the size of hers, pounded around the opening it was in. Like fucking a pussy far too big. It bumped here, thudded there, and my balls slapped the table and whacked by her bigger ones.

My body was tight, like a drawn bow, ready to snap, A cocked crossbow straining to release its bolt. Seeing only black until I opened them, seeing the leather covering the table. And she's there, back inside me, balls deep, rearranging my guts.