How I Met My Shemale Pt. 03

It was early in the morning after a satisfying sleep. The cadence of bird sounds gave way to the rise and fall of passing cars below. Check out time wasn't for hours, but deadlines always bothered me.

Cheryl slept soundly. I wondered what mood she would wake up in after my misconduct of the night before.

Lord, but she was beautiful. I was in love with every inch of her curvaceous form. I ran my fingers though her silky locks, baring her pretty face. Her lips were full and so very sensual in the light of the day to come. A stray strand of hair tickled her delicate nose. Curious at the private joy of surveying her, I caressed the small of her hip, and kissed her. Her response was immediate.

Smiling, she returned my kiss; turning to me, still asleep, she parted her lips.

Her breasts yielded under me; her nipples hardened amid whorls of my chest hair. I rested my thigh across her hips to test her reaction. I was not disappointed—she arched her back ever so slightly, pressing her engorged she-cock into my flesh.

I broke away from her lips, deciding instead to suck her breast buds. I couldn't resist wrapping my hand around her cock, and gave it a few long slow pulls. My thumb and forefinger lost contact with each other as my strokes crested her swollen glans. I'd made her nice and hard.

"Hey!" she said. "What the fuck do you think you're doing?" She bolted upright, knocked my hand away. "Not while I'm asleep." Her eyes welled up. She glared, repeating, "Never while I'm asleep."

I flopped onto my back; my cock pointed straight up. I watched her wrap a bed sheet around herself. She strode off to the bathroom. I looked away—her taut round ass swiveling under the sheet sent a surge charging to the tip of my erection. She paused in the doorway, glaring at me over her shoulder.

I rolled over on my side. Damn it all.

Drumming shower water lulled me off to sleep.

"Get up Romeo! C'mon!" she said. I blinked up at her. It was like we'd met for the first time. There must have been something in that unguarded moment—something honest and real. Her expression softened. She went on, "Check out's in like half an hour." She was fully dressed and smelled great—leather and Chanel Number five.

"Oh crap," I said. I didn't like rushed packing jobs. I always felt that's how things get left behind.

"Oh, just get going," said Cheryl. "Get our stuff in the car and we'll get breakfast. No big deal." I rose up, baring myself in the process. She glanced at my cock; the happy pride of ownership danced across her face.

I had to admire her standing outside in the hall. Angry fluorescent lights loomed overhead. "Got both the keys?" she asked. I couldn't speak.

The couple next door—the annoyed couple from the night before entered the hall, and stared us up and down—down their noses. Cheryl never batted an eye. Calm and cool, she turned her back to them, flipped her hair over one shoulder, and bent over to grab her purse. Her black leather mini rode up, revealing her stocking tops. No woman had a finer ass than hers. The man annoyed his wife with his hungry dropped-mouth expression.

"Let's get out of here," said Cheryl. Halfway down the hall, she grabbed my ass cheek just for the fuck of it.

Shadows cast by buildings and city structures flittered over the hood of our car. They became fewer and farther between as we reached the city limits. My thoughts drew inward; we had reached the open road. It was just the two of us, with her at the wheel. I waited for her to talk.

"Just so you know, I'm not mad at you."

Her voice surprised me, causing me to squint, to recall. She took a hand off the wheel, dropping it into my lap. I parted my legs, allowing her to explore.

"I like that you want me," she said. "A lot of guys wouldn't—not after finding my hard, nasty secret." My shaft tingled, growing under her insistent massaging hand.

"Well this guy wants you." I said. "More than anything."

"So where were you going next? You know what I mean? This morning?" she asked.

I leaned back with my hands behind my head. "I was pretty much playing it by ear. But that cock of yours sure looked like it needed a good sucking."

Cheryl tugged at the hem of her skirt. She shot me two sidelong glances. "Well, you want to?" Her eyelashes swept down, bearing down for a split second. With a deft motion, she unpinned her cock restraint. A shock wave traveled across her lap. Her shaft bobbed around under the fabric, tented, conducting the rhythm of the road. My mouth watered.

She pouted, fumbling for the cruise control and seat adjusters. I watched her knees rise to hold the wheel, allowing her to lift her ass off the seat, and pull her skirt up out of the way. She settled into her seat, and retook the wheel. Her she-cock was rock hard in the broad daylight.

I leaned over; the shoulder belt dug in, opposing my motion, just an inch short of taking her cock into my mouth. She groaned, palmed the top of my head. My tongue touched down into her juiced-up cock slit. I unlatched the belt, and took her in.

She was salty and sweet, writhing, twisting her thighs, humping upwards in time with the tunes playing on the stereo. I was in position, with one arm under her stockinged knees, the other around her backside, my head bobbing over her hard thighs.

Now and again, we met with oncoming traffic. She leaned forward, hiding me from view. Her tits rested fully on my head as I sucked her throbbing inches. I swirled my tongue around her sculpted cock head; she moaned, trembled. Her fingers tangled in my hair.

"Oh fuck! So good. Take me!" Her words vibrated straight to the tip of her cock. She tensed, pushing back from the wheel, crushing my arm behind her.

"Ah! I love you, you fucker! I'm coming!" I opened my eyes. She came in mid suck—a thick and sudden jolt pushed past my lips with her cock part way in my mouth. I closed my eyes, sucked her fully, catching her volleying cream spurts, swallowing hard.

I sat up. Cheryl sat recovering, staring into my eyes, all as in a dream. Her milk white breasts stood free above her brassiere, cleavage exaggerated between her elastic shoulder straps. One tit remained cupped in her hand.

A tall shadow towered along side us. I focused out the driver's window. A trucker leered down into our car, grinning and horny. One of his hands was out of sight—shoulder rolling and jumping. My lips were slick. My stomach lurched.

I tapped Cheryl on the knee; I motioned to her, urging her to look to the left.

Cheryl shrugged her shoulders, furrowed her brows at me. The trucker reached up. He pulled the cord, triggering a massive horn blast.

"Wha!" Cheryl covered her tits. She hit the brakes, swerving, sending white smoke pouring from our wheel wells. I flew forward, seat belt free. The truck veered to the outer edge of the highway. Gravel sprayed, black smoke reeled from the chrome stacks. He hauled ass down the road, the hell away from us.

"Holy shit!" All color drained from her face. I slid back into my seat, rubbing my sore elbows. I tipped my head back, and wiped my mouth. I could still taste her, but less so. She pursed her lips, shy and methodical in rearranging her clothes.

We were quiet for much of the remaining way home. I imagined my family, hearing of my demise on the highway. "He was with a what?"

He was with his woman. He died hap___

"Hey, you know what?" asked Cheryl.

"Hmm."

"Move in with me. My place is no palace, but move in with me anyway."

"Okay. Let's do it." There. Done and done.

We had a long leisurely shower at her place. I stood behind her, soaping her up. She leaned her head back over my shoulder, the water pelting down into her open mouth. I was in bliss pure and simple, massaging her slippery tits and torso. My cock was snug, poised neatly between her tight thighs. It was unbelievable.

I settled into bed beside her. Flipping onto her side, brandishing her bare ass, she drew one knee up to her chest. She was naked, save for black stockings and high heels—the ones she knew would drive me crazy. I crawled back along the sheets, and planted kisses on her creamy smooth ass cheeks. My tongue probed into her tight little hole, drawing a horny moan from her. "Ah! Here!" Impatient, she shoved her still pliable cock back between her legs. I held her glans just short of touching her puckered hole, trading tongue-lashings between them. Her precome slithered out, adding a viscous glaze to her opening.

She passed me her tube of KY lube and squeezed a dollop of cool clear jelly onto my fingers. "I'm letting you in, babe. Do me good, and I might let you in again."

Adjusting to the position, I kneaded the lube well into her tight anal ring. Entering, withdrawing with one finger, then two, I prepared her for my fuck shaft. She pressed back with every plunge, matching my speeding tempo. "Oh! Give me that cock."

I spread her opening with two fingers; I eased my hard bulb inside. My entire body tingled on entering. "Fuck me! Fuck my fresh little ass!" She went wild, enjoying her anal initiation, slamming back to meet my thrusts. Her ass clenched around my shuttling member, causing my loose cock sheath to surround my shaft as I pumped into her. Her loud sighs shocked me every time my cock head's girth stretched her asshole, nearing the limits of my exit strokes.

"Oh fuck! This is so__" She shuddered; she reached back and clutched her heel. The black stiletto spike of her shoe cleaved into me, right into my ass. Impaled, gripping her ankle, I drove into her balls deep. We remained locked together, delirious in a fuck embrace. I came deep in her depths, hips shaking, sweat pooling between our bodies.

I rolled over with my cock still locked inside, succeeding in pulling her over on top of me. With my hands tugging hard on her she-cock, squeezing her uptight balls, I made her come. It spouted out—arcs of it splattered beside her face, on her face, all over her heaving belly and tits. Her ejaculations, her crotch spasms milked me dry. I rubbed it all over her, soothing her sex-flushed skin. "That's something we'll do again. So good," she said. Her next sentence trailed off. She slept in my arms.

"Do you ever wonder__?"

"What? Oh. Good morning," I said.

"Yeah, yeah." Cheryl propped her head on her hand and peered into my eyes. Her fingers trilled over my nipples. She continued, "Like I was saying, do you ever wonder, or like are curious about pussies? You know. Touching one, licking one, going into one?"

"I am. No, was. But it's you and me now, and it's perfect," I replied. "How about you? Ever had the pleasure?" I asked.

She slapped my chest. "I've been close, but no, can't say as I have." It was the first mention of pussy between us, ever.

Classes started up again after the New Year. My concentration was shot. Close, she was close? How close, I wondered. I should have pressed for details. Our lives had blended together nicely, and I didn't want to screw things up.

I waited for her to mention it, especially while we watched sex videos. She was dismissive of the topic, but did dwell on it; heavy lidded glances scanned me for arousal. Some guy would be licking snatch—"That's gross," she would say. We never failed to have extra hot sex afterwards.

I stayed late at the university litho studio one night. Someone had polluted the water in the paper trough, and quite frankly, it stunk. I collected my things, and made my way home. It was Friday, so if we stayed in, it was lasagna night. Watching Cheryl eat my cooking aroused me.

I walked home that night. It was springtime; the water ran in the streets. I hummed along with the trickling sounds of water, weaving in and out of the cones of streetlights, pretending I was a spy on a mission. Nearing our place, I noticed a strange car parked outside; it had out of province plates.

I tried the door; finding it unlocked, I went in. Cheryl needed a lecture on urban safety.

"Hi dear. We have a guest," said Cheryl.

"A guest?" I asked. "That's a first." I kicked off my shoes, and stepped into the kitchen.

A mostly eaten pan of my lasagna sat on the counter, foil rolled back. Two wine bottles were out—one empty, one not. We did indeed have a guest.

I tipped my head. Our guest seemed shy; I said hello. She offered a 'hey', barely turning to look at me. She was a mature blonde lady of the heavier persuasion, seemed nice. She introduced herself as Joyce. I gathered she was a former teacher of Cheryl's. Why she was with us, I had no idea.

Her and Cheryl went back to their chat, a bit tipsy, but a happy sort of tipsy. I sat at the far end of the table, shoveling forkfuls of reheated pasta into my face. Cheryl was in the middle of telling her the story about her name change. Her hippy parents had named her She. The first chance she got, she changed it to Sherry, later to Cheryl. Her teacher still called her Sherry.

"Oops, sorry, Cheryl, do continue," said Joyce. I poured myself some wine while there was still some to be had.

"So anyways," said Cheryl, "I haven't heard from those hippies since they went off to some cult. I do love their money though."

"Ha! Money's good!" said Joyce, slapping the table. Cheryl caught the wine bottle in mid topple. They laughed like hell.

Joyce raised her arms over her head and yawned. I could tell she'd skipped wearing deodorant. I caught a glimpse her big, bra-stretching breasts. She blushed. She leaned in, brow knitted with drunken concern. Smiling, she asked, "And you are?"

I stood. "I am going to bed." They laughed again. They laughed some more when Cheryl slapped my ass as I left.

"Don't start without her! Women hate that!"

They stayed up late. Getting Cheryl to tell me about Joyce meant waking her up three times. Teacher, bla bla. Divorced, hard up. You wanna do me? Ha ha. Snore. Staying until she can get her act together. Oh shit. She promised her our bedroom, starting tomorrow. I didn't like the spare room at all. Go to sleep. Fuck.

Saturday morning was damn near the afternoon by the time the ladies woke up. We let Joyce choose a restaurant. Even so, she picked around at her food, insisted things be returned. Does this taste funny? And on and on. What a royal pain in the ass she was. At the end of it all, she slid her hand towards the bill. Her shoulders slumped when Cheryl laughed and grabbed it off the table. "Get the next one," said Cheryl. I hoped there wouldn't be too many next ones for Joyce and us.

The rest of the day was okay. Joyce had been around the city, but not for many years. Every now and then, she grew pensive, lost inside, stroking the white shadow on her left ring finger. Worse, were her odd flinches. Sometimes they went beyond compulsive neck extensions, spinal corrections. Sometimes her lips drew back in a sickening rectus, eyes bugged out and all. I looked away. Cheryl told me meds were to blame—lithium withdrawal, or some damn thing. "Cut her some slack dude. She was good to me." It was wearing on my nerves.

For the first time in our relationship, I refused Cheryl's bedtime advances. "Sorry. I'm tired," I said.

She cuddled up behind me. "Let me. Okay." I said no. "Listen," replied Cheryl, "Tonight's fine. Joyce is zonked out but good. Her new meds start tomorrow. Any little sound will wake her up. Get it?"

"Too bad. I'm too tired."

She persisted. She jabbed her cock up between my buttocks. "Let me do it."

"No."

"Yes," she said. I lay motionless on my side. Cheryl gave up on fucking me, but not on climaxing. Her squelching, masturbating fist smacked my ass flesh—her cock head's tip strained against my entrance. That I much I allowed.

"Take it!" She squirted into me. The bed shook. I smirked, begrudging her climax. "You bastard," she said. "What's your problem anyway? Sick of me or something?"

I said nothing. I slept facedown; her coveted spill trickled into my depths. I tried to think of what to say. Heat and humiliation swarmed. Out with it.

"My problem is I don't like boozed up people. One drink, that's cool. But it's been all week with it. That's all." That most of it.

"You're such a chick sometimes. No oral for you." She yawned. I waited for her to sleep. She slept. So much for pillow talk.

I had a short nap, woke up thirsty. I decided to call a friend of mine from across town. Maybe I could sack out there for the next little while. Damn, my phone book was under the bed—where Joyce slept. Fuck it, I needed it. Maybe I could sneak out before morning.

The door let out a squeak; Joyce stirred in her sleep. I stood rock-still, allowing my eyes to adjust to the light. I went in.

I stood over her, at her bedside. She was a damn fine looking woman, all splayed out like she was. She didn't bother cleaning off her makeup; mascara smeared the pillow. The red of her lipstick matched her lace teddy, fully visible from the waist up. There must be someone Cheryl could fix her up with, I thought. Then she would be out of here lots sooner.

I got the phonebook and made my way to the door. Joyce made a muffled sound. She was sleeping, touching herself with one hand, busy under the covers. She had one arm behind her head; her lips parted in a lusty sigh.

I ventured back in. Hell, she wasn't so bad in the low light. My cock rose as I watched.

I lowered my head to catch a whiff of her exposed underarm. Sweat of arousal glistened in her armpit, amid curls of soft blonde hair.

Her scent excited me; I went closer. Oh god, she did smell good, all sleeping and wanting it. My hand strayed down to cradle the underside of my cock. I wanted it too.

I admired her big supple breasts. I lifted the red lace away from her tits, and breathed on them, yearning to rest my face there. Her nipples stiffened; she smiled, eyes shut, quivering shut.

I straightened up; a generous drop of precome surged into my shaft.

Fuck it. Who will know? I held my cock slit shut and positioned my knob over her open mouth. Holding my breath, I released. The clear drop spilled out; my toes curled as it dripped on her tongue. "Good, tastes good."

She brought her masturbating fingers up, and moaned on them, licking, sucking. I made my get-away. The last I heard was her calling what I assumed was her ex's name.

Back in bed, Cheryl's voice was the next thing I heard. "Where were you?"

"Nowhere." I pretended to sleep. Cheryl found me erect.

"Yeah. I'll bet." She yanked my rod sharply, and let it slap back against my belly. "You better watch it."

"And I think Joyce needs to go," she said. I felt it more than I heard it. Yes, she should.

Joyce wasn't sitting on the couch when I came home that night. Guilt mixed with regret? What's the name for that? I wondered. Wait, her stuff was still there. "Oh, hey. Seen Cheryl around?" asked Joyce. There she was, drying her hair, fresh out of the shower. I looked away.

"Nope."

I made an excuse to go to my room and waited for Cheryl to come home. I sat dozing over my art presentation notes. Cheryl's voice woke me up.

"You serious?" she said. "Sleeping already?" She walked up behind me; her hot breath on my neck. "Turn around. Face me."

I obeyed. "Close your eyes. I went shopping." I heard a bag rustle. She undid my belt with me still seated. "Stand up. And no peeking."

She pulled my pants and shorts down. I stood with eyes closed, hoping to feel her lips on me. Something hard and cool grazed my cock.

"Don't look 'til I say so, understand?"

"Yes."

She arranged my privates in a curious way. She exhaled in annoyance—I was getting hard. Something clicked shut around my testicles, around the base of my cock. Another smaller click followed.

Cheryl exhaled a happy murmur. "Gotcha! Now look!"

"What the?" I looked down to find my cock flesh all bunched up, all in fleshy folds bulging, encased in a clear plastic device.