tagTranssexuals & CrossdressersDeepest Fantasies #05

Deepest Fantasies #05

byFireSiren©

Tomorrow came, but my only surprise was to take Sean shopping for girl clothes. Whispering his selections to me, he chose some impossibly short padded pink hotpants, a lacy white half shirt, white stockings, specialty high pink heels, and a matching hot pink wonderbra and panties. He wasn't allowed to wear them. "There will be a bigger surprise," I promised, but enacting the plan that hatched when I accepted that my ten-year crush came violently in women's clothing was harder than I anticipated.

"Please," I begged over the telephone, as I watched him casually lean on the rail outside the motel, cunniling a cigarette, "I really NEED it for someone special." As his soft lips tickled and teased the end of the butt, I must have sounded desperate enough to melt hearts because the voice on the other end softened.

"We have ONE still available, but it's SMALL," the receptionist said cautiously.

Restraining the urge to squeal, I surrendered my necessary information, gushed thanks, and hung up.

March wind whipped my short blonde hair into Sean's long dark locks as I stepped onto the balcony and slid my arms around his waist. I rubbed my face against his shoulder and draped a hand over his waist. His free hand slipped down and squeezed mine lightly.

"Hey angel," he murmured.

I struggled to keep my voice even, "Mmmm hey."

He grinned and tossed the cigarette away then turned to wrap me close to him. "Am I the reason your heart's beating like a jack rabbit?"

I kissed his lips soundly then giddily murmured, "Uh huh. Always. I want you to get your stuff together."

Confusion flickered in his wide grey-green eyes before he said, "Allright." Then, "Is something wrong, angel?"

I shook my head quickly and tried not to grin. "If you hurry, we can probably beat check out time," I frugally suggested.

"Where we going?" He asked, reaching for the door and opening it for me.

I didn't answer.

"Where we going," was Sean's mantra of the morning and afternoon. I staved him off with earnest answers like, "To get something to eat," and "to pick up more clothes for me," until I ran out of legitimate destinations. "To buy heroin," I finally exhaled in frustrated deflection.

"This doesn't quite look like the heroin neighborhood," he deduced as I parked the car behind a stone and brick two story.

"You'd be so surprised," I answered flippantly and locked the car door after him. An ornate copper sign outside read, "Ace Four."

Sean sent me a look of slow hope, wrought from too many nights of Texas Hold'em. "Is this...?" he whispered, swallowing hard.

I nodded to his unfinished question with a triumphant grin.

"How'd you know about it?" He asked, quickening breath channeling my earlier giddiness.

I squeezed his hand. "EVERYONE knows about Ace Four. Traditional family protests are a new gender bender's best form of free advertising."

I rapped with the bell shaped knocker at the side door, and a slit opened over a built in button-shaped microphone.

"Sean and Selina, four thirty, week," I said, adhering to the "name, time, duration" code given to me that morning.

The door swung into a cavern of vaulted ceilings, staircases, and plush carpeting then clicked shut behind us automatically.

Sean squeezed my hand nervously, our eyes drawn to a voluptuous woman with skin like dark cocoa as she sauntered down the steps. Below a pile of straight raven-black hair, her green-rimmed eyes swallowed my heart as she walked, and I gulped. Muscular thighs, framed by the black mesh sides of her floor-length corseted green and gold dress, gracefully propelled her toward us on three inch heels as if stone was air.

"My name's Julian," she said huskily and clasped our hands between hers, "Welcome to Ace Four."

The baritone of her voice knocked me a step back. "I...you..." I stammered, "jealous."

She grinned widely. "Nevermind that. We do the best with what we get baby," she throatily purred, "The rest is just drag."

Her mischievous catlike eyes fell on Sean then, and her smile widened even more. "So I hear you want suggestions on looking fab then looking man?" she asked smoothly.

Sean shot a nervous glance at me then nodded.

"Sean and I have some girl talk to talk," she said and handed me my key card. "Your room is through the arch, number three."

As I felt Sean's hand slip through mine, loss poked dully at my lower stomach. After his constant laid back warmth, I felt more alone than ever trudging to the car, through the empty arch, to our room with our things, and back again.

"First time?" a deep rumble prodded beside me once I took the time to actually stop with an arm full of duffle bag.

I nodded slightly.

"Where's your baby? Pretty women like you are never alone."

I turned my head toward the arch then glanced at the man standing behind a long counter decked with sex toys. Huge and as dark as Julian, his palms splayed nonchalantly across the edge of the glass. "With Julian," I whispered.

He smiled warmly and beckoned me over. "Relax. Come sit here with me," he urged.

I stepped toward the glass with its enchanting assortment of anal beads, cock-rings, gags, nipple clamps, vibrators, and yes, strap-on dildos. Blood rushed my lower body at the thought of Sean's pert little nipples trapped in the razor sharp teeth of clover clamps. I also didn't dare look too long at their selection of triple crowns or think too long on Sean's throbbing cock, squeezed and drooling for attention in one, unable to cum without permission. I shuddered. A few seconds was plenty long enough to incite my traitorous thighs to rub together.

"I'm Terry Cummings, the third," the man said, "but everyone just calls me Terry, and yes, that is my REAL name."

I didn't laugh but threw another look at the arch and bit my lip.

"Relax," Terry said softly, "Julian's not THAT good."

My eyes searched the case randomly. "What's that," I asked, pointing at a U-shaped dildo with a bulb at one end and a large smooth cock at the other.

Terry seemed more at ease now, as he pulled the display model out of the case. "That's the Feeldoe. It's a harnessless strap-vibe," he said with a proud smile as he put it in my hand. "Gets pretty good reviews, mostly from lesbians and peggers."

"Peggers?" I asked.

"Straight folks who like a bit of anal play," Terry answered nonchalantly.

I blushed, but he continued unfazed.

"It features a few ridges for clitoral stimulation, easy to clean, and six inches long by one and a half inches around," he concluded antiseptically.

"I want one," I exhaled without hesitation, overjoyed at the idea of not having to wear a funny looking set of underwear to fulfill Sean's biggest fantasy.

"One what?" Purred a familiar but breathy voice behind me.

Sean's steamy words sent shivers up the back of my neck as he rested a hand over my waist.

"Tha...aa..at," I moaned, pointing randomly near the case while I turned.

Julian had teased his hair into a loose glossy dark pile, shaved his black stubble, and trimmed his eyebrows neatly. A string of gleaming white pearls collared his throat. The virginal smell of berries and cream surrounded his soft skin, sweetening the pink micro-mini skirt and matching corseted halter hugging his skinny frame. Powder and makeup rounded out his lips and highlighted his sharp cheekbones, but I saw his eyes first. Huge and hazy green beneath curled sooty lashes and sexy silver liner, they begged silently for my approval, my acceptance, my love.

My knees momentarily quivered at that vulnerability, and I kissed tenderly along the flushed curve of his ear, whispering, "Wellllllll, don't you look sexy?"

He blushed and leaned into me with a shiver.

I ran a hand down his throat and touched the swell of his chest, glancing at Julian behind him.

"Breast forms," She said with a proud smile, gesturing at the bag in one of Sean's hands. "He cleans up very nice and has everything he needs now."

Sean whispered throatily against my neck, "I have a surprise for you too."

I swallowed a groan and kissed his knuckles then the soft hint of pink polish tinting his nails.

"Say thank you to Julian?" I murmured, still fixated on the feminine swell over his broad chest. "You look beautiful."

Sean shifted and bit his bottom lip. "Already did," he sighed then exhaled another thank you.

Julian waved a hand dismissively and smiled broadly as I thanked her also.

"Check out time is one-ish or five-ish on your last day," Terry said with a wolfish smile as he dropped a boxed Feeldoe into Sean's bag. "Please be loud. Julian likes it when her work is appreciated."

I took Sean's hand and slid my key card into the door furthest to the left.

The room seemed to warm with Sean at my side, and I pinned him against the door, kissing his lips hard. Our tongues tangled then focused on other dalliances, his skimming my ear and mine flicking over his collarbones. I lifted my mouth long enough to whisper, "You're my woman now."

Sean moaned his agreement and bucked into me.

I steered him toward the bed as my hands groped the tight corset, tugging the laces free impatiently. His moans came louder and closer together, and he ground his stiff rod against my thigh.

Pushing him down on the bed, I squeezed the breast forms.

"Ohmmmmm," Sean gasped and arched his back before panting, "clamps, surprise."

I tried to hide my pleasure, but the devilishly hot confession overwhelmed me, and I grinned and pressed my lips close enough to taste the sweet mint on his breath. "You dirty little girl," I purred, tugging the corset the rest of the way off.

His head bobbed quickly, and his back thrashed toward me as I pressed my hand over the fake breast.

"Do you like that?" I asked, grinding the hard pellet beneath the soft flesh-like rubber as I lapped his ear.

"Mmmm uh huh," he whimpered softly.

"Tell me how much," I commanded, leaning back as he rubbed his bulging crotch through the skimpy skin tight mini skirt. I slapped his hands away.

"Ohmmm please don't stop," he groaned, "God it feels so good."

I grinned and flipped him over on his stomach, sprawling him across the bed. "Lick your mistress you little slut," I ordered in my sweetest, softest voice, seating myself in front of his face and flipping up my skirt. Sean never let me down when it came to following directions in THAT voice.

He grabbed my hips and pulled me closer. I gasped as his tongue tip touched the soaked thong I wore and followed the thin strip of lace between my thighs. As I braced my boot heels against his ribs, forcing his stinging nipples into the bed, he moaned into my swollen lips and lapped frantically deeper.

"Mmmm, my little baby likes a bit of pain, does she?" I teased, steering his finger into my hot fluttering core with a soft moan.

Sean could only bob his head, and as punishment, I pushed my heels down again. He moaned even louder, his sweet wet mouth covering my aching bud. My insides burned, throbbing to the smooth hot stroke of his wonderful tongue. He tilted his finger inside me, and I squealed, arching as my body shamelessly demanded more of his shallow intimate strokes.

"Mmmm very good. Very good you little whore. Come here," I panted, biting my lower lip and clenching every muscle to keep from cumming as his finger slid from me. I hooked my pinky gently under his pearly collar and gave a soft tug, ripping the feeldoe out of its box with my other hand.

Sean crawled forward, opening his mouth instinctively.

"Suck," I commanded, holding the gleaming blue plastic to his lips. He gagged slightly as the big head slid down his throat, and I giggled. In a whisper of rustling lace, his panties slipped to his knees, and I wrapped his hand around his wet pulsing cock.

"Stroke," I ordered, my fingers cupping and milking his smooth heavy balls lovingly. I lifted a small complimentary bottle of strawberry lube from the black iron nightstand by the bed and drizzled it over my hand as I gently worked them from the center out. "Mmmmm now what's this?" I asked, grinning at the soft hum emanating from inside him.

Sean whimpered something close to "surprise," one fist flying over his cock while the other regularly pumped the toy in and out of his throat.

"Don't you dare cum," I warned him as I tugged the plug slowly from his ass.

His neck tilted for a hot moan, and he choked again before bringing the feeldoe back to a regular pace. A dribble of pre-cum oozed from the tip of his head, glistening dewily over the black satin sheets as it fell, and he slowed. "Ohmm...." he gasped miserably though I knew he was enjoying every little torture.

"That's right," I purred, my slick fingers teasing the tapered underside of his gorgeous thickly-veined cock. I licked my lips and stroked the tiny strip beneath the crown, restraining my urge to get on my knees and suck him until he exploded.

"Pleeeeeeease," he begged.

"Good girl," I whispered. "Now kneel up. I want to tease your little pussy."

Sean eagerly did as he was told, resting his face into one of the pillows and arching up high for me. As he did, the chains connecting the clamps swung then flattened under his weight, and he groaned, wagging his ass.

I grinned mischievously as I gazed at his body, utterly open and hot for me with his panties wadded around his knees, his stiff leaking rod brushing constantly over the soft stretchy pink skirt, and his balls hanging heavy and red. I slid a finger into him, and his hole gave easily, thanks to the plug. As I tugged it out, he squeezed, whimpering and bucking to keep it.

I couldn't resist and whacked his ass once. "That's for being too damn hot," I hissed.

"I'm sorry I'm so hot mistress," he grinned slightly, biting his lower lip.

"I don't believe you're very sorry," I accused as I slipped the huge pony into my soaked cleft and stroked lube up and down the shaft of the cock.

He caught my meaning immediately and moaned, nodding his head enthusiastically. "Please make me sorry Mistress. I've been so naughty," he gasped, hand straying to his cock and stroking feverishly again.

I glimpsed the fantasy in his sex hazed eyes and felt as if I could see his needs and wants as plainly as if they were written on paper for me. I spread him gently, tongue teasing from his tightly squeezing star downward. Sean jerked in my arms and whimpered needily.

"Sellllllllllllllina," he whimpered, "Ohmmm god, pleeeeeeeeeease."

I kissed the crease of his thigh then nuzzled my face to his balls and gently swirled one finger against his hole. "Do you want it?" I teased as I tenderly coaxed his blushing balls down.

Sean gasped and thrashed. "Oh fuck! Please fuck me... please," he begged.

I repeated the stroking motion, moaning softly against his puckering hole and thumping it with my tongue. My breath came heavy enough that I felt my heart beating in my throat, and I worked my hand over the feeldoe, lubing it as if it was my own hot heavy meat. As I turned the little vibe on, I squealed softly in surprise, grinding my teeth together then frantically fingering my boyfriend's hot little box with lube.

Sean arched again, and I slipped up behind him, kneeling at the corner of the bed. "Are you suuuuuuuure?" I groaned, rubbing the large head against his throbbing hole.

He didn't answer, but he bucked back, his stretched opening swallowing the head with one enthusiastic thrust. He winced slightly, and I held still, my hand slowly stroking his cock until he began to wiggle.

The buzzing against my clit throbbed unbearably, and I bit his arched back with a whimper. My hips pistoned into his, slipping forward with the lube until I was as deep as I could be. I tried to concentrate on Sean's face, drawn tight with pleasure, as his hand stroked roughly over his cock. Precum puddles dotted the sheets, and each movement sharply teased my humming clit.

I ground deep against him, and we both gasped, rocking together. Slipping my hands under his, I teased his well oiled balls, stroking between them and gently lifting them.

"OH fuck... Oh god... Selina," He gasped uncontrollably. His body shook in my arms, the sweet smell of our blended sweat rising on heavy expectant air.

"Ohmmm Sean, you're going to make me c-c-ummm... oh god," I bit down on my lower lip as he exploded in his hand, the tangy wetness of his arousal dousing his tiny skirt. My clit throbbed, and my insides tightened, squeezing the pony inside me mercilessly hard as I rocked against him, riding the amazing moment he'd just given me.

When my breath returned to normal, I gently untangled myself from my ungracious sprawl across his back. He winced as I slid the vibrating strap out of him, and I groaned as the seemingly-immense pony slipped from my stretched cleft. I put the toy down beside us and bundled him into my arms, tugging the breast forms away and gently easing the pressure of the clamps.

Sean whimpered and pressed closer to me.

"I know darling," I whispered, finally releasing them completely and tenderly petting his abused nipples with my lubed fingers. "I love you, Sean," I whispered to him, kissing tenderly across his temple.

"Mmmmm, I love you too angel," he sighed. "Thank you."

"You're welcome, I whispered then kissed his lips with a smile. "I figured I had you pegged."

He grinned widely. "Indeed angel... indeed."

Report Story

byFireSiren© 1 comments/ 23451 views/ 2 favorites

Share the love

Similar stories

Tags For This Story

Report a Bug

1 Pages:1

Please Rate This Submission:

Please Rate This Submission:

  • 1
  • 2
  • 3
  • 4
  • 5
Please wait
Recent
Comments
by Anonymous

If the above comment contains any ads, links, or breaks Literotica rules, please report it.
by Anonymous11/23/13

What a surprise.

If the above comment contains any ads, links, or breaks Literotica rules, please report it.

Show more comments or
Read All User Comments  or
Click here to leave your own comment on this submission!

Add a
Comment

Post a public comment on this submission (click here to send private anonymous feedback to the author instead).

Post comment as (click to select):

You may also listen to a recording of the characters.

Preview comment

Forgot your password?

Please wait

Change picture

Your current user avatar, all sizes:

Default size User Picture  Medium size User Picture  Small size User Picture  Tiny size User Picture

You have a new user avatar waiting for moderation.

Select new user avatar:

   Cancel