tagTranssexuals & Crossdressers1st Transsexual Affair

1st Transsexual Affair


Author's Note: This is a revised, edited version of a previous story. I listened to my critics and like this one better. Hope you do also.

1st Transsexual Affair

Paul's cock was hard as a rock and with a penchant for sleeping in the nude, its fat length pressed against luxurious satin sheets. The dream of searching for a urinal or bathroom now became reality. He stretched, groaned and yawned his way off the comfortable bed and padded across the room. The marble flooring was cool and with relief he emptied a full bladder, the tinkling water sounds echoing.

Rinsing out a dry mouth and splashing water on his face and hair he primped in front of the full length mirror: a little paunch in the middle but otherwise in good shape for late 40's, muscular and tanned with a touch of grey near around temples. The narcissist flexed biceps and admired his taut white ass.

In the quiet living room, he made coffee and lounged in the nude, glad to be alive. Transparent white curtains flowed inward with sea breezes, inviting the salty scent from the ocean just outside his balcony. Bermuda, lovely Bermuda.

Six months ago, Annie had died after a short but painful bout with cervical cancer and he regretted that their individual careers had kept them so busy, so far apart with never enough quality time. Twelve years of marriage abruptly ended, friends and relatives lovingly suggested a getaway, a vacation from the office and memories.

He sipped coffee while reflecting on the slower pace and simplified living here on this island paradise. The local cuisine was good Driving around on the motor scooters, swimming in warm waters and basking on the hot beach. He'd even managed to write some, all of which were healthy signs. Sea gulls and blue skies beckoned, he smiled and decided to put on the tight

Speed-o before making an appearance outside, enjoying the feel

of his balls sexily hugged within.

Parting the gauzy curtains, he stepped through the open patio door onto the brilliantly sunlit balcony, covered with bleached white seashells embedded into the concrete. Hanging ferns completed the million dollar scenic view towards the ultra green sea, coral reefs and beach below already dotted with colorful umbrellas and oiled vacationers. He'd spent little time out here admiring the panorama.

Immediately to the left another million dollar view caught his eye. A young topless woman lay face down on a large thirsty white beach towel, her hot pink toenails and crossed ankles swayed easily while casually flipping through a magazine. He drank in the sight of: smooth tanned legs, a powder blue thong wedged into the crack of luscious buns, a thick mound of fiery red hair neatly pinned atop and curvy breasts partially hidden by propped elbows.

Unaware of his presence the quiet voyeur enjoyed thirty seconds of ogling near nudity and fantasized massaging coconut oil onto her shapely back and shoulders or better yet spraying gobs of pent up semen there. His cock stirred against the confining material, another healthy sign.

Flipping a page, a bright red fingernail aimlessly tapped on a color picture. He followed her gaze onto lesbian photography from Penthouse magazine (my kind of girl!) causing his manhood to continue swelling.

Tearing his eyes away, he turned sideways, bent slightly and purposely re-arranged the chaise lounge, its legs scraping the patio deck. Guessing that the sun bather was now aware of his presence, he straightened to face her. Deep green eyes sparkled over sunglasses hovering on the tip of a dainty freckled nose, elegant dark eyebrows arched towards his Paul.

"Hello." She cheerfully said. Smiling, he returned the simple greeting while her self-assured eyes roamed over his chest, legs and tiny Speed-o. He safely spoke of the wonderful view and the accommodating weather.

"Did you just get in? I've been here for a few days...its quiet...looks like we share the same balcony..." She said while looking at the only separation: a short wrought iron railing. He explained he'd been here for two days, getting away from the rat race, catching up on sleep, touring some of the island, blah...blah.

Obviously friendly and wanting to talk, she launched into a chat about the island, where's she from and then abruptly sat up removing the shades, "Damn...I'm SO sorry! I'm Gwen..." Her exposed breasts were gorgeous. Small, girlish, perfectly round with a slight droop and bright pink, eraser sized nipples lovingly pierced with thin gold loops. He stared and extended his arm across, "Nice to...meet you Gwen. I'm Paul."

Her hand was warm with a firm shake and up closer; he guessed Gwen was late 20's, early 30's. Darting away from her captivating breasts, Gwen's eyes bore into his, searching in a friendly manner. Smiling and with no hesitation, "Do you like them? I had them done a year ago...and...never regretted it..."

"Well...umm...yeah...I mean...they look great..." He easily imagined lapping and sucking the constantly erect buds, jewelry clacking against his teeth, his pulse quickened.

God, she's young and brazen...delicious...do I dare continue this flirting with her...in the hopes of getting her into bed...don't get too far ahead now...it's just been so long...

"Ahh...Gwen...can I ask you something...something...ahh... kind of personal?"

"Of course Paul...anything..." The last word a whisper.

"I see you're reading...or looking at Penthouse. I don't know that many women that do...umm...so what do you like about it or...you know...whatever...?" He coolly asked knowing Guccione's creation is mostly a men's magazine for masturbation.

"Well...the photography's good...erotic. I like the outdoor settings. The women are almost too perfectly made up, you know...but they're beautiful and...arousing..."

"I agree..." Wondering if she's a les.

"So...are you alone...here?" He blurted out as neither of them wore rings, at least the finger variety.

"Oh yes. I guess...like you...came to relax, unwind...you know...get some of that "me" time. And you? Are you here with anyone?"

"No...oh no...not this time..." Their conversation was fluid, easy and comfortable. Immensely he enjoyed Gwen's attention and flirting ways. Her openness and bold mannerisms were a welcome change and as the details of their lives warmed up so did the blazing mid-day sun.

Teasingly he asked, "Aren't you afraid of getting that cute ass of yours sun burnt?"

"Oh? You think it's cute...do you?" She giggled, "I did put sun block on...but...hey...it is getting hot out here...would you like to come in for a cold drink or something?" Long cute eyelashes batted at Paul.

"Umm...yeah...sure..." Devilishly thinking about the something His chances with Gwen were getting better and better. Safely gauging the height of the wrought iron railing, Paul swung his right leg, straddling the boundary. Instantly Gwen moved forward, grasping his hand, "Careful now...we don't want to hurt the crown jewels...huh?" Her ribald laughter rolling across the balcony.

With her help, he maintained balance and smoothly got the other leg over, "Why thank you!" Paul looked down at her short frame, full kissable lips and a wide smile showing pure white teeth. Gwen gripped his hand with no intention of letting go and together they walked into the cooler inside of her flat, the ceiling fans providing breezy relief.

She led them into the small kitchen area, letting go of his hand to reach up for two red plastic tumblers. As his eyes adjusted to the inside darkness, he enjoyed the view of Gwen's nearly naked form, his cock misbehaving deliciously. Paul leaned back against the centralized Formica island. She side stepped towards the Whirlpool fridge for ice, tender cheeks rippling, the narrow strip of cloth tightly wedged within. Visually, Paul chewed her fleshy posterior, dragging his tongue along the hidden lingerie...

"Is Perrier okay Paul?" turning to catch his stare.

"Uh...oh...that's fine..." slightly embarrassed but knowing she must know, his erection telling the truth.

"I said Perrier...not...derriere..." She laughed, admiring the attention and handing him the half filled tumbler. Holding hers up for a toast, "Cheers!"

"Cheers...and...happy days!" He said barely "clinking" the rims before tasting the refreshing carbonation. Standing close, she sipped her drink, their arms touched and he knew it was right.

Paul calmly put the glass onto the counter, placed his hand against her cheek and ear, "Gwen...you're so cute...so nice...so sexy..." She looked up at him with smoldering eyes and moved her mouth onto his. The sudden kiss was electric and exciting. Paul pressed down, tasting the spearmint balm on Gwen's full warm lips. Mutually their lips slowly explored the new territory then mashed heatedly as passions began to ignite. The stiffened tip of Gwen's tongue darted into his open mouth, quickly and maddeningly retracting.

"God Gwen...you're...too...good to be true...mmm..." He gasped, missing kisses like these.

"You...kiss...good baby..." She breathed. Again their mouths became one, fervently sliding, pressing and exchanging small bursts of sexual energy. Paul's hand moved onto her shoulder and continued down to boldly cup her breast, toying with the loop. Gwen followed suit, tenderly flicking one of his nipples with a fingernail prompting groans of lust.

Her nails raked across his stomach and reaching the Speed-o, lightly traced the bulging outline of Paul's imprisoned cock pulsating against her inquisitive fingers.

"Ohh...my-y...somebody's hard. Ohh...yes-s...nice and big and hard." She rasped. "I wonder who-o did that? Huh...baby?"

Paul helplessly moaned, "Oh Gawd girl...as if...you don't know. Oh Gwen...you're so fucking sexy...so young..." On tiptoes she huskily whispered into his ear, "Guess I didn't tell you...I like older men...a lot..." Nipping and capturing his earlobe. Paul grinned and shivered small goose bumps, this was too good to be true.

Away from the office, the god damn phones, distanced from anyone he knew and making out with this tantalizing younger woman was heavenly. He actually loved Gwen's aggressiveness as she pressed her breasts against him, their open mouths and slick tongues dueling. Gwen's nimble fingers dipped under the waistband of his suit and pulled the already taut material upwards an inch or two.

Breathing deeply, Gwen...oh God...Gwen...are you...trying to seduce...me? Fuck...I'm so...turned on..."

"Me?" trying to sound innocent and giggling. "Hmmm. Think it's us, just the both of us...think I'm...just as horny as...you. You're such...a hunk..." stroking an already inflated ego.

Closing in on a sensitive nipple and between licks she asked, "Would you...would you...like to...see my...bedroom?"

"Oh yes...I think...I'd like that...to go there...yeah." Like honeymooners, arms around each others waist they walked down the short hallway, Paul's hand slipped, on purpose, down onto a cheek, palming and gripping her adorable ass.

Clenching her butt muscles, "Ooo. I guess you are an ass man...Hmm?"

"Well...let's just say...I'm partial to there...I mean...yours!" using her earlier descriptive word.

The perfume scented room was all woman: lotions and makeup items lined in front of a mirror atop the dresser and clothes in the process of being hung up or folded over the opened suitcase. Near the bed she sweetly kissed him and with palm flat against Paul's chest pushed him backwards onto the satin quilt giggling with anything but innocence.

Adding to his delight, Gwen turned to face the mirror. Comfortably propped on elbows he avidly watched as she removed the hair clips, delicate fingers ruffling through the locks. Conditioned waves of silky, red tresses drooped covering her shoulders and neck. Her deeply tanned skin looked even darker against the white furniture; both arms raised accentuating shoulder blades and sexy smooth underarms.

In the reflection, she winked at Paul while quickly applying fresh lipstick, coquettishly blowing him a kiss and turned to face him. Mimicking a lewd stripper, Gwen playfully tugged the piercings, sensually moving her palms across a flat tummy, her thumbs hooked under the thong's top.

"Paul...there's something I have to tell you...it's a bit of a surprise. I'm...a...transsexual..." Gwen confessed while pulling the frilly underwear to her knees, exposing penis and balls, Gwen's completely shaven genitals appeared juvenile and boyish sprouting from a smooth crotch.

His heart skipped a few beats and his mouth went dry. He'd seen a few pictures and video clips on websites of them: Shemales, trannys and other catchy names and Gwen was a he. Paul's mind flashed back to Boy Scout days, in private tents they'd sit in a circle and jerk off; curiously he'd indulged in sucking a close friend's dick but knew he wasn't destined to become a full fledged gay or homosexual. A small part of Paul felt that he'd been lured or tricked by Gwen but overwhelmingly thought she was incredibly erotic, sexy and here, in the anonymity of Bermuda, anything could happen.

"Paul? Baby...do you still...like me...? I mean...I don't want to scare...you away..."

"Oh Gwen...yes...yes...I do! You're fantastic...and pretty..." He felt lightheaded, under her spell, rubbing his stiff cock. Stepping free of the thong, she opened her legs to massage the ball sack and flaccid pink penis from its confinement.

"Baby...I have to tell you...I could just watch you...your sexy...hairy chest...and muscles...and handsome face...I could just masturbate while looking at you. Would you like that baby? Hmm? Paul...baby...you make my clit throb...yes...yes you do..." Sauntering towards him, hands on swaying hips.

He sat up, ravaging the approaching nude, a drop dead gorgeous woman with a tempting alternative to sex as he knew. Standing between his knees, Gwen's fingers sifted through Paul's hair, his hands reached to cup her buns and began kissing her feminine navel area. Everything seemed possible with this lovely amazing person as he licked his way down, closing his mouth over Gwen's cock, sucking in a natural motion, a sexy smooth abdomen waxed free of any stubble.

"Ooo...Paul...Yes-s-s-s-sssss...hmmm...I didn't...think...I

...wasn't sure...you know..." gently rocking her hips back and forth, pleasuring herself. Gwen's cock did not have an unpleasant taste; her penis stiffened rapidly but small enough to easily fit in his mouth and he imagined as Gwen suggested, her throbbing clit.

Unpredictably she pulled back, Paul's saliva coating the bloated red tip, "God baby...you suck me...so very good but...I want to see you now...please?" Gwen practically pulled him to his feet, throwing her arms around him, hugging and kissing his chest.

Sliding down his torso she knelt on the carpet and gripped the snug waistband of the Speed-o. Gwen pulled the material out and down, Paul's massive erection bobbed freely scant inches from her face.

"Oh Paul. It's huge, so big...so..."Verbally arousing him. Kicking the infernal Speed-o to the side he looked down and their eyes locked, "Paul...you've got the greatest cock...fuck...so fine..." Petite fingers could barely close around the base of his 8 inch thick shaft. Slowly moving the outer skin up and down, her other hand wickedly reaching under to caress his ass, a finger tracing along the crack and swollen balls.

Paul groaned aloud, tightening his sphincter, a clear droplet of pre cum oozed from the dark red mushroom head of his cock. Expertly Gwen increased her grip causing the blood to engorge his bulbous tip, "Ooo...somebody's leaking...God I love it...love the silky taste of pre cum...and...it's all mine..."

Her glossy lips formed an O enveloping the spongy head, the tip of her tongue flicked inside his pee hole. Lost in pleasure Paul deeply moaned with quivering knees. Gwen released the prize with a wet popping sound cooing, "Mmm-mmm-mmm...so sweet...Mmm...tasty...knew you would be..."licking her lips. "Baby you'd better sit down before you fall down." She chirped, giggling.

Reluctantly she let go of his straining hard-on, his ass easing onto the bed's quilt. Gwen's fingernails splayed against inner thighs, pushing them apart, comfortably scooting forward and ogling his accessible man flesh.

"Baby...God you're so hard...I'm gonna suck...this...tall monster dry. Would you like that Paul...sweetie?" As if a logical answer was needed. He grunted, propped on elbows to enjoy the show, her way.

Lustfully cupping his scrotum, her long tongue painted tiny circles before gently capturing each sensitive ball, mouthing them like candy. The fat length of Paul's stiff prick lay heavily against his stomach and Gwen ran the flat of her tongue long pulsating blue veins attentively laving the erogenous underside.

Moist lips and teeth surrounded the ridges of his engorged cock head and Gwen engulfed the pole inch by inch, incredibly deep throating him, its entirety lodged in her cavernous throat.

Deliriously, he gasped at Gwen's Linda Lovelace talents. No-one had ever managed to deep throat his John Thomas. Annie had, on occasion, jokingly teased that with his sizeable member, he should consider the porn industry.

Extricating herself off his cock and gulping air, Paul stared at the magenta penis, glistening with rivulets of Gwen's saliva. Her hand began a rhythmic pumping, using the available coating as a lubricant.

"Oh God...Gwen...I'm...so close. I can't hold back...please, yes...please...don't stop...," hips bucking uncontrollably.

"That's good baby...I want your cum...want you to shoot...in my mouth, yes," closing her sweet mouth over him. Sensing his orgasm, Gwen's fingers carefully encircled his balls with a delightful pressure, stroking the long slippery hard-on into her suctioning mouth.

"Arrrghh-Rrrr......Rrrr.....Ahhhh-h-h-h!" Paul yelled gutturally, intense pleasure swarmed through his prone body, powerfully spurting gobs of semen into the vacuuming Gwen.

"Ohhhhh-h-h-h-h God...Gwennnn-nnn!" Paul gripped at the quilt, toes curling through the mind blowing, ecstatic rush, ejaculating hot cum which Gwen eagerly swallowed. The rippling, intense waves coursing out of his cock began to ebb and diminish, leaving Paul gratified and worthless. Gwen, fully aware how sensitive the head of a spent cock can be, released her suctioning mouth but continued to milk the final savory drops sensually, eliciting numb, wordless moans from Paul.

Dazed he heard Gwen clearing the stickiness from her throat, "Wow...you came a lot...baby. I mean...loads of you...I love the taste of you...your cum...so good...a-hem..." Gulping and smacking her lips. Unable to move, the sweet minutes passed, Gwen layed her head on a thigh, his contented penis wilting in her grasp and with total secure satisfaction he drifted off.

Alarmed, he nervously jumped, imagining that Annie, in the midst of a guilt ridden dream had walked in on he and Gwen.

"You okay baby?"

"Oh yeah. Jeez girl...you knocked me out...just a silly dream...you know..." smiling up at the ceiling fan, luxuriating in his post orgasmic bliss.

Reality came around, "Oh shit! What time is it?"

"About 12:30..." Gwen answered.

Paul sat up, "Oh jeez...I forgot...lost track of time, I guess. Gwen...you're gonna think I'm awful...but...I paid this guy, this local guide...you know...I mean I already paid him...damn... to take me out snorkeling. Shit...you don't mind...do you?"

"Mind? Of course not...I mean...you just...forgot. Its okay." She smiled as he got up naked as a jay bird.

He hesitated by the door, "Gwen...I was thinking. I don't know...umm...should...would you like to have dinner later? I mean...if it's alright..." Feeling flustered like a school boy asking for a date.

"I'd love to...I'd love that Paul!" Kissing his cheek, "Just knock when you get back...when you're ready..."

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