1st Transsexual Affair

Hastily he dressed, packed the needed equipment and met his guide by the boat slip. It was a beautiful clear day, the underwater scenery was visually alive with spectacular colors and he had ample time to dwell on Gwen, sexy Gwen. Paul nodded off on the slow voyage back.

Showered, shaved and wearing shorts, a summery Polo shirt and sandals he rapped on the door labeled: 2-D. "C'mon in!" came Gwen's muffled voice. The familiar perfume scent lingered. Gwen was primping in front of the mirror like the fabulous transsexual that she was. Her hair was tied back, "Be right with you...just a sec..." He smiled, amazed with his good fortune.

Gwen took his breath away: her face perfectly made up, sleeveless white silk blouse, no bra, a very short dark blue skirt, crystalline studded earrings and leather sandals.

"You're beautiful." He sincerely whispered.

"Thank you Paul." Blushing.

Arm around her waist, he escorted Gwen towards a table and noticed a few men sizing her up. If they had any idea, if they only knew, he smirked secretly. The bar was loud but far enough away from their candlelit table where they conversed quietly, sipping Chablis, enjoying the prawns and each others' company.

Gwen told him she'd gone swimming in the ocean, wrote a couple of postcards and missed him. Paul loved her frankness.

"We should dance...would you like to?"

"You bet! Let's go..." leading Paul towards the small dance floor. The calypso band picked up the pace playing a quicker reggae sound for the incoming party-goers. Gwen was already swaying to an inner rhythm. Fingers snapping over her head. Bold, feisty t-girl's nipples erect under the silk. Paul felt un-coordinated using the best dance movements he knew but the people weren't watching him anyway. Gwen's sensual figure was magnetic. Masquerading as the perfect couple was exciting.

Her tanned arms locked around Paul's neck and pressed herself against him at the slower, romantic tune they played next.

"Do you have any idea how many hard-ons, out there, you're responsible for? You sexy...sexy...lovely girl..."

Hypnotically Gwen's soft eyes held him, "Paul...my big man...don't you know? There's only one hard-on...here...that I'm concerned about..." She gnawed her bottom lip, rubbing and grinding her crotch against his growing cock.

Lewdly and unconcerned about the stares, Paul's hand caressed and grabbed Gwen's right ass cheek, "Whew...could you be anymore...exciting? Umm...my place...or yours?" His complete urgency for sex evident.

"I...really don't have...a preference..." She whispered. The door to 2-C was unlocked. They kissed heatedly, removing clothes in the process, angling toward the spacious bed. Gwen playfully tugged on his freed cock, "I'll be right back...okay?" In the short interlude he brushed his teeth, lit the pillar candle on the dresser and sprawled nude on the bed, awaiting his lover.

Evidently hopping the metal railing, she entered like a dream through the balcony door's wispy curtain and sauntered towards Paul wearing only lacy, pink panties. Gwen placed a bottle onto the nightstand, her sizzling eyes focusing on Paul's naked body.

"Do you like these?" She asked, her fingers erotically caressing the underwear, roaming across the bulge in front and turning around for him, suggestively palming her supple derriere.

"Yes...yes I do like them. They're perfect..." Paul agreed, his cock growing bigger by the second. Gwen's long feline nails danced over the lacy leg openings. Like a strip teaser slowly, agonizingly, pulled her panties down, bending over to provide the voyeur a fabulous and unobstructed view of her star shaped anus and shaved balls.

"Like what you see...baby?" She teased; placing the silk panties over Paul's straining hard-on, stroking his thickening shaft with delightful fetish. Gwen did know how to make him groan.

"Have you ever worn panties...Paul baby? Hmm...they feel so sexy..." masturbating him, caressing his balls with them. Tucking the dainty wad under his scrotum, Gwen unscrewed the cap, a fragrant almond scent wafting near the bed. Pouring a liberal amount of the warming liquid into her palm, she drizzled a line across the front of his penis.

"Hmm...baby...you're going to like this. It's one of my favorites. It has...some...you know...some special herbs..." The herbs didn't mean a damn thing to Paul, his cock already reaching for the ceiling. Gwen's oiled fingers moved up and down his slick member. Paul spread his legs, incredibly aroused and couldn't remember when he'd been this hard, the only sounds were his rasping breath and Gwen's squishing fingers.

"It's...just...magnificent baby. Your cock is so fucking beautiful...so fucking hard...I love playing with you...love jerking you off..." briefly stopping, tightly gripping and encircling the base with thumb and index finger, his cock dark and purplish.

Huskily she whispered, "Baby...Paul baby...do you...do you want to fuck me?" making his head spin. He adored anal sex, although painful for Annie, she had always pleased him in that way, on special occasions.

"God yes...Gwen...I...want to...yes..."

Kneeling on the bed, she liberally coated his glistening hard-on, "Bareback...or?"

He'd never considered prophylactics on this trip, without blinking he said, "I trust you Gwen."

Efficiently, she poured more oil onto her fingers and reached around to apply lubricant on her backside. Breathlessly he watched as Gwen straddled his hips, positioning the head of his cock directly against her anus and began to move down. Her upper thighs flexed and Gwen's tiny brown eye barely opened, allowing his spongy cap inside. Motionless for a short respite, she continued to impale herself, his swollen erection slowly absorbed into her dark, taboo cave.

Opening his eyes, he realized his entire sword was sheathed and pulsating in her most secret place. Gwen winced ever so slightly, "You're...you...Paul, you are big..." her muscles slowly accommodating and accepting his sizable prick.

He looked up at her flushed face, pert little breasts swaying, her hands pinning his arms, "God...Gwen...you are so tight, so fucking tight..." Paul held her tense hips, carefully pumping his cock in and out two inches. As her breathing slowed he repeated, to three inches, then four. The pace quickened and his strokes lengthened, caught in her web of desire.

"Yes...fuck me Paul...fuck me hard...fuck my cunt. C'mon give it to me...that's it..."

They were a team now, moving together, his balls tightening, enjoying her x-rated speech and getting into it, "Oh yeah baby...take my cock...all of it...fuck...you're tight..."

His oiled cock pistoned, easily sliding in and out fucking Gwen like an animal, lost in another world. Gwen's world. This wasn't gay sex, he was fucking her lovely cunt. This wasn't another man. Her pierced nipples jostled near his mouth. Painted fingernails raked his chest. Her pretty face and sweet breath so close. And for the second time this day, Paul experienced another mind shattering orgasmic explosion, deliciously turning him inside out, volcanically emptying his cum into the wonderful vessel of Gwen.

Fingers gripped so tightly they left marks, pulling Gwen's flesh up and down, sawing and embedding his enormous prick deep in her bowels. Grunting in rapture, his yells and screams flared across the bedroom and through curious walls, empty and filled at the same time.

Paul gradually returned to Earth, the ceiling fan making a subtle whirring sound. Gwen hungrily clutched his erection. They remained intimately connected, sweat mingling. She had done it again, taken his breath away causing him to incoherently mutter words relating to immense pleasure and ecstatic numbness.

Gwen smiled widely, perhaps for her accomplishment of turning him to jelly and slowly began to ease herself off his bloated penis. Her tight elastic ring milking the last remnants of pleasure. The journey was tingling and the sensitive head of his cock came free, its semi-erectness gravitating, plopping wetly against his abdomen, warm droplets of semen cascaded out of her and onto his genitals.

"Be right back..." Gwen said heading for the bathroom and limply, selfishly Paul rolled onto his side, returning to that twilight, dreamlike state hardly aware of Gwen's return.

Strong insistent fingers massaged his aching shoulders with a familiar almond scent. Paul happily smiled knowing this wasn't a dream, Gwen was still here. The small tense knot on his neck dissipated due to her talented massage, she spoiled him.

Gwen hugged him, spooning her body against his. Her breasts mashed, legs and knees cupping and...her stiff cock pressed aggressively between his ass cheeks. He murmured surprise.

"Hum...'bout time...and...welcome back..." She teased, faintly moving her hips, rubbing and sliding her cock there. He sensed Gwen's need and felt an embarrassment or hesitation, quickly shooing them away, after all, anything's possible with her.

She rubbed his chest, "Baby...do you know...what I want? More than anything...?" Clenching his buttocks, he told her yes, he was pretty sure what she wanted and that is what he wanted also, to please her but admitted nervousness.

"Paul...baby...are you a virgin?" She demurely asked.

"Yes." He softly answered deciding to skip the details of experiences with fingers or experiments with dildos.

"Ooo...baby...you don't know what...you've...been missing. Oh...you'll like me...I'll be gentle...I promise Paul baby..." He was putty to be molded and controlled. Comfortably positioning Paul on his knees, cooing words of encouragement, a well oiled digit touched his anus causing a flinch.

"You're tense baby...relax...it's just me..." He looked back over his shoulder at Gwen, sitting on her haunches, her shiny pink penis, bigger than before, sprouted between naked thighs. The dual gender sight was quite erotic. The tip of her finger entered easily. Paul's sphincter muscles pleasantly collapsed tightly around the invader. Gwen used more oil inserting a second finger and he was ready.

The mattress sank as Gwen moved closer, pushing her cock forward, inserting half of the slippery erection into his virginal ass. The initial feeling was strangely exciting and devilish.

Gwen sighed while burying herself to the hilt. Paul barely felt her balls slapping against his. He was hers' now.

"C'mon bitch...are you my bitch? Yeah...I'm fucking my bitch now..." The sudden personality transformation surprised Paul. She increased the speed of her deep thrusts fucking him good. Gwen's right palm landed sharply, spanking his ass cheek, then again and again, her breathing loud and ragged. Paul felt like her bitch and loved that feeling.

"I'm...gonna...cum...baby...I'm gonna..." He felt her body stiffening.

"Fuck me Gwen...give it to me..." He whispered. Nails dug into his back while sighing in a high pitched squeal, pumping and slamming herself against his backside. Her unique wail of orgasm was loud and powerful. Gwen's pleasure was beautiful; she held back nothing, emptying her glass on this night.

Lessening her grip, "Oh Paul...fuck...you're beautiful..." making a sexy, hissing sound while pulling back, her softening cock withdrawing from his warm tunnel. Paul simply lay face down on the bed and Gwen plopped herself half on his body, half on the bed next to him, caressing his cheek lovingly. Fulfilled and both happy, the lovers fell fast asleep.

Paul's cock was hard as a rock and in the midst of his horny dream, it's fat length pressed against the luxurious satin sheets. It was late morning and he hadn't slept this deeply or for this long in months. He reached for Gwen and only found a crumpled pair of panties. Stretching and smiling, he entertained the thought of masturbating inside them.

Nude as always, he made coffee and looked out onto the balcony to the bright sun and no sign of his neighbor. He thought of dressing then spotted a blue envelope propped on the glass patio table. He darted out naked and it was addressed in feminine scrawl to Paul.

Dear Paul, Please forgive me for not saying good-bye properly. I didn't want to spoil our night together...I got a call from work, a sort of mini-crisis happening, I'm sure you know what that's like! Anyway they asked if I could come back early so I booked an early morning flight. Paul, you are truly wonderful, so courteous, a real gentlemen and very sexy. I truly cherished our short time together and its unlikely our paths will cross again, but thank you from the bottom of my heart.

Love always, Gwen

P.S. Write me e-mail if you wish. Would love that.

His vacation was heaven sent. He felt rejuvenated, rested and spent the last two days in Bermuda alone but not lonely. Back at the office the typical backlog awaited and he silently cursed for not delegating some of these issues but he tackled them avidly. Two nights later he and one of his managers, Stephen, had a working dinner at a fancy restaurant. "So, Paul how was your vacation? You know we missed you but I'm glad you got away...you know...Annie and everything."

"Oh, trust me...I really relaxed...such a beautiful island. So warm, snorkeling...great food and accommodations..."

His eyes twinkled suspiciously, "Did you...meet anyone?"

And the little alarm went off in his head; the pieces all fit together. Had he arranged for Gwen? It was all too perfect. Stephen was a sly one and generous. Perhaps he had. Paul smiled secretly. He had been duped but he wouldn't trade that night.

~To Be Continued~