Seeking Gwen

Paul's ethereal fingers sifted through the curly red hair as the warm, wet mouth eagerly fellated his straining cock. Saliva dribbled onto the feminine fingers that firmly held the base of his hardon. His hips stabbed upwards into the inviting sensation and Paul awoke perfectly in the middle of a wet dream. His manhood tickled against the smooth sheets, the soft fabric lightly clinging to dollops of white sperm and he grunted through a wonderful orgasm, whispering her name…"Gwen."

It had been a little over a month since the trip to Bermuda, meeting the sassy Gwen and spending the short day and a too short night with her. Upon returning home Paul focused on the piles of engaging paperwork, organizing, it seems was a good thing for him. The house was lonely without Annie but after work he kept busy with writing on the computer, daily workouts at the gym and dabbling in the kitchen.

On and off he'd thought of Gwen and how strange was that…thinking of "her"? Last night's dream was so vibrant, clear and real enough bringing him to orgasm. Gwen is so pretty, so feminine and yet has male genitalia, does that make me queer? Bisexual? Paul remembered a high school homosexual encounter. Tom, a future gay man had convinced Paul to simply enjoy the pleasure and stop being analytical, after all we all have latent homosexual tendencies.

Paul's initial she-male experience with Gwen rerouted some of his former thinking; admittedly he was extremely attracted to her…all of her. Many of the transsexual websites were tastefully and erotically inviting but the enticement and porn industry was really all about money. Paul couldn't confront his manager Stephen and frankly ask him the burning question: Was Gwen a prostitute?

Unhurriedly Paul took care of the Saturday chores: laundry, dry cleaners, food shopping etc and after a hearty lunch lounged on the sunny patio with a cold Corona. In his head Paul had drafted an e-mail message to Gwen, grappling for the perfect words and laughed at himself, needlessly worrying over something that should be natural.

Dear Gwen, Don't know if you remember me (Paul…we stayed at the same hotel) but thought I'd drop you a line to say hello and how are you? Came back from vacation to tons of work but its all going good here. If you get a chance or feel up to it please write back. I'd love to hear from you.

A friend…Paul

P.S. I'd rather be in fabulous Bermuda! •

Dear Paul, You are funny! Did you think I'd forget you? LOL! I am fine and thank you for asking, that means a lot. I was a little surprised to hear from you…pleasantly though. You're message was short and isn't it funny how work just dominates so much of our life? I think you're nice and enjoyed those hours we spent on the island. Write when you can. Take care.

Gwen

P.S. Hugs!

Paul waited several days to reply, he didn't want to appear aggressive or pushy and this was newer territory he was stepping into. Again he somewhat agonized for the perfect words and realized the words weren't the stumbling block. It was about her…and him…and sex…and…

Over the next month their e-mails were sporadic, friendly and inquisitive. Soon their messages evolved into a daily or nightly comfortable routine, mutually sharing bits of personal information, the trivialities of their day's happenings or just a quick note. Paul developed a clearer appreciation and sense of who Gwen is and he felt certain she found the same.

29 year old Gwen was born Wayne, grew up in the Chesapeake area, happy with lots of friends but knew she was somehow different from the other boys. In high school her sexuality and inner emotions steered her in another direction. During college years she gave in and decided to live a feminine life. Still in Chesapeake Gwen is an accountant with clients in the trucking/transportation industry, ports and such. In fact most of her associates know her only as Gwen. Working a lot from home, a modest two bedroom condo, she loves cats (currently 3 at home), playing piano, swimming, reading, old black and white movies, fresh air and sun.

Open minded and maintaining a private life, Gwen's sexual desires are diverse, preferring either gender. The closeness with her immediate family has waned, although not an outcast for obvious reasons. An older brother, Greg in New Hampshire, are much closer, they call and visit often.

48 year old Paul reciprocated, filling in the personal items of his life: childhood, school, college, and his middle management position with a cellular phone corporation in Tennessee, pastimes or hobbies which he thinks of as a very boring word. He carefully wrote of his wonderful marriage and the emotional loss of Annie.

Their friendship grew. Comfortably they exchanged work e-mail and actual residence addresses, cel phone numbers and pictures. It didn't surprise Paul that a 5 x 7 of Gwen taken in Bermuda sat near his monitor but something did come as a surprise one night while writing e-mail.

Paul: Gwen…I'd like to see you again.

Gwen: Really Paul? I'd like to see you as well but it's not like we live close to one another! LOL I'm sure we could arrange something…what did you have in mind?

Paul: To be honest I didn't have an exact plan…I just know that I wanted to see you, enjoy your company and wasn't sure how you would feel about that. Oh well. Let's see…maybe a weekend getaway? Somewhere we'd both like and can afford? Or maybe…you could come here? Tell me what you think.

Gwen: I'm glad you're honest, I think I knew that anyway and on that same note…sitting here and thinking about you feels nice…exciting…like a date or something. Silly me, huh? Oh Paul I'd LOVE to go back to Bermuda but a weekend seems too short! Love to spend more time diving, touring around, night life, local cuisine you know…LOL! Maybe some year! Your place sounds inviting. *Wink*Wink* Call me.

Everything with Gwen, Paul thought, seemed easy, uncomplicated and therefore possible. She had a way of making him feel free and therefore not uptight. Her voice was soft and sultry without the slightest hint of that fake homosexual lisp; Gwen's tone was natural with a happy, uplifting ring. As they chatted, Gwen described a particularly frustrating client and Paul listened but zeroed in on the scribbled desk blotter/calendar.

"Paul…do you have a calendar or appointment book or whatever you use nearby?"

He chuckled, caught, "Yes. I'm looking at it right now…" wondering if she was that intuitive or just…

"Yeah. Me too." Gwen giggled lightly. Comparing notes, the next month looked open and although there wasn't a huge choice of flights, Friday's tended to be early days and to Paul's relief Gwen had plenty of frequent flier miles.

"The airports not far…like 45 minutes with traffic, and it's fairly easy to re-arrange most anything so when you can book something…just e-mail me…"

"I'll let you know…and Paul?"

"Yes?"

"I'm anxious to see you."

"Me too Gwen…"Paul sighed, it was going to happen.

Gwen: Paul, I hope this is okay: Delta #545 arrives on Friday the 16^th at 9:30 pm, leave on Sunday, Delta #1636 at 12:35 pm. *Hugs*

Paul: See you soon! *Hugs*

It wasn't necessary to circle the date. Paul thought: Probably too late for dinner? No problem with work at all. Time to get the pace spiffed up, not like it's a mess anyway. Maybe some fresh cut flowers? Am I overdoing this?

The trip to the airport was smooth, after the rush hour and commuter traffic had eased however all the parking areas were nearly full due to the weekend comings and goings.

It was a short hike to the concourse entrance that accompanied all Delta flights including gate C-15. The overhead monitor blinked the green times, her flight would be delayed fifty minutes, likely more Friday congestion. Seated at one of the many airport bars Paul had a beer to calm down and accept the delay. To pass the time he flipped through a magazine someone had left, and then bought the Washington, DC newspaper. A steady stream of harried passengers scuffled along the carpeting, their tired faces and wrinkled clothing defined the extra endured hour crammed into small seating.

And there she was. Looking cool and stunning. Former thick red hair was dyed a shimmering jet black, long curly waves surrounded Gwen's oval face, somehow paled next to the dark tresses, eyebrows arched and a wide smile greeted Paul. Expensive sandals with thin leather strips criss-crossing halfway up Gwen's calves, smooth tanned legs ducked into a short tan skirt. A navy blue sweater casually draped over her shoulders, the loosened sleeves dangled across a silky white blouse and Paul knew that others' nearby were also sufficiently checking her out.

Hazel eyes bore into his and standing on tip toes Gwen brushed a friendly kiss on Paul's cheek, fingers firmly grasping his muscular arm, her delicate perfume wafted lightly into their close space, "Its good to see you…darling…" Gwen huskily whispered.

"Wow. You look good. I like your hair. It's…different. Very nice I mean!" Gwen's petite brown pocketbook nearly matched her simple carry on bag, her dainty fingers interlocked with his as they left the concourse, appearing as the perfect couple happily reunited and no-one noticed their age differences, not to mention her real gender.

The dashboard clock read 11:00 as Paul paid the attendant and zoomed away from the garage barriers, "Are you hungry at all?"

"Oh no. Thank you…I ate the greasy cuisine at the airport before leaving…" Gwen yawned. "It's been a very…long week…sorry…"

"Hey don't worry…just relax." Paul reassured her, pushing in a favorite Billy Joel CD. They chatted on and off and 45 minutes later he punched in the gate code, his sleek Frontier slithered through the quiet immaculately landscaped property.

"I'm on the 2^nd floor…nice view of the skyline and the pool." Paul said as they took the elevator up. His condo was spacious and dimly lit. Not at all bashful, Gwen didn't ask where the bathroom was, she found it. Paul smiled to himself, poured a glass of cold water, plopped on the couch and out of habit flicked on the news.

Gwen soon reappeared in a loose fitting, extra large violet night shirt and leaned over to kiss Paul's forehead. "Baby, I'm wicked tired…I'm sorry but I'm going to lie down for a bit. Okay?"

"Yeah, sure." Paul stammered, not expecting this and got up to show her around but bag in hand, Gwen headed directly for the bedroom as if she'd been here before. The nightly news was routinely depressing; he watched a few scenes from an old favorite movie then got on the computer until weariness approached.

Entering quietly he found Gwen on "his" side of the king sized bed, curled up under the comforter and sound asleep. Paul silently watched her for a minute, Gwen's mouth partly open, deep in la-la land. He had no intentions of disturbing her secure sleep. Closing the bathroom door he brushed his teeth, stripped and carefully slipped under the cotton sheets.

His dreams were the active type, traveling to a place that had a similarity but the people were all strangers, debating in a nonsensical way. Paul was driving along a deserted road and seeking…something.

Morning sunlight peeked around the edges of the opaque bedroom curtains; Paul blinked, rolled into the pillow and awakened slowly. His cock felt like petrified granite and bladder pain urged him towards relief and headed towards the toilet he realized Gwen was not in the bed. He smelled coffee and lazily slipped back into bed, glad it was Saturday.

"Good morning…" as Gwen appeared in the doorway.

"Good morning to you. I didn't want to wake you. Hope you don't mind but I made coffee. I'm…umm…an early riser and morning person as you can see." She beamed.

"Guess I don't need to tell you to make yourself at home…do I?" Paul chuckled. Standing next to the bed, Gwen's long fingernails lightly dragged across Paul's arm. "Sorry I fell asleep on ya. I was exhausted and your bed is SO comfy!" with another comfortable smile.

Arms crossed in front, she grasped the bottom of the nightshirt, lifting the fabric up and over her head. Paul's eyes drank in the sight: her unashamed smile, lovely sized breasts with pierced nipples and pink panties with dainty white lace around the leg openings. His cock stirred.

"Do you like it?" Gwen asked, her index finger pointing to the new belly button piercing.

"Yes…yes I do. It's you…sexy…"

She eased onto the large bed, kneeling in the other side of Paul and leaned down to kiss his mouth. He tasted coffee mixed with morning passion and hungrily kissed back. Gwen's fingers tangled within Paul's exposed hairy chest, roaming towards taut stomach muscles.

"Umm…I love your chest…so manly…" she murmured, the point of her tongue teasingly flicked against a nipple. Pushing aside the light sheet her hand quickly found his manhood, nimble fingers moving the skin up and down, bringing him fully erect.

"God, you're so hard. Is this a piss hardon Paul-ie?"

"Mmm…no…" He grunted, she grasped and began masturbating him. "No…I…I…already went…" Paul's ball sack stirred as Gwen kissed his stomach and slowly licked the tip of his cock.

"I've got just the thing for you…" leaving the bed and bending over to reach the overnight bag. Paul's cock continued to throb at the voyeuristic delight: one side of her underwear had wedged into the crease exposing a sexy tan line and an alabaster fleshy cheek. She returned with a small vial, unscrewed the top and drizzled a line of cinnamon scented oil upon his length, adding a few precious drops into her palm.

"You're going to like this…" She purred, spreading the slick mixture, massaging his growing penis, carefully fondling his swollen nuts. Red lacquered fingernails moved slickly up Paul's bloated dick, coating the skin, painting and smoothing the oil around the sensitive glan's tip.

"Oh God Paul. You've got the greatest cock. Huge. I love the shape, the way it feels in my hand. So hard. So stiff. I can't wait to taste your cum. Feed me. Look how hard you are. I could play with you for hours." The combination of Gwen's wording and fluid wrist movements had the desired effect: gasping, hips bucking uncontrollably and thrusting his swollen prick into her silken grasp.

Suddenly Gwen stopped, releasing her grip causing Paul's fat erection to plop onto pubic hair, "Now look what you've done. Bad boy." Gwen giggled, leaning back on her haunches showing Paul the small tented bulge pressed against the crotch of her panties. She deftly removed and cast them to the side; Paul stared again at the hairless pink prick standing at attention.

Receiving the same treatment, Gwen drizzled more of the oil onto her member and hissed delightfully. Numbly Paul watched as Gwen straddled atop, pressing her glistening shaft against his, rewarding him an exquisite sensation he'd never felt. The soft, sensitive underside of Gwen's penis sensuously rubbed along Paul's front. Gripping their well lubricated cocks together she slowly began to rock in a fucking motion.

The friction was slick, delicious and new, Gwen's penis slithered, finding a rhythm, oiled fingers caressed Paul's blood engorged cap. He moaned with pleasure.

"God…you're huge. The biggest cock I've ever seen. Do you want to fuck me?" Gwen lustfully whispered with half lidded hungry eyes.

"I…I…I want…to…do everything…with you…I…Ohh!" Paul gasped; the incessant motion of their erections rubbing together was too much.

"Ohh! Ohh! Fuck…Gwen...Ohh!" Paul's hips lurched upwards and a thick volley of cum ejaculated onto his stomach, Gwen's soft skin encouraging each pulsating spurt while he gripped the sheets and groaned through a spectacular mind blowing orgasm.

Blissfully spent, Paul felt Gwen's fingers touching and smearing the small pool of semen, "Wow…you came a lot…"

"Oh. What…you…do…to me…"

Blinking to focus, he looked up into smoldering eyes and heard the unmistakable liquid, crackling sound of Gwen masturbating. Jerking her cock, Paul felt sexy smooth balls lapping against his. An open palm propped against his chest to steady herself, Gwen's lovely breasts swayed so near. Paul lovingly tickled the white contoured undersides, fingering the gold loops and playfully tugged the rings.

"Yes! Oh God…yes! Pull…pull on them…now…" Eagerly Paul complied, testing her limits. Gwen's dark brown nipple flesh elongated and stretched painfully, eliciting only pleasurable sighs.

"I'm close…so close…"

"C'mon baby. Give me your cum. Let it go. Shoot all of it…onto me. I want you to…" Paul coaxed. The pace of Gwen's solo wrist action increased and she was there. Her sweet body went rigid, head thrown back and a high pitched wailing escaped.

"Huh…huh…ee…huh…uh…ee!" attaining her peak, warm droplets oozed onto Paul's midsection, with fascination he watched Gwen shudder and quiver from the intense feelings, milking every remnant of pleasure. She hunched forward and collapsed onto Paul, rolling over close to his side, her heart was beating wildly, hot breath rasping a bare shoulder. In the after glow his arm held Gwen securely.

"Whew. I love Saturday mornings…in bed…" She giggled minutes later, reached up to kiss him on the cheek and sprung up to retrieve a warm washcloth.

Paul sipped the strong coffee and Gwen attacked the container of fresh, chilled fruit and croissants. With the freedom of the day and the night ahead, they talked freely, eventually deciding to lounge by the pool for a bit. Gwen looked stunning n her skimpy, pale yellow bikini, hair tied back and dark sunglasses. Paul smiled to himself anticipating the small community's reaction as he arrived with the new "girlfriend".

"Paul? Be a dear and put lotion on my back…please?" She invited. Lying face down on a plush towel draped over the beach chaise, Paul leisurely smoothed the sun block over Gwen's neck, shoulders and back, stopping to untie the strap. Starting next with her feet, he slowly worked his way up closely shaved calves and legs ogling her tight buns.

"You've got a great ass…" he whispered.

"I'm glad that you like it." Gwen murmured. Conscious of a raging hardon bulge, Paul quickly plunged into the pool, swimming several laps energized by the cool refreshing water and abundant sunshine.

He prepared a sumptuous chef's salad for lunch which they devoured and flipped through many of Paul's old photo albums, everything from baby pictures, scenic trips and more recent. "She's beautiful Paul…your Annie…"

"Thank you Gwen…that's sweet. Hey, we should go shopping. I…uhh…would like to get you something."

"I love shopping!" She ecstatically exclaimed.

"Also…there's a really fine Italian restaurant o that end of town. Interested?" "Mmm…sounds great…" kissing Paul before bounding off to get dressed.

A colorful wrap around skirt swished atop Gwen's sandals as they walked hand in hand through the mall. Smiling, the beautiful creature yanked Paul into Victoria's Secret, each lustfully scanning the erotic lingerie and teeny bits of underwear. Without the least amount of embarrassment, Paul happily drifted through the store, picking up sacred women's undergarments. Gwen appeared holding up a smoky, see through negligee with a lace thong and matching bra. The skimpy sexy material was strictly for the visual…for his?