Bridging the Gap

By NPhillyDogg/Scedmark

Published on Jul 29, 2009

Transgender

BRIDGING THE GAP

Pt-1

It was 5 oclock pm when I walked into the neighborhood bar I knew HE used to frequent. I could feel all eyes fall on me as I sashayed over to the bar and took the first available seat at the counter. "Can I help you, miss...?" asked the bartender, looking at my budding cleavage as if he expected it to speak for me.

"Gin and tonic, please." I said simply, scanning the room to see if HE was here.

I bypassed by all the grinning faces staring at me as if I had just announced free drinks on me. I spotted HIM, sitting at the far end of the bar, sitting at a table taking to some of his old drinking buddies. He still looked good. A little older (but who wasn't), a little heavier, with a touch of gray in his usually jet black hair. He was in uniform, telling me that he still worked the same job from 10 years ago.

"This drink is compliments of the man seated at the end of the bar...!" smiled the bartender, placing my drink before me as he directed my vision to the young handsome man in glasses smiling back at me. He wore an expensive suit and had perfect wavy hair to go with his perfectly white straight teeth (probably a lawyer).

I smiled at him politely, then lifted my glass to him. I placed the rim up to my ruby red painted lips and took as sip as the man wandered his way down the bar towards me.

"Hi..." he said, smiling that perfect dental toothpaste commercial smile. "...my name's Harvey Carmichael. I'm a lawyer! And you are...?"

"Not interested!" I said, taking me drink as I got up from the bar and headed towards HIM.

I was wearing a tight fitted sundress which I knew hugged my curvy body in just the right places. The neckline plunged down towards the start of my ribcage, showing off my enhanced breasts as they mashed together like siamese twins. The dress stopped just above the knee, allowing a glimpse of thigh whenever the split opened too wide whenever I moved. My stiletto heels made a distinctive sound that caused attention to my walk as I sway my hips extra hard to prove the point that I was the baddest bitch to ever step foot in this bar.

As HE laughed at one of his friends' stupid jokes, I saw his eyes focus on me as I walked towards him. His eyes locked on me as I got closer. It was like moving in slow motion as I watched his eyes soak up my entire body from head to toe and back again.

I smiled at him faintly, just enough to let him know I noticed him watching me. As I turned the corner (heading towards the ladies room), I dropped my handkerchief (old cliché I know, but still very affective) on the floor.

"uh..., miss...! Miss...!!" I heard HIM say as I kept walking, ducking into the ladies room.

I stood on the inside of the door, listening as I heard his friends laughing at him, telling him that I was out of his league. I heard him say that he was only interested in giving me back my handkerchief, and that I was young enough to be his daughter. I waited a few minutes, pretending to use the powder room before leaving. As I opened the door, HE jumped up out of his seat to present me with my hankie.

"Miss..., you dropped this on your way to the ladies room..." he said ever so politely.

"Oh, thank you! I was looking for that!" I lied, touching his hand as he gave me my hankie. "My name's Alexandra..., what's yours...?" I asked.

"uh..., Lester...! Lester Wilcox!" he said, strangely.

"Are you alright...?" I asked, acting concerned, "Did I say something funny...?"

"oh no..., no...! It's just..., it's nothing." he said, blushing.

"No..., tell me...!" I flirted, touching his strong arm.

"Well..., it's just my wife's name was Alexandra...!" he said, boyishly.

"Wife...?" I asked, looking put off.

"Late wife!" he corrected. "She died in child birth, having my son! His name is Alex too..., named after her!" he explained, getting snickers from his friends whom thought he was blowing it by mentioning his dead wife and runaway son.

"How old is he...?" I asked, curiously.

"25!" he said, then added..., "I'm 45..., I had him when I was 20!"

"Does he look like you...?" I asked, feeling the muscles in his arms as he blushed.

"I..., uh..., I wouldn't know..., he ran away from home when he was 15!" he said, sorrowfully.

"awww..., I'm sorry to hear that...!" I pouted, sadly. "Come on..., let me buy you a drink!" I offered, catching him (and his friends) off guard. "I mean..., to thank you for finding my handkerchief...! It takes a girl forever to find just the right accessories!" I said, wittingly.

"I'm sure...!" smiled Lester, practically gushing. "But you don't have to buy me a drink..., the pleasure was all mine...!" he said, gentlemanly like.

"Will..., if you won't let ME buy you a drink..., would you at least buy me one...?" I asked, flipping the script.

"oh, uh..., sure...! Sure...! What would you like...?" he asked, giving his friends the shocked upward eyebrows when he thought I wasn't looking. I could see his friends in the wall mirror giving him the thumbs up as he walked me back towards the bar. We eased up to the counter, right beside Harvey the lawyer...

"I'd like a gin and ton!" I said, perkily.

"Okay! One gin and tonic for the lady...!" he ordered from the bartender. "And I'll take another beer...!" he added. I could see Harvey looking Lester up and down, wondering what the older man had that he didn't have? `Well..., ME for a start!' --I thought. "So Alexandra..., I've never seen you in this bar before..., do you come here often...?" he asked, making small talk.

"No. I used to live here a long time ago, but I moved away..., now I'm just...visiting!" I said, brushing my long blonde hair back off my shoulders to give him a better view of my cleavage.

I could see Lester trying not to look at them as he made polite conversation.

"Visiting family...?" he asked, diverting his eyes up to mine.

"Sort of." I said vaguely as the drinks came back. "What do you do for a living, Lester...?"

"I'm a security guard!" he said, looking somewhat embarrassed as if he might not measure up.

"Oh really...?" I asked, sounding excited. "Where at...?"

"Landon Industries!" said Lester, popping the cap to his newest beer. "They're a high tech computer software company..., I usually guard the entrance..."

"Wow..., sounds nice!" I said, taking a swig.

"What do you do, Alexandra...?" asked Lester. But before I could answer, he said..., "No wait..., let me guess...!" I stood still, posing with my hand on my hip as he openly eyed my body up and down before focusing back on my face. "You're an actress!" he said, confidently. I shook my head no. "Model...?" nope. "Singer...? Dancer...?" nope, nope. "Fashion designer...? Showgirl...?"

"Showgirl...??" I asked, pretending to be insulted.

"I didn't mean that in a nasty way..., I just meant..."

"What DID you mean...?" I asked, playfully.

"I meant..., with THAT body...!" he said, his voice trailing off as his eyes took me in almost as if for the first time.

I felt so bare standing before him right then, as if I hadn't had a stitch of clothing on. His eyes roamed all over me like a searchlight, taking me in in all my splendor and glory. I felt as if I had just emerged into womanhood for the first time in that moment, as if I had just been given approval by the pinnacle of maleness. "I'm sorry..., did I embarrass you...?" he asked, trying to read my thoughts.

"No..., --not at all, Lester." I said, taking another swig before sitting down my glass for the last time. "Lester...?" I asked, touching his broad manly shoulder. "...do you live far from here...?"

Pt-2

Two glasses of wine sit practically untouched on Lester Wilcox's living room table as I lay in his arms, kissing him as if we hadn't just met a mere hour ago. Lester had wanted to shower first, but I insisted that he stay with me, to keep me company on the sofa while listening to soft music.

I knew what I wanted, and I knew how to get it. After Lester came back with the two glasses of wine, I pounced on him, leaving my girly manners at the door. Lester was a bit taken aback by my aggressiveness, but he didn't complain as his hand wrapped around my waist.

Soon we were laid back against the cushions, his thick wet tongue burrowing into my mouth. I suckled his tongue, tasting the beer on his breath as his mustache tickled my upper lip. His big hand cupped my right breast, squeezing it with just the right amount of pressure as I reached down and felt his stiff cock through his pants.

Lester's cock was rock hard as I groped at it thought his uniform pants. He peeled back my blouse and bra, exposing my right nipple. I watched as he lowered his head and took my tit into his mouth.

"ohh...!" I sighed, feeling his lips wrap around my sensitive nipple as he began nibbling and sucking like a hungry 190 pound baby. "Ohh Lester...!" I moaned, as his hand moved up between my legs. I felt his fingers pull aside the lacey garment covering my womanly parts, as a spit wet finger slowly slipped inside me. "Ohh god Lester..., I want you so bad...!" I moaned, humping up against his hand.

"Oh man..., you don't know how badly I want you too...! Ever since I saw you walking up to me in the bar..." he groaned, abandoning my tits as I pushed him on his back against the other end of the couch.

With me on top, I tore at Lester's belt and unfastened his work pants until I was pulling out his stiff 8 and 1/2 inch cock. I looked down lovingly at the strong white tower of manliness, having waited so long to taste this wonder piece of man meat. I leaned forward, opening my painted mouth as I bent down and took his ramrod between my lips.

"Oooohhh Alex...!" he moaned as I sank my mouth down around his cock.

I felt Lester's hands in my hair, pulling my hair back into a ponytail so he could see me suck his cock. I wrapped my lips around the stiff tool, tasting the thick white column with my tongue before slurping my way back up to the head. "Damn..., you suck cock so good..." he moaned with delight.

He hadn't seen nothing yet.

I went back down on Lester's thick white cock, taking it deeper into my mouth until the fat cock head hit into the start of my throat. His body relaxed against the sofa cushions as he settled back for a long knob job, but I had other plans as I turned my head slightly leaning forward, opened my throat, then took him straight down into my esophagus inch by inch. "aahhhh, damn...! Where did you learn that...??" groaned Lester, loving the feel of my mouth on his cock as I buried his manhood into my throat.

I felt Lester's body tense as I buried my face in his hairy pubes, his long thick cock lodged balls deep in my throat. I felt his hands tighten in my hair as I churned his cock around in my throat for an 8 second count. I inhaled his pubic musk, breathing in the smell of his balls before lifting back up. I dragged my sexy lips up his spit slick column, sucking furiously on the head before plunging my throat back down on him full length. Lester gasped aloud as he threw his head back in ecstasy. I bobbed my head up and down on his pole rapidly, loving the taste of his big meaty sausage as it filled my greedy gullet to the brim.

"Stop..." warned Lester after a few minutes. I continued to suck, spurred on by the tiny bursts of pre-cum coming from his cock tip. I flickered my tongue across the head, licking away the cum drops before fucking my throat back down on his cock. "Stop, Alex...!" he begged, not wanting to cum yet. I could feel his hands trying to pry my head from his lap, but I had tasted his pre-cum, and was bound and determined to get the full load before I was through. "You're gonna make me cum if you keep sucking me like this...!" he warned my deaf ears.

I sucked and sucked that big hard cock, taking it from tip to base with each and every slurp of my lips. I hogged myself on his manhood, hungry for the creamy seed I knew he carried deep in his ball sac.

I felt Lester's cock starting to throb. I reached my hand in, milking the slick spit coated shaft with my palm as I slurped upon the head. "Oh shit, I'm cumming...!!" I heard Lester gasp, just before his cock head swelled and the first of 5 creamy spurts gushed out of his cock.

I felt the first spurt rush into my mouth, blasting my tongue and gums with the salty taste of sperm. Lester thrashed around on the sofa as his orgasm hit. I milked his cock with my hand, sucking the cum from the tip. I swallowed the first gulp, feeling the creamy sludge slide slimily down my throat as my mouth quickly filled with more cum. Lester's hands relaxed on my head as his orgasm slowly subsided. I could feel his cock wilting in my hand as I sucked away the last drops of cum. When I was done, I looked up at him and smiled.

"You're absolutely amazing...!" was all he said, pushing me onto my back on the other side of the couch. He pushed my legs open and pulled off my frilly panties. I saw him stair down at my pussy, licking his lips wantonly before going down on me.

"Ohh Lester...!" I gasped, feeling his mouth and tongue against my clitoris.

I looked down and watched this handsome, rugged, manly man eating my trimmed cunt, licking my pussy as if he hadn't eaten pussy in years. He flicked his tongue across the surface, sucking hard on the clit while gently kissing my inner thighs and fingering my wanton hole. Ever so often he would reach up and shove his fingers into my mouth, or squeeze my tits after pulling them out from my brassier.

I never felt more like a lady than when I looked down and watched this big strong man whom I admired and desired for so many years, feasting on my womanly parts as if they were tailor made just for him.

After about 20 minutes of eating my pussy, Lester worked his way back up my body, kissing and sucking his way across my tits and neck, until we were kissing full fledge like lovers.

I reached down and grabbed his once again erect cock, sliding the moist head up and down my cunt slit. Parting from his kiss, I spit into my palm, then reached down to lubricate my cunt before pulling Lester's cock up to the hole.

"Should I get a condom...?" he asked, concerned.

"Don't worry..., I can't have any babies...!" I assured him as he slowly sank in. "OOOHHH yes...! Yes daddy..., take my cunt...!" I whispered, sensually.

Lester leaned down on top of me and buried his cock inside me, grounding his hairy pubes against my mound. We were finally locked together, lock and key. So many years of patient anxiety came down to this one momentous moment. I hoped I would be able to contain myself.

Lester ground his cock around in my cunt for a few minutes, allowing me to get used to him (as he got used to me). Then slowly but surely he began to pump his hips, driving his thick fat cock in and out of me as I spread my legs around his waist.

I could hear him breathing in my ear with his face in the cushions behind me. I could feel his chest beating against mine, his slight beer gut pressed against my flat tummy as he fucked me in missionary position. I couldn't believe how good his cock felt sliding through me, as if it belonged there. After years of eager anticipation, it was finally happening. I finally had the cock of the man I've always loved the most deep inside me. I could feel the excitement building up inside me as I began to cum. I locked my thighs about his waist as I tightened the muscles in my vagina, milking his manhood again.

"Did you just cum, baby...?" he asked me, looking down into my face as I lay with my eyes closed.

"Yes..." I said, feeling embarrassed and ashamed.

"Yes what...?" he asked, looking into my face.

My mind searched for the correct term he was looking for...

"Yes daddy...!" I said, bringing a smile to his face.

"I love it when you call me that!" he said, burying his head in my neck as he resumed fucking.

I bit my lower lip as he slid that fat cock in and out of me. My cunt had begun to dry, and the friction was beginning to burn. I heard Lester moan as my cunt sucked at his cock, the pre-cum from the head of his dick the only lubricant lining the way. I had no idea how long it would take Lester to cum this second time, giving his age and all. He had me by a good 20 years. He didn't seem to mind the friction as he continued to hump away inside me. Ever so often he would pull out while I licked my palm to re-lube myself. He'd slide his cock back in and resume fucking, picking up where we left off.

My tits bounced up and down against his chest as he fucked me. I could feel the hairs of his hairy chest scratching the smooth delicate skin, making my nipple rock hard. I held onto his waist as he fucked, feeling the power behind each stroke as he speared me with his rod over and over. He picked up the pace after awhile, his thrusts getting deeper and stronger as his second climax neared. I could feel his hairy ball sac slapping against my ass with every inward stroke. After about a good 25 minutes of straight fucking, his cock finally swelled in my vagina, firing thick ropey load after ropey load into me.

"AAAAHHHHHH shit...!!" he yelled, cumming hard.

I felt his cock jerking inside of me as Lester squirmed around on top of me, filling my hungry cunt with his badly needed seed. I could almost feel the warm gush of manly fluids filling me, coating my insides and making me sloppy wet with his aftermath.

Lester collapsed on top of me, breathing hard as our heated bodies took time to cool down. I stroked my fingers across his back, feeling his cock soften inside of me. We lay like that for several minute, until I heard him starting to snore softly in my ear. I smiled to myself, knowing I had just satisfied him, giving him the ultimate gift anybody could bestow on another person. (an orgasm).

Ten minutes later I had to use the bathroom. I gently pushed Lester off of me, making him roll onto his side as I got up from the sofa. He pulled at me in his sleep, refusing to let me go until I assured him that I wasn't going anywhere. I kissed him lovingly on the forehead, brushing his thick salt and pepper head back for his brow, then tip-toed my way upstairs to use the bathroom.

Walking up the steps, I saw all the old family photos he still had hanging on the wall. Pictures of him and his late wife in her wedding dress, of him and his son (Alex) as a young child, and what looked like recent pictures of himself (Lester) older. As I got to the top of the stairs, I noticed the second bedroom door ajar. I walked over and peeked inside, sure I'd find a storage room or converted closet. I was surprised when I turned on the overhead light to find that it was Lester's son's bedroom, completely intact as if he'd never left.

I wandered into the room that time forgot, looking at the old posters of Madonna and Janet & Michael Jackson on the wall. The bed sheets were old and dusty, as if they hadn't been changed in years. In the closet were all the old clothes his son left behind, as if waiting for the day he would return. But what really caught my eye was the 10 birthday cards lined up on the dresser, each numbered with an age dating back to the year he disappeared.

A tear filled my eyes as I read the last card:

"To my son, Alex, wherever you may be,

I hope you are alive and well, and living the life you've always wanted. I regret what happened on that last day that I saw you. If I could, I would take it all back. Wherever you are, I hope you are happy. And I hope you take at least one minute on this, your 25th birthday, to think of me.

Your father, Love always, --Lester! xxooo"

As I read the card, a warm feeling of love and gratitude passed through me as I felt compelled to say out loud; "I love you too..., dad!"

Written by Eugene Marvin NPhillydogg@aol.com Look me up on Facebook for updates

Next: Chapter 2


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