tagTranssexuals & CrossdressersOld Friends, New Lovers

Old Friends, New Lovers

byLuckyBob©

I first met Ronnie when he was 16, His father, a Cuban exile, had hired me to customize a 37 foot cruiser, a big, beautiful boat. If you've read my stuff, you know that I'm a boat builder here in Florida. Oswaldo, Ronnie's dad, had come over from Cuba in 1963 and made a fortune as an insurance broker. He'd married a gorgeous Venezuelan lady, and Ronnie was their youngest son. Oswaldo was short and brown-skinned but his Venezuelan beauty queen was tall and fair-skinned, with startling black eyes and ruby red lips.

At 16, Ronnie was a budding punk rocker, with a short brush cut and a row of earrings in his left ear. I only really met him once, and his lisping voice and hand gestures indicated he wouldn't be playing first-string on the U. of Miami football squad. As we exchanged pleasantries, I glanced over at Oswaldo who had a wan, disappointed smile pasted on his face. Later, over drinks in his study, Oswaldo complained that his wife, the lovely Graciela, had spoiled their youngest child.

"So, you see," Oswaldo said with a sigh. "What kind of men you make when you spoil them as boys."

I nodded, patted my friend on the shoulder, and we downed more bourbon.

Oswaldo's finished boat was a work of art, and he kept inviting me to go fishing with him down in the Keys. I was always too busy. And, as first one and then another and another year passed, we saw less and less of each other. Then, one day as I was shopping in a local supermarket who should I run into in the frozen vegetable section but Graciela. She looked great, as usual. And as our eyes lit up in mutual surprise, I could see her straightening up to give me a better view of the other great fruit of Oswaldo's money - - her liposectioned, sculpted and fantastic body.

A couple of days later, Oswaldo called me. We chatted and he invited me down to the Dominican Republic, where he and Graciela had just finished building a new villa on the island's north shore. It just so happened that I would be in the DR in the next month, delivering a boat to an American record executive who had also just finished building his villa. I told Oswaldo I'd stop by.

So, in early June, under the boiling hot Caribbean sun, I drove my rented SUV up the long, curving private drive to Oswaldo and Graciela's blinding white villa. A couple of servants ran out to greet me and take my bags inside, where Oswaldo was waiting in the huge, cathedral-ceilinged living room. We had drinks and renewed our friendship.

About a half hour later, we heard a car pull up in front of the house and then Graciela's sweet voice filled the entry hall. She walked into the living room and we hugged and kissed each others' cheeks.

"Ronnie," Graciela called into the hallway, clapping her hands with joy. "Come and see who's come to visit us. Come see our first visitor to the new house."

Ronnie walked in from the hallway. He had grown up. Actually, he hadn't grown much taller than when he was sixteen. And, he was still slender. But his face was more mature. He had inherited his mother's high cheekbones and big eyes but his beautiful, smooth honey-toned skin showed a happy combination of his mother's ivory complexion and his dad's darker skin. He also had his mother's full, red lips. He was a good-looking 20 year-old, though more along the cute rather than the rugged lines.

When he saw me, a big, bright smile lit up his face. We shook hands and I noticed two things: his long, lustrous black hair that he wore in a pony tail and a whiff of some kind of perfume – sweet and nutty. As we shook, I also noticed his fingernails which were long and polished. I looked into his eyes and some kind of secret, warm familiarity seemed to pass between us.

That night we all ate dinner together. Oswaldo was merciless but also good-hearted in his teasing of Ronnie.

"Ronnie wants to go into interior decorating," Oswaldo said to me across the mahogany dining room table. "He'll do your place in Miami for a class project!"

We all laughed, even Ronnie.

"Of course, Jim," Ronnie said in his high-pitched, melodic voice. "But I'll expect to earn some extra credit."

He flashed his big brown eyes at me, and I could feel my crotch tingle.

After dinner we headed out to the wide veranda that gave out onto fantastic views of the deserted, white sand beach below us. Oswaldo's cel phone rang and he returned inside to do some business. Graciela twined her arm in mine.

"Jim," she said, flashing her white teeth. "It's so good to have you with us again. Oswaldo really needs a friend now. And, Ronnie hardly ever sees his dad. How long will you stay?"

I demurred. Maybe two days, maybe three days. Graciela urged me to stay the week and then departed for the kitchen where she needed to plan the week's meals with the cook.

Ronnie sidled over to me and we began chatting. He was a sweet kid, full of questions about me and about my business. He actually was interested in interior decorating and he understood quiet well how this choice and, really, his life conflicted with his dad's ideas. We joked around and laughed, and around midnight I pled sleepiness and told him I was heading up to my bedroom.

Ronnie raised his arms for a hug and as we hugged, I felt his hands rubbing circles around my shoulders. I also got a big whiff of his perfume or cologne. His hair, soft and long, smelled sweet.

"My father always calls you Big Jim," Ronnie whispered in my ear. "His big American friend. Will you be my big American friend?"

Ronnie giggled softly and squeezed my shoulders. I patted him on the back.

"Sure," I told Ronnie. "Call me your big American friend. In fact, call me anytime."

I laughed as we parted.

"See you tomorrow," Ronnie said with a wide smile.

Upstairs, I took a quick shower, flopped down on my bed, and slept like a baby.

The next day, Oswaldo apologized that he had some business to take care of in the capital. He would be gone for a day or two. He hoped I'd stay until his return and, thinking about all the work that waited for me back in the States, I agreed that I would. Graciela and I ate breakfast together and then I put on my running shorts and a tank top and headed out to the beach for my morning jog.

It was a perfect Caribbean morning - - bright sun, blue sky, blue ocean, and pure white sand. As I trucked along the beach, a pair of teen-aged Dominican girls waved to me and motioned me over to where they sat under a line of palm trees. I detoured and soon we were chatting and laughing. They were looking for an American boyfriend, they told me. And, I would do.

I told them I was flattered and very interested. The prettier one, dark-skinned and slender, put her arm around my waist.

"Come tonight to the Cibao bar," she leaned up to whisper in my ear. "I'll teach you how to dance bachata."

I gave her slim waist a squeeze and promised I would meet her on the dance floor. We kissed each other on the cheek and I headed back to Oswaldo's

Inside, I showered and went to the kitchen for an orange juice. Ronnie was sitting at the dining room table eating breakfast and looking very lonesome at the big empty table. I sat down at the table and we chatted.

He was wearing extremely short shorts and a midriff baring tank top. He had crossed his long, amber legs and was swinging them back and forth contentedly as we talked.

"Jim," he said with a smile. "I know a fantastic beach. Perfect sand, gentle surf. And, no tourists!"

"Sounds inviting," I replied.

"Yes, I am inviting . . .you," Ronnie answered with a laugh. "But we need to take one of my dad's boats. Are you game?"

I said I was and we agreed to meet on the boat dock in a half hour. I returned to my room to change into my swim trunks and met Ronnie at the dock. He had packed a bag which I helped him lug over the side of the boat.

"What's in here?" I asked him, toting the bulky bag into the cockpit of the boat.

"Oh," Ronnie answered. "The cook packed us a lunch, and I just packed some unmentionables."

We laughed and I started the boat. Ten minutes later we were whipping across the gentle waves of the Caribbean. Ronnie gave me directions and then clambered up to the prow of the boat for some tanning. He unloosened the band that held his pony tail together and his long, luxurious hair fluttered in the ocean breezes.

A little while and I saw a small, tree-dotted key appear off the bow. Ronnie sat up and gestured toward it with a smile. I steered the boat to the islet and pushed the little twelve-foot runabout up close to the beach. Hopping out into the warm waist-high water, I beached the boat and helped Ronnie out.

"Thank you, darling," he said, squeezing my upper arm.

We made our way up the beach of the deserted key and once under the cluster of palm trees, I dropped the bag. Ronnie got busy spreading out a big blanket and popped open a cold beer from the soft-sided cooler in the bag.

"Here you go, Jim," he said, passing me the beer. "Now, I need to go freshen up."

With a giggle, he stood, ran his hands through his long hair and headed over to the other side of the tiny palm tree grove. I took a long swig of ice cold beer and settled down on the blanket. Ronnie's shadow fell across me as he returned. I twisted my head up to look at him.

Wow. Freshen up indeed. Ronnie had changed into a white thong bikini. He had brushed out his hair and applied some lipstick to his full, pouty lips. He stood there above me, perched on long slender legs, his hands on his hips. I whistled in appreciation.

" You like?" he asked with a teasing smile.

"I like a lot," I answered with a smile.

"You know, Jim," he continued. "Nobody's going to see us out here. And, this is a bathing suit optional island."

I laughed, settled my beer on the blanket, raised my hips and shucked my bathing suit. I kept my tank top on. Ronnie whistled.

"You like?" I asked.

"Wow," Ronnie answered, licking his lips. "You really are my big American friend."

I guffawed and patted the blanket next to me. Ronnie settled his slender, long-legged body down onto the blanket next to me.

"I really don't want to burn out here," he said, turning his head toward me. "Be a friend and put some lotion on me. Will you?"

He reached into the bag and pulled out a bottle of coconut tanning oil.

"Friends help friends," I answered, taking the bottle from him.

Ronnie flipped over onto his stomach, revealing a round, firm ass. The thong strap disappeared between his two inviting cheeks.

I opened the bottle, poured a generous dollop of oil on my hands, and began to rub the slick, sweet-smelling stuff into his legs. They were long and firm, not muscular but taut and well-defined. As I worked my hands up his thighs, Ronnie murmured his approval. I got onto my knees and straddled his ass, working my slick hands up along his lower back and then onto his shoulders. Ronnie smiled and began to gently rub his ass up against my crotch. As I worked the oil into his shoulders, he moaned gently.

"Turn over," I said, giving his shoulders a firm squeeze.

"My pleasure," he answered, twisting his body under mine.

I murmured as he did. His body was tight. The bikini top he wore strained against his light brown skin. His stomach was flat and, looking down, I saw the bulge of his cock beneath his thong bottom. He settled back onto the blanket, his hands at his side, his long hair spread out around his lovely face, and a big smile plastered on his lips.

I began rubbing oil along his shoulders and upper chest. When I got to his bikini top, I slid my fingers under the cups and twisted my oily fingers around his already stiff nipples.

"Oh, god, Jim," he said with a squeal. "That feels good."

His hips began to undulate under me. I moved down, smothering him with the coconut oil. First, across his flat, hard stomach and then down along his thighs. Soon, Ronnie was writhing in pleasure as I kneaded his legs and stroked his inner thighs. Finally, with a grunt, he pushed me off. I rolled onto my back on the blanket and gazed at his brown, glistening body.

"What are you trying to do to me?" he asked mischievously, running his hand across his chest. "Don't you know how a girl gets all hot and bothered when a man treats her this way?"

I laughed and leaned back on the blanket. Ronnie slid over to lie on top of me. I felt his slick, hot body along my thighs and my chest. He propped his elbows on either side of my face.

"God, Jim," Ronnie whispered. "You're in great shape."

I thanked him.

"Hmmmm," Ronnie continued, running his hand through my chest hairs. "So big and burly. Such a macho hombre."

I laughed and Ronnie took his hand off my chest to stroke my cheek.

"Wow," Ronnie murmured. "Do you like me, Jim?"

I said I did as Ronnie began rolling his crotch against mine. I could feel his hard cock rubbing against mine.

"I'm such a little fag," Ronnie said, panting now and putting his hands on either side of my head to push his crotch harder against mine. "I'm just Daddy's little fag. Can you be my Daddy?"

He smiled wickedly and I groaned as he began humping his bikini bottom against my hardening dick.

"I know, Daddy," he whispered hoarsely. "I'm such a little bitch sometimes. But, I get so jealous that some other girl will steal my big Daddy away from me. That's why I'm such a little bitch sometimes."

With a groan, Ronnie slumped his head onto my neck and began squeezing my shoulders in his hands. I dropped my hands onto his tight ass and began kneading it roughly.

"Ohhh, yes," Ronnie gasped into my neck. "That's it daddy. I'm such a little fag, but I can't help it."

With a groan, Ronnie slid his hand down along my body to my bare cock. His warm, slick hand circled it. He began sliding his hand up and down my now erect dick.

"Hmmmm," he continued moaning into my neck. "I can't help it daddy. Your little girl just needs her daddy's big fat cock. Ohhhhhhh."

I began raising and lowering my hips to meet Ronnie's increasingly frantic stroking of my dick.

"That's it, daddy," Ronnie moaned. "Oh, I love your big fat dick. I'm just your little fag. Your little girl."

Ronnie raised his head to look into my eyes. His face wore a strained, eager look. He licked his lips. I took one hand off his ass and pushed it into his long, thick hair. I pulled his lips onto mine and Ronnie plunged his tongue into my mouth. He was whimpering now with pleasure. His hand began to shake my dick furiously. I rolled over on to my side, and Ronnie slid over onto his hip, his hand still clutching my cock and his lips still glued to mine. He began pulling on my dick even more furiously.

I reached down and yanked his thong down over his thighs. Ronnie's small, slender dick popped out into the bright sunlight. I cupped his balls in my hand and after a few tugs, I slid my hand between his thighs and began fingering his asshole.

Ronnie moaned and broke our kiss. He was panting and grunting as I slid my suntan-oiled finger into his tight asshole.

"Oh, Daddy," he almost shouted as my finger slid into his ass. "That's it daddy, fuck your little fag. Fuck me hard."

My cock was rock hard and, lost in his pleasure, Ronnie had stopped stroking it. I flipped him onto his back and pulled my finger out of his asshole. I pulled his bikini thong off his legs. Ronnie moaned and rolled back and forth on the blanket as I slipped the thong off his feet. Once his legs were free, he flung his arms back above his head, raised his knees, and spread his legs.

Ronnie's short, stiff cock bounced back and forth in the air as he pulled his knees up, revealing his small, brown asshole. I jabbed a finger roughly into his asshole and, with my other had wrapped around my cock, lowered my hips to his crotch.

He reached down to yank my finger out of him and then grabbed my cock and pushed it hard down onto his asshole. I planted my hands on either side of his head as he began playing my cockhead around his asshole.

"Fuck me, daddy," Ronnie moaned, jabbing my fat cockhead into his asshole. "I'm daddy's little fag. And I want your cock. I want it soooooo badly."

I grunted and pushed my hips forward. Ronnie gasped as my cock spread the tight muscle of his sphincter.

"All of it," he groaned. "Put all of that big fat cock into me. Pleeeeeeease, daddy."

With a thrust of my hips, I slid my cock all the way up Ronnie's hot shithole. He screamed. We froze together for a moment.

"Oh my god," Ronnie panted, a pained look on his face. "It's too fucking big. You're killing me."

I grinned and slowly began pulling my cock out of his asshole and then pushing it back in. Ronnie grunted with each thrust and soon had his long-nailed fingers buried into my back.

"Yes. Yes," he grunted with each thrust. "Give it to me, daddy. Give it to me."

Soon, I was banging away at Ronnie's ass with gusto. He was whimpering and sobbing. I reached down to give his dick a stroke, but he yanked my hand off his cock and jammed it into his mouth. He raised his ass up off the blanket to meet each of my thrusts and began sucking my fingers. The whole while his eyes were closed and he squinted in pleasure and pain.

Gradually, I slowed down my strokes as I felt my balls begin to tighten. We were panting together and together we began to relax our breathing.

"Not yet," I mumbled. "Not ready to cum yet."

Ronnie smiled and squeezed my ass with his free hand. He opened his big brown eyes and began slowly and lasciviously to suck my middle finger. He reached up with his other hand to grab my hair. I grinned. Then, suddenly, I pulled my cock out his asshole, pulled my hand out of his mouth and flipped him over onto his stomach.

"Ohhh," Ronnie squealed in surprise.

I smacked his ass hard and then ran my finger between his cheeks. Ronnie moaned with pleasure. I spread his ass cheeks and, brusquely, jammed my cock back into his asshole, squeezing his round, plump cheeks with one hand as I guided my cock back into him with the other. Ronnie groaned.

"Now, baby," I whispered into his ear. "Daddy is going to fuck your ass hard until he comes."

Ronnie sighed and pushed his head into the blanket. I began fucking him really hard, looping one arm around his waist and pulling him onto his knees. My hips rammed against his ass, shaking his cheeks, as I pushed my fat, engorged cock deeper and deeper into him.

"Oh, you dirty bastard," Ronnie shouted. "Fuck my ass, you motherfucker. Fuck it. Fuck it hard. Fuck me, daddy. Fuck me."

I complied, and soon my hard, rough thrusting had pushed Ronnie down onto the blanket, his ass raised upward to meet my cock. My dick felt thick and heavy as a baseball bat, and feeling his ass constrict around it, I gazed up through the palm fronds above us into the deep blue Caribbean sky. I squeezed my eyes shut with pleasure as I felt a climax rumbling up through my shaft.

"Oh, baby," I groaned, pushing my cock deep into Ronnie and holding it there. "Is my little fag ready for daddy to cum?"

Ronnie responded with gurgling sounds of pleasure and clutched the blanket in his hands.

With a groan, I felt my cock burst in pleasure. I rammed my hips tight against Ronnie's smooth, round ass and pushed him down deeper onto the blanket. Ronnie groaned as I emptied my load deep inside him, my impossibly hard cock twitching spasmodically. As I rode his ass to climax, Ronnie beat the blanket with the palms of his hands.

"Ay, cono," he shouted into the blanket. "That's it you motherfucker. That's it. Pour it all into my fag ass. Give it all to me you nasty man. You fucking nasty, hard man. Give it to me."

With a deep, shuddering sigh, I felt my cock shoot its final load into Ronnie, and I felt his ass squeeze my shaft. Groaning loudly to the sky, the sun, and the sand, I gave a final thrust into Ronnie and then slumped onto my elbows.

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byLuckyBob© 4 comments/ 83706 views/ 9 favorites

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