Beaches

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Straight guy falls into relationship with a shemale.
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earlbrowder
earlbrowder
1,127 Followers

A couple of things you should know about me: I'm not gay; I've always had this thing for dark-skinned women.

I graduated from the army at age 21 and headed home to the Bronx. Me and a buddy of mine started up a livery car service. We started with four cars. 15 years later, we had 100 cars and almost 200 drivers. We became the biggest car service in New York City. I got married at 23 - - to my best friend's sister. Rosie and w split up 10 years and three kids later. At age 36, I married Veronica, a 25 year-old dark-skinned Dominican woman, the sister of one of my drivers. Unfortunately, I spent the night before my 40th birthday in Atlantic City with Lucia, Veronica's 22 year-old niece. When Veronica found out, we ended up in divorce court. I'd had enough of the Bronx, enough of the 9 to 9, and enough of the same old faces. At 41, I sold my piece of the business for a hefty chunk of change to my partner. Then, I fulfilled a long-standing dream: I moved to a beach bungalow in Antigua, where I now live 8 months of the year. I keep an apartment in the Bronx and a house in upstate New York where I spend part of the summer.

I'd only been in Antigua, settling into a lazy, carefree life of beach, beer, and broads, for four or five months when my childhood friend, Rocco, flew down for a week. Rocco got bored fast, so on his second night we hit the local tourist clubs. My favorite pick-up spot was a joint called Juniors, a place with mellow lighting, a great bartender, and most weeks an assortment of gals staying across the road in the local 2 star resort.

On the night in question, Rocco and I were lounging at the bar talking to Bev, the bartender, and eyeing the imported flesh. I was joking with Bev about the sexiness of Jamaican women when Rocco elbowed me.

Check 'em out, said Rocco, as he gestured to a group of women entering the bar.

I swiveled toward the door and smiled in appreciation. A group of three women had just entered, each dressed to the nines and strutting their stuff like they meant business. All of the gals were tall and slender, but my attention was taken by the really cute black girl sandwiched between her two blonde friends. She was tall, slender, really dark-skinned with a wide mouth and big brown eyes. Her sundress was cut low to reveal two lovely tits and she swayed into the bar on the longest legs I'd ever seen.

Rocco and I waited for the girls to sit down and then I sent over an order of Beachcombers, Junior's proprietary concoction guaranteed to get a buzz on before the first sip went down. The waiter waved to us and then the girls waved. Rocco and I left the bar and joined the three women at their table.

I sat down next to the black girl, Rocco next to one of her blonde friends. This black chick gave me the kind of big, warm smile that sends a shiver down your dick. I slid next to her until our thighs were touching. Her name, she told me in a deep, sultry voice, was Jen. She was from cold, snowy Chicago and was dying to have some fun over the next four days. We joked around about Chicago and about the resort she was staying at. She asked me if I liked to dance and before I knew it, we were grooving together to some deep, slow reggae.

Jen felt great. I didn't want to push things, so I was very gentlemanly. I rested my hands on her waist, moved to the music, and sucked in the scent of her sweet perfume and the sight of her smooth black skin. She was really into the dancing and kept whispering little jokes and questions into my ear. After a couple of tunes, we sat back down and the girls started buying us drinks. Before I knew it I was wasted. I remember, blurrily, seeing Rocco leave with one of the blondes. And I remember trading tongue with Jen. What I remember most clearly is laughing and giggling with Jen as I accompanied her to her room. At the hotel room door, Jen and I did some hot necking, and I ran my hands up over her voluptuous ass and around her waist. I was so bombed, I started getting dizzy. I remember saying good night to her and watching her ass as it disappeared on long legs into the darkness of her room.

I stumbled home, unlocked my door, and fell into bed.

I woke up the next morning to bright sunlight cascading through the window and the sound of the surf 20 yards away. My mouth felt gummy and my body ached. Rocco was missing. Lucky bastard, I thought to myself. I washed up then drank some juice, fixed some coffee, and sat out on my porch in my boxers and t-shirt, soaking the sun's rays deep into my weary joints.

I must have fallen asleep because the next thing I knew I heard Jen's voice in my ear, whispering "Get up Jimmie, I'm here." I bolted upright and there she was.in front of me - - tall, dark, and lovely. I apologized and said hi. She laughed and explained that we'd made a date the night before for a day on the beach. I gulped and stood up. Jen looked great - - her long straight black hair was tied back in a ponytail, she wore dark, designer shades, a bikini top, a sarong covering her bikini bottom, and a pair of short-heeled beach shoes. I got her a cup of coffee while I went inside to change into my swim trunks. We headed down to the beach arm in arm - - her slender black arm looped around my tanned, hairy bicep.

She smiled as we walked to the beach and I ran my eyes hungrily over her fine body. She looked to be in her mid-twenties and had a pair of beautiful perky tits, probably 35C, a slender waist and wide ample hips on top of a round firm ass. This could be one helluva day at the beach, I thought to myself.

Sweat was already glistening across the top of her chest by the time we found a shady, secluded spot not more than 15 feet from the surf's edge. I spread out a blanket, tuned the radio into a local soca station, and we settled down together. Her shining black skin was like an aphrodisiac to me, and I could feel my cock stiffen with every glance at her body's abundant curves.

Baby, Jen said to me, you must be in such sad shape after last night. I can't believe how much you drank.

I laughed and told her how one problem with Antigua was that no one knew how to give a really good massage.

Laughing, Jen said, Ain't no Chicago girl ever said no to giving a good man what he needs. Turn over on your stomach, sugar.

I rolled over and Jen settled herself down on the small of my back. She began working over my shoulders with amazingly strong hands. She spread suntan oil in her palms and then slowly pushed and rubbed the oil into my shoulders and back muscles. I was in heaven and groaned as she worked at my upper arms.

Hey baby, I said to her, you still got that sarong on?

She laughed and answered, Not for long.

I felt her rise up off my back, saw the sarong drop next to us, and then felt her settle back down. As she continued massaging, I could feel my cock growing longer and fatter. At first, I tried to concentrate on the massage, it felt so good. But then, as my erection grew I started to really enjoy the feel of her weight on my body, and my tingling cock. Finally, I grabbed her hand as it came off my bicep and pulled her to the ground beside me. She lay on her back, panting, and I slid over to kiss her. Our mouths met and then our tongues rolled into each other, and I heard Jen give a deep moan.

As we kissed, I ran slid my right arm under her neck and ran my left hand down to her tits. They were so full and firm. Groaning myself, I pulled my mouth away from hers and licked my way down to her breasts. I pushed her bikini top up and ran my tongue around the dark, sweet skin of her breasts. Then I nibbled on her nipples and rolled each one between my lips. Jen groaned and pushed her hands through my hair, shoving my head back and forth over her tits as her nipples hardened.

Hmmmm, I mumbled, raising my head up, baby, you taste so good. I looked down between her tits, along her belly, to the taut red thong stretched across her hips.

Let's play some more, I laughed, as I ran my hand down along her belly and then along her inner thighs.

Jen moaned and clasped her hands behind her head, raising her ass off the ground and rolling her hips. Taking this as an invitation, I pulled my hand to her crotch, prepared to play with her pussy when . . .to my shocked surprise . . I felt something long and hard pressing against the silky fabric of her thong.

What the fuck? I asked as I grabbed what felt like a good-sized and growing cock trapped beneath the thong. What the fuck is this?

Jen was so carried away with her pleasure that she kept pushing her crotch against my hand. Please, please, daddy, she begged in a low, whimpering voice as she moved her hand onto mine, don't worry about that . . . .you're making me feel so good.

Jen squeezed my hand around her cock and then laid both her hands flat at her side, pressed into the ground. Her eyes were half shut in ecstasy as she continued to grind her pelvis against my hand. I was flabbergasted. Here was a beautiful, sexy black woman . . .built like a brick house . . moaning in pleasure . . .while her cock was hardening into something thick and long under my hand. I was shocked. It didn't make any sense. Jen continued to writhe. And, feeling my own cock fat and heavy in my trunks, I was driven by lust and some kind of weird curiosity to keep on going. As she rotated her hips against my hand, almost involuntarily, I found myself reciprocating - - rubbing and squeezing her dick while she continued to moan.

My own dick is about eight inches, and Jen's was at least that long and very thick. As I stroked her thong, I could just start to see its fat black tip poking up over the waist of her bikini bottom. Shit, I thought to myself, this is really fucking freaky. I felt my own cock getting rock hard. Jen was going wild, gyrating her hips and now playing with her tittties while I moved my hand up and down her dick in the time-worn jerk-off fashion. I pulled her dick faster and harder as her moans turned into quicker, shorter gasps.

Oh, oh, oh, baby, Jen gasped, oh baby, yeah, uh, daddy, daddy, yeah, baby.

By now a good two or three inches of her thick black cock were poking out of her thong and the sight of it drove me to a weird, pitched lust. Suddenly, I reached under her thong and grasped her cock in my hand, feeling its fat black hardness in my fist.


Oh Jen, I whispered. Come on baby, come on . . . cum baby . . .shoot it . . .oh you sexy little bitch . . .cum . . .cum for me.

As I chanted for her to cum, Jen twisted her nipples furiously, one in each long-nailed hand. Her ass was humping frantically off the beach and I rose up to get both hands around her cock, pulling on it like a madman. With a muffled shriek, Jen threw her hips into the air and held them there for a moment, her thighs and ass trembling with excitement. And then she came, her jiz shooting high into the air, her cock squeezed between my hands vibrating and jerking as she shot gallon after gallon into the sky.

Ohhhhhhhhh, Jen grunted. Ohhhhhh . . .yesssssssssssss.

She began to involuntarily pump her hips as her dick emptied itself. Her mouth hung open and her eyes were squeezed shut. Her hands cupped her tits and I watched the aftershock of her orgasm ripple across the tight muscles of her stomach. When the tremors passed, she dropped her hips back to the ground and let out a huge sigh. She pushed her hands into her hair and slowly tried to catch her breath. I was stunned as I watched her massive dick begin to relax and shrink. Gulping, I let go of her cock and flopped onto my back. I wiped the sweat off my brow, closed my eyes, tried to quiet my panting excitement, and wondered what it all meant.

A couple of seconds later, Jen rolled onto her side, facing me. I felt her hand caressing my chest, and then she kissed my cheek. I was too freaked to open my eyes.

Hey baby, Jen whispered. That was incredible. You're really good.

I smiled, still with my eyes shut.

That's a first for me, I said as I opened my eyes to find Jen's lovely face only inches from mine and felt her tits mashed against my ribs and chest.

Jen laughed. Tell me it wasn't good, she said, smiling.

I guess it was, I answered. It was definitely interesting.

Jen drew her long dark thigh over mine, and I felt her knee gently pushing at my balls.

My turn, she said with a grin.

I settled back as she began to rub her thigh against mine and run her hands over my chest and upper arms. I felt her lick, deliciously, down along my neck. Then, I felt her hand travel down across my belly and slide under my trunks. Soon, she was licking my nipples and stroking my dick in long slow gliding motions. Her hand felt marvelous and her tongue's work on my nipples was making me groan and squirm in pleasure. My cock started getting rock hard. Jen mumbled something and I opened my eyes to see her crawling down to my crotch. She pulled my trunks off and as I felt the warm sea breeze blow over my cock, she kneeled between my legs.

I watched her sexy black body nestled between my legs while Jen started licking my cock like it was a popsicle. Occasionally she'd look up at me, grinning. I was grinning too. I took her hair in my hands and spread it over my belly. Jen sucked on the tip of my dick until my hips began jerking in pleasure. Then, with a little moan, she inhaled my dick all the way into her mouth and started sucking. It was incredible. I'd never felt something so good. Her mouth worked its way down to the base of my cock, while she played with my balls. I started pumping my hips upward rhythmically, and Jen began riding my dick, grasping its base in one hand and sliding her mouth up and down it.

I felt my balls starting to boil and I grabbed her head in my hands, helping to push her mouth down on my upstrokes. Jen started frantically moaning and gobbling my cock, using her whole head to fuck my dick into her mouth. I could feel my load starting and I pumped my hips furiously into her mouth. She was gagging and moaning at the same time as I slammed my arms down on the sand and let loose a huge orgasm, blasting her hot mouth with gallon after gallon of cum. She fastened her mouth onto my dick as I came, locking her lips to my crotch like some kind of machine. We thrashed together wildly as I came, finally grabbing her head in my hands and groaning while I emptied into her mouth.

Drained, I slumped back in the sand. Jen released my cock from her mouth and slowly lapped up the cum that had spilled across my hips. Her hand still held my now shrinking dick.

Jesus, I groaned, you really know how to give head.

I stretched my body from head to toe and Jen let go of my cock to slide her body up over on top of mine. Resting her elbows in the sand on either side of my chest, she nestled her head under my chin and practically purred. I wrapped my arms around her smooth dark black back and lighly massaged her shoulders.

I like to keep my man happy, Jen whispered into my chest as we snuggled together.

I smiled and, wrapped together on the warm beach, we drifted off into a dreamy half-slumber. I awoke to the sound of gulls in the surf beyond us. I loved the feeling of her body on mine. I could feel her cock nestled next to mine, both limp and relaxed and tangled together in our wet pubic hairs.

Hey Jen, I whispered. I'm thirsty, let me go get something for us to drink. I heard her sigh sleepily and she rolled off of me onto her side. I sat up, leaned down to give her full, luscious lips a kiss and stood. Looking down, all I saw was a gorgeous black woman curled up on the beach blanket, her thong still covering her ass and her legs curled up to hide her eqiupment. She looked up with a smile.

Hurry back, Jen said.

I ran naked to my beach house, darted into the kitchen and grabbed a pitcher of iced tea and two glasses. When I got back outside, I saw Jen sitting up, her bare breasts jutting proudly into the air and a towel curled around her hips. I sat down next her and poured some iced tea.

Let's toast, I said.

Sure, she grinned, baring her pure white teeth. To what?

To firsts, I said. And to seconds.

We laughed and gulped our tea. I put mine down and told her I'd never been with a guy before. Jen smiled wanly and looked down. I apologized and told her I'd never been with a girl like her before. She brightened.

As I poured another iced tea, I asked her how she came to be so sexy. Slowly, with lots of pauses at first, Jen told her story. She'd grown up somewhere in the middle of a big family. Her father had been a minister; her mother a schoolteacher. She'd known, she told me as I settled into the beach blanket, from the time she was a little boy that she wanted to be a woman. When she was a teenager, she started wearing her sisters' panties. Then, when no one was home, she'd started wearing her older sisters' dresses, and skirts. Her mother suspected something was wrong with her son.

Then, one day, when Jen was 18 and had just started college, her father called her down to the family room. He swore that he wouldn't have a homosexual in his family. Jen began crying. This infuriated her father who, in a flash, grabbed her by the front of her shirt. The shirt ripped, revealing the black satin bra she'd stolen from her sister and worn every day for a week. Enraged, her father slapped her, then began to kick her. Jen's mother grabbed the minister, and Jen crawled into a corner. Jen was ordered to leave the house immediately. Luckily, Jen's older sister was more loving and open-minded. Jen moved in with her.

Jen said she'd never been with a man the whole time she was experimenting with women's clothes. When she moved in with her sister, she began a total transformation - - dressing all the time, wearing make-up, wigs, growing her nails, and trying to perfect her voice, her walk, and her gestures. She dropped out of college and never finished the fashion design program she'd started. Instead, she got a job as a receptionist with a downtown law firm. They all thought she was female.

No matter how much she scrimped, however, Jen couldn't save up enough money to start hormone therapy. Then she met a high-powered County judge, a 65 year-old guy with a trophy wife and an eye for young beauty. He took her out, wined and dined her. When she revealed her secret, he seemed even more enchanted. He set her up in her own apartment and paid for hormone treatments and some major plastic surgery. At first, all he asked in return was to take Jen shopping for clothes, watch her dress, and take her out to dinner as his date. Eventually, the more feminine she became, the more interested he became in watching her fuck someone. Soon, she and the judge were picking up young yuppies at trendy bars, taking them home, and setting up wild voyeur parties.

Jen grew tired of this scene after a while. The judge didn't. Just when she was ready to make a break, the old man died of a heart attack in the arms of his wife. He left Jen a tidy bequest in his will, and she was free. She continued working at the law firm but discontinued the judge's kinky games. After 4 or 5 months of searching for true love, she got depressed. It was hard enough for a young black woman to find the right kind of guy, even harder for a girl like her. Her friends convinced her to vacation in Antigua. And, Jen said with a giggle, on the plane down she'd sworn to herself that she'd have a wild, Caribbean fling to forget about Chicago and her woes.

Finishing her story, Jen gulped down the last of her iced tea and turned to me.

Well, she said, that's the whole sad tale. Whaddya think?

I laughed. It's pretty sad, I answered. But you're on vacation. You left all that shit behind with the snow and the wind and the traffic jams. Just like I did when I left the Bronx. Come on, I said as I stood up and offered her my hand, it's getting hot out here. Let's head inside.

earlbrowder
earlbrowder
1,127 Followers
12