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Rachel's Trip To Jamaica

"A religious, conservative young woman has her mind - and everything else - expanded in Jamaica."

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This is a true story.  My second wife and I got married in 1988, and we had not been married long when a girlfriend from her netball days turned up on our doorstep.  Her name was Rachel, and she had just returned from her big OE in London.  Having nowhere to stay, we put her up for a couple of weeks while she searched for a flat.

Rachel was just your average-looking girl next door type, but she wasn’t plain; her standout feature was her tits. They were large and firm.  At twenty-one, she was a year younger than my wife.  She had blond hair with olive skin and was about 5’4” tall.  She had a nice figure with ample curves - I had trouble trying not to stare at her tits every time I was in the room with her, which my wife noticed and gave me shit about.

Rachel came across as a very conservative, good catholic girl.  But I sensed an underlying conflict in her, and several times, I was certain she was coming on to me.  And I certainly felt a sense of her being available if I wanted.  I might add I did not, as being so newly married, I was several years away from even thinking about playing around.

She had passed through Jamaica on her way home and spent a week there at some beachside resort.  She couldn’t stop talking about the place.  One night my wife mentioned to me that Rachel had told her about a pretty raunchy sex experience while in Jamaica.  But she said Rachel would not elaborate much about it to her.

I was not surprised she would not open up to my wife fully; they both came across as pretty conservative.  However, I felt she may open up to me, and I was dying to get the details.  So a couple of days later, when my wife was not around, I brought up what my wife had revealed and pushed her to give me some details.  She opened up and, surprisingly, was very explicit in her descriptions of what had gone down, saying that she had been dying to tell someone about it.

Her story really surprised me, as she didn’t come across as a person that would have done any of the things she described.  She told me she had arrived in Kingston on a Friday and was due to fly out for NZ the following Saturday.  I’ll tell the story in the first person, just as she told it to me.

***

On landing in Kingston and walking across to the terminal, I was awakened to a host of unfamiliar sensations as I took in the Jamaican men on the tarmac.  And once through customs, the guy that carried my bag out to the resort’s van had my knees feeling a bit wobbly.  He was wearing shorts and a T-shirt that was torn in many places, exposing his dark, muscular frame.

I went to bed that night and masturbated myself to sleep, something I seldom did, as it had been hammered into me that self-gratification was a very bad thing.  The next day when I arose, my mind was pondering what I would do if a Jamaican guy were to chat me up.  I figured that as you only live once, I might never get back to Jamaica again.  So I spent the day looking around the shops and checking out every guy that came within fifty feet of me.  But I had little luck in getting the attention of anyone.

That night, I asked one of the male resort staff where all the action was.  He gave me directions to a nightclub a short taxi ride away and told me it would be humming as it was Saturday night.  I only had casual clothes with me. Still, I picked the sexiest attire I had and spent some time on my makeup before going out front and catching a taxi.

The night was a disaster; mostly American tourists and most of the women were prettier than me.  I only got asked up for a couple of dances, and that was by older boring American guys.

The next day, I decided to spend the day on the beach and work on my tan.  There were a few Jamaican guys around, but I soon found they were all staff.  Sometime in the afternoon, a handsome waiter approached and asked if I wanted a drink.  I tried flirting with him but was not getting a very strong response, and so I ordered a rum cocktail.  When he returned, I tried to get him to stay and talk for a bit, as the beach was not that busy.  But in a roundabout way, he explained that staff was forbidden to mingle with the guests, and he wandered off.

Later in the afternoon, he came back and asked if I wanted another drink, as he had seen that I had finished.  I told him, “Why not,” and when he returned with it, I asked him, point blank, how did one get to meet the locals.  I was fucking horny, and that fact overrode my normal reserved nature.

He glanced around, then quietly told me that I should walk over to the next bay, as that was a public beach and many local guys hung out there.  I was embarrassed as he winked at me and pointed to his left, showing the road that curved around the point.  I realised I must have seemed like a desperate woman of low virtue to him.

Anyway, the next day saw me walking out of the resort, beach bag over my shoulder, in the direction the guy had pointed.  It took a good half hour, and I was pretty hot when I got there.  I laid out my towel, down the far end of the beach, well past the majority of the beachgoers.   Dropping my sundress and bag on my towel, I headed straight into the sea.  I had purchased a sexy red bikini at the resort shop the night before.  It proved to be a poor choice as my boobs were almost bouncing out of the cups as I jogged down to the water.

Back on my towel, I spread myself out to catch the sun and, looking over my sunglasses, checked to see if there were any eligible guys around.  Disappointingly it was mostly local couples and families near me.  And the couple of men that did look to be single weren’t paying any attention to me.

Around midday, I wandered up to a beachside bar/cafe and bought some food and a drink.  Some guys were hanging around, and I picked out the best-looking of them and gave him a sexy smile.  He came over and offered to carry my food back to my towel, which I happily accepted.

But after some idle chatter, he moved back to the bar.  I was starting to feel deflated about my prospects.  However, sometime later, another of the other guys from the bar came down and sat beside me.

He introduced himself as Arley, and as he chatted away, I ran my eyes over his body, trying not to be too obvious.  He was probably a little over six feet, muscular and had a nice smile.  Obviously, he worked out, although I had to admit that all the guys here looked like they worked out.  He was quite presentable but tough looking, not the sort of guy I would take home to meet my mother or meet in a dark ally.

Still, I found myself quite attracted to him and felt myself getting a bit squishy between my legs.  Our conversation slowly became more interesting, with Arley dropping some not-to-subtle sexual innuendos on me.  Then out of the blue, he asked what I wanted, and while I was thinking how I could possibly indicate I wanted some sexual attention, he rattled off, “Marijuana, Coke, cheap local brewed rum, anything you want, I can get.”

I stuttered out that didn’t want any of those.  And he immediately asked if I smoked pot.  I replied that I had tried it a couple of times in London but that it had not done much for me.

“Ah! You need to try our weed, it is much better than anything you will get over there.” Replied Arley.

And he opened his bum bag and pulled out a joint.  I looked around, expecting to see the police rushing down the beach.  But the nearest people to us were a good twenty metres away and not showing the slightest interest in us.

Arley cocked his head at me, “Are you on? You really should give some Jamaican ganja a try.  Have a couple of tokes?”

My more conservative self was screaming, No!  But I found myself nodding okay to him.  And he lit it up, took a deep suck, and then handed it to me.  The first inhale made me cough, I did not smoke, so it was not a comfortable feeling.  But when I went to hand it back, he told me to take my time and have a couple more tokes.  The second time it was a little better, but I could not feel anything amazing happening, and so the third time, I took a much longer drag on it.

Just as I was about to hand the joint back to him and say that the stuff did not work on me, I felt a warm euphoria envelope my body.

Arley smiled at me, “Better than you have had before, eh!  Jamaica has the best Jolly Green in the world.  Have another drag I have plenty more here?”

I had sat up to try my first inhales but now wanted to lie back and relax.  So I lowered myself onto my side facing him and took another toke.

Arley leaned over and placed his hand behind my neck; he kneaded my neck muscles and told me to relax and enjoy it.  I think I drifted away for a bit, as when I came to my senses again, Arley was caressing my breasts.  When he saw I was aware of what he was doing and not freaking out, he flipped my bikini top up and let both my breasts swing free.

I just lay back and enjoyed his kneading of my nipples.  He then leaned in and took a nipple in his mouth.  I desperately looked around to see if people were watching but again found no one taking any notice of us, and I gave up all control.  I was extremely aroused, my body trembling with desire.

I jerked awake again, though, as I felt his fingers forcing their way down the front of my bikini bottoms and slipping in between my wet, already-swollen sex lips.  But I did not attempt to stop him, it felt too good.

He pushed me over onto my back and draped my sun frock over my thighs to cover his hand.  My breasts sat up proudly, firm yet soft.  I had seen some women topless when I arrived at the beach and figured I would not cause too much of a stir.  Still, I was incredibly self-conscious and way outside my comfort zone, and I lifted my hands to cover my breasts.

Arley pulled my hands away and pushed them down to my side, “I want to look at them as I make you cum,” he said, shifting his hand back under my sun-frock.

I felt him working my bikini bottoms off and lifting my head, watched him work them down my legs.  He sat up and looked around, then slipped them from my ankles and into his shorts pocket.  He arranged the material of my dress on my right hip so as to hide what he was up to and inserted two fingers deep inside me.  After a few good hard strokes, he held the dress up to let me watch him work.  I saw that the inside of my thighs were literally covered in a murky creamy juice.  Every time he pulled his fingers out, It hung in silvery strings from my pubic hair and swollen inner lips.

In no time, I felt my orgasm approaching.  Noticing this, he withdrew his fingers and started massaging my breasts.  I rolled towards him slightly, attempting to hide them from anyone near.  But he pushed me back and worked on my rock-hard nipples.

If he meant to delay my climax by leaving my fanny alone, it was not working.  The eroticism of being totally naked and exposed to other people, not a stone's throw away, was bringing me off.

“Need to cum,” I pleaded with him. “Please play with me again.” And I tried to push one of his hands down to my thighs.

“You want my fingers, then you put them in.” He said, pulling away from my hand and placing his hand on my lower stomach.

I reached down with both my hands, one taking hold of the dress and holding it steady to hide what he was doing to me, and with the other, I took his hand and directed his fingers into my very excited, eager cunt.

I spread my legs, moving my hips in time with his thrusts, trying to get his fingers even deeper.  Then moving my hand on his to let him know I wanted him to use three fingers.  I dropped my head back on the towel and tried to relax as he forced three fingers inside my throbbing cunt.  My orgasm struck suddenly; the flood of emotion had me arching my back in ecstasy.

The feeling of loss as he withdrew his fingers had me groping around between my legs, searching to hold his hand back.  And I was struck by a stronger wave of disappointment as he pushed me away and rolled me on my side, facing the people nearest to us.  But my disappointment was quickly replaced with elation as he cuddled in close behind me and ground his hips against my but.  I could feel his hardness as he reached over with a free hand and held my hands, as I had been attempting to pull my top down.

Then both of his hands were working around on my arse, and I felt him release his hard cock from his shorts.  I was still thrumming and sensitive from my climax but felt a searing need to be taken.  One of his hands was directing himself between my legs; the other reached over me again and worked on one of my incredibly hard, sensitive nipples.  I felt like they were going to burst. They were so swollen and erect.

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he rubbed his shaft over my wet, longing slit, and I lifted my left leg and arched my bum back against him.  He seemed to be having trouble penetrating my opening, so  I shifted into a position I thought would be more advantageous for him.  But he still seemed to be having some difficulty.

He whispered in my ear, “Shit, you’re tight; you're not a virgin, are you?”

And then, a painful spasm shook me as I felt him tear past my resisting labia.  Thankfully, when he heard my yelp of pain and saw me stiffen and jerk away, he held still to let me get used to it.    

He urged me to relax, and as I did so, he pushed into me again, stretching my cunt more than I thought was possible.

I had never felt anything like it before.  I had only had two men before, one when I lost my virginity the night before I left New Zealand for England.  The other, my boyfriend of the last year and a half, neither of them had felt anything like this.  I tried to look back and see if he was using a baseball bat on me.  But he pushed his head against my ear and again urged me to relax, “I’ll take it slowly. You will get used to it in a minute, and then I will make you think you are in heaven,”

For the next little while, I was fighting to remain silent and trying to hold still and not pull away from him.  He was patient, though and slowly worked more and more into my resisting sheath.  Slowly the pain eased and was replaced with a very needy arousal that had a multitude of salacious thoughts swamping my brain.

I had heard the snide remarks about black men's cocks being huge.  But in my mind, I pictured something a little larger than those I had already seen, and descriptions of foot-long monsters I just took to be exaggerated trollop.  But now I was having to re-evaluate my previous doubts, as this incredible cock he was now assaulting me with was provoking some filthy, carnal reactions in my body.

I don’t know if it was the marijuana, but my erogenous zones were overwhelmed with pleasure.  I couldn’t bear to have them touched, and yet I also wanted him to pinch and stroke me anywhere he chose.

I had forgotten all about anyone outside our small bubble of bliss.  People must have taken notice, as my body was jerking and twitching with his every thrust.  And as I felt Arley’s thrusting become more urgent.  I looked down between my legs and held my dress out from my body to see watch him thrusting into me.  The sight of his large black cock sliding in and out brought me to a climax.  A massive explosion of pleasure, and incredibly, seconds later, when I felt his intense release, a second surge of pleasure washed through my body.

I had never climaxed as hard and strong as that before.  I lay back on him, struggling to get more air in my lungs.  I was drenched with sweat, both his and my own.  When I could finally talk, I asked him for my bikini bottoms, as I needed to get into the sea.  He laughed and told me he would walk down with me, but I wasn’t getting my bottoms back. He helped me to my feet and, placing himself to my right and holding my towel, so I was somewhat obscured, he walked me down to the water.

I sat in the shallows, washing a bucket of cum from between my legs, then a little refreshed; he walked me back and shielded me as I pulled my sundress over my head.  I watched as he straightened himself and zipped up his fly.  His cock was at least two inches longer than my ex-boyfriend, but it was the girth that really made me gasp; it was thick, probably thicker than my wrist.

We sat and talked for a bit, then he organised himself and helped me to my feet.

“Come.  I’ll show you where I live, and we can have a refreshing drink at my place.” He said, walking me up towards the bar.

There were some expected ribald comments from the guys gathered there.  They had me blushing crimson as we stepped in past them.  Arley asked me to buy a couple of slices of their Lemon Meringue pie, as it was really good when you smoked.

Slipping the brown paper bag of pie into my beach bag, we were soon in amongst the rundown shacks leading away from the bay.  Five minutes or so later, he turned me towards a hut and opened the door for me to enter his one-room shack.  Two guys were sitting on the large single bed opposite the front door.  They were watching a show on the TV that sitting on a cabinet beside the door.

Arley introduced them as his brother, Tarone, and the second guy as their friend Bob.  And indicated that I should go sit with them on the bed while he made us a fruit drink.  I got the giggles, as his friend Bob had dreadlocks and was dressed so as to look like Bob Marley.  For some reason, this appeared funny to me, as he did not look very much like Bob Marley.  But I was to find that Bob actually sang in a band that played mostly Marley's music.

The guys offered me the joint they had just lit.  I took a couple of drags on it, feeling like a real pro now.  The bed was surprisingly clean; in fact, the room, in general, was cleaner and tidier than I would have expected from a bunch of guys.

The weed hit me hard, not sure if it was stronger than what I had had on the beach, but I was suddenly hungry and got up from the bed to retrieve the meringue pie.  This must have exposed my naked posterior to the guys, as they both made high squeaky sounds and then gave me some raunchy compliments.

Again the weed must have been very good, as I was way past feeling any embarrassment.  Arley handed me a plate for the pie and followed me to the bed with forks and our fruit drinks.  I wriggled back between Tarone and Bob, using the wall as a backrest; Arley sat next to Bob and rested back on the side wall.  In between toke's, we all consumed the Lemon Meringue pie.  It was delicious, the colours on the TV were extraordinary, and the music playing had me swaying my body to its beat.

I had obviously drifted away for a bit, caught up in all the heightened sensations and listening to the music.  But I slowly became aware, as if in a dream, that I had been lifted to my knees, and Arley was pulling my dress over my head.  Tarone unhooked my bikini top and threw it onto the floor, then pulled me back against him and began massaging my tits.  When Arley pulled my legs out, spread them wide and ducked his head between my thighs, I did put up some token resistance, knowing I should not be doing this with more than one man.  But then I gave in and just opened my legs wider as it felt so good.  I relaxed back into Tarone and closed my eyes, savouring these new, unaccustomed feelings.

Soon, when my hips were really grinding onto Arley’s face, Tarone slipped away from behind me, and I felt more than saw him getting undressed.  Then I felt the urge to see his body and snapped my mind back to reality.

He was younger than Arley, better looking and had a bigger build.  I lowered my eyes to check out his manhood and was not really surprised to see that he was very well endowed.

They manoeuvred me around to lie my head in Bob’s lap, and I knew Tarone was about to mount me from behind.  I objected and surprised myself by exclaiming, “No! I want to watch it entering me.”

Flicking me over onto my back, Tarone grabbed my legs and pulled my butt down to the edge of the bed, and Bob lifted my head and put a pillow under it.  Arley was standing there naked, taking pictures with a camera,  and as Tarone stepped between my legs, I got my first good look at both their erect cocks.  God, they were big; no wonder I had so much trouble accommodating Arley.

My body stiffened up as Tarone presented his big purple knob between my thighs.  Bob was now kneeling beside my head and telling me to relax.  He ran his fingers through my hair, trying to calm me.  “It will be okay,” he told me, “I’ve never seen a woman yet that couldn’t accommodate it, and you’ll be screaming for more once you get used to it.”

He was right, I knew, as the memory of Arley’s taking me not an hour ago still had my body itching for more.  And so I tried to relax and watched in awe as Tarone tried to feed his rod into my sore, battered cunt.

I lay back then, there were hands all over me, and they felt incredible.  Bob had released his cock from his shorts, and it was hard against the side of my face; his hands were busy kneading my tits and pinching on my nipples.  I was relieved to see that he was not much larger than my London boyfriend.  I had the urge to take him in my mouth but was distracted from that thought when Tarone growled that I was so tight he could not get anymore in.

Arley told him to wait, then returned with some oil, which he poured between my legs and over Tarone’s hands.  I dropped my hands down between my legs, and spreading them wide, I rubbed the oil between my engorged labia.  And then I gripped Tarone’s shaft and helped guide him into my eager cunt.

We worked together, my opening my legs wide and pushing back each time he thrust forward.  It was a little easier than it had been with Arley, but still, a slow process getting him fully embedded.  There was some pain, but it was bearable, as I knew now that it would disappear when my body got properly aroused.  The guys were all commenting about their luck in having a virgin, and I did not bother to correct them.  Their other comments about me being their dirty little virgin slut were actually turning me on.

Once Tarone got into his rhythm, I turned my head and took Bob’s beautiful black cock into my mouth.  I wonder what Arley was up to, and in my peripheral vision, saw that he was again taking pictures.  This should have caused me major concern, but it was only a fleeting thought as I occupied myself with the orgasm again, building to a crescendo.

They all fucked me at least twice, and I had several climaxes, the biggest one when Bob took me up the arse.  Something I had never experienced before.  Tarone tried to fuck me there also but gave up when he saw the pain he was inflicting.

As the light was starting to fade, Arley helped me back into my bikini top and dress but wasn’t going to give me back the bikini bottoms, saying he wanted them as a souvenir.  But I pleaded with him that I didn’t have the money to buy another bikini, and so he relented.  But he wouldn’t let me pull them on, and I had to promise to wear some sexy knickers the next day that he could keep.

He dropped me back to the resort on the back of his small beat-up motorbike.  I was glad it was fully dark when he dropped me off, as I must have looked like a bedraggled whore.  I certainly felt like one.  He told me he would pick me up midday tomorrow, and when he saw the hesitation on my face, he told me to be there or he would make a scene.

I showered and took in the state of my breasts, there was a hickey on the right one, and my nipples were almost sucked raw.  Once I had showered, I lay on my bed, wrapped only in a towel, running through my mind the events of the day.  Just thinking about the day quickly had me aroused.  I opened the towel and started playing with myself, massively turned on by the dull pain that I felt between my legs.

After bringing myself to a fast, satisfying orgasm, I dressed for dinner.  A couple joined me, introducing themselves as Stephanie and Marty.  They looked to be in their early forties, he seemed quite nice, but she was very stuck-up and posh.  They asked about my day, and I told them about my walk over to the next bay and sunbathing on the beach.

Steph gasped in mock horror, “Oh! Were you all right?  We were warned against going there, as it is plagued by local gigolos.”

My awkward reply, that I had seen none of that, did not sound very convincing, even to myself.  And I then proceeded to dig myself even deeper by adding an even more unconvincing explanation.  They both looked at me with disapproval written all over their faces.  This had me re-evaluating my meeting with Arley again, and as I walked back to my room, still blushing with embarrassment, I pondered how to get out of my planned liaison, on the morrow, without creating a scene.

But as I walked back to my room, pondering what I should do, I knew in my bones, I would be out front waiting for Arley to arrive the next day.

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Written by mingemuncher
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