Jamaica Surprise free porn video

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Work takes me to the Caribbean occasionally and one time I had a small team with me in Jamaica implementing a new computer system. There were four guys and Sally - blonde; mid-thirties, always showing her ample cleavage, full luscious lips and blue eyes. I’d often fantasised about her whilst stroking my cock in my lonely bed. There was one other girl, Sherry (real name Sherezada) who was of Indo-South American extraction; younger than Sally – perhaps late 20s, with a gorgeous nubile, small-breasted figure, olive skin and jet black shoulder-length hair - another object of my dreams.

The nature of the job meant that we were working staggered shifts. One particular mealtime there was just Sally and me. We talked a lot - avoiding work topics as much as possible. She started telling me about her complicated love life; about how she had an ex-fuck-buddy she was keeping at arms length in the UK and another local guy in Jamaica who told her he’d split with his girlfriend but Sally had found out otherwise. So she’d dumped the ‘two-timing little shit’. There was even a third on-off relationship with a neighbour back home, but that was ‘off’ at the moment. It sounded like she was a slut but I knew she wasn’t. She was just a friendly, loving woman

As we finished our meal she said how much she enjoyed talking with me and valued my advice and consolation. I told her she was almost like a daughter to me – in fact I was old enough to be her father. I also told her that if I were 20 years younger and not happily married I’d join her throng of admirers as she was a very attractive and sexy woman. Age had nothing to do with it, she said, and that it was looks, intelligence and personality and that I had plenty of all three. She leant forward to kiss me but I pulled back.

“Please let me kiss you,” she whispered.

“Not here – it’s too public - I’m married – You know my wife - People might see.”

“Just a kiss – that’s all – nothing more. Just a kiss to thank you for comforting me,” she said.

I took her hand and we left the restaurant and walked to the lift (elevator).

When it arrived, we were joined by another couple but they got out at the next floor. The doors closed and Sally pulled me to her and kissed me with her lovely full lips until the lift stopped at our floor. We got out, said our "good nights" and "thank yous" and went our separate ways. I turned to watch her hips swaying provocatively down the corridor and started to think of what-might-have-been.

Back at my room, I’d barely opened my door when my phone rang

“I need your help with something urgently. I’m in room 435.” It was Sally and she sounded as if she had a problem.

I dashed out and almost ran to her room. Sally opened the door wearing a long baggy T-shirt and told me to come in quickly.

I walked in past her. “What’s the problem?” and as I turned round she was pulling her T-shirt off over her head to reveal her magnificent tits and erect nipples. She had on only a small white thong and my eyes saw a little damp patch at the front. I’d only dreamed of her like this and now my dreams had come true.

“You’re the problem, John,“ she said as she stepped forward, wrapped her arms around me and kissed me – pushing her tongue into my mouth and pressing her naked body against my fully-clothed one. My hands glided over her beautiful curves as she pushed us both backwards onto the bed.

Lying down, I lost all sense of resistance. I stroked her body all over, squeezed her breasts and moved my face down to take her nipples in my mouth. I pulled off her thong and touched down her slit to find the nub of her clit, rubbed it gently and worked a finger into her juices. After a couple of minutes, she pushed me away and began pulling at my shirt and undressing me frantically. When she got to my cock it sprang out of my shorts. She took it in both hands and then put me into her mouth. I almost came at the first suck and the second suck but with the third suck she held the base of my erection tighter. I think she knew how close I was to cumming. Her free hand feathered up to the tip and down again.

“Listen,” I said. “We have to stop. We can’t go any further. We can’t fuck if that’s what you were thinking. I don’t have any condoms. I’m sorry to spoil the moment but this is all very quick and unexpected.”

“It’s OK. I’m on the pill.”

“That’s not the point. The point is that you’ve just told me about three boyfriends with whom you’ve had recent sex. I’m sure you’re OK, if you know what I mean, but I can’t risk going home to Jenny with any infection no matter how small.”

“They all wore condoms, but I know what you mean. For all I know you might have something. Joke! (She laughed). So let’s just have sex the Bill Clinton way.”Again she kissed me and went back to stroking my cock as I rubbed my fingers along her wet slit. Thank goodness I’d not killed the passion or the moment.

I knelt up next to her and with one hand massaged her tits and nipples as I two-finger-fucked her to orgasm with the other. All the time she was tossing my cock and, when she came, I came and shot white strings of cum all over her tummy and tits.

“Get some condoms tomorrow and we’ll do it properly,” she whispered as she came back down to earth.

After a while, I went back to my room and stroked my memories smelling the aroma of her cunt on my fingers as I drifted off to sleep – a very happy man.

~~~~~~~~~~~~~~~

I couldn’t concentrate on work the next day. Although I saw Sally a couple of times and exchanged glances and smiles, we didn’t get a chance to say anything alone. I had a text message “C U @ 8”.

“Try 2 stp me,” I replied

Back at the hotel, I bought a 3-pack of the extra, extra sensitive kind and went back to my room via the bar to calm my nerves. Some of the others were there and half-heartedly tried to persuade me to go clubbing with them but I said I’d got other plans. Little did they know what. In my room, I took a long shower and waited until the appointed hour.

8 o’clock came and I knocked on her door. She opened it but only poked her head around as she let me in. No wonder – she was naked.

We kissed as I felt her all over – where my dreams had woken me this morning. My hands moved down her back to the cleft of her bum and to her soft round cheeks and back up again.

“Did you get them?”

I reached into my pocket and showed her the goodies.

“Let’s get you undressed and hard again.”

“I’m already hard. I was hard all night and I’ve been hard all day. I’m priapic.” I said as she knelt down to undo my belt and zip. My cock flipped out and almost hit her in the face. Her tongue licked on my shaft and down to my balls and back up again. What started off as a hard cock was soon straining very, very hard. This blowjob was even better than yesterday. I had to stop her otherwise I’d blow my load in her mouth instead of her much-longed-for cunt.

“Let’s get on the bed and see how wet you are,” I said.

She got up off her knees and moved to sit on the edge of the bed and lay back with her legs open and knees bent. She looked amazing - just the bedside light to cast shadows on her beautiful body.

I leaned down to stroke her breasts and pinch her nipples and then strayed downwards. Her clit was larger than last night and she was already very wet.

“Have you been playing with yourself?” I asked.

“Certainly not,” she said. “My fingers haven’t been anywhere near my pussy tonight,” she said, but I couldn’t understand why she emphasized the word ‘my’.

She sat up and said, “let’s put that thing on you” and tore open the packet. She put the condom into her mouth and then rolled it over me with her lips. She was so good.

She lay down and raised her knees up and open, exposing her glorious shaved self to me. I was standing up and slowly pushed forward to feel the warmth of her cunt wrapping itself round me. I couldn’t feel her juices but I didn’t care. I was inside Sally’s beautiful cunt – slowly fucking her, moving in and out and listening to her sighs of pleasure. She lay there moving her hips forward to my pushing. I tweaked her juicy clit between my fingers and she moaned out loud. This was Heaven.

But then the bathroom door opened and I froze. “What the f…?”

Sherry stood silhouetted in the doorway – she was completely naked also. “That looks like fun.”

Sally laughed and told her that she either had to stand and watch or join in like we agreed because she wasn’t going to stop in the middle of a lovely fucking. I was speechless – rock hard still but unable to say anything. Going through my mind was the sight of Sherry’s beauty and the swaying movement around my cock down below. I thought about what Sally had said about “My fingers haven’t been anywhere near my pussy tonight.” It now struck me as to whose fingers had been on her pussy. Sherry’s, of course! This was getting better by the minute. I began to fuck Sally again but faster.

Sherry came and climbed onto the bed, facing me and placed her legs either side of Sally’s head. She lowered herself onto Sally’s face and a tongue that was pointing upwards in anticipation. I’d seen porno movies and a couple of live sex shows. I’d even had a threesome with my wife and another man but this was five million degrees separated from all of that. Here I was fucking a gorgeous blonde whilst she was licking the cunt of an Amazonian beauty.

They’d obviously done this before. Sherry was telling Sally how good it was and where to lick.

“Suck my cunt sweetheart and put you finger in my ass. That’s it – deeper, deeper!”.

Sherry pulled my hands up to feel her tits and leaned towards me to kiss me. Our triangle rocked together like this for what seemed ages but was probably only a couple of minutes. I moved one hand off Sherry’s tits down to find where the noise of Sally’s licking was coming from. I touched her hard clit and pushed lower to her hole. Sally sucked on my fingers and then I pushed two inside whilst Sally tongue-fucked her.

“Oh My God! Oh Fuck, Yes! Don’t stop!” screamed Sherry. “Don’t stop!”

Sally muttered through Sherry’s wet cunt for me to fuck her harder as she was cumming; Sherry grunted out loud and closed her eyes to concentrate on her own orgasm as I just went over the top and thrust umpteen spasms of cum into Sally. My balls drained every drop into her.

We all collapsed onto the bed. My condom was full to over-flowing when I took it off, but I remembered that I still had two more to use. As we fell asleep, with me in the middle, my erection in their hands and their thighs intertwined over mine, I vowed never to forget what had happened and to write it all down one day to share with others.

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Introduction:A Jamaican dance party turns into something moreJamaican Dance PartyThis is a true story about a Jamaican family and the parties they used to have every weekend. During the day there would be cooking and barbecue for all who came, mostly family but a few friends were allowed, like myself. I was friends with the eldest daughter, there was a younger daughter, and their parents. Cousins, aunts, uncles, etc. all came for the food, the drinks and the music. Once the sun went down it was...

1 year ago
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Jamaican Holiday Ch 14

Aftermath This brings us up to Dec 2010 and our most significant event - and introduces Robert, our Bull and future Master Dec 2010 -- It's been 6 years since that vacation to Jamaica. When we got back we intended to return to our normal Vanilla existence. But we couldn't -- too much had happened. As Jaye put it, the door had been opened to something deep inside both of us and it couldn't be shut. The first few weeks were exciting, as memories of Jamaica filled our heads and fueled our bedroom...

3 years ago
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JAMAICAN BARTENDER at a couples resort

Being a bartender in jamaica you will meet a lot of people from all around the world, I have been doing this for six years now. I am six feet one inches athletic build I workout at the gym as often as I can. The hotel that I tend bar has a lot of return visitors, so working there for so long I get to know a lot of them. On this trip the scott's is a couple that come every year Kim and Tom were very friendly, we chat and got...

2 years ago
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What a surprise2

She lifted herself up so he can slide under her pussy and started to feel for his cock to put in her mouth. Although she was still sleepy his cock tasted so good, she woke up sooner than what she expected. Steve just couldn't stop thrusting his tongue in and out of her juicy pussy. OOOOOOOOOOOOOOOOOHHHHHHHH Steve don't stop!!!. He covered her pussy with his mouth to suck more juice. Angie had his cock in her throat and tasted the pre-cum as he was ready to come. Cum in my mouth Angie...

2 years ago
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  • 17
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Stepdaughter Surprise2

After that awesome night with Nat and Molly things changed very little, at first. My 17 year old stepdaughter did not discuss it, and I was not going to push my luck. However, Nat did begin to be more of a tease around the house. In a subtle fashion, she would give me little smirks, rub against me in passing, and displayed more laxity in what she wore. She often would wear a tee shirt with no bra that had her tiny tittie’s nipples poking out. Under her tee shirt, she now wore only panties and...

4 years ago
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UnderwearSurprise

We recently visited my sister-in-law and spent 2 weeks there at her place in Tampa, Fla. They have pretty big home and have a woman come in everyday to tidy up the place. She actually prepared our rooms for us. She was about 45ish and in pretty decent shape. We had been there for the first week and i noticed the cleaning lady's schedule was pretty routine. Right down to catching her sniffing my underwear. She didn't think i saw her, but she would go in to get the dirty laundry and when she saw...

1 year ago
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Stepdaughter Surprise2

After that awesome night with Nat and Molly things changed very little, at first. My 17 year old stepdaughter did not discuss it, and I was not going to push my luck. However, Nat did begin to be more of a tease around the house. In a subtle fashion, she would give me little smirks, rub against me in passing, and displayed more laxity in what she wore. She often would wear a tee shirt with no bra that had her tiny tittie’s nipples poking out. Under her tee shirt, she now wore only panties and...

Taboo
2 years ago
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A pregnancysurprise

“I can’t imagine carrying a human inside me, your body is amazing” Tiffany said. “Yeah the gift of life is beautiful but everything aches” Kelly replied. “Thank you for doing this for me. What Kelly didn’t know was Tiffany was massaging her for her own pleasures. She’d had a crush on Kelly since she first saw her. Being that she was bi-sexual she found Kelly’s presence intoxicating. She wanted nothing more than to have her lips around her nipples. They made small talk while Tiffany...

3 years ago
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  • 14
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Jamaican Beauties Jaunt Ch 02

Chapter 2 — Challenges: He challenges her to prove she can be uninhibited. Notice: The author listed Jamaican Beauties Jaunt under Literotica’s umbrella category Novels and Novellas: Erotic fiction with a broader scope. However, the events in this chapter cover a variety of Literotica categories including: Exhibitionist & Voyeur: this chapter begins the story of a young Jamaican woman’s acceptance of the Seven Progressive Challenges and her accomplishment of the first two challenges: 1)...

2 years ago
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Jamaican Dick for Chub Bottom

Renald Gold drove his s****r’s blue 2012 Toyota Rav4 down the highway. The five-foot-nine, one-hundred-eighty-pound Jamaican had arrived in the U.S. only days before. He thought Texas was pretty cool for the most part. He was especially happy that a pretty young sissy had hit him up on Tagged. They conversed back and forth for the better part of the day. Prentiss Lewis was at home in the bathroom getting ready. His parents both worked the overnight shift at their respective jobs. He was an...

3 years ago
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Jamaican Night

I read on the internet that this weekend was the ‘freezy’ festival in my town, three nights of free live music, street food and DJs. I decided to go on that same Friday night to enjoy the atmosphere and the crowd even though I didn’t know any of the artists playing. My flat-mate Marcus decided to tag along. He checked with me whether his converse or shoes complemented his casual shorts and marcel outfit and we went for the classier shoes to give him a more mature look. Between me in my...

Quickie Sex
2 years ago
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Jamaican Dick for Chub Bottom

Renald Gold drove his sister’s blue 2012 Toyota Rav4 down the highway. The five-foot-nine, one-hundred-eighty-pound Jamaican had arrived in the U.S. only days before. He thought Texas was pretty cool for the most part. He was especially happy that a pretty young sissy had hit him up on Tagged. They conversed back and forth for the better part of the day.Prentiss Lewis was at home in the bathroom getting ready. His parents both worked the overnight shift at their respective jobs. He was an only...

3 years ago
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JAMAICAN VACATION PT 1 I DISCOVER BBC

Unfortunately, as soon as we arrived, Jeremy became engrossed in work issues, and had his face stuck in his laptop while our Jamaican vacation swirled around us. I was frustrated, but equally determined to enjoy my time in Jamaica, so I grudgingly left him in the room at our resort and took a towel (no bathing suit), and a book, down to the hotel pool for some sun. When I got to the pool, I picked a chaise lounge for sunning myself, and furtively glanced around to see who else was there. I...

3 years ago
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Jamaican Resort Day 1

Introduction: We Take a Wild Vacation This a 90% true story We were young, horny and in so much in love. We booked a vacation at a Jamaican resort. It was our honeymoon makeup. You were the hottest looking and smartest woman I had ever met. You dressed for the trip in a tight white T shirt and I could see your braless nipples pushing out. Your skirt was a very short white cotton. When you moved I could see your underwear. You dressed to accentuate your sexiness and you loved to flaunt your...

3 years ago
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Jamaican Vacation

Introduction: What happens in Jamaica stays in Jamaica The trip was booked for March into an all-inclusive resort that catered to couples and boldly advertised a clothing-optional beach. My wife almost immediately went on a diet to lose a few pounds. I didnt think she really needed to, but she wouldnt be deterred. Picture this, shes 52 weighing 125lbs, firm B cups with dark hard nipples, flat tummy and a bald little pussy. Why would she need to lose anything, but her mind was made up. The two...

1 year ago
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Jamaican Vacation turned Gay

The only silver lining of my fiancé calling off our wedding was that I still had a non-refundable trip to Jamaica already booked. The trip gave me something to look forward to after this nightmare of a month.So a few days after my original wedding date, I hopped on a plane and went on my planned honeymoon by myself.The resort was beautiful, and coming from New York in the winter, the weather was a welcome reprieve. The only bummer was they lost my checked bag, but I still had a few things in my...

1 year ago
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Jamaican men around me again

Jamaican men around me againThe flight to Jamaica had been extremely pleasant. As we disembarked, my loving Victor took my hand and held it for a momentThe contact with his soft skin made me warm, wet and my nipples got hard.The weather was sunny, with just a few small clouds set against a deep blue sky. The mild breeze made my summer dress billow and the humidity made the halter cling to my breasts. I was happy, here I was walking with my hubby as other men were looking at me with lust desire;...

1 year ago
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Jamaican Holiday Ch 07

Sunday – Ist Day as BBC slut wife We managed to get up and shower for a late breakfast, and my wife surprised me by not wearing her ever-present bra and panties to the dining room - only a T-shirt and shorts. The waiter, Andre, did his usual flirting, "Missy, ja look especially good this mahning! (his eyes on her chest) Didja have a fine night?" She blushed, and I thought her nipples pushed harder against their slight covering. "Yeah, I did!" she answered. "A fine Jamaican night, Missy?" he...

2 years ago
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Sex Night ndash Unexpected Surprises

My wife and I got married when we were both teenagers and have been married for over 20 years now. As you can imagine our Sex life was pretty crazy when we first married. Not only were we newlyweds but we were also full of teenaged hormones and inhibitions. It seemed like all we did was have Sex. Hot wild sex. 7 days a week most of the time several times a day.Now let’s fast forward about 22 years. We are still happily married and the proud parents of 4 c***dren. We’re both gainfully employed...

2 years ago
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Surprises

“I definitely have a different opinion of you now.” Jin’s words made me smile. It was something she had a talent for doing. Making me smile. She did that in our first messages on the dating app, and now that we had moved into the world of text messages, it was no different. “How so?” I asked. “That was not what I expected you to say,” she answered. “What?” I asked. “What did I say?” “You know,” she replied. “Oh…that last exchange? Let’s see…what did we say…?” I scrolled up in my messages on our...

First Time
1 year ago
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Jamaican Valentine

Tim had driven down so that we could fly out together. Sitting on the plane, I thought about how I had come to be here. After those great days in Chicago, he had begun calling me, and we had become close. I found him as gentle and considerate about most things as he was in bed. What was more, with a few carefully chosen images, he could light me up over the phone as easily as he did in person. Of course, I was at that point where his voice was enough to make me lubricate and begin to go there....

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