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Jamaica Surprise

"A brief cheating relationship with two work colleagues"

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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.

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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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Written by Mister_E
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