Caribbean Awakening Pt. 01

Jessica was really looking forward to the next 5 days. Sun, Sea, Sand, Sex?

Paul and Jess had been married for 20 years. They were both in their early 40's and have a great life. They had two teenage daughters, Casey and Beth, who were both at University studying to be a lawyer and a doctor.

Paul was 6' 1 tall and medium build with dark but greying hair. Jess was 5' 7, mousey blonde hair and had an hour glass figure. Even after having two children she still thought she had the curves and sex appeal to make her smile when she looked in the mirror. She was amazed how her tits had managed to stay fairly firm and upright even after all these years.

Paul had met Jess at college and although both had dated a number of people before they got together, they were both fairly naïve in terms of sexuality when they met.

They got on really well and Paul proposed after 9 months and within 3 months they were married. Jess got pregnant fairly quickly after they got married and a year after Casey was born she was pregnant with Beth. She didn't work for the first 12 years of the kids being born and a lot of the time she had to cope on her own as Paul was away on business trips all over the world.

She got a job doing admin in a busy local sales office when the kids went to secondary school and it was during that time that she found that she had something that a lot of guys liked. She didn't take it seriously and there was a lot of banter between the sales guys and her and they used to comment on how good she looked and some joked about her being a MILF.

Paul was in sales and worked for a large American company so travelled and worked away a lot. He was often stressed, as his sales targets were large, but he was always in the top 2% of the company in achieving those targets.

This year was no exception and he had smashed his target and as a reward was invited to the Global sales club which was awarded to the top 10 sales people in the company who had the highest achievement that year. The trip this year was to the Caribbean Island of Tobago and the invite extended to wives & partners but no kids.

Paul had been invited along with another top salesman from the UK, Tony. He would be bringing his wife Lisa along as well. Jess new Lisa from the company social events that were held every year including Christmas parties. Lisa was in her 30's but had no children and she worked full time as a fitness consultant at a large gym.

Jess had decided that she was going to enjoy herself on this vacation, even if Paul had to attend some company events during the stay. She had gone shopping the previous weekend and bought some new outfits to wear during the day and evening and also invested in a couple of new Skimpy bikini's, which she didn't normally wear on the family summer holidays. She also went and had a full body hair wax so for the first time she had a hairless pussy.

This feeling was very strange as she had always had some trimmed hair down there but this time there was nothing and it made her incredibly horny. The thought of being touched down there without any hair being in place was very exciting.

Paul and Jess had met Tony and Lisa at the airport early Thursday morning and after a long flight and transfers arrived at the hotel in Tobago around 2 in the afternoon. Although the company had spared no expense and booked them business class, they still wanted to take a nap before meeting in the bar with the rest of the sales club winners for the reception in the evening.

The weather was a glorious 32 degrees and from the airport to the hotel Jess could see a number of the local guys following her and Lisa with their eyes when they were walking and she had a smile on her face and thought "maybe this is going to be a good break".

After an afternoon nap and a shower, they got changed ready for the cocktail reception to be held at the hotel with all the winners of the global sales club. Jess was wearing one of her new dresses she had bought the weekend before. A figure hugging red dress with very thin shoulders straps and cut just above the knee in length. As the dress was fitted she thought about going knickerless, but decided that she would wear a high cut thong instead. She didn't wear a bra as she would use the tightness of the fabric across her chest to keep her tits in place. She did wonder if she got a bit excited that her nipples would stick out but that made it all the more exciting.

They entered the reception area and already there were people buzzing around the bar making introductions and sampling the free champagne that was being offered. Jess saw Lisa with her husband Tony and they walked towards the couple. Lisa was wearing a black cocktail dress that showed off her very sexy figure.

"Oh my god Lisa, you look absolutely stunning in that dress." Jess said.

"Thanks Jess, you look fab as well".

Lisa leaned across and in a low voice into Jess's ear.

"Nice tits Jess, I see you decided to go braless".

Jess smiled and said "I nearly went knickerless with this dress, but decided too much too soon." They both giggled at that.

"What are you two talking about?" Paul said.

"Just talking girl talk dear." Jess said to Paul.

The two couples mingled in with the crowd and Paul introduced Jess to a number of his colleagues from around the world including his boss, Tyler who was a black 6' 6" monster of a man who clearly worked out and stayed in shape.

"Hello Jess, nice to finally meet you." said Tyler.

"Paul has talked a lot about you when we have been out on meetings and with customers around the world. His description doesn't do you justice and you look absolutely fabulous tonight". He continued.

He took her by the hand and pulled her toward him to kiss her left and right on each cheek. Jess could feel the heat coming off this man and is presence excited her. She could feel a tingling in her pussy that she had only got a long time ago when she first met Paul. She had stirrings like this from the attention the sales guys had shown here in her office, at work, but not at this level.

"Let me introduce you to my wife Saskia." Tyler said.

Tyler's wife appeared by his side. Mid 30's stunning in a low cut green dress that hung effortlessly of her flawless skin. She had pert tits and voluptuous arse. It had a split up the side to her waist and clearly wasn't wearing any knickers.

If Jess was into women, she would have dropped to her knees and worshipped here there and then.

"Hi Jess, it's great to meet you and I am sure we will get to know each other over the coming days as we do our thing whilst the men do their thing." Saskia said.

The two ladies chatted and Saskia said she had met Tyler whilst on holiday here in Tobago as he was born here but moved to the US when he got his first break in sales.

Saskia was from Brazil and she had the body, confidence and personality to match Tyler's presence and ego.

The rest of the evening was spent chatting and mixing with the rest of the couples before they retired to their hotel room for tomorrow's fun packed day of activities. Paul & Jess got to the room and Jess was feeling horny as she couldn't get out of her head the touch and presence of Tyler when they met in the bar.

Jess needed to release that sexual tension and as soon as they were in bed she pulled the sheets back and took Paul in her mouth and started sucking on his cock like a hungry bear.

"Whoa Jess what's come over you, god you're like a dog on heat tonight." Paul said.

"Shut up, lay back and enjoy the ride." Jess said, to stop him talking.

Paul wasn't huge in the cock department but he rose to a good 7 inches when really turned on. She sucked and slurped on his cock like a pro, as she wanted him as stiff as possible to get the maximum pleasure out of his hot cock.

She stopped sucking his dick, straddled him and slid his cock into her very wet pussy. It felt good inside and she was thinking what if this was Tyler's big cock sliding in and out.

She was riding up and down groaning, as his cock was twitching inside her wet pussy. She leant backwards onto her arms to get his cock to rub up against her G spot to get the most pleasure out of the fuck. Paul sat up and was groping at her tits and rubbing her nipples between his fingers. He then pulled her off and turned her onto her hands and knees and slid his cock back into her wet pussy. He knew he didn't have long, as this position really turned him on and within a minute his cock was spurting cum into her pussy.

Jess felt his cock go limp and he slipped out of her and onto his back completely exhausted.

"My god that was fantastic." Paul Said. "You were amazing tonight. More of that please whilst we are here." and he turned over and fell asleep.

Jess was still on her hands and knees thinking.

"WTF has just happened. I was enjoying that and he came and that's it. What about my orgasm and me getting off? How dare he just finish and go to sleep."

She got off the bed, put on the complimentary silk robe and walked out onto the balcony. She sat on the wicker chain still feeling cum seeping out of her pussy thinking.

"I needed a big fuck and to have a massive orgasm, but tonight I am not."

She stood up and was looking over the balcony and she heard a noise coming from a balcony below. She peered over to see Tyler butt naked with his massive cock sliding into Saskia from behind. She had one leg lifted up onto the rail and his massive cock, all of 12 inches and as wide as her arm, sliding in and out of Saskia's pussy. She was groaning and moaning and had her fingers either side of his cock as it slid in and out.

"Fuck me baby, slide the big black cock deep into my pussy. I want you to fuck me hard and squirt the hot cum into my pussy." She heard Saskia say.

Jess was mesmerised by the sight of her husband's boss sliding his cock in and out of his wife's pussy. She felt her fingers sliding inside the robe and slipping into her own wet pussy.

She felt so hot and excited and wanted to jump down and take Tyler's cock in her mouth and wanted it slide into her wet pussy too.

Tyler grabbed Saskia's hair and pulled it back.

"I'm going put my hot seed in any hole I feel like tonight bitch."

He continued to thrust in and out of Saskia's wet pussy.

"I bet you wish you were fucking Paul's wife Jess tonight, up her tight little arse. I could see you checking her out at the bar this evening." Saskia said.

She was groaning even more now in between the thrusts as she was nearly coming to her own orgasm. Tyler moved one hand down off her hip and rubbed his big black thumb over her arsehole. He pushed it in and started making circular movements and then was sliding it in and out. He stayed silent and kept thrusting his hips in and out of Saskia's wet pussy.

Jess's fingers were sliding in and out of her wet pussy at speed. She knew she had to keep quiet so as to not disturb what was going on below her and she had to bite her lip to stop her groaning and crying out. She had four fingers in her pussy now and was rubbing her thumb up and down her clit as she was pushing in and out with her fingers.

She was so horny and with her other hand she sucked on a finger and started to rub around her butt hole. She had never really done anal before, but my god, what Saskia had said about Tyler fucking her arse, had made her even more horny.

Her finger slid slowly into her arse and she couldn't believe how easily it had slipped in and she felt a whole new pleasure. She knew she couldn't finish herself off in that standing position so sat back down on the balcony chair with her legs splayed wide and she moved her finger from her arse onto her clit to get the maximum feeling for an orgasm.

She was nearly fisting herself with one hand and rubbing her clit with the other and she felt her body shaking and a massive wave of sheer ecstasy overcame her. Her pussy flooded with liquid and squirted all over the balcony floor. That was the first time in 20 years she had actually squirted from an orgasm and she was drained.

"My god, I can't believe what I have just done." She thought.

She felt shocked but at the same time very excited. She peered over the balcony but Tyler and Saskia had moved back inside to probably finish off.

Jess moved back into the bedroom and went to the bathroom to wash herself down before getting into bed, where Paul was happily snoring away.

Jess drifted off to sleep thinking about that massive black cock of Tyler's sliding in and out of her pussy and arse and the huge amount of cum he would pump into her.

BEEP! BEEP! BEEP! BEEP!

"What the fuck is that?" Jess thought as she woke quickly.

"Morning honey. Sorry about the alarm, I had to set it as me and the boys are playing golf today and I wanted to get down to breakfast and meet the lads before we headed off." Paul excitedly said.

"I think you and the girls are lounging around the pool or something today. I will probably see you late afternoon." Paul said.

He changed into his shorts and top for golf and said, "See you later babe, mwah." and with that he quickly left the room without even a kiss and a hug.

Jess was still trying to open her eyes after waking up quickly and take in what Paul had said. She didn't really register the info until he had left the room.

She sat up and rubbed her eyes. She reached down and still felt wet from her activities the night before. She looked across at her watch and it was 8 o'clock in the morning. She thought a nice shower, walk casually down to breakfast around 9, meet the girls, chill and then get to the pool around 10 to 1030. She walked into the bathroom and the shower was huge. It could fit at least 3 people comfortably in it and the shower head hung down from the ceiling with a huge spray head. She turned on the shower and let it run until it was the right temperature and then stepped into the water and let it run over her head and down her body. She used the nicely scented soap all over her body, massaging her breasts and thighs, legs and bottom. She washed her hair with shampoo and conditioner and then stood letting the water run over her body. She reached down and ran a finger over her pussy lips thinking of what she had seen and done last night. She could feel her body responding and her juices begin to flow. Just the thought of what might happen made her horny.

"I had better not play with myself too much otherwise I will make myself sore and that's no good." she thought.

She finished off and stepped out of the shower and into the bedroom. She dried her hair, put on foundation makeup, put some casual shorts and a T shirt on and left the room to go to breakfast.

When she got down to the restaurant she saw Lisa was there and Saskia sitting at one of the tables with another lady she had seen in the bar last night.

"Good morning ladies." Jess said, "hope you all had a good sleep last night after the journey"

"I was asleep as soon as my head hit the pillow!" Lisa said, "don't think Tony was too happy though, but I was really tired and needed my beauty sleep."

"Me and Tyler just relaxed on the balcony after we left the bar and then went to bed." Saskia said. "It was a nice gentle way to wind down before sleep."

"Yeah right Saskia." Jess thought, "A gentle wind down with a hunk of meat thrusting into your pussy, I don't think so."

Jess saw Saskia smile at her and for a minute. She thought that Saskia knew that she had been spying on them from her balcony above.

"No she couldn't have." Jess thought. "I was very quiet and didn't make a noise even though it was one of the most powerful orgasms I had ever had."

Jess went off to the breakfast bar and got some fruit, bread and scrambled eggs.

"So what's the plan today then." Jess said.

Saskia piped up. "I think most ladies are going to be around the pool chilling and I think a couple have massages booked but other than that, it's a day of rest before some day activities from tomorrow onwards."

Jess was eating her breakfast and was sat next to Lisa. She leant over and gently whispered a question into her ear. "What did you think of Tyler?"

"In what way." Jess asked quietly.

"Well, have you seen the man. All muscle and I bet he's got a cock the size of an elephant's trunk."

Jess nearly spat her food out of her mouth. "Lisa, I didn't know you were like that."

"Babe, working at a fitness consultant you see a lot of guys who think they have it all. There are those who have muscle and there are those who have MUSCLE, mainly between the legs."

"So, have you... you know, seen this muscle." Jess asked.

"Hell yes. There is one guy in the gym who is always trying to corner me and asked for private lessons. He's not bad looking but when he gets that lycra on, his package sticks out a mile. He was either curling it up or he had a sock down there."

"What happened then." Jess asked excitedly.

"I called him out. I said "ok" to a private lesson and I managed it so that he was doing exercises that showed off his package. I had to help him with some of the stretching exercises and it was during one of those that my hand touched it."

"Touched it??" Jess asked.

"Yeah and it grew straight away. So much so he had to stop the stretching exercise because it was causing an issue."

"What happened next." Jess asked inquisitively.

"Well the private lesson was in a small group room, which doesn't have any windows and one door which can be locked." "He looked like he was in discomfort, so I quickly locked the door and went back over to him and pulled his lycra shorts right down."

"Oh my god how did he react." Jess asked.

"Well I thought he would shout out or be embarrassed, but this mighty large black cock sprang out at me, near my face and oh my word it was huge!"

"Did you ...?"

"I couldn't help it. It was right there and before I knew it my mouth was round the head of his cock and sucking on it." Lisa continued. "He was pushing his hips forwards and backwards fucking my mouth. I could only get about 3-4 inches in as it was so big."

"I had my hand around the rest of his shaft and was massaging his balls as well. He didn't last long and he came in my mouth. God there was so much of it, some was spilling out of my lips onto the floor."

"What happened then. Did you fuck him?" Jess asked.

"No the class time was nearly up and there was another class booked in there, so I quickly wiped up the spilled cum with my towel and he pulled his shorts up and we left. We didn't even talk to each other just looked and smiled and went our separate ways."

"Oh my god Lisa. I would never have thought that of you. I thought you were happy and in love and busy with work etc." Jess said.

"Lady, I have needs and when something like that presents itself you gotta take it. Seize the moment and no regrets."

That gave Jess something to ponder on as they left breakfast and went up to their rooms to get ready for the pool.

Jess decided to wear one of her new bikinis. Not too small but not too large with tie ups at the side of her bottoms and a bikini top that covered her tits but not too much. Enough to be sexy without flaunting it like a slut.

She headed down to the pool around 1030 and saw Lisa and Saskia on loungers with a spare one for Jess.

Lisa was in a high cut bikini but covered her assets well, Saskia was in a string bikini that literally was string. There was a piece of material covering her nipples and a piece over her pussy. Obviously no hair as a single strand would have stuck out from the size of that material.

The day was nice and chilled and they sat around the pool talking about all kinds of things work, beauty, fashion, husbands (how good or bad they were), sex (again how good or bad). Jess was drinking a mixture of water and cocktails so as not to get too pissed as she wanted to savour the day without getting hammered before the evening.