Caribbean Awakening Pt. 04

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The Caribbean adventure continues with the girls.
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Part 4 of the 6 part series

Updated 06/10/2023
Created 08/16/2020
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Caribbean Awakening Part 4 -- The saga continues

It had been a couple of weeks since Jess and Lisa had got back from the Global sales club, and they had been communicating constantly on WhatsApp about their break.

Lisa and Tony had taken their encounter and sexual exploits to another level in their relationship. Tony was really into Lisa using toys in their sex sessions and Lisa was loving the big black dildos she had bought for this fun.

Jess and Paul were like two different people. Their daughters had noticed this as well and loved the fact that their parents were more open, happy, and engaging. Casey and Beth had even been out shopping with Jess and bought her new clothes for work, now she was feeling so much more confident about herself and her body.

Rachel and Saskia were also on the WhatsApp group and a lot of messages and comments about the trip were relived, as well as looking to book a revisit to Tobago again.

They had found out that not long after Rachel and Brad had returned, they had had a big row and Rachel had moved out to a rented apartment. Rachel was upset, but relieved as it had been building for a while, and she said it was for the best for both of them as they had no kids or major responsibilities.

Saskia and Tyler were going from strength to strength, and he had been promoted to VP of sales for the US and she had been doing more work with her organic cosmetic company.

Jess, Lisa, Saskia, and Rachel had all agreed to come back to Tobago in Sept and had booked flights. It looked like Paul and Tony wouldn't be able to get the time off work at the same time, so Casey and Beth, Jess's daughters, were going instead.

Saskia mentioned to Jess and Lisa that there was a great little boutique that she went to near Covent Garden in London, that was great for holiday wear, and Trey, the owner, was the perfect host and would ensure they found what they were looking for.

With less than a month to go, Lisa and Jess arranged to meet up in London to have a girly day with lunch, and also go to the boutique Saskia had mentioned.

They met up for lunch just off of Tottenham Court road, at a lovely Tapas bar, and greeted each other with a big hug and kiss on the cheek.

"Wow Jess, you are looking bloody fab. You are so different from Tobago and you look stunning!"

"Thanks Lisa, the trip really made me realise how much I love what I have and wanted everyone to know. You look fab as well as always." Jess responded. "What have you been up to then since we got back?"

"Well, where do I start." Lisa said. "When we got back Tony was like a new man. He couldn't keep his hands off me and wanted sex a lot and not just straight boring sex, he wanted toys, anal, blowjobs the works!" she continued. "From the boring sex we used to have, he has really come out of his shell".

"Paul is the same." Jess said, "He has realised he has a very sexy wife, that needs to be looked after, but it's all about giving me confidence as well as to go out and enjoy life."

"I totally agree Jess." Lisa added. "You remember I told you about that black guy at the Gym whose cock I sucked after the private lesson, well it went one step further."

"Tell me more." Jess asked excitedly.

"Well, the first week back he hadn't shown up at any of the classes, so I had thought he had moved on." Lisa said. "The following Monday I showed up to do a class, and he was there with a big smile on his face." She added.

"So, what happened?" Jess asked.

"It was the last session of the day, so I didn't have any further classes." "He waited around after the class and come over to me." Lisa explained.

"I was a bit nervous, but he came across and put a hand on my arm and said."

"Great session Lisa, do you fancy a drink or something?"

I said to him, "Well after the last session we had, I would have thought you were after something else!"

"Wow Lisa you are so forward." Jess said.

"We didn't have to time to muck about as I wanted to get that massive cock of his out again." Lisa grinned. "We arranged to meet outside in the car park, as I know this place behind the sports centre where it's very private, in a small cluster of trees, and no-one can see you from the car park. When we got there, it didn't take long for him to get his cock out and me start sucking it. God it was bigger than I remembered and rock hard. I was squat on the floor with his huge cock slurping in and out of my mouth. He was pushing it hard to the back of my throat and he had also pulled up my sports top and was pinching my nipples between his fingers. God, my pussy was getting hot and wet at this stage." Lisa continued.

"God you are making me hot just talking about it Lisa." Jess squirmed. "What happened next?"

"Well, I was so wet I just had to have him fuck me. He pulled me up, turned me round and bent me over. He pulled my lycra shorts down and just ripped my G string off. He pushed his cock against my pussy, and it slid in deeper and deeper. I caught my breath as it went in but god it was so horny, and I was gushing as soon as he pushed it deep. He was pumping hard into my pussy and he had his thumb working in and out of my arsehole. After a couple of mins, I spurted out for him to fuck my arse, and he didn't waste any time. He pulled his cock out and pushed it hard against my arsehole. It slid up and oh my god I was in heaven. He had it all the way up and was soon really fucking me hard. It didn't take long, and he gasped and shot his load into my arse and it was squirting out and onto the ground."

"Fuck Lisa that is so hot, I would have pulled my knickers down finger fucked myself it we weren't in this restaurant." Jess whispered.

"Ha ha, it was very horny, and we just dressed and winked at each other, knowing that there would be a next time. Then we got into our cars and left." She finished.

"Did you tell Tony when you got home?" Jess asked.

"Nope, I just wanted to enjoy it for what it was..... Fun!" Lisa replied. "Anyway, enough about me, what have you done then since you have been back?"

"Well, my confidence has been through the roof since we came home, and I have new clothes for work and casual. Andy, the office manager, commented on how much I had changed since the trip and that I looked and acted so much different. He even gave me a sales job to do last week." Jess explained.

"What was that then?" Lisa asked.

"They had a property on their books that they hadn't been able to get rid of and someone had made an inquiry. Andy had asked if I wanted to try to sell the property as a trial run for maybe a new role."

"So, tell me all about it then. How did it go?" Lisa asked.

"Well, I went to the address and had dressed in my new work outfit, black skirt, white blouse and black jacket with heels. I wanted to make a good impression and look professional." Jess said. "I was supposed to be meeting the client, Trevor at the property to show him around."

"Did he turn up and what was he like?" Lisa asked intriguingly.

"He did, along with his business partner Adam. They were two fit black guys, who had been buying properties, renovating them, and renting them on, to executives at big companies."

"So, what happened, tell me all." Lisa asked frustratingly.

"I showed them round the fully furnished property, trying to be all professional, and we ended up on the top floor looking out over the balcony at the open fields beyond." Jess said.

"And......" Lisa pushed further.

"I wanted to be good and try and close the deal, but Trevor had said that they had been looking at other properties as well and didn't want to make a decision yet." Jess continued.

"Crap so nothing else happened?" Lisa asked.

"Well, I took the initiative and asked them what I needed to do to convince them this was the right property for them to make me an offer, and take it off the market." Jess continued. "I didn't expect what happened next."

"WHAT!!!!!" Lisa cried out.

"Trevor undid his trousers and pulled out this massive black cock." Jess said. "My mouth just dropped open as I looked at it."

"Would you suck on this?" Trevor had said.

"It felt like we were back in Tobago and I just dropped on my hands and knees and took it in my mouth." Jess continued. "I couldn't believe what I was doing but it just happened. Trevor's business partner then dropped his trousers and pulled his equally large cock out as well. I was on my knees sucking two big black cocks in a strangers house." Jess said.

"Oh my god, what happened next?" Lisa asked.

"They stood me up and I took off my jacket and blouse. They lifted me onto the bed in the room and I continued sucking Adam's cock, whilst Trevor pulled up my skirt spread my legs and had my soaking knickers pulled to one side licking my pussy." Jess explained. "Before I knew it, Trevor had his cock sliding into my already wet pussy and was sliding in and out. Fuck it was so hot and exciting. Everything we did in Tobago was just flooding back and I was loving it. After fucking me for a few minutes, Trevor pushed my legs up over my head and Adam grabbed my ankles. He licked my arsehole and pushed two fingers in and was sawing them in and out. I still had Adam's cock in my mouth and was trying to get as much of it down my throat as possible. Trevor then pushed his cock against my arsehole and I knew what was coming. God I wanted it so bad. He pushed firmly and it popped into my tight hole and I had a massive orgasm squirting my juices all over his cock. Adam tensed and shot a load down my throat and I had troubled swallowing it all."

"Your story is even hotter than mine, you dirty bitch." Lisa said.

"Trevor pulled out of me and Adam laid on the bed and I reverse cowgirled onto his fat cock into my arse. Trevor then pushed his cock up my pussy and within seconds I was coming again." "We fucked like that for about 10 mins and they both exploded in me and we were spent." Jess said. "We got dressed and it ended up I got the property sold, which was great news." Jess said excitedly.

"Well let's hope they give you more properties to sell and they are equally as good as this one." Lisa commented.

The two girls had their lunch, chatted more, and then walked down towards Covent Garden, where the boutique shop Saskia had told them about was.

They walked into the store and they were both met by this 6ft 4" black guy, who introduced himself as Trey.

"Hello ladies, you are both looking mighty fine. What can I help you with today?" Trey said.

"Well Trey, our friend Saskia told us about this place, and she said you were very accommodating and would know exactly how to help us with what we need." Jess said.

"Mmmmm Saskia, very fit, gorgeous Brazilian with a butt to die for." Trey continued.

Jess and Lisa looked at each other, turned back to Trey and in unison said, "That's the one." and they both chuckled like two silly schoolgirls.

"Well, you are in luck ladies. It's near the end of the day and you will be my last two customers of the day, so you get all my attention, and more, to help you find what you are looking for." He said, oozing with sexual confidence.

"Well." Lisa continued, "we are looking for a number of outfits for evening, casual, posh, sexy underwear and whatever else you think we may need to an adventure in Tobago."

"And whatever else you think you can give us that will help us on our way." Jess said, winking at Lisa and Trey.

"You both have gorgeous figures and I think we have a number of dresses that will appeal to you in a variety of colours and styles. Some I would suggest shouldn't be wore with underwear as I am sure both of you ladies wouldn't want your knicker line to be seen on your very nice arses." Trey said.

"One thing we have learnt from our last trip to Tobago is that our knickers don't last on us very long and so it seems logical to have dresses that suit our figures and don't hide much." Lisa stated.

Trey picked out some evening dresses for both Lisa and Jess along with some underwear for casual wearing, beach clothing and some bikini's. He pointed to the dressing rooms at the back of the store and said, "I will close up the shop so you girls will feel more comfortable, and I can give you my undivided attention."

"Thanks Trey." Lisa said and she and Jess walked towards the changing rooms at the back to try on the different outfits.

The changing rooms were actually 2 rooms divided by a curtain and you went through a door to get to them. It cut them off from the shop so customers couldn't see anyone getting changed. Lisa pulled the curtain back so both her and Jess were in one changing room.

"I love some of the outfits they have here. I have gone for a figure hugging, but also a short and sexy one, as I am sure I will wear these out in Tobago." Jess said.

Both Lisa and Jess got down to the knickers and bra to try on some of the dresses.

"Ooooh Jess I like the underwear, very sexy. Are they new since you come back from Tobago?" Lisa asked.

"Hell yes, I wanted to feel sexy all the time, not just when I was out or partying. This way I get to buy new clothes that make me feel great and also look good on me." Jess commented.

Lisa leant forward and gave Jess a smack on her exposed arse cheeks as she had a sexy see-through G string on.

Jess had on a sexy lace bra and knickers which also looked fab on her.

They both tried a number of dresses on, and they loved them. Lisa went to try on a short dress that only really finished just below her bum but was also very figure hugging.

"I don't think I can wear my underwear with this dress." Lisa said.

"You are right, you need to see what it looks like without them on." Jess sniggered.

Lisa unclipped her bra and peeled off her knickers so she could try the dress on.

Jess could see her lovely pussy and it was shaven and slightly glistening in the light.

"You feeling a bit moist down there Lisa." Jess asked.

"These clothes and the fact that Trey could burst in any minute is getting me wet, isn't it you?" Lisa said.

"My pussy has been soaking since we came into the store and I saw him. Do you think he will come in?" Jess said quizzically.

The timing couldn't have been more perfect. There was a knock at the door, it opened, and Trey appeared at the door. Lisa was completely naked, and Jess was stood in her bra and knickers.

"Oh god, I am sorry ladies, I should have waited when I knocked before entering." Trey said embarrassed.

"We were hoping you would come in and tell us what you thought of the outfits and give us some of that customer service Saskia had been talking about." Lisa said invitingly.

"MMMmmm. Well looking at the outfits you tried on, I would say you are well overdressed." Trey said with a beaming smile on his face.

He moved over to Lisa and put his arm around her face and planted a kiss on her lips. She opened her mouth and their tongues collided and explored each other's mouths. His hand dropped to her arse and gave her cheeks a good squeeze. Lisa bit his lip seductively and carried on tonguing him.

Jess moved across and was rubbing the front of his trousers and feeling his large cock growing under the material.

"It looks like those trousers weren't fit for purpose Trey. They are causing a restriction and its needs sorting." Jess said.

She unzipped his trousers and squatted down on the floor. She pulled his cock out and was massaging it in her hand and then planted her mouth over the end.

She was licking up and down his shaft and soon it was fully extended to its 11" of thick black meat.

"Oh my god that is enormous and it's so thick." Jess squealed.

"That's what Saskia said when she came to try on some outfits." Trey laughed.

Jess continued to suck his cock trying to get as much into her mouth as she could. Treys hand was now rubbing up and down between Lisa's legs and he could feel how very wet she was. He inserted a couple of fingers into her hot pussy and started pushing in and out.

Lisa was moaning into his mouth whilst still kissing him passionately. Jess wanted to impale herself on Trey's cock so stood up and took off her knickers and bra. There was a two-seater couch in the changing room, and she knelt on it with her butt sticking out and said to Trey, "Please put that huge black cock in my pussy. I am absolutely soaking wet for it."

Trey moved over to where Jess was knelt on the couch with her arse sticking out, waiting for him, and pushed the tip of his cock against her pussy lips. Juices were flowing already in anticipation and he pushed the head between her wet lips. He eased in and after a few inches Jess was groaning like a slut.

"Oh fuck, that is soooooo good. Push it in further and harder." She said between gritted teeth.

Lisa had sat on the floor under jess and was using her fingers to rub Jess's clit and take in the juices that were flowing from her Trey fucking Jess's wet pussy.

She pushed up and started licking her clit with her tongue and Jess was moaning and shouting, "I'm commmmiinnnnngggg oh fuck!"

She gushed all over Trey's cock and Lisa got a mouth full of hot pussy juices lapping it up. Trey was pushing his cock in and out feverishly now and Jess was having orgasm after orgasm.

"That pretty white arse looks like it needs good fucking as well." Trey said.

"Push it in hard Trey, I want that big block cock in my arse as well." Jess screamed.

Trey pulled out and rubbed his juiced-up cock up and down Jess's arse hole to make sure it was well lubricated before he entered. He pushed the head against her arsehole, and it popped in.

"Oh, my fucking god push it in hard, hard, please." Exclaimed Jess.

Trey pushed inch by inch until his balls were up against Jess's cheeks. He left it there for 10 secs and then slowly pulled out and pushed it back in again, slowly, slowly and then speeding up until the whole of his cock was sliding in an out at pace. Jess was thrashing away with Lisa still licking her clit underneath her. Jess was pulling on one of her nipples between her thumb and forefinger which heightened the pleasure even more.

"Fuck, I'm going to explode. Aaaaahhhhhhh!!!!" Trey tensed and dumped a bucket load into Jess's arse. There was so much is squirted out the sides and Lisa was on hand to catch it in her mouth and swallow it greedily.

Trey's cock slopped out of Jess's arse, and Lisa was there to scoop it into her mouth to suck off his cum and Jess's juices. It didn't take long, and Trey was rock hard again. Lisa's expect licking and sucking had given his cock life straight away.

"You are going to fuck me now Trey. I want you in my pussy and arse now!"

Lisa then laid back onto the couch and pulled her legs up near her head to give Trey as much exposure to her pussy and arse as she could.

He lined up his cock and rubbed it up and down her pussy crack.

"Wow, you are just as wet as Jess. You want this black cock don't you?" Trey asked.

"Oh yes, fuck me hard in all my holes as I am a white slut and need satisfying."

Jess had now swapped places with Lisa and she was under her arse to ensure that she got all the cum and juices flowing from Lisa's pussy.

Trey slid his cock into Lisa's pussy and pushed all the way up till he balls slapped her arse. He starting fucking her hard and each thrust made Lisa moan loudly with excitement.

"Harder, harder!" she kept saying.

Jess had sucked on her fingers and had started to push them into Lisa's arse to loosen it up for Trey.

"Fuck that feels good Jess" Lisa said as she put one more finger in.

Jess now had 4 fingers pushing their way into Jess's arse and was fucking it fast.

"I think she is ready for an arse fucking now Trey." Jess said.

"I don't need asking twice. You girls are so fucking hot I could do this all day!"

Jess took her fingers out of Lisa's arse and got onto the couch in a squatted position above Lisa's head.

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