I hailed a cab and told the driver to take me to St. Martin street. From what I have read St. Martin Street is like a red light district. There is a lot of of causal bars there but also there are strip clubs and some brothels. After about a 5 mile cab ride I arrived at St. Martin Street and paid the driver and proceeded to walk down the street. I pulled out my phone and re-looked at the picture of Nicole. Nicole had brunette hair, a pretty face, and massive natural looking breast for her short frame. By my guess she had DD’s and was about 5 ft tall. She also had a nice ass to go with it. She wasn’t thin but not fat either. Her body resembled a slightly chubbier Ariel Winters. My arousal was coming back and I proceeded to text Nicole.

“Nicole, this is Marcus Naomi’s friend, she said you were looking for a drinking buddy this evening,” I texted.
“Yes, I am always up for a new drinking buddy, especially ones that are cute like you,” she replied.
“I am on St. Martin Street, where are you located? I asked.
“Sparrows Bar” she texted back.

I pulled out my phone and saw that Sparrows Bar was 5 blocks up from me. I started to walk there anxiously waiting to meet Nicole in hopes of her ending my constant arousal. I arrived at Sparrows Bar and peaked in. It was an open air bar and looked a little run down but had a good vibe coming from it. I walked in and saw Nicole sitting at a table drinking a what appears to be a margarita on the rocks. I went up to her and introduced myself. She stood up and gave me hug while introducing herself. Nicole appeared to be in her mid 20’s, and was wearing a black lace top which revealed a black bra underneath that was having trouble containing her overflowing breasts. On her lower body she had on a pair of tight jeans with black high heals. She was very sexy and was dressed to show off her best features. I sat down in a chair close to her and ordered another vodka tonic.
As we sat there drinking we started talking about what brought us to the island. Nicole was an Italian American from New Jersey who was here to work in the banks. After a while of basic get to know you conversation Nicole changed the subject to more personnel.

“Naomi says you are single”, said Nicole.
“Yes, I just moved here a couple of days ago”, I replied.
“That’s good, I personally don’t believe in relationships”, stated Nicole.
“Why is that”, I questioned.

Nicole went on to tell me that she doesn’t want to dedicate herself to one person and wants be open to new adventures. Which is girl speak for fuck anyone she wants. I enjoyed where this conversation was going, it was leading to a promising evening.

“Naomi said you like smaller women”, Nicole said in a flirty tone.
“I enjoy many types of women”, I replied trying to avoid where this conversation was going.
“Yeah but she says your type is on the shorter side”, she fired back.
“I do find myself attracted to shorter women”, I said.
“Have you ever been with a short girl who has a pair of these”, Nicole said while grabbing her breast.
“I can say I have experienced those separately but never together”, I replied.
“Well if you play your cards right tonight might be your night”, Nicole replied.

After our flirtatious banter Nicole leaned over and whispered in my ear that she wanted another drink then proceeded to to give me a kiss. I stood up and went to the bar and ordered us more drinks. With drinks in hand I went back to the table where Nicole was in the process of texting someone. When I arrived at the table Nicole look up from her phone and put it back in her purse. I sat back down and handed her the drink. During our talking and drinking I felt Nicole grab crotch.

“What are you doing ” I questioned.
“Seeing what I am working with”, she replied.
“Does it meet your approval”, I asked.
“I will let you know later”, she said with a smile.

Nicole was definitely being a tease this evening but I was confident this teasing would end later tonight. After we had finished out latest round of drinks both of us were pretty drunk. I pulled out my phone and noticed it was still relatively early but due it to being a Friday night the bar was getting crowded. I noticed some guys looking at Nicole. I decided I had enough flirting for now and wanted to make a move. I asked Nicole if she wanted to get out of here and go for a walk. We got up and I paid our tab and proceeded out of the door.

Chapter 12

While we were walking down the street I had the chance to glance back and check out her ass. Nicole has a very round and tight ass. As we approached an alley I grabbed Nicole and pushed her around the corner and pinned her against the wall where I started to kiss her. In turn she inserted her tongue in my mouth. After several minutes to intense making out, I began to kiss her neck. During this kissing Nicole started to release soft moans. I released one of my hands from her arm and moved her hand down to crotch. She started to massage my cock from the outside of my pants. The kissing continued and she started to unbutton my pants and reach her hand down my underwear. As her hand was halfway down I stopped her because there was still some light out and people could see us. I whispered in her ear is there any where we can go. She grabbed my hand and I quickly re-buttoned my pants and followed her. We walked for another six blocks and reached large condo building. We entered the building and walked up four flights of stairs. We reached a door and Nicole pulled her keys out of her purse and unlocked the door.

We entered her apartment and proceed to the couch. Once we got to the ouch Nicole pushed me down and climbed on top of me. She then started to kiss me and take off her lace top. Once her top was off she I was able to get a better look at her magnificent breasts. We continued kiss and I started to place my hands and her tight ass. After about 10 minutes of animalistic making out Nicole put a stop to it. She Got off of me and led to the kitchen where she poured us some water.

“We need to hydrate before we move into the next activities of evening”, Nicole said.
“What do you have in mind”, I said with a big smile.
“I know Naomi told you about my oral skills, I think its time for you to see for yourself”, Nicole replied as she led me towards another room.

We made it into the bedroom and Nicole started to remove my shirt and pants. I then stood in front of her in my boxers with an erection that was starting to form. Nicole told me to wait on the bed and proceeded through door which I assumed was her bathroom. After a couple minutes Nicole came out of the bathroom dressed in a black bra,matching lace panties, and her black high heels from earlier this evening. She had a large tattoo of a flower that ran from her underwear line up the side of her body. She walked up to me and got down between my legs and pulled my boxers to the ground. My dick sprang out of my boxers where she then grabbed it before she was hit in the face by it. She took my hard cock and proceed to move her hand up and down then started to lick the tip of my penis. After licking my tip and then my entire shaft Nicole inserted the head of my cock in her mouth. She started to work the rest of cock into her mouth. She continued to guide my cock in and out of her mouth with her hand. Naomi was right Nicole gives terrific blow jobs. As she continued to work my cock in her mouth I grabbed the back of her head and started to make her take my member deeper into her mouth. We started to gain rhythm and she was able to make the entire 8 inches of my cock disappear into her mouth. Nicole’s ability to deep throat felt amazing. After a day of constant arousal I was about ready to release my cum into Nicole mouth. As I came into Nicole mouth she started to swallow it. Once I was finished cumming Nicole got off her knees and proceeded onto the bed.

She laid down next to me where we then became face to and started kissing while embracing. I reached my hand down and started to tug at her underwear. I was able to pull the down slightly. Once I had her underwear down I placed my hand on her shaved pussy and immediately felt her wetness. I then inserted two fingers got her while using my thumb to rub her clit. Nicole broke our kiss and started to moan. I continued to kiss her neck while I rubbed and fingered her sopping wet pussy. After several minutes of kissing and fingering I felt her vagina clamp down on my fingers which led me to believe she had an orgasm. After removing my juice soaked fingers from her pussy, Nicole sat up and removed her panties and then her bra which let her pale ample breast fall out. The breast were not firm but jiggly and sagged slightly. I grabbed a handful of her breast and proceed to put her nipple in my mouth. I circled my tongue and sucked on her nipple as she let a low moan out of her mouth. As I was caressing and sucking on her breast Nicole took her hand and grabbed my cock and started to move her hand up and down.

When she realized that I was ready for a second round she got and leaned over and grabbed a condom from her night stand. She opened the condom and removed it from the wrapper and started to roll it down my cock. Once the condom was on she stood up and straddled me. She then began to lower her body down towards my lap. She positioned herself just slightly above my erect cock. She then took her hand and guided my cock as she lowered her self onto it. My cock parted her pink lips and continued into she soaking wet hole. Nicole was not tight by any means but her up and down motion was very pleasurable. While she was riding me in a slow rhythmic motion I once again grabbed her breast and started sucking on it. Nicole started to let out moans which grew louder and louder as she got closer to orgasm. Nicole grabbed my head from her breast and moved it up to her lips where we proceeded to passionately kiss. During our kiss we stated to breath in unison. After several minutes of making out she broke the kiss then her body briefly shook and then I felt a tightening sensation on my cock. I suspected she had another orgasm.

After Nicole finished with her orgasm she grabbed my head and brought it to hers for another kiss. I broke the kiss and whispered into her ear my desire to fuck her doggy style. She got off of me and got onto her hands and knees where I proceeded behind her and led my dick into her juice covered pussy. I started fucking her with a slow steady rhythm and continued to quickly pick up speed until I was slamming my dick into her. Soft moans turned to loud yells of passion. I could see her breasts just flopping around as I continued to pound her swollen pussy. In the heat of the moment I grabbed her hair and started to pull on it as I worked her body.

“Fuck me like the dirty slut I am”, she yelled as I pulled her hair.

Nicole’s dirty talk pushed me over the edge and I unloaded a large amount of cum into the condom. I withdrew my flaccid cock from Nicole, and then just laid on the bed in exhaustion. Nicole got out of the bed and went to the bathroom and came back with damp rag where she proceeded to remove my condom and clean off my cock. After Nicole wiped me down she curled up into me and we started to kiss. After some brief moments of kissing and cuddling I looked at my phone and saw I had a text from Olivia.

“Want to meet up after I get off work”, Olivia texted.
“Sure, I am free most of the day”, I replied.
“Good I will come to your hotel after work and crawl into bed with you”, She texted.

As I was texting I looked at the time and saw it was on 11:00 pm. Nicole wanted to know if I wanted to go out to the bars. I declined and said that I need to get back to my hotel to pack since I was moving tomorrow. I got out of bed and started to put on my clothes. Once I was dressed I grabbed Nicole’s naked body and pulled her close to me where I kissed her mouth and inserted my fingers into her. I finally broke our kissing and finger session and said goodbye. Nicole said she would like to have rendezvous again and I replied it would be nice.

Chapter 13

I left Nicole’s condo and started to walk down the street. Though I would love to have continued my night with Nicole, I wanted to head back and be rested for Olivia. I walked a couple of blocks till I got to a busy street and a hailed a cab. After a about a 10 minute ride I reached my hotel. I entered into the hotel and stopped at the front desk to have a key put on hold for Olivia. I then went to the elevator and headed up to my room Once I reached my room I opened the door and went in. I noticed all the lights where on in the room and I heard noise from the closet. I walked through the bedroom and into the closet and saw Isabel in the process of packing my items.

“Isabel what are you doing packing so late at night”, I questioned.
“I am making sure all you stuff is ready for you to leave tomorrow”, Isabel said.
“I appreciate all your hard work”, I told her.
“Anything you need Mr. Marcus, I’m here to serve you”, she said.

I told Isabel that I was going to take a shower and head to bed so she could finish packing in the morning. Since Isabel has seen me naked before I had no issue with showering in front of her. I will admit it was a slight turn on for me to shower with her in eyesight. I removed my clothes and got into he shower. I washed the sex off of me for about 15 minutes then exited the shower. As I was exiting Isabel rushed over to me with a towel and started to dry me off. She started at the top and worked her way down. Once she was done drying me off she grabbed the robe and put it on me.

“Would you like a massage”, Isabel whispered in my year.
“No thank you I am very tired”, I replied.

After I passed on Isabel massage she got down on here knees and spread opened my robe. She reached up and grabbed my flaccid cock. She started with a light jerking motion then placed her lips on the tip of it. My cock was still in recovery mode and very sensitive. After a couple of minutes of Isabel playing with my cock I stopped her. I told Isabel I was tired and needed to go bed. She let go of of my dick and got up from her knees. I moved away from Isabel and went into the closet and removed my robe and put on some gym shorts and proceeded to bed. Isabel said good night to me and excused herself from the suite.

Chapter 14

I was awoken by a body hugging me. I rolled over and was immediately face to face with Olivia. She gave me a long and wet kiss before she let me get a couple of words out.

“What time is it”, I questioned.
“A quarter to 7”, She replied.
“Did you just get here”, I asked.
“No I have been here for about 20 minutes. I took a shower and changed my clothes”, she said.

Our conversation ended and we went back to the kissing. After several more minutes of kissing Olivia broke the kiss to tell me she wanted to get some more sleep before our day started. She rolled over and I became the big spoon of our cuddle. I started to run my hands over her bikini style underwear covered ass. I felt a swat to my hand during my caressing was her way of telling me to go to sleep.

I slept for a couple of more hours before I awoke again. Olivia was still sleeping so I messed around on my phone. I had several emails for Naomi stating they had arranged for me to have a bungalow at Crestview. There would be a rental car for me there as well. They arranged to have me and my things picked up at 2 pm this afternoon. During my stay I would be provided a live in maid that closely matched my criteria from yesterday. At about 11 o’clock Olivia turned towards me and gave me a good morning kiss. I kissed her back and we started to caress one another. She slipped her hand into my shorts and started to stroke my cock.

I broke our kiss and removed her tank top to expose her perky breasts. I lowered my mouth to her tits and started to suck and tease her tits with my mouth. During this teasing her breathing became heavy and her cock stroking increase it speed. I stopped our foreplay and went under the covers and removed her panties. I started to rub her clit and noticed her pussy was already glistening with wetness. I lowered my head deeper between her legs and started to lick her pussy. She took her hand and pushed my head father into her crotch and let out a loud moan, then released her grip from my head. After a minute of recovery she pulled me up out of the sheets and inserted her tongue into my mouth.

During our kissing session Olivia pulled my shorts down. She grabbed my cocked and teased the tip of it with her hand.

She broke the kiss and reached over to her purse on the night stand and grabbed a condom and slid it down my erect cock. She got up and straddled me in the reverse cowgirl position and lowered her dripping pussy onto my throbbing cock. He tight pussy grabbed my dick as she engulfed more of my cock inside of her. She started slowly and gradually increased her riding speed. I had a great view of her thick ass. As she increased in speed I started to smack her ass. During our rhythmic fucking we both seemed to be transferred into a euphoric state. While in this state we lost sense of reality and our surroundings. I continued to smack her ass and she yelled harder. Her cry’s for harder lead me to want to take charge. In a fluid motion I pushed Olivia off me and into a doggy style motion. I quickly re-entered Olivia’s soaking wet fuck hole and started to pound her with force. As I was dominating Olivia I noticed Isabel standing in the doorway of the bedroom.

Upon seeing Isabel I froze mid thrust. My pause caused Olivia to leave her altered state.

“Mr. Marcus, I am so sorry to barge in I I…..just wanted to finish your packing”, Isabel stammered.

As I was about to speak Olivia interrupted and said in a commanding but voice “Its fine just go in and finish the packing”.

Isabel hurried into the bathroom and then into the closet. During this brief pause I exited Olivia and laid back down. Olivia then go back on top of me and guided my cock back into her. She lowered her head to mine and kissed me.

“What are you doing”, I questioned.
“Hoping to get another orgasm “,she said with a smile.
“Isabel is right in the next room”, I stated.
“So, I’m sure she’s seen your cock before”, she said.

After that statement I fell silent and turned red and Olivia continued to ride me. After about 10 more minutes of fucking Olivia asked if I was close to cumming because she wanted to cum together. A minute later she whispered into my ear that she was cumming. I then released my load into the condom. As we came we kissed passionately.

Once we were though she rolled off of me and we cuddled up. She said she needed that after a long day of work. Olivia then asked why Isabel is packing. I told her that I was moving out to Crest View Estates to stay in a Bungalow for a couple of weeks. I told her since she some time off she should join me. Olivia said of course and kissed me. She then got out of bed and went into the bathroom completely naked. I heard her ask Isabel to order us some coffee and then she called me to join her in the shower.

As I walked into the bathroom Isabel passed by me. She looked down and stared at my cock that sill has some cum on the tip of it. I went into the shower and grabbed Olivia from the back. She then turned around and kissed me. I could tell by the amount of time and how she kissed me that she was into me in more than just a fling type of way. I to was very attracted to Olivia and enjoyed her personality. She then broke the kiss and asked if I had ever been inside of Isabel. I quickly responded no. She told me its fine if I had because we just met the other night and we are not exclusive. I told her no I have never had had sex with Isabel because she can’t go past oral. Olivia laughed and started to wash me. After about 25 minutes of fondling and washing Olivia and I exited the shower. Olivia went into the bedroom and pulled some clothes out of a bag she brought. She on a pink lace thong and then proceeded back to the bathroom with her cosmetic bag to finish up getting ready. As we were finishing up getting ready Isabel had returned with our coffee. Olivia entered into the living area and joined me for coffee. She was wearing a t-shirt with a pair of tight jeans and flats. Olivia had her hair done up in a ponytail an looked very casual and sexy.

We finished up our coffee and headed down to the hotel restaurant for some lunch since we slept through breakfast. When we got to the restaurant we were promptly seated and ordered our meals. While we waited for our meal Olivia told me she would go home after we ate and pack for the weekend then meet we out at Crest View Estates. We finished our lunch and we headed back up tot he rooms so Olivia could get her things. Olivia gathered her things and we kissed goodbye and she left. I had about and hour left before the car arrived to pick me up. I decided to make sure everything was packed and then sit and have a beer. After about 45 minutes and a couple of beers I decided to make my way down tot he lobby. As I was leaving the room the bell hops were coming into get my bags. I went down to the lobby and the concierge came up to me and said my car was ready for. I was escorted to a black luxury sedan. Once my luggage was loaded I was off to the next stage of my transition to becoming a resident of the island.