Ann's Girl trip to Jamaica

[Anns_boyfriend]

Ann and a good friend of hers Kayla just got back from a 10 day stay in Jamaica. I talked with Ann while she was there through email and here are a few adventures she had on her girl’s trip. These are her words as she wrote them to me...

Day 3,

Good morning babe, hope you are enjoying the time to yourself and not working too much. I wish you were here with me. It’s so beautiful here, we'll have to come here together. The first day here we did not do much, settled in to our room, which is amazing by the way, and walked around the resort to get familiar with the area. We were so tired that we were in bed by 10.

The staff are very friendly and I know they speak English but the Jamaican accent is so strong that it sounds like a complete different language. Yesterday morning we got up at 7 and got showered and ready to go for breakfast then down to the beach. Once on the beach we enjoyed a couple drinks while laying out on the lounge chairs enjoying the sun. Kayla helped me with lotioning my back and I did hers and this brought us lots of attention from the nearby guys. A few of them came to talk with us and hung out for a bit. One of the guys, Tyler was very good looking and very fit. I enjoyed looking at and talking with him lol. But that was it just talking, until later.

You'll enjoy this part babe, in the evening Kayla and had changed into dresses and went to dinner at one of the restaurants in the resort and we got seated right beside where Tyler and his friend Sam were sitting. Sam was the guy talking with Kayla earlier. I know she liked him but she wouldn't say so. Anyways they hadn't noticed us yet until we ordered our drinks and Tyler said he recognized my voice, he invited us to join them at their table and we accepted. Kayla sat next to Sam and I sat next to Tyler of course lol. We talked for a while and ordered food. I’m sure you don’t want to hear about the food right now but the food was amazing babe, you would love all the food here. Kayla seemed really interested in Sam and I was enjoying Tyler's company. We ordered another drink and when it arrived Tyler put his hand on my bare leg below the hem of my red dress. I flinched at the initial touch as I didn't expect it but placed my hand on his giving him the ok. I removed my hand and he left his on my leg. He was rubbing up and down my leg as we talked going up under my dress to the top of my leg. I shifted a little in my seat so that I was almost facing him, that way no one around us could see what was happening. As I shifted his hand brushed against my pussy, he leaned and said "are you not wearing any knickers"? I laughed at the word knickers and told him that I didn't wear them very much. He again purposely this time brushed his hand against my pussy and I smiled at him spreading my legs a little. He took the bait and began rubbing my pussy with his fingers. We continued to talk but it was becoming very hard to concentrate on what was being said with his fingers working my clit. I asked him if he wanted to get out of there and go for a walk on the beach. He removed his hand from my vag and stood up and said "let's go". I told Kayla that I would meet her back at our room in a couple hours and that I was going for a walk.

Are you stroking yourself yet reading this? I bet I've made you really hard already. But it gets better.
We got to the beach and walked a little and the he informed me that this was his last night there. I said to myself "just my luck meet a very hot guy on our second day and of course it’s his last night, so if anything was going to happen with him it had to happen tonight". We walked by a few of the lounge chairs and saw Kayla and Sam fucking on one of them. They never saw us walking by and Tyler said "looks like they are having fun" I grabbed his hand and said to him "let’s go over there by the water and have fun of our own" He looked at me and smiled then ran dragging me to the water’s edge and started kissing me hard while pulling my dress off over my head. I quickly pulled his shirt off and shirts and he did not disappoint. He body was magnificent though his cock was not as big as I had imagined but still quite nice. At least he knew how to use it lol. I lay down on the sand and he laid on top of me he kissed me good and then started pushing his hard cock inside me. I was still very wet from the attention in the restaurant and he slid in me easily. He fucked me on the sand for the next 20 minutes and I had 2 solid orgasms. He came soon after my second one all over my stomach and my tits. After that we laid there for a few minutes then he said he should get some sleep as he was leaving tomorrow morning early. He also added that he wished he was staying longer so that he could keep fucking me but that was not to be. When I got back to the room Kayla was there and looked embarrassed at what she had done. I told her about what I did and it made her feel more at ease. She asked me if was going to tell you and I filled her in on how you enjoy hearing about it or seeing it happen. She wasn't sure yet if she would tell her husband. Apparently they had talked about something like this happening here but she wasn't sure how serious he was about it. I told her to just say "I fucked someone" then see his reaction, tell it was just a joke if he gets upset. Lol

Hope you enjoyed this babe as much as I enjoyed fucking him. Love you lots and will write you again in a day or two.

Day 5.

Hi babe, sorry I haven't written in a couple days. I’m sure your mind is running wild but it has been an uneventful few days except for massages Kayla and I got today. Nothing too crazy but he did rub my entire body except my pussy and spent a lot of time on my tits and ass. It felt nice and I tried hinting to him to do more by raising my hips up when he was rubbing my ass and moaning when he massaged my tits but he didn't take the bait. Kayla said afterwards that she thought he was gay. Lol. She got laid again by her masseuse though lucky girl. She said he was really good at both the massage and the fucking. I should have just grabbed his hand and placed it on my vag or just blurted out for him to fuck me. Next time lol.

Anyways that’s about it for now hope you're having a good week thinking about me. lol

Day 6.

A few minutes after writing you last night I ran into the guy who massaged me, and Kayla was wrong he's definitely not gay. Lol We went to one of the bars last night after I wrote you and was sitting at the bar with Kayla when all of a sudden I feel 2 hands on my shoulders massaging. I looked back at him and he said "this one's free" then he sat down beside me and we started talking for a bit. Kayla said she was going to wonder around to give me some time alone with him and I thanked her and smiled. After about 15 minutes he asked if I wanted to go with him to the massage room where he would continue the free massage. Well you know me and my massages so of course I agreed.

We walked to the massage room and he asked me to undress and lay on the massage table. He went wash his hands while I undressed and came back and stood to my side and began rubbing my shoulders again. He didn't spend too much time on my shoulders, or back for that matter he's much like you and very much enjoyed rubbing my ass. He massaged every inch of my globes and that's when I figured I had to make a move before I left frustrated again. I raised my hips off the table and stuck my ass and pussy up in the air, but he kept just rubbing my ass, though his thumb on his right hand came very close to my aching pussy. I so badly wanted him to touch me so I turned around on the table so was now laying on my back, spread my legs and grabbed his hand and placed it on my pussy. I said "this is where I need attention now"! He looked at me and asked if I was sure and told him that I was never more sure.

Finally he was now rubbing my pussy with two fingers running over my clit then down my slit and the dipping then inside me. He kept this up for a while and his other hand was playing with my tits. It felt amazing to finally have him touching me like I wanted him to. With my right hand I reached for the front of his pants and felt a large hard bulge. With my eyes closed and still laying down I managed to undo the button and zipper on his pants and freed his hard 7 inch black cock. It felt great in my hand with my fingers wrapped around it. I stroked him gently as he fucked me with his fat fingers. His thumb rubbed my clit as his fingers penetrated me over and over until I orgasmed squeezing his fingers inside me with my convulsing pussy. I kept stroking his cock and told him that I wanted his dick inside my pussy. He got me to stand at the side of the table and bent me over it then entered me from behind. Babe, his cock felt so nice inside me I came so quickly again. He was rough with me pulling my hair and holding my arms back as he pounded his dick deep in me. It was incredible, I came once more with him fucking me like this and he told me he was going to cum to. I told him to cum inside my pussy and that I wanted to feel him shoot deep into me. He fucked me harder for a few more thrusts the shot straight up as I felt his first spew of cum hit my womb. He filled my cunt right up with his man juice. He kissed the back of my neck and said "free massages for the rest of your stay" I smiled and told him that for every massage I get then he can fuck me lol. He smiled and said that was a deal.

I put my dress back on and left to go back to the bar to see if Kayla was still there. I could feel his cum running out of me down my legs. Made me feel kinda naughty lol. Back at the bar I saw Kayla and she asked me where I went and I told her that massage guy is not gay. And she laughed then said "you're so bad" I just replied "and so are you” we laughed together then decided to call it a night.

I may go for a massage tonight and will write you tonight or tomorrow morning to fill you in.

Love you babe.

Day 8.

Hi babe hope you enjoyed my last email and played while reading it. Lol. The massage guy who fucked me was not working yesterday or today so no massage lol. I still don’t know his name, is that bad? Lol

Today I was sitting on the patio of our room while Kayla was out and saw a cute guy with his shirt off and a great chest and stomach doing some landscaping. I saw him look at me a few times and decided to tease him a little. I was wearing my black bikini top and my white short shorts. I went back inside and drew the curtain wide open. I kept looking out to make sure he was watching and walked back onto the patio. When he looked at me again I said "another beautiful day" he said something back to me and smiled but with his strong accent I have no idea what it was. I stood there for a couple minutes leaning forward against the patio railing. He started working on the bushes and shrubs that were right beside our room’s patio. I went inside and looked in the mirror above the bed which is directly in front of the patio to see if he was watching and when I saw he was I pulled my shorts off bending at the waist like I know you love. I stepped out of them and then took my bikini top off as well. I was standing naked with my back to him but I could see him watching me through the mirror. I walked away to the bathroom and went to my bag to grab my little vibrator. I walked back into the room and didn't look at him but in the corner of my eye I could see him watching me. I laid on the bed with my feet towards the patio door and spread my legs then rubbed my pussy with my hand. He was no longer doing any work. He just stood there staring at me. I turned on my vibe and started to rub it against my clit. It felt amazing knowing that he was out there watching me. My free hand was massaging my soft tits and pinching my nipples as I kept the vibe against my clit. I wanted to cum so badly and was really enjoying teasing this guy. Then my pussy took over my thoughts and it wanted a cock it wanted that workers cock. My plan was just to tease him while I played with myself but my pussy wanted more and you know what my pussy wants my pussy gets. I placed my vibrator on the bed and stood up then walked straight outside to where he was standing. He made no attempt to move he just stood there watching me walk naked towards him. Once I got to the patio I leaned over the railing again and said "well you just gonna stand there or are you gonna come fuck my pussy"? He was over the railing and had his shorts off before I even got back inside. I laid on the bed and spread my legs and he got right on top of me sliding his hard cock inside me. He was fucking me fast and hard. My pussy was quite happy to have his cock fucking it. Lol. I came pretty quickly as I had worked myself up pretty good and he came inside me soon after. It was quick but satisfying nonetheless. He got dressed and went back over the patio to finish his work. I put my shorts back on and a tank top then went out to meet up with Kayla. I did get lots of attention with no bra on throughout the day lol. You would have loved it.

Love you babe

Day 9.

Good morning babe. Last night after writing you Kayla and were sitting at the bar again and were just about to leave when I saw my massage guy walk in. Kayla saw him to and said "you stay and I’ll go back to the room". He was looking around the bar then saw me and smiled then walked over to me. We sat at the bar and had a drink then I asked him if he was good for a massage. He said "I was hoping you would ask". So off we went to the massage room and as we got in I removed my dress and sat on the edge of the table naked. He looked at me with a big smile and said "beautiful lady" I thanked him and asked for his name finally. His name is Benjamin as he walked behind me and began rubbing my shoulders. I turned around so that I was now facing him still sitting with my legs now on the other side of the table. I told him that I wasn't fair for me to be the only one undressed. He replied "ok man" and removed his shirt then his pants. Everyone here is in such great shape and he was no exception. Once his clothes were off I pulled him into me and kissed him as he willingly kissed me back. His hands were all over my body not massaging me but exploring every inch he could reach. I grabbed his already hardening cock and stroked him to full erection then moved my ass on the table to the edge and pulled his cock to my opening. He pushed forward and easily penetrated my very wet cunt and began fucking me at a slow rhythmic pace as we never broke the kiss. The last time he fucked me was only from behind but now I could with him in front of me I broke the kiss and laid back leaning on my arms a watched as his black cock slid in and out of my covered in my juices. I was thinking of you at that moment enjoying the view of him fucking me as your stroking your cock babe. He began fucking me harder now and at a much quicker pace. I threw my head back and enjoyed the fucking he was giving me. I came pretty quickly and my body shook so much I almost fell back off the table as my arms gave out. Luckily he was quick enough to catch me from falling back.

I stood up and beside him and he bent me over the table like our previous session. His hands were on my ass squeezing each cheek ad he pushed his hard cock back into my now dripping twat. He was furiously pounding me now and I was enjoying it tremendously. He moved his hands to my hips and pulled me hard against him with every thrust into me. I came again very quickly and as powerful as the last and he grunted loudly as I felt him swell and release his cum into me. His pulsating cock felt so good shooting streams of hot cum inside me. He collapsed on top of me and told me that he wanted me to stay there forever. I laughed and told him that you would probably object to that. He stood up surprised and said "you have a man" I told him that I did and that I had already to you about him and would be telling you about this time as well. That seemed to satisfy him and he grabbed me and kissed me hard and he told me to thank you for sharing me lol.

Well its tine for breakfast now and just thought I'd write you this morning to tell you about last night. I had 2 great ducks yesterday maybe I can make it 3 today lol. It’s our last full day here so let’s see what kind of trouble Kayla and I get into.

I’ll write you tonight or tomorrow morning if anything interesting happens.

Love you babe

Day 10.

Good morning babe,
We just finished packing up our bags and about to go for breakfast before catching our shuttle back to the airport. So I said that I would write if anything interesting happened and I guess something interesting did happen lol.
Right after breakfast we went to the pool and we got talking to a few guys that had just arrived. They were also from B.C., Kelowna to be exact. As we were laying there talking I rolled over onto my stomach to tan my backside and asked Kayla to help me out with lotion on my back. Stan, the most attractive one of the group and most talkative said "allow me" and he looked at me and I said sure why not. He applied the lotion to my shoulders and back then asked if I wanted my legs done as well. I told him that I did and he started with my feet then up my legs. If felt good having this young guys hands rubbing my legs moving closer to my crotch. I spread my legs slightly to make a little easier for him and he continued up the back of my thighs and inner thighs. I was wearing my Volcom bottom which you know shows a lot of cheek and he also coated my exposed cheeky parts. His hands went into the bottom of my bikini and squeezed my ass in both if his palms. I thanked him for his help and as he slid his hands out he deliberately moved his right hand in between my legs and touched my pussy inside my bottoms. I flinched not expecting it but it felt electrifying. We talked a little more than they left to go jet skiing.
In the afternoon Kayla and I went for massages and the place was very busy. We thought of coming back later but just then Benjamin saw us and waved for us to come in. He showed Kayla to one room and told her Amos would be right in and we went to our usual room. I’m sure you know what we did in there. Lol never got my free massage. As soon as the door had closed he looked at me and said "let’s give your man another story" and started kissing me right away. His clothes were off soon after and my bikini came off very quickly as well. We fucked the same as the previous two times from behind and I came a couple times. He came inside me again. Before I got dressed he asked if he could take a few selfies of us together and I was ok with that. He took one with his arm around me then one kissing me. It got a little hotter after that, one with his hands on my tits then my ass. He asked if I would hold his cock and bring it to my mouth then I noticed he was getting hard again so I began sucking his cock. He kept taking more pictures and then pulled me up and bent me over the table and fucked me one last time still taking pictures. A few minutes later he placed the phone down on the table beside me and gave me another load of his seamen inside me. We kissed and he told me that he would miss me very much. I gave him my Facebook so we could keep in touch.
Kayla had a great time with Amos as well. We went back to the room and had showers as I now had 2 loads of cum down my legs and in my pussy.

We went for dinner then decided to back to the room and get dolled up to go to the resorts club which was only maybe 50 yards from our room. I wore my short black dress and decided on no bra or panties and so did Kayla. She kept saying that she felt so naughty. We got to the club and it wasn't very busy so we got a table near the bar. We had a few drinks and talked about what a good time we had had over the last 9 days. Kayla said that she wants to do many more vacations with me lol. About an hour after we had gotten there we saw the group of guys that we had talked to at the pool earlier in the day. Stan noticed me right away and walked over with his friends and asked if he could join us. We of course agreed and they got themselves some drinks and shots for everyone and we talked for a while. Stan asked me to dance and we headed out to the crowded dance floor. He danced close to me telling me how hot I looked and that he enjoyed helping me with my lotion earlier. I told him the only part he probably enjoyed was his deliberate touch on my pussy. He laughed and said "no actually, though that was great, but I also loved lotioning your sexy ass"! I moved in closer to him and said "is it as sexy in this dress and turn my back to him rubbing my ass against his crotch. He put his arms around the front of me and whispered in my ear that it was that I had the sexiest ass on the resort. I blushed and thanked him then asked him if he wanted to come with me to my room. He agreed and as we walked by the table I told Kayla that I would be right back after Stan fucked me. She smiled and said have fun.

Once in the room he was all over me, my dress was now on the floor and he had his shirt off as he raised me in kisses and roaming hands. He laid me out on the bed and began licking my pussy. That’s when I internally chuckled thinking "thank god I had a shower before going to the club". He mouth and tongue worked magic on my pussy and clit and I came very quickly. I told him to take his shorts off so I could return the favor. He stood up and I was anticipating a big beautiful cock but it took everything I had to not burst out in laughter when I saw the smallest dick I had ever seen. Babe this thing was no bigger than your middle finger in length and girth and he was hard! I sucked on it for a bit but had to stop as I felt like I was just sucking a finger lol. I told him to fuck me so I laid back down on the bed and he joined me by climbing on top of me. I was feeling so disappointed because this guy was so fucking hot but I knew there was no way that dick was going to satisfy me. He put his cock inside me and was fucking me fast. Honestly babe it was horrible, I could barely tell he was in me at all. He was having a grand ole time though. He was kissing me which he was good at but it didn't make up for his lack of cock. He came very quickly which I was very thankful for so I could get back to the club.

We got dressed and headed back to the club, he could tell that something wasn't right because he kept asking me if I was alright. I didn't want to hurt him so I just kept saying that I was good.

Once back at the club I saw Kayla alone as the guys had dispersed. I joined her and she asked if I had fun with Stan. I raised my middle finger at her and said "that was his dick" she burst out laughing and at that moment Stan walked by and saw us. I’m sure at that moment he figured shit out. Lol I asked Kayla what had happened to all the other guys and she said one by one they left for younger girls. She that she was ok with that because she wasn't attracted to any of them. Stan was the only hot one of the group but his mini dick would have pissed her off lol.
We decided to go back to the bar where we had spent previous nights. The men there were more mature and sported bigger dicks Kayla added. We sat at the bar and I was hoping to see Benjamin again but that didn't happen. We were there for an hour but most of the guys that were there had their wives or girlfriends with them. And the fee single ones weren't anything special. The bartender was cute but he was very busy so didn't get to talk with him very much but I’m sure he would have been fun lol.

Kayla and I decided to call it a night then went back to our room. We ordered some room service because we were hungry. Kayla suggested that we get naked for the room service guy. I thought that was a great idea. We both undressed and sat in the room naked. There was a chill in the room from the air conditioning which had our nipples very erect. You would have loved this sight babe, both of us fully naked on our beds. When the knock came on the door Kayla said "you get it" she looked scared all of a sudden but didn't cover up. I said let’s do it together. We both walked to the door and Kayla said "I hope he's hot and if so I hope he has a big dick". We started giggling like school girls lol. I opened the door and there stood this young black guy no older than 22. His first words were "holy shit man". We asked him in with the cart of food and we sat together on Kayla’s bed watching him take the food from the cart and placing it on our table. He kept looking over at us asking how we're doing. Before I could say anything Kayla blurted out "Horny, we're very horny" we laughed a little. His reply was "I can see that". Kayla then said "would you be willing to give us a hand with our horniness"? He stopped what he was doing and started removing his clothes. First his shirt and exposed a very nicely toned stomach as every other guy that works here. Next came the moment of truth as he began to undo his pants. He slid them down and out sprung this huge 10 inch monster of a cock. Kayla looked at me and said "thank fucking god, now that’s a cock'! He joined us on the bed and went straight to eating my pussy. He was well educated in the art of eating pussy, bringing me to the edge and then backing off a little. Teasing the fuck out of me. Kayla had his cock in her mouth as much as she could put in there. It was very thick. Finally he let me cum and I had the biggest orgasm of my life that seemed to last for ages. It was incredible babe you would have cum just watching me cumming. Kayla and I switched positions and I now had his massive black cock in my mouth. The head was huge and felt so nice in my mouth. I couldn't wait to feel it in my cunt fucking me. Kayla didn’t last long either as she had an equally violent orgasm. He asked me to get my ass up in the air so he could fuck my horniness away. I positioned myself in front of him with my ass up high like he wanted. He took his big cock in his hand and placed the head against my pussy. He began pushing it in slowly easing it inch by inch. I was begging him to start fucking me. Kayla’s eyes were glued to his monster cock penetrating me. Babe his dick felt fucking amazing inside me. So glad that Stan was not the last cock I got here.

He fucked me hard and fast to one quick orgasm then asked Kayla to position herself right beside me in the same position. Kayla did as she was instructed and he eased himself into her as well as she began panting and loudly telling him to fuck her hard to. She looked over at me and stated how fucking well it felt and then I don’t know what came over us but we started kissing each other. Her mouth felt so soft and so very different from kiss a guy. I was rubbing my clit with my ass still up high while kissing Kayla. Then I felt him enter me again and thrusters deep into me a few times then back to Kayla doing the same thing. He kept telling us to keep kissing each other because he liked it a lot. This continued for the next thirty minutes taking turns fucking me then Kayla. We both came a few more times then he said he wanted to cum to and asked us to turn facing him and kiss each other. We turned facing him kissing each other while he was stroking his huge cock right in front of our faces. He shot his first stream of hot cum on my tits then the next on Kayla’s tits. Streams if cum just kept shooting out all over Kayla and I. He asked me to suck his cock clean which I did and then Kayla was licking my nipples clean. It felt weird but really nice having her lick and suck my nipples while I had his cock I’m my mouth. His cock began to soften and he backed off the bed thanking us for the best night he had ever had at work. We thanked him for his help with our horniness. He got dressed and left with his cart. Kayla and sat there naked enjoying our cold food still coated in his cum.

We talked about what had happened and both agreed that we had no idea what had come over us when we started kissing. Just very lost in the moment of lust and being very horny. She asked if we should shower before going to bed, then I said that we should keep his cum on us to show you and her husband. She said she had not told Tom yet and wasn't sure if she was going to so she was going to have a shower as she was smiling at me. Walking by she said "incredible vacation, let’s start planning our next one"! Off she went to the bathroom to shower. Part of me wanted to go join her in the shower and I’m sure you were probably hoping I was going to say I did but I’m sorry babe I didn't. I think that would have made things weird between her and me when we got back home. Or maybe not but didn't want to chance it. After her shower she came out still naked and I was still naked ad well and we just kept talking about the great time we had here. She wants to go to Barbados next with me lol. Time to start planning! Lol.

We went to bed and I slept like a baby. Woke up an hour ago and writing you now before breakfast and then be on my way home to you. Can't wait to see you tonight.

Love you lots babe.

The end...

Please comment, Ann and I would love to hear your thoughts, ideas and suggestions.

[roadrunner]

That was hot! Thanks for sharing it with us!

[jthemanifest]

I'm really loving your chronicles. Great stuff.

[go2guy]

Incredibly hot! Well written too. Ann's BF is a lucky guy.

[Anns_boyfriend]

Thanks guys, we're glad you enjoy the adventures

And yes go2guy, I am a very lucky guy.

[Crza96]

My fiance and I have a little roleplay story about a masseuse. So naturally I exploded like crazy at that part. HOT.

[cb3000]

Loved the story, I could see my Wife doing that! Only difference would be that she would leave me home locked in chastity!