Jess and Me Pt. 02

After we got to the room, we decided we would freshen up and go for a walk to check out the resort. We had dinner reservations in a couple hours, so we didn't have enough time to go to the pool or anything but plenty of time to grab a drink and check things out.

As we walked the resort, we discovered there was a quite pool and then an activities pool. The quite pool was not topless. It was more conservative and a relaxing environment. The activities pool was much livelier, had a DJ and had activities coordinators playing games with some of the guest. We went to the bar overlooking the pool and got ourselves a drink. We sat down and enjoyed the sites for a little bit. There was a 50/50 mix of ladies topless and some not. I looked at Jess and said, "see no pressure to go topless if you don't want to."

"I expected everyone to be topless. I also had imagined that everyone was going to be young and hot, and they really are not," she said laughing.

"I kind of figured that was the case the way you were talking on the flight now. This is what I was expecting. Most of the people to be just normal average bodies, some overweight and then you have some that are attractive and fit."

We finished our drinks and then headed back to the room to get changed and go to dinner. The rest of the first day was pretty casual. We were exhausted from traveling and we had come down from our buzz on the plane had made us tired. We had dinner and then went for a short walk on the beach before we headed back to our room for the night.

After the first couple days in Jess and I were in full swing of the resort. The first 2 days we spent by the activities pool and engaging in the nonstop excitement of the pool, playing games, etc. Going into day 3 we wanted a more activities optional setup. Just off the pool area, as you start to enter the beach area, were a row of cabana like lounging beds like that see at resorts. We found that we really liked these for just chilling and the pool/swim-up bar was only a few steps away keeping us close to the action if we so desired. The cabana bed allowed for sun or shade depending on your mood. With the pool behind us, we could relax and face towards the ocean which made for great views and people watching.

The first day we were in the cabana we were next to a group of people that were there for a wedding. They were a ton of fun and we started chatting with shortly them after we got situated. Jess was now accustomed to being topless the entire time we were on the beach or around the pool to the point that she no longer brought her bikini top with her. The groomsmen in the group did not try at all to hide their interest in looking at her body and I enjoyed the attention she would get from them. Jess and I were talking to the bride and groom when Jess said she was going to go get a drink from the bar. She asked if we wanted anything. The bride, who was not topless, said she would go with her to the bar, and they asked us if we wanted anything. The groom and I both said we would take a beer. About 10 minutes had passed and I looked around to see where Jess and the bride were. I saw that they were still at the bar, and they were about to do a shot with a couple of the groomsman, and several other people too. I loved watching Jess standing there topless with all these men around her, letting them take in her beautiful body. Her nipples are always in some state of erection and from her side profile I could see them poking out nice and fully hard in cool shade of the bar area. One of the groomsmen was standing particularly close to her. I watched him lean into her and tell her something. Jess just laughed and looked down at her nipples and just shrugged her shoulders and said something back. Then they all did their shots. I wonder what that was all about.

When Jess and the bride made their way back, they brought the groom and I a shot to catch us up along with our beers. The one groomsman who had leaned in to talk to Jess at the bar was with them. His name was Josh. He was a good-looking guy that was around my age in his early 30's. We spent the rest of the day hanging in our cabana or hanging out with the wedding party. I noticed that Josh spent most of the time hanging with Jess and me.

Josh was a friend of the groom who lived in California. The bridal party was from South Carolina, and he had flown in alone to meet the bridal party in Cancun. He was the only one in the bridal party that did not have a date. Naturally he gravitated towards us due to the freedom of not having a date there and of course two other simple facts; First, he and I had a lot in common and we were chatting quite a bit, the second more obvious reason was he clearly was enamored by Jess as I constantly found him staring at her tits, ass, and scantily clad pussy. Who could blame him though with her laying out topless and the small camel toe that her thin white bottoms created? I was doing the exact same thing, trying to still glimpses and I got to see her nude all the time. I loved the way her pussy looked in the thong bikini bottoms. They clung and outlined her pussy lips, and you could just make out her slit. It was clear to anyone who looked at her that her pussy was smooth underneath the thin fabric. It was mesmerizing to me as I am sure it was to Josh and others.

After some time, Jess and I had come back to the cabana and we laid back on the bed, propped up by pillows, so we could people watch and take in the beautiful view. We were just chilling and relaxing when after about 10 minutes Jess crawled over to me, kneeling up over my hips and legs and put her tits in my face. I briefly, and as discreetly as you can be on a beach, took her left and then her right nipping into my mouth and gave them a quick swirl with my tongue. As I gave her right nipple a last flick I looked beyond Jess and noticed Josh was about 20 feet away staring right at Jess's ass which happened to be pointing in his direction. Jess had her back arched and her ass and pussy pointed right out at ocean, at Josh and anyone else in that direction. Her pussy was still covered of course by her thong bottoms, but it still had to be quite a sight for Josh.

I pulled her down for a quick kiss then whispered into her ear. "You are giving Josh quite the view right now."

"Hmm. Really. I guess I didn't realize," she replied in a teasing voice that completely acknowledged her deviance. She gave me another kiss and then climbed off me and we laid there chatting for a while before rejoined the wedding party.

A bunch of the people in the wedding party were going to play volleyball, so Jess and I joined them. Josh and I were on the same team, and we started talking trash with Jess who was on the other team. Most of the women put their tops on to go play volleyball but Jess, who did not have hers with her, just went topless. We got to enjoy watching her play volleyball topless and in a thong. So sexy! When the game ended everyone got in the pool to cool off and we all went to the swim up bar. Josh again was by our side, and we enjoyed talking to him. Him was actually a pretty cool guy that I could easily hang out with which I think is what made his flirting with Jess so comfortable for both of us. He understood his boundaries and that made it even more enjoyable to have him checking Jess out and flirting with her.

Josh told us that since it was their last night, the entire wedding party was going out to a club outside the resort, and we should go with them. Sounded good to us as we had no plans, and everyone was quite drunk at this point and when you are drunk you tend to just agree with every idea that comes up.

"Hey Josh, we don't exactly know where we are going or where to meet up. What is the plan?" I asked.

"Were supposed to meet up at the bus outside the west entrance at 8:00. We have a private bus taking us to the club. If you guys want to meet me at the lobby bar, I will walk with you to the bus," he replied.

"Why don't you come by the suite instead for a drink first? I'll show you the watches I brought with me and then we can head down together to the bus," I replied. Josh was a big watch fan. He had commented on my watch earlier at the beach and through conversation I had told him I brought 6 high end watches with me (I am a bit of a watch freak too) and he was very interested in them.

"Sure, sounds good. 7:30 work for you?" he replied.

"Yep, perfect."

We wrapped up, said goodbye to everyone and headed back to our suite. Jess was tired and wanted to take a shower and a nap. She stripped down and jumped into the shower. Seeing her naked with a little small thong tan line from being in the sun the last 4 days was too much for me. I quickly stripped down and followed her into the shower. We took a nice long shower talking, bathing each other. I love washing her. I stood behind her and pulled her against me. My dick getting hard between her ass cheeks as I used soap to wash her breasts, tummy and then her pussy. I played with her clit a little bit getting her turned on. She turned around and took some soap and lathered up my dick getting me fully hard. She leaned into me and said, "I see you're all worked up. All those titties at the pool got you all horny?"

"It's the set of titties in front of me that all the men were staring at that has me all worked up. You looked so damn sexy out there," I replied.

"You like it when boys check out your girlfriend?"

"You know I do. Josh couldn't keep his eyes off you," I said.

"I know, he was not shy about it either. We were at the bar, and he looked right at my tits and said, 'is it chilly in here?' I looked down at my nipples and just shrugged and laughed. He said he was sorry and that it just kind of came out. I told him no big deal. He then said, 'you do look amazing. Here is to the cold weather'. I thought that was really funny and laughed."

"I saw him staring and your tits and say something to you and wondered what it was. That is funny and hot that he said that. I invited him to come by the suite for a drink before we go out. You should tease him a little, get him all frustrated," I said

"Oh yeah? Hmm, that could be fun. What do think I should do?" she asked.

"I have not thought it through yet, but I like the idea of you teasing him and seeing how he responds. It turns me on."

"I can tell. Your guy just got very hard." I looked down and she had my dick in her hand squeezing it hard making my head nice and rigid. She had her other hand underneath my balls massaging them while she stroked my dick.

"Let get out of the shower, I want to lick your pussy."

We got out of the shower, and I literally threw her on the bed. I rolled her over on her stomach and I started kissing her from her neck down to her ass. I then kissed each ass cheek and started to kiss down her right leg then kiss my way back up her left leg. Jess has the prettiest pussy and I love how you can see it from behind so well. If she arches her back even just a little you can see it poking out. You can even see her pussy a little from behind when she is standing which is such a huge turn on for me. Laying on the bed face down, you can clearly make out her pussy and then she arched her ass up at me and I could see her entire pussy and her asshole. I wanted to eat her pussy now not just lick it. There is a difference!

"Here lift up for a second," I told her. I had her sit up on her knees. I got 3 pillows and stacked them in front of her. "Ok, now lay down on these with your hips over the pillow." It was a little too high but that is ok. This positioned here so that her ass was up in the air arched at me with her pussy very accessible. I leaned in and started kissing around her ass again and then I licked my way up her inner thigh.

I slid down and laid on my stomach on the bed and moved into position to be able to lick her pussy from behind. I started by licking the sides of her lips and slowly worked my way into her slit. She was already very wet by the time I stuck my tongue between her lips and along her slit. I then started to lick towards her clit and tease it. The angle for her clit was not very good like this so I focused on her pussy licking her hole and taking her entire pussy into my mouth and sucking on each of her smaller lips a little bit. Then I started slowly working my way up her pussy again but lightly now and I started to lick around her ass hole. As it turns out, she told me later, nobody had ever licked her ass before, and she was shocked at how much she liked it. While I was licking her ass she really started to moan and grind so I got up on my knees and I wrapped my right arm around her leg so I could easily reach under her and get to her clit with my right hand. I then took my left hand and I slid first 1 finger and then a second into her very tight but wet pussy. I started to slowly work her clit with my right fingers, then I gently fingered here while I licked her ass. As she got more excited as I began working my fingers into her and started to focus on her G-SPOT. I started by putting pressure on it and massaging it faster as I continue to work her clit while licking her asshole. It didn't take long until she had an earth-shattering orgasm.

After she came, she kind of rested there as I sat behind her lightly rubbing her ass and gently stroking her pussy lips being sure to let her overly sensitive clit rest. Oh, want and mazing sight it is to stare at her ass and pussy arched up like that.

Jess rolled off the pillows and went down on me sucking my already hard dick. She slid up me and got on top of me, grabbed my dick and slid it into her wet pussy. She laid on me with her bare breasts against my chest and slowly started to grind on my dick.

"So, tell me what you want me to do for Josh when he gets here? I like how much that turned you on in the shower."

"I am not sure yet. Does it turn you on thinking about it?"

"It does. More now than when you first said it. I thought maybe it would be too much, too obvious but while you were licking me, I was thinking about someone being in the room watching us while you were licking me and it got me very turned on," she said.

"That is hot. You have no idea how erotic you looked like that. I could just sit back there and play with your pussy and ass for hours with you in that position. Were you imagining it was Josh or just someone random watching?" I asked.

"I think at first it was just someone seeing me exposed like that is what I was thinking about but then I imagined it was him watching because of what you said in the shower. I felt so exposed the way you had my lying on the pillows I felt totally exposed and vulnerable."

"So maybe I should tie you to the bed in that position and invite him in for a drink?"

"Yeah right. Don't get any crazy ideas like that," she said jokingly but at the same time with serious tone. "Hopefully you were not thinking of something that extreme when you invited him up here," she added now cautious about what I had in mind.

"No babe nothing like that at all don't worry. I am not sure what I was thinking but I thought it would be fun to tease him somehow since he clearly is very taken by you. I am not trying to setup a threesome or anything with him, but I thought it would be fun to do something you know."

"Ok good. I started to get a little worried there," she started grinding on my dick again as she had stopped moving during her questions of concern. "So, you must have something in mind then."

"Well, he has already seen your tits so that wouldn't be too surprising if he got a glimpse of them but at the same time, seeing someone's tits on the beach where other people are topless is quite a bit different then seeing them in an unexpected setting. Do you want him to see your pussy?"

"I don't know. Is that what you want?" she asked.

"Yeah, I kind of do. I think I have an idea but only if you want him to see your pussy."

"Tell me what your idea is and then I will tell you," she said as she was still slowly grinding on my cock.

"Well, my mind is kind of jumping around now with different ideas. At first, I was thinking something like a loose rob or you in a thin t-shirt while you were getting ready to go out and then he comes in and sees you in that outfit and gets a glimpse. Now, after all this talk and you grinding on my dick, I have a different idea that is much more bold but not sure you will want to do it. It might be too much," I said.

"Tell me, I'm getting excited waiting to hear what you're thinking. Your dick feels really good right now, I might cum again if I keep grinding like this."

"What if you were just nude and still getting ready when he got here? But instead of it being like an oh shit he accidently caught you nude or he got a brief peek, you just go around being nude, going about your business as though it is just completely natural that you would be nude. You finish getting ready nude because that is just natural for you regardless of if he is in the room or not." I told her.

"Oh wow. I was not expecting that. I thought you wanted me to drop my towel or let him see up my robe or something like that," she said kind of laughing a little. "That is a lot more then what I was thinking. I don't know if I could do that the way you described it."

"I know It's kind of allot but that is the vision I have stuck in my mind right now. I want to see his face when he sees you nude and I want him to get a good look. I want him to go to the party tonight and tell his buddies that he got to see you nude. They will all be jealous, and all get boners thinking about you nude."

"Oh babe. I'm going to cum...." She said as she had her second orgasm and then she relaxed on top of me. It took her about a minute to catch her breath and then she started to move again on my dick.

"Wow that came on quickly. I was not expecting that," I said to her.

"I know. I was getting turned on talking about it but then when you described that, having you guys look at me nude it just immediately pushed me over the edge. I was a bit surprised too that it turned me on so much." She leaned into my ear with her mouth and said quietly, "Do you really want him to see me nude?" I just shook my head yes and raised my hips to push farther into her pussy. "You want him to see all of me from head to toe?" she teased.

"Yes."

"You want me to stand in front of both of you and talk with my fully body on display for you two?"

"I think that would be so hot."

"You want him to see how smoothy my pussy is don't you?"

"Oh my god you're going to make me cum," that was all I could take. Hearing her describe her pussy for another man to see was too much. It put me over the edge.

We both lay there for a little while and took a short nap. When the alarm went off Jess got up and rinsed her body off in the shower. I watched her as she put lotion on, and I just admired how sexy she was. She really was a goddess.

I finally got up to get ready myself. I poured her some champagne to sip and myself a drink. Figured a little liquid courage to start the buzz back up wouldn't hurt my chances of this actually happening. Our suite had a separate "hair/makeup/dressing" type table just outside the bathroom but still in the bedroom. It was located directly in line with the living room area so if you are in the living room area looking into the bedroom you look directly at the dressing table. If Jess were facing the mirror getting ready and we were in the living room sitting area, we would be looking into the room and would see her back. As I watched her sitting there getting ready, I thought this would be the perfect angle for Josh and me to sit to get a glimpse (or hopefully more) of Jess getting ready. Regardless of the degree Jess was willing to go with this if Josh and I sat or congregated in this area It would not be too obvious for us to just catch glimpses of her while she is getting ready. That might be more comfortable for her, and it was definitely more natural of a setup. I brought it up to her to see if she was still up for my little fantasy.