Jess and Me Pt. 02

Jess was wearing a thin robe while she was finishing her hair and was just starting on her makeup. I walked over to her and asked, "So are you still up for a little fun with Josh or did that wear off after your orgasm?"

"I was waiting for you to say something. I was just thinking about that myself. Playing it out in my head you know. I am not sure if I can go all out the way you described it. I have butterflies thinking about it and I will probably chicken out. Maybe I could just keep this robe on and let it open up at the bottom or something like that. Let him get a little accidental peek. I know that is not what you were thinking but I am all nervous now and not sure I can be as confident as you described earlier," she replied.

"There is no pressure babe. It's a fantasy in my head and if you are not up for it no worries. Whatever happens, happens? You look perfect and so sexy in that thin robe. If you want to play a little with that, I would be very happy. I don't want to force you into anything and make you uncomfortable. I want it to be something you want to do too. Not just something to do for me. Whatever you are comfortable with is good with me. "

"Ok, I'll play around with the sash and see if I can get it to gap in a way that isn't too obvious but still lets him see me. Either way, I do have to hurry because I am actually running late now for real!"

She was right, I checked my watch and Josh was supposed to be there in 10 minutes. Being the devil I am I went to our mini bar and found us each a shot of tequila. She does not really like tequila shots, but this moment called for desperate measures. I took it into her and gave her one and said, "Maybe some liquid courage will help."

"Ugh. I hate this stuff. Isn't there anything else?"

"Nothing that will give you the kick of courage you need. It's one shot, just put it away and chase it." We said cheers and threw them back. Jess did not exactly enjoy it, but she finished it. Jess went back to getting ready and I went into the sitting area just outside the bedroom and rearranged the two chairs so that they both had an equally good view into our bedroom where Jess was getting ready. I moved the end table in between the chairs so it looked natural. I pulled the loveseat to the other side of the room so that nothing obstructed our view into the bedroom.

Then we heard the knock at the door. Jess immediately turned to me and looked at me with a very nervous face. At that moment I felt bad like I was forcing her to do something she did not want to do so I said, "Babe don't worry about it. You don't have to do anything at all. Just keep your robe on and finish getting ready. That in itself is sexy as hell, and it is more than anyone else in the world would do for me. So just keep doing what you're doing and don't worry."

She just turned back around to the mirror and said OK in a kind of defeated tone. Now I felt like a jerk like I made her feel bad. Ugh! I went to the door to let Josh in.

"Hey there, common in," I said.

"I grabbed this Tequila Monday when we went on an excursion. I didn't know what we would be drinking so I thought you guys might want to try some. It's really smooth you can sip it or do it as a shot." he said as he handed me the bottle. He looked around the room and said, "Damn this suite is bad ass. We just have standard hotel style rooms. Nothing like this."

"Thanks. Yeah, it's pretty nice. I like not feeling cramped so it nice. Here, come on in. Jess is still getting ready so it will be a few minutes yet," I said as I led him over to bar area. This put us with our back to the bedroom so he would not be able to see Jess just yet. I looked over my shoulder and said, "Jess, Josh is here. He brought some tequila. Come do a shot with us."

"Hey Josh! Give me a second to finish this eyelash," she replied back.

I got the glasses out and Josh started pouring us a shot. I picked up two of the glasses; one for Jess and one for me. Just as I turned to call her name again Jess came out of the room completely nude, no shoes, nothing, just completely nude. So much for catching Josh off guard...she completely caught me off guard and my jaw was hanging to the floor! I had the composure enough to close my yap just in time to see Josh turn around and see her. He was just as caught off guard as I was. His jaw dropped too, and I noticed his eyes scan her from head to toe.

In perfect timing Jess walked over without missing a beat like she was already dressed to go out and said casually as if she would of at the pool, "Hey Josh, great to see you. Sorry I am still getting ready. We fell asleep and completely lost track of time. I'll be ready in a few minutes or so." As she said this she walked up and took the glass from my hand. "To James and Tammy?" she toasted to the bride and groom. Josh and I agreed and the three of us said, "To James and Tammy", clinked classes and did the shot.

"Wow that was rough. Ugh, I need to take it easy, or I am not going to be able to make it through the night." Jess said, she handed me the empty glass, stood up on her tip toes and kissed me on the cheek and said, "Ok, I have to finish. Be out in a jiff."

I was all butterflies inside and my cock was almost completely hard in my pants. Where did that come from, I thought? I could not have planned that better and I was so turned on. I don't know if Josh got a real good look or not, but I sure hope he did because I could not wait to talk to Jess about it as soon as we got a chance. At this point I just went with the plan and directed Josh to the chairs and said, "Here let me show you the watches I brought with me."

He sat down and immediately I could tell he noticed you could see into the bedroom to where Jess was putting makeup on. The mirror went from the tabletop up to ceiling and she was now standing in front of the table and mirror with her back to us instead of sitting down in front of it like she was earlier. What a damn fine ass that girl has! As I said before, Jess has one of those pussies that you can just make out when looking from behind. Even when she is not trying to stick it out by arching her back you cand clearly make out her pussy lips. So, from our angle sitting, we could make out her pussy lips even better than you usually would if you were standing. We were seated only about 15-20ft from her, so it was not very far at all. Her ass was just so beautiful, and she had the best tan line from her thong making it even more sexy.

I got up and went to go get my watches to show Josh. As I got up to get them, I could see Josh in an adjacent mirror and his eyes were glued to Jess. I grabbed my travel case that had the watches in it from the room safe and then I grabbed 2 beers from the bar and brought them to where we were sitting. I handed the watch case to Josh and sat down beside him. As I started to show him the watches, Jess walked to the bathroom. To do this she had to turn and take a step towards us before making an immediate right turn into the bathroom. It was a quick move and by the time we both noticed the movement and looked up, she was already turned and heading into the bathroom. I doubt he saw much because I didn't see much either since it was such a quick movement.

We went back to the watches, and he was looking at one and I was telling him about it when Jess said from the bedroom, "That is my favorite one." We both immediately looked up and Jess was no longer looking in the mirror but was standing in the doorway now facing us only 8-10 feet away. From our angle sitting down we had the perfect vantage point to see her pussy perfectly. She was standing with her feet slightly apart holding her mascara. Her adorable slit and those beautiful smooth lips were perfectly visible. She has small inner lips that don't really hand down, but you could make those out too from our vantage point too. She then said, "He almost didn't bring that one with him and I asked him to bring it for me. I think it looks very manly and powerful," she said. We both never took our eyes off her as she was talking. If he didn't get an eyeful of her pussy now, then shame on him. Jess then turned around and went to the mirror to finish her makeup or whatever she was doing.

Josh and I finished looking at the watches and I put them away. I came and sat back down, and we were talking and enjoying the beer along with the sight of Jess's nude ass across from us. Then Jess did something I did not expect. She leaned forward into the mirror to put makeup on, and then she arched her back sticking her ass out some toward us. She held this position for like 20 seconds, then pulled away from the mirror and stood straight up again. She did something with her makeup on the table and once again leaned forward doing the same arching motion with her back and ass holding that position for another 20 seconds. She did this 4 separate times, each time we were treated to the most amazing view of her ass and pussy from behind. Once again, I keep pointing this out because it was very important that you understand this, being seated put us on the PERFECT angle and we could see perfectly between her legs at her pussy exposed as she arched her back and leaned forward. The last 2 times she leaned forward; she was actually on her tip toes a little giving us even a better angle. It makes me hard right now just thinking about it. That was one of the most erotic things I have ever seen a woman due. Makes me hard every time I think about it.

Jess then turned and went to the bed and picked up a tiny thong from the bed. She slipped it on, then we both watched her as she slipped her dress on over her body. It was a tight clingy number that hugged her body and came down to about mid-thigh. She slipped on her heels and did a few more things and then turned and went into the bathroom. When she came out, she said, "Ok, I'm ready," just like she was behind a closed door the entire time and nothing unusual had just taken place. She played it out perfectly.

That event is the main thing I wanted to share but I will share a few more tidbits from that night and the trip. Unfortunately, there was no exciting threesome or anything like that. We had only been dating about 9 weeks when this happened and our adventures into that world did not happen until after about a year of dating. But the night and trip still had some fun things worth mentioning. One of them was at the club that night.

We went to this club and after some drinking, chatting, etc., everyone was dancing. The main dance floor had this raised section in the middle of it. The raised section held about 40-50 people, so it was pretty big, and it had 4 sets of stairs leading up to it, one from each side. Jess and some of the brides' maids had made their way to the dancefloor and that stage. A few of us guys were out there too but the guys didn't go up on the stage. One of the great things about the stage was that while standing on the main floor you could see up Jess's dress easily. She had the tiniest thong panties on that barely covered her pussy. You could make out just the outer edge of her bald lips if you got the right angle and she held still long enough.

I had been on the main floor dancing with Jess at first. When her and the girls decided to go to the raised level I kind of backed away to just off the dancefloor and enjoyed the view of watching them and everyone else in the club dancing. There were two younger guys that were standing on the lower dancefloor, and both were looking up and watching Jess dance. Here and there they probably go a quick glimpse of her ass and maybe her panties and I am sure they were enjoying it immensely. One of the guys was holding a digital camera (pre smartphone days) and he took a picture of Jess dancing. Then him and his friend looked at the picture. I think he was trying to act like he was taking a normal picture but had hoped to maybe get a little bit up her skirt as well.

I walked over to them and said, "Here give me your camera, I'll get you a good picture." Now remember I am big guy, 6'5", bald and in good shape so the guy kind of looked at me like, oh shit we're in trouble. I said "Don't worry she is my girlfriend, I don't mind. I'll get you a good picture." He looked at me and handed me the camera. I yelled out to Jess to get her attention and then I told her to turn away from me. She looked confused but she did what I asked, and I took the camera and took a picture right up her skirt for the guys. Jess turned around with a big, surprised look on her face right after the flash went off and then said, "Let me see it."

She squatted down to look at the camera. This view right now is hard to explain but have you ever seen when a girl squats all the way down in a pair of heels and dress or skirt? Her ass will kind of rest on her heels in this position. When they do this, their pussies are point down like they are going to pee. Well, when jess squatted down you could make out her panties pulled tight against her pussy as she was looking at the camera. I am not sure if they noticed but I certainly did. Anyway, Jess looked at the picture, rolled her eyes and went back to dancing.

I looked at the picture with the guys and it was a nice shot up from between her legs of her bare ass and her panties were shifted enough that you could make out almost her entire very smooth right pussy lip. It was an incredible upskirt picture shot that is for sure. You should have seen their faces. They were in heaven. I gave him the camera back and said, "There you go. Think of it as a souvenir. No more pictures though, ok?" He shook his head yes and shook my hand and said, "You are a lucky man."

The other fun thing that happened was on our last day at the resort. Jess wore a pair of pajama shorts that were tight like boy shorts as her bathing suit bottoms. They had this cute little belt on them, her ass cheeks hung out and they tended to ride up on her give her a small camel toe. The best thing is that they were a light beige color and when they got wet, they were not fully transparent, but you could definitely see through them and see her bald pussy. We were in the pool at the swim up bar and hung out there for about an hour. Then we got out to back to our cabana area to go get some lunch. I told her I wanted to go first so I could watch her walk over and see how noticeable it was. Jess agreed and she dove under the water and swam over to the stairs area about 10 feet from us. I jumped out by the bar and went over to the cabana to wait for Jess.

As she got out of the water her bottoms were plastered to her. She adjusted them so they were not so stuck to her, but it did little to help the transparency. It was not like perfectly see through but if you were looking you could make out her pussy slit no problem. She came over and asked me, "Well how obnoxious is that?"

"It's not too bad. It's definitely something you can't wear at a public beach but it's not like fully transparent and as you walk you can tell you can see through but not see too much. When you stand still you can make out more. It shows just enough actually."

Jess laid down on the chase by me. I got up and went to go get us some snacks too much on. When I had come back Jess was talking to 3 guys from Italy. One was holding a soccer ball and they were all young like in their early 20's. I walked up and they just said that they wanted to see if they could get a picture with Jess, and she told them they would have to wait and ask me. I told them sure, here I will take it for you. They gave me their camera and the 3 of them sat on the chase and took a picture of Jess in the little shorts and of course she was topless. It was very hot, and they were in heaven. Of course, I completely enjoyed her being shown off like that and she enjoyed the attention.

It was one hell of a trip filled with a ton of fun. We went back to Cancun 3 more times in the next 2 years. 2 more times to the same resort and the last time we went to a completely nude resort in the River Maya area. Those stories are filled was some great stories that I look forward to sharing...but were not there yet.