Jess and Me

If you read the previous story, then you know that there are a few fetishes that really drove Jess and my relationship. They also developed into the catalysts of our sexual exploits through the years. The first story was how we opened the door to our mutual obsession with cock size. We will expand up on that as these stories continue but exhibitionism is the other dominant obsession that we both share. This story will focus on how we started to openly discuss exhibitionism and some of the earlier exploits that occurred.

To catch you up if needed, Jess is 5'6" tall, long blond hair, dark eyes, full firm breasts, a nicely long torso, flat tight stomach, long legs, perfect ass, a gorgeous tight small bald pussy with beautiful lips and a killer almost innocent smile to top it off. It literally was not until our first Cancun vacation that I realized just how beautiful she really was. Jess was standing by herself drinking a glass of wine waiting for me. I was about 50 feet away talking to someone when the guy paused, looked at Jess then said to me, "she is the most beautiful woman here." I looked over at Jess and it was then that I really took in just how beautiful she really is. I turned to the man and said, "you know the best part of it is? She does not even realize how beautiful she really is and is as beautiful on the inside as out." I meant it too. She knew she was hot and sexy but not in a conceded way and she did not realize how intense her beauty really was.

One thing that Jess did learn early on is that men liked to look at her and she enjoyed that. When she was younger, she said she had more of a slender dancer's build with small breasts, long legs, etc. She said she could always go without a bra because there was not much there to support. She would always wear a tank top around the house with either shorts, panties or sometimes nothing else on underneath her night shirts. Around when she turned 18, she continued to wear the same clothes but noticed how much attention she would get from men now that she had fully developed more into the build she has today.

We did talk a little bit about her exhibitionist side prior to this email chain and of course being together for 6 weeks at this point I had witnessed some of that behavior myself. So, this is conversation was me wanting to learn more about what she likes or would be willing to do. I love the idea of showing her off. I love how sexy she dressed when we would go out and I loved that other men would stare and look on with desire in their eyes. I was very excited to get her to someplace like Cancun where we could explore this side of her more. So here we go...

So, like last story, here is an early email chain regarding exhibitionism prior to us going on our first Cancun trip discussed in the first story. This is around 2005 when these conversations took place. Flip phones were the thing then. If you were in business, you had a Blackberry, but most people had flip phones. So texting was not as popular at the time. At work, messaging apps were blocked so we used to email a lot to communicate during business hours which is why the emails read more like a text message exchange then emails. Like before I have reformatted them to just the relevant conversations, but this is the actual email exchange that occurred between us.

Keep in mind that we had only been dating about 6 weeks and Jess was still only 20 at this point.

JESS: What are you doing?

ME: Looking at resorts in Cancun.

JESS: Seriously? I didn't think you were serious about that.

ME: Hell yeah I am. I am so ready to get out of this cold weather and get you on a beach in a bikini! You do want to go right?

JESS: Yes of course. I have never been there.

ME: Its fun. I love it there. Easy to get to, great prices, great parties, lots of fun! I want to find an adult only resort that is a bit on the wild side. Not Hedonism, not that crazy, but also not something like a Sandals or laid back either. A little edgy and wild.

JESS: That sounds fun. I don't know anything about Cancun, so I am no help at all.

ME: I think I found a resort. It's called Blue Bay Get Away. Its adults only, it has 2 main pools. One is a quite pool the other is a party pool. It is topless but not clothing optional and it sounds fun. It's also a very nice high-end resort. Here is the link check it out.

JESS: Wow that place looks amazing. You are serious about this aren't you?

ME: Well yeah. Why don't you believe me?

JESS: I don't know, I have never dated anyone that wanted to go to Cancun with me before. I am not sure I can afford it though.

ME: Don't be silly. You know I would never let you pay for anything like that. We just have to figure out the dates and I will get it booked.

JESS: You are amazing. I have definitely never had anyone pay for me to go on vacation before either. This is all very new to me, and I really don't know how to respond. It's a little bit overwhelming.

ME: Why? I'm your boyfriend and I want to take you on a trip. If we're going to date you had best get used to it! I want to go soon, like in 2 weeks. Just go for a 4-night trip long weekend. You only have to take 2 days off. What do you think?

JESS: Ill check but I am sure it is fine. I have a bunch of time built up. Wow. This is insane. This place looks amazing, and it does look wild!

ME: We need to get you some sexy bikini bottoms (you won't need your tops) and some sexy clothes for the trip.

JESS: You are funny! Just bottoms only huh? You think I am going to run around topless in front of a bunch of people I don't know?

ME: Yep, I sure do. A body like yours was meant to be seen.

JESS: I don't know if I could do it. I will have to see when we get there.

ME: What do you mean? You love looking sexy and you told me you like it when guys check you out. What about that party you were at when everyone went naked in the hot tub? You said you loved it being nude in front of everyone. I thought you liked that stuff.

JESS: That was different. I knew everyone and we were all very drunk.

ME: You will probably be drunk in Cancun too. I thought you would be up for going topless. I thought you would like that. Maybe we should go to a different style resort then.

JESS: No, this one looks fun. I am sure I will be ready to loosen up once I get there and get a drink in me, but I am bringing my tops with me not just the bottoms.

ME: You have gorgeous tits! I'd love to see you topless at the resort. That would turn me on.

JESS: Thank you babe. I am sure if everyone else is doing it I will too. It just caught me a little off guard is all. You move so fast! It was like, 'good morning' and then we got to 'topless in Cancun' in like 30 seconds. But I am sure this trip is going to be amazing. I am very excited

ME: You know you like to show off your body. You told me that. Also, you will never see these people again. The women will be jealous of you and the men will all have boners! Common admit it. Your pussy is tingling a little thinking about being all hot in the sun. You have your sunglasses on, your hair is up. Your body is glistening in the sun and the only thing on is some little bottoms. Your tits are completely exposed to everyone, your nipples can feel the cool breeze. We go up to get a drink and bartender can't take his eyes off your tits. As we walk back to our chairs holding hands, I notice how the men are catching glimpses of you and adjusting themselves. Now tell me that don't turn you on.

JESS: Wow. That is so vivid and hot. I could totally see us doing that. It's very hot. I want to fuck now!

ME: That's the spirit! So, think about it, you could have a sexy cover up, its slightly transparent. You put it on to go back to our room and as we walk through the hotel you can kind of make out your nipples through the cover up. Its vacation in paradise, it's not like here. You can completely let loose, and nobody is every going to say anything and you never have to see them again. How hot is that?

JESS: You have this all worked out, don't you?

ME: Yes of course. Common, tell me that doesn't turn you on thinking about it?

JESS: Yes.

ME: Why were you being so reserved? You already told me you like to show off your body.

JESS: I know but this is different just being topless walking around a bunch of people. I have never done that kind of stuff before.

ME: So, you like smaller audiences?

JESS: LOL. Kind of, I guess. I just have never been around a bunch of strangers almost nude. I have always had clothes on, and then I let someone steal a peak or I let more skin show then I am supposed to show. That kind of stuff.

ME: Like wearing a low-cut top showing cleavage? I love how your tops always show your cleavage. So sexy.

JESS: Yes, I like that too which is why most of my tops show cleavage. LOL

ME: How else do you like to show off?

JESS: Maybe a loose top with no bra that I know you can see down if I bend over or lets my nipples poke through.

ME: When is the last time you did that?

JESS: Went without a bra and bent over? I don't know exactly but I do it all the time. If I run to Starbucks in the morning, I almost always throw on a loose shirt with no bra and I have some V-necks too I wear sometimes. I don't try to hide it you know. If you get a look, you get a look. Its more about the guys in line then it is the workers.

ME: So, you don't really try to flash you just know that someone might get a look?

JESS: Well that too but sometimes, if I know someone is kind of looking, I will give them a chance to see down my shirt. The fabric is thin so you can make out my hard nipples easily in it. Some guys are just glued to hard nipples and if I see someone taking peeks and they don't look like a serial killer I will try to give them an extra peek. If there is a guy trying to catch a glance when I am at Starbucks, I will lean in to look at those drinks and little lunches they have in the that cooler in the line.

ME: Tell me about a time when you gave someone an extra peek.

JESS: I went to the Verizon store to get a new case. I wore a light pink loose shirt that had a loose V neck collar. I was leaning over looking at the cases and this guy came over to help. I stood up and told him what I was looking for and his eyes went immediately to my nipples poking through my shirt. So, I told him I was looking at these and I leaned forward to show him. I could see out of the corner of my eyes that he was looking down my shirt. I kept looking around trying to give him some peeks. It was fun because he was flustered and not sure how to act. I even stretched a few times pressing my tits against my shirt. It was actually quite funny.

ME: That is so hot. Did it turn you on to do that or was it just funny to you?

JESS: Both. I did think it was really funny though. Guys can be so simple, and he was young. Older guys are more fun to tease because they usually are not as blatant about it because I think it is kind of taboo for them.

ME: Is that how you usually flash then? With peeks down your shirts? Have you ever flashed your pussy?

JESS: No not just like that. And yes.

ME: Tell me about it?

JESS: Which time? LOL

ME: Oh boy! All of them!

JESS: Does this turn you on?

ME: YES!! I love it!

JESS: You do like to stare. You are easy, you are always checking out my tits and you are always trying to see up my skirt or my shorts even though you can look at me nude anytime you want.

ME: I like to try and see what other men see.

JESS: And have you seen down my shirt or caught a glimpse up my skirt?

ME: Yes, and yes. Those little burgundy running shorts you wear all the time around the house on the weekends are the best. You can always catch a glimpse up those or they might pull over when you sit down, and you can see clearly that you shave your pussy!

JESS: I love those shorts. They are my favorite.

ME: Because they are comfortable or because you can flash your pussy in them?

JESS: Both.

ME: So, you have flashed your pussy in them before?

JESS: Yes, but mostly I just wear them, and I know that unless I am being careful someone is probably going to get a glimpse. But they are comfortable for me because I like that and most of the time, I am not evening thinking about it anymore, but it turns me on sometimes when I think back and was like, "Hmm, I bet he got a look at my pussy, and I didn't even know it."

ME: Who is the "He?"

JESS: Oh, I don't know, you know what I mean. Like, just someone probably got a peek.

ME: You had someone in mind.

JESS: Well to be honest I know a few times when I flashed my pussy, and I didn't even realize it and I was not trying to at all. It just happened and I was really embarrassed but later it turned me on. You will think I am horrible though if I tell you who it was.

ME: Ok, enough of that. You should know by now I am not going to judge you and you better tell me who it was.

JESS: Ok but you can never tell anyone. I am totally trusting you. It was about a year ago and I was at home. It was in the morning, and I got up and I put my shorts on with a t-shirt. Nothing revealing about the t-shirt, but the shorts sometimes can be revealing, and I don't even know it. My mom's boyfriend Tim was already up, and he was in the living room in his chair drinking coffee and reading the paper. I grabbed some OJ, and a breakfast bar and I sat on that couch by the kitchen [the couch she is referring to is just to the right of the chair putting it on about a 45-degree angle from the chair Tim was in]. flipping through channels on the TV not really paying attention while I was eating. I reached for my drink, and I saw that Tim was looking my way and then looked away. I totally know that look away that men do when they are taking a peek, so I nonchalantly gave myself a look over. I was sitting with my left leg under me kind of and my right leg stretched out. I guess when I sat down my shorts kind of flopped over and most of my pussy was exposed. I was not fully on display, but you could make out the whole left side of it so, basically it was on fully display. As soon as I saw what he was checking out my entire face went flush, and my stomach immediately turned upside down in a panic. I totally did not mean to flash him that much and I didn't know what to do so I reached back and put my juice down and I straightened out my left leg which essentially blocked his view. Then a few minutes later I got up and I went to my room.

ME: Holy shit! I was not expecting that. I thought you were going to tell me you dropped your towel for the pizza guy or something like that. So, Tim saw your pussy?

JESS: He must have. I swear that is where he was looking.

ME: Was it pulled over far enough so he could see to your slit?

JESS: When I looked down, I could see my slit and a little of my lips so I am sure he could see the slit for sure.

ME: OMG that is hot. How long were you sitting like that?

JESS: For at least 10-15 minutes. I mean it was right there and he was only like 8 feet away.

ME: Wow! Did it turn you on?

JESS: Mostly I was just panicked. It makes me nervous just talking about it like I am going to get caught. I felt like my mom was going to walk in a catch me and kick me out of the house. I mean, they have been together like 7 years, and they are practically married. Last thing I wanted to do was to come between them.

ME: Yeah, I get that. But it's not like you were trying to do it. It just happened.

JESS: Yeah, that is what I told myself, but I didn't wear those shorts around the house for months after that and started wearing a heavier robe in the morning.

ME: So, it didn't turn you on at all? I mean that is what you really like is that candid experience and right there you got one. Be honest, it had to turn you on.

JESS: It did not at first because it scared me so badly. The next day though when I saw him it started to hit me that he got to see my pussy. Then I started wondering how many times something like that happened and I gave a peek and never realized it. Thinking about that was some of a turn on.

ME: Did you start to fantasize about it? About what he saw and if he liked it?

JESS: Yeah, a little. I just kept wondering to myself if he thought it was sexy or if he thought it was gross. It would make my stomach feel like butterflies when I would think about it for the longest time. I kept thinking; I wonder if he is comparing me to my mom which I could not get out of my head at first.

ME: He had to of thought it looked hot. I mean common, you're hot, you pussy is gorgeous. Any man would die to see your pussy. Believe me he was not grossed out and if he was comparing you to your mom then that means it turned him on. So, I know you don't still wear a robe around him because I have come by in the morning and seen you in those shorts. Did you flash him again?

JESS: Well, my mom and Tim never brough t it up so I just figured either he did not see, or he liked it or maybe he just didn't care. Either way I just figured it was an accident and I like to wear my shorts and feel free like that. If he gets another peek, then so be it. If he does not like it, he will say something to me. But I have not intentionally tried to flash him, but I also don't avoid it. So, who knows if he has seen anything since?

ME: I bet he has. Those things pull up all the time. I can't see your whole pussy, but I can see the edge of your pussy almost every time. I am sure he has seen the same.

JESS: Really? That much huh? I knew they rode up, but I just thought it showed some ass cheek more than anything.

ME: For the most part it just looks like they rode up on you and you can tell you have no panties on. It's not like obnoxious or anything.

JESS: Ok good because I like to wear those a lot when I am lounging.

ME: So, Cancun will be fun then because there will be plenty of opportunity to be exposed. I am looking forward to it.

That was the first extensive conversation we had about her exhibitionist side. For me it was very exciting, and I knew that Cancun was going to be a blast and filled with the freedom and opportunity to explore this further. We didn't go to Cancun for 3 more weeks from this conversation and there were more discussions and some casual events of her exhibitionism, but it was in Cancun that we really got our first taste of how far we would go to sh0ow her off.

I am going to try to keep this story to point of the one big event that happened in Cancun. There were more small events that I'll summarize at the end but won't go into deep detail about how they came about. The one big exhibitionist event though will get its due with full description of how that came about. To this day, as far as just a "pure exhibitionist" event, this was by far my favorite.

When we got to the resort it was early evening. We got to our rooms and Jess freshened up a little bit and then we decided to take a quick walk around the resort. For the flight down Jess had worn a long sundress. It was a light material and there was no hiding the fact that she did not have anything on underneath it. She wore a light crop style jean jacket with the dress so she would not be cold at times but for the most part she did not wear it. You could clearly see her hard nipples pushing through the material. It was a soiled earth tone greenish color, and it did nothing to hide her very erect nipples. Of course, I loved this. So did the flight attendant. We were in first class in the second row, and he was at our side taking in Jess's nipples more than anywhere else on the plane. We got pretty hammered on the flight down most of it due to all of his attention getting us drinks every 10 minutes.

As we walked through the airport you could tell by the way the dress hugged her ass that she did not have any panties on. If she had panties on you would have been able to see the lines of the strips that come around her hips but all you could make out were her hip bones and anyone who knows what to look for could tell that she was commando under her dress. I just love her sexiness and willingness to play these games with me I knew the trip would be fantastic.